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Inhibition of peroxynitrite-mediated oxidation of dopamine by flavonoid and phenolic antioxidants and their structural relationships.
J Neurochem. 1999 Jul; 73(1):247-53.JN

Abstract

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.

Authors+Show Affiliations

Antioxidant Research Centre, Guy's, King's and St. Thomas's School of Biomedical Sciences, King's College, London, England, UK.No affiliation info available

Pub Type(s)

Comparative Study
Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

10386977

Citation

Kerry, N, and C Rice-Evans. "Inhibition of Peroxynitrite-mediated Oxidation of Dopamine By Flavonoid and Phenolic Antioxidants and Their Structural Relationships." Journal of Neurochemistry, vol. 73, no. 1, 1999, pp. 247-53.
Kerry N, Rice-Evans C. Inhibition of peroxynitrite-mediated oxidation of dopamine by flavonoid and phenolic antioxidants and their structural relationships. J Neurochem. 1999;73(1):247-53.
Kerry, N., & Rice-Evans, C. (1999). Inhibition of peroxynitrite-mediated oxidation of dopamine by flavonoid and phenolic antioxidants and their structural relationships. Journal of Neurochemistry, 73(1), 247-53.
Kerry N, Rice-Evans C. Inhibition of Peroxynitrite-mediated Oxidation of Dopamine By Flavonoid and Phenolic Antioxidants and Their Structural Relationships. J Neurochem. 1999;73(1):247-53. PubMed PMID: 10386977.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Inhibition of peroxynitrite-mediated oxidation of dopamine by flavonoid and phenolic antioxidants and their structural relationships. AU - Kerry,N, AU - Rice-Evans,C, PY - 1999/7/1/pubmed PY - 1999/7/1/medline PY - 1999/7/1/entrez SP - 247 EP - 53 JF - Journal of neurochemistry JO - J Neurochem VL - 73 IS - 1 N2 - 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. SN - 0022-3042 UR - https://www.unboundmedicine.com/medline/citation/10386977/Inhibition_of_peroxynitrite_mediated_oxidation_of_dopamine_by_flavonoid_and_phenolic_antioxidants_and_their_structural_relationships_ L2 - https://onlinelibrary.wiley.com/resolve/openurl?genre=article&sid=nlm:pubmed&issn=0022-3042&date=1999&volume=73&issue=1&spage=247 DB - PRIME DP - Unbound Medicine ER -