title: Biosynthesis of eicosanoids by blood cells of the crab, Carcinus maenas.
abstract: Blood cells from the crab, Carcinus maenas, stimulated with calcium ionophore A23187, in the presence of exogenous fatty acid, produced cyclooxygenase, lipoxygenase and monooxygenase derivatives of eicosatetraenoic (20:4(n - 6)) and eicosapentaenoic (20:5(n - 3)) acids. Isolation, identification and quantification of these products was achieved using chiral and reverse phase-high performance liquid chromatography, gas-chromatography, radioimmunoassay and gas chromatography-mass spectrometry. The principle metabolites observed were 8-hydroxy fatty acids and 'E' series prostaglandins. Smaller amounts of thromboxane B2, 6-keto-prostaglandin F1 alpha and 5-, 9-, 11-, 12- and 15-hydroxy-eicosatetraenoic acids were also synthesised. Lipoxygenase, cyclooxygenase and cytochrome P-450 inhibitors were used to investigate the mode of product formation. Mixtures of hydroxy-fatty acid enantiomers were produced and the dominant chiral form varied with the position of the hydroxyl group. No leukotrienes or lipoxins were detected.
authors.affiliation: Biomedical and Physiological Research Group, School of Biological Sciences, University College of Swansea, U.K.
authors.forename: A J
authors.initials: AJ
authors.lastname: Hampson
authors.forename: A F
authors.initials: AF
authors.lastname: Rowley
authors.forename: S E
authors.initials: SE
authors.lastname: Barrow
authors.forename: R
authors.initials: R
authors.lastname: Steadman
mesh_terms: D000818:Animals; D001095:Arachidonic Acids / Q000494:pharmacology; D001773:Blood Cells / Q000187:drug effects / Q000201:enzymology*; D003386:Brachyura / Q000201:enzymology*; D000001:Calcimycin / Q000494:pharmacology; D002851:Chromatography, High Pressure Liquid; D016861:Cyclooxygenase Inhibitors / Q000494:pharmacology; D015777:Eicosanoids / Q000096:biosynthesis*; D004789:Enzyme Activation / Q000187:drug effects; D006458:Hemolymph / Q000201:enzymology; D006893:Hydroxyeicosatetraenoic Acids / Q000096:biosynthesis; D007213:Indomethacin / Q000494:pharmacology; D009637:Masoprocol / Q000494:pharmacology; D011335:Proadifen / Q000494:pharmacology
chemical_list: D001095:Arachidonic Acids; D016861:Cyclooxygenase Inhibitors; D015777:Eicosanoids; D006893:Hydroxyeicosatetraenoic Acids; D000001:Calcimycin; C022022:5-hydroxy-6,8,11,14-eicosatetraenoic acid; C027356:11-hydroxy-5,8,12,14-eicosatetraenoic acid; C047628:8-hydroxyeicosatetraenoic acid; D009637:Masoprocol; D011335:Proadifen; D007213:Indomethacin