Metabolism of icosa-5,11,14-trienoic acid in human platelets and the inhibition of arachidonic acid metabolism in human platelets by icosa-5,8,14-triynoic and icosa-5,11,14-triynoic acids

Add time:08/30/2019    Source:sciencedirect.com

Two fatty acids differing from arachidonic acid in lacking one of the internal double bonds (20:35,8,14 and 20:35,11,14) and their 1-C14 and acetylenic analogues were synthesized. 20:35,8,14 was not metabolized by human platelets but 20:35,11,14 yielded a small amount (1.5% conversion) of two hydroxy fatty acids in a three (11-hydroxy-5,12,14-icosatrienoic acid) to one (15-hydroxy-5,11,13-icosatrienoic acid) proportion. Indomethacin inhibited formation of both hydroxy fatty acids indicating that they are produced via cyclooxygenase. Both ethylenic acids were weak inhibitors of cyclooxygenase (substrate 20 μM arachidonic acid) (ID50: 8.8 μM 20:35,8,14; 11.2 μM 20:35,11,14) but were inactive against lipoxygenase (RD50 > 100 μM). Similarly, both acetylenic analogues were poor inhibitors of lipoxygenase (ID50: 23.4 μM 20:35,8,14; 47.8 μM 20:35,11,14) but although 20:35,8,14 was inactive against cyclooxygenase (ID50 > 100 μM) the 20:35,11,14 was a potent inhibitor (ID50: 0.35 μM). The results are interpreted on the basis that hydrogen removal by the lipoxygenase is from C10 and by the cyclooxygenase from C13 but only in 20:35,11,14 are these hydrogens (C13) located at the center of a 1,4 cis cis pentadiene system (ethylenic) or a 1,4 pentadiyne system (acetylenic).

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