First Total Synthesis of （±）-Latifolin and Its Antioxidant Mechanism

作     者：Yihua Dai Qiaoling Liu Zhifang Li Weifeng Chen Zhongli Liu 

作者机构：Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education Hangzhou Normal University Hangzhou Zhejiang 310012 China National Laboratory of Applied Organic Chemistry Lanzhou University Lanzhou Gansu 730000 China 

出 版 物：《Chinese Journal of Chemistry》 (中国化学（英文版）)

年 卷 期：2015年第33卷第11期

页      面：1287-1292页

核心收录：

学科分类：0832[工学-食品科学与工程（可授工学、农学学位）] 081704[工学-应用化学] 07[理学] 08[工学] 0817[工学-化学工程与技术] 070303[理学-有机化学] 0703[理学-化学] 083202[工学-粮食、油脂及植物蛋白工程] 

基　　金：This work was supported by the National Natural Science Foundation of China (Nos. 21202031  21472032) and Zhejiang Provincial Natural Science Foundation of China (No. Y4110297) 

主　　题：total synthesis latifolin antioxidant DPPH-scavenging density functional theory 

摘      要：The first total synthesis of （±）-latifolin has been accomplished in six steps and 47.8% overall yield. To understand the relative importance of phenolic O-H and benzhydryl C-H hydrogen on the antioxidant activity of latifolin, 2,2-diphenyl-1-picrylhydrazyl （DPPH） radical scavenging assay and density functional theory （DFT） studies were carried out. On scavenging DPPH radical in ethanol, the activity of latifolin （1） bearing phenolic hydrogen is remarkably higher than analogue 10 bearing no phenolic hydrogen. Therefore, Phenolic hydrogen is responsible for latifolin＇s antioxidant activity rather than benzhydryl C-H hydrogen. Furthermore, the 5-OH BDE is lower than 2＇-OH and 7-CH BDEs by a DFT calculation, respectively. Based on theoretical results it is definitely concluded that the phenolic 5-OH plays a major role in the antioxidant activity of latifolin.