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Gas Chromatography of Volatile Lipid Oxidation Products

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References

  • Andreoli R, Manini P, Corradi M, Mutti A, Niessen WM. Determination of patterns of biologically relevant aldehydes in exhaled breath condensate of healthy subjects by liquid chromatography/atmospheric chemical ionization tandem mass spectrometry. Rapid Commun Mass Spectrom. 2003;17:637–45.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Allan J. St. Angelo. Lipid oxidation in food. Critical Reviews in Food Science in Nutrition 1996;36:175–224.

    Google Scholar 

  • Bacot S, Bernoud-Hubac N, Baddas N, Chantegrel B, Deshayes C, Doutheau A, Lagarde M, Guichardant M. Covalent binding of hydroxy-alkenals 4-HDDE, 4-HHE, and 4-HNE to ethanolamine phospholipid subclasses. J Lipid Res. 2003;44:917–26.

    Article  CAS  PubMed  Google Scholar 

  • Bacot S, Bernoud-Hubac N, Chantegrel B, Deshayes C, Doutheau A, Ponsin G, Lagarde M, Guichardant M. Evidence for in situ ethanolamine phospholipid adducts with hydroxy-alkenals. J Lipid Res. 2007;48:816–25.

    Article  CAS  PubMed  Google Scholar 

  • Barrera G, Gentile F, Pizzimenti S, Canuto RA, Daga M, Arcaro A, Cetrangolo GP, Lepore A, Ferretti C, Dianzani C, Muzio G. Mitochondrial dysfunction in cancer and neurodegenerative diseases: spotlight on fatty acid oxidation and lipoperoxidation products. Antioxidants. 2016;5:1. Review.

    Article  Google Scholar 

  • Benedetti A, Comporti M, Fulceri R, Esterbauer H. Cytotoxic aldehydes originating from the peroxidation of liver microsomal lipids: identification of 4,5-dihydroxydecenal. Biochim Biophys Acta, Lipids Lipid Metab. 1984;9:172–81.

    Article  Google Scholar 

  • Calzada C, Colas R, Guillot N, Guichardant M, Laville M, Véricel E, Lagarde M. Subgram daily supplementation with docosahexaenoic acid protects low-density lipoproteins from oxidation in healthy men. Atherosclerosis. 2010;208:467–72.

    Article  CAS  PubMed  Google Scholar 

  • Castegna A, Lauderback CM, Mohmmad-Abdul H, Butterfield DA. Modulation of phospholipid asymmetry in synaptosomal membranes by the lipid peroxidation products, 4-hydroxynonenal and acrolein: implications for Alzheimer’s disease. Brain Res. 2004;1004:193–7.

    Article  CAS  PubMed  Google Scholar 

  • Cheng H. Volatile flavor compounds in yogurt: a review. Crit Rev Food Sci Nutr. 2010;50:938–50. Review.

    Article  CAS  PubMed  Google Scholar 

  • Chung F-L, Nath RG, Ocando J, Nishikawa A, Zhang L. Deoxyguanosine adducts of t-4-hydroxy-2-nonenal are endogenous DNA lesions in rodents and humans: detection and potential sources. Cancer Res. 1984;44:990–5.

    CAS  PubMed  Google Scholar 

  • Cohen G, Riahi Y, Shamni O, Guichardant M, Chatgilialoglu C, Ferreri C, Kaiser N, Sasson S. Role of lipid peroxidation and PPAR-δ in amplifying glucose-stimulated insulin secretion. Diabetes. 2011;60:2830–42.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Coulon L, Calzada C, Moulin P, Vericel E, Lagarde M. Activation of p38 mitogen-activated protein kinase/cytosolic phospholipase A2 cascade in hydroperoxide-stressed platelets. Free Radic Biol Med. 2003;35:616–25.

    Article  CAS  PubMed  Google Scholar 

  • Csala M, Kardon T, Legeza B, Lizák B, Mandl J, Margittai É, Puskás F, Száraz P, Szelényi P, Bánhegyi G. On the role of 4-hydroxynonenal in health and disease. Biochim Biophys Acta. 1852;2015:826–38. Review.

    Google Scholar 

  • Domingues RM, Domingues P, Melo T, Pérez-Sala D, Reis A, Spickett CM. Lipoxidation adducts with peptides and proteins: deleterious modifications or signaling mechanisms? J Proteomics. 2013;92:110–31. Review.

    Article  CAS  PubMed  Google Scholar 

  • Esterbauer H, Schaur RJ, Zollner H. Chemistry and biochemistry of 4-hydroxynonenal, malonaldehyde and related aldehydes. Free Radic Biol Med. 1991;11:81–128. Review.

    Article  CAS  PubMed  Google Scholar 

  • Ferderbar S, Pereira EC, Apolinário E, Bertolami MC, Faludi A, Monte O, Calliari LE, Sales JE, Gagliardi AR, Xavier HT, Abdalla DS. Cholesterol oxides as biomarkers of oxidative stress in type 1 and type 2 diabetes mellitus. Diabetes Metab Res Rev. 2007;23:35–42.

    Article  CAS  PubMed  Google Scholar 

  • Frankel EN. Lipid oxidation. Prog Lipid Res. 1980;19:1–2.

    Article  CAS  PubMed  Google Scholar 

  • Frankel EN. Volatile lipid oxidation products. Prog Lipid Res. 1982;22:1–3.

    Article  Google Scholar 

  • Frankel EN. Chemistry of free radical and singlet oxidation of lipids. Prog Lipid Res. 1984;23:197–221.

    Article  CAS  PubMed  Google Scholar 

  • Frankel EN. Secondary products of lipid oxidation. Chem Phys Lipids. 1987;44:2–4.

    Article  Google Scholar 

  • Fukuda M, Kanou F, Shimada N, Sawabe M, Saito Y, Murayama S, Hashimoto M, Maruyama N, Ishigami A. Elevated levels of 4-hydroxynonenal-histidine Michael adduct in the hippocampi of patients with Alzheimer’s disease. Biomed Res. 2009;30:227–33.

    Article  CAS  PubMed  Google Scholar 

  • Galasko DR, Peskind E, Clark CM, Quinn JF, Ringman JM, Jicha GA, Cotman C, Cottrell B, Montine TJ, Thomas RG, et al. Alzheimer’s disease cooperative study. Antioxidants for Alzheimer disease: a randomized clinical trial with cerebrospinal fluid biomarker measures. Arch Neurol. 2012;69:836–41.

    Article  PubMed  PubMed Central  Google Scholar 

  • Grasse LD, Lamé MW, Segall HJ. In vivo covalent binding of trans-4-hydroxy-2-hexenal to rat liver macromolecules. Toxicol Lett. 1985;29:43–9.

    Article  CAS  PubMed  Google Scholar 

  • Guichardant M, Taibi-Tronche P, Fay LB, Lagarde M. Covalent modifications of aminophospholipids by 4-hydroxynonenal. Free Radic Biol Med. 1998;25:1049–56.

    Article  CAS  PubMed  Google Scholar 

  • Guichardant M, Chantegrel B, Deshayes C, Doutheau A, Moliere P, Lagarde M. Specific markers of lipid peroxidation issued from n-3 and n-6 fatty acids. Biochem Soc Trans. 2004;32:139–40.

    Article  CAS  PubMed  Google Scholar 

  • Guichardant M, Bacot S, Molière P, Lagarde M. Hydroxy-alkenals from the peroxidation of n-3 and n-6 fatty acids and urinary metabolites. Prostaglandins Leukot Essent Fatty Acids. 2006;75:179–82. Review.

    Article  CAS  PubMed  Google Scholar 

  • Henderson AP, Bleasdale C, Delaney K, Lindstrom AB, Rappaport SM, Waidyanatha S, Watson WP, Golding BT. Evidence for the formation of Michael adducts from reactions of (E, E)-muconaldehyde with glutathione and other thiols. Bioorg Chem. 2005;33:363–73.

    Article  CAS  PubMed  Google Scholar 

  • Hoff HF, O’Neil J, Chisolm GM, Cole TB, Quehenberger O, Esterbauer H, Jurgens G. Modification of low density lipoprotein with 4-hydroxynonenal induces uptake by macrophages. Arteriosclerosis. 2009;9:538–49.

    Article  Google Scholar 

  • Honzatko A, Brichac J, Picklo MJ. Quantification of trans-4-hydroxy-2-nonenal enantiomers and metabolites by LC-ESI-MS/MS. J Chromatogr B Analyt Technol Biomed Life Sci. 2007;857:115–22.

    Article  CAS  PubMed  Google Scholar 

  • Hugo A, Souza L, Bragagnolo N. New method for the extraction of volatile lipid oxidation products from shrimp by headspace–solid-phase micro-extraction–gas chromatography–mass spectrometry and evaluation of the effect of salting and drying. J Agric Food Chem. 2014;62:590–9.

    Article  Google Scholar 

  • Ibrahim S, Guillot N, Pruneta-Deloche V, Charrière S, Calzada C, Guichardant M, Moulin P, Lagarde M, Ponsin G. Alterations in the transfer of phospholipids from very-low density lipoproteins to activated platelets in type 2 diabetes. Atherosclerosis. 2009;203:19–25.

    Article  Google Scholar 

  • Jayasena DD, Ahn DU, Nam KC, Jo C. Flavour chemistry of chicken meat: a review. Asian-Australas J Anim Sci. 2013;26:732–42.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Jeffrey BG, Weisinger HS, Neuringer M, Mitchell DC. The role of docosahexaenoic acid in retinal function. Lipids. 2001;36:859–71.

    Article  CAS  PubMed  Google Scholar 

  • Li D, Ellis EM. 4-Hydroxynonenal induces an increase in expression of receptor 1 for activating C kinase 1 (RACK1) in Chinese hamster V79-4 lung cells. Chem Biol Interact. 2014;213:13–20.

    Article  CAS  PubMed  Google Scholar 

  • Liu YM, Jinno H, Kurihara M, Miyata N, Toyo’oka T. Determination of 4-hydroxy-2-nonenal in primary rat hepatocyte cultures by liquid chromatography with laser induced fluorescence detection. Biomed Chromatogr. 1999;13:75–80.

    Article  CAS  PubMed  Google Scholar 

  • Long EK, Murphy TC, Leiphon LJ, Watt J, Morrow JD, Milne GL, Howard JR, Picklo Sr MJ. Trans-4-hydroxy-2-hexenal is a neurotoxic product of docosahexaenoic (22:6; n-3) acid oxidation. J Neurochem. 2008;105:714–24.

    Article  CAS  PubMed  Google Scholar 

  • Luo XP, Yazdanpanah M, Bhooi N, Lehotay DC. Determination of aldehydes and other lipid peroxidation products in biological samples by gas chromatography–mass spectrometry. Anal Biochem. 1995;228:294–8.

    Article  CAS  PubMed  Google Scholar 

  • Michalski MC, Calzada C, Makino A, Michaud S, Guichardant M. Oxidation products of polyunsaturated fatty acids in infant formulas compared to human milk-a preliminary study. Mol Nutr Food Res. 2008;52:1478–85.

    Article  CAS  PubMed  Google Scholar 

  • O’Brien-Coker IC, Perkins G, Mallet AI. Aldehyde analysis by high performance liquid chromatography/tandem mass spectrometry. Rapid Commun Mass Spectrom. 2001;15:920–8.

    Article  PubMed  Google Scholar 

  • Orioli M, Aldini G, Beretta G, Facino RM, Carini M. LC-ESI-MS/MS determination of 4-hydroxy-trans-2-nonenal Michael adducts with cysteine and histidine-containing peptides as early markers of oxidative stress in excitable tissues. J Chromatogr B Analyt Technol Biomed Life Sci. 2005;827:109–18.

    Article  CAS  PubMed  Google Scholar 

  • Portier K, Guichardant M, Debouzy JC, Crouzier D, Geraud I, Kirschvink N, Lekeux P, Fellmann N, Coudert J. In vitro effects of oxygen on physico-chemical properties of horse erythrocyte membrane. Environ Toxicol Pharmacol. 2007;23:340–6.

    Article  CAS  PubMed  Google Scholar 

  • Portier K, Crouzier D, Guichardant M, Prost M, Debouzy JC, Kirschvink N, Fellmann N, Lekeux P, Coudert J. Effects of high and low inspired fractions of oxygen on horse erythrocyte membrane properties, blood viscosity and muscle oxygenation during anaesthesia. Vet Anaesth Analg. 2009;36:287–98.

    Article  PubMed  Google Scholar 

  • Pryor WA, Porter NA. Suggested mechanisms for the production of 4-hydroxy-2-nonenal from the autoxidation of polyunsaturated fatty acids. Free Radic Biol Med. 1990;8:541–3. Review.

    Article  CAS  PubMed  Google Scholar 

  • Riahi Y, Cohen G, Shamni O, Sasson S. Signaling and cytotoxic functions of 4-hydroxyalkenals. Am J Physiol Endocrinol Metab. 2010a;299:E879–86.

    Article  CAS  PubMed  Google Scholar 

  • Riahi Y, Sin-Malia Y, Cohen G, Alpert E, Gruzman A, Eckel J, Staels B, Guichardant M, Sasson S. The natural protective mechanism against hyperglycemia in vascular endothelial cells: roles of the lipid peroxidation product 4-hydroxydodecadienal and peroxisome proliferator-activated receptor delta. Diabetes. 2010b;59:808–18.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Rosenfeld ME, Palinski W, Yla-Herttuala S, Butler S, Witztum JL. Oxidized low-density lipoprotein in experimental focal glomerulosclerosis. Arteriosclerosis. 1990;10:336–49.

    Article  CAS  PubMed  Google Scholar 

  • Salomon RG, Kaur K, Podrez E, Hoff HF, Krushinsky AV, Sayre LM. HNE-derived 2-pentylpyrroles are generated during oxidation of LDL, are more prevalent in blood plasma from patients with renal disease or atherosclerosis, and are present in atherosclerotic plaques. Chem Res Toxicol. 2000;13:557–64.

    Article  CAS  PubMed  Google Scholar 

  • Sayre LM, Arora PK, Iyer RS, Salomon RG. Pyrrole formation from 4-hydroxynonenal and primary amines. Chem Res Toxicol. 1993;6:19–22.

    Article  CAS  PubMed  Google Scholar 

  • Siegel SJ, Bieschke J, Powers ET, Kelly JW. The oxidative stress metabolite 4-hydroxynonenal promotes Alzheimer protofibril formation. Biochemistry. 2007;46:1503–10.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Siems WG, Hapner SJ, van Kuijk FJ. 4-hydroxynonenal inhibits Na(+)-K(+)-ATPase. Free Radic Biol Med. 1996;20:215–23.

    Article  CAS  PubMed  Google Scholar 

  • Soares AF, Guichardant M, Cozzone D, Bernoud-Hubac N, Bouzaïdi-Tiali N, Lagarde M, Géloën A. Effects of oxidative stress on adiponectin secretion and lactate production in 3 T3-L1 adipocytes. Free Radic Biol Med. 2005;38:882–9.

    Article  CAS  PubMed  Google Scholar 

  • Sultana R, Perluigi M, Butterfield DA. Lipid peroxidation triggers neurodegeneration: a redox proteomics view into the Alzheimer disease brain. Free Radic Biol Med. 2013;62:157–69.

    Article  CAS  PubMed  Google Scholar 

  • Szweda LI, Uchida K, Tsai L, Stadtman ER. Inactivation of glucose-6-phosphate dehydrogenase by 4-hydroxy-2-nonenal. Selective modification of an active-site lysine. J Biol Chem. 1993;268:3342–7.

    CAS  PubMed  Google Scholar 

  • Tsuchiya Y, Okada G, Kobayashi S, Chikuma T, Hojo H. 4-hydroxy-2-nonenal-modified glyceraldehyde-3-phosphate dehydrogenase is degraded by cathepsin G in rat neutrophils. Oxid Med Cell Longev. 2011;2011:213686.

    Article  PubMed  PubMed Central  Google Scholar 

  • Uchida K. Role of reactive aldehyde in cardiovascular diseases. Free Radic Biol Med. 2000;28:1685–96.

    Article  CAS  PubMed  Google Scholar 

  • Uchida K, Stadtmant ER. Covalent attachment of 4-hydroxynonenal to glyceraldehyde-3-phosphate dehydrogenase. A possible involvement of intra- and intermolecular cross-linking reaction. J Biol Chem. 1993;268:6388–93.

    CAS  PubMed  Google Scholar 

  • Uchida K, Hasui Y, Osawa T. Covalent attachment of 4-hydroxy-2-nonenal to erythrocyte proteins. J Biochem. 1997;122:1246–51.

    Article  CAS  PubMed  Google Scholar 

  • Vander Jagt DL, Hunsaker LA, Vander Jagt TJ, Gomez MS, Gonzales DM, Deck LM, Royer RE. Inactivation of glutathione reductase by 4-hydroxynonenal and other endogenous aldehydes. Biochem Pharmacol. 1997;53:1133–40.

    Article  CAS  PubMed  Google Scholar 

  • Vankuijk FJGM, Siakotos AN, Fong LG, Stephens RJ, Thomas DW. Quantitative measurement of 4-hydroxyalkenals in oxidized low-density lipoprotein by gas chromatography–mass spectrometry. Anal Biochem. 1995;224:420–4.

    Article  CAS  Google Scholar 

  • Vella RE, Pillon NJ, Zarrouki B, Croze ML, Koppe L, Guichardant M, Pesenti S, Chauvin MA, Rieusset J, Géloën A, Soulage CO. Ozone exposure triggers insulin resistance through muscle c-Jun N-terminal kinase activation. Diabetes. 2015;64:1011–24.

    Article  CAS  PubMed  Google Scholar 

  • Völkel W, Sicilia T, Pähler A, Gsell W, Tatschner T, Jellinger k, Leblhuber F, Riederer P, Lutz WK, Götz ME. Increased brain levels of 4-hydroxy-2-nonenal glutathione conjugates in severe Alzheimer’s disease. Neurochem Int. 2006;48:679–86.

    Article  PubMed  Google Scholar 

  • Warnke MM, Wanigasekara E, Singhal SS, Singhal J, Awasthi S, Armstrong DW. The determination of glutathione-4-hydroxynonenal (GSHNE), E-4-hydroxynonenal (HNE), and E-1-hydroxynon-2-en-4-one (HNO) in mouse liver tissue by LC-ESI-MS. Anal Bioanal Chem. 2008;392:1325–33.

    Article  CAS  PubMed  Google Scholar 

  • Wilkes JG, Conte ED, Kim Y, Holcomb M, Sutherland JB, Miller DW. Sample preparation for the analysis of flavors and off-flavors in foods. J Chromatogr A. 2000;880:3–33. Review.

    Article  CAS  PubMed  Google Scholar 

  • Williams TI, Lovell MA, Lynn BC. Analysis of derivatized biogenic aldehydes by LC tandem mass spectrometry. Anal Chem. 2005;77:3383–9.

    Article  CAS  PubMed  Google Scholar 

  • Winter CK, Segall HJ, Haddon WF. Formation of cyclic adducts of deoxyguanosine with the aldehydes trans-4-hydroxy-2-hexenal and trans-4-hydroxy-2-nonenal in vitro. Cancer Res. 1986;46:5682–6.

    CAS  PubMed  Google Scholar 

  • Zarrouki B, Soares AF, Guichardant M, Lagarde M, Géloën A. The lipid peroxidation end-product 4-HNE induces COX-2 expression through p38MAPK activation in 3 T3-L1 adipose cell. FEBS Lett. 2007;581:2394–400.

    Article  CAS  PubMed  Google Scholar 

  • Zheng R, Dragomir AC, Mishin V, Richardson JR, Heck DE, Laskin DL, Laskin JD. Differential metabolism of 4-hydroxynonenal in liver, lung and brain of mice and rats. Toxicol Appl Pharmacol. 2014;279:43–52.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

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Authors and Affiliations

  1. Inserm UMR 1060, Inra UMR 1397, IMBL, INSA-Lyon, Université de Lyon, F-69621, Villeurbanne, Lyon, France

    Michel Guichardant, Nathalie Bernoud Hubac, Baptiste Fourmaux, Madeleine Picq, Patrick Molière & Michel Lagarde

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  1. Michel Guichardant
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  2. Nathalie Bernoud Hubac
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  3. Baptiste Fourmaux
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  4. Madeleine Picq
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  5. Patrick Molière
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  6. Michel Lagarde
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Correspondence to Michel Guichardant .

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Editors and Affiliations

  1. Yong Loo Lin School of Medicine Centre for Life Sciences, Singapore, Singapore

    Markus R. Wenk

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Guichardant, M., Hubac, N.B., Fourmaux, B., Picq, M., Molière, P., Lagarde, M. (2016). Gas Chromatography of Volatile Lipid Oxidation Products. In: Wenk, M. (eds) Encyclopedia of Lipidomics. Springer, Dordrecht. https://doi.org/10.1007/978-94-007-7864-1_69-1

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