鱼藤根中鱼藤素的提取分离、抗肿瘤活性筛选及其构效关系研究
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摘要
以鱼藤根为对象,研究抗肿瘤活性成分鱼藤素的提取、分离、色谱光谱特征、抗肿瘤活性、稳定性及构效关系。本文第一章对鱼藤素的结构、提取分离、生物活性、自然资源、组织培养技术、超临界流体提取、分子模拟等进行了较为详细的论述。第二章采用超声波辅助浸提、索氏提取、振荡抽提3种方法提取鱼藤根中的鱼藤酮类化合物,应用柱层析、薄层层析,比较不同展开剂分离植物提取物中鱼藤酮类化合物的效果,HPLC检测各组分中鱼藤素的相对含量。结果表明:超声波辅助提取、索氏提取过程中选择氯仿为浸提剂较为适宜,振荡提取时采用丙酮为浸提剂可最大量提取植物根中鱼藤素,且杂质含量相对较少。以石油醚:乙酸乙酯:氯仿(6:1:1)为展开剂,可以较好的将鱼藤素与其他鱼藤酮类化合物分离。第三章探索了超临界CO_2流体萃取技术在提取鱼藤根中鱼藤素上的应用,对不同粒度、提取时间、夹带剂、夹带剂用量、夹带剂加入方式、提取压力、提取温度、CO_2流量等条件下提取鱼藤根中鱼藤素进行研究,建立超临界CO_2流体提取鱼藤素的最优工艺。结果显示:鱼藤根粒度30目、提取30min、直接向萃取釜中加入9ml甲醇、提取压力30MPa、温度55℃、CO_2流速25kg/h条件下,每10克鱼藤干粉提取出来的鱼藤素相对含量最高。提取率是氯仿浸提的1.6倍。第四章分别使用HPLC、UV、MS、FT-IR、1H NMR测定鱼藤素的指纹图谱特征。结果表明,鱼藤素分子量为394,鱼藤素UV光谱最大吸收峰为271.6nm。第五章比较并分析了鱼藤素对人急性白血病细胞系K562细胞株、人结肠癌细胞系BEL-7402细胞株、人肺癌细胞系A549细胞株的细胞增殖抑制测定。结果表明,鱼藤素能显著抑制人急性白血病细胞系K562细胞株和人肺癌细胞系A549细胞株,但对人结肠癌细胞系BEL-7402细胞株抑制率较低。第六章比较了鱼藤素及其结构类似物——羟基鱼藤素、脱氢鱼藤素在不同溶剂中的溶解性;同时采用高效液相色谱分析羟基鱼藤素、鱼藤素、脱氢鱼藤素的光稳定性、热稳定性、微波稳定性和耐酸碱性。结果表明,羟基鱼藤素、鱼藤素、脱氢鱼藤素在甲醇、乙醇、乙二醇、乙腈、丙酮、氯仿、四氯化碳、乙酸乙酯中具有良好的溶解性;光照条件下,鱼藤素发生不同程度的分解,羟基鱼藤素、脱氢鱼藤素则较为稳定;80℃水域加热、微波均未对羟基鱼藤素、鱼藤素、脱氢鱼藤产生影响;酸性条件下,三者也相对较稳定,碱性条件下,鱼藤素结构发生改变。第七章应用热力学研究鱼藤素合成途径中能量的变化,采用HyperChem模拟软件计算各反应过程中吸收、释放能量的大小。为鱼藤素全合成的改进提供理论依据。第八章应用分子模拟技术,采用分子力学优化鱼藤素分子构象,经分子动力学、Semi-empirical方法模拟计算鱼藤素分子不同外场下能量变化及电荷分布。模拟结果表明,鱼藤素在超低温条件下可与水分子形成氢键,室温下不易与水形成氢键。Semi-empirical理论CNDO/2方法预测结果显示,鱼藤素C环上的羰基易发生亲电反应。第九章探讨了鱼藤根氯仿提取物、鱼藤素在硅胶上的热力学和动力学吸附过程,结果表明,该过程中鱼藤根氯仿提取物在硅胶填料的最大吸附量为310.29,表观解离常数为44.19,1.0mg/ml鱼藤根氯仿提取物在硅胶填料的吸附速率常数为1.9972;鱼藤素在硅胶填料的最大吸附量为260.29,表观解离常数为40.67,0.39mg/ml鱼藤素在硅胶填料的吸附速率常数为1.6913。
Deguelin, as one of natural rotenoids, is consisted in Derris Lour and Tephrosia Pers. In the paper, its extraction, purification, stability, chromatogram, spectrum, anti-tumour activity and structure were studied, respectively. In chapter one, a detailed review is presented in the paper of advances in the research of the structure, extraction, separation, bioactivity, nature resource tissue culture techniques supercritical extraction and molecule simulation. In chapter two, three methods were applied to extract deguelin from Derris trifoliate Lour roots. Different solvents were used to separate rotenoids, such as deguelin, rotenone and tephrosin. The weight of total extract and the relative deguelin extraction efficiency were determined. It is clearly shown that the total amount of the extracted substance assisted by using ultrasound is a little lower than the Sohxlet or vibrating extraction method. However, deguelin extraction rate by using the ultrasound-assisted extraction is the highest. Furthermore, with respect of rotenoids separation, the solvent mixture of petroleum ether:chloroform:acetone at the ratio of 6:1:1 is found to be the most effective. In chapter three, super critical CO_2. extraction was used to extract deguelin from the roots of Derris trifoliata in different sample size, time, modifiers, modifiers quantity, modifiers adding modes, press, temperature and flux of CO_2. In order to extract deguelin from 10g roots of Derris trifoliate, the rational conditions are sample size of 30 mesh, time of extraction before dynamic extracting 30min, adding 9ml methanol as modifier into extraction tube, press 30MPa, temperature 55℃and flux of CO_2 25kg/h. In the condition, the maximum deguelin is extracted, which is 1.6 sizes higher than that is extracted by chloroform. In chapter four, HPLC, UV, MS, FT-IR and 1H NMR were used to analyze deguelin. It is clearly that the mass of deguelin is 394 and the maximum spectrum value of deguelin is 271.6. Chapter five studies the anti-tumour research of deguelin. And the results show deguelin is a wanderful substance to restrain the propagation of K562 and A549 cells, but take a little effect on BEL-7402 cells. Chapter six shows that the solubility of tephrosin, duguelin and dehydrodeguelin in variety of solvents was compared, and the effect of light, heat, microwave and pH on tephrosin, deguelin and dehydrodeguelin was determined by HPLC. Results show that tephrosin, deguelin and dehydrodeguelin are well dissolved in methanol, ethanol, glycol, acetonitrile, acetone, chloroform, carbon tetrachloride and ethyl acetate. Deguelin is decompounded by light while tephrosin and dehydrodeguelin are relatively steady. Tephrosin, deguelin and dehydrodeguelin are unchanged by heat and microwave. As pH is lower than 7, tephrosin duguelin and dehydrodeguelin are stability. However, the structure of duguelin is changed distinctly when pH is higher than 7. In chapter seven, HyperChem was used to study the energy which is absorbing or releasing in variety of reactions. This chapter may be usefully to improve the synthesis deguelin in the future study. In chapter eight, molecular mechanics geometry optimization was used to optimize the structure of deguelin. And the optimized structure was simulated by Molecular Dynamics and CNDO/2 methods of Semi-empirical. The simulation pays attention to the change of energy in different conditions and the distributing of charge in deguelin. As the results are shown, deguelin can form H-bonds with water in super-low temperature but not in room temperature. The C=O of deguelin is easy to be replaced by nucleophilic reactivity. In chapter nine, Absorption isotherm and absorption dynamic curve of Derris trifoliate Lour roots chloroform extract is studied. The results show that the maximal q ofsilica gel is 310.29, K_d is 44.19 and adsorption velocity value is 1.9972 for concentration1.0mg/mi. As for deguelin, the maximal q of silica gel is 260.29, K_d is 40.67 and adsorption velocity value is 1.6913 for concentration 0.39mg/ml.
Deguelin, as one of natural rotenoids, is consisted in Derris Lour and Tephrosia Pers. In the paper, its extraction, purification, stability, chromatogram, spectrum, anti-tumour activity and structure were studied, respectively. In chapter one, a detailed review is presented in the paper of advances in the research of the structure, extraction, separation, bioactivity, nature resource tissue culture techniques supercritical extraction and molecule simulation. In chapter two, three methods were applied to extract deguelin from Derris trifoliate Lour roots. Different solvents were used to separate rotenoids, such as deguelin, rotenone and tephrosin. The weight of total extract and the relative deguelin extraction efficiency were determined. It is clearly shown that the total amount of the extracted substance assisted by using ultrasound is a little lower than the Sohxlet or vibrating extraction method. However, deguelin extraction rate by using the ultrasound-assisted extraction is the highest. Furthermore, with respect of rotenoids separation, the solvent mixture of petroleum ether:chloroform:acetone at the ratio of 6:1:1 is found to be the most effective. In chapter three, super critical CO_2. extraction was used to extract deguelin from the roots of Derris trifoliata in different sample size, time, modifiers, modifiers quantity, modifiers adding modes, press, temperature and flux of CO_2. In order to extract deguelin from 10g roots of Derris trifoliate, the rational conditions are sample size of 30 mesh, time of extraction before dynamic extracting 30min, adding 9ml methanol as modifier into extraction tube, press 30MPa, temperature 55℃and flux of CO_2 25kg/h. In the condition, the maximum deguelin is extracted, which is 1.6 sizes higher than that is extracted by chloroform. In chapter four, HPLC, UV, MS, FT-IR and 1H NMR were used to analyze deguelin. It is clearly that the mass of deguelin is 394 and the maximum spectrum value of deguelin is 271.6. Chapter five studies the anti-tumour research of deguelin. And the results show deguelin is a wanderful substance to restrain the propagation of K562 and A549 cells, but take a little effect on BEL-7402 cells. Chapter six shows that the solubility of tephrosin, duguelin and dehydrodeguelin in variety of solvents was compared, and the effect of light, heat, microwave and pH on tephrosin, deguelin and dehydrodeguelin was determined by HPLC. Results show that tephrosin, deguelin and dehydrodeguelin are well dissolved in methanol, ethanol, glycol, acetonitrile, acetone, chloroform, carbon tetrachloride and ethyl acetate. Deguelin is decompounded by light while tephrosin and dehydrodeguelin are relatively steady. Tephrosin, deguelin and dehydrodeguelin are unchanged by heat and microwave. As pH is lower than 7, tephrosin duguelin and dehydrodeguelin are stability. However, the structure of duguelin is changed distinctly when pH is higher than 7. In chapter seven, HyperChem was used to study the energy which is absorbing or releasing in variety of reactions. This chapter may be usefully to improve the synthesis deguelin in the future study. In chapter eight, molecular mechanics geometry optimization was used to optimize the structure of deguelin. And the optimized structure was simulated by Molecular Dynamics and CNDO/2 methods of Semi-empirical. The simulation pays attention to the change of energy in different conditions and the distributing of charge in deguelin. As the results are shown, deguelin can form H-bonds with water in super-low temperature but not in room temperature. The C=O of deguelin is easy to be replaced by nucleophilic reactivity. In chapter nine, Absorption isotherm and absorption dynamic curve of Derris trifoliate Lour roots chloroform extract is studied. The results show that the maximal q ofsilica gel is 310.29, K_d is 44.19 and adsorption velocity value is 1.9972 for concentration1.0mg/mi. As for deguelin, the maximal q of silica gel is 260.29, K_d is 40.67 and adsorption velocity value is 1.6913 for concentration 0.39mg/ml.
引文
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