#METABOLOMICS WORKBENCH biswapriya_20180912_154656 DATATRACK_ID:1504 STUDY_ID:ST001056 ANALYSIS_ID:AN002145 PROJECT_ID:PR000873 VERSION 1 CREATED_ON December 17, 2019, 3:00 pm #PROJECT PR:PROJECT_TITLE Evaluation of the short-term effects of the allelochemical umbelliferone on PR:PROJECT_TITLE Triticum durum L. metabolism through GC-MS based untargeted metabolomics PR:PROJECT_SUMMARY Allelopathy is a plant defense mechanism by which they protect themselves from PR:PROJECT_SUMMARY competitive species using specialized biochemicals in the form of secretion or PR:PROJECT_SUMMARY volatiles released to the environment. Though, umbelliferone is a well-known PR:PROJECT_SUMMARY allelochemical, its mechanism of action in a short-term treatment is far from PR:PROJECT_SUMMARY established. We used ≈ 10–days old wheat seedlings treated with104 µM PR:PROJECT_SUMMARY umbelliferone over a time course experiment covering 6 times points, i.e., 0h, PR:PROJECT_SUMMARY 6h, 12h, 24h, 48h, and 96h and compared the metabolomic changes to control PR:PROJECT_SUMMARY (mock-treated) plants. Using gas chromatography mass-spectrometry (GC-MS) based PR:PROJECT_SUMMARY metabolomics efforts, we collectively obtained quantitative data on 177 PR:PROJECT_SUMMARY metabolites that were derivatized (either derivatized singly or multiple times) PR:PROJECT_SUMMARY or not representing 139 non-redundant (unique) metabolites. Out of these 139 PR:PROJECT_SUMMARY metabolites, 118 were associated with a unique HMDB identifier, while 113 were PR:PROJECT_SUMMARY associated with a KEGG identifier. Relative quantification of these metabolites PR:PROJECT_SUMMARY across the time-course of umbelliferone treatment, revealed 22 compounds PR:PROJECT_SUMMARY (sugars, fatty acids, secondary metabolites, organic acids, and amino acids) PR:PROJECT_SUMMARY that changed significantly (repeated measures ANOVA, P-value < 0.05) with time. PR:PROJECT_SUMMARY Using multivariate partial least squares discriminant analysis (PLS-DA) we PR:PROJECT_SUMMARY showed the grouping of samples based on time-course across the control and PR:PROJECT_SUMMARY umbelliferone treated plants, whereas the metabolite-metabolite Pearson PR:PROJECT_SUMMARY correlation revealed tightly formed clusters of umbelliferone-derived PR:PROJECT_SUMMARY metabolites, fatty acids, amino acids, and carbohydrates. Also, time-course of PR:PROJECT_SUMMARY umbelliferone treatment revealed, that phospho-L-serine, maltose, and PR:PROJECT_SUMMARY dehydroquinic acid were the top three metabolites showing highest importance in PR:PROJECT_SUMMARY discrimination among the time-points. The above indicate a system-wide changes PR:PROJECT_SUMMARY induced by umbelliferone, through dysregulation of primary as well as PR:PROJECT_SUMMARY specialized metabolism. PR:INSTITUTE University Mediterranea of Reggio Calabria PR:DEPARTMENT Dipartimento AGRARIA PR:LAST_NAME Araniti PR:FIRST_NAME Fabrizio PR:ADDRESS Department AGRARIA, University Mediterranea of Reggio Calabria, Località Feo di PR:ADDRESS Vito, SNC I-89124, Reggio Calabria RC, Italy PR:EMAIL fabrizio.araniti@unirc.it PR:PHONE +39-09651694283 PR:FUNDING_SOURCE Italian Ministry of Education, University and Research (MIUR), project SIR-2014 PR:FUNDING_SOURCE cod. RBSI14L9CE (MEDANAT). PR:PROJECT_COMMENTS NA PR:PUBLICATIONS In process PR:CONTRIBUTORS Misra B.B., Das, V., Landi M., Araniti F., #STUDY ST:STUDY_TITLE Evaluation of the short-term effects of the allelochemical umbelliferone on ST:STUDY_TITLE Triticum durum L. metabolism through GC-MS based untargeted metabolomics ST:STUDY_SUMMARY Allelopathy is a plant defense mechanism by which they protect themselves from ST:STUDY_SUMMARY competitive species using specialized biochemicals in the form of secretion or ST:STUDY_SUMMARY volatiles released to the environment. Though, umbelliferone is a well-known ST:STUDY_SUMMARY allelochemical, its mechanism of action in a short-term treatment is far from ST:STUDY_SUMMARY established. We used ≈ 10–days old wheat seedlings treated with104 µM ST:STUDY_SUMMARY umbelliferone over a time course experiment covering 6 times points, i.e., 0h, ST:STUDY_SUMMARY 6h, 12h, 24h, 48h, and 96h and compared the metabolomic changes to control ST:STUDY_SUMMARY (mock-treated) plants. Using gas chromatography mass-spectrometry (GC-MS) based ST:STUDY_SUMMARY metabolomics efforts, we collectively obtained quantitative data on 177 ST:STUDY_SUMMARY metabolites that were derivatized (either derivatized singly or multiple times) ST:STUDY_SUMMARY or not representing 139 non-redundant (unique) metabolites. Out of these 139 ST:STUDY_SUMMARY metabolites, 118 were associated with a unique HMDB identifier, while 113 were ST:STUDY_SUMMARY associated with a KEGG identifier. Relative quantification of these metabolites ST:STUDY_SUMMARY across the time-course of umbelliferone treatment, revealed 22 compounds ST:STUDY_SUMMARY (sugars, fatty acids, secondary metabolites, organic acids, and amino acids) ST:STUDY_SUMMARY that changed significantly (repeated measures ANOVA, P-value < 0.05) with time. ST:STUDY_SUMMARY Using multivariate partial least squares discriminant analysis (PLS-DA) we ST:STUDY_SUMMARY showed the grouping of samples based on time-course across the control and ST:STUDY_SUMMARY umbelliferone treated plants, whereas the metabolite-metabolite Pearson ST:STUDY_SUMMARY correlation revealed tightly formed clusters of umbelliferone-derived ST:STUDY_SUMMARY metabolites, fatty acids, amino acids, and carbohydrates. Also, time-course of ST:STUDY_SUMMARY umbelliferone treatment revealed, that phospho-L-serine, maltose, and ST:STUDY_SUMMARY dehydroquinic acid were the top three metabolites showing highest importance in ST:STUDY_SUMMARY discrimination among the time-points. The above indicate a system-wide changes ST:STUDY_SUMMARY induced by umbelliferone, through dysregulation of primary as well as ST:STUDY_SUMMARY specialized metabolism. ST:INSTITUTE Università Mediterranea di Reggio Calabria ST:DEPARTMENT Dipartimento AGRARIA ST:LAST_NAME Araniti ST:FIRST_NAME Fabrizio ST:ADDRESS Department AGRARIA, University Mediterranea of Reggio Calabria, Località Feo di ST:ADDRESS Vito, SNC I-89124, Reggio Calabria RC, Italy ST:EMAIL fabrizio.araniti@unirc.it ST:PHONE +39-09651694283 ST:NUM_GROUPS 3 ST:PUBLICATIONS In process #SUBJECT SU:SUBJECT_TYPE Plant SU:SUBJECT_SPECIES Triticum durum SU:TAXONOMY_ID 4567 SU:GENOTYPE_STRAIN cv. Opera SU:AGE_OR_AGE_RANGE 10 days SU:GENDER Not applicable #SUBJECT_SAMPLE_FACTORS: SUBJECT(optional)[tab]SAMPLE[tab]FACTORS(NAME:VALUE pairs separated by |)[tab]Additional sample data SUBJECT_SAMPLE_FACTORS - T1 Time:0h SUBJECT_SAMPLE_FACTORS - T2 Time:0h SUBJECT_SAMPLE_FACTORS - T3 Time:0h SUBJECT_SAMPLE_FACTORS - T4 Time:0h SUBJECT_SAMPLE_FACTORS - 6HUKR1 Time:6h SUBJECT_SAMPLE_FACTORS - 6HUKR2 Time:6h SUBJECT_SAMPLE_FACTORS - 6HUKR3 Time:6h SUBJECT_SAMPLE_FACTORS - 6HUKR4 Time:6h SUBJECT_SAMPLE_FACTORS - 6HUKR5 Time:6h SUBJECT_SAMPLE_FACTORS - 12HUKR1 Time:12h SUBJECT_SAMPLE_FACTORS - 12HUKR2 Time:12h SUBJECT_SAMPLE_FACTORS - 12HUKR3 Time:12h SUBJECT_SAMPLE_FACTORS - 12HUKR4 Time:12h SUBJECT_SAMPLE_FACTORS - 12HUKR5 Time:12h SUBJECT_SAMPLE_FACTORS - 24HUKR1 Time:24h SUBJECT_SAMPLE_FACTORS - 24HUKR2 Time:24h SUBJECT_SAMPLE_FACTORS - 24HUKR3 Time:24h SUBJECT_SAMPLE_FACTORS - 24HUKR4 Time:24h SUBJECT_SAMPLE_FACTORS - 24HUKR5 Time:24h SUBJECT_SAMPLE_FACTORS - 48HUKR1 Time:48h SUBJECT_SAMPLE_FACTORS - 48HUKR2 Time:48h SUBJECT_SAMPLE_FACTORS - 48HUKR3 Time:48h SUBJECT_SAMPLE_FACTORS - 48HUKR4 Time:48h SUBJECT_SAMPLE_FACTORS - 48HUKR5 Time:48h SUBJECT_SAMPLE_FACTORS - 96HUKR1 Time:96h SUBJECT_SAMPLE_FACTORS - 96HUKR2 Time:96h SUBJECT_SAMPLE_FACTORS - 96HUKR3 Time:96h SUBJECT_SAMPLE_FACTORS - 96HUKR4 Time:96h SUBJECT_SAMPLE_FACTORS - 96HUKR5 Time:96h SUBJECT_SAMPLE_FACTORS - 6HKR1 Time:6h SUBJECT_SAMPLE_FACTORS - 6HKR2 Time:6h SUBJECT_SAMPLE_FACTORS - 6HKR3 Time:6h SUBJECT_SAMPLE_FACTORS - 6HKR4 Time:6h SUBJECT_SAMPLE_FACTORS - 6HKR5 Time:6h SUBJECT_SAMPLE_FACTORS - 12HKR1 Time:12h SUBJECT_SAMPLE_FACTORS - 12HKR2 Time:12h SUBJECT_SAMPLE_FACTORS - 12HKR3 Time:12h SUBJECT_SAMPLE_FACTORS - 12HKR4 Time:12h SUBJECT_SAMPLE_FACTORS - 12HKR5 Time:12h SUBJECT_SAMPLE_FACTORS - 24HKR1 Time:24h SUBJECT_SAMPLE_FACTORS - 24HKR2 Time:24h SUBJECT_SAMPLE_FACTORS - 24HKR3 Time:24h SUBJECT_SAMPLE_FACTORS - 24HKR4 Time:24h SUBJECT_SAMPLE_FACTORS - 24HKR5 Time:24h SUBJECT_SAMPLE_FACTORS - 48HKR1 Time:48h SUBJECT_SAMPLE_FACTORS - 48HKR2 Time:48h SUBJECT_SAMPLE_FACTORS - 48HKR3 Time:48h SUBJECT_SAMPLE_FACTORS - 48HKR4 Time:48h SUBJECT_SAMPLE_FACTORS - 48HKR5 Time:48h SUBJECT_SAMPLE_FACTORS - 96HKR1 Time:96h SUBJECT_SAMPLE_FACTORS - 96HKR2 Time:96h SUBJECT_SAMPLE_FACTORS - 96HKR3 Time:96h SUBJECT_SAMPLE_FACTORS - 96HKR4 Time:96h SUBJECT_SAMPLE_FACTORS - 96HKR5 Time:96h SUBJECT_SAMPLE_FACTORS - RT Time:- SUBJECT_SAMPLE_FACTORS - m/z Time:- #COLLECTION CO:COLLECTION_SUMMARY Durum wheat seeds (Triticum durum L. cv. Opera) were germinated in Petri dishes CO:COLLECTION_SUMMARY (9 cm ) in a growth chamber at 25°C, 70% humidity and with a photoperiod of 16 CO:COLLECTION_SUMMARY : 8 (light : dark) and light intensity of 90 mol m-2 s-1 supplied by a cool CO:COLLECTION_SUMMARY white fluorescent lamp (Polylux XL FT8, 55W 8440). Immediately after germination CO:COLLECTION_SUMMARY uniform seedlings were transferred to a 4.5 l hydroponic system and grown in a CO:COLLECTION_SUMMARY modified Hoagland solution formulated as follows: KNO3 (1 mM); MgSO4 (100 µM); CO:COLLECTION_SUMMARY CaSO4 (400 µM); KCl (5 µM); K2SO4 (200 µM); KH2PO4 (175 µM); H3BO3 (2.5 CO:COLLECTION_SUMMARY µM); MnSO4 (0.2 µM); ZnSO4 (0.2 µM); NaMoO4 (0.05 µM); CuSO4 (0.05 µM); CO:COLLECTION_SUMMARY Fe-EDTA (200 µM). CO:SAMPLE_TYPE Plant CO:STORAGE_CONDITIONS -80℃ CO:COLLECTION_VIALS 2ml Eppendorf Screwcapped Round Bottom tubes CO:STORAGE_VIALS 2ml Eppendorf Screwcapped Round Bottom tubes CO:COLLECTION_TUBE_TEMP 4 C CO:ADDITIVES None #TREATMENT TR:TREATMENT_SUMMARY Seedlings (10 day old) were treated for 0 h (T0), 6 h (T1), 12 h (T2), 24 h (T3) TR:TREATMENT_SUMMARY and 96 h (T4) with nitrate (1 mM) and/ or umbelliferone (100 uM) TR:TREATMENT_PROTOCOL_COMMENTS Durum weath seeds were directly sown in hydroponic systems the 11/March/2018 and TR:TREATMENT_PROTOCOL_COMMENTS allowed to establish for 10 days. Nutritional Regime:Plant were grown in TR:TREATMENT_PROTOCOL_COMMENTS hydroponic solution composed as follow: KNO3 (1 mM); MgSO4 (100 µM); CaSO4 (400 TR:TREATMENT_PROTOCOL_COMMENTS µM); KCl (5 µM); K2SO4 (200 µM); KH h2PO4 (175 µM); H h3BO3 (2.5 µM); MnSO4 TR:TREATMENT_PROTOCOL_COMMENTS (0.2 µM); ZnSO4 (0.2 µM); NaMoO4 (0.05 µM); CuSO4 (0.05 µM); Fe-EDTA (200 TR:TREATMENT_PROTOCOL_COMMENTS µM). Plant Watering Regime: plants were cropped in hydroponic solution daily TR:TREATMENT_PROTOCOL_COMMENTS changed TR:TREATMENT Umbelliferone (Inhibitor: 100 uM), Time (0, 6, 12, 24, 48, 96 h) TR:TREATMENT_ROUTE Roots- Hydropony TR:TREATMENT_DOSE 100 uM TR:TREATMENT_DOSEVOLUME Umbelliferone (Inhibitor: 100 uM), Nitrate (1 mM) TR:TREATMENT_DOSEDURATION Time (0, 6, 12, 24, 48, 96 h) TR:TREATMENT_VEHICLE Hoagland Solution TR:PLANT_GROWTH_LOCATION Growth chambers belonging to the University Mediterranea of Reggio Calabria TR:PLANT_LIGHT_PERIOD 18h/6h light/dark TR:PLANT_HUMIDITY 60% Relative Humidity TR:PLANT_TEMP 25°C TR:PLANT_WATERING_REGIME See protocol comments TR:PLANT_NUTRITIONAL_REGIME See protocol comments TR:PLANT_ESTAB_DATE 2018-03-11 TR:PLANT_HARVEST_DATE 2018-03-25 TR:PLANT_GROWTH_STAGE Seedlings collected at the formation of second true leaves TR:PLANT_METAB_QUENCH_METHOD Immediately after collection snap frozen in liquid Nitrogen TR:PLANT_HARVEST_METHOD Full plants harvested manually (5 plants for replicate) TR:PLANT_STORAGE Snap frozen and powdered plant material stored at -80°C TR:TREATMENT_COMPOUND Umbelliferone (Inhibitor: 100 uM) #SAMPLEPREP SP:SAMPLEPREP_SUMMARY Freshly homogenized (100 mg) plant material were obtained for each biological SP:SAMPLEPREP_SUMMARY sample (plant) and replicates. These were transferred to a 2 ml microcentrifuge SP:SAMPLEPREP_SUMMARY round bottom screw cap tubes (Eppendorf). Extraction was done by adding 1400 µl SP:SAMPLEPREP_SUMMARY of methanol (at -20°C) and vortexing for 10 s after addition of 60 µl ribitol SP:SAMPLEPREP_SUMMARY (0.2 mg/ml stock in dH2O) as an internal quantitative standard for the polar SP:SAMPLEPREP_SUMMARY phase. Samples were transferred in a thermomixer at 70C and were shaken for SP:SAMPLEPREP_SUMMARY 10 min (950 rpm) and were then further centrifuged for 10 min at 11000 g. The SP:SAMPLEPREP_SUMMARY supernatants were collected and transferred to glass vials where 750 µl CHCl3 SP:SAMPLEPREP_SUMMARY (-20°C) and 1500 µl dH2O (4°C) were sequentially added. All the samples were SP:SAMPLEPREP_SUMMARY vortexed for 10 s and then centrifuged for another 15 min at 2200 g. Upper polar SP:SAMPLEPREP_SUMMARY phase ((150 µl ) for each replicate were collected, transferred to a 1.5 ml SP:SAMPLEPREP_SUMMARY tube and were dried in a vacuum concentrator without heating. Before freezing SP:SAMPLEPREP_SUMMARY and storing at -80°C, the tubes were filled with argon and placed in a plastic SP:SAMPLEPREP_SUMMARY bag with silica beads (for avoiding moisture and hydration during short-term SP:SAMPLEPREP_SUMMARY storage). Before derivatization, stored samples, were placed in a vacuum SP:SAMPLEPREP_SUMMARY concentrator for 30 minutes to eliminate any trace of humidity. Then, to the SP:SAMPLEPREP_SUMMARY dried samples, 40 µl methoxyamine hydrochloride (20 mg/ml in pyridine) were SP:SAMPLEPREP_SUMMARY added and incubated for 2 h in a Thermomixer (950 rpm) at 37 C. Methoxyaminated SP:SAMPLEPREP_SUMMARY samples were then silylated by adding 70 µl of MSTFA to the aliquots. Samples SP:SAMPLEPREP_SUMMARY were further shaken for 30 min at 37 C. SP:SAMPLEPREP_PROTOCOL_ID NA SP:SAMPLEPREP_PROTOCOL_FILENAME NA SP:SAMPLEPREP_PROTOCOL_COMMENTS NA SP:PROCESSING_METHOD Freshly homogenized (100 mg) plant material were obtained for each biological SP:PROCESSING_METHOD sample (plant) and replicates. These were transferred to a 2 ml microcentrifuge SP:PROCESSING_METHOD round bottom screw cap tubes (Eppendorf). Extraction was done by adding 1400 µl SP:PROCESSING_METHOD of methanol (at -20°C) and vortexing for 10 s after addition of 60 µl ribitol SP:PROCESSING_METHOD (0.2 mg/ml stock in ddH2O) as an internal quantitative standard for the polar SP:PROCESSING_METHOD phase. Samples were transferred in a thermomixer at 70C and were shaken for SP:PROCESSING_METHOD 10 min (950 rpm) and were then further centrifuged for 10 min at 11000 g. The SP:PROCESSING_METHOD supernatants were collected and transferred to glass vials where 750 µl CHCl3 SP:PROCESSING_METHOD (-20°C) and 1500 µl ddH2O (4°C) were sequentially added. All the samples were SP:PROCESSING_METHOD vortexed for 10 s and then centrifuged for another 15 min at 2200 g. Upper polar SP:PROCESSING_METHOD phase (150 µl ) for each replicate were collected, transferred to a 1.5 ml tube SP:PROCESSING_METHOD and were dried in a vacuum concentrator without heating. Before freezing and SP:PROCESSING_METHOD storing at -80°C, the tubes were filled with argon and placed in a plastic bag SP:PROCESSING_METHOD with silica beads (for avoiding moisture and hydration during short-term SP:PROCESSING_METHOD storage). SP:PROCESSING_STORAGE_CONDITIONS On ice SP:EXTRACTION_METHOD Freshly homogenized (100 mg) plant material were obtained for each biological SP:EXTRACTION_METHOD sample (plant) and replicates. These were transferred to a 2 ml microcentrifuge SP:EXTRACTION_METHOD round bottom screw cap tubes (Eppendorf). Extraction was done by adding 1400 µl SP:EXTRACTION_METHOD of methanol (at -20°C) and vortexing for 10 s after addition of 60 µl ribitol SP:EXTRACTION_METHOD (0.2 mg/ml stock in ddH2O) as an internal quantitative standard for the polar SP:EXTRACTION_METHOD phase. Samples were transferred in a thermomixer at 70C and were shaken for SP:EXTRACTION_METHOD 10 min (950 rpm) and were then further centrifuged for 10 min at 11000 g. The SP:EXTRACTION_METHOD supernatants were collected and transferred to glass vials where 750 µl CHCl3 SP:EXTRACTION_METHOD (-20°C) and 1500 µl ddH2O (4°C) were sequentially added. All the samples were SP:EXTRACTION_METHOD vortexed for 10 s and then centrifuged for another 15 min at 2200 g. Upper polar SP:EXTRACTION_METHOD phase (150 µl ) for each replicate were collected, transferred to a 1.5 ml tube SP:EXTRACTION_METHOD and were dried in a vacuum concentrator without heating. Before freezing and SP:EXTRACTION_METHOD storing at -80°C, the tubes were filled with argon and placed in a plastic bag SP:EXTRACTION_METHOD with silica beads (for avoiding moisture and hydration during short-term SP:EXTRACTION_METHOD storage). SP:EXTRACT_ENRICHMENT NA SP:EXTRACT_CLEANUP NA SP:EXTRACT_STORAGE 4℃ SP:SAMPLE_RESUSPENSION Dried for Derivatization SP:SAMPLE_DERIVATIZATION Methoxyaminatin + trimethylsilylation (MSTFA + 1% TMCS) SP:SAMPLE_SPIKING 60 µl ribitol (0.2 mg/ml stock in ddH2O) SP:SUBCELLULAR_LOCATION NA #CHROMATOGRAPHY CH:CHROMATOGRAPHY_SUMMARY The derivatized extracts were injected into a TG-5MS capillary column (30 m x CH:CHROMATOGRAPHY_SUMMARY 0.25 mm x 0.25 µm) (Thermo Fisher Scientific, Waltham, MA, USA) using a gas CH:CHROMATOGRAPHY_SUMMARY chromatograph apparatus (Trace GC 1310, Thermo Fisher Scientific, Waltham, MA, CH:CHROMATOGRAPHY_SUMMARY USA) equipped with a single quadrupole mass spectrometer (ISQ LT, Thermo Fisher CH:CHROMATOGRAPHY_SUMMARY Scientific, Waltham, Massachusetts, US). Injector and source were set at 250°C CH:CHROMATOGRAPHY_SUMMARY and 260°C temperature, respectively. One µl of sample was injected in CH:CHROMATOGRAPHY_SUMMARY splitless mode with a helium flow of 1 ml/min using the following programmed CH:CHROMATOGRAPHY_SUMMARY temperature: isothermal 5 min at 70 °C followed by a 5°C/ min ramp to 350 °C CH:CHROMATOGRAPHY_SUMMARY and a final 5 min heating at 330°C. CH:CHROMATOGRAPHY_TYPE GC CH:INSTRUMENT_NAME Trace GC 1310, Thermo Fisher Scientific CH:COLUMN_NAME TG-5MS CH:FLOW_RATE 1 ml/min CH:COLUMN_TEMPERATURE programmed temperature: isothermal 5 min at 70 °C followed by a 5°C/ min ramp CH:COLUMN_TEMPERATURE to 350 °C and a final 5 min heating at 330°C CH:METHODS_ID NA CH:INJECTION_TEMPERATURE 250 CH:INTERNAL_STANDARD Adonitol (0.0002mg/ml of pure water) 60 μL per sample CH:RETENTION_INDEX Alkanes mixture C10-C40 CH:RETENTION_TIME Alkanes mixture C10-C40 CH:OVEN_TEMPERATURE programmed temperature: isothermal 5 min at 70 °C followed by a 5°C/ min ramp CH:OVEN_TEMPERATURE to 350 °C and a final 5 min heating at 330°C CH:TRANSFERLINE_TEMPERATURE 250 CH:SAMPLE_SYRINGE_SIZE 10 μL CH:RANDOMIZATION_ORDER YES #ANALYSIS AN:ANALYSIS_TYPE MS AN:LABORATORY_NAME Laboratory of plant physiology and biochemestry of the agro-forestal systems AN:OPERATOR_NAME Fabrizio Araniti AN:SOFTWARE_VERSION Xcalibur 3.0.63 AN:ACQUISITION_DATE 22/05/18 till 31/05/18 AN:DATA_FORMAT .RAW (Thermo Fisher Scientific) #MS MS:INSTRUMENT_NAME ISQ LT, Thermo Fisher Scientific MS:INSTRUMENT_TYPE GC-ITQ MS:MS_TYPE EI MS:ION_MODE POSITIVE MS:MS_COMMENTS Mass spectra were recorded in electronic impact (EI) mode at 70 eV, scanning at MS:MS_COMMENTS 40-600 m/z range, scan time 0.2 sec. Mass spectrometric solvent delay was MS:MS_COMMENTS settled as 9 min. MS:ACQUISITION_DATE 22/05/18 till 31/05/18 MS:FRAGMENTATION_METHOD EI-MS MS:HELIUM_FLOW 1 ml/min MS:ION_SOURCE_TEMPERATURE 260 MS:IONIZATION_ENERGY 70 eV MS:MASS_ACCURACY Unit Resolution MS:PRECURSOR_TYPE Full scan MS:SOURCE_TEMPERATURE 260 MS:SCAN_RANGE_MOVERZ 40-600 #MS_METABOLITE_DATA MS_METABOLITE_DATA:UNITS Relative Abundance MS_METABOLITE_DATA_START Samples T1 T2 T3 T4 6HUKR1 6HUKR2 6HUKR3 6HUKR4 6HUKR5 12HUKR1 12HUKR2 12HUKR3 12HUKR4 12HUKR5 24HUKR1 24HUKR2 24HUKR3 24HUKR4 24HUKR5 48HUKR1 48HUKR2 48HUKR3 48HUKR4 48HUKR5 96HUKR1 96HUKR2 96HUKR3 96HUKR4 96HUKR5 Factors Time:0h Time:0h Time:0h Time:0h Time:6h Time:6h Time:6h Time:6h Time:6h Time:12h Time:12h Time:12h Time:12h Time:12h Time:24h Time:24h Time:24h Time:24h Time:24h Time:48h Time:48h Time:48h Time:48h Time:48h Time:96h Time:96h Time:96h Time:96h Time:96h (-)-Shikimic acid 241083476 203614423 226255275 285767780 158457332 168844586 152392561 143532241 105525954 218061226 240461961 195533166 171743429 221730112 164094667 155779372 208462733 234426902 234426902 164584980 161048877 147908218 114770730 103787360 103631254 113636047 (S,R)-Noscapine 1479159 1758581 335937 41696 348666 263735 290360 429295 304724 346692 1333413 1274744 212012 212012 172631 457512 1453263 1146685 1158913 1275450 1,2,4,5-Tetrazine 448052 531668 329896 733700 659453 1005761 247011 323872 905014 1081636 536211 367404 274649 284621 623859 442860 370944 93725 401470 425733 97377 96945 1,2,4,5-Tetrazine, 3,6-dimethyl- 2233486 2402524 2506519 2437958 2328839 289118 2261353 3356665 1636640 2421805 1795492 4094745 2408341 2504667 2504667 1335452 2325125 1606893 1655756 2036582 1,2-Ethenediol, 2TMS derivative 23619653 64254632 32287268 27728347 24601865 20019546 78628268 54856477 33462070 48195520 90597820 77504772 41928621 78762086 78762086 75322346 14313700 78693975 89711408 11467018 94525768 1,4-Butanediamine 174161709 124088874 38108201 3189696 206612787 26350657 32555257 28165096 28696252 191677409 4872412 214267408 37288753 17055751 23338738 12345311 34874683 165959578 11649825 186707166 1,5-cis,8-cis-Undecatriene-3,7-diol bis(trimethylsilyl)ether 7769926 8276790 28466403 7128224 717089310 11248644 824754514 12-[(2,4-dimethoxyphenyl)carbonyl]-6a,6b,10,11,11a,12-hexahydro-8,11-epoxyoxepino[4',5':3,4]pyrrolo[1,2-a]quinolin-7(8H)-one 1007702 882468 68683 1085337 859488 137211 956246 454095 979758 54543 54543 1167507 337713 1170835 1110651 12-HETE 538334 3787607 4496416 335691 1870738 214772 294761 394128 651577 3620431 4476852 8537224 4287706 751649 1621426 3639607 18-Methyl-nodecane-1,2-dio, trimethylsilyl ether 90375 1239106 221839 118984 230563 349775 299035 299035 1794622 195309 431213 1-Aminocyclopropane-1-carboxylic acid 3559782 317489 244829 487834 487503 2345419 199081 134360 228728 309058 351904 351904 319716 632686 367592 1-Buten-3-yne 862006 636805 838173 573588 854478 769711 1021301 1167571 1194829 1157791 364424 712464 854360 2143211 989134 1322220 2285748 1-Cyclohexyldimethylsilyloxy-3-phenylpropane 407094 395489 411562 420618 381146 1-Decylamine 1893351 1500383 870116 4967389 6792747 7876773 2030970 4902447 3197259 1901569 1876825 3329356 1313666 1329652 2341218 3850070 2607396 843430 5435098 47960232 47960232 1671894 1330378 3098868 1433463 3038695 1213541 1066128 1-FORMYL-8-(TRIISOPROPYLSILYL)OXY-2-METHYL-1BETA,2ALPHA,(4A)ALPHA,5,6,7,8BETA,(8A)BETA-OCTAHYDROPHTHALENE 310269 437233 324975 1-Hexanol, TMS derivative 808610856 1141067762 1323603652 597809158 853790312 1042544079 1224963959 966837041 1064025268 782515771 1081535197 668826513 1168460787 878392911 949849208 950329765 950329765 1320566236 1289333692 908117982 1190538728 817223055 846445803 763018256 1-Hydroxybenzotriazole 336432 777277 634512 1721920 1072954 651747 448936 730848 695215 309721 631314 2009263 628278 550261 745438 596074 544215 544215 961921 969694 244237 822304 734063 681882 1-TETRADECENE 1331947 888241 1115292 1408031 1359829 1404385 1011237 1248509 891916 677974 1254165 1392995 918296 737078 1809281 1259017 1502311 1502311 988844 894112 946624 720480 660420 763449 2-((2-Chloroethyl)ethylamino)ethanol, TMS derivative 1460536 1409446 1133341 1359544 1349830 1140417 1398463 1398463 2,2-DIMETHYLBUTANE 1115902 441233 2526346 3905735 818201 3174008 2949107 617561 1829719 2310954 275363 1047335 1521102 728987 1957982 1005392 1312793 183048 1681937 2725603 2725603 1735102 1123345 1568830 475809 1055287 1124501 872186 2,3-Butanediol, 2TMS derivative 30674569 44264707 60805533 80861521 63673214 41671359 269870847 243799459 110889739 128043171 117841278 11027361 8892645 9251764 2,6,11-TETRAMETHYLDODECANE 3369487 3979182 5330608 3106709 1909738 1537967 6242661 1783366 289534 681841 5835494 1652229 2994438 4853999 1429977 1429977 1629704 3104974 2,6-Bis(tert-butyl)phenol, TMS derivative 2157459 2963265 3024488 1383511 1483032 1656952 2216670 2029652 2-[(Trimethylsilyl)oxy]tetradecanoic acid, bis(trimethylsilyl) ester 38360133 28831051 12069690 16083363 2-AMINO-1-ETHANOL 127290642 95715667 105001723 121862087 49223862 113663159 99813459 159175473 97067718 129793977 53254001 60845594 36477701 128249678 66591040 79608317 43017440 43222739 120712005 144352210 144352210 120533151 74906291 107401631 63559466 36236793 40173563 40916314 2-Anilinoethanol, TMS derivative 8800556 4437844 4467037 5090615 4464061 9623799 2-BUTANOL 52437087 64734311 71592114 6427863 67346662 57946417 60062867 71268424 10696362 88864657 10363343 25286775 74796064 2-Ethyl-3-trimethylsilyloxy(trimethylsilyl)butyrate 80228517 12476018 93226603 191676670 52781979 80778692 80778692 214683350 59247654 202562726 226688807 2-Hydroxymandelic acid, ethyl ester, di-TMS 157695 143405 637304 479386 388037 715143 412035 410035 301264 314290 2-HYDROXYPYRIDINE 19329324 32882182 34015118 30956304 543595 19668808 108841948 69874650 31393602 26532862 13627088 10592292 17341618 2-Methoxyethanol, triisobutylsilyl ether 5906004 7291482 5981344 7894685 8624869 7600861 7592197 8274826 12211370 2-O-Glycerol-α-d-galactopyranoside, hexa-TMS 450807876 66904137 85049070 566569858 724842357 726352206 700363480 759252443 268636014 984147243 960186967 359220916 38399075 603743466 176540667 54224305 425437555 447032571 447032571 118866526 68786984 913014190 124294914 107239796 111521720 122079635 2-Pentamethyldisilyloxypropane 25547379 44920612 34238591 81582293 75859190 75859190 86540278 2-Pentene, 5-(pentyloxy)-, (E)- 370442 487181 641455 504409 1361893 320038 932218 520164 300156 394948 1056754 295254 666140 1107129 17977440 2-Pyrrolidone carboxylic acid, N-trimethylsilyl-, trimethylsilyl ester 90967841 3-Indolebutyric acid 526624 2956441 948713 3475144 572933 899309 709687 5724111 801045 4404262 1143906 2711654 920017 3540339 884069 3-METHYL-2-(TRIMETHYLSILYL)OXYBENZOIC ACIDTRIMETHYLSILYL ESTER 592433 516342 884832 314759 3-Methylene-1,4-bis(trimethylsilyloxy) butane 11909708 19222864 8484530 23742856 21077412 8242538 17440999 15058702 13256851 12589676 13112412 9957795 4-Aminomethylcyclohexane carboxylic acid, N,N-bis(trimethylsilyl)-, trimethylsilyl ester 5754342 4052344 4447055 6142160 6349968 5984723 6562521 5811463 4042005 5631147 5827924 4415501 1544708 2332675 121546717 4194357 61294987 544391 6013510 6187024 6187024 3888552 3982861 163989331 4348048 3854741 3766368 105559362 5-HETE 1060546 972816 1256250 967477 1330790 1472929 761783 921286 1331889 952325 198581 632217 1073437 1891558 1891558 1294966 2078365 1127587 207198 1987557 5-methoxytryptamine 4TMS major 1756867 583958 2871343 1726695 1296526 6-METHYL-4-TRIMETHYLSILYLMETHYL-5,6-DIHYDRO-2H-PYRAN 16824269 12660896 13898290 7-Hydroxyflavone 1068515 506520 870987 1176272 807182 968623 784583 1021583 1104812 1104812 885810 1369113 917520 92405 911976 Adonitol 352617080 274175123 293537386 20829999 409678862 388562532 403878767 404066938 306639789 328995288 332912480 225316754 379231433 8680532 283412687 1286736 64757384 16406583 16406583 313341243 284674262 Allantoate 2868298 5151101 6944704 7312878 6906126 7133178 6259855 1786418 5636930 6763574 2141222 4368910 7101446 5287638 5287638 6603447 2030174 1533097 1776894 1974900 Alpha-Terpineol 24108588 7502090 24639081 10226491 14562112 18657501 9069474 18406129 13831806 6273046 15938617 8707604 8543257 8382542 8382542 15309890 30552120 10386104 Arachidyl alcohol 464725 1673673 215091 1129586 1114121 1104369 467067 554575 838793 925982 1142636 221595 818569 304655 476473 317530 1273976 1273976 1580875 349376 447748 998047 300102 Bentazone 224649 337291 6662558 514569 20197696 551059 140426770 84429714 1277943 23471535 907098 37128783 473054 473054 2109203 1679298 18273548 1678392 1288548 192524 Benzamide, N-benzoyl-N-(4,5-dimethyl-1H-1,2,3-triazol-1-yl)- 1043146 1727199 1981135 871709 1496399 94334 431590 423895 634363 907715 755387 2264777 599625 1404679 1540805 1400246 883069 2453874 2393017 1481529 1419099 1527259 955802 Berberine 1435939 286469 340837 233301 300871 1424035 1433869 348420 1357953 279403 335512 1104832 101711 1025925 212381 304848 304848 308823 218168 236704 282104 beta-D-Glucopyranose,1-thio-,1-(5-(methylsulfinyl)-N-(sulfooxy)-4-pentenimidate 767822 785284 973716 206015 511247 445606 165793 222999 1748144 263152 6566918 2216592 143655 2387625 2067180 719931 584324 767714 767714 103688 4327150 136330 251941 581604 2248800 601853 Beta-Leucine 672019 267718 461354 786897 143282 378120 205784 162191 648700 424143 686634 734879 586672 363007 599293 938606 b-Hydroxypropiote 2308830 34520929 38173703 69056319 71571054 36710783 2501453 2372759 34150399 285213 1339338 538381 2419178 80166430 48025219 43157030 3639021 50635478 45700345 46694150 49708811 BIS(TERT-BUTYLDIMETHYLSILYL) ETHER 408506102 22972640 24450137 228699833 569152750 26617748 564104877 Bisdemethoxycurcumin 348636 191464 251335 185545 244621 271922 207671 302750 200561 475798 409150 104653 2816592 250988 313236 270772 253940 253940 754449 485870 257704 424416 798888 727377 837950 Bisphenol A monomethyl ether, TMS derivative 2313202274 2543487073 3316157709 2595126099 2616567572 1432297 2763367945 2189187822 2222144961 2164715953 Boric acid, 3TMS derivative 543677025 517721244 484175351 480323858 561208718 Butal 1535978700 491437547 1282232091 1429353978 618462426 1851916595 1662581635 316933758 1697634808 1353291650 89768859 1941597380 6837910 1388022670 1723515076 1723515076 6099544 1680723372 Butal, 2,3,4-tris[(trimethylsilyl)oxy]-3-[[(trimethylsilyl)oxy]methyl]-, O-methyloxime, (S)- 20709807 23991633 10132694 19998498 18144310 17560317 1603241 Butanoic acid, 1,1-dimethylethyl ester 1637830 1549247 1272954 1650778 3465918 1195529 1567358 4307313 2832944 2653938 1354486 1120039 1357633 1379250 1653078 1175434 1403145 811310 1114404 730425 Carbamic acid,(trimethylsilyl),(trimethylsilyloxy) 19131319 21094938 18378647 22490903 24278517 15501270 14348467 Carbamic acid,(trimethylsilyl)[(trimethylsilyl)oxy] trimethylsilyl ester 182005290 24573336 43052688 186364163 251973540 24226651 160068651 21041125 35062264 70715249 19806961 19268890 20846167 28722541 21470947 29089114 34323428 39470000 Choline 1748799 254329 2788399 1218481 2209880 1260996 1682446 359190 1671636 1386385 940019 1622272 649016 1410684 1534861 1534861 881151 1618637 416194 375772 Chrysin 3345474 70485 1083967 4437970 116343 3587667 3686031 1407639 703255 2252437 1041950 1126350 2033251 2033251 2047927 4588329 2964831 1672160 1763968 Citramalate 677763 757733 5931653 9848424 1534134 1502825 459792 974432 1026031 1625724 850402 1099381 1099381 2185222 4094438 922442 1068768 295540 1760123 Citrate 187929535 140730660 161707278 223119721 211818120 224598883 158247547 196402190 140006283 143809063 109087938 173927183 146152674 243388630 265564084 265564084 137534890 178515694 154149260 135753516 150481290 Coumarin 2003844696 1680110286 1745463957 2029644982 2242589160 1142077161 2237567423 2212222398 1794531340 2132151223 2129900770 850942727 1787932203 134303719 2330839921 1847301433 1854487616 494268 2213938045 2109300810 2109300810 1906225865 1715798680 2091676100 1774198854 1662221221 1707289403 1808278703 D-(-)-Fructose 248385145 351532652 128807711 112324157 189391460 418856839 459045875 113997798 364796799 374921798 374921798 271359173 424509744 D-(+)-Mannose 580618398 497465391 609977842 461024512 408260737 434790703 855974388 1028823468 870387652 600789219 561621487 1058242780 1118626818 D-Arabino-Hexonic acid, 3-deoxy-2,5,6-tris-O-(trimethylsilyl)-, γ-lactone 22925346 28049040 29084113 80005951 70636057 93063154 114636707 50324695 83941579 65098184 D-Glucose 148378798 110715299 124022269 174726260 241535367 196606442 202197577 157110467 146710554 132859648 194458972 17595147 13636489 176046 223206242 160895231 146138631 1528943 173311690 918137215 918137215 30791797 29753777 194076884 191096889 29849108 178064784 179509901 Dihydrojasmone 823734 400693 1123697 793197 568820 179617 503111 835222 757866 495094 231073 443265 553727 389688 389688 394671 1097580 251366 Dihydrophytol, TMS derivative 144129 276941 529083 190622 Dihydrouracil 540141623 375975 450042146 197903042 485248336 361905676 570039987 502048206 226186055 178654612 325071874 408126 24448967 249928835 404106612 404106612 124387692 422329997 DL-ALPHA,3,4-TRI(TRIMETHYLSILYL)OXY-PHENYLACETIC ACID TRIMETHYLSILYL ESTER 889746 145082 1452319 868837 514078 1089225 1065272 DL-Malic acid 856261325 872101484 975551104 972212120 899723767 883591741 869412554 810332641 768291937 1051012759 1128610660 1167551785 1064077841 819626254 684861557 688204496 1039957825 1064433103 1064433103 1016830910 1074044872 800361567 764262392 736516556 717824002 800240981 DL-Pyroglutamic acid 65513695 324306374 223211430 130246978 84070771 50993102 31561922 162137384 86240180 72690159 104963449 184997736 184997736 67708752 88882839 177046670 108338479 99827240 81139971 103654372 D-Mannose, 5TMS derivative 258419880 503592834 300971734 383270719 363652470 643018153 427766138 918515623 855580777 355315708 132380621 830549945 846593017 826437578 851213690 D-Ribose, 4TMS derivative 18422494 25666162 7920541 25179207 12989723 D-Threitol, 4TMS derivative 23001902 20496253 26037271 D-Xylopyranose, 4TMS derivative 20501742 19365449 22760813 30141035 24432950 23145950 49178963 49178963 18699750 53592587 28666558 26806928 27332476 D-Xylose, 4TMS derivative 26497084 22476417 23050176 20450372 28102699 11948628 17026930 17492486 Erythritol, 4TMS derivative 23975626 4617559 9278081 7005683 15566540 11056864 16737890 20343018 7374546 Ethamine, 2TMS derivative 1437454 1100616 1464837 2450603 1392675 1204937 262190 663979 408149 Ethyl α-D-glucopyranoside, 4TMS derivative 23616322 34346561 24298630 23741625 19812300 25224831 48161323 492102332 553123059 553123059 443874443 461195049 975234125 740124698 766948100 747944207 771469382 Ethylene glycol, 2TMS derivative 71200406 18250661 15177383 23735106 Formononetin 624284 524468 646174 700059 782489 773973 644014 840607 599463 322307 917662 764875 865500 321618 525193 GABA 22850924 15186823 35862791 28323116 45811088 33372567 20566912 23682122 31553906 31553906 30225972 1963075 Galactose oxime, 6TMS derivative 14048202 13800597 18903187 19890548 13623609 13899100 26958655 22283996 Gibberellin A4 686182 18107159 981727 948600 577506 1784934 970694 990707 694966 1032094 1032094 1263902 636071 15100715 3867682 2168569 2683494 Glutaric acid 940541 872271 771929 928585 751404 1025440 849634 631062 356808 645791 812670 212878 647979 786875 786875 939332 404533 5521307 1187076 Glyceric acid 12907035 16766755 18843968 17529178 19639832 21504777 12713734 26076328 22689318 13909149 11423263 14456922 16821584 19522828 19522828 13263811 11257587 14816031 8556835 Glycocholate 882483 1112010 274703 231596 335722 804949 139059 249604 50971 700362 269088 269088 119011 425526 856519 313033 742816 1171999 Glycylvaline 1710066 4836358 4612537 5639862 4481418 5269561 3673029 3298890 1524905 4552877 2880312 1937756 5246137 1698568 1746555 Glyoxylic acid 11959571 999308621 23268965 7787359 15134864 10162228 9287348 15358951 1003737985 2889520 100733143 17780438 1116551468 5624483 6061466 9706120 9706120 900034883 16450839 920343026 954792009 893460237 48985212 Hirsutine 211762 1382352 462954 608608 252341 346070 211487 259000 308559 308559 756143 508556 369437 Hirsutrin 11732037 16177460 18681437 22140123 14129196 13137326 12322167 11527939 16047697 16082024 23297165 16947821 10399100 14800674 15704609 15492842 15352774 15834943 Hydroxyatrazine 4514859 4827538 4745234 4945525 4617671 4864723 4826489 4198565 1801214 2507254 4722307 1932415 721724 4699928 5150682 5150682 4754634 1706764 1789818 2029922 Hydroxycotinine, TMS derivative 879090 1249903 1668378 561306 Hydroxylamine 534401132 563687721 843657802 671897667 819472230 648223911 712759124 470415462 775461413 603043019 305611521 482844172 422444702 948440548 651189899 489577810 473448611 784056674 824217326 824217326 567247566 493854963 750276411 502120280 474037745 476967343 544362136 Hydroxylamine, 3TMS derivative 816858863 624767332 Idonic acid, γ-lactone, 4TMS derivavative 112436666 109934401 125291492 138996043 171699849 146862715 146716100 Indole-3-acetate 4087488 3523057 1289120 6062066 2851430 2286778 4019476 4184781 1070002 1070002 2284161 2483732 1834306 2592486 Indomethacin 358279 512615 525408 631237 576918 310903 412334 379587 458562 545502 636951 1418280 601588 521867 433040 482510 110491 266213 266213 449136 214071 439503 446109 397469 433794 ISOBUTYL ACETATE 2189111 2961343 2535016 3546589 2288066 2574632 27107198 2825949 29185881 719373 2669754 1961946 2573383 3868150 3868150 1569438 6405772 2772526 L-5-Oxoproline 553416 1482654 778253 688463 1093380 1625169 396895 943923 379605 2428816 787580 427447 427447 193534 913206 1364589 Lactic Acid, 2TMS derivative 121230798 95655741 118917501 94805015 51589677 61140668 56734844 42895094 41460798 44609084 103996196 91658794 59584089 33827220 91942222 52559860 52559860 69990842 121320236 59202503 26705783 84230343 L-Arabitol 37839812 33066981 42167584 34252413 48072986 41329960 36378909 48841263 38631149 43353145 24310994 16931679 36914462 26712926 36226548 31350777 33265395 27150567 L-Aspartic acid 319317447 53835843 22834359 120166787 79465910 26479843 504020016 113584065 208866810 115594006 70373249 67161892 77989487 10111341 61301867 55778698 44335125 36401793 41809707 L-Aspartic acid, 2TMS derivative 70238112 201773727 161547171 154274966 76483785 Leucine 17051804 4347580 7963160 19363631 4553098 6197433 6194993 1256424 14137223 8973628 3143423 426012 10313098 3489148 2432114 12040826 9088118 9088118 13593291 2499480 1971569 L-Glutamic acid 326818708 206065640 224524138 311368470 283121746 311386780 355017734 322336081 250076776 223489904 233793643 214814451 190181588 278311447 205738437 263876860 394713936 315216464 315216464 257865483 232174551 328195221 248611592 268221660 258852916 285088707 L-Glutamine 4200150 5244406 2616841 14665274 1405551 2938142 863316 346689 2590222 120993926 129914 10810129 2251524 392079 128510854 146097747 146419676 L-Iditol 81856371 9560096 10485529 91058377 707368667 87759930 681811402 95208051 549248156 124926966 131529824 6237901 8624672 139495757 10236143 618564439 233017542 234276884 234276884 12159900 12621448 260733239 185659933 213887859 9007573 41796003 L-Lactic acid 1284841 1174967 582997 1806456 1403612 784391 667397 779319 587138 2115857 1405628 L-Proline 693614 359520 593243 478271 717625 503773 454295 229262 1198139 220591 418268 704687 560675 2183258 614573 316275 L-Serine 651710 23428490 26683932 36812578 82272642 110131844 105774183 56710379 24533875 17965197 427350 85887818 42623322 16896044 90338084 110657474 110657474 20318262 27434982 161824202 35010981 23074894 28398399 57447495 L-Threonine 627518420 17608863 30892402 23489092 25409993 15449305 101830 17743546 15740315 709378344 16184624 22438494 21787076 21787076 14219560 14554832 41623430 18033456 13596906 14525064 105875700 Luteolin-8-C-glucoside 366310908 704423312 496164582 2892596 2762038 396370839 529374989 512819614 4407730 524980543 7521773 6721873 258247489 808934723 808934723 3794053 19080326 609205499 4971572 Methoxyamine, TMS derivative 51614136 53400498 60257323 53605277 47984870 132170622 14347271 10677507 15861036 34276695 41359155 43345391 43345391 8334835 111299560 METHYL (2R,3R,4S)-3-(TERT-BUTYLDIMETHYLSILYLOXY)-2,4-DIMETHYLHEXANOATE 641012 755558 755558 219884 180920 647905 Methylmalote 61809650 8616848 196179042 15339475 208864300 196546349 7906094 174199741 912605595 223644068 223536440 223536440 10121898 834507040 243400621 799792770 869279921 N-alpha-(tert-Butoxycarbonyl)-L-histidine 4288324 3758652 4308664 3986738 4273366 630673 1764818 274806 912388 4585079 4585079 4041011 233288 Norspermidine 770795 70656 5392134 1956665 1610671 429435 1792571 7547917 411457 350484 255141 3437957 778521 2074419 N-PIPEROYLDIETHLAMINE 8518948 83193575 3605705 26656051 8491542 71181789 44056497 7808928 6614400 6614400 92816104 85991427 9328374 74204613 73138048 79224549 94963568 O-Acetylcarnitine 1058930 199259313 191184317 194496404 1658018 239360021 249070523 409764 1398860 1398860 758316 1998751 1655957 Octane, 2,6,6-trimethyl- 3938396 870956 1648025 2392538 1798522 5147890 1852721 1696856 1711538 4474255 1527368 550927 1492279 913642 1911914 4752880 4752880 1824118 1160349 469405 Octane, 2,7-dimethyl- 1824691 511650 1003414 1298639 2406962 1595820 444273 1383510 556273 1009784 480625 1224231 233689 1902316 1190310 1650239 603261 652107 652107 1362100 1162980 1311115 1766632 2135437 700152 865995 Octylamine 4470260 2163584 11451390 1030998 3637642 857666 1900536 3975496 1274347 1049640 1265945 1438466 2153368 3447457 1673208 2189263 1600661 1095086 1162989 2190944 Oleic acid 12182229 3057751 161980 148446 290407 250100 4333072 236481 178820 120430 120430 15656203 96486 104442 240262 120867 336690 Oxalic acid, 2TMS derivative 4943760 20393623 24894717 Palmitic acid 148010151 84726976 106265200 152527130 112042870 142161022 126345394 139091136 75544339 140230779 98076745 85999717 62529515 126238254 104921946 68976435 121393797 130446318 130446318 148109332 93586278 156838310 80369808 68610046 Palmitic Acid, TMS derivative 84001738 78136319 80720228 pelargonic acid 7980381 8048042 11801491 11390820 10699097 13857555 10995514 9726831 11067949 9232957 10937698 5583099 9712545 10295639 10295639 6549029 1498356 Penicillamine, 3TMS derivative 20575383 194908757 228727081 25506580 203154395 65748451 186583597 27662613 29578430 199699829 32810741 383318470 291194679 198876955 195311703 25219641 30354753 303334953 Phosphatidylcholine 22:0-18:2 160636 328050 259060 160951 345042 407327 312875 569267 322779 322779 1365853 376746 231929 Phosphatidylcholine lyso 17:1 1038263 1343838 312017 1268795 206833 1126476 356248 181722 409184 172513 72723 323245 253540 338181 Phosphoric acid, bis(trimethylsilyl) 2,3-bis[(trimethylsilyl)oxy]propyl ester 9717420 6530169 4821919 5151820 4667736 Phosphoric acid, bis[2,3-bis[(trimethylsilyl)oxy]propyl] trimethylsilyl ester 16793325 piperidine 26923089 11466518 17209960 31036618 16951146 18278343 19427543 6344715 18598024 16096812 23093347 9021351 15621997 15621997 5265597 18837387 386565 Propal, 2,3-bis[(trimethylsilyl)oxy]-, O-methyloxime, (S)- 20434124 76937659 48287049 42657513 375084568 Propanoic acid, 2-oxo-3-(trimethylsilyl)-, trimethylsilyl ester 83025804 56991380 116458000 113711673 96040006 122608003 116243498 15982386 15982386 139127324 132200324 83413319 170917421 Propanoic acid, 3-[[bis[(trimethylsilyl)oxy]phosphinyl]oxy]-2-[(trimethylsilyl)oxy]-, trimethylsilyl ester, (S)- 1949502 1949502 2485432 Propiote 422833881 1328667599 1861672932 94473616 485824492 519624588 446837723 127959190 1923975758 570529759 548130964 1158383 390804735 964148055 564643635 1515951128 2073310330 1455195 8360214 8360214 1407339030 19985793 1947015650 1359009546 1986696088 2014047813 Pyridine 280933 127899 321399 540236 1279249 1726506 183086 110277 148722 3291866 204083 703581 389876 840181 389587 Quercetin 3740478 262756 206434 335005 836075 23277689 434337 19628136 2915823 15355089 178635 178635 207900 18854445 10278616 530264 21638782 22440841 24603961 quinic acid 297636728 378135652 250254455 269620006 219946539 199065337 368046390 412294506 250967382 315253438 336610576 336610576 246745712 Quininic acid (5TMS) 308273129 342970104 189499646 395337808 334315447 236731638 195005852 256895584 261211606 236892965 224460809 208702769 227547412 ribitol 326132550 374156021 458730059 386790084 440725343 352031085 322805771 408897709 148306030 421290175 3591950 385907951 309775200 423359207 458265052 458265052 335826118 413893857 409907544 360302261 Seneciphylline 1110444 1671439 1945883 1729392 1650784 2021551 1278340 1220870 1850278 1990015 2097446 2678873 1399500 1725095 2369430 1554368 7605837 7605837 2105826 163710 1712037 1186485 1309028 1460333 Silane, dimethylbis[(trimethylsilyl)methyl]- 24356685 6972895 27974621 15513693 24070865 23791792 31001159 19287110 15527452 34568427 Silylamine, 1,1,1-trimethyl-N-[6-(trimethylsiloxy)-2-phthyl]- 7262401 3928918 Sotalol 7725299 1615114 1944964 5629271 7498595 1387050 3763118 1506407 1945326 14105018 2338562 5012992 793903 7660588 1155376 282413 4434475 4701157 4701157 1254919 2195067 251902 526153 Sphingomyelin d18:1-C19:0 533427 302239393 484801017 265111 228640 53896 378096041 5538361 504280338 489648866 264352 497031549 479656523 4416923 171557456 942235545 767551 584078360 908287730 669015271 695287515 Sphingomyelin d18:2-C23:0 1133757 703689 974305 1382250 781687 1535814 749041 537952 1207236 1207236 1114709 1901145 617278 869549 Stearic acid 149622231 209720966 161582135 78507533 97808616 86931563 102779283 97521132 74848743 162230 67895034 74283806 116606953 117073575 117073575 204012665 104154328 SUCCINIC ACID 61934726 34683401 41150395 65826188 67384552 68298627 68389091 68680427 38407337 62606475 61075129 33140369 29313450 2792719 77573388 38812256 36882030 68218720 68661760 68661760 44359312 37128310 68131399 34854594 31789223 31766781 37896617 Sucrose, 8TMS derivative 1534719813 1141922352 1265129059 1521962030 1511010005 1361172419 1419556235 1441636947 1094494676 2133379055 2436177809 1983002948 1864531714 1836054303 1386830647 1414790069 233416 1241317012 2050492198 2050492198 1610706375 1753450035 1956318194 1655073202 1675785199 1711843376 1682738654 Sulfurous acid, 2-ethylhexyl hexyl ester 3657606 2385121 5121162 1971581 5290789 4117533 959153 1384720 1194047 5260788 3643666 4106052 4784323 826447 2492588 Terbutaline, N-trifluoroacetyl-O,O,o-tris(trimethylsilyl)deriv. 202516 312804 threo-b-methylaspartate 402378 618812 265721 390509 898449 154583 302998 294772 384601 560448 560448 414593 313955 675887 1664458 359472 1279171 Thymidine 8023237 141756 7993760 7152982 7639157 8431221 7916492 6248789 2979411 7352951 7547578 2720229 Tranexamic acid, 3TMS derivative 122286053 TRANS-1-PROPENE-1,2,3-TRICARBOXYLIC ACID TRI(TRIMETHYLSILYL) ESTER 107513534 78526456 74334658 125040779 70327261 196481463 152505820 TRANS-2-BUTENE-1,4-DICARBOXYLIC ACID BIS(TRIMETHYLSILYL) ESTER 177403318 183755787 120844915 177739313 15173699 115549023 145309947 7592055 5688876 7209345 trans-Cinmic acid 61197559 34899707 38103193 62348609 22796849 30552696 24187267 61791446 31111030 86991203 46201383 48940500 59891220 54376913 54376913 74137602 39124058 44181282 43797554 Triethanolamine, 3TMS derivative 1384996 1196314 1270324 TRIS(TRIMETHYLSILYL)METHANE 21579645 6730525 4962596 4743886 6520572 3583768 1692043 8553426 5998656 2835897 1494977 9739895 7112818 Undecane, 4,7-dimethyl- 1752315 1353586 2764163 1799631 4935100 1045538 3983890 3086319 6195276 5047096 3541989 3162698 4814460 5928282 5193061 5207052 3793587 3114638 3440579 3961430 Valeric acid 410480 3265398 1729935 862232 503066 1058993 1498307 563657 3284172 8067100 476708 883360 3165353 660897 620779 436204 839396 3514845 36694799 8929034 8929034 1531288 2952051 367898 313408 181592 476283 370960 Valine, N-trimethylsilyl-, trimethylsilyl ester 14438369 13030425 9569263 α-Benzylphenethylamine 12731776 8273741 16665794 8569357 8516174 10321928 8942901 9857783 9834253 4215028 15032544 5833029 12504037 10697410 10697410 6456739 11946910 4782870 3765699 α-D-Lactose, 8TMS derivative 463827223 40274245 10805536 496605071 490813096 13178564 130412034 374711550 372972498 360478649 379521487 α-l-Galactofuranoside, methyl 6-deoxy-2,3,5-tris-O-(trimethylsilyl)- 6694298 6998697 8730008 5947228 9497074 7040104 8244760 7193382 14380630 10923035 10851303 12578922 α-L-Idopyranuronic acid, 5TMS derivative 66441186 33736496 40263644 72733061 64229164 62322409 59935709 62422756 29032728 78742204 85617926 49797637 39333204 80439500 39034709 34411264 78808369 87699497 87699497 44509973 51118403 91178863 52445632 43175528 43407094 41490863 α-Methyl-L-tyrosine, 3TMS derivative 82043010 80227459 80227459 51119763 160220185 51449620 71082902 66545477 79612465 β-d-Glucopyranoside, 2-[[4-(trimethylsilyl)oxy]phenyl]ethyl, tetrakis(trimethylsilyl) 2608896 22287899 8358102 β-Gentiobiose, octakis(trimethylsilyl) ether, methyloxime (isomer 1) 2481005 6355034 3701329 MS_METABOLITE_DATA_END #METABOLITES METABOLITES_START metabolite_name (-)-Shikimic acid (S,R)-Noscapine 1,2,4,5-Tetrazine 1,2,4,5-Tetrazine, 3,6-dimethyl- 1,2-Ethenediol, 2TMS derivative 1,4-Butanediamine 1,5-cis,8-cis-Undecatriene-3,7-diol bis(trimethylsilyl)ether 12-[(2,4-dimethoxyphenyl)carbonyl]-6a,6b,10,11,11a,12-hexahydro-8,11-epoxyoxepino[4',5':3,4]pyrrolo[1,2-a]quinolin-7(8H)-one 12-HETE 18-Methyl-nodecane-1,2-dio, trimethylsilyl ether 1-Aminocyclopropane-1-carboxylic acid 1-Buten-3-yne 1-Cyclohexyldimethylsilyloxy-3-phenylpropane 1-Decylamine 1-FORMYL-8-(TRIISOPROPYLSILYL)OXY-2-METHYL-1BETA,2ALPHA,(4A)ALPHA,5,6,7,8BETA,(8A)BETA-OCTAHYDROPHTHALENE 1-Hexanol, TMS derivative 1-Hydroxybenzotriazole 1-TETRADECENE 2-((2-Chloroethyl)ethylamino)ethanol, TMS derivative 2,2-DIMETHYLBUTANE 2,3-Butanediol, 2TMS derivative 2,6,11-TETRAMETHYLDODECANE 2,6-Bis(tert-butyl)phenol, TMS derivative 2-[(Trimethylsilyl)oxy]tetradecanoic acid, bis(trimethylsilyl) ester 2-AMINO-1-ETHANOL 2-Anilinoethanol, TMS derivative 2-BUTANOL 2-Ethyl-3-trimethylsilyloxy(trimethylsilyl)butyrate 2-Hydroxymandelic acid, ethyl ester, di-TMS 2-HYDROXYPYRIDINE 2-Methoxyethanol, triisobutylsilyl ether 2-O-Glycerol-α-d-galactopyranoside, hexa-TMS 2-Pentamethyldisilyloxypropane 2-Pentene, 5-(pentyloxy)-, (E)- 2-Pyrrolidone carboxylic acid, N-trimethylsilyl-, trimethylsilyl ester 3-Indolebutyric acid 3-METHYL-2-(TRIMETHYLSILYL)OXYBENZOIC ACIDTRIMETHYLSILYL ESTER 3-Methylene-1,4-bis(trimethylsilyloxy) butane 4-Aminomethylcyclohexane carboxylic acid, N,N-bis(trimethylsilyl)-, trimethylsilyl ester 5-HETE 5-methoxytryptamine 4TMS major 6-METHYL-4-TRIMETHYLSILYLMETHYL-5,6-DIHYDRO-2H-PYRAN 7-Hydroxyflavone Adonitol Allantoate Alpha-Terpineol Arachidyl alcohol Bentazone Benzamide, N-benzoyl-N-(4,5-dimethyl-1H-1,2,3-triazol-1-yl)- Berberine beta-D-Glucopyranose,1-thio-,1-(5-(methylsulfinyl)-N-(sulfooxy)-4-pentenimidate Beta-Leucine b-Hydroxypropiote BIS(TERT-BUTYLDIMETHYLSILYL) ETHER Bisdemethoxycurcumin Bisphenol A monomethyl ether, TMS derivative Boric acid, 3TMS derivative Butal Butal, 2,3,4-tris[(trimethylsilyl)oxy]-3-[[(trimethylsilyl)oxy]methyl]-, O-methyloxime, (S)- Butanoic acid, 1,1-dimethylethyl ester Carbamic acid,(trimethylsilyl),(trimethylsilyloxy) Carbamic acid,(trimethylsilyl)[(trimethylsilyl)oxy] trimethylsilyl ester Choline Chrysin Citramalate Citrate Coumarin D-(-)-Fructose D-(+)-Mannose D-Arabino-Hexonic acid, 3-deoxy-2,5,6-tris-O-(trimethylsilyl)-, γ-lactone D-Glucose Dihydrojasmone Dihydrophytol, TMS derivative Dihydrouracil DL-ALPHA,3,4-TRI(TRIMETHYLSILYL)OXY-PHENYLACETIC ACID TRIMETHYLSILYL ESTER DL-Malic acid DL-Pyroglutamic acid D-Mannose, 5TMS derivative D-Ribose, 4TMS derivative D-Threitol, 4TMS derivative D-Xylopyranose, 4TMS derivative D-Xylose, 4TMS derivative Erythritol, 4TMS derivative Ethamine, 2TMS derivative Ethyl α-D-glucopyranoside, 4TMS derivative Ethylene glycol, 2TMS derivative Formononetin GABA Galactose oxime, 6TMS derivative Gibberellin A4 Glutaric acid Glyceric acid Glycocholate Glycylvaline Glyoxylic acid Hirsutine Hirsutrin Hydroxyatrazine Hydroxycotinine, TMS derivative Hydroxylamine Hydroxylamine, 3TMS derivative Idonic acid, γ-lactone, 4TMS derivavative Indole-3-acetate Indomethacin ISOBUTYL ACETATE L-5-Oxoproline Lactic Acid, 2TMS derivative L-Arabitol L-Aspartic acid L-Aspartic acid, 2TMS derivative Leucine L-Glutamic acid L-Glutamine L-Iditol L-Lactic acid L-Proline L-Serine L-Threonine Luteolin-8-C-glucoside Methoxyamine, TMS derivative METHYL (2R,3R,4S)-3-(TERT-BUTYLDIMETHYLSILYLOXY)-2,4-DIMETHYLHEXANOATE Methylmalote N-alpha-(tert-Butoxycarbonyl)-L-histidine Norspermidine N-PIPEROYLDIETHLAMINE O-Acetylcarnitine Octane, 2,6,6-trimethyl- Octane, 2,7-dimethyl- Octylamine Oleic acid Oxalic acid, 2TMS derivative Palmitic acid Palmitic Acid, TMS derivative pelargonic acid Penicillamine, 3TMS derivative Phosphatidylcholine 22:0-18:2 Phosphatidylcholine lyso 17:1 Phosphoric acid, bis(trimethylsilyl) 2,3-bis[(trimethylsilyl)oxy]propyl ester Phosphoric acid, bis[2,3-bis[(trimethylsilyl)oxy]propyl] trimethylsilyl ester piperidine Propal, 2,3-bis[(trimethylsilyl)oxy]-, O-methyloxime, (S)- Propanoic acid, 2-oxo-3-(trimethylsilyl)-, trimethylsilyl ester Propanoic acid, 3-[[bis[(trimethylsilyl)oxy]phosphinyl]oxy]-2-[(trimethylsilyl)oxy]-, trimethylsilyl ester, (S)- Propiote Pyridine Quercetin quinic acid Quininic acid (5TMS) ribitol Seneciphylline Silane, dimethylbis[(trimethylsilyl)methyl]- Silylamine, 1,1,1-trimethyl-N-[6-(trimethylsiloxy)-2-phthyl]- Sotalol Sphingomyelin d18:1-C19:0 Sphingomyelin d18:2-C23:0 Stearic acid SUCCINIC ACID Sucrose, 8TMS derivative Sulfurous acid, 2-ethylhexyl hexyl ester Terbutaline, N-trifluoroacetyl-O,O,o-tris(trimethylsilyl)deriv. threo-b-methylaspartate Thymidine Tranexamic acid, 3TMS derivative TRANS-1-PROPENE-1,2,3-TRICARBOXYLIC ACID TRI(TRIMETHYLSILYL) ESTER TRANS-2-BUTENE-1,4-DICARBOXYLIC ACID BIS(TRIMETHYLSILYL) ESTER trans-Cinmic acid Triethanolamine, 3TMS derivative TRIS(TRIMETHYLSILYL)METHANE Undecane, 4,7-dimethyl- Valeric acid Valine, N-trimethylsilyl-, trimethylsilyl ester α-Benzylphenethylamine α-D-Lactose, 8TMS derivative α-l-Galactofuranoside, methyl 6-deoxy-2,3,5-tris-O-(trimethylsilyl)- α-L-Idopyranuronic acid, 5TMS derivative α-Methyl-L-tyrosine, 3TMS derivative β-d-Glucopyranoside, 2-[[4-(trimethylsilyl)oxy]phenyl]ethyl, tetrakis(trimethylsilyl) β-Gentiobiose, octakis(trimethylsilyl) ether, methyloxime (isomer 1) METABOLITES_END #END