Tripartilactam, a cyclobutane-bearing tricyclic lactam from a Streptomyces sp. in a dung beetle's brood ball

Org Lett. 2012 Mar 2;14(5):1258-61. doi: 10.1021/ol300108z. Epub 2012 Feb 23.

Abstract

Tripartilactam, a structurally unprecedented cyclobutane-bearing tricyclic lactam metabolite, was discovered from Streptomyces sp. isolated from a brood ball of the dung beetle, Copris tripartitus. The structure of this compound was elucidated by the combination of NMR, MS, UV, and IR spectroscopy and multistep chemical derivatization. Tripartilactam was evaluated as a Na(+)/K(+) ATPase inhibitor (IC(50) = 16.6 μg/mL).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Coleoptera / microbiology*
  • Cyclobutanes / chemistry*
  • Cyclobutanes / isolation & purification
  • Cyclobutanes / pharmacology
  • Feces / microbiology*
  • Humans
  • Lactams / chemistry*
  • Lactams / isolation & purification
  • Lactams / pharmacology
  • Molecular Structure
  • Sodium Potassium Chloride Symporter Inhibitors / chemistry*
  • Sodium Potassium Chloride Symporter Inhibitors / isolation & purification
  • Sodium Potassium Chloride Symporter Inhibitors / pharmacology
  • Streptomyces / chemistry*
  • Streptomyces / isolation & purification

Substances

  • Cyclobutanes
  • Lactams
  • Sodium Potassium Chloride Symporter Inhibitors
  • tripartilactam