A theoretical study of radical scavenging antioxidant activity of 3-styrylchromone derivatives using DFT based on quantum chemical descriptors

Abstract

Chromone (4H-chromen-4-one, 4H-1-benzopyran-4-one) heterocyclic compound has been widely used in traditional medicine, which has anti-allergy, anti-inflammation, anti-diabetes, anti-tumor, antibacterial and other pharmacological effects. To estimate the scavenging activity on free radical of 3-styrylchromone derivatives, we considered the physical and chemical properties of the molecule structure, orbital, and thermodynamics. The antioxidant activity of 3-styrylchromone derivatives was studied by density functional theory (DFT) in gas and water. A series of quantum chemical parameters were calculated to describe molecular properties and clarify the radical scavenging mechanism. Our study suggests that the antioxidant activity of scavenging free radicals is largely affected by molecular structure, especially the number of hydroxyl groups, hydrogen bonds, and conjugation effects. 3-styrylchromone derivatives containing pyrogallol structure may have potential antioxidant activity. The antioxidant ability of catechol structure is greater than pyrogallol structure. 1,4-pyrrole also has a positive effect on free radical scavenging, but the scavenging effect of 2-OH and 5-OH introduced by antioxidants was not obvious. The excellent correlations between the structure and the mentioned DFT-based descriptors lead us to predict good antioxidants.