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.
Mini-Reviews in Medicinal Chemistry
Title:α-Glucosidase activity of oleanolic acid and its oxidative metabolites: DFT and Docking studies
Volume: 15 Issue: 14
Author(s): El Hassane Anouar, Nur Shahidatul Shida Zakaria, Ali Alsalme and Syed Adnan Ali Shah
Affiliation:
Keywords: Chemical shifts, DFT, Docking, α-Glucosidase, NMR, TD-DFT, Oleanolic acid, UV/visible.
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.
Export Options
About this article
Cite this article as:
Hassane Anouar El, Shida Zakaria Nur Shahidatul, Alsalme Ali and Adnan Ali Shah Syed, α-Glucosidase activity of oleanolic acid and its oxidative metabolites: DFT and Docking studies , Mini-Reviews in Medicinal Chemistry 2015; 15 (14) . https://dx.doi.org/10.2174/1389557515666150724154044
DOI https://dx.doi.org/10.2174/1389557515666150724154044 |
Print ISSN 1389-5575 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5607 |
- Author Guidelines
- Graphical Abstracts
- Fabricating and Stating False Information
- Research Misconduct
- Post Publication Discussions and Corrections
- Publishing Ethics and Rectitude
- Increase Visibility of Your Article
- Archiving Policies
- Peer Review Workflow
- Order Your Article Before Print
- Promote Your Article
- Manuscript Transfer Facility
- Editorial Policies
- Allegations from Whistleblowers
Related Articles
-
Recent Progress of Medicinal Chemistry Research on Peroxisome Proliferator-Activated Receptor (PPAR) Ligands for the Treatment of Metabolic Syndrome
Current Bioactive Compounds Efficacy and Cardiovascular Safety of Antidiabetic Medications
Current Drug Safety Soybean and Processed Soy Foods Ingredients, and Their Role in Cardiometabolic Risk Prevention
Recent Patents on Food, Nutrition & Agriculture Does Osteoblast to Adipocyte Differentiation Play a Role in Osteoarthritis?
Current Rheumatology Reviews Diabetes and Heart Failure: Is it Hyperglycemia or Hyperinsulinemia?
Current Vascular Pharmacology The Relationship between Age-Related Kidney Dysfunction and Framingham Risk Score in Healthy People in China
Current Aging Science Withdrawal Notice: Ionic Liquid Mediated Synthesis of Schiff bases Bearing Thiazole and Indole Moieties
Current Organic Synthesis Lipoic Acid: A Novel Therapeutic Approach for Multiple Sclerosis and Other Chronic Inflammatory Diseases of the CNS
Endocrine, Metabolic & Immune Disorders - Drug Targets Negative Glucocorticoid Receptor Response Elements and their Role in Glucocorticoid Action
Current Pharmaceutical Design Application of Microdialysis in Clinical Pharmacology
Current Clinical Pharmacology Oxidative Stress: Meeting Multiple Targets in Pathogenesis of Diabetic Nephropathy
Current Drug Targets Effects of High Intensity Statin Therapy in the Treatment of Diabetic Dyslipidemia in Patients with Coronary Artery Disease
Current Pharmaceutical Design A Review on the Effects of New Anti-Diabetic Drugs on Platelet Function
Endocrine, Metabolic & Immune Disorders - Drug Targets Drainage of Cerebral Abscesses Prior to Valve Replacement in Stable Patients with Acute Left-Sided Infective Endocarditis
CNS & Neurological Disorders - Drug Targets Cardioprotector Activity of an Esteroidal Saponin: A Scientific and Technological Prospection
Recent Patents on Biotechnology Anti-Inflammatory Drugs and Statins for Arterial Stiffness Reduction
Current Pharmaceutical Design Roles of IL-6-gp130 Signaling in Vascular Inflammation
Current Cardiology Reviews Fibrate-Associated Adverse Effects Beyond Muscle and Liver Toxicity
Current Pharmaceutical Design Contraindications for Anticoagulation in Older Patients with Atrial Fibrillation: A Narrative Review
Current Drug Safety Graphical Abstracts
Medicinal Chemistry