An unusual mulinane diterpenoid from the Chilean plant Azorella trifurcata (Gaertn) Pers†
Carlos Areche,Beatriz Sepulveda,Aurelio San Martin,Mario Simirgiotis,Alvaro Cañete
Organic & Biomolecular Chemistry Pub Date : 06/25/2014 00:00:00 , 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 transsyntrans 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.

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