Antimalarial dihydroisocoumarins produced by Geotrichum sp., an endophytic fungus of Crassocephalum crepidioides

J Nat Prod. 2003 May;66(5):709-11. doi: 10.1021/np0205598.

Abstract

Three novel dihydroisocoumarin derivatives (1-3) with antimalarial, antituberculous, and antifungal activities have been isolated by bioassay-guided fractionation from an endophytic fungus, Geotrichum sp., collected from Crassocephalum crepidioides. Structures were established as 7-butyl-6,8-dihydroxy-3(R)-pent-11-enylisochroman-1-one (1), 7-but-15-enyl-6,8-dihydroxy-3(R)-pent-11-enylisochroman-1-one (2), and 7-butyl-6,8-dihydroxy-3(R)-pentylisochroman-1-one (3) using spectroscopic data.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antifungal Agents / chemistry
  • Antifungal Agents / isolation & purification*
  • Antifungal Agents / pharmacology
  • Antimalarials / chemistry
  • Antimalarials / isolation & purification*
  • Antimalarials / pharmacology
  • Antitubercular Agents / chemistry
  • Antitubercular Agents / isolation & purification*
  • Antitubercular Agents / pharmacology
  • Candida albicans / drug effects
  • Coumarins / chemistry
  • Coumarins / isolation & purification*
  • Coumarins / pharmacology
  • Geotrichum / chemistry*
  • Molecular Structure
  • Mycobacterium tuberculosis / drug effects
  • Nuclear Magnetic Resonance, Biomolecular
  • Plasmodium falciparum / drug effects
  • Stereoisomerism
  • Thailand

Substances

  • 7-but-15-enyl-6,8-dihydroxy-3(R)-pent-11-enylisochroman-1-one
  • 7-butyl-6,8-dihydroxy-3(R)-pent-11-enylisochroman-1-one
  • 7-butyl-6,8-dihydroxy-3(R)-pentylisochroman-1-one
  • Antifungal Agents
  • Antimalarials
  • Antitubercular Agents
  • Coumarins