Characterization and biological effects of di-hydroxylated compounds deriving from the lipoxygenation of ALA. - Archive ouverte HAL Access content directly
Journal Articles Journal of Lipid Research Year : 2013

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

(1) , (2) , (1) , (3) , (4) , (1) , (1)
1
2
3
4

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.
Fichier principal
Vignette du fichier
JLR_M._Liu.pdf (1.13 Mo) Télécharger le fichier
Origin : Files produced by the author(s)
Loading...

Dates and versions

inserm-00832286 , version 1 (04-06-2014)

Identifiers

Cite

Miao Liu, Ping Chen, Evelyne Véricel, 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, 2013, 54 (8), pp.2083-94. ⟨10.1194/jlr.M035139⟩. ⟨inserm-00832286⟩
251 View
477 Download

Altmetric

Share

Gmail Facebook Twitter LinkedIn More