Journal
FREE RADICAL BIOLOGY AND MEDICINE
Volume 49, Issue 6, Pages 984-991Publisher
ELSEVIER SCIENCE INC
DOI: 10.1016/j.freeradbiomed.2010.05.029
Keywords
Vitamin C; Dehydroascorbate; Glutathione; Mass spectrometry; Nuclear magnetic resonance; Jurkat cells; Free radicals
Funding
- Institute of Aging
- Canadian Institutes of Health Research
- Le Programme-Reseau de Formation Inter-disciplinaire en Recherche Sante et Vieillissement
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Glutathione (GSH) and ascorbate (ascorbic acid, vitamin C, ASC) are two critical water-soluble antioxidants in aerobic organisms. The reaction of ascorbate with reactive oxygen species leads to dehydroascorbate. It is generally accepted that GSH reduces dehydroascorbate (DHA) to give oxidized glutathione (GSSG) and ASC (2GSH + DHA -> GSSG + ASC) as a chemical pathway of ascorbate regeneration. Here, we report the formation of a novel conjugation product between GSH and the decomposition of DHA denoted as GS-DHA*. On the basis of MS and NMR analyses, the structure of GS-DHA* consists of an intact GSH moiety attached via the thiol group to a five-carbon fragment of DHA. The conjugation product appears as a mixture of four diastereomers with very similar proton and carbon chemical shifts. The formation of GS-DHA* adducts is demonstrated in Jurkat cells upon incubation with DHA in culture followed by analysis of the whole-cell extracts by HPLC coupled to tandem mass spectrometry. This novel conjugation product may be a useful biomarker of DHA stress and model system of protein modification. (C) 2010 Elsevier Inc. All rights reserved.
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