Target prediction and antioxidant analysis on isoflavones of demethyltexasin: a DFT study

Glycosylated flavonoids are often found in supplementary food sources and are structurally more active than aglycones, as the glycosyl unit offers better solubility, stability, and functionality. The most common glycosyl units present in most secondary metabolites are glucoside and rhamnoside attached to flavonoid moiety. In the present work, 4'-O-glycosylated (4'-O-glucoside and 4'-O-rhamnoside) demethyltexasin, a soy isoflavone bearing a chromen nucleus, is investigated through a green route aided by density functional theory. Antioxidant activity is computed via three different antioxidant mechanisms, in which hydrogen atom abstraction is facilitated effectively in both gas and solvent phases. The 6-OH site (A-ring) in both isoflavone demethyltexasin glucoside (DMTG) and isoflavone demethyltexasin rhamnoside (DMTR) acted as better radical scavenging sites. Charge localization in B-ring is well altered by the glycosyl and rhamnosyl groups attached. Target prediction analysis supports DMTG with good binding ability with the selected homosapien class targets. The results depict that even though the flavonoid possessing rhamnosyl unit induces charge delocalization at the 4'-O position, it offers resistance toward antioxidant activity when compared to glycosyl moeity. Graphical abstract The contour representation of antioxidants demethyltexasin 4'-O- glucoside (DMTG) and demethyltexasin 4'-O- rhamnoside (DMTR) against reactive oxygen species(ROS).