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Titolo:
Aldehydic lipid peroxidation products derived from linoleic acid
Autore:
Spiteller, P; Kern, W; Reiner, J; Spiteller, G;
Indirizzi:
Univ Bayreuth, Lehrstuhl Organ Chem 1, D-95440 Bayreuth, Germany Univ Bayreuth Bayreuth Germany D-95440 Chem 1, D-95440 Bayreuth, Germany
Titolo Testata:
BIOCHIMICA ET BIOPHYSICA ACTA-MOLECULAR AND CELL BIOLOGY OF LIPIDS
fascicolo: 3, volume: 1531, anno: 2001,
pagine: 188 - 208
SICI:
1388-1981(20010430)1531:3<188:ALPPDF>2.0.ZU;2-E
Fonte:
ISI
Lingua:
ENG
Soggetto:
CHROMATOGRAPHY-MASS-SPECTROMETRY; LOW-DENSITY-LIPOPROTEIN; GAS-CHROMATOGRAPHY; METHYL LINOLEATE; FATTY-ACIDS; ALPHA,BETA-UNSATURATED ALDEHYDES; CATALYZED TRANSFORMATION; ALPHA-HYDROXYALDEHYDES; THERMAL-DECOMPOSITION; LIQUID-CHROMATOGRAPHY;
Keywords:
lipid peroxidation; 2,4-decadienal; 4-hydroxy-2-nonenal; 2-butenal; 5-oxodecanal; 4,5-epoxy-2-decenal; 4-oxo-2-nonenal; 4,5-dihydroxy-2-decenal; buten-1,4-dial; 9-hydroxy-12-oxo-10-dodecenoic acid;
Tipo documento:
Review
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Citazioni:
101
Recensione:
Indirizzi per estratti:
Indirizzo: Spiteller, G Univ Bayreuth, Lehrstuhl Organ Chem 1, Univ Str 30, D-95440 Bayreuth, Germany Univ Bayreuth Univ Str 30 Bayreuth Germany D-95440 , Germany
Citazione:
P. Spiteller et al., "Aldehydic lipid peroxidation products derived from linoleic acid", BBA-MOL C B, 1531(3), 2001, pp. 188-208

Abstract

Lipid peroxidation (LPO) processes observed in diseases connected with inflammation involve mainly linoleic acid. Its primary LPO products, 9-hydroperoxy-10,12-octadecadienoic acid (9-HPODE) and 13-hydroperoxy-9,11-octadecadienoic acid (13-HPODE), decompose in multistep degradation reactions. Thesereactions were investigated in model studies: decomposition of either 9-HPODE or 13-HPODE by Fe2+ catalyzed air oxidation generates (with the exception of corresponding hydroxy and oxo derivatives) identical products in often nearly equal amounts, pointing to a common intermediate. Pairs of carbonyl compounds were recognized by reacting the oxidation mixtures with pentafluorobenzylhydroxylamine. Even if a pure lipid hydroperoxide is subjected todecomposition a great variety of products is generated, since primary products suffer further transformations. Therefore pure primarily decompositionproducts of HPODEs were exposed to stirring in air with or without addition of iron ions. Thus we observed that primary products containing the structural element R-CH=CH-CH=CH-CH=O add water and then they are cleaved by retroaldol reactions. 2,4-Decadienal is degraded in the absence of iron ions to 2-butenal, hexanal and 5-oxodecanal. Small amounts of buten-1,4-dial werealso detected. Addition of m-chloroperbenzoic acid transforms 2,4-decadienal to 4-hydroxy-2-nonenal. 4,5-Epoxy-2-decenal, synthetically available by treatment of 2,4-decadienal with dimethyldioxirane, is hydrolyzed to 4,5-dihydroxy-2-decenal. (C) 2001 Elsevier Science B.V. All rights reserved.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 02/04/20 alle ore 02:21:36