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
Unité de Recherche Œnologie, EA 4577, USC 1366 INRA, Bordeaux INP, Institut des Sciences de la Vigne et du Vin, 210 Chemin de Leysotte, 33882 Villenave d'Ornon, France.
Unité de Recherche Œnologie, EA 4577, USC 1366 INRA, Bordeaux INP, Institut des Sciences de la Vigne et du Vin, 210 Chemin de Leysotte, 33882 Villenave d'Ornon, France.
Food Res Int. 2020 Jun;132:109068. doi: 10.1016/j.foodres.2020.109068. Epub 2020 Feb 7.
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.
白藜芦醇是一种著名的葡萄酒成分。其浓度会因品种选择和酿酒工艺而有所不同。由于其酚类结构，白藜芦醇在高温或氧化条件下可能会发生转化，导致形成包括低聚物在内的各种衍生物。因此，本研究的目的是调查葡萄酒中这些衍生物的存在情况。在第一阶段，通过使用金属进行氧化偶联，从乙醇中的白藜芦醇实现了低聚芪的半合成。通过质谱和核磁共振光谱鉴定了四种新合成的白藜芦醇衍生物，包括两种新分子，氧化白藜芦醇F和氧化白藜芦醇G。在第二阶段，通过液相色谱 - 质谱联用对热处理后的红酒进行分析，证实了葡萄酒中存在其中一些化合物。最后，通过研究这些化合物预防脂多糖（LPS）诱导的RAW 264.7巨噬细胞系中一氧化氮（NO）和活性氧（ROS）产生上调的能力，评估了这些化合物的抗炎作用。
