Regulation of harmful Maillard reaction products and flavour in roast steak by precursors: A structure- and dose-dependent mechanism of plant polyphenols - 2025
Regulation of harmful Maillard reaction products and flavour in roast steak by precursors: A structure- and dose-dependent mechanism of plant polyphenols
Regulation of harmful Maillard reaction products and flavour in roast steak by precursors A structure- and dose-dependent mechanism of plant polyphenols.pdf
[en] The development of attractive flavor in roasted meat is accompanied by the formation of potentially harmful compounds such as AGEs and HAs. This study determined the effect of different types (epicatechin, rosmarinic acid, resveratrol, hesperidin, kaempferol, and curcumin) and concentrations (0.1 %, 0.2 %, 0.4 %) of plant polyphenols on AGEs and HAs in roast steak and explored the potential regulatory mechanisms of plant polyphenols on the key free amino acids, fatty acids, flavor compounds, AGEs and HAs. Polyphenol marination significantly inhibited AGEs and HAs (P < 0.05) and modified the flavor profile. A two-way ANOVA revealed a highly significant interaction between polyphenol type and concentration (P < 0.001). Notably, 0.4 % epicatechin was identified as the most effective treatment. Chemometric analysis identified eight key free amino acids and five key fatty acids as core precursors. The O2PLS model revealed that polyphenols achieve their dual benefit of simultaneously inhibiting harmful Maillard reaction products and enhancing flavor by strategically regulating a shared network of key precursors at the intersection of the Maillard reaction and lipid oxidation. This targeted intervention is achieved through a synergistic mechanism whereby polyphenols act as direct antioxidants, deplete key free amino acid and fatty acid precursors, and trap reactive carbonyl intermediates. The dominant mechanism depends on the chemical structure of the polyphenols themselves. Our findings decipher the structure- and dose-dependent mechanisms by which polyphenols co-regulate safety and flavor, thereby providing a rational strategy for the development of healthier roasted meat products without compromising sensory quality.
Disciplines :
Food science
Author, co-author :
Li, Mingyu ; Université de Liège - ULiège > TERRA Research Centre ; Integrated Laboratory of Processing Technology for Chinese Meat Dishes, Institute of Food Science and Technology, Chinese Academy of Agricultural Sciences, Beijing, China
Zhang, Zeyu; Integrated Laboratory of Processing Technology for Chinese Meat Dishes, Institute of Food Science and Technology, Chinese Academy of Agricultural Sciences, Beijing, China
Qu, Xia; Integrated Laboratory of Processing Technology for Chinese Meat Dishes, Institute of Food Science and Technology, Chinese Academy of Agricultural Sciences, Beijing, China
Wei, Wenhan; Integrated Laboratory of Processing Technology for Chinese Meat Dishes, Institute of Food Science and Technology, Chinese Academy of Agricultural Sciences, Beijing, China
Wang, Zhenyu; Integrated Laboratory of Processing Technology for Chinese Meat Dishes, Institute of Food Science and Technology, Chinese Academy of Agricultural Sciences, Beijing, China
Zhang, Chunjiang ; Integrated Laboratory of Processing Technology for Chinese Meat Dishes, Institute of Food Science and Technology, Chinese Academy of Agricultural Sciences, Beijing, China ; Institute of Urban Agriculture, Chinese Academy of Agricultural Sciences, Chengdu National Agricultural Science & Technology Center, Chengdu, 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, China ; Institute of Urban Agriculture, Chinese Academy of Agricultural Sciences, Chengdu National Agricultural Science & Technology Center, Chengdu, China
Language :
English
Title :
Regulation of harmful Maillard reaction products and flavour in roast steak by precursors: A structure- and dose-dependent mechanism of plant polyphenols
The authors acknowledge the financial support from the National Key Research and Development Program ( 2024YFD2101503 ), Sichuan Science and Technology Program (2024ZHCG0186), and Taishan Industrial Experts Programme of China.
Aaslyng, M.D., Meinert, L., Meat flavour in pork and beef – From animal to meal. Meat Science 132 (2017), 112–117, 10.1016/j.meatsci.2017.04.012.
Anand, P., Thomas, S.G., Kunnumakkara, A.B., Sundaram, C., Harikumar, K.B., Sung, B., Tharakan, S.T., Misra, K., Priyadarsini, I.K., Rajasekharan, K.N., Aggarwal, B.B., Biological activities of curcumin and its analogues (Congeners) made by man and mother nature. Biochemical Pharmacology 76:11 (2008), 1590–1611, 10.1016/j.bcp.2008.08.008.
Basappa Maheswarappa, N., Subbaiah, V., Muthupalani, M., Yamagani, P.K., Mohan, K., Keshapaga, U.R., Vaikkathukattil Asokan, S., Kalappurakkal, R.C., Antioxidant activity of carnosic acid and rosmarinic acid in raw and cooked ground chicken patties. Journal of the Science of Food and Agriculture 94:2 (2014), 273–279, 10.1002/jsfa.6248.
Bassam, S.M., Noleto-Dias, C., Farag, M.A., Dissecting grilled red and white meat flavor: Its characteristics, production mechanisms, influencing factors and chemical hazards. Food Chemistry, 371, 2022, 131139, 10.1016/j.foodchem.2021.131139.
Bayati, M., Poojary, M.M., Polyphenol autoxidation and prooxidative activity induce protein oxidation and protein-polyphenol adduct formation in model systems. Food Chemistry, 466, 2025, 142208, 10.1016/j.foodchem.2024.142208.
Chen, Q.C., Lu, K.Y., He, J.Y., Zhou, Q., Li, S.Q., Xu, H., Su, Y.T., Wang, M.F., Effects of seasoning addition and cooking conditions on the formation of free and protein-bound heterocyclic amines and advanced glycation end products in braised lamb. Food Chemistry, 446, 2024, 138850, 10.1016/j.foodchem.2024.138850.
Chu, J.B., Lin, S.Y., Yuan, Y., Zhang, S.Q., Zhang, S.M., Effects of quercetin and L-ascorbic acid on heterocyclic amines and advanced glycation end products production in roasted eel and lipid-mediated inhibition mechanism analysis. Food Chemistry, 441, 2024, 138394, 10.1016/j.foodchem.2024.138394.
Comert, E.D., Gokmen, V., Interactions of epicatechin and cysteine with certain other dicarbonyl scavengers during their reaction with methylglyoxal under simulated physiological conditions. Food Chemistry, 369, 2022, 130884, 10.1016/j.foodchem.2021.130884.
Deng, P., Yang, T., Chai, Z., Shen, X., Oz, F., Chen, Q., Wang, Z., He, Z., Chen, J., Zeng, M., Synergistic inhibition against heterocyclic amines in beef patties: Caused by carbonyl-trapping and toxicity-reducing of amino acid combinations. Food Research International, 180, 2024, 114057, 10.1016/j.foodres.2024.114057.
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, 10.1016/j.foodchem.2021.130865.
Frankel, E.N., Huang, S.W., Prior, E., Aeschbach, R., Evaluation of antioxidant activity of rosemary extracts, carnosol and carnosic acid in bulk vegetable oils and fish oil and their emulsions. Journal of the Science of Food and Agriculture 72:2 (1996), 201–208, 10.1002/(SICI)1097-0010(199610)72:2<201::AID-JSFA632>3.0.CO;2-Q.
Gu, M.H., Li, C., Ren, Y.Q., Chen, L., Li, S.B., Zhang, D.Q., Zheng, X.C., Exploring the effect of part differences on metabolite molecule changes in refrigerated pork: Identifying key metabolite compounds and their conversion pathways. Food Chemistry, 460, 2024, 140308, 10.1016/j.foodchem.2024.140308.
Han, D., Zhang, C.-H., Fauconnier, M.-L., Mi, S., Characterization and differentiation of boiled pork from Tibetan, sanmenxia and duroc × (Landrac × Yorkshire) pigs by volatiles profiling and chemometrics analysis. Food Research International, 130, 2020, 108910, 10.1016/j.foodres.2019.108910.
Hu, G.L., Peng, X.R., Gao, Y., Huang, Y.J., Li, X., Su, H.G., Qiu, M.H., Effect of roasting degree of coffee beans on sensory evaluation: Research from the perspective of major chemical ingredients. Food Chemistry, 331, 2020, 127329, 10.1016/j.foodchem.2020.127329.
Huang, S.T., Hung, Y.A., Yang, M.J., Chen, I.Z., Yuann, J.M.P., Liang, J.Y., Effects of epigallocatechin gallate on the stability of epicatechin in a photolytic process. Molecules, 24(4), 2019, 787, 10.3390/molecules24040787.
Huang, Y.C., Li, H.J., Huang, T., Li, F., Sun, J., Lipolysis and lipid oxidation during processing of Chinese traditional smoke-cured bacon. Food Chemistry 149 (2014), 31–39, 10.1016/j.foodchem.2013.10.081.
Hui, T., Fang, Z.F., Hamid, N., Ma, Q.L., Cai, K.Z., Effect of variable pressure-assisted immersion process using (-)-epicatechin on the color, flavor, and polycyclic aromatic hydrocarbons content in roasted beef meat. LWT-Food Science and Technology, 178, 2023, 114602, 10.1016/j.lwt.2023.114602.
Jan, R., Khan, M., Asaf, S., Lubna, Asif, S., Kim, K.M., Bioactivity and therapeutic potential of kaempferol and quercetin: New insights for plant and human health. Plants, 11(19), 2022, 2623, 10.3390/plants11192623.
Jiang, Z.D., Han, Z.S., Zhu, M.T., Wan, X.C., Zhang, L., Effects of thermal processing on transformation of polyphenols and flavor quality. Current Opinion in Food Science, 51, 2023, 101014, 10.1016/j.cofs.2023.101014.
Khan, I.A., Khan, A., Zou, Y., Zongshuai, Z., Xu, W., Wang, D., Huang, M., Heterocyclic amines in cooked meat products, shortcomings during evaluation, factors influencing formation, risk assessment and mitigation strategies. Meat Science, 184, 2022, 108693, 10.1016/j.meatsci.2021.108693.
Khan, M., Liu, H.L., Wang, J., Sun, B.G., Inhibitory effect of phenolic compounds and plant extracts on the formation of advance glycation end products: A comprehensive review. Food Research International, 130, 2020, 108933, 10.1016/j.foodres.2019.108933.
Li, M., Zhang, C., Wang, Z., Liu, N., Wu, R., Han, J., Wei, W., Blecker, C., Zhang, D., Simultaneous determination of advanced glycation end products and heterocyclic amines in roast/grilled meat by UPLC-MS/MS. Food Chemistry, 447, 2024, 138930, 10.1016/j.foodchem.2024.138930.
Liu, J.Q., Han, G., Wang, Y., Wang, Y.D., Liu, Z.Q., Dong, X.P., Effect of rosemary extract on volatile flavor profile and flavor source of skipjack tuna. Food Bioscience, 62, 2024, 105241, 10.1016/j.fbio.2024.105241.
Liu, S.Y., Sun, H.J., Ma, G., Zhang, T., Wang, L., Pei, H., Li, X., Gao, L.Y., Insights into flavor and key influencing factors of maillard reaction products: A recent update. Frontiers in Nutrition, 9, 2022, 973677, 10.3389/fnut.2022.973677.
Medina, S., Perestrelo, R., Santos, R., Pereira, R., Câmara, J.S., Differential volatile organic compounds signatures of apple juices from madeira Island according to variety and geographical origin. Microchemical Journal, 150, 2019, 104094, 10.1016/j.microc.2019.104094.
Meurillon, M., Engel, E., Mitigation strategies to reduce the impact of heterocyclic aromatic amines in proteinaceous foods. Trends in Food Science & Technology 50 (2016), 70–84, 10.1016/j.tifs.2016.01.007.
Nawaz, A., Irshad, S., Walayat, N., Li, Z.H., Qin, Z.D., Yuan, Z.H., Tang, S.S., Khan, M.R., Manoharadas, S., Luo, X.F., Effect of structurally different pectin combined with polyphenol on water distribution, protein oxidation and heterocyclic amines formation in meat-based snacks. LWT-Food Science and Technology, 193, 2024, 115754, 10.1016/j.lwt.2024.115754.
Oz, E., The presence of polycyclic aromatic hydrocarbons and heterocyclic aromatic amines in barbecued meatballs formulated with different animal fats. Food Chemistry, 352, 2021, 129378, 10.1016/j.foodchem.2021.129378.
Oz, E., Aoudeh, E., Murkovic, M., Toldra, F., Gomez-Zavaglia, A., Brennan, C., Proestos, C., Zeng, M., Oz, F., Heterocyclic aromatic amines in meat: Formation mechanisms, toxicological implications, occurrence, risk evaluation, and analytical methods. Meat Science, 205, 2023, 109312, 10.1016/j.meatsci.2023.109312.
Ping, C., Zhao, X., He, C., Zheng, Y., Zhang, H., Comparing effects of tangerine-peel (Citrus reticulata Blanco) age and concentration on deep-fried rabbit meat: Impact on heterocyclic aromatic amines, amino acids, and flavor compound formation. Food Chemistry X, 24, 2024, 101902, 10.1016/j.fochx.2024.101902.
Pyo, I.S., Yun, S., Yoon, Y.E., Choi, J.-W., Lee, S.-J., Mechanisms of aging and the preventive effects of resveratrol on age-related diseases. Molecules, 25(20), 2020, 4649, 10.3390/molecules25204649.
Qu, M., Chen, Q., Sun, B., Lv, M., Liu, L., Zhu, X., Advances in studies on the functional properties of polyphenols and their interactions with proteins and polysaccharides. Science and Technology of Food Industry 42:11 (2021), 405–413, 10.13386/j.issn1002-0306.2020070358.
Rafiq, S., Kaul, R., Sofi, S.A., Bashir, N., Nazir, F., Ahmad Nayik, G., Citrus peel as a source of functional ingredient: A review. Journal of the Saudi Society of Agricultural Sciences 17:4 (2018), 351–358, 10.1016/j.jssas.2016.07.006.
Rawel, H.M., Czajka, D., Rohn, S., Kroll, J., Interactions of different phenolic acids and flavonoids with soy proteins. International Journal of Biological Macromolecules 30:3 (2002), 137–150, 10.1016/S0141-8130(02)00016-8.
Rohn, S., Petzke, K.J., Rawel, H.M., Kroll, J., Reactions of chlorogenic acid and quercetin with a soy protein isolate – Influence on the in vivo food protein quality in rats. Molecular Nutrition & Food Research 50:8 (2006), 696–704, 10.1002/mnfr.200600043.
Shahidi, F., Zhong, Y., Revisiting the polar paradox theory: A critical overview. Journal of Agricultural and Food Chemistry 59:8 (2011), 3499–3504, 10.1021/jf104750m.
Shakoor, A., Zhang, C., Xie, J., Yang, X., Maillard reaction chemistry in formation of critical intermediates and flavour compounds and their antioxidant properties. Food Chemistry, 393, 2022, 133416, 10.1016/j.foodchem.2022.133416.
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, 436, 2024, 137742, 10.1016/j.foodchem.2023.137742.
Sugimura, T., Wakabayashi, K., Nakagama, H., Nagao, M., Heterocyclic amines: Mutagens/carcinogens produced during cooking of meat and fish. Cancer Science 95:4 (2004), 290–299, 10.1111/j.1349-7006.2004.tb03205.x.
Sun, J., Li, M.Y., Mu, X.Q., Chen, L., Zhang, D.Q., Fang, F., Niu, X.Y., Zhang, C.J., Unraveling the chemosensory attributes of braised beef prepared from different regions using GC-MS combined with multivariate data analysis. International Journal of Gastronomy and Food Science, 37, 2024, 100954, 10.1016/j.ijgfs.2024.100954.
Sun, X., Yu, Y., Saleh, A.S.M., Yang, X., Ma, J., Gao, Z., Zhang, D., Li, W., Wang, Z., Characterization of aroma profiles of chinese four most famous traditional red-cooked chickens using GC–MS, GC-IMS, and E-nose. Food Research International, 173, 2023, 113335, 10.1016/j.foodres.2023.113335.
Teng, H., Deng, H., Zhang, C., Cao, H., Huang, Q., Chen, L., The role of flavonoids in mitigating food originated heterocyclic aromatic amines that concerns human wellness. Food Science and Human Wellness 12:4 (2023), 975–985, 10.1016/j.fshw.2022.10.019.
Tian, Z.Q., Chen, S.S., Shi, Y.H., Wang, P.P., Wu, Y.N., Li, G.L., Dietary advanced glycation end products (dAGEs): An insight between modern diet and health. Food Chemistry, 415, 2023, 135735, 10.1016/j.foodchem.2023.135735.
Tian, H., Yu, J., Li, M., Li, J., Lu, Y., Yu, X., Lin, S., Zeng, X., Xu, X., Han, M., Effect of curcumin on the formation of polycyclic aromatic hydrocarbons in grilled chicken wings. Food Chemistry, 414, 2023, 135561, 10.1016/j.foodchem.2023.135561.
Troise, A.D., Fogliano, V., Vitaglione, P., Berton-Carabin, C.C., Interrelated routes between the maillard reaction and lipid oxidation in emulsion systems. Journal of Agricultural and Food Chemistry 68:43 (2020), 12107–12115, 10.1021/acs.jafc.0c04738.
Vahmani, P., Rolland, D.C., McAllister, T.A., Block, H.C., Proctor, S.D., Guan, L.L., Prieto, N., López-Campos, Ó., Aalhus, J.L., Dugan, M.E.R., Effects of feeding steers extruded flaxseed on its own before hay or mixed with hay on animal performance, carcass quality, and meat and hamburger fatty acid composition. Meat Science 131 (2017), 9–17, 10.1016/j.meatsci.2017.04.008.
Vignesh, A., Amal, T.C., Vasanth, K., Food contaminants: Impact of food processing, challenges and mitigation strategies for food security. Food Research International, 191, 2024, 114739, 10.1016/j.foodres.2024.114739.
Vistoli, G., De Maddis, D., Cipak, A., Zarkovic, N., Carini, M., Aldini, G., Advanced glycoxidation and lipoxidation end products (AGEs and ALEs): An overview of their mechanisms of formation. Free Radical Research 47:Suppl 1 (2013), 3–27, 10.3109/10715762.2013.815348.
Wang, R., Lin, S., Chu, J., Yuan, Y., Zhang, S., Effect of tea extracts on heterocyclic aromatic amines and advanced glycation end products in roasting Eleutheronema tetradactylum and lipid-mediated inhibition mechanism analysis. Food Bioscience, 59, 2024, 103979, 10.1016/j.fbio.2024.103979.
Xie, Y., Chen, X., Structures required of polyphenols for inhibiting advanced glycation end products formation. Current Drug Metabolism 14:4 (2013), 414–431, 10.2174/1389200211314040005.
Xiong, K., Li, M.-m., Chen, Y.-q., Hu, Y.-m., Jin, W., Formation and reduction of toxic compounds derived from the maillard reaction during the thermal processing of different food matrices. Journal of Food Protection, 87(9), 2024, 100338, 10.1016/j.jfp.2024.100338.
Xu, Q.-D., Yu, Z.-L., He, Q., Zeng, W.-C., Migration of phenolic compounds in meat during marinating process: Action rule, mass transfer and mechanism. LWT-Food Science and Technology, 185, 2023, 115192, 10.1016/j.lwt.2023.115192.
Yan, S., Wu, L., Xue, X., alpha-Dicarbonyl compounds in food products: Comprehensively understanding their occurrence, analysis, and control. Comprehensive Reviews in Food Science and Food Safety 22:2 (2023), 1387–1417, 10.1111/1541-4337.13115.
Yang, X., Blecker, C., Liu, H., Zhang, D., Wang, Z., Effect of plant polyphenols with different m-hydroxy and o-hydroxy groups on the inhibition of heterocyclic amines formation in roasted meat. Food Control, 153, 2023, 10.1016/j.foodcont.2023.109960.
Yu, D., Jing, D., Yang, F., Gao, P., Jiang, Q., Xu, Y., Yu, P., Xia, W., The factors influencing the flavor characteristics of frozen obscure pufferfish (Takifugu Obscurus) during storage: Ice crystals, endogenous proteolysis and oxidation. International Journal of Refrigeration 122 (2021), 147–155, 10.1016/j.ijrefrig.2020.10.028.
Zeng, J., Meng, N., Song, Y., Fan, X., Jiang, X., Cong, P., Liu, Y., Xue, C., Xu, J., Insight into the mechanism of maillard reaction and lipids mutually contribute to the flavor release of squid fillets during the drying process. Food Chemistry, 468, 2025, 142435, 10.1016/j.foodchem.2024.142435.
Zhang, S., Wang, R., Chu, J., Sun, C., Lin, S., Vegetable extracts: Effective inhibitors of heterocyclic aromatic amines and advanced glycation end products in roasted mackerel. Food Chemistry, 412, 2023, 135559, 10.1016/j.foodchem.2023.135559.
Zhang, N., Zhou, Q., Fan, D., Xiao, J., Zhao, Y., Cheng, K.-W., Wang, M., Novel roles of hydrocolloids in foods: Inhibition of toxic maillard reaction products formation and attenuation of their harmful effects. Trends in Food Science & Technology 111 (2021), 706–715, 10.1016/j.tifs.2021.03.020.
Zhong, Y., Shahidi, F., Antioxidant behavior in bulk oil: Limitations of polar paradox theory. Journal of Agricultural and Food Chemistry 60:1 (2012), 4–6, 10.1021/jf204165g.
Zhou, Q., Cheng, K.W., Xiao, J.B., Wang, M.F., The multifunctional roles of flavonoids against the formation of advanced glycation end products (AGEs) and AGEs-induced harmful effects. Trends in Food Science & Technology 103 (2020), 333–347, 10.1016/j.tifs.2020.06.002.
Zhou, M., Li, F., Chen, J., Wu, Q., Zou, Z., Research progress on natural bio-based encapsulation system of curcumin and its stabilization mechanism. Food Science and Technology, 42, 2022, e78422, 10.1590/fst.78422.
Zhu, M., Long, Y., Ma, Y., Chen, Y., Yu, Q., Xie, J., Li, B., Tian, J., Comparison of chemical and fatty acid composition of green coffee bean (Coffea arabica L.) from different geographical origins. LWT-Food Science and Technology, 140, 2021, 110802, 10.1016/j.lwt.2020.110802.
Zhu, H., Poojary, M.M., Andersen, M.L., Lund, M.N., Trapping of carbonyl compounds by epicatechin: Reaction kinetics and identification of epicatechin adducts in stored UHT milk. Journal of Agricultural and Food Chemistry 68:29 (2020), 7718–7726, 10.1021/acs.jafc.0c01761.