Remarkable biomimetic chemoselective aerobic oxidation of flavano-ellagitannins found in oak-aged wine

Emilie Petit; Dorothée Lefeuvre; Rémi Jacquet; Laurent Pouységu; Denis Deffieux; Stéphane Quideau

doi:10.1002/anie.201305839

Remarkable biomimetic chemoselective aerobic oxidation of flavano-ellagitannins found in oak-aged wine

Angew Chem Int Ed Engl. 2013 Oct 25;52(44):11530-3. doi: 10.1002/anie.201305839. Epub 2013 Sep 13.

Authors

Emilie Petit¹, Dorothée Lefeuvre, Rémi Jacquet, Laurent Pouységu, Denis Deffieux, Stéphane Quideau

Affiliation

¹ Université de Bordeaux, Institut des Sciences Moléculaires (CNRS-UMR 5255) and Institut Européen de Chimie et Biologie, 2 rue Robert Escarpit, 33607 Pessac Cedex (France).

PMID: 24039115
DOI: 10.1002/anie.201305839

Abstract

Under the auspices of Bacchus! Acutissimins, natural flavano-ellagitannins, occur in oak-aged wine as a result of a diastereoselective condensation reaction of the flavan-3-ol catechin, a component of grapes, with the C-glucosidic ellagitannin vescalagin, found in oak. The acutissimins are further converted into natural mongolicains and analogues of camelliatannin G in a remarkably chemoselective fashion by simple aerobic oxidation.

Keywords: biosynthesis; chemoselectivity; oxidation; tannins; wine.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Anticarcinogenic Agents / pharmacokinetics*
Antioxidants / pharmacokinetics*
Biomimetics
Diet
Humans
Hydrolyzable Tannins / chemistry*
Oxidation-Reduction
Wine / analysis*

Substances

Anticarcinogenic Agents
Antioxidants
Hydrolyzable Tannins
ellagitannin