环境中类固醇类内分泌干扰物的检测技术及其降解行为研究
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摘要
本文研究类固醇新的分析检测方法，降解行为及其环境分布，着重研究污水处理厂的污水样品的新萃取方法及各种新的联用技术，全文分为六章：
第一章概述了内分泌干扰物与活性最强的类固醇激素的研究热点，介绍了几种主要类固醇激素的生物功能、存在形式、环境命运和主要分析手段，对我国内分泌干扰物的研究状况进行了综述。
第二章将Triton X-114非离子表面活性剂作为浊点萃取溶剂应用于水样中雌激素类化合物的萃取富集，并与高效液相色谱结合，建立了这类化合物新的小体积，高富集效率的分析方法。该方法首先使一定浓度的Triton X-114非离子表面活性剂与待富集的样品盐溶液混合并在水浴中平衡，离心分离，而后弃去上层水溶液，取下层表面活性剂富集相20μL直接进样，进入液相色谱分离测定。实验优化了萃取过程中的影响因素如表面活性剂浓度、盐浓度、平衡温度平衡时间和离心时间等。该方法对于雌激素类化合物雌酮，雌二醇，雌三醇和孕酮的检测限分别为0.25、0.32、0.23和5.0 ng mL~(-1)。应用该方法测定了几种环境水样如自来水、养鱼水和生活污水中雌激素类化合物的含量。四类水样中均未测出雌激素类化合物，对雌激素进行加标回收，回收率分别为81.2—99.5％。Triton X-114作为浊点萃取剂具有浊点温度低，密度较高，有利于离心分离，价格低廉等优点。与传统液液萃取，固相萃取比较，整个萃取过程不需要任何有机溶剂，是一种绿色、高效的分析方法，适合大批量、小体积样品的快速检测。
第三章在浊点萃取雌激素的基础上继续探索浊点萃取在内分泌干扰物-酞酸酯中的应用。预期能够在相同条件下同时富集多种内分泌干扰物。并用于环境样品的处理。将Triton X-114非离子表面活性剂作为浊点萃取溶剂应用于水样中酞酸酯类化合物的萃取富集，并与高效液相色谱结合，建立了这类化合物新的分析方法。实验考察优化了萃取过程中的影响因素如表面活性剂浓度，盐浓度，平衡温度和平衡时间等。该方法对于酞酸酯类化合物邻苯二甲酸乙酯(DEP)、邻苯二甲酸乙基己酯(DEHP)和邻苯二甲酸环己酯(DCP)的检测限分别为2.0，3.8，1.0 ng．mL~(-1)。应用该方法测定了环境水样如包装塑料薄膜碎片溶出液和生活污水中酞酸酯类化合物的含量。水样中均未测出酞酸酯类化合物，对酞酸酯进行加标回收，回收率分别为85.8-103.2％。结果表明，可以用同样的条件同时萃取多种内分泌干扰物，达到同时快速检测的目的。
第四章建立了一种新的超高效液相色谱(UPLC)与紫外光谱联用技术分离检测水中雌酮，雌二醇，雌三醇和炔雌醇的方法。四种化合物在1.7分钟内可以完全达到基线分离，采用的反相色谱柱(50×2.1mm)填料粒径为1.7μm。样品先用固相萃取富集，浓缩后直接进样分析，四种雌激素化合物的回收率都大于90％，检测限在12.5-23.7 ng／L间，相对标准偏差介于7-11％之间。该方法成功应用于模拟自然水降解过程中雌二醇和炔雌醇的分析检测，48小时的连续监测结果显示，在该条件下，雌二醇的半衰期大约30小时，炔雌醇的半衰期大约为36小时。相对常规液相色谱方法，该方法具有灵敏度高、准确性好、操作方便的优点。适合大批量样品的快速检测和各种突发事件。对E2和EE2的动力学实验为我们的毒理实验提供了精确可靠的数据，可以指导实验室条件下开展雌激素暴露实验的投毒剂量和频率，以提供表观浓度与实际浓度相符的暴露环境。
第五章建立了高效、灵敏、可靠的HPLC-MS-MS联用技术分离检测污水中类固醇激素的方法，并对高碑店污水处理厂进水，出水及通惠河中类固醇污染状况及季节变化进行了为期半年的调查研究。类固醇的含量通过高灵敏度的HPLC-MS-MS进行测定，所建方法加标回收率在73-91％之间，检测限在0.1-1 ng／L。结果表明，采集的夏、秋、冬三个季节6批样品中，进水中所有类固醇化合物含量都很高，浓度在30-60 ng／L之间，但是经过二级处理后的所有出水和河水中的类固醇浓度明显降低，雌酮雌三醇和睾酮是最常被检出的物质，其浓度随季节变化呈现出规律性变化，孕酮没有检出，雌二醇、炔雌醇和雄烯二酮也分别有几次检出。浓度在几个ng／L水平，这一浓度已经高于雌激素对水生生物造成影响的最低浓度(＜0.1 ng／L)。由于类固醇激素化合物易通过食物链生物富集，因此对排放水要严格控制，不得作为渔业用水，以避免类固醇激素化合物的污染。此外，分析结果还说明现有的污水处理工艺还不能完全去除污水中的类固醇激素化合物，处理工艺还有待于进一步改进。长期暴露在类固醇下的通惠河中生物体的生长、发育和繁殖有深远的影响，应该结合毒理实验进行深入研究。
第六章由于HPLC-MS-MS价格昂贵，不能成为实验室常规仪器配置。因此期望能够建立一套适合普通实验室操作的分析方法。基于此目的，建立了大体积进样(Large volume injection，LVI)与GC-MS在线联用技术分离测定污水中雌激素的方法，本工作利用大体积进样技术程序升温气化的原理，对测定污水样中雌激素类化合物的效果进行了研究，选用N-O-bis-(trimethylsilyl)-trifluoroacetamide(含1％trimethylchlorosilane)作为衍生试剂，吡啶作反应介质，检测限在0.1 ng／L到0.33 ng／L之间，与传统分流／不分流进样技术进行了对比，灵敏度可高达10-50倍。同时优化了雌激素的衍生条件。研究表明，使用大体积进样方式，在不影响色谱分离度的同时，大大提高了仪器分析灵敏度，检测环境中的雌激素一直是繁琐，复杂的工作，要求高灵敏度的检测器，一般普通的GC-MS无法完成，运用该方法只需要在普通的GC-MS前加一个大体积进样器，就能够成功地检测到实际水样中的雌激素物质。可对环境水样中的痕量雌激素进行准确测定。用HPLC-MS-MS验证，结果吻合。
This paper studies the new analytical techniques for the determination of steroid hormones in water sample from the Sewage Treatment Plant (STP), which is focused on the new extraction procedures and new instrumental hyphenated techniques. It mainly consists of the following six parts.
In the first part, the definition of Endocrine disrupting compounds (EDC) and the most potent EDC categories --steroid hormones and their analytical techniques, environmental fate were introduced based on 110 previous references.
In the second part, a method based on cloud point extraction was developed to determine estrogens (estrone, estradiol, estriol, and progesterone) in environmental water samples by high-performance liquid chromatography separation and ultraviolet detection (HPLC-UV). The non-ionic surfactant Triton X-114 was chosen as extraction solvent. The parameters affecting extraction efficiency, such as concentrations of Triton X-114 and Na_2SO_4, equilibration temperature, equilibration time and centrifugation time were evaluated and optimized. Under the optimum conditions, preconcentration factors of 99, 73, 152, 86 and detection of limits of 0.23, 0.32, 0.25, 5.0 ng/mL for E3, E2, E1, P were obtained for 10-ml water sample. The proposed method was successfully applied to the determination of trace amount of estrogens in effluent water of the wastewater treatment plant (WWTP).
In the third part, based on the method for extraction of estrogens by cloud point extraction, a method was developed to determine phthalate esters (di-ethyl-phthalate, di-(2-ethylhexyl)-phthalate and di-cyclohexyl-phthalate) in environmental water samples by high-performance liquid chromatography separation and ultraviolet detection (HPLC-UV). The non-ionic surfactant Triton X-114 was chosen as extraction solvent. The parameters affecting extraction efficiency, such as concentrations of Triton X-114 and Na_2SO_4, equilibration temperature, equilibration time and centrifugation time were evaluated and optimized. Under the optimum conditions, preconcentration factors of 35, 88, 111 and detection of limits of 2.0, 3.8, 1.0 ng.ml~(-1) were obtained for DEP, DEHP and DCP in 10-ml water sample. The proposed method was successfully applied to the determination of trace amount of phathalate esters in effluent water of the wastewater treatment plant (WWTP) and the lixivium of plastic fragments.
In the fourth part, a new method for the determination of four estrogens, estriol, 17β-estradiol, 17α-ethynyl-estrodiol and estrone in water was established. The method involves solid-phase extraction of water samples and subsequent analysis of the extract by ultra-performance liquid chromatography (UPLC) coupled with an ultraviolet detector (UVD). Baseline separation was achieved for all the studied estrogens using a column (50×2.1mm) packed with 1.7 urn particle size stationary phase. The recoveries (>90%), detection limits (12.5-23.7 ng/L) and RSDs (7-11%) for the four estrogens were all satisfactory. The proposed method was successfully applied in determining the decrease of E2 and EE2 in simulative natural water. It was found that within 48 hours, the concentration of E2 decreased to 30% of its initial level (with a half-life of about 30 h), whereas EE2 decreased to 45% of its initial level (with a half-life of about 36 h). Low levels of E1 were found, while E3 was undetectable during the process.
In the fifth part, concentrations of natural and synthetic estrogens (estriol, 17β-estradiol, 17α-ethynyl-estrodiol, estrone, 17α-hydroxyprogesterone and progesterone) and androgens (testosterone, epitestosterone, methyltestosterone, 4-androstene-3, 17-dione) in the influent and effluent of the Gaobeidian sewage treatment plant (Beijing, China) and along the receiving river, the Tonghuihe River were determined by HPLC-MS-MS. The samples were collected during six months, so the seasonal variations of steroids were studied in the river. Estrone, estriol and testosterone were the dominant compounds (detected in all effluent samples), while estradiol, 17α-ethynylestradiol and 4-androstene-3, 17-dione were detected in two samples, and progesterone wasn't detected in all the effluent and receiving water samples. The recoveries of the analytes ranged from 73% to 91%, and the limits of quantification were in the range of 0.1-1 ng/L. The results indicated that the concentrations of steroids in winter were obviously higher than those in summer, which might be caused by temperature as the major factor in biodegradation process.
In the sixth part, a sensitive and automated method was presented for the determination of four estrogens (El, E2, E3, EE2) in wastewater by GC-MS equipped with a programmable temperature vaporizer (PTV-LV) injection port. N-O-bis-(trimethylsilyl)-trifluoroacetamide in pyridine containing 1% trimethylchlorosilane was chosen as derivatization reagent. The PTV-LV injection settings used herein could greatly improve the sensitivity of the analytical method. The proposed method offered detection limits ranging from 0.1 ng/L to 0.33 ng/L for four tested compounds, which was about 10 to 50 times more sensitive than the results achieved by the conventional 1μl splitless injection. The improved method was successfully applied to the analysis of estrogens in the wastewater, the result was proved by HPLC-MS-MS.
第一章概述了内分泌干扰物与活性最强的类固醇激素的研究热点，介绍了几种主要类固醇激素的生物功能、存在形式、环境命运和主要分析手段，对我国内分泌干扰物的研究状况进行了综述。
第二章将Triton X-114非离子表面活性剂作为浊点萃取溶剂应用于水样中雌激素类化合物的萃取富集，并与高效液相色谱结合，建立了这类化合物新的小体积，高富集效率的分析方法。该方法首先使一定浓度的Triton X-114非离子表面活性剂与待富集的样品盐溶液混合并在水浴中平衡，离心分离，而后弃去上层水溶液，取下层表面活性剂富集相20μL直接进样，进入液相色谱分离测定。实验优化了萃取过程中的影响因素如表面活性剂浓度、盐浓度、平衡温度平衡时间和离心时间等。该方法对于雌激素类化合物雌酮，雌二醇，雌三醇和孕酮的检测限分别为0.25、0.32、0.23和5.0 ng mL~(-1)。应用该方法测定了几种环境水样如自来水、养鱼水和生活污水中雌激素类化合物的含量。四类水样中均未测出雌激素类化合物，对雌激素进行加标回收，回收率分别为81.2—99.5％。Triton X-114作为浊点萃取剂具有浊点温度低，密度较高，有利于离心分离，价格低廉等优点。与传统液液萃取，固相萃取比较，整个萃取过程不需要任何有机溶剂，是一种绿色、高效的分析方法，适合大批量、小体积样品的快速检测。
第三章在浊点萃取雌激素的基础上继续探索浊点萃取在内分泌干扰物-酞酸酯中的应用。预期能够在相同条件下同时富集多种内分泌干扰物。并用于环境样品的处理。将Triton X-114非离子表面活性剂作为浊点萃取溶剂应用于水样中酞酸酯类化合物的萃取富集，并与高效液相色谱结合，建立了这类化合物新的分析方法。实验考察优化了萃取过程中的影响因素如表面活性剂浓度，盐浓度，平衡温度和平衡时间等。该方法对于酞酸酯类化合物邻苯二甲酸乙酯(DEP)、邻苯二甲酸乙基己酯(DEHP)和邻苯二甲酸环己酯(DCP)的检测限分别为2.0，3.8，1.0 ng．mL~(-1)。应用该方法测定了环境水样如包装塑料薄膜碎片溶出液和生活污水中酞酸酯类化合物的含量。水样中均未测出酞酸酯类化合物，对酞酸酯进行加标回收，回收率分别为85.8-103.2％。结果表明，可以用同样的条件同时萃取多种内分泌干扰物，达到同时快速检测的目的。
第四章建立了一种新的超高效液相色谱(UPLC)与紫外光谱联用技术分离检测水中雌酮，雌二醇，雌三醇和炔雌醇的方法。四种化合物在1.7分钟内可以完全达到基线分离，采用的反相色谱柱(50×2.1mm)填料粒径为1.7μm。样品先用固相萃取富集，浓缩后直接进样分析，四种雌激素化合物的回收率都大于90％，检测限在12.5-23.7 ng／L间，相对标准偏差介于7-11％之间。该方法成功应用于模拟自然水降解过程中雌二醇和炔雌醇的分析检测，48小时的连续监测结果显示，在该条件下，雌二醇的半衰期大约30小时，炔雌醇的半衰期大约为36小时。相对常规液相色谱方法，该方法具有灵敏度高、准确性好、操作方便的优点。适合大批量样品的快速检测和各种突发事件。对E2和EE2的动力学实验为我们的毒理实验提供了精确可靠的数据，可以指导实验室条件下开展雌激素暴露实验的投毒剂量和频率，以提供表观浓度与实际浓度相符的暴露环境。
第五章建立了高效、灵敏、可靠的HPLC-MS-MS联用技术分离检测污水中类固醇激素的方法，并对高碑店污水处理厂进水，出水及通惠河中类固醇污染状况及季节变化进行了为期半年的调查研究。类固醇的含量通过高灵敏度的HPLC-MS-MS进行测定，所建方法加标回收率在73-91％之间，检测限在0.1-1 ng／L。结果表明，采集的夏、秋、冬三个季节6批样品中，进水中所有类固醇化合物含量都很高，浓度在30-60 ng／L之间，但是经过二级处理后的所有出水和河水中的类固醇浓度明显降低，雌酮雌三醇和睾酮是最常被检出的物质，其浓度随季节变化呈现出规律性变化，孕酮没有检出，雌二醇、炔雌醇和雄烯二酮也分别有几次检出。浓度在几个ng／L水平，这一浓度已经高于雌激素对水生生物造成影响的最低浓度(＜0.1 ng／L)。由于类固醇激素化合物易通过食物链生物富集，因此对排放水要严格控制，不得作为渔业用水，以避免类固醇激素化合物的污染。此外，分析结果还说明现有的污水处理工艺还不能完全去除污水中的类固醇激素化合物，处理工艺还有待于进一步改进。长期暴露在类固醇下的通惠河中生物体的生长、发育和繁殖有深远的影响，应该结合毒理实验进行深入研究。
第六章由于HPLC-MS-MS价格昂贵，不能成为实验室常规仪器配置。因此期望能够建立一套适合普通实验室操作的分析方法。基于此目的，建立了大体积进样(Large volume injection，LVI)与GC-MS在线联用技术分离测定污水中雌激素的方法，本工作利用大体积进样技术程序升温气化的原理，对测定污水样中雌激素类化合物的效果进行了研究，选用N-O-bis-(trimethylsilyl)-trifluoroacetamide(含1％trimethylchlorosilane)作为衍生试剂，吡啶作反应介质，检测限在0.1 ng／L到0.33 ng／L之间，与传统分流／不分流进样技术进行了对比，灵敏度可高达10-50倍。同时优化了雌激素的衍生条件。研究表明，使用大体积进样方式，在不影响色谱分离度的同时，大大提高了仪器分析灵敏度，检测环境中的雌激素一直是繁琐，复杂的工作，要求高灵敏度的检测器，一般普通的GC-MS无法完成，运用该方法只需要在普通的GC-MS前加一个大体积进样器，就能够成功地检测到实际水样中的雌激素物质。可对环境水样中的痕量雌激素进行准确测定。用HPLC-MS-MS验证，结果吻合。
This paper studies the new analytical techniques for the determination of steroid hormones in water sample from the Sewage Treatment Plant (STP), which is focused on the new extraction procedures and new instrumental hyphenated techniques. It mainly consists of the following six parts.
In the first part, the definition of Endocrine disrupting compounds (EDC) and the most potent EDC categories --steroid hormones and their analytical techniques, environmental fate were introduced based on 110 previous references.
In the second part, a method based on cloud point extraction was developed to determine estrogens (estrone, estradiol, estriol, and progesterone) in environmental water samples by high-performance liquid chromatography separation and ultraviolet detection (HPLC-UV). The non-ionic surfactant Triton X-114 was chosen as extraction solvent. The parameters affecting extraction efficiency, such as concentrations of Triton X-114 and Na_2SO_4, equilibration temperature, equilibration time and centrifugation time were evaluated and optimized. Under the optimum conditions, preconcentration factors of 99, 73, 152, 86 and detection of limits of 0.23, 0.32, 0.25, 5.0 ng/mL for E3, E2, E1, P were obtained for 10-ml water sample. The proposed method was successfully applied to the determination of trace amount of estrogens in effluent water of the wastewater treatment plant (WWTP).
In the third part, based on the method for extraction of estrogens by cloud point extraction, a method was developed to determine phthalate esters (di-ethyl-phthalate, di-(2-ethylhexyl)-phthalate and di-cyclohexyl-phthalate) in environmental water samples by high-performance liquid chromatography separation and ultraviolet detection (HPLC-UV). The non-ionic surfactant Triton X-114 was chosen as extraction solvent. The parameters affecting extraction efficiency, such as concentrations of Triton X-114 and Na_2SO_4, equilibration temperature, equilibration time and centrifugation time were evaluated and optimized. Under the optimum conditions, preconcentration factors of 35, 88, 111 and detection of limits of 2.0, 3.8, 1.0 ng.ml~(-1) were obtained for DEP, DEHP and DCP in 10-ml water sample. The proposed method was successfully applied to the determination of trace amount of phathalate esters in effluent water of the wastewater treatment plant (WWTP) and the lixivium of plastic fragments.
In the fourth part, a new method for the determination of four estrogens, estriol, 17β-estradiol, 17α-ethynyl-estrodiol and estrone in water was established. The method involves solid-phase extraction of water samples and subsequent analysis of the extract by ultra-performance liquid chromatography (UPLC) coupled with an ultraviolet detector (UVD). Baseline separation was achieved for all the studied estrogens using a column (50×2.1mm) packed with 1.7 urn particle size stationary phase. The recoveries (>90%), detection limits (12.5-23.7 ng/L) and RSDs (7-11%) for the four estrogens were all satisfactory. The proposed method was successfully applied in determining the decrease of E2 and EE2 in simulative natural water. It was found that within 48 hours, the concentration of E2 decreased to 30% of its initial level (with a half-life of about 30 h), whereas EE2 decreased to 45% of its initial level (with a half-life of about 36 h). Low levels of E1 were found, while E3 was undetectable during the process.
In the fifth part, concentrations of natural and synthetic estrogens (estriol, 17β-estradiol, 17α-ethynyl-estrodiol, estrone, 17α-hydroxyprogesterone and progesterone) and androgens (testosterone, epitestosterone, methyltestosterone, 4-androstene-3, 17-dione) in the influent and effluent of the Gaobeidian sewage treatment plant (Beijing, China) and along the receiving river, the Tonghuihe River were determined by HPLC-MS-MS. The samples were collected during six months, so the seasonal variations of steroids were studied in the river. Estrone, estriol and testosterone were the dominant compounds (detected in all effluent samples), while estradiol, 17α-ethynylestradiol and 4-androstene-3, 17-dione were detected in two samples, and progesterone wasn't detected in all the effluent and receiving water samples. The recoveries of the analytes ranged from 73% to 91%, and the limits of quantification were in the range of 0.1-1 ng/L. The results indicated that the concentrations of steroids in winter were obviously higher than those in summer, which might be caused by temperature as the major factor in biodegradation process.
In the sixth part, a sensitive and automated method was presented for the determination of four estrogens (El, E2, E3, EE2) in wastewater by GC-MS equipped with a programmable temperature vaporizer (PTV-LV) injection port. N-O-bis-(trimethylsilyl)-trifluoroacetamide in pyridine containing 1% trimethylchlorosilane was chosen as derivatization reagent. The PTV-LV injection settings used herein could greatly improve the sensitivity of the analytical method. The proposed method offered detection limits ranging from 0.1 ng/L to 0.33 ng/L for four tested compounds, which was about 10 to 50 times more sensitive than the results achieved by the conventional 1μl splitless injection. The improved method was successfully applied to the analysis of estrogens in the wastewater, the result was proved by HPLC-MS-MS.
引文
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