New flavanol O-glycosides in grape and wine

Marie Zerbib; Jean Paul Mazauric; Emmanuelle Meudec; Christine Le Guernevé; Alexander Lepak; Bernd Nidetzky; Véronique Cheynier; Nancy Terrier; Cédric Saucier

doi:10.1016/j.foodchem.2018.06.019

New flavanol O-glycosides in grape and wine

Marie Zerbib, Jean Paul Mazauric, Emmanuelle Meudec, Christine Le Guernevé, Alexander Lepak, Bernd Nidetzky, Véronique Cheynier, Nancy Terrier, Cédric Saucier^*

^*Corresponding author for this work

Institute of Biotechnology and Biochemical Engineering (6510)

Research output: Contribution to journal › Article › peer-review

Abstract

The presence of monomeric and dimeric flavan-3-ol monohexosides was investigated in grapes and wines. Polyphenol extracts were prepared from grape seeds and skins (Syrah, Merlot, and Cabernet-Sauvignon) sampled at three different developmental stages. Different wines (Tannat, Alicante, Syrah, Merlot, and Grenache) were also studied. The different samples obtained were analyzed by UPLC-ESI-IT-MS. Specific molecular ions corresponding to flavan-3-ol hexosides were detected by using targeted molecular ions with specific m/z values: 451 for (epi)catechin hexosides, and 739 for procyanidin dimer hexosides. 4′-O-β-glucosyl-(+)-catechin and 7-O-β-glucosyl-(+)-catechin were obtained by using a glucosyl transferase from apple, UGT71A15, and their structures determined by NMR. These glucosylated monomers and the dimers were identified in all analyzed grape seed and several skin extracts at the different stages and in wines made from different varieties.

Original language	English
Pages (from-to)	441-448
Number of pages	8
Journal	Food Chemistry
Volume	266
DOIs	https://doi.org/10.1016/j.foodchem.2018.06.019
Publication status	Published - 15 Nov 2018

Keywords

Flavan-3-ol glycoside
Grape
Mass spectrometry
Wine

ASJC Scopus subject areas

Analytical Chemistry
Food Science

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10.1016/j.foodchem.2018.06.019

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title = "New flavanol O-glycosides in grape and wine",

abstract = "The presence of monomeric and dimeric flavan-3-ol monohexosides was investigated in grapes and wines. Polyphenol extracts were prepared from grape seeds and skins (Syrah, Merlot, and Cabernet-Sauvignon) sampled at three different developmental stages. Different wines (Tannat, Alicante, Syrah, Merlot, and Grenache) were also studied. The different samples obtained were analyzed by UPLC-ESI-IT-MS. Specific molecular ions corresponding to flavan-3-ol hexosides were detected by using targeted molecular ions with specific m/z values: 451 for (epi)catechin hexosides, and 739 for procyanidin dimer hexosides. 4′-O-β-glucosyl-(+)-catechin and 7-O-β-glucosyl-(+)-catechin were obtained by using a glucosyl transferase from apple, UGT71A15, and their structures determined by NMR. These glucosylated monomers and the dimers were identified in all analyzed grape seed and several skin extracts at the different stages and in wines made from different varieties.",

keywords = "Flavan-3-ol glycoside, Grape, Mass spectrometry, Wine",

author = "Marie Zerbib and Mazauric, {Jean Paul} and Emmanuelle Meudec and {Le Guernev{\'e}}, Christine and Alexander Lepak and Bernd Nidetzky and V{\'e}ronique Cheynier and Nancy Terrier and C{\'e}dric Saucier",

year = "2018",

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doi = "10.1016/j.foodchem.2018.06.019",

language = "English",

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AU - Zerbib, Marie

AU - Mazauric, Jean Paul

AU - Meudec, Emmanuelle

AU - Le Guernevé, Christine

AU - Lepak, Alexander

AU - Nidetzky, Bernd

AU - Cheynier, Véronique

AU - Terrier, Nancy

AU - Saucier, Cédric

PY - 2018/11/15

Y1 - 2018/11/15

N2 - The presence of monomeric and dimeric flavan-3-ol monohexosides was investigated in grapes and wines. Polyphenol extracts were prepared from grape seeds and skins (Syrah, Merlot, and Cabernet-Sauvignon) sampled at three different developmental stages. Different wines (Tannat, Alicante, Syrah, Merlot, and Grenache) were also studied. The different samples obtained were analyzed by UPLC-ESI-IT-MS. Specific molecular ions corresponding to flavan-3-ol hexosides were detected by using targeted molecular ions with specific m/z values: 451 for (epi)catechin hexosides, and 739 for procyanidin dimer hexosides. 4′-O-β-glucosyl-(+)-catechin and 7-O-β-glucosyl-(+)-catechin were obtained by using a glucosyl transferase from apple, UGT71A15, and their structures determined by NMR. These glucosylated monomers and the dimers were identified in all analyzed grape seed and several skin extracts at the different stages and in wines made from different varieties.

AB - The presence of monomeric and dimeric flavan-3-ol monohexosides was investigated in grapes and wines. Polyphenol extracts were prepared from grape seeds and skins (Syrah, Merlot, and Cabernet-Sauvignon) sampled at three different developmental stages. Different wines (Tannat, Alicante, Syrah, Merlot, and Grenache) were also studied. The different samples obtained were analyzed by UPLC-ESI-IT-MS. Specific molecular ions corresponding to flavan-3-ol hexosides were detected by using targeted molecular ions with specific m/z values: 451 for (epi)catechin hexosides, and 739 for procyanidin dimer hexosides. 4′-O-β-glucosyl-(+)-catechin and 7-O-β-glucosyl-(+)-catechin were obtained by using a glucosyl transferase from apple, UGT71A15, and their structures determined by NMR. These glucosylated monomers and the dimers were identified in all analyzed grape seed and several skin extracts at the different stages and in wines made from different varieties.

KW - Flavan-3-ol glycoside

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KW - Mass spectrometry

KW - Wine

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VL - 266

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JO - Food Chemistry

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ER -

New flavanol O-glycosides in grape and wine

Abstract

Keywords

ASJC Scopus subject areas

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