The lipoxins. Stereochemical identification and determination of their biosynthesis.
The stereochemistry and double bond geometry of a novel series of leukocyte-derived arachidonic acid metabolites, the lipoxins, was determined by comparison to pure unambiguous synthetic standards. The lipoxins were found to be a mixture of four lipoxin A isomers and two lipoxin B isomers. In determining the biosynthesis of these compounds, they were shown to be formed via a tetraene epoxide. In addition, it was shown that all of the lipoxin isomers formed by the incubation of 15-hydroperoxyeicosatetraenoic acid with human leukocytes were also formed by nonenzymatic hydrolysis of this tetraene epoxide.
D016718:Arachidonic Acid; D001095:Arachidonic Acids / Q000097:blood; D002851:Chromatography, High Pressure Liquid; D008401:Gas Chromatography-Mass Spectrometry; D006801:Humans; D006893:Hydroxyeicosatetraenoic Acids / Q000097:blood*; D007536:Isomerism; D007962:Leukocytes / Q000378:metabolism*; D017572:Leukotriene A4; D007975:Leukotriene B4 / Q000097:blood; D015289:Leukotrienes; D008054:Lipid Peroxides / Q000097:blood; D044045:Lipoxins; D008084:Lipoxygenase / Q000097:blood; D009682:Magnetic Resonance Spectroscopy
D001095:Arachidonic Acids; D006893:Hydroxyeicosatetraenoic Acids; D017572:Leukotriene A4; D015289:Leukotrienes; D008054:Lipid Peroxides; D044045:Lipoxins; C040527:lipoxin A4; D007975:Leukotriene B4; D016718:Arachidonic Acid; C025086:15-hydroperoxy-5,8,11,13-eicosatetraenoic acid; C042651:lipoxin B4; D008084:Lipoxygenase