Contribution of linoleic acid to the formation of advanced glycation end products in model systems during heat treatment

https://doi.org/10.17221/405/2016-CJFSCitation:Zhao X., Liu L., Yue L. (2017): Contribution of linoleic acid to the formation of advanced glycation end products in model systems during heat treatment. Czech J. Food Sci., 35: 367-375.
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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.
References:
Ahmad Muhammad Saeed, Pischetsrieder Monika, Ahmed Nessar (2007): Aged garlic extract and S-allyl cysteine prevent formation of advanced glycation endproducts. European Journal of Pharmacology, 561, 32-38  https://doi.org/10.1016/j.ejphar.2007.01.041
 
Ahmad S., Khan M. S., Akhter F., Khan M. S., Khan A., Ashraf J. M., Pandey R. P., Shahab U. (2014): Glycoxidation of biological macromolecules: A critical approach to halt the menace of glycation. Glycobiology, 24, 979-990  https://doi.org/10.1093/glycob/cwu057
 
Assar Shima H., Moloney Catherine, Lima Maria, Magee Ronald, Ames Jennifer M. (2009): Determination of N ɛ-(carboxymethyl)lysine in food systems by ultra performance liquid chromatography-mass spectrometry. Amino Acids, 36, 317-326  https://doi.org/10.1007/s00726-008-0071-4
 
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.
 
Campbell Lydia, Euston Stephen R., Ahmed Mohamed 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  https://doi.org/10.1016/j.foodchem.2015.09.002
 
Delatour Thierry, Hegele Jörg, Parisod Véronique, Richoz Janique, Maurer Sarah, Steven Matthew, Buetler Timo (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  https://doi.org/10.1016/j.chroma.2009.01.011
 
Han Lipeng, Li Lin, Li Bing, Zhao Di, Li Yuting, Xu Zhenbo, Liu Guoqin (2013): Glyoxal derived from triglyceride participating in diet-derived Nε-carboxymethyllysine formation. Food Research International, 51, 836-840  https://doi.org/10.1016/j.foodres.2013.01.051
 
Hedegaard Rikke V., Liu Ling, Skibsted Leif H. (2015): Quantification of radicals formed during heating of β-lactoglobulin with glucose in aqueous ethanol. Food Chemistry, 167, 185-190  https://doi.org/10.1016/j.foodchem.2014.06.118
 
Hull George L.J., Woodside Jayne V., Ames Jennifer M., Cuskelly Geraldine J. (2012): Nε-(carboxymethyl)lysine content of foods commonly consumed in a Western style diet. Food Chemistry, 131, 170-174  https://doi.org/10.1016/j.foodchem.2011.08.055
 
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.
 
Ifeduba Ebenezer A., Akoh Casimir C. (2015): Microencapsulation of stearidonic acid soybean oil in complex coacervates modified for enhanced stability. Food Hydrocolloids, 51, 136-145  https://doi.org/10.1016/j.foodhyd.2015.05.008
 
Kobue-Lekalake R.I. (2009): Sensory perception of bitterness and astringency in sorghum. [Doctoral thesis]. University of Pretoria, Pretoria, South Africa.
 
Liu Xiao, Liu Yu-Yang, Guo Jian, Yin Shou-Wei, Yang Xiao-Quan (2017): Microfluidization initiated cross-linking of gliadin particles for structured algal oil emulsions. Food Hydrocolloids, 73, 153-161  https://doi.org/10.1016/j.foodhyd.2017.07.001
 
Lokuruka MN (2011): Effects of processing on soybean nutrients and potential impact on consumer health: An overview. African Journal of Food, Agriculture, Nutrition and Development, 11, -  https://doi.org/10.4314/ajfand.v11i4.69170
 
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  https://doi.org/10.1016/j.foodchem.2012.07.008
 
Matiacevich Silvia B., Santagapita Patricio R., Buera M. Pilar (2005): Fluorescence from the Maillard Reaction and its Potential Applications in Food Science. Critical Reviews in Food Science and Nutrition, 45, 483-495  https://doi.org/10.1080/10408390591034472
 
Militello Valeria, Casarino Carlo, Emanuele Antonio, Giostra Antonella, Pullara Filippo, Leone Maurizio (2004): Aggregation kinetics of bovine serum albumin studied by FTIR spectroscopy and light scattering. Biophysical Chemistry, 107, 175-187  https://doi.org/10.1016/j.bpc.2003.09.004
 
Miyata T., Maeda K., Kurokawa K., van Ypersele de Strihou C. (1997): Hypothesis. Oxidation conspires with glycation to generate noxious advanced glycation end products in renal failure. Nephrology Dialysis Transplantation, 12, 255-258  https://doi.org/10.1093/ndt/12.2.255
 
Morales Francisco J, Jiménez-Pérez Salvio (2001): Free radical scavenging capacity of Maillard reaction products as related to colour and fluorescence. Food Chemistry, 72, 119-125  https://doi.org/10.1016/S0308-8146(00)00239-9
 
Navarra G., Giacomazza D., Leone M., Librizzi F., Militello V., Biagio P.L.S. (2009): Thermal aggregation and ion-induced cold-gelation of bovine serum albumin. Biophysics of Structure & Mechanism, 38: 437–446.
 
Niquet-Léridon Céline, Tessier Frédéric 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  https://doi.org/10.1016/j.foodchem.2010.10.111
 
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.
 
Raithore Smita, Bai Jinhe, Plotto Anne, Manthey John, Irey Mike, Baldwin Elizabeth (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  https://doi.org/10.3390/s151229787
 
Refsgaard H. H. F., Tsai L., Stadtman E. R. (2000): Modifications of proteins by polyunsaturated fatty acid peroxidation products. Proceedings of the National Academy of Sciences, 97, 611-616  https://doi.org/10.1073/pnas.97.2.611
 
Renzone Giovanni, Arena Simona, Scaloni Andrea (2015): Proteomic characterization of intermediate and advanced glycation end-products in commercial milk samples. Journal of Proteomics, 117, 12-23  https://doi.org/10.1016/j.jprot.2014.12.021
 
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.
 
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.
 
Shi Fei, Bai Bing, Ma Shufeng, Ji Shujuan, Liu Ling (2016): The inhibitory effects of γ-glutamylcysteine derivatives from fresh garlic on glycation radical formation. Food Chemistry, 194, 538-544  https://doi.org/10.1016/j.foodchem.2015.07.140
 
Skrt Mihaela, Benedik Evgen, Podlipnik Črtomir, Ulrih Nataša Poklar (2012): Interactions of different polyphenols with bovine serum albumin using fluorescence quenching and molecular docking. Food Chemistry, 135, 2418-2424  https://doi.org/10.1016/j.foodchem.2012.06.114
 
Spada Jordana C., Marczak Ligia D.F., Tessaro Isabel C., Cardozo Nilo S.M. (2015): Interactions between soy protein from water-soluble soy extract and polysaccharides in solutions with polydextrose. Carbohydrate Polymers, 134, 119-127  https://doi.org/10.1016/j.carbpol.2015.07.075
 
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.
 
Troise Antonio Dario, Fiore Alberto, Wiltafsky Markus, Fogliano Vincenzo (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  https://doi.org/10.1016/j.foodchem.2015.04.137
 
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.
 
Vistoli G., De Maddis 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, 3-27  https://doi.org/10.3109/10715762.2013.815348
 
Wadehra Akanksha, Patil Prasad Subhash (2016): Application of electronic tongues in food processing. Anal. Methods, 8, 474-480  https://doi.org/10.1039/C5AY02724A
 
Wilde Sandra Catharina, Treitz Christian, Keppler Julia Katharina, Koudelka Tomas, Palani Kalpana, Tholey Andreas, Rawel Harshadrai M., Schwarz Karin (2016): β-Lactoglobulin as nanotransporter – Part II: Characterization of the covalent protein modification by allicin and diallyl disulfide. Food Chemistry, 197, 1022-1029  https://doi.org/10.1016/j.foodchem.2015.11.011
 
Yilmaz Yusuf, Toledo Romeo (2005): Antioxidant activity of water-soluble Maillard reaction products. Food Chemistry, 93, 273-278  https://doi.org/10.1016/j.foodchem.2004.09.043
 
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  https://doi.org/10.3109/10715762.2013.812206
 
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.
 
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