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
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

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;
  • 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

  • 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( N ε-(carboxymethyl) lysine),CML)和羧乙基赖氨酸( N ε-(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。
    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
    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

    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
    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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