Advanced glycation end products; Heterocyclic amines; Roast/grilled meat; UPLC-MS/MS; Amines; Glycation End Products, Advanced; Chromatography, Liquid; Meat/analysis; Amines/chemistry; Glycation End Products, Advanced/analysis; Chromatography, High Pressure Liquid/methods; Tandem Mass Spectrometry/methods; Liquid Chromatography-Mass Spectrometry; High sensitivity; High-accuracy; Maillard reaction products; Meat products; Pretreatment methods; Simultaneous determinations; Chromatography, High Pressure Liquid; Meat; Tandem Mass Spectrometry; Analytical Chemistry; Food Science
Abstract :
[en] Advanced glycation end products (AGEs) and heterocyclic amines (HAs) are main harmful Maillard reaction products of meat products. Simultaneous quantification of both with high sensitivity, selectivity and accuracy remains a major challenge due to inconsistencies in their pre-treatment and instrumental methods and the different polarity of AGEs and HAs. We developed a method for the simultaneous determination of AGEs and HAs in roast/grilled meat by ultra-performance liquid chromatography coupled to tandem mass spectrometry (UPLC-MS/MS) using dynamic multiple reaction monitoring (D-MRM). The instrument parameters and pre-treatment method were optimized to achieve reasonably good separation and high response for the 11 target analytes within 8 min. From 10 to 200 ng/mL, the limits of detection (LODs) and limits of quantitation (LOQs) ranged from 0.3 to 5.5 μg/L and 0.9 to 6.3 μg/L, respectively, and the correlation coefficient (R2) was >0.99. It was acceptable to recoveries, standard deviations (RSDs), and matrix effects. Six types of roast/grilled meat samples were then tested using the developed method.
Disciplines :
Food science
Author, co-author :
Li, Mingyu ; Université de Liège - ULiège > TERRA Research Centre
Zhang, Chunjiang; Integrated Laboratory of Processing Technology for Chinese Meat Dishes, Institute of Food Science and Technology, Chinese Academy of Agricultural Sciences, Beijing 100193, China
Wang, Zhenyu; Integrated Laboratory of Processing Technology for Chinese Meat Dishes, Institute of Food Science and Technology, Chinese Academy of Agricultural Sciences, Beijing 100193, China
Liu, Na; Institute of Animal Science, Chinese Academy of Agricultural Sciences, Beijing 100193, China
Wu, Ruiyun; Integrated Laboratory of Processing Technology for Chinese Meat Dishes, Institute of Food Science and Technology, Chinese Academy of Agricultural Sciences, Beijing 100193, China
Han, Jiajing; Integrated Laboratory of Processing Technology for Chinese Meat Dishes, Institute of Food Science and Technology, Chinese Academy of Agricultural Sciences, Beijing 100193, China
Wei, Wenhan; Integrated Laboratory of Processing Technology for Chinese Meat Dishes, Institute of Food Science and Technology, Chinese Academy of Agricultural Sciences, Beijing 100193, China
Blecker, Christophe ; Université de Liège - ULiège > TERRA Research Centre > Technologie Alimentaire (TA)
Zhang, Dequan; Integrated Laboratory of Processing Technology for Chinese Meat Dishes, Institute of Food Science and Technology, Chinese Academy of Agricultural Sciences, Beijing 100193, China. Electronic address: dequan_zhang0118@126.com
Language :
English
Title :
Simultaneous determination of advanced glycation end products and heterocyclic amines in roast/grilled meat by UPLC-MS/MS.
The authors acknowledge the financial support from Shandong Province Key R&D Program (Action Plan for Revitalizing Science and Technology Innovation and Revitalization of Rural Areas) [Grant No. 2022TZXD0021], and Taishan Industrial Experts Programme of China.
Barzegar, F., Kamankesh, M., Mohammadi, A., Heterocyclic aromatic amines in cooked food: A review on formation, health risk-toxicology and their analytical techniques. Food Chemistry 280 (2019), 240–254.
Carvalho, A.M., Miranda, A.M., Santos, F.A., Loureiro, A.P.D.M., Fisberg, R.M., Marchioni, D.M., High intake of heterocyclic amines from meat is associated with oxidative stress. British Journal of Nutrition 113:8 (2015), 1301–1307.
Chang, C.-C., Zhang, D., Wang, Z., Chen, B.-H., Simultaneous determination of twenty heterocyclic amines in cooking oil using dispersive solid phase extraction (QuEChERS) and high performance liquid chromatography–electrospray-tandem mass spectrometry. Journal of Chromatography A 1585 (2019), 82–91.
Chen, G.J., Smith, J.S., Determination of advanced glycation endproducts in cooked meat products. Food Chemistry 168 (2015), 190–195.
Chen, J., He, Z.Y., Qin, F., Chen, J., Zeng, M.M., Formation of free and protein-bound heterocyclic amines in roast beef patties assessed by UPLC-MS/MS. Journal of Agricultural and Food Chemistry 65:22 (2017), 4493–4499.
Chen, J.H., Lin, X., Bu, C.H., Zhang, X.G., Role of advanced glycation end products in mobility and considerations in possible dietary and nutritional intervention strategies. Nutrition & Metabolism (London), 15(1), 2018, 72.
Cheng, W., Wang, X., Zhang, Z., Ma, L., Liu, G., Wang, Q., Cheng, K.-W., Development of an isotope dilution UHPLC–QqQ-MS/MS-based method for simultaneous determination of typical advanced glycation end products and acrylamide in baked and fried foods. Journal of Agricultural and Food Chemistry 69:8 (2021), 2611–2618.
Chevolleau, S., Bouville, A., Debrauwer, L., Development and validation of a modified QuEChERS protocol coupled to UHPLC-APCI-MS/MS for the simple and rapid quantification of 16 heterocyclic aromatic amines in cooked beef. Food Chemistry, 316, 2020, 126327.
Di Pino, A., Currenti, W., Urbano, F., Scicali, R., Piro, S., Purrello, F., Rabuazzo, A.M., High intake of dietary advanced glycation end-products is associated with increased arterial stiffness and inflammation in subjects with type 2 diabetes. Nutrition. Metabolism and Cardiovascular Diseases 27:11 (2017), 978–984.
Ding, X., Zhang, D., Liu, H., Wang, Z., Hui, T., Chlorogenic acid and Epicatechin: An efficient inhibitor of heterocyclic amines in charcoal roasted lamb meats. Food Chemistry, 368, 2022, 130865.
Dong, H., Xian, Y.P., Li, H.X., Bai, W.D., Zeng, X.F., Potential carcinogenic heterocyclic aromatic amines (HAAs) in foodstuffs: Formation, extraction, analytical methods, and mitigation strategies. Comprehensive Reviews in Food Science and Food Safety 19:2 (2020), 365–404.
Fang, J.J., Liu, C.X., Law, C.L., Mujumdar, A.S., Xiao, H.W., Zhang, C.J., Superheated steam processing: An emerging technology to improve food quality and safety. Critical Reviews in Food Science and Nutrition, 2022, 1–17.
Gross, G.A., Grüter, A., Quantitation of mutagegnic/carcinogenic heterocyclic aromatic amines in food products. Journal of Chromatography A 592:1–2 (1992), 271–278.
Hsiao, H.-Y., Chen, B.-H., Kao, T.-H., Analysis of heterocyclic amines in meat by the quick, easy, cheap, effective, rugged, and safe method coupled with LC-DAD-MS-MS. Journal of Agricultural and Food Chemistry 65:42 (2017), 9360–9368.
Huang, Y., Shi, T., Luo, X., Xiong, H., Min, F., Chen, Y., Nie, S., Xie, M., Determination of multi-pesticide residues in green tea with a modified QuEChERS protocol coupled to HPLC-MS/MS. Food Chemistry 275 (2019), 255–264.
Jian, S.-H., Yeh, P.-J., Wang, C.-H., Chen, H.-C., Chen, S.-F., Analysis of heterocyclic amines in meat products by liquid chromatography – Tandem mass spectrometry. Journal of Food and Drug Analysis 27:2 (2019), 595–602.
Lai, Y.W., Lee, Y.T., Cao, H., Zhang, H.L., Chen, B.H., Extraction of heterocyclic amines and polycyclic aromatic hydrocarbons from pork jerky and the effect of flavoring on formation and inhibition. Food Chemistry, 402, 2023, 134291.
Lee, H.H.L., Ha, S.K., Kim, Y., Hur, J., Simultaneous analysis of advanced glycation end products using dansyl derivatization. Food Chemistry, 432, 2024, 137186.
Li, L., Li, P., Tang, S., Xiao, C., Huang, Y., Wang, L., Shao, B., Detection of chemical contaminants in heat processed meat products based on UPLC-MS/MS. Journal of Food Composition and Analysis, 124, 2023, 105711.
Li, M.Y., Lu, J.N., Huang, Y.S., Wang, W.J., Xie, J.H., Xie, M.Y., Shen, M.Y., Quantitative assessment of furosine, furfurals, and advanced glycation end products in different types of commercially available cheeses. Food Control, 136, 2022.
Li, Y., Wu, Y., Quan, W., Jia, X., He, Z., Wang, Z., Zeng, M., Quantitation of furosine, furfurals, and advanced glycation end products in milk treated with pasteurization and sterilization methods applicable in China. Food Research International, 140, 2021, 110088.
Lu, J., Li, M., Huang, Y., Xie, J., Shen, M., Xie, M., A comprehensive review of advanced glycosylation end products and N- nitrosamines in thermally processed meat products. Food Control, 131, 2022.
Maillard, L., Action des acides amines sur les sucres: formation des melanoidines par voie methodique. 1912.
Poojary, M.M., Zhang, W., Greco, I., De Gobba, C., Olsen, K., Lund, M.N., Liquid chromatography quadrupole-Orbitrap mass spectrometry for the simultaneous analysis of advanced glycation end products and protein-derived cross-links in food and biological matrices. Journal of Chromatography A, 1615, 2020, 460767.
Quan, W., Jiao, Y., Li, Y., Xue, C., Liu, G., Wang, Z., Chen, J., Metabolic changes from exposure to harmful Maillard reaction products and high-fat diet on Sprague-Dawley rats. Food Research International, 141, 2021, 110129.
Shi, H., Gao, R., Liu, H., Wang, Z., Zhang, C., Zhang, D., Qualitative and quantitative assessment of key aroma compounds, advanced glycation end products and heterocyclic amines in different varieties of commercially roasted meat products. Food Chemistry, 2023, 137742.
Suleman, R., Hui, T., Wang, Z., Liu, H., Zhang, D., Comparative analysis of charcoal grilling, infrared grilling and superheated steam roasting on the colour, textural quality and heterocyclic aromatic amines of lamb patties. International Journal of Food Science & Technology 55:3 (2019), 1057–1068.
Szterk, A., Chemical state of heterocyclic aromatic amines in grilled beef: Evaluation by in vitro digestion model and comparison of alkaline hydrolysis and organic solvent for extraction. Food and chemical toxicology 62 (2013), 653–660.
Twarda-Clapa, A., Olczak, A., Białkowska, A.M., Koziołkiewicz, M., Advanced glycation end-products (AGEs): Formation, chemistry, classification, receptors, and diseases related to AGEs. Cells, 11(8), 2022, 1312.
Uribarri, J., Woodruff, S., Goodman, S., Cai, W.J., Chen, X., Pyzik, R., Vlassara, H., Advanced glycation end products in foods and a practical guide to their reduction in the diet. Journal of the American Dietetic Association 110:6 (2010), 911–916.
Wang, H., Chu, X., Du, P., He, H., He, F., Liu, Y., Abd El-Aty, A.M., Unveiling heterocyclic aromatic amines (HAAs) in thermally processed meat products: Formation, toxicity, and strategies for reduction – A comprehensive review. Food Chemistry: X, 19, 2023, 100833.
Wei, Q.Y., Liu, T., Sun, D.W., Advanced glycation end-products (AGEs) in foods and their detecting techniques and methods: A review. Trends in Food Science & Technology 82 (2018), 32–45.
Wei, S.Y., Yang, X., Lin, M.Y., Chen, N., Gao, X.Y., Hu, X.S., Zhu, Y.C., Development of a two-step pretreatment and UPLC-MS/MS-based method for simultaneous determination of acrylamide, 5-hydroxymethylfurfural, advanced glycation end products and heterocyclic amines in thermally processed foods. Food Chemistry, 430, 2024.
Xu, Y., Li, H., Liang, J., Ma, J., Yang, J., Zhao, X., Zhao, W., Bai, W., Zeng, X., Dong, H., High-throughput quantification of eighteen heterocyclic aromatic amines in roasted and pan-fried meat on the basis of high performance liquid chromatography-quadrupole-orbitrap high resolution mass spectrometry. Food Chemistry, 361, 2021.
Xue, C., Deng, P., Quan, W., Li, Y., He, Z., Qin, F., Zeng, M., Ginger and curcumin can inhibit heterocyclic amines and advanced glycation end products in roast beef patties by quenching free radicals as revealed by electron paramagnetic resonance. Food Control, 138, 2022, 109038.
Xue, C.Y., Quan, W., Li, Y., He, Z.Y., Qin, F., Wang, Z.J., Zeng, M.M., Mitigative capacity of L. and kaempferol on heterocyclic amines and advanced glycation end products in roasted beef patties and related mechanistic analysis by density functional theory. Food Chemistry, 385, 2022, 132660.
Yan, S., Zhang, M., Yuan, Y., Mu, G., Xu, H., Zhao, T., Wang, Y., Xue, X., Chaste honey in long term-storage: Occurrence and accumulation of Maillard reaction products, and safety assessment. Food Chemistry, 424, 2023, 136457.
Yu, L., Li, Y., Gao, C., Yang, Y., Zeng, M., Chen, J., Nε-carboxymethyl-lysine and Nε-carboxyethyl-lysine contents in commercial meat products. Food Research International, 155, 2022, 111048.
Yuan, X., Nie, C., Liu, H., Ma, Q., Peng, B., Zhang, M., Chen, Z., Li, J., Comparison of metabolic fate, target organs, and microbiota interactions of free and bound dietary advanced glycation end products. Critical Reviews in Food Science and Nutrition 63:19 (2021), 3612–3633.
Zhang, G., Zou, X., Mao, W., Chen, M., Heterocyclic aromatic amines and risk of kidney stones: A cross-sectional study in US adults. Frontiers in public health, 10, 2022, 935739.
Zhang, S.M., Wang, R.C., Chu, J.B., Sun, C.Y., Lin, S.Y., Vegetable extracts: Effective inhibitors of heterocyclic aromatic amines and advanced glycation end products in roasted mackerel. Food Chemistry, 412, 2023, 135559.
Zhu, Z., Huang, M., Cheng, Y., Khan, I.A., Huang, J., A comprehensive review of Nε-carboxymethyllysine and Nε-carboxyethyllysine in thermal processed meat products. Trends in Food Science & Technology 98 (2020), 30–40.
