内生真菌层出镰刀菌产生的硫代二酮哌嗪。

Thiodiketopiperazines produced by the endophytic fungus Epicoccum nigrum.

机构信息

Key Laboratory of Bioactive Substance and Resources Utilization of Chinese Herbal Medicine, Ministry of Education, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, No. 1 Xian Nong Tan Street, Beijing People's Republic of China.

出版信息

J Nat Prod. 2010 Jul 23;73(7):1240-9. doi: 10.1021/np1000895.

DOI:10.1021/np1000895

PMID:20550196

Abstract

Thirteen new thiodiketopiperazines, epicoccin I (1), ent-epicoccin G (2), and epicoccins J-T (3-13), together with six known diketopiperazines (14-19), have been isolated from the endophytic fungus Epicoccum nigrum. The structures of 1, 2, and 10 were confirmed by X-ray crystallography, and the absolute configurations of 2, 4, 6, and 8 were assigned using Moshers' method. Compounds 2, 6, 12, and 17 showed potent activities in vitro against the release of beta-glucuronidase in rat polymorphonuclear leukocytes induced by platelet-activating factor, with IC(50) values of 3.07, 4.16, 4.95, and 1.98 microM, respectively. None of the 19 compounds exhibited detectable cytotoxic activities toward six tumor cell lines (A549, Be-l7402, BGC-823, HCT-8, HCT-116, and A2780) in the MTT assay.

摘要

从内生真菌层出镰刀菌中分离得到了 13 个新的噻二酮哌嗪类化合物，包括 epicoccin I（1）、ent-epicoccin G（2）和 epicoccins J-T（3-13），以及 6 个已知的二酮哌嗪类化合物（14-19）。通过 X 射线晶体学确定了 1、2 和 10 的结构，并用 Moshers 法确定了 2、4、6 和 8 的绝对构型。化合物 2、6、12 和 17 对血小板激活因子诱导的大鼠多形核白细胞β-葡萄糖醛酸酶释放具有很强的体外抑制活性，IC50 值分别为 3.07、4.16、4.95 和 1.98μM。在 MTT 测定中，这 19 种化合物均无明显的细胞毒性活性，对 6 种肿瘤细胞系（A549、Be-l7402、BGC-823、HCT-8、HCT-116 和 A2780）均无明显的细胞毒性活性。