Chiroptical and Potential In Vitro Anti-Inflammatory Properties of Viniferin Stereoisomers from Grapevine (Vitis vinifera L)

Autor: Guillaume Buffeteau, Ruth Hornedo-Ortega, Julien Gabaston, Nicolas Daugey, Antonio Palos-Pinto, Anne Thienpont, Thierry Brotin, Jean-Michel Mérillon, Thierry Buffeteau, Pierre Waffo-Teguo
Přispěvatelé: Unité de Recherche Œnologie [Villenave d'Ornon] (OENO), Université de Bordeaux (UB)-Institut des Sciences de la Vigne et du Vin (ISVV)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE), Institut des Sciences Moléculaires (ISM), Université Montesquieu - Bordeaux 4-Université Sciences et Technologies - Bordeaux 1 (UB)-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Chimie - UMR5182 (LC), École normale supérieure de Lyon (ENS de Lyon)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Jazyk: angličtina
Rok vydání: 2022
Předmět:
Zdroj: Food Chemistry
Food Chemistry, 2022, 393, pp.133359. ⟨10.1016/j.foodchem.2022.133359⟩
ISSN: 0308-8146
1873-7072
DOI: 10.1016/j.foodchem.2022.133359⟩
Popis: International audience; Determination of stereochemistry and enantiomeric excess in chiral natural molecules is a research of great interest because enantiomers can exhibit different biological activities. Viniferin stilbene dimers are natural molecules present in grape berries and wine but also, in larger amount, in stalks of grapevine. Four stereoisomers of viniferin stilbene dimers (7aS,8aS)-E-ε-viniferin (1a), (7aR,8aR)-E-ε-viniferin (1b), (7aS,8aR)-Eε-viniferin (2a), and (7aR,8aS)-E-ω-viniferin (2b) were isolated from grapevine stalks of Cabernet Sauvignon, Merlot and Sauvignon Blanc, using a combination of centrifugal partition chromatography (CPC), preparative and chiral HPLC. The structure elucidation of these molecules was achieved by NMR whereas the absolute configurations of the four stereoisomers were investigated by vibrational circular dichroism spectroscopy in combination with density functional theory (DFT) calculations. This study unambiguously established the (+)-(7aS,8aS) and (+)-(7aR,8aS) configurations for E-ε-viniferin and E-ω-viniferin, respectively. Finally, we show that Cabernet Sauvignon provided the quasi enantiopure (+)-(7aS,8aS)-E-εviniferin compound which presents the best anti-inflammatory and anti-oxidant activities.
Databáze: OpenAIRE
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