Pseudoguanolide sesquiterpene lactones from Vernoniopsis caudata and their in vitro antiplasmodial activities

J Nat Prod. 2005 May;68(5):800-3. doi: 10.1021/np0401866.

Abstract

Two new helenanolide sesquiterpene lactones, 1 and 2, as well as one known related structure, 11alpha,13-dihydrohelenalin-[2-(1-hydroxyethyl)acrylate] (3), together with 4'-beta-d-O-glucopyranosyl-luteolin and ethyl 2,5-dihydroxycinnamate were isolated from an ethyl acetate extract of leaves of Vernoniopsis caudatawith potent antiplasmodial activity (IC50 1.6 microg/mL) in a preliminary biological screen. The structures of the new compounds were determined by spectroscopic techniques. The three sesquiterpene lactones 1-3 displayed strong in vitro antiplasmodial activity, with IC50 values of 1, 0.19, and 0.41 microM, respectively. However, these compounds also exhibited considerable cytotoxicity on KB cells (IC50 < 1 microM in each case).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antimalarials / chemistry
  • Antimalarials / isolation & purification*
  • Antimalarials / pharmacology
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification*
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Asteraceae / chemistry*
  • Drug Screening Assays, Antitumor
  • Humans
  • Inhibitory Concentration 50
  • KB Cells
  • Lactones / chemistry
  • Lactones / isolation & purification*
  • Lactones / pharmacology
  • Madagascar
  • Plant Leaves / chemistry
  • Plants, Medicinal / chemistry*
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification*
  • Sesquiterpenes / pharmacology
  • Sesquiterpenes, Guaiane
  • Tumor Cells, Cultured

Substances

  • Antimalarials
  • Antineoplastic Agents, Phytogenic
  • Lactones
  • Sesquiterpenes
  • Sesquiterpenes, Guaiane
  • helenalin-((2-hydroxyethyl-3-methyl)acrylate)
  • helenalin-(2-(1-hydroxyethyl)acrylate)