Jaa Ayoub, de Moura Patricia Homobono Brito, Valls-Fonayet Josep, Da Costa Grégory, Ruiz-Larrea María Begoña, Krisa Stéphanie, Ruiz-Sanz José Ignacio, Richard Tristan
Bordeaux INP, INRAE, Bordeaux Sciences Agro, OENO, UMR 1366, ISVV, University of Bordeaux, F-33140 Villenave d'Ornon, France.
Free Radicals and Oxidative Stress (FROS) Research Group, Department of Physiology, Medicine and Nursing School, University of the Basque Country UPV/EHU, 48940 Leioa, Spain.
Molecules. 2024 Dec 23;29(24):6067. doi: 10.3390/molecules29246067.
Resveratrol and its glucoside, piceid, are the primary stilbenes present in wine. These compounds are well known for their pharmaceutical properties. However, these compounds can undergo chemical transformations in wines, such as polymerization in the presence of metallic reagents. This study investigates the oxidative coupling of resveratrol and piceid to form dimers, including δ-viniferin and δ-viniferin-diglucoside. These dimers were synthesized using silver acetate. The formation of these stilbenes was monitored in wine model solutions and red wines. The results indicated that resveratrol and piceid underwent transformation during heat treatment, forming their respective dimers. The polymerization of both compounds is temperature-dependent, with higher conversion rates at elevated temperatures. Notably, piceid was more reactive than resveratrol in wine. Finally, the anti-inflammatory effects of these compounds were evaluated on the RAW 264.7 macrophage cell line.
白藜芦醇及其糖苷白藜芦醇苷是葡萄酒中存在的主要芪类化合物。这些化合物因其药学特性而广为人知。然而，这些化合物在葡萄酒中会发生化学转化，比如在金属试剂存在的情况下发生聚合反应。本研究调查了白藜芦醇和白藜芦醇苷的氧化偶联反应以形成二聚体，包括δ-葡萄素和δ-葡萄素二糖苷。这些二聚体是用醋酸银合成的。在葡萄酒模型溶液和红葡萄酒中监测了这些芪类化合物的形成。结果表明，白藜芦醇和白藜芦醇苷在热处理过程中发生了转化，形成了它们各自的二聚体。这两种化合物的聚合反应都与温度有关，在较高温度下转化率更高。值得注意的是，在葡萄酒中白藜芦醇苷比白藜芦醇更具反应活性。最后，对这些化合物在RAW 264.7巨噬细胞系上的抗炎作用进行了评估。
