Elucidating the antioxidant potential of some flavanones as MAO-B inhibitors through DAM, in silico molecular docking and computational analysis.

Abstract

Seven flavanones underwent computational evaluation to determine their effectiveness in filtering UV radiation and scavenging free radicals. The investigated flavanones exhibited enhanced radical scavenging capabilities relative to the parent flavanone, with Hesperidin demonstrating the highest EA and Qmax values, consistent with its antireductant activity. The remaining flavanones displayed lower IE values, suggesting their antioxidant efficacy. Spectroscopic analysis revealed that the HOMO-LUMO and HOMO-1-LUMO transitions are the primary electronic transitions in the UV-Visible spectra of the studied flavanones. Their absorption within the UV-A and UV-B range (260-345 nm) indicates potential utility as UV filters. Theoretical calculations demonstrate that the reactivity of flavanones is concentrated in ring [B], with a reactivity order of 3' > 4' > 2' > 6 > 7 > 5. The BDE values reveal that the 3'-OH group has the lowest value, followed by the 4' position, while hydrogen bonding is responsible for the increased BDE value at position 5. The values of ΔBDE and ΔAIP, relative to phenol, provide a framework for elucidating the preferred mechanism, HAT or SET, underlying the antioxidant behavior. Molecular docking simulations identified hesperetin, 2'-Hydroxyflavanone, 4'-Hydroxyflavanone, Eriodictyol, and Naringenin as potential MAO-B inhibitors, outperforming their synthetic counterparts in this regard.