Characterization and biological effects of di-hydroxylated compounds deriving from the lipoxygenation of ALA
| Autor: | Liu, Miao, Chen, Ping, Véricel, Evelyne, Lelli, Moreno, Beguin, Laetitia, Lagarde, Michel, Guichardant, Michel |
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| Přispěvatelé: | Cardiovasculaire, métabolisme, diabétologie et nutrition (CarMeN), Hospices Civils de Lyon (HCL)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut National des Sciences Appliquées de Lyon (INSA Lyon), Université de Lyon-Institut National des Sciences Appliquées (INSA)-Université de Lyon-Institut National des Sciences Appliquées (INSA)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Institut National de la Recherche Agronomique (INRA), Tea Science Department, College of Agriculture and Biotechnology, College of Agriculture and Biotechnology, Zhejiang University-Zhejiang University, ISA - Centre de RMN à très hauts champs, Institut des Sciences Analytiques (ISA), Institut de Chimie du CNRS (INC)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Centre National de la Recherche Scientifique (CNRS), 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., Institut National de la Recherche Agronomique (INRA)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Institut National des Sciences Appliquées de Lyon (INSA Lyon), Université de Lyon-Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Hospices Civils de Lyon (HCL), Centre de RMN à très hauts champs, École normale supérieure - Lyon (ENS Lyon)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Centre National de la Recherche Scientifique (CNRS)-École normale supérieure - Lyon (ENS Lyon)-Université Claude Bernard Lyon 1 (UCBL) |
| Jazyk: | angličtina |
| Rok vydání: | 2013 |
| Předmět: |
MESH: Humans
MESH: alpha-Linolenic Acid MESH: Hydroxylation MESH: Molecular Structure MESH: Anti-Inflammatory Agents Non-Steroidal MESH: Recombinant Proteins octadecatrienoic acid platelet aggrgation MESH: Structure-Activity Relationship MESH: Arachidonate 15-Lipoxygenase anti-inflammatory activity [SDV.AEN]Life Sciences [q-bio]/Food and Nutrition MESH: Blood Platelets 15 lipoxygenase |
| Zdroj: | Journal of Lipid Research Journal of Lipid Research, American Society for Biochemistry and Molecular Biology, 2013, 54 (8), pp.2083-94. ⟨10.1194/jlr.M035139⟩ |
| ISSN: | 0022-2275 |
| DOI: | 10.1194/jlr.M035139⟩ |
| Popis: | International audience; 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. |
| Databáze: | OpenAIRE |
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