Effect of Selected Plant Phenolics on Fe2+-EDTA-H2O2 System Mediated Deoxyribose Oxidation: Molecular Structure-Derived Relationships of Anti- and Pro-Oxidant Actions
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+-ethylenediaminetetraaceti...
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| Format: | Article |
| Language: | English |
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MDPI AG
2016-12-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/22/1/59 |
| _version_ | 1811229729393475584 |
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| author | Jeffrey de Graft-Johnson Dariusz Nowak |
| author_facet | Jeffrey de Graft-Johnson Dariusz Nowak |
| author_sort | Jeffrey de Graft-Johnson |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-04-12T10:18:13Z |
| format | Article |
| id | doaj.art-94fc13ccccd44e5c8195c0771b885c30 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-04-12T10:18:13Z |
| publishDate | 2016-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-94fc13ccccd44e5c8195c0771b885c302022-12-22T03:37:09ZengMDPI AGMolecules1420-30492016-12-012215910.3390/molecules22010059molecules22010059Effect of Selected Plant Phenolics on Fe2+-EDTA-H2O2 System Mediated Deoxyribose Oxidation: Molecular Structure-Derived Relationships of Anti- and Pro-Oxidant ActionsJeffrey de Graft-Johnson0Dariusz Nowak1Heart and Vascular Institute of North Florida, 2623 Centennial Blvd., Suite 102, Tallahassee, FL 32308, USADepartment of Clinical Physiology, Medical University of Lodz, Mazowiecka 6/8, 92-215 Lodz, PolandIn 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.http://www.mdpi.com/1420-3049/22/1/59hydroxyl radicalspolyphenolsplant phenolic acidsFenton system |
| spellingShingle | Jeffrey de Graft-Johnson Dariusz Nowak Effect of Selected Plant Phenolics on Fe2+-EDTA-H2O2 System Mediated Deoxyribose Oxidation: Molecular Structure-Derived Relationships of Anti- and Pro-Oxidant Actions Molecules hydroxyl radicals polyphenols plant phenolic acids Fenton system |
| title | Effect of Selected Plant Phenolics on Fe2+-EDTA-H2O2 System Mediated Deoxyribose Oxidation: Molecular Structure-Derived Relationships of Anti- and Pro-Oxidant Actions |
| title_full | Effect of Selected Plant Phenolics on Fe2+-EDTA-H2O2 System Mediated Deoxyribose Oxidation: Molecular Structure-Derived Relationships of Anti- and Pro-Oxidant Actions |
| title_fullStr | Effect of Selected Plant Phenolics on Fe2+-EDTA-H2O2 System Mediated Deoxyribose Oxidation: Molecular Structure-Derived Relationships of Anti- and Pro-Oxidant Actions |
| title_full_unstemmed | Effect of Selected Plant Phenolics on Fe2+-EDTA-H2O2 System Mediated Deoxyribose Oxidation: Molecular Structure-Derived Relationships of Anti- and Pro-Oxidant Actions |
| title_short | Effect of Selected Plant Phenolics on Fe2+-EDTA-H2O2 System Mediated Deoxyribose Oxidation: Molecular Structure-Derived Relationships of Anti- and Pro-Oxidant Actions |
| title_sort | effect of selected plant phenolics on fe2 edta h2o2 system mediated deoxyribose oxidation molecular structure derived relationships of anti and pro oxidant actions |
| topic | hydroxyl radicals polyphenols plant phenolic acids Fenton system |
| url | http://www.mdpi.com/1420-3049/22/1/59 |
| work_keys_str_mv | AT jeffreydegraftjohnson effectofselectedplantphenolicsonfe2edtah2o2systemmediateddeoxyriboseoxidationmolecularstructurederivedrelationshipsofantiandprooxidantactions AT dariusznowak effectofselectedplantphenolicsonfe2edtah2o2systemmediateddeoxyriboseoxidationmolecularstructurederivedrelationshipsofantiandprooxidantactions |