TY - JOUR
T1 - An unusual mulinane diterpenoid from the Chilean plant Azorella trifurcata (Gaertn) Pers
AU - Areche, Carlos
AU - Sepulveda, Beatriz
AU - Martin, Aurelio San
AU - Garcia-Beltrán, Olimpo
AU - Simirgiotis, Mario
AU - Cañete, Alvaro
PY - 2014/9/7
Y1 - 2014/9/7
N2 - 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.
AB - 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.
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U2 - 10.1039/c4ob00966e
DO - 10.1039/c4ob00966e
M3 - Article
C2 - 25008488
AN - SCOPUS:84905165590
SN - 1477-0520
VL - 12
SP - 6406
EP - 6413
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
IS - 33
ER -