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• W2895525051 startingPage "10108" @default.
• W2895525051 abstract "Zinc(II) enhances radical scavenging of the flavonoid kaempferol (Kaem) most significantly for the 1:1 Zn(II)-Kaem complex in equilibrium with the 1:2 Zn(II)-Kaem complex both with high affinity at 3-hydroxyl and 4-carboxyl coordination. In methanol/chloroform (7/3, v/v), 1:1 Zn(II)-Kaem complex reduces β-carotene radical cation, β-Car•+, with a second-order rate constant, 1.88 × 108 L·mol–1·s–1, while both Kaem and 1:2 Zn(II)-Kaem complex are nonreactive, as determined by laser flash photolysis. In ethanol, 1:1 Zn(II)-Kaem complex reduces the 2,2-diphenyl-1-picrylhydrazyl radical, DPPH•, with a second-order rate constant, 2.48 × 104 L·mol–1·s–1, 16 times and 2 times as efficient as Kaem and 1:2 Zn(II)-Kaem complex, respectively, as determined by stopped-flow spectroscopy. Density functional theory calculation results indicate significantly increased acidity of Kaem as ligand in 1:1 Zn(II)-Kaem complex other than in 1:2 Zn(II)-Kaem complex. Kaem in 1:1 Zn(II)-Kaem complex loses two protons (one from 3-hydroxyl and one from phenolic hydroxyl) forming 1:1 Zn(II)-(Kaem–2H) during binding with Zn(II), while Kaem in 1:2 Zn(II)-Kaem complex loses one proton in each ligand forming Zn(II)-(Kaem–H)2, as confirmed by UV–vis absorption spectroscopy. Zn(II)-(Kaem–2H) is a far stronger reductant than Kaem and Zn(II)-(Kaem–H)2 as determined by cyclic voltammetry. Significant rate increases for the 1:1 complex in both β-Car•+ scavenging by electron transfer and DPPH• scavenging by hydrogen atom transfer were ascribed to decreases of ionization potential and of bond dissociation energy of 4′-OH for deprotonated Zn(II)-(Kaem–2H), respectively. Increased phenol acidity of plant polyphenols by 1:1 coordination with Zn(II) may explain the unique function of Zn(II) as a biological antioxidant and may help to design nontoxic metal-based drugs derived from natural bioactive molecules." @default.
• W2895525051 created "2018-10-12" @default.
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• W2895525051 date "2018-10-08" @default.
• W2895525051 modified "2023-10-16" @default.
• W2895525051 title "Kaempferol Binding to Zinc(II), Efficient Radical Scavenging through Increased Phenol Acidity" @default.
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• W2895525051 doi "https://doi.org/10.1021/acs.jpcb.8b08284" @default.
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