Abstract
The toxic lipid peroxidation product, α,β,4-hydroxy-2-trans-nonenal (HNE) concentration, was measured in French fries (FF) from six local fast food restaurants. FF were purchased between 2 and 3 pm from all six restaurants. FF were also purchased at 12, 2, 4, 6 pm from one and at 1, 3, 5, 7 pm from another restaurant. Samples were analyzed for total fat, fatty acid distribution and for HNE by high performance liquid chromatography (HPLC). HNE was confirmed by HPLC/MS. HNE concentrations in FF from the 6 fast food restaurants were between 7.83 and 32.15 µg HNE/100 g FF and between 0.9 and 4.9 µg HNE/g extracted fat. HNE concentrations in FF purchased at 12, 2, 4, 6 pm were between 19.07 and 32.15 µg/g of FF and purchased at 1, 3, 5, 7 pm were between 7.47 and 10.21 µg HNE/100 g of FF. Differences in FA distribution were observed in the samples from some restaurants. FF which contained higher levels of linoleic acid (LA) also contained more HNE. It is clear that HNE is produced during the heating process of the frying oils and is incorporated into FF. Frequently consumed foods containing considerable amounts of HNE, a toxic aldehyde, may be a public health concern since HNE toxicity is related to a number of common pathological conditions.
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References
Tappel AL (1977) Protection against free radical lipid per oxidation reactions. Adv Exp Med Biol 97:111–131
Chang SS, Peterson RJ, Ho CT (1978) Chemical reactions involved in the deep-fat frying of foods. J Am Oil Chem Soc 55:718–727
Selke E, Rohwedder WK, Dutton HJ (1980) Volatile components from Trilinolein heated in air. J Am Oil Chem Soc 57:25–30
Frankel EN (1987) Secondary products of lipid oxidation. Chem Phys Lipids 44:73–85
Grosch W (1989) Compounds formed by peroxidation of lipids. Fat Sci Technol 91:1–6
Frankel EN (1998) Frying fats. In: Frankel EN (ed) Lipid oxidation. Oily Press, Dundee, pp 227–248
Choe E, Min David B (2006) Mechanisms and factors for edible oil oxidation. Comprehensive reviews in food science and food safety. Inst Food Technol 5:169–185
German JB (1999) Food processing and lipid oxidation. Adv Exp Med Biol 459:23–50
Kanner J (2007) Dietary advanced lipid oxidation end products are risk factors to human health. Mol Nutr Food Res 51:1094–1101
Esterbauer H, Zollner H, Schaur RJ (1988) Hydroxyalkenals: cytotoxic products of lipid peroxidation. ISI Atlas Sci Biochem 1:311–317
Witz G (1989) Biological interactions of α,β-unsaturated aldehydes. Free Rad Biol Med 7:333–349
Esterbauer H (1993) Cytotoxicity and genotoxicity of lipid oxidation products. Am J Clin Nutr 57:779S–786S
Oarada M, Miyazawa T, Fujimoto K, Ito E, Terao K, Kaneda T (1988) Degeneration of lymphoid tissues in mice with the oral intake of low molecular weight compounds formed during oil autooxidation. Agr Biol Chem 52:2101–2102
Witz G (1989) Biological interactions of α,β-unsaturated aldehydes. Free Rad Biol Med 7:333–349
Uchida K (2003) 4-hydroxy-2-nonenal: a product and mediator of oxidative stress. Prog Lipid Res 42:318–343
Esterbauer H, Schaur RJ, Zollner H (1991) Chemistry and biochemistry of 4-hydroxynonenal, malonaldehyde and related aldehydes. Free Rad Biol Med 11:81–128
Han IH, Csallany AS (2009) Formation of toxic α,β-unsaturated 4-hydroxy-aldehydes in thermally oxidized fatty acid methyl esters. J Am Oil Chem Soc 86:253–260
Grootveld M, Atherton MD, Sheerin AN, Hawkes J, Blake D, Richens TE, Silwood CJL, Lynch E, Claxson AWD (1998) In vivo absorption, metabolism and urinary excretion of α,β-unsaturated aldehydes in experimental animals. Relevance to the development of cardiovascular diseases by the dietary ingestion of thermally stressed polyunsaturated-rich culinary oils. J Clin Invest 101:1210–1218
Kritchevsky D (1991) Dietary fat and experimental atherosclerosis. Int J Tissue React 13:59–65
Parola M, Robino G (2001) Oxidative stress-related molecules and liver fibrosis. J Hepat 35:297–306
Owen AD, Schapira HA, Jenner P, Marsden CD (1997) Indices of oxidative stress in Parkinson’s disease, Alzheimer’s disease and dementia with Lewy bodies. J Neural Trans Suppl 51:167–173
Kruman I, Bruce-Keller AJ, Bredesen D, Waeg G, Mattson MP (1997) Evidence that 4-hydroxynonenal mediates oxidative stress induced neuronal apoptosis. J Neurosci 13:5089–5100
Keller JN, Mark RJ, Bruce AJ, Blane E, Rothstein JD, Uchida K, Mattson MP (1997) 4-hydroxynonenal, an aldehydic product of membrane lipid peroxidation, impairs glutamate transport and mitochondrial function in synaptosomes. Neuroscience 80:685–686
Subramanian R, Roediger F, Jordan B, Mattson MP, Keller GW, Butterfield DA (1997) The lipid peroxidation product, 4-hydroxy-2-trans-nonenal, alters the conformation of cortical synaptosomal membrane proteins. J Neurochem 69:1161–1169
Mark RJ, Lovell MA, Markebery WR, Uchida K, Mattson MP (1997) A role for 4-hydroxynonenal, an aldehydic product of lipid peroxidation in disruption of ion homeostasis and neuronal death induced by amyloid beta-peptide. J Neurochem 68:255–264
Mattson MP (1997) Central role of oxyradicals in the metabolism of amyloid beta-peptide cytotoxicity. Alzheimer’s Dis Rev 2:1–14
Hussain SP, Hofseth LS, Harris CC (2003) Radical causes of cancer. Nat Rev Cancer 3:276–285
Kaneda T, Miyazawa T (1987) Lipid peroxides and nutrition. World Rev Nutr Diet 50:186–214
Billek G (2000) Health aspects of thermoxidized oils and fats. Eur J Lipid Sci Technol 102:587–593
Seppanen CM, Csallany AS (2001) Simultaneous determination of lipophilic aldehydes by high-performance liquid chromatography in vegetable oil. J Am Oil Chem Soc 78:1253–1260
Seppanen CM, Csallany AS (2002) Formation of 4-hydroxynonenal, a toxic aldehyde, in soybean oil at frying temperature. Ibid 79:1033–1038
Seppanen CM, Csallany AS (2004) Incorporation of the toxic aldehyde 4-hydroxy-2-trans-nonenal into food fried in thermally oxidized soybean oil. J Am Oil Chem Soc 81:1137–1141
Yao D, Shi X, Li Wang, Gosnell BA, Chan C (2013) Characterization of differential cocaine metabolism in mouse and rat through metabolomics-guided metabolite profiling. Drug Metab and Disposition 41:79–88
Metcalf LD, Schmitz AA (1961) The rapid preparation of fatty acid esters for gas chromatographic analysis. Anal Chem 33:363–364
Guillen MD, Goicoechea E (2008) Toxic oxygenated α,β unsaturated aldehydes and their study in foods: a review. Crit Rev Food Sci Nutr 48:119–136
Scott-Miller M, Neuhouser ML, Stanford JL (2013) Consumption of deep-fried foods and risk of prostate cancer. Prostrate 73:960–963
Bonet B (2007) Clastogenic and cytotoxic effects of lipid peroxidation products generated in culinary oils submitted to thermal stress. Food Chem Toxicol 45:1963–1967
Nishikawa A, Sodum R, Chung FL (1992) Acute toxicity of trans-4-hydroxy-2-nonenal in Fisher 344 rats (corrected). Lipids 27(1):54–58
Wacker M, Wanek P, Eder E (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. Chem Biol Interact 137(3):269–283
Kang SC, Kim H-W, Kim KB, Kwack SJ, Ahn IY, Bae JY et al. (2011) Hepatoxicity and nephrotoxicity produced by 4-hydroxy-2-nonenal (4-HNE) following 4-week oral administration to Sprague-Dawley rats. J Toxicol Environ Health A 74(12):779–789
Keller Julia, Baradat Maryse, Jouanin Isabelle, Debrauwer Laurent (2015) “Twin Peaks”: searching for 4-hydroxynonenal urinary metabolites after oral administration in rats. Redox Biol 4:136–148
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This research was partly supported by the University of Minnesota, Agricultural Experiment Station.
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Csallany, A.S., Han, I., Shoeman, D.W. et al. 4-Hydroxynonenal (HNE), a Toxic Aldehyde in French Fries from Fast Food Restaurants. J Am Oil Chem Soc 92, 1413–1419 (2015). https://doi.org/10.1007/s11746-015-2699-z
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DOI: https://doi.org/10.1007/s11746-015-2699-z