title: Structure-function relationships of non-cyclic dioxygenase products from polyunsaturated fatty acids: poxytrins as a class of bioactive derivatives.
abstract: More and more attention is paid to omega-3 fatty acids because of their potential activities in preventing cardiovascular events. In this brief review, we focus on the lipoxygenase end-metabolites of two relevant nutrients belonging to the omega-3 family fatty acids: alpha-linolenic and docosahexaenoic acids, the latter being a prominent component of brain lipids. Dihydroxylated derivatives are described as well as their inhibitory effects on platelet aggregation and cyclooxygenase activities. We point out that only the dihydroxylated products with the trans,cis,trans/E,Z,E conjugated triene geometry exhibit those inhibitory activities. These properties being found with other polyunsaturated fatty acid oxygenated products sharing the same E,Z,E molecular motif, they have been collectively named poxytrins. From alpha-linolenic and docosahexaenoic acids, poxytrins are linotrins and protectin DX, respectively.
authors.affiliation: Université de Lyon, UMR Inserm 1060, INSA-Lyon, IMBL, Villeurbanne, France. Electronic address: michel.lagarde@insa-lyon.fr.
authors.forename: Michel
authors.initials: M
authors.lastname: Lagarde
authors.affiliation: Université de Lyon, UMR Inserm 1060, INSA-Lyon, IMBL, Villeurbanne, France.
authors.forename: Evelyne
authors.initials: E
authors.lastname: Véricel
authors.affiliation: Université de Lyon, UMR Inserm 1060, INSA-Lyon, IMBL, Villeurbanne, France.
authors.forename: Miao
authors.initials: M
authors.lastname: Liu
authors.affiliation: Université de Lyon, UMR Inserm 1060, INSA-Lyon, IMBL, Villeurbanne, France.
authors.forename: Ping
authors.initials: P
authors.lastname: Chen
authors.affiliation: Université de Lyon, UMR Inserm 1060, INSA-Lyon, IMBL, Villeurbanne, France.
authors.forename: Michel
authors.initials: M
authors.lastname: Guichardant
mesh_terms: D049308:Dioxygenases / Q000378:metabolism; D004281:Docosahexaenoic Acids / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology; D015525:Fatty Acids, Omega-3 / Q000737:chemistry* / Q000378:metabolism; D005231:Fatty Acids, Unsaturated / Q000737:chemistry* / Q000378:metabolism; D006801:Humans; D015394:Molecular Structure; D010974:Platelet Aggregation / Q000187:drug effects; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D017962:alpha-Linolenic Acid / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology
chemical_list: D015525:Fatty Acids, Omega-3; D005231:Fatty Acids, Unsaturated; D017962:alpha-Linolenic Acid; D004281:Docosahexaenoic Acids; D049308:Dioxygenases
keywords: Blood cells; Cyclo-oxygenases; Leukotrienes; Lipoxygenases; Prostanoids