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. |
2016 |
Bioorganic & Medicinal Chemistry Letters, 26 (14), pp. 3220-3222, 2016, ISSN: 0960-894x. |