%0 Journal Article %T Characterization and biological effects of di-hydroxylated compounds deriving from the lipoxygenation of ALA. %T Di-hydroxylated metabolites from ALA %+ Cardiovasculaire, métabolisme, diabétologie et nutrition (CarMeN) %+ Tea Science Department, College of Agriculture and Biotechnology %+ ISA - Centre de RMN à très hauts champs %+ Institut des Sciences Analytiques (ISA) %A Liu, Miao %A Chen, Ping %A Véricel, Evelyne %A Lelli, Moreno %A Beguin, Laetitia %A Lagarde, Michel %A Guichardant, Michel %Z This study was supported by Inserm and the French Ministry of Education and Research. Miao Liu is a Ph.D. student granted from the China Scholarship Council. %< avec comité de lecture %@ 0022-2275 %J Journal of Lipid Research %I American Society for Biochemistry and Molecular Biology %V 54 %N 8 %P 2083-94 %8 2013-08 %D 2013 %R 10.1194/jlr.M035139 %M 23740966 %K anti-inflammatory activity %K platelet aggrgation %K 15 lipoxygenase %K octadecatrienoic acid %Z Life Sciences [q-bio]/Food and NutritionJournal articles %X 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. %G English %2 https://inserm.hal.science/inserm-00832286/document %2 https://inserm.hal.science/inserm-00832286/file/JLR_M._Liu.pdf %L inserm-00832286 %U https://inserm.hal.science/inserm-00832286 %~ INSERM %~ HCL %~ CNRS %~ UNIV-LYON1 %~ INSA-LYON %~ INRA %~ ISA %~ INC-CNRS %~ AGREENIUM %~ CARMEN %~ INSA-GROUPE %~ UDL %~ UNIV-LYON %~ INRAE