title: Full characterization of PDX, a neuroprotectin/protectin D1 isomer, which inhibits blood platelet aggregation.
abstract: Our study aimed to establish the complete structure of the main dihydroxy conjugated triene issued from the lipoxygenation (soybean enzyme) of docosahexaenoic acid, named PDX, an isomer of protectin/neuroprotectin D1 (PD1/NPD1) described by Bazan and Serhan. NMR approaches and other chemical characterization (e.g. GC-MS, HPLC and LC-MS/MS) indicated that PDX is 10(S),17(S)-dihydroxy-docosahexa-4Z,7Z,11E,13Z,15E,19Z-enoic acid. The use of (18)O(2) and mass spectrometry showed that PDX is a double lipoxygenation product. Its structure differs from PD1, with E,Z,E geometry (PDX) instead of E,E,Z (PD1) and S configuration at carbon 10 instead of R. PDX inhibits human blood platelet aggregation at sub-micromolar concentrations.
authors.affiliation: Université de Lyon, Inserm UMR 870, Insa-Lyon, RMND/IMBL, Inra 1235, 69621 Villeurbanne, France.
authors.forename: P
authors.initials: P
authors.lastname: Chen
authors.forename: B
authors.initials: B
authors.lastname: Fenet
authors.forename: S
authors.initials: S
authors.lastname: Michaud
authors.forename: N
authors.initials: N
authors.lastname: Tomczyk
authors.forename: E
authors.initials: E
authors.lastname: Véricel
authors.forename: M
authors.initials: M
authors.lastname: Lagarde
authors.forename: M
authors.initials: M
authors.lastname: Guichardant
mesh_terms: D001093:Arachidonate 15-Lipoxygenase / Q000378:metabolism; D002244:Carbon / Q000737:chemistry; D004281:Docosahexaenoic Acids / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D008401:Gas Chromatography-Mass Spectrometry; D006801:Humans; D006878:Hydroxides / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D010974:Platelet Aggregation / Q000187:drug effects*; D013025:Glycine max / Q000201:enzymology; D013237:Stereoisomerism
chemical_list: D006878:Hydroxides; C487679:protectin D1; D004281:Docosahexaenoic Acids; D002244:Carbon; C031356:hydroxide ion; D001093:Arachidonate 15-Lipoxygenase