ZHANG, Jia-Rong; TROSSAT-MAGNIN, Claudine; BATHANY, Katell; NEGRONI, Luc; DELROT, Serge; CHAUDIÈRE, Jean

doi:10.3390/molecules27031047

ZHANG, Jia-Rong
Chimie et Biologie des Membranes et des Nanoobjets [CBMN]

TROSSAT-MAGNIN, Claudine

Ecophysiologie et Génomique Fonctionnelle de la Vigne [UMR EGFV]

BATHANY, Katell
Chimie et Biologie des Membranes et des Nanoobjets [CBMN]

Langue

Article de revue

Ce document a été publié dans

Molecules. 2022-02-03, vol. 27, n° 3, p. 1047

Résumé en anglais

Twelve polyphenols from three distinct families (dihydroflavonols, flavan-3-ols, and flavanones) were studied as potential substrates of anthocyanidin synthase from Vitis vinifera (VvANS). Only flavan-3-ols of (2R,3S) configuration having either a catechol or gallol group on ring B are accepted as substrates. Only dihydroflavonols of (2R,3R) configuration are accepted as substrates, but a catechol or gallol group is not mandatory. Flavanones are not substrates of VvANS. HPLC and MS/MS analyses of the enzymatic products showed that the VvANS-catalyzed oxidative transformation of (+)-dihydroflavonols, such as dihydroquercetin, dihydrokaempferol and dihydromyricetin, leads only to the corresponding flavonols. Among the flavan-3-ols recognized as substrates, (+)-gallocatechin was only transformed into delphinidin by VvANS, whereas (+)-catechin was transformed into three products, including two major products that were an ascorbate–cyanidin adduct and a dimer of oxidized catechin, and a minor product that was cyanidin. Data from real-time MS monitoring of the enzymatic transformation of (+)-catechin suggest that its products are all derived from the initial C3-hydroxylation intermediate, i.e., a 3,3-gem-diol, and their most likely formation mechanism is discussed.< Réduire

Mots clés en anglais

Anthocyanidin synthase

Vitis vinifera

2-oxoglutarate

Ascorbate

Dihydroflavonol

Flavanol

Catechin

Leucoanthocyanidin

Structure-activity relationship

Mass spectrometry

URI

https://oskar-bordeaux.fr/handle/20.500.12278/171900

DOI

http://dx.doi.org/10.3390/molecules27031047

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Oxidative Transformation of Dihydroflavonols and Flavan-3-ols by Anthocyanidin Synthase from Vitis vinifera

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Oxidative Transformation of Dihydroflavonols and Flavan-3-ols by Anthocyanidin Synthase from Vitis vinifera

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Résumé en anglais

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