染料木素乙酰阿魏酸酯的合成及其生物活性研究
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摘要
本论文分为四个部分
第一章:综述了黄酮类化合物和阿魏酸及其衍生物研究现状。阐明了本课题的研究意义和方向。
第二章:采用Schotten-Bamann反应合成染料木素-7-乙酰阿魏酸酯和染料木素-7,4'-二-乙酰阿魏酸酯,并对两种酯化产物进行了IR,~1H NMR,~(13)C NMR和MS表征。
第三章:采用几种化学及生物学模型考察了染料木素乙酰阿魏酸酯清除自由基能力、螯合金属离子能力及保护DNA免受自由基损伤能力。研究结果表明,染料木素酯化修饰物比染料木素具有更强的清除DPPH·、·OH~-自由基的能力,而保护DNA免受羟基自由基损伤能力与染料木素相当,但染料木素酯化修饰物比染料木素螯合金属Fe~(2+)离子的能力稍弱。此外,还探讨了酯化产物与其抗氧化及清除自由基活性之间的构效关系。
第四章:采用紫外,荧光和粘度法考察了染料木素-7-乙酰阿魏酸酯和染料木素-7,4'-二-乙酰阿魏酸酯与ctDNA的作用。结果表明,在ctDNA存在下,染料木素-7-乙酰阿魏酸酯和染料木素-7,4'-二-乙酰阿魏酸酯均发生了明显的减色反应。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,两种异黄酮酯与ctDNA之间具有较强的作用,键合方式主要为插入方式。
This paper consists of four parts.
Chapter 1: In this section, the status of flavoniods and ferulic acid and its derivative were reviewed. The significance and direction of the research were elucidated.
Chapter2: Two new compounds: genistein-7-acetylferulic acid ester and genistein-7,4'-di-acetyl-ferulic acid ester were firstly synthesized from ferulic acid and genistein based on Schotten-Bamann reaction. The structural characterization of the target compounds were conducted by, IR, ~1HNMR, ~(13)C NMR and MS spectra.
Chapter 3: The abilities of free radical scavenging and ferrous iron chelating and inhibition of hydroxyl radicals-mediated DNA degradation of genistein acetylferulic acid esters were evaluated by using various chemical and biological assays. The results showed that the abilities of two genistein acetylferulic acid esters were stronger than genistein on scavenging free radical of·DPPH and·OH. Two esters exhibited almost the same good protecting effect on DNA damage caused by hydroxyl radical as genistein. Ferrous ion chelating activities of two esters appeared to have abated somewhat than genistein. Furthermore, We studied their structure-effective relationship in this part.
Chapter 4: The interactions of genistein acetylferulic acid erters with calf thymusDNA(ctDNA) were investigated in this section by using means of UV spectra, fluorescent spectra and viscosity, respectively. The results showed that the UV spectra of genistein acetylferulic acid erters showed obviously hypochromism under the presence of ctDNA. In addition, the tested compounds could make the fluorescence intensity of EB-DNA system decreased sharply, and also increased the relative viscosity of ctDNA aqueous. The experimental results suggested that genistein acetylferulic acid erters could mainly bind to ctDNA by intercalation.
第一章:综述了黄酮类化合物和阿魏酸及其衍生物研究现状。阐明了本课题的研究意义和方向。
第二章:采用Schotten-Bamann反应合成染料木素-7-乙酰阿魏酸酯和染料木素-7,4'-二-乙酰阿魏酸酯,并对两种酯化产物进行了IR,~1H NMR,~(13)C NMR和MS表征。
第三章:采用几种化学及生物学模型考察了染料木素乙酰阿魏酸酯清除自由基能力、螯合金属离子能力及保护DNA免受自由基损伤能力。研究结果表明,染料木素酯化修饰物比染料木素具有更强的清除DPPH·、·OH~-自由基的能力,而保护DNA免受羟基自由基损伤能力与染料木素相当,但染料木素酯化修饰物比染料木素螯合金属Fe~(2+)离子的能力稍弱。此外,还探讨了酯化产物与其抗氧化及清除自由基活性之间的构效关系。
第四章:采用紫外,荧光和粘度法考察了染料木素-7-乙酰阿魏酸酯和染料木素-7,4'-二-乙酰阿魏酸酯与ctDNA的作用。结果表明,在ctDNA存在下,染料木素-7-乙酰阿魏酸酯和染料木素-7,4'-二-乙酰阿魏酸酯均发生了明显的减色反应。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,两种异黄酮酯与ctDNA之间具有较强的作用,键合方式主要为插入方式。
This paper consists of four parts.
Chapter 1: In this section, the status of flavoniods and ferulic acid and its derivative were reviewed. The significance and direction of the research were elucidated.
Chapter2: Two new compounds: genistein-7-acetylferulic acid ester and genistein-7,4'-di-acetyl-ferulic acid ester were firstly synthesized from ferulic acid and genistein based on Schotten-Bamann reaction. The structural characterization of the target compounds were conducted by, IR, ~1HNMR, ~(13)C NMR and MS spectra.
Chapter 3: The abilities of free radical scavenging and ferrous iron chelating and inhibition of hydroxyl radicals-mediated DNA degradation of genistein acetylferulic acid esters were evaluated by using various chemical and biological assays. The results showed that the abilities of two genistein acetylferulic acid esters were stronger than genistein on scavenging free radical of·DPPH and·OH. Two esters exhibited almost the same good protecting effect on DNA damage caused by hydroxyl radical as genistein. Ferrous ion chelating activities of two esters appeared to have abated somewhat than genistein. Furthermore, We studied their structure-effective relationship in this part.
Chapter 4: The interactions of genistein acetylferulic acid erters with calf thymusDNA(ctDNA) were investigated in this section by using means of UV spectra, fluorescent spectra and viscosity, respectively. The results showed that the UV spectra of genistein acetylferulic acid erters showed obviously hypochromism under the presence of ctDNA. In addition, the tested compounds could make the fluorescence intensity of EB-DNA system decreased sharply, and also increased the relative viscosity of ctDNA aqueous. The experimental results suggested that genistein acetylferulic acid erters could mainly bind to ctDNA by intercalation.
引文
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