ent-Beyerane diterpenoids from the heartwood of Excoecaria parvifolia

Mary H. Grace, Juan A. Faraldos, Mary Ann Lila, Robert M. Coates

Research output: Contribution to journalArticlepeer-review

Abstract

Chromatographic fractionations of the toluene extract of the heartwood of Excoecaria parvifolia collected in Australia resulted in the isolation of 12 beyerane diterpenes (1-12), and the triterpene, lupeol. Four of the isolated diterpenoids (5-7 and 12) have unusual structures: ent-3-oxa-beyer-15-en-2-one, (5); ent-15,16-epoxy-2-hydroxy-19-norbeyer-1,4-dien-3-one (6); methyl ent-2,4-seco-15,16-epoxy-4-oxo-3,19-dinorbeyer-15-en-2-oate (7); and ent-2,17-dihydroxy-19-norbeyer-1,4,15-trien-3-one (12). The structures were established by spectroscopic analyses, NMR data comparisons with similar diterpenes, and chemical correlations. All the diterpenes are assumed to have the same absolute configuration as the co-occurring (+)-stachenol (4). Diosphenol 2 and nor-lactone 5 exhibited significant potency in bioassays for cytotoxic activity against leukemia cells (L1210). Plausible biosynthetic pathways are proposed to explain the origin of the diterpene metabolites.

Original languageEnglish (US)
Pages (from-to)546-553
Number of pages8
JournalPhytochemistry
Volume68
Issue number4
DOIs
StatePublished - Feb 2007

Keywords

  • Cytotoxicity
  • Diosphenols
  • Diterpenoids
  • Euphorbiaceae
  • Excoecaria parvifolia
  • Heartwood
  • L1210
  • ent-Beyeranes

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Plant Science
  • Horticulture

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