Ponapensin, a cyclopenta[bc]benzopyran with potent NF-kappaB inhibitory activity from Aglaia ponapensis

Bioorg Med Chem Lett. 2007 Jan 1;17(1):109-12. doi: 10.1016/j.bmcl.2006.09.084. Epub 2006 Sep 30.

Abstract

Two new compounds, a cyclopenta[bc]benzopyran, ponapensin (1), and an aglaialactone, 5,6-desmethylenedioxy-5-methoxy-aglalactone (2), together with nine known compounds were isolated from the CHCl(3) soluble extract of the leaves and twigs of Aglaia ponapensis. Their structures were established by spectroscopic data interpretation. Ponapensin (1) exhibited significant NF-kappaB inhibitory activity in an Elisa assay, and was found to be more potent than the positive control rocaglamide. All of the compounds isolated were also tested in a panel of human cancer cell lines, with the known sterol E-volkendousin (3) and methyl rocaglate (aglafoline) found to be the only active substances.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Aglaia / chemistry*
  • Benzofurans / chemistry
  • Benzofurans / isolation & purification
  • Benzofurans / pharmacology
  • Benzopyrans / chemistry*
  • Benzopyrans / isolation & purification
  • Benzopyrans / pharmacology*
  • Cell Line, Tumor
  • Enzyme-Linked Immunosorbent Assay
  • Heterocyclic Compounds, 3-Ring / chemistry*
  • Heterocyclic Compounds, 3-Ring / isolation & purification
  • Heterocyclic Compounds, 3-Ring / pharmacology*
  • Humans
  • Molecular Structure
  • NF-kappa B / antagonists & inhibitors*
  • Plant Leaves / chemistry

Substances

  • 5,6-desmethylenedioxy-5-methoxyaglalactone
  • Benzofurans
  • Benzopyrans
  • Heterocyclic Compounds, 3-Ring
  • NF-kappa B
  • ponapensin
  • rocaglamide