Berkeleydione and berkeleytrione, new bioactive metabolites from an acid mine organism

Org Lett. 2004 Mar 18;6(6):1049-52. doi: 10.1021/ol049852k.

Abstract

[structure: see text] Two novel hybrid polyketide-terpenoid metabolites were isolated from a Penicillium sp. growing in the Berkeley Pit Lake of Butte, Montana. Their structures were deduced by spectroscopic analysis and confirmed by single-crystal X-ray analysis on berkeleydione (1). Both compounds inhibited matrix metalloproteinase-3 and caspase-1, and berkeleydione showed activity toward non-small-cell lung cancer in NCI's human cell line antitumor screen.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Acids
  • Caspase Inhibitors
  • Cell Line, Tumor
  • Crystallography, X-Ray
  • Drug Evaluation, Preclinical
  • Enzyme Inhibitors / analysis
  • Enzyme Inhibitors / isolation & purification*
  • Fresh Water / microbiology
  • Humans
  • Macrolides / analysis
  • Macrolides / isolation & purification*
  • Macrolides / pharmacology
  • Magnetic Resonance Spectroscopy
  • Matrix Metalloproteinase Inhibitors
  • Mining
  • Molecular Structure
  • Montana
  • Penicillium chrysogenum / chemistry*
  • Penicillium chrysogenum / isolation & purification
  • Penicillium chrysogenum / metabolism
  • Terpenes / analysis
  • Terpenes / isolation & purification*
  • Terpenes / pharmacology

Substances

  • Acids
  • Caspase Inhibitors
  • Enzyme Inhibitors
  • Macrolides
  • Matrix Metalloproteinase Inhibitors
  • Terpenes
  • berkeleydione
  • berkeleytrione