Molecules (May 2007)

Lupane Triterpenoids from Acacia mellifera with Cytotoxic Activity

  • Vassilios Roussis,
  • Christos Roussakis,
  • Dimitri Moreau,
  • Constantinos Vagias,
  • Dennis Abatis,
  • Charles Mutai

DOI
https://doi.org/10.3390/12051035
Journal volume & issue
Vol. 12, no. 5
pp. 1035 – 1044

Abstract

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Three new pentacyclic triterpenoids: (20R)-3-oxolupan-30-al (1), (20S)-3-oxolupan-30-al (2) and (20R)-28-hydroxylupen-30-al-3-one (3), along with (20S)-3β-hydroxylupan-30-al (4), the latter previously described as a constituent of an epimeric mixture, were isolated from Acacia mellifera. In addition, the known metabolites 30-hydroxylup-20-(29)-en-3-one (5), 30-hydroxylup-20-(29)-en-3β-ol (6), atranorin, methyl 2,4-dihydroxy-3,6 dimethyl benzoate, sitosterol-3β-O-glucoside and linoleic acid were found in the analyzed plant species for the first time. The structures of the new metabolites were elucidated by extensive spectroscopic analyses and their relative stereochemistry was determined by NOESY experiments. The new metabolite 3 exhibited significant cytotoxic activity against the NSCLC-N6 cell line, derived from a human non-small-cell bronchopulmonary carcinoma.

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