Inhibition of prostaglandin biosynthesis by triynoic acids

Prostaglandin biosynthesis from eicosa-8,11,14-trienoic acid in microsomes from bovine seminal vesicles is inhibited by acetylenic acids. Octadeca-6,9,12-triynoic acid and eicosa-8,11,14-triynoic acid are the most potent inhibitors. These acids both contain an ω-8 methylene group. Within the 20-carbon acetylenic acid series, inhibition decreases in the sequence eicosa-8,11,14-triynoic acid > eicosa-7,10,13-triynoic acid > eicosa-5,8,11-triynoic acid. Furthermore, eicosa-8,11,14-triynoic acid is a more potent inhibitor of arachidonic acid induced platelet aggregation than either eicosa-7,10,13-triynoic acid or eicosa-5,8,11-triynoic acid. The ω-8 methylene group is not the only determinent of inhibitory potency since docosa-10,13,16-triynoic acid is less potent than its 18 and 20 carbon analogs and all of these acids have an ω-8 methylene group.