Resveratrol transformation in red wine after heat treatment

[Display omitted] •Four resveratrol dimers were produced by oxidative coupling of resveratrol in ethanol.•Oxidative coupling reaction of resveratrol was faster and yield was higher using AgOAc.•Two of the produced dimers are reported for the first time: oxistilbenins F and G.•The compounds were iden...

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Published in:Food research international 2020-06, Vol.132, p.109068-109068, Article 109068
Main Authors: El Khawand, Toni, Valls Fonayet, Josep, Da Costa, Grégory, Hornedo-Ortega, Ruth, Jourdes, Michael, Franc, Céline, de Revel, Gilles, Decendit, Alain, Krisa, Stéphanie, Richard, Tristan
Format: Article
Language:English
Subjects:
Alcoholic Beverages - analysis
Animals
Anti-Inflammatory Agents - pharmacology
Anti-inflammatory effect
Hemisynthesis
Hot Temperature
Life Sciences
Lipopolysaccharides - pharmacology
Macrophages - drug effects
Mice
Nitric Oxide
Oxidative coupling
Phenols - analysis
RAW 264.7 Cells
Reactive Oxygen Species
Resveratrol
Resveratrol - chemistry
Resveratrol - pharmacology
Stilbene
Stilbenes - analysis
Wine
Wine - analysis
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Summary:[Display omitted] •Four resveratrol dimers were produced by oxidative coupling of resveratrol in ethanol.•Oxidative coupling reaction of resveratrol was faster and yield was higher using AgOAc.•Two of the produced dimers are reported for the first time: oxistilbenins F and G.•The compounds were identified and quantified in red wine after heat treatment.•The de novo synthetized compounds exhibited anti-inflammatory properties. Resveratrol is a well-known wine constituent. Its concentration can vary according to the cultivar choice and the winemaking process. Due to its phenolic structure, resveratrol could be transformed under high temperature or oxidative conditions, leading to the formation of various derivatives including oligomers. Hence, the goal of this study is to investigate the presence of these derivatives in wine. In the first stage, hemisynthesis of oligomeric stilbenes was achieved from resveratrol in ethanol by oxidative coupling using metals. Four de novo synthetized resveratrol derivatives were identified by MS and NMR spectroscopy including two new molecules, oxistilbenin F and oxistilbenin G. In the second stage, analysis of red wine after heat treatment by LC-MS confirmed the presence of some of these compounds in wine. Finally, the anti-inflammatory effects of the compounds were evaluated by studying their ability to prevent lipopolysaccharide (LPS)-induced upregulation of nitric oxide (NO) and reactive oxygen species (ROS) production in RAW 264.7 macrophage cell line.
ISSN:0963-9969
1873-7145
DOI:10.1016/j.foodres.2020.109068