Aplidiopsamine A, an antiplasmodial alkaloid from the temperate Australian ascidian, Aplidiopsis confluata

J Org Chem. 2010 Dec 3;75(23):8291-4. doi: 10.1021/jo101695v. Epub 2010 Nov 3.

Abstract

A polyaromatic alkaloid, aplidiopsamine A was isolated from the temperate Australian ascidian, Aplidiopsis confluata, and its structure was determined from interpretation of mass, 1D and 2D NMR spectra. Aplidiopsamine A is the first alkaloid to possess the tricyclic aromatic substructure 3H-pyrrolo[2,3-c]quinoline conjugated to an adenine. Aplidiopsamine A exhibited significant inhibition of growth of chloroquine resistant and sensitive strains of the malaria parasite, Plasmodium falciparum, and minimal toxicity toward human cells.

MeSH terms

  • Alkaloids / chemistry*
  • Alkaloids / isolation & purification
  • Alkaloids / pharmacology*
  • Animals
  • Antimalarials / chemistry*
  • Antimalarials / isolation & purification
  • Antimalarials / pharmacology*
  • Australia
  • Humans
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Structure
  • Plant Extracts / chemistry*
  • Plant Extracts / pharmacology*
  • Plasmodium falciparum / drug effects*
  • Plasmodium falciparum / isolation & purification
  • Pyrroles
  • Quinolines

Substances

  • Alkaloids
  • Antimalarials
  • Plant Extracts
  • Pyrroles
  • Quinolines
  • aplidiopsamine A