Formicins, N-Acetylcysteamine-Bearing Indenone Thioesters from a Wood Ant-Associated Bacterium

Org Lett. 2020 Jul 17;22(14):5337-5341. doi: 10.1021/acs.orglett.0c01584. Epub 2020 Jul 6.

Abstract

Formicins A-C (1-3) were discovered from Streptomyces sp. associated with wood ants. The structures of 1 and 2 were elucidated as indenone thioesters bearing N-acetylcysteamine based on spectroscopic analysis. The configurations of 1-3 were determined by the analysis of ROESY correlations, the phenylglycine methyl ester method, and chemical derivatization from 3 to 2. Formicin A inhibited the growth of human triple-negative breast cancer cells by regulating the liver kinase B1-mediated AMPK signaling pathway.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • AMP-Activated Protein Kinases / metabolism
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology*
  • Cell Line, Tumor
  • Esters / chemistry
  • Humans
  • Indenes / chemistry*
  • Indenes / pharmacology*
  • Signal Transduction / drug effects
  • Streptomyces / chemistry*

Substances

  • Antineoplastic Agents
  • Esters
  • Indenes
  • AMP-Activated Protein Kinases