Abstract
The eicosanoids are oxygenated products of arachidonic acid. Prostaglandins (PCs) are synthesized by cyclooxygenase; hydroxyeicosatetraenoic acids (HETEs) and leukotrienes (LTs) are synthesized by lipoxygenase (for reviews, see Hammarstrom, 1983; Lands, 1979). Prostaglandins are variations of the 20-carbon fatty acid prostanoic acid, and their nomenclature is based on the oxygen-derived substitutions in the five-membered ring and the number of double bonds in the two side chains. The carboxylic acid function is present in the α side chain, and the terminal methyl group is present in the β side chain. Thromboxanes and prostacyclin have a slightly modified ring structure. Lipoxygenase reaction products can occur as various isomers, depending upon where addition of oxygen takes place. The immediate precursors of HETEs are hydroperoxy derivatives (HPETEs). Further metabolism of HPETEs by dehydration to epoxides and addition of glutathione results in the synthesis of leukotrienes. Eicosanoids can also be synthesized from other fatty acids, such as eicosatrienoic acid (20:3, n-6) and eicosapentaenoic acid (20:5, n-6). Prostaglandins from arachidonic acid are the 2-series, e.g., PGE2. The l-series are products of 20:3 (n-6), and the 3-series are products of 20:5 (n-6).
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Abe M., Kawazoe Y., and Shigematsu N. (1985) Influence of salts on high performance liquid chromatography of leukotnenes. Anal. Biochem. 144, 417–422.
Bazan N. G., Bazan, H. E I’., Birkle D. L., and Rossowska M. (1987) Synthesis of leukotrienes in the frog retina and retinal pigment epithelium. J Neurosci Res, 18, 591–596.
Birkle D. L., Bazan H. E. P., and Bazan N. G. (1988) Use of Radiotracer Techniques and High Pressure Liquid Chromatography with Flow Scintillation Detection in the Analysis of Fatty Acids and Eicosanoids, in Progress in HPLC vol. 4 Flow Through Radioactivity Detectors in HPLC (Parvez H., Lucas-Reich S., and Pravez S., eds.) VNU International Science Press, Utrecht, Holland (in press).
Birkle D. L. and Bazan N.G (1984a) Effect of K+ depolarization on the synthesis of prostaglandins, hydroxyeicosatetra(5,8,11,14)enoic acid (HETE) and other eicosanoids in the rat retina: Evidence for esterification of 12-HETE in lipids. Biochim. Biophys. Acta 795, 564–573.
Birkle D. L. and Bazan N. G. (1984b) Lipoxygenase-and cyclooxygenasereaction products and incorporation into glycerolipids of radiolabeled arachidonic acid in the bovine retina. Prostaglandins 27, 203–206.
Careaga M. M. and Sprecher H (1984) Synthesis of two hydroxy fatty acids from 7,10,13,16,19-docosahexaenoic acid by human platelets. J Biol. Chem. 259, 14413–14417.
Claeys M., Bazan H. E. P., Birkle D. L, and Bazan N. G. (1986) Diacylglycerols interfere in straight phase HPLC analysis of lipoxygenase products of docosahexaenoic or arachidonic acid. Prostaglandins 32, 813–827.
Claeys M., Kivits G. A. A., Christ-Hazelhof E., and Nugteren D. H. (1985) Metabolic profile of linoleic acid in porcine leukocytes through the lipoxygenase pathway. Biochim. Biophys. Acta 837, 35–51.
Eling T., Tainer Ally A., and Warnock R. (1986) Separation of arachidonic acid metabolities by high-pressure liquid chromatography. Meth. Enzymol 86, 511–517.
Green K., Granstrom E., Samuelsson B., and Axen U. (1973) Methods for quantitative analyses of PGF2α, PGE2, 9α,11α-dihydroxy-15 ketoprost-5-enoic acid, and 9α,11α, 15-trihydroxyprost-5-enorc acid from body fluids using deuterated carriers and GC-MS. Anal. Biochem. 54, 434–453.
Hamilton J. G. and Karol R. J. (1982) High performance liquid chromatography (HPLC) of arachidonic acid metabolites. Prog. Lipid Res. 21, 155–170.
Hammarstrom S. (1983) Leukotrienes. Ann. Rev. Biochem. 52, 355–377.
Hensby C. (1977) Physical Methods in Prostglandins Research, in Prostaglandin Research, (Crabbe, P., ed.) Academic, New York.
Lands W.E.M. (1979) The biosynthesis and metabolism of prostaglandins. Ann Rev. Physiol. 41, 633–652.
Luderer J. R., Riley D. L., and Demers L. M. (1983) Rapid extraction of arachidonic acid metabolites utilizing octadecyl reversed-phase columns. J. Chromatogr 273, 402–409.
Metz S. A., Hall M. E., Timothy W. H., and Murphy R. C. (1982) Rapid extraction of leukotrienes from biologic fluids and quantitation by high-performance liquid chromatography. J. Chromatogr. 233, 193–201.
Nicosia S. and Galli G. (1976) Evaluation of prostaglandin biosynthesis in rat cerebral cortex by mass fragmentography. Adv. Mass Spectrom. Biochem. Med. 1, 457–464.
Pediconi M. F., Rodriguez deTurco E. and Bazan N. G. (1982) Diffusion of intracerebrally injected [l-14C] arachidonic acid and [2-3H]glycerol in the mouse brain. Effects of ischemia and electroconvulsive shock. Neurochem. Res. 7, 1435–1456.
Pediconi M. F., Rodriguez de Turco E. and Bazan N. G. (1983) Effects of post decapitation ischemia on the metabolism of [14C]arachidonic acid and [14C]palmitic acid in the mouse brain. Neurochem. Res. 8, 835–845.
Reddy T. S. and Bazan N. G. (1983) Kinetic properties of arachidonoyl coenzyme A synthetase in rat brain microsomes. Arch. Biochem. Biophys 226, 126–133.
Salmon T. A. and Flower R. J, (1982) Extraction and thin layer chromatography of arachidonic acid metabolites. Meth. Enzymol. 86, 477–493.
Saunders R. and Horrocks L. A. (1984) Simultaneous extraction and preparation for high performance liquid chromatography of prostaglandins and phospholipids. Anal. Biochem. 143, 71–75.
Schulz R. and Seeger W. (1986) Release of leukotrienes into the perfusate of calcium-ionophore stimulated rabbit lungs. Biochem. Pharmucol 35, 183–193
Smith B. J., Ross R. M., Ayers R., Wills M. R., and Savoy R. (1983) Rapid separation of prostaglandins by linear high performance thin layer chromatography J. Liquid Chromatogr. 7, 1265–1272.
Van Horne K. C (1985) Sorbant Extraction Technology Analytichem, International, California, pg. 82–83.
Varhagen J., Walstra P., Veldink G. A., and Vliegenthart J. F. G. (1984) Separation and quantitation of leukotrienes by reversed-phased high-performance liquid chromatography Prostaglandins Leukotrienes Med 13, 15–20.
Wolfe L. S. (1982) Eicosanoids: Prostaglandins, thromboxanes, leukotrienes and other derivatives of carbon-20 unsaturated fatty acids. J. Neurochem 38, 1–13
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1988 The Humana Press Inc.
About this protocol
Cite this protocol
Birkle, D.L., Bazan, H.E.P., Bazan, N.G. (1988). Analysis of Prostaglandins, Leukotrienes, and-Related Compounds in Retina and Brain. In: Boulton, A.A., Baker, G.B., Horrocks, L.A. (eds) Lipids and Related Compounds. Neuromethods, vol 7. Humana Press. https://doi.org/10.1385/0-89603-124-1:227
Download citation
DOI: https://doi.org/10.1385/0-89603-124-1:227
Publisher Name: Humana Press
Print ISBN: 978-0-89603-124-1
Online ISBN: 978-1-59259-612-6
eBook Packages: Springer Protocols