Issue 33, 2014

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

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

Supplementary files

Article information

Article type
Paper
Submitted
09 May 2014
Accepted
25 Jun 2014
First published
25 Jun 2014

Org. Biomol. Chem., 2014,12, 6406-6413

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

C. Areche, B. Sepulveda, A. S. Martin, O. Garcia-Beltrán, M. Simirgiotis and A. Cañete, Org. Biomol. Chem., 2014, 12, 6406 DOI: 10.1039/C4OB00966E

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