Jacaranone-derived glucosidic esters from Jacaranda glabra and their activity against Plasmodium falciparum

J Nat Prod. 2010 Apr 23;73(4):553-6. doi: 10.1021/np900528m.

Abstract

In a survey of plants from Ecuador with antiprotozoal activity, Jacaranda glabra was found to show promising activity against the Plasmodium falciparum K1 strain. Subsequently, activity-guided isolation of the dichloromethane extract from the leaves of J. glabra afforded four new phenylethanoid glucosides containing jacaranone-type moieties (1-4), named jacaglabrosides A-D. Their chemical structures were identified using NMR spectroscopy and MS techniques. The compounds were found to be active in vitro against the P. falciparum K1 strain (IC(50) 1, 1.02; 2, 0.56; 3, 0.56; and 4, 0.55 microg/mL) and generally possessed a low cytotoxicity toward L-6 cells, with the exception of compound 1 (IC(50) 1, 8.3; 2, >90; 3, 87; and 4, 85 microg/mL).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antimalarials / chemistry
  • Antimalarials / isolation & purification*
  • Antimalarials / pharmacology*
  • Benzoquinones / chemistry*
  • Ecuador
  • Esters
  • Glucosides / chemistry
  • Glucosides / isolation & purification*
  • Glucosides / pharmacology*
  • Myoblasts / drug effects
  • Nuclear Magnetic Resonance, Biomolecular
  • Parasitic Sensitivity Tests
  • Phenylacetates / chemistry
  • Plasmodium falciparum / drug effects*
  • Rats

Substances

  • Antimalarials
  • Benzoquinones
  • Esters
  • Glucosides
  • Phenylacetates
  • jacaranone
  • phenylacetic acid