Antimalarial activity of azafluorenone alkaloids from the Australian tree Mitrephora diversifolia

J Nat Prod. 2009 Aug;72(8):1538-40. doi: 10.1021/np900247f.

Abstract

Mass-directed isolation of the CH2Cl2/MeOH extract from the roots of the Australian tree Mitrephora diversifolia resulted in the purification of the new azafluorenone alkaloid 5,8-dihydroxy-6-methoxyonychine (1) together with the known natural product 5-hydroxy-6-methoxyonychine (2). The structures of 1 and 2 were determined by extensive 1D and 2D NMR and MS data analyses. Both compounds were isolated during a drug discovery program aimed at the identification of new antimalarial leads from a prefractionated natural product library. When tested against two different strains of the parasite Plasmodium falciparum (3D7 and Dd2), 2 displayed IC(50) values of 9.9 and 11.4 microM, respectively, while 1 showed minimal activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / isolation & purification*
  • Alkaloids / pharmacology*
  • Animals
  • Annonaceae / chemistry*
  • Antimalarials / chemistry
  • Antimalarials / isolation & purification*
  • Antimalarials / pharmacology*
  • Australia
  • Aza Compounds / chemistry
  • Aza Compounds / isolation & purification*
  • Aza Compounds / pharmacology*
  • Fluorenes / chemistry
  • Fluorenes / isolation & purification*
  • Fluorenes / pharmacology*
  • Humans
  • Molecular Structure
  • Plant Roots / chemistry
  • Plasmodium falciparum / drug effects*
  • Trees / chemistry

Substances

  • Alkaloids
  • Antimalarials
  • Aza Compounds
  • Fluorenes