染料木素的乳糖糖苷化修饰及其产物的结构表征和体外活性研究
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摘要
染料木素是大豆异黄酮中最具代表性的三羟基异黄酮，许多体外癌细胞培养研究证实，染料木素对乳腺癌、胃癌、肝癌、白血病及其它一些癌细胞系的生长、增殖具有抑制作用。治疗肿瘤最关键的是抑制肿瘤细胞的转移，Raz和Lotan证实在肿瘤细胞的表面存在与乳糖相连的凝集素，因此可以通过乳糖衍生物来阻断肿瘤细胞之间以及肿瘤细胞与宿主细胞之间的认知相互作用来防止肿瘤细胞的转移和扩散。乳糖还可以与肿瘤细胞表面受体结合，使结合乳糖的细胞毒药物可以长时间富集于肿瘤细胞附近，起到定向和协同治疗的效果。因此，将乳糖以糖苷的形式引到染料木素母体上，以期望乳糖的这种定向作用及乳糖与染料木素母体之间可能存在的协同作用而使形成的新化合物具有更好的抗癌活性，是本论文研究的主要课题。
本论文从改善染料木素在机体内作用的靶向性出发，对染料木素进行了乳糖糖苷化修饰。采用相转移催化的方法，以染料木素和溴代乙酰乳糖为原料，在稀碱溶液和二氯甲烷二相体系中，以四丁基溴化铵为相转移催化剂，首次合成了染料木素不同位置不同取代数目的染料木素乳糖苷，用聚酰胺和SephadexLH-20柱层析联用的方法分离得到了两种染料木素乳糖糖苷化修饰物，用IR，MS，~1H NMR，和~(13)C NMR等谱学手段对其结构进行了表征，确定其为染料木素7-O-β-D-吡喃乳糖苷和染料木素7，4′-二-O-β-D-吡喃乳糖苷。
在此基础上，对染料木素7，4′-二-O-β-D-毗喃乳糖苷和染料木素的三种体外活性进行了研究。采用连苯三酚的自氧化法，Fenton反应邻菲罗啉光度法和DPPH·自由基方法，研究了其清除超氧自由基、羟基自由基和DPPH·自由基的能力。结果表明两种化合物对三种自由基均具有一定的清除能力，且在同一浓度条件下染料木素7，4′-二-O-β-D-吡喃乳糖苷对三种自由基的清除能力都稍强于染料木素。
采用滤纸片法研究了两种化合物对枯草芽孢杆菌、金黄色葡萄球菌、大肠杆菌、变形杆菌、根霉、毛霉和曲霉等7种食品中常见微生物的抑制活性。结果表明这两种化合物对革兰氏阳性细菌(枯草芽孢杆菌和金黄色葡萄球菌)，革兰氏阴性细菌(大肠杆菌和变形杆菌)和真菌(根霉、毛霉和曲霉)均具有抑制活性。对同一种微生物来说，两种化合物的抑制活性差别不大。
采用了紫外法光谱法，荧光法光谱法和粘度法对两种化合物与DNA相互作用方式进行了研究，为两种化合物抗癌活性的研究提供一定的实验依据和有价值的参考信息。结果表明两种化合物与DNA存在弱的相互作用，其主要作用方式为沟面结合和静电结合的方式。
同时用荧光法研究了染料木素和染料木素7，4′-二-O-β-D-吡喃乳糖苷与牛血清蛋白(BSA)的作用的荧光猝灭方式，并计算其猝灭常数和结合常数。确定两种化合物对BSA的猝灭方式为形成了复合物的静态猝灭。染料木素与BSA作用的猝灭常数和结合常数分别为3.68×10~(13) L·mol~(-1)·S~(-1)和1.99×10~5L·mol~(-1)。染料木素7，4′-二-O-β-D-吡喃乳糖苷与BSA作用的猝灭常数和结合常数分别为6.33×10~(12) L·mol~(-1)·S~(-1)和6.60×10~4L·mol~(-1)。
Genistein is the presentative of 3-droxide isoflavone in soybean. The inhibitory of genistein on breast cancer, gastric cancer, leukaemia and other cancer has been proved by tumor cells in vitro. To inhibit metastases of cancer cells is the key to cure cancer. The lectin banding with lactose existed on the surface of tumor cells was verified by Raz and Lotan. So tumor metastasis can be prevented by absconding the cognition among tumour cells and the cognition between tumour cells and host cells by means of lactose derivative. Lactose can also bind with cell surface receptors, the result is that the medicine binding with lactose can inrich on the tumor cells for a long time.
To improve the targeting activity of genistein in vivo, chemical modification for genistein was carried out by using lactose, which has the potential selective affinity to the surface receptors of cancer cells. Two new compounds, genistein 7-O-β-D-lactoside and genistein 7,4'-di-O-β-D-lactoside, were synthesized by means of phase transfer catalysis, using genistein and O-acetyllactopyranosyl bromide as main raw materials and tetrabutylammonium bromide as catalyst and using KOH/CH_2Cl_2 two-phase system. They were isolated and purified by polyamide column and sephadex LH-20 column chromatography and characterized by IR, 1H NMR, 13C NMR and MS spectral data.
After the synthesis, the free radical (·OH,·O_2~-, DPPH·) scavenging activities of genistein and genistein 7,4'-di-O-β-D-lactoside were investigated by method of Pyrograllol Autoxidation and Fenton system by O-phenanthroline Spectrophotometry and DPPH free-radical. The results showed that free radical scavenging activities of genistein 7,4'-di-O-β-D-lactoside on·OH,·O_2~- and DPPH·were slightly stronger than that of genistein.
Antimicrobial acativities for seven common microbes(Bacillus Subtilis, Staphylococcus aureus, Escherichia coli, Proteus species, Rhizopus sp, Aspergillus sp and Mucor spp) in food were investigated with genistein and genistein 7,4'-di-O-β-D-lactoside by filter paper method. The results showed that both genistein and genistein 7,4'-di-O-β-D-lactoside exhibited antimicrobial activity to gram-positive bacterium, gram-negative bacterium and fugi.
The mechanism of the interaction between genistein, genistein 7,4'-di-O-β-D-lactoside and DNA by using UV spectra, fluorescent spectra and viscosity methods were reported. The results showed both genistein and genistein 7,4'-di-O-β-D-lactoside can bind to DNA with weak interaction. And they bind to DNA by groove binding and electrostatic interaction modes.
The fluorescence quenching mode between genistein, genistein 7,4'-di-O-β-D-lactoside and BSA by using fluorescence spectrum method were also studied. The experiment demonstrated that the quenching mechanism for the two compounds with BSA was static quenching process. The quenching constant of genistein was 3.68×10~(13) L·mol~(-1)·S~(-1) and that of genistein 7,4'-di-O-β-D-lactoside was 6.33×10~(12). The binding constant of genistein was 1.99×10~5L·mol~(-1) and that of genistein 7,4'-di-O-β-D- lactoside was 6.6×10~4L·mol~(-1).
本论文从改善染料木素在机体内作用的靶向性出发，对染料木素进行了乳糖糖苷化修饰。采用相转移催化的方法，以染料木素和溴代乙酰乳糖为原料，在稀碱溶液和二氯甲烷二相体系中，以四丁基溴化铵为相转移催化剂，首次合成了染料木素不同位置不同取代数目的染料木素乳糖苷，用聚酰胺和SephadexLH-20柱层析联用的方法分离得到了两种染料木素乳糖糖苷化修饰物，用IR，MS，~1H NMR，和~(13)C NMR等谱学手段对其结构进行了表征，确定其为染料木素7-O-β-D-吡喃乳糖苷和染料木素7，4′-二-O-β-D-吡喃乳糖苷。
在此基础上，对染料木素7，4′-二-O-β-D-毗喃乳糖苷和染料木素的三种体外活性进行了研究。采用连苯三酚的自氧化法，Fenton反应邻菲罗啉光度法和DPPH·自由基方法，研究了其清除超氧自由基、羟基自由基和DPPH·自由基的能力。结果表明两种化合物对三种自由基均具有一定的清除能力，且在同一浓度条件下染料木素7，4′-二-O-β-D-吡喃乳糖苷对三种自由基的清除能力都稍强于染料木素。
采用滤纸片法研究了两种化合物对枯草芽孢杆菌、金黄色葡萄球菌、大肠杆菌、变形杆菌、根霉、毛霉和曲霉等7种食品中常见微生物的抑制活性。结果表明这两种化合物对革兰氏阳性细菌(枯草芽孢杆菌和金黄色葡萄球菌)，革兰氏阴性细菌(大肠杆菌和变形杆菌)和真菌(根霉、毛霉和曲霉)均具有抑制活性。对同一种微生物来说，两种化合物的抑制活性差别不大。
采用了紫外法光谱法，荧光法光谱法和粘度法对两种化合物与DNA相互作用方式进行了研究，为两种化合物抗癌活性的研究提供一定的实验依据和有价值的参考信息。结果表明两种化合物与DNA存在弱的相互作用，其主要作用方式为沟面结合和静电结合的方式。
同时用荧光法研究了染料木素和染料木素7，4′-二-O-β-D-吡喃乳糖苷与牛血清蛋白(BSA)的作用的荧光猝灭方式，并计算其猝灭常数和结合常数。确定两种化合物对BSA的猝灭方式为形成了复合物的静态猝灭。染料木素与BSA作用的猝灭常数和结合常数分别为3.68×10~(13) L·mol~(-1)·S~(-1)和1.99×10~5L·mol~(-1)。染料木素7，4′-二-O-β-D-吡喃乳糖苷与BSA作用的猝灭常数和结合常数分别为6.33×10~(12) L·mol~(-1)·S~(-1)和6.60×10~4L·mol~(-1)。
Genistein is the presentative of 3-droxide isoflavone in soybean. The inhibitory of genistein on breast cancer, gastric cancer, leukaemia and other cancer has been proved by tumor cells in vitro. To inhibit metastases of cancer cells is the key to cure cancer. The lectin banding with lactose existed on the surface of tumor cells was verified by Raz and Lotan. So tumor metastasis can be prevented by absconding the cognition among tumour cells and the cognition between tumour cells and host cells by means of lactose derivative. Lactose can also bind with cell surface receptors, the result is that the medicine binding with lactose can inrich on the tumor cells for a long time.
To improve the targeting activity of genistein in vivo, chemical modification for genistein was carried out by using lactose, which has the potential selective affinity to the surface receptors of cancer cells. Two new compounds, genistein 7-O-β-D-lactoside and genistein 7,4'-di-O-β-D-lactoside, were synthesized by means of phase transfer catalysis, using genistein and O-acetyllactopyranosyl bromide as main raw materials and tetrabutylammonium bromide as catalyst and using KOH/CH_2Cl_2 two-phase system. They were isolated and purified by polyamide column and sephadex LH-20 column chromatography and characterized by IR, 1H NMR, 13C NMR and MS spectral data.
After the synthesis, the free radical (·OH,·O_2~-, DPPH·) scavenging activities of genistein and genistein 7,4'-di-O-β-D-lactoside were investigated by method of Pyrograllol Autoxidation and Fenton system by O-phenanthroline Spectrophotometry and DPPH free-radical. The results showed that free radical scavenging activities of genistein 7,4'-di-O-β-D-lactoside on·OH,·O_2~- and DPPH·were slightly stronger than that of genistein.
Antimicrobial acativities for seven common microbes(Bacillus Subtilis, Staphylococcus aureus, Escherichia coli, Proteus species, Rhizopus sp, Aspergillus sp and Mucor spp) in food were investigated with genistein and genistein 7,4'-di-O-β-D-lactoside by filter paper method. The results showed that both genistein and genistein 7,4'-di-O-β-D-lactoside exhibited antimicrobial activity to gram-positive bacterium, gram-negative bacterium and fugi.
The mechanism of the interaction between genistein, genistein 7,4'-di-O-β-D-lactoside and DNA by using UV spectra, fluorescent spectra and viscosity methods were reported. The results showed both genistein and genistein 7,4'-di-O-β-D-lactoside can bind to DNA with weak interaction. And they bind to DNA by groove binding and electrostatic interaction modes.
The fluorescence quenching mode between genistein, genistein 7,4'-di-O-β-D-lactoside and BSA by using fluorescence spectrum method were also studied. The experiment demonstrated that the quenching mechanism for the two compounds with BSA was static quenching process. The quenching constant of genistein was 3.68×10~(13) L·mol~(-1)·S~(-1) and that of genistein 7,4'-di-O-β-D-lactoside was 6.33×10~(12). The binding constant of genistein was 1.99×10~5L·mol~(-1) and that of genistein 7,4'-di-O-β-D- lactoside was 6.6×10~4L·mol~(-1).
引文
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