Abstract
A novel method of Maillard reaction performed under stepwise increase of temperature was proposed for the preparation of Maillard reaction intermediate (MRI) derived from fructose (Fru) and phenylalanine (Phe). The optimal formation conditions of MRI in aqueous medium were determined as follows: pH 7.4 and heating for 100 min at 100 °C. The purified MRI was characterized to be 1-amino-1-deoxyfructose derivative (C15H21NO7, 327 Da) by mass spectrometry and NMR. The methodological effectiveness of this new developed method was further verified. Although almost similar types of volatile compounds were identified in the three heated solutions of Fru-Phe mixture, Maillard reaction products (MRPs) and 1-amino-1-deoxyfructose derivatives, the concentration of total volatile compounds was 118.30 μg/L relative to the internal standard for Fru-Phe mixture and increased by 64.49 and 1024.64 μg/L for MRPs and 1-amino-1-deoxyfructose derivative, respectively. The results showed that more fresh flavors were controlled formed from 1-amino-1-deoxyfructose derivative compared with those from MRPs or Fru-Phe mixture during the subsequent heating treatment; thus, the 1-amino-1-deoxyfructose derivatives could be a great potential substitute of unstable MRPs or Fru-Phe mixture in preparation of flavoring.
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Abbreviations
- MRPs :
-
Maillard reaction products
- Fru :
-
fructose
- Phe :
-
phenylalanine
- Cys :
-
cysteine
- RP-HPLC :
-
reversed phase high performance liquid chromatography
- UPLC :
-
ultra performance liquid chromatography
- MS :
-
mass spectrometry
- HS-SPME :
-
headspace solid phase microextraction
- GC :
-
gas chromatography
References
Balagiannis, D. P. (2015). 10 - Predicting aroma formation with kinetic models. In J. K. Parker, S. Elmore, & L. Methven (Eds.), Flavour development, analysis and perception in food and beverages (pp. 211–233). Cambridge: Woodhead Publishing Series.
Coleman, W. M., & Chung, H. L. (2002). Pyrolysis GC–MS analysis of Amadori compounds derived from selected amino acids and glucose. Journal of Analytical and Applied Pyrolysis, 62(2), 215–223. https://doi.org/10.1016/S0165-2370(01)00118-8.
Davidek, T., Kraehenbuehl, K., Devaud, S., Robert, F., & Blank, I. (2005). Analysis of Amadori compounds by high-performance cation exchange chromatography coupled to tandem mass spectrometry. Analytical Chemistry, 77(1), 140–147. https://doi.org/10.1021/ac048925a.
Harohally, N. V., Srinivas, S. M., & Umesh, S. (2014). ZnCl2-mediated practical protocol for the synthesis of Amadori ketoses. Food Chemistry, 158, 340–344. https://doi.org/10.1016/j.foodchem.2014.02.094.
Hong, P. K., & Betti, M. (2016). Non-enzymatic browning reaction of glucosamine at mild conditions: relationship between colour formation, radical scavenging activity and α-dicarbonyl compounds production. Food Chemistry, 212, 234–243. https://doi.org/10.1016/j.foodchem.2016.05.170.
Huang, M., Zhang, X., & Karangwa, E. (2015). Comparation sensory characteristic, non-volatile compounds, volatile compounds and antioxidant activity of MRPs by novel gradient temperature-elevating and traditional isothermal methods. Journal of Food Science and Technology, 52(2), 858–866. https://doi.org/10.1007/s13197-013-1083-y.
Huang, M. G., Zhang, X. M., Eric, K., Abbas, S., Hayat, K., Liu, P., Xia, S. Q., & Jia, C. S. (2012). Inhibiting the color formation by gradient temperature-elevating Maillard reaction of soybean peptide-xylose system based on interaction of l-cysteine and Amadori compounds. Journal of Peptide Science, 18(5), 342–349. https://doi.org/10.1002/psc.2406.
Jakas, A., Katić, A., Bionda, N., & Horvat, Š. (2008). Glycation of a lysine-containing tetrapeptide by d-glucose and d-fructose—influence of different reaction conditions on the formation of Amadori/Heyns products. Carbohydrate Research, 343(14), 2475–2480. https://doi.org/10.1016/j.carres.2008.07.003.
Karangwa, E., Zhang, X., Murekatete, N., Masamba, K., Raymond, L. V., Shabbar, A., Zhang, Y., Duhoranimana, E., Muhoza, B., & Song, S. (2015). Effect of substrate type on sensory characteristics and antioxidant capacity of sunflower Maillard reaction products. European Food Research and Technology, 240(5), 939–960. https://doi.org/10.1007/s00217-014-2398-2.
Kaufmann, M., Meissner, P. M., Pelke, D., Mügge, C., & Kroh, L. W. (2016). Structure–reactivity relationship of Amadori rearrangement products compared to related ketoses. Carbohydrate Research, 428, 87–99. https://doi.org/10.1016/j.carres.2016.04.016.
Kocadağlı, T., & Gökmen, V. (2016). Multiresponse kinetic modelling of Maillard reaction and caramelisation in a heated glucose/wheat flour system. Food Chemistry, 211, 892–902. https://doi.org/10.1016/j.foodchem.2016.05.150.
Lin, J.-T., Liu, S.-C., Hu, C.-C., Shyu, Y.-S., Hsu, C.-Y., & Yang, D.-J. (2016). Effects of roasting temperature and duration on fatty acid composition, phenolic composition, Maillard reaction degree and antioxidant attribute of almond (Prunus dulcis) kernel. Food Chemistry, 190, 520–528. https://doi.org/10.1016/j.foodchem.2015.06.004.
Linetsky, M. D., Shipova, E. V., Legrand, R. D., & Argirov, O. O. (2005). Glucose-derived Amadori compounds of glutathione. Biochimica et Biophysica Acta (BBA) - General Subjects, 1724(1), 181–193. https://doi.org/10.1016/j.bbagen.2005.04.003.
Liu, J., Liu, M., He, C., Song, H., & Chen, F. (2015). Effect of thermal treatment on the flavor generation from Maillard reaction of xylose and chicken peptide. LWT - Food Science and Technology, 64(1), 316–325. https://doi.org/10.1016/j.lwt.2015.05.061.
Lotfy, S. N., Fadel, H. H. M., El-Ghorab, A. H., & Shaheen, M. S. (2015). Stability of encapsulated beef-like flavourings prepared from enzymatically hydrolysed mushroom proteins with other precursors under conventional and microwave heating. Food Chemistry, 187, 7–13. https://doi.org/10.1016/j.foodchem.2015.04.027.
Ma, J., Peng, X., Cheng, K.-W., Kong, R., Chu, I. K., Chen, F., & Wang, M. (2010). Effects of melamine on the Maillard reaction between lactose and phenylalanine. Food Chemistry, 119(1), 1–6. https://doi.org/10.1016/j.foodchem.2009.07.007.
Martins, S. I. F. S., Marcelis, A. T. M., & van Boekel, M. A. J. S. (2003). Kinetic modelling of Amadori N-(1-deoxy-d-fructos-1-yl)-glycine degradation pathways. Part I—reaction mechanism. Carbohydrate Research, 338(16), 1651–1663. https://doi.org/10.1016/S0008-6215(03)00173-3.
Michalska, A., Honke, J., Łysiak, G., & Andlauer, W. (2016). Effect of drying parameters on the formation of early and intermediate stage products of the Maillard reaction in different plum (Prunus domestica L.) cultivars. LWT - Food Science and Technology, 65, 932–938. https://doi.org/10.1016/j.lwt.2015.09.015.
Mottram, D. S. (2007). The Maillard reaction: source of flavour in thermally processed foods. In R. G. Berger (Ed.), Flavours and fragrances: chemistry, bioprocessing and sustainability (pp. 269–283). Berlin, Heidelberg: Springer Berlin Heidelberg.
Nashalian, O., & Yaylayan, V. A. (2016). In situ formation of the amino sugars 1-amino-1-deoxy-fructose and 2-amino-2-deoxy-glucose under Maillard reaction conditions in the absence of ammonia. Food Chemistry, 197(Pt A), 489–495. https://doi.org/10.1016/j.foodchem.2015.10.140.
Nursten, H. (2005). Inhibition of nonenzymic browning in foods. In J. F. Kennedy, & C. J. Knill (Eds.), The Maillard reaction (pp. 152–160). Cambridge: Royal Society of Chemistry. https://doi.org/10.1039/9781847552570.
Parker, J. K. (2015). 8 - Thermal generation or aroma. In J. K. Parker, J. S. Elmore, & L. Methven (Eds.), Flavour development, analysis and perception in food and beverages (pp. 151–185). Cambridge: Woodhead Publishing Series.
Patrignani, M., Rinaldi, G. J., & Lupano, C. E. (2016). In vivo effects of Maillard reaction products derived from biscuits. Food Chemistry, 196, 204–210. https://doi.org/10.1016/j.foodchem.2015.09.038.
Perez-Locas, C., & Yaylayan, V. A. (2010). The Maillard reaction and food quality deterioration. In L. H. Skibsted, J. Risbo, & M. L. Andersen (Eds.), Chemical deterioration and physical instability of food and beverages (pp. 70–94). Cambridge: Woodhead Publishing Series.
Rufián-Henares, J. A., & Pastoriza, S. (2016). Maillard reaction. In Encyclopedia of food and health (pp. 593–600). Oxford: Academic Press. https://doi.org/10.1016/B978-0-12-384947-2.00435-9.
Seisonen, S., Kivima, E., & Vene, K. (2015). Characterisation of the aroma profiles of different honeys and corresponding flowers using solid-phase microextraction and gas chromatography–mass spectrometry/olfactometry. Food Chemistry, 169, 34–40. https://doi.org/10.1016/j.foodchem.2014.07.125.
Sharma, S., & Kumar, R. (2016). Effect of temperature and storage duration of flowers on essential oil content and composition of damask rose (Rosa×damascena Mill.) under western Himalayas. Journal of Applied Research on Medicinal and Aromatic Plants, 3(1), 10–17. https://doi.org/10.1016/j.jarmap.2015.10.001.
Song, S., Li, S., Fan, L., Hayat, K., Xiao, Z., Chen, L., & Tang, Q. (2016). A novel method for beef bone protein extraction by lipase-pretreatment and its application in the Maillard reaction. Food Chemistry, 208, 81–88. https://doi.org/10.1016/j.foodchem.2016.03.062.
Souza, R. O. L., Fabiano, D. P., Feche, C., Rataboul, F., Cardoso, D., & Essayem, N. (2012). Glucose–fructose isomerisation promoted by basic hybrid catalysts. Catalysis Today, 195(1), 114–119. https://doi.org/10.1016/j.cattod.2012.05.046.
Stefanowicz, P., Kapczyńska, K., Kluczyk, A., & Szewczuk, Z. (2007). A new procedure for the synthesis of peptide-derived Amadori products on a solid support. Tetrahedron Letters, 48(6), 967–969. https://doi.org/10.1016/j.tetlet.2006.12.022.
Sun, L., & Zhuang, Y. (2012). Characterization of the Maillard reaction of enzyme-hydrolyzed wheat protein producing meaty aromas. Food and Bioprocess Technology, 5(4), 1287–1294. https://doi.org/10.1007/s11947-010-0406-5.
Trevisan, A. J. B., de Almeida Lima, D., Sampaio, G. R., Soares, R. A. M., & Markowicz Bastos, D. H. (2016). Influence of home cooking conditions on Maillard reaction products in beef. Food Chemistry, 196, 161–169. https://doi.org/10.1016/j.foodchem.2015.09.008.
Troise, A. D., Berton-Carabin, C. C., & Fogliano, V. (2016). Amadori products formation in emulsified systems. Food Chemistry, 199, 51–58. https://doi.org/10.1016/j.foodchem.2015.11.110.
Yu, X., Zhao, M., Hu, J., & Zeng, S. (2012). Formation and antioxidant activity of volatile compounds produced by heating glucose with tyrosine/histidine in water-ethanol and water-glycerol media. Food Chemistry, 133(4), 1394–1401. https://doi.org/10.1016/j.foodchem.2012.01.116.
Yu H, Ming Z. M. K., Seow Y X, et al. (2017). Kinetic Study of High-Intensity Ultrasound-Assisted Maillard Reaction in a Model System of D-Glucose and LMethionine[J]. Food and Bioprocess Technology, (5):1-13.
Zhao, M., Wang, Y., Huo, C., Li, C., Zhang, X., Peng, L., & Peng, S. (2009). Stereoselective synthesis of novel N-(α-l-arabinofuranos-1-yl)-l-amino acids. Tetrahedron: Asymmetry, 20(2), 247–258. https://doi.org/10.1016/j.tetasy.2009.01.014.
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The research was supported by the Science and Technology Key Project of State Tobacco Monopoly Administration 110201402039, the National Natural Science Foundation of China 31671826, and the National Key Research and Development Program of China 2017YFD0400105.
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Yang, J., Deng, S., Yin, J. et al. Preparation of 1-Amino-1-deoxyfructose Derivatives by Stepwise Increase of Temperature in Aqueous Medium and Their Flavor Formation Compared with Maillard Reaction Products. Food Bioprocess Technol 11, 694–704 (2018). https://doi.org/10.1007/s11947-017-2039-4
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DOI: https://doi.org/10.1007/s11947-017-2039-4