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

A.W. Boots; G.R.M.M. Haenen; G.J.M. den Hartog; A. Bast

doi:10.1016/S1388-1981(02)00247-0

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

A.W. Boots^*, G.R.M.M. Haenen, G.J.M. den Hartog, A. Bast

^*Corresponding author for this work

NUTRIM School of Nutrition and Translational Research in Metabolism

Research output: Contribution to journal › Article › Academic › peer-review

Abstract

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

Boots AW, Haenen GR, den Hartog GJ, Bast A.

Department of Pharmacology and Toxicology, Faculty of Medicine, Maastricht University, P.O. Box 616, 6200 MD Maastricht, The Netherlands. A.Boots@farmaco.unimaas.nl

Catechol-containing antioxidants are able to protect against lipid peroxidation by nonenzymatic scavenging of free radicals with their catechol moiety. During their antioxidant activity, catechol oxidation products such as semiquinone radicals and quinones are formed. These oxidation products of 4-methylcatechol inactivate the GSH-dependent protection against lipid peroxidation and the calcium sequestration in liver microsomes. This effect is probably due to arylation by oxidation products of 4-methylcatechol of free thiol groups of the enzymes responsible for the GSH-dependent protection and calcium sequestration, i.e. the free radical reductase and calcium ATPase. It is concluded that a catechol-containing antioxidant might shift radical damage from lipid peroxidation to sulfhydryl arylation

Original language	English
Pages (from-to)	279-284
Number of pages	6
Journal	Biochimica et Biophysica Acta-Molecular and Cell Biology of Lipids
Volume	1583
Issue number	3
DOIs	https://doi.org/10.1016/S1388-1981(02)00247-0
Publication status	Published - 1 Jan 2002

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10.1016/S1388-1981(02)00247-0

Cite this

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title = "Oxidative damage shifts from lipid peroxidation to thiol arylation by catechol-containing antioxidants",

abstract = "Oxidative damage shifts from lipid peroxidation to thiol arylation by catechol-containing antioxidants.Boots AW, Haenen GR, den Hartog GJ, Bast A.Department of Pharmacology and Toxicology, Faculty of Medicine, Maastricht University, P.O. Box 616, 6200 MD Maastricht, The Netherlands. A.Boots@farmaco.unimaas.nlCatechol-containing antioxidants are able to protect against lipid peroxidation by nonenzymatic scavenging of free radicals with their catechol moiety. During their antioxidant activity, catechol oxidation products such as semiquinone radicals and quinones are formed. These oxidation products of 4-methylcatechol inactivate the GSH-dependent protection against lipid peroxidation and the calcium sequestration in liver microsomes. This effect is probably due to arylation by oxidation products of 4-methylcatechol of free thiol groups of the enzymes responsible for the GSH-dependent protection and calcium sequestration, i.e. the free radical reductase and calcium ATPase. It is concluded that a catechol-containing antioxidant might shift radical damage from lipid peroxidation to sulfhydryl arylation",

author = "A.W. Boots and G.R.M.M. Haenen and {den Hartog}, G.J.M. and A. Bast",

year = "2002",

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T1 - Oxidative damage shifts from lipid peroxidation to thiol arylation by catechol-containing antioxidants

AU - Boots, A.W.

AU - Haenen, G.R.M.M.

AU - den Hartog, G.J.M.

AU - Bast, A.

PY - 2002/1/1

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N2 - Oxidative damage shifts from lipid peroxidation to thiol arylation by catechol-containing antioxidants.Boots AW, Haenen GR, den Hartog GJ, Bast A.Department of Pharmacology and Toxicology, Faculty of Medicine, Maastricht University, P.O. Box 616, 6200 MD Maastricht, The Netherlands. A.Boots@farmaco.unimaas.nlCatechol-containing antioxidants are able to protect against lipid peroxidation by nonenzymatic scavenging of free radicals with their catechol moiety. During their antioxidant activity, catechol oxidation products such as semiquinone radicals and quinones are formed. These oxidation products of 4-methylcatechol inactivate the GSH-dependent protection against lipid peroxidation and the calcium sequestration in liver microsomes. This effect is probably due to arylation by oxidation products of 4-methylcatechol of free thiol groups of the enzymes responsible for the GSH-dependent protection and calcium sequestration, i.e. the free radical reductase and calcium ATPase. It is concluded that a catechol-containing antioxidant might shift radical damage from lipid peroxidation to sulfhydryl arylation

AB - Oxidative damage shifts from lipid peroxidation to thiol arylation by catechol-containing antioxidants.Boots AW, Haenen GR, den Hartog GJ, Bast A.Department of Pharmacology and Toxicology, Faculty of Medicine, Maastricht University, P.O. Box 616, 6200 MD Maastricht, The Netherlands. A.Boots@farmaco.unimaas.nlCatechol-containing antioxidants are able to protect against lipid peroxidation by nonenzymatic scavenging of free radicals with their catechol moiety. During their antioxidant activity, catechol oxidation products such as semiquinone radicals and quinones are formed. These oxidation products of 4-methylcatechol inactivate the GSH-dependent protection against lipid peroxidation and the calcium sequestration in liver microsomes. This effect is probably due to arylation by oxidation products of 4-methylcatechol of free thiol groups of the enzymes responsible for the GSH-dependent protection and calcium sequestration, i.e. the free radical reductase and calcium ATPase. It is concluded that a catechol-containing antioxidant might shift radical damage from lipid peroxidation to sulfhydryl arylation

U2 - 10.1016/S1388-1981(02)00247-0

DO - 10.1016/S1388-1981(02)00247-0

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VL - 1583

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JO - Biochimica et Biophysica Acta-Molecular and Cell Biology of Lipids

JF - Biochimica et Biophysica Acta-Molecular and Cell Biology of Lipids

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