Kinetics of iron oxidation upon polyphenol binding

被引:110
作者
Perron, Nathan R. [1 ]
Wang, Hsiao C. [1 ]
DeGuire, Sean N. [1 ]
Jenkins, Michael [1 ]
Lawson, Mereze [1 ]
Brumaghim, Julia L. [1 ]
机构
[1] Clemson Univ, Dept Chem, Clemson, SC 29634 USA
关键词
RADICAL SCAVENGING CAPACITY; FERROUS IRON; DNA-DAMAGE; STABILITY-CONSTANTS; PHENOLIC-COMPOUNDS; METAL CHELATION; FENTON REACTION; OXYGEN REACTION; TEA CATECHINS; GALLIC ACID;
D O I
10.1039/c0dt00752h
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Polyphenol prevention of iron-mediated DNA damage occurs primarily through iron binding. Once bound, iron in the Fe(2+)-polyphenol complex autooxidizes to Fe(3+) in the presence of O(2). To determine the correlation between the rate of Fe(2+)-polyphenol autooxidation and polyphenol antioxidant ability, kinetic studies at pH = 6.0 in the presence of oxygen were performed using UV-vis spectrophotometry. Initial rates of iron-polyphenol complex oxidation for epigallocatechin gallate (EGCG), methyl-3,4,5-trihydroxybenzoate (MEGA), gallic acid (GA), epicatechin (EC), and methyl-3,4-dihydroxybenzoate (MEPCA) were in the range of 0.14-6.7 min(-1). Polyphenols with gallol groups have faster rates of iron oxidation than their catechol analogs, suggesting that stronger iron binding results in faster iron oxidation. Concentrations of polyphenol, Fe(2+), and O(2) were varied to investigate the dependence of the Fe(2+)-polyphenol autooxidation on these reactants for MEGA and MEPCA. For these analogous gallate and catecholate complexes of Fe(2+), iron oxidation reactions were first order in Fe(2+), polyphenol, and O(2), but gallate complexes show saturation behavior at much lower Fe(2+) concentrations. Thus, gallol-containing polyphenols promote iron oxidation at a significantly faster rate than analogous catechol-containing compounds, and iron oxidation rate also correlates strongly with polyphenol inhibition of DNA damage for polyphenol compounds with a single iron-binding moiety.
引用
收藏
页码:9982 / 9987
页数:6
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