Prenylemestrins A and B: Two Unexpected Epipolythiodioxopiperazines with a Thioethanothio Bridge from <i>Emericella</i> sp. Isolated by Genomic Analysis
Shanshan Chang, Meilian Cai, Tongmei Xiao, Yu‐Chuan Chen, Wuli Zhao, Liyan Yu, Rong‐Guang Shao, Wei Jiang, Tao Zhang, Maoluo Gan, Shuyi Si, Minghua Chen
Abstract
Prenylemestrins A and B (1 and 2, respectively), two unusual epipolythiodioxopiperazines featuring a thioethanothio bridge instead of a polysulfide bridge, were isolated from the fungus Emericella sp. CPCC 400858 guided by genomic analysis. Their structures were determined by extensive spectroscopic data, NMR and ECD calculations, and X-ray diffraction analysis. A plausible biosynthetic pathway for 1 and 2 was proposed on the basis of gene cluster analysis. Prenylemestrins A and B exhibited cytotoxicities against human chronic myelocytic leukemia cell lines K562 and MEG-01.
Topics & Concepts
Bridge (graph theory)ChemistryFungusStereochemistryK562 cellsGeneBiologyBiochemistryBotanyAnatomyMicrobial Natural Products and BiosynthesisNatural product bioactivities and synthesisPhytochemical compounds biological activities