基于HPLC-Q-TOF/MS和GC/MS的香丹注射液化学成分分析
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摘要
目的基于HPLC-Q-TOF/MS和GC/MS法分析香丹注射液的化学成分。方法水溶性成分分析采用Agilent TCC18色谱柱(250 mm×4. 6 mm,5μm);流动相0. 05%甲酸水-甲醇,梯度洗脱;柱温30℃;电喷雾离子源正负离子模式下对色谱流出物进行质谱检测,利用对照品、二级质谱信息及文献对各主要色谱峰进行归属;挥发油分析采用HP-5MS毛细管色谱柱(30 m×0. 25 mm,0. 25μm);程序升温,进样口温度260℃;体积流量1. 5 m L/min;进样量1μL;分流比1∶1; EI离子源,通过标准谱库检索并结合文献对主要色谱峰进行鉴定。结果香丹注射液中共鉴定出53个水溶性成分和9个挥发性成分。结论该方法准确稳定,重复性好,可用于香丹注射液的成分分析。
引文
[1]李斐,孟运莲.香丹注射液对大鼠脑缺血再灌注损伤的保护作用[J].中国现代药物应用,2010,4(1):25-27.
[2]李淑英.香丹注射液对气滞血瘀证疗效与安全性再评价[J].中国实验方剂学杂志,2012,18(21):318-320.
[3]尹永芹,朱俊访,沈志滨,等.神经网络分析香丹注射液抗心肌缺血有效成分的谱效相关性研究[J].中草药,2009,40(8):1284-1287.
[4]穆象山,张强,房信胜,等. HPLC-DAD同时测定香丹注射液中7种丹参酚酸类成分[J].中国中医药信息杂志,2012,19(12):56-58.
[5]袁继承,尹永芹,沈志滨,等. HPLC法测定香丹注射液中丹参素、原儿茶醛、咖啡酸、迷迭香酸、丹酚酸B和丹酚酸A[J].中草药,2009,40(S1):128-131.
[6] Xia Y Y,Liu F L,Feng F,et al. Characterization,quantitation and similarity evaluation of Codonopsis lanceolata from different regions in China by HPLC-Q-TQF-MS and chemometrics[J].J Food Compos Anal,2017,62:134-142.
[7] Zhai W Y,Liu J H,Liu Q,et al. Rapid identification and global characterization of multiple constituents from the essential oil of Cortex Dictamni based on GC-MS[J]. J Sep Sci,2017,40(12):2671-2681.
[8] Kang H J,Yang H J,Kim M J,et al. Metabolomic analysis of meju during fermentation by ultra performance liquid chromatography-quadrupole-time of flight mass spectrometry(UPLC-QTOF MS)[J]. Food Chem,2011,127(3):1056-1064.
[9] Calderón-Santiago M,Priego-Capote F,Jurado-Gámez B,et al.Optimization study for metabolomics analysis of human sweat by liquid chromatography-tandem mass spectrometry in high resolution mode[J]. J Chromatogr A,2014,1333:70-78.
[10] Liu A H,Guo H,Ye M,et al. Detection,characterization and identification of phenolic acids in Danshen using high-performance liquid chromatography with diode array detection and electrospray ionization mass spectrometry[J]. J Chromatogr A,2007,1161(1):170-182.
[11] Zeng G F,Xiao H B,Liu J X,et al. Identication of phenolic constituents in Radix Salvia miltiorrhizae by liquid chromatography/electrosprayionization mass spectrometry[J]. Rapid Commun Mass Sp,2006,20(3):499-506.
[12] Liu M H,Tong X,Wang J Y,et al. Rapid separation and identification of multiple constituents in traditional Chinese medicine formula Shenqi Fuzheng Injection by ultra-fast liquid chromatography combined with quadrupole-time-of-flight mass spectrometry[J]. J Pharmaceut Biomed Anal,2013,74:141-155.
[13] Lu Z W,Wang Q,Wang M L,et al. Using UHPLC Q-Trap/MS as a complementary technique to in-depth mine UPLC Q-TOF/MS data for identifying modified nucleosides in urine[J].J Chromatogr B,2017,1051:108-117.
[14] Yang G,Zhang H,Chen T M,et al. Metabolic analysis of osteoarthritis subchondral bone based on UPLC/Q-TOF-MS[J].Anal Bioanal Chem,2016,408(16):4275-4286.
[15] Zhu B J,Cao H T,Sun L M,et al. Metabolomics-based mechanisms exploration of Huang-Lian Jie-Du decoction on cerebral ischemia via UPLC-Q-TOF/MS analysis on rat serum[J]. J Ethnopharmacol,2018,216:147-156.
[16] Zhen J,Villaniab T S,Guo Y,et al. Phytochemistry,antioxidant capacity,total phenolic content and anti-inflammatory activity of Hibiscus sabdariffa leaves[J]. Food Chem,2016,190:673-680.
[17] Parejo I,Jauregui O,Sánchez-Rabaneda F S,et al. Separation and characterization of phenolic compounds in fennel(Foeniculum vulgare)using liquid chromatography-negative electrospray ionization tandem mass spectrometry[J]. J Agric Food Chem,2004,52(12):3679-3687.
[18] Zhang Q Q,Dong X,Liu X G,et al. Rapid separation and identification of multiple constituents in Danhong Injection by ultra-high performance liquid chromatography coupled to electrospray ionization quadrupole time-of-flight tandem mass spectrometry[J]. Chin J Nat Med,2016,14(2):147-160.
[19] Hao M L,Beta T. Qualitative and quantitative analysis of the major phenolic compounds as antioxidants in barley and flaxseed hulls using HPLC/MS/MS[J]. J Sci Food Agric,2012,92(10):2062-2068.
[20] Gruz J,Novák O,Strnad M. Rapid analysis of phenolic acids in beverages by UPLC-MS/MS[J]. Food Chem,2008,111(3):789-794.
[21] Liu A H,Lin Y H,Yang M,et al. Development of the fingerprints for the quality of the roots of Salvia miltiorrhiza and its related preparations by HPLC-DAD and LC-MSn[J]. J Chromatogr B,2007,846(1-2):32-41.
[22]王少敏,胡青,季申. GC/MS法和UPLC/Q-TOF-MS法研究丹香冠心注射液中的有效成分[J].中成药,2012,34(1):78-84.
[23] Guo W W,Beta T. Phenolic acid composition and antioxidant potential of insoluble and soluble dietary fibre extracts derived from select whole-grain cereals[J]. Food Res Int,2013,51(2):518-525.
[24] Tang J F,Li W X,Tan X J,et al. A novel and improved UHPLC-QTOF/MS method for the rapid analysis of the chemical constituents of Danhong injection[J]. Anal Methods,2016,8:2904-2914.
[25] Chen H,Zhang X M,Wang X M,et al. Qualitative analysis and simultaneous quantification of phenolic compounds in the aerial parts of Salvia miltiorrhiza by HPLC-DAD and ESI/MSn[J]. Phytochem Analysis,2011,22(3):247-257.
[26] Wang J,Wei N,Zhao H Z,et al. Global chemome study by LC coupled with DAD and ESI-Q-TOF MS of a composite traditional chinese medicine Qishenyiqi Dropping Pills[J]. Chromatographia,2010,72(5-6):431-440.
[27] Chen X F,Lou Z Y,Zhang H,et al. Identification of multiple components in Guanxinning injection using hydrophilic interaction liquid chromatography/time-of-flight mass spectrometry and reversed-phase liquid chromatography/time-offlight mass spectrometry[J]. Rapid Commun Mass Spectrom,2011,25(11):1661-1674.
[28] Zhao X,Yang D H,Xu F,et al. The in vivo absorbed constituents and metabolites of Danshen decoction in rats identified by HPLC with electrospray ionization tandem ion trap and time-offlight mass spectrometry[J]. Biomed Chromatogr,2015,29:285-304.
[29] Persson X M T,Bachnio-Zabielska A U,Jensen M D. Rapid measurement of plasma free fatty acid concentration and isotopic enrichment using LC/MS[J]. J Lipid Res,2010,51(9):2761-2765.
[30] Rameshkumar A,Sivasudha T,Jeyadevi R,et al. Profiling of phenolic compounds using UPLC–Q-TOF-MS/MS and nephroprotective activity of Indian green leafy vegetable Merremia emarginata(Burm. f.)[J]. Food Res Int,2013,50(1):94-101.
[31] Lv X J,Sun Z,Wang P L,et al. Chemical profiling and quantification of Dan-Deng-Tong-Nao-capsule using ultra high performance liquid chromatography coupled with high resolution hybrid quadruple-orbitrap mass spectrometry[J]. J Pharmaceut Biomed Anal,2018,148:189-194.
[32]刘洪玲. GC-MS法分析降香挥发油化学成分[J].中成药,2009,31(6):915-917.
[33] Zheng L H,Wang L,Guo X,et al. Essential oil composition from the seeds of Dalbergia odorifera T. Chen grown in Hainan,China[J]. J Food Agric Environ,2011,9(3&4):26-28
[34]李天略,纪明慧,舒火明,等.微波辅助提取-气相色谱-质谱法测定花梨木挥发油成分[J].理化检验(化学分册),2009,45(8):907-909.
[35]郭丽冰,王蕾,廖华卫.降香CO2超临界萃取物的GC-MS分析[J].广东药学院学报,2007,23(1):12-13.
[36] Li Z F,Wang Y W,Ouyang H,et al. A novel dereplication strategy for the identification of two new trace compounds in the extract of Gastrodia elata using UHPLC/Q-TOF-MS/MS[J]. J Chromatogr B,2015,988:45-52.
[37] Zhu T T,Liu X,Wang X L,et al. Profiling and analysis of multiple compounds in rhubarb decoction after processing by wine steaming using UHPLC-Q-TOF-MS coupled with multiple statistical strategies[J]. J Sep Sci,2016,39(15):3081-3090.
[38] Yuan L,Zhang Z Z,Hou Z G,et al. Rapid classification and identification of complex chemical compositions in traditional Chinese medicine based on UPLC-Q-TOF/MS coupled with data processing techniques using the Ku Die Zi injection as an example[J]. Anal Methods,2015,7:5210-5217.
[39] Santiva1ez-Veliz M,Moreno-Viguri E,Pérez-Silanes S,et al.Development,validation and application of a GC-MS method for the simultaneous detection and quantification of neutral lipid species in Trypanosoma cruzi[J]. J Chromatogr B,2017,1061-1062:225-232.
[40]姚卫峰,刘卉,陈汀,等.基于UPLC-TOF-MS基峰强度色谱图轮廓的香丹注射液快速质量分析[J].中国药房,2010,21(47):4468-4470.
[41]刘海燕,范玫玫,何明珍,等.降香挥发油的研究进展[J].中草药,2009,40(11):附3-5.
[42]赵祥升,魏建和,甘炳春,等. GC法同时测定降香中4个成分的含量[J].药物分析杂志,2012,32(3):395-399.
[43]张波,李佳,刘红燕,等.降香挥发油的研究进展[J].中国药师,2014,17(8):1403-1406.
[2]李淑英.香丹注射液对气滞血瘀证疗效与安全性再评价[J].中国实验方剂学杂志,2012,18(21):318-320.
[3]尹永芹,朱俊访,沈志滨,等.神经网络分析香丹注射液抗心肌缺血有效成分的谱效相关性研究[J].中草药,2009,40(8):1284-1287.
[4]穆象山,张强,房信胜,等. HPLC-DAD同时测定香丹注射液中7种丹参酚酸类成分[J].中国中医药信息杂志,2012,19(12):56-58.
[5]袁继承,尹永芹,沈志滨,等. HPLC法测定香丹注射液中丹参素、原儿茶醛、咖啡酸、迷迭香酸、丹酚酸B和丹酚酸A[J].中草药,2009,40(S1):128-131.
[6] Xia Y Y,Liu F L,Feng F,et al. Characterization,quantitation and similarity evaluation of Codonopsis lanceolata from different regions in China by HPLC-Q-TQF-MS and chemometrics[J].J Food Compos Anal,2017,62:134-142.
[7] Zhai W Y,Liu J H,Liu Q,et al. Rapid identification and global characterization of multiple constituents from the essential oil of Cortex Dictamni based on GC-MS[J]. J Sep Sci,2017,40(12):2671-2681.
[8] Kang H J,Yang H J,Kim M J,et al. Metabolomic analysis of meju during fermentation by ultra performance liquid chromatography-quadrupole-time of flight mass spectrometry(UPLC-QTOF MS)[J]. Food Chem,2011,127(3):1056-1064.
[9] Calderón-Santiago M,Priego-Capote F,Jurado-Gámez B,et al.Optimization study for metabolomics analysis of human sweat by liquid chromatography-tandem mass spectrometry in high resolution mode[J]. J Chromatogr A,2014,1333:70-78.
[10] Liu A H,Guo H,Ye M,et al. Detection,characterization and identification of phenolic acids in Danshen using high-performance liquid chromatography with diode array detection and electrospray ionization mass spectrometry[J]. J Chromatogr A,2007,1161(1):170-182.
[11] Zeng G F,Xiao H B,Liu J X,et al. Identication of phenolic constituents in Radix Salvia miltiorrhizae by liquid chromatography/electrosprayionization mass spectrometry[J]. Rapid Commun Mass Sp,2006,20(3):499-506.
[12] Liu M H,Tong X,Wang J Y,et al. Rapid separation and identification of multiple constituents in traditional Chinese medicine formula Shenqi Fuzheng Injection by ultra-fast liquid chromatography combined with quadrupole-time-of-flight mass spectrometry[J]. J Pharmaceut Biomed Anal,2013,74:141-155.
[13] Lu Z W,Wang Q,Wang M L,et al. Using UHPLC Q-Trap/MS as a complementary technique to in-depth mine UPLC Q-TOF/MS data for identifying modified nucleosides in urine[J].J Chromatogr B,2017,1051:108-117.
[14] Yang G,Zhang H,Chen T M,et al. Metabolic analysis of osteoarthritis subchondral bone based on UPLC/Q-TOF-MS[J].Anal Bioanal Chem,2016,408(16):4275-4286.
[15] Zhu B J,Cao H T,Sun L M,et al. Metabolomics-based mechanisms exploration of Huang-Lian Jie-Du decoction on cerebral ischemia via UPLC-Q-TOF/MS analysis on rat serum[J]. J Ethnopharmacol,2018,216:147-156.
[16] Zhen J,Villaniab T S,Guo Y,et al. Phytochemistry,antioxidant capacity,total phenolic content and anti-inflammatory activity of Hibiscus sabdariffa leaves[J]. Food Chem,2016,190:673-680.
[17] Parejo I,Jauregui O,Sánchez-Rabaneda F S,et al. Separation and characterization of phenolic compounds in fennel(Foeniculum vulgare)using liquid chromatography-negative electrospray ionization tandem mass spectrometry[J]. J Agric Food Chem,2004,52(12):3679-3687.
[18] Zhang Q Q,Dong X,Liu X G,et al. Rapid separation and identification of multiple constituents in Danhong Injection by ultra-high performance liquid chromatography coupled to electrospray ionization quadrupole time-of-flight tandem mass spectrometry[J]. Chin J Nat Med,2016,14(2):147-160.
[19] Hao M L,Beta T. Qualitative and quantitative analysis of the major phenolic compounds as antioxidants in barley and flaxseed hulls using HPLC/MS/MS[J]. J Sci Food Agric,2012,92(10):2062-2068.
[20] Gruz J,Novák O,Strnad M. Rapid analysis of phenolic acids in beverages by UPLC-MS/MS[J]. Food Chem,2008,111(3):789-794.
[21] Liu A H,Lin Y H,Yang M,et al. Development of the fingerprints for the quality of the roots of Salvia miltiorrhiza and its related preparations by HPLC-DAD and LC-MSn[J]. J Chromatogr B,2007,846(1-2):32-41.
[22]王少敏,胡青,季申. GC/MS法和UPLC/Q-TOF-MS法研究丹香冠心注射液中的有效成分[J].中成药,2012,34(1):78-84.
[23] Guo W W,Beta T. Phenolic acid composition and antioxidant potential of insoluble and soluble dietary fibre extracts derived from select whole-grain cereals[J]. Food Res Int,2013,51(2):518-525.
[24] Tang J F,Li W X,Tan X J,et al. A novel and improved UHPLC-QTOF/MS method for the rapid analysis of the chemical constituents of Danhong injection[J]. Anal Methods,2016,8:2904-2914.
[25] Chen H,Zhang X M,Wang X M,et al. Qualitative analysis and simultaneous quantification of phenolic compounds in the aerial parts of Salvia miltiorrhiza by HPLC-DAD and ESI/MSn[J]. Phytochem Analysis,2011,22(3):247-257.
[26] Wang J,Wei N,Zhao H Z,et al. Global chemome study by LC coupled with DAD and ESI-Q-TOF MS of a composite traditional chinese medicine Qishenyiqi Dropping Pills[J]. Chromatographia,2010,72(5-6):431-440.
[27] Chen X F,Lou Z Y,Zhang H,et al. Identification of multiple components in Guanxinning injection using hydrophilic interaction liquid chromatography/time-of-flight mass spectrometry and reversed-phase liquid chromatography/time-offlight mass spectrometry[J]. Rapid Commun Mass Spectrom,2011,25(11):1661-1674.
[28] Zhao X,Yang D H,Xu F,et al. The in vivo absorbed constituents and metabolites of Danshen decoction in rats identified by HPLC with electrospray ionization tandem ion trap and time-offlight mass spectrometry[J]. Biomed Chromatogr,2015,29:285-304.
[29] Persson X M T,Bachnio-Zabielska A U,Jensen M D. Rapid measurement of plasma free fatty acid concentration and isotopic enrichment using LC/MS[J]. J Lipid Res,2010,51(9):2761-2765.
[30] Rameshkumar A,Sivasudha T,Jeyadevi R,et al. Profiling of phenolic compounds using UPLC–Q-TOF-MS/MS and nephroprotective activity of Indian green leafy vegetable Merremia emarginata(Burm. f.)[J]. Food Res Int,2013,50(1):94-101.
[31] Lv X J,Sun Z,Wang P L,et al. Chemical profiling and quantification of Dan-Deng-Tong-Nao-capsule using ultra high performance liquid chromatography coupled with high resolution hybrid quadruple-orbitrap mass spectrometry[J]. J Pharmaceut Biomed Anal,2018,148:189-194.
[32]刘洪玲. GC-MS法分析降香挥发油化学成分[J].中成药,2009,31(6):915-917.
[33] Zheng L H,Wang L,Guo X,et al. Essential oil composition from the seeds of Dalbergia odorifera T. Chen grown in Hainan,China[J]. J Food Agric Environ,2011,9(3&4):26-28
[34]李天略,纪明慧,舒火明,等.微波辅助提取-气相色谱-质谱法测定花梨木挥发油成分[J].理化检验(化学分册),2009,45(8):907-909.
[35]郭丽冰,王蕾,廖华卫.降香CO2超临界萃取物的GC-MS分析[J].广东药学院学报,2007,23(1):12-13.
[36] Li Z F,Wang Y W,Ouyang H,et al. A novel dereplication strategy for the identification of two new trace compounds in the extract of Gastrodia elata using UHPLC/Q-TOF-MS/MS[J]. J Chromatogr B,2015,988:45-52.
[37] Zhu T T,Liu X,Wang X L,et al. Profiling and analysis of multiple compounds in rhubarb decoction after processing by wine steaming using UHPLC-Q-TOF-MS coupled with multiple statistical strategies[J]. J Sep Sci,2016,39(15):3081-3090.
[38] Yuan L,Zhang Z Z,Hou Z G,et al. Rapid classification and identification of complex chemical compositions in traditional Chinese medicine based on UPLC-Q-TOF/MS coupled with data processing techniques using the Ku Die Zi injection as an example[J]. Anal Methods,2015,7:5210-5217.
[39] Santiva1ez-Veliz M,Moreno-Viguri E,Pérez-Silanes S,et al.Development,validation and application of a GC-MS method for the simultaneous detection and quantification of neutral lipid species in Trypanosoma cruzi[J]. J Chromatogr B,2017,1061-1062:225-232.
[40]姚卫峰,刘卉,陈汀,等.基于UPLC-TOF-MS基峰强度色谱图轮廓的香丹注射液快速质量分析[J].中国药房,2010,21(47):4468-4470.
[41]刘海燕,范玫玫,何明珍,等.降香挥发油的研究进展[J].中草药,2009,40(11):附3-5.
[42]赵祥升,魏建和,甘炳春,等. GC法同时测定降香中4个成分的含量[J].药物分析杂志,2012,32(3):395-399.
[43]张波,李佳,刘红燕,等.降香挥发油的研究进展[J].中国药师,2014,17(8):1403-1406.