Phomopsis archeri 中的细胞毒性五环和四环芳香倍半萜。

Cytotoxic pentacyclic and tetracyclic aromatic sesquiterpenes from Phomopsis archeri.

机构信息

Natural Products Research Unit, Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen 40002, Thailand.

出版信息

J Nat Prod. 2011 Apr 25;74(4):609-13. doi: 10.1021/np100632g. Epub 2011 Feb 22.

DOI:10.1021/np100632g

PMID:21341709

Abstract

Three new sesquiterpenes, named phomoarcherins A-C (1-3), and four known compounds, kampanol A (4), R-mevalonolactone, ergosterol, and ergosterol peroxide, were isolated from the endophytic fungus Phomopsis archeri. These structures were established on the basis of spectroscopic evidence. The structure and absolute configuration of 1 were confirmed by X-ray crystallographic analysis of its p-bromobenzoate derivative (1a). Compounds 1-4 showed cytotoxicity against five cholangiocarcinoma cell lines (0.1-19.6 μg/mL), while 1 and 2 exhibited weak cytotoxicity against the KB cell line with IC(50) values of 42.1 and 9.4 μg/mL, respectively. In addition, compound 2 showed antimalarial activity against Plasmodium falciparum with an IC(50) value of 0.79 μg/mL.

摘要

从内生真菌拟茎点霉（Phomopsis archeri）中分离得到了三种新的倍半萜，分别命名为 phomoarcherins A-C（1-3），以及四种已知化合物，kampanol A（4）、R-甲羟戊酸内酯、麦角甾醇和麦角甾醇过氧化物。这些结构是基于光谱证据确定的。通过对其对溴苯甲酸酯衍生物（1a）的 X 射线晶体学分析，确定了 1 的结构和绝对构型。化合物 1-4 对五种胆管癌细胞系表现出细胞毒性（0.1-19.6 μg/mL），而化合物 1 和 2 对 KB 细胞系表现出较弱的细胞毒性，IC50 值分别为 42.1 和 9.4 μg/mL。此外，化合物 2 对恶性疟原虫（Plasmodium falciparum）表现出抗疟活性，IC50 值为 0.79 μg/mL。