Cytotoxic monoterpenoid indole alkaloids isolated from the barks of Voacanga africana Staph

Nat Prod Res. 2016;30(10):1144-9. doi: 10.1080/14786419.2015.1046132. Epub 2015 Jul 3.

Abstract

A new monoterpenoid indole alkaloid compound (1) and six known monoterpenoid indole alkaloids compounds (2-7) were isolated from the barks of Voacanga africana Staph. The structures were established by spectral analysis as ibogamine-16-carboxylic acid,17,20-didehydro-5,6-dioxo-10-methoxy-methyl ester (1), voacamine (2), vobasine (3), voacangine (4), voacristine (5), 19-epi-voacristine (6) and 19-epi-heyneanine (7). Compound 1 was confirmed by X-ray crystallographic analysis. All of the isolated compounds were evaluated for cytotoxicity against five cell lines (HEPG-2, A375, MDA-MB-231, SH-SY5Y, CT26). Among them, compounds 2 and 6 displayed significant inhibitory activities, compounds 3, 4 and 5 showed moderate inhibitory activities, while compounds 1 and 7 showed no inhibitory activities against the five cell lines.

Keywords: Voacanga africana Staph; cytotoxicity; monoterpenoid indole alkaloids.

MeSH terms

  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Bridged-Ring Compounds / isolation & purification
  • Bridged-Ring Compounds / pharmacology
  • Cell Line, Tumor / drug effects
  • Humans
  • Ibogaine / analogs & derivatives
  • Ibogaine / isolation & purification
  • Indole Alkaloids / isolation & purification
  • Molecular Structure
  • Plant Bark / chemistry
  • Secologanin Tryptamine Alkaloids / isolation & purification*
  • Secologanin Tryptamine Alkaloids / pharmacology*
  • Voacanga / chemistry*

Substances

  • Antineoplastic Agents, Phytogenic
  • Bridged-Ring Compounds
  • Indole Alkaloids
  • Secologanin Tryptamine Alkaloids
  • ibogamine
  • ibogamine-16-carboxylic acid,17,20-didehydro-5,6-dioxo-10-methoxy-methyl ester
  • vobasine
  • voacamine
  • Ibogaine
  • voacangine
  • voacristine