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. Author manuscript; available in PMC: 2012 May 1.
Published in final edited form as: Free Radic Biol Med. 2011 Mar 4;50(9):1163–1170. doi: 10.1016/j.freeradbiomed.2011.02.001

Scheme 1.

Scheme 1

Proposed mechanism of COX-DGLA peroxidation to form DGLA-derived free radicals via C-15 oxygenation, a peroxidation pathway similar to COX-AA [17].

Note that in both COX-AA and DGLA peroxidation, free radial reactions including formation of C-13 radicals, C-9/C-11 endoperoxide bridge (addition of the first O2), C-8 and C-12 cyclization, and C-15 oxygenation (via peroxidase activity of COX, addition of the second O2). The source of H needed for the β’-scission in this pathway could be hydrophilic COX channel residues Tyr-385, Tyr-348, and Ser-530, as well as H2O [29–30]. The proposed oxygen-centered radicals can be further decomposed to the other products, e.g. C-9 to C-11 elimination to form malonaldehyde.