混合模式固相萃取-高效液相色谱法测定牛奶中4种非甾体抗炎药残留

引用本文: 丁健桦, 徐文平, 朱玉玲. 混合模式固相萃取-高效液相色谱法测定牛奶中4种非甾体抗炎药残留[J]. 分析化学, 2023, 51(6): 1013-1023. doi: 10.19756/j.issn.0253-3820.211239 shu

Citation: DING Jian-Hua, XU Wen-Ping, ZHU Yu-Ling. Mixed-mode Solid Phase Extraction Coupled with High Performance Liquid Chromatography for Analysis of Non-steroidal Anti-inflammatory Drugs Residues in Bovine Milk[J]. Chinese Journal of Analytical Chemistry, 2023, 51(6): 1013-1023. doi: 10.19756/j.issn.0253-3820.211239 shu

混合模式固相萃取-高效液相色谱法测定牛奶中4种非甾体抗炎药残留

东华理工大学化学与材料学院, 南昌 330013

通讯作者: 朱玉玲,E-mail:zyl9568@ecut.edu.cn

基金项目:
江西省科技厅重点研发计划项目(No.20192BBG7008)和东华理工大学博士科研启动基金项目(No.DHBK2019145)资助。

摘要: 制备了咪唑离子液体功能化的混合模式硅胶吸附剂（Sil-IL），将其作为固相萃取（SPE）吸附剂，结合高效液相色谱-紫外检测方法（HPLC-UV），建立了测定牛奶中酮洛芬、萘普生、吲哚美辛和托芬那酸4种非甾体类抗炎药物（NSAIDs）的分析方法。通过红外光谱、拉曼光谱和元素分析对Sil-IL进行了表征，初步探索了Sil-IL对目标物的保留作用机理，考察了样品溶液的pH值、上样流速、淋洗液及洗脱溶剂体积等因素对SPE效率的影响。结果表明，Sil-IL对4种NSAIDs的保留主要通过疏水作用和阴离子交换作用，Sil-IL吸附剂对4种NSAIDs具有较好的萃取选择性和萃取效率。在优化的SPE条件下，托芬那酸的线性检测范围为4~1000 μg/L，其它3种NSAIDs的线性范围为3~1000 μg/L，相关系数（R²）为0.9996~0.9998，检出限为1.2~1.9 μg/kg（S/N=3），日内和日间精密度分别为1.0%~3.0%和1.9%~6.3%，加标回收率为90.8%~105.3%。本方法准确可靠、灵敏度高、背景干扰低小、操作简便，可用于奶制品中4种NSAIDs残留的同时检测。

关键词:

English

Mixed-mode Solid Phase Extraction Coupled with High Performance Liquid Chromatography for Analysis of Non-steroidal Anti-inflammatory Drugs Residues in Bovine Milk

School of Chemistry and Material Science, East China University of Technology, Nanchang 330013, China

Corresponding author: ZHU Yu-Ling, zyl9568@ecut.edu.cn

Received Date: 21 March 2021
Revised Date: 29 May 2023
Fund Project:
Supported by the Department of Science and Technology of Jiangxi Province (No. 20192BBG7008) and the Doctoral Research Fund of East China University of Technology (No. DHBK2019145).

Abstract: A imidazolium ionic liquid-functionalized silica (Sil-IL) was synthesized and used as mixed-mode sorbent for solid phase extraction (SPE) of non-steroidal anti-inflammatory drugs (NSAIDs, naproxen, ketoprofen, indoometacin and tolfenamic acid) residues from bovine milk. A method combining this mixed-mode SPE and high performance liquid chromatography-ultraviolet detector (HPLC-UV) was established for simultaneous analysis of four kinds of NSAIDs residues in bovine milk. The prepared Sil-IL was characterized by Fourier transform infrared spectra, Raman spectra and elemental analysis. Then the retention mechanism of NSAIDs on Sil-IL sorbent was explored and the parameters affecting the extraction efficiency were optimized. Experimental results showed that Sil-IL had good extraction selectivity and high extraction efficiency towards four kinds of NSAIDs. Meanwhile, the interaction between Sil-IL and NSAIDs was mainly hydrophobic and anion exchange interactions. Under optimal SPE conditions, good sensitivity was achieved with a limit of detection of 1.2-1.9 μg/kg. The method displayed good linear relationship in the concentration range of 3-1000 μg/L for ketoprofen, naproxen, indomethacin and 4-1000 μg/L for tolfenamic acid, with the correlation coefficient (R²) of 09996-0.9998. The intra-day and inter-day precision were 1.0%-3.0% and 1.9%-6.3%, respectively. The recoveries of four kinds of NSAIDs in bovine milk at two spiked levels were 90.8%-105.3% with relative standard deviations less than 6.1%. The established method was proved to be accurate, reliable, simple, sensitive and selective, and could be used for determination of NSAIDs residues in milk sample.

Key words:

Ionic liquid
/ Nonsteroidal anti-inflammatory drugs
/ Solid phase extraction
/ High performance liquid chromatography
/ Bovine milk

1. [1]
  VAN PAMEL E, DAESELEIRE E. Anal. Bioanal. Chem., 2015, 407(15):4485-4494.VAN PAMEL E, DAESELEIRE E. Anal. Bioanal. Chem., 2015, 407(15):4485-4494.
2. [2]
  HU Ting, PENG Tao, LI Xiao-Juan, CHEN Dong-Dong, DAI Han-Hui, ZHOU Yue-Ning, XIA Xi, DING Shuang-Yang, ZHU Ai-Ling, JIANG Hai-Yang. Chin. J. Anal. Chem., 2012, 40(2):236-242. 胡婷, 彭涛, 李晓娟, 陈冬东, 代汉慧, 周玥宁, 夏曦, 丁双阳, 朱爱玲, 江海洋. 分析化学, 2012, 40(2):236-242.
3. [3]
  FU De-Xing, FENG Yu-Fei. Chin. Gen. Pract., 2008, (2):136-138. 傅得兴, 封宇飞. 中国全科医学, 2008, (2):136-138.
4. [4]
  Commission Regulation (EU) No. 37/2010 of 22 December 2009 on Pharmacologically Active Substances and Their Classification Regarding Maximum Residue Limits in Foodstuffs of Animal Origin. Off. J. Eur. Union, L15:1-72.Commission Regulation (EU) No. 37/2010 of 22 December 2009 on Pharmacologically Active Substances and Their Classification Regarding Maximum Residue Limits in Foodstuffs of Animal Origin. Off. J. Eur. Union, L15:1-72.
5. [5]
  GB 31650-2019. National Food Safety Standard:Maximum Residue Limits for Veterinary Drugs in Foods. National Standards of the People's Republic of China. 食品安全国家标准-食品中兽药最大残留限量. 中华人民共和国国家标准. GB 31650-2019.
6. [6]
  TARTAGLIA A, KABIR A, D'AMBROSIO F, RAMUNDO P, ULUSOY S, ULUSOY H I, MERONE G M, SAVINI F, D'OVIDIO C, GRAZIA U D, FURTON K G, LOCATELLI M. J. Chromatogr. B, 2020, 1144:122082.TARTAGLIA A, KABIR A, D'AMBROSIO F, RAMUNDO P, ULUSOY S, ULUSOY H I, MERONE G M, SAVINI F, D'OVIDIO C, GRAZIA U D, FURTON K G, LOCATELLI M. J. Chromatogr. B, 2020, 1144:122082.
7. [7]
  SEIDI S, SANATI S E. Microchim. Acta, 2019, 186(5):297.SEIDI S, SANATI S E. Microchim. Acta, 2019, 186(5):297.
8. [8]
  MIRZAJANI R, KARDANI F, RAMEZANI Z. Microchem. J., 2019, 144:270-284.MIRZAJANI R, KARDANI F, RAMEZANI Z. Microchem. J., 2019, 144:270-284.
9. [9]
  LI W, HUANG L, GUO D, ZHAO Y, ZHU Y. J. Chromatogr. A, 2018, 1571:76-83.LI W, HUANG L, GUO D, ZHAO Y, ZHU Y. J. Chromatogr. A, 2018, 1571:76-83.
10. [10]
  SN/T 2190-2008. Determination of Residues of Non-steroidal Anti-inflammatory Drugs in Foodstuffs of Animal Origin for Import and Export:LC-MS/MS Method. Industry Standards of Entry-Exit Inspection and Quarantine of the People's Republic of China. 进出口动物源性食品中非甾体类抗炎药残留量检测方法液相色谱-质谱/质谱法. 中华人民共和国出入境检验检疫行业标准. SN/T 2190-2008.
11. [11]
  WANG Y, OU Y, XIE S, CHEN D, WANG X, PAN Y, WANG Y, HUANG L, CHENG G, QU W, LIU Z, TAO Y, YUAN Z. Food Anal. Methods, 2019, 12(6):1346-1368.WANG Y, OU Y, XIE S, CHEN D, WANG X, PAN Y, WANG Y, HUANG L, CHENG G, QU W, LIU Z, TAO Y, YUAN Z. Food Anal. Methods, 2019, 12(6):1346-1368.
12. [12]
  SHISHOV A, NECHAEVA D, BULATOV A. Microchem. J., 2019, 150:104080.SHISHOV A, NECHAEVA D, BULATOV A. Microchem. J., 2019, 150:104080.
13. [13]
  MARTA Z, BOBALY B, FEKETE J, MAGDA B, IMRE T, SZABO P T. J. Pharm. Biomed. Anal., 2018, 160:99-108.MARTA Z, BOBALY B, FEKETE J, MAGDA B, IMRE T, SZABO P T. J. Pharm. Biomed. Anal., 2018, 160:99-108.
14. [14]
  HUANG C, LI Y, YANG J, PENG J, TAN J, FAN Y, WANG L, CHEN J. Talanta, 2018, 190:15-22.HUANG C, LI Y, YANG J, PENG J, TAN J, FAN Y, WANG L, CHEN J. Talanta, 2018, 190:15-22.
15. [15]
  REINHOLDS I, PUGAJEVA I, ZACS D, LUNDANES E, RUSKO J, PERKONS I, BARTKEVICS V. Environ. Monit. Assess., 2017, 189(11):568.REINHOLDS I, PUGAJEVA I, ZACS D, LUNDANES E, RUSKO J, PERKONS I, BARTKEVICS V. Environ. Monit. Assess., 2017, 189(11):568.
16. [16]
  KANG J W, PARK S J, PARK H C, GEDI V, SO B J, LEE K J. Appl. Biochem. Biotechnol., 2014, 174(1):1-5.KANG J W, PARK S J, PARK H C, GEDI V, SO B J, LEE K J. Appl. Biochem. Biotechnol., 2014, 174(1):1-5.
17. [17]
  GOKTAS E F, KABIL E, ABIOZ F. Drug. Test. Anal., 2020, 12(8):1065-1077.GOKTAS E F, KABIL E, ABIOZ F. Drug. Test. Anal., 2020, 12(8):1065-1077.
18. [18]
  AVINO P, NOTARDONATO I, PASSARELLA S, RUSSO M V. Appl. Sci., 2020, 10(16):5441.AVINO P, NOTARDONATO I, PASSARELLA S, RUSSO M V. Appl. Sci., 2020, 10(16):5441.
19. [19]
  JI Y, DU Z, ZHANG H, ZHANG Y. Anal. Methods, 2014, 6(18):7294-7304.JI Y, DU Z, ZHANG H, ZHANG Y. Anal. Methods, 2014, 6(18):7294-7304.
20. [20]
  JAFARI Z, HADJMOHAMMADI M R. Anal. Methods, 2020, 12(36):4429-4437.JAFARI Z, HADJMOHAMMADI M R. Anal. Methods, 2020, 12(36):4429-4437.
21. [21]
  MEUCCI V, MINUNNI M, VANNI M, SGORBINI M, CORAZZA M, INTORRE L. Bioanalysis, 2014, 6(16):2147-2158.MEUCCI V, MINUNNI M, VANNI M, SGORBINI M, CORAZZA M, INTORRE L. Bioanalysis, 2014, 6(16):2147-2158.
22. [22]
  AZZOUZ A, JURADO-SANCHEZ B, SOUHAIL B, BALLESTEROS E. J. Agric. Food Chem., 2011, 59(9):5125-5132.AZZOUZ A, JURADO-SANCHEZ B, SOUHAIL B, BALLESTEROS E. J. Agric. Food Chem., 2011, 59(9):5125-5132.
23. [23]
  GUC M, SCHROEDER G. Appl. Sci., 2020, 10(12):4217.GUC M, SCHROEDER G. Appl. Sci., 2020, 10(12):4217.
24. [24]
  WANG Yi-Cong, LIU Lei-Lei. Chin. J. Chromatogr., 2021, 39(3):241-259. 王艺聪, 刘磊磊. 色谱, 2021, 39(3):241-259.
25. [25]
  YANG Xin-Yue, GAO Li, SUN Ya-Ming, ZHAO Wen-Jie, XIANG Guo-Qiang, JIANG Xiu-Ming, HE Li-Jun, ZHANG Shu-Sheng. Chin. J. Anal. Chem., 2020, 48(12):1607-1615. 杨新月, 高莉, 孙亚明, 赵文杰, 向国强, 江秀明, 何丽君, 张书胜. 分析化学, 2020, 48(12):1607-1615.
26. [26]
  BERTHOD A, RUIZ-ÁNGEL M J, CARDA-BROCH S. J. Chromatogr. A, 2018, 1559:2-16.BERTHOD A, RUIZ-ÁNGEL M J, CARDA-BROCH S. J. Chromatogr. A, 2018, 1559:2-16.
27. [27]
  TIAN M, YAN H, ROW K H. J. Chromatogr. B, 2009, 877(8-9):738-742.TIAN M, YAN H, ROW K H. J. Chromatogr. B, 2009, 877(8-9):738-742.
28. [28]
  ZHU Y, ZHANG W, LI L, WU C, XING J. Anal. Methods, 2014, 6(7):2102-2111.ZHU Y, ZHANG W, LI L, WU C, XING J. Anal. Methods, 2014, 6(7):2102-2111.
29. [29]
  JEDZINIAK P, SZPRENGIER-JUSZKIEWICZ T, PIETRUK K, SLEDZINSKA E, ZMUDZKI J. Anal. Bioanal. Chem., 2012, 403(10):2955-2963.JEDZINIAK P, SZPRENGIER-JUSZKIEWICZ T, PIETRUK K, SLEDZINSKA E, ZMUDZKI J. Anal. Bioanal. Chem., 2012, 403(10):2955-2963.
30. [30]
  KIBBEY C E, MEYERHOFF M E. Anal. Chem., 1993, 65(17):2189-2196.KIBBEY C E, MEYERHOFF M E. Anal. Chem., 1993, 65(17):2189-2196.

扫一扫看文章

计量

PDF下载量: 9
文章访问数: 795
HTML全文浏览量: 54

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

混合模式固相萃取-高效液相色谱法测定牛奶中4种非甾体抗炎药残留

通讯作者: 朱玉玲,E-mail:zyl9568@ecut.edu.cn

English

Mixed-mode Solid Phase Extraction Coupled with High Performance Liquid Chromatography for Analysis of Non-steroidal Anti-inflammatory Drugs Residues in Bovine Milk

Corresponding author: ZHU Yu-Ling, zyl9568@ecut.edu.cn

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南：你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

计量

通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

混合模式固相萃取-高效液相色谱法测定牛奶中4种非甾体抗炎药残留

通讯作者: 朱玉玲,E-mail:zyl9568@ecut.edu.cn

English

Mixed-mode Solid Phase Extraction Coupled with High Performance Liquid Chromatography for Analysis of Non-steroidal Anti-inflammatory Drugs Residues in Bovine Milk

Corresponding author: ZHU Yu-Ling, zyl9568@ecut.edu.cn

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

计量

文章相关

通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

CCS Chemistry：颜徐州、鲍哲南：你的皮肤可能是一片SPMs