Indole diketopiperazines from endophytic Chaetomium sp 88194 induce breast cancer cell apoptotic death

Scientific Reports
Fu-qian WangYonghui Zhang

Abstract

Diketopiperazines are important secondary metabolites of the fungi with variety bioactivities. Several species belonging to genus Chaetomium produce compounds of this class, such as chetomin. To identify new antitumor agents, secondary metabolites of fungus Chaetomium sp 88194 were investigated and three new indole diketopiperazines, Chaetocochins G (1), Oidioperazines E (2) and Chetoseminudin E (3), along with two known compounds Chetoseminudins C (4) and N-acetyl-β-oxotryptamine (5), were obtained. Chaetocochins G and Chetoseminudin E were recrystallized in CHCl3 containing a small amount of MeOH, and their structures with absolute configuration were established by spectroscopic data interpretation and single-crystal X-ray diffraction analysis. The absolute configuration of Oidioperazines E was defined by comparing of experimental and calculated electronic circular dichroism spectra. These isolates were also evaluated the anticancer activity, and Chaetocochins G displayed more potent cytotoxicity in MCF-7 cells than the common chemotherapeutic agent (5-fluorouracil) associated with G2/M cell cycle arrest. More importantly, Chaetocochins G induced cell apoptotic death via caspase-3 induction and proteolytic cleavage of poly (A...Continue Reading

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Citations

Nov 27, 2015·European Journal of Pharmacology·Zhang-Feng ZhongYi-Tao Wang
Jul 20, 2016·World Journal of Microbiology & Biotechnology·Jian-Hua WangChun-Shan Quan
Mar 30, 2017·Tumour Biology : the Journal of the International Society for Oncodevelopmental Biology and Medicine·Ailian Zhang, Jincheng Li
Nov 24, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Xiaohan WangLigang Zhou
Feb 4, 2021·Journal of Natural Products·Sharna-Kay Daley, Geoffrey A Cordell
Mar 3, 2020·Journal of Natural Products·Meng-Hua WangZhong-Mei Zou

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Methods Mentioned

BETA
X-ray
flow cytometry
column chromatography

Software Mentioned

modfit
GraphPad Prism
SHELXL
Gaussian
SPSS
confab
BALLOON

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