First Total Synthesis of (±)‐Latifolin and Its Antioxidant Mechanism |
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| Authors: | Yihua Dai Qiaoling Liu Zhifang Li Weifeng Chen Zhongli Liu |
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| Institution: | 1. Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou, Zhejiang 310012, China;2. National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, China |
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| Abstract: | 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. |
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| Keywords: | total synthesis latifolin antioxidant DPPH‐scavenging density functional theory |
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