Identification of new flavan-3-ol monoglycosides by UHPLC-ESI-Q-TOF in grapes and wine.
Flavan-3-ol monoglycosides, having four aglycons (+)-catechin, (-)-epicatechin, (-)-epigallocatechin and epicatechin gallate monomeric units, are detected for the first time in Vitis vinifera L. cv. Merlot grape seeds and wine. These compounds were analyzed in red wine, seed and skin extracts by electrospray ionization quadrupole time of flight mass spectrometry (MS) in negative mode. Fragment ions derived from retro-Diels Alder, heterocyclic ring fragmentation, benzofuran forming fragmentation and glycoside fragmentations were detected in targeted MS/MS mode. These compounds were not detected in skins; the comparative study showed evidence that these glycosylated compounds originate only from grape seeds. Our method allows for the identification of these glycosylated compounds based on their exact mass and their specific fragmentation pattern. However, exact glucose position on the monomeric units can not be determined. This work allowed us to partially identify 14 new flavan-3-ol monoglycosides, based on the exact mass of the molecular ions and their specific retro-Diels Alder, heterocyclic ring fragmentation, benzofuran forming fragmentation and glycoside fragmentations.
Enology Laboratory, Department of Chemistry, University of British Columbia, Okanagan Campus, Kelowna, British Columbia V1V 1V7, Canada.
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D002392:Catechin / Q000031:analogs & derivatives* / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D005419:Flavonoids / Q000737:chemistry*; D005638:Fruit / Q000737:chemistry; D006031:Glycosylation; D010936:Plant Extracts / Q000737:chemistry; D012639:Seeds / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods*; D053719:Tandem Mass Spectrometry; D027843:Vitis / Q000737:chemistry*; D014920:Wine / Q000032:analysis*
D005419:Flavonoids; D010936:Plant Extracts; C404987:flavan-3-ol; D002392:Catechin