17-keto-7(Z),10(Z),13(Z),15(E),19(Z)-Docosapentaenoic Acid Exclusive

Docosapentaenoic acid (DPA) is a ω-3 fatty acid found in fish oils. 17-oxo-7(Z),10(Z),13(Z),15(E),19(Z)-docosapentaenoic acid is a metabolite of lipoxygenase-mediated oxidation of DPA that is produced endogenously by aspirin-enhanced COX-2 activity.^1,2 It has been shown to activate Nrf2-dependent antioxidant gene expression, to act as a PPARγ agonist (EC₅₀ = ~200 nM), and to inhibit pro-inflammatory cytokine and nitric oxide production at biological concentration ranges (5-25 μM).²

17-Oxo-7(Z),10(Z),13(Z),15(E),19(Z)-docosapentaenoic acid (17-Oxo-DPA; 17-Oxo-7(Z),10(Z),13(Z),15(E),19(Z)-DPA) is an electrophilic oxo-derivative (EFOX) of the docosahexaenoic acid (DHA) (HY-B2167). 17-Oxo-7(Z),10(Z),13(Z),15(E),19(Z)-docosapentaenoic acid is generated during inflammation by COX-2-catalyzed mechanism in activated macrophages. 17-Oxo-7(Z),10(Z),13(Z),15(E),19(Z)-docosapentaenoic acid acts as an agonist for PPARγ and a modulator for NF-κB signaling pathway, inhibits the production of pro-inflammatory cytokines and nitric oxide, and exhibits anti-inflammatory efficacy[1].

PPARγ

1. Jie, M.S.F.L.K., and Pasha, M.K. Fatty acids, fatty acid analogues and their derivatives Nat. Prod. Rep. ,607-629(1998).
2. Groeger, A.L., Cipollina, C., Cole, M.P., et al. Cyclooxygenase-2 generates anti-inflammatory mediators from omega-3 fatty acids Nat. Chem. Biol. ,(2010).