Simultaneous Determination of 1-Methylimidazole, 2-Methylimidazole and 4-Methylimidazole in Sauced Meat Products by Ultra High Performance Liquid Chromatograhpy-Tandem Mass Spectrometry

Yuhang MIN; Luyao HUANG; Xiaoqin YU; Ying WANG

doi:10.13386/j.issn1002-0306.2020080139

Volume 42 Issue 10

May 2021

Turn off MathJax

Article Contents

Abstract

References

Science and Technology of Food Industry > 2021 > 42(10): 261-266. > DOI: 10.13386/j.issn1002-0306.2020080139

MIN Yuhang, HUANG Luyao, YU Xiaoqin, et al. Simultaneous Determination of 1-Methylimidazole, 2-Methylimidazole and 4-Methylimidazole in Sauced Meat Products by Ultra High Performance Liquid Chromatograhpy-Tandem Mass Spectrometry[J]. Science and Technology of Food Industry, 2021, 42(10): 261−266. (in Chinese with English abstract). doi: 10.13386/j.issn1002-0306. 2020080139.

Citation:

PDF (867 KB)

Simultaneous Determination of 1-Methylimidazole, 2-Methylimidazole and 4-Methylimidazole in Sauced Meat Products by Ultra High Performance Liquid Chromatograhpy-Tandem Mass Spectrometry

Sichuan Provincial Food and Drug Inspection Institute, Sichuan 610097, China

More Information

Received Date: August 16, 2020
Available Online: March 18, 2021

Graphical Abstract

Abstract

Abstract

An ultrahigh performance liquid chromatography-tandem mass spectorometric (HPLC-MS/MS) method was developed for the simultaneous determination of 1-methylimidazole (1-MEI), 2-methylimidazole (2-MEI) and 4-methylimidazole (4-MEI) in sauced meat products. The sample was extracted with water and the extracting solution was cleaned by Waters Oasis MCX SPEcolumn. The eluantwas dried under a stream of nitrogen and dissolved with initial mobile phase, the analytes were then separated by the Agilent Zorbax HILIC (2.1 mm×100 mm, 3.5 μm) using binary mobile phase gradient with acetonitrile and 5 mmol/L ammonium acetate. The compounds were ionized by positive electrospay, then detected under the multiple reaction monitoring (MRM) mode and quantified by the isotope internal standard method. The linearity of 1-MEI, 2-MEI and 4-MEI in the range from 30~400 ng/mL exhibited correlation coefficients greater than 0.9997. The limits of detection (LOD) and quantification (LOQ) were 10, 30 μg/kg. The average recoveries at three level spiked concentrations (30, 60, 300 μg/kg) ranged from 92.0% to 116.3%, with the relative standard deviations (n=6) between 0.70% and 3.96%. The method was applied to detect 36 sauced meat products, the 1-MEI was not detected in sauced meat products;the detection rate of 2-MEI was 5.5%, the content was 21.4~23.6 μg/kg, 4-MEI was detected in all of samples, the content was 3.1~306.6 μg/kg. The method was simple, rapid, sensitive and reliable, could be applied to determine1-MEI, 2-MEI and 4-MEI in sauced meat products.

FullText(HTML)

References (29)

References

[1]	J O Fernandes, M A Ferreira. Gas chromatographic-mss spectrometric determination of 4-(5) methylimidizazole in ammonia caramel colur using ion-pair extraction and derivatization with isobutylchloroformate[J]. Joural of Chromatography A,1997,786:299−308. doi: 10.1016/S0021-9673(97)00603-1
[2]	National Toxicology Program. Toxicology and carcinogenesis studies of 4-methylimidazole (Cas No. 822-36-6) in F344 /N rats and B6C3F1 mice (feed studies)[R]. U. S. Department of Health and Human Services, 2007.
[3]	OEHHA (Office of Environmental Health Assessment). 4-Methylimidazole (4-MEI) A Fact Sheet[EB/OL]. (2012-2-23)http://oehha.ca.gov/proposition-65/4-methylimidazole-4-mei-fact-sheet.
[4]	Irac. Agents classified by the iatc monographs, volumes 1[EB/OL]. (2017-4-13). http://monographs.iarc.fr/ENG/Classification/.
[5]	王颖, 黄璐瑶, 余晓琴, 等. 高效液相色谱-串联质谱法测定豆制品中3种甲基咪唑类化合物[J]. 中国卫生检验杂志,2018,28(4):415−417.
[6]	中华人民共和国国家卫生和计划生育委员会. GB 2760-2014 食品安全国家标准食品添加剂使用标准[S]. 北京: 中国标准出版社, 2015.
[7]	黄志勤, 屈海云. 分光光度法测定焦糖色中4-甲基咪唑[J]. 中国调味品,2005,6(6):52−54.
[8]	李继民, 王彦吉, 邹宁, 等. 紫外可见光谱法测定酱油中4-甲基咪唑含量[J]. 光谱实验室,2008,25(2):84−86.
[9]	陈小曼, 陈漾, 李攻科, 等. 表面增强拉曼光谱法测定饮料中4-甲基咪唑和2-甲基咪唑[J]. 分析化学,2016,44(5):816−821. .
[10]	郭小莉, 陈敏, 胡锦荣, 等. 气相色谱法测定酱油中的4-甲基咪唑[J]. 食品工业科技,2004,25(7):125−127.
[11]	彭向前, 冯玮, 石海英, 等. 气象色谱法同时检测焦糖色中的2-甲基咪唑和4-甲基咪唑[J]. 中国调味品,2012,37(8):83−85.
[12]	郭小莉, 陈敏, 张世湘, 等. 毛细管气相色谱法测定焦糖色中的4-甲基咪唑[J]. 食品科学,2005,26(2):169−171.
[13]	Casal S , Fernandes J O, Oliveria M B, et al. Gas chromatograph-mass spectrometric quantification of 4-(5)-methylimidazole in roasted coffee after ion-pair extraction[J]. Journal of Chromatography A,2002,967:285−291.
[14]	林晓珊, 杭义萍, 吴惠勤, 等. 气相色谱-串联质谱法测定焦糖色素中2-甲基咪唑和4-甲基咪唑[J]. 分析试验室,2011,30(11):85−88.
[15]	熊珺, 陈美玲, 赖毅东. 固相萃取-选择离子气质联用法测定调味料中的4-甲基咪唑[J]. 现代食品科技,2012,28(5):567−569.
[16]	荣维广, 宋宁慧, 阮华, 等. 固相萃取-高效液相色谱法测定焦糖色素中副产物2-甲基咪唑、4-甲基咪唑和2-乙酰基-4-(1, 2, 3, 4-四羟基丁基)咪唑[J]. 分析化学,2015,43(5):742−747.
[17]	Lee K G, Jiang H, T Shibamoto. Formation of carcinogenic 4-(5)-methylimidazole in caramel model systems: A role of sulphite[J]. Food Chemistry,2013,136:1165−1168. doi: 10.1016/j.foodchem.2012.09.025
[18]	张璐, 孔祥虹, 何强, 等. UPLC-MS-MS检测饮料中的4-甲基咪唑及其同分异构体2-甲基咪唑[J]. 食品科学,2014,35(8):244−248.
[19]	Wang J Y, W C Schuute. Simultaneous quantitation of 2-acetyl-4-tetrahydroxybutylimidazole, 2-and 4-methylimidazoles, and 5-hydroxymethylfurfural in beverages by ultrahigh-performance liquid chromatography-tandem mass spectrometry[J]. Journal of Agricultural and Food Chemistry,2012,60:917−921. doi: 10.1021/jf204476x
[20]	H Yamaguchi, T Masuda. Determination of 4-(5)-methylimidazole in soy sauce and other foods by LC-MS/MS after solid-phase extraction[J]. Journal of Agricultural and Food Chemistry,2011,59:9770−9775. doi: 10.1021/jf201736c
[21]	孟颖. 焦糖色素着色食品中甲基咪唑测定方法的研究及应用[D]. 太原: 山西大学. 2014.
[22]	林晓珊. 气相色谱-串联质谱技术在调味品有害物质分析中的应用研究[D]. 广州: 华南理工大学, 2011.
[23]	庞美蓉, 林钦, 戴明, 等. 超高效液相色谱-串联质谱法同步检测食品中的2-甲基咪唑及4-甲基咪唑[J]. 分析测试学报,2016,35(8):943−948.
[24]	李建平, 渠志华, 王辰, 等. 固相萃取-超高效液相色谱-串联质谱法测定啤酒中4-甲基咪唑的含量[J]. 中国食品卫生杂志,2016,28(5):610−613.
[25]	刘芸, 丁涛, 费晓庆, 等. 高效液相色谱-四级杆/静电场轨道阱高分表率质谱检测酱油中的4-甲基咪唑与2-甲基咪唑[J]. 分析测试学报,2015,34(4):381−387.
[26]	吴玉銮, 冼燕萍, 郭新东, 等. 分散固相萃取-超高效液相色谱-串联质谱法测定酱油中的2-甲基咪唑和4-甲基咪唑[J]. 食品安全质量检测学报,2014,5(5):1357−1364.
[27]	公丕学, 廉贞霞, 薛霞, 等. 固相萃取UPLC-MS/MS测定黄酒中2-甲基咪唑和4-甲基咪唑[J]. 食品研究与开发,2019,40(14):136−142.
[28]	Matuszewski B K. Standard line slpoes as a measure of a relative matrix effect in quantitative HPLC-MS bioanalysis[J]. Journal of Chromatography B,2006,830:293−300. doi: 10.1016/j.jchromb.2005.11.009
[29]	O'Halloran S, Ilett K F. Evaluation of a deuterium-labeled internal standard for the measurement of sirolimus by high-throughput HPLC electrospray ionization tandem mass spectrometry[J]. Clinical Cheistry,2008,54:1386−1389.