肺形草、菊三七的物质基础及分析方法研究
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摘要
中药现代化的重要目标之一是质量稳定、可控。如何提高中药的质量控制水平是中药现代化亟待解决的关键问题。而中药的物质基础和分析方法研究是提高中药质量控制水平的前提。
本文运用多种色谱及其联用技术,以肺形草、菊三七和参麦注射液为研究对象,分别研究建立中药三类化学成分-有效成分、有毒成分和无效成分的定性定量分析方法,为中药及其制剂的质量控制和合理应用提供科学依据。主要研究内容及成果如下:
1.采用多种色谱分离技术从肺形草的70%乙醇提取物中分离得到6个化合物。综合运用ESI-MS、TOF-MS、~1H NMR、~(13)C NMR、~1H-~1HCOSY、HMQC、HMBC等波谱学手段鉴定了它们的结构。其中4个为有较好抗氧化活性的(?)酮类化合物,其余2个为首次从双蝴蝶属植物中分离得到,且有1个为新化合物。
2.选用填料直径为1.8μm的快速分离高通量柱(RRHT),建立了肺形草中(?)酮类成分的含量测定方法。对所建色谱方法的信号采集、柱温、流速和进样体积等参数进行了优化,并进行了系统适用性试验。四种(?)酮在6分钟内实现了基线分离,浓度在0.75-300μg/ml之间时,标准曲线的相关系数(R~2)为0.9992-1.0000;检测限达0.1-0.3μg/ml。该方法实现了样品的快速分离,提高了检测灵敏度,降低了流动相的消耗。
3.研究建立了菊三七中PAs和PANOs的HPLC-ESI-MS~n定性分析方法。先对从菊三七中分得的3个PAs和1个PANO对照品直接进样分析,PANO有明显的[2M+H]~+峰(丰度通常为100%),再根据多级质谱碎片离子分别推导PAs和PANOs的裂解规律。然后以这些规律为基础,结合文献报道和生物合成途径,共鉴定或推测了20个PAs和PANOs,其中16个是首次从该植物中发现,tetrahydrosenecionine首次作为天然产物报道。
4.采用35 mM月桂酸-120 mM Tris-20%甲醇(v/v)的缓冲体系,建立了MEKC法测定菊三七中PAs含量的方法。千里光菲灵碱和千里光碱浓度在3.1-200μg/ml之间时,标准曲线的相关系数(R~2)为0.9916-0.9939;检测限达1.0μg/ml。相比传统的SDS-硼砂体系,具有分离效能高,分离时间短、电流强度小等优点。该方法适用于菊三七药材的质量控制。
5.研究建立了菊三七中PAs和PANOs的CZE-MS定量分析方法。缓冲液的组成为:20 mM醋酸铵-1%甲酸-5%甲醇(v/v)。采用电动进样-场放大样品堆积的在线富集技术,提高灵敏度30-200倍。PAs和PANOs的检测限分别达到0.01和0.1 ng/ml。该方法快速、灵敏,适用于中药中痕量PAs和PANOs的检测。
6.研究建立了HPLC-ELSD法测定参麦注射液中糖类成分含量的方法。色谱柱为氨基柱;流动相为乙腈-水体系。D-果糖、D-葡萄糖、蔗糖和麦芽糖的浓度在0.025～1.000 mg/ml之间时,标准曲线的相关系数(R~2)为0.9983-0.9992。另外采用苯酚-硫酸法和冷冻干燥法测定了参麦注射液中的总糖含量,并对这三种测定方法进行了比较。
As we all know, quality control is one of the key issues of the modernization for TCM. Studies on material foundation and analysis methods of TCM are the premise of quality control.
Tripterospermum Chinese (Migo) H. Smith (Feixingcao), Gynura segetum (Lour.) Merr. (Jusanqi) and Shenmai injection were chosen as objects for exploring the material foundation and analysis methods by chromatography and hyphenated techniques. In this thesis, systemic studies on the effective constituents, toxic constituents and ineffective constituents of TCM were carried out. The results supplied a scientific research methodology used for quality control and reasonable application of the TCM. The main innovation and academic contributions of this dissertation are presented as follows:
1. Column chromatography techniques were used to separate constituents from the 70% ethanol extract of the whole plants of T. Chinese and the structures of six compounds were elucidated by ESI-MS, TOF-MS, ~1H NMR, ~(13)C NMR, HMQC, ~1H-~1HCOSY, HMBC. Four of them were xanthones which had antioxidant activity, the other two of which one belonged to new compounds were isolated from the genus Tripterospermum for the first time.
2. Based on sub-2μm (1.8μm) column, a novel chromatography method was constructed. The chromatography parameters, such as signal acquisition, column temperature, flow rate and volume of sample injection, were optimized. SST was good enough to meet the quantitative analysis of xanthones in feixingcao. The four xanthones were baseline separated within 6 min. Linearity of the method was excellent with correlation coefficients (R~2) in the range of 0.9992-1.000 when the concentration of xanthones varied from 0.75 to 300μg/ml. Limit of detection was in the range of 0.1-0.3μg/ml. This method could provide high-speed separation and high sensitivity under ordinary pressure, meanwhile the consumption of mobile phase decreased.
3. In this study, pyrrolizidine alkaloids (PAs) and their corresponding N-oxides (PANOs) were extracted from the whole plant of G. segetum and analyzed by high performance liquid chromatography coupled to ion trap mass spectrometry. Identification of eluted peaks as PANOs was indicated by virtue of their MS and MS~n analysis, in addition to the [M+H]~+ adduct ion, characteristically showed a significant (usually 100% abundance) dimer adduct [2M+H]~+ that is not observed in the MS of the parent PAs. A total of 20 compounds were identified or tentatively characterized based on their mass spectra and possible biosynthetic pathways. Sixteen constituents were reported for the first time from G. segetum and tetrahydrosenecionine has not been previously reported as a natural product.
4. A novel, rapid and sensitive MEKC method was developed for the separation and determination of two hepatotoxic pyrrolizidine alkaloids in G. segetum within 8 min. The optimal running buffer containing 35 mM lauric acid, 120 mM Tris and 20% methanol (v/v) was employed. Linearity of the method was excellent with correlation coefficients (R~2) in the range of 0.9916-0.9939 when the concentration of PAs varied from 3.1 to 200μg/ml. Limit of detection of the two PAs was 1.0μg/ml. Compared with traditional SDS/inorganic bases system, this method provided high efficiencies, on account of its low ionic strength and therefore low conductivity. This method was suit for the quality control of Jusanqi.
5. A novel, rapid and high-sensitivity CZE-MS method was developed for the simultaneous determination of hepatotoxic pyrrolizidine alkaloids and N-oxides. The optimal running buffer containing 20 mM ammonium acetate, 1% formic acid and 5% methanol (v/v) was employed. Field-amplified sample stacking with electromigration-injection (FASS-EMI) was used for the on-line concentration of the alkaloids. This online preconcentration strategy resulted in sensitivity enhancement factors 30-fold for PAs and 200-fold for PANOs. The LOD was 0.01 ng/ml for the two PAs and was 0.1 ng/ml for the two PANOs. The method is suited to determination of trace amount PAs and PANOs in TCM.
6. The method of HPLC-ELSD for the analysis of contents of D-fructose, D-glucose, sucrose and maltose in Shenmai injection was established. Saccharides were separated by NH_2 column and the mobile phase was acetonitrile-water. Linearity of the method was excellent with correlation coefficients (R~2) in the range of 0.9983-0.9992 when the concentration of saccharides varied from 0.025 to 1.000 mg/ml. The total saccharide in Shenmai injection was also determined using Phenylhydrate-sulfuric acid and Freeze Drying methods. Furthermore, these three methods were compared seriously.
本文运用多种色谱及其联用技术,以肺形草、菊三七和参麦注射液为研究对象,分别研究建立中药三类化学成分-有效成分、有毒成分和无效成分的定性定量分析方法,为中药及其制剂的质量控制和合理应用提供科学依据。主要研究内容及成果如下:
1.采用多种色谱分离技术从肺形草的70%乙醇提取物中分离得到6个化合物。综合运用ESI-MS、TOF-MS、~1H NMR、~(13)C NMR、~1H-~1HCOSY、HMQC、HMBC等波谱学手段鉴定了它们的结构。其中4个为有较好抗氧化活性的(?)酮类化合物,其余2个为首次从双蝴蝶属植物中分离得到,且有1个为新化合物。
2.选用填料直径为1.8μm的快速分离高通量柱(RRHT),建立了肺形草中(?)酮类成分的含量测定方法。对所建色谱方法的信号采集、柱温、流速和进样体积等参数进行了优化,并进行了系统适用性试验。四种(?)酮在6分钟内实现了基线分离,浓度在0.75-300μg/ml之间时,标准曲线的相关系数(R~2)为0.9992-1.0000;检测限达0.1-0.3μg/ml。该方法实现了样品的快速分离,提高了检测灵敏度,降低了流动相的消耗。
3.研究建立了菊三七中PAs和PANOs的HPLC-ESI-MS~n定性分析方法。先对从菊三七中分得的3个PAs和1个PANO对照品直接进样分析,PANO有明显的[2M+H]~+峰(丰度通常为100%),再根据多级质谱碎片离子分别推导PAs和PANOs的裂解规律。然后以这些规律为基础,结合文献报道和生物合成途径,共鉴定或推测了20个PAs和PANOs,其中16个是首次从该植物中发现,tetrahydrosenecionine首次作为天然产物报道。
4.采用35 mM月桂酸-120 mM Tris-20%甲醇(v/v)的缓冲体系,建立了MEKC法测定菊三七中PAs含量的方法。千里光菲灵碱和千里光碱浓度在3.1-200μg/ml之间时,标准曲线的相关系数(R~2)为0.9916-0.9939;检测限达1.0μg/ml。相比传统的SDS-硼砂体系,具有分离效能高,分离时间短、电流强度小等优点。该方法适用于菊三七药材的质量控制。
5.研究建立了菊三七中PAs和PANOs的CZE-MS定量分析方法。缓冲液的组成为:20 mM醋酸铵-1%甲酸-5%甲醇(v/v)。采用电动进样-场放大样品堆积的在线富集技术,提高灵敏度30-200倍。PAs和PANOs的检测限分别达到0.01和0.1 ng/ml。该方法快速、灵敏,适用于中药中痕量PAs和PANOs的检测。
6.研究建立了HPLC-ELSD法测定参麦注射液中糖类成分含量的方法。色谱柱为氨基柱;流动相为乙腈-水体系。D-果糖、D-葡萄糖、蔗糖和麦芽糖的浓度在0.025～1.000 mg/ml之间时,标准曲线的相关系数(R~2)为0.9983-0.9992。另外采用苯酚-硫酸法和冷冻干燥法测定了参麦注射液中的总糖含量,并对这三种测定方法进行了比较。
As we all know, quality control is one of the key issues of the modernization for TCM. Studies on material foundation and analysis methods of TCM are the premise of quality control.
Tripterospermum Chinese (Migo) H. Smith (Feixingcao), Gynura segetum (Lour.) Merr. (Jusanqi) and Shenmai injection were chosen as objects for exploring the material foundation and analysis methods by chromatography and hyphenated techniques. In this thesis, systemic studies on the effective constituents, toxic constituents and ineffective constituents of TCM were carried out. The results supplied a scientific research methodology used for quality control and reasonable application of the TCM. The main innovation and academic contributions of this dissertation are presented as follows:
1. Column chromatography techniques were used to separate constituents from the 70% ethanol extract of the whole plants of T. Chinese and the structures of six compounds were elucidated by ESI-MS, TOF-MS, ~1H NMR, ~(13)C NMR, HMQC, ~1H-~1HCOSY, HMBC. Four of them were xanthones which had antioxidant activity, the other two of which one belonged to new compounds were isolated from the genus Tripterospermum for the first time.
2. Based on sub-2μm (1.8μm) column, a novel chromatography method was constructed. The chromatography parameters, such as signal acquisition, column temperature, flow rate and volume of sample injection, were optimized. SST was good enough to meet the quantitative analysis of xanthones in feixingcao. The four xanthones were baseline separated within 6 min. Linearity of the method was excellent with correlation coefficients (R~2) in the range of 0.9992-1.000 when the concentration of xanthones varied from 0.75 to 300μg/ml. Limit of detection was in the range of 0.1-0.3μg/ml. This method could provide high-speed separation and high sensitivity under ordinary pressure, meanwhile the consumption of mobile phase decreased.
3. In this study, pyrrolizidine alkaloids (PAs) and their corresponding N-oxides (PANOs) were extracted from the whole plant of G. segetum and analyzed by high performance liquid chromatography coupled to ion trap mass spectrometry. Identification of eluted peaks as PANOs was indicated by virtue of their MS and MS~n analysis, in addition to the [M+H]~+ adduct ion, characteristically showed a significant (usually 100% abundance) dimer adduct [2M+H]~+ that is not observed in the MS of the parent PAs. A total of 20 compounds were identified or tentatively characterized based on their mass spectra and possible biosynthetic pathways. Sixteen constituents were reported for the first time from G. segetum and tetrahydrosenecionine has not been previously reported as a natural product.
4. A novel, rapid and sensitive MEKC method was developed for the separation and determination of two hepatotoxic pyrrolizidine alkaloids in G. segetum within 8 min. The optimal running buffer containing 35 mM lauric acid, 120 mM Tris and 20% methanol (v/v) was employed. Linearity of the method was excellent with correlation coefficients (R~2) in the range of 0.9916-0.9939 when the concentration of PAs varied from 3.1 to 200μg/ml. Limit of detection of the two PAs was 1.0μg/ml. Compared with traditional SDS/inorganic bases system, this method provided high efficiencies, on account of its low ionic strength and therefore low conductivity. This method was suit for the quality control of Jusanqi.
5. A novel, rapid and high-sensitivity CZE-MS method was developed for the simultaneous determination of hepatotoxic pyrrolizidine alkaloids and N-oxides. The optimal running buffer containing 20 mM ammonium acetate, 1% formic acid and 5% methanol (v/v) was employed. Field-amplified sample stacking with electromigration-injection (FASS-EMI) was used for the on-line concentration of the alkaloids. This online preconcentration strategy resulted in sensitivity enhancement factors 30-fold for PAs and 200-fold for PANOs. The LOD was 0.01 ng/ml for the two PAs and was 0.1 ng/ml for the two PANOs. The method is suited to determination of trace amount PAs and PANOs in TCM.
6. The method of HPLC-ELSD for the analysis of contents of D-fructose, D-glucose, sucrose and maltose in Shenmai injection was established. Saccharides were separated by NH_2 column and the mobile phase was acetonitrile-water. Linearity of the method was excellent with correlation coefficients (R~2) in the range of 0.9983-0.9992 when the concentration of saccharides varied from 0.025 to 1.000 mg/ml. The total saccharide in Shenmai injection was also determined using Phenylhydrate-sulfuric acid and Freeze Drying methods. Furthermore, these three methods were compared seriously.
引文
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