First Total Synthesis of (±)-Latifolin and Its Antioxidant Mechanism
First Total Synthesis of (±)-Latifolin and Its Antioxidant Mechanism
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(/-)-Latifolin的首次全合成及其抗氧化机制
DOI：
10.1002/cjoc.201500505
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发表时间：
2015-11-01
影响因子：
5.4
通讯作者：
Liu, Zhongli
中科院分区：
文献类型：
--
作者：
Dai, Yihua;Liu, Qiaoling;Liu, Zhongli
首次全合成了（+/-）-latifolin，经6步反应，总收率47.8%。为了了解酚羟基和二苯甲基CH氢对latifolin抗氧化活性的相对重要性，进行了2，2-二苯基-1-苦基肼（DPPH）自由基清除实验和密度泛函理论（DFT）研究。在乙醇溶液中，含酚氢的宽叶芹素（1）清除DPPH自由基的活性显著高于不含酚氢的类似物10。因此，酚氢负责latifolin的抗氧化活性，而不是二苯甲基CH氢。此外，通过DFT计算，5-OH BDE分别低于2-OH和7-CH BDE。基于理论结果，可以肯定地得出结论，酚5-OH在latifolin的抗氧化活性中起主要作用。
The first total synthesis of (+/-)-latifolin has been accomplished in six steps and 47.8% overall yield. To understand the relative importance of phenolic OH and benzhydryl CH 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 CH 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.