Regular ArticleIdentification of 5-Keto-(7E,9E,11Z,14Z)-Eicosatetraenoic Acid as a Novel Nonenzymatic Rearrangement Product of Leukotriene A4
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Impact of myeloperoxidase-derived oxidants on the product profile of human 5-lipoxygenase
2015, Free Radical Biology and MedicineCitation Excerpt :This phenomenon was reported for the injection of 12-HpETE or 15-HpETE onto an HPLC column without prior reduction [31]. However, the measured product might also be 5-oxo-7E,9E,11Z,14Z-eicosatetraenoic acid, a further nonenzymatic hydrolysis product of LTA4 [25], differing only in the position of the double bonds. Gravel et al. described an MS/MS fragment with m/z 203 Da for 5-oxo-7E,9E,11Z,14Z-eicosatetraenoic acid [25], which is also used for the applied LC–ESI–MS/MS analysis of 5-oxo-ETE.
Inhibition of arachidonic acid metabolism and its implication on cell proliferation and tumour-angiogenesis
2009, International ImmunopharmacologyA one-step method of 10,17-dihydro(pero)xydocosahexa-4Z,7Z,11E,13Z,15E,19Z- enoic acid synthesis by soybean lipoxygenase
2006, Journal of Lipid ResearchCitation Excerpt :The spectrum lacked a proton resonance with δ 6.15–6.24 ppm, which would have been present if the compound had a conjugated 11E,13E or 13E,15E fragment. Such resonances have been reported for several compounds with conjugated E,E double bonds, for example, all-trans isomers of 9(S)- and 13(S)-hydroxy linoleyl alcohols (14), 9(S)- and 13(S)-hydroxy monolinoleoyl glycerols (15), 5,6-dihydroxyeicosapenta-7E,9E,11Z,14Z,17Z-enoic acid (16), 5-ketoeicosatetra-7E,9E,11Z,14Z-enoic acid (17), 14,15-dihydroxyeicosatetra-5Z,8Z,10E,12E-enoic acid (18), and 5,12(S)-dihydroxyeicosatetra-6E,8E,10E-enoic acid (19). Only three types of protons that belonged to the 11E,13Z,15E fragment were observed in the NMR experiments (Table 1, Figs. 1, 3, 4).
On the structure and synthesis of neuroprotectin D1, a novel anti-inflammatory compound of the docosahexaenoic acid family
2005, Journal of Lipid ResearchBiochemistry, biology and chemistry of the 5-lipoxygenase product 5-oxo-ETE
2005, Progress in Lipid Research