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.
%0 Journal Article
%1 RN183
%A Areche, C.
%A Sepulveda, B.
%A San Martin, A.
%A Garcia-Beltran, O.
%A Simirgiotis, M.
%A Canete, A.
%D 2014
%J Organic & Biomolecular Chemistry
%K compacta, cytoprotection, defense, dqcauchile madreporica, mucosal natural-products, skeleton
%N 33
%P 6406-6413
%R 10.1039/c4ob00966e
%T An Unusual Mulinane Diterpenoid from the Chilean Plant Azorella Trifurcata (Gaertn) Pers
%U /brokenurl#<Go to ISI>://WOS:000340437800014
%V 12
%X 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.
@article{RN183,
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.},
added-at = {2019-12-04T03:57:35.000+0100},
author = {Areche, C. and Sepulveda, B. and San Martin, A. and Garcia-Beltran, O. and Simirgiotis, M. and Canete, A.},
biburl = {https://www.bibsonomy.org/bibtex/23cd5e81493a9592dc7c14b7a57eeb538/dqcauchile},
doi = {10.1039/c4ob00966e},
interhash = {635d390a752e94f1ac9bc2e3314b7476},
intrahash = {3cd5e81493a9592dc7c14b7a57eeb538},
issn = {1477-0520},
journal = {Organic & Biomolecular Chemistry},
keywords = {compacta, cytoprotection, defense, dqcauchile madreporica, mucosal natural-products, skeleton},
number = 33,
pages = {6406-6413},
timestamp = {2019-12-04T03:58:17.000+0100},
title = {An Unusual Mulinane Diterpenoid from the Chilean Plant Azorella Trifurcata (Gaertn) Pers},
type = {Journal Article},
url = {/brokenurl#<Go to ISI>://WOS:000340437800014},
volume = 12,
year = 2014
}