Formation of adducts between 13-oxooctadecadienoic acid (13-OXO) and protein- derived thiols, in vivo and in vitro
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Quantification of bovine oxylipids during intramammary Streptococcus uberis infection
2015, Prostaglandins and Other Lipid MediatorsCitation Excerpt :Exposure to HPODE, especially 13-HPODE, induced apoptosis in T cells and endothelial cells suggesting 13-HPODE is particularly detrimental to cell survival and tissue health [46,47]. Linoleic acid-derived HODE isomers, 9- and 13-, can further be metabolized by NAD+ dehydrogenation to 9- and 13-oxoODE resulting in potent anti-inflammatory oxylipids [48,49]. In epithelial cells and macrophages, the oxoODEs robustly activate PPARγ, which contributes to limiting pro-inflammatory responses by reducing the expression of pro-inflammatory cytokines [19,49].
15-Hydroxyprostaglandin dehydrogenase generation of electrophilic lipid signaling mediators from hydroxy ω-3 fatty acids
2015, Journal of Biological ChemistryCitation Excerpt :However, the dehydrogenase(s) responsible for the oxidation of the hydroxyl group to a carbonyl has not been identified for many of these metabolites. 5-Hydroxyeicosatetraenoic acid (5-HETE) is oxidized by 5-hydroxyeicosanoid dehydrogenase (8, 9), and there is some evidence of a 13-hydroxyoctadecadienoic acid (13-HODE) dehydrogenase that converts 13-HODE and 9-HODE to their corresponding oxo-octadecadienoic acid metabolites (10). Notably, all of the 15PGDH substrates thus described are metabolites of arachidonic acid, with the exception of (5(S),12(R),18(R))-trihydroxy-6Z,8E,10E,14Z,16E-eicosapentaenoic acid (resolvin E1) (11).
Glutathione adducts of oxyeicosanoids
2002, Prostaglandins and Other Lipid MediatorsEnergy-dependent export of the 13-oxooctadecadienoic acid-glutathione conjugate from HT-29 cells and plasma membrane vesicles
2001, Biochimica et Biophysica Acta - Molecular and Cell Biology of LipidsPyridoxamine, an inhibitor of advanced glycation reactions, inhibits advanced lipoxidation reactions: Mechanism of action of pyridoxamine
2000, Journal of Biological ChemistryCitation Excerpt :In support of this mechanism, KODEs have been identified as products of both non-enzymatic (27, 28) and enzymatic (29, 30) peroxidation of LA and have also been detected by chemical methods in atherosclerotic plaque (31). Thiol compounds are known to react directly with KODEs, whereas their reaction with hydroperoxyoctadecadienoic acids requires autoxidizing conditions (Fe3+ and O2) (16, 17). PM also fails to react with lipid peroxides (prepared from LA using soybean lipoxygenase) under anti-oxidative conditions (anaerobic incubation in the presence of DTPA; data not shown.).