Isolation and structure determination of a sesquiterpene lactone (vernodalinol) from Vernonia amygdalina extracts

Pharm Biol. 2011 May;49(5):464-70. doi: 10.3109/13880209.2010.523429. Epub 2011 Feb 1.

Abstract

Context: Vernonia amygdalina Del. (VA; Asteraceae or Compositae) is a small tree growing throughout tropical Africa. It is widely used for food and medicinal purposes by local people. It was reported that it had several qualities, including anticancer activity.

Objective: A sesquiterpene lactone, vernodalinol, was isolated from VA leaves. The first reported source of vernodalinol was in 2009 from a different plant, only (1)H NMR spectrum and no detailed structural analysis were carried out. No whole spectroscopic data were provided.

Materials and methods: VA dried leaves were extracted with 85% ethanol followed by further separation into four fractions by liquid-liquid extraction technique using various solvents: hexane, chloroform, and n-butanol. Vernodalinol was separated from the n-butanol fraction by column chromatography. The biological activity of vernodalinol was evaluated in estrogen receptor-positive (ER(+)) human breast carcinoma cells (MCF-7) in vitro.

Results: Results indicated that vernodalinol (25 and 50 μg/mL) inhibited breast cancerous cell growth (DNA synthesis) by 34% (P < 0.025) and 40% (P < 0.025), respectively. It is reasonable to expect an LC(50) of 70-75 μg/mL for vernodalinol in MCF-7 cells.

Discussion and conclusion: Vernodalinol structure was confirmed using a battery of spectroscopic methods, 1D and 2D NMR, high-resolution mass spectrometry (HR-MS), UV, IR, and X-ray. These results suggest that vernodalinol, although it has some biological activity, is likely to work in concert with other ingredients responsible for the anticancer activity exhibited of VA.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Cell Line, Tumor
  • Crystallography, X-Ray
  • DNA / biosynthesis
  • Humans
  • Plant Extracts / analysis*
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification*
  • Sesquiterpenes / pharmacology
  • Vernonia / chemistry*

Substances

  • Plant Extracts
  • Sesquiterpenes
  • vernodalinol
  • DNA