Berkelic acid, a novel spiroketal with selective anticancer activity from an acid mine waste fungal extremophile

J Org Chem. 2006 Jul 7;71(14):5357-60. doi: 10.1021/jo060018d.

Abstract

Berkeley Pit Lake is an abandoned open-pit copper mine filled with 30 billion gallons of acidic, metal-contaminated water. This harsh environment is proving to be a source of unusual microorganisms that produce novel bioactive metabolites. Bioassay-guided fractionation using signal transduction enzyme assays led to the isolation of the novel spiroketal, berkelic acid 1, and of the known gamma-pyrone, spiciferone A 4. Berkelic acid has shown selective, nanomolar activity against OVCAR-3, an ovarian cancer cell line in the National Cancer Institute cell line screen. The isolation and characterization of these compounds are reported here.

Publication types

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

MeSH terms

  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / isolation & purification
  • Antineoplastic Agents / pharmacology*
  • Cell Line, Tumor
  • Drug Screening Assays, Antitumor
  • Heterocyclic Compounds, 2-Ring / chemistry
  • Humans
  • Magnetic Resonance Spectroscopy / methods
  • Magnetic Resonance Spectroscopy / standards
  • Molecular Conformation
  • Penicillium / chemistry*
  • Reference Standards
  • Sensitivity and Specificity
  • Spiro Compounds / chemistry*
  • Spiro Compounds / isolation & purification
  • Spiro Compounds / pharmacology*
  • Waste Products
  • Water / chemistry

Substances

  • Antineoplastic Agents
  • Heterocyclic Compounds, 2-Ring
  • Spiro Compounds
  • Waste Products
  • berkelic acid
  • spiciferone A
  • Water