有毒中药甘遂炮制后化学成分及减毒作用的研究
摘要
甘遂为大戟科植物甘遂Euphorbia kansui T.N.Liou ex T.P.Wang的干燥块根,产于陕西、山东、河南、甘肃等地,为常用毒性中药材之一。甘遂作为药用的记载可以追溯到2000年前的《神农本草经》,祖国传统医学认为甘遂性寒,味苦,有毒,归肺、肾、大肠经,具有泻水逐饮的功能,在临床上多用于肝硬化腹水、胸腔积液、咳喘、水肿、肿瘤等病症。现代研究发现其有明显的泻下、抗生育、抗肿瘤和免疫抑制等作用。
甘遂的化学成分研究可以追溯到上世纪四十年代,最早是由日本的柳田昌一等人对其进行了成分研究,此后甘遂化学成分的研究持续了多年~[1],发现甘遂中主要化学成分是三萜类和二萜类化合物。甘遂是有毒中药,生品具有皮肤刺激性、毒性、泻下等副作用,故临床常用其炮制品。药理实验研究表明甘遂醋制后其副作用显著下降,薄层层析实验证实甘遂醋制前后化学成分发生了改变,但目前国内外对甘遂生品化学成分研究较多,甘遂醋制后化学成分研究极少,故系统研究其炮制前后药理作用发生变化的物质基础是十分必要的,本研究即为研究其炮制后化学成分及毒性作用的变化,尤其是有毒成分的变化。
目的应用现代化学理论和分离分析技术,结合物理化学方法,对醋制甘遂进行系统研究,以获知甘遂醋制后药理活性改变的物质基础,为充分合理地开发利用此种植物资源奠定基础。
方法醋制甘遂的95%乙醇提取物经溶剂(石油醚、氯仿、乙酸乙酯、正丁醇)分步萃取,反复应用硅胶柱色谱、凝胶柱色谱、制备薄层及重结晶等手段,对醋制甘遂的提取物进行分离纯化,根据其物理化学性质并运用ESI-MS、NMR、IR等波谱方法,参考相关文献报道的数据,对所得化合物进行结构鉴定。同时对甘遂饮片的各提取部位的毒性进行研究,以期找出甘遂的毒性部位,探讨炮制对甘遂毒性的影响。
结果从醋制甘遂中共分离得到16个化合物,分别为:大戟醇(Ⅰ)、β-谷甾醇(Ⅱ)、β-谷甾醇-3-O-6′-硬脂酰葡萄糖苷(Ⅲ)、胡萝卜苷(Ⅳ)、棕榈酸(V)、麦芽酚(Ⅵ)、棕榈酸甘油酯(Ⅶ)、豆甾醇苷(Ⅷ)、5-羟基麦芽酚(Ⅸ)、丁二酸(Ⅹ)、尿嘧啶(Ⅺ)、蔗糖(Ⅻ)、甘遂萜酯B(ⅩⅢ)、齐墩果酸(ⅪⅤ)、熊果酸(ⅩⅤ)、β-D-果糖乙苷(ⅩⅥ)。甘遂各萃取部位药理实验研究表明:索氏提取法制备甘遂的供试液实验动物出现明显的中毒症状,毒性部位为石油醚部位。甘遂石油醚部位及醋甘遂石油醚部位小鼠毒性实验结果显示醋甘遂的毒性较甘遂生品的毒性减弱。
结论本实验从醋制甘遂分离鉴定了16个化合物,分别为:大戟醇(Ⅰ)、β-谷甾醇(Ⅱ)、β-谷甾醇-3-O-6′-硬脂酰葡萄糖苷(Ⅲ)、胡萝卜苷(Ⅳ)、棕榈酸(V)、麦芽酚(Ⅵ)、棕榈酸甘油酯(Ⅶ)、豆甾醇苷(Ⅷ)、5-羟基麦芽酚(Ⅸ)、丁二酸(Ⅹ)、尿嘧啶(Ⅺ)、蔗糖(Ⅻ)、甘遂萜酯B(ⅩⅢ)、齐墩果酸(ⅪⅤ)、熊果酸(ⅩⅤ)、β-D-果糖乙苷(ⅩⅥ)。其中有9个化合物为首次分离得到,分别为:Ⅵ、Ⅶ、Ⅷ、Ⅸ、Ⅹ、Ⅺ、ⅪⅤ、ⅩⅤ、ⅩⅥ。甘遂药理实验结果表明甘遂经炮制能降低其毒性,另外,经HPLC分析得出甘遂经炮制后大戟二烯醇的含量减少,醋制甘遂的毒性较甘遂生品的毒性减弱可能与甘遂中的大戟二烯醇成分含量减少有关。
Euphorbia kansui T. N. Liou ex T. P. Wang is abundantly distributed in the northwestern of China. The dried roots of Euphorbia kansui are known as“Kan Sui”in Chinese medicine. Euphorbia is cold in nature, bitter in taste and poisonous, gets in lung, kidney, large intestine, with the function of diarrhea. It was mostly used to treat cirrhotic ascites, pleural effusion, edema, cough and asthma, cancer and other illnesses. Modern pharmacological studies show that the plant has the function of diarrhea, the anti-fertility, anti-tumor and the role of immune suppression etc.
The chemical composition research of Euphorbia kansui can be traced back to the 1940s, it was done first by Japanese LiuTian chang yi and then out for years. The study of the chemical ingredients of Euphorbia kansui find that the main chemical compositions are triterpene and diterpenes. Euphorbia kansui is poisonous medicine, with skin irritation, polarity toxicity, lapactic action side effect. Pharmacological experimental research shows that the side effect of the processed Euphorbia kansui significantly dropped, and the TLC experiments confirm the chemical composition of the processed Euphorbia kansui changed before and after processing. At present, there is much research on Euphorbia kansui but little system study on the processed Euphorbia kansui. So it is very necessary for us to study the material foundation of pharmacological functions change before and after processing. This study will research the chemical changes before and after processing, especially the change of the poisonous ingredient.
Objectives With the application of modern chemistry theory and the technology of separation and analysis, combined with physical and chemical methods, the chemical constituents of the processed Euphorbia kansui T. N. Liou ex T. P. Wang were studied systemically, aiming at obtaining material base of pharmacological activities change before and after processing, developing and utilizing the plant resources rationally.
Methods By using colum chromatography such as PTLC, silica gel, polyamide and gel etc repeatedly, compounds were isolated and purified. On the basis of their chemical and physical properties and the spectra data of ESI-MS, NMR, IR etc, compared with data reported in literatures, the structures of the constituents were determined. Meanwhile, to research on the toxicity of extracted parts of Euphorbia kansui decoction pieces, then aim to find out toxicity parts and research into the influence of processing to the toxicity of Euphorbia kansui.
Results 16 compounds had been isolated from the extracts, they were: euphorbol(Ⅰ),β-sitosterol(Ⅱ), sitosterol-3-O-6′-stearoyl-β-D-glucopyrano side(Ⅲ), daucosterol(Ⅳ), palmitic acid(Ⅴ), maltol(Ⅵ), monpalmitin(Ⅶ), Stigmasterol-β-D- -glucoside(ⅤⅢ), 5-oxymaltol(Ⅸ), succinic acid(Ⅹ), uracil(Ⅺ), sucrose(Ⅻ), kansu- -inineB(ⅩⅢ), oleanic acid(ⅪⅤ), ursolic acid(ⅩⅤ),β-D-fructoside(ⅩⅥ). The pharm- -acologic experiments of each extracted part of Euphorbia kansui indicated that: solutions for testing of Euphorbia kansui which was preparated by soxhlet extraction, the experimental animals appear obvious poisoning symptoms, the toxicity parts is the petroleum ether part. The result of petroleum ether part of Euphorbia kansui and the petroleum ether part of the processed Euphorbia kansui toxicity tests to mice show that Euphorbia kansui is more toxic than the processed one. Conclusion During the isolation and identification of 16 compounds, they were: euphorbol(Ⅰ),β-sitosterol(Ⅱ), sitosterol-3-O-6′-stearoyl-β-D-glucopyrano side(Ⅲ), daucosterol(Ⅳ), palmitic acid(Ⅴ), maltol(Ⅵ), monpalmitin(Ⅶ), stigmasterol-β-D- -glucoside(ⅤⅢ), 5-oxymaltol(Ⅸ), succinic acid(Ⅹ), uracil(Ⅺ), sucrose(Ⅻ), kansu- -inineB(ⅩⅢ), oleanic acid(ⅪⅤ), ursolic acid(ⅩⅤ),β-D-fructoside(ⅩⅥ). 9 of them were isolated for the first time, they wereⅥ、Ⅶ、ⅤⅢ、Ⅸ、Ⅹ、Ⅺ、ⅪⅤ、ⅩⅤ、 ⅩⅥ. The pharmacologic experiments of Euphorbia kansui indicated that: the toxicity of Euphorbia kansui can reduced through decoction, in addition, the content of euphorbol decrease in Euphorbia kansui after processed which obtained by HPLC analysis. The processed Euphorbia kansui is less toxic than Euphorbia kansui may have some relation with composition of euphorbol in Euphorbia kansui.
甘遂的化学成分研究可以追溯到上世纪四十年代,最早是由日本的柳田昌一等人对其进行了成分研究,此后甘遂化学成分的研究持续了多年~[1],发现甘遂中主要化学成分是三萜类和二萜类化合物。甘遂是有毒中药,生品具有皮肤刺激性、毒性、泻下等副作用,故临床常用其炮制品。药理实验研究表明甘遂醋制后其副作用显著下降,薄层层析实验证实甘遂醋制前后化学成分发生了改变,但目前国内外对甘遂生品化学成分研究较多,甘遂醋制后化学成分研究极少,故系统研究其炮制前后药理作用发生变化的物质基础是十分必要的,本研究即为研究其炮制后化学成分及毒性作用的变化,尤其是有毒成分的变化。
目的应用现代化学理论和分离分析技术,结合物理化学方法,对醋制甘遂进行系统研究,以获知甘遂醋制后药理活性改变的物质基础,为充分合理地开发利用此种植物资源奠定基础。
方法醋制甘遂的95%乙醇提取物经溶剂(石油醚、氯仿、乙酸乙酯、正丁醇)分步萃取,反复应用硅胶柱色谱、凝胶柱色谱、制备薄层及重结晶等手段,对醋制甘遂的提取物进行分离纯化,根据其物理化学性质并运用ESI-MS、NMR、IR等波谱方法,参考相关文献报道的数据,对所得化合物进行结构鉴定。同时对甘遂饮片的各提取部位的毒性进行研究,以期找出甘遂的毒性部位,探讨炮制对甘遂毒性的影响。
结果从醋制甘遂中共分离得到16个化合物,分别为:大戟醇(Ⅰ)、β-谷甾醇(Ⅱ)、β-谷甾醇-3-O-6′-硬脂酰葡萄糖苷(Ⅲ)、胡萝卜苷(Ⅳ)、棕榈酸(V)、麦芽酚(Ⅵ)、棕榈酸甘油酯(Ⅶ)、豆甾醇苷(Ⅷ)、5-羟基麦芽酚(Ⅸ)、丁二酸(Ⅹ)、尿嘧啶(Ⅺ)、蔗糖(Ⅻ)、甘遂萜酯B(ⅩⅢ)、齐墩果酸(ⅪⅤ)、熊果酸(ⅩⅤ)、β-D-果糖乙苷(ⅩⅥ)。甘遂各萃取部位药理实验研究表明:索氏提取法制备甘遂的供试液实验动物出现明显的中毒症状,毒性部位为石油醚部位。甘遂石油醚部位及醋甘遂石油醚部位小鼠毒性实验结果显示醋甘遂的毒性较甘遂生品的毒性减弱。
结论本实验从醋制甘遂分离鉴定了16个化合物,分别为:大戟醇(Ⅰ)、β-谷甾醇(Ⅱ)、β-谷甾醇-3-O-6′-硬脂酰葡萄糖苷(Ⅲ)、胡萝卜苷(Ⅳ)、棕榈酸(V)、麦芽酚(Ⅵ)、棕榈酸甘油酯(Ⅶ)、豆甾醇苷(Ⅷ)、5-羟基麦芽酚(Ⅸ)、丁二酸(Ⅹ)、尿嘧啶(Ⅺ)、蔗糖(Ⅻ)、甘遂萜酯B(ⅩⅢ)、齐墩果酸(ⅪⅤ)、熊果酸(ⅩⅤ)、β-D-果糖乙苷(ⅩⅥ)。其中有9个化合物为首次分离得到,分别为:Ⅵ、Ⅶ、Ⅷ、Ⅸ、Ⅹ、Ⅺ、ⅪⅤ、ⅩⅤ、ⅩⅥ。甘遂药理实验结果表明甘遂经炮制能降低其毒性,另外,经HPLC分析得出甘遂经炮制后大戟二烯醇的含量减少,醋制甘遂的毒性较甘遂生品的毒性减弱可能与甘遂中的大戟二烯醇成分含量减少有关。
Euphorbia kansui T. N. Liou ex T. P. Wang is abundantly distributed in the northwestern of China. The dried roots of Euphorbia kansui are known as“Kan Sui”in Chinese medicine. Euphorbia is cold in nature, bitter in taste and poisonous, gets in lung, kidney, large intestine, with the function of diarrhea. It was mostly used to treat cirrhotic ascites, pleural effusion, edema, cough and asthma, cancer and other illnesses. Modern pharmacological studies show that the plant has the function of diarrhea, the anti-fertility, anti-tumor and the role of immune suppression etc.
The chemical composition research of Euphorbia kansui can be traced back to the 1940s, it was done first by Japanese LiuTian chang yi and then out for years. The study of the chemical ingredients of Euphorbia kansui find that the main chemical compositions are triterpene and diterpenes. Euphorbia kansui is poisonous medicine, with skin irritation, polarity toxicity, lapactic action side effect. Pharmacological experimental research shows that the side effect of the processed Euphorbia kansui significantly dropped, and the TLC experiments confirm the chemical composition of the processed Euphorbia kansui changed before and after processing. At present, there is much research on Euphorbia kansui but little system study on the processed Euphorbia kansui. So it is very necessary for us to study the material foundation of pharmacological functions change before and after processing. This study will research the chemical changes before and after processing, especially the change of the poisonous ingredient.
Objectives With the application of modern chemistry theory and the technology of separation and analysis, combined with physical and chemical methods, the chemical constituents of the processed Euphorbia kansui T. N. Liou ex T. P. Wang were studied systemically, aiming at obtaining material base of pharmacological activities change before and after processing, developing and utilizing the plant resources rationally.
Methods By using colum chromatography such as PTLC, silica gel, polyamide and gel etc repeatedly, compounds were isolated and purified. On the basis of their chemical and physical properties and the spectra data of ESI-MS, NMR, IR etc, compared with data reported in literatures, the structures of the constituents were determined. Meanwhile, to research on the toxicity of extracted parts of Euphorbia kansui decoction pieces, then aim to find out toxicity parts and research into the influence of processing to the toxicity of Euphorbia kansui.
Results 16 compounds had been isolated from the extracts, they were: euphorbol(Ⅰ),β-sitosterol(Ⅱ), sitosterol-3-O-6′-stearoyl-β-D-glucopyrano side(Ⅲ), daucosterol(Ⅳ), palmitic acid(Ⅴ), maltol(Ⅵ), monpalmitin(Ⅶ), Stigmasterol-β-D- -glucoside(ⅤⅢ), 5-oxymaltol(Ⅸ), succinic acid(Ⅹ), uracil(Ⅺ), sucrose(Ⅻ), kansu- -inineB(ⅩⅢ), oleanic acid(ⅪⅤ), ursolic acid(ⅩⅤ),β-D-fructoside(ⅩⅥ). The pharm- -acologic experiments of each extracted part of Euphorbia kansui indicated that: solutions for testing of Euphorbia kansui which was preparated by soxhlet extraction, the experimental animals appear obvious poisoning symptoms, the toxicity parts is the petroleum ether part. The result of petroleum ether part of Euphorbia kansui and the petroleum ether part of the processed Euphorbia kansui toxicity tests to mice show that Euphorbia kansui is more toxic than the processed one. Conclusion During the isolation and identification of 16 compounds, they were: euphorbol(Ⅰ),β-sitosterol(Ⅱ), sitosterol-3-O-6′-stearoyl-β-D-glucopyrano side(Ⅲ), daucosterol(Ⅳ), palmitic acid(Ⅴ), maltol(Ⅵ), monpalmitin(Ⅶ), stigmasterol-β-D- -glucoside(ⅤⅢ), 5-oxymaltol(Ⅸ), succinic acid(Ⅹ), uracil(Ⅺ), sucrose(Ⅻ), kansu- -inineB(ⅩⅢ), oleanic acid(ⅪⅤ), ursolic acid(ⅩⅤ),β-D-fructoside(ⅩⅥ). 9 of them were isolated for the first time, they wereⅥ、Ⅶ、ⅤⅢ、Ⅸ、Ⅹ、Ⅺ、ⅪⅤ、ⅩⅤ、 ⅩⅥ. The pharmacologic experiments of Euphorbia kansui indicated that: the toxicity of Euphorbia kansui can reduced through decoction, in addition, the content of euphorbol decrease in Euphorbia kansui after processed which obtained by HPLC analysis. The processed Euphorbia kansui is less toxic than Euphorbia kansui may have some relation with composition of euphorbol in Euphorbia kansui.
引文
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