Czech J. Food Sci., 2017, 35(5):367-375 | DOI: 10.17221/405/2016-CJFS
Contribution of linoleic acid to the formation of advanced glycation end products in model systems during heat treatmentFood Chemistry and Safety
- 1 College of Food Science, Shenyang Agricultural University, Shenyang, P.R. China
- 2 Beijing Ensoul Technology Ltd., Beijing, P.R. China
Advanced glycation end products (AGEs) are glycosylated metabolic products generated in vivo and are associated with aging-related diseases. They are also formed during heat treatment in food processing. In this work, we investigated the contribution of linoleic acid (LA) to AGE formation using a protein/glucose model. An electronic tongue, denaturing polyacrylamide gel electrophoresis, electron spin resonance spectroscopy, circular dichroism, and ultraperformance liquid chromatography-tandem mass spectrometry were used to analyse reaction intermediates and reactive radical formation. The results show that LA is the key factor responsible for the change in flavour including the rapid triggering of glycation reactions. The amount of lipid-induced reactive radicals was significantly higher than in the non-fat system, radical generation in the non-fat system was gradually quenched after a robust radical-yielding reaction in the first 25 minutes. Subsequent unsaturated lipid oxidation, and AGE accumulation surpass Maillard reaction-only outcomes. Initial LA-induced changes in protein structure are followed by glycation and are enhanced by hydrophobic interactions and increased carbonyl levels resulting from lipid oxidation. These findings implicate lipids and lipid oxidation as the main factors responsible for AGE formation during the processing of fat-rich unsaturated fatty acid-containing foods.
Keywords: glycation; linoleic acid; radical formation; flavour
Published: October 31, 2017 Show citation
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References
- Ahmad M.S., Pischetsrieder M., Ahmed N. (2007): Aged garlic extract and S-allyl cysteine prevent formation of Time (h) advanced glycation endproducts. European Journal of Pharmacology, 561: 32-38.
Go to original source...
Go to PubMed... - Assar S.H., Moloney C., Lima M., Magee R., Ames J.M. (2009): Determination of N ε-(carboxymethyl)lysine in food systems by ultra performance liquid chromatography-mass spectrometry. Amino Acids, 36: 317-326.
Go to original source...
Go to PubMed... - Baskaran R., Ravi R., Rajarathnam S. (2015): Thermal processing alters the chemical quality and sensory characteristics of sweetsop (Annona squamosa L.) and soursop (Annona muricata L.) pulp and nectar. Journal of Food Science, 81: S182-S188.
Go to original source...
Go to PubMed... - Campbell L., Euston S.R., Ahmed M.A. (2016): Effect of addition of thermally modified cowpea protein on sensory acceptability and textural properties of wheat bread and sponge cake. Food Chemistry, 194: 1230-1237.
Go to original source...
Go to PubMed... - Delatour T., Hegele J., Parisod V., Richoz J., Maurer S., Steven M., Buetler T. (2009): Analysis of advanced glycation endproducts in dairy products by isotope dilution liquid chromatography-electrospray tandem mass spectrometry. The particular case of carboxymethyllysine. Journal of Chromatography A, 1216: 2371-2381.
Go to original source...
Go to PubMed... - Han L., Li L., Li B., Zhao D., Li Y., Xu Z., Liu G. (2013): Glyoxal derived from triglyceride participating in dietderived N ε-carboxymethyllysine formation. Food Research International, 51: 836-840.
Go to original source... - Hedegaard R.V., Liu L., Skibsted L.H. (2015): Quantification of radicals formed during heating of β-lactoglobulin with glucose in aqueous ethanol. Food Chemistry, 167: 185-190.
Go to original source...
Go to PubMed... - Hull G.L.J., Woodside J.V., Ames J.M., Cuskelly G.J. (2012): N ε-(carboxymethyl)lysine content of foods commonly consumed in a Western style diet. Food Chemistry, 131: 170-174.
Go to original source... - Hutapea E.B., Parkanyová L., Parkanyová J., Miyahara M., Sakurai H., Pokorný J. (2004): Browning reactions between oxidised vegetable oils and amino acids. Czech Journal of Food Sciences, 22: 99-107.
Go to original source... - Ifeduba E.A., Akoh C.C. (2015): Microencapsulation of stearidonic acid soybean oil in complex coacervates modified for enhanced stability. Food Hydrocolloids, 51: 136-145.
Go to original source... - Kobue-Lekalake R.I. (2009): Sensory perception of bitterness and astringency in sorghum. [Doctoral thesis]. University of Pretoria, Pretoria, South Africa.
- Liu X., Liu Y.Y., Guo J., Yin S.W., Yang X.Q. (2017): Microfluidization initiated cross-linking of gliadin particles for structured algal oil emulsions. Food Hydrocolloids, 73: 153-161.
Go to original source... - Lokuruka M.N.I. (2011): Effects of processing on soybean nutrients and potential impact on consumer health: an overview. African Journal of Food, Agriculture, Nutrition and Development, 11: 5000-5017.
Go to original source... - Lu F.S.H., Nielsen N.S., Baron C.P., Jacobsen C. (2012): Oxidative degradation and non-enzymatic browning due to the interaction between oxidised lipids and primary amine groups in different marine PL emulsions. Food Chemistry, 135: 2887-2896.
Go to original source...
Go to PubMed... - Matiacevich S.B., Santagapita P.R., Pilar B.M. (2005): Fluorescence from the Maillard reaction and its potential applications in food science. Critical Reviews in Food Science and Nutrition, 45: 483-495.
Go to original source...
Go to PubMed... - Militello V., Casarino C., Emanuele A., Giostra A., Pullara F., Leone M. (2004): Aggregation kinetics of bovine serum albumin studied by FTIR spectroscopy and light scattering. Biophysical Chemistry, 107: 175-187.
Go to original source...
Go to PubMed... - Miyata T., Maehda K., Kurokawa K., Strihou C.V.Y.D. (1997): Oxidation conspires with glycation to generate noxious advanced glycation end-products in renal failure. Nephrology Dialysis Transplantation, 12: 255-258.
Go to original source...
Go to PubMed... - Morales F.J., Jiménez-Pérez S. (2001): Free radical scavenging capacity of Maillard reaction products as related to colour and fluorescence. Food Chemistry, 72: 119-125.
Go to original source... - Navarra G., Giacomazza D., Leone M., Librizzi F., Militello V., Biagio P.L.S. (2009): Thermal aggregation and ioninduced cold-gelation of bovine serum albumin. Biophysics of Structure & Mechanism, 38: 437-446.
Go to original source...
Go to PubMed... - Niquet-Léridon C., Tessier F.J. (2011): Quantification of Nε-carboxymethyl-lysine in selected chocolate-flavoured drink mixes using high-performance liquid chromatography-linear ion trap tandem mass spectrometry. Food Chemistry, 126: 655-663.
Go to original source... - Poulsen M.W., Hedegaard R.V., Andersen J.M., Courten B.D., Bügel S., Nielsen J., Skibsted L.H., Dragsted L.O. (2013): Advanced glycation endproducts in food and their effects on health. Food & Chemical Toxicology, 60: 10-37.
Go to original source...
Go to PubMed... - Raithore S., Bai J., Plotto A., Manthey J., Irey M., Baldwin E. (2015): Electronic tongue response to chemicals in orange juice that change concentration in relation to harvest maturity and citrus greening or huanglongbing (HLB) disease. Sensors, 15: 30062-30075.
Go to original source...
Go to PubMed... - Refsgaard H.H., Tsai L., Stadtman E.R. (2000): Modifications of proteins by polyunsaturated fatty acid peroxidation products. Proceedings of the National Academy of Sciences of the United State of America, 97: 611-616.
Go to original source...
Go to PubMed... - Renzone G., Arena S., Scaloni A. (2015): Proteomic characterization of intermediate and advanced glycation end-products in commercial milk samples. Journal of Proteomics, 117: 12-23.
Go to original source...
Go to PubMed... - Rondeau P., Navarra G., Cacciabaudo F., Leone M., Bourdon E., Militello V. (2010): Thermal aggregation of glycated bovine serum albumin. Biochimica et Biophysica Acta Proteins & Proteomics, 1804: 789-798.
Go to original source...
Go to PubMed... - Saeed S., Gillies D., Wagner G., Howell N.K. (2006): ESR and NMR spectroscopy studies on protein oxidation and formation of dityrosine in emulsions containing oxidised methyl linoleate. Food & Chemical Toxicology, 44: 1385-1392.
Go to original source...
Go to PubMed... - Shi F., Bai B., Ma S., Ji S., Liu L. (2015): The inhibitory effects of γ-glutamylcysteine derivatives from fresh garlic on glycation radical formation. Food Chemistry, 194: 538-544.
Go to original source...
Go to PubMed... - Skrt M., Benedik E., Podlipnik C., Ulrih N.P. (2011): Interactions of different polyphenols with bovine serum albumin using fluorescence quenching and molecular docking. Food Chemistry, 135: 2418-2424.
Go to original source...
Go to PubMed... - Spada J.C., Marczak L.D.F., Tessaro I.C., Cardozo N.S.M. (2015): Interactions between soy protein from watersoluble soy extract and polysaccharides in solutions with polydextrose. Carbohydrate Polymers, 134: 119-127.
Go to original source...
Go to PubMed... - Sun Q., Luo Y. (2011): Effect of Maillard reaction conditions on radical scavenging activity of porcine haemoglobin hydrolysate-sugar model system. International Journal of Food Science & Technology, 46: 358-364.
Go to original source... - Troise A.D., Fiore A., Wiltafsky M., Fogliano V. (2015): Quantification of Nε-(2-furoylmethyl)-l-lysine (furosine), Nε-(carboxymethyl)-l-lysine (CML), Nε-(carboxyethyl)l-lysine (CEL) and total lysine through stable isotope dilution assay and tandem mass spectrometry. Food Chemistry, 188: 357-364.
Go to original source...
Go to PubMed... - Udilova N., Jurek D., Marian B., Gille L., Schulte-Hermann R., Nohl H. (2003): Induction of lipid peroxidation in biomembranes by dietary oil components. Food & Chemical Toxicology, 41: 1481-1489.
Go to original source...
Go to PubMed... - Vistoli G., Maddis D.D., Cipak A., Zarkovic N., Carini M., Aldini G. (2013): Advanced glycoxidation and lipoxidation end products (AGEs and ALEs): an overview of their mechanisms of formation. Free Radical Research, 47 (S1): 3-27.
Go to original source...
Go to PubMed... - Wadehra A. (2016): Application of electronic tongues in food processing. Analytical Methods, 8: 474-480.
Go to original source... - Wilde S.C., Treitz C., Keppler J.K., Koudelka T., Palani K., Tholey A., Rawel H.M., Schwarz K. (2016): β-Lactoglobulin as nanotransporter - Part II: Characterization of the covalent protein modification by allicin and diallyl disulfide. Food Chemistry, 197: 1022-1029.
Go to original source...
Go to PubMed... - Yilmaz Y., Toledo R. (2005): Antioxidant activity of watersoluble Maillard reaction products. Food Chemistry, 93: 273-278.
Go to original source... - Yin J., Andersen M.L., Thomsen M.K., Skibsted L.H., Hedegaard R.V. (2013): Formation of radicals during heating lysine and glucose in solution with an intermediate water activity. Free Radical Research, 47: 643-650.
Go to original source...
Go to PubMed... - Zamora R., Hidalgo F.J. (2005): Coordinate contribution of lipid oxidation and Maillard reaction to the nonenzymatic food browning. Critical Reviews in Food Science & Nutrition, 45: 49-59.
Go to original source...
Go to PubMed...
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