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2-Imidazolethiones protect ascorbic acid from oxidation induced by copper.

R C Smith1, J Z Gore

  • 1Department of Animal and Dairy Sciences, Auburn University 36849-5415.

Biochimica Et Biophysica Acta
|June 20, 1990
PubMed
Summary

Copper ions accelerate ascorbic acid oxidation, but 2-imidazolethiones inhibit this process. These compounds bind copper, protecting ascorbic acid from degradation, suggesting a novel antioxidant mechanism.

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Area of Science:

  • Biochemistry
  • Oxidative Stress
  • Metal Ion Interactions

Background:

  • Ascorbic acid (Vitamin C) is susceptible to oxidation, a process influenced by metal ions.
  • Metal ions, particularly copper, can catalyze the oxidation of ascorbic acid to dehydroascorbic acid.
  • Understanding factors that modulate ascorbate oxidation is crucial for biological and nutritional science.

Purpose of the Study:

  • To investigate the effect of 2-imidazolethiones and related compounds on copper-ion-mediated ascorbic acid oxidation.
  • To elucidate the mechanism by which 2-imidazolethiones inhibit ascorbate oxidation in the presence of copper.

Main Methods:

  • Assessed the rate of ascorbic acid oxidation in the presence of copper ions.
  • Evaluated the inhibitory effects of 2-imidazolethiones, 2-imidazolones, and phenytoin on ascorbate oxidation.

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  • Utilized ultraviolet-visible spectroscopy to study the interaction between 2-imidazolethiones and copper ions.

    • Main Results:

    • Copper ions significantly accelerated ascorbic acid oxidation.
    • 2-imidazolethiones and sulfhydryl-containing compounds effectively inhibited this copper-induced oxidation.
    • 2-imidazolones and phenytoin did not show significant inhibitory effects.
    • 2-imidazolethiones formed complexes with copper, evidenced by changes in UV absorbance, yet still protected ascorbic acid.

    Conclusions:

    • 2-imidazolethiones act as potent inhibitors of copper-catalyzed ascorbic acid oxidation.
    • The protective effect is attributed to the complexation of copper ions by the free sulfhydryl (-SH) groups of 2-imidazolethiones.
    • These findings suggest a potential role for 2-imidazolethiones in managing oxidative stress related to metal ions.