test_moissonnage_selune
type: Agent

Characterization of oxygen metabolites from alpha-linolenic acid : Effect of anti-aggregatory and anti-inflammatory
type: Dataset
contact point: Organization
  fn: CCSD
keyword: high-performance-liquid-chromatography
keyword: nuclear-magnetic-resonance
keyword: human-leukocytes
keyword: acide-docosahexaenoique
keyword: acide-gras
keyword: sdvsalife-sciences-q-bioagricultural-sciences
keyword: docosahexaenoic-acid
keyword: biosciences
keyword: theses
keyword: fatty-acid
keyword: platelet-aggregation
keyword: agregation-plaquettaire
keyword: chromatographie-liquide-a-haute-performance
keyword: infoeu-reposemanticsdoctoralthesis
keyword: resonance-magnetique-nucleaire
keyword: mass-spectrometry
keyword: spectrometrue-de-masse
keyword: leucocytes-humains
landing page: https://theses.hal.science/tel-00952895
description: N-3 fatty acids, especially docosahexaenoic acid (DHA), play an important role in the prevention of cardiovascular diseases. One metabolite of DHA, protectin DX (PDX), an isomer of protectin D1 (PD1) (Chen P et al., 2009),possesses inhibits blood platelet aggregation. Similar compounds called "poxytrins", which have a conjugated triene with a E,Z,E geometry have also been synthesized from other polyunsaturated fatty acids (PUFA) by soybean lipoxygenase. They have anti-aggregating properties by inhibiting platelet cyclooxygenase and thromboxane A2 receptor (Chen P et al., 2011). In this thesis, we describe new dihydroxy compounds synthesized by the soybean 15-lipoxygenase from alpha-linolenic acid (18:3n-3), an essential PUFA that is consumed in the gram range in human adults . It is converted into monohydroxylated and dihydroxylated derivatives. These compounds were separated by reverse phase high performance liquid chromatography (HPLC) and characterized by gas chromatography-mass spectrometry (GC-MS) after appropriate derivatization. A main monohydroxylated fatty acid, 13(S)-octadecatrienoic acid (13(S)-OH-18:3) and four dihydroxylated fatty acids were detected. The last ones have all a characteristic UV spectrum with a maximum absorbance at 270 nm with two shoulder peaks at 260 and 280 nm. The UV spectra from two of them are superimposable to that of PDX, suggesting a E,Z,E geometry for their conjugated triene. The complete characterization of these compounds was performed by high field nuclear magnetic resonance (NMR) and by GC-MS. These are the 9(R),16(S)-dihydroxy-octadeca-10E,12E,14E-trienoic, 9(S),16(S)-dihydroxy-octadeca-10E,12E,14E-trienoic, 9(S),16(S)-dihydroxy-octadeca-10E,12Z,14E-trienoic and 9(R),16(S)-dihydroxy-octadeca-10E,12Z,14E-trienoic acids. They can also be synthesized by the (type 2) 15 human recombinant lipoxygenase. These dihydroxylated compounds (9,16-diHOTEs)were tested on isolated human blood platelets. We observed that only molecules con…
identifier: NNT: 2013ISAL0059
issued: 2026-05-06T05:21:27.603257
language: fr
modified: 2026-05-06T05:21:27.603261

Characterization of oxygen metabolites from alpha-linolenic acid : Effect of anti-aggregatory and anti-inflammatory
type: Distribution
access URL: https://theses.hal.science/tel-00952895
format: HTML
issued: 2026-05-06T05:21:27.631567
modified: 2026-05-06T05:21:27.573195