Protostane-Type Triterpenoids from Alisma orientale

Chem Biodivers. 2017 Dec;14(12). doi: 10.1002/cbdv.201700452.

Abstract

Twenty-eight protostane triterpenoids, including a new degraded one (1), nine new ones (2 - 10), and two new natural ones (11 and 12), have been isolated from the dried rhizomes of Alisma orientale. Alisol R (1) was the first 20,21,22,23,24,25,26,27-octanorprotostane triterpenoid. The absolute configurations of 25-methoxyalisol F (2) and 16β-hydroperoxyalisol B 23-acetate (3) were determined by X-ray diffraction analysis. In addition, alismaketone-B 23-acetate (28) showed potent vasorelaxant activity on endothelium-intact thoracic aorta rings precontracted with KCl.

Keywords: Alisma orientale; Alismataceae; Alismatis Rhizoma; Protostane triterpenoids; Vasorelaxant activity.

MeSH terms

  • 11-beta-Hydroxysteroid Dehydrogenases / antagonists & inhibitors
  • 11-beta-Hydroxysteroid Dehydrogenases / metabolism
  • Alisma / chemistry*
  • Alisma / metabolism
  • Animals
  • Aorta / drug effects
  • Aorta / metabolism
  • Humans
  • Magnetic Resonance Spectroscopy
  • Mice
  • Molecular Conformation
  • Plant Extracts / chemistry
  • Potassium Chloride / toxicity
  • Rats
  • Rhizome / chemistry
  • Rhizome / metabolism
  • Terpenes / chemistry*
  • Terpenes / metabolism
  • Terpenes / pharmacology
  • Triterpenes / chemistry
  • Triterpenes / isolation & purification
  • Triterpenes / pharmacology
  • Vasodilator Agents / chemistry
  • Vasodilator Agents / isolation & purification
  • Vasodilator Agents / pharmacology
  • X-Ray Diffraction

Substances

  • Plant Extracts
  • Terpenes
  • Triterpenes
  • Vasodilator Agents
  • alismaketone-B 23-acetate
  • Potassium Chloride
  • 11-beta-Hydroxysteroid Dehydrogenases