Oxidative Transformation of Dihydroflavonols and Flavan-3-ols by Anthocyanidin Synthase from Vitis vinifera
| dc.rights.license | open | en_US |
| hal.structure.identifier | Chimie et Biologie des Membranes et des Nanoobjets [CBMN] | |
| dc.contributor.author | ZHANG, Jia-Rong | |
| hal.structure.identifier | Ecophysiologie et Génomique Fonctionnelle de la Vigne [UMR EGFV] | |
| dc.contributor.author | TROSSAT-MAGNIN, Claudine
IDREF: 225347954 | |
| hal.structure.identifier | Chimie et Biologie des Membranes et des Nanoobjets [CBMN] | |
| dc.contributor.author | BATHANY, Katell | |
| hal.structure.identifier | Chimie et Biologie des Membranes et des Nanoobjets [CBMN] | |
| dc.contributor.author | NEGRONI, Luc | |
| hal.structure.identifier | Ecophysiologie et Génomique Fonctionnelle de la Vigne [UMR EGFV] | |
| dc.contributor.author | DELROT, Serge
IDREF: 058711503 | |
| hal.structure.identifier | Chimie et Biologie des Membranes et des Nanoobjets [CBMN] | |
| dc.contributor.author | CHAUDIÈRE, Jean | |
| dc.date.accessioned | 2023-02-08T14:44:35Z | |
| dc.date.available | 2023-02-08T14:44:35Z | |
| dc.date.issued | 2022-02-03 | |
| dc.identifier.issn | 1420-3049 | en_US |
| dc.identifier.uri | https://oskar-bordeaux.fr/handle/20.500.12278/171900 | |
| dc.description.abstractEn | 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. | |
| dc.language.iso | EN | en_US |
| dc.rights | Attribution 3.0 United States | * |
| dc.rights.uri | http://creativecommons.org/licenses/by/3.0/us/ | * |
| dc.subject.en | Anthocyanidin synthase | |
| dc.subject.en | Vitis vinifera | |
| dc.subject.en | 2-oxoglutarate | |
| dc.subject.en | Ascorbate | |
| dc.subject.en | Dihydroflavonol | |
| dc.subject.en | Flavanol | |
| dc.subject.en | Catechin | |
| dc.subject.en | Leucoanthocyanidin | |
| dc.subject.en | Structure-activity relationship | |
| dc.subject.en | Mass spectrometry | |
| dc.title.en | Oxidative Transformation of Dihydroflavonols and Flavan-3-ols by Anthocyanidin Synthase from Vitis vinifera | |
| dc.type | Article de revue | en_US |
| dc.identifier.doi | 10.3390/molecules27031047 | en_US |
| dc.subject.hal | Sciences du Vivant [q-bio]/Biologie végétale | en_US |
| bordeaux.journal | Molecules | en_US |
| bordeaux.page | 1047 | en_US |
| bordeaux.volume | 27 | en_US |
| bordeaux.hal.laboratories | Ecophysiologie et Génomique Fonctionnelle de la Vigne (EGFV) - UMR 1287 | en_US |
| bordeaux.issue | 3 | en_US |
| bordeaux.institution | Université de Bordeaux | en_US |
| bordeaux.institution | Bordeaux Sciences Agro | en_US |
| bordeaux.institution | INRAE | en_US |
| bordeaux.institution | Bordeaux INP | |
| bordeaux.institution | CNRS | |
| bordeaux.peerReviewed | oui | en_US |
| bordeaux.inpress | non | en_US |
| hal.identifier | hal-03979080 | |
| hal.version | 1 | |
| hal.date.transferred | 2023-02-08T14:44:38Z | |
| hal.export | true | |
| dc.rights.cc | CC BY | en_US |
| bordeaux.COinS | ctx_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.jtitle=Molecules&rft.date=2022-02-03&rft.volume=27&rft.issue=3&rft.spage=1047&rft.epage=1047&rft.eissn=1420-3049&rft.issn=1420-3049&rft.au=ZHANG,%20Jia-Rong&TROSSAT-MAGNIN,%20Claudine&BATHANY,%20Katell&NEGRONI,%20Luc&DELROT,%20Serge&rft.genre=article |
