Induction of apoptosis in HuH-7 cancer cells by monoterpene and beta-carboline indole alkaloids isolated from the leaves of Tabernaemontana elegans

Bioorg Med Chem Lett. 2009 Aug 1;19(15):4255-8. doi: 10.1016/j.bmcl.2009.05.104. Epub 2009 May 30.

Abstract

Three known (1-3) and a novel (4) monoterpene indole alkaloids have been isolated from the methanol extract of leaves of Tabernaemontana elegans and their structures were elucidated by a series of spectroscopic experiments, involving NMR, MS, UV, and IR techniques. The isolated monoterpene indole alkaloids along with previously described beta-carbolines (5-7) from the same specimen were studied for their apoptosis induction activity in human hepatoma HuH-7 cells. Methodology for apoptosis induction studies included cell viability assays, nuclear morphology assessments, and general caspase-3-like activity assays. The monoterpene indole alkaloids, tabernaemontanine (1) and vobasine (3) showed the most promising apoptosis induction profile in HuH-7 cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids
  • Apoptosis*
  • Carbolines / chemistry*
  • Cell Line, Tumor
  • Drug Design
  • Humans
  • Indole Alkaloids / chemical synthesis*
  • Indole Alkaloids / pharmacology
  • Magnetic Resonance Spectroscopy
  • Models, Chemical
  • Models, Molecular
  • Molecular Conformation
  • Plant Extracts / metabolism*
  • Plant Leaves / metabolism*
  • Tabernaemontana / metabolism*

Substances

  • Alkaloids
  • Carbolines
  • Indole Alkaloids
  • Plant Extracts
  • vobasine