以形态分析为基础的砷及砷生物代谢过程与产物的表征研究
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摘要
本文以形态分析技术为主要研究手段,围绕与生物砷代谢相关的三个热点问题包括中药材,干海产品中砷的食用安全性、正常肝细胞与肝癌细胞代谢差异性以及砷生物代谢过程中砷蛋白的主要存在形态展开研究,获得了一系列有意义的结果及新认识。主要研究内容及所得成果总结如下:
第一章,对国内外在砷形态分析及砷生物代谢的近期研究及相关研究成果进行了简单的介绍和评述,并在此基础上归纳出与砷生物代谢相关的三个砷的“矛盾”特性;确定了本研究论文的研究重点及主要研究内容。
第二章,建立了三价无机砷(AsIII)、五价无机砷(AsV)、二甲基砷酸(DMA)、一甲基砷酸(MMA)、砷甜菜碱(AsB)和砷胆碱(AsC)六种形态砷的分离方法,采用梯度洗脱法使六种不同形态砷在15min内得到较好分离。并用盐酸浸提和超声溶剂提取两种前处理方法对中药材中不同形态砷进行提取,建立了高效液相色谱-电感耦合等离子体质谱(HPLC-ICP-MS)联用技术进行中药材中砷形态分析的方法,并用于6种中药材中砷形态的分析。研究发现中药材中砷主要以无机砷AsV和As III形态存在,此外动物性药材中还存在微量的砷甜菜碱(AsB)。
第三章,根据干海产品中不同形态砷的性质不同,采用不同提取剂,建立了丙酮-甲醇-稀盐酸连续提取的方法,并对该方法所采用的各种试剂进行了优化。研究显示该提取方法对干海产品中的各种形态砷具有较高的提取效率,三步总提取效率可达87-115%。在此基础上对不同性质的干海产品中的砷代谢产物进行了分析,并采用高效液相色谱-电喷雾飞行时间质谱(HPLC-TOF-MS)对未知砷代谢产物进行了表征。结果显示,尽管干海产品中含砷量较高,但在动物性干海产品中砷主要以无毒的砷甜菜碱(AsB)形式存在,约占总可提取砷量的62.0-72.7%;而在植物性干海产品中砷主要以毒性较低的砷糖类物质存在,约占总可提取砷量的63.5-92.7%。因此可以推断干海产品的总体毒性较低。
第四章,在对比了多种消解方法的基础上,建立了微波消解-电感耦合等离子体质谱法(Microwave digestion-ICP-MS)测定细胞中砷总量的分析方法。此外,本研究还建立了高效液相色谱-电感耦合等离子体质谱(HPLC-ICP-MS)联用技术进行正常人体肝细胞(Chang肝细胞)中砷形态的分析方法。研究发现Chang肝细胞中存在两种无法用已有商业化的砷形态标准表征的砷形态。本工作通过化学合成法制备了这两种砷形态标准,并采用标准加入法确定出该两种未知砷形态分别为一甲基亚砷酸(MMAIII)和一甲基一硫代砷酸(MMTA)。通过对正常肝细胞(Chang肝细胞)和肝癌细胞(QGY-7703肝癌细胞)砷代谢产物的对比发现,肝癌细胞对砷的代谢能力较弱。此外,由于在肝癌细胞中未检测到二甲基砷酸(DMAV)和一甲基一硫代砷酸(MMTA),因而可推测这两种代谢产物的缺失与肝癌细胞受到抑制有关,并在此研究基础上根据砷甲基化代谢的机理推测了肝癌细胞受到抑制的原因。
第五章,采用组分分析法将染砷小鼠肝脏按其不同的物理化学特性分为多个组分分别加以分析。结果显示小鼠肝脏中砷主要以自由态存在,占总砷含量的42.3-72.8%。其次为砷与不可溶蛋白结合态,占总砷含量的18.4-33.4%。砷与可溶性蛋白结合态含量最少,占总砷含量的8.8-24.3%。此外,研究发现多种砷代谢产物均可与小鼠肝脏中的蛋白结合,其中又以二甲基砷-蛋白结合态的含量最高。通过对三价砷化物(AsIII、MMAIII和DMAIII)与五价砷化物(AsV、MMAV和DMAV)与小鼠肝脏蛋白的亲和力强弱关系的对比,发现三价砷化物与蛋白的亲和力约为五价砷蛋白结合率的2倍,结合体内实验结果最终确定出小鼠肝脏内的砷蛋白主要以二甲基亚砷酸与蛋白结合物(DMAIII-protein)形态存在。此外,本研究还发现一(二)硫代砷化物(MMTA,DMDTA)是砷代谢过程中较易出现的代谢产物,而且这类物质是以与其对应的一(二)甲基亚砷酸(MMAIII,DMAIII)为代谢起点。
本文以形态分析技术为主要研究手段,较系统地探讨了干海产品和中药材中砷及其化合物的存在形态及分布特点,填补了该方面研究的空白;同时消除了国内外对我国海产品及中药材中砷毒性的猜测与质疑,具有重要的社会效益和经济效益。此外,通过对生物砷代谢过程中砷代谢产物的表征和对比研究,探讨了硫代砷化物的来源,砷对肝癌细胞生长有抑制作用这一现象的化学机理以及小鼠体内砷蛋白的主要存在形态,这些研究结果会为人们更好地理解砷生物代谢过程并利用砷的化合物进行癌症治疗提供相关的分析方法学,科学信息及技术支持。
Three hot topics related to arsenic metabolism were systematically studied in this dissertation, and these include: 1) consumption risk assessment of dry seafood products and Chinese traditional herbs, 2) the difference between normal liver cells and carcinogenic liver cells in arsenic metabolism , and 3) the major existing forms of arsenic-protein during arsenic metabolism in rats,. The contents and major results of the study are outlined as follows:
A brief review related to arsenic speciation and arsenic metabolism was made in the first chapter. Three seemingly conflicting characteristics about arsenic metabolism were summarized based on the recent literature survey.
In the 2nd chapter, the hyphenated technique of HPLC-ICP-MS was developed for the separation and sequential determination of 6 arsenic species including arsenobetaine (AsB), arsenocholine (AsC), arsenite (AsIII), arsenate (AsV), monomethylarsonic acid (MMAV) and dimethylarsinic acid (DMAV). The method developed was then applied for the speciation analysis of arsenic in a varity of Chinese medicinal herbs. The study indicated that As (Ⅴ), As (Ⅲ) were the main chemical species in Chinese medicinal herbs, however, only a limited amount of AsB was found in the animal herbs studied.
In the 3rd chapter, a sequential extraction procedure followed by HPLC-ICP-MS analysis was developed for the quantitative analysis of arsenic species in dry seafood products (DSPs). The excellent extraction efficiency could be obtained after three steps extraction (87-115%). A variety of DSPs samples were analyzed using novel extraction method established in the present work. It was observed that the type of arsenic species in the animal DSPs are different from those of the botanic ones. In the animal DSPs, Arsenobetaine (AsB) was the dominate specie, which occupied 62.0-72.7% of the total extractable arsenic in DSPs. Contrary to this, in botanic DSPs, three arsenosugars, DMA-glycerol ribose, DMA-phosphate ribose and DMA-sulfate ribose, identified with HPLC-TOF-MS, were the dominate species. The total content of these 3 species in the samples were in the range of 63.5-92.7%, indicating that the overall toxicity of DSPs were relatively low.
Three digestion methods including microwave digestion, cold digestion and obturator digestion were systematically studied in the 4th chapter. The comparative results showed that the microwave digestion was the most efficient method for arsenic determination in samples. Based on the total arsenic determination, arsenic speciation in Chang liver cells (reference material) were performed to identify the arsenic metabolites after their incubation. Two unknown arsenic metabolites, which were speculated as monomethylarsonous acid (MMAIII) and monomethylmonothioarsonic acid (MMTA), were found in the cells. Due to the absence of commercial standards, the MMAIII and MMTA in hepatocytes were tentatively identified and characterized using standard addition method. Furthermore, arsenic metabolites in normal liver cells (Chang liver cells) and carcinogenic liver cells (QGY-7703 cells) were compared by analyzing their arsenic metabolism efficiency. The results indicated that the arsenic metabolism efficiency of carcinogenic liver cells (QGY-7703 cells) was much lower than that of the normal liver cells. Based on the information that both DMAV and MMTA in QGY-7703 cells was undetected, it is speculated that the loss of those two arsenicals was related to the inhabitation of carcinogenic liver cells during arsenic metabolism.
In the 5th chapter, arsenic metabolites in rat liver were characterized and speciated using fractional analysis. The rat liver homogenates were separated into 5 fractions based on their different physical and chemical properties and analyzed using HPLC-ICP-MS. The results showed that most of the arsenicals in rat liver exist in free states, which accounts for 42.3-72.8% of the total arsenic. The next was arsenicals binding to non-soluble protein, which accounts for 18.4-33.4%. Arsenicals bond to soluble protein was the least abundant component, which accounts for 8.8-24.3%. Moreover, several kinds of arsenicals could bind to protein in rat liver, and the major component was in the form of dimethylated arsenicals-protein. An investigation of the affinity between arsenicals with different valence and protein suggested that trivalent arsenicals were much easier to bind to protein than those of pentavalent arsenicals. The present study indicated that the dimethylarsinic acid bond to protein (DMAIII-protein) was the major forms of arsenical-protein binding in rat liver. In addition, Arsenicals incubation in vitro showed that mono (di) methylthioarsenicals, including Dimethyldithioarsinic acid (DMDTA) and monomethylmonothioarsonic acid (MMTA) were the common arsenic metabolites in rat liver, which were derived from the metabolism of Monomethylarsonous acid (MMAIII) and Dimethylarsinous acid (DMAIII) in mammals.
In the present work, the chemical species and distributions of arsenic in dry seafood products and Chinese traditional herbs were systematically studied. The results might play an important role in well understanding the principle of arsenic toxicity in seafood and Chinese herbs. Moreover, on a basis of the identification and comparison of arsenic metabolites obtained in vivo/vitro, the origination of Thioarsenicals, mechanism of grown inhibition of carcinogenic liver cells after arsenic incubation and major components of arsenic-protein in rat liver were discussed. The above studies and the scientific results might offer useful analytical methodology, scientific information and technical support to the scientists who are working in these areas.
第一章,对国内外在砷形态分析及砷生物代谢的近期研究及相关研究成果进行了简单的介绍和评述,并在此基础上归纳出与砷生物代谢相关的三个砷的“矛盾”特性;确定了本研究论文的研究重点及主要研究内容。
第二章,建立了三价无机砷(AsIII)、五价无机砷(AsV)、二甲基砷酸(DMA)、一甲基砷酸(MMA)、砷甜菜碱(AsB)和砷胆碱(AsC)六种形态砷的分离方法,采用梯度洗脱法使六种不同形态砷在15min内得到较好分离。并用盐酸浸提和超声溶剂提取两种前处理方法对中药材中不同形态砷进行提取,建立了高效液相色谱-电感耦合等离子体质谱(HPLC-ICP-MS)联用技术进行中药材中砷形态分析的方法,并用于6种中药材中砷形态的分析。研究发现中药材中砷主要以无机砷AsV和As III形态存在,此外动物性药材中还存在微量的砷甜菜碱(AsB)。
第三章,根据干海产品中不同形态砷的性质不同,采用不同提取剂,建立了丙酮-甲醇-稀盐酸连续提取的方法,并对该方法所采用的各种试剂进行了优化。研究显示该提取方法对干海产品中的各种形态砷具有较高的提取效率,三步总提取效率可达87-115%。在此基础上对不同性质的干海产品中的砷代谢产物进行了分析,并采用高效液相色谱-电喷雾飞行时间质谱(HPLC-TOF-MS)对未知砷代谢产物进行了表征。结果显示,尽管干海产品中含砷量较高,但在动物性干海产品中砷主要以无毒的砷甜菜碱(AsB)形式存在,约占总可提取砷量的62.0-72.7%;而在植物性干海产品中砷主要以毒性较低的砷糖类物质存在,约占总可提取砷量的63.5-92.7%。因此可以推断干海产品的总体毒性较低。
第四章,在对比了多种消解方法的基础上,建立了微波消解-电感耦合等离子体质谱法(Microwave digestion-ICP-MS)测定细胞中砷总量的分析方法。此外,本研究还建立了高效液相色谱-电感耦合等离子体质谱(HPLC-ICP-MS)联用技术进行正常人体肝细胞(Chang肝细胞)中砷形态的分析方法。研究发现Chang肝细胞中存在两种无法用已有商业化的砷形态标准表征的砷形态。本工作通过化学合成法制备了这两种砷形态标准,并采用标准加入法确定出该两种未知砷形态分别为一甲基亚砷酸(MMAIII)和一甲基一硫代砷酸(MMTA)。通过对正常肝细胞(Chang肝细胞)和肝癌细胞(QGY-7703肝癌细胞)砷代谢产物的对比发现,肝癌细胞对砷的代谢能力较弱。此外,由于在肝癌细胞中未检测到二甲基砷酸(DMAV)和一甲基一硫代砷酸(MMTA),因而可推测这两种代谢产物的缺失与肝癌细胞受到抑制有关,并在此研究基础上根据砷甲基化代谢的机理推测了肝癌细胞受到抑制的原因。
第五章,采用组分分析法将染砷小鼠肝脏按其不同的物理化学特性分为多个组分分别加以分析。结果显示小鼠肝脏中砷主要以自由态存在,占总砷含量的42.3-72.8%。其次为砷与不可溶蛋白结合态,占总砷含量的18.4-33.4%。砷与可溶性蛋白结合态含量最少,占总砷含量的8.8-24.3%。此外,研究发现多种砷代谢产物均可与小鼠肝脏中的蛋白结合,其中又以二甲基砷-蛋白结合态的含量最高。通过对三价砷化物(AsIII、MMAIII和DMAIII)与五价砷化物(AsV、MMAV和DMAV)与小鼠肝脏蛋白的亲和力强弱关系的对比,发现三价砷化物与蛋白的亲和力约为五价砷蛋白结合率的2倍,结合体内实验结果最终确定出小鼠肝脏内的砷蛋白主要以二甲基亚砷酸与蛋白结合物(DMAIII-protein)形态存在。此外,本研究还发现一(二)硫代砷化物(MMTA,DMDTA)是砷代谢过程中较易出现的代谢产物,而且这类物质是以与其对应的一(二)甲基亚砷酸(MMAIII,DMAIII)为代谢起点。
本文以形态分析技术为主要研究手段,较系统地探讨了干海产品和中药材中砷及其化合物的存在形态及分布特点,填补了该方面研究的空白;同时消除了国内外对我国海产品及中药材中砷毒性的猜测与质疑,具有重要的社会效益和经济效益。此外,通过对生物砷代谢过程中砷代谢产物的表征和对比研究,探讨了硫代砷化物的来源,砷对肝癌细胞生长有抑制作用这一现象的化学机理以及小鼠体内砷蛋白的主要存在形态,这些研究结果会为人们更好地理解砷生物代谢过程并利用砷的化合物进行癌症治疗提供相关的分析方法学,科学信息及技术支持。
Three hot topics related to arsenic metabolism were systematically studied in this dissertation, and these include: 1) consumption risk assessment of dry seafood products and Chinese traditional herbs, 2) the difference between normal liver cells and carcinogenic liver cells in arsenic metabolism , and 3) the major existing forms of arsenic-protein during arsenic metabolism in rats,. The contents and major results of the study are outlined as follows:
A brief review related to arsenic speciation and arsenic metabolism was made in the first chapter. Three seemingly conflicting characteristics about arsenic metabolism were summarized based on the recent literature survey.
In the 2nd chapter, the hyphenated technique of HPLC-ICP-MS was developed for the separation and sequential determination of 6 arsenic species including arsenobetaine (AsB), arsenocholine (AsC), arsenite (AsIII), arsenate (AsV), monomethylarsonic acid (MMAV) and dimethylarsinic acid (DMAV). The method developed was then applied for the speciation analysis of arsenic in a varity of Chinese medicinal herbs. The study indicated that As (Ⅴ), As (Ⅲ) were the main chemical species in Chinese medicinal herbs, however, only a limited amount of AsB was found in the animal herbs studied.
In the 3rd chapter, a sequential extraction procedure followed by HPLC-ICP-MS analysis was developed for the quantitative analysis of arsenic species in dry seafood products (DSPs). The excellent extraction efficiency could be obtained after three steps extraction (87-115%). A variety of DSPs samples were analyzed using novel extraction method established in the present work. It was observed that the type of arsenic species in the animal DSPs are different from those of the botanic ones. In the animal DSPs, Arsenobetaine (AsB) was the dominate specie, which occupied 62.0-72.7% of the total extractable arsenic in DSPs. Contrary to this, in botanic DSPs, three arsenosugars, DMA-glycerol ribose, DMA-phosphate ribose and DMA-sulfate ribose, identified with HPLC-TOF-MS, were the dominate species. The total content of these 3 species in the samples were in the range of 63.5-92.7%, indicating that the overall toxicity of DSPs were relatively low.
Three digestion methods including microwave digestion, cold digestion and obturator digestion were systematically studied in the 4th chapter. The comparative results showed that the microwave digestion was the most efficient method for arsenic determination in samples. Based on the total arsenic determination, arsenic speciation in Chang liver cells (reference material) were performed to identify the arsenic metabolites after their incubation. Two unknown arsenic metabolites, which were speculated as monomethylarsonous acid (MMAIII) and monomethylmonothioarsonic acid (MMTA), were found in the cells. Due to the absence of commercial standards, the MMAIII and MMTA in hepatocytes were tentatively identified and characterized using standard addition method. Furthermore, arsenic metabolites in normal liver cells (Chang liver cells) and carcinogenic liver cells (QGY-7703 cells) were compared by analyzing their arsenic metabolism efficiency. The results indicated that the arsenic metabolism efficiency of carcinogenic liver cells (QGY-7703 cells) was much lower than that of the normal liver cells. Based on the information that both DMAV and MMTA in QGY-7703 cells was undetected, it is speculated that the loss of those two arsenicals was related to the inhabitation of carcinogenic liver cells during arsenic metabolism.
In the 5th chapter, arsenic metabolites in rat liver were characterized and speciated using fractional analysis. The rat liver homogenates were separated into 5 fractions based on their different physical and chemical properties and analyzed using HPLC-ICP-MS. The results showed that most of the arsenicals in rat liver exist in free states, which accounts for 42.3-72.8% of the total arsenic. The next was arsenicals binding to non-soluble protein, which accounts for 18.4-33.4%. Arsenicals bond to soluble protein was the least abundant component, which accounts for 8.8-24.3%. Moreover, several kinds of arsenicals could bind to protein in rat liver, and the major component was in the form of dimethylated arsenicals-protein. An investigation of the affinity between arsenicals with different valence and protein suggested that trivalent arsenicals were much easier to bind to protein than those of pentavalent arsenicals. The present study indicated that the dimethylarsinic acid bond to protein (DMAIII-protein) was the major forms of arsenical-protein binding in rat liver. In addition, Arsenicals incubation in vitro showed that mono (di) methylthioarsenicals, including Dimethyldithioarsinic acid (DMDTA) and monomethylmonothioarsonic acid (MMTA) were the common arsenic metabolites in rat liver, which were derived from the metabolism of Monomethylarsonous acid (MMAIII) and Dimethylarsinous acid (DMAIII) in mammals.
In the present work, the chemical species and distributions of arsenic in dry seafood products and Chinese traditional herbs were systematically studied. The results might play an important role in well understanding the principle of arsenic toxicity in seafood and Chinese herbs. Moreover, on a basis of the identification and comparison of arsenic metabolites obtained in vivo/vitro, the origination of Thioarsenicals, mechanism of grown inhibition of carcinogenic liver cells after arsenic incubation and major components of arsenic-protein in rat liver were discussed. The above studies and the scientific results might offer useful analytical methodology, scientific information and technical support to the scientists who are working in these areas.
引文
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