Abstract
This study aimed to investigate the ability of curcumin to convert asparagine into acrylamide during heating at different temperatures. Binary and ternary model systems of asparagine–curcumin and asparagine–curcumin–fructose were used to determine the role of curcumin on acrylamide formation in competitive and uncompetitive reaction conditions. The results indicated that curcumin could potentially contribute to acrylamide formation under long-term heating conditions as long as asparagine was present in the medium. The amount of acrylamide formed in the ternary system was slightly higher than in the binary system during heating (p < 0.05), because of the higher concentrations of carbonyl compounds initially available. The kinetic trends were similar in both model systems evidencing that fructose reacted with asparagine more rapidly than curcumin. The data reveal that acrylamide formation in the temperature range of 150–200°C obeys Arrhenius law with activation energy of 79.1 kJ/mole. Data of this work showed the possibility that antioxidants having a carbonyl compound can react directly with ASN leading to acrylamide. The addition of antioxidants to foods may increase the formation of acrylamide upon long-term heating if free sugar concentration is low and ASN concentration is relatively high.
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References
Acar OC, Gökmen V (2009) Investigation of acrylamide formation on bakery products using a crust-like model. Mol Nutr Food Res 53(12):1521–1525
Amrein TM, Andres L, Manzardo GGG, Amado R (2006) Investigations on the promoting effect of ammonium hydrogen carbonate on the formation of acrylamide in model systems. J Agric Food Chem 54(26):10253–10261
Brat P, Bassama J, Bohuon P, Boulanger R, Gunata Z (2010) Study of acrylamide mitigation in model system: effect of pure phenolic compounds. Food Chem 123(2):558–562
Capuano E, Fogliano V (2011) Acrylamide and 5-hydroxymethylfurfural (HMF): a review on metabolism, toxicity, occurrence in food and mitigation strategies. LWT Food SciTechnol 44:793–810
Corke H, Zhu F, Cai YZ, Ke JX (2009) Evaluation of the effect of plant extracts and phenolic compounds on reduction of acrylamide in an asparagine/glucose model system by RP-HPLC-DAD. J Sci Food Agric 89(10):1674–1681
FAO (2004) Curcumin. Chemical and Technical Assessment, 61st JECFA
Granda C, Moreira RG (2005) Kinetics of acrylamide formation during traditional and vacuum frying of potato chips. J Food Process Eng 28:478–493
Granvogl M, Jezussek M, Koehler P, Schieberle P (2004) Quantitation of 3-aminopropionamide in potatoes––a minor but potent precursor in acrylamide formation. J Agric Food Chem 52(15):4751–4757
Hidalgo FJ, Zamora R, Delgado RM (2010) Model reactions of acrylamide with selected amino compounds. J Agric Food Chem 58(3):1708–1713
IARC (1994) Monographs on the evaluation of carcinogenic risks to humans. Some industrial chemicals. International Agency for Research on Cancer. Lyon 60:389–433
Knol JJ, Van Loon WAM, Linssen JPH, Ruck AL, Van Boekel MAJS, Voragen AGJ (2005) Toward a kinetic model for acrylamide formation in a glucose–asparagine model system. J Agric Food Chem 53:6133–6139
Kotsiou K, Tasioula-Margari M, Capuano E, Fogliano V (2011) Effect of standard phenolic compounds and olive oil phenolic extracts on acrylamide formation in an emulsion system. Food Chem 124:242–247
Koutsidis G, De la Fuente A, Dimitriou C, Kakoulli A, Wedzicha BL, Mottram DS (2008) Acrylamide and pyrazine formation in model systems containing asparagine. J Agric Food Chem 56(15):6105–6112
Locas CP, Yaylayan VA (2008) Further insight into thermally and pH-induced generation of acrylamide from glucose/asparagine model systems. J Agric Food Chem 56:6069–6074
Mottram DS, Wedzicha BL, Dodson AT (2002) Acrylamide is formed in the Maillard reaction. Nature 419(6906):448–449
Napolitano A, Morales F, Sacchi R, Fogliano V (2008) Relationship between virgin olive oil phenolic compounds and acrylamide formation in fried crisps. J Agric Food Chem 56:2034–2040
Ou SY, Shi JJ, Huang CH, Zhang GW, Teng JW, Jiang Y, Yang BR (2010) Effect of antioxidants on elimination and formation of acrylamide in model reaction systems. J Hazard Mater 182(1–3):863–868
Senyuva HZS, Gokmen V (2005) Study of acrylamide in coffee using an improved liquid chromatography mass spectrometry method: Investigation of colour changes and acrylamide formation in coffee during roasting. Food Addit Contam 22:214–220
Stadler RH, Blank I, Varga N, Robert F, Hau J, Guy PA, Robert MC, Riediker S (2002) Acrylamide from Maillard reaction products. Nature 419(6906):449–450
Stadler RH, Robert F, Riediker S, Varga N, Davidek T, Devaud S, Goldmann T, Hau J, Blank I (2004) In-depth mechanistic study on the formation of acrylamide and other vinylogous compounds by the Maillard reaction. J Agric Food Chem 52(17):5550–5558
Tareke E, Rydberg P, Karlsson P, Eriksson S, Tornqvist M (2002) Analysis of acrylamide, a carcinogen formed in heated foodstuffs. J Agric Food Chem 50(17):4998–5006
Yaylayan VA, Stadler RH (2005) Acrylamide formation in food: A mechanistic perspective. J AOAC Int 88(1):262–267
Yaylayan VA, Wnorowski A, Locas CP (2003) Why asparagine needs carbohydrates to generate acrylamide. J Agric Food Chem 51(6):1753–1757
Zamora R, Hidalgo FJ, Delgado RM, Navarro JL (2010) Asparagine decarboxylation by lipid oxidation products in model systems. J Agric Food Chem 58(19):10512–10517
Zhang Y, Zhang Y (2008) Effect of natural antioxidants on kinetic behavior of acrylamide formation and elimination in low-moisture asparagine–glucose model system. J Food Eng 85(1):105–115
Zyzak DV, Sanders RA, Stojanovic M, Tallmadge DH, Eberhart BL, Ewald DK, Gruber DC, Morsch TR, Strothers MA, Rizzi GP, Villagran MD (2003) Acrylamide formation mechanism in heated foods. J Agric Food Chem 51(16):4782–4787
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Hamzalıoğlu, A., Mogol, B.A., Lumaga, R.B. et al. Role of curcumin in the conversion of asparagine into acrylamide during heating. Amino Acids 44, 1419–1426 (2013). https://doi.org/10.1007/s00726-011-1179-5
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DOI: https://doi.org/10.1007/s00726-011-1179-5