葡萄酒中氨基甲酸乙酯的研究进展
详细信息    查看全文 | 推荐本文 |
  • 英文篇名:Ethyl Carbamate in Wine: A Review
  • 作者:刘洋 ; 李运奎 ; 韩富亮 ; 王婉妮 ; 刘亮
  • 英文作者:LIU Yang;LI Yunkui;HAN Fuliang;WANG Wanni;LIU Liang;College of Enology, Northwest A & F University;Shaanxi Engineering Research Center for Viti-viniculture;Heyang Experimental Demonstration Station of Viticulture, Northwest A & F University;
  • 关键词:葡萄酒 ; 氨基甲酸乙酯 ; 形成机制 ; 影响因素 ; 调控措施 ; 食品安全
  • 英文关键词:wine;;ethyl carbamate;;formation mechanism;;effect factors;;regulatory strategies;;food safety
  • 中文刊名:SPKX
  • 英文刊名:Food Science
  • 机构:西北农林科技大学葡萄酒学院;陕西省葡萄与葡萄酒工程技术研究中心;西北农林科技大学合阳葡萄试验示范站;
  • 出版日期:2019-04-15
  • 出版单位:食品科学
  • 年:2019
  • 期:v.40;No.596
  • 基金:“十三五”国家重点研发计划重点专项(2016YFD0400500);; 陕西省重点研发计划资助项目(2017NY-184)
  • 语种:中文;
  • 页:SPKX201907042
  • 页数:7
  • CN:07
  • ISSN:11-2206/TS
  • 分类号:297-303
摘要
氨基甲酸乙酯是一种广泛存在于葡萄酒等发酵食品中的致癌物质,具有致突变性、多位点致癌性以及免疫抑制性和心率抑制性。本文对葡萄酒中氨基甲酸乙酯的危害、国际限量标准、质量浓度变化、形成机制、影响因素及调控消除手段进行了系统综述,以期为提高我国葡萄酒安全性提供科学依据。
        Ethyl carbamate(EC), a carcinogen commonly found in wine and other fermented foods, has mutagenicity,multisite carcinogenicity, immunosuppressing and heart rate inhibitory activity. This article presents a systematic review of the health hazards and formation mechanism of EC in wine, worldwide maximum residue limits for it as well as changes in its concentration during wine storage, the factors affecting it and regulatory strategies to reduce and even eliminate it. With this review, we hope to provide a scienti?c basis for improving the safety of wines in China.
引文
[1]AUTHORITY E F S.Ethyl carbamate and hydrocyanic acid in food and beverages scientific opinion of the panel on contaminants[J].European Food Safety Authority Journal,2007,5(10):1-44.DOI:10.2903/j.efsa.2007.551.
    [2]OUGH C S.Ethylcarbamate in fermented beverages and foods.I.naturally occurring ethylcarbamate[J].Journal of Agricultural and Food Chemistry,1976,24(2):323-328.DOI:10.1021/jf60204a033.
    [3]GOWD V,SU H,KARLOVSKY P,et al.Ethyl carbamate:an emerging food and environmental toxicant[J].Food Chemistry,2018,248:312-321.DOI:10.1016/j.foodchem.2017.12.072.
    [4]国家进出口商品检验局.出口酒类中氨基甲酸乙酯残留量检验方法:SN 0285-1993[S].北京:中国标准出版社,1994:1-8.
    [5]ZHOU W Y,FANG R S,CHEN Q H.Effect of gallic and protocatechuic acids on the metabolism of ethyl carbamate in Chinese yellow rice wine brewing[J].Food Chemistry,2017,233:174-181.DOI:10.1016/j.foodchem.2017.04.113.
    [6]WU P,CAI C,SHEN X,et al.Formation of ethyl carbamate and changes during fermentation and storage of yellow rice wine[J].Food Chemistry,2014,152(6):108-112.DOI:10.1016/j.foodchem.2013.11.135.
    [7]FANG R S,DONG Y C,LI H J,et al.Ethyl carbamate formation regulated by Saccharomyces cerevisiae ZJU in the processing of Chinese yellow rice wine[J].International Journal of Food Science and Technology,2015,50(3):626-632.DOI:10.1111/ijfs.12665.
    [8]WU H M,CHEN L,PAN G S,et al.Study on the changing concentration of ethyl carbamate in yellow rice wine during production and storage by gas chromatography/mass spectrometry[J].European Food Research and Technology,2012,235(5):779-782.DOI:10.1007/s00217-012-1807-7.
    [9]LAGO L O,NICOLLI K P,MARQUES A B,et al.Influence of ripeness and maceration of the grapes on levels of furan and carbonyl compounds in wine:simultaneous quantitative determination and assessment of the exposure risk to these compounds[J].Food Chemistry,2017,230:594-603.DOI:10.1016/j.foodchem.2017.03.090.
    [10]MORENO-ARRIBAS M V,SUáLDEA B A B,LONVAUD-FUNELA.Metabolomic approaches in the study of wine benefits in human health[M].Berlin:Springer International Publishing,2016:3-26.DOI:10.1007/978-3-319-24514-0_1.
    [11]XUE J,FU F,LIANG M,et al.Ethyl carbamate production kinetics during wine storage[J].South African Journal of Enology and Viticulture,2015,36(2):277-284.DOI:10.21548/36-2-961.
    [12]李华,王仁俊.氨基甲酸乙酯对蟾蜍心电活动的影响[J].沈阳师范大学学报(自然科学版),2016,34(3):263-266.DOI:10.3969/j.issn.1673-5862.2016.03.002.
    [13]徐彩菊,蔡德雷,宋燕华,等.氨基甲酸乙酯对小鼠免疫功能的影响[J].浙江预防医学,2015,27(4):362-365.DOI:10.19485/j.cnki.issn1007-0931.2015.04.010.
    [14]JIAO Z H,DONG Y C,CHEN Q H.Ethyl carbamate in fermented beverages:presence,analytical chemistry,formation mechanism,and mitigation proposals[J].Comprehensive Reviews in Food Science and Food Safety,2014,13(4):611-626.DOI:10.1111/1541-4337.12084.
    [15]WEBER J V,SHARYPOV V I.Ethyl carbamate in foods and beverages:a review[J].Environmental Chemistry Letters,2009,7(3):233-247.DOI:10.1007/s10311-008-0168-8.
    [16]PARK K,LIEM A,STEWART B C,et al.Vinyl carbamate epoxide,a major strong electrophilic,mutagenic and carcinogenic metabolite of vinyl carbamate and ethyl carbamate(urethane)[J].Carcinogenesis,1993,14(3):441-450.DOI:10.1093/carcin/14.3.441.
    [17]SAKANO K,OIKAWA S,HIRAKU Y,et al.Metabolism of carcinogenic urethane to nitric oxide is involved in oxidative DNAdamage[J].Free Radical Biology and Medicine,2002,33(5):703-714.DOI:10.1016/S0891-5849(02)00969-3.
    [18]ADDITIVES J F W E,ORGANIZATION W H.Evaluation of certain food contaminants:sixty-fourth report of the Joint FAO/WHO Expert Committee on Food Additives[J].World Health Organization Technical Report,2015,930(3):1-99.
    [19]STEVENS D F,OUGH C S.Ethyl carbamate formation:reaction of urea and citrulline with ethanol in wine under low to normal temperature conditions[J].American Journal of Enology and Viticulture,1993,44(3):309-312.
    [20]ZIMMERLI B,SCHLATTER J.Ethyl carbamate:analytical methodology,occurrence,formation,biological activity and risk assessment[J].Mutation Research/Genetic Toxicology,1991,259(3/4):325-350.DOI:10.1016/0165-1218(91)90126-7.
    [21]THORGEIRSSON U P,DALGARD D W,REEVES J,et al.Tumor incidence in a chemical carcinogenesis study of nonhuman primates[J].Regulatory Toxicology and Pharmacology,1994,19(2):130-151.DOI:10.1006/rtph.1994.1013.
    [22]CHUN S H,CHA Y N,KIM C.Urethane increases reactive oxygen species and activates extracellular signal-regulated kinase in RAW 264.7macrophages and A549 lung epithelial cells[J].Archives of Pharmacal Research,2013,36(6):775-782.DOI:10.1007/s12272-013-0104-8.
    [23]BEMIS J C,LABASH C,AVLASEVICH S L,et al.Rat Pig-a mutation assay responds to the genotoxic carcinogen ethyl carbamate but not the non-genotoxic carcinogen methyl carbamate[J].Mutagenesis,2015,30(3):343-347.DOI:10.1093/mutage/geu084.
    [24]LIU H C,CUI B,XU Y,et al.Ethyl carbamate induces cell death through its effects on multiple metabolic pathways[J].Chemico-Biological Interactions,2017,277:21-32.DOI:10.1016/j.cbi.2017.08.008.
    [25]BARRON C C,MOORE J,TSAKIRIDIS T,et al.Inhibition of human lung cancer cell proliferation and survival by wine[J].Cancer Cell International,2014,14(1):1-13.DOI:10.1186/1475-2867-14-6.
    [26]STOEWSAND G S,ANDERSON J L,MUNSON L.Inhibition by wine of tumorigenesis induced by ethyl carbamate(urethane)in mice[J].Food and Chemical Toxicology,1991,29(5):291-295.DOI:10.1016/0278-6915(91)90199-H.
    [27]周景文,堵国成,陈坚.发酵食品有害氨(胺)类代谢物:形成机制和消除策略[J].中国食品学报,2011,11(9):8-25.DOI:10.3969/j.issn.1009-7848.2011.09.002.
    [28]CHEN D W,REN Y P,ZHONG Q D,et al.Ethyl carbamate in alcoholic beverages from China:levels,dietary intake,and risk assessment[J].Food Control,2017,72:283-288.DOI:10.1016/j.foodcont.2015.10.047.
    [29]杨晓丽,郑凤娥,王冬妍,等.酒中氨基甲酸乙酯的产生及危害分析[J].品牌与标准化,2014,35(2):20-21.DOI:10.3969/j.issn.1674-4977.
    [30]FLAMINI R,TRALDI P.Mass spectrometry in grape and wine chemistry[M].Hoboken:John Wiley&Sons,Inc.,2010:241-278.DOI:10.1002/9780470552926.ch8.
    [31]LACHENMEIER D W,LIMA M C,NóBREGA I C,et al.Cancer risk assessment of ethyl carbamate in alcoholic beverages from Brazil with special consideration to the spirits cacha?a and tiquira[J].BMCCancer,2010,10(1):266-280.DOI:10.1186/1471-2407-10-266.
    [32]LACHENMEIER D,KANTERES F,KUBALLA T,et al.Ethyl carbamate in alcoholic beverages from Mexico(Tequila,Mezcal,Bacanora,Sotol)and Guatemala(Cuxa):market survey and risk assessment[J].International Journal of Environmental Research and Public Health,2009,6(12):349-360.DOI:10.3390/ijerph6010349.
    [33]LEE K G.Analysis and risk assessment of ethyl carbamate in various fermented foods[J].European Food Research&Technology,2013,236(5):891-898.DOI:10.1007/s00217-013-1953-6.
    [34]许宏贤,段钢.酒中氨基甲酸乙酯及尿素的研究进展[J].酿酒科技,2012,33(6):92-95.DOI:10.13746/j.njkj.2012.06.084.
    [35]MO W M,HE H L,XU X M,et al.Simultaneous determination of ethyl carbamate,chloropropanols and acrylamide in fermented products,flavoring and related foods by gas chromatography-triple quadrupole mass spectrometry[J].Food Control,2014,43(8):251-257.DOI:10.1016/j.foodcont.2014.03.033.
    [36]FU Z,YANG L L,MA LY,et al.Occurrence of ethyl carbamate in three types of Chinese wines and its possible reasons[J].Food Science&Biotechnology,2016,25(4):949-953.DOI:10.1007/s10068-016-0155-y.
    [37]梁萌萌,薛洁,张敬,等.葡萄酒中氨基甲酸乙酯的分析与控制[J].酿酒科技,2013,34(3):40-43.DOI:10.13746/j.njkj.2013.03.028.
    [38]CA?AS I P M,ROMERO G E,ALONSO G S,et al.Amino acids and biogenic amines during spontaneous malolactic fermentation in Tempranillo red wines[J].Journal of Food Composition and Analysis,2008,21(8):731-735.DOI:10.1016/j.jfca.2007.11.002.
    [39]CERRETI M,FIDALEO M,BENUCCI I,et al.Assessing the potential content of ethyl carbamate in white,red,and roséwines as a key factor for pursuing urea degradation by purified acid urease[J].Journal of Food Science,2016,81(7):1603-1612.DOI:10.1111/1750-3841.13344.
    [40]ROMERO S V,REGUANT C,BORDONS A,et al.Potential formation of ethyl carbamate in simulated wine inoculated with Oenococcus oeni and Lactobacillus plantarum[J].International Journal of Food Science&Technology,2009,44(6):1206-1213.DOI:10.1111/j.1365-2621.2009.01948.x.
    [41]付方圆,薛洁,梁萌萌,等.葡萄酒贮存过程中氨基甲酸乙酯含量的变化[J].食品与发酵工业,2014,40(8):34-39.DOI:10.13995/j.cnki.11-1802/ts.2014.08.019.
    [42]邹弯,魏玉洁,王德良,等.葡萄酒贮存过程中氨基甲酸乙酯动力学反应[J].食品与发酵工业,2016,42(4):32-37.DOI:10.13995/j.cnki.11-1802/ts.201604007.
    [43]WANG P H,SUN J Y,LI X M,et al.Contribution of citrulline to the formation of ethyl carbamate during Chinese rice wine production[J].Food Additives&Contaminants:Part A,2014,31(4):587-592.DOI:10.1080/19440049.2013.878869.
    [44]ARENA M E,SAGUIR F M,MANCA D N M.Arginine,citrulline and ornithine metabolism by lactic acid bacteria from wine[J].International Journal of Food Microbiology,1999,52(3):155-161.DOI:10.1016/S0168-1605(99)00133-6.
    [45]董兴全,丁燕.葡萄酒中氨基甲酸乙酯的形成机理及影响因素[J].酿酒科技,2014,35(12):47-52.DOI:10.13746/j.njkj.2014.0312.
    [46]BELL S,HENSCHKE P A.Implications of nitrogen nutrition for grapes,fermentation and wine[J].Australian Journal of Grape and Wine Research,2005,11(3):242-295.DOI:10.1111/j.1755-0238.2005.tb00028.x.
    [47]MIRA D O R,LIU S,PATCHETT M L,et al.Ethyl carbamate precursor citrulline formation from arginine degradation by malolactic wine lactic acid bacteria[J].FEMS Microbiology Letters,2000,183(1):31-35.DOI:10.1016/S0378-1097(99)00624-2.
    [48]VRANCKEN G,RIMAUX T,WECKX S,et al.Environmental pH determines citrulline and ornithine release through the arginine deiminase pathway in Lactobacillus fermentum IMDO 130101[J].International Journal of Food Microbiology,2009,135(3):216-222.DOI:10.1016/j.ijfoodmicro.2009.07.035.
    [49]AZEVEDO Z,COUTO J A,HOGG T.Citrulline as the main precursor of ethyl carbamate in model fortified wines inoculated with Lactobacillus hilgardii:a marker of the levels in a spoiled fortified wine[J].Letters in Applied Microbiology,2002,34(1):32-36.DOI:10.1046/j.1472-765x.2002.01045.x.
    [50]ZHAO X R,DU G C,ZOU H J,et al.Progress in preventing the accumulation of ethyl carbamate in alcoholic beverages[J].Trends in Food Science&Technology,2013,32(2):97-107.DOI:10.1016/j.tifs.2013.05.009.
    [51]MORENO-ARRIBAS M V,SUáLDEA B A B,MARANGON M,et al.Wine safety,consumer preference,and human health[M].Berlin:Springer International Publishing,2016:97-116.DOI:10.1007/978-3-319-24514-0_5.
    [52]ARENA M E,LISI M S,DE NADRA M M C,et al.Wine composition plays an important role in the control of carcinogenic precursor formation by Lactobacillus hilgardii X1 B[J].Journal of the Science of Food and Agriculture,2013,93(1):142-148.DOI:10.1002/jsfa.5741.
    [53]张健,刘国新,张颖,等.尿素醇解反应的影响因素及动力学研究[J].天津科技大学学报,2014,29(5):6-9.DOI:10.13364/j.issn.1672-6510.2014.05.002.
    [54]ARAQUE I,BORDONS A,REGUANT C.Effect of ethanol and low pH on citrulline and ornithine excretion and arc gene expression by strains of Lactobacillus brevis and Pediococcus pentosaceus[J].Food Microbiology,2013,33(1):107-113.DOI:10.1016/j.fm.2012.09.005.
    [55]UTHURRY C A,LEPE J A S,LOMBARDERO J,et al.Ethyl carbamate production induced by selected yeasts and lactic acid bacteria in red wine[J].Food Chemistry,2006,94(2):262-270.DOI:10.1016/j.foodchem.2004.11.017.
    [56]ARENA M E,DE NADRA M M C.Influence of ethanol and low pH on arginine and citrulline metabolism in lactic acid bacteria from wine[J].Research in Microbiology,2005,156(8):858-864.DOI:10.1016/j.resmic.2005.03.010.
    [57]OUGH C S.Ethylcarbamate in fermented beverages and foods.II.possible formation of ethylcarbamate from diethyl dicarbonate addition to wine[J].Journal of Agricultural and Food Chemistry,1976,24(2):328-331.DOI:10.1021/jf60204a034.
    [58]ZHAO X R,ZOU H J,FU J W,et al.Nitrogen regulation involved in the accumulation of urea in Saccharomyces cerevisiae[J].Yeast,2013,30(11):437-447.DOI:10.1002/yea.2980.
    [59]HASNIP S,CAPUTI A,CREWS C,et al.Effects of storage time and temperature on the concentration of ethyl carbamate and its precursors in wine.[J].Food Additives and Contaminants,2004,21(12):1155-1161.DOI:10.1080/10.1080/02652030400019851.
    [60]魏玉洁,付方圆,武顺,等.葡萄酒酵母car1基因表达量与EC含量相关性的研究[J].食品与发酵工业,2015,46(8):59-64.DOI:10.13995/j.cnki.11-1802/ts.201508011.
    [61]MARKS V D,VAN DER MERWE G K,VAN VUUREN H J J.Transcriptional profiling of wine yeast in fermenting grape juice:regulatory effect of diammonium phosphate[J].FEMS Yeast Research,2003,3(3):269-287.DOI:10.1016/S1567-1356(02)00201-5.
    [62]GUO X W,LI Y Z,GUO J,et al.Reduced production of ethyl carbamate for wine fermentation by deleting CAR1 in Saccharomyces cerevisiae[J].Journal of Industrial Microbiology&Biotechnology,2016,43(5):671-679.DOI:10.1007/s10295-016-1737-7.
    [63]ARAQUE I,GIL J,CARRETéR,et al.Detection of arc genes related with the ethyl carbamate precursors in wine lactic acid bacteria[J].Journal of Agricultural and Food Chemistry,2009,57(5):1841-1847.DOI:10.1021/jf803421w.
    [64]LASIK M.The application of malolactic fermentation process to create good-quality grape wine produced in cool-climate countries:a review[J].European Food Research and Technology,2013,237(6):843-850.DOI:10.1007/s00217-013-2083-x.
    [65]INGLEDEW W M,MAGNUS C A,PATTERSON J R.Yeast foods and ethyl carbamate formation in wine[J].American Journal of Enology&Viticulture,1987,38(4):332-335.
    [66]UTHURRY C A,VARELA F,COLOMO B,et al.Ethyl carbamate concentrations of typical Spanish red wines[J].Food Chemistry,2004,88(3):329-336.DOI:10.1016/j.foodchem.2004.01.063.
    [67]LARCHER R,MOSER S,MENOLLI A U,et al.Ethyl carbamate formation in sub-optimal wine storage conditions and influence of the yeast starter[J].Journal International Des Sciences De La Vigne Et Du Vin,2013,47(1):65-68.DOI:10.20870/oeno-one.2013.47.1.1535.
    [68]TERRADE N,DE ORDU?A M R.Impact of winemaking practices on arginine and citrulline metabolism during and after malolactic fermentation[J].Journal of Applied Microbiology,2006,101(2):406-411.DOI:10.1111/j.1365-2672.2006.02978.x.
    [69]FIDALEO M,ESTI M,MORESI M.Assessment of urea degradation rate in model wine solutions by acid urease from Lactobacillus fermentum[J].Journal of Agricultural and Food Chemistry,2006,54(17):6226-6235.DOI:10.1021/jf060934s.
    [70]DIXON N E,GAZZOLA T C,BLAKELEY R L,et al.Letter:Jack bean urease(EC 3.5.1.5).a metalloenzyme.a simple biological role for nickel?[J].Journal of the American Chemical Society,1975,97(14):4131-4133.DOI:10.1021/ja00847a045.
    [71]TRAMPER J,ZHU Y.Modern biotechnology[M].Wageningen:Wageningen Academic Publishers,2011:95-111.DOI:10.3920/978-90-8686-725-7_6.
    [72]SOUFLEROS E H,BOULOUMPASI E,TSARCHOPOULOS C,et al.Primary amino acid profiles of Greek white wines and their use in classification according to variety,origin and vintage[J].Food Chemistry,2003,80(2):261-273.DOI:10.1016/S0308-8146(02)00271-6.
    [73]ZHANG Z W,LU X X,TIAN Y P,et al.High-sensitive electrochemical determination of ethyl carbamate using urethanase and glutamate dehydrogenase modified electrode[J].Electroanalysis,2017,29(2):481-488.DOI:10.1002/elan.201600421.

© 2004-2018 中国地质图书馆版权所有 京ICP备05064691号 京公网安备11010802017129号

地址:北京市海淀区学院路29号 邮编:100083

电话:办公室:(+86 10)66554848;文献借阅、咨询服务、科技查新:66554700