| 论文题目: | Chloropupukeanolides C–E, cytotoxic pupukeanane chlorides with a spiroketal skeleton from Pestalotiopsis fici. |
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| 作者: | Ling Liu#, Torsten Bruhn#, Liangdong Guo, Daniel C. G. Götz, Reto Brun, August Stich, Yongsheng Che* and Gerhard Bringmann*. |
| 联系作者: | 车永胜 |
| 刊物名称: | Chemistry–A European Journal |
| 期: | 9 |
| 卷: | 17 |
| 页: | 17(9): 2604–2613 |
| 年份: | 2011 |
| 影响因子: | 5.476 |
| 论文下载: | 下载地址 |
| 摘要: | Chloropupukeanolides C-E (8-10), three highly functionalized secondary metabolites featuring a novel spiroketal skeleton derived from the chlorinated tricyclo-[4.3.1.0(3, 7)]-decane (pupukeanane) and the 2,6-dihydroxy-4-methylbenzoic acid moieties, were isolated from the scale-up fermentation extract of the plant endophytic fungus Pestalotiopsis fici. The constitutions of compounds 8-10 were elucidated primarily by NMR experiments. Their relative configurations were deduced by analogy to metabolites 4-6, which were previously isolated from the same fungus. The absolute configuration of 8 was assigned by X-ray crystallography and those of 9 and 10 by quantum-chemical CD calculations. Biogenetically, chloropupukeanolides C-E (8-10) are presumably derived from the same oxidation-induced Diels-Alder reaction pathway as compounds 1 and 4-7, via the putative biosynthetic precursors 2 and 3. The opposite configurations of the complete "Southern parts" of 8 and 9 suggests that this Diels-Alder reaction is stereochemically not very selective. Compounds 8-10 showed significant cytotoxicity against a small panel of human tumor cell lines and weak activities against the pathogens of tropical diseases. |
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