Curcumin-glutathione interactions and the role of human glutathione S- transferase P1-1

Sanjay Awasthi, Utpal Pandya, Sharad S. Singhal, James T. Lin, Varatharasa Thiviyanathan, William E. Seifert, Yogesh C. Awasthi, G. A.S. Ansari

Research output: Contribution to journalArticle

103 Scopus citations

Abstract

Curcumin (diferuloylmethane), a yellow pigment of turmeric with antioxidant properties has been shown to be a cancer preventative in animal studies. It contains two electrophilic α, β-unsaturated carbonyl groups, which can react with nucleophilic compounds such as glutathione (GSH), but formation of the GSH-curcumin conjugates has not previously been demonstrated. In the present studies, we investigated the reactions of curcumin with GSH and the effect of recombinant human glutathione S- transferase(GST)P1-1 on reaction kinetics. Glutathionylated products of curcumin identified by FAB-MS and MALDI-MS included mono- and di- glutathionyl-adducts of curcumin as well as cyclic rearrangement products of GSH adducts of feruloylmethylketone (FMK) and feruloylaldehyde (FAL). The presence of GSTP1-1 significantly accelerated the initial rate of GSH- mediated consumption of curcumin in 10 mM potassium phosphate, pH 7.0, and 1 mM GSH. GSTP1-1 kinetics determined using HPLC indicated substrate inhibition (apparent K(m) for curcumin of 25 ± 11 μM, and apparent K(i) for curcumin of 8 ± 3 μM). GSTP1-1 was also shown to catalyze the reverse reaction leading to the formation of curcumin from GSH adducts of FMK and FAL. (C) 2000 Elsevier Science Ireland Ltd.

Original languageEnglish (US)
Pages (from-to)19-38
Number of pages20
JournalChemico-Biological Interactions
Volume128
Issue number1
DOIs
StatePublished - Aug 15 2000

Keywords

  • Curcumin
  • Glutathione
  • S-transferase

ASJC Scopus subject areas

  • Toxicology

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    Awasthi, S., Pandya, U., Singhal, S. S., Lin, J. T., Thiviyanathan, V., Seifert, W. E., Awasthi, Y. C., & Ansari, G. A. S. (2000). Curcumin-glutathione interactions and the role of human glutathione S- transferase P1-1. Chemico-Biological Interactions, 128(1), 19-38. https://doi.org/10.1016/S0009-2797(00)00185-X