title: 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 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.
authors.affiliation: Departamento de Química, Facultad de Ciencias, Universidad de Chile, Casilla 653, Santiago, Chile. areche@uchile.cl.
authors.forename: Carlos
authors.initials: C
authors.lastname: Areche
authors.forename: Beatriz
authors.initials: B
authors.lastname: Sepulveda
authors.forename: Aurelio
authors.initials: A
authors.lastname: San Martin
authors.forename: Olimpo
authors.initials: O
authors.lastname: Garcia-Beltrán
authors.forename: Mario
authors.initials: M
authors.lastname: Simirgiotis
authors.forename: Alvaro
authors.initials: A
authors.lastname: Cañete
mesh_terms: D000818:Animals; D019661:Apiaceae / Q000737:chemistry*; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification / Q000627:therapeutic use*; D000431:Ethanol / Q000008:administration & dosage; D005033:Ethylmaleimide; D005756:Gastritis / Q000139:chemically induced / Q000188:drug therapy*; D006851:Hydrochloric Acid / Q000008:administration & dosage; D007213:Indomethacin; D051379:Mice; D019331:NG-Nitroarginine Methyl Ester; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification / Q000627:therapeutic use*; D012430:Ruthenium Red
chemical_list: D004224:Diterpenes; D010936:Plant Extracts; C113748:mulinane; D012430:Ruthenium Red; D000431:Ethanol; D005033:Ethylmaleimide; D006851:Hydrochloric Acid; D019331:NG-Nitroarginine Methyl Ester; D007213:Indomethacin