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综述植物化学成分及其代谢物的定性和定量分析.doc

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Recent developments in qualitative and quantitative analysis of phytochemical constituents and their metabolites using liquid chromatography–mass spectrometry Haifeng Wua, , Jian Guob, , Shilin Chena, , Xin Liuc, , Yan Zhoud, , Xiaopo Zhanga, , Xudong Xua, , a Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100193, PR China b Department of DMPK, AstraZeneca Pharmaceuticals, 35 Gatehouse Drive, Waltham, MA 02451, USA c Beijing Entry-Exit Inspection and Quarantine Bureau, Beijing 100026, PR China d Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, PR China Corresponding author at: Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences and Peking Union Medical College, No.151, Malianwa North Road, Haidian District, Beijing 100193, PR China. Tel.: +86 10 5783 3296; fax: +86 10 5783 3296. Received 14 May 2012 Revised 30 August 2012 Accepted 2 September 2012 Available online 11 September 2012 http://dx.doi.org/10.1016/j.jpba.2012.09.004, How to Cite or Link Using DOI Permissions & Reprints View full text Purchase$31.50 1. Introduction 2. Qualitative analysis 3. Quantitative analysis 4. Application of LC–MS in fingerprinting analysis 5. Conclusions Acknowledgments References Abstract Over the past few years, the applications of liquid chromatography coupled with mass spectrometry (LC–MS) in natural product analysis have been dramatically growing because of the increasingly improved separation and detection capabilities of LC–MS instruments. In particular, novel high-resolution hybrid instruments linked to ultra-high-performance LC and the hyphenations of LC–MS with other separation or analytical techniques greatly aid unequivocal identification and highly sensitive quantification of natural products at trace concentrations in complex matrices. With the aim of providing an up-to-date overview of LC–MS applications on the analysis of plant-derived compounds, papers published within the latest years (2007–2012) involving qualitative and quantitative analysis of phytochemical constituents and their metabolites are summarized in the present review. After briefly describing the general characteristics of natural products analysis, the most remarkable features of LC–MS and sample preparation techniques, the present paper mainly focuses on screening and characterization of phenols (including flavonoids), alkaloids, terpenoids, steroids, coumarins, lignans, and miscellaneous compounds in respective herbs and biological samples, as well as traditional Chinese medicine (TCM) prescriptions using tandem mass spectrometer. Chemical fingerprinting analysis using LC–MS is also described. Meanwhile, instrumental peculiarities and methodological details are accentuated. Keywords Liquid chromatography; Mass spectrometry; Medicinal plants; Traditional Chinese medicine; Fingerprinting 抽象在过去的几年中，液相色谱与质谱联用（LC-MS）在天然产物分析的应用都得到了显着增长，因为日益提高的分离和检测能力的LC-MS仪器。特别是，新颖的高分辨率混合工具与其他分离或分析技术链接到超高性能LC的LC-MS和断字大大有助于在复杂基质中的微量浓度的明确识别和天然产品的高度敏感的定量。提供最新的植物性化合物的分析概述LC-MS应用的目的，论文发表在最近几年（2007-2012年），涉及的植物化学成分及其代谢物的定性和定量分析总结在本次审查中。在简要说明天然产物的分析，最显着的特点LC-MS和样品制备技术的一般特点，本论文主要集中在酚类物质（包括类黄酮），生物碱，萜类化合物，类固醇，香豆素，木脂素类化合物的筛选和鉴定，和杂项在各自的草药化合物和生物样品，以及中国传统医学（中医）处方使用串联质谱仪。化学指纹分析用LC-MS也被描述。同时，仪器的特点和方法的细节突出。 Figures and tables from this article: Fig. 1.Chemical structures of caged xanthones (1–15) identified from G. hanburyi. Reproduced with permission from [89]. 氧杂蒽酮的化学结构（1-15）确定 Figure options View in workspace Fig. 2.UHPLC–MS chromatograms of the standard xanthones and the crude extracts of G. hanburyi. (A) UHPLC chromatograms of 12 standard xanthones, (B) TIC of the 12 standard xanthones, (C) UHPLC chromatograms of the crude extracts of G. hanburyi, (D) TIC of the crude extracts of G. hanburyi. 。2。UHPLC-MS色谱图的标准呫吨酮和G. hanburyi粗提物中。（A）（B）UHPLC色谱图的12个标准氧杂蒽酮，TIC的12个标准氧杂蒽酮（C）UHPLC色谱G. hanburyi粗提物中，（D）议会的粗提物的G. hanburyi。 Reproduced with permission from [89]. Figure options View in workspace Fig. 3.(A) MS/MS spectra of isogambogenin (13) of selected [M+H]+ at m/z 615, (B) MS/MS/MS spectra of selected ion at m/z 491 from m/z 615, (C) MS/MS spectra of isomorellinol (14) of selected [M+H]+ at m/z 547, (D) MS/MS/MS spectra of selected ion at m/z 461 from m/z 547, (E) MS/MS spectra of compound 15 of selected [M+H]+ at m/z 545, (F) MS/MS/MS spectra of selected ion at m/z 461 from m/z 545 (collision energy at 30eV). 图。3。（A）MS /，MS谱isogambogenin（13）选定的[M+ H] + m / z为615，（B）选择离子从m / z615，m / z为491 MS / MS / MS谱（C）MS / MS，光谱isomorellinol（14）选择[M+ H] + m / z为547（D）MS / MS / MS谱的选择离子为m / z461 M / Z547，（E）MS/ MS谱的化合物15，所选的[M + H]+为m/ z545（F）MS / MS/ MS谱图，从m / z545（碰撞能量30 eV的选择离子为m / z461）。 Reproduced with permission from [89]. Figure options View in workspace Fig. 4.Proposed fragment pathways of [M+H]+ for: (A) isogambogenin (13), (B) isomorellinol (14), (C) 15. Reproduced with permission from [89]. Figure options View in workspace Fig. 5.HSCCC chromatogram of gamboge extract (190mg). Fraction I (17.26mg), fr. II (5.48mg), fr. III (3.81mg), fr. IV (3.56mg), fr. V (7.66mg), fr. VI (3.21mg), fr. VII (8.21mg), fr. VIII (35.25mg), fr. IX (76.78mg), fr. X (6.04mg), fr. XI (4.34mg). Reproduced with permission from [92]. 图。4。已提议片段途径的[M + H]+为：（A）isogambogenin（13），（B）isomorellinol（14），（C）15。转载许可[89]。 Figure options View in workspace Fig. 6.Scheme of the HPLC on-line coupled to ESI-MS and DPPH assay. The arrows indicate flow directions. 图。6。计划的HPLC上线耦合到：ESI-MS法和DPPH。箭头表示流动方向。 Reproduced with permission from [95]. Figure options View in workspace Fig. 7.The overview of the NMR/LC–MS parallel dynamic spectroscopy (NMR/LC–MS PDS) combined with an uncompleted separation strategy for simultaneous structure identification of natural products in crude extract. 图。 7。未完成的同时进行结构鉴定天然产物粗提物中分离策略，结合NMR/ LC-MS，并行动态光谱仪（NMR / LC-MS PDS）的概述。 Reproduced with permission from [96]. Figure options View in workspace Fig. 8.Proposed metabolic pathways for human liver phase 1 metabolism of isoliquiritigenin. 图。8。建议第1阶段人类肝脏代谢，异甘草素的代谢途径。 Reproduced with permission from [100]. Figure options View in workspace Fig. 9.The schematic diagram of VEGFR-CMC-on-line-LC–MS system. UV: ultraviolet detector; DAD/MS: diode array detector/mass spectrometer detector; 1D CMC column: the VEGFR-CMC column playing as the first dimensional column. 2D analytical column: the VP-ODS column playing as the second dimensional column. 图。 9。VEGFR-CMC-线LC-MS系统的示意图。 UV：紫外检测器，DAD / MS：二极管阵列检测/质谱法等检测;一维CMC柱中：VEGFR-军委纵队打的第一维列。二维分析柱：VP-ODS柱打的第二维列。 Reproduced with permission from [109]. Figure options View in workspace Fig. 10.Framework for high-throughput screening of cardio-protective compounds from medicinal plant extracts. 。10。从药用植物提取物的保护心血管的化合物的高通量筛选的框架。 Reproduced with permission from [155]. Figure options View in workspace Fig. 11.UHPLC–QTOF base peak intensity (BPI) chromatograms of six Meconopsis species for identification: (a–f) BPI of ESI (+) TOF-MS from M. torquata; M. racemosa; M. integrifolia; M. quintuplinervia; M. betonicifolia; M. horridula. 图。 11。UHPLC-QTOF基峰强度（BPI）色谱绿绒蒿物种识别：（A-F）BPI的ESI（+）TOF-MS从M. torquata; M.鹃，M. integrifolia，M. quintuplinervia，; M.betonicifolia; M. horridula。 Reproduced with permission from [175]. Figure options View in workspace Fig. 12.Structures assigned in the extracts of Meconopsis species. 图。 12。绿绒蒿属物种的提取物中分配的结构。 Reproduced with permission from [175]. Figure options View in workspace