Title: Prostaglandin(s)
Literature References: A family of biologically potent lipid acids first discovered in seminal fluid and extracts of accessory genital glands of man and sheep: von Euler, Arch. Exp. Pathol. Pharmakol. 175, 78 (1934); Klin. Wochenschr. 14, 1182 (1935). Isoln: Bergstrom, Sjovall, US 3069322 and US 3598858 (1962, 1971); Samuelsson, J. Biol. Chem. 238, 3229 (1963). Also found in lower concns in other organs: idem, Biochim. Biophys. Acta 84, 707 (1964). The single non-mammalian source of prostaglandin intermediates, or syntons, is the gorgonian sea whip or sea fan, Plexaura homomalla: Weinheimer, Spraggins, Tetrahedron Lett. 1969, 5185; Schneider et al., J. Am. Chem. Soc. 94, 2122 (1972). Prostaglandins are named as derivatives of prostanoic acid. Prostaglandins are divided into the types E, F, A, B, C, and D based on functions in the cyclopentane ring. Numerical subscripts refer to the number of unsaturations in the side chains; a or b subscripts refer to the configuration of substituents in the ring. Six naturally occurring prostaglandins, E1, E2, E3, F1a, F2a, F3a, are considered primary in that no one is derived from another in the living organism. First structural and stereochemical elucidations: Bergstrom et al., Acta Chem. Scand. 16, 501 (1962); eidem, J. Biol. Chem. 238, 3555 (1963). Absolute config: Nugteren et al., Nature 212, 38 (1966). First total synthesis of racemic PGE1 and PGF1a: Corey et al., J. Am. Chem. Soc. 90, 3245 (1968). Review of synthetic studies: Pike, Fortschr. Chem. Org. Naturst. 28, 313 (1970); Axen et al., in The Total Synthesis of Natural Products vol. 1, J. ApSimon, Ed. (Wiley-Interscience, New York, 1973) pp 81-143; Clarkson in Progress in Organic Chemistry vol. 8, W. Carruthers, J. K. Sutherland, Eds. (Wiley, New York, 1973) pp 1-28. Book: J. S. Bindra, R. Bindra, Prostaglandin Synthesis (Academic Press, New York, 1977). Biosynthesis occurs by enzymatic conversion of unsaturated twenty-carbon fatty acids. Review of biosynthetic studies: Samuelsson, Prog. Biochem. Pharmacol. 5, 109 (1969). Review of metabolism: Samuelsson et al., Ann. N.Y. Acad. Sci. 180, 138 (1971). Biological activities include stimulation of smooth muscle, dilation of small arteries, bronchial dilation, lowering of blood pressure, inhibition of gastric secretion, of lipolysis, and of platelet aggregation, induction of labor, abortion, and menstruation, and increase in ocular pressure. Implicated also in dysmenorrhea, inflammatory reactions, nasal vasoconstriction, kidney function, and in autonomic neurotransmission. Reviews of pharmacological and biochemical aspects: Horton, Experientia 21, 113 (1965); Weeks, Annu. Rev. Pharmacol. 12, 317 (1972); Hinman, Annu. Rev. Biochem. 41, 161 (1972). Review of biological activities of synthetic prostaglandins: Ramwell et al., Nature 221, 1251 (1969). Review of analytical and preparative techniques: "Prostaglandins and Arachidonate Metabolites" in Methods Enzymol. 86, 705, (1982) . General reviews: Bergstrom, Science 157, 382 (1967); Bergstrom et al., Pharmacol. Rev. 20, 1 (1968); Ramwell, Shaw, Recent Prog. Horm. Res. 26, 139 (1970); Pike, Sci. Am. 225, 84 (Nov., 1971); Bindra, Bindra, Progress in Drug Research vol. 17 (Birkhäuser Verlag, Basel, 1973) pp 410-487. Books: The Prostaglandins vols. 1, 2, P. Ramwell, Ed. (Plenum Press, New York, 1973, 1974); Prostaglandins in Cardiovascular and Renal Function, A. Scriabine et al., Eds. (Spectrum Publications, New York, 1980) 498 pp; Cardiovascular Pharmacology of the Prostaglandins, A. Herman, Ed. (Raven Press, New York, 1982) 472 pp.

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