十一种酚类化合物的高效液相色谱测定方法研究
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摘要
酚类化合物是广泛分布于植物之中的一类复杂的化合物，是人类食物中一种普遍存在的组分。酚类化合物包括酚酸、黄酮和其它化合物。其中，酚酸和黄酮类化合物均具有显著的生理和药理活性，对一些常见病、多发病有重要的生理作用。本论文结合离线柱前反应和流动相添加剂增敏等多种手段，建立了十一种酚类化合物的高效液相色谱分析方法。该研究对于一些中药材、中药制剂及蔬菜中酚类化合物的质量控制以及进一步拓宽高效液相色谱法的应用范围具有重要意义。全文共分四章，作者的主要工作有以下四点：
1、建立了测定双黄连注射液中咖啡酸和黄芩苷，半枝莲药材中原儿茶酸、p-香豆酸和木樨草素及杜仲叶中没食子酸、绿原酸、p-香豆酸、芦丁和槲皮素含量的HPLC方法。实验结果表明，双黄连注射液中咖啡酸和黄芩苷的回收率分别为99．7％和108．0％，相对标准偏差(RSD)分别为1．2％和1．6％；半枝莲药材中三种化合物的回收率均在95．3～106．4％之间，RSD均在1．5～5．6％之间；杜仲叶中五种酚类成分的回收率均在97．8～106．4％之间，RSD均在1．6～3．3％之间。该研究为双黄连注射液中咖啡酸和黄芩苷两种成分的同时测定、半枝莲药材和杜仲叶的进一步开发及内在质量控制提供了科学的依据。
2、建立了高效液相色谱-二极管阵列检测器-电化学检测器(HPLC-DAD-ECD)联用技术同时分离测定鱼腥草、小蓟、马齿苋和蒲公英等药食两用品中绿原酸、咖啡酸、阿魏酸、芦丁、槲皮素和木樨草素等含量的新方法。实验结果表明，六种酚类化合物标准曲线线性良好(r≥0．9996)，回收率在94．0％～102．5％(RSD≤2．8％)之间。与HPLC-DAD法相比较，对于测定具有电化学活性的化合物，HPLC-ECD法更灵敏。与HPLC-DAD或HPLC-ECD单一方法相比较，HPLC-ECD-DAD法具有快速、简便和对多种化合物实现同时测定的优点。
3、采用离线的柱前反应，建立了HPLC-ECD-DAD联用技术研究绿原酸、阿魏酸和槲皮素清除羟自由基(·OH)能力的新方法，并将该方法用于中草药杜仲、紫花地丁、桑叶、白毛根和金银花等清除·OH能力的研究。研究表明，绿原酸、阿魏酸、槲皮素的半数清除浓度(IC_(50))顺序为：绿原酸>阿魏酸>槲皮素；每毫升含5毫克杜仲、紫花地丁、桑叶、白毛根和金银花粉末样品的50％甲醇提取液的清除率分别为：58．3％，6．5％，10．2％，8．6％，37．3％。该法为识别中药中抗氧化组分提供了一种简便而有效的途径。
4、以十二烷基磺酸钠为增敏剂，建立了测定三种中药材和两种蔬菜中芹菜素含量的反相高效液相色谱电化学的新方法。实验表明，芹菜素的线性范围为0．14～177．27μg·mL~(-1)(r=0．9999)；回收率为96．0～103．7％(RSD≤2．5％)。与HPLC-DAD方法相比较，该方法的灵敏度更高。
The phenol compound, including phenol acid, flavonoid and other compound, widely exists in the natural plants, and is a kind of ubiquitous complex compound in the mankind foods. The phenol acid and flavonoid among the phenol compound possess the remarkable biological and pharmacological activity and can be used to treat some common or frequent disease. In this thesis, the HPLC method combined with off - line pre - column reaction or enhancive sensitivity by mobile phase addition agent was established to detect the eleven phenol compounds. The present studies hold very important significances in both the quality control of Chinese traditional medicine and the broadening application range of HPLC. This thesis consists of four chapters. The author's main works are as follows:
1. The determination methods of two compounds (caffeic acid and baicalin) in Shuanghuanglian injection, three compounds (protocatechuic acid, p - coumaric acid and luteolin) in Scutellaria barbata, and five compounds (gallic acid, chlorogenic acid, p - coumaric acid, lutin and quercetin) in Folium Eucommiae leaves were established by HPLC, respectively. The experiment results showed that the recoveries of caffeic acid and baicalin in Shuanghuanglian injection were 108.0% (RSD=1.2%, n=5) and 99.7% (RSD = 1.6%, n = 5); the recoveries of three compounds in Scutellaria barbata ranged from 95.3% to 106.4% with RSDs of 1.5-5.6%; and the recoveries of five compounds in Folium Eucommiae leaves ranged from 97.8% to 106.4% with RSDs of 1.6-3.3%. The studies are reproducible and accurate, which can be used for the simultaneous determination of caffeic acid and baicalin in Shuanghuanglian injection, and provide both the scientific basis for the further exploitation and the quality control of Scutellaria barbata and Folium Eucommiae leaves.
2. An HPLC - ECD-DAD method for simultaneous separation and determination of the contents of chlorogenic acid, caffeic acid, ferulic acid, lutin, quercetin and luteolin in Houttuynia cordata, Cirsium setosum, Portulaca Oleracea L and Taraxacum mongolicum was established. As a result, all calibration curves showed good linearity (r≥0.9996) and the average recoveries of six compounds ranged from 94.0% to 102.5% (RSD≤2.8%). Compared with HPLC - DAD, HPLC -ECD is more sensitive for determination of electrochemical active compounds. Compared with HPLC-DAD or HPLC - ECD, HPLC - ECD - DAD is a rapid, simple and performs simultaneous determination method of multi - components.
3. A new method of HPLC - ECD - DAD using off- line pre - column reaction for the investigation of hydroxyl radical scavenging capacity of chlorogenic acid, ferulic acid and quercetin was established. Moreover, the method was utilized to investigate hydroxyl radical scavenging capacity of Eucommia ulmoides, Viola yedoensis, Mulberry leaf, Imperata eylindrica and Lonicera japonica thumb. As a result, the 50% inhibition concentration (IC_(50)) order of hydroxyl radical scavenging of three compounds was chlorogenic acid > ferulic acid > quercetin. The hydroxyl radical scavenging of Eucommia ulmoides, Viola yedoensis, Mulberry leaf, Imperata eylindrica and Lonicera japonica thumb was 58.3%, 6.5%, 10.2%, 8.6% and 37.3%, respectively. The method can be utilized to identify the components of the Chinese herb with antioxidation function.
4. Using sodium dodecylsulfonate as sensitizer, a new HPLC - ECD method for determination of apigenin in three Chinese herbs and two vegetables was established. As a result, the linear range of apigenin was 0.14-177.27μg·mL~(-1)(r = 0.9999). The recoveries were 96.0 - 103.7% (RSD≤2.5%). Compared with HPLC - DAD, this new method is more sensitive.
1、建立了测定双黄连注射液中咖啡酸和黄芩苷，半枝莲药材中原儿茶酸、p-香豆酸和木樨草素及杜仲叶中没食子酸、绿原酸、p-香豆酸、芦丁和槲皮素含量的HPLC方法。实验结果表明，双黄连注射液中咖啡酸和黄芩苷的回收率分别为99．7％和108．0％，相对标准偏差(RSD)分别为1．2％和1．6％；半枝莲药材中三种化合物的回收率均在95．3～106．4％之间，RSD均在1．5～5．6％之间；杜仲叶中五种酚类成分的回收率均在97．8～106．4％之间，RSD均在1．6～3．3％之间。该研究为双黄连注射液中咖啡酸和黄芩苷两种成分的同时测定、半枝莲药材和杜仲叶的进一步开发及内在质量控制提供了科学的依据。
2、建立了高效液相色谱-二极管阵列检测器-电化学检测器(HPLC-DAD-ECD)联用技术同时分离测定鱼腥草、小蓟、马齿苋和蒲公英等药食两用品中绿原酸、咖啡酸、阿魏酸、芦丁、槲皮素和木樨草素等含量的新方法。实验结果表明，六种酚类化合物标准曲线线性良好(r≥0．9996)，回收率在94．0％～102．5％(RSD≤2．8％)之间。与HPLC-DAD法相比较，对于测定具有电化学活性的化合物，HPLC-ECD法更灵敏。与HPLC-DAD或HPLC-ECD单一方法相比较，HPLC-ECD-DAD法具有快速、简便和对多种化合物实现同时测定的优点。
3、采用离线的柱前反应，建立了HPLC-ECD-DAD联用技术研究绿原酸、阿魏酸和槲皮素清除羟自由基(·OH)能力的新方法，并将该方法用于中草药杜仲、紫花地丁、桑叶、白毛根和金银花等清除·OH能力的研究。研究表明，绿原酸、阿魏酸、槲皮素的半数清除浓度(IC_(50))顺序为：绿原酸>阿魏酸>槲皮素；每毫升含5毫克杜仲、紫花地丁、桑叶、白毛根和金银花粉末样品的50％甲醇提取液的清除率分别为：58．3％，6．5％，10．2％，8．6％，37．3％。该法为识别中药中抗氧化组分提供了一种简便而有效的途径。
4、以十二烷基磺酸钠为增敏剂，建立了测定三种中药材和两种蔬菜中芹菜素含量的反相高效液相色谱电化学的新方法。实验表明，芹菜素的线性范围为0．14～177．27μg·mL~(-1)(r=0．9999)；回收率为96．0～103．7％(RSD≤2．5％)。与HPLC-DAD方法相比较，该方法的灵敏度更高。
The phenol compound, including phenol acid, flavonoid and other compound, widely exists in the natural plants, and is a kind of ubiquitous complex compound in the mankind foods. The phenol acid and flavonoid among the phenol compound possess the remarkable biological and pharmacological activity and can be used to treat some common or frequent disease. In this thesis, the HPLC method combined with off - line pre - column reaction or enhancive sensitivity by mobile phase addition agent was established to detect the eleven phenol compounds. The present studies hold very important significances in both the quality control of Chinese traditional medicine and the broadening application range of HPLC. This thesis consists of four chapters. The author's main works are as follows:
1. The determination methods of two compounds (caffeic acid and baicalin) in Shuanghuanglian injection, three compounds (protocatechuic acid, p - coumaric acid and luteolin) in Scutellaria barbata, and five compounds (gallic acid, chlorogenic acid, p - coumaric acid, lutin and quercetin) in Folium Eucommiae leaves were established by HPLC, respectively. The experiment results showed that the recoveries of caffeic acid and baicalin in Shuanghuanglian injection were 108.0% (RSD=1.2%, n=5) and 99.7% (RSD = 1.6%, n = 5); the recoveries of three compounds in Scutellaria barbata ranged from 95.3% to 106.4% with RSDs of 1.5-5.6%; and the recoveries of five compounds in Folium Eucommiae leaves ranged from 97.8% to 106.4% with RSDs of 1.6-3.3%. The studies are reproducible and accurate, which can be used for the simultaneous determination of caffeic acid and baicalin in Shuanghuanglian injection, and provide both the scientific basis for the further exploitation and the quality control of Scutellaria barbata and Folium Eucommiae leaves.
2. An HPLC - ECD-DAD method for simultaneous separation and determination of the contents of chlorogenic acid, caffeic acid, ferulic acid, lutin, quercetin and luteolin in Houttuynia cordata, Cirsium setosum, Portulaca Oleracea L and Taraxacum mongolicum was established. As a result, all calibration curves showed good linearity (r≥0.9996) and the average recoveries of six compounds ranged from 94.0% to 102.5% (RSD≤2.8%). Compared with HPLC - DAD, HPLC -ECD is more sensitive for determination of electrochemical active compounds. Compared with HPLC-DAD or HPLC - ECD, HPLC - ECD - DAD is a rapid, simple and performs simultaneous determination method of multi - components.
3. A new method of HPLC - ECD - DAD using off- line pre - column reaction for the investigation of hydroxyl radical scavenging capacity of chlorogenic acid, ferulic acid and quercetin was established. Moreover, the method was utilized to investigate hydroxyl radical scavenging capacity of Eucommia ulmoides, Viola yedoensis, Mulberry leaf, Imperata eylindrica and Lonicera japonica thumb. As a result, the 50% inhibition concentration (IC_(50)) order of hydroxyl radical scavenging of three compounds was chlorogenic acid > ferulic acid > quercetin. The hydroxyl radical scavenging of Eucommia ulmoides, Viola yedoensis, Mulberry leaf, Imperata eylindrica and Lonicera japonica thumb was 58.3%, 6.5%, 10.2%, 8.6% and 37.3%, respectively. The method can be utilized to identify the components of the Chinese herb with antioxidation function.
4. Using sodium dodecylsulfonate as sensitizer, a new HPLC - ECD method for determination of apigenin in three Chinese herbs and two vegetables was established. As a result, the linear range of apigenin was 0.14-177.27μg·mL~(-1)(r = 0.9999). The recoveries were 96.0 - 103.7% (RSD≤2.5%). Compared with HPLC - DAD, this new method is more sensitive.
引文
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