Characterization and biological effects of di-hydroxylated compounds deriving from the lipoxygenation of ALA.: Di-hydroxylated metabolites from ALA

Abstract : We have recently described a di-hydroxylated compound called protectin DX (PDX) which derives from docosahexaenoic acid (DHA) by double lipoxygenation. PDX exhibits anti-aggregatory and anti-inflammatory properties, that are also exhibited by similar molecules, called poxytrins, which possess the same E,Z,E conjugated triene geometry, and are synthesized from other polyunsaturated fatty acids with 22 or 20 carbons. Here we present new biological activities of di-hydroxylated metabolites deriving from α-linolenic acid (18:3n-3) treated by soybean 15-lipoxygenase (sLOX). We show that 18:3n-3 is converted by sLOX into mainly 13(S)-OH-18:3 after reduction of the hydroperoxide product. But surprisingly, and in contrast to DHA which is metabolized into only one di-hydroxylated compound, 18:3n-3 leads to four di-hydroxylated fatty acid isomers. We report here the complete characterization of these compounds using high field NMR and GC-MS techniques, and some of their biological activities. These compounds are: 9(R),16(S)-dihydroxy-10E,12E,14E-octadecatrienoic acid, 9(S),16(S)-dihydroxy-10E,12E,14E-octadecatrienoic acid, 9(S),16(S)-dihydroxy-10E,12Z,14E-octadecatrienoic acid, and 9(R),16(S)-dihydroxy-10E,12Z,14E-octadecatrienoic acid. They can also be synthesized by the human recombinant 15-lipoxygenase (type 2). Their inhibitory effect on blood platelet and anti-inflammatory properties were compared with those already reported for PDX.
Type de document :
Article dans une revue
Journal of Lipid Research, American Society for Biochemistry and Molecular Biology, 2013, 54 (8), pp.2083-94. 〈10.1194/jlr.M035139〉
Liste complète des métadonnées

Littérature citée [21 références]  Voir  Masquer  Télécharger

http://www.hal.inserm.fr/inserm-00832286
Contributeur : Evelyne Vericel <>
Soumis le : mercredi 4 juin 2014 - 14:50:03
Dernière modification le : mardi 17 juillet 2018 - 15:50:09
Document(s) archivé(s) le : jeudi 4 septembre 2014 - 10:37:40

Fichier

JLR_M._Liu.pdf
Fichiers produits par l'(les) auteur(s)

Identifiants

Collections

Citation

Miao Liu, Ping Chen, Evelyne Vericel, Moreno Lelli, Laetitia Beguin, et al.. Characterization and biological effects of di-hydroxylated compounds deriving from the lipoxygenation of ALA.: Di-hydroxylated metabolites from ALA. Journal of Lipid Research, American Society for Biochemistry and Molecular Biology, 2013, 54 (8), pp.2083-94. 〈10.1194/jlr.M035139〉. 〈inserm-00832286〉

Partager

Métriques

Consultations de la notice

532

Téléchargements de fichiers

307