Seven pairs of new enantiomeric sesquiterpenoids from Curcuma phaeocaulis

Bioorg Chem. 2020 Jun:99:103820. doi: 10.1016/j.bioorg.2020.103820. Epub 2020 Apr 7.

Abstract

Seven pairs of new enantiomeric sesquiterpenoids, (+)/(-)-phaeocauline A - G [(+)/(-)-1-7], were isolated from the rhizomes of Curcuma phaeocaulis by chiral HPLC separation. Their structures, including absolute configurations, were determined by spectroscopic analyses and ECD data. The isolates were assessed for vasorelaxant, anti-platelet aggregative, and neuroprotective activities. Enantiomers (+)-1 and (-)-1 showed similar activity against abnormal platelet aggregation induced by arachidonic acid, while their C-4 epimers (+)-2 and (-)-2 were inactive, which indicated that those effects were stereoselective, but not enantioselective. Compounds (+)/(-)-3-5 exhibited vasorelaxant effects against KCl-induced contraction of rat aortic rings.

Keywords: Anti-platelet aggregative activity; Chiral separation; Curcuma phaeocaulis; Enantiomers; Sesquiterpenoids; Vasorelaxant activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Aorta / drug effects*
  • Aorta / metabolism
  • Curcuma / chemistry*
  • Dose-Response Relationship, Drug
  • Molecular Structure
  • Neuroprotective Agents / chemistry
  • Neuroprotective Agents / isolation & purification
  • Neuroprotective Agents / pharmacology*
  • Platelet Aggregation / drug effects
  • Potassium Chloride / antagonists & inhibitors*
  • Potassium Chloride / pharmacology
  • Rats
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification
  • Sesquiterpenes / pharmacology*
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Neuroprotective Agents
  • Sesquiterpenes
  • Potassium Chloride