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Action of 1-(11-selenadodecyl)-glycerol and 1-(11-selenadodecyl)-3-trolox-glycerol against lipid peroxidation

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Lipids

Abstract

The antioxidant action on lipid peroxidation of the synthesized selenium compounds 1-(11-selenadodecyl)-glycerol (SeG) and 1-(11-selenadodecyl)-3-Trolox-glycerol (SeIrG, where Trolox=6-hydroxyl-2,5,7,8-tetramethylchroman-2-carboxylic acid) was investigated. We compared the reactivity of the selenium compounds toward peroxyl radicals and their inhibitory effect on lipid peroxidation, induced by several kinds of initiating species such as azo compounds, metal ions, and superoxide/nitric oxide in solution, micelles, membranes, and rat plasma. SeTrG, but not SeG, scavenged peroxyl radicals. SeG reduced methyl linoleate hydroperoxides in organic solution and in methyl linoleate micelles oxidized by ferrous ion (Fe2+)/ascorbic acid. In rat plasma SeG and SeTrG decreased the formation of lipid hydroperoxides generated by hydrophilic azo compounds. SeG and SeTrG spared α-tocopherol (α-TOH) consumption in multilamellar vesicle membranes oxidized by hydrophilic or lipophilic initiators, and only SeTrG spared α-TOH in superoxide/nitric oxide oxidized membranes. In rat plasma oxidized by radical initiators (either hydrophilic or lipophilic) or superoxide/nitric oxide, SeTrG suppressed α-TOH consumption, but SeG had no effect. The two selenium-containing compounds showed inhibitory effects on lipid peroxidation that depended on their structure, the medium where they acted, and the oxidant used.

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Abbreviations

A:

absorbance

AA:

ascorbic acid

AAPH:

2,2′-azobis(2-amidinopropane) dihydrochloride

AMVN:

2,2′-azobis(2,4-dimethyl-valeronitrile)

CA:

caffeic acid

DOPAC:

3,4-dihydroxyphenylacetic acid

DPBQ:

N,N′-diphenyl-p-benzoqninone diimine

DPPD:

N,N′-diphenyl-p-phenylendiamine

ebselen:

2-phenyl-1,2-benzoisoselenazol-3(2H)-one

MeO-AMVN:

2,2′-azobis(4-methoxy-2,4-dimethylvaleronitrile)

MeLOH:

methyl linoleate alcohols

MeLOOH:

methyl linoleate hydroperoxides

MLV:

multilamellar vesicles

PMC:

2,2,5,7,8-pentamethyl-6-chromanol

SeG:

1-(11-selenadodecyl)-glycerol

SeTrG:

1-(11-selenadodecyl)-3-Troloxglycerol

SIN:

1,3-morpholinosydnonimine hydrochloride

Trolox:

6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid

α-TOH:

α-tocopherol

Tox-3:

tocotrienols

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Authors and Affiliations

  1. Lipid Chemistry Department, Institute of Organic Chemistry, Bulgarian Academy of Sciences, 1113, Sofia, Bulgaria

    Violeta Raneva & Nedyalka Yanishlieva

  2. Department of Chemistry, Norwegian University of Science and Technology, N-7491, Trondheim, Norway

    Jon Erik Aaseng, Vassilia Partali & Hans-Richard Sliwka

  3. Human Stress Signal Research Center, Advanced Institute for Science and Technology, 563-8577, Ikeda, Japan

    Yasukazu Yoshida & Etsuo Niki

  4. First Department of Biochemistry, Teikyo University School of Medicine, 2-11-1 Kaga, Itabashi-ku, 173-8605, Tokyo, Japan

    Violeta Raneva, Hiroyuki Shimasaki, Yumi Furukawa & Nobuo Ueta

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  1. Violeta Raneva
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  2. Hiroyuki Shimasaki
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Correspondence to Violeta Raneva.

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Raneva, V., Shimasaki, H., Furukawa, Y. et al. Action of 1-(11-selenadodecyl)-glycerol and 1-(11-selenadodecyl)-3-trolox-glycerol against lipid peroxidation. Lipids 37, 633–640 (2002). https://doi.org/10.1007/s11745-002-0943-x

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  • DOI: https://doi.org/10.1007/s11745-002-0943-x

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