Molecular modeling and DFT studies on the antioxidant activity of Centaurea scoparia flavonoids and molecular dynamics simulation of their interaction with β-lactoglobulin

Emadeldin M. Kamel; Albandari Bin-Ammar; Ashraf A. El-Bassuony; Mohammed M. Alanazi; Ali Altharawi; Ahmad F. Ahmeda; Ashwag S. Alanazi; Al Mokhtar Lamsabhi; Ayman M. Mahmoud

doi:10.1039/D3RA01661G

Molecular modeling and DFT studies on the antioxidant activity of Centaurea scoparia flavonoids and molecular dynamics simulation of their interaction with β-lactoglobulin†

Emadeldin M. Kamel,

^a Albandari Bin-Ammar,^b Ashraf A. El-Bassuony,^a Mohammed M. Alanazi,^c Ali Altharawi,^d Ahmad F. Ahmeda,^ef Ashwag S. Alanazi,^g Al Mokhtar Lamsabhi

^hi and Ayman M. Mahmoud

*^jk

Author affiliations

* Corresponding authors

^a Chemistry Department, Faculty of Science, Beni-Suef University, Beni-Suef 62514, Egypt

^b Department of Clinical Nutrition, College of Applied Medical Sciences, University of Hail, Saudi Arabia

^c Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia

^d Department of Pharmaceutical Chemistry, College of Pharmacy, Prince Sattam Bin Abdulaziz University, Al-Kharj 11942, Saudi Arabia

^e Department of Basic Medical Sciences, College of Medicine, Ajman University, Ajman 346, United Arab Emirates

^f Center of Medical and Bio-allied Health Sciences Research, Ajman University, Ajman 346, United Arab Emirates

^g Department of Pharmaceutical Sciences, College of Pharmacy, Princess Nourah bint Abdulrahman University, Riyadh, Saudi Arabia

^h Departamento de Química, Módulo 13, Universidad Autónoma de Madrid, Campus de Excelencia UAM-CSIC Cantoblanco, Madrid 28049, Spain

ⁱ Institute for Advanced Research in Chemical Sciences (IAdChem), Universidad Autónoma de Madrid, Madrid 28049, Spain

^j Physiology Division, Zoology Department, Faculty of Science, Beni-Suef University, Salah Salim St., Beni-Suef 62514, Egypt
E-mail: ayman.mahmoud@science.bsu.edu.eg

^k Department of Life Sciences, Faculty of Science and Engineering, Manchester Metropolitan University, Manchester M1 5GD, UK

Abstract

Plants of the genus Centaurea have been widely used as natural therapeutics in different countries. This study investigated the antioxidant–structure activity relationship of eight flavonoids isolated from Centaurea scoparia using DFT studies and in vitro radical scavenging and xanthine oxidase (XO) inhibition assays, and to correlate the theoretical values with the experimental findings. Docking analysis was carried out to explore the binding modes of the isolated phytochemicals with XO and bovine β-lactoglobulin (BLG). Interactions of the isolated compounds with BLG were studied using molecular dynamics (MD) simulations which revealed the involvement of hydrogen bonding. The root-mean-square deviation (RMSD) of BLG and BLG-flavonoid complexes reached equilibrium and fluctuated during the 10 ns MD simulations. The radius of gyration (Rg) and solvent accessible surface area (SASA) revealed that various systems were stabilized at approximately 2500 ps. In addition, the RMS fluctuations profile indicated that the ligand's active site exerted rigidity behavior during the simulation. The hydrogen atom transfer (HAT) and the energies of hydrogen abstractions were estimated by calculating the bond dissociation enthalpy (BDE) of O–H in gas phase and water. The isolated compounds showed radical scavenging and XO inhibitory activities along with binding affinity with XO as revealed in silico. The BDE was linked to the radical scavenging processes occurring in polar solvents. These processes are single electron transfer followed by proton transfer (SET-PT) and sequential proton loss electron transfer (SPLET). Our calculations indicated the agreement between the calculated results and the experimentally measured antioxidant activity of the flavonoids isolated from C. scoparia.

This article is part of the themed collection: 2023 RSC Advances Popular Advances Collection

RSC Advances

Molecular modeling and DFT studies on the antioxidant activity of Centaurea scoparia flavonoids and molecular dynamics simulation of their interaction with β-lactoglobulin†

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Molecular modeling and DFT studies on the antioxidant activity of Centaurea scoparia flavonoids and molecular dynamics simulation of their interaction with β-lactoglobulin

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