白桦酮酸和黄酮类物质的溶解度测定以及模型预测
发布时间：2018-07-20 10:34
【摘要】：白桦酮酸作为合成抗肿瘤药物白桦脂酸的关键中间体,具有很多诸如抗炎、抗菌、抗肿瘤等生物活性。黄酮类物质广泛存在于蔬菜、水果、谷物、根茎、花卉当中,并且在这些成分被分离出之前人们就已经发现此类物质对人类健康十分有益。另外很多体外实验证明,黄酮类物质具有很好的抗衰老,抗过敏,抗病毒,抗癌等生物活性。白桦酮酸以及黄酮类物质多种多样的生物活性也使得它们在很长一段时间里引起了有机化学合成和药理学研究的兴趣。为了更加高效地从植物提取物中分离纯化出一些生物活性成分,需要通过测定此类成分在不同溶剂中的溶解度数据来完成对溶剂的筛选工作。对于天然活性物质在各种溶剂体系中的固-液相平衡研究,能够为优化工艺提供理论依据和指导,在化工生产和设计中应用十分广泛。本论文第一章为文献综述部分,首先介绍了选择的几种天然产物的研究背景。白桦酮酸以及黄酮类物质根皮素、根皮苷、柚皮苷二氢查尔酮的研究历史、生物活性以及合成方法等。其次介绍了新型绿色溶剂天然低共熔溶剂的研究背景,物理化学性质和应用前景。然后介绍了固-液平衡体系的基本理论框架,以及目前理论模型的发展趋势。最后在上述内容的基础上介绍了本论文的选题意义以及主要研究内容。论文第二章建立了一种新型的使用摄像头代替肉眼观察的动态法测定溶解度装置,该装置精确度高,操作方便,并且能够实现测定过程的自动化和可视化。然后使用该装置测定了白桦酮酸在多种有机溶剂中的溶解度,以及柚皮苷二氢查尔酮在几种纯溶剂和混合溶剂中的溶解度。论文第三章采用加热法配制了柠檬酸+葡萄糖+水(CiGH),氯化胆碱+柠檬酸+水(CCiH),氯化胆碱+葡萄糖+水(CGH)四种天然低共熔溶剂,并对此类溶剂的密度、粘度等物理化学性质进行深入探讨。然后使用平衡法测定黄酮类物质根皮素、根皮苷和柚皮苷二氢查尔酮在新型绿色溶剂NADES中的溶解度。论文第四章使用传统的活度系数法中的经验方程Apelblat方程和λh方程对实验数据进行拟合,得到良好的拟合效果。同时使用python语言编写程序,计算溶解度数据的NRTL模型参数和UNIQUAC参数。发现在纯溶剂中的溶解度数据拟合效果良好,混合溶剂效果并不理想。除此之外还对每一个体系的溶解过程中的溶解热进行了计算和讨论。论文第五章详细介绍了量子化学中COSMO计算的过程,并使用COSMO-RS模型预测白桦酮酸在多种有机溶剂体系中的溶解度数据,得到不错的拟合效果。与传统的热力学方法相比,具有更加深远的意义。同时本章还使用了通用训练模型方法结合Jouban-Acree模型与Abraham溶解参数来对黄酮类物质在乙醇+水体系中的大量溶解度数据进行训练,训练得到的方程拟合实验数据结果良好。该模型得到的参数在工业上对黄酮类物质的纯化结晶等方面的应用有很好的指导意义。最后一章我们总结了所有的实验工作以及理论计算结果,认识到其中的一些不足之处,并提出后续的研究展望。
[Abstract]:Betula ketoacid is a key intermediate in the synthesis of anticancer drugs, Betula platyphylla, which has many biological activities, such as anti-inflammatory, antiseptic, and anti-tumor. Flavonoids are widely found in vegetables, fruits, Cereals, rhizomes, flowers, and before these components are separated, people have found that such substances are very beneficial to human health. In addition, many in vitro experiments have proved that flavonoids have good antiaging, antiallergic, antiviral and anticancer activities. The various biological activities of betulinic acid and flavonoids have caused their interest in organic chemistry and pharmacokinetics for a long time. In order to more efficiently from plants The separation and purification of some bioactive components in the extract requires the determination of the solvent by determining the solubility data in different solvents. The study on the solid liquid equilibrium of the natural active substances in various solvent systems can provide theoretical basis and guidance for the optimization of the process and the production and design of the chemical industry. The first chapter of this paper is the literature review. First, it introduces the research background of several natural products selected. The study history, biological activity and synthesis methods of Betula ketonic acid and flavonoids, pyeoloside, naringin two, and the synthesis method are introduced. Secondly, new green solvent natural low eutectic solution is introduced. The research background, physical and chemical properties and application prospects of the agent. Then the basic theoretical framework of the solid liquid equilibrium system and the development trend of the current theoretical model are introduced. Finally, the significance and main contents of this thesis are introduced on the basis of the above content. The second chapter of the paper has established a new type of camera instead of a camera. A dynamic method for the determination of the solubility of the dissolubility for the naked eye, with high accuracy, convenient operation, and the ability to automate and visualize the determination process. The solubility of Betula acid in a variety of organic solvents and the solubility of naringin two in several pure solvents and mixed solvents were measured. In the third chapter, four kinds of natural low eutectic solvents, including citric acid + glucose + water (CiGH), choline chloride + citric acid + water (CCiH), choline chloride + glucose + water (CGH), are prepared by heating method, and the physical and chemical properties of such solvents as density and viscosity are discussed. Then, the equilibrium method is used to determine the flavonoid, chloroglucoside, and chloroglucoside. The solubility of naringin two hydrogen chalcone in a new green solvent NADES. In the fourth chapter, the experimental data are fitted with the empirical equation Apelblat equation and lambda h equation in the traditional activity coefficient method, and a good fitting effect is obtained. At the same time, the program is compiled with the python language to calculate the NRTL model parameters and UNIQUAC of the solubility data. It is found that the solubility data in pure solvents have good fitting effect, and the effect of mixed solvent is not ideal. In addition, the dissolution heat in the dissolution process of each system is calculated and discussed. The fifth chapter of the paper describes the process of COSMO calculation in quantum chemistry and uses the COSMO-RS model to predict the Betula ketoacid. The solubility data in the organic solvent system can get a good fitting effect. Compared with the traditional thermodynamic method, it has more far-reaching significance. At the same time, this chapter also uses the general training model method combined with the Jouban-Acree model and the Abraham dissolving parameters to make a large amount of solubility data of flavonoids in the ethanol + water system. The results of the experimental data are good. The parameters obtained in this model have good guiding significance in the application of the purification and crystallization of flavonoids in industry. In the last chapter, we summarized all the experimental work and theoretical calculation results, recognized some of the shortcomings, and put forward the follow-up. The research prospect.
【学位授予单位】：浙江大学
【学位级别】：博士
【学位授予年份】：2017
【分类号】：O629;O645.12
[Abstract]:Betula ketoacid is a key intermediate in the synthesis of anticancer drugs, Betula platyphylla, which has many biological activities, such as anti-inflammatory, antiseptic, and anti-tumor. Flavonoids are widely found in vegetables, fruits, Cereals, rhizomes, flowers, and before these components are separated, people have found that such substances are very beneficial to human health. In addition, many in vitro experiments have proved that flavonoids have good antiaging, antiallergic, antiviral and anticancer activities. The various biological activities of betulinic acid and flavonoids have caused their interest in organic chemistry and pharmacokinetics for a long time. In order to more efficiently from plants The separation and purification of some bioactive components in the extract requires the determination of the solvent by determining the solubility data in different solvents. The study on the solid liquid equilibrium of the natural active substances in various solvent systems can provide theoretical basis and guidance for the optimization of the process and the production and design of the chemical industry. The first chapter of this paper is the literature review. First, it introduces the research background of several natural products selected. The study history, biological activity and synthesis methods of Betula ketonic acid and flavonoids, pyeoloside, naringin two, and the synthesis method are introduced. Secondly, new green solvent natural low eutectic solution is introduced. The research background, physical and chemical properties and application prospects of the agent. Then the basic theoretical framework of the solid liquid equilibrium system and the development trend of the current theoretical model are introduced. Finally, the significance and main contents of this thesis are introduced on the basis of the above content. The second chapter of the paper has established a new type of camera instead of a camera. A dynamic method for the determination of the solubility of the dissolubility for the naked eye, with high accuracy, convenient operation, and the ability to automate and visualize the determination process. The solubility of Betula acid in a variety of organic solvents and the solubility of naringin two in several pure solvents and mixed solvents were measured. In the third chapter, four kinds of natural low eutectic solvents, including citric acid + glucose + water (CiGH), choline chloride + citric acid + water (CCiH), choline chloride + glucose + water (CGH), are prepared by heating method, and the physical and chemical properties of such solvents as density and viscosity are discussed. Then, the equilibrium method is used to determine the flavonoid, chloroglucoside, and chloroglucoside. The solubility of naringin two hydrogen chalcone in a new green solvent NADES. In the fourth chapter, the experimental data are fitted with the empirical equation Apelblat equation and lambda h equation in the traditional activity coefficient method, and a good fitting effect is obtained. At the same time, the program is compiled with the python language to calculate the NRTL model parameters and UNIQUAC of the solubility data. It is found that the solubility data in pure solvents have good fitting effect, and the effect of mixed solvent is not ideal. In addition, the dissolution heat in the dissolution process of each system is calculated and discussed. The fifth chapter of the paper describes the process of COSMO calculation in quantum chemistry and uses the COSMO-RS model to predict the Betula ketoacid. The solubility data in the organic solvent system can get a good fitting effect. Compared with the traditional thermodynamic method, it has more far-reaching significance. At the same time, this chapter also uses the general training model method combined with the Jouban-Acree model and the Abraham dissolving parameters to make a large amount of solubility data of flavonoids in the ethanol + water system. The results of the experimental data are good. The parameters obtained in this model have good guiding significance in the application of the purification and crystallization of flavonoids in industry. In the last chapter, we summarized all the experimental work and theoretical calculation results, recognized some of the shortcomings, and put forward the follow-up. The research prospect.
【学位授予单位】：浙江大学
【学位级别】：博士
【学位授予年份】：2017
【分类号】：O629;O645.12
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