Inhibition of Peroxynitrite-Mediated Oxidation of Dopamine by Flavonoid and Phenolic Antioxidants and Their Structural Relationships
| Autor: | Catherine Rice-Evans, Nicole Kerry |
|---|---|
| Rok vydání: | 2002 |
| Předmět: |
Antioxidant
Coumaric Acids Dopamine medicine.medical_treatment Biochemistry Antioxidants Catechin Ferulic acid Structure-Activity Relationship Cellular and Molecular Neuroscience chemistry.chemical_compound Caffeic Acids Phenols Nitration medicine Caffeic acid Organic chemistry Tyrosine Chromatography High Pressure Liquid Flavonoids Nitrates Monophenol Monooxygenase food and beverages chemistry Propionates Oxidation-Reduction Peroxynitrite medicine.drug |
| Zdroj: | Journal of Neurochemistry. 73:247-253 |
| ISSN: | 1471-4159 0022-3042 |
| DOI: | 10.1046/j.1471-4159.1999.0730247.x |
| Popis: | The interaction between peroxynitrite and dopamine and the inhibition of this reaction by plant-derived antioxidants have been investigated. Peroxynitrite promoted the oxidation of dopamine to 6-hydroxyindole-5-one as characterised by HPLC and photodiode array spectra, akin to the products of the tyrosinase-dopamine reaction, but no evidence of dopamine nitration was obtained. Although peroxynitrite did not cause nitration of dopamine in vitro, the catecholamine is capable of inhibiting the formation of 3-nitrotyrosine from peroxynitrite-mediated nitration of tyrosine. The plant-derived phenolic compounds, caffeic acid and catechin, inhibited peroxynitrite-mediated oxidation of dopamine. This effect is attributed to the ability of catechol-containing antioxidants to reduce peroxynitrite through electron donation, resulting in their oxidation to the corresponding o-quinones. The antioxidant effect of caffeic acid and catechin was comparable to that of the endogenous antioxidant, glutathione. In contrast, the structurally related monohydroxylated hydroxycinnamates, p-coumaric acid and ferulic acid, which inhibit tyrosine nitration through a mechanism of competitive nitration, did not inhibit peroxynitrite-induced dopamine oxidation. The findings of the present study suggest that certain plant-derived phenolics can inhibit dopamine oxidation. |
| Databáze: | OpenAIRE |
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