毛细管电泳在研究二苯乙烯类化合物光诱导顺反异构化反应及环境水样中氨和烷基胺测定中的应用
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摘要
二苯乙烯类化合物在自然界一般同时以顺、反异构体两种形式存在,但仅有反式异构体具有抗肿瘤、抗氧化、抗炎保肝等多种生物活性,且在光照条件下反式能够转化为顺式,从而引起该类潜能药物前体化合物丧失相应的活性。所以通过光谱、色谱、毛细管电泳等多种分析手段研究该类化合物的光诱导异构化反应对进一步开发和利用二苯乙烯类化合物是十分重要的。
本学位论文将毛细管电泳、紫外可见光谱及核磁共振波谱方法相结合对光敏性的二苯乙烯类化合物白藜芦醇苷和苷元、土大黄苷和苷元及脱氧土大黄苷和苷元等的光诱导顺反异构化反应进行了研究。考察了不同照射时间和照射光波长对异构化反应的影响,得到了产物和反应物的立体化学结构信息,计算出了异构化反应的速率常数,并在此基础上探讨了反应的机理。
本学位论文在综述前人工作的基础上,主要进行了以下几个方面具有创新性的研究工作：
1.利用毛细管电泳和紫外可见光谱法,系统考察了影响白藜芦醇苷及其苷元的光诱导顺反异构化反应的各类因素,并通过实验数据计算了反应转化比率和速率常数,对反应机理作了初步探讨。
2.用毛细管电泳分离测定了光诱导的土大黄苷和苷元顺反异构反应的反应物和产物,考察了光照时间和波长对异构化反应的影响,测定了反应速率常数并对实验结果进行了解释,并通过紫外可见光度法证明了毛细管电泳实验结果的有效性及准确性。此外,还通过核磁共振波谱确定了产物的分子结构。
3.首次考察了β-CD与脱氧土大黄苷元的包合作用对紫外光诱导异构化反应的影响,探讨了包合方式、测定了反应速率常数并对实验结果进行了解释。
4.以NBD-C1为衍生试剂,建立了同时分离测定氨和22种烷基胺的毛细管胶束电泳激光诱导荧光检测新方法。该方法已成功用于环境水样中氨及烷基胺类污染物的检测。论文共分五章：
第一章：介绍了研究化学反应动力学的各类常用方法,重点综述了毛细管电泳用于化学反应动力学研究的几种模式及其近年来在研究化学反应动力学方面的发展趋势和应用。
第二章：利用高效毛细管电泳和紫外可见分光光度法对白藜芦醇苷及其苷元的光诱导顺反异构化反应进行了研究,对影响该反应的各种因素包括溶液浓度、照射光源波长、照射时间、溶剂极性进行了系统考察,并对反应机理进行了初步探讨。测得白藜芦醇苷和苷元及其顺式异构体的甲醇水溶液的最大紫外吸收波长分别为305/285 nm和319/291 nm。实验结果表明溶液浓度越稀对光越敏感；照射光源的波长大于化合物的最大吸收波长时对异构化反应的影响更为显著；随照射时间增长,异构化反应比例增大,进入平衡状态后,反应物与产物的浓度不再变化,365 nm光源照射下反式白藜芦醇苷元转化75%,白藜芦醇苷转化58%；带有可吸收紫外光的发色团的丙酮溶剂一定程度上会抑制顺反异构化；最大紫外吸收波长高于白藜芦醇苷元的最大紫外吸收波长的紫外吸收剂也能够抑制其顺反异构化。
第三章：通过毛细管区带电泳研究了光诱导土大黄苷及其苷元的顺反异构反应。该方法3 min内完成了对光照射后样品中的反应物和产物的定量检测。研究了各个反应条件包括不同的光照时间和照射波长对反应产率的影响,计算了反应转化比率和反应速率常数；并用紫外可见分光光度法对毛细管电泳方法所得实验结果进行了验证；用核磁共振波谱对反应产物的分子结构进行了鉴定,排除了反式异构体经光诱导反应后生成除顺式产物外的其他副产物的可能性。
第四章：利用毛细管电泳研究了光诱导脱氧土大黄苷及其苷元的顺反异构化反应。该方法在4min内可完成反式反应物和顺式产物及副产物的分离测定,依据实验数据求得异构化反应的转化比率和速率常数。结合紫外光谱法考察了光诱导异构化反应前后化合物的光谱变化,并用紫外光谱对CD包合物进行表征,考察了p-环糊精(p-CD)与脱氧土大黄苷的包合过程对脱氧土大黄苷紫外光诱导异构化反应的影响,结果表明与CD的包合作用加速了光诱导异构化过程,计算所得反应速率常数大于CD不存在时的反应速率常数。
第五章：以NBD-Cl为衍生试剂,建立了一种同时分离测定氨和22种烷基胺的毛细管胶束电泳-激光诱导荧光新方法,对衍生和电泳分离的条件进行了优化。最佳衍生条件为：衍生试剂NBD-Cl浓度为15 mM,硼砂衍生缓冲溶液浓度30mM,pH9.0,70℃下反应20 min。最佳的分离条件为：分离缓冲溶液为20 mM硼砂-25 mM SDS-7 mMβ-CD-10%乙睛-0.5 mM尿素,pH 9.70,分离电压25 kV。该体系在19 min内分离了氨和22种烷基胺,迁移时间和峰面积的相对标准偏差分别小于0.72%和1.87%。该方法已成功应用于测定环境水样包括湖水、池塘水和黄河水中的氨及烷基胺污染物,回收率在90.2%到110.8%之间,结果令人满意。
Stilbene compounds normally existed in both cis- and trans- forms in nature, but only trans-isomer has antitumor, antioxidant, anti-inflammatory and other biological activities, and in the condition of light the trans-isomer can transformed into cis-isomer, which led to the lose of activities of such precursor compound of potential drug. Therefore, through spectroscopy, chromatography, capillary electrophoresis and other analytical tools to study the light-induced cis-trans isomerization of these compounds is very important for the further development and use of stilbene compounds.
This dissertation mainly focused on the study of light-induced isomerization of stilbenes, including resveratrol, piceid, rhapontigenin, rhaponticin, desoxyrhaponticin and desoxyrhapontigenin using capillary electrophoresis, UV- Vis and NMR spectrum. The effects of irradiation time and wavelength of light were studied, and the stereo chemistry structure characteristics were obtaind. And the rate constant of the isomerization was also calculated. On the basis of experiment, the mechanism of reaction was discussed.
On the basis of previous literatures, some original studies were carried out as follows:
1. The effects of various factors on the light-induced isomerization of resveratrol and piceid were studied by CE-DAD system and UV-Vis spectrum. On the basis of experiment, the reaction conversion rate and the rate constant were calculated. Furthermore, the mechanism of reaction was preliminarily discussed.
2. The determinations of trans- reactant and cis- product of the light induced isomerization of rhapontigenin and rhaponticin were performed through the capillary electrophoresis. The effects of the irradiation time and wavelength were investigated. The experiment result of CE was further verified by UV-Vis spectrum, and the stereochemistry molecular structure was confirmed by NMR.
3. The effect of the complexation of P-CD and desxoyrhapontigenin on the light-induced isomerization was discussed for the first time, and studied the way of complexation, calculated the rate constant of isomerization, futher explained the experimental results.
4. A selective and sensitive method was developed for simultaneous determination of ammonia and 22 aliphatic amines by micellar electrokinetic chromatography (MEKC) with laser-induced fluorescence detection (LIF) using NBD-Cl as derivatization reagent. The method was successfully applied for the determination of aliphatic amines and ammonia in environment water samples.
This dissertation consists of five chapters:
Chapter 1:This chapter introduced various methods for the study of chemical reaction dynamics, focus on the several common modes, developments and applications of capillary electrophoresis in the study of chemical reaction dynamics.
Chapter 2:Qualitive and quantitive research of light-induced isomerization of resveratrol and piceid were performed by CE and UV- Vis spectrum. The effects of reaction conditions on the isomerization were evaluated, including the concentration of solution, wavelength of irradiation light, irradiation time, different solvents and UV absorbents. On the basis of experiment, the mechanism of reaction was preliminarily discussed. The maximum UV absorption wavelengths of methanol solution of RES, piceid and each cis-isomer were 305/285 nm and 319/291nm, respectively. The results showed that the more dilute solution was more sensitive to light; when the wavelength of light source is longer than the maximum UV absorption wavelengths of compounds, the effect on isomerization is more significant; with the irradiation time increases, the proportion of isomerization increased, when it reached the equilibrium state, the concentrations of reactants and products did not change anymore; under the irradiation of 365 nm, trans RES converted 75%, piceid converted 58%; acetone solvent with UV-absorbing chromophore inhibited the cis-trans isomerization to some extent; The UV absorbents whose maximum UV absorption wavelength longer than the maximum UV absorption wavelength of RES are also able to inhibit the isomerization of RES.
Chapter 3:The determinations of trans- material and cis- product of the light induced isomerization of rhapontigenin and rhaponticin were performed through capillary zone electrophoretic. The samples after irrdiation were directly injected and analyzed by CZE-DAD, and the experiment was finishied in 3 minutes. The effects of various reaction conditions including different irradiation time, wavelength of light on the yield of isomerization were studied. And the result was further verified by UV- Vis spectrum, and the stereochemistry molecular structure were confirmed by NMR, excluded the possibility of existence of by-product.
Chapter 4:Study of the light-induced isomerization of DOR and DG was performed by capillary electrophoresis. Using 30 mM borax, pH 2.5 background buffer completed the separation of the cis-product and trans-reactant within 4 minutes and the rate constant of isomerization was 0.0189 min-1. The UV-Vis spectra before and after UV irradiation were also studied. And UV spectra of the CD inclusion complex were characterized to investigate the effect ofβ-cyclodextrin (β-CD) and deoxy glycosides inclusion on the isomerization. The results showed that the cooperation with CD accelerated the process of light-induced isomerization, the reaction rate constant was 0.0268 min-1, which is bigger than the rate constant when the CD does not exist.
Chapter 5:A selective and sensitive method was developed for separation and simultaneous determination of 22 aliphatic amines and ammonia by MEKC-LIF using NBD-Cl as derivatization reagent. And the detailed conditions of derivatization and separationand were discussed. The optimum deirvatization conditions were:1.5 mM NBD-Cl,30 mM borax derivatization buffer, pH 9.0,70℃, incubation time was 20 min; The optimum separation conditions were:20 mM borax separation buffer,25 mM SDS,7 mMβ-CD,10% acetonitrile and 0.5 mM urea at pH 9.70, separation voltage was 25 kV.22 aliphatic amines and ammonia were separated in a short 19 min analysis time and the relative standard deviations for migration time and peak areas were less than 0.72% and 1.73%, respectively. The method was successfully applied for the quantification of aliphatic amines and ammonia in environmental water samples, including aquarium water, lake water and the yellow river water, and the reconvenes were in the range of 90.2% to 110.8%, the result is satisfied.
本学位论文将毛细管电泳、紫外可见光谱及核磁共振波谱方法相结合对光敏性的二苯乙烯类化合物白藜芦醇苷和苷元、土大黄苷和苷元及脱氧土大黄苷和苷元等的光诱导顺反异构化反应进行了研究。考察了不同照射时间和照射光波长对异构化反应的影响,得到了产物和反应物的立体化学结构信息,计算出了异构化反应的速率常数,并在此基础上探讨了反应的机理。
本学位论文在综述前人工作的基础上,主要进行了以下几个方面具有创新性的研究工作：
1.利用毛细管电泳和紫外可见光谱法,系统考察了影响白藜芦醇苷及其苷元的光诱导顺反异构化反应的各类因素,并通过实验数据计算了反应转化比率和速率常数,对反应机理作了初步探讨。
2.用毛细管电泳分离测定了光诱导的土大黄苷和苷元顺反异构反应的反应物和产物,考察了光照时间和波长对异构化反应的影响,测定了反应速率常数并对实验结果进行了解释,并通过紫外可见光度法证明了毛细管电泳实验结果的有效性及准确性。此外,还通过核磁共振波谱确定了产物的分子结构。
3.首次考察了β-CD与脱氧土大黄苷元的包合作用对紫外光诱导异构化反应的影响,探讨了包合方式、测定了反应速率常数并对实验结果进行了解释。
4.以NBD-C1为衍生试剂,建立了同时分离测定氨和22种烷基胺的毛细管胶束电泳激光诱导荧光检测新方法。该方法已成功用于环境水样中氨及烷基胺类污染物的检测。论文共分五章：
第一章：介绍了研究化学反应动力学的各类常用方法,重点综述了毛细管电泳用于化学反应动力学研究的几种模式及其近年来在研究化学反应动力学方面的发展趋势和应用。
第二章：利用高效毛细管电泳和紫外可见分光光度法对白藜芦醇苷及其苷元的光诱导顺反异构化反应进行了研究,对影响该反应的各种因素包括溶液浓度、照射光源波长、照射时间、溶剂极性进行了系统考察,并对反应机理进行了初步探讨。测得白藜芦醇苷和苷元及其顺式异构体的甲醇水溶液的最大紫外吸收波长分别为305/285 nm和319/291 nm。实验结果表明溶液浓度越稀对光越敏感；照射光源的波长大于化合物的最大吸收波长时对异构化反应的影响更为显著；随照射时间增长,异构化反应比例增大,进入平衡状态后,反应物与产物的浓度不再变化,365 nm光源照射下反式白藜芦醇苷元转化75%,白藜芦醇苷转化58%；带有可吸收紫外光的发色团的丙酮溶剂一定程度上会抑制顺反异构化；最大紫外吸收波长高于白藜芦醇苷元的最大紫外吸收波长的紫外吸收剂也能够抑制其顺反异构化。
第三章：通过毛细管区带电泳研究了光诱导土大黄苷及其苷元的顺反异构反应。该方法3 min内完成了对光照射后样品中的反应物和产物的定量检测。研究了各个反应条件包括不同的光照时间和照射波长对反应产率的影响,计算了反应转化比率和反应速率常数；并用紫外可见分光光度法对毛细管电泳方法所得实验结果进行了验证；用核磁共振波谱对反应产物的分子结构进行了鉴定,排除了反式异构体经光诱导反应后生成除顺式产物外的其他副产物的可能性。
第四章：利用毛细管电泳研究了光诱导脱氧土大黄苷及其苷元的顺反异构化反应。该方法在4min内可完成反式反应物和顺式产物及副产物的分离测定,依据实验数据求得异构化反应的转化比率和速率常数。结合紫外光谱法考察了光诱导异构化反应前后化合物的光谱变化,并用紫外光谱对CD包合物进行表征,考察了p-环糊精(p-CD)与脱氧土大黄苷的包合过程对脱氧土大黄苷紫外光诱导异构化反应的影响,结果表明与CD的包合作用加速了光诱导异构化过程,计算所得反应速率常数大于CD不存在时的反应速率常数。
第五章：以NBD-Cl为衍生试剂,建立了一种同时分离测定氨和22种烷基胺的毛细管胶束电泳-激光诱导荧光新方法,对衍生和电泳分离的条件进行了优化。最佳衍生条件为：衍生试剂NBD-Cl浓度为15 mM,硼砂衍生缓冲溶液浓度30mM,pH9.0,70℃下反应20 min。最佳的分离条件为：分离缓冲溶液为20 mM硼砂-25 mM SDS-7 mMβ-CD-10%乙睛-0.5 mM尿素,pH 9.70,分离电压25 kV。该体系在19 min内分离了氨和22种烷基胺,迁移时间和峰面积的相对标准偏差分别小于0.72%和1.87%。该方法已成功应用于测定环境水样包括湖水、池塘水和黄河水中的氨及烷基胺污染物,回收率在90.2%到110.8%之间,结果令人满意。
Stilbene compounds normally existed in both cis- and trans- forms in nature, but only trans-isomer has antitumor, antioxidant, anti-inflammatory and other biological activities, and in the condition of light the trans-isomer can transformed into cis-isomer, which led to the lose of activities of such precursor compound of potential drug. Therefore, through spectroscopy, chromatography, capillary electrophoresis and other analytical tools to study the light-induced cis-trans isomerization of these compounds is very important for the further development and use of stilbene compounds.
This dissertation mainly focused on the study of light-induced isomerization of stilbenes, including resveratrol, piceid, rhapontigenin, rhaponticin, desoxyrhaponticin and desoxyrhapontigenin using capillary electrophoresis, UV- Vis and NMR spectrum. The effects of irradiation time and wavelength of light were studied, and the stereo chemistry structure characteristics were obtaind. And the rate constant of the isomerization was also calculated. On the basis of experiment, the mechanism of reaction was discussed.
On the basis of previous literatures, some original studies were carried out as follows:
1. The effects of various factors on the light-induced isomerization of resveratrol and piceid were studied by CE-DAD system and UV-Vis spectrum. On the basis of experiment, the reaction conversion rate and the rate constant were calculated. Furthermore, the mechanism of reaction was preliminarily discussed.
2. The determinations of trans- reactant and cis- product of the light induced isomerization of rhapontigenin and rhaponticin were performed through the capillary electrophoresis. The effects of the irradiation time and wavelength were investigated. The experiment result of CE was further verified by UV-Vis spectrum, and the stereochemistry molecular structure was confirmed by NMR.
3. The effect of the complexation of P-CD and desxoyrhapontigenin on the light-induced isomerization was discussed for the first time, and studied the way of complexation, calculated the rate constant of isomerization, futher explained the experimental results.
4. A selective and sensitive method was developed for simultaneous determination of ammonia and 22 aliphatic amines by micellar electrokinetic chromatography (MEKC) with laser-induced fluorescence detection (LIF) using NBD-Cl as derivatization reagent. The method was successfully applied for the determination of aliphatic amines and ammonia in environment water samples.
This dissertation consists of five chapters:
Chapter 1:This chapter introduced various methods for the study of chemical reaction dynamics, focus on the several common modes, developments and applications of capillary electrophoresis in the study of chemical reaction dynamics.
Chapter 2:Qualitive and quantitive research of light-induced isomerization of resveratrol and piceid were performed by CE and UV- Vis spectrum. The effects of reaction conditions on the isomerization were evaluated, including the concentration of solution, wavelength of irradiation light, irradiation time, different solvents and UV absorbents. On the basis of experiment, the mechanism of reaction was preliminarily discussed. The maximum UV absorption wavelengths of methanol solution of RES, piceid and each cis-isomer were 305/285 nm and 319/291nm, respectively. The results showed that the more dilute solution was more sensitive to light; when the wavelength of light source is longer than the maximum UV absorption wavelengths of compounds, the effect on isomerization is more significant; with the irradiation time increases, the proportion of isomerization increased, when it reached the equilibrium state, the concentrations of reactants and products did not change anymore; under the irradiation of 365 nm, trans RES converted 75%, piceid converted 58%; acetone solvent with UV-absorbing chromophore inhibited the cis-trans isomerization to some extent; The UV absorbents whose maximum UV absorption wavelength longer than the maximum UV absorption wavelength of RES are also able to inhibit the isomerization of RES.
Chapter 3:The determinations of trans- material and cis- product of the light induced isomerization of rhapontigenin and rhaponticin were performed through capillary zone electrophoretic. The samples after irrdiation were directly injected and analyzed by CZE-DAD, and the experiment was finishied in 3 minutes. The effects of various reaction conditions including different irradiation time, wavelength of light on the yield of isomerization were studied. And the result was further verified by UV- Vis spectrum, and the stereochemistry molecular structure were confirmed by NMR, excluded the possibility of existence of by-product.
Chapter 4:Study of the light-induced isomerization of DOR and DG was performed by capillary electrophoresis. Using 30 mM borax, pH 2.5 background buffer completed the separation of the cis-product and trans-reactant within 4 minutes and the rate constant of isomerization was 0.0189 min-1. The UV-Vis spectra before and after UV irradiation were also studied. And UV spectra of the CD inclusion complex were characterized to investigate the effect ofβ-cyclodextrin (β-CD) and deoxy glycosides inclusion on the isomerization. The results showed that the cooperation with CD accelerated the process of light-induced isomerization, the reaction rate constant was 0.0268 min-1, which is bigger than the rate constant when the CD does not exist.
Chapter 5:A selective and sensitive method was developed for separation and simultaneous determination of 22 aliphatic amines and ammonia by MEKC-LIF using NBD-Cl as derivatization reagent. And the detailed conditions of derivatization and separationand were discussed. The optimum deirvatization conditions were:1.5 mM NBD-Cl,30 mM borax derivatization buffer, pH 9.0,70℃, incubation time was 20 min; The optimum separation conditions were:20 mM borax separation buffer,25 mM SDS,7 mMβ-CD,10% acetonitrile and 0.5 mM urea at pH 9.70, separation voltage was 25 kV.22 aliphatic amines and ammonia were separated in a short 19 min analysis time and the relative standard deviations for migration time and peak areas were less than 0.72% and 1.73%, respectively. The method was successfully applied for the quantification of aliphatic amines and ammonia in environmental water samples, including aquarium water, lake water and the yellow river water, and the reconvenes were in the range of 90.2% to 110.8%, the result is satisfied.
引文
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