“Twin peaks”: Searching for 4-hydroxynonenal urinary metabolites after oral administration in rats

Seppanen, 2002, Formation of 4-hydroxynonenal, a toxic aldehyde, in soybean oil at frying temperature, Journal of American Oil Chemists' Society, 79, 1033, 10.1007/s11746-002-0598-z Seppanen, 2004, Incorporation of the toxic aldehyde 4-hydroxy-2-trans-nonenal into food fried in thermally oxidized soybean oil, Journal of American Oil Chemists' Society, 81, 1137, 10.1007/s11746-004-1031-3 Sakai, 1995, A lipid peroxidation-derived aldehyde, 4-hydroxy-2-nonenal, contents in several fish meats, Fisheries Sciences, 61, 527, 10.2331/fishsci.61.527 Sakai, 2006, Effect of NaCl on the lipid peroxidation-derived aldehyde, 4-hydroxy-2-nonenal, formation in boiled pork, Bioscience, Biotechnology and Biochemistry, 70, 815, 10.1271/bbb.70.815 Surh, 2007, 4-Hydroxy-2-alkenals in polyunsaturated fatty acids-fortified infant formulas and other commercial food products, Food Additives and Contaminants, 24, 1209, 10.1080/02652030701422465 Gasc, 2007, 4-Hydroxynonenal in foodstuffs: heme concentration, fatty acid composition and freeze-drying are determining factors, Redox Report, 12, 40, 10.1179/135100007X162257 Nishikawa, 1992, Acute toxicity of trans-4-hydroxy-2-nonenal in Fisher 344 rats [corrected], Lipids, 27, 54, 10.1007/BF02537060 Segall, 1985, Trans-4-hydroxy-2-hexenal: a reactive metabolite from the macrocyclic pyrrolizidine alkaloid senecionine, Science, 229, 472, 10.1126/science.4012327 Wacker, 2001, Detection of 1,N2-propanodeoxyguanosine adducts of trans-4-hydroxy-2-nonenal after gavage of trans-4-hydroxy-2-nonenal or induction of lipid peroxidation with carbon tetrachloride in F344 rats, Chemico-Biological Interactions, 137, 269, 10.1016/S0009-2797(01)00259-9 Kang, 2011, Hepatotoxicity and nephrotoxicity produced by 4-hydroxy-2-nonenal (4-HNE) following 4-week oral administration to Sprague-Dawley rats, Journal of Toxicology and Environmental Health A, 74, 779, 10.1080/15287394.2011.567952 Alary, 1995, Mercapturic acid conjugates as urinary end metabolites of the lipid peroxidation product 4-hydroxy-2-nonenal in the rat, Chemical Research in Toxicology, 8, 34, 10.1021/tx00043a004 Alary, 1998, Identification of novel urinary metabolites of the lipid peroxidation product 4-hydroxy-2-nonenal in rats, Chemical Research in Toxicology, 11, 1368, 10.1021/tx980068g De Zwart, 1996, Disposition in rat of [2–3H]-trans-4-hydroxy-2,3-nonenal, a product of lipid peroxidation, Xenobiotica, 26, 1087, 10.3109/00498259609167424 Winter, 1987, Distribution of trans-4-hydroxy-2-hexenal and tandem mass spectrometric detection of its urinary mercapturic acid in the rat, Drug Metabolism and Disposition, 15, 608 Bravais, 1995, Synthesis of 4-hydroxy[4-3H]-2(E)-nonen-1-al-diethylacetal, Journal of Labelled Compounds and Radiopharmaceuticals, 36, 471 Jouanin, 2008, Synthesis of the lipid peroxidation product 4-hydroxy-2(E)-nonenal with13C stable isotope incorporation, Journal of Labelled Compounds and Radiopharmaceuticals, 51, 87 Baradat, 2011, 4-hydroxy-2(E)-nonenal metabolism differs in Apc(+/+) cells and in Apc(Min/+) cells: it may explain colon cancer promotion by heme iron, Chemical Research in Toxicology, 24, 1984, 10.1021/tx2003036 Jouanin, 2011, Liquid chromatography/electrospray ionisation mass spectrometric tracking of 4-hydroxy-2(E)-nonenal biotransformations by mouse colon epithelial cells using [1,2-13C2]-4-hydroxy-2(E)-nonenal as stable isotope tracer, Rapid Communications in Mass Spectrometry, 25, 2675, 10.1002/rcm.5033 2012 Laurent, 2000, Metabolism of 4-hydroxynonenal, a cytotoxic product of lipid peroxidation, in rat precision-cut liver slices, Toxicology Letters, 114, 203, 10.1016/S0378-4274(99)00301-X Siems, 1997, Metabolic fate of 4-hydroxynonenal in hepatocytes: 1,4-dihydroxynonene is not the main product, Journal of Lipid Research, 38, 612, 10.1016/S0022-2275(20)37269-2 Grune, 1997, Identification of metabolic pathways of the lipid peroxidation product 4-hydroxynonenal in situ perfused rat kidney, Journal of Lipid Research, 38, 1660, 10.1016/S0022-2275(20)37184-4 Jin, 2014, Catabolism of (2E)-4-hydroxy-2-nonenal via ω- and ω-1-Oxidation stimulated by ketogenic diet, Journal of Biological Chemistry, 289, 32327, 10.1074/jbc.M114.602458 Guéraud, 1999, In vivo involvement of cytochrome P450 4A family in the oxidative metabolism of the lipid peroxidation product trans-4-hydroxy-2-nonenal, using PPARalpha-deficient mice, Journal of Lipid Research, 40, 152, 10.1016/S0022-2275(20)33350-2 Aoyama, 1990, Clofibrate-inducible rat hepatic P450s IVA1 and IVA3 catalyze the Omega- and (omega-1)-hydroxylation of fatty acids and the Omega-hydroxylation of prostaglandins E1 and F2 alpha, Journal of Lipid Research, 31, 1477, 10.1016/S0022-2275(20)42618-5 Mulder, 1990 Blachier, 2010, Luminal sulfide and large intestine mucosa: friend or foe?, Amino Acids, 39, 335, 10.1007/s00726-009-0445-2 Schreier, 2010, Hydrogen sulfide scavenges the cytotoxic lipid oxidation product 4-HNE, Neurotoxocity Research, 17, 249, 10.1007/s12640-009-9099-9 Weisiger, 1980, Thiol S-methyltransferase: suggested role in detoxication of intestinal hydrogen sulfide, Biochemical Pharmacology, 29, 2885, 10.1016/0006-2952(80)90029-5 Arias, 1994 Dick, 2001, Antioxidative function and substrate specificity of NAD(P)H-dependent alkenal/one oxidoreductase. A new role for leukotriene B4 12-hydroxydehydrogenase/15-oxoprostaglandin 13-reductase, Journal of Biological Chemistry, 276, 40803, 10.1074/jbc.M105487200 Levsen, 2005, Structure elucidation of phase II metabolites by tandem mass spectrometry: an overview, Journal of Chromatography A, 1067, 55, 10.1016/j.chroma.2004.08.165 Pierre, 2006, New marker of colon cancer risk associated with heme intake: 1,4-dihydroxynonane mercapturic acid, Cancer Epidemiology, Biomarkers and Prevention, 15, 2274, 10.1158/1055-9965.EPI-06-0085 Peiro, 2005, Dihydroxynonene mercapturic acid, a urinary metabolite of 4-hydroxynonenal, as a biomarker of lipid peroxidation, Biofactors (Oxford England), 24, 89, 10.1002/biof.5520240110 Pierre, 2007, Apc mutation induces resistance of colonic cells to lipoperoxide-triggered apoptosis induced by faecal water from haem-fed rats, Carcinogenesis, 28, 321, 10.1093/carcin/bgl127