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Molecules 2017, 22(1), 59; doi:10.3390/molecules22010059

Effect of Selected Plant Phenolics on Fe2+-EDTA-H2O2 System Mediated Deoxyribose Oxidation: Molecular Structure-Derived Relationships of Anti- and Pro-Oxidant Actions

1
Heart and Vascular Institute of North Florida, 2623 Centennial Blvd., Suite 102, Tallahassee, FL 32308, USA
2
Department of Clinical Physiology, Medical University of Lodz, Mazowiecka 6/8, 92-215 Lodz, Poland
*
Author to whom correspondence should be addressed.
Academic Editor: Maurizio Battino
Received: 26 November 2016 / Revised: 17 December 2016 / Accepted: 24 December 2016 / Published: 31 December 2016
(This article belongs to the Section Natural Products)
View Full-Text   |   Download PDF [2539 KB, uploaded 31 December 2016]   |  

Abstract

In the presence of transition metal ions and peroxides, polyphenols, well-known dietary antioxidants, can act as pro-oxidants. We investigated the effect of 13 polyphenols and their metabolites on oxidative degradation of deoxyribose by an OH generating Fenton system (Fe2+-ethylenediaminetetraacetic acid (EDTA)-H2O2). The relationship between phenolics pro-oxidant/anti-oxidant effects and their molecular structure was analyzed using multivariate analysis with multiple linear regression and a backward stepwise technique. Four phenolics revealed a significant inhibitory effect on OH-induced deoxyribose degradation, ranging from 54.4% ± 28.6% (3,4-dihydroxycinnamic acid) to 38.5% ± 10.4% (catechin) (n = 6), correlating with the number of –OH substitutions (r = 0.58). Seven phenolics augmented the oxidative degradation of deoxyribose with the highest enhancement at 95.0% ± 21.3% (quercetin) and 60.6% ± 12.2% (phloridzin). The pro-oxidant effect correlated (p < 0.05) with the number of –OH groups (r = 0.59), and aliphatic substitutes (r = −0.22) and weakly correlated with the occurrence of a catechol structure within the compound molecule (r = 0.17). Selective dietary supplementation with phenolics exhibiting pro-oxidant activity may increase the possibility of systemic oxidative stress in patients treated with medications containing chelating properties or those with high plasma concentrations of H2O2 and non-transferrin bound iron. View Full-Text
Keywords: hydroxyl radicals; polyphenols; plant phenolic acids; Fenton system hydroxyl radicals; polyphenols; plant phenolic acids; Fenton system
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de Graft-Johnson, J.; Nowak, D. Effect of Selected Plant Phenolics on Fe2+-EDTA-H2O2 System Mediated Deoxyribose Oxidation: Molecular Structure-Derived Relationships of Anti- and Pro-Oxidant Actions. Molecules 2017, 22, 59.

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