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Vitamin C-Induced Decomposition of Lipid Hydroperoxides to Endogenous Genotoxins

Science  15 Jun 2001:
Vol. 292, Issue 5524, pp. 2083-2086
DOI: 10.1126/science.1059501

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Abstract

Epidemiological data suggest that dietary antioxidants play a protective role against cancer. This has led to the proposal that dietary supplementation with antioxidants such as vitamin C (vit C) may be useful in disease prevention. However, vit C has proved to be ineffective in cancer chemoprevention studies. In addition, concerns have been raised over potentially deleterious transition metal ion–mediated pro-oxidant effects. We have now determined that vit C induces lipid hydroperoxide decomposition to the DNA-reactive bifunctional electrophiles 4-oxo-2-nonenal, 4,5-epoxy-2(E)-decenal, and 4-hydroxy-2-nonenal. The compound 4,5-Epoxy-2(E)-decenal is a precursor of etheno-2′-deoxyadenosine, a highly mutagenic lesion found in human DNA. Vitamin C–mediated formation of genotoxins from lipid hydroperoxides in the absence of transition metal ions could help explain its lack of efficacy as a cancer chemoprevention agent.

  • * To whom correspondence should be addressed. E-mail: ian{at}spirit.gcrc.upenn.edu

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