2016 |
Sepulveda, B; Quispe, C; Simirgiotis, M; Garcia-Beltran, O; Areche, C Bioorganic & Medicinal Chemistry Letters, 26 (14), pp. 3220-3222, 2016, ISSN: 0960-894x. Resumen | Enlaces | BibTeX | Etiquetas: azorella biotransformation, compacta, cuatrecasasii, gastric madreporica microbial mulinane, transformation, ulcer @article{RN288, title = {Gastroprotective Effects of New Diterpenoid Derivatives from Azorella Cuatrecasasii Mathias & Constance Obtained Using a Beta-Cyclodextrin Complex with Microbial and Chemical Transformations}, author = { B. Sepulveda and C. Quispe and M. Simirgiotis and O. Garcia-Beltran and C. Areche}, url = {/brokenurl#<Go to ISI>://WOS:000377471400003}, doi = {10.1016/j.bmcl.2016.05.081}, issn = {0960-894x}, year = {2016}, date = {2016-01-01}, journal = {Bioorganic & Medicinal Chemistry Letters}, volume = {26}, number = {14}, pages = {3220-3222}, publisher = {2016 Elsevier Ltd.}, abstract = {Mulinane diterpenoids isolated from Azorella species have displayed gastroprotective effects in animal models. In this study we have transformed the main constituent, mulin-11,13-dien-20 oic acid from this plant using the filamentous fungus Mucor plumbeus and a beta-cyclodextrin inclusion complex and we have obtained two main products with good yields (33% and 15% for compound 4 and 5, respectively) for further preparation of semisynthetic derivatives to evaluate their gastroprotective effects. In addition, one of the compounds isolated from Azorella cuatrecasasii was new (9-epi-13 alpha-hydroxymulinene 1). Six new derivatives 4a-4c and 5a-5c were then prepared by simple chemical transformations. The structures of all compounds were elucidated by spectroscopic means based on 1D and 2D-NMR techniques. Some 8 diterpenes were evaluated for their gastroprotective effects in the ethanol/HCl-induced ulcer model in mice at 20 mg/kg. The highest gastroprotective activity was shown by 7 alpha,16-dihydroxymulin-11,13-dien- 20-oic acid 5, which was higher than the reference drug lansoprazole, while 16-hydroxymulin-11,13- dien-20-oic acid 4 was as active as lansoprazole.}, keywords = {azorella biotransformation, compacta, cuatrecasasii, gastric madreporica microbial mulinane, transformation, ulcer}, pubstate = {published}, tppubtype = {article} } Mulinane diterpenoids isolated from Azorella species have displayed gastroprotective effects in animal models. In this study we have transformed the main constituent, mulin-11,13-dien-20 oic acid from this plant using the filamentous fungus Mucor plumbeus and a beta-cyclodextrin inclusion complex and we have obtained two main products with good yields (33% and 15% for compound 4 and 5, respectively) for further preparation of semisynthetic derivatives to evaluate their gastroprotective effects. In addition, one of the compounds isolated from Azorella cuatrecasasii was new (9-epi-13 alpha-hydroxymulinene 1). Six new derivatives 4a-4c and 5a-5c were then prepared by simple chemical transformations. The structures of all compounds were elucidated by spectroscopic means based on 1D and 2D-NMR techniques. Some 8 diterpenes were evaluated for their gastroprotective effects in the ethanol/HCl-induced ulcer model in mice at 20 mg/kg. The highest gastroprotective activity was shown by 7 alpha,16-dihydroxymulin-11,13-dien- 20-oic acid 5, which was higher than the reference drug lansoprazole, while 16-hydroxymulin-11,13- dien-20-oic acid 4 was as active as lansoprazole. |
2014 |
studillo-Saavedra, L; Gutierrez, M; Quesada, L; San-Martin, A; Espinoza, L; Penailillo, P New Diterpenes from Azorella Spinosa Artículo de revista Natural Product Communications, 9 (1), pp. 9-12, 2014, ISSN: 1934-578x. Resumen | Enlaces | BibTeX | Etiquetas: azorella, compacta, diterpenes, triterpenoids, umbelliferae @article{RN179, title = {New Diterpenes from Azorella Spinosa}, author = { L. studillo-Saavedra and M. Gutierrez and L. Quesada and A. San-Martin and L. Espinoza and P. Penailillo}, url = {/brokenurl#<Go to ISI>://WOS:000330552200005}, issn = {1934-578x}, year = {2014}, date = {2014-01-01}, journal = {Natural Product Communications}, volume = {9}, number = {1}, pages = {9-12}, abstract = {Two new diterpenes,2-acetoxy-13-hydroxy-mulin-11-ene and 2-acetoxy-mulin-11, 13-diene,have been isolated from the aerial parts of Azorella spinosa and their structures determined by spectroscopic and conventional chemical methods. Furthermore, 2, 13-dihydroxy-mulin-11-ene was obtained using a basic hydrolysis of the first compound. Two diterpenes reported for other Azorella species have also been found, namely mulinolic acid and 13 beta-hydroxyazorellane, as well as the triterpene lactone of ursolic acid,quercetin, and 7-hydroxycoumarin. The compounds were evaluated using antibacterial, antioxidant and enzymatic assays; no significant activity was detected.}, keywords = {azorella, compacta, diterpenes, triterpenoids, umbelliferae}, pubstate = {published}, tppubtype = {article} } Two new diterpenes,2-acetoxy-13-hydroxy-mulin-11-ene and 2-acetoxy-mulin-11, 13-diene,have been isolated from the aerial parts of Azorella spinosa and their structures determined by spectroscopic and conventional chemical methods. Furthermore, 2, 13-dihydroxy-mulin-11-ene was obtained using a basic hydrolysis of the first compound. Two diterpenes reported for other Azorella species have also been found, namely mulinolic acid and 13 beta-hydroxyazorellane, as well as the triterpene lactone of ursolic acid,quercetin, and 7-hydroxycoumarin. The compounds were evaluated using antibacterial, antioxidant and enzymatic assays; no significant activity was detected. |
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. |
2013 |
Quesada, L; Gutierrez, M; studillo-Saavedra, L; San-Martin, A; Fuentes, E; Palomo, I; Penailillo, P Determination of Antibacterial, Antioxidant, Antiplatelet and Inhibition of Cholinesterase Activities from the Methanolic Extracts of Azorella Species (Apiaceae) Artículo de revista Boletin Latinoamericano Y Del Caribe De Plantas Medicinales Y Aromaticas, 12 (1), pp. 99-107, 2013, ISSN: 0717-7917. Resumen | Enlaces | BibTeX | Etiquetas: alzheimers-disease, antibacterial, antioxidant, antiplatelet, azorella, cholinesterase, compacta, diterpenoids, phenolics, products, total yareta @article{RN114, title = {Determination of Antibacterial, Antioxidant, Antiplatelet and Inhibition of Cholinesterase Activities from the Methanolic Extracts of Azorella Species (Apiaceae)}, author = { L. Quesada and M. Gutierrez and L. studillo-Saavedra and A. San-Martin and E. Fuentes and I. Palomo and P. Penailillo}, url = {/brokenurl#<Go to ISI>://WOS:000314060700011}, issn = {0717-7917}, year = {2013}, date = {2013-01-01}, journal = {Boletin Latinoamericano Y Del Caribe De Plantas Medicinales Y Aromaticas}, volume = {12}, number = {1}, pages = {99-107}, abstract = {In this study, we investigated the potential antibacterial, antioxidant and anti-platelet activities and the inhibition of cholinesterase from the methanolic extracts obtained from aerial parts of the two species of Azorella: A. spinosa (Constitution, Chile) and A. monantha (Torres del Paine, Enladrillado and Paso Vergara). All extracts showed only moderate inhibitory activity on acetylcholinesterase (AChE), the most active extract with IC50 = 27 mu g/mL was A. spinosa. Inhibition of platelet aggregation induced by ADP presented maximal aggregation to 70 and 57% on extracts of A. spinosa and A. monantha (Paso Vergara), respectively. The most active extract with antioxidant effect was A. spinosa with IC50 of 28.72 mu g/mL. Antibacterial activity of the extract on Escherichia coli, Pseudomonas aeruginosa and Acinetobacter baumannii was not present. The extracts of A. spinosa and A. monantha (Paso Vergara) presented the best results on the activities that were evaluated.}, keywords = {alzheimers-disease, antibacterial, antioxidant, antiplatelet, azorella, cholinesterase, compacta, diterpenoids, phenolics, products, total yareta}, pubstate = {published}, tppubtype = {article} } In this study, we investigated the potential antibacterial, antioxidant and anti-platelet activities and the inhibition of cholinesterase from the methanolic extracts obtained from aerial parts of the two species of Azorella: A. spinosa (Constitution, Chile) and A. monantha (Torres del Paine, Enladrillado and Paso Vergara). All extracts showed only moderate inhibitory activity on acetylcholinesterase (AChE), the most active extract with IC50 = 27 mu g/mL was A. spinosa. Inhibition of platelet aggregation induced by ADP presented maximal aggregation to 70 and 57% on extracts of A. spinosa and A. monantha (Paso Vergara), respectively. The most active extract with antioxidant effect was A. spinosa with IC50 of 28.72 mu g/mL. Antibacterial activity of the extract on Escherichia coli, Pseudomonas aeruginosa and Acinetobacter baumannii was not present. The extracts of A. spinosa and A. monantha (Paso Vergara) presented the best results on the activities that were evaluated. |
2016 |
Bioorganic & Medicinal Chemistry Letters, 26 (14), pp. 3220-3222, 2016, ISSN: 0960-894x. |
2014 |
New Diterpenes from Azorella Spinosa Artículo de revista Natural Product Communications, 9 (1), pp. 9-12, 2014, ISSN: 1934-578x. |
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. |
2013 |
Determination of Antibacterial, Antioxidant, Antiplatelet and Inhibition of Cholinesterase Activities from the Methanolic Extracts of Azorella Species (Apiaceae) Artículo de revista Boletin Latinoamericano Y Del Caribe De Plantas Medicinales Y Aromaticas, 12 (1), pp. 99-107, 2013, ISSN: 0717-7917. |