Antioxidant potential of orientin: A combined experimental and DFT approach

The antioxidant activity of the bioactive fractions obtained from the leaves of Rhynchosia capitata is evaluated for its capacity to reduce ferric ions. In vitro antihemolytic analysis for the separated erythrocytes of Wistar rat blood cells exhibits maximum inhibition value for ethyl acetate (1202.55 ± 9.46) than ethanol fraction (424.57 ± 12.04). Gas and solvent phase studies of structural and molecular characteristics of C-glycosyl flavonoid, orientin present in the bioactive fraction of R. capitata is investigated through hydrogen atom transfer mechanism (HAT) using DFT/B3LYP/6-311G(d,p) level of theory. Interestingly, the intramolecular hydrogen bonding formed between 3′-O and 4′-H makes 3′-OH as the active site which is supported by its bond dissociation energy values. The computed values of the adiabatic ionization potential, electron affinity, hardness, softness, electronegativity and electrophilic index indicate that orientin possess good radical scavenging activity. In this study, role of molecular electrostatic potential and electron density distribution map in predicting the importance of B-ring are analyzed and reported. Spin density distribution analysis for the radicals is formed by summing of spin on rings A, B and C. The most active system able to transfer a hydrogen atom is orientin compared to vitexin and the bond dissociation enthalpy follows the order benzene > ethyl acetate > water.