4.8 Article

Prenylemestrins A and B: Two Unexpected Epipolythiodioxopiperazines with a Thioethanothio Bridge from Emericella sp. Isolated by Genomic Analysis

Journal

ORGANIC LETTERS
Volume 24, Issue 32, Pages 5941-5945

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c02187

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Funding

  1. CAMS Innovation Fund for Medical Sciences (CIFMS) [2021-I2M-1-028, 2021-I2M-1-054, 2021-I2M-1-055]
  2. National Natural Science Foundation of China (NNSFC) [81302675, 82104047, 81630089]

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In this study, two unusual compounds, 1 and 2, were isolated from the fungus Emericella sp. CPCC 400858 based on genomic analysis. These compounds, featuring a unique structure, showed cytotoxicity against chronic myelocytic leukemia cells.
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.

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