Identification of COX inhibitors in the hexane extract of Japanese horse chestnut (Aesculus turbinata) seeds

J Vet Med Sci. 2007 Jul;69(7):709-12. doi: 10.1292/jvms.69.709.

Abstract

Japanese horse chestnut (Aesculus turbinata) seed extract inhibits the activity of cyclooxygenase (COX), but its active constituents have not been identified. In the present study, COX inhibitors were isolated from the hexane extract of this seed by means of 4 steps of liquid chromatography and were identified by gas chromatography/mass spectrometry and nuclear magnetic resonance. The COX inhibitors in the extract of Japanese horse chestnut seeds were identified as linoleic acid, linolenic acid, and oleic acid. Their efficacies were in the following order: linolenic acid = linoleic acid > oleic acid. These active constituents are C18 unsaturated fatty acids; stearic acid, a C18 saturated fatty acid, had no activity. Linolenic acid and linoleic acid had high selectivity toward COX-2 (selectivity index = 10), whereas oleic acid had no selectivity. Considering the efficacy and yield of each fatty acid, linoleic acid may be the principal COX inhibitor in this seed.

MeSH terms

  • Aesculus / chemistry*
  • Cyclooxygenase Inhibitors / chemistry*
  • Cyclooxygenase Inhibitors / isolation & purification
  • Cyclooxygenase Inhibitors / pharmacology*
  • Gas Chromatography-Mass Spectrometry
  • Inhibitory Concentration 50
  • Japan
  • Linoleic Acid / chemistry
  • Linoleic Acid / isolation & purification
  • Linoleic Acid / pharmacology
  • Nuclear Magnetic Resonance, Biomolecular
  • Oleic Acid / chemistry
  • Oleic Acid / isolation & purification
  • Oleic Acid / pharmacology
  • Seeds / chemistry
  • alpha-Linolenic Acid / chemistry
  • alpha-Linolenic Acid / isolation & purification
  • alpha-Linolenic Acid / pharmacology

Substances

  • Cyclooxygenase Inhibitors
  • alpha-Linolenic Acid
  • Oleic Acid
  • Linoleic Acid