@prefix dcat: . @prefix dct: . @prefix foaf: . @prefix vcard: . @prefix xsd: . a dcat:Dataset ; dct: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 containing a conjugated triene with a E,Z,E geometry are able to inhibit platelet aggregation induced by collagen, and inhibit sheep cyclooxygenase-1 (COX-1). The anti-inflammatory properties of these products were also studied. All 9,16-diHOTEs isomers having a conjugated triene with a E,Z,E geometry, inhibit human recombinant cyclooxygenase-2 (COX-2) and only 9(R),16(S)-dihydroxy-octadeca-10E,12Z,14E-trienoic acid inhibits polymorphonuclear leukocytes (PMN) 5-lipoxygenase which is involved in the leukotriene synthesis from arachidonic acid. In conclusion, the E,Z,E dihydroxlated compounds from 18:3n-3, as well as PDX, inhibiting the COX-1 and 2 activities appear to be anti-aggregatory and anti-inflammatory agents. These results provide pharmacological perspectives to nutritional recommendations promoting the intake of alpha-linolenic acid. """ ; dct:identifier "NNT: 2013ISAL0059" ; dct:issued "2026-05-06T05:21:27.603257"^^xsd:dateTime ; dct:language "fr" ; dct:modified "2026-05-06T05:21:27.603261"^^xsd:dateTime ; dct:publisher ; dct:title "Characterization of oxygen metabolites from alpha-linolenic acid : Effect of anti-aggregatory and anti-inflammatory" ; dcat:contactPoint [ a vcard:Organization ; vcard:fn "CCSD" ] ; dcat:distribution ; dcat:keyword "acide-docosahexaenoique", "acide-gras", "agregation-plaquettaire", "biosciences", "chromatographie-liquide-a-haute-performance", "docosahexaenoic-acid", "fatty-acid", "high-performance-liquid-chromatography", "human-leukocytes", "infoeu-reposemanticsdoctoralthesis", "leucocytes-humains", "mass-spectrometry", "nuclear-magnetic-resonance", "platelet-aggregation", "resonance-magnetique-nucleaire", "sdvsalife-sciences-q-bioagricultural-sciences", "spectrometrue-de-masse", "theses" ; dcat:landingPage . a dcat:Distribution ; dct:format "HTML" ; dct:issued "2026-05-06T05:21:27.631567"^^xsd:dateTime ; dct:modified "2026-05-06T05:21:27.573195"^^xsd:dateTime ; dct:title "Characterization of oxygen metabolites from alpha-linolenic acid : Effect of anti-aggregatory and anti-inflammatory" ; dcat:accessURL . a foaf:Agent ; foaf:name "test_moissonnage_selune" . a foaf:Document .