Synthesis and Biological Properties of Prostaglandin Endoperoxides, Thromboxanes and Prostacyclins

Abstract

Prostaglandins continue to be a major and fast-developing area of research in the chemical and biological sciences. Increasing evidence has recently prompted some researchers to suggest that the important physiological actions of these hormones are exerted by their unstable arachidonic acid pathway intermediates, the endoperoxides, thromboxanes, and prostacyclin. The importance of these substances in physiology and medicine and the challenge they pose to synthetic chemistry place them in the forefront of chemical and biochemical investigation. Current biological research has greatly benefited by synthetic advances which have made available large quantities of some of these naturally occurring intermediates and several analogs with increased stabilities. Following a brief review of the primary prostaglandins, the present article describes recent biosynthetic developments, partial and total syntheses of prostaglandin endoperoxide analogs, thromboxane B2, and prostacyclins, and the biological properties of these molecules.

Bioorganic Chemistry

“…Another practical application of biological oxidation is to be found in the biosynthesis of the prostaglandins (201,202). In nature, they are synthesized by selective oxidation of a C20 fatty acid precursor that contains three or four double bonds.…”

Synthesis and biological properties of pinane-thromboxane A2, a selective inhibitor of coronary artery constriction, platelet aggregation, and thromboxane formation.

“…1) for an unstable (half-life of about 30 s at pH 7.4 and 370C) substance with potent thrombotic and smooth muscle contracting properties that they named thromboxane A2 (TA2). The isolation or chemical synthesis of this important member of the arachidonic acid cascade (2) has not yet been achieved. Furthermore, no analogs of this structurally unusual molecule have been reported to date.…”

Isolation of Four Novel Carotanoids as Possible Metabolites of Rugosic Acid A inRosa rugosaLeaves

“…Compounds 3, 4, 5 and 6 are considered to be the initial metabolites of 2. The hypothetical metabolic pathway, resembling several rearrangements of PGH 2 on the peroxide bridge, 9,10) is considered to undergo an enzymatic regulation in, the leaf tissue. Consequently, these metabolites are expected to playa significant role in the tissue, and a biochemical study should be carried out as well as biosynthetic study on rugosal A (1).…”