2014 |
Salgado, F; Areche, C; Sepulveda, B; Simirgiotis, M J; Caceres, F; Quispe, C; Quispe, L; Cano, T A New Mulinane Diterpenoid from the Cushion Shrub Azorella Compacta Growing in Peru Artículo de revista Pharmacognosy Magazine, 10 (39), pp. 543-548, 2014, ISSN: 0973-1296. Resumen | Enlaces | BibTeX | Etiquetas: acids activity, apiaceae, azorella carbon compacta, crassifolium, diterpenoids, gastroprotective madreporica, mulinanes, natural-products, skeleton, umbelliferae @article{RN185, title = {A New Mulinane Diterpenoid from the Cushion Shrub Azorella Compacta Growing in Peru}, author = { F. Salgado and C. Areche and B. Sepulveda and M.J. Simirgiotis and F. Caceres and C. Quispe and L. Quispe and T. Cano}, url = {/brokenurl#<Go to ISI>://WOS:000341875000014}, doi = {10.4103/0973-1296.139807}, issn = {0973-1296}, year = {2014}, date = {2014-01-01}, journal = {Pharmacognosy Magazine}, volume = {10}, number = {39}, pages = {543-548}, abstract = {Background: Azorella compacta is a rare yellow-green compact resinous cushion shrub growing from the high Andes of southern Per to northwestern Argentina, and which is a producer of biologically active and unique diterpenoids. Objective: This study investigated the secondary metabolites present in a Peruvian sample of Azorella compacta and the evaluation of gastroprotective activity of the isolated compounds in a gastric-induced ulcer model in mice. Material and Methods: Six secondary metabolites (diterpenoids 1-6) present in the dichloromethane (DCM) extract of A. compacta growing in Per were isolated by a combination of Sephadex LH-20 permeation and silica gel chromatography and their chemical structures were elucidated by spectroscopic methods (NMR) and molecular modeling. The gastroprotective activity of the new compound 1 was evaluated on the HCl/EtOH-induced gastric lesion model in mice and compared to the activity showed by the known compounds. Results: A new mulinane diterpene along with five known diterpenoids have been isolated from a Peruvian sample of A. compacta and the gastroprotective results show that compound 1 is less active than the other known mulinane diterpenoids isolated. Conclusions: A. compacta growing in Per showed the presence of the new mulinane 1, which was poorly active in the HCl/EtOH-induced gastric lesion model in mice. Indeed, the activity was lower than other diterpenoids (2-6) showing an oxygenated function at C-16 or/and C-20, which confirm the role of an oxygenated group (OH or carboxylic acid) for the gastroprotective activity of mulinane compounds.}, keywords = {acids activity, apiaceae, azorella carbon compacta, crassifolium, diterpenoids, gastroprotective madreporica, mulinanes, natural-products, skeleton, umbelliferae}, pubstate = {published}, tppubtype = {article} } Background: Azorella compacta is a rare yellow-green compact resinous cushion shrub growing from the high Andes of southern Per to northwestern Argentina, and which is a producer of biologically active and unique diterpenoids. Objective: This study investigated the secondary metabolites present in a Peruvian sample of Azorella compacta and the evaluation of gastroprotective activity of the isolated compounds in a gastric-induced ulcer model in mice. Material and Methods: Six secondary metabolites (diterpenoids 1-6) present in the dichloromethane (DCM) extract of A. compacta growing in Per were isolated by a combination of Sephadex LH-20 permeation and silica gel chromatography and their chemical structures were elucidated by spectroscopic methods (NMR) and molecular modeling. The gastroprotective activity of the new compound 1 was evaluated on the HCl/EtOH-induced gastric lesion model in mice and compared to the activity showed by the known compounds. Results: A new mulinane diterpene along with five known diterpenoids have been isolated from a Peruvian sample of A. compacta and the gastroprotective results show that compound 1 is less active than the other known mulinane diterpenoids isolated. Conclusions: A. compacta growing in Per showed the presence of the new mulinane 1, which was poorly active in the HCl/EtOH-induced gastric lesion model in mice. Indeed, the activity was lower than other diterpenoids (2-6) showing an oxygenated function at C-16 or/and C-20, which confirm the role of an oxygenated group (OH or carboxylic acid) for the gastroprotective activity of mulinane compounds. |
2013 |
Areche, C; Rojas-Alvarez, F; Campos-Briones, C; Lima, C; Perez, E G; Sepulveda, B Further Mulinane Diterpenoids from Azorella Compacta Artículo de revista Journal of Pharmacy and Pharmacology, 65 (8), pp. 1231-1238, 2013, ISSN: 0022-3573. Resumen | Enlaces | BibTeX | Etiquetas: acids activity, azorella carbon compacta, crassifolium, diterpenoid, gastric gastroprotective laretia-acaulis, lesions, llareta, mulinane, natural-products, rats, skeleton, ulcer @article{RN116, title = {Further Mulinane Diterpenoids from Azorella Compacta}, author = { C. Areche and F. Rojas-Alvarez and C. Campos-Briones and C. Lima and E.G. Perez and B. Sepulveda}, url = {/brokenurl#<Go to ISI>://WOS:000321504500014}, doi = {10.1111/jphp.12083}, issn = {0022-3573}, year = {2013}, date = {2013-01-01}, journal = {Journal of Pharmacy and Pharmacology}, volume = {65}, number = {8}, pages = {1231-1238}, 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., keywords findings The new diterpenoids, 13-hydroxymulinane (1), mulin-11,13-dien-20-ol (2), 13-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), 13-hydroxyazorellane (5), 13-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 20mg/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.}, keywords = {acids activity, azorella carbon compacta, crassifolium, diterpenoid, gastric gastroprotective laretia-acaulis, lesions, llareta, mulinane, natural-products, rats, skeleton, ulcer}, pubstate = {published}, tppubtype = {article} } 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., keywords findings The new diterpenoids, 13-hydroxymulinane (1), mulin-11,13-dien-20-ol (2), 13-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), 13-hydroxyazorellane (5), 13-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 20mg/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. |
2014 |
A New Mulinane Diterpenoid from the Cushion Shrub Azorella Compacta Growing in Peru Artículo de revista Pharmacognosy Magazine, 10 (39), pp. 543-548, 2014, ISSN: 0973-1296. |
2013 |
Further Mulinane Diterpenoids from Azorella Compacta Artículo de revista Journal of Pharmacy and Pharmacology, 65 (8), pp. 1231-1238, 2013, ISSN: 0022-3573. |