α-Glucosidase activity of oleanolic acid and its oxidative metabolites: DFT and Docking studies

Author(s): El Hassane Anouar, Nur Shahidatul Shida Zakaria, Ali Alsalme, Syed Adnan Ali Shah.

Journal Name: Mini-Reviews in Medicinal Chemistry

Volume 15 , Issue 14 , 2015

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Abstract:

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.

Keywords: Chemical shifts, DFT, Docking, α-Glucosidase, NMR, TD-DFT, Oleanolic acid, UV/visible.

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Article Details

VOLUME: 15
ISSUE: 14
Year: 2015
Page: [1148 - 1158]
Pages: 11
DOI: 10.2174/1389557515666150724154044
Price: $58

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