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^*

^*Korrespondierende/r Autor/-in für diese Arbeit

Institut für Biotechnologie und Bioprozesstechnik (6510)

Publikation: Beitrag in einer Fachzeitschrift › Artikel › Begutachtung

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.

Originalsprache	englisch
Seiten (von - bis)	441-448
Seitenumfang	8
Fachzeitschrift	Food Chemistry
Jahrgang	266
DOIs	https://doi.org/10.1016/j.foodchem.2018.06.019
Publikationsstatus	Veröffentlicht - 15 Nov. 2018

ASJC Scopus subject areas

Analytische Chemie
Lebensmittelwissenschaften

Zugriff auf Dokument

10.1016/j.foodchem.2018.06.019

Andere Dateien und Links

http://www.scopus.com/inward/record.url?scp=85048439711&partnerID=8YFLogxK

Dieses zitieren

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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",

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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

KW - Grape

KW - Mass spectrometry

KW - Wine

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