Isolation and antimalarial activity of alkaloids from Pseudoxandra cuspidata

Planta Med. 2006 Aug;72(10):894-8. doi: 10.1055/s-2006-947184. Epub 2006 Aug 10.

Abstract

A novel and very unusual azaanthracene alkaloid, 1-aza-7,8,9,10-tetramethoxy-4-methyl-2-oxo-1,2-dihydroanthracene ( 1) and a new diastereoisomer of the bis-benzylisoquinoline alkaloid rodiasine, 1 S,1' R-rodiasine ( 2), as well as the alkaloids O-methylpunjabine ( 3) and O-methylmoschatoline ( 4) have been isolated from Pseudoxandra cuspidata bark, used in French Guiana as an antimalarial. Their structures were elucidated by spectroscopic analyses, especially 2D-NMR techniques (ADEQUATE and NOESY). We found that the antimalarial activity of this bark was mostly due to bis-benzylisoquinoline 1 S,1' R-rodiasine ( 2) (IC (50)= 1 microM) also displaying a low cytotoxicity.

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*
  • Cell Line, Tumor
  • Humans
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Bark / chemistry
  • Plasmodium falciparum / drug effects
  • Toxicity Tests

Substances

  • Alkaloids
  • Antimalarials