Anthecularin: a novel sesquiterpene lactone from Anthemis auriculata with antiprotozoal activity

J Org Chem. 2007 Oct 12;72(21):8103-6. doi: 10.1021/jo701751w. Epub 2007 Sep 20.

Abstract

Anthecularin (1), a minor sesquiterpene lactone with a novel ring system was isolated from Greek Anthemis auriculata (Asteraceae). Its structure was elucidated by means of NMR, HRMS, and X-ray crystallography. Anthecularin showed antitrypanosomal (IC50=10.1 microg/mL) and antiplasmodial activity (IC50=23.3 microg/mL) and inhibited two key enzymes of the plasmodial type II fatty acid biosynthesis pathway, PfFabI and PfFabG (IC50 values=14 and 28.3 microg/mL, respectively). A probable biogenesis of 1 is also proposed and discussed.

MeSH terms

  • Animals
  • Anthemis / chemistry*
  • Antimalarials / isolation & purification
  • Antimalarials / pharmacology
  • Antiprotozoal Agents / isolation & purification*
  • Antiprotozoal Agents / pharmacology
  • Crystallography, X-Ray
  • Lactones / isolation & purification*
  • Lactones / pharmacology
  • Models, Molecular
  • Molecular Structure
  • Plant Components, Aerial / chemistry
  • Plasmodium falciparum / drug effects
  • Plasmodium falciparum / enzymology
  • Sesquiterpenes / isolation & purification*
  • Sesquiterpenes / pharmacology
  • Stereoisomerism

Substances

  • Antimalarials
  • Antiprotozoal Agents
  • Lactones
  • Sesquiterpenes
  • anthecularin