2015 |
Areche, C; Benites, J; Cornejo, A; Ruiz, L M; Garcia-Beltran, O; Simirgiotis, M J; Sepulveda, B Seco-Taondiol, an Unusual Meroterpenoid from the Chilean Seaweed Stypopodium Flabelliforme and Its Gastroprotective Effect in Mouse Model Artículo de revista Marine Drugs, 13 (4), pp. 1726-1738, 2015, ISSN: 1660-3397. Resumen | Enlaces | BibTeX | Etiquetas: activity, algae, antiproliferative cytoprotection defense, epitaondiol, isoepitaondiol, meroditerpenoids, mucosal natural-products, zonale @article{RN238, title = {Seco-Taondiol, an Unusual Meroterpenoid from the Chilean Seaweed Stypopodium Flabelliforme and Its Gastroprotective Effect in Mouse Model}, author = { C. Areche and J. Benites and A. Cornejo and L.M. Ruiz and O. Garcia-Beltran and M.J. Simirgiotis and B. Sepulveda}, url = {/brokenurl#<Go to ISI>://WOS:000353715900008}, doi = {10.3390/md13041726}, issn = {1660-3397}, year = {2015}, date = {2015-01-01}, journal = {Marine Drugs}, volume = {13}, number = {4}, pages = {1726-1738}, abstract = {Ten known meroterpenoids and the new meroterpenoid 7 were isolated from the Chilean seaweed Stypopodium flabelliforme as their acetylated derivatives. Furthermore, the known metabolite taondiol has been isolated for the first time from this species. The molecular structure of the new metabolite was determined by spectroscopic methods based on 1D- and 2D-NMR. Isolation of 7 represents a keywords step toward a better understanding of the biogenesis of this class of meroterpenoids. Among the meroditerpenoids isolated, stypodiol, isoepitaondiol, epitaondiol and sargaol exhibited gastroprotective activity on the HCl/Ethanol-induced gastric lesions model in mice. Regarding the mode of gastroprotective action, the activity of epitaondiol was reversed significantly when animals were pretreated with indomethacin, N-ethylmaleimide and N-nitro-l-arginine methyl ester (L-NAME) suggesting that prostaglandins, sulfhydryl groups and nitric oxide are involved in their mode of gastroprotective action. In the case of sargaol the gastroprotective activity was attenuated with indomethacin and N-ethylmaleimide, which suggests that prostaglandins and sulfhydryl groups are also involved in the mode of action using this model.}, keywords = {activity, algae, antiproliferative cytoprotection defense, epitaondiol, isoepitaondiol, meroditerpenoids, mucosal natural-products, zonale}, pubstate = {published}, tppubtype = {article} } Ten known meroterpenoids and the new meroterpenoid 7 were isolated from the Chilean seaweed Stypopodium flabelliforme as their acetylated derivatives. Furthermore, the known metabolite taondiol has been isolated for the first time from this species. The molecular structure of the new metabolite was determined by spectroscopic methods based on 1D- and 2D-NMR. Isolation of 7 represents a keywords step toward a better understanding of the biogenesis of this class of meroterpenoids. Among the meroditerpenoids isolated, stypodiol, isoepitaondiol, epitaondiol and sargaol exhibited gastroprotective activity on the HCl/Ethanol-induced gastric lesions model in mice. Regarding the mode of gastroprotective action, the activity of epitaondiol was reversed significantly when animals were pretreated with indomethacin, N-ethylmaleimide and N-nitro-l-arginine methyl ester (L-NAME) suggesting that prostaglandins, sulfhydryl groups and nitric oxide are involved in their mode of gastroprotective action. In the case of sargaol the gastroprotective activity was attenuated with indomethacin and N-ethylmaleimide, which suggests that prostaglandins and sulfhydryl groups are also involved in the mode of action using this model. |
2014 |
Areche, C; Sepulveda, B; Martin, San A; Garcia-Beltran, O; Simirgiotis, M; Canete, A An Unusual Mulinane Diterpenoid from the Chilean Plant Azorella Trifurcata (Gaertn) Pers Artículo de revista Organic & Biomolecular Chemistry, 12 (33), pp. 6406-6413, 2014, ISSN: 1477-0520. Resumen | Enlaces | BibTeX | Etiquetas: compacta, cytoprotection, defense, madreporica, mucosal natural-products, skeleton @article{RN183, title = {An Unusual Mulinane Diterpenoid from the Chilean Plant Azorella Trifurcata (Gaertn) Pers}, author = { C. Areche and B. Sepulveda and A. San Martin and O. Garcia-Beltran and M. Simirgiotis and A. Canete}, url = {/brokenurl#<Go to ISI>://WOS:000340437800014}, doi = {10.1039/c4ob00966e}, issn = {1477-0520}, year = {2014}, date = {2014-01-01}, journal = {Organic & Biomolecular Chemistry}, volume = {12}, number = {33}, pages = {6406-6413}, abstract = {Four new mulinane-type diterpenoids besides the known compounds mulin-11,13-dien-20-oic acid, 13 alpha-hydroxyazorellane, 13 beta-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, 7 alpha-acetoxy-9-epi-13 beta-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 = 55mg 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.}, keywords = {compacta, cytoprotection, defense, madreporica, mucosal natural-products, skeleton}, pubstate = {published}, tppubtype = {article} } Four new mulinane-type diterpenoids besides the known compounds mulin-11,13-dien-20-oic acid, 13 alpha-hydroxyazorellane, 13 beta-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, 7 alpha-acetoxy-9-epi-13 beta-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 = 55mg 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. |
2015 |
Seco-Taondiol, an Unusual Meroterpenoid from the Chilean Seaweed Stypopodium Flabelliforme and Its Gastroprotective Effect in Mouse Model Artículo de revista Marine Drugs, 13 (4), pp. 1726-1738, 2015, ISSN: 1660-3397. |
2014 |
An Unusual Mulinane Diterpenoid from the Chilean Plant Azorella Trifurcata (Gaertn) Pers Artículo de revista Organic & Biomolecular Chemistry, 12 (33), pp. 6406-6413, 2014, ISSN: 1477-0520. |