Structure–antioxidant activity relationships of dendrocandin analogues determined using density functional theory

Abstract

Quantum-chemical calculations based on the density functional theory (DFT) at the B3LYP/6-311 + + G(2d,2p)//B3LYP/6-31G(d,p) level were employed to study the relationship between the antioxidant properties and chemical structures of six dendrocandin (DDCD) analogues in the gas phase and two solvents (methanol and water). The hydrogen atom transfer (HAT), electron-transfer-proton-transfer (ET-PT), and sequential proton-loss-electron-transfer (SPLET) mechanisms are explored. The highest occupied molecular orbital (HOMO), lowest unoccupied molecular orbital (LUMO), reactivity indices (η, μ, ω, ω + , and ω -), and molecular electrostatic potentials (MEPs) were also evaluated. The results suggest that the D ring plays an important role in mediating the antioxidant activity of DDCDs. For all the studied compounds, indicating that HAT was identified as the most favorable mechanism, whereas the SPLET mechanism was the most thermodynamically favorable pathway in polar solvents. The results of our study should aid in the development of new or modified antioxidant compounds.

Antioxidant Activity Evaluation and Assessment of the Binding Affinity to HSA of a New Catechol Hydrazinyl-Thiazole Derivative

“…Literature reports in the field of phenolic compounds indicate that the main antiradical mechanism of this class of compounds is by hydrogen atom transfer (HAT). The antiradical activity of the phenolic compounds correlates well with the easiness of the hydrogen atom’s release from the phenol groups, which in turn correlates with the bond dissociation enthalpy (BDE) [ 13 , 14 , 15 , 16 ].…”

“…radical activity of the phenolic compounds correlates well with the easiness of the hydrogen atom's release from the phenol groups, which in turn correlates with the bond dissociation enthalpy (BDE) [13][14][15][16].…”

Experimental and Theoretical Investigation of Antioxidant Activity of Some Derivatives With Coumarin Scaffold

“…The reactive oxygen and nitrogen species cause damage to cell membranes having a negative effect on important components of our body like nucleic acids, proteins and lipids. Oxidative stress has been linked to numerous diseases including inflammation, cancers, atherosclerosis, diabetes, ischemic stroke, Alzheimer's disease [5,34,36]. Oxygen heterocycles exhibit diverse biological activities due in part to the similarities with many natural and synthetic molecules with known biological activity.…”