文章基本信息

标题：(−)- and (+)-Securidanes A and B, Natural Triarylmethane Enantiomers Structure and Bioinspired Total Synthesis
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作者：B. Zhou ; D. X. Liu ; X. J. Yuan 等
期刊名称：Research
电子版ISSN：2639-5274
出版年度：2018
卷号：2018
页码：1-9
DOI：10.1155/2018/2674182
语种：English
出版社：American Association for the Advancement of Science
摘要：Two pairs of enantiomers, (−) and (+)-securidanes A (1 and 2) and B (3 and 4) featuring unprecedented triarylmethane (TAM) skeletons, were isolated from Securidaca inappendiculata. Their structures were established by spectroscopic data, X-ray crystallography, and CD analysis. A plausible biosynthetic pathway for 1−4 based on the co-isolated precursors was proposed. Bioinspired total synthesis of 1−4 was completed in high yield, which in turn corroborated the biosynthetic hypothesis. Compounds 1−4 showed good inhibition against protein tyrosine phosphatase 1B (PTP1B). The molecular docking demonstrated that the strongest inhibitor 3 (IC50 = 7.52 μM) reaches deeper into the binding pocket and has an additional H-bond.