Synthesis of analogues of gingerol and shogaol, the active pungent principles from the rhizomes of Zingiber officinale and evaluation of their anti-platelet aggregation effects

Int J Mol Sci. 2014 Mar 4;15(3):3926-51. doi: 10.3390/ijms15033926.

Abstract

The present study was aimed at discovering novel biologically active compounds based on the skeletons of gingerol and shogaol, the pungent principles from the rhizomes of Zingiber officinale. Therefore, eight groups of analogues were synthesized and examined for their inhibitory activities of platelet aggregation induced by arachidonic acid, collagen, platelet activating factor, and thrombin. Among the tested compounds, [6]-paradol (5b) exhibited the most significant anti-platelet aggregation activity. It was the most potent candidate, which could be used in further investigation to explore new drug leads.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Catechols / chemical synthesis
  • Catechols / pharmacology*
  • Dose-Response Relationship, Drug
  • Drug Evaluation, Preclinical
  • Fatty Alcohols / chemical synthesis
  • Fatty Alcohols / pharmacology*
  • Ginger / chemistry*
  • Hydrogenation
  • Models, Chemical
  • Molecular Structure
  • Oxidation-Reduction
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology
  • Platelet Aggregation / drug effects
  • Platelet Aggregation Inhibitors / chemical synthesis
  • Platelet Aggregation Inhibitors / pharmacology*
  • Platelet Count
  • Rabbits
  • Rhizome / chemistry*

Substances

  • Catechols
  • Fatty Alcohols
  • Plant Extracts
  • Platelet Aggregation Inhibitors
  • shogaol
  • gingerol