逆流色谱分离异构体分子研究进展
|
摘要
逆流色谱是一种连续高效的液-液分配色谱技术,近年来已广泛应用于天然产物、合成产物中目标成分的分离纯化,在异构体分子的制备分离中也发挥了一定优势。本文以异构体类型分类总结,总结了近年来逆流色谱在构造异构体、立体异构体等异构体分子分离中的应用研究进展。
Countercurrent chromatography belongs to liquid-liquid partition chromatographic technique using no solid support and it has been widely applied in separation of components from natural products and synthetic mixtures,it also has an advantage in the separation and preparation of isomers.The applications of countercurrent chromatography in the separation of structural isomers and stereoisomers are reviewed in this paper according to the classification of isomers.
Countercurrent chromatography belongs to liquid-liquid partition chromatographic technique using no solid support and it has been widely applied in separation of components from natural products and synthetic mixtures,it also has an advantage in the separation and preparation of isomers.The applications of countercurrent chromatography in the separation of structural isomers and stereoisomers are reviewed in this paper according to the classification of isomers.
引文
[1]TANIMURA T,PISANO JJ,ITO Y,et al.Droplet countercurrent chromatography[J].Science,1970,169(3940):54
[2]ITO Y,SANDLIN J,BOWERS WG.High-speed preparative counter-current chromatography with a coil planet centrifuge[J].J Chromatogr A,1982,244(2):247
[3]ITO Y.Foam countercurrent chromatography based on dual countercurrent systems[J].J Liq Chromatogr,1985,8(12):2131
[4]ITOY,KITAZUMEE,BHATNAGARM,etal.Cross-axis synchronous flow-through coil planet centrifuge(type XLL):Ⅰ.Design of the apparatus and studies on retention of stationary phase[J].J Chromatogr A,1991,538(1):59
[5]张虎,沈芒芒,颜继忠,等.逆流色谱中多种洗脱模式的应用研究进展[J].中国现代应用药学,2014,31(5):628ZHANG H,SHEN MM,YAN JZ,et al.Progress of different elution modes of counter-current chromatography[J].Chin J Mod Appl Pharm,2014,31(5):628
[6]邸多隆,郑媛媛,陈小芬,等.高速逆流色谱技术分离纯化天然产物中黄酮类化合物的研究进展[J].分析化学,2011,39(2):269DI DL,ZHENG YY,CHEN XF,et al.Advance of application of high speed counter-current chromatography in separation and purification of flavonoids[J].Chin J Anal Chem,2011,39(2):269
[7]王尉,杜宁,周晓晶,等.高速逆流色谱技术在天然产物研究方面的应用[J].现代科学仪器,2010(4):123WANG W,DU N,ZHOU XJ,et al.Application of high-speed countercurrent chromatography in the research of natural botanic products[J].Mod Sci Instrum,2010(4):123
[8]陈小芬,黄新异,郑媛媛,等.高速逆流色谱分离纯化天然产物中生物碱类成分的应用进展[J].中草药,2011,42(5):1026CHEN XF,HUANG XY,ZHENG YY,et al.Application of high-speed counter-current chromatography in separation and purification for alkaloids in natural products[J].Chin Tradit Herb Drugs,2011,42(5):1026
[9]蒋志国,陈文学,刘四新.高速逆流色谱分离制备白胡椒中单萜类化合物[J].食品与发酵工业,2011,37(3):202JIANG ZG,CHEN WX,LIU SX.Study on the separation of monoterpenes from Pipernigrum L.by high-speed counter-current chromatography[J].Food Ferment Ind,2011,37(3):202
[10]裴圣洲.有机化学中的异构现象[J].武汉教育学院学报,1995(6):61PEI SZ.Isomerism in organic chemistry[J].J Wuhan Inst Educ,1995(6):61
[11]许辉.二氯硝基苯同分异构体结晶分离的基础研究[D].扬州:扬州大学,2014XU H.Fundamental Research on Crystallization Separation of Dichloronitrobenzene Isomers[D].Yangzhou:Yangzhou University,2014
[12]陈阳生,李明娟.骨化三醇的分离及结构测定[J].中国医疗前沿月刊,2009,4(3):105CHEN YS,LI MJ.Determination of chemical constituent and configuration of calcitriol[J].China Healthcare Front,2009,4(3):105
[13]龙安禄,周元敬,贾广飞,等.动力学拆分方法的研究进展[J].贵州师范学院学报,2015,31(9):11LONG AL,ZHOU YJ,JIA GF,et al.Research status of kinetic resolution method[J].J Guizhou Educ Univ,2015,31(9):11
[14]赵磊,赵平.膜分离拆分对映异构体研究进展[J].河北工业科技,2009,26(1):53ZHAO L,ZHAO P.Research development of enantiomer separation by membrane process[J].Hebei J Ind Sci Technol,2009,26(1):53
[15]LAINT KE,MEGURO J,ISO S,et al.Separation of geometric isomersofmetalβ-diketonatesbysupercriticalfluid chromatography[J].J Sep Sci,2015,16(6):372
[16]JAREMKO M,KASAI Y,BARGINEAR MF,et al.Tamoxifen metaboliteisomerseparationandquantificationbyliquid chromatography-tandem mass spectrometry[J].Anal Chem,2010,82(24):10186
[17]杨沐,钟文英,侯雯.手性药物分析方法研究进展[J].药学进展,2014(3):209YANG M,ZHONG WY,HOU W.Advances in research on analytical methods of chiral drugs[J].Prog Pharm Sci,2014(3):209
[18]WAN IW,ARSAD SR,MAAROF H,et al.Chiral separation of four stereoisomers of ketoconazole drugs using capillary electrophoresis[J].Chirality,2015,27(3):223
[19]CHU C,ZHANG SD,TONG SQ,et al.Elution-extrusion counter-current chromatography for the separation of two pairs of isomeric monoterpenes from Paeoniae Alba Radix[J].J Sep Sci,2015,38(17):3110
[20]WEISZ A,MAZZOLA EP,MURPHY CM,et al.Preparative separation of isomeric sulfophthalic acids by conventional and pH-zone-refining counter-current chromatography[J].J Chromatogr A,2002,966(1-2):111
[21]HANT,CAOXL,XUJ,etal.Separationofthepotential G-quadruplex ligands from the butanol extract of Zanthoxylum ailanthoides Sieb.&Zucc.by countercurrent chromatography and preparative high performance liquid chromatography[J].J Chromatogr A,2017,1507:104
[22]WEISZ A,MAZZOLA EP,MATUSIK JE.Preparative separation of isomeric 2-(2-quinolinyl)-1H-indene-1,3(2H)-dione monosulfonicacidsofthecoloradditiveD&CYellowNo.10(quinoline yellow)by pH-zone-refining counter-current chromatography[J].J Chromatogr A,2001,923(1-2):87
[23]TONG SQ,YAN JZ,GUAN YX.Preparative separation of isomeric caffeoylquinic acids from Flos Lonicerae by pH-zone-refining counter-current chromatography[J].J Chromatogr A,2008,1212(1):48
[24]LIU WN,LUO JG,KONG LY.Application of complexation high-speed counter-current chromatography in the separation of 5-hydroxyisoflavone isomers from Belamcanda chinensis(L.)DC[J].J Chromatogr A,2011,1218(14):1842
[25]TANGQF,LIUJ,XUEJ,etal.Preparativeisolationand purification of two new isomeric diterpenoid alkaloids from Aconitum coreanum by high-speed counter-current chromatography[J].J Chromatogr B,2008,872(1-2):181
[26]GUO W,WANG L,GAO Y,et al.Isolation of isochlorogenic acid isomers in flower buds of Lonicera japonica by high-speed counter-current chromatography and preparative high performance liquid chromatography[J].J Chromatogr B,2015,981-982:27
[27]CHEN T,LI HM,ZOU DL,et al.Separation of three anthraquinone glycosides including two isomers by preparative high-performance liquidchromatographyandhigh-speedcountercurrent chromatography from Rheum tanguticum Maxim.ex Balf.[J].J Sep Sci,2016,39(16):3105
[28]LI HM,CHEN T,SUN J,et al.Separation of six xanthones from Swertia franchetiana by high-speed countercurrent chromatography[J].J Sep Sci,2017,40(11):2515
[29]LIUD,SUZ,WANGC,etal.Separationoffiveisomers ofdihydroxybenzoicacidbyhigh-speedcounter-current chromatography with dual-rotation elution method[J].J Chromatogr Sci,2009,47(5):345
[30]LI P,WANG YL,GUO ZY,et al.Separation of three bioactive isomers from Bidens pilosa by countercurrent chromatography[J].J Liq Chromatogr Relat Technol,2014,37(18):2598
[31]LIU Y,FRIESEN JB,KLEIN LL,et al.The Generally Useful Estimate of Solvent Systems(GUESS)method enables the rapid purification of methylpyridoxine regioisomers by countercurrent chromatography[J].J Chromatogr A,2015,1426:248
[32]HE S,LU Y,WU B,et al.Isolation and purification of antioxidative isomeric polyphenols from the roots of Parthenocissus laetevirens by counter-current chromatography[J].J Chromatogr A,2007,1151(1-2):175
[33]WEISZ A,IDINA A,BEN-ARI J,et al.Preparative separation of isomeric and stereoisomeric dicarboxylic acids by pH-zone-refining counter-current chromatography[J].J Chromatogr A,2007,1151(1-2):82
[34]HE MF,DU WK,DU QB,et al.Isolation of the retinal isomers from the isomerization of all-trans-retinal by flash countercurrent chromatography[J].J Chromatogr A,2013,1271(1):67
[35]LI WC,WANG XY,LIN PC,et al.Preparative separation and purification of four cis-trans isomers of coumaroylspermidine analogs from safflower by high-speed counter-current chromatography[J].J Chromatogr B,2013,938(9):75
[36]郑烨,颜继忠,童胜强.逆流色谱技术在手性分离中的研究进展[J].药物分析杂志,2013,33(4):536ZHENGY,YANJZ,TONGSQ.Researchprogresson countercurrent chromatography in enantioseparations[J].Chin J Pharm Anal,2013,33(4):536
[37]吕迎春,樊竹青.逆流色谱技术在手性分离方面的应用[J].云南化工,2014(5):44LüYC,FAN ZQ.Application of countercurrent chromatography on chiral separation[J].Yunnan Chem Technol,2014(5):44
[38]袁黎明.手性逆流色谱的研究进展[J].色谱,2016,34(1):44YUAN LM.Progress of chiral countercurrent chromatograghy[J].Chin J Chromatogr,2016,34(1):44
[39]DOMON B,HOSTETTMANN K,KOVACEVIC K,et al.Separation of the enantiomers of(±)-norephedrine by rotation locular counter-current chromatography[J].J Chromatogr A,1982,250(1):149
[40]CAI Y,YAN Z,ZI M,et al.Preparative enantioseparation of DL–α-Methylbenzylaminebyhigh-Speedcountercurrent chromatography using L-(+)-tartaric acid as chiral selector[J].J Liq Chromatogr Relat Technol,2007,30(9-10):1489
[41]LüYC,YAN ZH,MA C,et al.Preparative enantioseparation of ofloxacin by high speed countercurrent chromatography using L-(+)-tartaric acid as chiral selector[J].J Liq Chromatogr Relat Technol,2010,33(13):1328
[42]TONG S,ZHENG Y,YAN J,et al.Preparative enantioseparation ofβ-blocker drugs by counter-current chromatography using dialkyl L-tartrate as chiral selector based on borate coordination complex[J].J Chromatogr A,2012,1263:74
[43]LüL,BU Z,LU M,et al.Stereoselective separation ofβ-adrenergic blocking agents containing two chiral centers by countercurrent chromatography[J].J Chromatogr A,2017,1513:235
[44]SUN G,TANG K,ZHANG P,et al.Separation of phenylsuccinic acid enantiomers using biphasic chiral recognition high-speed countercurrent chromatography[J].J Sep Sci,2014,37(14):1736
[45]OLIVEROS L,FRANCOPUERTOLAS P,MINGUILLON C,et al.Donor-acceptor chiral centrifugal partition chromatography:complete resolution of two pairs of amino-acid derivatives with a chiralⅡdonor selector[J].J Liq Chromatogr,1994,17(11):2301
[46]MA Y,ITO Y.Chiral separation by high-speed countercurrent chromatography[J].Anal Chem,1995,17(1):65
[47]MA Y,ITO Y,BERTHOD A.A chromatographic method for measuring Kf of enantiomer-chiral selector complexes[J].J Liq Chromatogr Relat Technol,1999,22(19):2945
[48]TONG SQ,SHEN MM,CHENG DP,et al.Chiral ligand exchange high-speed countercurrent chromatography:mechanism and application in enantioseparation of aromaticα-hydroxyl acids[J].J Chromatogr A,2014,1360:110
[49]PEREZ AM,MINGUILLON C.Retention of fluorinated chiral selectors in biphasic fluorinated solvent systems and its application to the separation of enantiomers by countercurrent chromatography[J].J Chromatogr A,2010,1217(7):1094
[50]DELGADO B,PéREZ E,SANTANO MC,et al.Enantiomer separation by counter-current chromatography.Optimisation and drawbacks in the use of L-proline derivatives as chiral selectors[J].J Chromatogr A,2005,1092(1):36
[51]TONGSQ,WANGX,SHENM,etal.Enantioseparationof 3-phenyllactic acid by chiral ligand exchange countercurrent chromatography[J].J Sep Sci,2017,40(8):1834
[52]BREINHOLT J,LEHMANN SV,VARMING AR.Enantiomer separation of 7-des-methyl-ormeloxifene using sulfated beta-cyclodextrin in countercurrent chromatography[J].Chirality,2015,11(10):768
[53]WEIY,DUS,ITOY.Enantioseparationoflomefloxacin hydrochloride by high-speed counter-current chromatography using sulfated-β-cyclodextrin as a chiral selector[J].J Chromatogr B,2010,878(28):2937
[54]YUANLM,LIUJC,YANZH,etal.Enantioseparationof chlorpheniramine by high speed countercurrent chromatography using carboxymethyl-β-cyclodextrin as chiral selector[J].J Liq Chromatogr Relat Technol,2005,28(19):3057
[55]AI P,LIU CJ,ZI M,et al.Enantioseparation of aminoglutethimide by high-speed counter current chromatography using carboxymethly-β-cyclodextrin as chiral selector[J].Chin Chem Lett,2006,17(6):787
[56]TONGSQ,YANJZ,GUANYX,etal.Separationofα-cyclohexylmandelic acid enantiomers using biphasic chiral recognition high-speed counter-current chromatography[J].J Chromatogr A,2010,1217(18):3044
[57]TONG SQ,GUAN Y,YAN JZ,et a1.Enantiomeric separation of(R,S)-naproxen by recycling high speed counter-current chromatography with hydroxypropyl-β-cyclodextrin as chiral selector[J].J Chromatogr A,2011,1218(32):5434
[58]TONG SQ,YAN JZ,GUAN XY,et a1.Enantioseparation of phenyl-succinic acid by high speed counte-current chromatography using hydroxypropyl-β-cyclodextrin as chiral selector[J].J Chromatogr A,2011,1218(33):5602
[59]TONG SQ,ZHENG Y,YAN JZ.Application and comparison of high performance liquid chromatography and high speed counter-current chromatography in enantioseparation of(±)-2-phenylpropionic acid[J].J Chromatogr A,2013,1281(6):79
[60]TONG SQ,ZHENG Y,YAN JZ.Enantioseparation of chiral aromatic acids by multiple dual mode counter-current chromatography using hydroxypropyl-β-cyclodextrin as chiral selector[J].J Sep Sci,2013,36(12):2035
[61]CHAO H,XU J,WANG X,et al.Enantioseparation of racemic trans-δ-viniferin using high speed counter-current chromatography based on induced circular dichroism technology[J].J Chromatogr A,2014,1324:164
[62]DURET PH,FOUCAULT A,MARGRAFF R.Vancomycin as a chiral selector in centrifugal partition chromatography[J].J Liq Chromatogr Relat Technol,2000,23(2):295
[63]PEREZ E,SANTOS MJ,MINGUILLON C.Application of cellulose and amylose arylcarbamates as chiral selectors in counter-current chromatography[J].J Chromatogr A,2006,1107(1):165
[64]FRANCO P,BLANC J,OBERLEITNER WR,et al.Enantiomer separation by countercurrent chromatography using cinchona alkaloid derivatives as chiral selectors[J].Anal Chem,2002,74(16):4175
[65]OYA S,SNYDER JK.Chiral resolution of a carboxylic acid using droplet counter-current chromatography[J].J Chromatogr A,1986,370:333
[66]RUBIO N,IGNATOVA S,MINGUILLON C,et al.Multiple dual-mode countercurrent chromatography applied to chiral separations usinga(S)-naproxenderivativeaschiralselector[J].J Chromatogr A,2009,1216(48):8505
[67]KIME,KOOBYM,CHUNGDS.Chiralcounter-current chromatography of gemifloxacin guided by capillary electrophoresis using(+)-(18-crown-6)-tetracarboxylic acid as a chiral selector[J].J Chromatogr A,2004,1045(1-2):119
[68]袁黎明,谌学先,刘国祥,等.高速逆流色谱对芦荟有效成分的制备性分离研究[J].分析化学,2003,31(2):251YUAN LM,CHEN XX,LIU GX,et al.Study on the preparation of effective components of aloe by high speed counter current chromatography[J].Chin J Anal Chem,2003,31(2):251
[69]黄丹凤,曹学丽,赵华,等.高速逆流色谱与硅胶柱色谱结合分离制备高纯度芦荟素异构体[J].色谱,2006,24(1):42HUANG DF,CAO XL,ZHAO H,et al.Preparative separation of aloin diastereoisomers by high-speed countercurrent chromatography combined with silica gel column chromatography[J].Chin J Chromatogr,2006,24(1):42
[70]张琦,李燕,党培育,等.应用高速逆流色谱分离纯化芦荟苷[J].食品工业科技,2011(4):283ZHANG Q,LI Y,DANG PY,et al.Separation and purification of aloin from aloe by high-speed counter-current chromatography[J].Sci Technol Food Ind,2011(4):283
[71]HAN QB,SONG JZ,QIAO C F,et al.Preparative separation of gambogic acid and its C-2 epimer using recycling high-speed counter-current chromatography[J].J Chromatogr A,2006,1127(1-2):298
[72]PARK SB,KIM YS.Simultaneous separation of three isomeric sennosides from senna leaf(Cassia acutifolia)using counter-current chromatography[J].J Sep Sci,2015,38(20):3502
[73]WANG X,LL,BU Z,et al.Separation of epimeric aromatic acid(-)-menthol esters by countercurrent chromatography using hydroxypropyl-β-cyclodextrin as an additive[J].J Sep Sci,2017,40(9):2045
[2]ITO Y,SANDLIN J,BOWERS WG.High-speed preparative counter-current chromatography with a coil planet centrifuge[J].J Chromatogr A,1982,244(2):247
[3]ITO Y.Foam countercurrent chromatography based on dual countercurrent systems[J].J Liq Chromatogr,1985,8(12):2131
[4]ITOY,KITAZUMEE,BHATNAGARM,etal.Cross-axis synchronous flow-through coil planet centrifuge(type XLL):Ⅰ.Design of the apparatus and studies on retention of stationary phase[J].J Chromatogr A,1991,538(1):59
[5]张虎,沈芒芒,颜继忠,等.逆流色谱中多种洗脱模式的应用研究进展[J].中国现代应用药学,2014,31(5):628ZHANG H,SHEN MM,YAN JZ,et al.Progress of different elution modes of counter-current chromatography[J].Chin J Mod Appl Pharm,2014,31(5):628
[6]邸多隆,郑媛媛,陈小芬,等.高速逆流色谱技术分离纯化天然产物中黄酮类化合物的研究进展[J].分析化学,2011,39(2):269DI DL,ZHENG YY,CHEN XF,et al.Advance of application of high speed counter-current chromatography in separation and purification of flavonoids[J].Chin J Anal Chem,2011,39(2):269
[7]王尉,杜宁,周晓晶,等.高速逆流色谱技术在天然产物研究方面的应用[J].现代科学仪器,2010(4):123WANG W,DU N,ZHOU XJ,et al.Application of high-speed countercurrent chromatography in the research of natural botanic products[J].Mod Sci Instrum,2010(4):123
[8]陈小芬,黄新异,郑媛媛,等.高速逆流色谱分离纯化天然产物中生物碱类成分的应用进展[J].中草药,2011,42(5):1026CHEN XF,HUANG XY,ZHENG YY,et al.Application of high-speed counter-current chromatography in separation and purification for alkaloids in natural products[J].Chin Tradit Herb Drugs,2011,42(5):1026
[9]蒋志国,陈文学,刘四新.高速逆流色谱分离制备白胡椒中单萜类化合物[J].食品与发酵工业,2011,37(3):202JIANG ZG,CHEN WX,LIU SX.Study on the separation of monoterpenes from Pipernigrum L.by high-speed counter-current chromatography[J].Food Ferment Ind,2011,37(3):202
[10]裴圣洲.有机化学中的异构现象[J].武汉教育学院学报,1995(6):61PEI SZ.Isomerism in organic chemistry[J].J Wuhan Inst Educ,1995(6):61
[11]许辉.二氯硝基苯同分异构体结晶分离的基础研究[D].扬州:扬州大学,2014XU H.Fundamental Research on Crystallization Separation of Dichloronitrobenzene Isomers[D].Yangzhou:Yangzhou University,2014
[12]陈阳生,李明娟.骨化三醇的分离及结构测定[J].中国医疗前沿月刊,2009,4(3):105CHEN YS,LI MJ.Determination of chemical constituent and configuration of calcitriol[J].China Healthcare Front,2009,4(3):105
[13]龙安禄,周元敬,贾广飞,等.动力学拆分方法的研究进展[J].贵州师范学院学报,2015,31(9):11LONG AL,ZHOU YJ,JIA GF,et al.Research status of kinetic resolution method[J].J Guizhou Educ Univ,2015,31(9):11
[14]赵磊,赵平.膜分离拆分对映异构体研究进展[J].河北工业科技,2009,26(1):53ZHAO L,ZHAO P.Research development of enantiomer separation by membrane process[J].Hebei J Ind Sci Technol,2009,26(1):53
[15]LAINT KE,MEGURO J,ISO S,et al.Separation of geometric isomersofmetalβ-diketonatesbysupercriticalfluid chromatography[J].J Sep Sci,2015,16(6):372
[16]JAREMKO M,KASAI Y,BARGINEAR MF,et al.Tamoxifen metaboliteisomerseparationandquantificationbyliquid chromatography-tandem mass spectrometry[J].Anal Chem,2010,82(24):10186
[17]杨沐,钟文英,侯雯.手性药物分析方法研究进展[J].药学进展,2014(3):209YANG M,ZHONG WY,HOU W.Advances in research on analytical methods of chiral drugs[J].Prog Pharm Sci,2014(3):209
[18]WAN IW,ARSAD SR,MAAROF H,et al.Chiral separation of four stereoisomers of ketoconazole drugs using capillary electrophoresis[J].Chirality,2015,27(3):223
[19]CHU C,ZHANG SD,TONG SQ,et al.Elution-extrusion counter-current chromatography for the separation of two pairs of isomeric monoterpenes from Paeoniae Alba Radix[J].J Sep Sci,2015,38(17):3110
[20]WEISZ A,MAZZOLA EP,MURPHY CM,et al.Preparative separation of isomeric sulfophthalic acids by conventional and pH-zone-refining counter-current chromatography[J].J Chromatogr A,2002,966(1-2):111
[21]HANT,CAOXL,XUJ,etal.Separationofthepotential G-quadruplex ligands from the butanol extract of Zanthoxylum ailanthoides Sieb.&Zucc.by countercurrent chromatography and preparative high performance liquid chromatography[J].J Chromatogr A,2017,1507:104
[22]WEISZ A,MAZZOLA EP,MATUSIK JE.Preparative separation of isomeric 2-(2-quinolinyl)-1H-indene-1,3(2H)-dione monosulfonicacidsofthecoloradditiveD&CYellowNo.10(quinoline yellow)by pH-zone-refining counter-current chromatography[J].J Chromatogr A,2001,923(1-2):87
[23]TONG SQ,YAN JZ,GUAN YX.Preparative separation of isomeric caffeoylquinic acids from Flos Lonicerae by pH-zone-refining counter-current chromatography[J].J Chromatogr A,2008,1212(1):48
[24]LIU WN,LUO JG,KONG LY.Application of complexation high-speed counter-current chromatography in the separation of 5-hydroxyisoflavone isomers from Belamcanda chinensis(L.)DC[J].J Chromatogr A,2011,1218(14):1842
[25]TANGQF,LIUJ,XUEJ,etal.Preparativeisolationand purification of two new isomeric diterpenoid alkaloids from Aconitum coreanum by high-speed counter-current chromatography[J].J Chromatogr B,2008,872(1-2):181
[26]GUO W,WANG L,GAO Y,et al.Isolation of isochlorogenic acid isomers in flower buds of Lonicera japonica by high-speed counter-current chromatography and preparative high performance liquid chromatography[J].J Chromatogr B,2015,981-982:27
[27]CHEN T,LI HM,ZOU DL,et al.Separation of three anthraquinone glycosides including two isomers by preparative high-performance liquidchromatographyandhigh-speedcountercurrent chromatography from Rheum tanguticum Maxim.ex Balf.[J].J Sep Sci,2016,39(16):3105
[28]LI HM,CHEN T,SUN J,et al.Separation of six xanthones from Swertia franchetiana by high-speed countercurrent chromatography[J].J Sep Sci,2017,40(11):2515
[29]LIUD,SUZ,WANGC,etal.Separationoffiveisomers ofdihydroxybenzoicacidbyhigh-speedcounter-current chromatography with dual-rotation elution method[J].J Chromatogr Sci,2009,47(5):345
[30]LI P,WANG YL,GUO ZY,et al.Separation of three bioactive isomers from Bidens pilosa by countercurrent chromatography[J].J Liq Chromatogr Relat Technol,2014,37(18):2598
[31]LIU Y,FRIESEN JB,KLEIN LL,et al.The Generally Useful Estimate of Solvent Systems(GUESS)method enables the rapid purification of methylpyridoxine regioisomers by countercurrent chromatography[J].J Chromatogr A,2015,1426:248
[32]HE S,LU Y,WU B,et al.Isolation and purification of antioxidative isomeric polyphenols from the roots of Parthenocissus laetevirens by counter-current chromatography[J].J Chromatogr A,2007,1151(1-2):175
[33]WEISZ A,IDINA A,BEN-ARI J,et al.Preparative separation of isomeric and stereoisomeric dicarboxylic acids by pH-zone-refining counter-current chromatography[J].J Chromatogr A,2007,1151(1-2):82
[34]HE MF,DU WK,DU QB,et al.Isolation of the retinal isomers from the isomerization of all-trans-retinal by flash countercurrent chromatography[J].J Chromatogr A,2013,1271(1):67
[35]LI WC,WANG XY,LIN PC,et al.Preparative separation and purification of four cis-trans isomers of coumaroylspermidine analogs from safflower by high-speed counter-current chromatography[J].J Chromatogr B,2013,938(9):75
[36]郑烨,颜继忠,童胜强.逆流色谱技术在手性分离中的研究进展[J].药物分析杂志,2013,33(4):536ZHENGY,YANJZ,TONGSQ.Researchprogresson countercurrent chromatography in enantioseparations[J].Chin J Pharm Anal,2013,33(4):536
[37]吕迎春,樊竹青.逆流色谱技术在手性分离方面的应用[J].云南化工,2014(5):44LüYC,FAN ZQ.Application of countercurrent chromatography on chiral separation[J].Yunnan Chem Technol,2014(5):44
[38]袁黎明.手性逆流色谱的研究进展[J].色谱,2016,34(1):44YUAN LM.Progress of chiral countercurrent chromatograghy[J].Chin J Chromatogr,2016,34(1):44
[39]DOMON B,HOSTETTMANN K,KOVACEVIC K,et al.Separation of the enantiomers of(±)-norephedrine by rotation locular counter-current chromatography[J].J Chromatogr A,1982,250(1):149
[40]CAI Y,YAN Z,ZI M,et al.Preparative enantioseparation of DL–α-Methylbenzylaminebyhigh-Speedcountercurrent chromatography using L-(+)-tartaric acid as chiral selector[J].J Liq Chromatogr Relat Technol,2007,30(9-10):1489
[41]LüYC,YAN ZH,MA C,et al.Preparative enantioseparation of ofloxacin by high speed countercurrent chromatography using L-(+)-tartaric acid as chiral selector[J].J Liq Chromatogr Relat Technol,2010,33(13):1328
[42]TONG S,ZHENG Y,YAN J,et al.Preparative enantioseparation ofβ-blocker drugs by counter-current chromatography using dialkyl L-tartrate as chiral selector based on borate coordination complex[J].J Chromatogr A,2012,1263:74
[43]LüL,BU Z,LU M,et al.Stereoselective separation ofβ-adrenergic blocking agents containing two chiral centers by countercurrent chromatography[J].J Chromatogr A,2017,1513:235
[44]SUN G,TANG K,ZHANG P,et al.Separation of phenylsuccinic acid enantiomers using biphasic chiral recognition high-speed countercurrent chromatography[J].J Sep Sci,2014,37(14):1736
[45]OLIVEROS L,FRANCOPUERTOLAS P,MINGUILLON C,et al.Donor-acceptor chiral centrifugal partition chromatography:complete resolution of two pairs of amino-acid derivatives with a chiralⅡdonor selector[J].J Liq Chromatogr,1994,17(11):2301
[46]MA Y,ITO Y.Chiral separation by high-speed countercurrent chromatography[J].Anal Chem,1995,17(1):65
[47]MA Y,ITO Y,BERTHOD A.A chromatographic method for measuring Kf of enantiomer-chiral selector complexes[J].J Liq Chromatogr Relat Technol,1999,22(19):2945
[48]TONG SQ,SHEN MM,CHENG DP,et al.Chiral ligand exchange high-speed countercurrent chromatography:mechanism and application in enantioseparation of aromaticα-hydroxyl acids[J].J Chromatogr A,2014,1360:110
[49]PEREZ AM,MINGUILLON C.Retention of fluorinated chiral selectors in biphasic fluorinated solvent systems and its application to the separation of enantiomers by countercurrent chromatography[J].J Chromatogr A,2010,1217(7):1094
[50]DELGADO B,PéREZ E,SANTANO MC,et al.Enantiomer separation by counter-current chromatography.Optimisation and drawbacks in the use of L-proline derivatives as chiral selectors[J].J Chromatogr A,2005,1092(1):36
[51]TONGSQ,WANGX,SHENM,etal.Enantioseparationof 3-phenyllactic acid by chiral ligand exchange countercurrent chromatography[J].J Sep Sci,2017,40(8):1834
[52]BREINHOLT J,LEHMANN SV,VARMING AR.Enantiomer separation of 7-des-methyl-ormeloxifene using sulfated beta-cyclodextrin in countercurrent chromatography[J].Chirality,2015,11(10):768
[53]WEIY,DUS,ITOY.Enantioseparationoflomefloxacin hydrochloride by high-speed counter-current chromatography using sulfated-β-cyclodextrin as a chiral selector[J].J Chromatogr B,2010,878(28):2937
[54]YUANLM,LIUJC,YANZH,etal.Enantioseparationof chlorpheniramine by high speed countercurrent chromatography using carboxymethyl-β-cyclodextrin as chiral selector[J].J Liq Chromatogr Relat Technol,2005,28(19):3057
[55]AI P,LIU CJ,ZI M,et al.Enantioseparation of aminoglutethimide by high-speed counter current chromatography using carboxymethly-β-cyclodextrin as chiral selector[J].Chin Chem Lett,2006,17(6):787
[56]TONGSQ,YANJZ,GUANYX,etal.Separationofα-cyclohexylmandelic acid enantiomers using biphasic chiral recognition high-speed counter-current chromatography[J].J Chromatogr A,2010,1217(18):3044
[57]TONG SQ,GUAN Y,YAN JZ,et a1.Enantiomeric separation of(R,S)-naproxen by recycling high speed counter-current chromatography with hydroxypropyl-β-cyclodextrin as chiral selector[J].J Chromatogr A,2011,1218(32):5434
[58]TONG SQ,YAN JZ,GUAN XY,et a1.Enantioseparation of phenyl-succinic acid by high speed counte-current chromatography using hydroxypropyl-β-cyclodextrin as chiral selector[J].J Chromatogr A,2011,1218(33):5602
[59]TONG SQ,ZHENG Y,YAN JZ.Application and comparison of high performance liquid chromatography and high speed counter-current chromatography in enantioseparation of(±)-2-phenylpropionic acid[J].J Chromatogr A,2013,1281(6):79
[60]TONG SQ,ZHENG Y,YAN JZ.Enantioseparation of chiral aromatic acids by multiple dual mode counter-current chromatography using hydroxypropyl-β-cyclodextrin as chiral selector[J].J Sep Sci,2013,36(12):2035
[61]CHAO H,XU J,WANG X,et al.Enantioseparation of racemic trans-δ-viniferin using high speed counter-current chromatography based on induced circular dichroism technology[J].J Chromatogr A,2014,1324:164
[62]DURET PH,FOUCAULT A,MARGRAFF R.Vancomycin as a chiral selector in centrifugal partition chromatography[J].J Liq Chromatogr Relat Technol,2000,23(2):295
[63]PEREZ E,SANTOS MJ,MINGUILLON C.Application of cellulose and amylose arylcarbamates as chiral selectors in counter-current chromatography[J].J Chromatogr A,2006,1107(1):165
[64]FRANCO P,BLANC J,OBERLEITNER WR,et al.Enantiomer separation by countercurrent chromatography using cinchona alkaloid derivatives as chiral selectors[J].Anal Chem,2002,74(16):4175
[65]OYA S,SNYDER JK.Chiral resolution of a carboxylic acid using droplet counter-current chromatography[J].J Chromatogr A,1986,370:333
[66]RUBIO N,IGNATOVA S,MINGUILLON C,et al.Multiple dual-mode countercurrent chromatography applied to chiral separations usinga(S)-naproxenderivativeaschiralselector[J].J Chromatogr A,2009,1216(48):8505
[67]KIME,KOOBYM,CHUNGDS.Chiralcounter-current chromatography of gemifloxacin guided by capillary electrophoresis using(+)-(18-crown-6)-tetracarboxylic acid as a chiral selector[J].J Chromatogr A,2004,1045(1-2):119
[68]袁黎明,谌学先,刘国祥,等.高速逆流色谱对芦荟有效成分的制备性分离研究[J].分析化学,2003,31(2):251YUAN LM,CHEN XX,LIU GX,et al.Study on the preparation of effective components of aloe by high speed counter current chromatography[J].Chin J Anal Chem,2003,31(2):251
[69]黄丹凤,曹学丽,赵华,等.高速逆流色谱与硅胶柱色谱结合分离制备高纯度芦荟素异构体[J].色谱,2006,24(1):42HUANG DF,CAO XL,ZHAO H,et al.Preparative separation of aloin diastereoisomers by high-speed countercurrent chromatography combined with silica gel column chromatography[J].Chin J Chromatogr,2006,24(1):42
[70]张琦,李燕,党培育,等.应用高速逆流色谱分离纯化芦荟苷[J].食品工业科技,2011(4):283ZHANG Q,LI Y,DANG PY,et al.Separation and purification of aloin from aloe by high-speed counter-current chromatography[J].Sci Technol Food Ind,2011(4):283
[71]HAN QB,SONG JZ,QIAO C F,et al.Preparative separation of gambogic acid and its C-2 epimer using recycling high-speed counter-current chromatography[J].J Chromatogr A,2006,1127(1-2):298
[72]PARK SB,KIM YS.Simultaneous separation of three isomeric sennosides from senna leaf(Cassia acutifolia)using counter-current chromatography[J].J Sep Sci,2015,38(20):3502
[73]WANG X,LL,BU Z,et al.Separation of epimeric aromatic acid(-)-menthol esters by countercurrent chromatography using hydroxypropyl-β-cyclodextrin as an additive[J].J Sep Sci,2017,40(9):2045