Gastroprotective effects of new diterpenoid derivatives from Azorella cuatrecasasii Mathias & Constance obtained using a b-cyclodextrin complex with microbial and chemical transformations
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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. (C) 2016 Elsevier Ltd. All rights reserved.
FONDECYT Iniciacion, Universidad de Ibague project
Artículo de publicación ISI
Quote ItemBioorganic & Medicinal Chemistry Letters. Volumen: 26 Número: 14 Páginas: 3220-3222
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