肉制品中杂环胺类物质的形成机制及控制技术的研究进展
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摘要
杂环胺是一类极易在烧烤类肉制品加工过程中产生的物质,过量摄入具有致癌或致突变风险。本文综述了肉制品加工过程中杂环胺类物质(包括氨基-咪唑-氮杂芳烃和氨基-咔啉类)的形成机制;分析了影响肉制品加工过程中杂环胺类物质形成因素,包括加工条件(温度与时间)、烹饪方法、前体物质含量和原料肉中水分含量;重点综述了杂环胺类物质的控制技术,如改善加工方式(微波加热预处理、包裹隔热食品辅料、酒类腌制)、添加外源抑制物如植物性天然抗氧化物(香辛料、茶叶提取物、果蔬及果蔬提取物)、保水性物质(纤维素、壳聚糖、淀粉)等,为加工肉制品中杂环胺的控制技术研发与应用提供理论指导与方法参考。
Heterocyclic aromatic amines are a class of substances that are easily produced during the processing of roasted meat products. Over-consumption may be carcinogenic or mutagenic. The formation mechanism of heterocyclic aromatic amines(including aminoimidazoaza-aromatics and amino-carbolines)in the processing of meat products were reviewed. The formation factors of heterocyclic amines in the processing of meat products were reviewed,including the processing conditions(temperature and time),processing methods,the content of precursor substances,and the moisture content of raw meat;the control technologies of heterocyclic aromatic amines were reviewed emphatically,such as the improvement of processing methods(microwave heating pretreatment,Wine pickling),adding exogenous inhibitors such as plant natural antioxidants(spices,tea extract,fruits and vegetables and fruit and vegetable extracts),water retention substances(cellulose,chitosan,starch),etc.,it provided theoretical guidance and reference for developing and applying control technology of heterocyclic amine in meat products.
Heterocyclic aromatic amines are a class of substances that are easily produced during the processing of roasted meat products. Over-consumption may be carcinogenic or mutagenic. The formation mechanism of heterocyclic aromatic amines(including aminoimidazoaza-aromatics and amino-carbolines)in the processing of meat products were reviewed. The formation factors of heterocyclic amines in the processing of meat products were reviewed,including the processing conditions(temperature and time),processing methods,the content of precursor substances,and the moisture content of raw meat;the control technologies of heterocyclic aromatic amines were reviewed emphatically,such as the improvement of processing methods(microwave heating pretreatment,Wine pickling),adding exogenous inhibitors such as plant natural antioxidants(spices,tea extract,fruits and vegetables and fruit and vegetable extracts),water retention substances(cellulose,chitosan,starch),etc.,it provided theoretical guidance and reference for developing and applying control technology of heterocyclic amine in meat products.
引文
[1]Szterk A.Heterocyclic aromatic amines in grilled beef:The influence of free amino acids,nitrogenous bases,nucleosides,protein and glucose on HAAs content[J].Journal of Food Composition&Analysis,2015,40:39-46.
[2]Sugimura T,Nagao M.Mutagenic factors in cooked foods[J].Crc Critical Reviews in Toxicology,1979,6(3):189-209.
[3]Sugimura T.Food and cancer[J].Toxicology,2002,181-182:17-21.
[4]Gibis M.Heterocyclic aromatic amines in cooked meat products:causes,formation,occurrence,and risk assessment[J].Comprehensive Reviews in Food Science&Food Safety,2016,15(2):269-302.
[5]郭海涛.加工条件对羊肉制品中杂环胺含量的影响[D].北京:中国农业科学院,2013.
[6]梅竞博.肉加工中杂环胺形成规律及控制技术的研究[D].天津:天津科技大学,2012.
[7]徐琦.水产品加热过程中12种杂环胺类化合物的变化规律研究[D].青岛:中国海洋大学,2012.
[8]万可慧.牛肉干制品中杂环胺的形成与控制研究[D].南京:南京农业大学,2013.
[9]Waller G,Feather M.The maillard reaction in foods and nutrition[M].Washington DC,1983:507-519.
[10]Milic'B L,Djilas S M,Canadanovic'-brunet J M.Synthesis of some heterocyclic aminoim idazoazarenes[J].Food Chemistry,1993,46(3):273-276.
[11]Bordas M,Moyano E,Puignou L,et al.Formation and stability of heterocyclic amines in a meat flavour model system:Effect of temperature,time and precursors[J].Journal of Chromatography B Analytical Technologies in the Biomedical&Life Sciences,2004,802(1):11-17.
[12]Yaylayan V Jocelyn ParéJ R R,Laing P,et al.The maillard reaction in food processing,human nutrition and physiology[M].Basel:Birkhuser,1990:115
[13]潘晗.酱肉中norharman和harman形成机理的研究[D].北京:中国农业科学院,2014.
[14]Oz F,Zikirov E.The effects of sous-vide cooking method on the formation ofheterocyclic aromatic amines in beef chops[J].LWT-Food Science and Technology,2015,64(1):120-125.
[15]Gibis M,Kruwinnus M,Weiss J.Impact of different panfrying conditions on the formation of heterocyclic aromatic amines and sensory quality in fried bacon[J].Food Chemistry,2015,168(23):383-389.
[16]Kondjoyan A,Chevolleau S,Grèv E E,et al.Formation of heterocyclic amines in slices of longissimus thoracis beef muscle subjected to jets of superheated steam[J].Food Chemistry,2010,119(1):19-26.
[17]Ke爧kekogˇlu 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 Science,2014,96(4):1446-1451.
[18]Skog K.Cooking procedures and food mutagens:A literature review[J].Food&Chemical Toxicology An International Journal Published for the British Industrial Biological Research Association,1993,31(9):655-675.
[19]Lee H,Lin M Y,Chan S C.Formation and identification of carcinogenic heterocyclic aromatic amines in boiled pork juice[J].Mutation Research/fundamental&Molecular Mechanisms of Mutagenesis,1994,308(1):77-88.
[20]Skog K,Jaegers TAD M.Incorporation of14C-glucose into mutagenic heterocyclic amines[M].Maillard Reactions in Chemistry,Food and Health,2005:147-152.
[21]Tai C Y,Lee K H,Chen B H.Effects of various additives on the formation of heterocyclic amines in fried fish fibre[J].Food Chemistry,2001,75(3):309-316.
[22]Zamora R,Alcón E,Hidalgo F J.Effect of amino acids on the formation of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine(Ph IP)in creatinine/phenylalanine and creatinine/phenylalanine/4-oxo-2-nonenal reaction mixtures[J].Food Chemistry,2013,141(4):4240-4245.
[23]Borgen E,Solyakov A,Skog K.Effects of precursor composition and water on the formation of heterocyclic amines in meat model systems[J].Food Chemistry,2001,74(1):11-19.
[24]Persson E,Sj9holm A I,Skog K.Effect of high water-holding capacity on the formation of heterocyclic amines in fried beefburgers[J].Journal of Agricultural&Food Chemistry,2003,51(15):4472-4477.
[25]Soladoye O P,Shand P,Dugan M E R,et al.Influence of cooking methods and storage time on lipid and protein oxidation and heterocyclic aromatic amines production in bacon[J].Food Research International,2017,99(1):660-669.
[26]Tengilimoglu-Metin M M,Hamzalioglu A,Gokmen V,et al.Inhibitory effect of hawthorn extract on heterocyclic aromatic amine formation in beef and chicken breast meat[J].Meat Science,2017,99(Pt 1):586-595.
[27]Liao G Z,Wang G Y,Zhang Y J,et al.Formation of heterocyclic amines during cooking of duck meat[J].Food Additives&Contaminants Part A Chemistry Analysis Control Exposure&Risk Assessment,2012,29(11):1668-1678.
[28]Jinap S,Mohdmokhtar M S,Farhadian A,et al.Effects of varying degrees of doneness on the formation of heterocyclic aromatic amines in chicken and beef satay[J].Meat Science,2013,94(2):202-207.
[29]黄鸣,黎锡流,李泽坤.微波与远红外线加热在食品加工中的应用[J].现代食品科技,2002,18(2):60-63.
[30]鄢嫣.烤肉中杂环胺的形成规律的研究[D].无锡:江南大学,2015.
[31]Busquets R,Mitjans D,Puignou L,et al.Quantification of heterocyclic amines from thermally processed meats selected from a small-scale population-based study[J].Molecular Nutrition&Food Research,2010,52(12):1408-1420.
[32]孟德敬.啤酒酿造过程中超氧化物歧化酶的研究[D].无锡:江南大学,2008.
[33]王晓宇.葡萄酒抗氧化活性及其检测方法的研究[D].咸阳:西北农林科技大学,2008.
[34]Viegas O,Moreira P S,Ferreira I M.Influence of beer marinades on reduction of carcinogenic heterocyclic aromatic amines in charcoal-grilled pork meat[J].Food Additives&Contaminants Part A Chemistry Analysis Control Exposure&Risk Assessment,2015,32(3):315-323.
[35]Rice-Evans C,Miller N,Paganga G.Antioxidant properties of phenolic compounds[J].Trends in Plant Science,1997,2(4):152-159.
[36]Arora D S,Kaur J.Antimicrobial activity of spices[J].International Journal of Antimicrobial Agents,1999,12(3):257-262.
[37]Jinap S,Iqbal S Z,Selvamr M P.Effect of selected local spices marinades on the reduction ofheterocyclic aminesin grilled beef[J].LWT-Food Science and Technology,2015,63(2):919-926.
[38]Zeng M,Zhang M,He Z,et al.Inhibitory profiles of chilli()pepper and capsaicin on heterocyclic amine formation inroast beef patties[J].Food Chemistry,2017,221:404-411.
[39]潘素君.不同类型茶多酚的抗氧化作用和抑菌效果的研究[D].长沙:湖南农业大学,2001.
[40]Jamali M A,Zhang Y,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):173-186.
[41]Rounds L,Havens C M,Feinstein Y,et al.Plant extracts,spices,and essential oils inactivate Escherichia coli O157∶H7 and reduce formation of potentially carcinogenic heterocyclic amines in cooked beef patties[J].Journal of Agricultural&Food Chemistry,2012,60(14):3792-3799.
[42]Sabally K,Sleno L,Jauffrit J A,et al.Inhibitory effects of apple peel polyphenol extract on the formation of heterocyclic amines in pan fried beef patties[J].Meat Science,2016,117:57-62.
[43]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 Chemistry,2012,134(2):766-774.
[44]Tengilimoglu-Metin M M,Kizil M.Reducing effect of artichoke extract on heterocyclic aromatic amine formation in beef and chicken breast meat[J].Meat Science,2017,134:68-75.
[45]Gibis M,Weiss J.Inhibitory Effect of cellulose fibers on the formation of heterocyclic aromatic amines in grilled beef patties[J].Food Chemistry,2017,229(15):828-836.
[46]Oz F,Kiziz M,Zaman A,et al.The effects of direct addition of low and medium molecular weight chitosan on the formation of heterocyclic aromatic amines in beef chop[J].LWT-Food Science and Technology,2016,65:861-867.
[47]鄢嫣,曾茂茂,陈洁,等.不同添加量的大豆分离蛋白和淀粉对烤猪肉中杂环胺形成的影响[J].食品工业科技,2016,37(22):324-328.
[2]Sugimura T,Nagao M.Mutagenic factors in cooked foods[J].Crc Critical Reviews in Toxicology,1979,6(3):189-209.
[3]Sugimura T.Food and cancer[J].Toxicology,2002,181-182:17-21.
[4]Gibis M.Heterocyclic aromatic amines in cooked meat products:causes,formation,occurrence,and risk assessment[J].Comprehensive Reviews in Food Science&Food Safety,2016,15(2):269-302.
[5]郭海涛.加工条件对羊肉制品中杂环胺含量的影响[D].北京:中国农业科学院,2013.
[6]梅竞博.肉加工中杂环胺形成规律及控制技术的研究[D].天津:天津科技大学,2012.
[7]徐琦.水产品加热过程中12种杂环胺类化合物的变化规律研究[D].青岛:中国海洋大学,2012.
[8]万可慧.牛肉干制品中杂环胺的形成与控制研究[D].南京:南京农业大学,2013.
[9]Waller G,Feather M.The maillard reaction in foods and nutrition[M].Washington DC,1983:507-519.
[10]Milic'B L,Djilas S M,Canadanovic'-brunet J M.Synthesis of some heterocyclic aminoim idazoazarenes[J].Food Chemistry,1993,46(3):273-276.
[11]Bordas M,Moyano E,Puignou L,et al.Formation and stability of heterocyclic amines in a meat flavour model system:Effect of temperature,time and precursors[J].Journal of Chromatography B Analytical Technologies in the Biomedical&Life Sciences,2004,802(1):11-17.
[12]Yaylayan V Jocelyn ParéJ R R,Laing P,et al.The maillard reaction in food processing,human nutrition and physiology[M].Basel:Birkhuser,1990:115
[13]潘晗.酱肉中norharman和harman形成机理的研究[D].北京:中国农业科学院,2014.
[14]Oz F,Zikirov E.The effects of sous-vide cooking method on the formation ofheterocyclic aromatic amines in beef chops[J].LWT-Food Science and Technology,2015,64(1):120-125.
[15]Gibis M,Kruwinnus M,Weiss J.Impact of different panfrying conditions on the formation of heterocyclic aromatic amines and sensory quality in fried bacon[J].Food Chemistry,2015,168(23):383-389.
[16]Kondjoyan A,Chevolleau S,Grèv E E,et al.Formation of heterocyclic amines in slices of longissimus thoracis beef muscle subjected to jets of superheated steam[J].Food Chemistry,2010,119(1):19-26.
[17]Ke爧kekogˇlu 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 Science,2014,96(4):1446-1451.
[18]Skog K.Cooking procedures and food mutagens:A literature review[J].Food&Chemical Toxicology An International Journal Published for the British Industrial Biological Research Association,1993,31(9):655-675.
[19]Lee H,Lin M Y,Chan S C.Formation and identification of carcinogenic heterocyclic aromatic amines in boiled pork juice[J].Mutation Research/fundamental&Molecular Mechanisms of Mutagenesis,1994,308(1):77-88.
[20]Skog K,Jaegers TAD M.Incorporation of14C-glucose into mutagenic heterocyclic amines[M].Maillard Reactions in Chemistry,Food and Health,2005:147-152.
[21]Tai C Y,Lee K H,Chen B H.Effects of various additives on the formation of heterocyclic amines in fried fish fibre[J].Food Chemistry,2001,75(3):309-316.
[22]Zamora R,Alcón E,Hidalgo F J.Effect of amino acids on the formation of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine(Ph IP)in creatinine/phenylalanine and creatinine/phenylalanine/4-oxo-2-nonenal reaction mixtures[J].Food Chemistry,2013,141(4):4240-4245.
[23]Borgen E,Solyakov A,Skog K.Effects of precursor composition and water on the formation of heterocyclic amines in meat model systems[J].Food Chemistry,2001,74(1):11-19.
[24]Persson E,Sj9holm A I,Skog K.Effect of high water-holding capacity on the formation of heterocyclic amines in fried beefburgers[J].Journal of Agricultural&Food Chemistry,2003,51(15):4472-4477.
[25]Soladoye O P,Shand P,Dugan M E R,et al.Influence of cooking methods and storage time on lipid and protein oxidation and heterocyclic aromatic amines production in bacon[J].Food Research International,2017,99(1):660-669.
[26]Tengilimoglu-Metin M M,Hamzalioglu A,Gokmen V,et al.Inhibitory effect of hawthorn extract on heterocyclic aromatic amine formation in beef and chicken breast meat[J].Meat Science,2017,99(Pt 1):586-595.
[27]Liao G Z,Wang G Y,Zhang Y J,et al.Formation of heterocyclic amines during cooking of duck meat[J].Food Additives&Contaminants Part A Chemistry Analysis Control Exposure&Risk Assessment,2012,29(11):1668-1678.
[28]Jinap S,Mohdmokhtar M S,Farhadian A,et al.Effects of varying degrees of doneness on the formation of heterocyclic aromatic amines in chicken and beef satay[J].Meat Science,2013,94(2):202-207.
[29]黄鸣,黎锡流,李泽坤.微波与远红外线加热在食品加工中的应用[J].现代食品科技,2002,18(2):60-63.
[30]鄢嫣.烤肉中杂环胺的形成规律的研究[D].无锡:江南大学,2015.
[31]Busquets R,Mitjans D,Puignou L,et al.Quantification of heterocyclic amines from thermally processed meats selected from a small-scale population-based study[J].Molecular Nutrition&Food Research,2010,52(12):1408-1420.
[32]孟德敬.啤酒酿造过程中超氧化物歧化酶的研究[D].无锡:江南大学,2008.
[33]王晓宇.葡萄酒抗氧化活性及其检测方法的研究[D].咸阳:西北农林科技大学,2008.
[34]Viegas O,Moreira P S,Ferreira I M.Influence of beer marinades on reduction of carcinogenic heterocyclic aromatic amines in charcoal-grilled pork meat[J].Food Additives&Contaminants Part A Chemistry Analysis Control Exposure&Risk Assessment,2015,32(3):315-323.
[35]Rice-Evans C,Miller N,Paganga G.Antioxidant properties of phenolic compounds[J].Trends in Plant Science,1997,2(4):152-159.
[36]Arora D S,Kaur J.Antimicrobial activity of spices[J].International Journal of Antimicrobial Agents,1999,12(3):257-262.
[37]Jinap S,Iqbal S Z,Selvamr M P.Effect of selected local spices marinades on the reduction ofheterocyclic aminesin grilled beef[J].LWT-Food Science and Technology,2015,63(2):919-926.
[38]Zeng M,Zhang M,He Z,et al.Inhibitory profiles of chilli()pepper and capsaicin on heterocyclic amine formation inroast beef patties[J].Food Chemistry,2017,221:404-411.
[39]潘素君.不同类型茶多酚的抗氧化作用和抑菌效果的研究[D].长沙:湖南农业大学,2001.
[40]Jamali M A,Zhang Y,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):173-186.
[41]Rounds L,Havens C M,Feinstein Y,et al.Plant extracts,spices,and essential oils inactivate Escherichia coli O157∶H7 and reduce formation of potentially carcinogenic heterocyclic amines in cooked beef patties[J].Journal of Agricultural&Food Chemistry,2012,60(14):3792-3799.
[42]Sabally K,Sleno L,Jauffrit J A,et al.Inhibitory effects of apple peel polyphenol extract on the formation of heterocyclic amines in pan fried beef patties[J].Meat Science,2016,117:57-62.
[43]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 Chemistry,2012,134(2):766-774.
[44]Tengilimoglu-Metin M M,Kizil M.Reducing effect of artichoke extract on heterocyclic aromatic amine formation in beef and chicken breast meat[J].Meat Science,2017,134:68-75.
[45]Gibis M,Weiss J.Inhibitory Effect of cellulose fibers on the formation of heterocyclic aromatic amines in grilled beef patties[J].Food Chemistry,2017,229(15):828-836.
[46]Oz F,Kiziz M,Zaman A,et al.The effects of direct addition of low and medium molecular weight chitosan on the formation of heterocyclic aromatic amines in beef chop[J].LWT-Food Science and Technology,2016,65:861-867.
[47]鄢嫣,曾茂茂,陈洁,等.不同添加量的大豆分离蛋白和淀粉对烤猪肉中杂环胺形成的影响[J].食品工业科技,2016,37(22):324-328.