Oxidative damage shifts from lipid peroxidation to thiol arylation by catechol-containing antioxidants

Boots, Agnes W.; Haenen, Guido R.M.M.; Hartog, G.J.M. den; Bast, Aalt

doi:10.1016/s1388-1981(02)00247-0

Cited by 56 publications

(32 citation statements)

References 24 publications

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“…In this way the reactivity becomes more selective by converting the non-selective reactivity of radicals into a relatively selective thiol reactivity of the oxidized flavonoid. Reaction of these oxidized flavonoids with reactive thiols of essential proteins results in cellular toxicity [1,5]. The reactivity of oxidized monoHER towards thiols, e.g.…”

Section: Discussionmentioning

confidence: 99%

The contribution of the major metabolite 4′-O-methylmonoHER to the antioxidant activity of the flavonoid monoHER

Lemmens¹,

Herst²,

Housmans³

et al. 2015

Chemico-Biological Interactions

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Section: Discussionmentioning

confidence: 99%

The contribution of the major metabolite 4′-O-methylmonoHER to the antioxidant activity of the flavonoid monoHER

Lemmens¹,

Herst²,

Housmans³

et al. 2015

Chemico-Biological Interactions

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“…Its potent ROS scavenging activity is attributed to its inherent number of hydroxyl substitutions, which correlates with its electron-donating ability (Morel et al, 1993;Rice-Evans et al, 1996;Boots et al, 2008). Nevertheless, this electron-donating capacity has also been positively correlated with toxicity ; quercetin forms catechol oxidation products, such as semiquinones and quinones that could alter redox homeostasis, limiting the initial positive effects (Boots et al, 2002). This is likely the basis of one critical aspect of the neuroprotective profile of quercetin in vitro, resulting in a narrow concentration range of protective capacity.…”

Section: Quercetin Neuroprotective Mechanismsmentioning

confidence: 99%

Life or death: Neuroprotective and anticancer effects of quercetin

Dajas¹

2012

Journal of Ethnopharmacology

310

177

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“…Oxidized flavonoids readily and specifically adduct thiol groups. Hence, oxidized flavonoids may threat vital cellular compounds containing a critical thiol group [4,5]. Apparently, a paradox is hidden in the functioning of an antioxidant flavonoid.…”

Section: Introductionmentioning

confidence: 99%

The Minor Structural Difference between the Antioxidants Quercetin and 4'O-Methylquercetin Has a Major Impact on Their Selective Thiol Toxicity

Lemmens

Vrolijk

Bouwman

et al. 2014

IJMS

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Antioxidants act as intermediates by picking up the high unselective reactivity of radicals and transferring it to other molecules. In this process the reactivity is reduced and becomes selective. This channeling of the reactivity can cause selective toxicity. The antioxidant quercetin is known to channel the reactivity towards thiol groups. The present study compares the thiol reactivity of quercetin with that of 4′O-methylquercetin (tamarixetin) towards creatine kinase (CK), a vital protein that contains a critical thiol moiety. Our results showed that oxidized quercetin and oxidized tamarixetin both adduct CK, which then loses its enzymatic function. Ascorbate, an important representative of the antioxidant network, is able to prevent adduction to and thus the inhibition of the enzyme by tamarixetin but not by quercetin. Apparently, tamarixetin is less thiol toxic than quercetin, because—rather than adduction to CK—tamarixetin quinone prefers to pass reactivity to the antioxidant network, i.e., to ascorbate. The findings exemplify that radical scavenging flavonoids pick up the reactivity of radicals and act as a pivot in directing the way the reactivity is channeled. A mere minor structural difference of only one methyl moiety between quercetin and tamarixetin appears to have a high impact on the selective, thiol toxicity.

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Oxidative damage shifts from lipid peroxidation to thiol arylation by catechol-containing antioxidants

Cited by 56 publications

References 24 publications

The contribution of the major metabolite 4′-O-methylmonoHER to the antioxidant activity of the flavonoid monoHER

The contribution of the major metabolite 4′-O-methylmonoHER to the antioxidant activity of the flavonoid monoHER

Life or death: Neuroprotective and anticancer effects of quercetin

The Minor Structural Difference between the Antioxidants Quercetin and 4'O-Methylquercetin Has a Major Impact on Their Selective Thiol Toxicity

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