Further mulinane diterpenoids from Azorella compacta

Carlos Areche, Francisca Rojas-Alvarez, Carolina Campos-Briones, Carlos Lima, Edwin G. Pérez, Beatriz Sepúlveda

Resultado de la investigación: Article

16 Citas (Scopus)

Resumen

Objectives The chemical study of a dichloromethane extract from Azorella compacta was directed to the isolation of characteristic mulinane and azorellane diterpenoids in order to determine their gastroprotective activity. Methods Usual chromatographic techniques on the extract led to the isolation of 12 compounds, which were identified by their spectroscopic properties. The HCl/ethanol-induced gastric lesions model in mice was used to determine the gastroprotective activity. Key findings The new diterpenoids, 13β-hydroxymulinane (1), mulin-11,13-dien-20-ol (2), 13α- methoxyazorellanol (3) and mulin-11,13-dien-18-acetoxy-16,20-dioic acid (12) were isolated from A. compacta. The known diterpenoids mulin-11,13-dien-20-oic acid (4), 13α-hydroxyazorellane (5), 13β-hydroxyazorellane (6), mulinic acid (7), mulinolic acid (8) and azorellanol (9), and the aromatic compounds 5,7-dihydroxychromone (10) and isoflavonoid biochanin A (11), were also obtained from the extract. Compounds 6, 9 and 12 at 20 mg/kg reduced gastric lesions by 69%, 71% and 73%, respectively, being statistically similar to lansoprazole at the same dose. Conclusions The results corroborate the intraspecific chemical variations detected previously in specimens of A. compacta collected at different Chilean latitudes. A high concentration of azorellanol (9) could account in part for some of the therapeutic properties attributed to this species, in particular in ulcer treatment. Most of the mulinane and azorellane diterpenoids isolated in this study showed relevant gastroprotective activity at a low dose in the bioassay.

Idioma originalEnglish
Páginas (desde-hasta)1231-1238
Número de páginas8
PublicaciónJournal of Pharmacy and Pharmacology
Volumen65
N.º8
DOI
EstadoPublished - 1 ago 2013

Huella dactilar

Apiaceae
Diterpenes
Acids
Stomach
Lansoprazole
Methylene Chloride
Biological Assay
Ulcer
Ethanol
mulinane
azorellane

ASJC Scopus subject areas

  • Pharmacology
  • Pharmaceutical Science

Citar esto

Areche, C., Rojas-Alvarez, F., Campos-Briones, C., Lima, C., Pérez, E. G., & Sepúlveda, B. (2013). Further mulinane diterpenoids from Azorella compacta. Journal of Pharmacy and Pharmacology, 65(8), 1231-1238. https://doi.org/10.1111/jphp.12083
Areche, Carlos ; Rojas-Alvarez, Francisca ; Campos-Briones, Carolina ; Lima, Carlos ; Pérez, Edwin G. ; Sepúlveda, Beatriz. / Further mulinane diterpenoids from Azorella compacta. En: Journal of Pharmacy and Pharmacology. 2013 ; Vol. 65, N.º 8. pp. 1231-1238.
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abstract = "Objectives The chemical study of a dichloromethane extract from Azorella compacta was directed to the isolation of characteristic mulinane and azorellane diterpenoids in order to determine their gastroprotective activity. Methods Usual chromatographic techniques on the extract led to the isolation of 12 compounds, which were identified by their spectroscopic properties. The HCl/ethanol-induced gastric lesions model in mice was used to determine the gastroprotective activity. Key findings The new diterpenoids, 13β-hydroxymulinane (1), mulin-11,13-dien-20-ol (2), 13α- methoxyazorellanol (3) and mulin-11,13-dien-18-acetoxy-16,20-dioic acid (12) were isolated from A. compacta. The known diterpenoids mulin-11,13-dien-20-oic acid (4), 13α-hydroxyazorellane (5), 13β-hydroxyazorellane (6), mulinic acid (7), mulinolic acid (8) and azorellanol (9), and the aromatic compounds 5,7-dihydroxychromone (10) and isoflavonoid biochanin A (11), were also obtained from the extract. Compounds 6, 9 and 12 at 20 mg/kg reduced gastric lesions by 69{\%}, 71{\%} and 73{\%}, respectively, being statistically similar to lansoprazole at the same dose. Conclusions The results corroborate the intraspecific chemical variations detected previously in specimens of A. compacta collected at different Chilean latitudes. A high concentration of azorellanol (9) could account in part for some of the therapeutic properties attributed to this species, in particular in ulcer treatment. Most of the mulinane and azorellane diterpenoids isolated in this study showed relevant gastroprotective activity at a low dose in the bioassay.",
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Areche, C, Rojas-Alvarez, F, Campos-Briones, C, Lima, C, Pérez, EG & Sepúlveda, B 2013, 'Further mulinane diterpenoids from Azorella compacta', Journal of Pharmacy and Pharmacology, vol. 65, n.º 8, pp. 1231-1238. https://doi.org/10.1111/jphp.12083

Further mulinane diterpenoids from Azorella compacta. / Areche, Carlos; Rojas-Alvarez, Francisca; Campos-Briones, Carolina; Lima, Carlos; Pérez, Edwin G.; Sepúlveda, Beatriz.

En: Journal of Pharmacy and Pharmacology, Vol. 65, N.º 8, 01.08.2013, p. 1231-1238.

Resultado de la investigación: Article

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T1 - Further mulinane diterpenoids from Azorella compacta

AU - Areche, Carlos

AU - Rojas-Alvarez, Francisca

AU - Campos-Briones, Carolina

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AU - Pérez, Edwin G.

AU - Sepúlveda, Beatriz

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N2 - Objectives The chemical study of a dichloromethane extract from Azorella compacta was directed to the isolation of characteristic mulinane and azorellane diterpenoids in order to determine their gastroprotective activity. Methods Usual chromatographic techniques on the extract led to the isolation of 12 compounds, which were identified by their spectroscopic properties. The HCl/ethanol-induced gastric lesions model in mice was used to determine the gastroprotective activity. Key findings The new diterpenoids, 13β-hydroxymulinane (1), mulin-11,13-dien-20-ol (2), 13α- methoxyazorellanol (3) and mulin-11,13-dien-18-acetoxy-16,20-dioic acid (12) were isolated from A. compacta. The known diterpenoids mulin-11,13-dien-20-oic acid (4), 13α-hydroxyazorellane (5), 13β-hydroxyazorellane (6), mulinic acid (7), mulinolic acid (8) and azorellanol (9), and the aromatic compounds 5,7-dihydroxychromone (10) and isoflavonoid biochanin A (11), were also obtained from the extract. Compounds 6, 9 and 12 at 20 mg/kg reduced gastric lesions by 69%, 71% and 73%, respectively, being statistically similar to lansoprazole at the same dose. Conclusions The results corroborate the intraspecific chemical variations detected previously in specimens of A. compacta collected at different Chilean latitudes. A high concentration of azorellanol (9) could account in part for some of the therapeutic properties attributed to this species, in particular in ulcer treatment. Most of the mulinane and azorellane diterpenoids isolated in this study showed relevant gastroprotective activity at a low dose in the bioassay.

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Areche C, Rojas-Alvarez F, Campos-Briones C, Lima C, Pérez EG, Sepúlveda B. Further mulinane diterpenoids from Azorella compacta. Journal of Pharmacy and Pharmacology. 2013 ago 1;65(8):1231-1238. https://doi.org/10.1111/jphp.12083