热加工食品中杂环胺形成及抑制机制
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摘要
杂环胺是富含蛋白质的食品原料在热加工过程中产生的危害物,种类众多,且同一杂环胺有多条生成途径。本文主要综述了杂环胺的形成途径以及抑制机制,喹啉类和喹喔啉类可通过肌酸酐、葡萄糖和氨基酸的美拉德反应途径以及自由基途径形成;吡啶类(2-氨基-1甲基-6苯基-咪唑并[4,5-b]吡啶)可由苯丙氨酸的热解产物苯乙醛与肌酸酐经过一系列复杂的反应生成;氨基咔啉类主要是蛋白或氨基酸在250℃以上发生降解和热分解生成。添加酚类抗氧化剂、香辛料提取物、大蒜、洋葱、维生素等组分,可以清除自由基、捕获苯乙醛、抑制美拉德反应等机制对喹(喔)啉类和吡啶类(2-氨基-1甲基-6苯基-咪唑并[4,5-b]吡啶)等生成进行抑制。为有效阻断杂环胺的生成,去除其潜在危害提供理论支撑。
Heterocyclic amines are the hazardous materials produced by protein-rich food materials during thermal processing. There are many types of heterocyclic amines, and the same heterocyclic amine has multiple routes of formation. This paper reviewed the formation of heterocyclic amines and their inhibitory mechanisms, imidazoquinolines and imidazoquinoxalines could be formed by the Maillard reaction of creatinine, glucose and amino acids, and the free radical pathway. The 2-amino-1-methyl-6-phenyl-imidazo[4,5-b]pyridine could be formed by phenylacetaldehyde, phenylalanine pyrolysis product, and creatinine through a series of complex reactions. Aminoporphyrins were mainly fromed from proteins or amino acids that degraded and thermally decomposed at temperatures above 250 ℃. The addition of phenolic antioxidants, spice extracts, garlic, oinions, vitamins and other components could eliminate free radicals, capture phenylacetaldehyde, and inhibit Maillard reaction and other mechanisms to inhibit the generation of imidazoquino(xa)lines and pyridine 2-amino-1-methyl-6-phenyl-imidazole and [4,5-b] pyridine. It provides theoretical support for effectively blocking the generation of heterocyclic amines and removing their potential hazards.
Heterocyclic amines are the hazardous materials produced by protein-rich food materials during thermal processing. There are many types of heterocyclic amines, and the same heterocyclic amine has multiple routes of formation. This paper reviewed the formation of heterocyclic amines and their inhibitory mechanisms, imidazoquinolines and imidazoquinoxalines could be formed by the Maillard reaction of creatinine, glucose and amino acids, and the free radical pathway. The 2-amino-1-methyl-6-phenyl-imidazo[4,5-b]pyridine could be formed by phenylacetaldehyde, phenylalanine pyrolysis product, and creatinine through a series of complex reactions. Aminoporphyrins were mainly fromed from proteins or amino acids that degraded and thermally decomposed at temperatures above 250 ℃. The addition of phenolic antioxidants, spice extracts, garlic, oinions, vitamins and other components could eliminate free radicals, capture phenylacetaldehyde, and inhibit Maillard reaction and other mechanisms to inhibit the generation of imidazoquino(xa)lines and pyridine 2-amino-1-methyl-6-phenyl-imidazole and [4,5-b] pyridine. It provides theoretical support for effectively blocking the generation of heterocyclic amines and removing their potential hazards.
引文
[1]Turesky RJ,Konorev D,Fan XY,et al.Effect of cytochrome P450reductase deficiency on 2-amino-9H-pyrido[2,3-b]indole metabolism and DNA adduct formation in liver and extrahepatic tissues of mice[J].Chem Res Toxicol,2015,28(12):2400-2410.
[2]Xiao S,Guo JS,Yun BH,et al.Biomonitoring DNA adducts of cooked meat carcinogens in human prostate by nano liquid chromatography-high resolution tandem mass spectrometry:Identification of2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine DNA adduct[J].Anal Chem,2016,88(24):12508-12515.
[3]Pezdirc M,Zegura B,Filipic M.Genotoxicity and induction of DNAdamage responsive gens by food-borne heterocyclic aromatic amines in human hepatoma HepG2 cells[J].Food Chem Toxicol,2013,59:386-394.
[4]Shabbir MA,Raza A,Anjum FM,et al.Effect of thermal treatment on meat proteins with special reference to heterocyclic aromatic amines(HAAs)[J].Crit Rev Food Sci Nutr,2015,55(1):82-93.
[5]Gibis M.Heterocyclic aromatic amines in cooked meat products:causes,formation,occurrence,and risk assessment[J].Compr Rev Food Sci Food Saf,2016,15:269-302.
[6]Meurillon M,Engel E.Mitigation strategies to reduce the impact of heterocyclic aromatic amines in proteinaceous foods[J].Trends Food Sci Technol,2016,50:70-84.
[7]Barbir A,Linseisen J,Hermann S,et al.Effects of phenotypes in heterocyclic aromatic amine(HCA)metabolism-related genes on the association of HCA intake with the risk of colorectal adenomas[J].Cancer Causes Control,2012,23:1429-1442.
[8]IARC.Some naturally occurring substances:food items and constituents,heterocyclic aromatic amines and mycotoxins,in IARC Monographs on the Evaluation of Carcinogenic Risks of Chemicals to Humans,No.56[Z].1993.
[9]Augustsson K,Skog K,Jagerstad M,et al.Dietary heterocyclic amines and cancer of the colon,rectum,bladder,and kidney:A population-based study[J].Lancet,1999,353:703-707.
[10]Sinha R,Kulldorff M,Swanson CA,et al.Dietary heterocyclic amines and the risk of lung cancer among Missouri women[J].Cancer Res,2000,60:3753-3756.
[11]Pearson AM,Chen CH,Gray JI,et al.Mechanism(s)involved in meat mutagen formation and inhibition[J].Free Radic Biol Med,1992,13(2):161-167.
[12]Jagerstad M,Laser-Reutersward A,Oste R,et al.Creatinine and maillard reaction products as precursors of mutagenic compounds formed in fried beef[M].Washington:Waller&Feather,1986.
[13]Skog K,Jagerstad M.Incorporation of carbon atoms from glucose into¨the food mutagens MeIQx and 4,8-DiMeIQx using carbon-14-labeled glucose in a model system[J].Carcinogene,1993,14:2027-2031.
[14]Skog K,Jagerstad M.Incorporation of 14C-glucose into mutagenic heterocyclic amines[M].I UK:Woodhead Publishing,2005.
[15]Murkovic M,Weber HJ,Geiszler S,et al.Formation of the food associated carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine(PhIP)in model systems[J].Food Chem,1999,65(2):233-237.
[16]Zamora R,Alcon E,Hidalgo FJ.Ammonia and formaldehyde participate in the formation of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine(PhIP)in addition to create(ni)ne and phenylacetaldehyde[J].Food Chem,2014,155,74-80.
[17]Hidalgo FJ,Navarro JL,Zamora R.Structure-activity relationship(SAR)of phenolics for 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine(PhIP)formation in phenylalanine/creatinine reaction mixtures including(or not)oxygen and lipid hydroperoxides[J].J Agric Food Chem,2018,66:255-264.
[18]Gibis M,Weiss J.Formation of heterocyclic amines in salami and ham pizza toppings during baking of frozen pizza[J].J Food Sci,2013,78:C832-C838.
[19]Rahman U,Sahar A,Khan MI,et al.Production of heterocyclic aromatic amines in meat:Chemistry,health risks and inhibition:A review[J].LWT-Food Sci Technol,2014,59,229-233.
[20]Arvidsson P,Van-Boekel MAJS,Skog K,et al.Kinetics of formation of polar heterocyclic amines in a meat model system[J].J Food Sci,1997,62:911-916.
[21]Arvidsson P,Van-Boekel MAJS,Skog K,et al.Formation of heterocyclic amines in a meat juice model system[J].J Food Sci,1999,64:216-221.
[22]Xiong YL.Inhibition of hazardous compound formation in muscle foods by antioxidative phytophenols[Z].2017.
[23]Alaejos MS,Afonso AM.Factors that affect the content of heterocyclic aromatic amines in foods[J].Compr Rev Food Sci Food Saf,2016,15:269-302.
[24]Rannou C,Laroque D,Renault E.Mitigation strategies of acrylamide,furans,heterocyclic amines and browning during the Maillard reaction in food[J].Food Res Int,2016,90:154-176.
[25]Vitaglione P,Fogliano V.Use of antioxidants to minimize the human health risk associated to mutagenic/carcinogenic heterocyclic amines in food[J].J Chromatogra B,2004,802:189-199.
[26]Janoszka B.Heterocyclic amines and azaarenes in pan-fried meat and its gravy fried without additives and in the presence of onion and garlic[J].Food Chem,2010,120:463-473.
[27]Soladoye OP,Shand P,Dugan MER.Influence of cooking methods and storage time on lipid and protein oxidation and heterocyclic aromatic amines production in bacon[J].Food Res Int,2017,99:660-669.
[28]Chiu CP,Yang DY,Chen BH.Formation of heterocyclic amines in cooked chicken legs[J].J Food Protect,1998,61(6):712-719.
[29]Felton JS,Knize MG,Roper M,et al.Chemical analysis,prevention,and low-level dosimetry of heterocyclic amines from cooked food[J].Cancer Res,1992,52(7):2103-2107.
[30]Felton JS,Fultz E,Dolbeare FA,et al.Effect of microwave pretreatment on heterocyclic aromatic amine mutagens/carcinogens in fried beef patties[J].Food Chem Toxicol,1994,32(10):897-903.
[31]Abdulkarim BG,Smith JS.Heterocyclic amines in fresh and processed meat products[J].J Agric Food Chem,1998,46(11):4680-4687.
[32]Stavric B,Matula TI,Lau BPY,et al.Analysis of cold cuts for the presence of mutagenic heterocyclic aromatic amines[J].Faseb J,1996,10(3):485,2799.
[33]Zimmerli B,Rhyn P,Zoller O,et al.Occurrence of heterocyclic aromatic amines in the Swiss diet:Analytical methods,exposure estimation and risk assessment[J].Food Addit Contam,2001,18(6):533-551.
[34]Skog K,Augustsson K,Steineck G,et al.Polar¨and non-polar heterocyclic amines in cooked fish and meat products and their corresponding pan residues[J].Food Chem Toxicol,1997,35(6):555-565.
[35]Jaeger H,Janositz A,Knorr D.The Maillard reaction and its control during food processing.The potential of emerging technologies[J].Pathol Biol,2010,58:207-213.
[36]Lund MN,Ray CA.Control of Maillard reactions in foods:Strategies and chemical mechanisms[J].J Agric Food Chem,2017,65(23):4537-4552.
[37]Kikugawa K.Involvement of free radicals in the formation of heterocyclic amines and prevention by antioxidants[J].Cancer Lett,1999,143:123-126.
[38]Gibis M,Weiss J.Antioxidant capacity and inhibitory effect of grape seed and rosemary extract in marinades on the formation of heterocyclic amines in fried beef patties[J].Food Chem,2012,134:766-774.
[39]Zeng MM,Zhang MR,He ZY,et al.Inhibitory profiles of chilli pepper and capsaicin on heterocyclic amine formation in roast beef patties[J].Food Chem,2017,221:404-411.
[40]Zhang Y,Luo Z,Shao ZP,et al.Effects of antioxidants of bamboo leaves and flavonoids on 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine(PhIP)formation in chemical model systems[J].J Agric Food Chem,2014,62:4798-4802.
[41]Yu CD,Shao ZP,Liu B,et al.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[J].J Food Sci,2016,81(8):1908-1913.
[42]Viegas O,Moreira PS,Ferreira I.Influence of beer marinades on the reduction of carcinogenic heterocyclic aromatic amines in charcoal-grilled pork meat[J].Food Addit Contam:Part A,2015,32(3):315-323.
[43]Jamali MA,Zhang YW,Teng H,et al.Inhibitory effect of Rosa rugosa tea extract on the formation of heterocyclic amines in meat patties at different temperatures[J].Molecules,2016,21(2):173.
[44]Keskekoglu H,Uren A.Inhibitory effects of pomegranate seed extract on the formation of heterocyclic aromatic amines in beef and chicken meatballs after cooking by four different methods[J].Meat Sci,2014,96(4):1446-1451.
[45]Yu D,Chen MS,Yu SJ.Effect of sugarcane molasses extract on the formation of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine(PhIP)in a model system[J].Food Chem,2016,197(Part A):924-929.
[46]Lu F,Kuhnle GK,Cheng QF.Vegetable oil as fat replacer inhibits formation of heterocyclic amines and polycyclic aromatic hyrdocarbons in reduced fat pork patties[J].Food Control,2017,81:113-125.
[47]Cheng KW,Chen F,Wang MF.Inhibitory activities of dietary phenolic compounds on heterocyclic amine formation in both chemical model system and beef patties[J].Mol Nutr Food Res,2007,51(8):969-976.
[48]Zeng MM,Li Y,He ZY,et al.Effect of phenolic compounds from spices consumed in China on heterocyclic amine profiles in roast beef patties by UPLC-MS/MS and multivariate analysis[J].Meat Sci,2016,116:50-57.
[49]Wong D,Cheng KW,Wang MF.Inhibition of heterocyclic amine formation by water-soluble vitamins in maillard reaction model systems and beef patties[J].Food Chem,2012,133:760-766.
[50]Zhou B,Zhao YL,Wang XC,et al.Unraveling the inhibitory effect of dihydromyricetin on heterocyclic aromatic amines formation[J].J Sci Food Agric,2018,98(5):1988-1994.
[51]Linghu ZY,Karim F,Smith JS.Amino acids inhibitory effects and mechanism on 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine(PhIP)formation in the maillard reaction model systems[J].J Food Sci,2017,82(12):3037-3045.
[52]Kataoka H,Miyake M,Saito K,et al.Formation of heterocyclic amine-amino acid adducts by heating in a model system[J].Food Chem,2012,130:725-729.
[53]Shin HS,Strasburg GM,Gray JI.A model system study of the inhibition of heterocyclic aromatic amine formation by organosulfur compounds[J].J Agric Food Chem,2002,50:7684-7690.
[54]Gibis M.Effect of oil marinades with garlic,onion,and lemon juice on the formation of heterocyclic aromatic amines in fried beef patties[J].J Agric Food Chem,2007,55:10240-10247.
[55]Krone CA,Yeh SM,Iwaoka WT.Mutagen formation during commercial processing of foods[J].Environ Health Perspect,1986,67:75-88.
[2]Xiao S,Guo JS,Yun BH,et al.Biomonitoring DNA adducts of cooked meat carcinogens in human prostate by nano liquid chromatography-high resolution tandem mass spectrometry:Identification of2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine DNA adduct[J].Anal Chem,2016,88(24):12508-12515.
[3]Pezdirc M,Zegura B,Filipic M.Genotoxicity and induction of DNAdamage responsive gens by food-borne heterocyclic aromatic amines in human hepatoma HepG2 cells[J].Food Chem Toxicol,2013,59:386-394.
[4]Shabbir MA,Raza A,Anjum FM,et al.Effect of thermal treatment on meat proteins with special reference to heterocyclic aromatic amines(HAAs)[J].Crit Rev Food Sci Nutr,2015,55(1):82-93.
[5]Gibis M.Heterocyclic aromatic amines in cooked meat products:causes,formation,occurrence,and risk assessment[J].Compr Rev Food Sci Food Saf,2016,15:269-302.
[6]Meurillon M,Engel E.Mitigation strategies to reduce the impact of heterocyclic aromatic amines in proteinaceous foods[J].Trends Food Sci Technol,2016,50:70-84.
[7]Barbir A,Linseisen J,Hermann S,et al.Effects of phenotypes in heterocyclic aromatic amine(HCA)metabolism-related genes on the association of HCA intake with the risk of colorectal adenomas[J].Cancer Causes Control,2012,23:1429-1442.
[8]IARC.Some naturally occurring substances:food items and constituents,heterocyclic aromatic amines and mycotoxins,in IARC Monographs on the Evaluation of Carcinogenic Risks of Chemicals to Humans,No.56[Z].1993.
[9]Augustsson K,Skog K,Jagerstad M,et al.Dietary heterocyclic amines and cancer of the colon,rectum,bladder,and kidney:A population-based study[J].Lancet,1999,353:703-707.
[10]Sinha R,Kulldorff M,Swanson CA,et al.Dietary heterocyclic amines and the risk of lung cancer among Missouri women[J].Cancer Res,2000,60:3753-3756.
[11]Pearson AM,Chen CH,Gray JI,et al.Mechanism(s)involved in meat mutagen formation and inhibition[J].Free Radic Biol Med,1992,13(2):161-167.
[12]Jagerstad M,Laser-Reutersward A,Oste R,et al.Creatinine and maillard reaction products as precursors of mutagenic compounds formed in fried beef[M].Washington:Waller&Feather,1986.
[13]Skog K,Jagerstad M.Incorporation of carbon atoms from glucose into¨the food mutagens MeIQx and 4,8-DiMeIQx using carbon-14-labeled glucose in a model system[J].Carcinogene,1993,14:2027-2031.
[14]Skog K,Jagerstad M.Incorporation of 14C-glucose into mutagenic heterocyclic amines[M].I UK:Woodhead Publishing,2005.
[15]Murkovic M,Weber HJ,Geiszler S,et al.Formation of the food associated carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine(PhIP)in model systems[J].Food Chem,1999,65(2):233-237.
[16]Zamora R,Alcon E,Hidalgo FJ.Ammonia and formaldehyde participate in the formation of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine(PhIP)in addition to create(ni)ne and phenylacetaldehyde[J].Food Chem,2014,155,74-80.
[17]Hidalgo FJ,Navarro JL,Zamora R.Structure-activity relationship(SAR)of phenolics for 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine(PhIP)formation in phenylalanine/creatinine reaction mixtures including(or not)oxygen and lipid hydroperoxides[J].J Agric Food Chem,2018,66:255-264.
[18]Gibis M,Weiss J.Formation of heterocyclic amines in salami and ham pizza toppings during baking of frozen pizza[J].J Food Sci,2013,78:C832-C838.
[19]Rahman U,Sahar A,Khan MI,et al.Production of heterocyclic aromatic amines in meat:Chemistry,health risks and inhibition:A review[J].LWT-Food Sci Technol,2014,59,229-233.
[20]Arvidsson P,Van-Boekel MAJS,Skog K,et al.Kinetics of formation of polar heterocyclic amines in a meat model system[J].J Food Sci,1997,62:911-916.
[21]Arvidsson P,Van-Boekel MAJS,Skog K,et al.Formation of heterocyclic amines in a meat juice model system[J].J Food Sci,1999,64:216-221.
[22]Xiong YL.Inhibition of hazardous compound formation in muscle foods by antioxidative phytophenols[Z].2017.
[23]Alaejos MS,Afonso AM.Factors that affect the content of heterocyclic aromatic amines in foods[J].Compr Rev Food Sci Food Saf,2016,15:269-302.
[24]Rannou C,Laroque D,Renault E.Mitigation strategies of acrylamide,furans,heterocyclic amines and browning during the Maillard reaction in food[J].Food Res Int,2016,90:154-176.
[25]Vitaglione P,Fogliano V.Use of antioxidants to minimize the human health risk associated to mutagenic/carcinogenic heterocyclic amines in food[J].J Chromatogra B,2004,802:189-199.
[26]Janoszka B.Heterocyclic amines and azaarenes in pan-fried meat and its gravy fried without additives and in the presence of onion and garlic[J].Food Chem,2010,120:463-473.
[27]Soladoye OP,Shand P,Dugan MER.Influence of cooking methods and storage time on lipid and protein oxidation and heterocyclic aromatic amines production in bacon[J].Food Res Int,2017,99:660-669.
[28]Chiu CP,Yang DY,Chen BH.Formation of heterocyclic amines in cooked chicken legs[J].J Food Protect,1998,61(6):712-719.
[29]Felton JS,Knize MG,Roper M,et al.Chemical analysis,prevention,and low-level dosimetry of heterocyclic amines from cooked food[J].Cancer Res,1992,52(7):2103-2107.
[30]Felton JS,Fultz E,Dolbeare FA,et al.Effect of microwave pretreatment on heterocyclic aromatic amine mutagens/carcinogens in fried beef patties[J].Food Chem Toxicol,1994,32(10):897-903.
[31]Abdulkarim BG,Smith JS.Heterocyclic amines in fresh and processed meat products[J].J Agric Food Chem,1998,46(11):4680-4687.
[32]Stavric B,Matula TI,Lau BPY,et al.Analysis of cold cuts for the presence of mutagenic heterocyclic aromatic amines[J].Faseb J,1996,10(3):485,2799.
[33]Zimmerli B,Rhyn P,Zoller O,et al.Occurrence of heterocyclic aromatic amines in the Swiss diet:Analytical methods,exposure estimation and risk assessment[J].Food Addit Contam,2001,18(6):533-551.
[34]Skog K,Augustsson K,Steineck G,et al.Polar¨and non-polar heterocyclic amines in cooked fish and meat products and their corresponding pan residues[J].Food Chem Toxicol,1997,35(6):555-565.
[35]Jaeger H,Janositz A,Knorr D.The Maillard reaction and its control during food processing.The potential of emerging technologies[J].Pathol Biol,2010,58:207-213.
[36]Lund MN,Ray CA.Control of Maillard reactions in foods:Strategies and chemical mechanisms[J].J Agric Food Chem,2017,65(23):4537-4552.
[37]Kikugawa K.Involvement of free radicals in the formation of heterocyclic amines and prevention by antioxidants[J].Cancer Lett,1999,143:123-126.
[38]Gibis M,Weiss J.Antioxidant capacity and inhibitory effect of grape seed and rosemary extract in marinades on the formation of heterocyclic amines in fried beef patties[J].Food Chem,2012,134:766-774.
[39]Zeng MM,Zhang MR,He ZY,et al.Inhibitory profiles of chilli pepper and capsaicin on heterocyclic amine formation in roast beef patties[J].Food Chem,2017,221:404-411.
[40]Zhang Y,Luo Z,Shao ZP,et al.Effects of antioxidants of bamboo leaves and flavonoids on 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine(PhIP)formation in chemical model systems[J].J Agric Food Chem,2014,62:4798-4802.
[41]Yu CD,Shao ZP,Liu B,et al.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[J].J Food Sci,2016,81(8):1908-1913.
[42]Viegas O,Moreira PS,Ferreira I.Influence of beer marinades on the reduction of carcinogenic heterocyclic aromatic amines in charcoal-grilled pork meat[J].Food Addit Contam:Part A,2015,32(3):315-323.
[43]Jamali MA,Zhang YW,Teng H,et al.Inhibitory effect of Rosa rugosa tea extract on the formation of heterocyclic amines in meat patties at different temperatures[J].Molecules,2016,21(2):173.
[44]Keskekoglu H,Uren A.Inhibitory effects of pomegranate seed extract on the formation of heterocyclic aromatic amines in beef and chicken meatballs after cooking by four different methods[J].Meat Sci,2014,96(4):1446-1451.
[45]Yu D,Chen MS,Yu SJ.Effect of sugarcane molasses extract on the formation of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine(PhIP)in a model system[J].Food Chem,2016,197(Part A):924-929.
[46]Lu F,Kuhnle GK,Cheng QF.Vegetable oil as fat replacer inhibits formation of heterocyclic amines and polycyclic aromatic hyrdocarbons in reduced fat pork patties[J].Food Control,2017,81:113-125.
[47]Cheng KW,Chen F,Wang MF.Inhibitory activities of dietary phenolic compounds on heterocyclic amine formation in both chemical model system and beef patties[J].Mol Nutr Food Res,2007,51(8):969-976.
[48]Zeng MM,Li Y,He ZY,et al.Effect of phenolic compounds from spices consumed in China on heterocyclic amine profiles in roast beef patties by UPLC-MS/MS and multivariate analysis[J].Meat Sci,2016,116:50-57.
[49]Wong D,Cheng KW,Wang MF.Inhibition of heterocyclic amine formation by water-soluble vitamins in maillard reaction model systems and beef patties[J].Food Chem,2012,133:760-766.
[50]Zhou B,Zhao YL,Wang XC,et al.Unraveling the inhibitory effect of dihydromyricetin on heterocyclic aromatic amines formation[J].J Sci Food Agric,2018,98(5):1988-1994.
[51]Linghu ZY,Karim F,Smith JS.Amino acids inhibitory effects and mechanism on 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine(PhIP)formation in the maillard reaction model systems[J].J Food Sci,2017,82(12):3037-3045.
[52]Kataoka H,Miyake M,Saito K,et al.Formation of heterocyclic amine-amino acid adducts by heating in a model system[J].Food Chem,2012,130:725-729.
[53]Shin HS,Strasburg GM,Gray JI.A model system study of the inhibition of heterocyclic aromatic amine formation by organosulfur compounds[J].J Agric Food Chem,2002,50:7684-7690.
[54]Gibis M.Effect of oil marinades with garlic,onion,and lemon juice on the formation of heterocyclic aromatic amines in fried beef patties[J].J Agric Food Chem,2007,55:10240-10247.
[55]Krone CA,Yeh SM,Iwaoka WT.Mutagen formation during commercial processing of foods[J].Environ Health Perspect,1986,67:75-88.