基于亲水作用色谱和串联质谱联用的细胞分裂素分析方法研究
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摘要
天然的细胞分裂素是七大植物激素的一种，在植物的生长和发育过程中起重要作用。它能够促进细胞分裂和分化，促进根的形成和生长，消除顶端优势，延缓叶片衰老等，几乎影响着植物体从胚胎形成到衰老的整个生长发育过程。精确测定植物组织中细胞分裂素的含量，对进一步了解细胞分裂素在植物体内的生物学作用意义重大。由于植物基质复杂，细胞分裂素含量少，植物体内各种酶的存在会导致细胞分裂素在几种形式之间不断转化、代谢和降解，对细胞分裂素的定性和定量分析困难重重。因此，寻找选择性好，灵敏度高的分析方法非常迫切。尽管近年来针对细胞分裂素的分析方法均有报道，但寻找更加简便、快速、实用的新方法依然是细胞分裂素分析的研究热点之一。本论文致力于开发新型的样品预处理方法和分离方法用于细胞分裂素的定量分析。主要内容如下：
1.评述了细胞分裂素的研究概况，着重介绍了植物样品中细胞分裂素的样品制备、分离、检测技术以及目前分析科学领域新型的样品前处理方法和分离技术。
2.采用P(AMPS-co-EGDMA)聚合物整体柱作为聚合物整体柱微萃取（PMME）的萃取介质对复杂植物样品中的细胞分裂素进行富集与纯化；并以硅胶柱为分离柱，首次建立了细胞分裂素的亲水作用色谱（HILIC）分离方法。PMME材料制备简单，操作简便，节省溶剂,萃取效率高；HILIC无需梯度洗脱，在等度洗脱下即可有效分离多种细胞分裂素及干扰物， HILIC模式下高有机溶剂含量的流动相很大程度上提高了与质谱联用的灵敏度；而以电喷雾串联质谱（ESI-MS/MS）为检测系统，更进一步提高了定性能力和分析灵敏度。我们将这种PMME-HILIC-MS/MS方法成功用于水稻、拟南芥、油菜中细胞分裂素的测定，为复杂植物样品中细胞分裂素的定量分析提供了一种可靠、实用的方法。
3.采用C_(18)和混合模式（silica@C_8/SO_3H）SPE的串联组合，成功建立了一种简单、快速的一步固相萃取法用于定量分析植物组织中的内源性细胞分裂素。植物提取液在过C_(18)小柱除掉部分色素和酯类物质后，不经过浓缩和重新定容，即可直接在混合模式SPE柱上上样，并得到较高的回收率（绝对回收率>80%）。此方法避免了冗长的溶剂浓缩和多次活化步骤，可极大缩短前处理时间，实现快速、高效、高通量的萃取。
4.在第三部分内容的基础上，建立了以P（MAA-co-EGDMA）聚合物整体柱为在线富集柱的的串联固相萃取-在线富集-亲水作用色谱串联质谱联用方法（tandem SPE-online trapping-HILIC-MS/MS）定量分析植物中的内源性细胞分裂素。基于自动进样器与双六通阀双泵的全自动在线富集系统，能够进一步除杂，并实现大体积上样，避免了因进样量受限而造成的样品损失，提高了检测灵敏度。串联固相萃取与在线富集系统的结合，在简化前处理步骤，加快前处理的速度的同时，将检测灵敏度提高了一个数量级以上。我们考察了此方法所需的最低植物用量，结果表明，仅需20mg甚至更少的植物样品即可对多种细胞分裂素准确定量。此方法的建立对研究植物激素代谢机制和生理机能等有较好的应用价值。
5.制备了新型的Fe_3O_4/SiO_2/poly（AMPS-co-EGDMA）磁性聚合物并将其作为磁固相萃取介质（MSPE）用于细胞分裂素的富集。实验证明，合成的磁性聚合物具有大比表面和多孔结构，对细胞分裂素有较好的富集能力。MSPE的分散萃取模式可直接用于大体积液体样品中痕量细胞分裂素的分析，其磁分离能力使细胞分裂素的富集操作简便快速。MSPE与HILIC-MS/MS联用简单快速，可作为分析植物基质中细胞分裂素的常用方法。
Naturally occurring cytokinins (CKs) are a group of plant hormones whichregulate a wide variety of physiological and developmental processes in plants, suchas promotion of cell devision and differentiation, influence of shoot formation anddevelopment, control of apical dominace and leaf senescence. Accurate determinationof CKs in plant tissues is of great significance for in-depth understanding of theirbiological function. However, the complicated matrix of plant extracts, theextremely low concentration levels of CKs and the presence of enzymes, which canlead to the transformantion and degradation of CKs, make their quantificationbeseting with difficulties. Thus, a highly sensitive, selective and reliable method foridentification and quantification of CKs is particularly required. In recent reports,several technologies have been used in the fields of CKs analysis. However, todevelop simpler, quicker and more practical approaches are still the hotspots.
In this dissertation, the author is devoted to the development of new samplepretreatment methods and separation technologies for CKs quantitative analysis.The major contents of this dissertation are described as follows:
1. The development of CK analysis was reviewed. Emphasis is laid on thetechniques for sample preparation, separation and detection of CKs and theintroduction of new pretreatment methods and separation technologies in separationscience.
2. A sensitive assay of CKs was developed using polymer monolithmicroextraction/hydrophilic interaction chromatography/electrospray ionization-tandem mass spectrometry (PMME/HILIC/ESI-MS/MS). The extraction wasperformed on a poly(2-acrylamido-2-methyl-1-propanesulfonic acid-co-ethylenedimethacrylate)(poly(AMPS-co-EDMA)) capillary monolith and the subsequentseparation was carried out on a Luna silica column in HILIC mode. PMME is a novelsolvent-free and convenient technique with small sample consumption, and HILICcan provide better separation with isocratic elution and higher sensitivity whencoupled with MS detector. Finally, the developed method was applied to the determination of CKs in various samples including Oryza sativa, Arabidopsis thalianaand oil seed rape and demonstrated to be an alternatively reliable and sensitive toolfor CKs studies.
3. A simple and rapid one-step tandem solid phase extraction (SPE) method bycombining C_(18)and mixed mode SPE (silica@C8/SO_3H) was developed for thedetermination of CKs in plant samples. The tandem SPE offers a high recoverygreater than80%and an advantage for convenient analysis due to the compatibility ofthe extraction solvent (Bieleski solvent) for plant samples and the sampling solvent ofsilica@C8/SO_3H cartridge, which avoids the concentration of samples in a largevolume of modified Bieleski extraction solvent followed by a redissolving step andcan greatly reduce the time of sample preparation. This method can achieve rapid,efficient and high-throughput extraction toward CKs.
4. Based on the third part, a rapid and highly sensitive analytical method for thedetermination of plant CKs was developed by employing tandem solid phaseextraction (C_(18)and silica@C8/SO_3H cartridges) and online trapping technique coupledwith HILIC-MS/MS (tandem SPE-online trapping-HILIC-MS/MS). Poly (methacrylicacid-ethylene glycol dimethacrylate)(poly(MAA-co-EGDMA) monolith and HILICwere used as the online trapping column and separation mode, respectively, whichimproved the detection sensitivity of CKs by at least one order of magnitudecompared with other previously reported methods. In this respect, only20mg of planttissue were required for simultaneous quantitative analysis of major CKs in plantsamples. Using this method we successfully determined the concentration of theendogenous CKs in three plant samples, which demonstrated the potential applicationof this method on the highly sensitive detection of CKs in small amount plant samplesfor the studies of plant metabolism and physiology.
5. A2-acrylamido-2-methyl-1-propanesulfonic acid-co-ethylene glycoldimethacrylate magnetic copolymer (Fe_3O_4/SiO_2/poly(AMPS-co-EGDMA)) wasprepared and used as a magnetic solid phase extraction (MSPE) medium for recoveryof endogenous CKs from plant extracts. This magnetic porous polymer wasdemonstrated to have high extraction capacity toward CKs in plants due to its good specificity, large surface area and porous structure. The dispersion extraction mode ofMSPE can be directly used for analysis of large-volume sample solvents with traceCKs, and the magnetic property made the procedure simple and rapid. In addition,coupling with HILIC–MS/MS, a rapid, simple, and effective MSPE–HILIC–MS/MSanalytical method for the quantitative analysis of endogenous CKs in Oryza sativaroots was successfully established.
1.评述了细胞分裂素的研究概况，着重介绍了植物样品中细胞分裂素的样品制备、分离、检测技术以及目前分析科学领域新型的样品前处理方法和分离技术。
2.采用P(AMPS-co-EGDMA)聚合物整体柱作为聚合物整体柱微萃取（PMME）的萃取介质对复杂植物样品中的细胞分裂素进行富集与纯化；并以硅胶柱为分离柱，首次建立了细胞分裂素的亲水作用色谱（HILIC）分离方法。PMME材料制备简单，操作简便，节省溶剂,萃取效率高；HILIC无需梯度洗脱，在等度洗脱下即可有效分离多种细胞分裂素及干扰物， HILIC模式下高有机溶剂含量的流动相很大程度上提高了与质谱联用的灵敏度；而以电喷雾串联质谱（ESI-MS/MS）为检测系统，更进一步提高了定性能力和分析灵敏度。我们将这种PMME-HILIC-MS/MS方法成功用于水稻、拟南芥、油菜中细胞分裂素的测定，为复杂植物样品中细胞分裂素的定量分析提供了一种可靠、实用的方法。
3.采用C_(18)和混合模式（silica@C_8/SO_3H）SPE的串联组合，成功建立了一种简单、快速的一步固相萃取法用于定量分析植物组织中的内源性细胞分裂素。植物提取液在过C_(18)小柱除掉部分色素和酯类物质后，不经过浓缩和重新定容，即可直接在混合模式SPE柱上上样，并得到较高的回收率（绝对回收率>80%）。此方法避免了冗长的溶剂浓缩和多次活化步骤，可极大缩短前处理时间，实现快速、高效、高通量的萃取。
4.在第三部分内容的基础上，建立了以P（MAA-co-EGDMA）聚合物整体柱为在线富集柱的的串联固相萃取-在线富集-亲水作用色谱串联质谱联用方法（tandem SPE-online trapping-HILIC-MS/MS）定量分析植物中的内源性细胞分裂素。基于自动进样器与双六通阀双泵的全自动在线富集系统，能够进一步除杂，并实现大体积上样，避免了因进样量受限而造成的样品损失，提高了检测灵敏度。串联固相萃取与在线富集系统的结合，在简化前处理步骤，加快前处理的速度的同时，将检测灵敏度提高了一个数量级以上。我们考察了此方法所需的最低植物用量，结果表明，仅需20mg甚至更少的植物样品即可对多种细胞分裂素准确定量。此方法的建立对研究植物激素代谢机制和生理机能等有较好的应用价值。
5.制备了新型的Fe_3O_4/SiO_2/poly（AMPS-co-EGDMA）磁性聚合物并将其作为磁固相萃取介质（MSPE）用于细胞分裂素的富集。实验证明，合成的磁性聚合物具有大比表面和多孔结构，对细胞分裂素有较好的富集能力。MSPE的分散萃取模式可直接用于大体积液体样品中痕量细胞分裂素的分析，其磁分离能力使细胞分裂素的富集操作简便快速。MSPE与HILIC-MS/MS联用简单快速，可作为分析植物基质中细胞分裂素的常用方法。
Naturally occurring cytokinins (CKs) are a group of plant hormones whichregulate a wide variety of physiological and developmental processes in plants, suchas promotion of cell devision and differentiation, influence of shoot formation anddevelopment, control of apical dominace and leaf senescence. Accurate determinationof CKs in plant tissues is of great significance for in-depth understanding of theirbiological function. However, the complicated matrix of plant extracts, theextremely low concentration levels of CKs and the presence of enzymes, which canlead to the transformantion and degradation of CKs, make their quantificationbeseting with difficulties. Thus, a highly sensitive, selective and reliable method foridentification and quantification of CKs is particularly required. In recent reports,several technologies have been used in the fields of CKs analysis. However, todevelop simpler, quicker and more practical approaches are still the hotspots.
In this dissertation, the author is devoted to the development of new samplepretreatment methods and separation technologies for CKs quantitative analysis.The major contents of this dissertation are described as follows:
1. The development of CK analysis was reviewed. Emphasis is laid on thetechniques for sample preparation, separation and detection of CKs and theintroduction of new pretreatment methods and separation technologies in separationscience.
2. A sensitive assay of CKs was developed using polymer monolithmicroextraction/hydrophilic interaction chromatography/electrospray ionization-tandem mass spectrometry (PMME/HILIC/ESI-MS/MS). The extraction wasperformed on a poly(2-acrylamido-2-methyl-1-propanesulfonic acid-co-ethylenedimethacrylate)(poly(AMPS-co-EDMA)) capillary monolith and the subsequentseparation was carried out on a Luna silica column in HILIC mode. PMME is a novelsolvent-free and convenient technique with small sample consumption, and HILICcan provide better separation with isocratic elution and higher sensitivity whencoupled with MS detector. Finally, the developed method was applied to the determination of CKs in various samples including Oryza sativa, Arabidopsis thalianaand oil seed rape and demonstrated to be an alternatively reliable and sensitive toolfor CKs studies.
3. A simple and rapid one-step tandem solid phase extraction (SPE) method bycombining C_(18)and mixed mode SPE (silica@C8/SO_3H) was developed for thedetermination of CKs in plant samples. The tandem SPE offers a high recoverygreater than80%and an advantage for convenient analysis due to the compatibility ofthe extraction solvent (Bieleski solvent) for plant samples and the sampling solvent ofsilica@C8/SO_3H cartridge, which avoids the concentration of samples in a largevolume of modified Bieleski extraction solvent followed by a redissolving step andcan greatly reduce the time of sample preparation. This method can achieve rapid,efficient and high-throughput extraction toward CKs.
4. Based on the third part, a rapid and highly sensitive analytical method for thedetermination of plant CKs was developed by employing tandem solid phaseextraction (C_(18)and silica@C8/SO_3H cartridges) and online trapping technique coupledwith HILIC-MS/MS (tandem SPE-online trapping-HILIC-MS/MS). Poly (methacrylicacid-ethylene glycol dimethacrylate)(poly(MAA-co-EGDMA) monolith and HILICwere used as the online trapping column and separation mode, respectively, whichimproved the detection sensitivity of CKs by at least one order of magnitudecompared with other previously reported methods. In this respect, only20mg of planttissue were required for simultaneous quantitative analysis of major CKs in plantsamples. Using this method we successfully determined the concentration of theendogenous CKs in three plant samples, which demonstrated the potential applicationof this method on the highly sensitive detection of CKs in small amount plant samplesfor the studies of plant metabolism and physiology.
5. A2-acrylamido-2-methyl-1-propanesulfonic acid-co-ethylene glycoldimethacrylate magnetic copolymer (Fe_3O_4/SiO_2/poly(AMPS-co-EGDMA)) wasprepared and used as a magnetic solid phase extraction (MSPE) medium for recoveryof endogenous CKs from plant extracts. This magnetic porous polymer wasdemonstrated to have high extraction capacity toward CKs in plants due to its good specificity, large surface area and porous structure. The dispersion extraction mode ofMSPE can be directly used for analysis of large-volume sample solvents with traceCKs, and the magnetic property made the procedure simple and rapid. In addition,coupling with HILIC–MS/MS, a rapid, simple, and effective MSPE–HILIC–MS/MSanalytical method for the quantitative analysis of endogenous CKs in Oryza sativaroots was successfully established.
引文
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