α-Glucosidase activity of oleanolic acid and its oxidative metabolites: DFT and Docking studies
| Autor: | El Hassane Anouar, Ali Alsalme, Nur Shahidatul Shida Zakaria, Syed Adnan Ali Shah |
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| Rok vydání: | 2015 |
| Předmět: |
Pharmacology
Chemistry Stereochemistry Chemical shift Molecular Conformation alpha-Glucosidases General Medicine Carbon-13 NMR Molecular Docking Simulation Enzyme Activation Solvent chemistry.chemical_compound Docking (molecular) Drug Discovery Bathochromic shift Proton NMR Humans Quantum Theory Glycoside Hydrolase Inhibitors Oleanolic Acid Oxidation-Reduction Oleanolic acid |
| Zdroj: | Mini-Reviews in Medicinal Chemistry. 15:1148-1158 |
| ISSN: | 1389-5575 |
| Popis: | A natural pentacyclic triterpenoid oleanolic acid 1 and its biotransformed metabolites 2-3 are potential α-glucosidase inhibitors. To elucidate the inhibitory mechanism of compounds 1, 2 and 3 against α-glucosidase, we calculated (i) their electronic and optical properties using DFT and TD-DFT at the B3LYP/6-31G(d) level in gas and IEF-PCM solvent; and (ii) their binding energies to α-glucosidase via docking study. DFT results showed that the α-glucosidase inhibtion is mainly depend on the polarity parameters of the studied compounds. Docking results revealed that the activity increased with binding energies (i.e. the stability of ligand-receptor complex). The specroscopic data of oleanolic acid 1 and its metabolites 2 and 3 are well predicetd for 13C NMR chemical shifts (R2=99%) and 1H NMR chemical shifts (R2=90%); and for (ii) UV/vis spectra. The assignments and interpretation of NMR chemical shifts and bathochromic shift of λMAX absorption bands are discussed. |
| Databáze: | OpenAIRE |
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