染料木素葡萄糖苷的合成及其生物活性研究
摘要
本论文分为四个部分。
第1章综述了近年来黄酮类化合物糖苷化修饰的研究进展情况，阐明了课题研究的意义及方向。
第2章采用相转移催化法合成了染料木素葡萄糖苷化合物，并对合成及纯化条件进行了探讨，对产物进行了IR，~1H NMR，~(13)C NMR和MS结构表征。
第3章分别采用Fenton反应-邻菲罗啉显色法、邻苯三酚自氧化法和紫外可见分光光度法，考察染料木素及其葡萄糖苷化学修饰物清除·OH、·O_2~-和DPPH自由基能力。结果显示，染料木素糖苷修饰物清除三种自由基能力与其母体相比无显著提高。
第4章采用紫外、荧光、粘度等方法研究了染料木素及其葡萄糖苷化学修饰物与小牛胸腺DNA的作用。结果表明，在ctDNA存在下，染料木素及其葡萄糖苷的紫外吸收光谱产生明显的减色效应。另外，受试物均能有效猝灭EB-DNA体系的荧光，并使ctDNA溶液的粘度增大。据此推断，染料木素及其葡萄糖苷以部分插入及氢键作用与ctDNA结合。
This paper consists of four parts.
Chapter 1 In this section, advances in glycosidation modification of flavoniodswere reviewed. The significance and direction of the research were elucidated.
Chapter 2 The conditions for synthesis and purification of genistein glucosidesby phase transfer catalyzed method was investigated, and the structuralcharacterization of target compound was also conducted by IR, ~1H NMR, ~(13)C NMRand MS spectra in this part.
Chapter 3 The abilities of genistein and their derivatives in free radicalscavenging of·OH and·O_2~- and DPPH were exploited by using Fenton reaction withO-phenanthroline chromogenic reaction, pyrogallol autoxidation method and UV-visspectrophotometry, respectively. The results show that the abilities of glycosidederivatives of genistein in scavenging of the three free radicals were not obviouslyimproved compared withgenistein.
Chapter 4 The interactions of genistein, genistein glucoside and genistein7,4'-di-O-β- D- glucoside with calf thymus DNA(ctDNA) were investigated in thissection by using means of UV spectra, fluorescent spectra and viscosity, respectively.The results showed that the UV spectra of genistein and its glucosides showedobviously hypochromism under the presence of ctDNA. In addition, the testedcompounds could make the fluorescence intensity of EB-DNA system decreasedsharply, and also increased the relative viscosity of ctDNA aqueous. Theexperimental results suggested that genistein and its glucosides could bind to ctDNAby combination of partly intercalation and hydrogen bonding mode.
第1章综述了近年来黄酮类化合物糖苷化修饰的研究进展情况，阐明了课题研究的意义及方向。
第2章采用相转移催化法合成了染料木素葡萄糖苷化合物，并对合成及纯化条件进行了探讨，对产物进行了IR，~1H NMR，~(13)C NMR和MS结构表征。
第3章分别采用Fenton反应-邻菲罗啉显色法、邻苯三酚自氧化法和紫外可见分光光度法，考察染料木素及其葡萄糖苷化学修饰物清除·OH、·O_2~-和DPPH自由基能力。结果显示，染料木素糖苷修饰物清除三种自由基能力与其母体相比无显著提高。
第4章采用紫外、荧光、粘度等方法研究了染料木素及其葡萄糖苷化学修饰物与小牛胸腺DNA的作用。结果表明，在ctDNA存在下，染料木素及其葡萄糖苷的紫外吸收光谱产生明显的减色效应。另外，受试物均能有效猝灭EB-DNA体系的荧光，并使ctDNA溶液的粘度增大。据此推断，染料木素及其葡萄糖苷以部分插入及氢键作用与ctDNA结合。
This paper consists of four parts.
Chapter 1 In this section, advances in glycosidation modification of flavoniodswere reviewed. The significance and direction of the research were elucidated.
Chapter 2 The conditions for synthesis and purification of genistein glucosidesby phase transfer catalyzed method was investigated, and the structuralcharacterization of target compound was also conducted by IR, ~1H NMR, ~(13)C NMRand MS spectra in this part.
Chapter 3 The abilities of genistein and their derivatives in free radicalscavenging of·OH and·O_2~- and DPPH were exploited by using Fenton reaction withO-phenanthroline chromogenic reaction, pyrogallol autoxidation method and UV-visspectrophotometry, respectively. The results show that the abilities of glycosidederivatives of genistein in scavenging of the three free radicals were not obviouslyimproved compared withgenistein.
Chapter 4 The interactions of genistein, genistein glucoside and genistein7,4'-di-O-β- D- glucoside with calf thymus DNA(ctDNA) were investigated in thissection by using means of UV spectra, fluorescent spectra and viscosity, respectively.The results showed that the UV spectra of genistein and its glucosides showedobviously hypochromism under the presence of ctDNA. In addition, the testedcompounds could make the fluorescence intensity of EB-DNA system decreasedsharply, and also increased the relative viscosity of ctDNA aqueous. Theexperimental results suggested that genistein and its glucosides could bind to ctDNAby combination of partly intercalation and hydrogen bonding mode.
引文
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