title: Remarkable biomimetic chemoselective aerobic oxidation of flavano-ellagitannins found in oak-aged wine.
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.
authors.affiliation: 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).
authors.forename: Emilie
authors.initials: E
authors.lastname: Petit
authors.forename: Dorothée
authors.initials: D
authors.lastname: Lefeuvre
authors.forename: Rémi
authors.initials: R
authors.lastname: Jacquet
authors.forename: Laurent
authors.initials: L
authors.lastname: Pouységu
authors.forename: Denis
authors.initials: D
authors.lastname: Deffieux
authors.forename: Stéphane
authors.initials: S
authors.lastname: Quideau
mesh_terms: D016588:Anticarcinogenic Agents / Q000493:pharmacokinetics*; D000975:Antioxidants / Q000493:pharmacokinetics*; D032701:Biomimetics; D004032:Diet; D006801:Humans; D047348:Hydrolyzable Tannins / Q000737:chemistry*; D010084:Oxidation-Reduction; D014920:Wine / Q000032:analysis*
chemical_list: D016588:Anticarcinogenic Agents; D000975:Antioxidants; D047348:Hydrolyzable Tannins; C013515:ellagitannin
keywords: biosynthesis; chemoselectivity; oxidation; tannins; wine