title: The antioxidant effect of imine resveratrol analogues.
abstract: Twenty five Imine resveratrol analogues (IRAs) were synthesized, replacing the C=C bond in resveratrol with CN bond, as well as substitution modifications on aromatic rings. Radical scavenging activities against DPPH, along with singlet oxygen quenching capacities were evaluated, and further confirmed using density functional theory calculations (DFT). It was found that IRAs bearing ortho-OH on B ring have better radical scavenging activities against DPPH than resveratrol, these compounds were also found to be effective (1)O(2) quenchers. Theoretical studies on the reaction mechanism of these compounds with (1)O(2) suggest that the 1,3-addition to a double bond with a -OH group with the formation of allylic hydroperoxide is the most probable reaction route.
authors: Department of Chemistry, Yuquan Campus, Zhejiang University, No. 38, Zheda Road, Hangzhou 310027, Zhejiang, PR China.
authors: Jing
authors: J
authors: Lu
authors: Chang
authors: C
authors: Li
authors: Yun-Feng
authors: YF
authors: Chai
authors: De-Yu
authors: DY
authors: Yang
authors: Cui-Rong
authors: CR
authors: Sun
mesh_terms: D000975:Antioxidants / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D001713:Biphenyl Compounds / Q000737:chemistry; D004578:Electron Spin Resonance Spectroscopy; D007097:Imines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D010851:Picrates / Q000737:chemistry; D000077185:Resveratrol; D026082:Singlet Oxygen / Q000737:chemistry; D013267:Stilbenes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D000975:Antioxidants; D001713:Biphenyl Compounds; D007097:Imines; D010851:Picrates; D013267:Stilbenes; D026082:Singlet Oxygen; C004931:1,1-diphenyl-2-picrylhydrazyl; D000077185:Resveratrol