Organic & Biomolecular Chemistry 2014-09-07

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

Carlos Areche, Beatriz Sepulveda, Aurelio San Martin, Olimpo Garcia-Beltrán, Mario Simirgiotis, Alvaro Cañete

Index: Org. Biomol. Chem. 12(33) , 6406-13, (2014)

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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.