Chojalactones A-C, cytotoxic butanolides isolated from Streptomyces sp. cultivated with mycolic acid containing bacterium

Org Lett. 2015 Mar 20;17(6):1501-4. doi: 10.1021/acs.orglett.5b00385. Epub 2015 Mar 5.

Abstract

The soil-derived bacterium, Streptomyces sp. CJ-5, was cocultured with the mycolic acid-containing bacterium Tsukamurella pulmonis TP-B0596. The combined culture method significantly enhanced the production of the secondary metabolites in Streptomyces sp. CJ-5, leading to the isolation of three novel butanolide chojalactones A-C (1-3), with unusual γ-butyrolactone scaffolds. The complete structures, including the absolute configurations of 1-3, were determined based on spectroscopic data and total syntheses. In methylthiazole tetrazolium (MTT) assays, 1 and 2 showed moderate cytotoxicity against P388 cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 4-Butyrolactone / analogs & derivatives
  • 4-Butyrolactone / chemistry
  • 4-Butyrolactone / isolation & purification*
  • 4-Butyrolactone / pharmacology*
  • Animals
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Drug Screening Assays, Antitumor
  • Humans
  • Leukemia P388
  • Molecular Structure
  • Mycolic Acids / analysis
  • Streptomyces / chemistry*

Substances

  • Antineoplastic Agents
  • Mycolic Acids
  • chojalactone A
  • chojalactone B
  • chojalactone C
  • 4-Butyrolactone