A pair of tirucallane C₂₇-triterpenoid cyclopentenone epimers from the stem barks of Aphanamixis grandifolia

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• 作者：Jun-Song Wang^a ; Yao Zhang^a ; Xiao-Bing Wang^a ; Dan-Dan Wei^a ; Jun Luo^a ; Jian-Guang Luo^a ; Ming-Hua Yang^a ; He-Quan Yao^b ; Hong-Bin Sun^b ; Ling-Yi Kong^a ; ^{cpu_lykong@126.com}
• 关键词：Aphagranins A and B ; Density functional theory (DFT) calculation ; Electronic circular dichroism (ECD) ; Antiproliferative activities ; Meliaceae
• 刊名：Tetrahedron Letters
• 出版年：2012
• 期刊代码：109_00404039
• 类别：ch
• 出版时间：4 April, 2012
• 卷：53
• 期：14
• 页码：1705-1709
• 文件大小：478 K

摘要

Two novel tirucallane C₂₇-triterpenoid epimers, aphagranins A (Font">1) and B (2), featuring an unprecedented enolized cyclopentenone presented in the side-chain at C-17, were isolated from the stem barks of Aphanamixis grandifolia. Extensive spectroscopic analyses helped the establishment of the structures of the two isolates, whose absolute configurations were determined using density functional theory (DFT) calculations of optical rotation, and electronic circular dichroism (ECD). Remarkable discrepancies in the inhibitory activities against the growth of six lines of human cancer cells (MCF-7, A549, HepG2, Bel-7402, SGC-7901, and BGC-823) were found for the two epimers: with IC₅₀ less than 10 渭M, aphagranin A exhibited much stronger antiproliferative activity than aphagranin B, showing no such activities with IC₅₀ over 20 渭M.