加速溶剂萃取和分子印迹技术在农药残留分析中的应用研究
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摘要
近年来，农产品质量安全问题日益成为社会关注的焦点之一。在对复杂的农产品农药残留的检测中，前处理是样品分析过程中关键的一步。尤其是一些待测物浓度很低的样品。为了更好分离、纯化和富集，以便获得可靠的结果、较好的重现性和较高的灵敏度，建立更快速、高效、操作简便且环保的前处理方法在生物样品分析中显得尤为重要。
加速溶剂萃取(ASE)技术已经成为一种常用绿色分离技术，能够在多种样品中萃取出不同种类的农药残留。与传统的提取方法比较，ASE具有操作简便，减少有机溶剂对环境的污染，省时省溶剂，萃取操作完全自动化的特点。分子印迹聚合物(MIPs)是制备对特定分子具有专一性结合能力的高分子技术。MIPs具有亲和性好、选择性高、抗干扰性强、稳定性好，使用寿命长以及应用范围广等优点。目前，两种技术己在农残检测、天然药物分离以及色谱分析等领域得到广泛应用。加速溶剂萃取技术与分子印迹-固相萃取技术相结合可以极大的提高复杂样品前处理的选择性，实现复杂生物样品中农药残留的快速、有效分离。
本文第一章绪论部分简要的对加速溶剂萃取技术和分子印迹技术的研究进展进行了介绍。
第二章建立了加速溶剂萃取-硅胶柱净化-高效液相色谱分析的方法，用于检测烟草中氯虫苯甲酰胺和螺螨酯的残留。实验中对萃取条件进行了优化，包括：萃取溶剂、萃取温度和萃取时长等。对硅胶柱净化手段及色谱条件进行了研究，采用高效液相色谱-二极管阵列检测器的方法对待测物进行测定。在最优条件下，氯虫苯甲酰胺和螺螨酯均表现出了良好的线性范围（r>0.999），方法定量限(LOQ)为氯虫苯甲酰胺16.5μg/kg，螺螨酯66.5μg/kg。回收率为氯虫苯甲酰胺88.5–102%(RSDs=2.7–6.9%)，螺螨酯87.7–98.5%(RSDs=1.8–5.9%)；本方法简单、快速、有效，可以用于烟草中农药残留的分析。
第三章建立了加速溶剂萃取-固相萃取-高效液相色谱的方法，用于8种根类药食两用植物样品中环丙氨嗪及其代谢物三聚氰胺的测定。实验中分别对分离和检测方法的条件进行了探讨和优化，确定了对环境无污染的水作为萃取溶剂使用，应用Waters C18柱作为反相色谱分离柱。在最佳条件下，得到很好的线性回归方程（R=0.9998）。方法的定量限为环丙氨嗪2.15μg/kg，三聚氰胺2.51μg/kg，均低于各自最大允许残留量三个数量级。本方法能够检测出μg/kg水平的环丙氨嗪和三聚氰胺，已通过液相色谱-质谱的方法进行了确证。方法可以对药食两用植物中环丙氨嗪和三聚氰胺进行快速、高灵敏、高精度测定，且费用低廉。
第四章通过分子模拟计算和红外及核磁共振氢谱实验验证，对三聚氰胺为模板分子，甲基丙烯酸为功能单体合成分子印迹聚合物的分子识别机理进行了研究。发现三聚氰胺的氨基与甲基丙烯酸的羧基能够结合成比氢键更稳定的酰胺基。键合研究显示三聚氰胺分子印迹聚合物对三聚氰胺显示出极好的结合能力及选择性。
第五章第一部分建立了一种高选择性和灵敏度的分子印迹固相萃取-超高效液相色谱用来检测牛奶中环丙胺嗪、三聚氰胺、三聚氰胺二酰胺和三聚氰胺一酰胺的方法。方法中应用三聚氰胺分子印迹聚合物做吸附剂可以有效去除牛奶基质对测定的影响。在最佳条件下，方法在0.013~6.667μg/mL范围内具有良好的线性(r>0.999)，相对标准偏差介于2.2-4.6%之间。方法定量限介于1.3ng/mL-6.7ng/mL之间。该方法可以用于选择萃取、分离、测定牛奶及其他奶制品中的三聚氰胺及其相关化合物。
第五章第二部分建立了一种加速溶剂萃取-分子印迹固相萃取-超高效液相色谱的方法来检测肉类中环丙胺嗪、三聚氰胺和双氰胺。方法中采用水作为萃取溶剂，应用三聚氰胺的分子印迹聚合物作为固相萃取的吸附剂对肉类样品进行了处理。实验中对加速溶剂萃取条件和流动相进行了优化。应用ACQUITY UPLC BEH HILIC柱，在最佳条件下，三种待测物线性回归方程的系数均为0.9999。方法定量限低至双氰胺1.675μg/kg、三聚氰胺5μg/kg和环丙胺嗪3.325μg/kg，远低于国家及国际规定的最大允许残留量，方法具有较高的检测能力。三种浓度的标准添加回收率为：88.7–107%，RSDs为1.1–8.3%。方法可以对肉类中双氰胺、三聚氰胺和环丙氨嗪进行快速、高灵敏、高精度测定。
In recent years, increasing attention has been paid to the quality and safety (QS) ofproducts and foodstuffs. In the determination of pesticide residues in agricultural productssamples, sample preparation is very important, because the matrix is complicated andconcentration of analyte is very low. It is important to develop fast, efficient, simple andgreen sample preparation method in order to obtain reliable, repeatable analytical result.
Accelerated solvent extraction (ASE) is a new green extraction technique. ASE canextract different classes of pesticides residues which exist in numerous kinds of plant originfoods. It possesses many advantages such as easy to operate, less pollution to theenvironment by the organic solvent, less time, less solvent and automatic in the extractionprocedures comparing with other traditional extraction methods. Molecularly imprintedpolymers are specific polymer materials that have the selective binding ability to theparticular molecules. Molecularly imprinted polymers have many advantages of good affinity,high selectivity, powerful anti-interference performance, better stability, as well as long lifeand wide range of applications. Molecular imprinting technology had been used in manyfields such as pesticide residues analysis, food analysis, environmental monitoring, naturalproducts separation and chromatographic analysis. The selectivity of complex samplespretreatment was increased greatly when the accelerated-solvent-extraction technology andmolecularly-imprinted-solid-phase-extraction technology were applied together. And thepesticide residues in complex biological samples can be separated and enriched quickly andeffectively.
First of all, it is described that the history and development of the accelerated solventextraction technology and molecularly imprinted technology, and the research advance wasreviewed.
In chapter2, a new method for the determination of chlorantraniliprole (CAP) andspirodiclofen (SDF) residues in tobacco was developed by using liquid chromatography withdiode-array detection (LC-DAD) after accelerated solvent extraction (ASE) and silica gel clean-up. The conditions of ASE, silica gel clean-up and LC were investigated and optimized.A Waters C18column (250×4.6mm ID,5μm) was used for the LC using a mobile phasecomposed of methanol and water (90:10, v/v). Under optimal conditions, the linearity wassatisfactory in the range of0.03–1.5μg/mL with a correlation coefficient of0.9994for CAPand0.13–2.5μg/mL with a correlation coefficient of0.9991for SDF. The method limit ofquantification (LOQ) was16.5μg/kg for CAP, and64.3μg/kg for SDF, which is lower thantheir maximum residue limits (MRLs). The recoveries were88.5–102%with relative standarddeviations (RSDs) of2.7–6.9%for CAP, and87.7–98.5%with RSDs of1.8–5.9%for SDF.The proposed method is simple, rapid and effective, and provides the sensitivity and linearitynecessary for analysis of the pesticides in tobacco.
In chapter3, a highly sensitive method was developed for the determination of theresidues of cyromazine (CYR) and its metabolite, melamine(MEL), in herbal and edible plantsamples by using reversed phase high-performance liquid chromatography–diode-arraydetection (RP-HPLC-DAD) with accelerated solvent extraction and solid phase extractioncleanup. The conditions of separation and detection were investigated and optimized. AWaters C18column (250x4.6mm，i.d.,5μm) was used for the RP-HPLC, with a mobilephase composed of0.1%trifluoroacetic acid solution and methanol (85:15, v/v, pH2.6).Under the optimized conditions, good linearity was achieved with a correlation coefficient of0.9998. The limits of quantification of the method were2.15μg/kg for CYR and2.51μg/kgfor MEL, which are maximum residue limits as low as three orders of magnitude. Therecovery values at three spiked concentrations were in the range of96.2–107.1%with relativestandard deviations (RSDs) of1.1–5.7%for CYR, and92.7–104.9%with RSDs of1.7–6.1%for MEL. The proposed method allows detection at levels as low as μg/kg levels for CYR andMEL. The method was validated by liquid chromatography–tandem mass spectrometry, andcan be used for the routine determination of CYR and MEL in herbal and edible plantsamples with the characteristics of speed, high sensitivity and accuracy, and low consumptionof reagents.
In chapter4, molecular recognition mechanisms for melamine molecularly imprintedpolymers synthesized in ethanol-water system with melamine as template and methacrylicacid as organic functional monomer were examined by the molecular simulation and theexperimental validation with IR and1H NMR. It was found that amino in melamin withcarboxyl group of methacrylic can be combined to be more stable amido goup than hydrogenbond. Binding study demonstrated that the MIPs showed excellent affinity and highselectivity to melamine.
In chapter5section1, a highly selective molecularly imprinted solid-phase extraction(MISPE) combined with ultra-performance liquid chromatography-PDA detection wasdeveloped for the simultaneous isolation and determination of cyromazine, melamine,ammeline and ammelide in milk samples. The new melamine molecularly imprintedpolymers (MIPs) was applied as a special sorbent for the selective solid-phase extraction(SPE) of melamine and it’s analogues from milk samples, showing high selectivity andaffinity to the melamine and cyromazine in milk. Used the MIPs as SPE sorbents couldeffectively eliminate the interferences of the milk matrix. Under the optimized conditions,good linearity of the method was obtained in a range of0.013~6.667μg/mL with thecorrelation coefficient of>0.999and the relative standard division of2.0–7.4%. The limits ofquantitation of this method were in a range of1.3ng/mL-6.7ng/mL. The proposed methodcould be applied for the selective extraction, separation and determination of melamine andit’s related compounds in milk samples.
In chapter5section2, a highly sensitive method was developed for the determination ofthe residues of cyromazine(CYR), melamine(MEL) anddicyandiamide (DICY) in animaltissue samples by using ultra-high-performance liquid chromatography(UPLC)–PDA eλdetection with accelerated solvent extraction and MISPE cleanup. The conditions ofseparation and detection were investigated and optimized. A ACQUITY UPLC BEH HILIC(100x2.1mm，i.d.,1.7μm) was used for the UPLC, with a mobile phase composed of0.77‰ammonium acetate-acetic acid (pH=4.7) and methanol (4:96, v/v). Under theoptimized conditions, good linearity was achieved with a correlation coefficient of0.9999. The limits of quantification of the method were1.675μg/kg for DICY,5μg/kg for MEL and3.325μg/kg for CYR. The recovery values at three spiked concentrations were in the range of91.2-107%with relative standard deviations (RSDs) of1.7–8.3%for DICY,89.1–105%withRSDs of1.1–6.6%for MEL, and88.7–104%with RSDs of2.1–6.1%for CYR. The proposedmethod can be used for the routine determination of DICY, MEL and CYR in complexbiological samples with the characteristics of high sensitivity, accuracy, and speed.
加速溶剂萃取(ASE)技术已经成为一种常用绿色分离技术，能够在多种样品中萃取出不同种类的农药残留。与传统的提取方法比较，ASE具有操作简便，减少有机溶剂对环境的污染，省时省溶剂，萃取操作完全自动化的特点。分子印迹聚合物(MIPs)是制备对特定分子具有专一性结合能力的高分子技术。MIPs具有亲和性好、选择性高、抗干扰性强、稳定性好，使用寿命长以及应用范围广等优点。目前，两种技术己在农残检测、天然药物分离以及色谱分析等领域得到广泛应用。加速溶剂萃取技术与分子印迹-固相萃取技术相结合可以极大的提高复杂样品前处理的选择性，实现复杂生物样品中农药残留的快速、有效分离。
本文第一章绪论部分简要的对加速溶剂萃取技术和分子印迹技术的研究进展进行了介绍。
第二章建立了加速溶剂萃取-硅胶柱净化-高效液相色谱分析的方法，用于检测烟草中氯虫苯甲酰胺和螺螨酯的残留。实验中对萃取条件进行了优化，包括：萃取溶剂、萃取温度和萃取时长等。对硅胶柱净化手段及色谱条件进行了研究，采用高效液相色谱-二极管阵列检测器的方法对待测物进行测定。在最优条件下，氯虫苯甲酰胺和螺螨酯均表现出了良好的线性范围（r>0.999），方法定量限(LOQ)为氯虫苯甲酰胺16.5μg/kg，螺螨酯66.5μg/kg。回收率为氯虫苯甲酰胺88.5–102%(RSDs=2.7–6.9%)，螺螨酯87.7–98.5%(RSDs=1.8–5.9%)；本方法简单、快速、有效，可以用于烟草中农药残留的分析。
第三章建立了加速溶剂萃取-固相萃取-高效液相色谱的方法，用于8种根类药食两用植物样品中环丙氨嗪及其代谢物三聚氰胺的测定。实验中分别对分离和检测方法的条件进行了探讨和优化，确定了对环境无污染的水作为萃取溶剂使用，应用Waters C18柱作为反相色谱分离柱。在最佳条件下，得到很好的线性回归方程（R=0.9998）。方法的定量限为环丙氨嗪2.15μg/kg，三聚氰胺2.51μg/kg，均低于各自最大允许残留量三个数量级。本方法能够检测出μg/kg水平的环丙氨嗪和三聚氰胺，已通过液相色谱-质谱的方法进行了确证。方法可以对药食两用植物中环丙氨嗪和三聚氰胺进行快速、高灵敏、高精度测定，且费用低廉。
第四章通过分子模拟计算和红外及核磁共振氢谱实验验证，对三聚氰胺为模板分子，甲基丙烯酸为功能单体合成分子印迹聚合物的分子识别机理进行了研究。发现三聚氰胺的氨基与甲基丙烯酸的羧基能够结合成比氢键更稳定的酰胺基。键合研究显示三聚氰胺分子印迹聚合物对三聚氰胺显示出极好的结合能力及选择性。
第五章第一部分建立了一种高选择性和灵敏度的分子印迹固相萃取-超高效液相色谱用来检测牛奶中环丙胺嗪、三聚氰胺、三聚氰胺二酰胺和三聚氰胺一酰胺的方法。方法中应用三聚氰胺分子印迹聚合物做吸附剂可以有效去除牛奶基质对测定的影响。在最佳条件下，方法在0.013~6.667μg/mL范围内具有良好的线性(r>0.999)，相对标准偏差介于2.2-4.6%之间。方法定量限介于1.3ng/mL-6.7ng/mL之间。该方法可以用于选择萃取、分离、测定牛奶及其他奶制品中的三聚氰胺及其相关化合物。
第五章第二部分建立了一种加速溶剂萃取-分子印迹固相萃取-超高效液相色谱的方法来检测肉类中环丙胺嗪、三聚氰胺和双氰胺。方法中采用水作为萃取溶剂，应用三聚氰胺的分子印迹聚合物作为固相萃取的吸附剂对肉类样品进行了处理。实验中对加速溶剂萃取条件和流动相进行了优化。应用ACQUITY UPLC BEH HILIC柱，在最佳条件下，三种待测物线性回归方程的系数均为0.9999。方法定量限低至双氰胺1.675μg/kg、三聚氰胺5μg/kg和环丙胺嗪3.325μg/kg，远低于国家及国际规定的最大允许残留量，方法具有较高的检测能力。三种浓度的标准添加回收率为：88.7–107%，RSDs为1.1–8.3%。方法可以对肉类中双氰胺、三聚氰胺和环丙氨嗪进行快速、高灵敏、高精度测定。
In recent years, increasing attention has been paid to the quality and safety (QS) ofproducts and foodstuffs. In the determination of pesticide residues in agricultural productssamples, sample preparation is very important, because the matrix is complicated andconcentration of analyte is very low. It is important to develop fast, efficient, simple andgreen sample preparation method in order to obtain reliable, repeatable analytical result.
Accelerated solvent extraction (ASE) is a new green extraction technique. ASE canextract different classes of pesticides residues which exist in numerous kinds of plant originfoods. It possesses many advantages such as easy to operate, less pollution to theenvironment by the organic solvent, less time, less solvent and automatic in the extractionprocedures comparing with other traditional extraction methods. Molecularly imprintedpolymers are specific polymer materials that have the selective binding ability to theparticular molecules. Molecularly imprinted polymers have many advantages of good affinity,high selectivity, powerful anti-interference performance, better stability, as well as long lifeand wide range of applications. Molecular imprinting technology had been used in manyfields such as pesticide residues analysis, food analysis, environmental monitoring, naturalproducts separation and chromatographic analysis. The selectivity of complex samplespretreatment was increased greatly when the accelerated-solvent-extraction technology andmolecularly-imprinted-solid-phase-extraction technology were applied together. And thepesticide residues in complex biological samples can be separated and enriched quickly andeffectively.
First of all, it is described that the history and development of the accelerated solventextraction technology and molecularly imprinted technology, and the research advance wasreviewed.
In chapter2, a new method for the determination of chlorantraniliprole (CAP) andspirodiclofen (SDF) residues in tobacco was developed by using liquid chromatography withdiode-array detection (LC-DAD) after accelerated solvent extraction (ASE) and silica gel clean-up. The conditions of ASE, silica gel clean-up and LC were investigated and optimized.A Waters C18column (250×4.6mm ID,5μm) was used for the LC using a mobile phasecomposed of methanol and water (90:10, v/v). Under optimal conditions, the linearity wassatisfactory in the range of0.03–1.5μg/mL with a correlation coefficient of0.9994for CAPand0.13–2.5μg/mL with a correlation coefficient of0.9991for SDF. The method limit ofquantification (LOQ) was16.5μg/kg for CAP, and64.3μg/kg for SDF, which is lower thantheir maximum residue limits (MRLs). The recoveries were88.5–102%with relative standarddeviations (RSDs) of2.7–6.9%for CAP, and87.7–98.5%with RSDs of1.8–5.9%for SDF.The proposed method is simple, rapid and effective, and provides the sensitivity and linearitynecessary for analysis of the pesticides in tobacco.
In chapter3, a highly sensitive method was developed for the determination of theresidues of cyromazine (CYR) and its metabolite, melamine(MEL), in herbal and edible plantsamples by using reversed phase high-performance liquid chromatography–diode-arraydetection (RP-HPLC-DAD) with accelerated solvent extraction and solid phase extractioncleanup. The conditions of separation and detection were investigated and optimized. AWaters C18column (250x4.6mm，i.d.,5μm) was used for the RP-HPLC, with a mobilephase composed of0.1%trifluoroacetic acid solution and methanol (85:15, v/v, pH2.6).Under the optimized conditions, good linearity was achieved with a correlation coefficient of0.9998. The limits of quantification of the method were2.15μg/kg for CYR and2.51μg/kgfor MEL, which are maximum residue limits as low as three orders of magnitude. Therecovery values at three spiked concentrations were in the range of96.2–107.1%with relativestandard deviations (RSDs) of1.1–5.7%for CYR, and92.7–104.9%with RSDs of1.7–6.1%for MEL. The proposed method allows detection at levels as low as μg/kg levels for CYR andMEL. The method was validated by liquid chromatography–tandem mass spectrometry, andcan be used for the routine determination of CYR and MEL in herbal and edible plantsamples with the characteristics of speed, high sensitivity and accuracy, and low consumptionof reagents.
In chapter4, molecular recognition mechanisms for melamine molecularly imprintedpolymers synthesized in ethanol-water system with melamine as template and methacrylicacid as organic functional monomer were examined by the molecular simulation and theexperimental validation with IR and1H NMR. It was found that amino in melamin withcarboxyl group of methacrylic can be combined to be more stable amido goup than hydrogenbond. Binding study demonstrated that the MIPs showed excellent affinity and highselectivity to melamine.
In chapter5section1, a highly selective molecularly imprinted solid-phase extraction(MISPE) combined with ultra-performance liquid chromatography-PDA detection wasdeveloped for the simultaneous isolation and determination of cyromazine, melamine,ammeline and ammelide in milk samples. The new melamine molecularly imprintedpolymers (MIPs) was applied as a special sorbent for the selective solid-phase extraction(SPE) of melamine and it’s analogues from milk samples, showing high selectivity andaffinity to the melamine and cyromazine in milk. Used the MIPs as SPE sorbents couldeffectively eliminate the interferences of the milk matrix. Under the optimized conditions,good linearity of the method was obtained in a range of0.013~6.667μg/mL with thecorrelation coefficient of>0.999and the relative standard division of2.0–7.4%. The limits ofquantitation of this method were in a range of1.3ng/mL-6.7ng/mL. The proposed methodcould be applied for the selective extraction, separation and determination of melamine andit’s related compounds in milk samples.
In chapter5section2, a highly sensitive method was developed for the determination ofthe residues of cyromazine(CYR), melamine(MEL) anddicyandiamide (DICY) in animaltissue samples by using ultra-high-performance liquid chromatography(UPLC)–PDA eλdetection with accelerated solvent extraction and MISPE cleanup. The conditions ofseparation and detection were investigated and optimized. A ACQUITY UPLC BEH HILIC(100x2.1mm，i.d.,1.7μm) was used for the UPLC, with a mobile phase composed of0.77‰ammonium acetate-acetic acid (pH=4.7) and methanol (4:96, v/v). Under theoptimized conditions, good linearity was achieved with a correlation coefficient of0.9999. The limits of quantification of the method were1.675μg/kg for DICY,5μg/kg for MEL and3.325μg/kg for CYR. The recovery values at three spiked concentrations were in the range of91.2-107%with relative standard deviations (RSDs) of1.7–8.3%for DICY,89.1–105%withRSDs of1.1–6.6%for MEL, and88.7–104%with RSDs of2.1–6.1%for CYR. The proposedmethod can be used for the routine determination of DICY, MEL and CYR in complexbiological samples with the characteristics of high sensitivity, accuracy, and speed.
引文
[1] Picó Y, Font G, Moltó J C, et al. Pesticide residue determination in fruit and vegetables by liquidchromatography-mass spectrometry[J]. Journal of Chromatography A,2000,882(1-2):153-173.
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