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The reversibility of the glutathionyl-quercetin adduct spreads oxidized quercetin-induced toxicity.

Abstract：

:Quercetin is one of the most prominent dietary antioxidants. During its antioxidant activity, quercetin becomes oxidized into its o-quinone/quinone methide QQ. QQ is toxic since it instantaneously reacts with thiols of, e.g., proteins. In cells, QQ will initially form an adduct with glutathione (GSH), giving GSQ. We have found that GSQ is not stable; it dissociates continuously into GSH and QQ with a half life of 2min. Surprisingly, GSQ incubated with 2-mercapto-ethanol (MSH), a far less reactive thiol, results in the conversion of GSQ into the MSH-adduct MSQ. A similar conversion of GSQ into relatively stable protein thiol-quercetin adducts is expected. With the dithiol dihydrolipoic acid (L(SH)(2)), quercetin is formed out of GSQ. These results indicate that GSQ acts as transport and storage of QQ. In that way, the initially highly focussed toxicity of QQ is dispersed by the formation of GSQ that finally spreads QQ-induced toxicity, probably even over cells.

journal_name

Biochem Biophys Res Commun

journal_title

Biochemical and biophysical research communications

authors

Boots AW,Balk JM,Bast A,Haenen GR

doi

10.1016/j.bbrc.2005.10.031

subject

Has Abstract

pub_date

2005-12-16 00:00:00

pages

923-9

issue

2

eissn

0006-291X

issn

1090-2104

pii

S0006-291X(05)02267-9

journal_volume

338

pub_type

杂志文章

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