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来自植物内生真菌甘氏木霉的新细胞松弛素的立体化学测定

Stereochemical determination of new cytochalasans from the plant endophytic fungus Trichoderma gamsii.

作者信息

Chen Lin, Liu Yue-Tao, Song Bo, Zhang Hong-Wu, Ding Gang, Liu Xing-Zhong, Gu Yu-Cheng, Zou Zhong-Mei

机构信息

Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, PR China.

Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, PR China.

出版信息

Fitoterapia. 2014 Jul;96:115-22. doi: 10.1016/j.fitote.2014.04.009. Epub 2014 Apr 18.

DOI:10.1016/j.fitote.2014.04.009
PMID:24752139
Abstract

Three new cytochalasans, trichalasins E (1), F (2) and H (7), together with four known analogues, trichalasin C (3), aspochalasin K (4), trichalasin G (5) and aspergillin PZ (8), were isolated from one endophytic fungus Trichoderma gamsii inhabiting in the traditional medicinal plant Panax notoginseng (BurK.) F.H. Chen. Trichalasins E (1) contains a unique hydroperoxyl group, which is the first report in all known analogues, whereas trichalasin H (7) possesses the rare 6/5/6/6/5 pentacyclic skeleton with 12-oxatricyclo [6.3.1.0(2,7)] moiety as that of aspergillin PZ (8). The relative configurations of the new compounds were characterized by analysis of coupling constants and ROESY correlations, and the absolute configurations of trichalasins E (1), H (7) and aspergillin PZ (8) were determined by modified Mosher's reaction. In addition, compounds 1-5, 7 and 8 were tested cytotoxic activities against several cancer cell lines.

摘要

从生长于传统药用植物三七(Panax notoginseng (BurK.) F.H. Chen)中的一株内生真菌哈茨木霉(Trichoderma gamsii)中分离得到了三种新的细胞松弛素,即曲拉菌素E(1)、F(2)和H(7),以及四种已知类似物,曲拉菌素C(3)、曲霉孢菌素K(4)、曲拉菌素G(5)和曲霉青霉素PZ(8)。曲拉菌素E(1)含有一个独特的氢过氧基,这在所有已知类似物中尚属首次报道,而曲拉菌素H(7)具有罕见的6/5/6/6/5五环骨架,带有与曲霉青霉素PZ(8)相同的12-氧杂三环[6.3.1.0(2,7)]部分。通过偶合常数分析和ROESY相关对新化合物的相对构型进行了表征,并通过改良的莫舍尔反应确定了曲拉菌素E(1)、H(7)和曲霉青霉素PZ(8)的绝对构型。此外,对化合物1-5、7和8进行了针对几种癌细胞系的细胞毒性活性测试。

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