DFT Studies on the Antioxidant Activity of Naringenin and Its Derivatives: Effects of the Substituents at C3

Abstract

The radical scavenging activity of a flavonoid is largely influenced by its structure. The effects of the substituents at C3 position on the antioxidant activity of naringenin were carried out using the density functional theory (DFT) method. The reaction enthalpies related with the three well-established mechanisms were analyzed. Excellent correlations were found between the reaction enthalpies and Hammett sigma constants. Equations obtained from the linear regression can be helpful in the selection of suitable candidates for the synthesis of novel naringenin derivatives with enhanced antioxidant properties. In the gas and benzene phases, the antioxidant activity of naringenin was enhanced by the electron-donating substituents via weakening the bond dissociation enthalpy (BDE). In the water phase, it was strengthened by electron-withdrawing groups—via lowering the proton affinity (PA). The electronic effect of the substituent on the BDE of naringenin is mainly governed by the resonance effect, while that on the ionization potential (IP) and PA of naringenin is mainly controlled by the field/inductive effect.

Antioxidant Properties and Structure-Antioxidant Activity Relationship of Allium Species Leaves

“…Catechin (3,3′,4′,5,7-pentahydroxyflavan) is a compound commonly found in several types of green tea, cocoa, red grapes and onions [ 49 , 120 , 131 , 132 , 133 ]. It also can be found and isolated from A. schoenoprasum [ 62 ].…”

Analysis of Conformational, Structural, Magnetic, and Electronic Properties Related to Antioxidant Activity: Revisiting Flavan, Anthocyanidin, Flavanone, Flavonol, Isoflavone, Flavone, and Flavan-3-ol

“…Different computational approaches have been used to investigate flavonoid structures. 3 , 31 , 37 , 38 Recently, Zheng et al performed a comparative study focusing on the interactions of the hydrogens in the solvated systems of 5,7-dihydroxy-2-(3,4-dihydroxyphenyl)-chrome-4-one (luteolin) using DFT (B3LYP method) and concluded that luteolin presents a nonplanar conformation. 37 Similarly, Matteini et al.…”

Cassia fistula Leaves; UHPLC-QTOF-MS/MS Based Metabolite Profiling and Molecular Docking Insights to Explore Bioactives Role towards Inhibition of Pancreatic Lipase

“…Many therapeutic agents have been identified in medicinal plants. However, some of these medicinal plants might contain a wide variety of chemical compounds, often with undetermined biological properties [ 62 ]. The antioxidant activities of polyphenolic compounds depend upon their ability to resist harmful effects of free radical species.…”