Density functional theory calculations for resveratrol.
The calculations based on the density functional theory (DFT) have been used to study the structure-activity of resveratrol in the chain reaction of autooxidation. According to the geometry obtained by using a B3LYP/6-31G**, the HOMO, LUMO of resveratrol and the spin density, the single electron distribution of the 4'- and 5-radical of resveratrol were calculated, it was found that resveratrol is a potential antioxidant. The 4'-hydroxyl group of resveratrol is more reactive than 3- and 5-positions because of the resonance effects. The dominant structure of the resveratrol radicals is a semiquinone structure which determines the stability of radicals, and the unpaired electron is mainly distributed to the O-atom and its ortho and para positions. The antioxidant activity of resveratrol is related to the spin density and the unpaired electron distribution of the O-atom.
Modern Biological Research Center, Yunnan University, Kunming 650091, People's Republic of China. huaicao@public.km.yn.cn
Huai
H
Cao
Xulin
X
Pan
Cong
C
Li
Chun
C
Zhou
Fengyi
F
Deng
Taohong
T
Li
D000975:Antioxidants / Q000737:chemistry; D005609:Free Radicals / Q000737:chemistry; D008956:Models, Chemical; D015394:Molecular Structure; D010084:Oxidation-Reduction; D000077185:Resveratrol; D013267:Stilbenes / Q000737:chemistry* / Q000494:pharmacology; D013329:Structure-Activity Relationship; D013816:Thermodynamics
D000975:Antioxidants; D005609:Free Radicals; D013267:Stilbenes; D000077185:Resveratrol