Structure-function relationships of non-cyclic dioxygenase products from polyunsaturated fatty acids: Poxytrins as a class of bioactive derivatives

• Poxytrins are double dioxygenase end-products of PUFA with an E,Z,E conjugated triene.
• This short review focuses on Protectin DX from DHA and linotrins from ALA.
• Poxytrins inhibit platelet aggregation and cell cyclooxygenases (COX-1 and COX-2).
• Poxytrins with the R,S stereochemistry appear slightly more potent than the S,S.

More and more attention is paid to omega-3 fatty acids because of their potential activities in preventing cardiovascular events. In this brief review, we focus on the lipoxygenase end-metabolites of two relevant nutrients belonging to the omega-3 family fatty acids: alpha-linolenic and docosahexaenoic acids, the latter being a prominent component of brain lipids. Dihydroxylated derivatives are described as well as their inhibitory effects on platelet aggregation and cyclooxygenase activities. We point out that only the dihydroxylated products with the trans,cis,trans/E,Z,E conjugated triene geometry exhibit those inhibitory activities. These properties being found with other polyunsaturated fatty acid oxygenated products sharing the same E,Z,E molecular motif, they have been collectively named poxytrins. From alpha-linolenic and docosahexaenoic acids, poxytrins are linotrins and protectin DX, respectively.