液相色谱方法用于复杂体系的分离分析研究
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摘要
论文将高效液相色谱、开管柱色谱、制备色谱、色谱-质谱联用等现代色谱技术应用于两类复杂体系-中草药提取物和卟啉类催化剂的分离分析研究。主要研究内容包括两部分:第一部分以杜仲(Eucommia ulmoides)中降血压活性成分为目标,应用各种色谱技术对杜仲中环烯醚萜类和木脂素化合物进行了提取、分离、分析与结构表征研究,将升血压组分与降血压成分分离,得到了5种活性单体化合物—京尼平苷酸、京尼平苷、松脂醇二葡萄糖苷、丁香脂素二葡萄糖苷和绿原酸,所得到的单体采用HPLC、UV、IR、HNMR、LC-MS等仪器手段进行定性、定量分析,确定了其结构;第二部分系统地研究了5,10,15,20-四苯基卟啉钴(CoTPP)及其中间产物5,10,15,20-四苯基卟啉(TPP)的合成、分离纯化及其纯度检测方法,制备了高纯度的对照品。所提纯的产品采用HPLC、UV-VIS、IR、HPLC-MS等仪器分析手段进行定性、定量表征,确证其结构。建立了仿生催化氧化环己烷技术工业化应用中CoTPP催化剂浓度的HPLC定量分析方法,为仿生催化剂CoTPP的研制、大规模生产和工业应用提供了实验依据与基础。
具体内容摘要如下:
1.杜仲中活性成分的提取
系统地研究了常规溶剂提取法、酶提取法、半仿生提取法和超临界CO_2提取法从杜仲中提取京尼平苷酸(GPA)、京尼平苷(GPS)、桃叶珊瑚甙(AU)、松脂醇二葡萄糖甙(PDG)、丁香脂素二葡萄糖苷(SDG)和绿原酸(CA)的方法,对这四种方法的提取效果进行了比较,得到了最优提取工艺—半仿生提取法。
2.硅胶柱色谱制备杜仲中活性成分
采用硅胶柱色谱法制备得到高纯度的京尼平苷、京尼平苷酸、松脂醇二葡萄糖苷和丁香脂素二葡萄糖苷单体,所得京尼平苷酸、京尼平苷、松脂醇二葡萄糖苷和丁香脂素二葡萄糖苷纯度分别为98.69%、96.54%、92.18%和93.77%。
3.制备型反相高效液相色谱制备杜仲中活性成分
采用制备型反相高效液相色谱制备得到高纯度的京尼平苷、京尼平苷酸、和绿原酸单体,所得京尼平苷酸、京尼平苷和绿原酸纯度分别为95.61%,93.28%和96.57%,并以京尼平苷酸为例,采用前沿分析法研究了其在C_(18)柱上的吸附机理。
4.杜仲中活性成分的纯度测定和结构鉴定
采用HPLC-DAD建立了两种方法分别测定杜仲中的木脂素类化合物、环烯醚萜类化合物和绿原酸(CA)。(1)建立了同时测定杜仲中松脂醇二葡萄糖苷和丁香脂素二葡萄糖苷的高效液相色谱方法。(2)建立了同时测定杜仲中京尼平苷酸、京尼平苷和绿原酸的反相高效液相色谱方法。
从杜仲中分离得到5个化合物经化学分析、波谱分析分别鉴定为丁香脂素二葡萄糖苷、松脂醇二葡萄糖苷京尼平苷酸、京尼平苷、绿原酸。采用静脉注射的方式对杜仲提取物的降压作用作了初步探讨,动物实验结果表明,环烯醚萜类提取物的降压效果显著,最大降压效应、最大降压百分比及作用维持时间在不同剂量组间存在显著性差异。静脉注射杜仲提取物可致SHR大鼠血压下降,这种降压作用呈剂量依赖性。
5.RP-HPLC用于杜仲原药材指纹图谱的研究
采用RP-HPLC建立了杜仲原药材指纹图谱。以京尼平苷酸作为参照物,确定杜仲原药材指纹图谱中的20个共有峰,并用炮制后的杜仲药材检验了指纹图谱。
6.CoTPP和TPP的纯化
采用溶剂萃取分离-氧化铝柱层析的方法得到了高纯度的TPP,四苯基卟啉纯度可达99.85%、总回收率达88.98%:利用CoTPP和TPP在溶剂A中的溶解性不同实现了CoTPP的纯化,纯化收率达81.95%以上,纯化后CoTPP纯度由29.57%、38.79%、32.34%提高到76.41%、81.37%、74.29%。
7.RP-HPLC法测定TPP
采用反相高效液相色谱法测定TPP的含量。流动相为甲醇:水=85:15(v/v),TPP浓度在0.5μg/mL-2.5μg/mL之间线性关系良好,加标回收率在95.2%-106.1%之间。该法简便快速。采用UV-VIS、IR、LC-ESI-MS等仪器分析手段对TPP的结构进行了表征。
8.RP-HPLC法测定CoTPP
研究建立了CoTPP的反相HPLC测定方法。流动相为甲醇:乙腈:氯仿=7:3:1(v/v),CoTPP浓度在1.0μg/mL-5.0μg/mL之间线性关系良好,加标回收率为95.05%-102.4%,RSD为0.54%。采用UV-VIS、IR等仪器分析手段鉴定了CoTPP的结构,确认了目标化合物的合成。
9.CoTPP和TPP测定方法在工业中实际应用
结合项目应用单位的实际情况,研究建立了同时测定CoTPP和TPP的反相HPLC方法。以甲醇:乙腈:氯仿=7:3:1(v/v)作流动相,方法快速、方便,精密度和准确度高,研究成果在仿生催化氧化环己烷生产环己酮的工业化试验中应用良好。
Two complicated systems,namely extract from Chinese traditional herb and porphine catalyst,were studied by the high performance liquid chromatography,open column chromatography,preparative high performance liquid chromatography,or liquid chromatography with mass spectrometry.The main content consists of two parts:(1)considering the bioactive components from Eucommia ulmoides as object,extraction, separation,determination and characterization of iridoids and lignans from Eucommia ulmoides were studied.Five bioactive compounds were attained and identified as geniposidic acid,geniposide,pinoresinol diglucoside,syringaresinol diglucoside,and chlorogenic acid by means of HPLC,UV,IR,1HNMR and MS.(2)Purification,characterization and determination of 5,10,15,20-tetraphenylporphine cobalt(CoTPP)and its middle product 5,10,15,20-tetraphenylporphine(TPP)were studied systematically by means of column chromatography,HPLC,UV-VIS,IR and HPLC-MS.It provided the method for large-scale produce of porphine catalyst and the industrial application of cyclohexane biomimetic catalytic oxidation to produce cyclohexanone.
Details are as following:
1.Extraction bioactive components from Eucommia ulmoides
Extraction methods using solvent extraction(SE),enzyme-assisted aqueous extraction(EE),semi-bionic extraction(SBE)and supercritical CO2 fluid extraction(SFE)were evaluated for the yields of geniposidic acid,geniposide,pinoresinol diglucoside,syringaresinol diglucoside, aucubin and chlorogenic acid from Eucommia ulmoides.Semi-bionic extraction was chosen for its high yields.
2.Preparation bioactive components from Eucommia ulmoides by silica gel column chromatography
Geniposidic acid,geniposide,pinoresinol diglucoside,and syringaresinol diglucoside were prepared by silica gel column chromatography.The purities of geniposidic acid,geniposide,pinoresinol diglucoside,and syringaresinol diglucoside were 98.69%,96.54%, 92.18%,and 93.77%,respectively.
3.Preparation bioactive components from Eucommia ulmoides by preparative high performance liquid chromatography
Geniposidic acid,geniposide,and chlorogenic acid were prepared by preparative high performance liquid chromatography.The purities of geniposidic acid,geniposide,and chlorogenic acid were 95.61%,93.28% and 96.57%,respectively.The adsorption mechanism of geniposidic acid on C_(18)column was studied by frontal analysis.
4.Determination and characterization of bioactive components from Eucommia ulmoides
Two methods base on high performance liquid chromatography coupled with photodiode array detector(HPLC-DAD)were established to determination of lignans,iridoids and chlorogenic acid,respectively.(1) Pinoresinol diglucoside and syringaresinol diglucoside were separated and analyzed on a Kromasil RP-C_(18)column by HPLC;(2)Geniposidic acid,geniposide,and chlorogenic acid were separated and determined by HPLC.
Five bioactive components from Eucommia ulmoides were identified as syringaresinol diglucoside,pinoresinol diglucoside,geniposidic acid, geniposide,and chlorogenic acid by chemical and spectra analysis.The animal experimental result indicated that there were significantly statistic differences in maximum effectiveness,maximum effective percentage and duration between two different groups and that intravenous administration of the extract of Eucommia ulmioides dose-dependently reduced blood pressure in the SHRs.
5.Study fingerprint ofEucommia ulmioides by HPLC
HPLC fingerprint Spectrum ofEucommia ulmioides was established. Chromatography conditions:column,Kromasil RP-C_(18)column;mobile phase,methanol-0.1%acetic acid(20:80,v/v);detection wavelength,240 nm;flow rate,0.8 mL/min;and injection volume,20μL.Geniposidic acid was used as the reference compound.
6.Purification of CoTPP and TPP
TPP was separated and purified through extraction and aluminum oxide column chromatography.The purity of purified product was 99.85%.The total recovery was 88.98%.CoTPP was separated through extraction(using efficient solvent A)and was purified by crystallization. The purity of purified CoTPP was from 29.57%,38.79%,32.34%to 76.41%,81.37%,and 74.29%,respectively.The recovery was 85.13%.
7.Quantification of TPP by RP-HPLC
TPP was determined by the reversed phase high performance liquid chromatography.The mobile phase consisted of methanol-water(85:15, v/v)and the quantitative analysis was conducted with calibration curve method.The result indicated that the calibration curve was linear in the range of 0.5-2.5μg/mL of TPP with r=0.9993,the minimum detection limits to 0.2μg/mL and the recoveries were between 95.2%and 106.1%. The structure of TPP was identified by means of UV-VIS,IR,LC-ESI-MS.
8.Quantification of CoTPP by RP-HPLC
CoTPP was determined by HPLC.The mobile phase consisted of methanol-acetonitrile-chloroform(7:3:1,v/v)and the quantitative analysis was conducted with calibration curve method.The result indicated the calibration curve was linear in the range of 1.0-5.0μg/mL of CoTPP with r=0.9997,the minimum examination limits to 0.5μg/mL and the recoveries were between 95.05%and 102.4%.The structure was identified by means of UV-VIS,IR.
9.Industrial application of analytical method
Simultaneous determination of CoTPP and TPP by HPLC.The mobile phase consisted of methanol- acetonitrile- chloroform(7:3:1,v/v) and the quantitative method was rapid,simple and precise.This method provided excellent results in industrial application to produce cyclohexanone.
具体内容摘要如下:
1.杜仲中活性成分的提取
系统地研究了常规溶剂提取法、酶提取法、半仿生提取法和超临界CO_2提取法从杜仲中提取京尼平苷酸(GPA)、京尼平苷(GPS)、桃叶珊瑚甙(AU)、松脂醇二葡萄糖甙(PDG)、丁香脂素二葡萄糖苷(SDG)和绿原酸(CA)的方法,对这四种方法的提取效果进行了比较,得到了最优提取工艺—半仿生提取法。
2.硅胶柱色谱制备杜仲中活性成分
采用硅胶柱色谱法制备得到高纯度的京尼平苷、京尼平苷酸、松脂醇二葡萄糖苷和丁香脂素二葡萄糖苷单体,所得京尼平苷酸、京尼平苷、松脂醇二葡萄糖苷和丁香脂素二葡萄糖苷纯度分别为98.69%、96.54%、92.18%和93.77%。
3.制备型反相高效液相色谱制备杜仲中活性成分
采用制备型反相高效液相色谱制备得到高纯度的京尼平苷、京尼平苷酸、和绿原酸单体,所得京尼平苷酸、京尼平苷和绿原酸纯度分别为95.61%,93.28%和96.57%,并以京尼平苷酸为例,采用前沿分析法研究了其在C_(18)柱上的吸附机理。
4.杜仲中活性成分的纯度测定和结构鉴定
采用HPLC-DAD建立了两种方法分别测定杜仲中的木脂素类化合物、环烯醚萜类化合物和绿原酸(CA)。(1)建立了同时测定杜仲中松脂醇二葡萄糖苷和丁香脂素二葡萄糖苷的高效液相色谱方法。(2)建立了同时测定杜仲中京尼平苷酸、京尼平苷和绿原酸的反相高效液相色谱方法。
从杜仲中分离得到5个化合物经化学分析、波谱分析分别鉴定为丁香脂素二葡萄糖苷、松脂醇二葡萄糖苷京尼平苷酸、京尼平苷、绿原酸。采用静脉注射的方式对杜仲提取物的降压作用作了初步探讨,动物实验结果表明,环烯醚萜类提取物的降压效果显著,最大降压效应、最大降压百分比及作用维持时间在不同剂量组间存在显著性差异。静脉注射杜仲提取物可致SHR大鼠血压下降,这种降压作用呈剂量依赖性。
5.RP-HPLC用于杜仲原药材指纹图谱的研究
采用RP-HPLC建立了杜仲原药材指纹图谱。以京尼平苷酸作为参照物,确定杜仲原药材指纹图谱中的20个共有峰,并用炮制后的杜仲药材检验了指纹图谱。
6.CoTPP和TPP的纯化
采用溶剂萃取分离-氧化铝柱层析的方法得到了高纯度的TPP,四苯基卟啉纯度可达99.85%、总回收率达88.98%:利用CoTPP和TPP在溶剂A中的溶解性不同实现了CoTPP的纯化,纯化收率达81.95%以上,纯化后CoTPP纯度由29.57%、38.79%、32.34%提高到76.41%、81.37%、74.29%。
7.RP-HPLC法测定TPP
采用反相高效液相色谱法测定TPP的含量。流动相为甲醇:水=85:15(v/v),TPP浓度在0.5μg/mL-2.5μg/mL之间线性关系良好,加标回收率在95.2%-106.1%之间。该法简便快速。采用UV-VIS、IR、LC-ESI-MS等仪器分析手段对TPP的结构进行了表征。
8.RP-HPLC法测定CoTPP
研究建立了CoTPP的反相HPLC测定方法。流动相为甲醇:乙腈:氯仿=7:3:1(v/v),CoTPP浓度在1.0μg/mL-5.0μg/mL之间线性关系良好,加标回收率为95.05%-102.4%,RSD为0.54%。采用UV-VIS、IR等仪器分析手段鉴定了CoTPP的结构,确认了目标化合物的合成。
9.CoTPP和TPP测定方法在工业中实际应用
结合项目应用单位的实际情况,研究建立了同时测定CoTPP和TPP的反相HPLC方法。以甲醇:乙腈:氯仿=7:3:1(v/v)作流动相,方法快速、方便,精密度和准确度高,研究成果在仿生催化氧化环己烷生产环己酮的工业化试验中应用良好。
Two complicated systems,namely extract from Chinese traditional herb and porphine catalyst,were studied by the high performance liquid chromatography,open column chromatography,preparative high performance liquid chromatography,or liquid chromatography with mass spectrometry.The main content consists of two parts:(1)considering the bioactive components from Eucommia ulmoides as object,extraction, separation,determination and characterization of iridoids and lignans from Eucommia ulmoides were studied.Five bioactive compounds were attained and identified as geniposidic acid,geniposide,pinoresinol diglucoside,syringaresinol diglucoside,and chlorogenic acid by means of HPLC,UV,IR,1HNMR and MS.(2)Purification,characterization and determination of 5,10,15,20-tetraphenylporphine cobalt(CoTPP)and its middle product 5,10,15,20-tetraphenylporphine(TPP)were studied systematically by means of column chromatography,HPLC,UV-VIS,IR and HPLC-MS.It provided the method for large-scale produce of porphine catalyst and the industrial application of cyclohexane biomimetic catalytic oxidation to produce cyclohexanone.
Details are as following:
1.Extraction bioactive components from Eucommia ulmoides
Extraction methods using solvent extraction(SE),enzyme-assisted aqueous extraction(EE),semi-bionic extraction(SBE)and supercritical CO2 fluid extraction(SFE)were evaluated for the yields of geniposidic acid,geniposide,pinoresinol diglucoside,syringaresinol diglucoside, aucubin and chlorogenic acid from Eucommia ulmoides.Semi-bionic extraction was chosen for its high yields.
2.Preparation bioactive components from Eucommia ulmoides by silica gel column chromatography
Geniposidic acid,geniposide,pinoresinol diglucoside,and syringaresinol diglucoside were prepared by silica gel column chromatography.The purities of geniposidic acid,geniposide,pinoresinol diglucoside,and syringaresinol diglucoside were 98.69%,96.54%, 92.18%,and 93.77%,respectively.
3.Preparation bioactive components from Eucommia ulmoides by preparative high performance liquid chromatography
Geniposidic acid,geniposide,and chlorogenic acid were prepared by preparative high performance liquid chromatography.The purities of geniposidic acid,geniposide,and chlorogenic acid were 95.61%,93.28% and 96.57%,respectively.The adsorption mechanism of geniposidic acid on C_(18)column was studied by frontal analysis.
4.Determination and characterization of bioactive components from Eucommia ulmoides
Two methods base on high performance liquid chromatography coupled with photodiode array detector(HPLC-DAD)were established to determination of lignans,iridoids and chlorogenic acid,respectively.(1) Pinoresinol diglucoside and syringaresinol diglucoside were separated and analyzed on a Kromasil RP-C_(18)column by HPLC;(2)Geniposidic acid,geniposide,and chlorogenic acid were separated and determined by HPLC.
Five bioactive components from Eucommia ulmoides were identified as syringaresinol diglucoside,pinoresinol diglucoside,geniposidic acid, geniposide,and chlorogenic acid by chemical and spectra analysis.The animal experimental result indicated that there were significantly statistic differences in maximum effectiveness,maximum effective percentage and duration between two different groups and that intravenous administration of the extract of Eucommia ulmioides dose-dependently reduced blood pressure in the SHRs.
5.Study fingerprint ofEucommia ulmioides by HPLC
HPLC fingerprint Spectrum ofEucommia ulmioides was established. Chromatography conditions:column,Kromasil RP-C_(18)column;mobile phase,methanol-0.1%acetic acid(20:80,v/v);detection wavelength,240 nm;flow rate,0.8 mL/min;and injection volume,20μL.Geniposidic acid was used as the reference compound.
6.Purification of CoTPP and TPP
TPP was separated and purified through extraction and aluminum oxide column chromatography.The purity of purified product was 99.85%.The total recovery was 88.98%.CoTPP was separated through extraction(using efficient solvent A)and was purified by crystallization. The purity of purified CoTPP was from 29.57%,38.79%,32.34%to 76.41%,81.37%,and 74.29%,respectively.The recovery was 85.13%.
7.Quantification of TPP by RP-HPLC
TPP was determined by the reversed phase high performance liquid chromatography.The mobile phase consisted of methanol-water(85:15, v/v)and the quantitative analysis was conducted with calibration curve method.The result indicated that the calibration curve was linear in the range of 0.5-2.5μg/mL of TPP with r=0.9993,the minimum detection limits to 0.2μg/mL and the recoveries were between 95.2%and 106.1%. The structure of TPP was identified by means of UV-VIS,IR,LC-ESI-MS.
8.Quantification of CoTPP by RP-HPLC
CoTPP was determined by HPLC.The mobile phase consisted of methanol-acetonitrile-chloroform(7:3:1,v/v)and the quantitative analysis was conducted with calibration curve method.The result indicated the calibration curve was linear in the range of 1.0-5.0μg/mL of CoTPP with r=0.9997,the minimum examination limits to 0.5μg/mL and the recoveries were between 95.05%and 102.4%.The structure was identified by means of UV-VIS,IR.
9.Industrial application of analytical method
Simultaneous determination of CoTPP and TPP by HPLC.The mobile phase consisted of methanol- acetonitrile- chloroform(7:3:1,v/v) and the quantitative method was rapid,simple and precise.This method provided excellent results in industrial application to produce cyclohexanone.
引文
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