白藜芦醇类似物结构与抗氧化活性关系研究

Structure-Antioxidant Activity Relationship of Resveratrol and its Analogues

本研究在白藜芦醇(A)结构的基础上设计了6种白藜芦醇类似物(B-G),采用量子化学密度泛函理论(DFT)计算方法,在气相和溶剂中研究了白藜芦醇及其6种类似物的结构与抗氧化活性的关系。对三种抗氧化机制:抽氢反应(HAT)机制、逐步电子转移质子转移(SET-PT)机制、质子优先损失电子转移(SPLET)机制进行了研究。计算结果表明,在气相中抽氢反应机制是化合物清除自由基活性的最主要机制,在极性溶剂中SPLET机制是热力学上最有利的途径,而在所有环境中SET-PT机制都不是最主要的机制。

Based on the structure of resveratrol( A),six resveratrol analogues( B-G) were designed. Then the relationship between the structure and antioxidant activity of resveratrol and its derivatives were studied in the gas phase and solvents using quantum chemical calculations based on the density functional theory( DFT). The three main working mechanisms,H-atom transfer( HAT),single electron transfer-proton transfer( SET-PT) and sequential proton loss electron transfer( SPLET) were investigated. The result showed that HAT would be the most favorable mechanism for explaining the radical-scavenging activity of four compounds in the gas phase,whereas the SPLET mechanism would be the thermodynamically favorable pathway in polar solvents. The calculations suggested that,SET-PT was not the most preferred mechanism in all environments studied.