Inhibition of the formation of the neurotoxin 5-S-cysteinyl-dopamine by polyphenols

David Vauzour, Katerina Vafeiadou, Jeremy P. E. Spencer

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36 Citations (Scopus)


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.
Original languageEnglish
Pages (from-to)340-6
Number of pages7
JournalBiochemical and Biophysical Research Communications
Issue number2
Publication statusPublished - 19 Oct 2007


  • Chromatography, High Pressure Liquid
  • Dopamine
  • Flavonoids
  • Mass Spectrometry
  • Monophenol Monooxygenase
  • Neurotoxins
  • Phenols
  • Polyphenols


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