甘草活性成分的模拟移动床和二维液相色谱分离
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摘要
甘草作为一种公认的天然药用植物,其使用历史久远,应用领域也十分广泛。迄今为止,已发现甘草中含有大量活性成分,主要为三萜类和黄酮类化合物。药理作用研究表明:这些活性成分具有抗HIV病毒、抗SARS病毒、抗肿瘤、抗氧化等多种重要的药理活性。
长期以来,甘草活性成分的提取分离是分离科学领域的重要研究内容之一,但由于甘草化学成分复杂,且有些活性成分含量甚微,使用传统的吸附及提取工艺有效的纯化高纯度的活性成分一直面临着巨大的挑战。模拟移动床色谱和二维液相色谱作为天然活性成分分离中的新技术,发展潜力巨大。利用模拟移动床色谱可以实现样品的连续分离制备,二维液相色谱可以更有效的实现多组分的分离提纯。本文的研究内容主要是用模拟移动床色谱和二维液相色谱分离纯化甘草中的活性成分。
为了得到适合模拟移动床色谱的进样原料,对甘草总黄酮原料进行了前处理并对前处理过程进行了优化,前处理包括萃取与制备单柱分离。通过正交设计实验得到了原料的最佳萃取条件。在非线性色谱理论分析及实验分析的基础上,给出了非线性条件下萃取物在单柱富集甘草苷的过程中进样浓度与进样体积的优化值。
在非线性条件下,首次使用模拟移动床色谱分离了甘草中重要活性成分甘草苷,所用设备为实验室自行设计研制的三带模拟移动床。根据模拟移动床进样原料的具体情况,提出二组分近似的竞争Langmuir模型作为甘草苷及其难分离杂质的吸附等温线模型,通过逆法得到吸附等温线参数。在此基础上,利用三角形方法并结合实际情况确定了模拟移动床的操作参数。确定的模拟移动床操作参数分别为Ⅰ带流速2 mL/min,Ⅱ带流速2 mL/min,进样流速2 mL/h,切换时间为8 min。经模拟移动床色谱分离得到了纯度为85%的甘草苷纯化物,甘草苷回收率为90.4%。此纯化物经重结晶后处理,最终得到纯度超过97%的甘草苷产品。
首次探讨了甘草苷的二维液相色谱分离方法。在分析规模条件下,研究了甘草提取物中甘草苷在不同二维液相色谱分离模式组合下的分离,本部分所讨论的二维色谱模式包括排阻色谱/反相色谱、正相色谱/反相色谱和反相色谱/反相色谱。在上述二维模式下,通过选择色谱条件及洗脱馏分的切割时间,得到了高纯度的甘草苷纯化物。在半制备规模条件下,使用自行构建的二维正相/反相液相色谱体系,分别实现了甘草苷的离线与在线分离,其中在线第二维中使用C18和NH2的混合固定相,具有富集甘草苷的作用。
系统研究了甘草中多种活性成分的离线二维液相色谱分离。所分离的主要目标活性成分包括甘草三萜类中的甘草酸和18β-甘草次酸以及黄酮类中的甘草苷、异甘草素和甘草查尔酮乙。通过选择确定适合上述甘草活性成分分离的二维反相/反相体系为:第一维使用SB C18固定相,第二维使用CN固定相,两维均使用体积比为2:3、pH值为6的乙腈水溶液作流动相。在此基础上,考察了进样浓度、进样体积、温度和流速因素对甘草活性成分二维分离的影响,结果表明:在所选范围内,进样浓度、进样体积对甘草活性成分的二维分离影响不显著;温度对甘草活性成分的二维分离有明显的影响;降低流速有利于提高活性成分的纯度。
本文的研究结果表明,用模拟移动床色谱和二维液相色谱分离甘草活性成分是可行且有效的。本文的结果及所用方法对其他天然活性成分的分离提纯具有借鉴作用。
Licorice,an important medicinal plant,has been used in many fields for many years.So far,it has been found that there are many active components in licorice. Most of these active components belong to triterpenoids and flavonoids.The researches on the pharmacological function of the active components show that they possess many important activities,such as anti-HIV,anti-SARS,anti-tumor,anti-oxidative activities,and so on.
For a long time,the extraction and separation of active components from licorice are one of important issues in separation science.Because of the complexity of the chemical components of licorice and the lower content of some active components in licorice,the efficient purification of active components from licorice is very difficult using the traditional extraction and adsorption processes.However,simulated moving bed(SMB) chromatography and two-dimensional liquid chromatography(2D LC), which are two new techniques for separation of natural active components,present huge potentials.The continuous preparative separation can be accomplished by SMB, the separation and purification of multi-component can be achieved more effectively by 2D LC.In this work,the separation and purification of active components from licorice by SMB and 2D LC were studied mainly.
To gain the sample suitable for feeding to SMB,the pretreatment processes, including extraction and separation by preparative column,were carried out to treat the total flavonoids of licorice and the pretreatment processes were optimized.The optimal conditions for extraction were obtained through orthogonal experiments. Considering the nonlinear chromatographic theory and the experimental analysis,the optimized values of injection concentration and injection volume for preparative chromatography was founded to enrich the content of liquiritin.
Under nonlinear conditions,the separation of liquiritin was for the first time studied with the three zones SMB set up in our laboratory.Liquiritin is an important active component in licorice.According to the specific situation of the sample fed into SMB,competitive Langmuir model of two-component approximation was put forwarded to describe adsorption behaviors of liquiritin and its nearest neighbor,the isotherm parameters were determined by inverse method.Based on this,the operational parameters of SMB were determined by Triangle Method and they were listed as follows.The flow rate of zoneⅠwas 2 mL/min,the flow rate of zoneⅡwas 2 mL/min,the flow rate of feed was 2 mL/h,and switching time was 8 min.85%pure of liquiritin product was achieved by three zones SMB.The recovery of liquiritin was 90.4%.The extract from SMB was recrystallized and eventually over 97%pure of liquiritin product was obtained.
The separation of liquiritin by 2D LC was firstly explored.In the condition of analytical scale,the purification of liquiritin from extract of licorice by 2D LC was studied under different 2D modes,including SEC×RP,NP×RP and RP×RP.For the 2D modes mentioned above,liquiritin with high purity were gained through the selection of chromatographic conditions and cut time of the fractions.In the condition of semi-preparative scale,the purifications of liquiritin by off-line and on-line NP-RP constructed by myself were performed respectively.The mixed materials of C18 and NH2 stationary phases were used in the second dimension for the on-line 2D separation,to enrich liquiritin in this dimension.
In this work,the off-line 2D separation of the mixture of multiple active components was studied systematically.The target active components included glycyrrhizic acid,18β-glycyrrhetinic acid,liquiritin,isoliquiritigenin,and licochalcone B.And the former two of them belong to triterpenoids and the latter three of them to flavonoids.The selected 2D RP-RP system suitable for the separation of the mixture above was as follows.The SB C18 stationary phase was used in the first dimension,CN stationary phase was used in the second dimension,the mobile phase of acitonitrile-water(2:3,v/v) with pH 6 was used in both dimensions.The effects of the influencing factors on 2D separation,including injection concentration, injection volume,temperature and flow rate,were discussed.And the results showed that in the selected range the effects of injection concentration and injection volume on the 2D separation of active components were not remarkable,while the effect of temperature was distinct.The decreasing of flow rate facilitated the gain of active components with high purities.
The results of this study show that it is feasible and efficient to separate the active components in licorice by SMB and 2D LC.The obtained results and the used methods could be referred for the separation of other natural active components.
长期以来,甘草活性成分的提取分离是分离科学领域的重要研究内容之一,但由于甘草化学成分复杂,且有些活性成分含量甚微,使用传统的吸附及提取工艺有效的纯化高纯度的活性成分一直面临着巨大的挑战。模拟移动床色谱和二维液相色谱作为天然活性成分分离中的新技术,发展潜力巨大。利用模拟移动床色谱可以实现样品的连续分离制备,二维液相色谱可以更有效的实现多组分的分离提纯。本文的研究内容主要是用模拟移动床色谱和二维液相色谱分离纯化甘草中的活性成分。
为了得到适合模拟移动床色谱的进样原料,对甘草总黄酮原料进行了前处理并对前处理过程进行了优化,前处理包括萃取与制备单柱分离。通过正交设计实验得到了原料的最佳萃取条件。在非线性色谱理论分析及实验分析的基础上,给出了非线性条件下萃取物在单柱富集甘草苷的过程中进样浓度与进样体积的优化值。
在非线性条件下,首次使用模拟移动床色谱分离了甘草中重要活性成分甘草苷,所用设备为实验室自行设计研制的三带模拟移动床。根据模拟移动床进样原料的具体情况,提出二组分近似的竞争Langmuir模型作为甘草苷及其难分离杂质的吸附等温线模型,通过逆法得到吸附等温线参数。在此基础上,利用三角形方法并结合实际情况确定了模拟移动床的操作参数。确定的模拟移动床操作参数分别为Ⅰ带流速2 mL/min,Ⅱ带流速2 mL/min,进样流速2 mL/h,切换时间为8 min。经模拟移动床色谱分离得到了纯度为85%的甘草苷纯化物,甘草苷回收率为90.4%。此纯化物经重结晶后处理,最终得到纯度超过97%的甘草苷产品。
首次探讨了甘草苷的二维液相色谱分离方法。在分析规模条件下,研究了甘草提取物中甘草苷在不同二维液相色谱分离模式组合下的分离,本部分所讨论的二维色谱模式包括排阻色谱/反相色谱、正相色谱/反相色谱和反相色谱/反相色谱。在上述二维模式下,通过选择色谱条件及洗脱馏分的切割时间,得到了高纯度的甘草苷纯化物。在半制备规模条件下,使用自行构建的二维正相/反相液相色谱体系,分别实现了甘草苷的离线与在线分离,其中在线第二维中使用C18和NH2的混合固定相,具有富集甘草苷的作用。
系统研究了甘草中多种活性成分的离线二维液相色谱分离。所分离的主要目标活性成分包括甘草三萜类中的甘草酸和18β-甘草次酸以及黄酮类中的甘草苷、异甘草素和甘草查尔酮乙。通过选择确定适合上述甘草活性成分分离的二维反相/反相体系为:第一维使用SB C18固定相,第二维使用CN固定相,两维均使用体积比为2:3、pH值为6的乙腈水溶液作流动相。在此基础上,考察了进样浓度、进样体积、温度和流速因素对甘草活性成分二维分离的影响,结果表明:在所选范围内,进样浓度、进样体积对甘草活性成分的二维分离影响不显著;温度对甘草活性成分的二维分离有明显的影响;降低流速有利于提高活性成分的纯度。
本文的研究结果表明,用模拟移动床色谱和二维液相色谱分离甘草活性成分是可行且有效的。本文的结果及所用方法对其他天然活性成分的分离提纯具有借鉴作用。
Licorice,an important medicinal plant,has been used in many fields for many years.So far,it has been found that there are many active components in licorice. Most of these active components belong to triterpenoids and flavonoids.The researches on the pharmacological function of the active components show that they possess many important activities,such as anti-HIV,anti-SARS,anti-tumor,anti-oxidative activities,and so on.
For a long time,the extraction and separation of active components from licorice are one of important issues in separation science.Because of the complexity of the chemical components of licorice and the lower content of some active components in licorice,the efficient purification of active components from licorice is very difficult using the traditional extraction and adsorption processes.However,simulated moving bed(SMB) chromatography and two-dimensional liquid chromatography(2D LC), which are two new techniques for separation of natural active components,present huge potentials.The continuous preparative separation can be accomplished by SMB, the separation and purification of multi-component can be achieved more effectively by 2D LC.In this work,the separation and purification of active components from licorice by SMB and 2D LC were studied mainly.
To gain the sample suitable for feeding to SMB,the pretreatment processes, including extraction and separation by preparative column,were carried out to treat the total flavonoids of licorice and the pretreatment processes were optimized.The optimal conditions for extraction were obtained through orthogonal experiments. Considering the nonlinear chromatographic theory and the experimental analysis,the optimized values of injection concentration and injection volume for preparative chromatography was founded to enrich the content of liquiritin.
Under nonlinear conditions,the separation of liquiritin was for the first time studied with the three zones SMB set up in our laboratory.Liquiritin is an important active component in licorice.According to the specific situation of the sample fed into SMB,competitive Langmuir model of two-component approximation was put forwarded to describe adsorption behaviors of liquiritin and its nearest neighbor,the isotherm parameters were determined by inverse method.Based on this,the operational parameters of SMB were determined by Triangle Method and they were listed as follows.The flow rate of zoneⅠwas 2 mL/min,the flow rate of zoneⅡwas 2 mL/min,the flow rate of feed was 2 mL/h,and switching time was 8 min.85%pure of liquiritin product was achieved by three zones SMB.The recovery of liquiritin was 90.4%.The extract from SMB was recrystallized and eventually over 97%pure of liquiritin product was obtained.
The separation of liquiritin by 2D LC was firstly explored.In the condition of analytical scale,the purification of liquiritin from extract of licorice by 2D LC was studied under different 2D modes,including SEC×RP,NP×RP and RP×RP.For the 2D modes mentioned above,liquiritin with high purity were gained through the selection of chromatographic conditions and cut time of the fractions.In the condition of semi-preparative scale,the purifications of liquiritin by off-line and on-line NP-RP constructed by myself were performed respectively.The mixed materials of C18 and NH2 stationary phases were used in the second dimension for the on-line 2D separation,to enrich liquiritin in this dimension.
In this work,the off-line 2D separation of the mixture of multiple active components was studied systematically.The target active components included glycyrrhizic acid,18β-glycyrrhetinic acid,liquiritin,isoliquiritigenin,and licochalcone B.And the former two of them belong to triterpenoids and the latter three of them to flavonoids.The selected 2D RP-RP system suitable for the separation of the mixture above was as follows.The SB C18 stationary phase was used in the first dimension,CN stationary phase was used in the second dimension,the mobile phase of acitonitrile-water(2:3,v/v) with pH 6 was used in both dimensions.The effects of the influencing factors on 2D separation,including injection concentration, injection volume,temperature and flow rate,were discussed.And the results showed that in the selected range the effects of injection concentration and injection volume on the 2D separation of active components were not remarkable,while the effect of temperature was distinct.The decreasing of flow rate facilitated the gain of active components with high purities.
The results of this study show that it is feasible and efficient to separate the active components in licorice by SMB and 2D LC.The obtained results and the used methods could be referred for the separation of other natural active components.
引文
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