Reductive addition of glutathione to p-benzoquinone, 2-hydroxy-p-benzoquinone, and p-benzoquinone epoxides. Effect of the hydroxy- and glutathionyl substituents on p-benzohydroquinone autoxidation

Chemico-biological Interactions
A Brunmark, E Cadenas

Abstract

The reductive addition of GSH to p-benzoquinones, 2-hydroxy-p-benzoquinone, and 2,3-epoxy-p-benzoquinones with different degree of methyl substitution was studied in terms of absorption spectral changes and autoxidation reactions. The nucleophilic addition of GSH to p-benzoquinone yields a glutathionyl-p-benzohydroquinone product with maximal absorption at lambda 303nm. This compound autoxidizes slowly--but at a rate 8-fold higher than the parent hydroquinone--to glutathionyl-p-benzoquinone, which reveals maximal absorption at lambda 367 nm. The autoxidation of the glutathionyl derivative is accompanied by O2 consumption and H2O2 formation. The nucleophilic addition of GSH to either 2-hydroxy-p-benzoquinone or 2,3-epoxy-p-benzoquinone yields the same primary molecular product, 2-hydroxy-5-glutathionyl-p-benzohydroquinone, a compound that shows maximal absorption at lambda 300 nm and autoxidizes at rates substantially higher (44-fold) than the parent glutathionyl hydroquinone lacking a -OH substituent. The autoxidation product, 2-hydroxy-5-glutathionyl-p-benzoquinone, reveals maximal absorbance at lambda 343 nm as well as a resolved absorption band at longer wavelengths (lambda 520 nm), the latter contributed by the -OH substitu...Continue Reading

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Citations

Jan 1, 1991·Chemico-biological Interactions·P J O'Brien
May 19, 1995·Chemico-biological Interactions·S AhmadG S Rao
Jan 1, 1989·Free Radical Biology & Medicine·A Brunmark, E Cadenas
Oct 1, 1992·Free Radical Biology & Medicine·A BindoliD J Deeble
Jun 7, 2002·Toxicology·Antonio E AlegriaMaria Luz Martín-Martín
Jun 6, 2009·Proceedings of the National Academy of Sciences of the United States of America·Yang SongGarry R Buettner
Sep 8, 2012·The Journal of Biological Chemistry·Abigail R GreenChulHee Kang
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Jan 1, 1991·Chemico-biological Interactions·G S Rao

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