An unusual mulinane diterpenoid from the Chilean plant Azorella trifurcata (Gaertn) Pers

Org Biomol Chem. 2014 Sep 7;12(33):6406-13. doi: 10.1039/c4ob00966e.

Abstract

Four new mulinane-type diterpenoids besides the known compounds mulin-11,13-dien-20-oic acid, 13α-hydroxyazorellane, 13β-hydroxyazorellane, mulinolic acid, azorellanol, and mulin-11,13-dien-18-acetoxy-16,20-dioic acid were isolated from the Chilean plant Azorella trifurcata. One of the new metabolites isolated, 7α-acetoxy-9-epi-13β-hydroxymulinane, possesses a new trans-syn-trans arrangement in a tricyclic ring system not previously encountered in nature. Among the mulinane diterpenoids isolated, mulin-11,13-dien-20-oic acid showed the gastroprotective effect on HCl-EtOH-induced gastric lesions in mice (ED50 = 55 mg kg(-1)). Regarding the mode of gastroprotective action for this active compound, its effect was reduced by pre-treatment of the mice with indomethacin and N-ethylmaleimide, suggesting that prostaglandins and sulfhydryl compounds are positively involved in the gastroprotective activity using this model.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Apiaceae / chemistry*
  • Diterpenes / chemistry
  • Diterpenes / isolation & purification
  • Diterpenes / therapeutic use*
  • Ethanol / administration & dosage
  • Ethylmaleimide
  • Gastritis / chemically induced
  • Gastritis / drug therapy*
  • Hydrochloric Acid / administration & dosage
  • Indomethacin
  • Mice
  • NG-Nitroarginine Methyl Ester
  • Plant Extracts / chemistry
  • Plant Extracts / isolation & purification
  • Plant Extracts / therapeutic use*
  • Ruthenium Red

Substances

  • Diterpenes
  • Plant Extracts
  • mulinane
  • Ruthenium Red
  • Ethanol
  • Ethylmaleimide
  • Hydrochloric Acid
  • NG-Nitroarginine Methyl Ester
  • Indomethacin