Antifungal azaphilones from the fungus Chaetomium cupreum CC3003

J Nat Prod. 2006 Jun;69(6):891-5. doi: 10.1021/np060051v.

Abstract

Three new azaphilones named rotiorinols A-C (1-3), two new stereoisomers, (-)-rotiorin (4) and epi-isochromophilone II (5), and a known compound, rubrorotiorin (6), were isolated from the fungus Chaetomium cupreum CC3003. Structures were established on the basis of spectroscopic evidence. The absolute configuration of 1 was determined by the modified Mosher's method along with an X-ray analysis of its acetate derivative, as well as by chemical transformation. Compounds 1, 3, 4, and 6 exhibited antifungal activity against Candida albicans with IC50 values of 10.5, 16.7, 24.3, and 0.6 microg/mL, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antifungal Agents / chemistry
  • Antifungal Agents / isolation & purification*
  • Antifungal Agents / pharmacology
  • Benzopyrans / chemistry
  • Benzopyrans / isolation & purification*
  • Benzopyrans / pharmacology
  • Candida albicans / drug effects
  • Chaetomium / chemistry*
  • Crystallography, X-Ray
  • Dose-Response Relationship, Drug
  • Inhibitory Concentration 50
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Pigments, Biological / chemistry
  • Pigments, Biological / isolation & purification*
  • Pigments, Biological / pharmacology
  • Stereoisomerism
  • Thailand

Substances

  • Antifungal Agents
  • Benzopyrans
  • Pigments, Biological
  • azaphilone