A novel cyclooxygenase-inhibitory stilbenolignan from the seeds of Aiphanes aculeata

Org Lett. 2001 Jul 12;3(14):2169-71. doi: 10.1021/ol015985j.

Abstract

[structure: see text] Aiphanol (1), a novel stilbenolignan, along with isorhapontigenin (2), piceatannol (3), and luteolin, were isolated by bioassay-guided fractionation from the seeds of Aiphanes aculeata Willd. (Arecaceae). The structure of compound 1 was elucidated by spectroscopic methods. Compound 1 is based on an unprecedented stilbenolignan skeleton in which a stilbene moiety is linked with a phenylpropane unit through a dioxane bridge. Compounds 1 and 2 exhibited significant inhibitory activities against cyclooxygenases-1 and -2.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Cyclooxygenase 1
  • Cyclooxygenase 2
  • Cyclooxygenase 2 Inhibitors
  • Cyclooxygenase Inhibitors / chemistry
  • Cyclooxygenase Inhibitors / isolation & purification*
  • Cyclooxygenase Inhibitors / pharmacology
  • Flavonoids / chemistry
  • Flavonoids / isolation & purification
  • Flavonoids / pharmacology
  • Isoenzymes / antagonists & inhibitors
  • Isoenzymes / metabolism
  • Luteolin
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Plants, Medicinal / chemistry*
  • Prostaglandin-Endoperoxide Synthases / metabolism
  • Seeds / chemistry
  • Stilbenes / chemistry
  • Stilbenes / isolation & purification*
  • Stilbenes / pharmacology
  • Structure-Activity Relationship

Substances

  • Cyclooxygenase 2 Inhibitors
  • Cyclooxygenase Inhibitors
  • Flavonoids
  • Isoenzymes
  • Stilbenes
  • aiphanol
  • isorhapontigenin
  • 3,3',4,5'-tetrahydroxystilbene
  • Cyclooxygenase 1
  • Cyclooxygenase 2
  • Prostaglandin-Endoperoxide Synthases
  • Luteolin