#METABOLOMICS WORKBENCH jord001_20250201_151607 DATATRACK_ID:5587 STUDY_ID:ST003998 ANALYSIS_ID:AN006591 PROJECT_ID:PR002503
VERSION             	1
CREATED_ON             	June 23, 2025, 4:27 pm
#PROJECT
PR:PROJECT_TITLE                 	Untargeted Metabolomics and In silico Screening of Sisymbrium officinale:
PR:PROJECT_TITLE                 	Identification of Flavonoid Glycosides as Potential Anti-Inflammatory Agents
PR:PROJECT_SUMMARY               	Sisymbrium officinale (SO), often referred to as "the plant of singers," is a
PR:PROJECT_SUMMARY               	revered traditional Mediterranean medicinal herb known for its applications in
PR:PROJECT_SUMMARY               	treating inflammatory diseases. Despite its historical use, comprehensive
PR:PROJECT_SUMMARY               	metabolomics and in silico studies validating its anti-inflammatory effects
PR:PROJECT_SUMMARY               	remain scarce. The study reported here seeks to uncover and characterize the
PR:PROJECT_SUMMARY               	bioactive compounds within SO, providing a critical step in identifying
PR:PROJECT_SUMMARY               	potential anti-inflammatory agents. To achieve this, we extracted plant
PR:PROJECT_SUMMARY               	compounds using various solvents with differing polarities, i.e., water,
PR:PROJECT_SUMMARY               	methanol, ethanol, acetone, and chloroform. These extractions were followed by
PR:PROJECT_SUMMARY               	phase separation (polar phase and nonpolar phase) of crude extracts.
PR:PROJECT_SUMMARY               	Additionally, we employed GC-MS and LC-MS (polar phase and nonpolar phase)
PR:PROJECT_SUMMARY               	spectroscopy to obtain a preliminary quantification of the diverse functional
PR:PROJECT_SUMMARY               	groups in the SO extracts.We also carried out inflammatory bioassay analysis
PR:PROJECT_SUMMARY               	followed by chemometrics and in silico screening.
PR:INSTITUTE                     	King Abdullah University of Science and Technology
PR:LAST_NAME                     	Kahfi
PR:FIRST_NAME                    	Jordan
PR:ADDRESS                       	Thuwal, Thuwal, Makkah, 23955, Saudi Arabia
PR:EMAIL                         	jordan.kahfi@kaust.edu.sa
PR:PHONE                         	0541244806
#STUDY
ST:STUDY_TITLE                   	Untargeted Metabolomics and In silico Screening of Sisymbrium officinale:
ST:STUDY_TITLE                   	Identification of Flavonoid Glycosides as Potential Anti-Inflammatory Agents
ST:STUDY_SUMMARY                 	Sisymbrium officinale (SO), often referred to as "the plant of singers," is a
ST:STUDY_SUMMARY                 	revered traditional Mediterranean medicinal herb known for its applications in
ST:STUDY_SUMMARY                 	treating inflammatory diseases. Despite its historical use, comprehensive
ST:STUDY_SUMMARY                 	metabolomics and in silico studies validating its anti-inflammatory effects
ST:STUDY_SUMMARY                 	remain scarce. The study reported here seeks to uncover and characterize the
ST:STUDY_SUMMARY                 	bioactive compounds within SO, providing a critical step in identifying
ST:STUDY_SUMMARY                 	potential anti-inflammatory agents. To achieve this, we extracted plant
ST:STUDY_SUMMARY                 	compounds using various solvents with differing polarities, i.e., water,
ST:STUDY_SUMMARY                 	methanol, ethanol, acetone, and chloroform. These extractions were followed by
ST:STUDY_SUMMARY                 	phase separation (polar phase and nonpolar phase) of crude extracts.
ST:STUDY_SUMMARY                 	Additionally, we employed GC-MS and LC-MS (polar phase and nonpolar phase)
ST:STUDY_SUMMARY                 	spectroscopy to obtain a preliminary quantification of the diverse functional
ST:STUDY_SUMMARY                 	groups in the SO extracts. GC-MS analysis resulted in the identification of SO
ST:STUDY_SUMMARY                 	primary metabolites including sugars (rhamnose, trehalose, fructopyranose,
ST:STUDY_SUMMARY                 	myo-inositol, etc.), amino acids (glycine, lysine, valine, etc.), and fatty
ST:STUDY_SUMMARY                 	acids (linolenic acid, norlinolenic acid, aminovaleric acid, etc.). The LC-MS
ST:STUDY_SUMMARY                 	analysis of both polar and nonpolar fraction resulted in diverse secondary
ST:STUDY_SUMMARY                 	metabolite groups including alkaloids (tetramethylpyrazine, pilocarpine),
ST:STUDY_SUMMARY                 	flavonoids (apigetrin, cynaroside, vitexin 4-O-glucoside, kaempferol, galangin,
ST:STUDY_SUMMARY                 	naringenin, etc.), and plant sterols (zymosterol). The bioassay analysis showed
ST:STUDY_SUMMARY                 	that methanol, ethanol, and acetone possess the highest anti-inflammatory
ST:STUDY_SUMMARY                 	activity through NO suppresion of RAW 264.7 macrophage cells. Further,
ST:STUDY_SUMMARY                 	chemometrics and in silico screening (molecular docking and ADMET) resulted in
ST:STUDY_SUMMARY                 	two flavonoid glycosides, apigetrin and 3-O-α-L-arabinopyranoside, as potential
ST:STUDY_SUMMARY                 	anti-inflammatory compounds that suppress the activity of human inducible NO
ST:STUDY_SUMMARY                 	synthase (iNOS, PDB ID: 3E7G), endothelial NOS (eNOS, PDB ID: 6AV7), and
ST:STUDY_SUMMARY                 	neuronal NOS (nNOS, PDB ID: 6CID). These findings pave the ways for further
ST:STUDY_SUMMARY                 	validation studies including isolation, purification, in vitro, and in vivo
ST:STUDY_SUMMARY                 	analysis.
ST:INSTITUTE                     	King Abdullah University of Science and Technology
ST:LAST_NAME                     	Kahfi
ST:FIRST_NAME                    	Jordan
ST:ADDRESS                       	Thuwal, Thuwal, Makkah, 23955, Saudi Arabia
ST:EMAIL                         	jordan.kahfi@kaust.edu.sa
ST:PHONE                         	0541244806
#SUBJECT
SU:SUBJECT_TYPE                  	Plant
SU:SUBJECT_SPECIES               	Sisymbrium officinale
SU:TAXONOMY_ID                   	203582
#FACTORS
#SUBJECT_SAMPLE_FACTORS:         	SUBJECT(optional)[tab]SAMPLE[tab]FACTORS(NAME:VALUE pairs separated by |)[tab]Raw file names and additional sample data
SUBJECT_SAMPLE_FACTORS           	-	A1	Sample source:Leaves | Treatment:Acetone Crude Extract	Replicate=Technical replicate 1; RAW_FILE_NAME(Raw File Name GC)=A1-GC; RAW_FILE_NAME(Raw File Name LC Positive)=A1-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=A1-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=A1-NP
SUBJECT_SAMPLE_FACTORS           	-	A2	Sample source:Leaves | Treatment:Acetone Crude Extract	Replicate=Technical replicate 2; RAW_FILE_NAME(Raw File Name GC)=A2-GC; RAW_FILE_NAME(Raw File Name LC Positive)=A2-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=A2-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=A2-NP
SUBJECT_SAMPLE_FACTORS           	-	A3	Sample source:Leaves | Treatment:Acetone Crude Extract	Replicate=Technical replicate 3; RAW_FILE_NAME(Raw File Name GC)=A3-GC; RAW_FILE_NAME(Raw File Name LC Positive)=A3-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=A3-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=A3-NP
SUBJECT_SAMPLE_FACTORS           	-	A4	Sample source:Leaves | Treatment:Acetone Crude Extract	Replicate=Technical replicate 4; RAW_FILE_NAME(Raw File Name GC)=A4-GC; RAW_FILE_NAME(Raw File Name LC Positive)=A4-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=A4-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=A4-NP
SUBJECT_SAMPLE_FACTORS           	-	A5	Sample source:Leaves | Treatment:Acetone Crude Extract	Replicate=Technical replicate 5; RAW_FILE_NAME(Raw File Name GC)=A5-GC; RAW_FILE_NAME(Raw File Name LC Positive)=A5-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=A5-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=A5-NP
SUBJECT_SAMPLE_FACTORS           	-	C1	Sample source:Leaves | Treatment:Chloroform Crude Extract	Replicate=Technical replicate 1; RAW_FILE_NAME(Raw File Name GC)=C1-GC; RAW_FILE_NAME(Raw File Name LC Positive)=C1-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=C1-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=C1-NP
SUBJECT_SAMPLE_FACTORS           	-	C2	Sample source:Leaves | Treatment:Chloroform Crude Extract	Replicate=Technical replicate 2; RAW_FILE_NAME(Raw File Name GC)=C2-GC; RAW_FILE_NAME(Raw File Name LC Positive)=C2-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=C2-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=C2-NP
SUBJECT_SAMPLE_FACTORS           	-	C3	Sample source:Leaves | Treatment:Chloroform Crude Extract	Replicate=Technical replicate 3; RAW_FILE_NAME(Raw File Name GC)=C3-GC; RAW_FILE_NAME(Raw File Name LC Positive)=C3-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=C3-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=C3-NP
SUBJECT_SAMPLE_FACTORS           	-	C4	Sample source:Leaves | Treatment:Chloroform Crude Extract	Replicate=Technical replicate 4; RAW_FILE_NAME(Raw File Name GC)=C4-GC; RAW_FILE_NAME(Raw File Name LC Positive)=C4-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=C4-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=C4-NP
SUBJECT_SAMPLE_FACTORS           	-	C5	Sample source:Leaves | Treatment:Chloroform Crude Extract	Replicate=Technical replicate 5; RAW_FILE_NAME(Raw File Name GC)=C5-GC; RAW_FILE_NAME(Raw File Name LC Positive)=C5-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=C5-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=C5-NP
SUBJECT_SAMPLE_FACTORS           	-	E1	Sample source:Leaves | Treatment:Ethanol Crude Extract	Replicate=Technical replicate 1; RAW_FILE_NAME(Raw File Name GC)=E1-GC; RAW_FILE_NAME(Raw File Name LC Positive)=E1-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=E1-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=E1-NP
SUBJECT_SAMPLE_FACTORS           	-	E2	Sample source:Leaves | Treatment:Ethanol Crude Extract	Replicate=Technical replicate 2; RAW_FILE_NAME(Raw File Name GC)=E2-GC; RAW_FILE_NAME(Raw File Name LC Positive)=E2-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=E2-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=E2-NP
SUBJECT_SAMPLE_FACTORS           	-	E3	Sample source:Leaves | Treatment:Ethanol Crude Extract	Replicate=Technical replicate 3; RAW_FILE_NAME(Raw File Name GC)=E3-GC; RAW_FILE_NAME(Raw File Name LC Positive)=E3-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=E3-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=E3-NP
SUBJECT_SAMPLE_FACTORS           	-	E4	Sample source:Leaves | Treatment:Ethanol Crude Extract	Replicate=Technical replicate 4; RAW_FILE_NAME(Raw File Name GC)=E4-GC; RAW_FILE_NAME(Raw File Name LC Positive)=E4-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=E4-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=E4-NP
SUBJECT_SAMPLE_FACTORS           	-	E5	Sample source:Leaves | Treatment:Ethanol Crude Extract	Replicate=Technical replicate 5; RAW_FILE_NAME(Raw File Name GC)=E5-GC; RAW_FILE_NAME(Raw File Name LC Positive)=E5-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=E5-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=E5-NP
SUBJECT_SAMPLE_FACTORS           	-	M1	Sample source:Leaves | Treatment:Methanol Crude Extract	Replicate=Technical replicate 1; RAW_FILE_NAME(Raw File Name GC)=M1-GC; RAW_FILE_NAME(Raw File Name LC Positive)=M1-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=M1-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=M1-NP
SUBJECT_SAMPLE_FACTORS           	-	M2	Sample source:Leaves | Treatment:Methanol Crude Extract	Replicate=Technical replicate 2; RAW_FILE_NAME(Raw File Name GC)=M2-GC; RAW_FILE_NAME(Raw File Name LC Positive)=M2-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=M2-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=M2-NP
SUBJECT_SAMPLE_FACTORS           	-	M3	Sample source:Leaves | Treatment:Methanol Crude Extract	Replicate=Technical replicate 3; RAW_FILE_NAME(Raw File Name GC)=M3-GC; RAW_FILE_NAME(Raw File Name LC Positive)=M3-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=M3-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=M3-NP
SUBJECT_SAMPLE_FACTORS           	-	M4	Sample source:Leaves | Treatment:Methanol Crude Extract	Replicate=Technical replicate 4; RAW_FILE_NAME(Raw File Name GC)=M4-GC; RAW_FILE_NAME(Raw File Name LC Positive)=M4-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=M4-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=M4-NP
SUBJECT_SAMPLE_FACTORS           	-	M5	Sample source:Leaves | Treatment:Methanol Crude Extract	Replicate=Technical replicate 5; RAW_FILE_NAME(Raw File Name GC)=M5-GC; RAW_FILE_NAME(Raw File Name LC Positive)=M5-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=M5-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=M5-NP
SUBJECT_SAMPLE_FACTORS           	-	W1	Sample source:Leaves | Treatment:Water Crude Extract	Replicate=Technical replicate 1; RAW_FILE_NAME(Raw File Name GC)=W1-GC; RAW_FILE_NAME(Raw File Name LC Positive)=W1-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=W1-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=W1-NP
SUBJECT_SAMPLE_FACTORS           	-	W2	Sample source:Leaves | Treatment:Water Crude Extract	Replicate=Technical replicate 2; RAW_FILE_NAME(Raw File Name GC)=W2-GC; RAW_FILE_NAME(Raw File Name LC Positive)=W2-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=W2-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=W2-NP
SUBJECT_SAMPLE_FACTORS           	-	W3	Sample source:Leaves | Treatment:Water Crude Extract	Replicate=Technical replicate 3; RAW_FILE_NAME(Raw File Name GC)=W3-GC; RAW_FILE_NAME(Raw File Name LC Positive)=W3-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=W3-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=W3-NP
SUBJECT_SAMPLE_FACTORS           	-	W4	Sample source:Leaves | Treatment:Water Crude Extract	Replicate=Technical replicate 4; RAW_FILE_NAME(Raw File Name GC)=W4-GC; RAW_FILE_NAME(Raw File Name LC Positive)=W4-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=W4-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=W4-NP
SUBJECT_SAMPLE_FACTORS           	-	W5	Sample source:Leaves | Treatment:Water Crude Extract	Replicate=Technical replicate 5; RAW_FILE_NAME(Raw File Name GC)=W5-GC; RAW_FILE_NAME(Raw File Name LC Positive)=W5-LCPos; RAW_FILE_NAME(Raw File Name LC Negative)=W5-LCNeg; RAW_FILE_NAME(LC Nonpolar phase - Positive)=W5-NP
#COLLECTION
CO:COLLECTION_SUMMARY            	The leaf sample was collected from wild Sisymbrium officinale Plant grown in in
CO:COLLECTION_SUMMARY            	the mountainous regions of Hebron, Palestine in February 2023.
CO:SAMPLE_TYPE                   	Leaves
#TREATMENT
TR:TREATMENT_SUMMARY             	Sisymbrium officinale leaves were lyophilized and extracted with different type
TR:TREATMENT_SUMMARY             	of solvent (water, ethanol, methanol, acetone, and chloroform). The dried crude
TR:TREATMENT_SUMMARY             	extracts were subjected for liquid-liquid phase separation: polar phase and
TR:TREATMENT_SUMMARY             	nonpolar phase prior GC-MS and LC-MS analysis
#SAMPLEPREP
SP:SAMPLEPREP_SUMMARY            	SO powder (25 mg) was mixed with 2.0 mL of each different solvent: water,
SP:SAMPLEPREP_SUMMARY            	methanol, ethanol, ethyl acetate, and acetone. The mixtures were sonicated in
SP:SAMPLEPREP_SUMMARY            	ice bath (15 minutes) to avoid excessive heating, macerated on a shaker
SP:SAMPLEPREP_SUMMARY            	overnight (25 °C, 1400 rpm, 17 hours) to ensure maximum extraction, and
SP:SAMPLEPREP_SUMMARY            	centrifuged (25 °C, 14,000X g, 10 minutes) to separate the debris and extracted
SP:SAMPLEPREP_SUMMARY            	materials. The supernatant was transferred into new labelled tubes (water,
SP:SAMPLEPREP_SUMMARY            	methanol, ethanol, ethyl acetate, and acetone) and stored at -20 °C.
#CHROMATOGRAPHY
CH:CHROMATOGRAPHY_SUMMARY        	A Thermo Vanquish was used for the analysis of the polar phase secondary
CH:CHROMATOGRAPHY_SUMMARY        	metabolites. Chromatographic separation of the liquid-phase chemical components
CH:CHROMATOGRAPHY_SUMMARY        	was achieved using a C18 column (2.1 × 100 mm, 1.7µm) Waters, Milford, MA,
CH:CHROMATOGRAPHY_SUMMARY        	USA, coupled to a UPLC BEH C18 column (2.1 × 10mm, 1.7µm) with a flow rate of
CH:CHROMATOGRAPHY_SUMMARY        	0.4 mL/min. Two solutions were used for the mobile phase, namely Solution A
CH:CHROMATOGRAPHY_SUMMARY        	(100% water; 0.1% formic acid) and Solution B (100% acetonitrile; 0.1% formic
CH:CHROMATOGRAPHY_SUMMARY        	acid).
CH:CHROMATOGRAPHY_TYPE           	Reversed phase
CH:INSTRUMENT_NAME               	Thermo Vanquish
CH:COLUMN_NAME                   	Waters ACQUITY UPLC BEH C18 (100 x 2.1mm,1.7um)
CH:SOLVENT_A                     	100% water; 0.1% formic acid
CH:SOLVENT_B                     	100% acetonitrile; 0.1% formic acid
CH:FLOW_GRADIENT                 	The gradient was linearly changed as follows: 0−2 min, 100% B; 2−9 min from
CH:FLOW_GRADIENT                 	100% B to 85% B; 9−14 min from 85% B to 50% B; 14−17 min from 50% B to
CH:FLOW_GRADIENT                 	100%B, 17.1−20 min, 100% B for column re-equilibration.
CH:FLOW_RATE                     	0.4 mL/min
CH:COLUMN_TEMPERATURE            	35°C
#ANALYSIS
AN:ANALYSIS_TYPE                 	MS
#MS
MS:INSTRUMENT_NAME               	Thermo Orbitrap ID-X Tribrid
MS:INSTRUMENT_TYPE               	Orbitrap
MS:MS_TYPE                       	ESI
MS:ION_MODE                      	NEGATIVE
MS:MS_COMMENTS                   	The Thermo Orbitrap ID-X tribrid was used. This instrument was operated using
MS:MS_COMMENTS                   	following parameters: sheath gas at 50 arb, auxiliary gas at 10 arb, spray
MS:MS_COMMENTS                   	voltage at +3.5 kV in positive mode and 2.5kV, capillary temperature at 300
MS:MS_COMMENTS                   	◦C, auxiliary gas heater temperature at 350°C, s-lens RF level at 60%. Full
MS:MS_COMMENTS                   	scan parameters: m/z range from 50 to 500; mass resolution, 60,000; AGC target,
MS:MS_COMMENTS                   	3e6; maximum IT, 100ms. DDA parameters: m/z range from 50 to 500, TopN, 3
MS:MS_COMMENTS                   	(fragments the 3 ions with top intensities from the previous full scan
MS:MS_COMMENTS                   	spectrum); intensity threshold to trigger MS/MS acquisition, 2e4; dynamic
MS:MS_COMMENTS                   	exclusion, 6 s; combined MSMS CE at 10, 30, 40, 70, 90 eV, mass resolution,
MS:MS_COMMENTS                   	30,000; AGC target, 1e5; maximum IT, 50ms; m/z isolation window within 1.
#MS_METABOLITE_DATA
MS_METABOLITE_DATA:UNITS	AUC
MS_METABOLITE_DATA_START
Samples	A1	A2	A3	A4	A5	E1	E2	E3	E4	E5	C1	C2	C3	C4	C5	M1	M2	M3	M4	M5	W1	W2	W3	W4	W5
Factors	Sample source:Leaves | Treatment:Acetone Crude Extract	Sample source:Leaves | Treatment:Acetone Crude Extract	Sample source:Leaves | Treatment:Acetone Crude Extract	Sample source:Leaves | Treatment:Acetone Crude Extract	Sample source:Leaves | Treatment:Acetone Crude Extract	Sample source:Leaves | Treatment:Ethanol Crude Extract	Sample source:Leaves | Treatment:Ethanol Crude Extract	Sample source:Leaves | Treatment:Ethanol Crude Extract	Sample source:Leaves | Treatment:Ethanol Crude Extract	Sample source:Leaves | Treatment:Ethanol Crude Extract	Sample source:Leaves | Treatment:Chloroform Crude Extract	Sample source:Leaves | Treatment:Chloroform Crude Extract	Sample source:Leaves | Treatment:Chloroform Crude Extract	Sample source:Leaves | Treatment:Chloroform Crude Extract	Sample source:Leaves | Treatment:Chloroform Crude Extract	Sample source:Leaves | Treatment:Methanol Crude Extract	Sample source:Leaves | Treatment:Methanol Crude Extract	Sample source:Leaves | Treatment:Methanol Crude Extract	Sample source:Leaves | Treatment:Methanol Crude Extract	Sample source:Leaves | Treatment:Methanol Crude Extract	Sample source:Leaves | Treatment:Water Crude Extract	Sample source:Leaves | Treatment:Water Crude Extract	Sample source:Leaves | Treatment:Water Crude Extract	Sample source:Leaves | Treatment:Water Crude Extract	Sample source:Leaves | Treatment:Water Crude Extract
2-(Acetylamino)hexanoic acid	31766254.29	28621939.96	21584518.59	25804605	28557871.46	38252.51717	8932.081886	7372.020017	120171.5987	45070.37145	5859159.839	6220571.49	6325729.975	6270480.953	6105167.029	4368191.692	4889679.709	4643009.941	5339462.113	4871810.801	329416.1765	183846.2415	203036.1059	309120.4612	213646.1953
3-tert-Butyladipic acid	4224531.168	4212794.529	3566578.997	4184464.236	4395731.053	21178.84012	385292.8842	261984.085	490973.9382	751959.4331	3250700.737	3793517.679	3481678.341	3052730.704	3567301.056	2791326.555	3334174.372	3001205	3323303.923	3342832.68	3823766.236	3930689.709	3770998.872	4008700.7	3264539.544
4-Nitrophenol	1568596.63	1340548.021	972293.2099	1338055.95	1351861.335	2070926.367	25963674.03	9861227.697	15329205.88	8350870.06	21433175.72	20949007.73	15532633.14	34457580.33	41544627.04	16169825.81	24706377.13	16200829.48	18166170.67	22745529.82	3240387.91	5252972.328	4879966.83	5101252.002	6248060.662
4-Oxoproline	1351904.12	779697.4904	1133523.195	1296668.218	452509.1008	117685.5225	46958.58472	29673.09791	1854710.021	785789.1906	25470256.02	32898853.17	29340309.23	34602707.94	30171859.48	19506070.05	32491881.85	21882004.55	30366753.4	32965025.5	31226089.72	30593613.02	26303771.19	31370107.21	29809641.48
6-Hydroxycaproic acid	10704614.34	10247521.77	6083041.992	9747687.211	10158850.78	427150.8911	36394.12726	40333.05922	62169.8238	45497.97831	677358.8529	1186167.501	982741.6053	1091094.382	1060699.839	535605.0628	1096633.586	661792.4184	873190.381	1314681.283	1523259.599	1451204.671	1150380.156	1538861.562	1402755.314
Acetoxyacetic acid	48319119.86	35269726.56	33888334.49	45335798.84	36303772.04	643895.634	282832.9691	287021.8503	489556.4544	236958.6325	2959379.454	3619088.212	1745185.639	3804779.783	3504945.021	1392603.994	1543554.132	1565682.098	1858426.102	2658801.989	1137736.488	1085336.763	1059614.745	1132767.89	1186940.541
Cynaroside	562888.3	406072.7052	389126.5781	454791.4637	334063.3725	4733.941545	9395.986313	6268.06778	189487.9485	14706.02905	4344823.421	5920131.182	5794605.369	6022493.331	5293540.55	3360016.102	6278989.954	3888091.196	5552243.32	5278816.29	390624.265	114690.716	145967.6518	73708.87453	624573.8388
D-(+)-Tryptophan	11455480.29	9909003.166	6335970.177	11114994.64	7752809.747	88366.16823	4784884.188	4483458.44	2612957.864	6362550.356	2470847.836	3273015.25	3130304.899	2391059.021	3051632.413	956128.2579	1978886.032	1115622.113	1799734.366	1840130.011	57928.78947	98405.8854	72738.69394	113331.6599	55543.11435
DL-β-Leucine	4543031.06	4181913.762	3069893.855	3815557.691	4111733	16856.65029	33269.89156	5634.562325	738912.9083	151492.1273	4255359.733	4889208.249	4359727.228	4730036.644	4818361.2	3758426.83	5061731.301	3639788.047	4921970.668	5126739.896	6594492.479	6546807.317	5689063.905	6725174.092	6380455.114
Dodecanedioic acid	13130588.32	12026618.05	9481420.823	11406254.6	12205918.8	44599.32587	17663.51796	10742.568	540995.9069	112909.8578	5958437.638	8078903.664	7889073.676	8815810.214	8249957.984	4949434.806	9492451.425	5643604.249	7910205.525	8026167.918	2810007.635	2776188.971	2285300.605	2691771.687	2857859.094
Gluconic acid	51158077	29610447.87	37350845.11	47111967.37	28795630.84	178630.9623	5502.122282	5345.139717	147765.8347	7852.278548	3530721.138	3842195.173	4001326.983	5608966.29	3638053.345	1910449.156	3744230.896	2814697.855	3007414.285	3381640.507	57344.12856	55460.27999	53705.51498	56784.7995	61165.42147
Glutaric acid	125925.0348	114981.2249	132240.3427	158082.5254	119830.0355	16998.62718	12597301.26	10058999.54	6351779.758	7717176.397	4400438.475	5137875.98	4543447.285	6381759.355	5136204.297	2515947.025	5395348.977	3441254.243	4212016.088	3793257.969	4932189.375	4955861.547	4372499.155	5156117.454	5036285.711
Hispidulin	4833625.568	4555382.586	3500943.101	4620208.867	4337575.665	7987095.904	3155384.358	2132128.406	1765704.188	1665364.736	1146971.675	1688654.429	990083.7948	1470272.411	1405489.706	988820.844	1748330.438	1186835.721	1398678.195	1679119.792	709750.0852	819154.6458	656423.4501	775515.8922	1003237.79
Isocitric acid	785486.9376	489583.5178	714805.855	551460.1759	629711.4185	807010.1893	124671.3663	92812.84968	481463.8842	3169544.273	25151217.77	26065131.37	28785475.65	29123802.98	26230386.25	24564412.15	27815336.63	25345640.57	26405427.18	29441667.14	21900937.76	22929469.23	23273989.41	21797732.71	21818017.07
Isophthalic acid	1169015.676	846404.8705	499349.0627	833170.1024	840885.4782	51428.16925	20656.85988	21351.59275	110096.3167	33637.71879	3560679.637	4778330.405	5156626.589	4019723.903	3989059.155	3632801.763	5130820.392	4102173.243	6676728.355	6432899.757	11156864.09	11028407.78	9044753.359	4174380.44	9586815.94
L-Histidine	33264.03917	72988.95606	51472.0364	31103.60778	47560.69816	19475.4937	17310.80281	14917.86784	57863.55085	55679.33679	2648544.221	1895090.762	3437681.786	2970323.056	2617241.126	1363835.002	2895767.535	1781228.073	2236608.437	2635478.242	788195.969	585830.436	704833.8967	798008.8461	1778998.042
L-Homoserine	34323520.92	34630611.93	26631497.79	31018347.35	34063191.77	67391.62941	1244087.311	572250.5398	950410.8877	1032783.68	10887189.86	12432303.07	10979348.98	9427220.875	12055818.03	9455954.014	14414300.15	8129947.289	11193709.85	11769788.92	127215724.9	125034159.4	109538814.1	133593133	112182165.4
Ornithine	11668841.16	9658569.059	8857170.135	9663638.98	9799180.214	70651.88461	49095.83935	49457.42075	50184.72964	23247.71189	134870.043	475658.9654	414020.5449	426657.9662	501629.9809	360468.5919	522787.6543	368445.2954	181451.424	735924.1039	863419.9891	902698.7671	873883.6277	851290.7943	922078.5579
Pimelic acid	141711.8697	199155.2135	96492.46883	237565.8495	80746.66651	83822.95963	2879907.569	1659253.191	1005011.736	1005490.905	565964.654	1022699.591	729159.9738	884004.9973	760072.9839	703618.6227	1236825.576	867208.6724	1241487.209	1447525.786	1441546.63	1185185.087	960712.6993	1195911.64	1491461.864
α-Cyano-3-hydroxycinnamic acid	2423390.857	2289160.799	1663820.966	1752193.571	2129904.995	18479.29626	33019384	5550458.43	14400043.91	16037795.69	2922572.624	5872049.816	3500716.86	5098049.628	3935045.297	2918522.792	7571201.343	5428584.445	7814149.566	10994664.92	4383782.899	3363127.974	3376179.185	4766023.29	3531739.843
MS_METABOLITE_DATA_END
#METABOLITES
METABOLITES_START
metabolite_name	Formula	Annot. DeltaMass [ppm]	Calc. MW	RT [min]	Pubchem CID	INCHI_KEY
2-(Acetylamino)hexanoic acid	C8 H15 N O3	0.52	173.1053	5.019	306142  	JDMCEGLQFSOMQH-UHFFFAOYSA-N  
3-tert-Butyladipic acid	C10 H18 O4	0.03	202.1205	4.71	5192	CXMXRPHRNRROMY-UHFFFAOYSA-N
4-Nitrophenol	C11 H13 N O2	0.22	191.0947	5.967	980	BTJIUGUIPKRLHP-UHFFFAOYSA-N
4-Oxoproline	C5 H7 N O3	1.62	129.0428	0.932	107541	HFXAFXVXPMUQCQ-BYPYZUCNSA-N
6-Hydroxycaproic acid	C6 H12 O3	0.31	132.0787	5.09	14490	IWHLYPDWHHPVAA-UHFFFAOYSA-N
Acetoxyacetic acid	C4 H6 O4	-1.32	118.0265	1.509	83766  	MLXDUYUQINCFFV-UHFFFAOYSA-N
Cynaroside	C21 H20 O11	-0.08	448.1005	5.277	5280637  	PEFNSGRTCBGNAN-QNDFHXLGSA-N  
D-(+)-Tryptophan	C11 H12 N2 O2	0.14	204.0899	3.375	9060	QIVBCDIJIAJPQS-SECBINFHSA-N
DL-β-Leucine	C14 H31 N	0.18	213.2457	6.418	5281612	MBNGWHIJMBWFHU-UHFFFAOYSA-N
Dodecanedioic acid	C6 H13 N O2	1.01	131.0948	5.137	857	ROHFNLRQFUQHCH-UHFFFAOYSA-N
Gluconic acid	C12 H22 O4	-0.83	230.1516	5.756	5281616	VCCRNZQBSJXYJD-UHFFFAOYSA-N
Glutaric acid	C6 H12 O7	-0.5	196.0582	1.22	10690	RGHNJXZEOKUKBD-SQOUGZDYSA-N
Hispidulin	C5 H8 O4	1.45	132.0425	2.277	743	JFCQEDHGNNZCLN-UHFFFAOYSA-N
Isocitric acid	C10 H12 N4 O5	0.13	268.0808	0.946	135398641	UGQMRVRMYYASKQ-KQYNXXCUSA-N
Isophthalic acid	C27 H30 O14	0.48	578.1638	5.071	477826  	HXTFHSYLYXVTHC-TUURGLJWSA-N  
L-Histidine	C6 H9 N3 O2	0.75	155.0696	0.854	6274	HNDVDQJCIGZPNO-YFKPBYRVSA-N
L-Homoserine	C4 H9 N O3	0.3	119.0583	0.909	12647	UKAUYVFTDYCKQA-VKHMYHEASA-N
Ornithine	C5 H12 N2 O2	0.2	132.0899	0.905	6262	AHLPHDHHMVZTML-BYPYZUCNSA-N
Pimelic acid	C7 H12 O4	0.8	160.0737	4.643	385	WLJVNTCWHIRURA-UHFFFAOYSA-N
α-Cyano-3-hydroxycinnamic acid	C21 H20 O11	0.21	448.1007	5.564	5353398  	HPLNTJVXWMJLNJ-XBXARRHUSA-N
METABOLITES_END
#END