%0 Journal Article %1 RN288 %A Sepulveda, B. %A Quispe, C. %A Simirgiotis, M. %A Garcia-Beltran, O. %A Areche, C. %D 2016 %I 2016 Elsevier Ltd. %J Bioorganic & Medicinal Chemistry Letters %K azorella biotransformation, compacta, cuatrecasasii, dqcauchile gastric madreporica microbial mulinane, transformation, ulcer, %N 14 %P 3220-3222 %R 10.1016/j.bmcl.2016.05.081 %T Gastroprotective Effects of New Diterpenoid Derivatives from Azorella Cuatrecasasii Mathias & Constance Obtained Using a Beta-Cyclodextrin Complex with Microbial and Chemical Transformations %U /brokenurl#<Go to ISI>://WOS:000377471400003 %V 26 %X 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.

@article{RN288, 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. }, added-at = {2019-12-04T03:57:35.000+0100}, author = {Sepulveda, B. and Quispe, C. and Simirgiotis, M. and Garcia-Beltran, O. and Areche, C.}, biburl = {https://www.bibsonomy.org/bibtex/225b2b3cb84cb9b0991b4991502939946/dqcauchile}, doi = {10.1016/j.bmcl.2016.05.081}, interhash = {8f88620c9c8ee758de817e7cc6aa95b2}, intrahash = {25b2b3cb84cb9b0991b4991502939946}, issn = {0960-894x}, journal = {Bioorganic & Medicinal Chemistry Letters}, keywords = {azorella biotransformation, compacta, cuatrecasasii, dqcauchile gastric madreporica microbial mulinane, transformation, ulcer,}, number = 14, pages = {3220-3222}, publisher = {2016 Elsevier Ltd.}, timestamp = {2019-12-04T03:58:17.000+0100}, title = {Gastroprotective Effects of New Diterpenoid Derivatives from Azorella Cuatrecasasii Mathias & Constance Obtained Using a Beta-Cyclodextrin Complex with Microbial and Chemical Transformations}, type = {Journal Article}, url = {/brokenurl#<Go to ISI>://WOS:000377471400003}, volume = 26, year = 2016 }