5,8,11,14-Eicosatetraenoic acid

Extracts from Clavularia viridis and also many other coral species convert arachidonic acid to the prostanoidpreclavulone-A via 8-( f )-hydroperoxy-5,ll,14( Z), QfEj-eicosatetraenoic acid. The carbocyclization is considered to occur from allene oxide and oxidopentadienyl cation intermediates. An enantioselective total synthesis of preclavulone-A was developed to assist the biosynthetic research. 

Prostaglandins, together with related compounds called thromboxanes and leukotrienes, make up a class of compounds called eicosanoids because they are derived biologically7 from 5,8,11,14-eicosatetraenoic acid, or arachidonic... 

We have already stressed the potential importance of lipid-rich membranes in the skin as potential targets for ROS-induced damage and ageing of human skin is morphologically identical to changes found by peroxidative processes (Serri et al., 1977). The involvement of AA metabolites in skin disease, and in particular psoriasis, has been the subject of much recent interest. Studies have included topical and intradermal administrations of AA metabolites, and assay of such products in clinical specimens. Results show that concentration of AA, 12-hydroxy-eicosatetraenoic acid (12-HETE), PG and leu-kotrienes are increased in psoriatic lesions (Hammarstrom etal., 1975 Camp etal., 1983 Brain etal., 1984 Duell et al., 1988) and also that full-thickness epidermis from normal and diseased skin has the enzymatic capacity to convert AA to some of the same metabolites (Hammarstrom etal., 1975, 1979 Camp etal., 1983 Brain etal., 1984 Ziboh et al., 1984 DueU et al., 1988). The biological effect of both 12-HETE and leukotrienes was confirmed by both topical application and intradermal injection, which caused epidermal inflammation and... 

Chan, C.C., Duhamel, L. and Ford-Hutchison, A. (1985). Leukotriene B4 and 12-hydroxy eicosatetraenoic acid stimulate epidermal proliferation in vivo in the guinea pig. J. Invest. Dermatol. 85, 333-334. 

Hammarstrom, S., Hamberg, M., Samuelsson, B., Duell, E.A., Stawiski, M. and Voorhees, J.J. (1975). Increased concentrations of non-esterified arachidonic acid, 12L-hydroxy-5,8,10,14-eicosatetraenoic acid, prostaglandin E2 and prostaglandin F2 in epidermis of psoriasis. Proc. Natl Acad. Sci. USA 72, 5130-5134. 

WooUard, P.M. (1986). Stereochemical differences between 12-hydroxy-5,8,10,14-eicosatetraenoic acid in platelets and psoriatic lesions. Biochem. Biophys. Res. Commun. 136, 169-176. 

Figure 7. Dependence of BP oxidation by ram seminal vesicle micro-somes on the concentration of different hydroperoxides. Abbreviations used are 20 4, arachidonic acid 15-HPEA, 15-hydroperoxy-eicosatetraenoic acid t-BuOOH, t-butyl hydroperoxide. The structure is PGG2 is given in Figure 1.

Synthesis of 5(S)-hydroxy-6(R)-(N-[1-11C]acetyi)cysteinyi-7, 9-trans-11, 14-cis-eicosatetraenoic acid... 

Eicosatetraenoic acid 5,8,11,14,17-Eicosapentenoic acid 4,7,10,13,16,19-Docosahexenoic acid Tetracosanoic acid 15-Tetracoseanoic acid 2-Hydroxytetracosanoic acid... 

Powell PK, Wolf I, Jin R, et al. Metabolism of arachidonic acid to 20-hydroxy-5,8,11, 14-eicosatetraenoic acid by P450 enzymes in human liver involvement of CYP4F2 and CYP4A11. J Pharmacol Exp Ther 1998 285(3) 1327-1336. 

An intravenous infusion of PAF causes rapid (within 60 s) intravascular platelet aggregation, thrombocytopenia and platelet factor 4 release, as well as a profound and reversible neutropenia, due to enhanced aggregation and adherence of these cells. In vitro, PAF effects on neutrophils are dependent upon extracellular Ca2+ and Mg2+ and occur within 60 s of addition. The addition of inhibitors of 5-lipoxygenase activity (e.g. ETYA, 5,8,11,14-eicosatetraenoic acid and NDGA, nordihydroguaiaretic acid) - but not those... 

Arachidonic (A5.8,ii,i4-eicosatetraenoic) acid Oleic (A -octadecaenoic) acid... 

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