A novel labdane-type trialdehyde from myoga (Zingiber mioga Roscoe) that potently inhibits human platelet aggregation and human 5-lipoxygenase

Biosci Biotechnol Biochem. 2006 Oct;70(10):2494-500. doi: 10.1271/bbb.60226. Epub 2006 Oct 7.

Abstract

We screened myoga extracts for inhibitors of human platelet aggregation and human 5-lipoxygenase. We identified a novel labdane type of diterpene, together with three known diterpenes (miogadial and galanals A and B) from the flower buds of myoga. Spectroscopic data indicated the structure of the new compound to be 12(E)-labdene-15,16,(8beta)17-trial (miogatrial). Miogatrial and miogadial were potent inhibitors of human platelet aggregation and human 5-lipoxygenase (5-LOX). The sesquiterpene, polygodial, also exhibited strong inhibitory activity against human platelet aggregation and 5-LOX. On the other hand, galanals A and B did not have inhibitory activity in either experimental system. It thus appears that a 3-formyl-3-butenal structure was essential for the potent inhibition of human platelet aggregation and human 5-LOX.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry
  • Aldehydes / isolation & purification
  • Aldehydes / pharmacology*
  • Diterpenes / chemistry
  • Diterpenes / isolation & purification
  • Diterpenes / pharmacology
  • Drug Evaluation, Preclinical
  • Flowers / chemistry
  • Humans
  • Lipoxygenase Inhibitors*
  • Molecular Structure
  • Platelet Aggregation Inhibitors / chemistry*
  • Platelet Aggregation Inhibitors / isolation & purification
  • Platelet Aggregation Inhibitors / pharmacology
  • Spectrum Analysis
  • Structure-Activity Relationship
  • Zingiberaceae / chemistry*

Substances

  • Aldehydes
  • Diterpenes
  • Lipoxygenase Inhibitors
  • Platelet Aggregation Inhibitors
  • labdane