乌药、锦灯笼药效物质及质量评价方法研究
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摘要
中药药效物质不清楚、质量评价方法不可靠以及作用机制不明确是目前制约中药现代化进程的主要因素。为此,本论文围绕中药药效物质、质量控制及药代动力学三个方面,以乌药和锦灯笼为研究载体,综合运用多种研究模式和现代仪器分析手段,对乌药保肝作用以及锦灯笼抗炎作用的药效物质基础进行了研究,建立了两种药材的质量评价方法,并初步探明了锦灯笼相关药效成分的药代动力学性质。本论文主要研究内容及学术贡献如下：
1.利用现代色谱分离方法对浙江台州道地药材乌药的95%乙醇提取物进行了系统分离,共分得13个化合物,并根据其理化性质和现代波谱学技术(包括UV、IR,1HNMR、13C NMR, HMQC、HMBC、NOESY、COSY和HRMS等)鉴定了它们的结构,分别为Linderagalactone B(1),Linderagalactone D(2), Linderagalactone E(3),3-eudesmene-1β,11-diol(4),Linderagalactone A(5), Linderagalactone C(6),羟基香樟内酯(7),Strychnistenolide (8),8-hydroxyisogermafurenolide(9), Atractylenolide Ⅲ (10),乌药内酯(11),乌药醚内酯(12)和新乌药内酯(13),除化合物4外,其余均为倍半萜内酯类化合物,化合物1、2、3、5和6为新化合物。另外,通过人肝细胞(HepG2) H2O2损伤模型对所得化合物的保肝活性进行了筛选,发现大部分化合物均具有肝细胞保护活性,其中化合物3、7、11和12活性较好。本研究初步揭示了乌药保肝作用的药效物质基础,并发现了5个新化合物,从而为乌药相关新药的开发和其合理质量评价方法的建立提供了科学依据。
2.建立了锦灯笼抗炎活性部位及其灌胃给药后大鼠血浆的HPLC-DAD指纹图谱分析方法,比较给药前后大鼠血浆成分的变化情况,发现提取物灌胃后被大鼠吸收入血的成分有20多个。以给药后血浆指纹图谱为指导,定向地从锦灯笼提取物中分离制备锦灯笼血中移行成分,进行结构鉴定。结果分离得到9个化合物,并鉴定了它们的结构,其中7个为酸浆苦素类化合物。通过体外细胞炎症模型筛选,并结合相关文献调研,确定酸浆苦素类化合物为锦灯笼抗炎药效的主要物质基础。本研究对进一步建立锦灯笼合理的质量评价方法和探索其药代动力学性质具有重要的指导意义。
3.采用UPLC-ESI-MS/MS技术,分别建立了乌药和锦灯笼中5个倍半萜类和5个酸浆苦素类药效成分的定量分析方法,经相应的方法学考察,证明所建方法分析速度快,且准确、稳定、可靠,并将所建方法成功应用于不同产地药材中相关成分的定量分析和质量评价。此外,还对4,7-二脱氢新酸浆苦素B的3个转化产物进行了鉴定。研究证明本文所建方法可用于相关药材及其制剂的质量评价；而且,本研究还拓展了UPLC-MS/MS技术在中药定量分析领域的应用范围,为乌药与锦灯笼的合理质量评价提供了新的分析方法。
4.运用UPLC-DAD-ESI-MS/MS技术,分别建立了乌药和锦灯笼活性部位的指纹图谱质量评价方法和主要指纹峰质谱裂解规律及结构鉴定的质谱分析方法。从乌药提取物中定性鉴别出3个生物碱类化合物和8个倍半萜及其内酯类化合物；总结了酸浆苦素类化合物的质谱裂解规律,从锦灯笼活性提取部位定性鉴别出19个化合物,其中14个为酸浆苦素类化合物。最后运用所建立的UPLC分析方法结合相似度分析和主成分分析(PCA),分别对采集到的13批乌药和31批锦灯笼样品的品质进行了评价。本研究为倍半萜和酸浆苦素类化合物的快速发现提供了参考数据,为乌药和锦灯笼的质量控制提供了新的评价方法,并且为UPLC-MS/MS技术在中药及其复方物质基础快速分析鉴定中的应用提供了借鉴和参考。
5.运用UPLC-ESI-MS/MS技术,以锦灯笼中的酸浆苦素D、酸浆苦素G和4,7-二脱氢新酸浆苦素B为该药材的代表性药效成分,研究了锦灯笼提取物在大鼠灌胃给药和主要成分尾静脉注射时的药代动力学性质。考察了4,7-二脱氢新酸浆苦素B与鼠肝微粒体孵育时产生的Ⅰ相代谢产物,通过MS/MS分析鉴定了其中的8个代谢物,并初步推测出4,7-二脱氢新酸浆苦素B在体外大鼠肝微粒体中的代谢途径。
Currently, the severest challenges for the modernization of Traditional Chinese Medicine (TCM) are the unclear of pharmacodynamic materials and action mechanism, and the unreliable quality control methods. For this reason, taking Lindera aggregata (Wu-yao) and Phyhalis alkekengi (Chinese lantern) as the research carriers, this dissertation accordingly focused on the investigation of pharmacodynamic materials, quality control methods and related pharmacokinetics of the two TCMs, by combination of multiple research modes and modern instrument analytical techniques. Ultimately, the pharmacodynamic materials of Lindera aggregata and Phyhalis alkekengi for hepatoprotective and anti-inflammatory activities, respectively, were clarified; the reliable quality control methods of the two TCM were established, and the main pharmacokinetics features of Phyhalis alkekengi were revealed. The main innovation and academic contributions of this dissertation are presented as follows:
1.13compounds were isolated from95%ethanol extract of Lindera aggregata that collected from Taizhou, Zhejiang province, by using modern chromatographic techniques. Structures of the13compounds were identified by physico-chemical properties and modern spectral techniques (including UV, IR,1H NMR,13C NMR, HMQC, HMBC, NOESY, COSY and HRMS). They were Linderagalactone B (1), Linderagalactone D (2), Linderagalactone E (3),3-eudesmene-1β,11-diol (4), Linderagalactone A (5), Linderagalactone C (6), Hydroxylindestenolide (7), Strychnistenolide (8),8-hydroxyisogermafurenolide (9), Atractylenolide Ⅲ (10), Linderalactone (11), Linderane (12) and Neolinderalactone (13). They were all sesquiterpene lactones except for4, and1,2,3,5and6were new compounds. Among them,3,7,11and12showed highly hepatoprotective activity against H2O2-induced oxidative damages on HepG2cells. This research clarified the pharmacodynamic materials of Lindera aggregata for hepatoprotective, and found some new compounds. These results provided the theoretical basis and scientific reference for quality control, new drug development and application of Lindera aggregata.
2. Based on the established HPLC fingerprint of Phyhalis alkekengi (Chinese lantern) preparations (CLP), analysis and comparison were carried out among the HPLC profiles of rat plasma (samples obtained after intragastric administration of CLP), CLP and blank plasma, about twenty compounds of CLP were found absorbed into blood. Then, directed by the drug contented plasma's fingerprint, the isolation, purification and identification of the absorbed constituents were performed,9compounds were isolated and indentified, and7of them belonged to physalins. Finally, through in vitro anti-inflammatory mode, combining with literature researchs, physalins were determined to be the pharmacodynamic materials of CLP for anti-inflammatory activity. This research is very important for establishing quality evaluation methods and exploring pharmacokinetic properties of Phyhalis alkekengi.
3. UPLC-MS/MS methods were established to evaluate the quality of Lindera aggregata and Phyhalis alkekengi through simultaneous quantitation of5sesquiterpene lactones and5physalins, respectively. The results showed that the developed methods had good linearity, precision, accuracy and sensitivity for the determination of the active compounds. Finally, these simple, rapid and reliable methods were successfully applied to determine the sesquiterpene lactones and physalins in Lindera aggregata and Phyhalis alkekengi samples from different areas of China. Otherwise, this study found that4,7-didehydrophysalin B was instable under room temperature, and its3transformation products were detected and identified for the first time. This study laid a solid foundation for the establishment of comprehensive quality control methods of Lindera aggregata and Phyhalis alkekengi.
4. Chromatographic fingerprinting analysis methods of Lindera aggregata and Phyhalis alkekengL were established using UPLC-DAD-MS/MS, respectively. MS fragmentation behavior and UV characteristics of sesquiterpene lactones and physalins were also investigated. According to the UPLC retention behavior, the diagnostic UV spectra and the molecular structural information provided by MS/MS spectra,11fingerprint peaks were identified from Lindera aggregata (including3alkaloids and8sesquiterpene lactones), and19fingerprint peaks were identified from Phyhalis alkekengi (14of them belonged to physalins). Finally, the established fingerprinting methods were applied to evaluate the quality of13Lindera aggregata and31Phyhalis alkekengi samples through similarity and PCA. The proposed methods provide a scientific technical platform for the quality control of TCM and the rapidly study of chemical components of TCM.
5. An UPLC-MS/MS method was developed for the quantification of3major active ingredients (physalin D, physalin G and4,7-didehydroneophysalin B) of CLP in rat plasma. The developed method provided a simple sample preparation and a stable analytical result for the determination of these physalins in plasma samples. This method was successfully applied to the determination of the3major components of Phyhalis alkekengi in rat plasma after intragastric or intravenous administration. In addition, the metabolism of4,7-didehydroneophysalin B in liver microsomes was investigated. Eight metabolites were identified by MS/MS data, and metabolic pathways of4,7-didehydroneophysalin B were deduced.
1.利用现代色谱分离方法对浙江台州道地药材乌药的95%乙醇提取物进行了系统分离,共分得13个化合物,并根据其理化性质和现代波谱学技术(包括UV、IR,1HNMR、13C NMR, HMQC、HMBC、NOESY、COSY和HRMS等)鉴定了它们的结构,分别为Linderagalactone B(1),Linderagalactone D(2), Linderagalactone E(3),3-eudesmene-1β,11-diol(4),Linderagalactone A(5), Linderagalactone C(6),羟基香樟内酯(7),Strychnistenolide (8),8-hydroxyisogermafurenolide(9), Atractylenolide Ⅲ (10),乌药内酯(11),乌药醚内酯(12)和新乌药内酯(13),除化合物4外,其余均为倍半萜内酯类化合物,化合物1、2、3、5和6为新化合物。另外,通过人肝细胞(HepG2) H2O2损伤模型对所得化合物的保肝活性进行了筛选,发现大部分化合物均具有肝细胞保护活性,其中化合物3、7、11和12活性较好。本研究初步揭示了乌药保肝作用的药效物质基础,并发现了5个新化合物,从而为乌药相关新药的开发和其合理质量评价方法的建立提供了科学依据。
2.建立了锦灯笼抗炎活性部位及其灌胃给药后大鼠血浆的HPLC-DAD指纹图谱分析方法,比较给药前后大鼠血浆成分的变化情况,发现提取物灌胃后被大鼠吸收入血的成分有20多个。以给药后血浆指纹图谱为指导,定向地从锦灯笼提取物中分离制备锦灯笼血中移行成分,进行结构鉴定。结果分离得到9个化合物,并鉴定了它们的结构,其中7个为酸浆苦素类化合物。通过体外细胞炎症模型筛选,并结合相关文献调研,确定酸浆苦素类化合物为锦灯笼抗炎药效的主要物质基础。本研究对进一步建立锦灯笼合理的质量评价方法和探索其药代动力学性质具有重要的指导意义。
3.采用UPLC-ESI-MS/MS技术,分别建立了乌药和锦灯笼中5个倍半萜类和5个酸浆苦素类药效成分的定量分析方法,经相应的方法学考察,证明所建方法分析速度快,且准确、稳定、可靠,并将所建方法成功应用于不同产地药材中相关成分的定量分析和质量评价。此外,还对4,7-二脱氢新酸浆苦素B的3个转化产物进行了鉴定。研究证明本文所建方法可用于相关药材及其制剂的质量评价；而且,本研究还拓展了UPLC-MS/MS技术在中药定量分析领域的应用范围,为乌药与锦灯笼的合理质量评价提供了新的分析方法。
4.运用UPLC-DAD-ESI-MS/MS技术,分别建立了乌药和锦灯笼活性部位的指纹图谱质量评价方法和主要指纹峰质谱裂解规律及结构鉴定的质谱分析方法。从乌药提取物中定性鉴别出3个生物碱类化合物和8个倍半萜及其内酯类化合物；总结了酸浆苦素类化合物的质谱裂解规律,从锦灯笼活性提取部位定性鉴别出19个化合物,其中14个为酸浆苦素类化合物。最后运用所建立的UPLC分析方法结合相似度分析和主成分分析(PCA),分别对采集到的13批乌药和31批锦灯笼样品的品质进行了评价。本研究为倍半萜和酸浆苦素类化合物的快速发现提供了参考数据,为乌药和锦灯笼的质量控制提供了新的评价方法,并且为UPLC-MS/MS技术在中药及其复方物质基础快速分析鉴定中的应用提供了借鉴和参考。
5.运用UPLC-ESI-MS/MS技术,以锦灯笼中的酸浆苦素D、酸浆苦素G和4,7-二脱氢新酸浆苦素B为该药材的代表性药效成分,研究了锦灯笼提取物在大鼠灌胃给药和主要成分尾静脉注射时的药代动力学性质。考察了4,7-二脱氢新酸浆苦素B与鼠肝微粒体孵育时产生的Ⅰ相代谢产物,通过MS/MS分析鉴定了其中的8个代谢物,并初步推测出4,7-二脱氢新酸浆苦素B在体外大鼠肝微粒体中的代谢途径。
Currently, the severest challenges for the modernization of Traditional Chinese Medicine (TCM) are the unclear of pharmacodynamic materials and action mechanism, and the unreliable quality control methods. For this reason, taking Lindera aggregata (Wu-yao) and Phyhalis alkekengi (Chinese lantern) as the research carriers, this dissertation accordingly focused on the investigation of pharmacodynamic materials, quality control methods and related pharmacokinetics of the two TCMs, by combination of multiple research modes and modern instrument analytical techniques. Ultimately, the pharmacodynamic materials of Lindera aggregata and Phyhalis alkekengi for hepatoprotective and anti-inflammatory activities, respectively, were clarified; the reliable quality control methods of the two TCM were established, and the main pharmacokinetics features of Phyhalis alkekengi were revealed. The main innovation and academic contributions of this dissertation are presented as follows:
1.13compounds were isolated from95%ethanol extract of Lindera aggregata that collected from Taizhou, Zhejiang province, by using modern chromatographic techniques. Structures of the13compounds were identified by physico-chemical properties and modern spectral techniques (including UV, IR,1H NMR,13C NMR, HMQC, HMBC, NOESY, COSY and HRMS). They were Linderagalactone B (1), Linderagalactone D (2), Linderagalactone E (3),3-eudesmene-1β,11-diol (4), Linderagalactone A (5), Linderagalactone C (6), Hydroxylindestenolide (7), Strychnistenolide (8),8-hydroxyisogermafurenolide (9), Atractylenolide Ⅲ (10), Linderalactone (11), Linderane (12) and Neolinderalactone (13). They were all sesquiterpene lactones except for4, and1,2,3,5and6were new compounds. Among them,3,7,11and12showed highly hepatoprotective activity against H2O2-induced oxidative damages on HepG2cells. This research clarified the pharmacodynamic materials of Lindera aggregata for hepatoprotective, and found some new compounds. These results provided the theoretical basis and scientific reference for quality control, new drug development and application of Lindera aggregata.
2. Based on the established HPLC fingerprint of Phyhalis alkekengi (Chinese lantern) preparations (CLP), analysis and comparison were carried out among the HPLC profiles of rat plasma (samples obtained after intragastric administration of CLP), CLP and blank plasma, about twenty compounds of CLP were found absorbed into blood. Then, directed by the drug contented plasma's fingerprint, the isolation, purification and identification of the absorbed constituents were performed,9compounds were isolated and indentified, and7of them belonged to physalins. Finally, through in vitro anti-inflammatory mode, combining with literature researchs, physalins were determined to be the pharmacodynamic materials of CLP for anti-inflammatory activity. This research is very important for establishing quality evaluation methods and exploring pharmacokinetic properties of Phyhalis alkekengi.
3. UPLC-MS/MS methods were established to evaluate the quality of Lindera aggregata and Phyhalis alkekengi through simultaneous quantitation of5sesquiterpene lactones and5physalins, respectively. The results showed that the developed methods had good linearity, precision, accuracy and sensitivity for the determination of the active compounds. Finally, these simple, rapid and reliable methods were successfully applied to determine the sesquiterpene lactones and physalins in Lindera aggregata and Phyhalis alkekengi samples from different areas of China. Otherwise, this study found that4,7-didehydrophysalin B was instable under room temperature, and its3transformation products were detected and identified for the first time. This study laid a solid foundation for the establishment of comprehensive quality control methods of Lindera aggregata and Phyhalis alkekengi.
4. Chromatographic fingerprinting analysis methods of Lindera aggregata and Phyhalis alkekengL were established using UPLC-DAD-MS/MS, respectively. MS fragmentation behavior and UV characteristics of sesquiterpene lactones and physalins were also investigated. According to the UPLC retention behavior, the diagnostic UV spectra and the molecular structural information provided by MS/MS spectra,11fingerprint peaks were identified from Lindera aggregata (including3alkaloids and8sesquiterpene lactones), and19fingerprint peaks were identified from Phyhalis alkekengi (14of them belonged to physalins). Finally, the established fingerprinting methods were applied to evaluate the quality of13Lindera aggregata and31Phyhalis alkekengi samples through similarity and PCA. The proposed methods provide a scientific technical platform for the quality control of TCM and the rapidly study of chemical components of TCM.
5. An UPLC-MS/MS method was developed for the quantification of3major active ingredients (physalin D, physalin G and4,7-didehydroneophysalin B) of CLP in rat plasma. The developed method provided a simple sample preparation and a stable analytical result for the determination of these physalins in plasma samples. This method was successfully applied to the determination of the3major components of Phyhalis alkekengi in rat plasma after intragastric or intravenous administration. In addition, the metabolism of4,7-didehydroneophysalin B in liver microsomes was investigated. Eight metabolites were identified by MS/MS data, and metabolic pathways of4,7-didehydroneophysalin B were deduced.
引文
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