Targeted identification of metabolites was performed by using the homemade database GrapeMetabolomics (around 1100 grape and wine metabolites)[1]. Predicted chromatographic retention times of compounds (Rt) were calculated by using the ACD/ChromGenius V2015 software (Advanced Chemistry Development, Inc., Toronto, ON, Canada, www.acdlabs.com). The calibration curve was calculated by using the Rt of metabolites previously identified in grape using the same chromatographic method.
Ref:
[1] Flamini R, De Rosso M, De Marchi F, et al. An innovative approach to grape metabolomics: stilbene profiling by suspect screening analysis. Metabolomics. 2013;9(6):1 243-1253
"],"repository":["MetaboLights"],"study_status":["Public"],"ptm_modification":[""],"instrument_platform":["Liquid Chromatography MS - alternating - reverse phase"],"chromatography_protocol":["Analyses were performed using a UHPLC Agilent 1290 Infinity system coupled to Agilent 1290 Infinity Autosampler (G4226A). Analyses were performed in both positive and negative ionization modes by recording data in full scan acquisition using Agilent MassHunter version B.04.00 (B4033.2) software. Chromatographic conditions: Zorbax reversed-phase column (RRHD SB-C18 3 × 150 mm, 1.8 μm) (Agilent Technologies, Santa Clara, CA), mobile phase composed by (a) 0.1% (v/v) aqueous formic acid and (b) 0.1% (v/v) formic acid in acetonitrile. Gradient elution program: 5% B isocratic for 8 min, from 5% to 45% B in 10 min, from 45% to 65% B in 5 min, from 65% to 90% in 4 min, and 90% B 10 min isocratic. Flow rate: 0.4 ml/min. Sample injection 10 μL; column temperature 35 °C. False positives were checked by analysis after each sample of a blank composed by mobile phases A/B 1:1 (v/v)
"],"publication":["Elucidations on the structures of some putative flavonoids identified in postharvest withered grapes (Vitis vinifera L.) by quadrupole time-of-flight mass spectrometry. 10.1002/jms.4639. PMID:32885551"],"submitter_name":["Mirko De Rosso"],"submitter_affiliation":["CREA-Viticulture & Enology Research Center"],"organism_part":["berry"],"technology_type":["mass spectrometry"],"disease":[""],"extraction_protocol":["20 berries were weighed and homogenized using liquid nitrogen, and the powder was extracted using pure methanol in ratio 2:1 (ml/g) under stirring for 20 min. A water volume equal to the mean weight loss of the sample (ml/g) and 200 μL of internal standard (IS) 40,5,7-trihydroxy flavanone 500 mg/L of solution were added, and the solution was centrifuged at 10 °C for 20 min. The supernatant was filtered through Acrodisc GHP 0.22-μm filter (Waters) by collecting the solution in a vial for LC/MS analysis. For each variety, 3 samples were prepared, and 2 replicate analyses of each sample were performed. Semiquantitative data of flavonoids were estimated as μg IS/kg fresh grape on the normalized intensity of the [M–H]− signals.
"],"organism":["Vitis vinifera"],"full_dataset_link":["https://www.ebi.ac.uk/metabolights/MTBLS1804"],"author":["Annarita Panighel.","Mirko De Rosso.","Riccardo Flamini.","Antonio Dalla Vedova."],"data_transformation_protocol":["Acquisition software Agilent MassHunter Qualitative Analysis B.05.00 (5.0.519.0) was used.
Overall identification score of compounds calculated by weighted average of the isotopic pattern signals (Wmass=100, Wabundance=60, Wspacing=50).
"],"study_factor":["Compound"],"submitter_email":["mirko.derosso@crea.gov.it"],"sample_collection_protocol":["15 kg each of Raboso Piave and Corvina grape was collected in 2013 from CREA-VE vine germplasm (Spresiano, Treviso, Italy), and the samples were stored in warehouse for 2 mths under controlled conditions of temperature (18 ± 2 °C), RH (40%),and air flow (0.3 m/s). After 60 days of dehydration, which corresponded to around 40% of grape berry weight loss, 3 samples of each variety formed by collecting berries from different clusters were frozen. Standards of myricetin-3-O-glucoside, quercetin, quercetin-3-O-glucoside, isorhamnetin-3-O-glucoside, kaempferol-3-O-glucoside, rutin, procyanidin B1, procyanidin B2, (+)-catechin, (−)-epicatechin, (−)-epicatechin-3-O-gallate, rhamnetin, and tamarixetin were purchased from Extrasynthese (Genay, France); 5-O- methylquercetin (azaleatin) was purchased from Carbosynth Ltd.(Compton, Berkshire, UK); trans-resveratrol, piceatannol, E-piceid,40,5,7-trihydroxy flavanone (naringenin), isorhamnetin (30-O- methylquercetin), and morin (3,5,7,20,40-pentahydroxyflavone) were purchased from Sigma-Aldrich (Milan, Italy). δ-Viniferin was provided by CT Chrom (Marly, Switzerland). Z-piceid was produced by photoisomerization of the E-isomer. E-ε viniferin was extracted from lignified vine cane of Gamaret according to the method by Pezet et al. [1]. Pinoquercetin (6-C-methylquercetin) was extracted from Quercus robusta bark chips using methanol, and the extract was purified by performing SPE-C18.
Ref:
[1] Pezet R, Perret C, Jean-Denis JB, Tabacchi R, Gindro K, Viret O. Delta-viniferin, a resveratrol dehydrodimer: one of the major stilbenes synthesized by stressed grapevine leaves. J Agric Food Chem. 2003 Aug 27;51(18):5488-92. doi: 10.1021/jf030227o. PMID: 12926902
"],"omics_type":["Metabolomics"],"study_design":["ultra-performance liquid chromatography-mass spectrometry","tandem mass spectrometry","grape withering","dihydromyricetin-hexoside","taxifolin-pentoside","peonidin-pentoside","flavonoids","(+)-dihydromyricetin","tetrahydroxyflavanone-hexoside"],"curator_keywords":["ultra-performance liquid chromatography-mass spectrometry","tandem mass spectrometry","grape withering","dihydromyricetin-hexoside","taxifolin-pentoside","peonidin-pentoside","flavonoids","(+)-dihydromyricetin","tetrahydroxyflavanone-hexoside"],"mass_spectrometry_protocol":["Ultra-High Performance Liquid Chromatography (UHPLC) Agilent 1290 Infinity system coupled to Agilent 1290 Infinity Autosampler (G4226A) and Agilent 6540 accurate-mass Quadrupole-Time of Flight (Q-TOF) Mass Spectrometer (nominal resolution 40.000) and Dual Agilent Jet Stream Ionization source (Agilent Technologies, Santa Clara, CA).
QTOF conditions: sheath gas nitrogen, 10 L/min at 400 °C; dehydration gas, 8 L/min at 350 °C; nebulizer pressure, 60 psi; nozzle voltage, 0 kV (negative mode) and 1 kV (positive mode); capillary voltage ±3.5 kV in positive and negative ion modes. Signals recorded in the m/z 100–1700 range at acquisition rate 2 spectra/s. Mass calibrations were performed by using standard mix G1969-85000 (Supelco Inc.) with residual error for the expected masses between ±0.2 ppm. Negative ionization lock masses: trifluoroacetic acid (TFA) anion at m/z 112.9856 and HP-0921 at m/z 966.0007 (ion [M+HCOO]−); positive ionization lock masses, purine at m/z 121.0509 and HP-0921 at m/z 922.0098.
MS/MS conditions: fragmentation of parent ions selected in the m/z 100–1700 range using collision energies of between 20 and 60 eV. Acquisition rate: 2 spectra/s.
"],"metabolite_name":["3,5,7,4'-tetrahydroxyflavanone-7-O-hexoside","peonidin-O-pentoside","taxifolin-O-pentoside","3,5,7,4'-tetrahydroxyflavanone-3-O-hexoside","dihydromyricetin-O-hexoside"],"pubmed_abstract":["Grape dehydration is an oenological process used for production of high-quality reinforced and sweet wines. High-resolution mass spectrometry (ultrahigh-performance liquid chromatography/quadrupole time-of-flight [UHPLC/QTOF]) was used to deepen the characterization of some flavonoids previously proposed in Corvina and Raboso Piave withered grapes. By performing a targeted data analysis workflow and orthogonal identification approaches (tandem mass spectrometry [MS/MS]), in silico fragmentation, and calculation of putative retention time), elucidation on the structures of six compounds previously proposed was achieved (taxifolin-pentoside, two tetrahydroxyflavanone-hexoside derivatives, a tetrahydroxy-dimethoxyflavanone-hexoside derivative, a pentahydroxyflavone, and peonidin-O-pentoside); and the structures of four putative new grape flavonoids were characterized (dihydromyricetin-O-hexoside, taxifolin-di-O-hexoside, isorhamnetin, and a pinoquercetin isomer). Findings enlarge the panorama of flavonoids in grape and of their possible biosynthetic pathways."],"pubmed_title":["Elucidations on the structures of some putative flavonoids identified in postharvest withered grapes (Vitis vinifera L.) by quadrupole time-of-flight mass spectrometry."],"pubmed_authors":["De Rosso Mirko M, Panighel Annarita A, Dalla Vedova Antonio A, Flamini Riccardo R"],"pubmed_abstract_synonyms":["Water, close to, screening, Pathway, anatomical protrusion, 2 Phenyl Chromenes, findings, Water Stress, (2R, Tandem, Wines, Liquid Chromatography, 4H-1-benzopyran-4-one, Bioflavonoid, 2-Phenyl-Benzopyrans, Spectrum Analyses, Mass Spectrometry Mass Spectrometry, Spectrum Analysis, 3-dihydro-3, protrusion, Spectroscopy, near to, 2-Phenyl-Chromene, 2 Phenyl Benzopyrans, Workflows, MS, TOF, dihydroquercetin, Mass, symptoms, 2, 4, 5, Analysis, Work Flow, 2-Phenyl-Chromenes, Biosynthetic, Mass Spectrum Analyses, tandem MS, Mass Spectroscopy, Mass Spectrum Analysis, Mass Spectrum, pentahydroxyflavone, Analyses, MS/MS, Flavonoid, MS2, 2 Phenyl Benzopyran, Spectrometry, signs, Pathways, Mass Spectrometry, Mass Spectrometry-Mass Spectrometry, dihydro-myricetin, 7-trihydroxy-2-(3, Biosynthetic Pathway., data analysis, 2 Phenyl Chromene, Bioflavonoids, data processing, spine, Data, approaches, Stress, vicinity of, 5-trihydroxyphenyl)-, 3R)-, Data Analyses, Work Flows, 2-Phenyl-Benzopyran"],"name_synonyms":["Mass Spectrum Analysis, Mass Spectrum, 2 Phenyl Chromenes, Analyses, Flavonoid, Vitis vinifera, 2 Phenyl Benzopyran, Spectrometry, Bioflavonoid, 2-Phenyl-Benzopyrans, Raisins, Spectrum Analyses, Spectrum Analysis, Spectroscopy, 2-Phenyl-Chromene, 2 Phenyl Benzopyrans, 2 Phenyl Chromene, Bioflavonoids, MS, TOF, Raisin, Mass, Mass., wine grape, Grapes, Grape, Analysis, Vitis vinifera subsp. vinifera, 2-Phenyl-Chromenes, Mass Spectrum Analyses, 2-Phenyl-Benzopyran, Mass Spectroscopy"],"pubmed_title_synonyms":["Mass Spectrum Analysis, Mass Spectrum, 2 Phenyl Chromenes, Analyses, Flavonoid, Vitis vinifera, 2 Phenyl Benzopyran, Spectrometry, Bioflavonoid, 2-Phenyl-Benzopyrans, Raisins, Spectrum Analyses, Spectrum Analysis, Spectroscopy, 2-Phenyl-Chromene, 2 Phenyl Benzopyrans, 2 Phenyl Chromene, Bioflavonoids, MS, TOF, Raisin, Mass, Mass., wine grape, Grapes, Grape, Analysis, Vitis vinifera subsp. vinifera, 2-Phenyl-Chromenes, Mass Spectrum Analyses, 2-Phenyl-Benzopyran, Mass Spectroscopy"],"description_synonyms":["Water, close to, screening, Pathway, anatomical protrusion, 2 Phenyl Chromenes, findings, Water Stress, (2R, Tandem, Wines, Liquid Chromatography, 4H-1-benzopyran-4-one, Bioflavonoid, 2-Phenyl-Benzopyrans, Spectrum Analyses, Mass Spectrometry Mass Spectrometry, Spectrum Analysis, 3-dihydro-3, protrusion, Spectroscopy, near to, 2-Phenyl-Chromene, 2 Phenyl Benzopyrans, Workflows, MS, TOF, dihydroquercetin, Mass, symptoms, 2, 4, 5, Analysis, Work Flow, 2-Phenyl-Chromenes, Biosynthetic, Mass Spectrum Analyses, tandem MS, Mass Spectroscopy, Mass Spectrum Analysis, Mass Spectrum, pentahydroxyflavone, Analyses, MS/MS, Flavonoid, MS2, 2 Phenyl Benzopyran, Spectrometry, signs, Pathways, Mass Spectrometry, Mass Spectrometry-Mass Spectrometry, dihydro-myricetin, 7-trihydroxy-2-(3, Biosynthetic Pathway., data analysis, 2 Phenyl Chromene, Bioflavonoids, data processing, spine, Data, approaches, Stress, vicinity of, 5-trihydroxyphenyl)-, 3R)-, Data Analyses, Work Flows, 2-Phenyl-Benzopyran"],"additional_accession":[]},"is_claimable":false,"name":"Elucidations on the structures of some putative flavonoids identified in postharvest withered grapes (Vitis vinifera L.) by quadrupole time-of-flight mass spectrometry","description":"Grape dehydration is an oenological process used for production of high-quality reinforced and sweet wines. High-resolution mass spectrometry (ultrahigh-performance liquid chromatography/quadrupole time-of-flight [UHPLC/QTOF]) was used to deepen the characterization of some flavonoids previously proposed in Corvina and Raboso Piave withered grapes. By performing a targeted data analysis workflow and orthogonal identification approaches (tandem mass spectrometry [MS/MS]), in silico fragmentation, and calculation of putative retention time), elucidation on the structures of six compounds previously proposed was achieved (taxifolin-pentoside, two tetrahydroxyflavanone-hexoside derivatives, a tetrahydroxy-dimethoxyflavanone-hexoside derivative, a pentahydroxyflavone, and peonidin-O-pentoside); and the structures of four putative new grape flavonoids were characterized (dihydromyricetin-O-hexoside, taxifolin-di-O-hexoside, isorhamnetin, and a pinoquercetin isomer). Findings enlarge the panorama of flavonoids in grape and of their possible biosynthetic pathways.","dates":{"publication":"2021-12-09","submission":"2020-06-16"},"accession":"MTBLS1804","cross_references":{"pubmed":["32885551"]}}