Abstract
This study employed a widely targeted metabolomics approach combined
with flavoromics evaluation to systematically analyze dynamic metabolic
variations under four processing techniques: fresh EUL (XY),
traditionally dried EUL (HG), green tea processed EUL (GT), and black
tea processed EUL (BT). A total of 1839 non-volatile metabolites and
289 volatile metabolites were identified. Key affected metabolites
included amino acids (e.g., essential amino acids upregulated 90 % in
HG), lipids (oxidized fatty acids elevated in BT), phenolic acids (23 %
increase in GT), flavonoids (120+ downregulated in BT), nucleotides,
and terpenoids. Each processing method demonstrates unique advantages:
HG preserves amino acids, GT enhances catechin content, and BT
optimizes secondary metabolites. This study provides the first
comprehensive metabolic map of EUL processing, offering a scientific
foundation for standardizing product quality and developing functional
applications.
Keywords: Eucommia ulmoides leaves, Tea, processing method, Widely
targeted metabolomics, Flavoromics evaluation, Functional metabolites
Highlights
* •
Eucommia ulmoides leaf tea from different processing methods were
characterized by widely targeted metabolomics approach.
* •
A total of 2127 (non-volatile and volatile) metabolites were
observed in differently treated Eucommia ulmoides leaf tea.
* •
The BT treatment helped release secondary metabolites (e.g.
flavonoids and alkaloids, etc.), but it reduced amino acids.
* •
The GT treatment could enhance the content of flavonoids, phenolic
acids and tannins.
* •
The HG treatment method effectively retained some of the original
substances in XY.
1. Introduction
Eucommia ulmoides leaf (EUL), a dual-purpose medicinal and edible
resource from the Eucommiaceae family, has been documented in the
Chinese Pharmacopoeia for its traditional therapeutic effects in
nourishing the liver/kidney, strengthening musculoskeletal function,
and regulating blood pressure. Contemporary pharmacological studies
have further elucidated its multifunctional bioactivities, including
antihypertensive ([33]Guo et al., 2020), antidiabetic, antioxidant
([34]Li et al., 2022), and anti-osteoporotic properties. With the
rising popularity of EUL-derived tea products, comprehensive
characterization of its bioactive composition under different
processing conditions has become a research priority.
Existing studies predominantly focus on conventional chemical markers
(e.g., total flavonoids, chlorogenic acid) in specific processing
methods ([35]Peng et al., 2021; [36]Shi et al., 2022). However, these
analytical approaches provide fragmented metabolite profiles, failing
to capture the holistic metabolic reprogramming induced by processing.
Such limitations substantially hinder our understanding of synergistic
effects between processing parameters and functional components, thus
constraining the value-added utilization of EUL resources.
Emerging advancements in metabolomics offer promising solutions. Widely
targeted metabolomics analysis, a novel approach amalgamating the
expansiveness inherent in nontargeted metabolomics with the precision
of targeted metabolomics([37]Lozada et al., 2023), has demonstrated
exceptional performance in tracking metabolic dynamics during food
processing ([38]Baky et al., 2022; [39]Dossou et al., 2022; [40]Gaffney
et al., 2021; [41]Nguyen et al., 2024; Y. [42]Xiao et al., 2022). This
study pioneers the application of this approach to EUL processing
research. Through systematic analysis of non-volatile/volatile
metabolomes of EUL from different processing, integrated with
flavoromics evaluation, we aim to address three critical scientific
questions: (1) processing-specific regulation patterns of
characteristic metabolite networks in EUL; (2) directional
transformation mechanisms of key functional components (amino acids,
phenolic acids, flavonoids); (3) correlations between process
optimization and product quality enhancement. The findings will
establish a theoretical foundation for standardizing EUL tea production
and developing functional food products.
2. Materials and methods
2.1. Materials and reagents
EUL was obtained from the plants grown at the Jishou University
planting base in Jishou City (109°72′E; 28°32′),(Hunan Province,
China). Species: E. ulmoides Oliv.; Month of harvest: June.
Methanol (MeOH), acetonitrile (ACN), and n-hexane (Hex) for liquid
chromatography grade solvents (HPLC) were purchased from Merck
(Darmstadt, Germany), and formic acid was purchased from Sigma Aldrich
(St. Louis, Missouri). Analytically pure sodium chloride (NaCl) was
obtained from Sinopharm Chemical Reagent Co Ltd. (Shanghai, China).
2.2. Processing of EUL prepared by different processes
2.2.1. Fresh leaves (XY)
Fresh EUL, with a consistent size, were carefully harvested and
subsequently washed twice using distilled water.
2.2.2. Low temperature drying (HG)
HG Preparation Process: fresh EUL (1.67 kg) → low temperature
drying(75 °C, 3 h)(selected per Chinese Pharmacopoeia guidelines to
protect heat-sensitive compounds).
Following the guidelines outlined in the current Chinese Pharmacopoeia.
2.2.3. Processing in operating procedure of black tea (BT)
BT operating procedure: fresh EUL
(1.95 kg) → spreading(11h) → withering(28 °C,
8 h) → rolling(25 min) → fermentation(28 °C, 5 h) (optimized based on
preliminary trials to balance enzymatic oxidation and metabolite
preservation) → low temperature drying(75 °C, 2.5 h) (selected per
Chinese Pharmacopoeia guidelines to protect heat-sensitive compounds).
2.2.4. Processing in operating procedure of green tea (GT)
GT Preparation Process: fresh EUL
(1.26 kg) → spreading(1 h) → removing(100–120 °C,
4.5 min) → rolling(10 min) → low temperature drying(75 °C, 3 h)
(selected per Chinese Pharmacopoeia guidelines to protect
heat-sensitive compounds).
Samples were weighed, frozen in liquid nitrogen, and stored at −80 °C
for further study.
2.3. Sensory evaluation
The sensory evaluation was approved by the Ethics Committee of Jishou
University (Approval No.JSDX-2024-0131), and written informed consent
was obtained from all participants.The sensory evaluation was conducted
by a team of five trained panelists (three males and two females, aged
20–30 years) in accordance with the Chinese National Standard GB/T
23776–2018, which aligns with ISO 8586:2012 guidelines for sensory
assessor training. All participants were informed about the experiment
and its details and volunteered to join. The specific details of the
assessment were conducted according to the Chinese National Sensory
Evaluation Method for Tea (GB/T 23776–2018), and the samples were
randomly presented to all assessors. Firstly, 200 g of each tea sample
was placed in a white square tray to evaluate the appearance of the
samples. Subsequently, 3 g of each sample was steeped in 150 mL of
boiling water for 5 min, and the tea broth was filtered and placed in a
white porcelain cup. In this cup, the panelists assessed the quality
and gave scores for color, aroma, and taste accordingly. Finally, a
score was given for the appearance of the steeped leaves based on the
observation of the brewed samples. The overall quality score is
calculated on a 100-point scale: The total quality score is the sum of
the values of each component, with a maximum of 100 points. The
components and their respective weights are as follows: dry tea contour
(25 %), soup color (10 %), aroma (25 %), taste (30 %), and appearance
of infused leaves (10 %).
2.4. Non-volatile metabolites
2.4.1. Preparation process of different samples for UPLC-MS/MS analysis
Using vacuum freeze-drying technology, place the biological samples in
a lyophilizer (Scientz-100F), then grinding (30 Hz, 1.5 min) the
samples to powder form using a grinder (MM 400, Retsch). Next, weigh
50 mg of sample powder using an electronic balance (MS105DΜ) and add
1200 μL of −20 °C pre-cooled 70 % methanolic aqueous internal standard
extract (less than 50 mg added at the rate of 1200 μL extractant per
50 mg sample). Vortex once every 30 min for 30 s, for a total of 6
times. After centrifugation (rotation speed 12,000 rpm, 3 min), the
supernatant was aspirated, and the sample was filtered through a
microporous membrane (0.22 μm pore size) and stored in the injection
vial for UPLC-MS/MS analysis.
2.4.2. UPLC and ESI-QTRAP-MS/MS conditions
The sample extracts were analyzed using an ultra-performance liquid
chromatography-electrospray ionization-triple quadrupole-linear ion
trap mass spectrometry (UPLC-ESI-QTRAP-MS/MS) system. The UPLC system
(ExionLC™ AD, SCIEX) was coupled with a hybrid triple quadrupole-linear
ion trap mass spectrometer (6500 Q TRAP, SCIEX).The analytical
conditions were as follows, UPLC: column, Agilent™ SB-C18 (1.8 μm,
2.1 mm * 100 mm). The mobile phase was consisted of solvent A, pure
water with 0.1 % formic acid, and solvent B, acetonitrile with 0.1 %
formic acid. Sample measurements were performed with a gradient program
that employed the starting conditions of 95 % A, 5 % B. Within 9 min, a
linear gradient to 5 % A, 95 % B was programmed, and a composition of
5 % A, 95 % B was kept for 1 min. Subsequently, a composition of 95 %
A, 5.0 % B was adjusted within 1.1 min and kept for 2.9 min. The flow
velocity was set as 0.35 mL per minute. The column oven was set to
40 °C. The injection volume was 2 μL. The effluent was alternatively
connected to an ESI-triple quadrupole-linear ion trap (QTRAP)-MS. Data
acquisition and processing were performed using Analyst TF 1.6.3
software (SCIEX).
The ESI source operation parameters were as follows: source temperature
500 °C; ion spray voltage (IS) 5500 V (positive ion mode)/−4500 V
(negative ion mode); ion source gas I (GSI), gas II(GSII), curtain gas
(CUR) was set at 50, 60, and 25 psi, respectively; the
collision-activated dissociation (CAD) was high. QQQ scans were
acquired as MRM experiments with collision gas (nitrogen) set to
medium. DP (declustering potential) and CE (collision energy) for
individual MRM transitions was done with further DP and CE
optimization. A specific set of MRM transitions were monitored for each
period according to the metabolites eluted within this period.
2.4.3. Qualification and quantification of non-volatile metabolites
The data obtained from UPLC-TripleTOF6600 were characterized for
nonvolatiles by more accurate mass, retention time and isotope ratios
with a commercial database from Metware (Hubei, China). After obtaining
the metabolite profiling data of different samples, peak area
integration was performed for all the substance chromatographic peaks
and the integration was corrected for the mass spectrometry peaks of
the same metabolite in different samples among them ([43]Fraga et al.,
2010).
2.5. Analysis of volatile metabolites
2.5.1. Preparation process of different samples for GC–MS analysis
Materials were harvested, weighted, immediately frozen in liquid
nitrogen, and stored at −80 °C until needed. Samples were ground to a
powder in liquid nitrogen.
500 mg (1 mL) of the powder was transferred immediately to a 20 mL
head-space vial (Agilent, Palo Alto, CA, USA), containing NaCl
saturated solution, to inhibit any enzyme reaction. The vials were
sealed using crimp-top caps with TFE‑silicone headspace septa
(Agilent). At the time of SPME analysis, each vial was placed in 60 °C
for 5 min, then a 120 μm DVB/CWR/PDMS fibre (Agilent) was exposed to
the headspace of the sample for 15 min at 60 °C.
2.5.2. Acquisition conditions for GC–MS analysis
After sampling, desorption of the VOCs from the fibre coating was
carried out in the injection port of the GC apparatus (Model 8890;
Agilent) at 250 °C for 5 min in the splitless mode. The identification
and quantification of VOCs was carried out using an Agilent Model 8890
GC and a 7000D mass spectrometer (Agilent), equipped with a
30 m × 0.25 mm × 0.25 μm DB-5MS (5 % phenyl-polymethylsiloxane, Agilent
J&W Scientific, Folsom, CA, USA) capillary column. Helium was used as
the carrier gas at a linear velocity of 1.2 mL/min. The injector
temperature was kept at 250 °C and the detector at 280 °C. The oven
temperature was programmed from 40 °C (3.5 min), increasing at 10 °C
/min to 100 °C, at 7 °C /min to 180 °C, at 25 °C /min to 280 °C, hold
for 5 min. Mass spectra was recorded in electron impact (EI) ionisation
mode at 70 eV. The quadrupole mass detector, ion source and transfer
line temperatures were set, respectively, at 150, 230 and 280 °C. The
MS was selected ion monitoring (SIM) mode was used for the
identification and quantification of analytes.Data analysis were
performed using MassHunter Qualitative Analysis B.06.00 (Agilent
Technologies).
LC internal standards: Specified the use of 2-Chlorophenylalanine (98 %
purity, J&K Scientific, Lot LBCOR15, CAS:14091–11-3), with QC samples
for system monitoring.
2.5.3. Qualification and quantification of volatile metabolites
Based on multi-species, literature, some specimens, and retention
index, the database is established independently. Then Selected Ion
Monitoring (SIM) mode for accurate scanning, 1 quantitative ion and 2–3
qualitative ions for each compound respectively. All the ions to be
detected in each group were detected separately in time periods
according to the order of peak appearance; if the retention time of the
detected peaks was consistent with the standard reference and the
selected ions all appeared in the mass spectra of the samples after
deduction of the background, the substance was judged to be the
substance; the quantitative ions were selected for the integration of
the chromatographic peaks and the calibration work, to enhance the
accuracy of the quantification.
GC internal standards: Specified the use of deuterated
3-Hexanone-2,2,4,4-d4 (CDN Isotopes, Canada, CAS:24588–54-3), with QC
samples for system monitoring.
2.5.4. rOAV metabolite calculations
Relative odor activity value (rOAV) is a method for determining the key
flavor compounds of a food established in combination with the sensory
thresholds of the compounds, and is used to clarify the contribution of
each aroma compound to the overall aroma profile of the sample. The
application of this method can identify the causes of the same or
different flavors from EUL of different processing processes. Generally
rOAV ≥1 suggests that the compound has a direct contribution to the
flavor of the sample. According to literature([44]Huang et al., 2022)
([45]Xue et al., 2022), an rOAV analysis was performed with the
following formula:
[MATH: rOAVi=CiTi :MATH]
In the formula,
[MATH: rOAVi :MATH]
is the relative odor activity value of compound i, and
[MATH: Ci :MATH]
is the relative content of the compound (μg/g or μg/mL);
[MATH: Ti :MATH]
is the threshold of the compound (Threshold, μg/g or μg/mL).
The threshold values,
[MATH: Ti :MATH]
were obtained from reputable databases: The Good Scents Company
([46]http://www.thegoodscentscompany.com), Perflavory Information
System ([47]http://perflavory.com), Flavor Ingredient Library
([48]https://www.femaflavor.org/flavor-library), LRI & Odor
([49]http://www.odour.org.uk/odour/index.html), and Food Flavor Lab
([50]http://foodflavorlab.cn/#/home).
2.5.5. Metabolomics analysis and network visualisation
PCA: Unsupervised PCA (principal component analysis) was performed
using the prcomp function in R. prior to analysis, missing values in
the metabolite data were imputed with zeros, and the data matrix was
normalized by unit variance scaling to reduce technical variability.
The data was unit variance scaled before unsupervised PCA.
Hierarchical Cluster Analysis and Pearson Correlation Coefficients: The
HCA (hierarchical cluster analysis) results of samples and metabolites
were presented as heatmaps with dendrograms, while Pearson Correlation
Coefficients (PCC) between samples were calculated by the cor function
in R and presented as only heatmaps. Both HCA and PCC were carried out
by R package ComplexHeatmap. For HCA, normalized signal intensities of
metabolites (unit variance scaling) are visualized as a color spectrum.
Differential metabolites selected: For two-group analysis, differential
metabolites were determined by VIP (VIP > 1) and absolute Log[2]FC
(|Log[2]FC| ≥ 1.0). VIP values were extracted from OPLS-DA result,
which also contain score plots and permutation plots, was generated
using R package MetaboAnalystR. The data was logging transform (log[2])
and mean centering before OPLS-DA. In order to avoid overfitting, a
permutation test (200 permutations) was performed.
KEGG annotation and enrichment analysis: Identified metabolites were
annotated using KEGG Compound database
([51]http://www.kegg.jp/kegg/compound/), annotated metabolites were
then mapped to KEGG Pathway database
([52]http://www.kegg.jp/kegg/pathway.html). Pathways with significantly
regulated metabolites mapped to were then fed into MSEA (metabolite
sets enrichment analysis), their significance was determined by
hypergeometric test's p-values.
3. Results and discussion
3.1. Sensory evaluation analysis of EUL with different processing techniques
The operating procedure and different product of EUL is shown in
[53]Fig.1A. The brewing soup color of each sample is shown in
[54]Fig.1B. The corresponding scoring is detailed in [55]Table 1. The
investigation revealed that BT processing had the most pronounced
impact on the color and flavor profile of EUL tea. The soup brewed
directly from fresh EUL exhibited a shiny of color and a refreshing
taste. In contrast, the HG process yielded a tea of light-yellow hue
with an astringent taste. Meanwhile, the GT processing resulted in a
tea of apricot color and a noticeable bitter taste.
Fig.1.
[56]Fig.1
[57]Open in a new tab
A Flow chart of different process preparation of EUL; B Brewing soup
color of different samples.
Table 1.
Total score table of different processed Eucommia ulmoides
leaves (EUL), (including Contour, Liquor color, Aroma, Taste, Infused
leaf, Total points, Ranking).
Item Contour
__________________________________________________________________
####
__________________________________________________________________
Liquor colo
__________________________________________________________________
####
__________________________________________________________________
Aroma
__________________________________________________________________
####
__________________________________________________________________
Taste
__________________________________________________________________
-30 %
__________________________________________________________________
Infused leaf
__________________________________________________________________
-10 %
__________________________________________________________________
Total points Ranking
Evaluation Score Evaluation Score Evaluation Score Evaluation Score
Evaluation Score
XY Sturdy、bloom 21.1 Shiny 8.46 Slightly grass odour 21.1 Grass
taste、pale and watery 25.9 Far and tender 8.2 85.4 1
HG Flat、dry 20.8 Light yellow 7.7 Grass odour 20.5 Grassy and
astringent 24.6 Even 7.23 80.9 2
GT Slightly tight、dull green 22.3 Apricot 7.93 Grass odour 19.9 Grassy
taste 、slightly bitter 22 Open 7.4 79.6 3
BT Tight curled 21.3 red and clear 8.7 Strong grass odour 18.9 Strong
grassy taste、slightly pungent taste 22.4 Slightly open 7.67 78.9 4
[58]Open in a new tab
3.2. Non-volatile metabolite profiles and dynamics of XY, HG, BT, GT
In this study, a wide range of targeted metabolomics methods was
employed to monitor the XY, HG, BT, and GT samples. In total, 1839
nonvolatile metabolites (12 subclasses) were structurally detected or
annotated, and identified using the Metware database. ([59]Fig.2 A,
[60]Table 2) Among them are 352 flavonoids (19 %), 313 phenolic acids
(17 %), 216 amino acids (12 %) and their derivatives, 157 alkaloids
(9 %), 144 lipids (8 %), 117 organic acids (6 %), 105 terpenoids (6 %),
81 lignans and coumarins, 78 nucleotides and their derivatives, 17
quinones, 12 tannin and 247 other metabolites (including alcohols,
lactones, aldehydes, chromone, sugars, ketones, vitamins, stilbenes and
others). As shown in [61]Fig.2B and [62]2C the superposition analysis
of the total ion current maps of Quality Control Sample(QC)samples in
positive and negative ion modes showed good reproducibility.
Fig. 2.
[63]Fig. 2
[64]Open in a new tab
A show a pie chart of the distribution of nonvolatile metabolites; B
and C show the superimposed analysis of the total ion current maps of
the QC samples in positive and negative ion modes; D shows the PCA
scores of the nonvolatile.
Table 2.
Summary table of non-volatile metabolite compositions, classifications
and relative content of substances in different processed EUL.
Index Compounds Class
s 1,4-Dihydro-1-Methyl-4-oxo-3-pyridinecarboxamide Alkaloids
MWS0687 1-Methyl-6-Oxo-1,6-Dihydropyridine-3-Carboxamide Alkaloids
pmf0290 2-Hydroxypyridine Alkaloids
MWS1787 2-Picoline; 2-Methylpyridine Alkaloids
pme1738 3-Carbamyl-1-methylpyridinium;(1-Methylnicotinamide) Alkaloids
pma6298 3-Hydroxypyridine Alkaloids
Zblp001009 3-pyridine-methanol-O-β-d-glucopyranosyl Alkaloids
Wayp004564 4-hydroxy-4-(3-pyridyl)-butanoic acid Alkaloids
pmf0291 4-Hydroxypyridine Alkaloids
MWS2032 6-Methylnicotinamide Alkaloids
MWSmce016 Nicotinic Acid Methyl Ester(Methyl Nicotinate) Alkaloids
MWSslk076 Nicotinic acid N-oxide Alkaloids
MWS3270 Quinolinic Acid Alkaloids
Yacp000453 3-hydroxy-1-methylpyrrolidin-2-one* Alkaloids
Zmsp000878 4-Hydroxy-5-(2-oxo-1-pyrrolidinyl)benzoic acid* Alkaloids
MWStz073 5-Hydroxy-2-pyrrolidinone Alkaloids
MWStz081 Piperlotine C; 1-(3,4,5-Trimethoxycinnamoyl)pyrrolidine
Alkaloids
MWS1860 Pyrrolidin Alkaloids
MWSmce157 Stachydrine Alkaloids
MWSslk106 2-Phenylethylamine Alkaloids
MWS2076 2-Aminophenol Alkaloids
MWSmce462 4-Hydroxybenzylamine Alkaloids
Lmgp000796 4-Hydroxymandelonitrile Alkaloids
MWS0435 Acetaminophen Alkaloids
pma0101 Caffeoylagmatine Alkaloids
pmp001244 Caffeoylcholine Alkaloids
Hmcp009963 Candicine Alkaloids
pmp001176 Dihydrocaffeoyltyramine Alkaloids
MWSmce521 Dobutamine Alkaloids
mws4002 Dopamine Alkaloids
MWStz070 N-(2-Hydroxy-4-methoxyphenyl)acetamide Alkaloids
Wagp001741 N-(gamma-L-glutamyl)tyramine O-glucoside Alkaloids
pmb0492 N′,N″,N″‘-p-Coumaroyl-cinnamoyl-caffeoyl spermidine Alkaloids
pma0702 N1,N8-Bis(sinapoyl)spermidine Alkaloids
Zdcp003644 N-Caffeoylputrescine Alkaloids
pmb0496 N-Feruloylagmatine Alkaloids
Lmhp003013 N-Feruloyl-Cadaverine Alkaloids
MWSmce098 Nonivamide Alkaloids
pmb0490 p-Coumaroylputrescine Alkaloids
Lmqp002784 Salicylamide Alkaloids
pmp001214 Sinapine Alkaloids
NK10246260 2,4-Dihydroxyquinoline Alkaloids
Lahp002608 3,5-Dihydro-2H-Furo[3,2-C]Quinolin-4-One* Alkaloids
Ladp002935 3-quinolinecarboxylic acid Alkaloids
Lmgp001898 4,6-Dihydroxyquinoline Alkaloids
Ladp002110 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid
Alkaloids
Lmlp002044 8-Hydro-4,7-dimethoxyfuranaquinoline Alkaloids
Wcjp002598 8-hydroxyquinoline Alkaloids
MWSslk057 9-Aminoacridine Alkaloids
mws0393 Quinine Alkaloids
Wasn002329 Xanthurenic Acid 8-O-Glucoside Alkaloids
MWStz063 2-Ethyl-2,6,6-trimethylpiperidin-4-one Alkaloids
MWSmce460 2-Piperidone Alkaloids
pmp001198 6-Deoxyfagomine Alkaloids
MWSmce338 N-Hydroxypipecolic acid Alkaloids
pmb0782 Piperidine Alkaloids
pmb1912 10-Formyltetrahydrofolic Acid Alkaloids
MWS2050 1-Aminopropan-2-ol* Alkaloids
MWS4401 1-Methylguanidine Alkaloids
mws0982 1-Methylhistamine Alkaloids
Lmxn006423 2(3H)-Benzothiazolone Alkaloids
MWStz152 2-(Acetylamino)-3-phenyl-2-propenoic acid* Alkaloids
MWSmce645 2-(Aminooxy)Acetic Acid Alkaloids
MWSslk118 2,2’-Cyclouridine Alkaloids
MWS1855 2,5-Dimethyl pyrazine Alkaloids
MWS2063 2,6-Dimethylaniline Alkaloids
MWSmce557 2-Acetyl-3-ethylpyrazine Alkaloids
MWS1936 2-Methyl-5-nitroimidazole-1-ethanol Alkaloids
Hmgp002327 3-amino-2-naphthoic acid* Alkaloids
MWS1777 3-Chloroaniline Alkaloids
MWSmce128 4(3H)-Quinazolinone Alkaloids
Hmtp000776 4,5,6-Trihydroxy-2-cyclohexen-1-ylideneacetonitrile
Alkaloids
Wccp001401 4-[2-formyl-5-(hydroxymethyl)pyrrol-1-yl]butanoic acid
Alkaloids
Lamp000484 4-Methylazetidine-2-Carboxylic acid* Alkaloids
pma3649 5-Aminolevulinic Acid* Alkaloids
MWS2072 5-Nitrobenzimidazole Alkaloids
Wbjp004368 8-Hydroxy-harmine Alkaloids
MWSmce207 Acetylpyrazine Alkaloids
pmb0501 Agmatine Alkaloids
MWS3105 Aniline Alkaloids
MWSmce331 Azetidine-2-carboxylic acid* Alkaloids
pmb0069 Benzamide Alkaloids
MWSmce548 Betaine Alkaloids
MWS1792 Butylamine Alkaloids
pme1841 Cadaverine Alkaloids
mws2218 Caffeine Alkaloids
pmb0484 Choline Alkaloids
MWS1784 Cyclohexylamine Alkaloids
MWSmce526 Daminozide Alkaloids
MWSslk100 Diphenylamine Alkaloids
mws1346 DL-2-Aminoadipic acid* Alkaloids
pme0066 Guanidinoacetate Alkaloids
Wcdp010864 Hexadecanamide Alkaloids
pmp001269 Hexadecyl ethanolamine Alkaloids
pma2987 Histidinol Alkaloids
MWSmce448 Imidazol-1-yl-acetic acid* Alkaloids
MWSmce118 Imidazole-4-Acetic Acid* Alkaloids
MWSmce461 L-Azetidine-2-carboxylic acid* Alkaloids
pme1002 L-Tyramine Alkaloids
mws1383 Lumichrome Alkaloids
Zasp102439 m-Aminophenylacetylene Alkaloids
Zahp014087 N-(12-methyltetradecyl)propionamide* Alkaloids
Lmmp002080 N-(4-Aminobutyl)benzamide Alkaloids
Zajp000573 N-(4-oxopentyl)-acetamide* Alkaloids
Wbjp002336 N,N-diethyl-5-hydroxytryptamineoxalate Alkaloids
MWS3020 N-Acetylcadaverine Alkaloids
pme2693 N-Acetylputrescine Alkaloids
Smcp000882 N-benzoyl-2-aminoethyl-β-D-glucopyranoside Alkaloids
HJKP000649 N-benzylformamide Alkaloids
pmp001287 N-Benzylmethylene isomethylamine Alkaloids
MWS0700 Neopterin Alkaloids
pmp000476 N-Isobutyl-4,5-epoxy-2E-decaenamide Alkaloids
MWSmce571 N-Methylbenzylamine Alkaloids
Qmdp090606 N-Methyltetrahydropalmatine Alkaloids
mws0983 N-Oleoylethanolamine Alkaloids
Zmpp000906 Norepinephrine Alkaloids
MWSslk108 O-Acetyl-l-carnitine Alkaloids
Wbjp001169 o-Carboxy-5-hydroxytryptamine Alkaloids
Zahp013600 Octadec-2-enamide* Alkaloids
Wccp011838 Octadec-8-enamide* Alkaloids
Zahp012577 Octadecadienamide Alkaloids
pmb1754 O-Phosphocholine Alkaloids
pma0948 Phenylethanolamine Alkaloids
pme2292 Putrescine Alkaloids
mws0017 Spermidine Alkaloids
mws0018 Spermine Alkaloids
Hamp012107 Stearamide* Alkaloids
Wcfp007836 Tetradecyldiethanolamine Alkaloids
MWS1919 Thiazole Alkaloids
MWS0812 Trimethylamine N-Oxide* Alkaloids
Wbmp002283 Α-hydroxyquinoline Alkaloids
Cmyp003522 3’-Hydroxy-N-methylcoclaurine Alkaloids
MWSmce709 Isoquinoline Alkaloids
MWStz108 1-Ethoxycarbonyl-β-Carboline Alkaloids
Zmbp002538 1-Methoxy-indole-3-acetamide* Alkaloids
MWStz282 3-Hydroxy-3-acetonyloxindole* Alkaloids
pmb0819 3-Indoleacetonitrile Alkaloids
Hmmp001310 3-Indoleacrylic acid* Alkaloids
pme2244 3-Indolepropionic acid Alkaloids
pmc0682 4-Aminoindole Alkaloids
mws0597 5-Hydroxyindole-3-acetic acid Alkaloids
pme2836 5-Hydroxytryptophol Alkaloids
mws0333 5-Methoxytryptamine Alkaloids
Lmyn002540 Dioxindole-3-acetyl-3-O-glucoside Alkaloids
pmb1096 Indole Alkaloids
pme1651 Indole-3-acetic acid (IAA) Alkaloids
mws0103 Indole-3-carboxaldehyde Alkaloids
mws1417 Indole-3-carboxylic acid* Alkaloids
mws0102 Indole-5-carboxylic acid* Alkaloids
pmb0818 Methoxyindoleacetic acid Alkaloids
Hmyp002656 Methyl dioxindole-3-acetate Alkaloids
pmb0769 N-(p-Coumaroyl)serotonin Glucoside Alkaloids
mws0677 N-Acetyl-5-hydroxytryptamine Alkaloids
mws0620 N-Methyltryptamine Alkaloids
MWSmce314 Oxindole Alkaloids
mws0005 Tryptamine Alkaloids
MWStz201 β-Carboline-1-propanoic acid Alkaloids
Zbqn002320 (4-(2-oxopropoxy)phenyl)-L-alanine Amino acids and
derivatives
MWS00330g 1-Amino-1-cyclobutane-carboxylic-acid* Amino acids and
derivatives
MWS0933 1-Methylhistidine* Amino acids and derivatives
Zmmp001941 2-Amino-3,4-dihydroxybutanoic acid-3-O-arabinoside Amino
acids and derivatives
MWS04528 2-Amino-4-sulfinobutanoic acid Amino acids and derivatives
Zmdp000441 3-(Allylsulphinyl)-L-alanine Amino acids and derivatives
MWS04491 3,4-Dehydro-DL-proline Amino acids and derivatives
MWS1039a 3-Amino-2-methylpropanoic acid Amino acids and derivatives
pme2914 3-Hydroxy-3-methylpentane-1,5-dioic acid Amino acids and
derivatives
MWS04559g 3-Hydroxy-L-phenylalanine* Amino acids and derivatives
pme0181 3-Methyl-L-Histidine* Amino acids and derivatives
MWS2010 3-nitro-L-tyrosine Amino acids and derivatives
Zbqp003444 4-amino-5-oxo-5-(pentylamino)pentanoic acid Amino acids and
derivatives
pme2758 4-Hydroxy-L-glutamic acid Amino acids and derivatives
MWSmce190 4-Hydroxy-L-Isoleucine Amino acids and derivatives
mws3109 4-Hydroxy-L-phenylglycine Amino acids and derivatives
pme2566 5-L-Glutamyl-L-amino acid Amino acids and derivatives
Zbqp000949 5-methyl 1-propyl L-glutamate Amino acids and derivatives
mws0263 5-Oxo-L-Proline* Amino acids and derivatives
MWS0813 5-Oxoproline* Amino acids and derivatives
MWS201401 Ala-Asn Amino acids and derivatives
pme3351 Allysine(6-Oxo DL-Norleucine) Amino acids and derivatives
MWS201384 Arg-Gly Amino acids and derivatives
Zmdp000292 Arginine methyl ester* Amino acids and derivatives
MWS201387 Asn-Arg Amino acids and derivatives
MWS201389 Asn-Gln Amino acids and derivatives
MWS201388 Asn-Hyp Amino acids and derivatives
MWS201391 Asn-Ile Amino acids and derivatives
MWS201449 Asn-Leu Amino acids and derivatives
MWS201408 Asp-Glu Amino acids and derivatives
MWS201455 Asp-Lys* Amino acids and derivatives
pmf0470 cis-4-Hydroxy-D-proline* Amino acids and derivatives
MWStz261 Cyclo(D-Leu-L-Pro)* Amino acids and derivatives
MWStz205 Cyclo(D-Phe-L-Pro)* Amino acids and derivatives
MWStz083 Cyclo(D-Val-L-Pro) Amino acids and derivatives
Zazp002547 cyclo-(Gly-Phe) Amino acids and derivatives
MWStz091 Cyclo(L-Ala-L-Pro) Amino acids and derivatives
MWStz170 Cyclo(L-Leu-trans-4-hydroxy-L-Pro) Amino acids and derivatives
MWStz211 Cyclo(L-Phe-trans-4-hydroxy-L-Pro) Amino acids and derivatives
Lmrj002793 Cyclo(Phe-Glu) Amino acids and derivatives
Lmhp001430 Cyclo(Pro-Glu) Amino acids and derivatives
Lmhp002764 Cyclo(Pro-Leu)* Amino acids and derivatives
MWStz255 Cyclo(Pro-Phe)* Amino acids and derivatives
Lmrj002244 Cyclo(Pro-Pro) Amino acids and derivatives
Lmrj002698 Cyclo(Pro-Val) Amino acids and derivatives
Lmrj001341 Cyclo(Ser-Pro) Amino acids and derivatives
ML10181668 Cycloleucine Amino acids and derivatives
MWS0611 D-Alanyl-D-Alanine* Amino acids and derivatives
MWS04555g D-Allo-Isoleucine* Amino acids and derivatives
MWS1926 DL-Leucine* Amino acids and derivatives
mws0224 DL-Methionine Amino acids and derivatives
MWS00275g DL-O-tyrosine Amino acids and derivatives
MWSmce056 DL-Tryptophan* Amino acids and derivatives
mws4532g D-Ornithine Amino acids and derivatives
MWS201444 Gln-Gly Amino acids and derivatives
MWS201469 Glu-Arg Amino acids and derivatives
MWS201465 Glu-Phe Amino acids and derivatives
MWS20672 Glu-Phe-Ala Amino acids and derivatives
MWS4296 Glycylphenylalanine* Amino acids and derivatives
MWS4309 Glycyl-tryptophan Amino acids and derivatives
MWS201428 Gly-Glu Amino acids and derivatives
MWS20645 Gly-Tyr* Amino acids and derivatives
pme2853 Hexanoyl-L-glycine Amino acids and derivatives
Zbqp002414 h-gamma-Glu-leu-oh Amino acids and derivatives
MWS201405 His-Tyr Amino acids and derivatives
MWS04447 Homoproline Amino acids and derivatives
MWS201398 Hyp-Ser Amino acids and derivatives
MWS201397 Hyp-Val Amino acids and derivatives
MWS201424 Ile-Asn Amino acids and derivatives
pme2074 Jasmonoyl-L-Isoleucine Amino acids and derivatives
MWS00411g L-2-Aminoadipate* Amino acids and derivatives
pme0128 L-Alanyl-L-Alanine* Amino acids and derivatives
mws4176 L-Alanyl-L-Phenylalanine Amino acids and derivatives
pme2679 L-Allo-isoleucine Amino acids and derivatives
mws0260 L-Arginine Amino acids and derivatives
mws0001 L-Asparagine Amino acids and derivatives
mws0219 L-Aspartic Acid* Amino acids and derivatives
mws0629 L-Aspartyl-L-Phenylalanine Amino acids and derivatives
pme0116 L-Carnosine Amino acids and derivatives
pme0008 L-Citrulline Amino acids and derivatives
Hmsp000364 L-Cyclopentylglycine Amino acids and derivatives
pme2773 L-Cystathionine Amino acids and derivatives
mws0875 L-Cysteinyl-L-glycine Amino acids and derivatives
mws0221 L-Cystine Amino acids and derivatives
Lmbp001216 L-Dihomomethionine Amino acids and derivatives
MWS201461 Leu-Arg Amino acids and derivatives
MWS201437 Leu-Asp Amino acids and derivatives
pme0014 L-Glutamic acid Amino acids and derivatives
pme0193 l-Glutamine Amino acids and derivatives
mws0217 L-Glycine Amino acids and derivatives
mws5041 L-Glycyl-L-isoleucine* Amino acids and derivatives
mws5042 L-Glycyl-L-phenylalanine* Amino acids and derivatives
pme0124 L-Glycyl-L-proline Amino acids and derivatives
mws0254 L-Histidine Amino acids and derivatives
mws0193 L-Homocitrulline Amino acids and derivatives
pme0057 L-Homocysteine Amino acids and derivatives
pme2890 L-Homocystine Amino acids and derivatives
Lmbp000123 L-Homomethionine Amino acids and derivatives
MWS00123g L-Homophenylalanine Amino acids and derivatives
mws0671 L-Homoserine* Amino acids and derivatives
mws0258 L-Isoleucine* Amino acids and derivatives
Lmrj002087 L-Isoleucyl-l-Aspartate Amino acids and derivatives
MWS00327g L-Isoserine Amino acids and derivatives
mws0227 L-Leucine* Amino acids and derivatives
Lmhp002031 L-Leucyl-L-Leucine Amino acids and derivatives
mws5035 L-Leucyl-L-phenylalanine Amino acids and derivatives
pme0026 l-Lysine Amino acids and derivatives
pmb0962 l-Lysine-Butanoic Acid Amino acids and derivatives
pme1210 L-Methionine Amino acids and derivatives
pme1419 L-Methionine methyl ester Amino acids and derivatives
pme2617 L-Methionine Sulfoxide Amino acids and derivatives
mws1587 L-Norleucine* Amino acids and derivatives
pme0021 L-Phenylalanine Amino acids and derivatives
mws0636 L-Phenylalanyl-L-phenylalanine Amino acids and derivatives
pme0006 L-Proline* Amino acids and derivatives
Lmhp001461 L-Prolyl-L-Leucine Amino acids and derivatives
Lmhp001732 L-Prolyl-L-Phenylalanine Amino acids and derivatives
Zmzn000113 L-threo-3-Methylaspartate Amino acids and derivatives
mws0230 L-Threonine* Amino acids and derivatives
mws0282 L-Tryptophan Amino acids and derivatives
MWS20627g L-Tyrosinamide Amino acids and derivatives
mws0250 L-Tyrosine* Amino acids and derivatives
MWS1771 L-Tyrosine methyl ester Amino acids and derivatives
mws0256 L-Valine Amino acids and derivatives
Wcdp000380 L-Valinol Amino acids and derivatives
Lmhp001670 L-Valyl-L-Leucine Amino acids and derivatives
Lmhp002001 L-Valyl-L-Phenylalanine Amino acids and derivatives
MWS201403 Lys-Ala Amino acids and derivatives
MWS201411 Lys-Asn Amino acids and derivatives
MWS201412 Lys-Asp* Amino acids and derivatives
MWS201419 Lys-Gly Amino acids and derivatives
MWS201464 Lys-Phe Amino acids and derivatives
MWS201436 Lys-Thr Amino acids and derivatives
MWS201471 Lys-Tyr Amino acids and derivatives
pmb0034 L-α-Glutamyl-L-Glutamic Acid Amino acids and derivatives
Zmdp002216 L-γ-Glutamyl-L-leucine Amino acids and derivatives
MWS201470 Met-Arg Amino acids and derivatives
MWS201399 Met-Asn Amino acids and derivatives
MWSmce585 Methyl 3-aminopropanoate Amino acids and derivatives
pme0109 Methyldopa Amino acids and derivatives
MWS201421 Met-Phe Amino acids and derivatives
MWS201429 Met-Ser Amino acids and derivatives
MWS201430 Met-Thr Amino acids and derivatives
Wayn001257 N-(1-Deoxy-1-fructosyl)Leucine Amino acids and derivatives
Wayp001024 N-(1-Deoxy-1-fructosyl)Valine Amino acids and derivatives
MWS1933 N-(2-Methylbenzoyl)glycine Amino acids and derivatives
mws0124 N-(3-Indolylacetyl)-L-alanine Amino acids and derivatives
MWS04412 N(6),N(6)-Dimethyl-l-lysine Amino acids and derivatives
Zbqn004590 N-(acetyl)phenylalanine Amino acids and derivatives
MWS5164 N,N′-Dimethylarginine;SDMA* Amino acids and derivatives
pme3033 N,N-Dimethylglycine* Amino acids and derivatives
Smjp002269 N-[3-(4-Hydroxyphenyl)acryloyl]-L-tyrosine Amino acids and
derivatives
MWS20987 N5-(1-Iminoethyl)-L-ornithine Amino acids and derivatives
pme0122 N6-Acetyl-l-lysine Amino acids and derivatives
MWSslk120 N-Acetyl-DL-phenylalanine Amino acids and derivatives
pme0170 N-Acetyl-L-Arginine Amino acids and derivatives
pme0075 N-Acetyl-L-glutamic acid Amino acids and derivatives
pme0137 N-Acetyl-l-Glutamine Amino acids and derivatives
pme0253 N-Acetyl-L-leucine Amino acids and derivatives
MWSslk140 N-Acetyl-L-Methionine Amino acids and derivatives
Zmgn002106 N-Acetyl-L-phenylalanine Amino acids and derivatives
pme3382 N-Acetyl-L-threonine Amino acids and derivatives
pmb2591 N-Acetyl-L-Tryptophan Amino acids and derivatives
mws0520 N-Acetyl-L-tyrosine Amino acids and derivatives
MWS4471 N-Alpha-Acetyl-L-Asparagine Amino acids and derivatives
Zbqn003921 N-carboxy-N-(2-oxo-2-phenylethyl)-L-alanine Amino acids and
derivatives
MWS00204g N-Ethylglycine* Amino acids and derivatives
NK10251888 NG,NG-Dimethyl-L-arginine* Amino acids and derivatives
mws0736 N-Glycyl-L-leucine* Amino acids and derivatives
Lmqp000427 N-Methyl-Trans-4-Hydroxy-L-Proline Amino acids and
derivatives
MWS5209 N-Methyl-α-aminoisobutyric acid Amino acids and derivatives
Zmjp000182 N-Monomethyl-L-arginine* Amino acids and derivatives
MWS3166 N-Palmitoylglycine Amino acids and derivatives
Zmyn000155 N-α-Acetyl-L-ornithine Amino acids and derivatives
MWS201054 O-Acetyl-L-homoserine Amino acids and derivatives
mws1050 O-Acetylserine Amino acids and derivatives
MWS20633g O-phosphate-L-tyrosine Amino acids and derivatives
mws3133 Oxaceprol Amino acids and derivatives
mws4134 Oxiglutatione Amino acids and derivatives
MWS201439 Phe-His Amino acids and derivatives
MWS201458 Phe-Ile Amino acids and derivatives
mws0715 Phenylacetyl-l-glutamine Amino acids and derivatives
MWS201478 Phe-Ser Amino acids and derivatives
MWS201442 Phe-Thr Amino acids and derivatives
MWS201414 Pro-Asn Amino acids and derivatives
MWS201415 Pro-Asp Amino acids and derivatives
Zbqn001255 propyl-L-alanine Amino acids and derivatives
MWS201466 Pro-Trp Amino acids and derivatives
mws4516 Pyroglutamic acid Amino acids and derivatives
Zmdp000976 S-(2-Carboxypropyl)cysteine Amino acids and derivatives
pme1286 S-(5′-Adenosy)-L-homocysteine Amino acids and derivatives
MWStz103 S-(5′-Adenosyl)-L-methionine Amino acids and derivatives
mws0582 S-(Methyl)glutathione Amino acids and derivatives
MWS201440 Ser-Glu Amino acids and derivatives
MWS201443 Ser-Lys Amino acids and derivatives
MWS201381 Ser-Trp Amino acids and derivatives
Lcsp002417 Ser-Val-Leu Amino acids and derivatives
Zmdp000972 S-Methyl-L-cysteine Amino acids and derivatives
MWS20966 S-methyl-L-thiocitrulline Amino acids and derivatives
MWS201477 Thr-Thr Amino acids and derivatives
mws0216 Trans-4-Hydroxy-L-proline* Amino acids and derivatives
pmp001257 Tridecanoylglycine Amino acids and derivatives
Zmzp000145 Trimethyllysine Amino acids and derivatives
MWS201187 Trp-His Amino acids and derivatives
MWS201480 Tyr-Ala Amino acids and derivatives
MWS201479 Tyr-Gly* Amino acids and derivatives
MWS201451 Val-His Amino acids and derivatives
MWS201400 Val-Trp Amino acids and derivatives
Zbqp003189 Val-Val Amino acids and derivatives
Zmdp001647 γ-Glutamyl-L-valine Amino acids and derivatives
Zmdp001663 γ-glutamylmethionine Amino acids and derivatives
Zmdn001564 γ-Glutamylphenylalanine Amino acids and derivatives
Zmdp001857 γ-Glutamyltyrosine Amino acids and derivatives
Zmmp003443 γ-Glu-Trp Amino acids and derivatives
Zmdp001718 γ-L-Glutamyl-S-allyl-L-cysteine Amino acids and derivatives
Zmdp000446 γ-L-Glutamyl-S-methyl-L-cysteine Amino acids and derivatives
mws1068 Kaempferol (3,5,7,4’-Tetrahydroxyflavone) Flavonoids
MWSHY0136 Kaempferol-3-O-glucoside (Astragalin)* Flavonoids
pme2954 Quercetin Flavonoids
mws0091 Quercetin-3-O-glucoside (Isoquercitrin) Flavonoids
mws0045 Quercetin-3-O-rhamnoside(Quercitrin) Flavonoids
MWSHY0067 Quercetin-3-O-rutinoside (Rutin)* Flavonoids
MWSHY0065 Catechin* Flavonoids
Lajp002810 Procyanidin A4 Flavonoids
Lmsp004137 3,4,2′,4′,6’-Pentahydroxychalcone Flavonoids
Wcfp003437 3-Prenyl-4,2′,4′-Trihydroxychalcone Flavonoids
pmn001716 Carthamone* Flavonoids
HJN055 Dihydrocharcone-4’-O-glucoside* Flavonoids
Labn004865 Hydroxy isoliquiritigenin glucoside* Flavonoids
Lasp002993 Isobavachalcone glucoside Flavonoids
Lmlp006175 Isosalipurposide (Phlorizin Chalcone) Flavonoids
pme2960 Naringenin chalcone; 2′,4,4′,6’-Tetrahydroxychalcone*
Flavonoids
Cmxp005429 Okanin Flavonoids
zjgp122004 Okanin-3’-O-β-D-glucoside* Flavonoids
Cmxp003975 Okanin-4’-O-glucoside(Marein)* Flavonoids
pme1201 Phloretin Flavonoids
mws2118 Phloretin-2’-O-glucoside (Phlorizin) Flavonoids
Zbpn005555 Phloretin-4’-O-glucoside (Trilobatin)* Flavonoids
Hmmn003343 Sappanchalcone Flavonoids
Hmpn005101 Sieboldin Flavonoids
Zbbp005255 Aureusidin Flavonoids
Cmxn006627 Maritimetin Flavonoids
Jmgn005927 2-hydroxynaringenin Flavonoids
Lmsp004301 3′,5,5′,7-Tetrahydroxyflavanone-7-O-glucoside* Flavonoids
Hmqn003268 5,7,3′,4′,5’-Pentahydroxydihydroflavone Flavonoids
Jmgn004021 6-C-Glucosyl-2-Hydroxynaringenin Flavonoids
Zbsp007084 Butin; 7,3′,4′-Trihydroxyflavanone* Flavonoids
HJN090 Butin-7-O-glucoside* Flavonoids
MWSslk252 Didymin (Isosakuranetin-7-O-rutinoside)* Flavonoids
Hmhp005335 Dihydrobaicalein Flavonoids
mws0064 Eriodictyol (5,7,3′,4’-Tetrahydroxyflavanone)* Flavonoids
HJN086 Eriodictyol-3’-O-glucoside* Flavonoids
MWS20145 Eriodictyol-7-O-glucoside* Flavonoids
MWSHY0092 Eriodictyol-7-O-Rutinoside (Eriocitrin) Flavonoids
pmb3023 Eriodictyol-8-C-glucoside* Flavonoids
pmb0628 Eriodictyol-8-C-glucoside-4’-O-glucoside Flavonoids
Lmqn009304 Eucalyptin (5-Hydroxy-7,4′-dimethoxy-6,8-dimethylflavone)
Flavonoids
mws0463 Hesperetin Flavonoids
pmb2970 Hesperetin-5,7-di-O-glucoside Flavonoids
pme1598 Hesperetin-5-O-glucoside Flavonoids
Lmzp002365 Hesperetin-7-O-glucoside Flavonoids
MWSHY0019 Hesperetin-7-O-neohesperidoside(Neohesperidin)* Flavonoids
MWSHY0116 Hesperetin-7-O-rutinoside (Hesperidin)* Flavonoids
Lahp003599 Homoeriodictyol-7,4′-di-O-β-D-glucopyranoside Flavonoids
pme1611 Isohemiphloin Flavonoids
Labp005025 Malonyl isoSakuranin Flavonoids
MWSHY0017 Naringenin (5,7,4′-Trihydroxyflavanone)* Flavonoids
HJN087 Naringenin-4’-O-glucoside* Flavonoids
pma0724 Naringenin-6-C-Glucoside Flavonoids
pmp000394 Naringenin-7-O-(2”-O-apiosyl)glucoside Flavonoids
pma0791 Naringenin-7-O-(6″-malonyl)glucoside Flavonoids
mws1179 Naringenin-7-O-glucoside (Prunin)* Flavonoids
mws0046 Naringenin-7-O-Neohesperidoside(Naringin)* Flavonoids
mws1066 Naringenin-7-O-Rutinoside(Narirutin)* Flavonoids
Lmzn001875 Naringenin-7-O-Rutinoside-4’-O-glucoside Flavonoids
mws1454 Persicoside Flavonoids
mws0789 Pinocembrin (Dihydrochrysin) Flavonoids
HJN078 Pinocembrin-7-O-(2”-O-arabinosyl)glucoside Flavonoids
HJAP135 Pinocembrin-7-O-(6”-O-malonyl)glucoside Flavonoids
Lmyp004617 Pinocembrin-7-O-glucoside (Pinocembroside)* Flavonoids
HJN076 Pinocembrin-7-O-neohesperidoside Flavonoids
mws0791 Poncirin (Isosakuranetin-7-O-neohesperidoside)* Flavonoids
mws0914 3,5,7-Trihydroxyflavanone (Pinobanksin) Flavonoids
mws1174 3-O-Acetylpinobanksin Flavonoids
mws1094 Aromadendrin (Dihydrokaempferol) Flavonoids
Lmtn002796 Aromadendrin-7-O-glucoside* Flavonoids
Cmsp004086 Dihydrokaempferide Flavonoids
Lmmn004625 Dihydrokaempferol-7-O-glucoside* Flavonoids
HJN104 Dihydromyricetin-3-O-glucoside Flavonoids
mws0044 Taxifolin(Dihydroquercetin) Flavonoids
Zbxn003562 Taxifolin-2-O-glucoside Flavonoids
Xmsn002700 Taxifolin-3’-O-glucoside Flavonoids
mws1361 Taxifolin-3-O-rhamnoside (Astilbin) Flavonoids
MWSHY0130 Taxifolin-7-O-rhamnoside Flavonoids
Lmdp003110 2,6,7,4’-Tetrahydroxyisoflavanone Flavonoids
Lmqn006260 2′,3′,4′,5,7-Pentahydroxyflavone* Flavonoids
Zajp007311 3′,4′,5′,5,7-Pentamethoxyflavone* Flavonoids
Lmtp003948 3′,5′,5,7-Tetrahydroxy-4′-methoxyflavanone-3’-O-glucoside
Flavonoids
Wagp009079 3,5,6,7,8,4’-Hexamethoxyflavone Flavonoids
Zbqn006065 3,5,7,2’-Tetrahydroxyflavone; Datiscetin* Flavonoids
MWSslk146 4’-O-Glucosylvitexin Flavonoids
Zmjp004875 5,6,3′,4’-Tetrahydroxy-3,7-dimethoxyflavone Flavonoids
Zmjp004852 5,6,3′,4’-Tetrahydroxy-3,7-dimethoxyflavone-6-O-glucoside*
Flavonoids
Zmhn003257 5,7,2′-Trihydroxy-8-methoxyflavone* Flavonoids
Hmmp007513 5,7-Dihydroxy-6,3′,4′,5′-tetramethoxyflavone
(Arteanoflavone)* Flavonoids
Zmhp003514 6,7,8-Tetrahydroxy-5-methoxyflavone Flavonoids
Zmyn003693 6-Hydroxy-2′-methoxyflavone Flavonoids
Hmcn002875 6-Hydroxyluteolin Flavonoids
Hmcn001884 6-Hydroxyluteolin 5-glucoside* Flavonoids
MWS20151 Apigenin; 4′,5,7-Trihydroxyflavone Flavonoids
MWS20148 Apigenin-4’-O-glucoside* Flavonoids
Lmtp002942 Apigenin-6,8-di-C-arabinoside* Flavonoids
mws1073 Apigenin-6,8-di-C-glucoside (Vicenin-2) Flavonoids
Lmtp002474 Apigenin-6-C-(2″-glucosyl)arabinoside Flavonoids
pmp000237 Apigenin-6-C-(2″-glucuronyl)xyloside Flavonoids
Lmnp102580 Apigenin-6-C-(2″-xylosyl)glucoside* Flavonoids
Lmtp002822 Apigenin-6-C-arabinoside-8-C-xyloside* Flavonoids
MWSHY0008 Apigenin-6-C-glucoside (Isovitexin)* Flavonoids
Hmgp003664 Apigenin-6-C-rhamnoside Flavonoids
MWSHY0021 Apigenin-7,4′-dimethyl ether Flavonoids
pmb0571 Apigenin-7-O-(2″-glucosyl)arabinoside Flavonoids
pmp000585 Apigenin-7-O-(6″-malonyl)glucoside Flavonoids
Lmpp003930 Apigenin-7-O-(6″-p-Coumaryl)glucoside Flavonoids
MWSHY0189 Apigenin-7-O-glucoside(Cosmosiin)* Flavonoids
pmb2991 Apigenin-7-O-glucoside-4’-O-rutinoside Flavonoids
pme0368 Apigenin-7-O-rutinoside (Isorhoifolin) Flavonoids
Lmtp002642 Apigenin-8-C-(2″-glucosyl)arabinoside Flavonoids
Lmnp202580 Apigenin-8-C-(2″-xylosyl)glucoside* Flavonoids
pmb0681 Apigenin-8-C-Arabinoside Flavonoids
MWSHY0181 Apigenin-8-C-Glucoside (Vitexin)* Flavonoids
Lakn002234 Catechin glucosyl glucoside Flavonoids
Lmyp005841 Chrysin-7-O-glucoside Flavonoids
Lazp002140 Chrysoeriol glucosyl xylosyl glucoside Flavonoids
Zmxp002867 Chrysoeriol-5,7-di-O-glucoside Flavonoids
pmb2999 Chrysoeriol-5-O-glucoside Flavonoids
pmb0587 Chrysoeriol-7-O-(2”-O-glucuronyl)glucoside Flavonoids
pmp001289 Chrysoeriol-7-O-(2”-O-glucuronyl)glucuronide Flavonoids
Zbsn005918 Chrysoeriol-7-O-(6″-acetyl)glucoside* Flavonoids
pmb3012 Chrysoeriol-7-O-glucoside Flavonoids
pmb3002 Chrysoeriol-7-O-rutinoside Flavonoids
pmb2997 Chrysoeriol-7-O-Sophoroside-5-O-glucuronide Flavonoids
Zmjp009119 Chrysosplenetin
(5,4’-Dihydroxy-3,6,7,3′-tetramethoxyflavone)* Flavonoids
mws0058 Diosmetin (5,7,3′-Trihydroxy-4′-methoxyflavone)* Flavonoids
pmp000579 Diosmetin-7-O-galactoside* Flavonoids
Hmmp004965 Diosmetin-7-O-glucoside* Flavonoids
MWSHY0190 Diosmetin-7-O-rutinoside (Diosmin) Flavonoids
Lmyn006227 Galangin (3,5,7-Trihydroxyflavone) Flavonoids
Lmlp005572 Galangin-7-O-glucoside Flavonoids
MWSslk237 Hispidulin-7-O-glucoside(Homoplantaginin)* Flavonoids
Zbzp003056 Isoorientin-7-O-glucoside* Flavonoids
Lmlp002990 Isosaponarin(Isovitexin-4’-O-glucoside) Flavonoids
mws1292 Isoschaftoside Flavonoids
Smhp004476 Isovitexin-2”-O-xyloside* Flavonoids
Hmmp003156 Isovitexin-7-O-glucoside(Saponarin) Flavonoids
Lmyp003837 Isovitexin-7-O-glucoside-2”-O-rhamnoside Flavonoids
pmp000236 Isovitexin-8-O-xyloside Flavonoids
Lmqp003887 Kaempferol-3-O-xylosyl(1 → 2)glucoside Flavonoids
Lmfn001893 Leucocyanidin Flavonoids
pme0088 Luteolin (5,7,3′,4’-Tetrahydroxyflavone) Flavonoids
MWS20147 Luteolin-3’-O-glucoside Flavonoids
Hmpp003270 Luteolin-4’-O-glucoside* Flavonoids
HJAP010 Luteolin-6,8-di-C-arabinoside Flavonoids
MWSHY0016 Luteolin-6-C-glucoside (Isoorientin) Flavonoids
Lmnp002413 Luteolin-6-C-glucoside-7-O-rhamnoside Flavonoids
Zmxp003107 Luteolin-7,3′-di-O-glucoside Flavonoids
Zmlp003063 Luteolin-7-O-(2”-O-rhamnosyl)rutinoside* Flavonoids
Hmjn004446 Luteolin-7-O-(6″-caffeoyl)rhamnoside Flavonoids
pmp000587 Luteolin-7-O-(6″-malonyl)glucoside* Flavonoids
Hmqp003184 Luteolin-7-O-(6″-malonyl)glucoside-5-O-arabinoside
Flavonoids
Zbsp004156 Luteolin-7-O-(6″-malonyl)glucoside-5-O-rhamnoside Flavonoids
Hmpp002612 Luteolin-7-O-gentiobioside Flavonoids
MWSHY0104 Luteolin-7-O-glucoside (Cynaroside)* Flavonoids
MWSHY0121 Luteolin-7-O-glucuronide Flavonoids
Lmmp003487 Luteolin-7-O-glucuronide-(2 → 1)-glucuronide Flavonoids
MWSHY0080 Luteolin-7-O-neohesperidoside (Lonicerin)* Flavonoids
Hmqp002870 Luteolin-7-O-Sophoroside-5-O-arabinoside Flavonoids
HJAP012 Luteolin-8-C-arabinoside Flavonoids
Hmlp003068 Meratin* Flavonoids
Hmmn004152 Neoeriocitrin Flavonoids
Hmgp002148 Nepetin-7-O-alloside* Flavonoids
Hmgp002036 Nepetin-7-O-glucoside(Nepitrin)* Flavonoids
mws0043 Nobiletin (5,6,7,8,3′,4’-Hexamethoxyflavone) Flavonoids
Ybnn007052 Norartocarpetin Flavonoids
Zmjp003031 Orientin-2”-O-galactoside* Flavonoids
pmb0636 Orientin-7-O-arabinoside Flavonoids
Zbjp003056 Orientin-7-O-glucoside* Flavonoids
Lmsp004632 Scutellarein (5,6,7,4’-Tetrahydroxyflavone) Flavonoids
mws0055 Tangeretin (4′,5,6,7,8-Pentamethoxyflavone)* Flavonoids
mws0920 Tricetin (5,7,3′,4′,5’-Pentahydroxyflavone) Flavonoids
Lmzp004885 Tricin (5,7,4′-Trihydroxy-3′,5′-dimethoxyflavone) Flavonoids
Hmmp002324 Tricin-4’-O-rutinoside-7-O-rutinoside Flavonoids
pmb3042 Tricin-5-O-Glucoside Flavonoids
pmb0713 Tricin-7-O-(2”-O-glucosyl)glucoside Flavonoids
pmb3045 Tricin-7-O-Glucuronide Flavonoids
Lmgp004959 Tricin-7-O-neohesperidoside* Flavonoids
Hmgp003086 Tricin-7-O-rutinoside* Flavonoids
Lcyp000688 Verecundin(Pinocembrin-5-glucoside)* Flavonoids
Zbsn003878 Vicenin-3 Flavonoids
pmp001111 Violanthin Flavonoids
Zmjp003291 Vitexin-2”-O-galactoside Flavonoids
pme3227 Vitexin-2”-O-rhamnoside Flavonoids
Zmjp003463 Vitexin-2”-O-xyloside Flavonoids
Lmcp004624 3-Methylkaempferol Flavonoids
Lmjp003655 6-C-MethylKaempferol-3-glucoside* Flavonoids
pma0214 6-C-Methylquercetin-3-O-glucoside* Flavonoids
Lmmp002963 6-C-Methylquercetin-3-O-rutinoside* Flavonoids
Zmhp102730 6-Hydroxykaempferol-3,6-O-Diglucoside Flavonoids
pmp001312 6-Hydroxykaempferol-3,7,6-O-triglycoside Flavonoids
Zmhp002640 6-Hydroxykaempferol-3-O-Rutinoside-6-O-glucoside* Flavonoids
pmp001311 6-Hydroxykaempferol-6,7-O-Diglucoside Flavonoids
pmp001309 6-Hydroxykaempferol-7-O-glucoside Flavonoids
Lmjp003295 6-Methoxykaempferol-3-O-glucoside* Flavonoids
mws2186 Avicularin(Quercetin-3-O-α-L-arabinofuranoside)* Flavonoids
MWSHY0077 Fisetin Flavonoids
Lmmp002143 Gossypetin-3-O-(6″-malonyl)glucoside* Flavonoids
Lmmp001947 Gossypetin-3-O-glucoside* Flavonoids
Lmmp002904 Gossypetin-3-O-glucoside-8-O-xyloside Flavonoids
Zmhp003784 Gossypetin-7-O-(3″-glucosyl)rhamnoside; Rhodioflavonoside
Flavonoids
Zmhp004034 Gossypetin-7-O-rhamnoside; Rhodiolgin Flavonoids
Zmhp003716 Herbacetin-7-O-rhamnoside-8-O-glucoside; Rhodionidin*
Flavonoids
pmb0645 Hesperetin-6-C-glucoside-7-O-glucoside Flavonoids
pmb0618 Hesperetin-8-C-glucoside-3’-O-glucoside Flavonoids
mws0066 Isorhamnetin; 3′-Methoxy-3,4′,5,7-Tetrahydroxyflavone
Flavonoids
Hmcp001578 Isorhamnetin-3,7-O-diglucoside Flavonoids
[65]Li512111 Isorhamnetin-3-O-(6″-acetylglucoside) Flavonoids
Zbpp002027 Isorhamnetin-3-O-(6″-malonyl)glucoside* Flavonoids
Hmcp001658 Isorhamnetin-3-O-(6″-malonyl)glucoside-7-O-glucoside
Flavonoids
Hmcp002316 Isorhamnetin-3-O-arabinoside Flavonoids
Lmgp005640 Isorhamnetin-3-O-Galactoside; Cacticin Flavonoids
Zbpp001992 Isorhamnetin-3-O-Glucoside* Flavonoids
MWSHY0064 Isorhamnetin-3-O-neohesperidoside* Flavonoids
Zbpp001877 Isorhamnetin-3-O-rutinoside* Flavonoids
MWSHY0135 Isorhamnetin-3-O-rutinoside (Narcissin)* Flavonoids
Hmmp002240 Isorhamnetin-3-O-rutinoside-7-O-(2”-O-glucosyl)glucuronate
Flavonoids
HJAP128 Isorhamnetin-3-O-rutinoside-7-O-rhamnoside Flavonoids
Hmcp002207 Isorhamnetin-7-O-glucoside (Brassicin)* Flavonoids
Zbjn005825 Kaempferide-3-O-(6’-O-acetyl)glucoside* Flavonoids
Zmcn003728 Kaempferol-3,7-O-diglucoside Flavonoids
MWSHY0201 Kaempferol-3,7-O-dirhamnoside (Kaempferitrin) Flavonoids
Lmyp003500 Kaempferol-3-O-(2″-galloyl)galactoside* Flavonoids
Lmdp004819
Kaempferol-3-O-(2″-sinapoyl)glucosyl-(1 → 2)-(6″-malonyl)glucoside
Flavonoids
Hmln001836 Kaempferol-3-O-(6”-Acetyl)glucosyl-(1 → 3)-Galactoside
Flavonoids
Lmyp003599 Kaempferol-3-O-(6″-galloyl)glucoside* Flavonoids
Lmdp004892 Kaempferol-3-O-(6″-malonyl)galactoside* Flavonoids
Lmmp003817 Kaempferol-3-O-(6″-malonyl)glucoside* Flavonoids
Hmcp001629 Kaempferol-3-O-(6″-Malonyl)glucoside-7-O-Glucoside
Flavonoids
Lmmn003398 Kaempferol-3-O-(6”-O-acetyl)glucoside Flavonoids
Xmyp004945 Kaempferol-3-O-(6”-Rhamnosyl-2″-Glucosyl)Glucoside
(Camelliaside A) Flavonoids
pmn001637 Kaempferol-3-O-arabinoside (Juglanin) Flavonoids
Hmcp001858 Kaempferol-3-O-arabinoside-7-O-rhamnoside Flavonoids
mws0913 Kaempferol-3-O-galactoside (Trifolin)* Flavonoids
Lmsp004670 Kaempferol-3-O-glucoside-7-O-rhamnoside* Flavonoids
Lmzn001894 Kaempferol-3-O-glucuronide Flavonoids
Lmjp002867 Kaempferol-3-O-neohesperidoside* Flavonoids
pmp001105 Kaempferol-3-O-neohesperidoside-7-O-glucoside* Flavonoids
mws0919 Kaempferol-3-O-rhamnoside (Afzelin)(Kaempferin) Flavonoids
pme1605 Kaempferol-3-O-robinobioside(Biorobin) Flavonoids
mws1035 Kaempferol-3-O-robinoside-7-O-rhamnoside (Robinin)* Flavonoids
MWSHY0050 Kaempferol-3-O-rutinoside(Nicotiflorin)* Flavonoids
Lmsp003161 Kaempferol-3-O-sophoroside-7-O-rhamnoside* Flavonoids
Lmqp002170 Kaempferol-3-O-sophorotrioside Flavonoids
Xmyp005654 Kaempferol-4’-O-glucoside* Flavonoids
HJAP023 Kaempferol-6,8-di-C-glucoside-7-O-glucoside Flavonoids
mws0089 Kaempferol-7-O-glucoside* Flavonoids
pme0321 Kaempferol-7-O-rhamnoside Flavonoids
HJAP005 Laricitrin-3-O-glucoside* Flavonoids
Hmcp002187 Limocitrin-3-O-galactoside* Flavonoids
pme3514 Morin* Flavonoids
Lmfn004065 Morin-3-O-arabinoside* Flavonoids
Lmfn004036 Morin-3-O-lyxoside* Flavonoids
Lmfp004055 Morin-3-O-xyloside* Flavonoids
mws0032 Myricetin Flavonoids
Lmtp004126 Myricetin-3-O-(6″-malony)glucoside* Flavonoids
pmn001640 Myricetin-3-O-arabinoside Flavonoids
Lmdp002969 Myricetin-3-O-galactoside* Flavonoids
mws0056 Myricetin-3-O-rhamnoside (Myricitrin) Flavonoids
mws1045 Myricetin-3-O-rutinoside Flavonoids
Lmpp003465 Myricetin-3-O-β-D-glucoside* Flavonoids
Zahp003364 myricetin-3-O-β-d-xylopyranosyl-(1 → 2)-β-D-glucopyranoside
Flavonoids
Lakp003108 Myricetindiglucoside Flavonoids
Lmjp003231 Patuletin-3-O-glucoside* Flavonoids
Hmgp001996 Quercetagetin; 3,3′,4′,5,6,7-Hexahydroxyflavone Flavonoids
Lmfp003403 Quercetagetin-7-O-glucoside(Quercetagitrin)* Flavonoids
Lmcp004369 Quercetin-3′,4′-dimethyl ether Flavonoids
Zbsp004438 Quercetin-3,4’-O-di-glucoside Flavonoids
Zmcp002666 Quercetin-3,7-Di-O-glucoside* Flavonoids
Zmcp003530 quercetin-3-hydroxyferuloyldiglucoside Flavonoids
Lmyp003588 Quercetin-3-O-(2″,6”-O-digalloyl)-glucoside Flavonoids
pmn001644 Quercetin-3-O-(2”-O-acetyl)glucuronide Flavonoids
Lmdp004221
Quercetin-3-O-(2”-O-caffeoyl)glucoside-(1 → 2)-(6″-Malonyl)glucoside
Flavonoids
pmp000596 Quercetin-3-O-(2”-O-galactosyl)glucoside Flavonoids
Lmfp005436 Quercetin-3-O-(2”-O-galloyl)Arabinoside Flavonoids
MWSHY0142 Quercetin-3-O-(2”-O-galloyl)galactoside Flavonoids
Lmmp003266 Quercetin-3-O-(2”-O-malonyl)glucoside-7-O-arabinoside
Flavonoids
Lmjp003360 Quercetin-3-O-(2”-O-malonyl)sophoroside-7-O-arabinoside
Flavonoids
Lmbp002336 Quercetin-3-O-(2”-O-rhamnosyl)galactoside* Flavonoids
HJAP127 Quercetin-3-O-(2”-O-Rhamnosyl)rutinoside Flavonoids
Hmcp001618 Quercetin-3-O-(2”-O-Xylosyl)rutinoside Flavonoids
Hmln002199 Quercetin-3-O-(6”-O-acetyl)galactoside Flavonoids
Zmsp004363 Quercetin-3-O-(6”-O-acetyl)glucoside Flavonoids
Hmln001682 Quercetin-3-O-(6”-O-acetyl)glucosyl-(1 → 3)-Galactoside
Flavonoids
Zbsp004136 Quercetin-3-O-(6”-O-arabinosyl)glucoside* Flavonoids
MWSHY0199 Quercetin-3-O-(6”-O-galloyl)galactoside Flavonoids
pmb0706 Quercetin-3-O-(6”-O-malonyl)glucosyl-5-O-glucoside Flavonoids
Lmdp004426 Quercetin-3-O-[2”-O-(6″‘-sinapoyl)glucosyl]glucoside
Flavonoids
Lmfp002421 Quercetin-3-O-[rhamnosyl(1 → 2)glucosyl]-5-O-glucoside*
Flavonoids
Lmdp003286 Quercetin-3-O-alloside; Isohyperoside* Flavonoids
mws4183 Quercetin-3-O-arabinoside Flavonoids
MWSHY0113 Quercetin-3-O-galactoside (Hyperin)* Flavonoids
Lmsp004166 Quercetin-3-O-glucoside-7-O-rhamnoside* Flavonoids
Lmjp002461 Quercetin-3-O-neohesperidoside* Flavonoids
Hmcp001769 Quercetin-3-O-rhamnosyl(1 → 2)arabinoside Flavonoids
Lssp210058 Quercetin-3-O-robinobioside* Flavonoids
Lmmp002334 Quercetin-3-O-rutinoside-7-O-glucoside* Flavonoids
Lnrp102163 Quercetin-3-O-rutinoside-7-O-rhamnoside Flavonoids
Lmjp002596 Quercetin-3-O-sambubioside* Flavonoids
Lmjp003206 Quercetin-3-O-Sambubioside-5-O-Glucoside Flavonoids
MWSHY0162 Quercetin-3-O-sophoroside (Baimaside) Flavonoids
Lmsp002982 Quercetin-3-O-sophoroside-7-O-rhamnoside* Flavonoids
Lmdp003509 Quercetin-3-O-xyloside (Reynoutrin)* Flavonoids
Lmmp003306 Quercetin-3-O-xylosyl(1 → 2)arabinoside Flavonoids
Zmgp002857 Quercetin-3-O-α-rhamnosyl (1 → 2)-[α-rhamnosyl
(1 → 6)]-β-glucoside Flavonoids
Lssp210052 Quercetin-3-rutinoside-7-galactoside Flavonoids
mws0856 Quercetin-4’-O-glucoside (Spiraeoside)* Flavonoids
Lmfn003760 Quercetin-4’-O-glucuronide Flavonoids
Smgp004575 Quercetin-5-O-β-D-glucoside* Flavonoids
Lmmp002995 Quercetin-7-O-(2″-malonyl)glucosyl-5-O-glucoside Flavonoids
pmp000589 Quercetin-7-O-(6″-malonyl)glucoside Flavonoids
pmb0709 Quercetin-7-O-(6″-malonyl)glucosyl-5-O-glucoside Flavonoids
mws1329 Quercetin-7-O-glucoside Flavonoids
Zbsp004301 Quercetin-7-O-rutinoside* Flavonoids
Lmmp002755 Quercetin-7-O-rutinoside-4’-O-glucoside Flavonoids
Lmjp002906 Rhamnetin-3-O-Glucoside* Flavonoids
Zmpp002571 Robinetin Flavonoids
pmb0565 Syringetin-3-O-glucoside Flavonoids
mws2627 Tamarixetin (3,3′,5,7-Tetrahydroxy-4′-Methoxyflavone)
Flavonoids
Zmhp005139 Tamarixetin-3-O-(6″-malonyl)glucoside* Flavonoids
Lahp003408 2-(3,4-dihydroxyphenyl)-4 h-chromene-3,5,7-triol-glucoside
Flavonoids
Lmmp003109 3’-O-Methyl-epicatechin Flavonoids
pme3285 Afzelechin (3,5,7,4’-Tetrahydroxyflavan) Flavonoids
mws0355 Catechin gallate* Flavonoids
pmn001416 Catechin-(7,8-bc)-4α-(3,4-dihydroxyphenyl)-dihydro-2-(3H)-one
Flavonoids
pmn001415 Catechin-(7,8-bc)-4β-(3,4-dihydroxyphenyl)-dihydro-2-(3H)-one
Flavonoids
Zajn002491 catechin-4-β-D-galactopyranoside* Flavonoids
pmb2947 Catechin-catechin-catechin Flavonoids
mws1422 Epiafzelechin Flavonoids
pme0460 Epicatechin* Flavonoids
mws1397 Epicatechin gallate* Flavonoids
HJN041 Epicatechin glucoside Flavonoids
Zmdn002400 Epicatechin-3’-O-β-D-glucopyranoside* Flavonoids
Zmdn002049 Epicatechin-4’-O-β-D-glucopyranoside* Flavonoids
pmb3114 Epicatechin-epiafzelechin Flavonoids
MWSHY0098 Epigallocatechin Flavonoids
mws0034 Epigallocatechin-3-gallate* Flavonoids
Lajp003377 Fisetinidol-(4α,6)-gallocatechin Flavonoids
mws0049 Gallocatechin Flavonoids
mws2220 Gallocatechin 3-O-gallate* Flavonoids
Lajp002779 Gallocatechin-(4α- > 8)-Catechin-(4α- > 8)-Catechin
Flavonoids
pmb2586 Gallocatechin-(4α → 8)-catechin Flavonoids
Lmmp000897 Gallocatechin-(4α → 8)-gallocatechin Flavonoids
Wbtp004753 1,2,3,7,8-pentahydroxy-6-methylanthracene-9,10-dione
Flavonoids
Wbtn006715 1,2,4,5,8-pentahydroxy-6-methylanthracene-9,10-dione*
Flavonoids
Wbtp004961 1,2,4,5-tetrahydroxy-7-(hydroxymethyl)anthracene-9,10-dione
Flavonoids
Wbtp004863
4-(beta-d-Glucopyranosyl)-7-methoxy-1,3,6-trihydroxy-9H-xanthene-9-one
Flavonoids
pmn001477 4-C-Glucose-1,3,6-trihydroxy-7-methoxyxanthone Flavonoids
Satp005088
5-hydroxy-7-(2-hydroxypropyl)-2-(3-hydroxy-2-(4-hydroxy-3,5-dimethoxybe
nzyl)propyl)-chromone Flavonoids
Wbtn006810 6,7-dihydroxy-1,3-dimethoxyxanthen-9-one* Flavonoids
Lcsn003955 Maesopsin Flavonoids
pmn001370 Pinoresinol-4,4’-O-diglucoside Lignans and Coumarins
pmn001369 1-Hydroxypineolin Diglucoside Lignans and Coumarins
pmn001375 1-Hydroxypinoresinol-1-O-Glucoside Lignans and Coumarins
Zmcn003729 1-Hydroxypinoresinol-4’-O-Glucoside Lignans and Coumarins
Lmmn002260 5′-Methoxyisolariciresinol-9’-O-glucoside Lignans and
Coumarins
WaYn005928 Buddlenol B* Lignans and Coumarins
WaYn006596 Buddlenol C Lignans and Coumarins
WaYn006188 Buddlenol E* Lignans and Coumarins
Lazn006616 Buddlenol F Lignans and Coumarins
Zmdn003480 Cycloolivil-6-O-glucoside Lignans and Coumarins
Lmsp004450 Dehydrodiconiferyl alcohol Lignans and Coumarins
Cmsp003083 Dehydrodiconiferyl alcohol-4-O-glucoside* Lignans and
Coumarins
Lmsp003655 Dehydrodiconiferyl alcohol-gamma’-O-glucoside* Lignans and
Coumarins
Lmtn002596 Dihydrodehydrodiconiferyl alcohol-4-O-glucoside* Lignans and
Coumarins
Lskp211385 dihydrosesamin Lignans and Coumarins
Lskp211249 epieudesmin Lignans and Coumarins
MWSHC20189 Epipinoresinol* Lignans and Coumarins
Lazn003893 Erythro-Guaiacylglycerol-β-Coniferyl Ether Lignans and
Coumarins
Lazn006735 Erythro-Guaiacylglycerol-β-O-4′-dehydrodisinapyl Ether
Lignans and Coumarins
Lazn005262 Erythro-Guaiacylglycerol-β-Sinapyl Ether Lignans and
Coumarins
WaYn003112 Erythro-Guaiacylglycerol-β-threo-syringylglycerol Ether
Lignans and Coumarins
pmn001371 Eucommin A Lignans and Coumarins
Lhhp102922 Fargesin Lignans and Coumarins
Lazn002951 Guaiacylglycerol-β-Guaiacyl Ether Lignans and Coumarins
Lazn002030 Guaiacylglycerol-β-Guaiacyl Ether glucoside Lignans and
Coumarins
Hmgn004139 Isohydroxymatairesinol Lignans and Coumarins
Lmmn003748 Isolariciresinol Lignans and Coumarins
Lmmn002274 Isolariciresinol-9’-O-glucoside* Lignans and Coumarins
Cmsp005051 Isolariciresinol-9-O-glucoside Lignans and Coumarins
Zmdn003762 Isosyringinoside Lignans and Coumarins
HJN083 Lariciresinol-4’-O-glucoside Lignans and Coumarins
Hmcn002743 Lirioresinol A Lignans and Coumarins
Lmmn003020 Lyoniresinol Lignans and Coumarins
Cmmn005231 Massoniresinol; Vladinol A Lignans and Coumarins
Lssp210087 Matairesinol Lignans and Coumarins
Lmmn003875 Medioresinol Lignans and Coumarins
pmn001372 Medioresinol-4,4′-di-O-glucoside Lignans and Coumarins
Rfmb056 Medioresinol-4’-O-(6″‘-acetyl)glucoside Lignans and Coumarins
Hmln002100 Nortrachelogenin-4-O-glucoside Lignans and Coumarins
pmn001376 Olivil Lignans and Coumarins
Lhmp121010 Olivil Monoacetate Lignans and Coumarins
Lmnn102709 Olivil-4’-O-glucoside Lignans and Coumarins
mws0097 Pinoresinol* Lignans and Coumarins
Rfmb25702 Pinoresinol-4-O-(6″-acetyl)glucoside Lignans and Coumarins
pmn001378 Pinoresinol-4-O-glucoside Lignans and Coumarins
Lskp211262 Secoisolariciresinol Lignans and Coumarins
Lmtn003096 Secoisolariciresinol 4-O-glucoside Lignans and Coumarins
MWSmce499 Secoisolariciresinol diglucoside Lignans and Coumarins
Cmsn002480 Secoisolariciresinol-9’-O-glucoside Lignans and Coumarins
MWS20152 Syringaresinol Lignans and Coumarins
Rfmb26201 Syringaresinol-4’-O-(6″-acetyl)glucoside Lignans and
Coumarins
MWSHC2047 Syringaresinol-4’-O-glucoside; Acanthoside B Lignans and
Coumarins
MWSmce159 6,7-Dihydroxy-4-methylcoumarin Lignans and Coumarins
Zbsp004940 6-Hydroxy-7-methoxycoumarin* Lignans and Coumarins
zjgp122320 6-hydroxycoumarin Lignans and Coumarins
mws0987 6-MethylCoumarin Lignans and Coumarins
MWSslk135 7,8-Dihydroxy-4-methylcoumarin Lignans and Coumarins
Walp004391 7-C-Glucosylcoumarin* Lignans and Coumarins
Hmqn002118 7-Hydroxycoumarin;Umbelliferone Lignans and Coumarins
mws1075 7-Methoxycoumarin Lignans and Coumarins
Lhkp101525 Apiosylskimmin (Adicardin) Lignans and Coumarins
pmn001492 Ayapin Lignans and Coumarins
MWSmce301 Coumarin-3-carboxylic Acid Lignans and Coumarins
mws1074 Daphnetin Lignans and Coumarins
Cmyn001328 Daphnin* Lignans and Coumarins
MWSmce232 Dicumarol Lignans and Coumarins
mws1013 Esculetin (6,7-Dihydroxycoumarin) Lignans and Coumarins
Lmbn001162 Esculetin-7-O-glucoside* Lignans and Coumarins
pmb3093 Esculetin-7-O-quinic acid Lignans and Coumarins
mws1015 Esculin (6,7-Dihydroxycoumarin-6-O-glucoside)* Lignans and
Coumarins
mws1014 Fraxetin (7,8-Dihydroxy-6-methoxycoumarin) Lignans and
Coumarins
MWSmce025 Fraxetin-8-O-glucoside (Fraxin) Lignans and Coumarins
Lmjp003090 Isofraxidin-7-O-glucoside Lignans and Coumarins
Lcyp000676 Isoscopoletin-β-D-glucoside* Lignans and Coumarins
MWSslk171 Nodakenin Lignans and Coumarins
Lmwp102713 Peucedanol* Lignans and Coumarins
MWSCX014 Scopoletin (7-Hydroxy-6-methoxycoumarin)* Lignans and
Coumarins
Hmbp002498 Scopoletin-7-O-xylosyl(1 → 6)glucoside* Lignans and
Coumarins
Lhqp101805 Skimmin (7-Hydroxycoumarin-7-O-glucoside) Lignans and
Coumarins
Lmjp002764 Umckalin (7-hydroxy-5,6-dimethoxycoumarin) Lignans and
Coumarins
Qmzp101901 Zanthoxyloside* Lignans and Coumarins
Wcdp010162 1-Monolinolenoyl-Rac-Glycerol* Lipids
MWSmce549 1-Monomyristin Lipids
pmb0296 1-Oleoyl-Sn-Glycerol Lipids
Zbfn008434 1-O-Linoleoyl-3-O-galactopyranosyl-L-glycerol Lipids
Wagn011658 1-Palmitoyl-Sn-Glycerol 3-O-Diglucoside Lipids
pmb1562 1-Stearidonoyl-Glycerol Lipids
Lmhp011562 1-α-Linolenoyl-glycerol* Lipids
Lmhp009773 1-α-Linolenoyl-glycerol-3-O-glucoside* Lipids
Wagn012030 2-Palmitoyl-Sn-Glycerol 3-O-Diglucoside Lipids
Lmhp011388 2-α-Linolenoyl-glycerol* Lipids
Lmhp008513 2-α-Linolenoyl-glycerol-1,3-di-O-glucoside Lipids
Lmhp009526 2-α-Linolenoyl-glycerol-1-O-glucoside* Lipids
Lmfp009701 Glycerol 9(E),11(Z),13(E)-octadecatrienoyl ester* Lipids
Walp013004 Glycidyl Linoleate Lipids
WaYn012231 LPG(18:2(9Z,12Z)/0:0) Lipids
Hmyn007168 LysoPG 16:0 Lipids
Hmyn007087 LysoPI 16:0 Lipids
Sazp010264 Monogalactosyldiacylglycerol Lipids
Lmsp010763 Monolinolenin* Lipids
Hmyp007792 PE(oxo-11:0/16:0) Lipids
Lmqn008024 PS(18:2) Lipids
mws0120 Choline Alfoscerate Lipids
pmb2221 4-Hydroxysphinganine; Phytosphingosine Lipids
pmp001264 Hexadecylsphingosine Lipids
pmd0130 LysoPC 14:0 Lipids
pmb2319 LysoPC 15:0* Lipids
Lmhp009129 LysoPC 15:0(2n isomer)* Lipids
pmb2260 LysoPC 15:1 Lipids
pmb0855 LysoPC 16:0 Lipids
pmd0132 LysoPC 16:0(2n isomer) Lipids
pmp001270 LysoPC 16:1* Lipids
Lmhp008833 LysoPC 16:1(2n isomer)* Lipids
pmb0863 LysoPC 16:2(2n isomer) Lipids
pmb2406 LysoPC 17:0* Lipids
Lmhp010515 LysoPC 17:0(2n isomer)* Lipids
Lmhp009590 LysoPC 17:1 Lipids
Lmhp008718 LysoPC 17:2 Lipids
mws0126 LysoPC 18:0 Lipids
pmd0136 LysoPC 18:0(2n isomer) Lipids
Lmhp010190 LysoPC 18:1(2n isomer) Lipids
pmp001251 LysoPC 18:2(2n isomer) Lipids
pmb0865 LysoPC 18:3(2n isomer) Lipids
Hmqp006235 LysoPC 18:4 Lipids
pmb2228 LysoPC 19:0 Lipids
Lmhp010908 LysoPC 19:1 Lipids
Lmhp007598 LysoPC 19:2(2n isomer) Lipids
Lmhp011549 LysoPC 20:1 Lipids
pmd0147 LysoPC 20:2* Lipids
pmd0146 LysoPC 20:2(2n isomer)* Lipids
Lmhp009890 LysoPC 20:3 Lipids
pmb0864 LysoPE 14:0* Lipids
Lmhp008337 LysoPE 14:0(2n isomer)* Lipids
Lmhp009187 LysoPE 15:0 Lipids
Lmhp008885 LysoPE 15:0(2n isomer) Lipids
Lmhp008440 LysoPE 15:1 Lipids
pmb0876 LysoPE 16:0 Lipids
pmd0160 LysoPE 16:0(2n isomer) Lipids
Lmhp009034 LysoPE 16:1* Lipids
Lmhp008763 LysoPE 16:1(2n isomer)* Lipids
Lmhp010162 LysoPE 17:0 Lipids
Lmhp009769 LysoPE 17:1* Lipids
Lmhp009464 LysoPE 17:1(2n isomer)* Lipids
pmb0883 LysoPE 18:0 Lipids
mws0289 LysoPE 18:1* Lipids
pmb0856 LysoPE 18:1(2n isomer)* Lipids
pmb0881 LysoPE 18:2 Lipids
pmb0874 LysoPE 18:2(2n isomer) Lipids
Lmhp008801 LysoPE 18:3 Lipids
Lmhp008589 LysoPE 18:3(2n isomer) Lipids
Lmhp008233 LysoPE 18:4 Lipids
Lmhp010040 LysoPE 20:3* Lipids
Lmhp009802 LysoPE 20:3(2n isomer)* Lipids
Lmbn006152 (9Z,11E)-Octadecadienoic acid* Lipids
MWSslk133 1,14-Tetradecanedioic Acid Lipids
pmn001686 10,16-Dihydroxypalmitic acid Lipids
Zmpn003698 11,14,17-Eicosatrienoic acid* Lipids
mws2623 11-Octadecanoic acid(Vaccenic acid)* Lipids
Lmbn005487 12,13-DHOME; (9Z)-12,13-Dihydroxyoctadec-9-enoic acid Lipids
mws5045 12-Hydroxydodecanoic acid Lipids
Lmbn009444 12-Hydroxyoctadec-9-Enoic Acid; Ricinoleic acid Lipids
Zmyn004548 12-Oxo-phytodienoic acid Lipids
Lmbn005369 13(S)-HODE;13(S)-Hydroxyoctadeca-9Z,11E-dienoic acid* Lipids
Zmzn003953 13(s)-hydroperoxy-(9z,11e,15z)-octadecatrienoic acid Lipids
MWS80007 13-Hydroperoxy-9Z,11E-octadecadienoic acid* Lipids
Lmbn005443 13-KODE; (9Z,11E)-13-Oxooctadeca-9,11-dienoic acid* Lipids
MWS2430 13-methylmyristic acid Lipids
pmb2804 13S-Hydroperoxy-9Z,11E-octadecadienoic acid Lipids
Zmyn005026 16-Methylheptadecanoic acid Lipids
Zmyn004676 17-Hydroxylinolenic acid Lipids
pmf0297 1-Eicosanol Lipids
pmf0293 1-Octadecanol Lipids
Zmyn005384 2R-Hydroxyoctadecanoic Acid* Lipids
Zmyn005252 3-Hydroxy-palmitic acid methyl ester Lipids
Wcdp006929 4-Oxo-9,11,13,15-Octadecatetraenoic Acid Lipids
pmb0885 4-Oxo-9Z,11Z,13E,15E-Octadecatetraenoic Acid Lipids
MWS2673 5,6-DiHETrE[(±)5,6-dihydroxy-8Z,11Z,14Z-eicosatrienoic acid]
Lipids
Lmbn005287 7S,8S-DiHODE;
(9Z,12Z)-(7S,8S)-Dihydroxyoctadeca-9,12-dienoic acid* Lipids
pmb2636 8,15-Dihydroxy-5,9,11,13-eicosatetraenoic acid Lipids
Lmbn005662 9(10)-EpOME;(9R,10S)-(12Z)-9,10-Epoxyoctadecenoic acid
Lipids
pmn001694 9,10,13-Trihydroxy-11-Octadecenoic Acid Lipids
Lmbn004240 9,10-Dihydroxy-12,13-epoxyoctadecanoic acid Lipids
Lmbn003970 9,12,13-TriHOME;
9(S),12(S),13(S)-Trihydroxy-10(E)-octadecenoic acid Lipids
pmn001691 9,12,13-Trihydroxy-10,15-octadecadienoic acid Lipids
pmb2791 9-Hydroperoxy-10E,12,15Z-octadecatrienoic acid Lipids
pmb2786 9-Hydroxy-10,12,15-octadecatrienoic acid* Lipids
Zmyn004449 9-Hydroxy-12-oxo-10(E),15(Z)-octadecadienoic acid Lipids
pmn001689 9-Hydroxy-12-oxo-15(Z)-octadecenoic acid* Lipids
Rfmb087 9-Hydroxy-13-oxo-10-octadecenoic Acid Lipids
WaYn010298 9-Hydroxyoctadeca-6,10,12,15-Tetraenoic Acid Lipids
Wcdp007645 9-Oxo-10,12-Octadecadienoic Acid Lipids
pmb2787 9-Oxo-10E,12Z-octadecadienoic acid Lipids
Zmjn004133 9S-Hydroperoxy-10E,12Z-octadecadienoic acid Lipids
Rfmb091 9S-Hydroxy-10E,12Z-octadecadienoic acid* Lipids
Wafn011571 alpha-Hydroxylinoleic acid* Lipids
pmf0397 Arachidic acid Lipids
Zbfn013528 Beta-Hydroxypalmitic Acid* Lipids
MWS0552 Cis-10-Pentadecenoic Acid(C15:1) Lipids
Lmbn005923 Crepenynic acid Lipids
Lmbn006210 Dihomo-gamma-linolenic acid; (8Z,11Z,14Z)-Icosatrienoic
acid* Lipids
MWS4295 DL-2-hydroxystearic acid* Lipids
Lmhn012602 Docosenoic acid Lipids
mws0474 Dodecanedioic aicd Lipids
pmb2640 Dodecanoic acid (Lauric acid) Lipids
pmn001606 Eicosenoic acid Lipids
mws0396 Elaidic Acid* Lipids
MWSslk132 Hexadecanedioic acid Lipids
Zadn009075 Hydroperoxylinoleic acid* Lipids
Wafn015217 Hydroxyicosanoic Acid Lipids
mws1491 Linoleic acid* Lipids
Yalp008047 Methyl 12-phenyldodecanoate Lipids
pmb1650 Octadeca-11E,13E,15Z-trienoic acid Lipids
Wcdp009119 Octadeca-9,12,15-trienoic acid Lipids
YC512118 Oleamide (9-Octadecenamide) Lipids
pmf0395 Oleic acid Lipids
pme2827 Palmitaldehyde Lipids
mws1488 Palmitic acid Lipids
Lmyn012331 Petroselinic acid* Lipids
pmb0889 Punicic acid (9Z,11E,13Z-octadecatrienoic acid) Lipids
mws1489 Stearic Acid Lipids
Lmsn004901 Tetracosanoic Acid (Lignoceric acid) Lipids
MWS5231 Tridecanedioic acid Lipids
MWS1900 Undecanedioic acid Lipids
mws0367 α-Linolenic Acid* Lipids
mws0366 γ-Linolenic Acid* Lipids
mws0663 1,7-Dimethylxanthine Nucleotides and derivatives
MWSmce295 1-beta-D-Arabinofuranosyluracil Nucleotides and derivatives
mws0847 1-Methyladenine Nucleotides and derivatives
pme0166 1-Methylxanthine Nucleotides and derivatives
pme3967 2-(Dimethylamino)guanosine* Nucleotides and derivatives
pmb0374 2-Aminopurine Nucleotides and derivatives
pme3961 2’-Deoxyadenosine* Nucleotides and derivatives
pme3184 2’-Deoxyadenosine-5′-monophosphate Nucleotides and derivatives
pme1194 2’-Deoxycytidine Nucleotides and derivatives
pme1184 2’-Deoxyguanosine Nucleotides and derivatives
pmc0066 2’-Deoxyinosine-5′-monophosphate Nucleotides and derivatives
pmb2507 2-Deoxyribose-1-phosphate Nucleotides and derivatives
mws0863 2-Deoxyribose-5′-phosphate Nucleotides and derivatives
Hmhp001812 2’-O-Methyladenosine Nucleotides and derivatives
mws0874 3′-Adenylic Acid Nucleotides and derivatives
pme1266 3-Methylxanthine Nucleotides and derivatives
pme0152 5,6-Dihydro-5-methyluracil Nucleotides and derivatives
pme0151 5,6-Dihydrouracil Nucleotides and derivatives
Lmqp000329 5-Aminoimidazole ribonucleotide Nucleotides and derivatives
pme1474 5’-Deoxy-5′-(methylthio)adenosine Nucleotides and derivatives
MWSmce116 5’-Deoxyadenosine* Nucleotides and derivatives
MWS2910 5-Methyl-2’-Deoxycytidine Nucleotides and derivatives
mws0572 5-Methylcytosine Nucleotides and derivatives
MWSslk102 6-Chloropurine Nucleotides and derivatives
MWS4525 6-O-methylguanine Nucleotides and derivatives
pme3968 7-Methylguanine Nucleotides and derivatives
pme2801 7-Methylxanthine Nucleotides and derivatives
MWS2984 8-Azaguanine Nucleotides and derivatives
mws0724 8-Hydroxyguanosine Nucleotides and derivatives
mws1060 9-(Arabinosyl)hypoxanthine Nucleotides and derivatives
Wcjp001256 9-Alpha-Ribofuranosyladenine* Nucleotides and derivatives
Zmsp001773 9-Arabinosyladenine* Nucleotides and derivatives
MWSHC2054 Adenine Nucleotides and derivatives
pme0230 Adenosine* Nucleotides and derivatives
Zmjn001030 Adenosine 2’-Phosphate Nucleotides and derivatives
pme2117 Adenosine 5′-diphosphate Nucleotides and derivatives
pmb0981 Adenosine 5′-monophosphate Nucleotides and derivatives
pme1173 Allopurinol Nucleotides and derivatives
mws1715 Cordycepin (3’-Deoxyadenosine)* Nucleotides and derivatives
MWSmce333 Crotonoside; 2-Hydroxyadenosine Nucleotides and derivatives
mws0884 Cyclic 3′,5′-Adenylic acid Nucleotides and derivatives
ML10180524 Cytarabine Nucleotides and derivatives
pme3732 Cytidine Nucleotides and derivatives
MWSslk257 Cytidine 5′-monophosphate(Cytidylic acid) Nucleotides and
derivatives
mws0255 Cytosine Nucleotides and derivatives
MWS5083 Flavin Single Nucleotide(FMN) Nucleotides and derivatives
pme1109 Guanine Nucleotides and derivatives
pme1178 Guanosine Nucleotides and derivatives
mws0609 Guanosine 3′,5′-cyclic monophosphate Nucleotides and
derivatives
pmb0998 Guanosine 5′-monophosphate Nucleotides and derivatives
pme0033 Hypoxanthine Nucleotides and derivatives
pme1119 Inosine Nucleotides and derivatives
pmb0532 Inosine 5′-monophosphate Nucleotides and derivatives
MWS5173 Isocytosine Nucleotides and derivatives
pme0183 Isoguanine Nucleotides and derivatives
pmb0964 Isopentenyladenine-7-N-glucoside Nucleotides and derivatives
mws0984 L-Sepiapterin Nucleotides and derivatives
Lmcp002302 N6-(2-Hydroxyethyl)adenosine* Nucleotides and derivatives
pme2060 N6-Isopentenyladenine Nucleotides and derivatives
MWS4354 N6-methyladenosine Nucleotides and derivatives
pmb0197 N7-Methylguanosine Nucleotides and derivatives
pme2651 NADP (Nicotinamide adenine dinucleotide phosphate) Nucleotides
and derivatives
pmb0530 Nicotinic acid adenine dinucleotide Nucleotides and derivatives
pme2746 Riboflavin 5′-Adenosine Diphosphate Nucleotides and derivatives
pmf0289 Riboprine Nucleotides and derivatives
pmc0281 Ribosyladenosine Nucleotides and derivatives
pme3337 Succinyladenosine Nucleotides and derivatives
mws0251 Thymine Nucleotides and derivatives
pme0257 Uracil Nucleotides and derivatives
mws0248 Uridine Nucleotides and derivatives
pme3007 Uridine 5′-diphosphate Nucleotides and derivatives
pmb2922 Uridine 5′-diphospho-d-glucose Nucleotides and derivatives
pme3188 Uridine 5′-monophosphate Nucleotides and derivatives
Zmfn000481 Uridine-5’-Diphosphate-D-Xylose Nucleotides and derivatives
Zmjp000966 Vidarabine Nucleotides and derivatives
pme0256 Xanthine Nucleotides and derivatives
mws0668 Xanthosine Nucleotides and derivatives
mws0675 β-Nicotinamide mononucleotide Nucleotides and derivatives
pme3154 Mevalonic acid Organic acids
mws0277 Quinic Acid Organic acids
mws4052 1-Aminocyclopropane-1-carboxylic acid* Organic acids
MWS4396 1-Hydroxy-2-Naphthoic Acid Organic acids
Rfmb320 1-Methylpiperidine-2-carboxylic acid* Organic acids
Lmgn004461 2-(1,3-Dihydroxy-but-2-enylidene)-6-methyl-3-oxo-heptanoic
acid Organic acids
Lcsn006884 2,2′-(3-methylcyclohexane-1,1-diyl)diacetic acid Organic
acids
Wmzn000227 2,2-Dimethylsuccinic acid Organic acids
Zmgn000503 2,3-Dihydroxy-3-Methylbutanoic Acid Organic acids
pme0278 2,6-Diaminooimelic acid Organic acids
Wccp000476 2-[(1R)-1-carboxyethoxy]propanoic acid Organic acids
Lmbn001609 2-Acetyl-2-Hydroxybutanoic Acid Organic acids
Zbqp000579 2-amino-3-(1H-pyrazol-1-yl)propanoic acid Organic acids
mws0236 2-Aminoethanesulfonic acid Organic acids
pme3017 2-Aminoisobutyric acid* Organic acids
Lmbn001288 2-Hydroxy-2-methyl-3-oxobutanoic acid Organic acids
Lmrn002746 2-Hydroxy-4-methylpentanoic acid Organic acids
Zmgn000216 2-Hydroxyethylphosphonic acid Organic acids
Zmyn000247 2-Hydroxyglutaric Acid* Organic acids
Lmmn003323 2-Hydroxyhexadecanoic acid* Organic acids
mws0341 2-Hydroxyisocaproic acid Organic acids
Lcsn006335 2-Hydroxymyristic acid Organic acids
Zmyn002323 2-Hydroxyphenylacetic acid Organic acids
pmb3101 2-Isopropylmalic Acid Organic acids
Lmgn002091 2-Methyl-3-oxoadipic acid Organic acids
Lmgn000224 2-Methyl-3-oxosuccinic acid Organic acids
mws0924 2-Methylglutaric acid* Organic acids
mws0473 2-Methylsuccinic acid* Organic acids
pme2589 2-Oxoadipic acid Organic acids
mws2124 2-Phosphoglycolate Organic acids
pme1216 2-Picolinic acid Organic acids
Zmgn001448 2-Propylmalic Acid* Organic acids
Lmbn002072 2-Propylsuccinic acid* Organic acids
MWS5147 3-(Methylthio)Propionic Acid Organic acids
ML10176345 3-Dehydroshikimic acid Organic acids
MWSmce362 3-Ethoxy-3-oxopropanoic acid Organic acids
Hmhn002738 3-Furoic acid Organic acids
Zmpn000638 3-Guanidinopropionic acid Organic acids
Lmbn001676 3-Hydroxy-3-Methyl-2-Oxopentanoic Acid* Organic acids
mws0576 3-Hydroxybutyric acid Organic acids
MWS3036 3-Hydroxyglutaric acid* Organic acids
MWS2417 3-Hydroxymandelate Organic acids
pme2601 3-Hydroxypropanoic acid Organic acids
Lmbn001754 3-Isopropylmalic Acid* Organic acids
Lmbn001718 3-Methyl-2-oxopentanoic acid Organic acids
Lmbn000216 3-Methylmalic acid* Organic acids
Lmgn000242 4,5,6-Trihydroxy-2-oxohexanoic acid Organic acids
Zmtn001464 4,8-Dihydroxyquinoline-2-carboxylic acid Organic acids
pme0295 4-Acetamidobutyric acid Organic acids
mws0567 4-Guanidinobutyric acid Organic acids
mws0373 4-Methyl-2-oxovalerate Organic acids
MWS5238 4-Phenylbutyric acid Organic acids
Lmbn001467 5-Acetamidopentanoic Acid Organic acids
MWSslk038 6-Acetamidohexanoic acid Organic acids
pme0274 6-Aminocaproic acid Organic acids
mws0972 6-Hydroxyhexanoic acid Organic acids
Lmtn004049 Abscisic acid Organic acids
mws0208 Adipic Acid* Organic acids
pme3096 Aminomalonic acid Organic acids
Lmyp003934 Anacardic acid Organic acids
mws0237 Azelaic acid Organic acids
mws0489 Benzoylformic acid Organic acids
mws0425 Citraconic acid Organic acids
mws0281 Citric Acid Organic acids
WaYn000716 Citric Acid diglucoside Organic acids
ML10197929 Creatine Organic acids
pme1936 Creatinine Organic acids
pme1730 D-Erythronolactone Organic acids
Lmmn000806 Dimethylmalonic acid* Organic acids
MWS0274 DL-3-Phenyllactic acid* Organic acids
mws0267 DL-Glyceric Acid Organic acids
MWS1709 D-Malic acid* Organic acids
MWSmce183 D-Mandelic acid Organic acids
pme3034 Ethylmalonic acid* Organic acids
mws0376 Fumaric acid* Organic acids
Wasn001627 Glucosyl 2,3-Dihydroxy-2-Methylbutanoic Acid Organic acids
Wasn003258 Glucosyl 2-Hydroxy-4-Methylpentanoic Acid Organic acids
pme0243 Glutaric acid* Organic acids
Lmhn007953 Hexylitaconic acid Organic acids
Lcsn002137 Homovanillic acid sulfate Organic acids
ML10172161 Hydroxypyruvic acid* Organic acids
MWS1882 Iminodiacetic acid* Organic acids
Zmyn000453 Isocitric Acid Organic acids
Zmgn000217 Itaconic acid Organic acids
Zmjp003163 Jasmonic acid Organic acids
Lcsn000415 Keto-Deoxy-Nonulonic acid Organic acids
mws0275 L-Malic acid* Organic acids
MWS0811 L-Pipecolic Acid Organic acids
mws0262 L-Tartaric acid Organic acids
pme0271 Maleic acid* Organic acids
Wayn000504 Malic acid-1-O-diglucoside Organic acids
pme1975 Malonic acid Organic acids
Lmyn002403 Mandelic acid-β-glucoside Organic acids
MWS2040 Methanesulfonic acid Organic acids
MWSmce536 Methyl 2-furoate Organic acids
pme0220 Methyl jasmonate Organic acids
mws0470 Methylmalonic acid* Organic acids
MWS5136 Mono-Methyl Glutarate* Organic acids
Lmmn002164 Monomethyl succinate* Organic acids
Lmyn000160 Mucic acid Dimethyl Ester Organic acids
mws1167 Oxalacetic acid Organic acids
pmf0096 Oxalic acid Organic acids
mws0159 Phenylpyruvic acid Organic acids
mws2125 Phosphoenolpyruvate Organic acids
Lmsn015919 Phytic acid Organic acids
Zmjn001813 Pimelic acid* Organic acids
mws0601 Pyrrole-2-carboxylic acid Organic acids
mws0154 Shikimic acid Organic acids
mws0242 Suberic Acid Organic acids
mws0192 Succinic acid* Organic acids
Lmgn000219 Succinic semialdehyde Organic acids
Lmbn000193 Tartronate semialdehyde* Organic acids
pme3009 trans-Aconitic acid Organic acids
pme2380 α-Ketoglutaric acid Organic acids
mws0147 β-Hydroxyisovaleric acid Organic acids
pme3011 γ-Aminobutyric acid Organic acids
Zmdp000917 δ-Guanidinovaleric acid Organic acids
Lasp003143 1,4-Benzodioxin-6-propanol Others
pmf0174 1-Decanol* Others
Lmqp006559 2-Amino-1,3-eicosanediol Others
pmf0175 2-Decanol* Others
Jmzn006005 3,4-methylenedioxy cinnamyl alcohol Others
pmf0256 3-Methyl-1-pentanol Others
pmn001380 Eucommiol Others
MWS0618 Pantothenol Others
Hmjp000461 3-O-Glucoside-3-hydroxy-y-butyrolactone Others
MWS2056 Delta-Hexalactone Others
Cmyp007180 Dihydroactinidiolide Others
pmb0128 δ-Tridecalactone Others
Waln010743
1-(2,3-dihydroxypropoxy)-3-(((2-(dimethylamino)ethoxy)(hydroxy)phosphor
yl)oxy)propan-2-yl (11Z,14Z)-octadeca-11,14-dienoate Others
Waln009920
1-(2,3-dihydroxypropoxy)-3-(((2-(dimethylamino)ethoxy)(hydroxy)phosphor
yl)oxy)propan-2-yl (8E,11Z,14Z)-octadeca-8,11,14-trienoate Others
Waln010449
1-(2,3-dihydroxypropoxy)-3-(((2-(dimethylamino)ethoxy)(hydroxy)phosphor
yl)oxy)propan-2-yl (E)-hexadec-9-enoate Others
Waln011704
1-(2,3-dihydroxypropoxy)-3-(((2-(dimethylamino)ethoxy)(hydroxy)phosphor
yl)oxy)propan-2-yl (Z)-14-Octadecenoic Acid Others
WaYn011606
1-(2,3-dihydroxypropoxy)-3-(((2-(dimethylamino)ethoxy)(hydroxy)phosphor
yl)oxy)propan-2-yl heptadecanoate Others
Waln011524
1-(2,3-dihydroxypropoxy)-3-(((2-(dimethylamino)ethoxy)(hydroxy)phosphor
yl)oxy)propan-2-yl palmitate* Others
Wcdp006741 1-(9Z,12Z-Octadecadienoyl)-Sn-Glycero-3-Phosphocholine
Others
Walp007738 14-Amino-15-hydroxy-11-methylpentadecanoic acid Others
Wcsn010224 14-hydroxy-2,6,10-trimethylpentadeca-2,5,10-trien-4-one*
Others
WaYn011395
2-(2,3-dihydroxypropoxy)-3-(((2-(dimethylamino)ethoxy)(hydroxy)phosphor
yl)oxy)propan-2-yl (Z)-14-Octadecenoic Acid Others
Waln011009
2-(2,3-dihydroxypropoxy)-3-(((2-(dimethylamino)ethoxy)(hydroxy)phosphor
yl)oxy)propyl (11Z,14Z)-octadeca-11,14-dienoate Others
Waln010192
2-(2,3-dihydroxypropoxy)-3-(((2-(dimethylamino)ethoxy)(hydroxy)phosphor
yl)oxy)propyl (8E,11Z,14Z)-octadeca-8,11,14-trienoate Others
Waln011222
2-(2,3-dihydroxypropoxy)-3-(((2-(dimethylamino)ethoxy)(hydroxy)phosphor
yl)oxy)propyl palmitate* Others
Lhyp111013 2(4H)-benzofuranone Others
Zahp011689 2,2-dimethylchromene-6-carboxylic acid Others
Hasp010605 2,3-dihydroxypropyl (9Z,12Z,15Z)-octadeca-9,12,15-trienoate
Others
Walp008255 2-aminodocoSane-1,5,7,21-tetraol Others
Walp007192 2-aminodocoSane-1,6,19,20,21-pentaol Others
Walp004995 2-Aminododecane-1,3,4-triol Others
Walp004752 2-Aminododecane-1,4-diol Others
pmb0302 2-Aminoethylphosphonate Others
WaYp007721 2-Aminohexadecane-1,16,16-triol Others
Walp007043 2-Aminohexadecane-1,4-diol* Others
WaYp006462 2-Aminohexadecane-1,5,15-triol Others
Walp007214 2-Aminohexadecane-1,5,6-triol Others
Walp008158 2-AminoicoSane-1,5,19-triol Others
Walp007190 2-AminoicoSane-1,5,7,19-tetraol Others
Walp007137 2-AminoicoSane-1,6,18,19,20-pentaol Others
WaYp007695 2-Aminooctadecane-1,16,18,18-tetraol Others
Walp008102 2-Aminooctadecane-1,4-diol Others
Walp007188 2-Aminooctadecane-1,5,7,17-tetraol Others
WaYp007548 2-Aminotetradecan-1-ol Others
Walp004906 2-Aminotetradecane-1,11,13-triol Others
Walp006011 2-Aminotetradecane-1,4-diol* Others
Walp006175 2-Aminotetradecane-1,5,11-triol Others
WaYp005128 2-Aminotetradecane-1,5,13-triol Others
Walp005087 2-Aminotetradecane-1,5,7,11-tetraol Others
Wagp006039 2-Hexylphosphoric Acid Others
Wagp002530 2-Methoxy-1-benzofuran-5-carbaldehyde Others
Wcgp003250 2-Methyl-3-hydroxyindan-1-one Others
Wagp002074 3-(1-hydroxyethyl)-4-methylpentane-1,4-diol O-Glucoside
Others
Wcgp006109
3-(2-hydroxyethyl)-5,7-dimethoxy-4-methyl-2H-1-benzopyran-2-one* Others
Wdbn005328
3,3’-Bis(3,4-dihydro-4-hydroxy-6,8-dimethoxy-2H-1-benzopyran) Others
Lskp211267 3-Ethyl-7-hydroxyphthalide Others
Wchn004015 3-Hydroxy-1-(4′-hydroxy-3′-methoxyphenyl)-propan-1-one
Others
Wagp005869 3-Hydroxy-beta-ionol 3-(6″-Malonyl)Glucoside Others
Wagp005297 3-Hydroxy-beta-ionol 3-Glucoside* Others
Wcdp001930 3ξ-(1ξ-hydroxyethyl)-7-hydroxy-1-isobenzofuranone Others
Saln003418 4-(Beta-D-Glucopyranosyloxy)-2,4′,6-Trihydroxybenzophenone
Others
Wagp001892 4-(Beta-D-Glucopyranosyloxy)-2-Pentanol Others
Wcsn010254
4-[3-(4,8-dimethylnona-3,7-dienyl)-3-methyloxiran-2-yl]butan-2-one*
Others
Zmmp002106 4-methyl-1,5,2,3-dioxadiazinan-2-amine Others
pmb0764 4-Methyl-5-thiazoleethanol Others
zjgp122321 4-O-acetyl-3-O-caffeoyl-2-C-methyl-D-erythronate* Others
Wcgp003276 5-(2-hydroxypropyl)-3H-2-benzofuran-1-one Others
Zbzp007397 5,6,7,7a-tetrahydro-4,4,7a-trimethyl-2(4H)-benzofuranone
Others
Wcgp009361
5,7-diethoxy-3-(2-hydroxyethyl)-4-methyl-2H-1-benzopyran-2-one Others
Lmln001856
5,7-Dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)-4H-chromen-3-yl-alloside
Others
Zahn007990 5-hydroxy-3,4-dimethyl-5-pentylfuran-2(5H)-one Others
Lhmp122205 5-O-Methyllatifolin Others
Wcsn010496 6,10,14-Trimethylpentadeca-5,9-Diene-2,13-Dione Others
Hahn002084 6’-O-caffeoylcatalpol* Others
Wcsn011125 Ethyl
15,16-dihydroxy-5,9-dimethyloctadeca-4,6,8,10,13-pentaenoate Others
Lhhp120823 Eugenyl formate Others
Wasn003817 Glucosyl 5,8-dihydroxy-2,6-dimethylocta-2,6-dienoic acid
Others
Wasn005621 Glucosyl 9-hydroxy-3-methyldec-2-enoic acid Others
Wcdp004275 Lauramine oxide Others
Wcdp006912 Lauryldiethanolamine* Others
Lcsp012679 linolenoylethanolamine Others
Lmhp001671 Noreugenin-7-O-glucoside* Others
Wcdp010708 Octadeca-2,9,12,15-tetraen-1-ol Others
Waln006120 Octyl 6-O-Alpha-L-Arabinopyranosyl-Beta-D-Glucopyranoside
Others
MWS20159 Phenyl-β-D-glucopyranoside Others
zjgp122326 Pyridine-4-formyl-O-β-D-glucopyranoside* Others
Zmsn110105 Rumexobtusifolius Others
Wcdp005264 Tetradecasphinganine* Others
MWSmce581 2,4-Dihydroxybenzaldehyde Others
Lmbn001981 2,5-Dihydroxybenzaldehyde* Others
Lmbn005172 2,6-Dimethoxybenzaldehyde* Others
MWS1844 2-Pentyl-3-phenyl-2-propenal Others
Wmlp000056 3,5-Dimethoxy-4-hydroxybenzaldehyde Others
Lmbn002737 3-Methylbenzaldehyde Others
MWSmce644 4-Acetoxy-3-Ethoxybenzaldehyde Others
Zmdp000376 4-Guanidinobutanal Others
mws0628 4-Hydroxybenzaldehyde Others
MWSCX017 4-hydroxyphenyl acrylaldehyde* Others
MWS1852 4-Methoxybenzaldehyde Others
MWS20172 5-Hydroxymethylfurfural Others
MWSmce040 Isovanillin Others
Hmgn001653 Protocatechualdehyde* Others
mws1350 Syringaldehyde; 4-Hydroxy-3,5-Dimethoxybenzaldehyde Others
mws0458 Vanillin; 4-Hydroxy-3-Methoxybenzaldehyde* Others
Hmyp002315 3,5,7,4’-Tetrahydroxy-Coumaronochromone Others
Hmsp003093 3,7-Dihydroxychromen-4-one Others
Layp002880 5,7-Dihydroxychromone glucoside Others
MWSHY0141 7-Hydroxy-4-chromone Others
Zmzp006646 Capillarisin Others
MWSmce658 Noreugenin; 5,7-Dihydroxy-2-Methylchromone Others
pmp000307 Sec-O-glucosylhamaudol Others
Lmqn000432 1-(sn-Glycero-3-phospho)-1D-myo-inositol Others
pme2529 1,5-Anhydro-D-glucitol Others
MWS0559 1,6-anhydro-β-d-glucose Others
Wafn004792 1-O-Acetyl-Glucopyranose 6-Decanoate Others
Zmyn000268 2,3-Dihydroxypropanal Others
Zmyn000230 2-Dehydro-3-deoxy-L-arabinonate* Others
Lmbn000198 3-Dehydro-L-Threonic Acid* Others
Lcsn000341 3’-Fucosyllactose Others
Zmgn000447 3-Phospho-D-glyceric acid Others
Wasn000977 4-O-galactopyranosylxylose Others
Wasn000495 6-O-alpha-L-arabinopyranosyl-d-glucopyranose Others
Jmbn003202 Butyl Beta-D-Fructopyranoside Others
Hmqp001042 Butyl beta-D-glucoside Others
Lmsn000954 Dambonitol Others
ML10171848 D-Arabinono-1,4-lactone* Others
MWSmce676 D-Arabinose* Others
mws0437 D-Arabitol* Others
MWSmce203 D-Cellobiose Others
Zmzn000079 D-Erythrose-4-phosphate Others
mws1164 d-Fructose* Others
MWS2442 d-Fructose 6-Phosphate* Others
mws1595 D-Fucose* Others
Zmpn000199 D-Galactaric acid Others
pmf0139 D-Galactose* Others
mws1189 D-Galacturonic acid* Others
MWSmce220 D-Glucono-1,5-lactone* Others
pme3705 D-Glucoronic acid* Others
pmb0786 D-Glucosamine Others
Zmyn000110 D-Glucosamine 1-phosphate Others
mws4170 d-Glucose* Others
Zmyn000083 d-Glucose 1,6-bisphosphate Others
mws0866 d-Glucose 6-phosphate* Others
mws1090 d-Glucose-1-phosphate* Others
mws4175 D-Glucurono-6,3-lactone Others
Lmxn000380 Digalactosylglycerol Others
Zmzn000078 Dihydroxyacetone phosphate Others
MA10039641 d-Lactose* Others
MWSmce682 DL-Xylose* Others
Lmsn000381 D-Maltose* Others
mws1593 D-Maltotetraose Others
mws1155 d-Mannitol* Others
pmf0138 D-Mannose* Others
pme0500 D-Melezitose Others
mws1589 D-Panose* Others
mws2104 D-Pinitol Others
Zmgn000173 d-Ribose Others
Zmyn000108 D-Saccharic acid Others
pme3163 D-Sedoheptuiose 7-phosphate Others
mws0214 D-Sorbitol Others
pme0519 D-Sucrose* Others
pme2134 d-Threitol* Others
mws0889 D-Threonic Acid Others
pma0134 D-Threose Others
mws0264 D-Trehalose* Others
pme2237 Dulcitol* Others
mws0344 D-Xylonic acid Others
mws1080 Galactinol Others
pmb3081 Glucaric acid-1-Phosphate Others
pme0534 Gluconic acid Others
MWSmce113 Guaifenesin Others
Hmln000297 Inositol* Others
mws5038 Isomaltulose* Others
MWSmce165 L-Fucitol Others
pme2435 L-Fucose* Others
MWSmce576 l-Glucose* Others
pme2253 L-Gulono-1,4-Lactone* Others
MWSmce199 L-Xylose* Others
MWS1983 Maltitol Others
MWS0442 Maltotriose Others
MWSmce486 Manninotriose Others
mws1333 Melibiose Others
pmf0283 Meso-Erythritol* Others
mws2608 N-Acetyl-D-galactosamine Others
pme2755 N-Acetyl-D-glucosamine Others
pmb3079 N-Acetyl-D-glucosamine-1-phosphate Others
mws4174 N-Acetyl-D-mannosamine Others
mws4163 Nystose Others
Hmqp000191 Planteose Others
pme2125 Raffinose* Others
mws0854 Rhamnose* Others
mws0213 Ribitol* Others
pma6455 Ribulose-5-phosphate Others
Lmqn000351 Rutinose Others
Hmcn000192 Sedoheptulose Others
Lmmn000214 Solatriose Others
Zmpn000095 Sorbitol-6-phosphate Others
Lmqn000213 Stachyose Others
mws1089 Sucrose-6-phosphate Others
mws2523 Trehalose 6-phosphate Others
Lmdn000248 Verbascose Others
pme0513 Xylitol* Others
MWSslk225 1-Indanone Others
Zmgp004297 1-phenyl-7-(4-hydroxyphenyl)-4-ene-3-heptanone Others
Lasp003640 2,4-Dihydroxy-6-methoxyacetophenone Others
Lafp003256 3,4’-Dihydroxy-3′,5′-dimethoxypropiophenone Others
pmp001119 3,5-Dihydroxy-2,4-dimethoxy-9H-fluoren-9-one Others
Lmyp003951 3-Hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)propan-1-one
Others
MWSslk095 4-Hydroxy-2,5-dimethyl-3(2H)furanone Others
MWS20181 4’-Hydroxy-3′-methoxyacetophenone (Acetovanillone) Others
MWSmce466 4-Hydroxyacetophenone Others
MWSmce283 4’-Hydroxypropiophenone Others
Wbtn006721 6,8-dihydroxy-3-methyl-9-oxoxanthene-1-carboxylic acid*
Others
MWSslk226 Benzylacetone Others
Wbmp003302 Frambinone Others
MWSHC20159 Roseoside Others
Lmtp004146 Santalin Others
MWS0434 Trans-dehydrorosinone Others
Wasn000528 2-O-α-d-Glucopyranosyl-l-ascorbic acid Others
pme2596 4-Pyridoxic acid Others
pmb0801 4-Pyridoxic acid-O-glucoside Others
pme2266 Biotin Others
MA10039492 Dehydroascorbic acid Others
mws1337 D-Pantothenic Acid Others
MWSmce690 Erythorbic Acid; Isoascorbic Acid Others
Wasn001007 Isoascorbic acid 2-O-glucoside Others
MWSmce039 Isonicotinic acid Others
pma1751 N-(beta-D-Glucosyl)nicotinate* Others
mws0133 Nicotinamide Others
pma3101 Nicotinate D-ribonucleoside Others
pme0490 Nicotinic acid (Vitamin B3) Others
pme2165 Orotic acid (Vitamin B13) Others
pme3511 Orotidine Others
MWSmce674 Phylloquinone (Vitamin K1) Others
Zmjp000624 Pyridoxal Others
mws0655 Pyridoxal-5′-phosphate Others
pme1383 Pyridoxine Others
pmb0790 Pyridoxine-5’-O-diglucoside Others
pmb0789 Pyridoxine-5’-O-glucoside Others
pme1306 Pyridoxine-5′-phosphate Others
pme2289 Retinol (Vitamin A1) Others
mws0232 Riboflavin (Vitamin B2) Others
MWSmce489 2,3,5,4’-Tetrahydroxystilbene-2-O-glucoside Others
Lmtp004915 3,5-Dihydroxy-3′,4′-diacetoxylstilbene-3-O-glucoside Others
MWSmce484 Astringin Others
Zmhn001970 Piceid (3,4′,5-Trihydroxystilbene-3-O-glucoside) Others
mws0021 Resveratrol Others
mws0178 Chlorogenic acid (3-O-Caffeoylquinic acid)* Phenolic acids
mws2108 Cryptochlorogenic acid (4-O-Caffeoylquinic acid)* Phenolic
acids
pmn001382 Isochlorogenic acid A* Phenolic acids
[66]Li512115 Isochlorogenic acid B* Phenolic acids
pmn001384 Isochlorogenic acid C* Phenolic acids
MWSprf004 Neochlorogenic acid (5-O-Caffeoylquinic acid)* Phenolic acids
mws1358 Pyrocatechol Phenolic acids
Zbfn002690 1-(4-Hydroxybenzoyl)Glucose; 25,545–07-7 Phenolic acids
pmn001681 1-(4-Methoxyphenyl)-1-propanol Phenolic acids
Lmfn001337 1,2,3-Tri-O-galloyl-β-d-glucose* Phenolic acids
Zbyn004414 1,2,4,6-tetra-O-galloyl-β-d-glucose Phenolic acids
Zmdn003203 1,2,6-Tri-O-galloyl-β-d-glucose* Phenolic acids
Lmsn004534 1,2-Di-O-galloyl-6-O-Cinnamoyl-β-d-glucose Phenolic acids
Lmfn001209 1,3,6-Tri-O-galloyl-β-d-glucose* Phenolic acids
Cmbp005523 1,3-O-Dicaffeoylglycerol Phenolic acids
mws1584 1,3-O-Dicaffeoylquinic Acid (Cynarin) Phenolic acids
Lmsn003088 1,4,6-Tri-O-galloyl-β-d-glucose* Phenolic acids
Wmhn001495 1,4-Di-O-Galloyl-d-glucose Phenolic acids
Waxn004217 1,5-O-dicaffeoyl-3-O-glucoside-quinic acid Phenolic acids
Lmsn004322 1,6-Di-O-caffeoyl-β-d-glucose* Phenolic acids
Lmsn004659 1,6-Di-O-galloyl-2-O-Feruloyl-β-d-glucose Phenolic acids
mws0748 1-Caffeoylquinic acid Phenolic acids
pmp000086 1-Feruloyl-sn-glycerol Phenolic acids
MWS2066 1-Naphthol* Phenolic acids
Wasn002933 1-O-(3,4,5-Trimethoxybenzoyl)-B-D-Glucopyranoside Phenolic
acids
Lmtn000940 1-O-(3,4-Dihydroxy-5-methoxy-benzoyl)-glucoside Phenolic
acids
Lmnn002886 1’-O-(3,4-Dihydroxyphenethyl)-O-caffeoyl-glucoside Phenolic
acids
Lmsn002288 1-O-Caffeoyl-(6-O-glucosyl)-β-d-glucose Phenolic acids
Lmsn004690 1-O-Caffeoyl-3-O-galloyl-4,6-(S)-HHDP-β-d-glucose Phenolic
acids
Lmsn002937 1-O-Caffeoyl-6-O-galloyl-β-d-glucose Phenolic acids
Hmbp003234 1-O-Caffeoylglycerol Phenolic acids
pmn001420 1-O-Caffeoyl-β-d-glucose* Phenolic acids
Lmsn002887 1-O-Caffeoyl-β-D-xylose Phenolic acids
Lmsp004521 1-O-Cinnamoyl-4,6-(S)-HHDP-β-d-glucose Phenolic acids
pma3724 1-O-Feruloylquinic acid Phenolic acids
Zmhn002422 1-O-Feruloyl-β-d-glucose Phenolic acids
Lmsn004323 1-O-Galloyl-2-O-Feruloyl-β-d-glucose Phenolic acids
Lmsn003644 1-O-Galloyl-6-O-Feruloyl-β-d-glucose Phenolic acids
Lmsn001014 1-O-Galloyl-β-d-glucose* Phenolic acids
pmb2871 1-O-Gentisoyl-β-D-glucoside* Phenolic acids
Lmsn005321 1-O-p-Coumaroyl-2-O-galloyl-4,6-(S)-HHDP-β-d-glucose
Phenolic acids
pmb3068 1-O-p-Coumaroylquinic acid Phenolic acids
pmn001419 1-O-p-Coumaroyl-β-d-glucose* Phenolic acids
pmn001320 1-O-p-Cumaroylglycerol Phenolic acids
Zbjn003642 1-O-rhamnose-3-O-Caffeoyl Quinic Acid Phenolic acids
Lmsn002247 1-O-Salicyloyl-β-d-glucose* Phenolic acids
HJN003 1-O-Sinapoyl-β-d-glucose Phenolic acids
Lmtn002565 1-O-Vanilloyl-d-Glucose Phenolic acids
Zbln003341
2-(2-(3,4-dihydroxyphenyl)-2-methoxyethoxy)-6-(hydroxymethyl)tetrahydro
-2H-pyran-3,4,5-tri Phenolic acids
Jmwn002117 2-(3,4-dihydroxyphenyl)ethanediol 1-O-β-D-glucopyranoside*
Phenolic acids
pme3083 2-(Formylamino)benzoic acid Phenolic acids
MWSslk138 2,3,4-Trihydroxybenzoic acid Phenolic acids
Lafp002342 2,3-Dihydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)propan-1-one
Phenolic acids
mws0639 2,3-Dihydroxybenzoic Acid* Phenolic acids
MWSmce490 2′,4′,6′-Trihydroxyacetophenone Phenolic acids
Xmbp001692 2,4,6-Trihydroxybenzoic acid Phenolic acids
mws0885 2,4-Dihydroxybenzoic acid Phenolic acids
Lmbn013410 2,4-Di-Tert-Butylphenol* Phenolic acids
mws0180 2,5-Dihydroxybenzoic acid; Gentisic Acid* Phenolic acids
Lmdp002901 2,6-Dihydroxy-4-isopropylphenyl-1-O-β-D-glucoside Phenolic
acids
MWSmce587 2,6-Dimethoxybenzoic acid Phenolic acids
Wmyn000217 2,6-dimethoxy-hydroquinone-4-O-β-D-glucopyranoside Phenolic
acids
Lmln010063 2,6-Di-tert-butylphenol* Phenolic acids
NK10253223 2-Amino-3-methoxybenzoic acid Phenolic acids
MWSmce342 2-Caffeoyl-L-tartaric acid (Caftaric acid) Phenolic acids
pmp000087 2-Feruloyl-sn-glycerol Phenolic acids
Lmgp002452 2-Glucosyloxy-(4-hydroxyphenyl)acetic acid (Dhurrin acid)
Phenolic acids
Lmrn001951 2-Hydroxy-3-(4-Hydroxyphenyl)Propanoic Acid Phenolic acids
MWS2001 2-Hydroxy-3,5-dinitrobenzoic acid Phenolic acids
Lmrn003000 2-Hydroxy-3-phenylpropanoic acid Phenolic acids
Lmbn001930 2-Hydroxybenzaldehyde (Salicylaldehyde) Phenolic acids
Lmmn001643 2-Hydroxycinnamic acid* Phenolic acids
Hmsn002948 2-Hydroxyphenol-1-O-glucosyl(6 → 1)rhamnoside Phenolic acids
MWS2069 2-Methoxy-4-methylphenol Phenolic acids
Zmyn002919 2-Methylbenzoic acid Phenolic acids
MWS1875 2-Naphthol* Phenolic acids
Zmzn002575 2-Nitrophenol Phenolic acids
Zbfn003867 2-O-(3,4-dihydroxyphenylacetyl)-6-O-caffeoylglucoside
Phenolic acids
Zbfn004301 2-O-(4-carboxylic acid phenethyl)-6-O-caffeoyl glucoside
Phenolic acids
Wacn002584 2-O-Caffeoylhydroxycitric Acid Phenolic acids
Lmhn102068 2-O-Caffeoylmalic acid Phenolic acids
Hmln000873 2-O-Galloyl-d-glucose Phenolic acids
Wacn003131 2-O-P-Coumaroylhydroxycitric Acid Phenolic acids
HJN093 2-O-Salicyl-6-O-Galloyl-d-Glucose Phenolic acids
Lakn001671 2-β-D-Glucopyranosyloxy-5-hydroxy-phenylacetic acid Phenolic
acids
Lakn003294 2-β-D-Glucopyranosyloxy-5-hydroxyphenylacetic
acidmethylester* Phenolic acids
HJAP051 3-(3,4,5-Trimethoxyphenyl)propan-1-ol Phenolic acids
MWS3046 3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid Phenolic acids
mws0346 3-(3-Hydroxyphenyl)-propionic acid Phenolic acids
MWSmce713 3-(4-Hydroxyphenyl)-1-propanol Phenolic acids
mws0467 3-(4-Hydroxyphenyl)-propionic acid* Phenolic acids
HJN102 3,4,5-Tricaffeoylquinic acid Phenolic acids
pmn001517 3,4,5-Trimethoxyphenyl-1-O-Glucoside Phenolic acids
Zmhn004909 3,4-Digalloylshikimic acid Phenolic acids
Jmwp002208 3,4-dihydroxy phenylethanol Phenolic acids
pme2598 3,4-Dihydroxybenzeneacetic acid* Phenolic acids
mws0183 3,4-Dihydroxybenzoic acid (Protocatechuic acid)* Phenolic acids
Jmwn002172 3,4-dihydroxyphenylethanol-β-D-glucopyranoside Phenolic
acids
Lckn000312
3,4-dihydroxy-β-phenylethoxy-O-α-L-rhamnopyranosyl(1 → 3)-6-O-caffeoyl(
cis)-β-D-glucopyranoside* Phenolic acids
MWSmce332 3,4-Dimethoxycinnamic acid Phenolic acids
mws0612 3,4-Dimethoxyphenyl acetic acid Phenolic acids
Zbjn003262 3,4-O-di-Caffeoyl-1-O-glucoside Quinic Acid Phenolic acids
Wmzn002116 3,5-Dicaffeoylquinic acid Phenolic acids
pmn001525 3,5-Digalloylshikimic acid Phenolic acids
HJN037 3,5-Dihydroxy-4-methoxybenzoic acid; 4-O-Methylgallic Acid
Phenolic acids
MWSmce454 3,5-Dihydroxyacetophenone Phenolic acids
MWS1944 3,5-Dihydroxytoluene Phenolic acids
Lmsn004970 3,6-Di-O-caffeoyl glucose* Phenolic acids
MA10107783 3-[(1-Carboxyvinyl)oxy]benzoic acid Phenolic acids
Jmwn002494 3-[4-(β-D-glucopyranoside)-phenylacrylic]-acid Phenolic
acids
mws0444 3-Aminosalicylic acid Phenolic acids
MWSHC20102 3-Hydroxy-1-(4-Hydroxy-3-Methoxyphenyl)Propan-1-One Phenolic
acids
pmn001690 3-Hydroxy-4-isopropylbenzylalcohol-3-O-glucoside Phenolic
acids
MWSslk066 3-Hydroxy-4-methoxybenzoic acid; Isovanillic Acid Phenolic
acids
pmn001521 3-Hydroxy-5-Methylphenol-1-O-(6’-Galloyl)Glucoside* Phenolic
acids
pmn001511 3-Hydroxy-5-Methylphenol-1-O-Glucoside Phenolic acids
Lmgp002593 3-hydroxybenzaldehyde Phenolic acids
Lmyn004439 3-Hydroxyl-5-methylphenol-1-O-β-D-(6′-galloyl)glucoside*
Phenolic acids
MWS4301 3-hydroxyphenylacetic acid* Phenolic acids
MWS3149 3-Methoxybenzoic acid Phenolic acids
Zmgn001989 3-Methylcatechol Phenolic acids
MWS2058 3-Methylsalicylic Acid Phenolic acids
WaYp004929 3-O-(p-coumaroyl) 3-Hydroxy-3-methylglutaric acid* Phenolic
acids
Zbln002999
3-O,6-O-bis(3-methoxy-4-hydroxy-trans-cinnamoyl)-β-D-fructofuranosyl2-O
,6-O-diacetyl-α-D-glucopyranoside|1-O-Acetyl-3-O,6-O-bis[3-(4-hydroxy-3
-methoxyphenyl)acryloyl]-β-D-fructofuranosyl1-O,2-O,6-O-triacetyl-α-D-g
lucopyranoside Phenolic acids
Zaln004082 3-O-caffeoylshikimic acid* Phenolic acids
pmb0752 3-O-Feruloylquinic acid Phenolic acids
pmb2833 3-O-Feruloylquinic acid-O-glucoside* Phenolic acids
Hmln000659 3-O-Galloyl-d-glucose* Phenolic acids
MWSmce387 3-O-Methylgallic acid Phenolic acids
Lmsp004151 3-O-p-Coumaroyl-4,6-(S)-HHDP-β-d-glucose Phenolic acids
pmn001421 3-O-p-Coumaroylquinic acid* Phenolic acids
pmb3064 3-O-p-Coumaroylquinic acid-O-glucoside Phenolic acids
pmb3075 3-O-p-Coumaroylshikimic acid Phenolic acids
pmb3072 3-O-p-Coumaroylshikimic acid-O-glucoside Phenolic acids
Lmtn003598 3-Prenyl-4-O-glucosyloxy-4-hydroxybenzoic acid Phenolic
acids
Lmyn003835 4-(3,4,5-Trihydroxybenzoxy)benzoic acid Phenolic acids
Walp002129 4-Acetoxy-3-Methoxybenzoic Acid glucoside Phenolic acids
mws1336 4-Aminobenzoic acid Phenolic acids
ML10177402 4-Aminosalicylic acid Phenolic acids
Zaln004057 4-caffeoylshikimic acid* Phenolic acids
Jmwn004308
4-Dihydroxyphenethoxy-8-O-[6-O-(4-O-glucosyl)feruloyl]glucoside
Phenolic acids
MWSslk155 4-Hydroxy-3-methoxymandelate Phenolic acids
mws0749 4-Hydroxybenzoic acid Phenolic acids
Wayn001856 4-Hydroxybenzoic acid 4-(6-O-sulfo)glucopyranoside Phenolic
acids
HJN025 4-Hydroxybenzyl Alcohol Phenolic acids
MWSmce370 4-Hydroxyphenylacetic acid* Phenolic acids
MWS5206 4-Hydroxyphenyllactic Acid* Phenolic acids
pmb2795 4-Methoxycinnamic acid Phenolic acids
Lmbn004847 4-Methoxyphenylpropionic acid Phenolic acids
mws0566 4-Methylcatechol Phenolic acids
Zmyn002321 4-Methylphenol Phenolic acids
pme2828 4-Nitrophenol Phenolic acids
Wafn002319 4-O-(3’-O-alpha-d-Glucopyranosyl)caffeoylquinic acid
Phenolic acids
Wafn002874 4-O-(4’-O-alpha-d-Glucopyranosyl)caffeoylquinic acid
Phenolic acids
Zmhn002643 4-O-(6’-O-Glucosyl-4″-hydroxybenzoyl)-4-hydroxybenzyl
alcohol Phenolic acids
Zbln003174 4”-O-Acetylverbascoside Phenolic acids
Wdtp010604 4-Octylphenol-1-O-glucuronide Phenolic acids
Lmqn000859 4-O-Glucosyl-2-hydroxy-6-methoxyacetophenone Phenolic acids
Zmhn000892 4-O-Glucosyl-3,4-dihydroxybenzyl alcohol Phenolic acids
Zmhn001358 4-O-Glucosyl-4-hydroxybenzoic acid* Phenolic acids
Zmhn002227 4-O-Glucosyl-sinapate Phenolic acids
pma6460 4-O-p-Coumaroylquinic acid Phenolic acids
pma0110 4-O-Sinapoylquinic acid Phenolic acids
Hmhn003518 4-O-β-D-glucopyranosylferulic acid Phenolic acids
Hmtn001120 5-(2-Hydroxyethyl)-2-O-glucosylphenol Phenolic acids
MWSmce001 5-Acetylsalicylic acid Phenolic acids
pmn001516 5-Galloylshikimic acid Phenolic acids
Lmmn003663 5-Glucosyloxy-2-Hydroxybenzoic acid methyl ester Phenolic
acids
Lmzn001582 5′-Glucosyloxyjasmanic acid Phenolic acids
MWSHC20125 5-O-Caffeoylshikimic acid Phenolic acids
pmb2554 5-O-Feruloyl quinic acid glucoside* Phenolic acids
Lmgn003073 5-O-Feruloylquinic acid Phenolic acids
Zmhn001703 5-O-Galloyl-D-hamamelose* Phenolic acids
pmb3074 5-O-p-Coumaroylquinic acid* Phenolic acids
Ymjm000116 6-O-Acetylarbutin Phenolic acids
Lman003972 6-O-Caffeoylarbutin Phenolic acids
Zmhn001793 6-O-Caffeoyl-d-glucose* Phenolic acids
Hmbn002692 6’-O-Feruloyl-D-sucrose Phenolic acids
Zmhn002334 6-O-Feruloyl-β-d-glucose Phenolic acids
Lmfn000604 6-O-Galloyl-β-d-glucose* Phenolic acids
Lmsn003628 6’-O-Sinapoylsucrose Phenolic acids
Zmxn003874 7,8-Dihydro-Buddlenol B Phenolic acids
Smcn001947 Acteoside; Verbascoside* Phenolic acids
Lmqp002761 Alnusonol Phenolic acids
Lmtn002233 Androsin Phenolic acids
pmb2654 Anthranilate-1-O-Sophoroside Phenolic acids
mws1078 Anthranilic Acid Phenolic acids
MWSmce675 Arbutin Phenolic acids
Labn003910 Benzyl B-Primeveroside* Phenolic acids
mws1297 Benzyl glucoside Phenolic acids
Hmln003529 Benzyl β-primeveroside Phenolic acids
Lmtn002324 Benzyl-(2”-O-glucosyl)glucoside* Phenolic acids
Cmjn004337 Benzyl-(2”-O-xylosyl)glucoside* Phenolic acids
Lmyn003028 Benzyl-β-gentiobioside* Phenolic acids
Lmwp011196 Bis(2-ethylhexyl)phthalate* Phenolic acids
mws2120 Brevifolin carboxylic acid Phenolic acids
MWSmce341 Butyl isobutyl phthalate* Phenolic acids
mws2212 Caffeic acid Phenolic acids
MWSCX015 Caffeic aldehyde Phenolic acids
Zbfn002396 Caffeoyl-O-mannitol Phenolic acids
Labn003679 Caffeyl alcohol 4-O-β-D-glucopyranoside Phenolic acids
MWS0550 Cinnamaldehyde Phenolic acids
mws2213 Cinnamic acid Phenolic acids
mws0906 Coniferin Phenolic acids
mws0093 Coniferyl alcohol Phenolic acids
Hmsn002272 Demethyl coniferin Phenolic acids
Lmlp012720 Dibutyl phthalate* Phenolic acids
Lmgp003989 Dicaffeoylshikimic acid Phenolic acids
pmn001513 Digallic Acid Phenolic acids
Lmlp001436 Dihydrocaffeic acid Phenolic acids
Lmmn000774 Dihydrocaffeoylglucose* Phenolic acids
Lmxp011770 Diisobutyl phthalate* Phenolic acids
Lmmp010562 Diisooctyl Phthalate* Phenolic acids
MWSslk097 Dimethyl phthalate Phenolic acids
Lmzn001983 D-Threo-guaiacylglycerol-7-O-β-D-glucoside Phenolic acids
Lazn001573 Erythro-Guaiacylglycerol Phenolic acids
mws2184 Ethyl caffeate Phenolic acids
MWSslk006 Ethyl Vanillate Phenolic acids
mws0014 Ferulic acid* Phenolic acids
Hmmn002544 Ferulic acid-4-O-glucoside Phenolic acids
pmb0108 Feruloyl syringic acid Phenolic acids
Lmhn003074 Feruloylmalic acid Phenolic acids
mws0024 Gallic acid Phenolic acids
pmb2928 Gallic acid-4-O-glucoside Phenolic acids
Hmtn001302 Glucosyloxybenzoic acid Phenolic acids
MWSHC2022 Glucosyringic acid Phenolic acids
Cmyp005063 Grandidentatin Phenolic acids
pme1292 Homogentisic acid* Phenolic acids
WaYn002313 Homosyringic Acid 4’-O-Glucoside Phenolic acids
mws0117 Homovanillic acid; 4-Hydroxy-3-methoxyphenylacetic acid
Phenolic acids
pmb3056 Homovanilloylquinic acid Phenolic acids
Lmyn002435 Hydrangeifolin I Phenolic acids
MA10014775 Hydroquinone Phenolic acids
Wafn003070 Hydroxyferulic acid glucoside Phenolic acids
MWSmce264 Hydroxytyrosol Phenolic acids
Hmgp001944 Isoacteoside Phenolic acids
pme0422 Isoferulic Acid* Phenolic acids
Lmmn001294 Koaburaside* Phenolic acids
[67]Li512113 Maleoyl-caffeoylquinic acid Phenolic acids
MWS1776 m-Cresol Phenolic acids
MWSmce680 Mequinol Phenolic acids
Hmtn001288 Methyl 2,4-dihydroxyphenylacetate* Phenolic acids
Lmbn004790 Methyl 3-(3-hydroxy-4-methoxyphenyl)propanoate* Phenolic
acids
Lmcn002982 Methyl 3-O-Methyl Gallate Phenolic acids
Zmgn004894 Methyl 4-hydroxybenzoate* Phenolic acids
Wafn002807 methyl 4-O-galloylchlorogenate Phenolic acids
Hmdn001963 Methyl Brevifolincarboxylate Phenolic acids
Lmdn003756 Methyl caffeate Phenolic acids
MWSHC20168 Methyl cumalate* Phenolic acids
MWSmce230 Methyl gallate Phenolic acids
Wbsp004755 Methyl Hydroxycinnamate Phenolic acids
Lmmn002179 Methylsalicylate-2-O-glucoside Phenolic acids
mws0145 O-Anisic acid (2-Methoxybenzoic acid)* Phenolic acids
pme1439 p-Coumaric acid* Phenolic acids
MWSslk144 p-Coumaric acid ethyl ester Phenolic acids
mws1195 p-Coumaric acid methyl ester Phenolic acids
Zmhn002301 p-Coumaric acid-4-O-glucoside* Phenolic acids
Lmhn002926 p-Coumaroylmalic acid Phenolic acids
pmb3055 p-Coumaroylquinic acid-4’-O-glucuronide Phenolic acids
MWS1846 Phenoxyacetic acid* Phenolic acids
MWS1848 Phenyl acetate Phenolic acids
Hmhn003067 Phenylpropionic acid-O-β-D-glucopyranoside Phenolic acids
NK10264324 Phloroglucinol; 1,3,5-Benzenetriol Phenolic acids
Hmhn000927 Phloroglucinol-1-O-β-D-glucopyranoside Phenolic acids
pme0282 Phthalic acid Phenolic acids
pmp001285 Phthalic anhydride Phenolic acids
Lmln001195 Picein (4-Acetylphenyl-glucoside) Phenolic acids
mws1506 Plantamajoside Phenolic acids
MWS2070 Propyl 4-hydroxybenzoate Phenolic acids
Wasn004683 Protocatechuic acid 1-O-(Glucosylvanilloyl) Phenolic acids
Wasn005073 Protocatechuic acid 4-O-(2”-O-Vanilloyl)Glucoside Phenolic
acids
Lakn002165 Protocatechuic acid glucosyl xyloside Phenolic acids
MWSmce501 Protocatechuic Acid Methyl Ester Phenolic acids
pmn001367 Protocatechuic acid-4-O-glucoside* Phenolic acids
mws0025 Pyrogallol Phenolic acids
pmb3317 Quinacyl syringic acid Phenolic acids
pmn001710 Rosmarinic acid-3’-O-glucoside Phenolic acids
mws1521 Salicin Phenolic acids
MWSmce274 Salicyl Alcohol Phenolic acids
Lmgn001670 Salicylic acid Phenolic acids
pmb3142 Salicylic acid-2-O-glucoside Phenolic acids
mws2367 Salidroside Phenolic acids
Hmsn002598 Salirepin Phenolic acids
Lmbp002309 Sinapaldehyde-4-O-Glucoside Phenolic acids
mws4085 Sinapic acid Phenolic acids
pme3443 Sinapinaldehyde Phenolic acids
pma0149 Sinapoyl malate Phenolic acids
Lmgn004359 SinapoylcaffeoylQuinic acid O-glucose Phenolic acids
mws0853 Sinapyl alcohol* Phenolic acids
Zmln000899 Syringaldehyde-4-O-glucoside Phenolic acids
mws0027 Syringic acid Phenolic acids
pmb0824 Syringic acid-4-O-(6″-feruloyl)glucoside Phenolic acids
mws0011 Syringin Phenolic acids
Lmgn002253 Syringoylcaffeoylquinic acid-d-glucose Phenolic acids
Hmqn000843 Tachioside Phenolic acids
pme0281 Terephthalic acid Phenolic acids
pmb0751 Trans-5-O-(p-Coumaroyl)shikimate Phenolic acids
pmn001523 Trigallic acid Phenolic acids
mws2368 Tyrosol; 4-Hydroxyphenylethanol Phenolic acids
MWSslk092 Usnic acid Phenolic acids
mws0028 Vanillic acid Phenolic acids
Lmqp002627 Vanillic acid methyl ester Phenolic acids
Zmhn001883 Vanillic acid-4-O-glucoside Phenolic acids
Jmwn002620 Vanillic Acid-4-O-Glucuronide Phenolic acids
MWSmce632 Vanillin acetate Phenolic acids
Zmtn001661 Vanilloloside Phenolic acids
Lmhn002321 Vnilloylcaffeoyltartaric acid Phenolic acids
Lmhn002051 Vnilloylmalic acid Phenolic acids
Lmhn001386 Vnilloyltartaric acid Phenolic acids
Lmbn002648 α-Hydroxycinnamic Acid* Phenolic acids
Zbln001290 β-Hydroxy-(3,4-dihydroxyphenylethanolyl)-glucoside Phenolic
acids
Hmln002996 β-Hydroxyacteoside Phenolic acids
Hmgn002038 β-Oxoacteoside Phenolic acids
MA10079134 1,2,4-Trihydroxyanthraquinone Quinones
MWS20169 2,5-dihydroxy-1-methoxy-anthraquinone Quinones
Zbn004863 3-Hydroxymorindone-6β-primeveroside Quinones
Zbn006783 5,6-Dihydroxylucidin Quinones
Zbn004415 5,6-Dihydroxylucidin-3β-primeveroside Quinones
Zmdn006929 Aloe-Emodin-9-Anthrone Quinones
Zdhn005610 Citreorosein Quinones
Wcfn008271 Danthron; 1,8-Dihydroxyanthraquinone Quinones
Zbqn006094 Pseudopurpurin(1,2,4-trihydroxy-3-carboxyanthraquinone)
Quinones
Wmcp000011 Rheic Acid Quinones
pmn001338 Rhein-8-O-glucoside Quinones
Zbln013951
1-(3′-methoxy-4′-hydroxybenzyl)-2,7-dihydroxy-4-methoxyphenanthrene
Quinones
Zbln007388 4,6-dimethoxy-9,10-dihydrophenanthrene-2,3,7-triol Quinones
Lmqp003022 2,3-Dihydro-1,4-naphthoquinone Quinones
Wmhp000055 2,5-Dimethoxybenzoquinone* Quinones
Zmsp001834 2,6-Dimethoxy-1,4-benzoquinone* Quinones
Wchn003984 1,4,8-Trihydroxynaphthalene-1-O-glucoside* Quinones
pme0432 Procyanidin A2 Tannins
mws0836 Procyanidin B1 Tannins
MWSHY0171 Procyanidin B2 Tannins
pme0436 Procyanidin B3 Tannins
pmn001667 Procyanidin B4 Tannins
Lssp210081 Procyanidin B5 Tannins
pmn001646 Procyanidin C1 Tannins
pmn001647 Procyanidin C2 Tannins
Zmlp005013 3,3’-O-Dimethylellagic Acid Tannins
Lmqn004838 3-O-Methylellagic acid Tannins
Hmdn001667 Ellagic acid-4-O-glucoside Tannins
Lmyn004187 Flavogallonic Acid Dilactone Tannins
mws1629 Aucubin Terpenoids
mws1565 Geniposide Terpenoids
mws1574 Geniposidic acid* Terpenoids
Lafp004533 (6R,9R)-3-Oxo-α-ionol-β-D-malonyl-glucoside Terpenoids
Qmjp080407 14(15)-Bisnor-13-oxolabd-8(17),11(E)-dien-19-oic acid
Terpenoids
Qmjp080402 15,16-Bisnor-13-oxo-8(17),11-labdadien-19-ol Terpenoids
Wdzp007419 1β-hydroxy-β-cyperone Terpenoids
Wbmp003788 3,4-Dihydroxy-7,8-dihydro-β-ionone-4-O-β-D-glucoside
Terpenoids
Labp004808 3-Oxo-Alpha-Ionol diglucoside Terpenoids
Wcfp005519 5-hydroxyindene-1,3-dione Terpenoids
Lmqp003432 6,9-Dihydroxy-7-megastigmen-3-one Terpenoids
Hmcn000773 6’-O-Glucosylaucubin Terpenoids
Zjyp102922 Humula-3(12),7(13),9(E)-triene-2,6-diol Terpenoids
MWSmce096 Nootkatone Terpenoids
Hmlp013407 β-Eudesmol Terpenoids
Cmbn004962 10-O-[(E)-p-Coumaroyl]-geniposidic acid Terpenoids
Qmdp112605 1-Oxo-Eucommiol Terpenoids
Lmdn003075 3,4-Dihydroverbenalin Terpenoids
Cmbn003318 5-Hydroxy-10-O-(p-methoxycinnamoyl)adoxosidic acid
Terpenoids
Lmdn001560 6-DeoxyCatalpol Terpenoids
Zbbn002910 6”-O-sinapoyl-7-O-caffeoyl-geniposide Terpenoids
pmp001070 6”-O-Trans-Sinapoylgenipin gentiobioside Terpenoids
Wbmn003453 6-O-Vanilloylajugol Terpenoids
Hmmn003964 7-Deoxyloganic acid Terpenoids
Sacn001940 8-Epiloganic acid Terpenoids
MWSslk186 8-O-Acetylharpagide Terpenoids
pmn001587 Asperulosidic acid Terpenoids
pmp001045 Bartsioside Terpenoids
Hmlp008487 Blumenol C Terpenoids
mws1562 Catalpol Terpenoids
MWS1962 cis-Citral Terpenoids
pmn001586 Deacetylasperulosidic acid Terpenoids
MWSHC20122 Dehydrovomifoliol Terpenoids
MWSmce434 Gardenoside Terpenoids
Lmdn001501 Gardoside* Terpenoids
MWSmce115 Genipin Terpenoids
pmp001059 Genipin-1-O-(2”-O-apiosyl)glucoside Terpenoids
Lhjp111633 Glucosylasperuloside Terpenoids
Wmbn000547 Harpagide Terpenoids
pmp001048 Ixoroside Terpenoids
pmp000691 Loganetin Terpenoids
Zbyn002745 Loganic acid Terpenoids
Lmjp004816 Loliolide Terpenoids
pmn001585 Monotropein Terpenoids
Cmrn001591 Mussaenosidic acid Terpenoids
Lmyp004084 Perillyl alcohol Terpenoids
Cmhp003670 Secologanin Terpenoids
pmp001053 Shanzhiside Terpenoids
mws1526 Sweroside Terpenoids
Lmpn004676 Verminoside* Terpenoids
Hmmp003004 Vogeloside Terpenoids
mws1429 Vomifoliol (Blumenol A) Terpenoids
Labn003976 Vomifoliol 9-[Xylosyl-(1 → 6)-Glucoside] Terpenoids
mws1515 α-Ionone Terpenoids
pmf0314 cis-Abienol Terpenoids
Cmmn012461 Dehydroabietic acid Terpenoids
MWSslk208 Kaurenoic Acid* Terpenoids
Lmbn014696 Pimaric acid* Terpenoids
Wbmn011269 Vitexilactone Terpenoids
Llhp011701 11,12-epoxy-13-hydroxy-3-Oxooleanane-28-oic acid
gamma-lactone (Liquidambaric Lactone) Terpenoids
pmn001427 16,23:16,30-Diepoxydammar-24-ene-3,20-diol (Jujubogenin)*
Terpenoids
Lskp211493 2,19-Dihydroxy-3-oxo-24-norolean-12-en-28-oic acid
Terpenoids
pmn001426 2,3,19-trihydroxyurs-12-en-28-oic acid (Euscaphic acid)*
Terpenoids
MWSmce394 2,3,19-Trihydroxyurs-12-en-28-oic acid (Tormentic acid)*
Terpenoids
Smpn009230 2,3,23-Trihydroxyolean-12-en-28-oic acid* Terpenoids
Lmqp008286 2,3,23-Trihydroxyolean-12-en-28-oic acid (Arjunolic acid)
Terpenoids
Hmjn003948 2,3,6-Trihydroxyurs-12-en-28-oic acid (Madasiatic acid)*
Terpenoids
Wbmn009545 2,3-Diacetoxy-18-hydroxyoleana-5,12-dien-28-oic acid
Terpenoids
Smpn011792 2,3-Dihydroxy-12-ursen-28-oic acid* Terpenoids
Lmzn106284 2,3-Dihydroxylup-20(29)-en-28-oic acid (Alphitolic acid)*
Terpenoids
pmn001706 2,3-Dihydroxyolean-12-en-28-oic acid (2-Hydroxyoleanolic
acid)* Terpenoids
Hmjn008136 2,3-Dihydroxyoleana-11,13(18)-dien-28-oic acid (Camaldulenic
acid) Terpenoids
Lmsn012627 2,3-Dihydroxyurs-12,18-dien-28-oic acid Terpenoids
Zmpn008194 2,3-Dihydroxyurs-12-en-28-oic acid (Corosolic acid)*
Terpenoids
[68]Li512114 2,3-Dihydroxyurs-12-en-28-oic acid methyl ester (Corosolic
acid methyl ester) Terpenoids
mws1610 2,3-Dihydroxyurs-12-en-29-oic acid (Maslinic acid)* Terpenoids
Lssp210085 3,11-dioxo-β-oleorene Terpenoids
pmn001591 3,19,23-Trihydroxyurs-12-en-28-oic acid (Rutundic acid)
Terpenoids
Lmzn006169 3,19-Dihydroxyurs-12-en-28-oic acid (Pomolic acid)*
Terpenoids
Lhnp110101 3,20-Dihydroxyurs-21-en-28-oic acid (Oleanderic acid)
Terpenoids
Hmbn005207 3,23-Dihydroxyolean-12-en-28-oic acid (Hederagenin)*
Terpenoids
pmp000441 3-Hydroxy-11-oxours-12-en-28-oic acid (11-Keto-ursolic acid)
Terpenoids
MWSHC20176 3-Hydroxylup-20(29)-en-28-oic acid (Betulinic acid)
Terpenoids
mws1389 3-Hydroxyolean-12-en-28-oic acid (Oleanolic acid)* Terpenoids
Lmsp102910 3-Hydroxyolean-12-ene-27,28-dioic acid (Cincholic acid)
Terpenoids
MWSmce052 3-Hydroxyurs-12-en-28-oic acid (3-Epiursolic acid) Terpenoids
Lssp210084 3-Hydroxyurs-12-en-28-oic acid (Ursolic acid) Terpenoids
Lmmn009550 3-Oxo-9,19-cyclolanost-24-en-26-oic acid (Mangiferonic
acid)* Terpenoids
MWSmce134 3-Oxolup-20(29)-en-28-oic acid (Betulonic acid)* Terpenoids
Lmyn012771 3-Oxoolean-18-en-28-oic acid (Moronic acid)* Terpenoids
Ymjm000099 3-Oxooleana-11,13(18)-dien-28-oic acid Terpenoids
Lmzn006795 3-Oxours-12-en-28-oic acid (Ursonic acid)* Terpenoids
Lmhn011365 Morolic acid* Terpenoids
Hmcp005697 Olean-13(18)-en-3-one (δ-Amyrenone) Terpenoids
Lmqn012798 Urs-12(13)-en-3-one-28-oic acid* Terpenoids
Lmxn001694 6”-O-β-D-Glucosyl-8-O-acetylharpagide Terpenoids
Lmxn003152 8-Epiloganin Terpenoids
Zadn003162 Ajugoside Terpenoids
Smhn002274 Blumenol C glucoside; Byzantionoside B* Terpenoids
Zadp003164 Dehydrololiolide Terpenoids
pmn001381 Eucommioside Terpenoids
Zmdn003368 eucomoside A Terpenoids
Zmdn004697 eucomoside B Terpenoids
Zmdn004845 eucomoside C Terpenoids
Lmlp002205 Isololiolide Terpenoids
[69]Open in a new tab
Based on the above results, a non-supervised PCA model was conducted to
further examine QC and tested samples ([70]Fig. 2D). The four groups of
EUL were distinctly differentiated, with the QC samples located in the
center of all tested samples. This result validated reliability and
reproducibility of this experiment. Additionally, the result confirmed
that non-volatile metabolites determined in the four groups of EUL were
obviously distinct. The significant separation of BT in PC1 (40.9 %) is
attributed to fermentation-specific metabolites such as esters and
phenolic acids, while the differences between GT and HG in PC2
(16.53 %) stem from the impact of thermal processing on lipid
metabolism.This result suggested that the BT was the most different
from the other groups, followed by the GT and HG, while the metabolites
were more similar within the other groups.
3.3. Differential metabolites in XY, HG, BT, GT
The OPLS-DA analysis demonstrated statistically significant
differences, filtering the four samples for substantial differences in
nonvolatile metabolites based on conditions of VIP ≥ 1,
FC ≥ 2(or ≤ 0.5) and p < 0.05. Prior to this further analysis, the
OPLS-DA analysis needs to be validated. The Q^2 values between XY and
BT, XY and HG, XY and GT, BT and HG, BT and GT, and HG and GT were
0.988, 0.978, 0.975, 0.989, 0.992, and 0.957, respectively (Fig. S1).
Q^2 represents the predictive power, while R^2Y and R^2X reveal the
explanatory power of the Y and X matrices, separately. All pairwise
comparisons of R^2Y and Q^2 scores turned out to be higher than 0.9,
which implies that the model is good. In addition, a total of 200
randomized permutation tests were also conducted to validate the
OPLS-DA model, and the p-values were found to be below 0.005,
indicating an excellent model. Therefore, the implemented OPLS-DA model
is stable, meaningful and can be used for further screening of
differential metabolites.
The data of OPLS-DA results were combining the grouping of specific
samples and visualizing the results through volcano plots ([71]Fig.3A).
A total of 975 (440 up-regulated) metabolites were found to be
significantly different between BT and XY, 665 (349 up-regulated)
between HG and XY, 706 (273 up-regulated) between GT and XY, 986 (419
up-regulated) between BT and HG, 1115 (558 up-regulated) between BT and
GT, and 560 (171 up-regulated) between GT and HG. In addition, two
different trends were found for the differential metabolites screened
in the four samples of this study ([72]Fig. 3B). For example, one part
of the metabolites in BT showed higher levels than in XY, while the
other half of the metabolites in BT showed lower levels than in XY.
Fig. 3.
[73]Fig. 3
[74]Open in a new tab
A. Volcano plots of nonvolatile metabolites in the two-by-two
comparison groups, in order of BT vs. XY, HG vs. XY, GT vs. XY, BT vs.
HG, BT vs.GT, HG vs.GT. Note: Each point in the volcano diagram
represents a metabolite, where green points represent down-regulated
differential metabolites, red points represent up-regulated
differential metabolites, and gray points represent metabolites that
were detected but the difference was not significant; the horizontal
coordinate represents the logarithm of the multiplicity of the
difference of the relative content of a metabolite between the two
groups of samples (log[2]). FC), the larger the absolute value of the
horizontal coordinate, the larger the difference in relative content of
the substance between the two groups of samples. VIP + FC + P-value
screening conditions: the vertical coordinate indicates the
significance level of the difference (−log[10] P-value), the size of
the dot represents the VIP value. VIP + FC screening condition: the
vertical coordinate represents the VIP value, the larger the value of
the vertical coordinate, the more significant the difference is, and
the more reliable the differential metabolite obtained by screening. B.
Horizontal coordinates represent the grouping of samples, vertical
coordinates represent the normalized relative metabolite content, Sub
class represents the number of metabolite classes with the same trend,
and total: represents the number of metabolites in the class.
To better summarize and analyze the dynamics of metabolites between
different treatments of EUL, a clustered heat map analysis was
performed as in Supplemental Fig. S2 & Fig. S3 A-K. These
differentially regulated nonvolatile metabolites were mainly focusing
on flavonoids, phenolic acids, amino acids and their derivatives
([75]Table 3). As shown in [76]Fig. 4, the classification of
significant differences in the comparison between BT vs. XY showed that
alkaloids, amino acids and their derivatives, and flavonoids were
significantly down-regulated, with the number of flavonoids
down-regulated reaching more than 120. While phenolic acids, organic
acids, and other classes existed significant up-regulation. The
withering process during black tea processing can result in a highly
significant positive correlation between free amino acids in the
withered leaves and flavonoids in the finished black tea. This explains
that amino acids and their derivatives are correlated with the
decreasing trend of both flavonoids. The decrease in flavonoids is also
consistent with previous experimental studies by Li et al. that the
fermentation process leads to this result([77]Li et al., 2017).
Furthermore, in the HG vs. XY, besides the significant increase in the
number of up-regulated amino acids and their derivatives after the
drying process, reaching more than 90 species, there was also a more
pronounced up-regulation of lipids, nucleotides and their derivatives,
and alkaloids. While the down-regulation of heterocyclic compounds and
terpenoids increased in the number. This indicates that drying is very
favorable for the production of amino acids and their derivatives, but
not for terpenoids and heterocyclic compounds. In the GT vs. XY, the
number of down-regulation of lipids was the most significant, reaching
almost 80. While the number of up-regulation of phenolic acids,
flavonoids, amino acids and their derivatives was significantly higher.
It indicates that the GT processing leads to a decrease in the content
of lipids, but an increase in the content of some phenolic acids and
flavonoids.
Table 3.
Table of major differences in composition between groups of
non-volatile metabolites of different processed EUL.
Index Compounds Class BT_vs_XY_Type GT_vs_XY_Type HG_vs_XY_Type
mws0178 Chlorogenic acid (3-O-Caffeoylquinic acid)* Phenolic acids down
– –
mws2108 Cryptochlorogenic acid (4-O-Caffeoylquinic acid)* Phenolic
acids down – –
pmn001382 Isochlorogenic acid A* Phenolic acids – up –
[78]Li512115 Isochlorogenic acid B* Phenolic acids – up –
pmn001384 Isochlorogenic acid C* Phenolic acids – up –
MWSprf004 Neochlorogenic acid (5-O-Caffeoylquinic acid)* Phenolic acids
down – –
mws1358 Pyrocatechol Phenolic acids – up –
mws1068 Kaempferol (3,5,7,4’-Tetrahydroxyflavone) Flavonoids up down
down
MWSHY0136 Kaempferol-3-O-glucoside (Astragalin)* Flavonoids down – –
pme2954 Quercetin Flavonoids up – –
mws0091 Quercetin-3-O-glucoside (Isoquercitrin) Flavonoids down – –
mws0045 Quercetin-3-O-rhamnoside(Quercitrin) Flavonoids down – –
MWSHY0065 Catechin* Flavonoids down up –
Lajp002810 Procyanidin A4 Flavonoids down – –
pmn001370 Pinoresinol-4,4’-O-diglucoside Lignans and Coumarins down – –
mws0836 Procyanidin B1 Tannins down – –
MWSHY0171 Procyanidin B2 Tannins down – –
pme0436 Procyanidin B3 Tannins down – –
pmn001667 Procyanidin B4 Tannins down – –
Lssp210081 Procyanidin B5 Tannins down – –
pmn001646 Procyanidin C1 Tannins down – –
pmn001647 Procyanidin C2 Tannins down – –
mws1629 Aucubin Terpenoids down – –
mws1565 Geniposide Terpenoids – – –
mws1574 Geniposidic acid* Terpenoids down – –
MWS00330g 1-Amino-1-cyclobutane-carboxylic-acid* Amino acids and
derivatives – – up
MWS0933 1-Methylhistidine* Amino acids and derivatives up – –
Zmmp001941 2-Amino-3,4-dihydroxybutanoic acid-3-O-arabinoside Amino
acids and derivatives down – up
Zmdp000441 3-(Allylsulphinyl)-L-alanine Amino acids and derivatives – –
up
MWS04491 3,4-Dehydro-DL-proline Amino acids and derivatives – down –
pme2914 3-Hydroxy-3-methylpentane-1,5-dioic acid Amino acids and
derivatives up – –
MWS04559g 3-Hydroxy-L-phenylalanine* Amino acids and derivatives down
down –
MWS2010 3-nitro-L-tyrosine Amino acids and derivatives down – –
Zbqp003444 4-amino-5-oxo-5-(pentylamino)pentanoic acid Amino acids and
derivatives down – –
pme2758 4-Hydroxy-L-glutamic acid Amino acids and derivatives down – up
MWSmce190 4-Hydroxy-L-Isoleucine Amino acids and derivatives down – –
mws0263 5-Oxo-L-Proline* Amino acids and derivatives – up –
MWS0813 5-Oxoproline* Amino acids and derivatives – up –
MWS201384 Arg-Gly Amino acids and derivatives – up up
Zmdp000292 Arginine methyl ester* Amino acids and derivatives down up
up
MWS201391 Asn-Ile Amino acids and derivatives down – up
MWS201449 Asn-Leu Amino acids and derivatives down – up
MWS201455 Asp-Lys* Amino acids and derivatives – – up
pmf0470 cis-4-Hydroxy-D-proline* Amino acids and derivatives down – up
MWStz261 Cyclo(D-Leu-L-Pro)* Amino acids and derivatives – up up
MWStz205 Cyclo(D-Phe-L-Pro)* Amino acids and derivatives – up –
MWStz083 Cyclo(D-Val-L-Pro) Amino acids and derivatives – up up
Zazp002547 cyclo-(Gly-Phe) Amino acids and derivatives down – up
MWStz091 Cyclo(L-Ala-L-Pro) Amino acids and derivatives – up –
MWStz170 Cyclo(L-Leu-trans-4-hydroxy-L-Pro) Amino acids and derivatives
– – up
MWStz211 Cyclo(L-Phe-trans-4-hydroxy-L-Pro) Amino acids and derivatives
– – up
Lmrj002793 Cyclo(Phe-Glu) Amino acids and derivatives down up –
Lmhp002764 Cyclo(Pro-Leu)* Amino acids and derivatives – up up
MWStz255 Cyclo(Pro-Phe)* Amino acids and derivatives – up –
Lmrj002244 Cyclo(Pro-Pro) Amino acids and derivatives – up –
Lmrj001341 Cyclo(Ser-Pro) Amino acids and derivatives down up up
ML10181668 Cycloleucine Amino acids and derivatives – – –
MWS0611 D-Alanyl-D-Alanine* Amino acids and derivatives down – –
MWS04555g D-Allo-Isoleucine* Amino acids and derivatives down – up
MWS1926 DL-Leucine* Amino acids and derivatives down – up
mws0224 DL-Methionine Amino acids and derivatives down – up
MWSmce056 DL-Tryptophan* Amino acids and derivatives down – up
mws4532g D-Ornithine Amino acids and derivatives – – –
MWS201465 Glu-Phe Amino acids and derivatives down – up
MWS20672 Glu-Phe-Ala Amino acids and derivatives down – up
MWS4296 Glycylphenylalanine* Amino acids and derivatives down – up
MWS4309 Glycyl-tryptophan Amino acids and derivatives – up up
MWS20645 Gly-Tyr* Amino acids and derivatives down – up
Zbqp002414 h-gamma-Glu-leu-oh Amino acids and derivatives down – –
MWS201405 His-Tyr Amino acids and derivatives down – up
MWS04447 Homoproline Amino acids and derivatives up up up
MWS201398 Hyp-Ser Amino acids and derivatives – – up
MWS201397 Hyp-Val Amino acids and derivatives – down down
MWS201424 Ile-Asn Amino acids and derivatives – – up
pme2074 Jasmonoyl-L-Isoleucine Amino acids and derivatives up up up
pme0128 L-Alanyl-L-Alanine* Amino acids and derivatives down – –
mws4176 L-Alanyl-L-Phenylalanine Amino acids and derivatives down – up
pme2679 L-Allo-isoleucine Amino acids and derivatives down – up
mws0260 L-Arginine Amino acids and derivatives down – up
mws0001 L-Asparagine Amino acids and derivatives – – up
mws0219 L-Aspartic Acid* Amino acids and derivatives down up down
mws0629 L-Aspartyl-L-Phenylalanine Amino acids and derivatives down –
up
pme0116 L-Carnosine Amino acids and derivatives down – –
pme0008 L-Citrulline Amino acids and derivatives – – –
Hmsp000364 L-Cyclopentylglycine Amino acids and derivatives up up –
mws0875 L-Cysteinyl-L-glycine Amino acids and derivatives – up –
Lmbp001216 L-Dihomomethionine Amino acids and derivatives down – –
MWS201461 Leu-Arg Amino acids and derivatives – – up
MWS201437 Leu-Asp Amino acids and derivatives down up up
pme0014 L-Glutamic acid Amino acids and derivatives down – –
pme0193 l-Glutamine Amino acids and derivatives down – down
mws5041 L-Glycyl-L-isoleucine* Amino acids and derivatives down up up
mws5042 L-Glycyl-L-phenylalanine* Amino acids and derivatives down – up
pme0124 L-Glycyl-L-proline Amino acids and derivatives down up up
mws0254 L-Histidine Amino acids and derivatives down up up
pme0057 L-Homocysteine Amino acids and derivatives – – –
pme2890 L-Homocystine Amino acids and derivatives down – up
Lmbp000123 L-Homomethionine Amino acids and derivatives down – –
MWS00123g L-Homophenylalanine Amino acids and derivatives up – –
mws0671 L-Homoserine* Amino acids and derivatives – – –
mws0258 L-Isoleucine* Amino acids and derivatives down – up
Lmrj002087 L-Isoleucyl-l-Aspartate Amino acids and derivatives down –
up
MWS00327g L-Isoserine Amino acids and derivatives – down down
mws0227 L-Leucine* Amino acids and derivatives down – up
Lmhp002031 L-Leucyl-L-Leucine Amino acids and derivatives down – up
mws5035 L-Leucyl-L-phenylalanine Amino acids and derivatives down – up
pme0026 l-Lysine Amino acids and derivatives down – down
pmb0962 l-Lysine-Butanoic Acid Amino acids and derivatives up up up
pme1210 L-Methionine Amino acids and derivatives down – up
pme1419 L-Methionine methyl ester Amino acids and derivatives down down
down
pme2617 L-Methionine Sulfoxide Amino acids and derivatives – – up
mws1587 L-Norleucine* Amino acids and derivatives down – up
pme0021 L-Phenylalanine Amino acids and derivatives down – up
mws0636 L-Phenylalanyl-L-phenylalanine Amino acids and derivatives down
– up
pme0006 L-Proline* Amino acids and derivatives – – up
Lmhp001461 L-Prolyl-L-Leucine Amino acids and derivatives down – up
Lmhp001732 L-Prolyl-L-Phenylalanine Amino acids and derivatives – – up
Zmzn000113 L-threo-3-Methylaspartate Amino acids and derivatives down –
–
mws0230 L-Threonine* Amino acids and derivatives – – –
mws0282 L-Tryptophan Amino acids and derivatives down up up
mws0250 L-Tyrosine* Amino acids and derivatives down down –
MWS1771 L-Tyrosine methyl ester Amino acids and derivatives down – –
mws0256 L-Valine Amino acids and derivatives down – up
Wcdp000380 L-Valinol Amino acids and derivatives – down down
Lmhp001670 L-Valyl-L-Leucine Amino acids and derivatives down – up
Lmhp002001 L-Valyl-L-Phenylalanine Amino acids and derivatives down –
up
MWS201412 Lys-Asp* Amino acids and derivatives – up up
MWS201471 Lys-Tyr Amino acids and derivatives – up up
pmb0034 L-α-Glutamyl-L-Glutamic Acid Amino acids and derivatives down
down –
Zmdp002216 L-γ-Glutamyl-L-leucine Amino acids and derivatives down down
–
MWS201470 Met-Arg Amino acids and derivatives up up up
MWS201399 Met-Asn Amino acids and derivatives down – up
MWSmce585 Methyl 3-aminopropanoate Amino acids and derivatives – down
down
MWS201421 Met-Phe Amino acids and derivatives down down up
MWS201429 Met-Ser Amino acids and derivatives – – up
MWS201430 Met-Thr Amino acids and derivatives – – up
Wayn001257 N-(1-Deoxy-1-fructosyl)Leucine Amino acids and derivatives –
up up
Wayp001024 N-(1-Deoxy-1-fructosyl)Valine Amino acids and derivatives up
up up
MWS04412 N(6),N(6)-Dimethyl-l-lysine Amino acids and derivatives down –
up
Zbqn004590 N-(acetyl)phenylalanine Amino acids and derivatives – – –
MWS5164 N,N′-Dimethylarginine;SDMA* Amino acids and derivatives down –
up
pme3033 N,N-Dimethylglycine* Amino acids and derivatives – down down
MWS20987 N5-(1-Iminoethyl)-L-ornithine Amino acids and derivatives – –
up
pme0122 N6-Acetyl-l-lysine Amino acids and derivatives down – –
MWSslk120 N-Acetyl-DL-phenylalanine Amino acids and derivatives up – up
pme0170 N-Acetyl-L-Arginine Amino acids and derivatives – – up
pme0137 N-Acetyl-l-Glutamine Amino acids and derivatives up – –
pme0253 N-Acetyl-L-leucine Amino acids and derivatives up – up
MWSslk140 N-Acetyl-L-Methionine Amino acids and derivatives – – up
pmb2591 N-Acetyl-L-Tryptophan Amino acids and derivatives – down down
mws0520 N-Acetyl-L-tyrosine Amino acids and derivatives up – –
Zbqn003921 N-carboxy-N-(2-oxo-2-phenylethyl)-L-alanine Amino acids and
derivatives up – –
MWS00204g N-Ethylglycine* Amino acids and derivatives – down down
NK10251888 NG,NG-Dimethyl-L-arginine* Amino acids and derivatives down
– up
mws0736 N-Glycyl-L-leucine* Amino acids and derivatives down up up
Lmqp000427 N-Methyl-Trans-4-Hydroxy-L-Proline Amino acids and
derivatives down – –
MWS5209 N-Methyl-α-aminoisobutyric acid Amino acids and derivatives –
up –
Zmjp000182 N-Monomethyl-L-arginine* Amino acids and derivatives down up
–
Zmyn000155 N-α-Acetyl-L-ornithine Amino acids and derivatives down – up
MWS201054 O-Acetyl-L-homoserine Amino acids and derivatives – – –
mws1050 O-Acetylserine Amino acids and derivatives down down down
MWS20633g O-phosphate-L-tyrosine Amino acids and derivatives – up up
mws3133 Oxaceprol Amino acids and derivatives – – –
mws4134 Oxiglutatione Amino acids and derivatives down – –
MWS201458 Phe-Ile Amino acids and derivatives down down up
MWS201478 Phe-Ser Amino acids and derivatives down – up
MWS201442 Phe-Thr Amino acids and derivatives down – up
MWS201415 Pro-Asp Amino acids and derivatives down – –
mws4516 Pyroglutamic acid Amino acids and derivatives – – –
pme1286 S-(5′-Adenosy)-L-homocysteine Amino acids and derivatives down
– up
MWStz103 S-(5′-Adenosyl)-L-methionine Amino acids and derivatives up –
–
MWS201381 Ser-Trp Amino acids and derivatives down up up
Lcsp002417 Ser-Val-Leu Amino acids and derivatives down – up
Zmdp000972 S-Methyl-L-cysteine Amino acids and derivatives down down –
MWS20966 S-methyl-L-thiocitrulline Amino acids and derivatives – – –
MWS201477 Thr-Thr Amino acids and derivatives – – –
mws0216 Trans-4-Hydroxy-L-proline* Amino acids and derivatives down –
up
pmp001257 Tridecanoylglycine Amino acids and derivatives down – down
Zmzp000145 Trimethyllysine Amino acids and derivatives down up –
MWS201187 Trp-His Amino acids and derivatives up – –
MWS201480 Tyr-Ala Amino acids and derivatives – – up
MWS201479 Tyr-Gly* Amino acids and derivatives down – up
MWS201400 Val-Trp Amino acids and derivatives down – up
Zbqp003189 Val-Val Amino acids and derivatives up up up
Zmdp001647 γ-Glutamyl-L-valine Amino acids and derivatives down – –
Zmdp001663 γ-glutamylmethionine Amino acids and derivatives – – –
Zmdp001857 γ-Glutamyltyrosine Amino acids and derivatives down – –
Zmmp003443 γ-Glu-Trp Amino acids and derivatives down – up
Zmdp001718 γ-L-Glutamyl-S-allyl-L-cysteine Amino acids and derivatives
down – –
Zmdp000446 γ-L-Glutamyl-S-methyl-L-cysteine Amino acids and derivatives
up – –
Zbfn002690 1-(4-Hydroxybenzoyl)Glucose; 25,545–07-7 Phenolic acids up –
–
Lmfn001337 1,2,3-Tri-O-galloyl-β-d-glucose* Phenolic acids – up –
Zmdn003203 1,2,6-Tri-O-galloyl-β-d-glucose* Phenolic acids – up –
Lmfn001209 1,3,6-Tri-O-galloyl-β-d-glucose* Phenolic acids – up –
mws1584 1,3-O-Dicaffeoylquinic Acid (Cynarin) Phenolic acids – – –
Lmsn003088 1,4,6-Tri-O-galloyl-β-d-glucose* Phenolic acids – up –
Wmhn001495 1,4-Di-O-Galloyl-d-glucose Phenolic acids up up –
Waxn004217 1,5-O-dicaffeoyl-3-O-glucoside-quinic acid Phenolic acids –
up –
mws0748 1-Caffeoylquinic acid Phenolic acids down – –
pmp000086 1-Feruloyl-sn-glycerol Phenolic acids up – –
Wasn002933 1-O-(3,4,5-Trimethoxybenzoyl)-B-D-Glucopyranoside Phenolic
acids down – –
Lmtn000940 1-O-(3,4-Dihydroxy-5-methoxy-benzoyl)-glucoside Phenolic
acids down – –
Lmsn002288 1-O-Caffeoyl-(6-O-glucosyl)-β-d-glucose Phenolic acids down
up –
Lmsn004690 1-O-Caffeoyl-3-O-galloyl-4,6-(S)-HHDP-β-d-glucose Phenolic
acids – – –
Hmbp003234 1-O-Caffeoylglycerol Phenolic acids – – down
Zmhn002422 1-O-Feruloyl-β-d-glucose Phenolic acids down – –
Lmsn004323 1-O-Galloyl-2-O-Feruloyl-β-d-glucose Phenolic acids down – –
Lmsn001014 1-O-Galloyl-β-d-glucose* Phenolic acids down – –
pmb2871 1-O-Gentisoyl-β-D-glucoside* Phenolic acids down – –
pmb3068 1-O-p-Coumaroylquinic acid Phenolic acids up – –
pmn001320 1-O-p-Cumaroylglycerol Phenolic acids up – –
Lmsn002247 1-O-Salicyloyl-β-d-glucose* Phenolic acids down up –
HJN003 1-O-Sinapoyl-β-d-glucose Phenolic acids up – –
Lmtn002565 1-O-Vanilloyl-d-Glucose Phenolic acids down up –
Zbln003341
2-(2-(3,4-dihydroxyphenyl)-2-methoxyethoxy)-6-(hydroxymethyl)tetrahydro
-2H-pyran-3,4,5-tri Phenolic acids – up –
Jmwn002117 2-(3,4-dihydroxyphenyl)ethanediol 1-O-β-D-glucopyranoside*
Phenolic acids down – –
pme3083 2-(Formylamino)benzoic acid Phenolic acids up – –
MWSslk138 2,3,4-Trihydroxybenzoic acid Phenolic acids up – –
Lafp002342 2,3-Dihydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)propan-1-one
Phenolic acids up – –
mws0639 2,3-Dihydroxybenzoic Acid* Phenolic acids up – –
MWSmce490 2′,4′,6′-Trihydroxyacetophenone Phenolic acids down down down
mws0885 2,4-Dihydroxybenzoic acid Phenolic acids up – –
mws0180 2,5-Dihydroxybenzoic acid; Gentisic Acid* Phenolic acids up – –
Lmdp002901 2,6-Dihydroxy-4-isopropylphenyl-1-O-β-D-glucoside Phenolic
acids down – –
Wmyn000217 2,6-dimethoxy-hydroquinone-4-O-β-D-glucopyranoside Phenolic
acids down – –
NK10253223 2-Amino-3-methoxybenzoic acid Phenolic acids – down –
pmp000087 2-Feruloyl-sn-glycerol Phenolic acids up – –
Lmgp002452 2-Glucosyloxy-(4-hydroxyphenyl)acetic acid (Dhurrin acid)
Phenolic acids up down up
Lmbn001930 2-Hydroxybenzaldehyde (Salicylaldehyde) Phenolic acids up –
–
Lmmn001643 2-Hydroxycinnamic acid* Phenolic acids up – up
Zmyn002919 2-Methylbenzoic acid Phenolic acids up up up
Zmzn002575 2-Nitrophenol Phenolic acids up – –
Lmhn102068 2-O-Caffeoylmalic acid Phenolic acids down – up
Hmln000873 2-O-Galloyl-d-glucose Phenolic acids down – –
Wacn003131 2-O-P-Coumaroylhydroxycitric Acid Phenolic acids down – –
Lakn001671 2-β-D-Glucopyranosyloxy-5-hydroxy-phenylacetic acid Phenolic
acids – – –
MWS3046 3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid Phenolic acids up
down down
mws0346 3-(3-Hydroxyphenyl)-propionic acid Phenolic acids up down down
MWSmce713 3-(4-Hydroxyphenyl)-1-propanol Phenolic acids – – –
HJN102 3,4,5-Tricaffeoylquinic acid Phenolic acids – up up
pmn001517 3,4,5-Trimethoxyphenyl-1-O-Glucoside Phenolic acids down – –
pme2598 3,4-Dihydroxybenzeneacetic acid* Phenolic acids – down –
mws0183 3,4-Dihydroxybenzoic acid (Protocatechuic acid)* Phenolic acids
up – –
mws0612 3,4-Dimethoxyphenyl acetic acid Phenolic acids up down –
Wmzn002116 3,5-Dicaffeoylquinic acid Phenolic acids – – –
pmn001525 3,5-Digalloylshikimic acid Phenolic acids up up –
HJN037 3,5-Dihydroxy-4-methoxybenzoic acid; 4-O-Methylgallic Acid
Phenolic acids up – –
MWSmce454 3,5-Dihydroxyacetophenone Phenolic acids up – –
MWS1944 3,5-Dihydroxytoluene Phenolic acids up up –
mws0444 3-Aminosalicylic acid Phenolic acids – down –
MWSHC20102 3-Hydroxy-1-(4-Hydroxy-3-Methoxyphenyl)Propan-1-One Phenolic
acids – – –
pmn001690 3-Hydroxy-4-isopropylbenzylalcohol-3-O-glucoside Phenolic
acids down – up
MWSslk066 3-Hydroxy-4-methoxybenzoic acid; Isovanillic Acid Phenolic
acids – down down
pmn001511 3-Hydroxy-5-Methylphenol-1-O-Glucoside Phenolic acids up – –
Lmgp002593 3-hydroxybenzaldehyde Phenolic acids up – –
Lmyn004439 3-Hydroxyl-5-methylphenol-1-O-β-D-(6′-galloyl)glucoside*
Phenolic acids up – –
MWS4301 3-hydroxyphenylacetic acid* Phenolic acids up down –
MWS3149 3-Methoxybenzoic acid Phenolic acids up up up
Zmgn001989 3-Methylcatechol Phenolic acids up – –
MWS2058 3-Methylsalicylic Acid Phenolic acids up up up
Zaln004082 3-O-caffeoylshikimic acid* Phenolic acids down – –
pmb0752 3-O-Feruloylquinic acid Phenolic acids – – up
pmb2833 3-O-Feruloylquinic acid-O-glucoside* Phenolic acids down – –
Hmln000659 3-O-Galloyl-d-glucose* Phenolic acids down – –
MWSmce387 3-O-Methylgallic acid Phenolic acids up – –
pmb3064 3-O-p-Coumaroylquinic acid-O-glucoside Phenolic acids down – –
pmb3075 3-O-p-Coumaroylshikimic acid Phenolic acids up up –
Lmtn003598 3-Prenyl-4-O-glucosyloxy-4-hydroxybenzoic acid Phenolic
acids – up –
Lmyn003835 4-(3,4,5-Trihydroxybenzoxy)benzoic acid Phenolic acids down
– –
mws1336 4-Aminobenzoic acid Phenolic acids up down –
Zaln004057 4-caffeoylshikimic acid* Phenolic acids down – –
mws0749 4-Hydroxybenzoic acid Phenolic acids up down down
HJN025 4-Hydroxybenzyl Alcohol Phenolic acids – up –
MWSmce370 4-Hydroxyphenylacetic acid* Phenolic acids up down down
MWS5206 4-Hydroxyphenyllactic Acid* Phenolic acids up down down
pmb2795 4-Methoxycinnamic acid Phenolic acids up – –
Lmbn004847 4-Methoxyphenylpropionic acid Phenolic acids up – –
mws0566 4-Methylcatechol Phenolic acids – up –
Zmyn002321 4-Methylphenol Phenolic acids up – down
Wafn002874 4-O-(4’-O-alpha-d-Glucopyranosyl)caffeoylquinic acid
Phenolic acids – – –
Zmhn000892 4-O-Glucosyl-3,4-dihydroxybenzyl alcohol Phenolic acids down
– –
Zmhn001358 4-O-Glucosyl-4-hydroxybenzoic acid* Phenolic acids down – –
Zmhn002227 4-O-Glucosyl-sinapate Phenolic acids – up –
pma0110 4-O-Sinapoylquinic acid Phenolic acids – down –
Hmhn003518 4-O-β-D-glucopyranosylferulic acid Phenolic acids down – –
Hmtn001120 5-(2-Hydroxyethyl)-2-O-glucosylphenol Phenolic acids down –
–
pmn001516 5-Galloylshikimic acid Phenolic acids up – –
Lmmn003663 5-Glucosyloxy-2-Hydroxybenzoic acid methyl ester Phenolic
acids down up –
Lmzn001582 5′-Glucosyloxyjasmanic acid Phenolic acids up – –
MWSHC20125 5-O-Caffeoylshikimic acid Phenolic acids down – –
pmb2554 5-O-Feruloyl quinic acid glucoside* Phenolic acids down – –
Zmhn001703 5-O-Galloyl-D-hamamelose* Phenolic acids down – –
Ymjm000116 6-O-Acetylarbutin Phenolic acids – – up
Zmhn001793 6-O-Caffeoyl-d-glucose* Phenolic acids up – –
Hmbn002692 6’-O-Feruloyl-D-sucrose Phenolic acids down – –
Zmhn002334 6-O-Feruloyl-β-d-glucose Phenolic acids down – –
Lmfn000604 6-O-Galloyl-β-d-glucose* Phenolic acids down – –
Zmxn003874 7,8-Dihydro-Buddlenol B Phenolic acids up down –
Lmqp002761 Alnusonol Phenolic acids down down down
Lmtn002233 Androsin Phenolic acids down – –
pmb2654 Anthranilate-1-O-Sophoroside Phenolic acids down – –
MWSmce675 Arbutin Phenolic acids down – –
Labn003910 Benzyl B-Primeveroside* Phenolic acids – – –
mws1297 Benzyl glucoside Phenolic acids up – –
Lmtn002324 Benzyl-(2”-O-glucosyl)glucoside* Phenolic acids – – up
Cmjn004337 Benzyl-(2”-O-xylosyl)glucoside* Phenolic acids – – –
Lmyn003028 Benzyl-β-gentiobioside* Phenolic acids – up up
mws2120 Brevifolin carboxylic acid Phenolic acids down – –
mws2212 Caffeic acid Phenolic acids – up up
Zbfn002396 Caffeoyl-O-mannitol Phenolic acids down – –
Labn003679 Caffeyl alcohol 4-O-β-D-glucopyranoside Phenolic acids up –
–
MWS0550 Cinnamaldehyde Phenolic acids down down down
mws2213 Cinnamic acid Phenolic acids up – up
mws0906 Coniferin Phenolic acids up – –
mws0093 Coniferyl alcohol Phenolic acids up – –
Hmsn002272 Demethyl coniferin Phenolic acids – up up
Lmgp003989 Dicaffeoylshikimic acid Phenolic acids up up –
pmn001513 Digallic Acid Phenolic acids – up –
Lmmn000774 Dihydrocaffeoylglucose* Phenolic acids – – –
Lazn001573 Erythro-Guaiacylglycerol Phenolic acids up down –
mws2184 Ethyl caffeate Phenolic acids up up up
MWSslk006 Ethyl Vanillate Phenolic acids up – –
mws0014 Ferulic acid* Phenolic acids up down –
Hmmn002544 Ferulic acid-4-O-glucoside Phenolic acids down – –
mws0024 Gallic acid Phenolic acids – up –
pmb2928 Gallic acid-4-O-glucoside Phenolic acids down – –
Hmtn001302 Glucosyloxybenzoic acid Phenolic acids – up up
MWSHC2022 Glucosyringic acid Phenolic acids – – up
Cmyp005063 Grandidentatin Phenolic acids – down up
pme1292 Homogentisic acid* Phenolic acids – – –
WaYn002313 Homosyringic Acid 4’-O-Glucoside Phenolic acids down – –
mws0117 Homovanillic acid; 4-Hydroxy-3-methoxyphenylacetic acid
Phenolic acids up – –
pmb3056 Homovanilloylquinic acid Phenolic acids down – –
Lmyn002435 Hydrangeifolin I Phenolic acids – up up
MA10014775 Hydroquinone Phenolic acids down – up
Wafn003070 Hydroxyferulic acid glucoside Phenolic acids down up up
MWSmce264 Hydroxytyrosol Phenolic acids down – –
pme0422 Isoferulic Acid* Phenolic acids up down –
Lmmn001294 Koaburaside* Phenolic acids – – –
[79]Li512113 Maleoyl-caffeoylquinic acid Phenolic acids up – –
MWS1776 m-Cresol Phenolic acids up down –
Hmtn001288 Methyl 2,4-dihydroxyphenylacetate* Phenolic acids – down
down
Zmgn004894 Methyl 4-hydroxybenzoate* Phenolic acids up up up
Hmdn001963 Methyl Brevifolincarboxylate Phenolic acids up up up
Lmdn003756 Methyl caffeate Phenolic acids – – –
MWSHC20168 Methyl cumalate* Phenolic acids up – –
MWSmce230 Methyl gallate Phenolic acids up up –
Wbsp004755 Methyl Hydroxycinnamate Phenolic acids up – –
Lmmn002179 Methylsalicylate-2-O-glucoside Phenolic acids down – –
mws0145 O-Anisic acid (2-Methoxybenzoic acid)* Phenolic acids up up up
pme1439 p-Coumaric acid* Phenolic acids up – –
MWSslk144 p-Coumaric acid ethyl ester Phenolic acids up down down
Lmhn002926 p-Coumaroylmalic acid Phenolic acids up up –
pmb3055 p-Coumaroylquinic acid-4’-O-glucuronide Phenolic acids down – –
MWS1846 Phenoxyacetic acid* Phenolic acids up – –
MWS1848 Phenyl acetate Phenolic acids – – –
NK10264324 Phloroglucinol; 1,3,5-Benzenetriol Phenolic acids down up –
Hmhn000927 Phloroglucinol-1-O-β-D-glucopyranoside Phenolic acids down
up –
pme0282 Phthalic acid Phenolic acids up – –
mws1506 Plantamajoside Phenolic acids down – –
Wasn004683 Protocatechuic acid 1-O-(Glucosylvanilloyl) Phenolic acids
down – –
MWSmce501 Protocatechuic Acid Methyl Ester Phenolic acids up up –
pmn001367 Protocatechuic acid-4-O-glucoside* Phenolic acids down – –
pmb3317 Quinacyl syringic acid Phenolic acids down – –
pmn001710 Rosmarinic acid-3’-O-glucoside Phenolic acids down – –
mws1521 Salicin Phenolic acids up – –
MWSmce274 Salicyl Alcohol Phenolic acids up down –
Lmgn001670 Salicylic acid Phenolic acids up up up
pmb3142 Salicylic acid-2-O-glucoside Phenolic acids down – –
mws2367 Salidroside Phenolic acids down – –
Lmbp002309 Sinapaldehyde-4-O-Glucoside Phenolic acids down – –
mws4085 Sinapic acid Phenolic acids up – –
pme3443 Sinapinaldehyde Phenolic acids up up up
pma0149 Sinapoyl malate Phenolic acids down – –
Lmgn004359 SinapoylcaffeoylQuinic acid O-glucose Phenolic acids down –
–
Zmln000899 Syringaldehyde-4-O-glucoside Phenolic acids – – –
mws0027 Syringic acid Phenolic acids up – –
pmb0824 Syringic acid-4-O-(6″-feruloyl)glucoside Phenolic acids down –
–
mws0011 Syringin Phenolic acids down – –
Hmqn000843 Tachioside Phenolic acids – up –
pme0281 Terephthalic acid Phenolic acids up – –
pmn001523 Trigallic acid Phenolic acids down up –
mws2368 Tyrosol; 4-Hydroxyphenylethanol Phenolic acids up up up
MWSslk092 Usnic acid Phenolic acids up up –
mws0028 Vanillic acid Phenolic acids up down down
Lmqp002627 Vanillic acid methyl ester Phenolic acids – – –
Zmhn001883 Vanillic acid-4-O-glucoside Phenolic acids – – –
Jmwn002620 Vanillic Acid-4-O-Glucuronide Phenolic acids up – –
MWSmce632 Vanillin acetate Phenolic acids up – –
Zmtn001661 Vanilloloside Phenolic acids down – –
Lmhn002051 Vnilloylmalic acid Phenolic acids up – up
Lmbn002648 α-Hydroxycinnamic Acid* Phenolic acids up down down
Zbln001290 β-Hydroxy-(3,4-dihydroxyphenylethanolyl)-glucoside Phenolic
acids down – –
Hmln002996 β-Hydroxyacteoside Phenolic acids down – –
Hmgn002038 β-Oxoacteoside Phenolic acids – – –
mws0663 1,7-Dimethylxanthine Nucleotides and derivatives up up –
MWSmce295 1-beta-D-Arabinofuranosyluracil Nucleotides and derivatives
up – up
mws0847 1-Methyladenine Nucleotides and derivatives down – –
pme3967 2-(Dimethylamino)guanosine* Nucleotides and derivatives – up up
pmb0374 2-Aminopurine Nucleotides and derivatives down – up
pme3961 2’-Deoxyadenosine* Nucleotides and derivatives down up up
pme3184 2’-Deoxyadenosine-5′-monophosphate Nucleotides and derivatives
down – –
pme1194 2’-Deoxycytidine Nucleotides and derivatives – up up
pme1184 2’-Deoxyguanosine Nucleotides and derivatives – – up
pmc0066 2’-Deoxyinosine-5′-monophosphate Nucleotides and derivatives up
– –
pmb2507 2-Deoxyribose-1-phosphate Nucleotides and derivatives – down –
mws0863 2-Deoxyribose-5′-phosphate Nucleotides and derivatives – – –
Hmhp001812 2’-O-Methyladenosine Nucleotides and derivatives up up up
mws0874 3′-Adenylic Acid Nucleotides and derivatives down up up
pme1266 3-Methylxanthine Nucleotides and derivatives – – –
pme0152 5,6-Dihydro-5-methyluracil Nucleotides and derivatives down – –
pme0151 5,6-Dihydrouracil Nucleotides and derivatives – – up
Lmqp000329 5-Aminoimidazole ribonucleotide Nucleotides and derivatives
down – –
pme1474 5’-Deoxy-5′-(methylthio)adenosine Nucleotides and derivatives
up up up
MWSmce116 5’-Deoxyadenosine* Nucleotides and derivatives – – up
MWS2910 5-Methyl-2’-Deoxycytidine Nucleotides and derivatives down – up
mws0572 5-Methylcytosine Nucleotides and derivatives – up up
MWSslk102 6-Chloropurine Nucleotides and derivatives – – –
MWS4525 6-O-methylguanine Nucleotides and derivatives – up up
pme3968 7-Methylguanine Nucleotides and derivatives – up –
pme2801 7-Methylxanthine Nucleotides and derivatives – – up
MWS2984 8-Azaguanine Nucleotides and derivatives up up up
mws0724 8-Hydroxyguanosine Nucleotides and derivatives – – –
mws1060 9-(Arabinosyl)hypoxanthine Nucleotides and derivatives up – up
Wcjp001256 9-Alpha-Ribofuranosyladenine* Nucleotides and derivatives
down – up
Zmsp001773 9-Arabinosyladenine* Nucleotides and derivatives down – up
MWSHC2054 Adenine Nucleotides and derivatives up – up
pme0230 Adenosine* Nucleotides and derivatives down – up
Zmjn001030 Adenosine 2’-Phosphate Nucleotides and derivatives – – up
pme2117 Adenosine 5′-diphosphate Nucleotides and derivatives down –
down
pmb0981 Adenosine 5′-monophosphate Nucleotides and derivatives down –
down
pme1173 Allopurinol Nucleotides and derivatives up – up
mws1715 Cordycepin (3’-Deoxyadenosine)* Nucleotides and derivatives
down up up
MWSmce333 Crotonoside; 2-Hydroxyadenosine Nucleotides and derivatives –
– up
mws0884 Cyclic 3′,5′-Adenylic acid Nucleotides and derivatives up up up
ML10180524 Cytarabine Nucleotides and derivatives up up up
pme3732 Cytidine Nucleotides and derivatives up up up
MWSslk257 Cytidine 5′-monophosphate(Cytidylic acid) Nucleotides and
derivatives – – up
mws0255 Cytosine Nucleotides and derivatives up up up
MWS5083 Flavin Single Nucleotide(FMN) Nucleotides and derivatives – –
down
pme1109 Guanine Nucleotides and derivatives up up up
pme1178 Guanosine Nucleotides and derivatives – up up
mws0609 Guanosine 3′,5′-cyclic monophosphate Nucleotides and
derivatives up up up
pmb0998 Guanosine 5′-monophosphate Nucleotides and derivatives down – –
pme0033 Hypoxanthine Nucleotides and derivatives up – up
pmb0532 Inosine 5′-monophosphate Nucleotides and derivatives down –
down
MWS5173 Isocytosine Nucleotides and derivatives – – up
pme0183 Isoguanine Nucleotides and derivatives up up up
Lmcp002302 N6-(2-Hydroxyethyl)adenosine* Nucleotides and derivatives –
up up
pme2060 N6-Isopentenyladenine Nucleotides and derivatives up – –
MWS4354 N6-methyladenosine Nucleotides and derivatives up up up
pmb0197 N7-Methylguanosine Nucleotides and derivatives down – up
pmb0530 Nicotinic acid adenine dinucleotide Nucleotides and derivatives
down – –
pme2746 Riboflavin 5′-Adenosine Diphosphate Nucleotides and derivatives
– up –
pmf0289 Riboprine Nucleotides and derivatives up – up
pme3337 Succinyladenosine Nucleotides and derivatives – – up
mws0248 Uridine Nucleotides and derivatives up – up
pmb2922 Uridine 5′-diphospho-d-glucose Nucleotides and derivatives – up
–
pme3188 Uridine 5′-monophosphate Nucleotides and derivatives – up up
Zmfn000481 Uridine-5’-Diphosphate-D-Xylose Nucleotides and derivatives
– up –
Zmjp000966 Vidarabine Nucleotides and derivatives down – up
pme0256 Xanthine Nucleotides and derivatives up – –
mws0668 Xanthosine Nucleotides and derivatives up – up
mws0675 β-Nicotinamide mononucleotide Nucleotides and derivatives –
down –
Lmsp004137 3,4,2′,4′,6’-Pentahydroxychalcone Flavonoids down – –
pmn001716 Carthamone* Flavonoids down – –
HJN055 Dihydrocharcone-4’-O-glucoside* Flavonoids down up –
Labn004865 Hydroxy isoliquiritigenin glucoside* Flavonoids down – –
Lmlp006175 Isosalipurposide (Phlorizin Chalcone) Flavonoids – – –
pme2960 Naringenin chalcone; 2′,4,4′,6’-Tetrahydroxychalcone*
Flavonoids – down –
Cmxp005429 Okanin Flavonoids – down –
zjgp122004 Okanin-3’-O-β-D-glucoside* Flavonoids down – –
Cmxp003975 Okanin-4’-O-glucoside(Marein)* Flavonoids down – –
pme1201 Phloretin Flavonoids down down down
mws2118 Phloretin-2’-O-glucoside (Phlorizin) Flavonoids down up –
Hmmn003343 Sappanchalcone Flavonoids – – –
Hmpn005101 Sieboldin Flavonoids down – –
Zbbp005255 Aureusidin Flavonoids – down –
Cmxn006627 Maritimetin Flavonoids up down down
Jmgn005927 2-hydroxynaringenin Flavonoids down down –
Hmqn003268 5,7,3′,4′,5’-Pentahydroxydihydroflavone Flavonoids – – –
Jmgn004021 6-C-Glucosyl-2-Hydroxynaringenin Flavonoids down – –
Zbsp007084 Butin; 7,3′,4′-Trihydroxyflavanone* Flavonoids – down –
HJN090 Butin-7-O-glucoside* Flavonoids – up –
MWSslk252 Didymin (Isosakuranetin-7-O-rutinoside)* Flavonoids up up up
Hmhp005335 Dihydrobaicalein Flavonoids up down down
mws0064 Eriodictyol (5,7,3′,4’-Tetrahydroxyflavanone)* Flavonoids –
down –
HJN086 Eriodictyol-3’-O-glucoside* Flavonoids – – –
MWS20145 Eriodictyol-7-O-glucoside* Flavonoids down – –
pmb3023 Eriodictyol-8-C-glucoside* Flavonoids down – –
Lmqn009304 Eucalyptin (5-Hydroxy-7,4′-dimethoxy-6,8-dimethylflavone)
Flavonoids up up up
mws0463 Hesperetin Flavonoids up down down
pmb2970 Hesperetin-5,7-di-O-glucoside Flavonoids down – –
pme1598 Hesperetin-5-O-glucoside Flavonoids down – –
MWSHY0019 Hesperetin-7-O-neohesperidoside(Neohesperidin)* Flavonoids –
– –
Lahp003599 Homoeriodictyol-7,4′-di-O-β-D-glucopyranoside Flavonoids –
up –
Labp005025 Malonyl isoSakuranin Flavonoids down – –
MWSHY0017 Naringenin (5,7,4′-Trihydroxyflavanone)* Flavonoids – down –
HJN087 Naringenin-4’-O-glucoside* Flavonoids – – –
pma0724 Naringenin-6-C-Glucoside Flavonoids down – down
mws1179 Naringenin-7-O-glucoside (Prunin)* Flavonoids down – –
mws1454 Persicoside Flavonoids down – –
mws0789 Pinocembrin (Dihydrochrysin) Flavonoids up down –
mws0791 Poncirin (Isosakuranetin-7-O-neohesperidoside)* Flavonoids – up
–
mws0914 3,5,7-Trihydroxyflavanone (Pinobanksin) Flavonoids – down –
mws1094 Aromadendrin (Dihydrokaempferol) Flavonoids – down –
Lmtn002796 Aromadendrin-7-O-glucoside* Flavonoids down – –
Lmmn004625 Dihydrokaempferol-7-O-glucoside* Flavonoids down – –
mws0044 Taxifolin(Dihydroquercetin) Flavonoids – down –
Zbxn003562 Taxifolin-2-O-glucoside Flavonoids – up –
Xmsn002700 Taxifolin-3’-O-glucoside Flavonoids down – –
Lmdp003110 2,6,7,4’-Tetrahydroxyisoflavanone Flavonoids – – –
Lmqn006260 2′,3′,4′,5,7-Pentahydroxyflavone* Flavonoids up – –
Lmtp003948 3′,5′,5,7-Tetrahydroxy-4′-methoxyflavanone-3’-O-glucoside
Flavonoids down – –
Zbqn006065 3,5,7,2’-Tetrahydroxyflavone; Datiscetin* Flavonoids – down
–
Zmjp004875 5,6,3′,4’-Tetrahydroxy-3,7-dimethoxyflavone Flavonoids up –
–
Zmjp004852 5,6,3′,4’-Tetrahydroxy-3,7-dimethoxyflavone-6-O-glucoside*
Flavonoids – up –
Zmhn003257 5,7,2′-Trihydroxy-8-methoxyflavone* Flavonoids – down –
Hmmp007513 5,7-Dihydroxy-6,3′,4′,5′-tetramethoxyflavone
(Arteanoflavone)* Flavonoids down down down
Zmhp003514 6,7,8-Tetrahydroxy-5-methoxyflavone Flavonoids up up –
Zmyn003693 6-Hydroxy-2′-methoxyflavone Flavonoids – up up
Hmcn002875 6-Hydroxyluteolin Flavonoids up – –
Hmcn001884 6-Hydroxyluteolin 5-glucoside* Flavonoids down – –
MWS20151 Apigenin; 4′,5,7-Trihydroxyflavone Flavonoids – down –
MWS20148 Apigenin-4’-O-glucoside* Flavonoids down – –
mws1073 Apigenin-6,8-di-C-glucoside (Vicenin-2) Flavonoids – – –
Lmtp002474 Apigenin-6-C-(2″-glucosyl)arabinoside Flavonoids up up –
pmp000237 Apigenin-6-C-(2″-glucuronyl)xyloside Flavonoids down – –
MWSHY0021 Apigenin-7,4′-dimethyl ether Flavonoids up up up
pmp000585 Apigenin-7-O-(6″-malonyl)glucoside Flavonoids down – –
Lmpp003930 Apigenin-7-O-(6″-p-Coumaryl)glucoside Flavonoids down down
down
MWSHY0189 Apigenin-7-O-glucoside(Cosmosiin)* Flavonoids up up up
pmb2991 Apigenin-7-O-glucoside-4’-O-rutinoside Flavonoids down – –
pme0368 Apigenin-7-O-rutinoside (Isorhoifolin) Flavonoids down – down
Lmtp002642 Apigenin-8-C-(2″-glucosyl)arabinoside Flavonoids up up –
Lakn002234 Catechin glucosyl glucoside Flavonoids down – –
Lmyp005841 Chrysin-7-O-glucoside Flavonoids down – –
Lazp002140 Chrysoeriol glucosyl xylosyl glucoside Flavonoids down – –
pmb2999 Chrysoeriol-5-O-glucoside Flavonoids – – –
pmb0587 Chrysoeriol-7-O-(2”-O-glucuronyl)glucoside Flavonoids – up –
Zbsn005918 Chrysoeriol-7-O-(6″-acetyl)glucoside* Flavonoids – – –
pmb3012 Chrysoeriol-7-O-glucoside Flavonoids – – –
pmb3002 Chrysoeriol-7-O-rutinoside Flavonoids up – –
Zmjp009119 Chrysosplenetin
(5,4’-Dihydroxy-3,6,7,3′-tetramethoxyflavone)* Flavonoids down down
down
mws0058 Diosmetin (5,7,3′-Trihydroxy-4′-methoxyflavone)* Flavonoids –
down –
pmp000579 Diosmetin-7-O-galactoside* Flavonoids down – –
Lmyn006227 Galangin (3,5,7-Trihydroxyflavone) Flavonoids – down –
Lmlp005572 Galangin-7-O-glucoside Flavonoids down – –
MWSslk237 Hispidulin-7-O-glucoside(Homoplantaginin)* Flavonoids up – –
Zbzp003056 Isoorientin-7-O-glucoside* Flavonoids down – –
Lmlp002990 Isosaponarin(Isovitexin-4’-O-glucoside) Flavonoids up up up
Lmyp003837 Isovitexin-7-O-glucoside-2”-O-rhamnoside Flavonoids down – –
Lmfn001893 Leucocyanidin Flavonoids down up up
pme0088 Luteolin (5,7,3′,4’-Tetrahydroxyflavone) Flavonoids – down –
MWS20147 Luteolin-3’-O-glucoside Flavonoids down – –
Hmpp003270 Luteolin-4’-O-glucoside* Flavonoids down – –
MWSHY0016 Luteolin-6-C-glucoside (Isoorientin) Flavonoids down – –
Zmlp003063 Luteolin-7-O-(2”-O-rhamnosyl)rutinoside* Flavonoids down – –
Hmjn004446 Luteolin-7-O-(6″-caffeoyl)rhamnoside Flavonoids up up up
pmp000587 Luteolin-7-O-(6″-malonyl)glucoside* Flavonoids – – –
MWSHY0104 Luteolin-7-O-glucoside (Cynaroside)* Flavonoids down – –
MWSHY0121 Luteolin-7-O-glucuronide Flavonoids – – –
MWSHY0080 Luteolin-7-O-neohesperidoside (Lonicerin)* Flavonoids – –
down
Hmlp003068 Meratin* Flavonoids down – –
Hmmn004152 Neoeriocitrin Flavonoids – up –
Hmgp002036 Nepetin-7-O-glucoside(Nepitrin)* Flavonoids down – –
Ybnn007052 Norartocarpetin Flavonoids up down down
Zmjp003031 Orientin-2”-O-galactoside* Flavonoids down – –
Zbjp003056 Orientin-7-O-glucoside* Flavonoids down – –
Lmsp004632 Scutellarein (5,6,7,4’-Tetrahydroxyflavone) Flavonoids – – –
mws0920 Tricetin (5,7,3′,4′,5’-Pentahydroxyflavone) Flavonoids up down
–
Lmzp004885 Tricin (5,7,4′-Trihydroxy-3′,5′-dimethoxyflavone) Flavonoids
up up –
pmb3045 Tricin-7-O-Glucuronide Flavonoids down – –
Lcyp000688 Verecundin(Pinocembrin-5-glucoside)* Flavonoids down – –
Zbsn003878 Vicenin-3 Flavonoids up up –
pmp001111 Violanthin Flavonoids down – –
Zmjp003291 Vitexin-2”-O-galactoside Flavonoids – – –
pme3227 Vitexin-2”-O-rhamnoside Flavonoids down – –
Lmjp003655 6-C-MethylKaempferol-3-glucoside* Flavonoids down – –
Zmhp102730 6-Hydroxykaempferol-3,6-O-Diglucoside Flavonoids – – –
pmp001312 6-Hydroxykaempferol-3,7,6-O-triglycoside Flavonoids – – up
pmp001311 6-Hydroxykaempferol-6,7-O-Diglucoside Flavonoids down – –
pmp001309 6-Hydroxykaempferol-7-O-glucoside Flavonoids – – –
Lmjp003295 6-Methoxykaempferol-3-O-glucoside* Flavonoids – – –
MWSHY0077 Fisetin Flavonoids – – –
Lmmp002143 Gossypetin-3-O-(6″-malonyl)glucoside* Flavonoids down up –
Lmmp001947 Gossypetin-3-O-glucoside* Flavonoids down – –
Lmmp002904 Gossypetin-3-O-glucoside-8-O-xyloside Flavonoids – up –
Zmhp003784 Gossypetin-7-O-(3″-glucosyl)rhamnoside; Rhodioflavonoside
Flavonoids – up –
pmb0645 Hesperetin-6-C-glucoside-7-O-glucoside Flavonoids – – up
pmb0618 Hesperetin-8-C-glucoside-3’-O-glucoside Flavonoids down – –
mws0066 Isorhamnetin; 3′-Methoxy-3,4′,5,7-Tetrahydroxyflavone
Flavonoids up – –
Hmcp001578 Isorhamnetin-3,7-O-diglucoside Flavonoids down – –
Hmcp001658 Isorhamnetin-3-O-(6″-malonyl)glucoside-7-O-glucoside
Flavonoids down – –
Lmgp005640 Isorhamnetin-3-O-Galactoside; Cacticin Flavonoids – – –
Zbpp001992 Isorhamnetin-3-O-Glucoside* Flavonoids – – –
MWSHY0064 Isorhamnetin-3-O-neohesperidoside* Flavonoids – – –
Zbpp001877 Isorhamnetin-3-O-rutinoside* Flavonoids down – –
Hmcp002207 Isorhamnetin-7-O-glucoside (Brassicin)* Flavonoids – – –
MWSHY0201 Kaempferol-3,7-O-dirhamnoside (Kaempferitrin) Flavonoids down
– down
Lmdp004819
Kaempferol-3-O-(2″-sinapoyl)glucosyl-(1 → 2)-(6″-malonyl)glucoside
Flavonoids down down –
Lmdp004892 Kaempferol-3-O-(6″-malonyl)galactoside* Flavonoids down – –
Lmmp003817 Kaempferol-3-O-(6″-malonyl)glucoside* Flavonoids – – –
Hmcp001629 Kaempferol-3-O-(6″-Malonyl)glucoside-7-O-Glucoside
Flavonoids down – –
Lmmn003398 Kaempferol-3-O-(6”-O-acetyl)glucoside Flavonoids down – –
Xmyp004945 Kaempferol-3-O-(6”-Rhamnosyl-2″-Glucosyl)Glucoside
(Camelliaside A) Flavonoids – – up
mws0913 Kaempferol-3-O-galactoside (Trifolin)* Flavonoids down – –
Lmsp004670 Kaempferol-3-O-glucoside-7-O-rhamnoside* Flavonoids – – down
mws1035 Kaempferol-3-O-robinoside-7-O-rhamnoside (Robinin)* Flavonoids
down – –
Lmsp003161 Kaempferol-3-O-sophoroside-7-O-rhamnoside* Flavonoids down –
–
Lmqp002170 Kaempferol-3-O-sophorotrioside Flavonoids down – –
Xmyp005654 Kaempferol-4’-O-glucoside* Flavonoids down – –
HJAP023 Kaempferol-6,8-di-C-glucoside-7-O-glucoside Flavonoids down – –
mws0089 Kaempferol-7-O-glucoside* Flavonoids down – –
pme3514 Morin* Flavonoids up – –
mws0032 Myricetin Flavonoids – up –
Lmtp004126 Myricetin-3-O-(6″-malony)glucoside* Flavonoids down up –
pmn001640 Myricetin-3-O-arabinoside Flavonoids down up up
Lmdp002969 Myricetin-3-O-galactoside* Flavonoids down – –
Lmpp003465 Myricetin-3-O-β-D-glucoside* Flavonoids down – –
Zahp003364 myricetin-3-O-β-d-xylopyranosyl-(1 → 2)-β-D-glucopyranoside
Flavonoids down up –
Lakp003108 Myricetindiglucoside Flavonoids down up up
Hmgp001996 Quercetagetin; 3,3′,4′,5,6,7-Hexahydroxyflavone Flavonoids
up – –
Lmfp003403 Quercetagetin-7-O-glucoside(Quercetagitrin)* Flavonoids down
up –
Lmcp004369 Quercetin-3′,4′-dimethyl ether Flavonoids – – –
Zmcp002666 Quercetin-3,7-Di-O-glucoside* Flavonoids down – –
Zmcp003530 quercetin-3-hydroxyferuloyldiglucoside Flavonoids – – –
Lmyp003588 Quercetin-3-O-(2″,6”-O-digalloyl)-glucoside Flavonoids down
down down
Lmdp004221
Quercetin-3-O-(2”-O-caffeoyl)glucoside-(1 → 2)-(6″-Malonyl)glucoside
Flavonoids down – down
pmp000596 Quercetin-3-O-(2”-O-galactosyl)glucoside Flavonoids – – –
Lmfp005436 Quercetin-3-O-(2”-O-galloyl)Arabinoside Flavonoids up down
down
MWSHY0142 Quercetin-3-O-(2”-O-galloyl)galactoside Flavonoids – – up
Lmmp003266 Quercetin-3-O-(2”-O-malonyl)glucoside-7-O-arabinoside
Flavonoids down – –
Lmjp003360 Quercetin-3-O-(2”-O-malonyl)sophoroside-7-O-arabinoside
Flavonoids – – up
Hmcp001618 Quercetin-3-O-(2”-O-Xylosyl)rutinoside Flavonoids – – up
Hmln002199 Quercetin-3-O-(6”-O-acetyl)galactoside Flavonoids – – –
Zmsp004363 Quercetin-3-O-(6”-O-acetyl)glucoside Flavonoids – up up
Hmln001682 Quercetin-3-O-(6”-O-acetyl)glucosyl-(1 → 3)-Galactoside
Flavonoids down – –
Zbsp004136 Quercetin-3-O-(6”-O-arabinosyl)glucoside* Flavonoids – – –
MWSHY0199 Quercetin-3-O-(6”-O-galloyl)galactoside Flavonoids – – down
pmb0706 Quercetin-3-O-(6”-O-malonyl)glucosyl-5-O-glucoside Flavonoids
down – –
Lmfp002421 Quercetin-3-O-[rhamnosyl(1 → 2)glucosyl]-5-O-glucoside*
Flavonoids down – –
Lmdp003286 Quercetin-3-O-alloside; Isohyperoside* Flavonoids down – –
MWSHY0113 Quercetin-3-O-galactoside (Hyperin)* Flavonoids down – –
Hmcp001769 Quercetin-3-O-rhamnosyl(1 → 2)arabinoside Flavonoids down –
–
Lnrp102163 Quercetin-3-O-rutinoside-7-O-rhamnoside Flavonoids – – up
Lmjp002596 Quercetin-3-O-sambubioside* Flavonoids – – –
Lmsp002982 Quercetin-3-O-sophoroside-7-O-rhamnoside* Flavonoids down –
–
Lmdp003509 Quercetin-3-O-xyloside (Reynoutrin)* Flavonoids down – –
Lmmp003306 Quercetin-3-O-xylosyl(1 → 2)arabinoside Flavonoids – – –
Zmgp002857 Quercetin-3-O-α-rhamnosyl (1 → 2)-[α-rhamnosyl
(1 → 6)]-β-glucoside Flavonoids – up –
mws0856 Quercetin-4’-O-glucoside (Spiraeoside)* Flavonoids down – –
Lmfn003760 Quercetin-4’-O-glucuronide Flavonoids – up –
Smgp004575 Quercetin-5-O-β-D-glucoside* Flavonoids – – –
pmp000589 Quercetin-7-O-(6″-malonyl)glucoside Flavonoids down – –
mws1329 Quercetin-7-O-glucoside Flavonoids down – –
Lmjp002906 Rhamnetin-3-O-Glucoside* Flavonoids down – –
Zmpp002571 Robinetin Flavonoids down – –
mws2627 Tamarixetin (3,3′,5,7-Tetrahydroxy-4′-Methoxyflavone)
Flavonoids up up –
Lahp003408 2-(3,4-dihydroxyphenyl)-4 h-chromene-3,5,7-triol-glucoside
Flavonoids down – –
Lmmp003109 3’-O-Methyl-epicatechin Flavonoids down – –
pme3285 Afzelechin (3,5,7,4’-Tetrahydroxyflavan) Flavonoids down – –
mws0355 Catechin gallate* Flavonoids up up up
pmn001416 Catechin-(7,8-bc)-4α-(3,4-dihydroxyphenyl)-dihydro-2-(3H)-one
Flavonoids down – –
pmn001415 Catechin-(7,8-bc)-4β-(3,4-dihydroxyphenyl)-dihydro-2-(3H)-one
Flavonoids down – –
Zajn002491 catechin-4-β-D-galactopyranoside* Flavonoids down – –
pmb2947 Catechin-catechin-catechin Flavonoids down – –
pme0460 Epicatechin* Flavonoids down up –
mws1397 Epicatechin gallate* Flavonoids up up up
HJN041 Epicatechin glucoside Flavonoids down – –
Zmdn002400 Epicatechin-3’-O-β-D-glucopyranoside* Flavonoids down – –
Zmdn002049 Epicatechin-4’-O-β-D-glucopyranoside* Flavonoids down – –
pmb3114 Epicatechin-epiafzelechin Flavonoids down – –
MWSHY0098 Epigallocatechin Flavonoids – up –
mws0034 Epigallocatechin-3-gallate* Flavonoids – up –
Lajp003377 Fisetinidol-(4α,6)-gallocatechin Flavonoids down – –
mws0049 Gallocatechin Flavonoids down up up
mws2220 Gallocatechin 3-O-gallate* Flavonoids – up –
Lajp002779 Gallocatechin-(4α- > 8)-Catechin-(4α- > 8)-Catechin
Flavonoids down – –
Lmmp000897 Gallocatechin-(4α → 8)-gallocatechin Flavonoids down – –
Wbtp004753 1,2,3,7,8-pentahydroxy-6-methylanthracene-9,10-dione
Flavonoids down – –
Wbtn006715 1,2,4,5,8-pentahydroxy-6-methylanthracene-9,10-dione*
Flavonoids up – –
Wbtp004961 1,2,4,5-tetrahydroxy-7-(hydroxymethyl)anthracene-9,10-dione
Flavonoids down – –
pmn001477 4-C-Glucose-1,3,6-trihydroxy-7-methoxyxanthone Flavonoids
down – –
Satp005088
5-hydroxy-7-(2-hydroxypropyl)-2-(3-hydroxy-2-(4-hydroxy-3,5-dimethoxybe
nzyl)propyl)-chromone Flavonoids up – –
Wbtn006810 6,7-dihydroxy-1,3-dimethoxyxanthen-9-one* Flavonoids – down
–
Lcsn003955 Maesopsin Flavonoids – down –
MA10079134 1,2,4-Trihydroxyanthraquinone Quinones – – –
MWS20169 2,5-dihydroxy-1-methoxy-anthraquinone Quinones up up –
Zbn006783 5,6-Dihydroxylucidin Quinones up – –
Zmdn006929 Aloe-Emodin-9-Anthrone Quinones up down –
Zdhn005610 Citreorosein Quinones up down down
Zbqn006094 Pseudopurpurin(1,2,4-trihydroxy-3-carboxyanthraquinone)
Quinones up – –
Wmcp000011 Rheic Acid Quinones up – –
pmn001338 Rhein-8-O-glucoside Quinones down – –
Zbln013951
1-(3′-methoxy-4′-hydroxybenzyl)-2,7-dihydroxy-4-methoxyphenanthrene
Quinones down down down
Zbln007388 4,6-dimethoxy-9,10-dihydrophenanthrene-2,3,7-triol Quinones
up down down
Wmhp000055 2,5-Dimethoxybenzoquinone* Quinones up – –
Zmsp001834 2,6-Dimethoxy-1,4-benzoquinone* Quinones up – –
pmn001369 1-Hydroxypineolin Diglucoside Lignans and Coumarins – up –
pmn001375 1-Hydroxypinoresinol-1-O-Glucoside Lignans and Coumarins down
– –
Zmcn003729 1-Hydroxypinoresinol-4’-O-Glucoside Lignans and Coumarins –
– –
WaYn005928 Buddlenol B* Lignans and Coumarins up down –
WaYn006596 Buddlenol C Lignans and Coumarins up – –
WaYn006188 Buddlenol E* Lignans and Coumarins up – –
Lazn006616 Buddlenol F Lignans and Coumarins up – –
Lmsp004450 Dehydrodiconiferyl alcohol Lignans and Coumarins up down –
Cmsp003083 Dehydrodiconiferyl alcohol-4-O-glucoside* Lignans and
Coumarins – – –
Lmsp003655 Dehydrodiconiferyl alcohol-gamma’-O-glucoside* Lignans and
Coumarins – – –
Lmtn002596 Dihydrodehydrodiconiferyl alcohol-4-O-glucoside* Lignans and
Coumarins down – –
Lskp211385 dihydrosesamin Lignans and Coumarins up down –
MWSHC20189 Epipinoresinol* Lignans and Coumarins – down –
Lazn003893 Erythro-Guaiacylglycerol-β-Coniferyl Ether Lignans and
Coumarins up down –
Lazn006735 Erythro-Guaiacylglycerol-β-O-4′-dehydrodisinapyl Ether
Lignans and Coumarins up down –
Lazn005262 Erythro-Guaiacylglycerol-β-Sinapyl Ether Lignans and
Coumarins up – –
WaYn003112 Erythro-Guaiacylglycerol-β-threo-syringylglycerol Ether
Lignans and Coumarins up – –
Lhhp102922 Fargesin Lignans and Coumarins – – –
Lazn002951 Guaiacylglycerol-β-Guaiacyl Ether Lignans and Coumarins up –
–
Hmgn004139 Isohydroxymatairesinol Lignans and Coumarins – up –
Lmmn003748 Isolariciresinol Lignans and Coumarins up down –
Lmmn002274 Isolariciresinol-9’-O-glucoside* Lignans and Coumarins down
– –
HJN083 Lariciresinol-4’-O-glucoside Lignans and Coumarins – – –
Hmcn002743 Lirioresinol A Lignans and Coumarins up – –
Lmmn003020 Lyoniresinol Lignans and Coumarins – down –
Cmmn005231 Massoniresinol; Vladinol A Lignans and Coumarins – – –
Lssp210087 Matairesinol Lignans and Coumarins up down –
Lmmn003875 Medioresinol Lignans and Coumarins – down down
Rfmb056 Medioresinol-4’-O-(6″‘-acetyl)glucoside Lignans and Coumarins
up – –
pmn001376 Olivil Lignans and Coumarins up down –
mws0097 Pinoresinol* Lignans and Coumarins – down –
pmn001378 Pinoresinol-4-O-glucoside Lignans and Coumarins up up up
Lskp211262 Secoisolariciresinol Lignans and Coumarins – – up
MWSmce499 Secoisolariciresinol diglucoside Lignans and Coumarins – – –
Cmsn002480 Secoisolariciresinol-9’-O-glucoside Lignans and Coumarins up
– –
MWS20152 Syringaresinol Lignans and Coumarins up up –
MWSHC2047 Syringaresinol-4’-O-glucoside; Acanthoside B Lignans and
Coumarins up – –
Hmqn002118 7-Hydroxycoumarin;Umbelliferone Lignans and Coumarins up
down –
mws1075 7-Methoxycoumarin Lignans and Coumarins – – up
Lhkp101525 Apiosylskimmin (Adicardin) Lignans and Coumarins down – –
pmn001492 Ayapin Lignans and Coumarins up – –
MWSmce301 Coumarin-3-carboxylic Acid Lignans and Coumarins up – up
mws1074 Daphnetin Lignans and Coumarins – down –
Cmyn001328 Daphnin* Lignans and Coumarins down up up
mws1013 Esculetin (6,7-Dihydroxycoumarin) Lignans and Coumarins – down
–
Lmbn001162 Esculetin-7-O-glucoside* Lignans and Coumarins down up up
pmb3093 Esculetin-7-O-quinic acid Lignans and Coumarins down – –
mws1015 Esculin (6,7-Dihydroxycoumarin-6-O-glucoside)* Lignans and
Coumarins down up up
MWSmce025 Fraxetin-8-O-glucoside (Fraxin) Lignans and Coumarins – up up
Lcyp000676 Isoscopoletin-β-D-glucoside* Lignans and Coumarins down – –
Lmwp102713 Peucedanol* Lignans and Coumarins up – –
MWSCX014 Scopoletin (7-Hydroxy-6-methoxycoumarin)* Lignans and
Coumarins up – –
Lhqp101805 Skimmin (7-Hydroxycoumarin-7-O-glucoside) Lignans and
Coumarins – – –
Lmjp002764 Umckalin (7-hydroxy-5,6-dimethoxycoumarin) Lignans and
Coumarins – – down
Qmzp101901 Zanthoxyloside* Lignans and Coumarins down – –
Lasp003143 1,4-Benzodioxin-6-propanol Others – – –
Jmzn006005 3,4-methylenedioxy cinnamyl alcohol Others – up –
pmn001380 Eucommiol Others up – –
Cmyp007180 Dihydroactinidiolide Others up – –
pmb0128 δ-Tridecalactone Others up – –
Waln010743
1-(2,3-dihydroxypropoxy)-3-(((2-(dimethylamino)ethoxy)(hydroxy)phosphor
yl)oxy)propan-2-yl (11Z,14Z)-octadeca-11,14-dienoate Others – down –
Waln009920
1-(2,3-dihydroxypropoxy)-3-(((2-(dimethylamino)ethoxy)(hydroxy)phosphor
yl)oxy)propan-2-yl (8E,11Z,14Z)-octadeca-8,11,14-trienoate Others –
down –
Waln010449
1-(2,3-dihydroxypropoxy)-3-(((2-(dimethylamino)ethoxy)(hydroxy)phosphor
yl)oxy)propan-2-yl (E)-hexadec-9-enoate Others – down up
Waln011704
1-(2,3-dihydroxypropoxy)-3-(((2-(dimethylamino)ethoxy)(hydroxy)phosphor
yl)oxy)propan-2-yl (Z)-14-Octadecenoic Acid Others – down –
WaYn011606
1-(2,3-dihydroxypropoxy)-3-(((2-(dimethylamino)ethoxy)(hydroxy)phosphor
yl)oxy)propan-2-yl heptadecanoate Others – down up
Waln011524
1-(2,3-dihydroxypropoxy)-3-(((2-(dimethylamino)ethoxy)(hydroxy)phosphor
yl)oxy)propan-2-yl palmitate* Others – down –
Wcdp006741 1-(9Z,12Z-Octadecadienoyl)-Sn-Glycero-3-Phosphocholine
Others – down –
Wcsn010224 14-hydroxy-2,6,10-trimethylpentadeca-2,5,10-trien-4-one*
Others – down –
WaYn011395
2-(2,3-dihydroxypropoxy)-3-(((2-(dimethylamino)ethoxy)(hydroxy)phosphor
yl)oxy)propan-2-yl (Z)-14-Octadecenoic Acid Others – down –
Waln011009
2-(2,3-dihydroxypropoxy)-3-(((2-(dimethylamino)ethoxy)(hydroxy)phosphor
yl)oxy)propyl (11Z,14Z)-octadeca-11,14-dienoate Others – down up
Waln010192
2-(2,3-dihydroxypropoxy)-3-(((2-(dimethylamino)ethoxy)(hydroxy)phosphor
yl)oxy)propyl (8E,11Z,14Z)-octadeca-8,11,14-trienoate Others – down –
Waln011222
2-(2,3-dihydroxypropoxy)-3-(((2-(dimethylamino)ethoxy)(hydroxy)phosphor
yl)oxy)propyl palmitate* Others – down up
Lhyp111013 2(4H)-benzofuranone Others down – –
Hasp010605 2,3-dihydroxypropyl (9Z,12Z,15Z)-octadeca-9,12,15-trienoate
Others down down –
pmb0302 2-Aminoethylphosphonate Others – up up
Wagp002074 3-(1-hydroxyethyl)-4-methylpentane-1,4-diol O-Glucoside
Others down – –
Wcgp006109
3-(2-hydroxyethyl)-5,7-dimethoxy-4-methyl-2H-1-benzopyran-2-one* Others
up – –
Wdbn005328
3,3’-Bis(3,4-dihydro-4-hydroxy-6,8-dimethoxy-2H-1-benzopyran) Others up
– –
Lskp211267 3-Ethyl-7-hydroxyphthalide Others – – –
Wagp005297 3-Hydroxy-beta-ionol 3-Glucoside* Others down – –
Wcdp001930 3ξ-(1ξ-hydroxyethyl)-7-hydroxy-1-isobenzofuranone Others
down – –
Wagp001892 4-(Beta-D-Glucopyranosyloxy)-2-Pentanol Others down – –
Wcsn010254
4-[3-(4,8-dimethylnona-3,7-dienyl)-3-methyloxiran-2-yl]butan-2-one*
Others – down –
Zmmp002106 4-methyl-1,5,2,3-dioxadiazinan-2-amine Others down – up
pmb0764 4-Methyl-5-thiazoleethanol Others up up up
zjgp122321 4-O-acetyl-3-O-caffeoyl-2-C-methyl-D-erythronate* Others
down – –
Zbzp007397 5,6,7,7a-tetrahydro-4,4,7a-trimethyl-2(4H)-benzofuranone
Others up up –
Wcgp009361
5,7-diethoxy-3-(2-hydroxyethyl)-4-methyl-2H-1-benzopyran-2-one Others
up – –
Lmln001856
5,7-Dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)-4H-chromen-3-yl-alloside
Others down up –
Zahn007990 5-hydroxy-3,4-dimethyl-5-pentylfuran-2(5H)-one Others – up
up
Lhmp122205 5-O-Methyllatifolin Others – up –
Wcsn010496 6,10,14-Trimethylpentadeca-5,9-Diene-2,13-Dione Others –
down –
Hahn002084 6’-O-caffeoylcatalpol* Others up – –
Wcsn011125 Ethyl
15,16-dihydroxy-5,9-dimethyloctadeca-4,6,8,10,13-pentaenoate Others –
down –
Lhhp120823 Eugenyl formate Others – up –
Wasn005621 Glucosyl 9-hydroxy-3-methyldec-2-enoic acid Others up – –
Lcsp012679 linolenoylethanolamine Others – – down
Lmhp001671 Noreugenin-7-O-glucoside* Others down – –
MWSmce581 2,4-Dihydroxybenzaldehyde Others up up –
Lmbn001981 2,5-Dihydroxybenzaldehyde* Others up down down
Wmlp000056 3,5-Dimethoxy-4-hydroxybenzaldehyde Others up down down
Lmbn002737 3-Methylbenzaldehyde Others – – –
MWSmce644 4-Acetoxy-3-Ethoxybenzaldehyde Others up up up
Zmdp000376 4-Guanidinobutanal Others down – –
mws0628 4-Hydroxybenzaldehyde Others up – up
MWSCX017 4-hydroxyphenyl acrylaldehyde* Others up down down
MWS1852 4-Methoxybenzaldehyde Others up down –
MWS20172 5-Hydroxymethylfurfural Others – up –
Hmgn001653 Protocatechualdehyde* Others up down down
mws1350 Syringaldehyde; 4-Hydroxy-3,5-Dimethoxybenzaldehyde Others up –
–
mws0458 Vanillin; 4-Hydroxy-3-Methoxybenzaldehyde* Others up up up
Hmyp002315 3,5,7,4’-Tetrahydroxy-Coumaronochromone Others down – –
Layp002880 5,7-Dihydroxychromone glucoside Others down up up
Zmzp006646 Capillarisin Others up up –
MWSmce658 Noreugenin; 5,7-Dihydroxy-2-Methylchromone Others – down –
MWS0559 1,6-anhydro-β-d-glucose Others up – up
Wafn004792 1-O-Acetyl-Glucopyranose 6-Decanoate Others up – –
Lcsn000341 3’-Fucosyllactose Others down – –
Zmgn000447 3-Phospho-D-glyceric acid Others down – down
ML10171848 D-Arabinono-1,4-lactone* Others – – –
Zmzn000079 D-Erythrose-4-phosphate Others down – down
MWS2442 d-Fructose 6-Phosphate* Others – – –
MWSmce220 D-Glucono-1,5-lactone* Others up up –
Zmyn000110 D-Glucosamine 1-phosphate Others down – –
mws0866 d-Glucose 6-phosphate* Others – up –
mws1090 d-Glucose-1-phosphate* Others – up –
mws4175 D-Glucurono-6,3-lactone Others – up –
Lmxn000380 Digalactosylglycerol Others – down –
MA10039641 d-Lactose* Others down – –
Lmsn000381 D-Maltose* Others – – –
mws1593 D-Maltotetraose Others up – up
pme0500 D-Melezitose Others up – up
mws1589 D-Panose* Others up – –
pme3163 D-Sedoheptuiose 7-phosphate Others down down down
pme0519 D-Sucrose* Others – – –
mws0889 D-Threonic Acid Others up – –
pma0134 D-Threose Others – up –
mws0264 D-Trehalose* Others – – –
mws1080 Galactinol Others – – –
pmb3081 Glucaric acid-1-Phosphate Others – down down
MWSmce113 Guaifenesin Others up up up
pme2253 L-Gulono-1,4-Lactone* Others up up up
MWS1983 Maltitol Others – – –
MWS0442 Maltotriose Others up – –
mws1333 Melibiose Others down – –
mws2608 N-Acetyl-D-galactosamine Others up – –
pmb3079 N-Acetyl-D-glucosamine-1-phosphate Others – down up
mws4174 N-Acetyl-D-mannosamine Others up – –
mws4163 Nystose Others up – –
pme2125 Raffinose* Others up – –
Lmmn000214 Solatriose Others down down down
Lmqn000213 Stachyose Others up – –
mws1089 Sucrose-6-phosphate Others – up up
mws2523 Trehalose 6-phosphate Others – up up
MWSslk225 1-Indanone Others – down –
Lafp003256 3,4’-Dihydroxy-3′,5′-dimethoxypropiophenone Others up – –
Lmyp003951 3-Hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)propan-1-one
Others – – down
MWSslk095 4-Hydroxy-2,5-dimethyl-3(2H)furanone Others down – –
MWSmce466 4-Hydroxyacetophenone Others up – –
MWSmce283 4’-Hydroxypropiophenone Others up – –
Wbtn006721 6,8-dihydroxy-3-methyl-9-oxoxanthene-1-carboxylic acid*
Others – down –
MWSslk226 Benzylacetone Others – down down
Wbmp003302 Frambinone Others down up up
MWSHC20159 Roseoside Others – – –
Lmtp004146 Santalin Others down – –
MWS0434 Trans-dehydrorosinone Others up up up
Wasn000528 2-O-α-d-Glucopyranosyl-l-ascorbic acid Others down – –
pmb0801 4-Pyridoxic acid-O-glucoside Others down – –
MA10039492 Dehydroascorbic acid Others down – down
MWSmce690 Erythorbic Acid; Isoascorbic Acid Others – up –
Wasn001007 Isoascorbic acid 2-O-glucoside Others down – –
MWSmce039 Isonicotinic acid Others up – up
mws0133 Nicotinamide Others up up up
pma3101 Nicotinate D-ribonucleoside Others up – up
pme0490 Nicotinic acid (Vitamin B3) Others up – –
pme3511 Orotidine Others up – up
MWSmce674 Phylloquinone (Vitamin K1) Others down – down
Zmjp000624 Pyridoxal Others down – down
mws0655 Pyridoxal-5′-phosphate Others down – down
pme1383 Pyridoxine Others up down –
pmb0790 Pyridoxine-5’-O-diglucoside Others down – –
pmb0789 Pyridoxine-5’-O-glucoside Others down – –
pme1306 Pyridoxine-5′-phosphate Others up – –
pme2289 Retinol (Vitamin A1) Others down – –
mws0232 Riboflavin (Vitamin B2) Others up up up
MWSmce489 2,3,5,4’-Tetrahydroxystilbene-2-O-glucoside Others down –
down
Lmtp004915 3,5-Dihydroxy-3′,4′-diacetoxylstilbene-3-O-glucoside Others
– up –
MWSmce484 Astringin Others up – –
mws0021 Resveratrol Others up – –
Zmlp005013 3,3’-O-Dimethylellagic Acid Tannins up – –
Lmyn004187 Flavogallonic Acid Dilactone Tannins down – –
pme1738 3-Carbamyl-1-methylpyridinium;(1-Methylnicotinamide) Alkaloids
up up –
pma6298 3-Hydroxypyridine Alkaloids – up –
Zblp001009 3-pyridine-methanol-O-β-d-glucopyranosyl Alkaloids down – –
pmf0291 4-Hydroxypyridine Alkaloids – up –
MWS3270 Quinolinic Acid Alkaloids up – –
Yacp000453 3-hydroxy-1-methylpyrrolidin-2-one* Alkaloids – – up
Zmsp000878 4-Hydroxy-5-(2-oxo-1-pyrrolidinyl)benzoic acid* Alkaloids
down – –
MWStz081 Piperlotine C; 1-(3,4,5-Trimethoxycinnamoyl)pyrrolidine
Alkaloids – – –
MWS1860 Pyrrolidin Alkaloids down – up
MWSmce157 Stachydrine Alkaloids up – –
MWSslk106 2-Phenylethylamine Alkaloids down – –
MWS2076 2-Aminophenol Alkaloids – up –
MWSmce462 4-Hydroxybenzylamine Alkaloids – down –
Lmgp000796 4-Hydroxymandelonitrile Alkaloids down – up
MWS0435 Acetaminophen Alkaloids up – –
pma0101 Caffeoylagmatine Alkaloids – up up
pmp001244 Caffeoylcholine Alkaloids – up –
Hmcp009963 Candicine Alkaloids down down down
MWSmce521 Dobutamine Alkaloids down down down
MWStz070 N-(2-Hydroxy-4-methoxyphenyl)acetamide Alkaloids down down –
Wagp001741 N-(gamma-L-glutamyl)tyramine O-glucoside Alkaloids down – –
pmb0492 N′,N″,N″‘-p-Coumaroyl-cinnamoyl-caffeoyl spermidine Alkaloids
down – up
Zdcp003644 N-Caffeoylputrescine Alkaloids down – –
pmb0496 N-Feruloylagmatine Alkaloids down up up
Lmhp003013 N-Feruloyl-Cadaverine Alkaloids – – down
MWSmce098 Nonivamide Alkaloids – up –
pmb0490 p-Coumaroylputrescine Alkaloids – – –
Lmqp002784 Salicylamide Alkaloids down – –
Lahp002608 3,5-Dihydro-2H-Furo[3,2-C]Quinolin-4-One* Alkaloids down –
up
Ladp002935 3-quinolinecarboxylic acid Alkaloids – – up
Lmgp001898 4,6-Dihydroxyquinoline Alkaloids – – –
Ladp002110 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid
Alkaloids down – –
Wcjp002598 8-hydroxyquinoline Alkaloids down – up
Wasn002329 Xanthurenic Acid 8-O-Glucoside Alkaloids down – –
MWStz063 2-Ethyl-2,6,6-trimethylpiperidin-4-one Alkaloids up up up
pmp001198 6-Deoxyfagomine Alkaloids down – up
pmb0782 Piperidine Alkaloids down – up
MWStz152 2-(Acetylamino)-3-phenyl-2-propenoic acid* Alkaloids – – –
MWSmce645 2-(Aminooxy)Acetic Acid Alkaloids up up up
MWSslk118 2,2’-Cyclouridine Alkaloids – up –
MWS2063 2,6-Dimethylaniline Alkaloids down down –
MWSmce557 2-Acetyl-3-ethylpyrazine Alkaloids – down –
MWS1936 2-Methyl-5-nitroimidazole-1-ethanol Alkaloids – – down
Hmgp002327 3-amino-2-naphthoic acid* Alkaloids down – up
MWS1777 3-Chloroaniline Alkaloids – up up
MWSmce128 4(3H)-Quinazolinone Alkaloids – up –
Hmtp000776 4,5,6-Trihydroxy-2-cyclohexen-1-ylideneacetonitrile
Alkaloids – – up
Lamp000484 4-Methylazetidine-2-Carboxylic acid* Alkaloids – – up
pma3649 5-Aminolevulinic Acid* Alkaloids down – up
MWS2072 5-Nitrobenzimidazole Alkaloids – up –
Wbjp004368 8-Hydroxy-harmine Alkaloids down – –
MWSmce207 Acetylpyrazine Alkaloids – – –
pmb0501 Agmatine Alkaloids – up up
MWS3105 Aniline Alkaloids – – –
MWSmce331 Azetidine-2-carboxylic acid* Alkaloids down – –
MWSmce548 Betaine Alkaloids up up –
mws2218 Caffeine Alkaloids up up up
pmb0484 Choline Alkaloids – down down
MWS1784 Cyclohexylamine Alkaloids down – –
mws1346 DL-2-Aminoadipic acid* Alkaloids up – –
MWSmce448 Imidazol-1-yl-acetic acid* Alkaloids up – –
MWSmce461 L-Azetidine-2-carboxylic acid* Alkaloids down – –
pme1002 L-Tyramine Alkaloids down – –
Zasp102439 m-Aminophenylacetylene Alkaloids down – up
Zajp000573 N-(4-oxopentyl)-acetamide* Alkaloids up up up
pme2693 N-Acetylputrescine Alkaloids – up up
Smcp000882 N-benzoyl-2-aminoethyl-β-D-glucopyranoside Alkaloids – up up
pmp001287 N-Benzylmethylene isomethylamine Alkaloids down – up
MWS0700 Neopterin Alkaloids up down –
MWSmce571 N-Methylbenzylamine Alkaloids down – –
Qmdp090606 N-Methyltetrahydropalmatine Alkaloids down down –
mws0983 N-Oleoylethanolamine Alkaloids up – –
Zmpp000906 Norepinephrine Alkaloids up down –
Wbjp001169 o-Carboxy-5-hydroxytryptamine Alkaloids down – –
pmb1754 O-Phosphocholine Alkaloids down – –
pma0948 Phenylethanolamine Alkaloids up – up
MWS1919 Thiazole Alkaloids down – –
Wbmp002283 Α-hydroxyquinoline Alkaloids down – up
Cmyp003522 3’-Hydroxy-N-methylcoclaurine Alkaloids up down –
MWSmce709 Isoquinoline Alkaloids down – up
MWStz108 1-Ethoxycarbonyl-β-Carboline Alkaloids – down down
Zmbp002538 1-Methoxy-indole-3-acetamide* Alkaloids down – up
MWStz282 3-Hydroxy-3-acetonyloxindole* Alkaloids up – –
pmb0819 3-Indoleacetonitrile Alkaloids down – up
Hmmp001310 3-Indoleacrylic acid* Alkaloids down – up
pme2244 3-Indolepropionic acid Alkaloids up up up
pmc0682 4-Aminoindole Alkaloids down – –
mws0597 5-Hydroxyindole-3-acetic acid Alkaloids down up –
pme2836 5-Hydroxytryptophol Alkaloids – down –
mws0333 5-Methoxytryptamine Alkaloids down down down
Lmyn002540 Dioxindole-3-acetyl-3-O-glucoside Alkaloids down – –
pmb1096 Indole Alkaloids down – up
pme1651 Indole-3-acetic acid (IAA) Alkaloids – up up
mws0103 Indole-3-carboxaldehyde Alkaloids up up –
mws1417 Indole-3-carboxylic acid* Alkaloids up down –
mws0102 Indole-5-carboxylic acid* Alkaloids up down –
pmb0818 Methoxyindoleacetic acid Alkaloids down – up
Hmyp002656 Methyl dioxindole-3-acetate Alkaloids down – –
mws0677 N-Acetyl-5-hydroxytryptamine Alkaloids down – –
mws0620 N-Methyltryptamine Alkaloids down – –
mws0005 Tryptamine Alkaloids – – up
Qmjp080407 14(15)-Bisnor-13-oxolabd-8(17),11(E)-dien-19-oic acid
Terpenoids up down –
Qmjp080402 15,16-Bisnor-13-oxo-8(17),11-labdadien-19-ol Terpenoids –
down down
Wdzp007419 1β-hydroxy-β-cyperone Terpenoids up down down
Hmcn000773 6’-O-Glucosylaucubin Terpenoids – – –
Zjyp102922 Humula-3(12),7(13),9(E)-triene-2,6-diol Terpenoids up up up
MWSmce096 Nootkatone Terpenoids – – down
Zbbn002910 6”-O-sinapoyl-7-O-caffeoyl-geniposide Terpenoids up – –
pmp001070 6”-O-Trans-Sinapoylgenipin gentiobioside Terpenoids – – –
Wbmn003453 6-O-Vanilloylajugol Terpenoids – – –
Hmmn003964 7-Deoxyloganic acid Terpenoids down – –
Sacn001940 8-Epiloganic acid Terpenoids down – –
pmn001587 Asperulosidic acid Terpenoids – – up
mws1562 Catalpol Terpenoids up up up
pmn001586 Deacetylasperulosidic acid Terpenoids down – –
MWSmce434 Gardenoside Terpenoids – up up
Lmdn001501 Gardoside* Terpenoids down – –
MWSmce115 Genipin Terpenoids up down down
Lhjp111633 Glucosylasperuloside Terpenoids – up –
pmp000691 Loganetin Terpenoids – – –
Zbyn002745 Loganic acid Terpenoids down – –
Lmjp004816 Loliolide Terpenoids – – –
pmn001585 Monotropein Terpenoids down – –
Cmrn001591 Mussaenosidic acid Terpenoids down – –
Cmhp003670 Secologanin Terpenoids – up –
pmp001053 Shanzhiside Terpenoids down – –
mws1526 Sweroside Terpenoids down up up
Lmpn004676 Verminoside* Terpenoids up – –
mws1429 Vomifoliol (Blumenol A) Terpenoids up – –
Labn003976 Vomifoliol 9-[Xylosyl-(1 → 6)-Glucoside] Terpenoids up – –
mws1515 α-Ionone Terpenoids up – –
Cmmn012461 Dehydroabietic acid Terpenoids down down down
MWSslk208 Kaurenoic Acid* Terpenoids up – –
Wbmn011269 Vitexilactone Terpenoids – down down
Llhp011701 11,12-epoxy-13-hydroxy-3-Oxooleanane-28-oic acid
gamma-lactone (Liquidambaric Lactone) Terpenoids up – up
pmn001427 16,23:16,30-Diepoxydammar-24-ene-3,20-diol (Jujubogenin)*
Terpenoids – up –
Lskp211493 2,19-Dihydroxy-3-oxo-24-norolean-12-en-28-oic acid
Terpenoids up – –
pmn001426 2,3,19-trihydroxyurs-12-en-28-oic acid (Euscaphic acid)*
Terpenoids up up –
MWSmce394 2,3,19-Trihydroxyurs-12-en-28-oic acid (Tormentic acid)*
Terpenoids – up up
Smpn009230 2,3,23-Trihydroxyolean-12-en-28-oic acid* Terpenoids up up
up
Lmqp008286 2,3,23-Trihydroxyolean-12-en-28-oic acid (Arjunolic acid)
Terpenoids up – –
Hmjn003948 2,3,6-Trihydroxyurs-12-en-28-oic acid (Madasiatic acid)*
Terpenoids up up up
Lmzn106284 2,3-Dihydroxylup-20(29)-en-28-oic acid (Alphitolic acid)*
Terpenoids – up up
pmn001706 2,3-Dihydroxyolean-12-en-28-oic acid (2-Hydroxyoleanolic
acid)* Terpenoids – up up
Hmjn008136 2,3-Dihydroxyoleana-11,13(18)-dien-28-oic acid (Camaldulenic
acid) Terpenoids up up –
Lmsn012627 2,3-Dihydroxyurs-12,18-dien-28-oic acid Terpenoids up up –
Zmpn008194 2,3-Dihydroxyurs-12-en-28-oic acid (Corosolic acid)*
Terpenoids – up up
[80]Li512114 2,3-Dihydroxyurs-12-en-28-oic acid methyl ester (Corosolic
acid methyl ester) Terpenoids – – up
mws1610 2,3-Dihydroxyurs-12-en-29-oic acid (Maslinic acid)* Terpenoids
– up up
Lssp210085 3,11-dioxo-β-oleorene Terpenoids – up up
pmn001591 3,19,23-Trihydroxyurs-12-en-28-oic acid (Rutundic acid)
Terpenoids – up –
Lhnp110101 3,20-Dihydroxyurs-21-en-28-oic acid (Oleanderic acid)
Terpenoids – up up
Hmbn005207 3,23-Dihydroxyolean-12-en-28-oic acid (Hederagenin)*
Terpenoids – – up
MWSHC20176 3-Hydroxylup-20(29)-en-28-oic acid (Betulinic acid)
Terpenoids – up –
mws1389 3-Hydroxyolean-12-en-28-oic acid (Oleanolic acid)* Terpenoids –
up up
Lmsp102910 3-Hydroxyolean-12-ene-27,28-dioic acid (Cincholic acid)
Terpenoids up – –
Lmmn009550 3-Oxo-9,19-cyclolanost-24-en-26-oic acid (Mangiferonic
acid)* Terpenoids up – –
Ymjm000099 3-Oxooleana-11,13(18)-dien-28-oic acid Terpenoids up up up
Lmhn011365 Morolic acid* Terpenoids up up up
Lmqn012798 Urs-12(13)-en-3-one-28-oic acid* Terpenoids up up up
Lmxn001694 6”-O-β-D-Glucosyl-8-O-acetylharpagide Terpenoids up – up
Zadn003162 Ajugoside Terpenoids – – up
Smhn002274 Blumenol C glucoside; Byzantionoside B* Terpenoids down – –
Zadp003164 Dehydrololiolide Terpenoids – – –
pmn001381 Eucommioside Terpenoids up – –
Zmdn003368 eucomoside A Terpenoids – up up
Zmdn004697 eucomoside B Terpenoids up – –
Zmdn004845 eucomoside C Terpenoids up up –
Lmlp002205 Isololiolide Terpenoids – – –
Rfmb320 1-Methylpiperidine-2-carboxylic acid* Organic acids up up up
Lcsn006884 2,2′-(3-methylcyclohexane-1,1-diyl)diacetic acid Organic
acids – – –
Wmzn000227 2,2-Dimethylsuccinic acid Organic acids down down down
pme0278 2,6-Diaminooimelic acid Organic acids down – –
Wccp000476 2-[(1R)-1-carboxyethoxy]propanoic acid Organic acids – – –
Lmbn001609 2-Acetyl-2-Hydroxybutanoic Acid Organic acids up – –
Zbqp000579 2-amino-3-(1H-pyrazol-1-yl)propanoic acid Organic acids down
up up
mws0236 2-Aminoethanesulfonic acid Organic acids – up –
pme3017 2-Aminoisobutyric acid* Organic acids – down down
Lmbn001288 2-Hydroxy-2-methyl-3-oxobutanoic acid Organic acids up – –
Lmrn002746 2-Hydroxy-4-methylpentanoic acid Organic acids – – –
Lmmn003323 2-Hydroxyhexadecanoic acid* Organic acids up – –
mws0341 2-Hydroxyisocaproic acid Organic acids up – –
Lcsn006335 2-Hydroxymyristic acid Organic acids up – –
Zmyn002323 2-Hydroxyphenylacetic acid Organic acids up – –
mws0924 2-Methylglutaric acid* Organic acids up – –
mws0473 2-Methylsuccinic acid* Organic acids – – –
pme1216 2-Picolinic acid Organic acids up – up
Lmbn002072 2-Propylsuccinic acid* Organic acids up – –
MWS5147 3-(Methylthio)Propionic Acid Organic acids – – down
MWSmce362 3-Ethoxy-3-oxopropanoic acid Organic acids down – –
Hmhn002738 3-Furoic acid Organic acids down – –
Lmbn001676 3-Hydroxy-3-Methyl-2-Oxopentanoic Acid* Organic acids up up
up
Lmbn000216 3-Methylmalic acid* Organic acids down – –
Zmtn001464 4,8-Dihydroxyquinoline-2-carboxylic acid Organic acids up –
–
pme0295 4-Acetamidobutyric acid Organic acids up – –
mws0373 4-Methyl-2-oxovalerate Organic acids up – –
Lmbn001467 5-Acetamidopentanoic Acid Organic acids up – –
MWSslk038 6-Acetamidohexanoic acid Organic acids down down –
pme0274 6-Aminocaproic acid Organic acids down – up
mws0972 6-Hydroxyhexanoic acid Organic acids up down down
Lmtn004049 Abscisic acid Organic acids up – up
mws0208 Adipic Acid* Organic acids up – –
pme3096 Aminomalonic acid Organic acids up – –
Lmyp003934 Anacardic acid Organic acids up down up
mws0237 Azelaic acid Organic acids up – –
mws0489 Benzoylformic acid Organic acids down down down
mws0425 Citraconic acid Organic acids – up –
WaYn000716 Citric Acid diglucoside Organic acids down – –
Lmmn000806 Dimethylmalonic acid* Organic acids – – –
MWS0274 DL-3-Phenyllactic acid* Organic acids up up up
mws0267 DL-Glyceric Acid Organic acids – – –
MWSmce183 D-Mandelic acid Organic acids up down down
Wasn001627 Glucosyl 2,3-Dihydroxy-2-Methylbutanoic Acid Organic acids –
– down
Wasn003258 Glucosyl 2-Hydroxy-4-Methylpentanoic Acid Organic acids up –
–
MWS1882 Iminodiacetic acid* Organic acids down up –
Zmjp003163 Jasmonic acid Organic acids up down down
MWS0811 L-Pipecolic Acid Organic acids – – –
Wayn000504 Malic acid-1-O-diglucoside Organic acids up up up
Lmyn002403 Mandelic acid-β-glucoside Organic acids up – –
MWS2040 Methanesulfonic acid Organic acids up – –
MWSmce536 Methyl 2-furoate Organic acids – – –
pme0220 Methyl jasmonate Organic acids up – –
mws0470 Methylmalonic acid* Organic acids up – –
MWS5136 Mono-Methyl Glutarate* Organic acids up up up
Lmmn002164 Monomethyl succinate* Organic acids – – –
Lmyn000160 Mucic acid Dimethyl Ester Organic acids – – –
mws1167 Oxalacetic acid Organic acids up – up
mws0159 Phenylpyruvic acid Organic acids up – –
mws2125 Phosphoenolpyruvate Organic acids – up down
Zmjn001813 Pimelic acid* Organic acids up – –
mws0242 Suberic Acid Organic acids up – –
mws0192 Succinic acid* Organic acids up – –
Lmgn000219 Succinic semialdehyde Organic acids up – –
pme2380 α-Ketoglutaric acid Organic acids up – –
mws0147 β-Hydroxyisovaleric acid Organic acids up – –
Wcdp010162 1-Monolinolenoyl-Rac-Glycerol* Lipids – down down
pmb0296 1-Oleoyl-Sn-Glycerol Lipids – down –
Zbfn008434 1-O-Linoleoyl-3-O-galactopyranosyl-L-glycerol Lipids down
down –
Wagn011658 1-Palmitoyl-Sn-Glycerol 3-O-Diglucoside Lipids down down –
pmb1562 1-Stearidonoyl-Glycerol Lipids down down –
Lmhp011562 1-α-Linolenoyl-glycerol* Lipids – down down
Lmhp009773 1-α-Linolenoyl-glycerol-3-O-glucoside* Lipids – – –
Wagn012030 2-Palmitoyl-Sn-Glycerol 3-O-Diglucoside Lipids – down –
Lmhp011388 2-α-Linolenoyl-glycerol* Lipids – down down
Lmhp008513 2-α-Linolenoyl-glycerol-1,3-di-O-glucoside Lipids down down
–
Lmhp009526 2-α-Linolenoyl-glycerol-1-O-glucoside* Lipids – – –
Lmfp009701 Glycerol 9(E),11(Z),13(E)-octadecatrienoyl ester* Lipids –
down down
Walp013004 Glycidyl Linoleate Lipids – down down
WaYn012231 LPG(18:2(9Z,12Z)/0:0) Lipids down down down
Hmyn007168 LysoPG 16:0 Lipids down down down
Sazp010264 Monogalactosyldiacylglycerol Lipids – down down
Lmsp010763 Monolinolenin* Lipids – down down
Hmyp007792 PE(oxo-11:0/16:0) Lipids down up up
Lmqn008024 PS(18:2) Lipids down down –
mws0120 Choline Alfoscerate Lipids down – down
pmb2221 4-Hydroxysphinganine; Phytosphingosine Lipids down up up
pmd0130 LysoPC 14:0 Lipids – down up
pmb2319 LysoPC 15:0* Lipids up down –
Lmhp009129 LysoPC 15:0(2n isomer)* Lipids – down –
pmb2260 LysoPC 15:1 Lipids up down –
pmb0855 LysoPC 16:0 Lipids – down –
pmd0132 LysoPC 16:0(2n isomer) Lipids – down –
pmp001270 LysoPC 16:1* Lipids up down up
Lmhp008833 LysoPC 16:1(2n isomer)* Lipids – down –
pmb0863 LysoPC 16:2(2n isomer) Lipids – down up
pmb2406 LysoPC 17:0* Lipids – down –
Lmhp010515 LysoPC 17:0(2n isomer)* Lipids up down up
Lmhp009590 LysoPC 17:1 Lipids – down up
Lmhp008718 LysoPC 17:2 Lipids up down up
mws0126 LysoPC 18:0 Lipids – down –
pmd0136 LysoPC 18:0(2n isomer) Lipids – down –
Lmhp010190 LysoPC 18:1(2n isomer) Lipids – down –
pmp001251 LysoPC 18:2(2n isomer) Lipids – down up
pmb0865 LysoPC 18:3(2n isomer) Lipids – down –
Hmqp006235 LysoPC 18:4 Lipids – down up
pmb2228 LysoPC 19:0 Lipids – down –
Lmhp010908 LysoPC 19:1 Lipids – down –
Lmhp007598 LysoPC 19:2(2n isomer) Lipids up down –
Lmhp011549 LysoPC 20:1 Lipids – down –
pmd0147 LysoPC 20:2* Lipids – down –
pmd0146 LysoPC 20:2(2n isomer)* Lipids – down –
Lmhp009890 LysoPC 20:3 Lipids – down –
pmb0864 LysoPE 14:0* Lipids down – up
Lmhp008337 LysoPE 14:0(2n isomer)* Lipids down – up
Lmhp009187 LysoPE 15:0 Lipids down down up
Lmhp008885 LysoPE 15:0(2n isomer) Lipids down – up
Lmhp008440 LysoPE 15:1 Lipids down – up
pmb0876 LysoPE 16:0 Lipids down down up
pmd0160 LysoPE 16:0(2n isomer) Lipids down down up
Lmhp009034 LysoPE 16:1* Lipids down down –
Lmhp008763 LysoPE 16:1(2n isomer)* Lipids down down –
Lmhp010162 LysoPE 17:0 Lipids down – up
Lmhp009769 LysoPE 17:1* Lipids down down up
Lmhp009464 LysoPE 17:1(2n isomer)* Lipids down down up
pmb0883 LysoPE 18:0 Lipids down down up
mws0289 LysoPE 18:1* Lipids down – up
pmb0856 LysoPE 18:1(2n isomer)* Lipids down down up
pmb0881 LysoPE 18:2 Lipids down – up
pmb0874 LysoPE 18:2(2n isomer) Lipids down – up
Lmhp008801 LysoPE 18:3 Lipids down – up
Lmhp008589 LysoPE 18:3(2n isomer) Lipids down – up
Lmhp008233 LysoPE 18:4 Lipids down – up
Lmhp010040 LysoPE 20:3* Lipids down down up
Lmhp009802 LysoPE 20:3(2n isomer)* Lipids down – up
pmn001686 10,16-Dihydroxypalmitic acid Lipids up up up
mws2623 11-Octadecanoic acid(Vaccenic acid)* Lipids – down down
Zmyn004548 12-Oxo-phytodienoic acid Lipids – down down
Lmbn005369 13(S)-HODE;13(S)-Hydroxyoctadeca-9Z,11E-dienoic acid* Lipids
– down down
Zmzn003953 13(s)-hydroperoxy-(9z,11e,15z)-octadecatrienoic acid Lipids
up up up
MWS80007 13-Hydroperoxy-9Z,11E-octadecadienoic acid* Lipids up up up
Lmbn005443 13-KODE; (9Z,11E)-13-Oxooctadeca-9,11-dienoic acid* Lipids
up down –
MWS2430 13-methylmyristic acid Lipids up up up
pmb2804 13S-Hydroperoxy-9Z,11E-octadecadienoic acid Lipids – down down
Zmyn004676 17-Hydroxylinolenic acid Lipids up down down
Zmyn005384 2R-Hydroxyoctadecanoic Acid* Lipids up – –
Zmyn005252 3-Hydroxy-palmitic acid methyl ester Lipids up – –
Wcdp006929 4-Oxo-9,11,13,15-Octadecatetraenoic Acid Lipids up down –
pmb0885 4-Oxo-9Z,11Z,13E,15E-Octadecatetraenoic Acid Lipids up down –
MWS2673 5,6-DiHETrE[(±)5,6-dihydroxy-8Z,11Z,14Z-eicosatrienoic acid]
Lipids – down –
Lmbn005287 7S,8S-DiHODE;
(9Z,12Z)-(7S,8S)-Dihydroxyoctadeca-9,12-dienoic acid* Lipids up up up
Lmbn005662 9(10)-EpOME;(9R,10S)-(12Z)-9,10-Epoxyoctadecenoic acid
Lipids up down down
pmn001694 9,10,13-Trihydroxy-11-Octadecenoic Acid Lipids up down –
Lmbn004240 9,10-Dihydroxy-12,13-epoxyoctadecanoic acid Lipids up – up
Lmbn003970 9,12,13-TriHOME;
9(S),12(S),13(S)-Trihydroxy-10(E)-octadecenoic acid Lipids up down –
pmn001691 9,12,13-Trihydroxy-10,15-octadecadienoic acid Lipids up down
–
pmb2791 9-Hydroperoxy-10E,12,15Z-octadecatrienoic acid Lipids up down
down
pmb2786 9-Hydroxy-10,12,15-octadecatrienoic acid* Lipids up down –
Zmyn004449 9-Hydroxy-12-oxo-10(E),15(Z)-octadecadienoic acid Lipids –
down down
pmn001689 9-Hydroxy-12-oxo-15(Z)-octadecenoic acid* Lipids up down –
Rfmb087 9-Hydroxy-13-oxo-10-octadecenoic Acid Lipids up – –
WaYn010298 9-Hydroxyoctadeca-6,10,12,15-Tetraenoic Acid Lipids up –
down
Wcdp007645 9-Oxo-10,12-Octadecadienoic Acid Lipids up down down
pmb2787 9-Oxo-10E,12Z-octadecadienoic acid Lipids up down down
Zmjn004133 9S-Hydroperoxy-10E,12Z-octadecadienoic acid Lipids – – –
Rfmb091 9S-Hydroxy-10E,12Z-octadecadienoic acid* Lipids – down down
Wafn011571 alpha-Hydroxylinoleic acid* Lipids – down down
Zbfn013528 Beta-Hydroxypalmitic Acid* Lipids up – –
Lmbn005923 Crepenynic acid Lipids – down –
MWS4295 DL-2-hydroxystearic acid* Lipids up – –
mws0396 Elaidic Acid* Lipids – down down
MWSslk132 Hexadecanedioic acid Lipids up – –
Zadn009075 Hydroperoxylinoleic acid* Lipids up down –
Yalp008047 Methyl 12-phenyldodecanoate Lipids – down down
Lmyn012331 Petroselinic acid* Lipids – down down
mws0367 α-Linolenic Acid* Lipids – down down
mws0366 γ-Linolenic Acid* Lipids – down down
[81]Open in a new tab
Fig. 4.
[82]Fig. 4
[83]Open in a new tab
Variations of metabolites groups in different samples. A, B, C shows
the up/down and number of adjustments bars for BT vs. XY, HG vs. XY,
and GT vs XY., respectively. D: Venny for HG vs. XY and GT vs. XY and
RT vs. XY.
XY as the core group and comparing it one-to-one with the other three
samples, their nonvolatile metabolites formed a Venn diagram ([84]Fig.
4D), with both common and unique metabolites between the different
control groups. The result revealed those were 266 overlapping
significantly differential metabolites among the three pairwise
comparisons. These 266 metabolites are considered key metabolites that
might be differently regulated during each processing treatment.
Compared to the other two groups, there were 79 metabolites specific to
HG vs. XY. And 144 metabolites specific to the GT vs. XY group, and a
high number of 439 metabolites specific to BT vs. XY. It is illustrated
again that the BT treatment makes a great impact on the non-volatile
metabolites in EUL.
3.3.1. Amino acids and their derivatives
Amino acids are often associated with aroma, flavor and freshness.
Methionine, valine, lysine and threonine, etc. are necessary for human
body. Moreover, many amino acids are the flavor enhancers.
Among the processing methods, the HG is most conducive to producing the
amino acid content beneficial for the human body in EUL leaves, with
the GT process ranking in second. In the heatmap the amino acid and
their derivatives (Fig. S3A), the relative content varies from red to
green, with the HG group exhibiting a concentration of red, while the
BT group shows a concentration of dark green.
Based on data from Table S3, the BT still caused a substantial decrease
in the amino acid content of fresh EUL. Most of the down-regulated
amino acids were related to bitterness, which may indicate that BT
processing can reduce bitterness and astringency. The reason might be
that amino acids undergo deamination, decarboxylation, and Maillard
reaction during withering to produce various alcohols and aldehydes as
aroma substances([85]Jin-jie et al., 2013). In addition, during
fermentation, most of the amino acids provide nitrogen and carbon
sources for microorganisms, and combine with tea polyphenols and sugars
to form quinones, aldehydes, acids, alcohols, pigments and other
substances under enzymatic action, thus the amino acids are
down-regulated([86]Shao et al., 2022).
In GT, there were more up-regulated metabolites than down-regulated
amino acid and derivatives, and mostly small-molecule peptides in the
up-regulated substances. Especially, cyclosmall peptides with proline,
which is heat stable, should be the marker for GT. This association
could be attributed to the diminished activity of hydrolytic enzymes
during the green tea processing ([87]Yiding et al., 2014). This results
in a decrease in the ability to convert substances such as proteins and
polypeptides into free amino acids, ultimately resulting in an
increased formation of small molecule peptides.
In HG, the random degraded peptides with 2 to 3 amino acid residues are
the main up-regulated metabolites, and the fructosyl amino acid which
is probably produced by heat stress should be recognized as the marker,
for N-(1-deoxy-1-fructosyl) leucine and N-(1-deoxy-1-fructosyl) valine
upregulated for over 60 folds. This can indicate that EUL HG process
than the GT process makes them show different variation obviously.
Furthermore, some important amino acids including L-tryptophan,
L-leucine, L-phenylalanine, L-arginine, and L-methionine showed
different levels of content increase after HG compared to XY.
L-tryptophan, L-phenylalanine and L-tyrosine are precursors for natural
products such as pigments, indole compounds, alkaloids,
phenylpropanoids and hormones([88]Maeda & Dudareva, 2012).
Conversely, the concentration of glutamic acid and lysine, recognized
as flavor enhancers, is substantially higher in XY compared to other
samples. In contrast, aspartic acid, another flavor enhanced amino
acid, is mainly increased in the BT process. This indicate that BT
processed EUL should possess different flavor in contrast to XY
significantly.
3.3.2. Lipids
Both glycerides and glycerophospholipids are major lipids for energy
substrate accumulation in plant leaves ([89]Kimura et al., 2019). They
can be hydrolyzed and oxidized in enzymatic and nonenzymatic way, also
can be hydroxylated in enzymatic way. In this research, 144 nonvolatile
lipid metabolites were detected belonging to the following five
categories: free fatty acids, glycerides, lysoglycerophospholipid,
hydroxylated fatty acid and oxidized fatty acid. In BT, almost all of
the up-regulated lipids were hydroxylated and oxidized fatty acid, it
should contribute to that the fermentative microorganism use lipid as
oxidative substrates to obtain energy. In HG, nearly all of the
up-regulated lipids were lysoglycerophospholipid, especially
lysophosphatidylethanolamine (LPE) and lysophosphatidylcholin (LPC). It
should contribute to free fatty acid loss in the thermos pyrolysis of
glycerides. In GT, longer/shorter chain fatty acids such as arachidic
acid(C20), docosenoic acid(C22), myristic acid(C14) and random
unsaturated octadecanoic(C18) were upregulated, it should be
contributed to a rapid thermal oxidation.
From the Heat map of lipid classes (Fig. S3B), α-linolenic acid and
γ-linolenic acid showed downward adjustments in both the GT process and
HG process, and there was no significant change in BT processing. The
reason is that each process has different water distribution speed,
black tea after withering for a long time. And room temperature water
loss is not as fast as removing and drying. Reducing water causes the
concentration of lipoxygenase (LPO) to rise, therefore lipids like
linolenic acid are converted to volatiles by the enzyme([90]Dongqing,
2001).
Furthermore, glyceride metabolites were down-regulated after different
processes. May be attributed to autoxidation, photo-oxidation and
enzymatic oxidation during processing ([91]Shahidi & Hossain, 2022).
3.3.3. Flavonoids
Flavonoids are generally present in EUL in the form of glycosides or
carbon sugar groups, but also in free form. Flavonoids are also
important coloring substances in tea, for example, quercetin gives tea
a green color([92]Wang et al., 2021).
In this study, the number of significant up- and down-regulation of the
three comparison groups, BT vs. XY, GT vs. XY, and HG vs. XY, were 33,
43, 21, and 121, 32, 18, respectively. It is observed that the
metabolite content of flavonoids was decreased after the BT process,
while the HG treatment had a somewhat lesser effect on the total
quantity of flavonoids.
In BT, plenty of dissociated flavonoids and a few flavonoid glycosides
increased rapidly, for example, the contents of isorhamnetin,
tamarixetin, quercetin, morin, and kaempferol increased by 11.80-,
11.01-, 9.88-, 7.51-, and 6.44-fold, respectively. That is to say, the
fermentation microorganisms hydrolyzed a great many of flavonoid
glycosides by glycosidase in BT process. Pick quercetin and its
glycosides as an example, those associated with dicarbohydrate, rare or
modified monosaccharides such as quercetin −3-O-rhamnosyl(1 → 2)
arabinoside, quercetin-7-O-rutinoside etc. decreased distinctly, but
flavonoids monomer, such as quercetin and naringin, increased evidently
in BT process. It might be because fermentation allows glycosides to be
degraded by the action of enzymes ([93]Jingyi, M., et al., 2023).
Reducing compounds such as catechins and proanthocyanidins A4 are
consumed in microbial processes. The fermentation process in turn leads
to further conversion of catechins ([94]Dongqing, 2001).
In GT, the apparent change is flavonoid gallate and rare flavonoid
glycosides increased obviously. Catechin, epicatechin, gallocatechin,
epigallocatechin etc. were all existed in the form associated with
gallate. And didymin, poncirin, myricetin, apigenin-7-O-glucoside and
isovitexin-4’-O-glucoside, which were not present in XY, increased
significantly after processing. The other significant increase is in
catechins, the major components of freshness, bitterness and
astringency in green tea. After the GT processing, there was a partial
down-regulation of chalcone analogs, which are important precursor
substances of catechins. This may be the reason for the up-regulation
of catechins. The GT processing can also enhance part of the flavonoid
content, to play its medicinal properties are still beneficial, but the
bitterness and astringency cannot be less like the BT processing.
In HG, there was also a tendency for some catechins and homologs to be
significantly up-regulated. However, the multiplicity was not as high
as after the GT processing and the existed form of catechins were
polymer or modified glycosides, for example,
gallocatechin-(4α → 8)-catechin and 3’-O-Methyl-epicatechin. But in
general,
Overall, HG is the lest different process from fresh leaves. And the BT
treatments cause the flavonoids to drop even more, where the withering
treatment is crucial for reducing the bitter and astringent flavonoids
in the tea. Also, after prolonged withering and fermentation, the ester
catechins will decrease and the enzyme activity will be similarly
inhibited([95]Shao et al., 2022).
3.3.4. Phenolic acids
The phenolic acid active substances in EUL are mainly composed of
chlorogenic acid and their related metabolites (isochlorogenic acid,
chlorogenic acid A/B/C, 1-caffeoyl- quinic acid, etc.) and gallic acid
(GA) and its associated compounds, caffeic acid and its homologs and
derivatives (caffeic aldehyde, etc.) and quinic acid derivatives.
(hydroquinone, Koaburaside etc.). In the heat map of phenolic
acids(Fig.S4D) in this study, both dark red and dark green colors are
mostly concentrated in the BT, indicating significant up- and
down-regulation changes. and is significantly different from the other
three samples.
Chlorogenic acid, cryptochlorogenic acid and neochlorogenic acid were
significantly down-regulated by 0.36-, 0.43- and 0.23- fold only after
the BT processing, while isochlorogenic acid A/B/C was up-regulated by
about 2-fold only after the GT processing. Phenolic compounds originate
from the biosynthetic pathways of shikimic acid, phenylpropanoid, and
flavonoids([96]Tohge et al., 2017). Chlorogenic acid was down-regulated
after the BT processing, while chlorogenic acid did not change much
after the GT and HG processing. This is similar to previous studies
because of the fermentation stage of black tea processing and the
gradual reduction of enzymes([97]Sha et al., 2008). In another words,
in BT processing microorganism utilized the reducing force of
chlorogenic acid and promote the biosynthesis of other pre-chlorogenic
acid metabolites. And HG/GT processing maintain the concentration of
chlorogenic acid, but the higher temperature of GT processing promotes
the production of isochlorogenic acid by additioning of another caffeic
acid to the 1′,3′ or 5′ hydroxyl of quinic acid.
Gallic acid (GA) and its associated compounds should also be markers of
GT processing EUL. Gallic acid, digallic acid, trigallic acid and other
gallate associated carbohadrate or modified by methyl were all
increased uniquely in GT than other processing EUL. So, GT processing
would bring more astringency for this feature.
Caffeic acid and its homologs and derivatives are tightly related to GT
processing. And caffeic acid has good hepatoprotective, anti-diabetic
and anti-tumor effects ([98]Mirzaei et al., 2021). Almost all the
simple caffeol modified compounds were increased in GT, such as caffeic
acid, 1-caffeoylquinic acid, 3-O-caffeoylshikimic acid,
dihydrocaffeoylglucose etc.
Quinic acid derivatives widely existed in XY, GT and HG, but only a few
derivatives existed in BT. But, it is interesting that the etherifying
quinic acid glucoside which is improved to be a potential antiviral and
anti-inflammatory activity were determined so high in BT processing,
and hydroquinone increased obviously in GT and HG which maybe cauesd by
high temperature stimulation on quinic acid.
In BT, metabolites increased also include O-anisic acid, gentisic acid,
ferulic acid, isoferulic acid, p-coumaric acid, hydroxycinnamic acid,
and sinapyl alcohol. Those are all functional substances which should
contribute to fermentation microrganism.
In HG, cinnamic acid, desmethylpinobanksin, 2-methylbenzoic acid, and
3-methylsalicylic acid were all up-regulated by 5-folds or more.
Cinnamic acid improves glucose tolerance in the body and stimulates
insulin secretion outside the body to achieve anti-diabetic effect
([99]Hafizur et al., 2015). Cinnamaldehyde has the potential to be
converted into cinnamyl alcohol and methyl cinnamate and cinnamic acid
in the body, from the heatmap (Fig.S4D) this is the reason why the
fresh leaves contain more cinnamyl alcohol than other processed
samples.
3.3.5. Nucleotides and derivatives
A total of 69 significantly differentiated metabolites of nucleotides
and their derivatives were screened. According to the three comparative
groups of BT vs. XY, GT vs. XY and HG vs. XY, the highest number of
up-regulation was found in HG vs. XY, followed by GT vs. XY and BT vs.
XY. The highest number of down-regulation was found in the group of BT
vs. XY. It can be seen that the HG treatment improves the content of
nucleotides and their derivatives better.
Common nucleotide and those compounds can be used as reducing force
such as NAD and NADP were all found to increase in fresh EUL. HG
processing boosted the production of most nucleotides and derivatives
include the common nucleotides, such as adenosine(A), guanosine(G),
thymine(T), cytidine(C) and their modified molecules. These should
contribute to the thermo-decomposition of nuclear acid. BT processing
promoted the production of 1,7-dimethylxanthine, 3-methylxanthine,
which are the precursor of caffeine. And also, their xanthine, a purine
degradation intermediate, should be picked as the typic metabolite of
BT processing. Then, GT processing promoted the production of methyl
modification nucleotides and especially stimulated the accumulation of
inosine 5′-monophosphate (IMP), a flavor enhancer which would endow the
flavor of GT auxiliary.
3.3.6. Alkaloids
Alkaloids, as a natural ingredient, can achieves significant
anti-hepatocellular carcinogenic effects. It is reached using a variety
of mechanisms to inhibit proliferation, such as metastasis and
angiogenesis, to promote apoptosis and autophagy, and to regulate
various cancer-related genes and pathways, etc.([100]Liu et al., 2019).
From the comparison of the number of significant up- and
down-regulations in these three groups (BT vs. XY, GT vs. XY, and HG
vs. XY), HG vs. XY was the most up-regulated and BT vs. XY was the most
down-regulated. The variated alkaloids in EUL were mainly composed of
amines, amides, quinoline and derivatives, indoles, quinolinic acid and
nuclear bases derivatives. Based on the heatmap of the alkaloid classes
(Fig.S3F), there was less red color lumps in the XY sample, and there
were significant red color lumps in BT, GT, and HG. This suggests any
one of the treatments would have a significant effect on the content of
the different alkaloids.
BT processing promoted the production of caffeine, quinine, indole
carboxylic acid and Octadec-2-enamide. The content of metabolites such
as indole ketone, quinine, and quinolinic acid in BT showed a
significant increasing trend (Fig.S3F), whereas salicylamide,
benzamide, and cyclohexylamine showed a significant decreasing trend.
Notably, caffeine was up-regulated 120-fold after BT/GT processing.
This indicates that the BT processing stimulated the increase in
caffeine content more than the other two processes. Quinolinic acid was
up-regulated in black tea processing only and not in the other two
processes.
The HG processing promoted the idolization, hydroxylation and
carbonitridation, more than 20 metabolites such as indole,
8-hydroxyquinoline, isoquinoline, and 3-Indoleacetonitrile,
4-Hydroxymandelonitrile were significantly more abundant than other
samples.
GT processing should be marked by the production of active polyamines
(PAs). Spermine, spermidine, agmatine, caffeoylagmatine, stearamide and
dopamine etc. were increased only in GT processing EUL. PAs are not
only one of the plant growth regulators, but also the essential
metabolites to tumor cell cycle. Recent data indicate that polyamines
can play a major role in regulating the anti-tumor immune response,
thus likely contributing to the existence of immunologically ‘cold’
tumors that do not respond to immune checkpoint blockade ([101]Holbert
et al., 2022).
3.3.7. Organic acids
Organic acids are not only key intermediates for decomposing carbon
compounds, but also coordinate flavors, providing acidity and fruit
flavors. Since the rankings of the number of upward and downward
adjustments in the organic acids category were BT vs. XY, HG vs. XY and
GT vs. XY. In addition, from the organic acids heatmap (Fig. S3G), it
could be seen that the red color lumps concentrated in the BT sample,
meaning that BT processing still favors the enhancement of organic
acids.
Firstly, methyl jasmonate was up-regulated up to 89-fold in the BT
group and was investigated as a substance with a floral aroma. It has
also been shown to be a phytohormone. ([102]Besson et al., 2018).
Secondly, in GT, the up-regulation multiplier is not as high as the
up-regulation multiplier of organic acids after the BT processing.
Finally, from the organic acids heatmap (Fig. S3G), it could be seen
that the red color lumps concentrated in the BT sample, meaning that
the BT processing favors the production of organic acids.
3.3.8. Lignans
Lignans are one of the most researched components of EUL. The active
ingredients in Eucommia lignans are mainly pinosylvin diglucoside and
butyrophilin diglucoside. However, neither of these two substances were
among the significantly different metabolites in the BT vs. XY, GT vs.
XY, and HG vs. XY groups. Among the three groups, the highest number of
upregulations was found in BT vs. XY; and the lowest number of
downregulations was found in GT vs. XY. Finally, judging from the
lignin Heatmap (Fig. S3H), the red color is concentrated in the BT
sample, so it is clear that the EUL leaves after the BT processing are
the highest in lignin content.
Pinoresinol, epipinoresinol, eucommin A, and buddlenol B/E/F, which
amounts were enhanced just in the processing of BT, should be
identified as the marker of lignans of EUL. Pinoresinol and
epipinoresinol is the residue of pinosylvin diglucoside, and had been
proved to be the effective antihypertensive drug by recent research.
Otherwise, pinoresinol-4,4’-O-diglucoside and secoisolariciresinol
diglucoside existed in GT processing, which had been identified to anti
hypertension.
3.3.9. Tannin
There were 12 non-volatile metabolites tannins in the four samples
tested, 9 (8 down-regulated) of them were significantly different
metabolites. And the differential metabolites were only present in the
BT vs. XY group. It contains proanthocyanidins, which are condensed
tannins and are the end products of the flavonoid biosynthesis pathway.
It is recognized for its strong antioxidant activity, in addition to
anticancer, anti-glycemic and neuroprotective effects([103]Rauf et al.,
2019). In addition, the heatmap (Fig. S3I) showed that the
proanthocyanidins in fresh EUL were relatively abundant, especially in
GT processing and it would further decompose after BT processing. The
proanthocyanidins content of GT only raised a bit higher than XY and
was differed from that of HG obviously, but all the three samples
contained similar content of tannin.
3.3.10. Terpenes
Terpenes are generally derived from mevalonate, and come into being the
hot area in E. ulmoides, many terpenes, especially 5 new iridoid
molecules were identified and analyzed in recent years ([104]Lv et al.,
2023; [105]Takamura et al., 2007).
105 terpene nonvolatile metabolites were detected in this study. Among
them, 71 were significantly different in the three comparison groups of
BT vs. XY, GT vs. XY, and HG vs. XY. With BT vs. XY being the group
with the highest number of up- and down-regulations. In general, BT, GT
and HG treatments raised the terpene content. In the Heatmap of
terpenes (Fig. S3J), it can be seen that the red color of the BT
samples is more concentrated, further illustrating the benefits of the
BT processing on the rise of terpene content.
It is clear that BT processing has a beneficial effect on some free
terpene rise. EUL leaves have important terpene actives, especially
iridoid and its derivatives, such as geniposide, geniposidic acid, etc.
Almost all of them got increase in BT processing, while verminoside,
kaurenoic acid were also raised. But it is worth to point out that the
aucubin, geniposide, genipenic acid and gardoside down-regulated
obviously in BT processing. These should contribute to glycoside
shedding caused by fermentation microrganis. Conversely, GT and HG
processing enhance the accumulation of aucubin, geniposide, genipenic
acid and gardoside.
3.3.11. Sugar (carbohydrates)
BT processing also increased the acidification of monocarbohydrate and
some nonreduced carbohydrate, for example, concentration of
D-glucoronic acid, D-galacturonic acid, D-xylonic acid raised obviously
and raffinose, fucose, xylitol, fructose and rhamnose were much higher
than XY and other treatments. That is to say, BT EUL would possess a
special sweet taste.
GT processing raised the concentration of sucrose, manitol, dulcitol
etc. and promoted the carbohydrate phosphorylation, for instance,
contents of d-fructose 6-phosphate, d-glucose 1,6-bisphosphate,
d-glucose 6-phosphate, d-glucose 1-phosphate were all higher than other
processing.
3.4. Volatile metabolite profiles and dynamics of XY, HG, RT, GT
A total of 289 ([106]Table 4) volatile metabolites belonging to 16
classes were found in XY, HG, RT, and GT. According to [107]Fig. 5A,
the heterocyclic class had the largest proportion (50), followed by
esters (46), terpenoids (41), hydrocarbons (35), alcohols (28),
aldehydes (27), ketones (26), aromatics (13), amines (6), phenols (5),
acids (3), nitrogen-containing compounds (3), sulfur-containing
compounds (3), ethers (1), lipids (1), and other volatile metabolites
(1), and other volatile metabolites (1), and other volatile metabolites
(1), lipids (1) and other volatile metabolites (1).
Table 4.
Summary table of volatile metabolite composition, classification and
relative content of substances in different processed EUL.
Index Compounds Class Odor
NMW0057 Glutarimide Amine –
XMW0711 Formamide, N-phenyl- Amine –
XMW1471 1-ButanAmine, N-methyl-N-2-propenyl- Amine –
NMW0013 Benzylamine Amine –
WMW0092 1-OctanAmine,N-methyl- Amine –
XMW0545 Benzenemethanamine, N-(1-methylethyl)- Amine –
XMW0735 Benzenemethanol, .alpha.-2-propenyl- Alcohol –
WMW0187 2-Hexanol Alcohol chemical, winey, fruity, fatty, terpenic,
cauliflower
D373 2,4-Heptadien-1-ol, (E,E)- Alcohol green, fruity, nutty, cheese
KMW0102 1-Hexanol Alcohol ethereal, fusel, oily, fruity, alcoholic,
sweet, green
w02 2,4-Decadien-1-ol Alcohol fatty, waxy, citrus, melon
KMW0092 2-Furanmethanol Alcohol alcoholic, chemical, musty, sweet,
caramel, bread, coffee
KMW0323 Benzyl Alcohol Alcohol floral, rose, phenol, balsamic
WMW0127 3-Octen-1-ol, (Z)- Alcohol fresh, fatty, grassy, melon, green,
cortex, herbal, earthy, fusel, spicy
KMW0194 2-Octanol Alcohol fresh, spicy, green, woody, herbal, earthy
KMW0355 trans,cis-2,6-Nonadien-1-ol Alcohol green, cucumber, oily,
violet, leafy
XMW0424 2,6-Dimethyl-1-nonen-3-yn-5-ol Alcohol –
KMW0629 1-Dodecanol Alcohol earthy, soapy, waxy, fatty, honey, coconut
KMW0344 1-Nonanol Alcohol fresh, clean, fatty, floral, rose, orange,
dusty, wet, oily
XMW1072 (E)-2,6-Dimethylocta-5,7-dien-2-ol Alcohol –
KMW0098 3-Hexen-1-ol, (Z)- Alcohol fresh, green, grass, foliage,
vegetable, herbal, oily
XMW1307 Cyclohexanol, 1-methyl- Alcohol –
XMW0642 Cyclohexanol, 3,5-dimethyl- Alcohol –
XMW0434 4-Hexen-1-ol, acetate Alcohol –
WMW0103 2-Cyclopentylethanol Alcohol –
D387 1-Hexanol, 3,5,5-trimethyl- Alcohol grassy, green, weedy, floral,
earthy, aldehydic, hay, straw, leafy
NMW0022 Benzenemethanol, .alpha.-methyl- Alcohol fresh, sweet,
gardenia, hyacinth
KMW0276 1-Octanol Alcohol intense citrus, rose
XMW1233 3-Cyclopentyl-1-propanol Alcohol –
XMW0410 1-Nonen-4-ol Alcohol –
KMW0294 2-Octen-1-ol, (E)- Alcohol green, citrus, vegetable, fatty
NMW0038 Benzenemethanol, 4-methyl- Alcohol mild, floral
KMW0376 2-Nonanol Alcohol rose
KMW0588 3-Cyclohexene-1-ethanol, .beta.,4-dimethyl- Alcohol fruity,
herbal
w08 Naphthalene, 1-methyl- Aromatics naphthyl, chemical, medicinal,
camphor
XMW0916 (5-bromopentyl)-Benzene Aromatics –
KMW0070 Benzene, 1,3-dimethyl- Aromatics plastic
XMW0659 Benzene, n-butyl- Aromatics –
KMW0060 Toluene Aromatics sweet
KMW0404 Naphthalene Aromatics pungent, dry, tarry
XMW0790 6,7-Dimethyl-1,2,3,5,8,8a-hexahydronaphthalene Aromatics –
WMW0227 Benzene, 1,4-dichloro- Aromatics –
KMW0115 Styrene Aromatics penetrating, balsamic, gasoline
KMW0273 Benzene, 1,2,4,5-tetramethyl- Aromatics rancid, sweet
KMW0307 Benzene, 1-methyl-4-(1-methylethenyl)- Aromatics phenol, spicy,
clove, guaiacol
XMW0539 3,4-Dimethoxytoluene Aromatics –
XMW0041 Benzene, 1,2-dimethoxy-4-(1-propenyl)- Aromatics spicy, clove,
blossom, carnation, woody
XMW0615 Phenol, m-tert-butyl- Phenol –
D356 3-Methoxy-5-methylphenol Phenol oakmoss, fruity, iodine, woody,
hay
KMW0175 Phenol Phenol phenol, medicinal
XMW0791 Phenol, 4-methyl-2-nitro- Phenol –
NMW0112 Phenol, 2-(1,1-dimethylethyl)- Phenol –
D265 Dodecanenitrile Nitrogen compounds citrus, orange, peel, metallic,
spicy
D355 2,6-Octadienenitrile, 3,7-dimethyl-, (Z)- Nitrogen compounds
citral, lemon, aldehydic, metallic
XMW0762 Imidodicarbonic diamide Nitrogen compounds –
D94 Benzenemethanethiol Sulfur compounds sharp, alliaceous, onion,
sulfury, garlic, horseradish, minty, coffee
KMW0162 Dimethyl triSulfur compounds Sulfur compounds sulfury, cooked
onion, savory, meaty
D98 Benzene, (methylthio)- Sulfur compounds toluene, solvent, spicy,
woody, sawdust
XMW1464 Benzene, (butoxymethyl)- Ether floral, rose
XMW0269 2-Methylbutanoic anhydride Others –
KMW0435 2-Decenal, (Z)- Aldehyde tallow
KMW0570 2-Dodecenal, (E)- Aldehyde citrus, metallic, mandarin, orange,
waxy, aldehydic
KMW0068 3-Hexenal, (Z)- Aldehyde green, fatty, grassy, weedy, fruity,
apple
KMW0066 Hexanal Aldehyde aldehyde, grassy, green, leafy, vinegar
XMW1118 CyclohexanecarboxAldehyde Aldehyde –
XMW0294 10-Undecenal Aldehyde waxy, aldehydic, rose, mandarin, citrus,
soapy, fatty
XMW0255 BenzAldehyde, 2,4-dimethyl- Aldehyde naphthyl, cherry, almond,
spice, vanilla
XMW0089 4-Decenal, (E)- Aldehyde fresh, aldehydic, citrus, orange,
mandarin, tangerine, green, fatty
KMW0088 2-Hexenal, (E)- Aldehyde green, grassy
WMW0069 2-Propenal, 3-phenyl- Aldehyde sweet, spicy, aldehydic,
aromatic, balsamic, cinnamyl, resinous, honey, powdery
XMW0246 OxiranecarboxAldehyde, 3-methyl-3-(4-methyl-3-pentenyl)-
Aldehyde –
KMW0243 (E)-2-Octenal Aldehyde fresh, cucumber, fatty, green, herbal,
banana, waxy, leafy
D401 2-Isopropyl-5-methylhex-2-enal Aldehyde herbal, lavender, woody,
green, blueberry, tomato
XMW0170 BenzAldehyde, 3-ethyl- Aldehyde –
KMW0407 2,4-Nonadienal, (E,E)- Aldehyde fatty, melon, waxy, green,
violet, leafy, cucumber, tropical, fruity, chicken
XMW0526 AcetAldehyde, (3,3-dimethylcyclohexylidene)-, (Z)- Aldehyde –
KMW0123 4-Heptenal, (Z)- Aldehyde oily, fatty, green, dairy, milky,
creamy
KMW0122 Heptanal Aldehyde fresh, aldehydic, fatty, green, herbal, wine,
ozonous
KMW0129 2,4-Hexadienal, (E,E)- Aldehyde sweet, green, spicy, floral,
citrus
KMW0158 BenzAldehyde Aldehyde sweet, bitter, almond, cherry
KMW0343 2-Nonenal Aldehyde fatty, green, waxy, cucumber, melon
XMW0679 AcetAldehyde, tetramer Aldehyde –
KMW0361 BenzAldehyde, 4-ethyl- Aldehyde bitter, almond, sweet, anisic
XMW0675 2,6,6-Trimethylcyclohexa-1,4-dienecarbAldehyde Aldehyde –
XMW0217 cis-7-Decen-1-al Aldehyde citrus, aldehydic, cucumber
XMW0189 3-Cyclohexene-1-acetAldehyde, .alpha.,4-dimethyl- Aldehyde
spicy, herbal
KMW0475 (2E,4Z)-2,4-Decadienal Aldehyde fried, fatty, geranium, green,
waxy
XMW1237 3-Pentenoic Acid, 2,2-dimethyl- Acid –
NMW0209 Undecylenic Acid Acid sweet, woody
KMW0096 Butanoic Acid, 3-methyl- Acid sour, stinky, feet, sweaty,
cheese, tropical
KMW0386 cis-Dihydrocarvone Terpenoids herbal, warm
KMW0556 Naphthalene,
decahydro-4a-methyl-1-methylene-7-(1-methylethenyl)-,
[4aR-(4a.alpha.,7.alpha.,8a.beta.)]- Terpenoids herbal
KMW0296 Cyclohexene, 1-methyl-4-(1-methylethylidene)- Terpenoids
citrus, pine
NMW0093 D-Verbenone Terpenoids –
KMW0606 .alpha.-Muurolene Terpenoids woody
XMW1138 6-Octen-1-ol, 7-methyl-3-methylene- Terpenoids –
NMW0101 Ascaridole Terpenoids –
KMW0217 d-Limonene Terpenoids citrus
XMW0006 (+)-3-Carene Terpenoids sweet
NMW0041 (E)-4,8-Dimethylnona-1,3,7-triene Terpenoids –
KMW0595 1,3-Cyclohexadiene, 5-(1,5-dimethyl-4-hexenyl)-2-methyl-,
[S-(R*,S*)]- Terpenoids spice, fresh, sharp
KMW0604
(1S,2E,6E,10R)-3,7,11,11-Tetramethylbicyclo[8.1.0]undeca-2,6-diene
Terpenoids green, woody, weedy
D197 3-Oxatricyclo[4.1.1.0(2,4)]octane, 2,7,7-trimethyl- Terpenoids
green
NMW0104 2,6-Octadien-1-ol, 3,7-dimethyl- Terpenoids –
WMW0040 trans-.beta.-Ocimene Terpenoids sweet, herbal
NMW0034 Fenchone Terpenoids herbal, cedar leaf, bitter, thuja, camphor,
earthy, woody
XMW0913 cis-Chrysanthenol Terpenoids –
KMW0453 Linalyl acetate Terpenoids sweet, green, citrus, bergamot,
lavender, woody
KMW0526 2-Buten-1-one, 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-,
(E)- Terpenoids apple, rose, honey, tobacco, sweet
KMW0582 .beta.-Guaiene Terpenoids sweet, woody, dry, guaiacwood, spicy,
powdery
KMW0199 .beta.-Myrcene Terpenoids musty, balsamic, spice
NMW0075 Cyclohexanol, 1-methyl-4-(1-methylethylidene)- Terpenoids
terpineol, lilac
NMW0113 6-Octen-1-ol, 3,7-dimethyl-, formate Terpenoids bergamot,
cucumber, rose, apricot, peach, plum
KMW0254 1,5-Heptadien-4-one, 3,3,6-trimethyl- Terpenoids herbal, honey,
minty, berry
KMW0479 1,3-Cyclohexadiene-1-carboxaldehyde, 2,6,6-trimethyl-
Terpenoids fresh, herbal, phenol, metallic, rosemary, tobacco, spicy
WMW0194 Thujone Terpenoids cedar leaf
NMW0087 2-Oxabicyclo[2.2.2]octan-6-one, 1,3,3-trimethyl- Terpenoids –
WMW0215 .beta.-Ocimene Terpenoids apple, pear, fruity
D407 7-Octen-4-ol, 2-methyl-6-methylene-, (S)- Terpenoids –
KMW0291 Linalool Terpenoids floral, green
KMW0312 Furan, 3-(4-methyl-3-pentenyl)- Terpenoids woody
XMW0780 2,6-Dimethyl-1,3,5,7-octatetraene, E,E- Terpenoids –
XMW0542 1-Cyclohexene-1-carboxaldehyde, 4-(1-methylethyl)- Terpenoids –
KMW0388 Carveol Terpenoids minty, spearmint, cool, green, herbal,
caraway, spicy
XMW0766 Cyclohexanone, 5-methyl-2-(1-methylethylidene)- Terpenoids
minty
WMW0003 Eremophilene Terpenoids –
XMW0548 Bicyclo[7.2.0]undecane, 10,10-dimethyl-2,6-bis(methylene)-,
[1S-(1R*,9S*)]- Terpenoids –
WMW0007
[1S-(1.alpha.,7.alpha.,8a.beta.)]-1,2,3,5,6,7,8,8a-octahydro-1,4-dimeth
yl-7-(1-methylethenyl)-Azulene Terpenoids –
XMW0817
(1S,5S,6R)-6-Methyl-2-methylene-6-(4-methylpent-3-en-1-yl)bicyclo[3.1.1
]heptane Terpenoids –
D328
(5R,10R)-10-Methyl-6-methylene-2-(propan-2-ylidene)spiro[4.5]dec-7-ene
Terpenoids –
XMW0157
(2R,3R,6S)-6-Isopropyl-3-methyl-2-(prop-1-en-2-yl)-3-vinylcyclohexanone
Terpenoids –
XMW0422 3,5-Dimethyldodecane Hydrocarbons –
NMW0010 Dicyclopentadiene Hydrocarbons –
D266 1-Tridecene Hydrocarbons –
KMW0079 Octane Hydrocarbons gasoline
XMW0771 1,5-Cyclooctadiene, 3,4-dimethyl- Hydrocarbons –
XMW0279 E-1-Methoxy-4-hexene Hydrocarbons –
XMW0121 1-Nonene, 4,6,8-trimethyl- Hydrocarbons –
WMW0126 1,3-Hexadiene, 3-ethyl-2-methyl- Hydrocarbons nutty
XMW0159 2,6,10-Trimethyltridecane Hydrocarbons –
XMW0099 Decane, 2,3,5-trimethyl- Hydrocarbons –
XMW0265 Tetradecane, 2,6,10-trimethyl- Hydrocarbons –
WMW0213 Heptane, 2,4-dimethyl- Hydrocarbons –
XMW0403 Nonane, 2,5-dimethyl- Hydrocarbons –
KMW0137 Nonane Hydrocarbons linseed, oily, oily, sweaty
KMW0306 Undecane Hydrocarbons alkane
KMW0551 Tetradecane Hydrocarbons mild, waxy
KMW0208 Decane Hydrocarbons alkane
XMW0420 Undecane, 2,9-dimethyl- Hydrocarbons –
XMW0253 Undecane, 5-methyl- Hydrocarbons –
XMW0373 Undecane, 2-methyl- Hydrocarbons –
XMW0367 Undecane, 2,4-dimethyl- Hydrocarbons –
XMW1065 Octane, 2,6,6-trimethyl- Hydrocarbons –
XMW0023 4-methyl-1-(1-methylethyl)-Bicyclo[3.1.0]hex-2-ene Hydrocarbons
–
XMW0884 5-Hexenal, 4-methylene- Hydrocarbons –
XMW0202 cis-2,6-Dimethyl-2,6-octadiene Hydrocarbons –
XMW0649 Nonane, 2,6-dimethyl- Hydrocarbons –
XMW0196 Decane, 4-methyl- Hydrocarbons pungent
WMW0082 1,10-Undecadiene Hydrocarbons –
XMW0499 Undecane, 3,4-dimethyl- Hydrocarbons –
XMW0243 Undecane, 2,5-dimethyl- Hydrocarbons –
WMW0145 Undecane, 4,6-dimethyl- Hydrocarbons –
XMW0110 Dodecane, 4,6-dimethyl- Hydrocarbons –
KMW0488 Tridecane Hydrocarbons alkane
w07 1H-Indene, 1-ethylidene- Hydrocarbons –
XMW0097 1,5-Cycloundecadiene, 8,8-dimethyl-9-methylene- Hydrocarbons –
KMW0046 2-Hexanone Ketone fruity, fungal, meaty, buttery
KMW0067 3-Penten-2-one, 4-methyl- Ketone pungent, earthy, vegetable,
acrylate
XMW0162 3-Penten-2-one, 4-(acetyloxy)-, (Z)- Ketone –
XMW0900 3-Cyclohexen-1-one, 3,5,5-trimethyl- Ketone –
XMW0637 Cyclobutanone, 2,2,3-trimethyl- Ketone –
KMW0176 5-Hepten-2-one, 6-methyl- Ketone herbal, green, citrus, musty,
lemon grass
D110 Bicyclo[3.1.1]heptan-3-one, 2-hydroxy-2,6,6-trimethyl- Ketone –
KMW0280 3,5-Octadien-2-one Ketone fruity, fatty, mushroom
XMW0648 3-Hexanone, 2,2-dimethyl- Ketone –
XMW0201 4-Hexen-3-one Ketone pungent, ethereal, spicy, green, tropical,
metallic
D340 3-Hexanone, 1-phenyl- Ketone –
XMW1378 4,6-Octadiyn-3-one, 2-methyl- Ketone –
WMW0205 2,5-Octanedione Ketone –
NMW0773 Cyclohexanone Ketone minty, acetone
D206 1,2-Cyclohexanedione Ketone sweet, acorn, nut skin, maple,
caramel, brothy
XMW0486 Cyclohexanone, 2,2,6-trimethyl- Ketone pungent, thujone,
labdanum, honey, cistus
D413 4-Methyl-5-nonanone Ketone –
XMW0008 Isophorone Ketone cool, woody, sweet, green, camphor, fruity,
musty, cedarwood, tobacco, leathery
NMW0070 1,2-Propanedione, 1-phenyl- Ketone plastic, buttery, honey
XMW0181 5-Hepten-2-one, 4,6-dimethyl- Ketone –
XMW0177 Ethanone, 1-(2-methyl-1-cyclopenten-1-yl)- Ketone –
w41 3-Octen-2-one, (E)- Ketone herbal, mushroom
KMW0230 3-Octen-2-one Ketone earthy, spicy, herbal, sweet, mushroom,
hay, blueberry
XMW0909 2,6,6-Trimethylbicyclo[3.2.0]hept-2-en-7-one Ketone –
NMW0040 Benzyl methyl ketone Ketone almond
XMW0583 Ethanone, 1-(3-hydroxyphenyl)- Ketone –
KMW0182 Furan, 2-pentyl- Heterocyclic compound fruity, green, earthy,
beany, vegetable, metallic
KMW0190 Pyrazine, trimethyl- Heterocyclic compound nut skin, earthy,
powdery, cocoa, baked, potato, roasted, peanut, hazelnut, musty
WMW0081 cis-2-(2-Pentenyl)furan Heterocyclic compound –
XMW0115 5-Methyloxazolidine Heterocyclic compound –
D81 2-Furanpropanoic acid, ethyl ester Heterocyclic compound pineapple,
fruity, spicy, jammy
NMW0201 Phenmetrazine Heterocyclic compound –
XMW0914 Ethanone, 1-(1H-pyrazol-4-yl)- Heterocyclic compound –
D188 Pyrazinamide Heterocyclic compound –
XMW0484 Furan, 2-propyl- Heterocyclic compound –
NMW0215 N,N-Dimethyl-1,2,3-trithian-5-Amine Heterocyclic compound –
XMW0132 Pyridine, 2,3,4,5-tetrahydro- Heterocyclic compound –
D191 2-Hexanoylfuran Heterocyclic compound sweet, fruity, ketonic,
green, apricot, peach
XMW0714 3-Acetyl-1H-pyrroline Heterocyclic compound roasted
XMW0533 3-Methylbenzothiophene Heterocyclic compound –
NMW0217 1H-Pyrrolizine-7-methanol, 2,3,5,7a-tetrahydro-1-hydroxy-,
(1S-cis)- Heterocyclic compound –
XMW0483 1H-Pyrrole-2-carboxAldehyde Heterocyclic compound musty, beefy,
coffee
XMW1208 1H-Tetrazole Heterocyclic compound –
XMW0532 1H-Pyrazole-1-carboximidamide, 3,5-dimethyl- Heterocyclic
compound –
KMW0425 Benzothiazole Heterocyclic compound meaty, vegetable, brown,
cooked, beefy, coffee
KMW0286 Pyrazine, 2-methoxy-3-(1-methylethyl)- Heterocyclic compound
beany, pea, earthy, chocolate, nutty
KMW0365 2-((3,3-Dimethyloxiran-2-yl)methyl)-3-methylfuran Heterocyclic
compound green, earthy, citrus
KMW0126 Pyrazine, 2,6-dimethyl- Heterocyclic compound ethereal, cocoa,
nutty, roasted, roasted, meaty, beefy, brown, coffee, buttermilky
XMW0412 3-Acetyl-2,5-dimethyl furan Heterocyclic compound sweet, musty,
nutty, earthy, cocoa, corn, leathery
KMW0266 2-Thiophenemethanethiol Heterocyclic compound roasted, coffee,
fishy
KMW0264 Pyrazine, 3-ethyl-2,5-dimethyl- Heterocyclic compound potato,
cocoa, roasted, nutty
XMW0445 6-Ethyl-5,6-dihydro-2H-pyran-2-one Heterocyclic compound –
KMW0097 2-Methyl-3-furanthiol Heterocyclic compound sulfury, meaty,
fishy, metallic
XMW0517 Thiophene, 3-ethyl- Heterocyclic compound styrene
XMW0444 1,2,4,5-Tetrazin-3-Amine Heterocyclic compound –
KMW0132 Pyrazine, 2,3-dimethyl- Heterocyclic compound nutty, nut skin,
cocoa, peanut, buttery, coffee, walnut, caramel, roasted
XMW0065 Fomepizole Heterocyclic compound –
XMW0289 2-Acetyl-5-methylfuran Heterocyclic compound strong, musty,
nutty, hay, coconut, coumarin, milky
XMW0051 4-Pyridinecarboxaldehyde Heterocyclic compound fruity
NMW0011 Benzofuran Heterocyclic compound aromatic
XMW0042 3H-1,2,4-Triazol-3-one, 1,2-dihydro- Heterocyclic compound –
XMW0267 2-Ethylpiperidine Heterocyclic compound –
XMW0076 1H-Pyrrole-3‑carbonitrile Heterocyclic compound –
KMW0240 Ethanone, 1-(1H-pyrrol-2-yl)- Heterocyclic compound musty, nut
skin, maraschino, cherry, coumarin, licorice, walnut, bread
XMW1203 2,5-Furandione, dihydro-3-methyl- Heterocyclic compound –
D364 2-Ethoxy-3-methylpyrazine Heterocyclic compound hazelnut, roasted,
almond, pineapple, earthy
XMW0168 3-Butylthiophene Heterocyclic compound –
XMW1429 1-(2-Hydroxyethyl)-1,2,4-triazole Heterocyclic compound –
XMW0644 1H-Imidazole, 2-propyl- Heterocyclic compound –
NMW0059 4-Aminopyridine Heterocyclic compound –
KMW0380 Pyrazine, 2-methoxy-3-(2-methylpropyl)- Heterocyclic compound
green bell pepper, pea, galbanum
XMW1317 8-Azabicyclo[3.2.1]octane, 3-chloro-8-methyl- Heterocyclic
compound –
NMW0110 Picolinamide Heterocyclic compound –
KMW0539 2(5H)-Furanone, 5-ethyl- Heterocyclic compound spice
D274 2H-1-Benzopyran-2-one, 3-methyl- Heterocyclic compound –
NMW0210 Furo[3,4-c]pyridin-1(3H)-one, 7-hydroxy-6-methyl- Heterocyclic
compound –
mws0366 γ-Linolenic Acid* Lipids –
NMW0758 1-Butanol, 3-methyl-, formate Ester plum, black currant,
ethereal, vinegar, dry earthy, fruity, green
NMW0016 Acetic acid, cyclohexyl ester Ester fruity, sweet, musty,
ethereal
KMW0568 2H-Pyran-2-one, tetrahydro-6-pentyl- Ester creamy, coconut,
fruity
XMW1401 n-Valeric acid cis-3-hexenyl ester Ester green, fruity, apple,
pear, kiwi, unripe, banana, tropical
XMW1240 Hexanoic acid, 2-methylbutyl ester Ester ethereal
KMW0557 Benzoic acid, 2-hydroxy-, ethyl ester Ester caramel,
pepperminty
KMW0373 Benzoic acid, ethyl ester Ester fruity, dry, musty, sweet,
wintergreen
KMW0605 Pentanoic acid, 1-ethenyl-1,5-dimethyl-4-hexenyl ester Ester
fruity, lavender, apricot, citrus
XMW0881 2-Butenoic acid, 3-methyl-, methyl ester Ester –
XMW1310 Isobutyl isovalerate Ester sweet, fruity, apple, raspberry,
green, banana
w32 Acetic acid, heptyl ester Ester fruity, green, sweet
XMW0803 Iso-3-thujyl acetate Ester –
KMW0449 Bicyclo[2.2.1]heptan-2-ol, 1,7,7-trimethyl-, formate, endo-
Ester green, earthy, herbal, balsamic, pine
XMW0933 Bicyclo[3.1.1]hept-2-en-6-ol, 2,7,7-trimethyl-, acetate,
[1S-(1.alpha.,5.alpha.,6.beta.)]- Ester –
XMW0180 2-Propenoic acid, 2-methoxyethyl ester Ester –
D112 Benzeneacetic acid, methyl ester Ester floral, honey, spice, waxy,
sweet
WMW0087 Butanoic Acid, 3-methylbutyl ester Ester fruity, green,
apricot, pear, banana
NMW0122 Geranyl formate Ester fresh, rose, neroli, tea, rose, green
XMW1308 1-Octyl trifluoroacetate Ester –
D240 Propanoic acid, 2,2-dimethyl-, pentyl ester Ester –
XMW0073 3-Methylheptyl acetate Ester –
D143 Benzenepropanoic acid, methyl ester Ester honey, fruity, wine,
balsamic, floral
w43 2-Oxepanone Ester –
NMW0037 Butanoic acid, 3-methyl-, 3-methylbutyl ester Ester sweet,
fruity, green, ripe apple, jammy, tropical
D271 Propanoic acid, hexyl ester Ester pear, green, fruity, musty,
rotten
D357 2-Propanol, 1-(dimethylamino)-, acetate (ester) Ester –
w29 4-Pentenyl Acetate Ester green, plastic, weedy, acrylate,
vegetable, metallic, cooked meat, sulfury
XMW0299 Butanoic acid, butyl ester Ester fruity, banana, pineapple,
green, cherry, tropical fruit, ripe fruit, juicy fruity
D417 3-Hexen-1-ol, acetate, (E)- Ester sharp, fruity, green, cortex,
hyacinth, narcissus, rummy, unripe banana, pear
WMW0210 2-Hexen-1-ol, acetate, (E)- Ester sweet, privet, green, fresh,
apple skin, banana, peel, waxy, apple
XMW1221 Acetic acid, (propylthio)-, methyl ester Ester –
D133 4-Heptanol, 2,6-dimethyl-, acetate Ester herbal, rhubarb, floral,
lilac, banana
D305 Butanoic acid, 2-methyl-, 3-methylbutyl ester Ester sweet, fruity,
citrus, cherry, blueberry, apple
XMW1127 Formic acid, octyl ester Ester fruity, rose, orange, waxy,
cucumber
XMW1071 Butanoic acid, cyclopentyl ester Ester –
KMW0350 Acetic acid, phenylmethyl ester Ester sweet, floral, fruity,
jasmin, fresh
XMW1079 Butanoic acid, 1-methylhexyl ester Ester fruity, green,
vegetable, cheese, walnut
XMW0213 Isopentyl hexanoate Ester fruity, banana, apple, pineapple,
green
KMW0411 1,6-Octadien-3-ol, 3,7-dimethyl-, formate Ester citrus, herbal,
bergamot, lavender, soapy, fatty, green, woody
KMW0421 Methyl salicylate Ester caramel, pepperminty
KMW0441 Benzeneacetic acid, ethyl ester Ester minty
XMW0937 (1R,5S,6R)-2,7,7-Trimethylbicyclo[3.1.1]hept-2-en-6-yl acetate
Ester –
D346 Methyl 6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carboxylate Ester –
KMW0585 Citronellyl isobutyrate Ester sweet, fruity, floral, geranium,
tropical
D158 2-Phenoxyethyl isobutyrate Ester green, fruity, waxy, apple,
nuances
KMW0610 Bornyl isovalerate Ester valerian, camphor, tropical
[108]Open in a new tab
Fig. 5.
[109]Fig. 5
[110]Open in a new tab
Pie chart of volatile metabolites(PC1 = 50.15 %,PC2 = 32.07 %); 5B PCA
score of volatile metabolites.
The PCA score plot of volatile metabolites showed ([111]Fig. 5B), BT
showed a significant separation from the other groups, suggesting that
the BT processing has a significant effect on the volatiles of EUL.
Additionally, HG was below the QC sample and also showed a tendency to
separate from the other groups, indicating that the volatile
metabolites were not as close to the GT group as the nonvolatile
metabolites, and these two groups still had differences in volatile
metabolites. However, GT and XY are very close to each other, this
suggests that the the GT process does not have much effect on the
volatiles.
Then, according to the table of significant volatile metabolites
([112]Table 5) of the two-by-two comparison groups (BT vs. XY, GT vs.
XY, HG vs. XY), it can be found that there are 12 categories of the
main significant volatiles, mainly esters, aldehydes, alcohols, ketones
and so on. After the BT processing, there were 14 volatile metabolites
with up-regulation multiples of 100 times or more, mainly focusing on
esters and aldehydes. 1-ethenyl-1,5-dimethyl-4-hexenyl ester, is
fruity, lavender, apricot, citrusy. Methyl salicylate in it is the
aroma component of black tea in general. It is obtained by enzymatic
hydrolysis of glycoside aroma precursors in the leaf tissue after
twisting. Similarly, there is up-regulation of benzoic acid as well as
pyrazines and pyridines, which are aroma components contained in black
tea processing. Both the GT process and HG caused a decrease in methyl
salicylate. Thermal cleavage and esterification reactions of the GT
processing resulted in the up-regulation of 11 substances, mainly
heterocyclic compounds. There are 19 substances with significant upward
adjustments for the HG, mainly esters and alcohols. Secondary
metabolites alcohols, aldehydes, etc. may be produced as a result of
the degradation of lipids which then undergo further oxidation
([113]Shahidi & Hossain, 2022). It is speculated that the enzyme
activity affects the rise of volatile components because the GT process
is killed and the enzyme is inactivated due to high temperature. While
the other two processes have the participation of enzymes, the main
mechanism has to be further investigated.
Table 5.
Table of major differences in composition between groups of volatile
metabolites of different processed EUL.
Index Compounds Class I Odor BT_vs_XY_Type GT_vs_XY_Type HG_vs_XY_Type
KMW0182 Furan, 2-pentyl- Heterocyclic compound fruity, green, earthy,
beany, vegetable, metallic – – –
KMW0386 cis-Dihydrocarvone Terpenoids herbal, warm down down down
NMW0057 Glutarimide Amine – – – down
KMW0190 Pyrazine, trimethyl- Heterocyclic compound nut skin, earthy,
powdery, cocoa, baked, potato, roasted, peanut, hazelnut, musty – down
down
WMW0081 cis-2-(2-Pentenyl)furan Heterocyclic compound – up down down
NMW0758 1-Butanol, 3-methyl-, formate Ester plum, black currant,
ethereal, vinegar, dry earthy, fruity, green down down down
KMW0556 Naphthalene,
decahydro-4a-methyl-1-methylene-7-(1-methylethenyl)-,
[4aR-(4a.alpha.,7.alpha.,8a.beta.)]- Terpenoids herbal – down down
KMW0296 Cyclohexene, 1-methyl-4-(1-methylethylidene)- Terpenoids
citrus, pine – down down
XMW0735 Benzenemethanol, .alpha.-2-propenyl- Alcohol – down down down
KMW0046 2-Hexanone Ketone fruity, fungal, meaty, buttery down down down
w08 Naphthalene, 1-methyl- Aromatics naphthyl, chemical, medicinal,
camphor – – down
NMW0016 Acetic acid, cyclohexyl ester Ester fruity, sweet, musty,
ethereal – down down
NMW0093 D-Verbenone Terpenoids – up down down
KMW0606 .alpha.-Muurolene Terpenoids woody – down down
XMW0916 (5-bromopentyl)-Benzene Aromatics – – down down
XMW0422 3,5-Dimethyldodecane Hydrocarbons – – down –
KMW0568 2H-Pyran-2-one, tetrahydro-6-pentyl- Ester creamy, coconut,
fruity – down down
XMW0115 5-Methyloxazolidine Heterocyclic compound – down down down
KMW0067 3-Penten-2-one, 4-methyl- Ketone pungent, earthy, vegetable,
acrylate down down down
XMW0162 3-Penten-2-one, 4-(acetyloxy)-, (Z)- Ketone – – – up
XMW0900 3-Cyclohexen-1-one, 3,5,5-trimethyl- Ketone – down down down
XMW1138 6-Octen-1-ol, 7-methyl-3-methylene- Terpenoids – down down down
D81 2-Furanpropanoic acid, ethyl ester Heterocyclic compound pineapple,
fruity, spicy, jammy down down down
XMW1401 n-Valeric acid cis-3-hexenyl ester Ester green, fruity, apple,
pear, kiwi, unripe, banana, tropical down down down
NMW0101 Ascaridole Terpenoids – down down down
XMW1240 Hexanoic acid, 2-methylbutyl ester Ester ethereal down down
down
KMW0435 2-Decenal, (Z)- Aldehyde tallow – – up
D266 1-Tridecene Hydrocarbons – – down down
XMW0615 Phenol, m-tert-butyl- Phenol – – down down
KMW0557 Benzoic acid, 2-hydroxy-, ethyl ester Ester caramel,
pepperminty up down down
KMW0570 2-Dodecenal, (E)- Aldehyde citrus, metallic, mandarin, orange,
waxy, aldehydic up up –
NMW0201 Phenmetrazine Heterocyclic compound – up up –
D265 Dodecanenitrile Nitrogen compounds citrus, orange, peel, metallic,
spicy – down down
KMW0068 3-Hexenal, (Z)- Aldehyde green, fatty, grassy, weedy, fruity,
apple down down down
KMW0079 Octane Hydrocarbons gasoline down down down
KMW0066 Hexanal Aldehyde aldehyde, grassy, green, leafy, vinegar down
down down
KMW0217 d-Limonene Terpenoids citrus – – down
XMW0771 1,5-Cyclooctadiene, 3,4-dimethyl- Hydrocarbons – up down down
XMW0914 Ethanone, 1-(1H-pyrazol-4-yl)- Heterocyclic compound – down
down down
KMW0373 Benzoic acid, ethyl ester Ester fruity, dry, musty, sweet,
wintergreen up down down
D188 Pyrazinamide Heterocyclic compound – down down down
KMW0605 Pentanoic acid, 1-ethenyl-1,5-dimethyl-4-hexenyl ester Ester
fruity, lavender, apricot, citrus up – –
XMW0637 Cyclobutanone, 2,2,3-trimethyl- Ketone – down down down
WMW0187 2-Hexanol Alcohol chemical, winey, fruity, fatty, terpenic,
cauliflower down down down
XMW0279 E-1-Methoxy-4-hexene Hydrocarbons – down down down
XMW0484 Furan, 2-propyl- Heterocyclic compound – down down down
XMW0881 2-Butenoic acid, 3-methyl-, methyl ester Ester – down down down
XMW1118 CyclohexanecarboxAldehyde Aldehyde – up – –
KMW0176 5-Hepten-2-one, 6-methyl- Ketone herbal, green, citrus, musty,
lemon grass up up –
XMW0006 (+)-3-Carene Terpenoids sweet down down down
XMW0121 1-Nonene, 4,6,8-trimethyl- Hydrocarbons – – down down
WMW0126 1,3-Hexadiene, 3-ethyl-2-methyl- Hydrocarbons nutty – – –
w32 Acetic acid, heptyl ester Ester fruity, green, sweet – down up
XMW0803 Iso-3-thujyl acetate Ester – – down down
NMW0215 N,N-Dimethyl-1,2,3-trithian-5-Amine Heterocyclic compound – –
down down
XMW0294 10-Undecenal Aldehyde waxy, aldehydic, rose, mandarin, citrus,
soapy, fatty – down down
XMW0132 Pyridine, 2,3,4,5-tetrahydro- Heterocyclic compound – – – up
D373 2,4-Heptadien-1-ol, (E,E)- Alcohol green, fruity, nutty, cheese up
up up
NMW0041 (E)-4,8-Dimethylnona-1,3,7-triene Terpenoids – up – –
XMW0255 BenzAldehyde, 2,4-dimethyl- Aldehyde naphthyl, cherry, almond,
spice, vanilla up – –
D191 2-Hexanoylfuran Heterocyclic compound sweet, fruity, ketonic,
green, apricot, peach down down down
D110 Bicyclo[3.1.1]heptan-3-one, 2-hydroxy-2,6,6-trimethyl- Ketone – –
– –
KMW0449 Bicyclo[2.2.1]heptan-2-ol, 1,7,7-trimethyl-, formate, endo-
Ester green, earthy, herbal, balsamic, pine up down down
XMW0159 2,6,10-Trimethyltridecane Hydrocarbons – up up –
KMW0595 1,3-Cyclohexadiene, 5-(1,5-dimethyl-4-hexenyl)-2-methyl-,
[S-(R*,S*)]- Terpenoids spice, fresh, sharp – down down
KMW0604
(1S,2E,6E,10R)-3,7,11,11-Tetramethylbicyclo[8.1.0]undeca-2,6-diene
Terpenoids green, woody, weedy – down down
XMW0714 3-Acetyl-1H-pyrroline Heterocyclic compound roasted – down down
D197 3-Oxatricyclo[4.1.1.0(2,4)]octane, 2,7,7-trimethyl- Terpenoids
green – down down
KMW0280 3,5-Octadien-2-one Ketone fruity, fatty, mushroom up – –
XMW0933 Bicyclo[3.1.1]hept-2-en-6-ol, 2,7,7-trimethyl-, acetate,
[1S-(1.alpha.,5.alpha.,6.beta.)]- Ester – up – down
XMW0533 3-Methylbenzothiophene Heterocyclic compound – down down –
NMW0104 2,6-Octadien-1-ol, 3,7-dimethyl- Terpenoids – – – –
D356 3-Methoxy-5-methylphenol Phenol oakmoss, fruity, iodine, woody,
hay – down down
NMW0217 1H-Pyrrolizine-7-methanol, 2,3,5,7a-tetrahydro-1-hydroxy-,
(1S-cis)- Heterocyclic compound – – down down
XMW0180 2-Propenoic acid, 2-methoxyethyl ester Ester – down down down
KMW0102 1-Hexanol Alcohol ethereal, fusel, oily, fruity, alcoholic,
sweet, green – down down
XMW0648 3-Hexanone, 2,2-dimethyl- Ketone – up down down
XMW0483 1H-Pyrrole-2-carboxAldehyde Heterocyclic compound musty, beefy,
coffee down down down
XMW1208 1H-Tetrazole Heterocyclic compound – down down down
WMW0040 trans-.beta.-Ocimene Terpenoids sweet, herbal up down –
XMW0659 Benzene, n-butyl- Aromatics – up down up
NMW0034 Fenchone Terpenoids herbal, cedar leaf, bitter, thuja, camphor,
earthy, woody down down down
XMW0532 1H-Pyrazole-1-carboximidamide, 3,5-dimethyl- Heterocyclic
compound – down down down
XMW0099 Decane, 2,3,5-trimethyl- Hydrocarbons – – down down
XMW0913 cis-Chrysanthenol Terpenoids – – – down
D112 Benzeneacetic acid, methyl ester Ester floral, honey, spice, waxy,
sweet up down down
XMW0089 4-Decenal, (E)- Aldehyde fresh, aldehydic, citrus, orange,
mandarin, tangerine, green, fatty down down down
D355 2,6-Octadienenitrile, 3,7-dimethyl-, (Z)- Nitrogen compounds
citral, lemon, aldehydic, metallic up down down
KMW0425 Benzothiazole Heterocyclic compound meaty, vegetable, brown,
cooked, beefy, coffee – down down
KMW0453 Linalyl acetate Terpenoids sweet, green, citrus, bergamot,
lavender, woody down down down
w02 2,4-Decadien-1-ol Alcohol fatty, waxy, citrus, melon up – down
KMW0526 2-Buten-1-one, 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-,
(E)- Terpenoids apple, rose, honey, tobacco, sweet – down down
XMW0265 Tetradecane, 2,6,10-trimethyl- Hydrocarbons – – down down
KMW0060 Toluene Aromatics sweet – – up
WMW0213 Heptane, 2,4-dimethyl- Hydrocarbons – up up –
KMW0092 2-Furanmethanol Alcohol alcoholic, chemical, musty, sweet,
caramel, bread, coffee down down down
KMW0088 2-Hexenal, (E)- Aldehyde green, grassy – down down
XMW0201 4-Hexen-3-one Ketone pungent, ethereal, spicy, green, tropical,
metallic down down down
KMW0175 Phenol Phenol phenol, medicinal – – down
KMW0323 Benzyl Alcohol Alcohol floral, rose, phenol, balsamic up down
down
WMW0127 3-Octen-1-ol, (Z)- Alcohol fresh, fatty, grassy, melon, green,
cortex, herbal, earthy, fusel, spicy – down –
KMW0286 Pyrazine, 2-methoxy-3-(1-methylethyl)- Heterocyclic compound
beany, pea, earthy, chocolate, nutty down down down
KMW0365 2-((3,3-Dimethyloxiran-2-yl)methyl)-3-methylfuran Heterocyclic
compound green, earthy, citrus down down down
KMW0404 Naphthalene Aromatics pungent, dry, tarry down down down
XMW0790 6,7-Dimethyl-1,2,3,5,8,8a-hexahydronaphthalene Aromatics – up
down down
WMW0069 2-Propenal, 3-phenyl- Aldehyde sweet, spicy, aldehydic,
aromatic, balsamic, cinnamyl, resinous, honey, powdery up – down
NMW0122 Geranyl formate Ester fresh, rose, neroli, tea, rose, green –
down down
D340 3-Hexanone, 1-phenyl- Ketone – – – down
KMW0582 .beta.-Guaiene Terpenoids sweet, woody, dry, guaiacwood, spicy,
powdery – down down
WMW0227 Benzene, 1,4-dichloro- Aromatics – down down down
XMW1378 4,6-Octadiyn-3-one, 2-methyl- Ketone – down down down
D240 Propanoic acid, 2,2-dimethyl-, pentyl ester Ester – – – up
XMW0073 3-Methylheptyl acetate Ester – up – up
XMW0269 2-Methylbutanoic anhydride Others – down down down
NMW0075 Cyclohexanol, 1-methyl-4-(1-methylethylidene)- Terpenoids
terpineol, lilac up down down
XMW0246 OxiranecarboxAldehyde, 3-methyl-3-(4-methyl-3-pentenyl)-
Aldehyde – up down down
NMW0113 6-Octen-1-ol, 3,7-dimethyl-, formate Terpenoids bergamot,
cucumber, rose, apricot, peach, plum down down down
D143 Benzenepropanoic acid, methyl ester Ester honey, fruity, wine,
balsamic, floral up – down
NMW0209 Undecylenic Acid Acid sweet, woody – down down
WMW0205 2,5-Octanedione Ketone – up – –
NMW0773 Cyclohexanone Ketone minty, acetone – – –
KMW0137 Nonane Hydrocarbons linseed, oily, oily, sweaty – – up
KMW0126 Pyrazine, 2,6-dimethyl- Heterocyclic compound ethereal, cocoa,
nutty, roasted, roasted, meaty, beefy, brown, coffee, buttermilky – up
–
KMW0194 2-Octanol Alcohol fresh, spicy, green, woody, herbal, earthy –
up up
KMW0243 (E)-2-Octenal Aldehyde fresh, cucumber, fatty, green, herbal,
banana, waxy, leafy down down –
D206 1,2-Cyclohexanedione Ketone sweet, acorn, nut skin, maple,
caramel, brothy – down down
KMW0254 1,5-Heptadien-4-one, 3,3,6-trimethyl- Terpenoids herbal, honey,
minty, berry – down down
XMW0412 3-Acetyl-2,5-dimethyl furan Heterocyclic compound sweet, musty,
nutty, earthy, cocoa, corn, leathery – down down
KMW0306 Undecane Hydrocarbons alkane – down down
KMW0355 trans,cis-2,6-Nonadien-1-ol Alcohol green, cucumber, oily,
violet, leafy down down down
XMW0711 Formamide, N-phenyl- Amine – up down down
XMW0424 2,6-Dimethyl-1-nonen-3-yn-5-ol Alcohol – – down down
KMW0479 1,3-Cyclohexadiene-1-carboxaldehyde, 2,6,6-trimethyl-
Terpenoids fresh, herbal, phenol, metallic, rosemary, tobacco, spicy up
– –
KMW0551 Tetradecane Hydrocarbons mild, waxy – down down
KMW0629 1-Dodecanol Alcohol earthy, soapy, waxy, fatty, honey, coconut
up up –
XMW0420 Undecane, 2,9-dimethyl- Hydrocarbons – down down down
w43 2-Oxepanone Ester – – down –
KMW0266 2-Thiophenemethanethiol Heterocyclic compound roasted, coffee,
fishy – – –
KMW0264 Pyrazine, 3-ethyl-2,5-dimethyl- Heterocyclic compound potato,
cocoa, roasted, nutty up up –
XMW0445 6-Ethyl-5,6-dihydro-2H-pyran-2-one Heterocyclic compound – down
down down
XMW0486 Cyclohexanone, 2,2,6-trimethyl- Ketone pungent, thujone,
labdanum, honey, cistus up down down
D413 4-Methyl-5-nonanone Ketone – – – up
WMW0194 Thujone Terpenoids cedar leaf – down down
NMW0037 Butanoic acid, 3-methyl-, 3-methylbutyl ester Ester sweet,
fruity, green, ripe apple, jammy, tropical – – –
D94 Benzenemethanethiol Sulfur compounds sharp, alliaceous, onion,
sulfury, garlic, horseradish, minty, coffee – down down
D401 2-Isopropyl-5-methylhex-2-enal Aldehyde herbal, lavender, woody,
green, blueberry, tomato – – –
D271 Propanoic acid, hexyl ester Ester pear, green, fruity, musty,
rotten – – –
XMW0008 Isophorone Ketone cool, woody, sweet, green, camphor, fruity,
musty, cedarwood, tobacco, leathery – down down
XMW0253 Undecane, 5-methyl- Hydrocarbons – down down down
XMW0373 Undecane, 2-methyl- Hydrocarbons – – down down
KMW0344 1-Nonanol Alcohol fresh, clean, fatty, floral, rose, orange,
dusty, wet, oily down down down
XMW0170 BenzAldehyde, 3-ethyl- Aldehyde – up down down
XMW1072 (E)-2,6-Dimethylocta-5,7-dien-2-ol Alcohol – down down down
NMW0070 1,2-Propanedione, 1-phenyl- Ketone plastic, buttery, honey up
down down
KMW0407 2,4-Nonadienal, (E,E)- Aldehyde fatty, melon, waxy, green,
violet, leafy, cucumber, tropical, fruity, chicken up down down
NMW0087 2-Oxabicyclo[2.2.2]octan-6-one, 1,3,3-trimethyl- Terpenoids –
up down down
XMW0526 AcetAldehyde, (3,3-dimethylcyclohexylidene)-, (Z)- Aldehyde –
up down down
KMW0123 4-Heptenal, (Z)- Aldehyde oily, fatty, green, dairy, milky,
creamy – – –
KMW0122 Heptanal Aldehyde fresh, aldehydic, fatty, green, herbal, wine,
ozonous – – –
XMW1471 1-ButanAmine, N-methyl-N-2-propenyl- Amine – down down down
XMW0517 Thiophene, 3-ethyl- Heterocyclic compound styrene down down
down
KMW0098 3-Hexen-1-ol, (Z)- Alcohol fresh, green, grass, foliage,
vegetable, herbal, oily – down down
D357 2-Propanol, 1-(dimethylamino)-, acetate (ester) Ester – up down
down
KMW0096 Butanoic Acid, 3-methyl- Acid sour, stinky, feet, sweaty,
cheese, tropical down down down
XMW0023 4-methyl-1-(1-methylethyl)-Bicyclo[3.1.0]hex-2-ene Hydrocarbons
– up – –
XMW0444 1,2,4,5-Tetrazin-3-Amine Heterocyclic compound – – – –
KMW0132 Pyrazine, 2,3-dimethyl- Heterocyclic compound nutty, nut skin,
cocoa, peanut, buttery, coffee, walnut, caramel, roasted – down down
KMW0115 Styrene Aromatics penetrating, balsamic, gasoline down down
down
w29 4-Pentenyl Acetate Ester green, plastic, weedy, acrylate,
vegetable, metallic, cooked meat, sulfury – down –
XMW0884 5-Hexenal, 4-methylene- Hydrocarbons – – down –
XMW1307 Cyclohexanol, 1-methyl- Alcohol – – – –
KMW0129 2,4-Hexadienal, (E,E)- Aldehyde sweet, green, spicy, floral,
citrus – – up
XMW0065 Fomepizole Heterocyclic compound – down down down
KMW0158 BenzAldehyde Aldehyde sweet, bitter, almond, cherry up – –
XMW0289 2-Acetyl-5-methylfuran Heterocyclic compound strong, musty,
nutty, hay, coconut, coumarin, milky – down down
XMW0181 5-Hepten-2-one, 4,6-dimethyl- Ketone – up down down
XMW0642 Cyclohexanol, 3,5-dimethyl- Alcohol – down down –
KMW0162 Dimethyl triSulfur compounds Sulfur compounds sulfury, cooked
onion, savory, meaty down – –
XMW0051 4-Pyridinecarboxaldehyde Heterocyclic compound fruity up – –
XMW0299 Butanoic acid, butyl ester Ester fruity, banana, pineapple,
green, cherry, tropical fruit, ripe fruit, juicy fruity – – –
XMW0202 cis-2,6-Dimethyl-2,6-octadiene Hydrocarbons – – down down
XMW0434 4-Hexen-1-ol, acetate Alcohol – down down down
XMW0177 Ethanone, 1-(2-methyl-1-cyclopenten-1-yl)- Ketone – – down down
WMW0103 2-Cyclopentylethanol Alcohol – down down down
NMW0011 Benzofuran Heterocyclic compound aromatic – up –
D417 3-Hexen-1-ol, acetate, (E)- Ester sharp, fruity, green, cortex,
hyacinth, narcissus, rummy, unripe banana, pear down down down
WMW0210 2-Hexen-1-ol, acetate, (E)- Ester sweet, privet, green, fresh,
apple skin, banana, peel, waxy, apple up down down
NMW0013 Benzylamine Amine – down down down
w41 3-Octen-2-one, (E)- Ketone herbal, mushroom – down down
XMW1221 Acetic acid, (propylthio)-, methyl ester Ester – up down down
WMW0215 .beta.-Ocimene Terpenoids apple, pear, fruity up down down
KMW0230 3-Octen-2-one Ketone earthy, spicy, herbal, sweet, mushroom,
hay, blueberry up down down
XMW0076 1H-Pyrrole-3‑carbonitrile Heterocyclic compound – up down up
KMW0240 Ethanone, 1-(1H-pyrrol-2-yl)- Heterocyclic compound musty, nut
skin, maraschino, cherry, coumarin, licorice, walnut, bread down down
down
D387 1-Hexanol, 3,5,5-trimethyl- Alcohol grassy, green, weedy, floral,
earthy, aldehydic, hay, straw, leafy – – –
XMW0196 Decane, 4-methyl- Hydrocarbons pungent up – up
NMW0022 Benzenemethanol, .alpha.-methyl- Alcohol fresh, sweet,
gardenia, hyacinth – down down
D364 2-Ethoxy-3-methylpyrazine Heterocyclic compound hazelnut, roasted,
almond, pineapple, earthy down down down
KMW0276 1-Octanol Alcohol intense citrus, rose down down up
WMW0082 1,10-Undecadiene Hydrocarbons – – down down
WMW0092 1-OctanAmine,N-methyl- Amine – – down down
D133 4-Heptanol, 2,6-dimethyl-, acetate Ester herbal, rhubarb, floral,
lilac, banana – down down
XMW0168 3-Butylthiophene Heterocyclic compound – – down down
XMW1429 1-(2-Hydroxyethyl)-1,2,4-triazole Heterocyclic compound – –
down down
XMW0644 1H-Imidazole, 2-propyl- Heterocyclic compound – – down down
D407 7-Octen-4-ol, 2-methyl-6-methylene-, (S)- Terpenoids – – down down
KMW0291 Linalool Terpenoids floral, green – down down
D305 Butanoic acid, 2-methyl-, 3-methylbutyl ester Ester sweet, fruity,
citrus, cherry, blueberry, apple – – –
XMW1233 3-Cyclopentyl-1-propanol Alcohol – up – –
XMW0410 1-Nonen-4-ol Alcohol – up – –
KMW0294 2-Octen-1-ol, (E)- Alcohol green, citrus, vegetable, fatty down
down up
NMW0038 Benzenemethanol, 4-methyl- Alcohol mild, floral – down down
D98 Benzene, (methylthio)- Sulfur compounds toluene, solvent, spicy,
woody, sawdust – – –
XMW0909 2,6,6-Trimethylbicyclo[3.2.0]hept-2-en-7-one Ketone – up – –
XMW1127 Formic acid, octyl ester Ester fruity, rose, orange, waxy,
cucumber – down up
KMW0307 Benzene, 1-methyl-4-(1-methylethenyl)- Aromatics phenol, spicy,
clove, guaiacol – down down
KMW0312 Furan, 3-(4-methyl-3-pentenyl)- Terpenoids woody – down down
XMW1071 Butanoic acid, cyclopentyl ester Ester – – – up
XMW0780 2,6-Dimethyl-1,3,5,7-octatetraene, E,E- Terpenoids – – down
down
KMW0343 2-Nonenal Aldehyde fatty, green, waxy, cucumber, melon – down
down
NMW0059 4-Aminopyridine Heterocyclic compound – down down down
XMW0679 AcetAldehyde, tetramer Aldehyde – down – down
KMW0350 Acetic acid, phenylmethyl ester Ester sweet, floral, fruity,
jasmin, fresh up down down
KMW0361 BenzAldehyde, 4-ethyl- Aldehyde bitter, almond, sweet, anisic
up – –
XMW0539 3,4-Dimethoxytoluene Aromatics – up down down
XMW0542 1-Cyclohexene-1-carboxaldehyde, 4-(1-methylethyl)- Terpenoids –
up down down
XMW0499 Undecane, 3,4-dimethyl- Hydrocarbons – down down down
XMW0675 2,6,6-Trimethylcyclohexa-1,4-dienecarbAldehyde Aldehyde – up
down down
KMW0380 Pyrazine, 2-methoxy-3-(2-methylpropyl)- Heterocyclic compound
green bell pepper, pea, galbanum down down down
KMW0376 2-Nonanol Alcohol rose up – –
WMW0145 Undecane, 4,6-dimethyl- Hydrocarbons – down down down
KMW0388 Carveol Terpenoids minty, spearmint, cool, green, herbal,
caraway, spicy up down down
XMW0766 Cyclohexanone, 5-methyl-2-(1-methylethylidene)- Terpenoids
minty – down down
XMW0213 Isopentyl hexanoate Ester fruity, banana, apple, pineapple,
green down down down
XMW1317 8-Azabicyclo[3.2.1]octane, 3-chloro-8-methyl- Heterocyclic
compound – up down down
KMW0411 1,6-Octadien-3-ol, 3,7-dimethyl-, formate Ester citrus, herbal,
bergamot, lavender, soapy, fatty, green, woody up down down
XMW0545 Benzenemethanamine, N-(1-methylethyl)- Amine – up down down
XMW0189 3-Cyclohexene-1-acetAldehyde, .alpha.,4-dimethyl- Aldehyde
spicy, herbal up down –
KMW0421 Methyl salicylate Ester caramel, pepperminty up down down
XMW0762 Imidodicarbonic diamide Nitrogen compounds – down down down
XMW1464 Benzene, (butoxymethyl)- Ether floral, rose up – down
XMW0583 Ethanone, 1-(3-hydroxyphenyl)- Ketone – up down down
XMW0791 Phenol, 4-methyl-2-nitro- Phenol – down down down
KMW0441 Benzeneacetic acid, ethyl ester Ester minty – – down
XMW0937 (1R,5S,6R)-2,7,7-Trimethylbicyclo[3.1.1]hept-2-en-6-yl acetate
Ester – up – down
NMW0110 Picolinamide Heterocyclic compound – up down down
NMW0112 Phenol, 2-(1,1-dimethylethyl)- Phenol – up – down
XMW0110 Dodecane, 4,6-dimethyl- Hydrocarbons – – down down
KMW0475 (2E,4Z)-2,4-Decadienal Aldehyde fried, fatty, geranium, green,
waxy – down down
KMW0488 Tridecane Hydrocarbons alkane – down down
D346 Methyl 6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carboxylate Ester –
– down down
w07 1H-Indene, 1-ethylidene- Hydrocarbons – – – down
XMW0041 Benzene, 1,2-dimethoxy-4-(1-propenyl)- Aromatics spicy, clove,
blossom, carnation, woody – down down
KMW0539 2(5H)-Furanone, 5-ethyl- Heterocyclic compound spice – – –
D274 2H-1-Benzopyran-2-one, 3-methyl- Heterocyclic compound – – down
down
WMW0003 Eremophilene Terpenoids – – down down
NMW0210 Furo[3,4-c]pyridin-1(3H)-one, 7-hydroxy-6-methyl- Heterocyclic
compound – – down down
XMW0097 1,5-Cycloundecadiene, 8,8-dimethyl-9-methylene- Hydrocarbons –
– down down
KMW0585 Citronellyl isobutyrate Ester sweet, fruity, floral, geranium,
tropical – down down
KMW0588 3-Cyclohexene-1-ethanol, .beta.,4-dimethyl- Alcohol fruity,
herbal – down down
D158 2-Phenoxyethyl isobutyrate Ester green, fruity, waxy, apple,
nuances – down down
XMW0548 Bicyclo[7.2.0]undecane, 10,10-dimethyl-2,6-bis(methylene)-,
[1S-(1R*,9S*)]- Terpenoids – – down down
WMW0007
[1S-(1.alpha.,7.alpha.,8a.beta.)]-1,2,3,5,6,7,8,8a-octahydro-1,4-dimeth
yl-7-(1-methylethenyl)-Azulene Terpenoids – up – –
XMW0817
(1S,5S,6R)-6-Methyl-2-methylene-6-(4-methylpent-3-en-1-yl)bicyclo[3.1.1
]heptane Terpenoids – – down down
D328
(5R,10R)-10-Methyl-6-methylene-2-(propan-2-ylidene)spiro[4.5]dec-7-ene
Terpenoids – – down down
KMW0610 Bornyl isovalerate Ester valerian, camphor, tropical – down
down
XMW0157
(2R,3R,6S)-6-Isopropyl-3-methyl-2-(prop-1-en-2-yl)-3-vinylcyclohexanone
Terpenoids – – down down
[114]Open in a new tab
3.5. Flavoromics analysis
Radar plotting (Fig. S4) for flavor characterization of differential
metabolites using one-to-one comparisons of the detected volatile
fractions. The top 10 sensory flavors with the highest number of
annotations were selected for plotting, with green, fruity, and sweet
being the three standout flavors. This is consistent with the results
of this experiment tasted by the panelists, where 4 samples tasted of a
strong grassy flavor.
Further combining the differential metabolite flavor wheels for each
comparison group (Fig.S5), there were 21 major differential metabolites
for green flavor in BT vs. XY, 36 in GT vs. XY, and 33 in HG vs. XY.
Hexanal dominated the grassy flavor in GT, while BT exhibited higher
methyl salicylate, a marker for floral notes. This aligns with
Aspergillus spp.-mediated esterification in dark tea fermentation. It
shows that the BT processing is able to relatively reduce the
generation of green flavor, and the GT process has the strongest green
flavor. The study by [115]Hu et al. (2020) showed that hexanal is
capable of producing grassy and green odor at a low threshold, which is
one of the volatiles responsible for the green odor in EUL. The next
comparison was for fruity flavors, with 18 fruity key differentiators
for BT vs. XY; 24 for GT vs. XY; and 25 for HG vs. XY. This suggests
that the BT process does not add fruity flavors well, while the HG/GT
treatments are more capable. Lastly, the sweetness comparison shows
that the HG treatment is not very different from the GT treatment in
terms of the level of sweetness, while the BT treatment will be a
little less sweet.
The top 10 sensory flavors with the highest number of annotations were
selected for Sankey map (Fig. S6) based on screening criteria for each
of the difference comparison groups. The differential volatile
metabolites of the two groups, GT vs. XY and HG vs. XY, showed a
significant downward trend. Whereas the BT vs. XY groups showed a
partial upward trend, proving once again that the the BT process is
capable of stimulating the production of flavor volatiles. The BT vs.
GT and BT vs. HG showed a trend of significant metabolite
up-regulation, while GT vs. HG showed partial up-regulation.
3.6. KEGG enrichment analysis of differential metabolites from EUL with
different processing methods
After enrichment analysis of differential metabolites in comparative
groups of EUL with different processing methods, the KEGG database was
further used to characterize the partitioning of these compounds in
different pathways ([116]Fig. 6). As [117]Fig. 6, the differential
metabolites of EUL under different processing methods were mainly
involved in 43 different metabolic pathways, and the common pathways
involved were, zeatin biosynthesis, plant hormone signal transduction,
and α-linolenic acid metabolism. The differences in metabolic responses
between the different treatment groups were mainly in the pathways
related to amino acid metabolism, further confirming the substantial
effects of different processing on the individual components of EUL. In
the spectrum of metabolic pathways. The differences in metabolic
responses between BT vs XY are mainly in glucosinolate biosynthesis,
2-0xocarboxylic acid metabolism, purine metabolism, phenylalanine
metabolism, aminoacyl- tRNA biosynthesis and other related pathways.
The metabolic pathways expressed in GT vs XY were: alpha-linolenic acid
metabolism, flavonoid biosynthesis, linoleic acid metabolism, plant
hormone signal transduction, folate biosynthesis. The main metabolic
pathways enriched in HG vs XY were nucleotide metabolism, purine
metabolism, aminoacyl-tRNA biosynthesis, alpha-Linolenic acid
metabolism, and ABC. Overall, KEGG enrichment analysis revealed that
different processing methods significantly affected pathways such as
amino acid metabolism (ko00270), flavonoid biosynthesis (ko00941), and
lipid oxidation (ko00591) ([118]Fig. 6A).The HG process
(low-temperature drying) significantly upregulated essential amino
acids (e.g., phenylalanine, histidine) ([119]Table 3), likely due to
enhanced proteolytic enzyme activity during drying ([120]Maeda &
Dudareva, 2012). In contrast, amino acid reduction in BT (black tea
processing) may result from microbial consumption during fermentation
to generate volatiles (e.g., methyl salicylate) ([121]LUO, et al.,
2021. GT (green tea processing) increased catechins but degraded
antioxidant flavonoids (e.g., quercetin) due to high-temperature
inactivation of oxidative enzymes ([122]Rigling et al., 2021). The
widespread downregulation of flavonoids in BT ([123]Fig. 4A) correlates
with PPO-mediated oxidation and polymerization ([124]Dongqing, 2001).
Hydroxylated fatty acids in BT ([125]Table 3) may arise from microbial
β-oxidation during fermentation, while lysophospholipid enrichment in
HG could stem from thermal degradation of triglycerides ([126]Maeda &
Dudareva, 2012).the different metabolic pathways mainly control the
metabolism of bioactive compounds (e.g., amino acids, phenolic acids,
flavonoids, nucleotides, lipids, monosaccharides, carbohydrates, and
alkaloids), in agreement with the observation of differential
compounds.
Fig. 6.
[127]Fig. 6
[128]Open in a new tab
Bubble diagram for KEGG pathway enrichment analysis (A: BT vs. XY; B:
GT vs. XY; C: HG vs. XY).
4. Conclusion
A broadly targeted metabolomics approach was used to identify and
analyze metabolites from fresh EUL (XY), traditionally dried EUL (HG),
green tea processed EUL (GT), and black tea processed EUL (BT). A total
of 1839 non-volatile metabolites (including 12 subclasses) and 289
volatile metabolites (including 16 subclasses) were identified and
detected. A total of 1503 differential compounds, consisting mainly of
amino acids, lipids, phenolic acids, flavonoids, nucleotides,
terpenoids and alkaloids, were observed in the different comparison
groups. BT processing significantly reduced the content of amino acids,
but enriched the content of various secondary metabolites (e.g.
phenolic acids, organic acids, flavonoids, monosaccharides, and
alkaloids) at the EUL level. GT processing, on the other hand, is
significantly downregulated in the presence of lipids, but the high
levels are concentrated in substances such as flavonoids, phenolic
acids, and tannins. HG processing makes amino acids, lipids, etc. more
upregulated and also retains some of the original substances in XY very
well. Overall, different processing methods for EUL functionality,
value and other aspects can each have their own advantages, to improve
the quality of EUL products have a positive significance. In addition,
BT processing can also be considered as the optimal processing method
for EUL to produce the respective secondary metabolites, and the other
two methods also have some processing significance and advantages. The
processing of EUL should be based on the selection of suitable methods
according to the processing objectives required in actual
production.The results of this study provide insights into the
mechanism of changes in some metabolites caused by different
processing. It also provides health activity evaluation of metabolites
produced by different processes of Eucommia ulmoides tea, which can be
used as a functional reference for Eucommia ulmoides tea processing. In
subsequent studies, in-depth investigation of the evolutionary
trajectory of volatile and non-volatile products in the middle of EUL
using different processing techniques can be explored, as well as
further investigation of whether the flavor profile can be further
improved.
The following are the supplementary data related to this article.
Supplementary fig S1.
[129]Supplementary fig S1
[130]Open in a new tab
OPLS-DA model validation plot; Note: The horizontal coordinates
represent the model R^2Y，Q^2 values, and the vertical coordinates are
the frequency of the model classification effects in 200 random
permutation experiments. In the figure, the orange color represents the
random grouping model R^2Y, the purple color represents the random
grouping model Q^2, and the values represented by the black arrows are
the R^2X, R^2Y, and Q^2 values of the original model.
Supplementary fig S2.
[131]Supplementary fig S2
[132]Open in a new tab
Heat map of cluster analysis of different processing processes of
EUL；Note: Horizontal is the sample name, vertical is the metabolite
information, Group is the grouping, and different colors are filled
with different values obtained by normalizing different relative
contents (red for high, green for low).
Supplementary fig S3.
[133]Supplementary fig S3
[134]Open in a new tab
Thermograms of non-volatile metabolites of various classes of
differently processed Cortex Eucommia leave. (A-K represent one class
of substances each. A: Amino acids and their derivatives; B: Lipids; C:
Flavonoids; D: Phenolic acids; E: Nucleotides and their derivatives; F:
Alkaloids; G: Organic acids; H: Lignans: I: Tannins; J: Terpenoids; K:
Other classes).
Supplementary fig S4.
[135]Supplementary fig S4
[136]Open in a new tab
Radar plot of sensory flavor characterization of differential
metabolites across comparison groups; Note: The outermost circle name
indicates the organoleptic flavor profile, and the number corresponding
to the green dot indicates the number of occurrences of the
corresponding organoleptic flavor profile, i.e., the number of
differential metabolites annotated to that organoleptic flavor profile.
Supplementary fig S5.
[137]Supplementary fig S5
[138]Open in a new tab
Differential metabolite flavor wheel plots for each comparison group;
Note: the innermost circle is the differential comparison group, the
second circle is the top 10 sensory flavor profiles with the highest
number of differential metabolites annotated to the comparison group,
the number in parentheses indicates the number of differential
metabolites annotated to the sensory flavor profile, and the outermost
circle indicates the differential metabolites, if the number of
differential metabolites annotated to a sensory flavor profile If the
number of differential metabolites annotated to an organoleptic flavor
profile exceeds 10, the top 10 differential metabolites with the
largest VIP values are displayed.
Supplementary material 1
Clustering heatmap of amino acids and their derivatives metabolites
from differently processed Eucommia ulmoides leaves
[139]mmc6.pdf^ (31KB, pdf)
Supplementary material 2
Clustering heatmap of lipid metabolites from differently processed
Eucommia ulmoides leaves
[140]mmc7.pdf^ (26KB, pdf)
Supplementary material 3
Clustering heatmap of flavonoid metabolites from differently processed
Eucommia ulmoides leaves
[141]mmc8.pdf^ (49.5KB, pdf)
Supplementary material 4
Clustering heatmap of phenolic acid metabolites from differently
processed Eucommia ulmoides leaves
[142]mmc9.pdf^ (42.5KB, pdf)
Supplementary material 5
Clustering heatmap of nucleotide and their derivatives metabolites from
differently processed Eucommia ulmoides leaves
[143]mmc10.pdf^ (16.5KB, pdf)
Supplementary material 6
Clustering heatmap of alkaloid metabolites from differently processed
Eucommia ulmoides leaves
[144]mmc11.pdf^ (26.1KB, pdf)
Supplementary material 7
Clustering heatmap of organic acid metabolites from differently
processed Eucommia ulmoides leaves
[145]mmc12.pdf^ (21KB, pdf)
Supplementary material 8
Clustering heatmap of lignin metabolites from differently processed
Eucommia ulmoides leaves
[146]mmc13.pdf^ (13.5KB, pdf)
Supplementary material 9
Clustering heatmap of tannin metabolites from differently processed
Eucommia ulmoides leaves
[147]mmc14.pdf^ (7.9KB, pdf)
Supplementary material 10
Clustering heatmap of terpenoid metabolites from differently processed
Eucommia ulmoides leaves
[148]mmc15.pdf^ (22.8KB, pdf)
Supplementary material 11
Clustering heatmap of other metabolites from differently processed
Eucommia ulmoides leaves
[149]mmc16.pdf^ (35.9KB, pdf)
Supplementary material 12
Names of graphs and tables used in the article and related descriptions
[150]mmc17.docx^ (18.8KB, docx)
CRediT authorship contribution statement
Yiyun Lin: Writing – original draft, Investigation, Formal analysis,
Data curation. Hui Ouyang: Writing – review & editing, Writing –
original draft, Supervision, Project administration, Funding
acquisition, Conceptualization. Ruobing Li: Methodology, Investigation.
Yunzhe Shao: Methodology, Investigation. Xiangrong Tian: Writing –
review & editing, Investigation. Yongkang Zhang: Supervision,
Resources.
Declaration of competing interest
The authors declare that they have no known competing financial
interests or personal relationships that could have appeared to
influence the work reported in this paper.
Acknowledgments