Pestalachlorides A-C, antifungal metabolites from the plant endophytic fungus Pestalotiopsis adusta

Bioorg Med Chem. 2008 Sep 1;16(17):7894-9. doi: 10.1016/j.bmc.2008.07.075. Epub 2008 Jul 30.

Abstract

Pestalachlorides A-C (1-3), three new chlorinated benzophenone derivatives, have been isolated from cultures of an isolate of the plant endophytic fungus Pestalotiopsis adusta. The structures of these compounds were determined mainly by NMR spectroscopy, and the structures of 1 and 3 were further confirmed by X-ray crystallography. Pestalachloride A (1) was obtained as a mixture of two inseparable atropisomers (1a and 1b), whereas pestalachloride C (3) was found to be a racemic mixture. Compounds 1 and 2 displayed significant antifungal activities against three plant pathogens.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anisoles / chemistry*
  • Anisoles / isolation & purification
  • Anisoles / pharmacology*
  • Antifungal Agents / chemistry*
  • Antifungal Agents / isolation & purification
  • Antifungal Agents / pharmacology*
  • Ascomycota / chemistry*
  • Benzofurans / chemistry*
  • Benzofurans / isolation & purification
  • Benzofurans / pharmacology*
  • Benzoxepins / chemistry*
  • Benzoxepins / isolation & purification
  • Benzoxepins / pharmacology*
  • Crystallography, X-Ray
  • Fusarium / drug effects*
  • Gibberella / drug effects*
  • Indans / chemistry*
  • Indans / isolation & purification
  • Indans / pharmacology*
  • Isoindoles / chemistry*
  • Isoindoles / isolation & purification
  • Isoindoles / pharmacology*
  • Magnetic Resonance Spectroscopy / methods
  • Magnetic Resonance Spectroscopy / standards
  • Microbial Sensitivity Tests
  • Models, Molecular
  • Molecular Structure
  • Reference Standards
  • Resorcinols / chemistry*
  • Resorcinols / isolation & purification
  • Resorcinols / pharmacology*
  • Stereoisomerism
  • Verticillium / drug effects*

Substances

  • Anisoles
  • Antifungal Agents
  • Benzofurans
  • Benzoxepins
  • Indans
  • Isoindoles
  • Resorcinols
  • pestalachloride A
  • pestalachloride B
  • pestalachloride C