Evaluation of Jatropha isabelli natural products and their synthetic analogs as potential antimalarial therapeutic agents

Eur J Med Chem. 2013 Jul:65:376-80. doi: 10.1016/j.ejmech.2013.04.030. Epub 2013 Apr 23.

Abstract

Protozoal diseases such as malaria are a leading world health concern. We screened a library of fractionated natural products to identify new potential therapeutic leads and discovered that jatrophone (a product of Jatropha isabelli) exerts significant activity against Plasmodium falciparum strains 3D7 and K1. A focused jatrophone-scaffold library was synthesized to evaluate jatrophone's mode of action and identify more selective analogs. Compounds 25 and 32 of this natural product-inspired compound library exhibited micromolar EC50 values against strains 3D7 and K1, thus providing a new antimalarial molecular scaffold. Our report describes an efficient derivatization approach used to evaluate the structure-activity relationship of jatrophone analogs in search of potential new antimalarial agents.

Keywords: 1-butyl-3-methylimidazolium tetrafluoroborate; Antimalarial agents; Conjugated additions; Jatropha isabelli; Jatrophone; N-bromosuccinimide; NBS; PAMPA; Plasmodium falciparum; [bmim][BF(4)]; mCPBA; meta-chloroperoxybenzoic acid; parallel artificial membrane permeability assay.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antiprotozoal Agents / chemistry
  • Antiprotozoal Agents / isolation & purification
  • Antiprotozoal Agents / pharmacology*
  • Biological Products / chemistry
  • Biological Products / isolation & purification
  • Biological Products / pharmacology*
  • Dose-Response Relationship, Drug
  • Jatropha / chemistry*
  • Molecular Conformation
  • Parasitic Sensitivity Tests
  • Plasmodium falciparum / drug effects*
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Antiprotozoal Agents
  • Biological Products