Effect of plant polyphenols with different m-hydroxy and o-hydroxy groups on the inhibition of heterocyclic amines formation in roasted meat - 1-s2.0-S0956713523003602-main.pdf
[en] To elucidate the regulation of different structures of polyphenolic compounds with m-hydroxy and o-hydroxy groups inhibiting the formation of different heterocyclic amines (HAs), the reactions between classified polyphenols (cover flavonoids, phenolic acids, stilbenes, coumarins, chalcones, and with different hydroxyl groups) and roasted lamb patties were studied, and then validated in model systems in vitro. The results indicated that the chalcone, coumarin, and stilbene compounds were more efficient to inhibit the HAs generation in roasted lamb patties in comparison with the flavonoids, while phenolic acid had the worst effect. Besides, polyphenols inhibit the formation of HAs through a synergistic action of scavenging free radicals and trapping active carbonyls. Polyphenols with m-hydroxyl structures have a stronger inhibition of PhIP1, Harman and Norharman by capturing the reaction intermediate carbonyl compounds. Polyphenols with the o-hydroxyl group had a stronger inhibitory effect on MeIQx by scavenging free radicals. It was concluded that the ability of polyphenols to inhibit different HAs can be predicted by their m-hydroxyl and o-hydroxyl groups.
Disciplines :
Food science
Author, co-author :
Yang, Xiaoyue; Institute of Food Science and Technology, Chinese Academy of Agricultural Sciences, Beijing, China ; Key Laboratory of Agro-Products Processing, Ministry of Agriculture and Rural Affairs, Beijing, China ; Department of Food Science and Formulation, Gembloux Agro-Bio Tech, University of Liège, Gembloux, Belgium
Blecker, Christophe ; Université de Liège - ULiège > TERRA Research Centre > Technologie Alimentaire (TA)
Liu, Huan; Institute of Food Science and Technology, Chinese Academy of Agricultural Sciences, Beijing, China ; Key Laboratory of Agro-Products Processing, Ministry of Agriculture and Rural Affairs, Beijing, China
Zhang, Dequan; Institute of Food Science and Technology, Chinese Academy of Agricultural Sciences, Beijing, China ; Key Laboratory of Agro-Products Processing, Ministry of Agriculture and Rural Affairs, Beijing, China
Wang, Zhenyu; Institute of Food Science and Technology, Chinese Academy of Agricultural Sciences, Beijing, China ; Key Laboratory of Agro-Products Processing, Ministry of Agriculture and Rural Affairs, Beijing, China
Language :
English
Title :
Effect of plant polyphenols with different m-hydroxy and o-hydroxy groups on the inhibition of heterocyclic amines formation in roasted meat
This work was financially supported by National Key R&D Program of China ( 2019YFC1606200 ), Beijing Innovation Consortium of Agriculture Research System ( BAIC06-2022 ), and National Agricultural Science and Technology Innovation Program (meat science and nutrition engineering).
Alaejos, M.S., Afonso, A.M., Factors that affect the content of heterocyclic aromatic amines in foods. Comprehensive Reviews in Food Science and Food Safety 10 (2011), 52–108, 10.1111/j.1541-4337.2010.00141.x.
Amić, D., Davidović-Amić, D., Beslo, D., Rastija, V., Lucić, B., Trinajstić, N., SAR and QSAR of the antioxidant activity of flavonoids. Current Medicinal Chemistry 14:7 (2007), 827–845, 10.2174/092986707780090954.
Bao, X., Miao, J., Huang, Y., Lai, K., Revealing a key inhibitory mechanism of 2-amino-3,8-dimethylimidazo[4,5-f] quinoxaline via trapping of methylglyoxal. Journal of Food Science 85:7 (2020), 2090–2097, 10.1111/1750-3841.15305.
Barba, F.J., Roohinejad, S., Ishikawa, K., Leong, S.Y., Bekhit, A.E.D.A., Saraiva, J.A., Electron spin resonance as a tool to monitor the influence of novel processing technologies on food properties. Trends in Food Science & Technology 100 (2020), 77–87, 10.1016/j.tifs.2020.03.03.
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, 10.1016/j.foodchem.2018.12.058.
Boada, L.D., Henríquez-Hernández, L.A., Luzardo, O.P., The impact of red and processed meat consumption on cancer and other health outcomes: Epidemiological evidences. Food and Chemical Toxicology: An International Journal Published for the British Industrial Biological Research Association 92 (2016), 236–244, 10.1016/j.fct.2016.04.008.
Cai, Y.Z., Sun, M., Xing, J., Luo, Q., Corke, H., Structure-radical scavenging activity relationships of phenolic compounds from traditional Chinese medicinal plants. Life Sciences 78:25 (2006), 2872–2888, 10.1016/j.lfs.2005.11.004.
Cheng, K.W., Wong, C.C., Chao, J., Lo, C., Chen, F., Chu, I.K., et al. Inhibition of mutagenic PhIP formation by epigallocatechin gallate via scavenging of phenylacetaldehyde. Molecular Nutrition & Food Research 53:6 (2009), 716–725, 10.1002/mnfr.200800206.
Cheng, K.W., Wong, C.C., Cho, C.K., Chu, I.K., Sze, K.H., Lo, C., et al. Trapping of phenylacetaldehyde as a key mechanism responsible for naringenin's inhibitory activity in mutagenic 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine formation. Chemical Research in Toxicology 21:10 (2008), 2026–2034, 10.1021/tx800220h.
Chen, X., Jia, W., Zhu, L., Mao, L., Zhang, Y., Recent advances in heterocyclic aromatic amines: An update on food safety and hazardous control from food processing to dietary intake. Comprehensive Reviews in Food Science and Food Safety 19:1 (2020), 124–148, 10.1111/1541-4337.12511.
Chen, L., Kang, Y.H., Antioxidant and enzyme inhibitory activities of Plebeian herba (Salvia plebeia R. Br.) under different cultivation conditions. Journal of Agricultural and Food Chemistry 62:10 (2014), 2190–2197, 10.1021/jf404570s.
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.
Falowo, A.B., Fayemi, P.O., Muchenje, V., Natural antioxidants against lipid-protein oxidative deterioration in meat and meat products: A review. Food Research International 64 (2014), 171–181, 10.1016/j.foodres.2014.06.022.
Gibis, M., Heterocyclic aromatic amines in cooked meat products: Causes, formation, occurrence, and risk assessment. Comprehensive Reviews in Food Science and Food Safety 15:2 (2016), 269–302, 10.1111/1541-4337.12186.
Hidalgo, F.J., Aguilar, I., Zamora, R., Model studies on the effect of aldehyde structure on their selective trapping by phenolic compounds. Journal of Agricultural and Food Chemistry 65:23 (2017), 4736–4743, 10.1021/acs.jafc.7b01081.
Hui, T., Li, Y., Chen, R., Yang, X., Liu, H., Wang, Z., et al. Formation and prediction of PhIP, Harman, and Norharman in chemical model systems containing Epicatechin under various reaction conditions. Journal of Agricultural and Food Chemistry 69:49 (2021), 14975–14984, 10.1021/acs.jafc.1c05698.
Kikugawa, K., Involvement of free radicals in the formation of heterocyclic amines and prevention by antioxidants. Cancer Letters 143:2 (1999), 123–126, 10.1016/s0304-3835(99)00140-8.
Lucić, B., Amić, D., Trinajstić, N., Antioxidant QSAR modeling as exemplified on polyphenols. Methods in Molecular Biology 477 (2008), 207–218, 10.1007/978-1-60327-517-0_16.
Lund, M., Reactions of plant polyphenols in foods: Impact of molecular structure. Trends in Food Science & Technology 112 (2021), 241–251, 10.1016/j.tifs.2021.03.056.
Milic, B.L., Djilas, S.M., Canadanovic-Brunet, J. M. Synthesis of some heterocyclic aminoimidazoazarenes. Food Chemistry 46 (1993), 273–276, 10.1016/0308-8146(93)90118-Y.
Murkovic, M., Weber, H.-J., Geiszler, S., Fröhlich, K., Pfannhauser, W., Formation of the food associated carcinogen 2-amino-1-methyl-6phenylimidazo[4,5-b]pyridine (PhIP) in model systems. Food Chemistry 65 (1999), 233–237, 10.15302/J-FASE-2017182.
Musa, K.H., Abdullah, A., Al-Haiqi, A., Determination of DPPH free radical scavenging activity: Application of artificial neural networks. Food Chemistry 194 (2016), 705–711, 10.1016/j.foodchem.2015.08.038.
Oguri, A., Suda, M., Totsuka, Y., Sugimura, T., Wakabayashi, K., Inhibitory effects of antioxidants on formation of heterocyclic amines. Mutation Research 402:1–2 (1998), 237–245, 10.1016/s0027-5107(97)00303-5.
Özdestan, Ö., Kaçar, E., Keşkekoğlu, H., Üren, A., Development of a new extraction method for heterocyclic aromatic amines determination in cooked meatballs. Food Analytical Methods 7 (2013), 116–126, 10.1007/s12161-013-9607-7.
Pearson, A.M., Chen, C., Gray, J.I., Aust, S.D., Mechanism(s) involved in meat mutagen formation and inhibition. Free Radical Biology & Medicine 13:2 (1992), 161–167, 10.1016/0891-5849(92)90078-u.
Rönner, B., Lerche, H., Bergmüller, W., Freilinger, C., Severin, T., Pischetsrieder, M., Formation of tetrahydro-β-carbolines and β-carbolines during the reaction of L-tryptophan with D-glucose. Journal of Agricultural and Food Chemistry 48:6 (2000), 2111–2116, 10.1021/jf991237l.
Salazar, R., Arámbula-Villa, G., Hidalgo, F.J., Zamora, R., Structural characteristics that determine the inhibitory role of phenolic compounds on 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) formation. Food Chemistry 151 (2014), 480–486, 10.1016/j.foodchem.2013.11.105.
Santhakumar, A.B., Battino, M., Alvarez-Suarez, J.M., Dietary polyphenols: Structures, bioavailability and protective effects against atherosclerosis. Food and Chemical Toxicology: An International Journal Published for the British Industrial Biological Research Association 113 (2018), 49–65, 10.1016/j.fct.2018.01.022.
Seyoum, A., Asres, K., El-Fiky, F.K., Structure-radical scavenging activity relationships of flavonoids. Phytochemistry 67:18 (2006), 2058–2070, 10.1016/j.phytochem.2006.07.002.
Skog, K., Jägerstad, M., Incorporation of 14C-glucose into mutagenic heterocyclic amines. Labuza, T.P., Reineccius, G.A., Monnie, V.M., O'Brien, J., Baynes, J.W., (eds.) Maillard reactions in chemistry, food and health, 2005, Woodhead Publishing, Cambridge, UK, 147–152.
Stoesser, R., Klein, J., Peschke, S., Zehl, A., Cämmerer, B., Kroh, L.W., On the time behaviour of the concentration of pyrazinium radical cations in the early stage of the Maillard reaction. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 67:5 (2007), 1161–1168, 10.1016/j.saa.2006.10.003.
Suleman, R., Wang, Z., Hui, T., Pan, T., Liu, H., Zhang, D., Utilization of Asian spices as a mitigation strategy to control heterocyclic aromatic amines in charcoal grilled lamb patties. Journal of Food Processing and Preservation, 43(11), 2019, e14182, 10.1111/jfpp.14182.
Teng, J., Hu, X., Tao, N., Wang, M., Impact and inhibitory mechanism of phenolic compounds on the formation of toxic Maillard reaction products in food. Frontiers of Agricultural Science and Engineering 5:3 (2018), 321–329, 10.15302/J-FASE-2017182.
Vauzour, D., Rodriguez-Mateos, A., Corona, G., Oruna-Concha, M.J., Spencer, J.P., Polyphenols and human health: Prevention of disease and mechanisms of action. Nutrients 2:11 (2010), 1106–1131, 10.3390/nu2111106.
Vitaglione, P., Fogliano, V., Use of antioxidants to minimize the human health risk associated to mutagenic/carcinogenic heterocyclic amines in food. Journal of Chromatography, B: Analytical Technologies in the Biomedical and Life Sciences 802:1 (2004), 189–199, 10.1016/j.jchromb.2003.09.029.
Xiong, Y.L., Inhibition of hazardous compound formation in muscle foods by antioxidative phytophenols. Annals of the New York Academy of Sciences 1398:1 (2017), 37–46, 10.1111/nyas.13368.
Yu, C., Shao, Z., Liu, B., Zhang, Y., Wang, S., Inhibition of 2-Amino-1-methyl-6-phenylimidazo [4,5-b]pyridine (PhIP) formation by alkoxy radical scavenging of flavonoids and their quantitative structure-activity relationship in a model system. Journal of Food Science 81:8 (2016), C1908–C1913, 10.1111/1750-3841.13381.
Zamora, R., Hidalgo, F.J., Formation of heterocyclic aromatic amines with the structure of aminoimidazoazarenes in food products. Food Chemistry, 313, 2020, 126128, 10.1016/j.foodchem.2019.126128.
Zöchling, S., Murkovic, M., Formation of the heterocyclic aromatic amine PhIP: Identification of precursors and intermediates. Food Chemistry 79 (2002), 125–134, 10.1016/S0308-8146(02)00214-5.