A pyrimidine-beta-carboline and other alkaloids from Annona foetida with antileishmanial activity

J Nat Prod. 2006 Feb;69(2):292-4. doi: 10.1021/np050422s.

Abstract

Bioassay-guided fractionation of the bark extract of Annona foetida afforded a new antileishmanial pyrimidine-beta-carboline alkaloid, N-hydroxyannomontine (1), together with the previously reported annomontine (2), O-methylmoschatoline (3), and liriodenine (4). The structure of compound 1 was established on the basis of extensive 1D and 2D NMR and MS analyses. This is the third reported pyrimidine-beta-carboline-type alkaloid and is particularly important for Annona genus chemotaxonomy. In addition, all compounds exhibit in vitro antileishmanial activity against promastigote forms of Leishmania braziliensis. Compounds 2 and 4 showed better activity than compounds 1 and 3 against L. braziliensis. Compound 2 was not active against L. guyanensis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / isolation & purification*
  • Alkaloids / pharmacology*
  • Animals
  • Annona / chemistry*
  • Antiprotozoal Agents / chemistry
  • Antiprotozoal Agents / isolation & purification*
  • Antiprotozoal Agents / pharmacology*
  • Brazil
  • Carbolines / chemistry
  • Carbolines / isolation & purification*
  • Carbolines / pharmacology*
  • Leishmania / drug effects*
  • Molecular Structure
  • Plants, Medicinal / chemistry*
  • Pyrimidines / chemistry
  • Pyrimidines / isolation & purification*
  • Pyrimidines / pharmacology*

Substances

  • Alkaloids
  • Antiprotozoal Agents
  • Carbolines
  • N-hydroxyannomontine
  • Pyrimidines
  • annomontine