Aryl ketones from Acronychia pedunculata with cyclooxygenase-2 inhibitory effects

Chem Biodivers. 2005 Apr;2(4):463-9. doi: 10.1002/cbdv.200590026.

Abstract

1-[2,4-Dihydroxy-6-methoxy-3,5-bis(3-methylbut-2-en-1-yl)phenyl]ethanone (1), and a new aryl ketone, named acrovestenol (2), were isolated as cyclooxygenase-2 (COX-2) inhibitory principles from a CH2Cl2 extract of the bark of Acronychia pedunculata by a bioassay-guided fractionation procedure. Compound 2 inhibited COX-2 with an IC50 value of 142.0+/-2.15 microM, compared to the COX-2 inhibitory reference compound NS-398 with an IC50 value of 11.3+/-1.12 microM. Compound 1 inhibited COX-2-catalyzed PG biosynthesis with 68% at a concentration of 500 microM. The structures were determined by UV, IR, and 1D- and 2D-NMR, including TOCSY, HSQC-DEPT, and HMBC, and MS investigations.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetophenones / chemistry*
  • Acetophenones / pharmacology*
  • Cyclooxygenase 2 Inhibitors / chemistry*
  • Cyclooxygenase 2 Inhibitors / pharmacology*
  • Ketones / chemistry*
  • Ketones / pharmacology*
  • Molecular Structure
  • Plant Bark / chemistry
  • Rutaceae / chemistry*

Substances

  • 1-(2,4-dihydroxy-6-methoxy-3,5-bis(3-methylbut-2-en-1-yl)phenyl)ethanone
  • Acetophenones
  • Cyclooxygenase 2 Inhibitors
  • Ketones
  • acrovestenol