I 金鸡纳生物碱衍生物的合成方法研究 II 龙胆苦苷衍生物的合成及其对CVB3和SIV的体外抑制作用
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摘要
1.金鸡纳生物碱衍生物的合成方法研究
金鸡纳生物碱衍生物是不对称双羟化反应最优秀的催化剂,这类衍生物在不对称有机合成中的应用非常广泛。本论文对龙胆苦苷进行不对称双羟化结构修饰时,利用的手性配体即是金鸡纳生物碱衍生物,因而本文对其合成方法进行了研究。
传统的金鸡纳生物碱的合成方法均存在一些缺点,如反应件条反苛刻、反应时间长、缚酸剂安全性差以及难以选择性地获得单取代金鸡纳生物碱配体等。本文对金鸡纳碱衍生物的合成方法进行了研究,完成了以下研究内容:
首次采用微波辐射法合成四种不同类型的金鸡纳生物碱衍生物,系统地考察微波辐射功率、温度、反应时间、催化剂和缚酸剂的种类及投料量等参数对合成这四类衍生物的影响,优化各反应条件;同时采用常规溶剂法分别合成这些衍生物,对常规溶剂法和微波辐射法进行了比较。结论:与常规合成法相比,微波辐射法可快速、高产率的合成金鸡纳碱衍生物,降低了反应成本、减少了环境污染,特别是可选择性地得到单取代或双取代衍生物,是一种合成金鸡纳碱衍生物的新方法,该方法已经申请国家专利。
2.龙胆苦苷衍生物的合成及体外抑制CVB3作用
柯萨奇B3病毒(CVB3)是最主要的嗜心肌病毒,可以引起急性或慢性心肌炎,重者表现为进行性心衰,心律失常或猝死,已成为损害人类健康的常见病。虽然应用西药治疗VMC有一些成效,但效果均不很满意,临床试验表明中药对治疗VMC有一定优势。因此,从中药活性成分中寻找有效的抗CVB3的药物和先导化合物,成为治疗VMC的研究热点。龙胆苦苷(GPS)存在于龙胆科龙胆属植物中,属于裂环环烯醚萜类化合物,研究表明它具有显著的抗乙肝病毒、抑菌、抗炎作用。本文以龙胆苦苷为研究对象,进行了以下研究:
(1)龙胆苦苷衍生物的合成
首次对龙胆苦苷进行结构修饰,获得了三种衍生物:乙酰化龙胆苦苷衍生物A,立体构型不同的双羟化龙胆苦苷衍生物B和C。
(2)龙胆苦苷及其衍生物体外抑制CVB3作用
通过CVB3感染原代培养大鼠乳鼠心肌细胞的方法建立了病毒性心肌炎体外实验模型,首次研究了龙胆苦苷及其衍生物对CVB3的体外抑制作用及机制,初步探讨了龙胆苦苷抑制CVB3病毒的构效关系。结果显示龙胆苦苷具有较好的体外抑制CVB3作用,可抑制进入细胞内CVB3病毒的复制合成,降低病毒感染后心肌细胞酶AST和LDH的释放量;龙胆苦苷体外抗CVB3作用强于衍生物A、衍生物B和C,降低或增大脂溶性均不利于龙胆苦苷对CVB3的抑制,8-C构型不同对心肌细胞的毒性差别影响很大。
3.龙胆苦苷及其衍生物体外抑制SIV作用
艾滋病感染性强,死亡率高,迄今为止,全球已经有2000余万人死于艾滋病,但目前尚未有可以治愈的特效药。用于临床的叠氮胸苷AZT、双脱氧肌苷DDC等药物疗效欠佳,毒副作用大,价格昂贵,因而寻找有效的抗HIV药物是摆在各国学者面前的迫切任务。
本文研究证实龙胆苦苷具有较好的体外抗CVB3作用,在此基础上,进一步研究了其体外抗猴免疫缺陷病毒(SIV)活性。采用SIV和相应的CEMx-174细胞系统为模型,通过对抗原阳性细胞抑制率、CPE等指标的测试,研究了龙胆苦苷及其衍生物对SIV的体外抑制作用,并初步探讨了其抗SIV的构效关系。结果显示衍生物A具有体外高度抑制SIV作用,效果优于龙胆苦苷,衍生物B和C不具有体外抑制SIV的活性,龙胆苦苷末端双键是其抗病毒的活性部位。
1 Synthesis of Cinchona Alkaloid Ligands
Some disadvantages of conventional cinchona alkaloid ligand synthesis methods include high activities of acid-binding agent, rigorous reaction conditions, long reaction times, difficulties in preparation of the mono-cinchona alkaloid-derived ligands with high yield, use of toxic solvents, and significant amounts of waste product.
In this study, we design and synthesize four kinds of different cinchona alkaloid ligands by the microwave irradiation method. The effects of irradiation power and temperature, irradiation time, catalysts and acid-binding agents on the yield are discussed in detail. The four kinds of cinchona alkaloid ligands were synthesized under the optimal mivrowave conditions with good yields in short reaction time and with no solvent pollution. The four kinds of cinchona alkaloid ligands were also synthesized using conventional methods. The difference between the conventional method and the microwave irradiation method is discussed. The results showed that under microwave irradiation, the reactions proceeded much faster and at a lower cost with higher yields of mono-cinchona alkaloid-derived ligands.
2 Antiviral Effects of Gentiopicroside against Coxsackievirus B3 and its Mechanisms in Vitro
Coxsackievirus B3 (CVB3), a member of the Picornaviridae family that contains a single-stranded and positive-sense RNA genome, causes viral myocarditis (VMC) and can further develop into dilated cardiomyopathy in humans. Although the pathogenesis of CVB3 has been extensively studied in murine models and much work has been performed on the development of vaccines and therapeutic agents against CVB3, no virus-specific preventive or therapeutic procedures have been available to protect humans against enterovirus-induced heart muscle disease. In recent years, many countries are paying more and more attention to looking for anti-virus agents from Chinese medicinal herbs.
Gentiopicroside (GPS), a secoiridoid glycoside isolated from traditional Chinese herbs, has various bioactivities, such as antibacterial, free radical scavenging and antiviral activities. However, little information is available in the literature about GPS’s effects against CVB3 and the underlying mechanisms.
(1) Synthesis of derivatives of GPS
In the present research, three derivatives of GPS were synthesized: derivative A, derivative B, and derivative C.
(2) Antiviral effects of GPS and its derivatives
We determined the antiviral effects of GPS and its derivatives against CVB3 in vitro based on primary culture of myocardial cells of newborn SD rats. The results showed that GPS exhibited obvious antiviral effects in vitro. GPS inhibited pathologic change of cultured cardiac cells induced by CVB3. It also prevented the reproduction of CVB3 in myocardial cells and led to a significant decrease in activities of Aspartate transaminases (AST) and Lactic dehydrogenase (LDH) in myocardial cells compared with infected control groups. The antiviral effects of GPS were superior to those of the two derivatives.
3 Antiviral Effects of Gentiopicroside and its Derivatives against SIV in vitro
To date, approximately 2 million people have died from AIDS, but there is still no safe, effective vaccine against the human immunodeficiency virus (HIV). Treatment of HIV-infected individuals with one or more drugs (AZT or DDC etc.) that interfere with the viral life cycle has provided a significant therapeutic benefit by reducing the clinical symptoms and prolonging the life of infected individuals. These therapies are not perfect, however, because they do not eradicate the virus, and treatment fatigue and/or the emergence of drug resistant strains eventually occurs which frequently heralds an increase in virus. So, the development of an effective drug is an urgent goal to control the global HIV epidemic.
In the present study, we investigated the antiviral effect of GPS and its derivatives against simian immunodeficiency virus (SIV) in vitro. SIV and CEMx-174 cell system were employed as the models. The effects of GPS and compound A on antigen positive inhibitory rate, production of SIV virus, cytopathic effect and antigen positive inhibitory rate were studied. The viability of normal (control) and infected CEMx174 cells was determined by MTT assay. The results showed that compound A has a greater inhibitory effect on the activity of SIV in vitro when compared to GPS. Compounds B and C had no antiviral effects against SIV in vitro.
金鸡纳生物碱衍生物是不对称双羟化反应最优秀的催化剂,这类衍生物在不对称有机合成中的应用非常广泛。本论文对龙胆苦苷进行不对称双羟化结构修饰时,利用的手性配体即是金鸡纳生物碱衍生物,因而本文对其合成方法进行了研究。
传统的金鸡纳生物碱的合成方法均存在一些缺点,如反应件条反苛刻、反应时间长、缚酸剂安全性差以及难以选择性地获得单取代金鸡纳生物碱配体等。本文对金鸡纳碱衍生物的合成方法进行了研究,完成了以下研究内容:
首次采用微波辐射法合成四种不同类型的金鸡纳生物碱衍生物,系统地考察微波辐射功率、温度、反应时间、催化剂和缚酸剂的种类及投料量等参数对合成这四类衍生物的影响,优化各反应条件;同时采用常规溶剂法分别合成这些衍生物,对常规溶剂法和微波辐射法进行了比较。结论:与常规合成法相比,微波辐射法可快速、高产率的合成金鸡纳碱衍生物,降低了反应成本、减少了环境污染,特别是可选择性地得到单取代或双取代衍生物,是一种合成金鸡纳碱衍生物的新方法,该方法已经申请国家专利。
2.龙胆苦苷衍生物的合成及体外抑制CVB3作用
柯萨奇B3病毒(CVB3)是最主要的嗜心肌病毒,可以引起急性或慢性心肌炎,重者表现为进行性心衰,心律失常或猝死,已成为损害人类健康的常见病。虽然应用西药治疗VMC有一些成效,但效果均不很满意,临床试验表明中药对治疗VMC有一定优势。因此,从中药活性成分中寻找有效的抗CVB3的药物和先导化合物,成为治疗VMC的研究热点。龙胆苦苷(GPS)存在于龙胆科龙胆属植物中,属于裂环环烯醚萜类化合物,研究表明它具有显著的抗乙肝病毒、抑菌、抗炎作用。本文以龙胆苦苷为研究对象,进行了以下研究:
(1)龙胆苦苷衍生物的合成
首次对龙胆苦苷进行结构修饰,获得了三种衍生物:乙酰化龙胆苦苷衍生物A,立体构型不同的双羟化龙胆苦苷衍生物B和C。
(2)龙胆苦苷及其衍生物体外抑制CVB3作用
通过CVB3感染原代培养大鼠乳鼠心肌细胞的方法建立了病毒性心肌炎体外实验模型,首次研究了龙胆苦苷及其衍生物对CVB3的体外抑制作用及机制,初步探讨了龙胆苦苷抑制CVB3病毒的构效关系。结果显示龙胆苦苷具有较好的体外抑制CVB3作用,可抑制进入细胞内CVB3病毒的复制合成,降低病毒感染后心肌细胞酶AST和LDH的释放量;龙胆苦苷体外抗CVB3作用强于衍生物A、衍生物B和C,降低或增大脂溶性均不利于龙胆苦苷对CVB3的抑制,8-C构型不同对心肌细胞的毒性差别影响很大。
3.龙胆苦苷及其衍生物体外抑制SIV作用
艾滋病感染性强,死亡率高,迄今为止,全球已经有2000余万人死于艾滋病,但目前尚未有可以治愈的特效药。用于临床的叠氮胸苷AZT、双脱氧肌苷DDC等药物疗效欠佳,毒副作用大,价格昂贵,因而寻找有效的抗HIV药物是摆在各国学者面前的迫切任务。
本文研究证实龙胆苦苷具有较好的体外抗CVB3作用,在此基础上,进一步研究了其体外抗猴免疫缺陷病毒(SIV)活性。采用SIV和相应的CEMx-174细胞系统为模型,通过对抗原阳性细胞抑制率、CPE等指标的测试,研究了龙胆苦苷及其衍生物对SIV的体外抑制作用,并初步探讨了其抗SIV的构效关系。结果显示衍生物A具有体外高度抑制SIV作用,效果优于龙胆苦苷,衍生物B和C不具有体外抑制SIV的活性,龙胆苦苷末端双键是其抗病毒的活性部位。
1 Synthesis of Cinchona Alkaloid Ligands
Some disadvantages of conventional cinchona alkaloid ligand synthesis methods include high activities of acid-binding agent, rigorous reaction conditions, long reaction times, difficulties in preparation of the mono-cinchona alkaloid-derived ligands with high yield, use of toxic solvents, and significant amounts of waste product.
In this study, we design and synthesize four kinds of different cinchona alkaloid ligands by the microwave irradiation method. The effects of irradiation power and temperature, irradiation time, catalysts and acid-binding agents on the yield are discussed in detail. The four kinds of cinchona alkaloid ligands were synthesized under the optimal mivrowave conditions with good yields in short reaction time and with no solvent pollution. The four kinds of cinchona alkaloid ligands were also synthesized using conventional methods. The difference between the conventional method and the microwave irradiation method is discussed. The results showed that under microwave irradiation, the reactions proceeded much faster and at a lower cost with higher yields of mono-cinchona alkaloid-derived ligands.
2 Antiviral Effects of Gentiopicroside against Coxsackievirus B3 and its Mechanisms in Vitro
Coxsackievirus B3 (CVB3), a member of the Picornaviridae family that contains a single-stranded and positive-sense RNA genome, causes viral myocarditis (VMC) and can further develop into dilated cardiomyopathy in humans. Although the pathogenesis of CVB3 has been extensively studied in murine models and much work has been performed on the development of vaccines and therapeutic agents against CVB3, no virus-specific preventive or therapeutic procedures have been available to protect humans against enterovirus-induced heart muscle disease. In recent years, many countries are paying more and more attention to looking for anti-virus agents from Chinese medicinal herbs.
Gentiopicroside (GPS), a secoiridoid glycoside isolated from traditional Chinese herbs, has various bioactivities, such as antibacterial, free radical scavenging and antiviral activities. However, little information is available in the literature about GPS’s effects against CVB3 and the underlying mechanisms.
(1) Synthesis of derivatives of GPS
In the present research, three derivatives of GPS were synthesized: derivative A, derivative B, and derivative C.
(2) Antiviral effects of GPS and its derivatives
We determined the antiviral effects of GPS and its derivatives against CVB3 in vitro based on primary culture of myocardial cells of newborn SD rats. The results showed that GPS exhibited obvious antiviral effects in vitro. GPS inhibited pathologic change of cultured cardiac cells induced by CVB3. It also prevented the reproduction of CVB3 in myocardial cells and led to a significant decrease in activities of Aspartate transaminases (AST) and Lactic dehydrogenase (LDH) in myocardial cells compared with infected control groups. The antiviral effects of GPS were superior to those of the two derivatives.
3 Antiviral Effects of Gentiopicroside and its Derivatives against SIV in vitro
To date, approximately 2 million people have died from AIDS, but there is still no safe, effective vaccine against the human immunodeficiency virus (HIV). Treatment of HIV-infected individuals with one or more drugs (AZT or DDC etc.) that interfere with the viral life cycle has provided a significant therapeutic benefit by reducing the clinical symptoms and prolonging the life of infected individuals. These therapies are not perfect, however, because they do not eradicate the virus, and treatment fatigue and/or the emergence of drug resistant strains eventually occurs which frequently heralds an increase in virus. So, the development of an effective drug is an urgent goal to control the global HIV epidemic.
In the present study, we investigated the antiviral effect of GPS and its derivatives against simian immunodeficiency virus (SIV) in vitro. SIV and CEMx-174 cell system were employed as the models. The effects of GPS and compound A on antigen positive inhibitory rate, production of SIV virus, cytopathic effect and antigen positive inhibitory rate were studied. The viability of normal (control) and infected CEMx174 cells was determined by MTT assay. The results showed that compound A has a greater inhibitory effect on the activity of SIV in vitro when compared to GPS. Compounds B and C had no antiviral effects against SIV in vitro.
引文
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