Cycloartane-type triterpenes from the leaves of Homonoia riparia with VEGF-induced angiogenesis inhibitory activity

J Nat Prod. 2012 Jul 27;75(7):1312-8. doi: 10.1021/np300224k. Epub 2012 Jun 25.

Abstract

Six new cycloartane-type triterpenes (1-6), 24-methylenecycloartane-3β,6β,7β-triol (1), 24-methylenecycloartane-3β,6β,7β,16β-tetraol (2), 24-methylenecycloartane-3β,6β,16β-triol (3), 24-methylenecycloartane-3β,7β,16β-triol 3-O-β-d-xylopyranoside (4), 24-methylenecycloartane-3β,6β,16β-triol 3-O-β-d-xylopyranoside (5), and 24-methylenecycloartane-3β,6β,7β-triol 3-O-β-d-xylopyranoside (6), were isolated from the leaves of Homonoia riparia, together with one known compound, 24-methylenecycloartane-3β,6β,7β,16β-tetraol 3-O-β-d-xylopyranoside (7). The structures of the new triterpenes were established by spectroscopic studies and from chemical evidence, and the inhibitory effects of compounds 1 and 3-7 on VEGF-induced vascular permeability were examined in vivo in rats using the Miles assay. In addition, the inhibitory effect of 7 on VEGF-induced tube formation by HUVECs in vitro was investigated.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Angiogenesis Inhibitors / chemistry
  • Angiogenesis Inhibitors / isolation & purification*
  • Angiogenesis Inhibitors / pharmacology*
  • Animals
  • Euphorbiaceae / chemistry*
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Leaves / chemistry
  • Rats
  • Stereoisomerism
  • Triterpenes / chemistry
  • Triterpenes / isolation & purification*
  • Triterpenes / pharmacology*
  • Vascular Endothelial Growth Factor A / pharmacology*
  • Vietnam

Substances

  • Angiogenesis Inhibitors
  • Triterpenes
  • Vascular Endothelial Growth Factor A
  • cycloartane