Regular Article7-HETE, 10-HETE, and 13-HETE Are Major Products of NADPH-Dependent Arachidonic Acid Metabolism in Rat Liver Microsomes: Analysis of Their Stereochemistry, and the Stereochemistry of Their Acid-Catalyzed Rearrangement
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Monolayer autoxidation of arachidonic acid to epoxyeicosatrienoic acids as a model of their potential formation in cell membranes
2022, Journal of Lipid ResearchCitation Excerpt :After mixing 50 mg arachidonic acid with 200 mg chromatographic silica in 4 ml hexane then decanting the solvent, the arachidonate absorbed on the silica was estimated as 38–40 mg as determined from subsequent assay of the excess remaining in the hexane solution. After drying the silica/arachidonic acid and conducting the monolayer autoxidations in ambient air at 60°C or 37°C, aliquots of the reactions were analyzed by LC-MS. As illustrated in Fig. 1, a preliminary analysis using relatively short retention times on reversed-phase LC-MS showed a profile of EET products detected as the [M-1]− ions at m/z 319 that matched the retention times of a mixture of the four authentic standards, known to elute in the order 14,15-, 11,12-, 8,9-, and 5,6-EETs (23, 24). From the monolayer autoxidation, the peak corresponding to 14,15-EET and the small extra peak immediately after it at 5.3 min gave characteristic product ions of m/z 175 and 219 diagnostic for a 14,15-epoxide (25–28).
Enantioselective high-performance liquid chromatography analysis of oxygenated polyunsaturated fatty acids
2019, Free Radical Biology and MedicineOxidant-specific biomarkers of oxidative stress. Association with atherosclerosis and implication for antioxidant effects
2018, Free Radical Biology and MedicineCitation Excerpt :Further, various CYP enzymes oxidize PUFA and cholesterol to give rise to hydroxy fatty acids and hydroxycholesterol (OHCh) respectively [65]. The production of 7-, 8-, 9-, 10-, 11-, 12-, 13-, 15-0.16-0.17-, 18-, 19-, and 20-HETEs from arachidonic acid by CYP enzymes has been reported [90]. The three bis-allylic products, 7-, 10-, and 13-HETEs, may rearrange to more stable conjugated diene HETEs.
Therapies targeting lipid peroxidation in traumatic brain injury
2016, Brain ResearchBiosynthesis, biological effects, and receptors of hydroxyeicosatetraenoic acids (HETEs) and oxoeicosatetraenoic acids (oxo-ETEs) derived from arachidonic acid
2015, Biochimica et Biophysica Acta - Molecular and Cell Biology of Lipids