Inhibition of the formation of the neurotoxin 5-S-cysteinyl-dopamine by polyphenols |
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Authors: | Vauzour David Vafeiadou Katerina Spencer Jeremy P E |
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Institution: | Molecular Nutrition Group, School of Chemistry, Food and Pharmacy, The University of Reading, Whiteknights Campus, Reading RG6 6AP, UK. |
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Abstract: | The death of nigral neurons in Parkinson's disease is thought to involve the formation of the endogenous neurotoxin, 5-S-cysteinyl-dopamine. In the present study, we show that the polyphenols, (+)-catechin and caffeic acid, which contain a catechol moiety, inhibit tyrosinase-induced formation of 5-S-cysteinyl-dopamine via their capacity to undergo tyrosinase-induced oxidation to yield cysteinyl-polyphenol adducts. In contrast, the inhibition afforded by the flavanone, hesperetin, was not accompanied by the formation of cysteinyl-hesperetin adducts, indicating that it may inhibit via direct interaction with tyrosinase. Whilst the stilbene resveratrol also inhibited 5-S-cysteinyl-dopamine formation, this was accompanied by the formation of dihydrobenzothiazine, a strong neurotoxin. Our data indicate that the inhibitory effects of polyphenols against 5-S-cysteinyl-dopamine formation are structure-dependent and shed further light on the mechanisms by which polyphenols exert protection against neuronal injury relevant to neurodegenerative diseases. |
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Keywords: | 5-S-Cysteinyl-dopamine Tyrosinase Neurodegeneration Parkinson disease Catechin Hesperetin Caffeic acid Resveratrol |
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