Molecular modeling and DFT studies on the antioxidant activity of Centaurea scoparia flavonoids and molecular dynamics simulation of their interaction with β-lactoglobulin
EntidadUAM. Departamento de Química
EditorRoyal Society of Chemistry
Fecha de edición2023-04-19
10.1039/d3ra01661gRSC Advances 13.18 (2023): 12361 - 12374
Versión del editorhttps://doi.org/10.1039/d3ra01661g
MateriasAntioxidants; Atoms; Binding Energy; Electron Transitions; Flavonoids; Hydrogen; Química
Derechos© 2023 The Author(s)
Esta obra está bajo una licencia de Creative Commons Reconocimiento-NoComercial 4.0 Internacional.
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
Google Scholar:Kamel, Emadeldin M. - Bin-Ammar, Albandari - El-Bassuony, Ashraf A. - Alanazi, Mohammed M. - Altharawi, Ali - Ahmeda, Ahmad F. - Alanazi, Ashwag S. - Lamsabhi, Al Mokhtar - Mahmoud, Ayman M.
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