JOURNAL OF LIGHT INDUSTRY

CN 41-1437/TS  ISSN 2096-1553

COFs材料磁固相萃取-HPLC-MS/MS法测定烘焙食品中两种主要晚期糖基化终末产物

余晶晶 ,  史莉莉 ,  刘雨欣 ,  陈满堂 ,  刘瑞红 ,  刘伟

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余晶晶, 史莉莉, 刘雨欣, 等. COFs材料磁固相萃取-HPLC-MS/MS法测定烘焙食品中两种主要晚期糖基化终末产物[J]. 轻工学报, 2023, 38(6): 52-61. doi: 10.12187/2023.06.007
引用本文: 余晶晶, 史莉莉, 刘雨欣, 等. COFs材料磁固相萃取-HPLC-MS/MS法测定烘焙食品中两种主要晚期糖基化终末产物[J]. 轻工学报, 2023, 38(6): 52-61. doi: 10.12187/2023.06.007
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YU Jingjing, SHI Lili, LIU Yuxin, et al. Determination of two major advanced glycation end products in baked food using HPLC-MS/MS based on COFs material magnetic solid phase extraction[J]. Journal of Light Industry, 2023, 38(6): 52-61. doi: 10.12187/2023.06.007
Citation: YU Jingjing, SHI Lili, LIU Yuxin, et al. Determination of two major advanced glycation end products in baked food using HPLC-MS/MS based on COFs material magnetic solid phase extraction[J]. Journal of Light Industry, 2023, 38(6): 52-61. doi: 10.12187/2023.06.007
shu

COFs材料磁固相萃取-HPLC-MS/MS法测定烘焙食品中两种主要晚期糖基化终末产物

  • 1. 中国烟草总公司郑州烟草研究院, 河南 郑州 450001;

  • 2. 河南工业大学 粮油食品学院, 河南 郑州 450001

    • 作者简介: 余晶晶(1982-),女,湖北省黄冈市人,中国烟草总公司郑州烟草研究院副研究员,博士,主要研究方向为分析化学。E-mail:yujingjing307@163.com;

  • 基金项目: 国家自然科学基金青年科学基金项目（31901768）

  • 中图分类号: TS251.5

Determination of two major advanced glycation end products in baked food using HPLC-MS/MS based on COFs material magnetic solid phase extraction

  • 1. Zhengzhou Tobacco Research Institute of CNTC, Zhengzhou 450001, China;

  • 2. School of Food Science and Technology, Henan University of Technology, Zhengzhou 450001, China

  • Received Date: 2023-07-11
    Accepted Date: 2023-10-16

    CLC number: TS251.5

  • 摘要: 为实现烘焙食品中晚期糖基化终末产物（Advanced Glycation End Products，AGEs）的准确、高灵敏测定，建立基于磁性共价有机骨架（Covalent Organic Frameworks，COFs）材料的磁固相萃取（Magnetic Solid Phase Extraction，MSPE）技术，实现烘焙食品中两种主要AGEs，即羧甲基赖氨酸（Nε-（carboxymethyl） lysine），CML）和羧乙基赖氨酸（Nε-（carboxyethyl） lysine，CEL）的选择性、高效富集，并结合高效液相色谱-串联质谱法对其进行定量分析。结果表明：所合成的磁性COFs材料具有较大的比表面积和较高的磁化强度，适合应用于MSPE技术。MSPE的适宜条件为吸附剂用量20 mg，涡旋萃取时间20 min，洗脱溶剂选用5%氨水/甲醇溶液，洗脱溶剂体积4 mL，洗脱时间15 min。CML和CEL的检出限分别为2.05 ng/mL和2.31 ng/mL，定量限分别为6.83 ng/mL和7.71 ng/mL；日内及日间精密度良好（RSD日内≤4.74%，RSD日间≤5.38%）；在饼干、坚果2种典型样品基质中，CML和CEL的加标回收率分别为90.70%~108.74%、85.50%~113.00%。将本文所建立的分析方法应用于市售的26种烘焙食品中CML和CEL的含量测定发现，饼干、糕点类烘焙食品中二者含量分别为（9.60±0.16）~（78.10±1.12） mg/kg、（4.37±0.23）~（26.70±1.27） mg/kg；坚果类烘焙食品中二者含量分别为（6.49±0.13）~（82.00±0.98） mg/kg、（6.65±0.30）~（55.90±0.67） mg/kg，该方法能有效净化样品，显著降低基质效应，定量分析准确性较高，且所合成的磁性COFs材料可再生使用5次，适合烘焙食品中CML和CEL的检测。
    Abstract: To achieve accurate and highly sensitive determination of advanced glycation end products (AGEs) in baked food, a magnetic solid phase extraction (MSPE) technique based on magnetic covalent organic frameworks (COFs) material was established to achieve the selective and efficient enrichment of two major AGEs (i.e. Nε-(carboxymethyl)lysine (CML) and Nε-(carboxyethyl)lysine (CEL)) in baked foods. The quantitative analysis of CML and CEL was conducted with high performance liquid chromatography tandem mass spectrometry (HPLC-MS/MS) method. Results showed that the synthesized magnetic COFs material showed big specific surface area and strong magnetism, which was suitable for MSPE. The optimum conditions of MSPE were as follows:the amount of adsorbent was 20 mg, the time of vortex extraction was 20 min, the elution solvent was 5% ammonia/methanol solution, the volume of elution solvent was 4 mL, the elution time was 15 min. The limits of detection of CML and CEL for the established method were 2.05 ng/mL and 2.31 ng/mL, respectively, while the limits of quantification were 6.83 ng/mL and 7.71 ng/mL, respectively. And intra-day and inter-day precisions were good (RSDintra-day ≤ 4.74%, RSDinter-day ≤ 5.38%). The recoveries of CML and CEL in typical food matrixes (i.e. biscuits and nuts) were in the range of 90.70%~108.74% and 85.50%~113.00%, respectively. Applying the analytical method established in this article to the determination of CML and CEL contents in 26 commercially available baked goods, it was found that the contents of CML and CEL in biscuits and pastries were in the range of (9.60±0.16)~(78.10±1.12) mg/kg, and (4.37±0.23)~(26.70±1.27) mg/kg, respectively; while the contents of CML and CEL in nuts were in the range of (6.49±0.13)~(82.00±0.98) mg/kg, and (6.65±0.30)~(55.90±0.67) mg/kg, respectively. The established method could effectively purify samples and significantly reduce matrix effect, and thus showed high accuracy for quantitative analysis. Furthermore, the synthesized magnetic COFs material could be recycled for 5 times, which was suitable for the determination of CML and CEL in baked food.
    1. [1]

      SINGH R, BARDEN A, MORI T, et al.Advanced glycation end-products:A review[J].Diabetologia, 2001, 44(2):129-146.

    2. [2]

      SONG Q H, LIU J J, DONG L Y, et al.Novel advances in inhibiting advanced glycation end product formation using natural compounds[J].Biomed Pharmacother, 2021, 140(12):111750.

    3. [3]

      CUI H P, YU J H, ZHAI Y, et al.Formation and fate of Amadori rearrangement products in Maillard reaction[J].Trends in Food Science & Technology, 2021, 115:391-408.

    4. [4]

      EVENS L, BELIËN H, DELUYKER D, et al.The impact of advanced glycation end-products (AGEs) on proliferation and apoptosis of primary stem cells:A systematic review[J].Stem Cells International, 2020, 2020:8886612.

    5. [5]

      PEPPA M, MAVROEIDI I.Experimental animal studies support the role of dietary advanced glycation end products in health and disease[J].Nutrients, 2021, 13(10):3467.

    6. [6]

      YUAN X J, NIE C X, LIU H C, et al.Comparison of metabolic fate, target organs, and microbiota interactions of free and bound dietary advanced glycation end products[J].Critical Reviews in Food Science and Nutrition, 2021, 26:1-22.

    7. [7]

      TWARDA-CLAPA A, OLCZAK A, BIAŁKOWSKA A M, et al.Advanced glycation end-products (AGEs):Formation, chemistry, classification, receptors, and diseases related to AGEs[J].Cells, 2022, 11(8):1312.

    8. [8]

      KUZAN A.Toxicity of advanced glycation end products[J].Biomedical Reports, 2021, 14(5):46.

    9. [9]

      CEPAS V, MANIG F, MAYO J C, et al.In vitro evaluation of the toxicological profile and oxidative stress of relevant diet-related advanced glycation end products and related 1, 2-dicarbonyls[J].Oxidative Medicine and Cellular Longevity, 2021, 2021:9912240.

    10. [10]

      DAI J Z, CHEN H, CHAI Y M.Advanced glycation end products (AGEs) induce apoptosis of fibroblasts by activation of NLRP3 inflammasome via reactive oxygen species (ROS) signaling pathway[J].Medical Science Monitor, 2019, 25:7499-7508.

    11. [11]

      PAN S, GUAN Y T, MA Y P, et al.Advanced glycation end products correlate with breast cancer metastasis by activating RAGE/TLR4 signaling[J].BMJ Open Diabetes Research & Care, 2022, 10(2):e002697.

    12. [12]

      SUZUKI R, FUJIWARA Y, SAITO M, et al.Intracellular accumulation of advanced glycation end products induces osteoblast apoptosis via endoplasmic reticulum stress [J].Journal of Bone and Mineral Research, 2020, 35(10):1992-2003.

    13. [13]

      AN X F, ZHANG L, YAO Q M, et al.The receptor for advanced glycation endproducts mediates podocyte heparanase expression through NF-kappa B signaling pathway [J].Molecular and Cellular Endocrinology, 2018, 470:14-25.

    14. [14]

      YING L W, SHEN Y, ZHANG Y, et al.Association of advanced glycation end products with diabetic retinopathy in type 2 diabetes mellitus[J].Diabetes Research and Clinical Practice, 2021, 177:108880.

    15. [15]

      MOLDOGAZIEVA N T, MOKHOSOEV I M, MEL'NIKOVA T I, et al.Oxidative stress and advanced lipoxidation and glycation end products (ALEs and AGEs) in aging and age-related diseases [J].Oxidative Medicine and Cellular Longevity, 2019, 2019:3085756.

    16. [16]

      BROWNLEE M, VLASSARAl H, CERAMI A, Nonenzymatic glycosylation and the pathogenesis of diabetic complications[J].Annals of Internal Medicine, 1984, 101(4):527-537.

    17. [17]

      INAN-EROGLU E, AYAZ A, BUYUKTUNCER Z.Formation of advanced glycation endproducts in foods during cooking process and underlying mechanisms:A comprehensive review of experimental studies[J].Nutrition Research Reviews, 2020, 33(1):77-89.

    18. [18]

      ZHU Z, HUANG S, KHAN I A, et al.The effect of oxidation and Maillard reaction on formation of Nε-carboxymethyllysine and Nε-carboxyethyllysine in prepared chicken breast [J].Cyta-Journal of Food, 2019, 17(1):685-694.

    19. [19]

      RIBEIRO P, TAVARES J F, COSTA M, et al.Effect of reducing dietary advanced glycation end products on obesity-associated complications:A systematic review[J].Nutrition Reviews, 2019, 77(10):725-734.

    20. [20]

      WANG S W, ZHENG L L, ZHENG X Y, et al.Chitosan inhibits advanced glycation end products formation in chemical models and bakery food[J].Food Hydrocolloids, 2022, 128:107600.

    21. [21]

      林钦, 郑小严, 陈纯, 等.UPLC-Q-TOF/MS在烘焙食品中羧甲基赖氨酸和羧乙基赖氨酸检测中的应用[J].分析测试学报, 2017, 36(3):297-304.

    22. [22]

      BEISSWENGER P J, HOWELL S K, RUSSELL G, et al.Detection of diabetic nephropathy from advanced glycation endproducts (AGEs) differs in plasma and urine, and is dependent on the method of preparation[J].Amino Acids, 2014, 46(2):311-319.

    23. [23]

      TAREKE E, FORSLUND A, LINDH C H, et al.Isotope dilution ESILC-MS/MS for quantification of free and total Nε-(1-carboxymethyl)-L-lysine and free Nε-(1-carboxyethyl)-L-lysine:Comparison of total Nε-(1-carboxymethyl)-L-lysine levels measured with new method to ELISA[J].Food Chemistry, 2013, 141(4):4253-4259.

    24. [24]

      CHARISSOU A, AIT-AMEUR L, BIRLOUEZ-ARAGON I.Evaluation of a gas chromatography/mass spectrometry method for the quantification of carboxymethyllysine in food samples[J].Journal of Chromatography A, 2007, 1140(1/2):189-194.

    25. [25]

      NOMI Y, ANNAKA H, SATO S, et al.Simultaneous quantitation of advanced glycation end products in soy sauce and beer by liquid chromatography-tandem mass spectrometry without ion-pair reagents and derivatization[J].Journal of Agricultural and Food Chemistry, 2016, 64:8397-8405.

    26. [26]

      YU J J, LIU K J, WANG S, et al.Analytical determination of CML and CEL in oral use tobacco products by HPLC-MS/MS method [J].Microchemical Journal, 2021, 168:106338.

    27. [27]

      GAO C H, LIN G, LEI Z X, et al.Facile synthesis of core-shell structured magnetic covalent organic framework composite nanospheres for selective enrichment of peptides with simultaneous exclusion of proteins[J].Journal of Materials Chemistry B, 2017, 5(36):7496-7503.

    28. [28]

      MA Y Y, ZHAO Y X, XU X T, et al.Magnetic covalent organic framework immobilized gold nanoparticles with high efficiency catalytic performance for chemiluminescent detection of pesticide triazophos[J].Talanta, 2021, 235:122798.

    29. [29]

      ZHANG W F, ZHANG Y H, ZHANG G R, et al.Facile preparation of a cationic COF functionalized magnetic nanoparticles and its use for the determination of nine hydroxylated polycyclic aromatic hydrocarbons in smokers' urine[J].Analyst, 2019, 144(19):5829-5841.

    30. [30]

      WANG L, BAO J, WANG L, et al.One-pot synthesis and bioapplication of amine-functionalized magnetite nanoparticles and hollow nanospheres[J].Chemistry A European Journal, 2010, 12(24):6341-6347.

    31. [31]

      TAN J, NAMUANGRUK S, KONG W F, et al.Manipulation of amorphous-to-crystalline transformation:Towards the construction of covalent organic framework hybrid microspheres with NIR photothermal conversion ability[J].Angewandte Chemie International Edition, 2016, 55(45):13979-13984.

    32. [32]

      HE S J, ZENG T, WANG S H, et al.Facile synthesis of magnetic covalent organic framework with three-dimensional bouquet-like structure for enhanced extraction of organic targets[J].ACS Applied Materials & Interfaces, 2017, 9(3):2959-2965.

    33. [33]

      ZHAO X, YOU J, SUO Y, et al.Determination of aliphatic amines from soil and wastewater of a paper mill by pre-column derivatization using HPLC and tandem mass spectrometry (HPLC-MS/MS)[J].Journal of Liquid Chromatography & Related Technologies, 2007, 30:1963-1979.

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余晶晶, 史莉莉, 刘雨欣, 等. COFs材料磁固相萃取-HPLC-MS/MS法测定烘焙食品中两种主要晚期糖基化终末产物[J]. 轻工学报, 2023, 38(6): 52-61. doi: 10.12187/2023.06.007
引用本文: 余晶晶, 史莉莉, 刘雨欣, 等. COFs材料磁固相萃取-HPLC-MS/MS法测定烘焙食品中两种主要晚期糖基化终末产物[J]. 轻工学报, 2023, 38(6): 52-61. doi: 10.12187/2023.06.007
shu
YU Jingjing, SHI Lili, LIU Yuxin, et al. Determination of two major advanced glycation end products in baked food using HPLC-MS/MS based on COFs material magnetic solid phase extraction[J]. Journal of Light Industry, 2023, 38(6): 52-61. doi: 10.12187/2023.06.007
Citation: YU Jingjing, SHI Lili, LIU Yuxin, et al. Determination of two major advanced glycation end products in baked food using HPLC-MS/MS based on COFs material magnetic solid phase extraction[J]. Journal of Light Industry, 2023, 38(6): 52-61. doi: 10.12187/2023.06.007
shu

COFs材料磁固相萃取-HPLC-MS/MS法测定烘焙食品中两种主要晚期糖基化终末产物

    作者简介:余晶晶(1982-),女,湖北省黄冈市人,中国烟草总公司郑州烟草研究院副研究员,博士,主要研究方向为分析化学。E-mail:yujingjing307@163.com
  • 1. 中国烟草总公司郑州烟草研究院, 河南 郑州 450001;
  • 2. 河南工业大学 粮油食品学院, 河南 郑州 450001
  • 收稿日期: 2023-07-11
  • 录用日期: 2023-10-16
基金项目:  国家自然科学基金青年科学基金项目（31901768）

摘要: 为实现烘焙食品中晚期糖基化终末产物（Advanced Glycation End Products，AGEs）的准确、高灵敏测定，建立基于磁性共价有机骨架（Covalent Organic Frameworks，COFs）材料的磁固相萃取（Magnetic Solid Phase Extraction，MSPE）技术，实现烘焙食品中两种主要AGEs，即羧甲基赖氨酸（Nε-（carboxymethyl） lysine），CML）和羧乙基赖氨酸（Nε-（carboxyethyl） lysine，CEL）的选择性、高效富集，并结合高效液相色谱-串联质谱法对其进行定量分析。结果表明：所合成的磁性COFs材料具有较大的比表面积和较高的磁化强度，适合应用于MSPE技术。MSPE的适宜条件为吸附剂用量20 mg，涡旋萃取时间20 min，洗脱溶剂选用5%氨水/甲醇溶液，洗脱溶剂体积4 mL，洗脱时间15 min。CML和CEL的检出限分别为2.05 ng/mL和2.31 ng/mL，定量限分别为6.83 ng/mL和7.71 ng/mL；日内及日间精密度良好（RSD日内≤4.74%，RSD日间≤5.38%）；在饼干、坚果2种典型样品基质中，CML和CEL的加标回收率分别为90.70%~108.74%、85.50%~113.00%。将本文所建立的分析方法应用于市售的26种烘焙食品中CML和CEL的含量测定发现，饼干、糕点类烘焙食品中二者含量分别为（9.60±0.16）~（78.10±1.12） mg/kg、（4.37±0.23）~（26.70±1.27） mg/kg；坚果类烘焙食品中二者含量分别为（6.49±0.13）~（82.00±0.98） mg/kg、（6.65±0.30）~（55.90±0.67） mg/kg，该方法能有效净化样品，显著降低基质效应，定量分析准确性较高，且所合成的磁性COFs材料可再生使用5次，适合烘焙食品中CML和CEL的检测。

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