生物碱的高效液相色谱分离分析与纯化制备研究进展
|
摘要
生物碱是天然产物中药用活性较好的一类化合物,在分离科学与技术领域,生物碱的分离一直是一个研究热点和难点问题。近年来,随着高效液相色谱填料和分离方法的发展,生物碱的分离分析和纯化制备有了长足的进步。该文主要针对碱性化合物的峰形拖尾问题,综述了高效液相色谱理论的发展和色谱分离技术的进步,以及近年来新型色谱填料和分离方法在生物碱分离分析和纯化制备中的应用,并对其前景进行了展望。
Alkaloids are a class of natural compounds with good pharmacological properties.In the field of separation science and technology,alkaloid separation has always been a hot and difficult problem.In recent years,with the development of high performance liquid chromatography(HPLC) materials and separation methods,great progresses in alkaloid analysis and preparation have been achieved.In this article,the theoretical development and technological advances with respect to peak tailing problems of basic compounds are summarized,and the applications of HPLC in natural alkaloid analysis and preparation are discussed.The further development of HPLC separation on alkaloids is also looked forward.
Alkaloids are a class of natural compounds with good pharmacological properties.In the field of separation science and technology,alkaloid separation has always been a hot and difficult problem.In recent years,with the development of high performance liquid chromatography(HPLC) materials and separation methods,great progresses in alkaloid analysis and preparation have been achieved.In this article,the theoretical development and technological advances with respect to peak tailing problems of basic compounds are summarized,and the applications of HPLC in natural alkaloid analysis and preparation are discussed.The further development of HPLC separation on alkaloids is also looked forward.
引文
[1] Wishart D S,Knox C,Guo A C,Shrivastava S,Hassanali M,Stothard P,Chang Z,Woolsey J.Nucleic Acids Res.,2006,34(S1):668-672.
[2] Cordell G A,Quinn-Beattie M L,Farnsworth N R.Phytother.Res.,2001,15(3):183-205.
[3] Cushnie T P,Cushnie B,Lamb A J.Int.J.Antimicrob.Ag.,2014,44(5):377-386.
[4] Amirkia V,Heinrich M.Phytochem.Lett.,2014,10(16):xlviii-liii.
[5] Shi X Z,Li G K,Liang Z,Guo Z M,Ye M L,Yan J Y,Xu G W.Chem.Bull.(石先哲,李攻科,梁振,郭志谋,叶明亮,闫竞宇,许国旺.化学通报),2014,77(7):720-730.
[6] Li R P,Huang J X.Process.Chem.(李瑞萍,黄骏雄.化学进展),2004,16(2):273-283.
[7] Sticher O.Nat.Prod.Rep.,2008,25(3):517-554.
[8] Bucar F,Wube A,Schmid M.Nat.Prod.Rep.,2013,30(4):525-545.
[9] Mcchesney J D,Rodenburg D L.Curr.Opin.Biotech.,2014,25(1):111-113.
[10] Zhang H,Wang S S,Li W,Wang Y Q,Xue X Y,Liang X M.World Sci.Technol.(张慧,王世盛,李伟,王亚琴,薛兴亚,梁鑫淼.世界科学技术),2009,11(2):253-256.
[11] Jin H L,Zhao J Q,Zhou W J,Shen A J,Yang F,Liu Y F,Guo Z M,Zhang X L,Tao Y D,Peng X J,Liang X M.Rsc.Adv.,2015,5(76):62134-62141.
[12] Zhao Y Y,Guo Z M,Zhang X L,Liang X M,Zhang Y K.J.Sep.Sci.,2010,33(9):1224-1230.
[13] Li X L,Huang R Q,Liu Y F,Jin H L,Wan H H,Zhao J Q,Zhao W J,Liang X M.Anal.Methods,2014,6(14):5183-5190.
[14] Li W,Wang S S,Feng J T,Xiao Y S,Xue X Y,Zhang H,Wang Y Q,Liang X M.Magn.Reson.Chem.,2009,47(10):902-908.
[15] Mccalley D V.J.Chromatogr.A,2010,1217(6):858-880.
[16] Zhang J,Jin Y,Liu Y F,Xiao Y S,Feng J T,Xue X Y,Zhang X L,Liang X M.J.Sep.Sci.,2009,32(9):1401-1406.
[17] Stadalius M A,Berus J S,Snyder L R.LC GC N.Am.,1988,6(6):494-500.
[18] Nawrocki J.J.Chromatogr.A,1997,779(1/2):29-71.
[19] Huang X J,Yang X L,Liu X L,Wang J D.Chem.Reagents(黄晓佳,杨新立,刘学良,王俊德.化学试剂),2001,23(2):77-81.
[20] O?sullivan G P,Scully N M,Glennon J D.Anal.Lett.,2010,43(10/11):1609-1629.
[21] Méndez A,Bosch E,Rosés M,Neue U D.J.Chromatogr.A,2003,986(1):33-44.
[22] Buckenmaier S M C,Mccalley D V,Euerby M R.Anal.Chem.,2002,74(18):4672-4681.
[23] H?gglund I,St?hlberg J.J.Chromatogr.A,1997,761(1/2):3-11.
[24] Neue U D,Wheat T E,Mazzeo J R,Mazza C B,Cavanaugh J Y,Xia F,Diehl D M.J.Chromatogr.A,2004,1030(1/2):123-134.
[25] Mccalley D V.Anal.Chem.,2006,78(8):2532-2538.
[26] Gritti F,Guiochon G.Anal.Chem.,2004,76(16):4779-4789.
[27] Gritti F,Guiochon G.J.Chromatogr.A,2005,1095(1/2):27-39.
[28] Gritti F,Guiochon G.Anal.Chem.,2005,77(4):1020-1030.
[29] Davies N H,Euerby M R,Mccalley D V.J.Chromatogr.A,2006,1119(1):11-19.
[30] Liu L,Fan Z C,Zhang Z Q.Chin.J.Pharm.Anal.(刘岚,范智超,张志琪.药物分析杂志),2010(2):236-239.
[31] Gritti F,Georges G.J.Chromatogr.A,2004,1033(1):43-55.
[32] Mccalley D V.Anal.Chem.,2003,75(14):3404-3410.
[33] Liu X X,Pan Y,Wang L,Liu L J.Chin.Phar.J.(刘学湘,潘扬,王丽,刘亮镜.中国药学杂志),2010,45(9):698-701.
[34] Wang Y,Tian M L,Bi W T,Row K H.Int.J.Mol.Sci.,2009,10(6):2591-2610.
[35] Cheng Y F,Walter T H,Lu Z L,Iraneta P,Alden B A,Gendreau C,Neue U D,Grassi J M,Carmody J L,O?gara J E,Fisk R P.LC GC N.Am.,2000,18(11):1162-1173.
[36] Davies N H,Euerby M R,Mccalley D V.J.Chromatogr.A,2008,1178(1/2):71-78.
[37] Wang C R,Guo Z M,Zhang J,Zeng J,Zhang X L,Liang X M.J.Sep.Sci.,2011,34(1):53-58.
[38] Fallas M M,Buckenmaier S M C,Mccalley D V.J.Chromatogr.A,2012,1235:49-59.
[39] Wang C R,Guo Z M,Long Z,Zhang X L,Liang X M.J.Chromatogr.A,2013,1281(6):60-66.
[40] Guo Z M,Wang C R,Liang T,Liang X M.J.Chromatogr.A,2010,1217(27):4555-4560.
[41] Gritti F,Guiochon G.J.Chromatogr.A,2014,1372:42-54.
[42] Flanagan R J,Harvey E J,Spencer E P.Forensic.Sci.Int.,2001,121(1/2):97-102.
[43] Long Z,Wang C R,Guo Z M,Zhang X L,Nordahl L,Liang X M.J.Chromatogr.A,2012,1256(18):67-71.
[44] Davies N H,Euerby M R,Mccalley D V.J.Chromatogr.A,2007,1138(1/2):65-72.
[45] Zou X,Fang Y N,Qu Z Y,Shi X,Liu X,Wang B,Chen M.J.Harbin Univ.Comm.:Nat.Sci.Ed.(邹翔,方月妮,曲中原,石鑫,刘欣,汪波,陈敏.哈尔滨商业大学学报:自然科学版),2016,32(3):257-260.
[46] Zhu Y L,Fang H H,Wei H Z,Liu S N,Duan Y Q,Gong M,Rao Y.Chin.J.Exp.Tradit.Med.Form.(朱益雷,方海红,魏惠珍,刘晟楠,段奕倩,龚明,饶毅.中国实验方剂学杂志),2016,(12):75-78.
[47] Lin H Y,Su C,Duan T X,Huang J M,Sun Y K,Wang Y,Ji J J,Dong J,Liu Y G.Mod.Chin.Med.(林宏英,苏畅,段天璇,黄建梅,孙毅坤,王玥,冀娇娇,董洁,刘永刚.中国现代中药),2015,17(3):208-211.
[48] Long Z,Guo Z M,Acworth I N,Liu X G,Jin Y,Liu X,Liu L,Liang L.Talanta,2016,151(5):239-244.
[49] Qing Z X,Liu X B,Wu H M,Cheng P,Liu Y S,Zeng J G.Anal.Methods,2015,7(5):1866-1871.
[50] Le P M,Mccooeye M,Windust A.Anal.Bioanal.Chem.,2013,405(13):4487-4498.
[51] Liu Q,Jiang S Y,Tian S J.Chin.J.Mod.Appl.Pharm.(刘琼,姜舜尧,田颂九.中国现代应用药学),2004,21(1):64-67.
[52] Long Z,Guo Z M,Xue X Y,Zhang X L,Nordahl L,Liang X M.Anal.Chim.Acta,2013,804:304-312.
[53] Taujenis L,Olsauskaite V,Padarauskas A.Acta Chromatogr.,2015,27(2):373-385.
[54] Zhuo R J,Wang L,Wang L X,Xiao H B,Cai S Q.Chin.J.Chrom.(卓荣杰,王莉,王龙星,肖红斌,蔡少青.色谱),2010,28(4):379-382.
[55] Long Z.The Analysis and Purification of Basic Compounds.Dalian:Dalian Institute of Chemical Physics,Chinese Academy of Sciences(龙珍.碱性化合物的色谱分离分析与分离纯化制备.大连:中国科学院大连化学物理研究所),2014.
[56] Huang J Y,Tong L,Ding L.Prog.Pharm.Sci.(黄竞怡,佟玲,丁黎.药学进展),2015,39(5):357-363.
[57] Wei X D,Shen H L,Wang L J,Meng Q Y,Liu W J.J.Anal.Methods Chem.,2016,Article ID 9752735.
[58] Zhang J C.Study on the Chromatographic Separation Method of Alkaloids in the Huperzia Serrata.Dalian:Dalian University of Technology(张敬彩.中药千层塔中生物碱成分的色谱分离方法研究.大连:大连理工大学),2013.
[59] Long Z,Guo Z M,Xue X Y,Zhang X,Liang X.J.Sep.Sci.,2013,36(24):3845-3852.
[60] Fang L,Liu Y Q,Yang B,Wang X.Huang L Q.J.Sep.Sci.,2011,34(19):2545-2558.
[61] Hu R L,Pan Y J.Trac-Trend.Anal.Chem.,2012,40:15-27.
[62] Niu L L,Xie Z S,Cai T X,Wu P,Xue P,Chen X L,Wu Z Y,Ito Y,Li F M,Yang F Q.J.Sep.Sci.,2011,34(9):987-994.
[63] Sun C L,Li J,Wang X,Duan W J,Zhang T Y,Ito Y.J.Chromatogr.A,2014,1370:156-161.
[64] Zhang Y,Wang C R,Wang L,Parks G S,Zhang X L,Guo Z M,Ke Y X,Li K W,Kim M K,Vo B,Borrelli E,Ge G B,Yang L,Wang Z W,Garcia-Fuster M J,Luo Z D,Liang X M,Civelli O.Curr.Biol.,2014,24(2):117-123.
[65] Zhang Y,Wang C R,Guo Z M,Zhang X L,Wang Z W,Liang X M,Civelli O.J.Ethnopharmacol.,2014,155(3):1597-1602.
[66] Long Z,Zhang Y,Guo Z M,Wang L,Xue X Y,Zhang X L,Wang S S,Wang Z W,Civelli O,Liang X M.Planta.Med.,2014,80(13):1124-1130.
[67] Du N N,Liu Y F,Zhang X L,Wang J X,Zhao J Q,He J,Zhou H,Mei L J,Liang X M.Sci.Rep.,2017,7:46067.
[68] Li K Y,Zhu W Y,Fu Q,Ke Y X,Jin Y,Liang X M.Analyst,2013,138(11):3313-3320.
[2] Cordell G A,Quinn-Beattie M L,Farnsworth N R.Phytother.Res.,2001,15(3):183-205.
[3] Cushnie T P,Cushnie B,Lamb A J.Int.J.Antimicrob.Ag.,2014,44(5):377-386.
[4] Amirkia V,Heinrich M.Phytochem.Lett.,2014,10(16):xlviii-liii.
[5] Shi X Z,Li G K,Liang Z,Guo Z M,Ye M L,Yan J Y,Xu G W.Chem.Bull.(石先哲,李攻科,梁振,郭志谋,叶明亮,闫竞宇,许国旺.化学通报),2014,77(7):720-730.
[6] Li R P,Huang J X.Process.Chem.(李瑞萍,黄骏雄.化学进展),2004,16(2):273-283.
[7] Sticher O.Nat.Prod.Rep.,2008,25(3):517-554.
[8] Bucar F,Wube A,Schmid M.Nat.Prod.Rep.,2013,30(4):525-545.
[9] Mcchesney J D,Rodenburg D L.Curr.Opin.Biotech.,2014,25(1):111-113.
[10] Zhang H,Wang S S,Li W,Wang Y Q,Xue X Y,Liang X M.World Sci.Technol.(张慧,王世盛,李伟,王亚琴,薛兴亚,梁鑫淼.世界科学技术),2009,11(2):253-256.
[11] Jin H L,Zhao J Q,Zhou W J,Shen A J,Yang F,Liu Y F,Guo Z M,Zhang X L,Tao Y D,Peng X J,Liang X M.Rsc.Adv.,2015,5(76):62134-62141.
[12] Zhao Y Y,Guo Z M,Zhang X L,Liang X M,Zhang Y K.J.Sep.Sci.,2010,33(9):1224-1230.
[13] Li X L,Huang R Q,Liu Y F,Jin H L,Wan H H,Zhao J Q,Zhao W J,Liang X M.Anal.Methods,2014,6(14):5183-5190.
[14] Li W,Wang S S,Feng J T,Xiao Y S,Xue X Y,Zhang H,Wang Y Q,Liang X M.Magn.Reson.Chem.,2009,47(10):902-908.
[15] Mccalley D V.J.Chromatogr.A,2010,1217(6):858-880.
[16] Zhang J,Jin Y,Liu Y F,Xiao Y S,Feng J T,Xue X Y,Zhang X L,Liang X M.J.Sep.Sci.,2009,32(9):1401-1406.
[17] Stadalius M A,Berus J S,Snyder L R.LC GC N.Am.,1988,6(6):494-500.
[18] Nawrocki J.J.Chromatogr.A,1997,779(1/2):29-71.
[19] Huang X J,Yang X L,Liu X L,Wang J D.Chem.Reagents(黄晓佳,杨新立,刘学良,王俊德.化学试剂),2001,23(2):77-81.
[20] O?sullivan G P,Scully N M,Glennon J D.Anal.Lett.,2010,43(10/11):1609-1629.
[21] Méndez A,Bosch E,Rosés M,Neue U D.J.Chromatogr.A,2003,986(1):33-44.
[22] Buckenmaier S M C,Mccalley D V,Euerby M R.Anal.Chem.,2002,74(18):4672-4681.
[23] H?gglund I,St?hlberg J.J.Chromatogr.A,1997,761(1/2):3-11.
[24] Neue U D,Wheat T E,Mazzeo J R,Mazza C B,Cavanaugh J Y,Xia F,Diehl D M.J.Chromatogr.A,2004,1030(1/2):123-134.
[25] Mccalley D V.Anal.Chem.,2006,78(8):2532-2538.
[26] Gritti F,Guiochon G.Anal.Chem.,2004,76(16):4779-4789.
[27] Gritti F,Guiochon G.J.Chromatogr.A,2005,1095(1/2):27-39.
[28] Gritti F,Guiochon G.Anal.Chem.,2005,77(4):1020-1030.
[29] Davies N H,Euerby M R,Mccalley D V.J.Chromatogr.A,2006,1119(1):11-19.
[30] Liu L,Fan Z C,Zhang Z Q.Chin.J.Pharm.Anal.(刘岚,范智超,张志琪.药物分析杂志),2010(2):236-239.
[31] Gritti F,Georges G.J.Chromatogr.A,2004,1033(1):43-55.
[32] Mccalley D V.Anal.Chem.,2003,75(14):3404-3410.
[33] Liu X X,Pan Y,Wang L,Liu L J.Chin.Phar.J.(刘学湘,潘扬,王丽,刘亮镜.中国药学杂志),2010,45(9):698-701.
[34] Wang Y,Tian M L,Bi W T,Row K H.Int.J.Mol.Sci.,2009,10(6):2591-2610.
[35] Cheng Y F,Walter T H,Lu Z L,Iraneta P,Alden B A,Gendreau C,Neue U D,Grassi J M,Carmody J L,O?gara J E,Fisk R P.LC GC N.Am.,2000,18(11):1162-1173.
[36] Davies N H,Euerby M R,Mccalley D V.J.Chromatogr.A,2008,1178(1/2):71-78.
[37] Wang C R,Guo Z M,Zhang J,Zeng J,Zhang X L,Liang X M.J.Sep.Sci.,2011,34(1):53-58.
[38] Fallas M M,Buckenmaier S M C,Mccalley D V.J.Chromatogr.A,2012,1235:49-59.
[39] Wang C R,Guo Z M,Long Z,Zhang X L,Liang X M.J.Chromatogr.A,2013,1281(6):60-66.
[40] Guo Z M,Wang C R,Liang T,Liang X M.J.Chromatogr.A,2010,1217(27):4555-4560.
[41] Gritti F,Guiochon G.J.Chromatogr.A,2014,1372:42-54.
[42] Flanagan R J,Harvey E J,Spencer E P.Forensic.Sci.Int.,2001,121(1/2):97-102.
[43] Long Z,Wang C R,Guo Z M,Zhang X L,Nordahl L,Liang X M.J.Chromatogr.A,2012,1256(18):67-71.
[44] Davies N H,Euerby M R,Mccalley D V.J.Chromatogr.A,2007,1138(1/2):65-72.
[45] Zou X,Fang Y N,Qu Z Y,Shi X,Liu X,Wang B,Chen M.J.Harbin Univ.Comm.:Nat.Sci.Ed.(邹翔,方月妮,曲中原,石鑫,刘欣,汪波,陈敏.哈尔滨商业大学学报:自然科学版),2016,32(3):257-260.
[46] Zhu Y L,Fang H H,Wei H Z,Liu S N,Duan Y Q,Gong M,Rao Y.Chin.J.Exp.Tradit.Med.Form.(朱益雷,方海红,魏惠珍,刘晟楠,段奕倩,龚明,饶毅.中国实验方剂学杂志),2016,(12):75-78.
[47] Lin H Y,Su C,Duan T X,Huang J M,Sun Y K,Wang Y,Ji J J,Dong J,Liu Y G.Mod.Chin.Med.(林宏英,苏畅,段天璇,黄建梅,孙毅坤,王玥,冀娇娇,董洁,刘永刚.中国现代中药),2015,17(3):208-211.
[48] Long Z,Guo Z M,Acworth I N,Liu X G,Jin Y,Liu X,Liu L,Liang L.Talanta,2016,151(5):239-244.
[49] Qing Z X,Liu X B,Wu H M,Cheng P,Liu Y S,Zeng J G.Anal.Methods,2015,7(5):1866-1871.
[50] Le P M,Mccooeye M,Windust A.Anal.Bioanal.Chem.,2013,405(13):4487-4498.
[51] Liu Q,Jiang S Y,Tian S J.Chin.J.Mod.Appl.Pharm.(刘琼,姜舜尧,田颂九.中国现代应用药学),2004,21(1):64-67.
[52] Long Z,Guo Z M,Xue X Y,Zhang X L,Nordahl L,Liang X M.Anal.Chim.Acta,2013,804:304-312.
[53] Taujenis L,Olsauskaite V,Padarauskas A.Acta Chromatogr.,2015,27(2):373-385.
[54] Zhuo R J,Wang L,Wang L X,Xiao H B,Cai S Q.Chin.J.Chrom.(卓荣杰,王莉,王龙星,肖红斌,蔡少青.色谱),2010,28(4):379-382.
[55] Long Z.The Analysis and Purification of Basic Compounds.Dalian:Dalian Institute of Chemical Physics,Chinese Academy of Sciences(龙珍.碱性化合物的色谱分离分析与分离纯化制备.大连:中国科学院大连化学物理研究所),2014.
[56] Huang J Y,Tong L,Ding L.Prog.Pharm.Sci.(黄竞怡,佟玲,丁黎.药学进展),2015,39(5):357-363.
[57] Wei X D,Shen H L,Wang L J,Meng Q Y,Liu W J.J.Anal.Methods Chem.,2016,Article ID 9752735.
[58] Zhang J C.Study on the Chromatographic Separation Method of Alkaloids in the Huperzia Serrata.Dalian:Dalian University of Technology(张敬彩.中药千层塔中生物碱成分的色谱分离方法研究.大连:大连理工大学),2013.
[59] Long Z,Guo Z M,Xue X Y,Zhang X,Liang X.J.Sep.Sci.,2013,36(24):3845-3852.
[60] Fang L,Liu Y Q,Yang B,Wang X.Huang L Q.J.Sep.Sci.,2011,34(19):2545-2558.
[61] Hu R L,Pan Y J.Trac-Trend.Anal.Chem.,2012,40:15-27.
[62] Niu L L,Xie Z S,Cai T X,Wu P,Xue P,Chen X L,Wu Z Y,Ito Y,Li F M,Yang F Q.J.Sep.Sci.,2011,34(9):987-994.
[63] Sun C L,Li J,Wang X,Duan W J,Zhang T Y,Ito Y.J.Chromatogr.A,2014,1370:156-161.
[64] Zhang Y,Wang C R,Wang L,Parks G S,Zhang X L,Guo Z M,Ke Y X,Li K W,Kim M K,Vo B,Borrelli E,Ge G B,Yang L,Wang Z W,Garcia-Fuster M J,Luo Z D,Liang X M,Civelli O.Curr.Biol.,2014,24(2):117-123.
[65] Zhang Y,Wang C R,Guo Z M,Zhang X L,Wang Z W,Liang X M,Civelli O.J.Ethnopharmacol.,2014,155(3):1597-1602.
[66] Long Z,Zhang Y,Guo Z M,Wang L,Xue X Y,Zhang X L,Wang S S,Wang Z W,Civelli O,Liang X M.Planta.Med.,2014,80(13):1124-1130.
[67] Du N N,Liu Y F,Zhang X L,Wang J X,Zhao J Q,He J,Zhou H,Mei L J,Liang X M.Sci.Rep.,2017,7:46067.
[68] Li K Y,Zhu W Y,Fu Q,Ke Y X,Jin Y,Liang X M.Analyst,2013,138(11):3313-3320.