Why B-ring is the active center for genistein to scavenge peroxyl radical: a DFT study.
The structure-activity relationship for genistein to scavenge peroxyl radical was clarified by density functional theory (DFT) calculations using the B3LYP/6-31G(d,p) method. It was revealed that the conjugation of an electron-withdrawing 1,4-pyrone group with A-ring of genistein was not beneficial to enhance the radical-scavenging activities. Thus, hydroxyl in B-ring became the active center of genistein to scavenge peroxyl radical.
Zhang
Hong-Yu
HY
Laboratory for Computational Biology, Shandong Provincial Research Center for Bioinformatic Engineering and Technique, Shandong University of Technology, Zibo 255049, PR China. zhanghy@sdut.edu.cn
Wang
Lan-Fen
LF
Sun
You-Min
YM
D016166:Free Radical Scavengers / Q000737:chemistry / Q000494:pharmacology; D019833:Genistein / Q000737:chemistry* / Q000494:pharmacology*; D006878:Hydroxides / Q000737:chemistry; D008956:Models, Chemical; D010545:Peroxides / Q000737:chemistry*; D011753:Pyrones / Q000737:chemistry; D013329:Structure-Activity Relationship; D013816:Thermodynamics
D016166:Free Radical Scavengers; D006878:Hydroxides; D010545:Peroxides; D011753:Pyrones; C049375:perhydroxyl radical; D019833:Genistein