单糖高效液相色谱法检测技术研究进展
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摘要
高效液相色谱法因操作简单、高效和灵敏度高成为单糖分析的重要方法之一。文章介绍几种常用单糖分析的高效液相色谱方法,即液相色谱示差折光检测法、液相色谱蒸发光散射检测法、PMP柱前衍生化检测法、对氨基苯甲酸柱前衍生法、邻氨苯甲酸衍生法、柱后衍生法,指出它们的优缺点,并从灵敏度、操作方法、精确度等方面进行分析比较。
High performance liquid chromatography(HPLC)is one of the most important factors in monosaccharide analysis due to its simple operation,and high efficiency and sensitivity.In this study,several commonly used methods were described,for the analysis of monosaccharides by high performance liquid chromatography,i.e.,liquid chromatography differential refractive index detection,liquid chromatography evaporative light scattering detection,PMP pre-column derivatization detection,para-aminobenzoic acid pre-column derivatization,the o-aminobenzoic acid derivative method and post-column derivatization method.Moreover,the advantages and disadvantages of these methods were demonstrated,and the sensitivity,operation method,and accuracy were compared and analyzed among these methods.
High performance liquid chromatography(HPLC)is one of the most important factors in monosaccharide analysis due to its simple operation,and high efficiency and sensitivity.In this study,several commonly used methods were described,for the analysis of monosaccharides by high performance liquid chromatography,i.e.,liquid chromatography differential refractive index detection,liquid chromatography evaporative light scattering detection,PMP pre-column derivatization detection,para-aminobenzoic acid pre-column derivatization,the o-aminobenzoic acid derivative method and post-column derivatization method.Moreover,the advantages and disadvantages of these methods were demonstrated,and the sensitivity,operation method,and accuracy were compared and analyzed among these methods.
引文
[1]GOMIS D B,TAMAYO D M,ALONSO J M.Determination of monosaccharides in cider by reversed-phase liquid chromatography[J].Analytica Chimica Acta,2001,436(1):173-180.
[2]尤婷婷,姜燕,张海悦,等.蹄叶槖吾叶多糖提取工艺优化及单糖组成研究[J].天然产物研究与开发,2016(1):136-141.
[3]RUIZ-CALERO V,PUIGNOU L,GALCERAN M T.Determination of glycosaminoglycan monosaccharides by capillary electrophoresis using laser-induced fluorescence detection[J].JChromatogr B AnalytTechnol Biomed Life Sci,2003,791(1):193-202.
[4]ZOLLO F,IORIZZI M,FESTA C,et al.L-Cysteine(3-nitrophenyl)methyl ester hydrochloride:a new chiral reagent in the sugar analysis[J].Letters in Organic Chemistry,2017,14(2):69-73.
[5]RUMPEL C,DIGNAC M F.Gas chromatographic analysis of monosaccharides in a forest soil profile:Analysis by gas chromatography after trifluoroacetic acid hydrolysis and reduction-acetylation[J].Soil Biology&Biochemistry,2006,38(6):1 478-1 481.
[6]贾鹏禹,孙蕊,彭绪玲,等.配位体交换色谱法测定槐米废渣水解液单糖成分[J].天然产物研究与开发,2017(5):800-804.
[7]HAYES R,AHMED A,EDGE T,et al.Core-shell particles:preparation,fundamentals and applications in high performance liquid chromatography[J].Journal of Chromatography A,2014,1 357:36.
[8]YOU Lv,YANG Xing-bin,ZHAO Yan,et al.Separation and quantification of component monosaccharides of the tea polysaccharides from Gynostemma pentaphyllum by HPLC with indirect UV detection[J].Food Chemistry,2009,112(3):742-746.
[9]SINGH V,PANDA S,KAUR H,et al.Solvation behavior of monosaccharides in aqueous protic ionic liquid solutions:Volumetric,calorimetric and NMR spectroscopic studies[J].Fluid Phase Equilibria,2016,421:24-32.
[10]AKABANE M,YAMAMOTO A,AIZAWA S,et al.Simultaneous enantioseparation of monosaccharides derivatized with L-tryptophan by reversed phase HPLC[J].Analytical Sciences the International Journal of the Japan Society for Analytical Chemistry,2014,30(7):739.
[11]郭怀忠,李胜男,吴芳,等.单糖紫外衍生方法的改进与应用[J].中国实验方剂学杂志,2017(2):32-36.
[12]郝桂堂,陈尚卫,朱松,等.对氨基苯甲酸衍生化高效液相色谱法分析多糖中的单糖及糖醛酸组成[J].色谱,2007,25(1):75-79.
[13]梁军,夏永刚,杨炳友,等.基于氨基苯甲酸衍生化HPLC-FLD分析中药多糖单糖组成[J].中医药学报,2016,44(6):13-15.
[14]FANG Jing-jing,QIN Guo-chen,MA Jun,et al.Quantification of plant cell wall monosaccharides by reversed-phase liquid chromatography with 2-aminobenzamide pre-column derivatization and a non-toxic reducing reagent 2-picoline borane[J].Journal of Chromatography A,2015,1 414:122-128.
[15]张璐瑶,赵峡,陈欢欢.糖类化合物PMP衍生分析进展[J].分析测试学报,2016,35(3):367-372.
[16]DAI Jun,WU Yan,CHEN Shang-wei,et al.Sugar compositional determination of polysaccharides from Dunaliellasalina by modified RP-HPLC method of precolumnderivatization with 1-phenyl-3-methyl-5-pyrazolone[J].Carbohydrate Polymers,2010,82(3):629-635.
[17]BAI Wei-dong,FANG Xiao-di,ZHAO Wen-hong,et al.Determination of oligosaccharides and monosaccharides in Hakka rice wine by precolumn derivation high-performance liquid chromatography[J].Journal of Food&Drug Analysis,2015,23(4):645.
[18]李卫燕,李萍,曹蔚.柱前衍生化高效液相色谱法测定当归酸性多糖单糖组成的新方法[J].科学技术与工程,2015,15(10):151-154.
[19]王媛媛,张晖,杨俊松,等.柱前衍生化高效液相色谱法分析9种多糖中的单糖组成[J].济宁医学院学报,2016,39(4):241-244.
[20]汪名春,聂陈志鹏,朱培蕾,等.莴苣茎水溶性多糖的单糖组成及免疫调节活性研究[J].食品与机械,2016,34(5):148-151.
[21]宋叶涵,李冬梅,杨静峰,等.三种色谱法分析鲍鱼生殖腺多糖的单糖组成[J].食品与机械,2012,28(2):44-47.
[22]段月,刘敦华,李世瑶,等.不同生长期枸杞多糖变化规律及特性研究[J].食品与机械,2016,32(12):55-59.
[23]MARKUS Windwarder,RUDOLF Figl,ELISABETH Svehla,et al.“Hypermethylation”of anthranilic acid-labeled sugars confers the selectivity required for liquid chromatography-mass spectrometry[J].Analytical Biochemistry,2016,514:24-31.
[24]程宾,梁成罡,杨化新.柱前衍生化反相高效液相色谱法定量测定重组人促卵泡激素中的单糖[J].药物分析杂志,2008(9):1 454-1 458.
[25]赵鑫.1-萘硼酸柱后衍生高效液相色谱荧光法测定单糖的研究[D].石家庄:河北师范大学,2013:50-55.
[26]FANG Huo,ZHANG Zhi-mei,WANG Jian-jun,et al.Research advances in detection techniques of high performance liquid chromatography-refractive index detector[J].Animal Husbandry and Feed Science,2014(2):87-90.
[27]LAKKA N S,PRAVEEN B N V V D,REDDY C S.Simple and sensitive RP-HPLC/RID method for the determination of triclofos sodium[J].Journal of the Indian Chemical Society,2017,94:53-58.
[28]姜红,但晓梦,胡远华,等.HPLC-RID法测定氨基葡萄糖的含量[J].中国药品标准,2013,14(4):259-263.
[29]刘泰然,李洁,刘平,等.高效液相色谱-示差折光法测定保健食品中的低聚木糖[J].中国食品卫生杂志,2012,24(2):132-135.
[30]于雷,李晓坤,张华锋,等.RP-HPLC-RID法同时测定怀地黄中单糖、低聚糖的含量[J].药物分析杂志,2013(6):977-982.
[31]欧阳华学,黎源倩,肖全伟.高效液相色谱法同时测定枸杞中单糖和低聚糖的含量[J].四川大学学报:医学版,2007,38(6):1 040-1 042.
[32]刘潇潇,戴慧贤,刘学华,等.HPLC示差折光检测法同时测定参芪扶正注射液中单糖和寡糖的含量[J].中国药房,2012(12):1 139-1 141.
[33]郭秀春,郭小白,张苗苗,等.莱茵-埃农氏法和高效液相色谱-示差折光法检测奶粉中乳糖和蔗糖的比较研究[J].食品科学,2016,37(12):139-143.
[34]张进杰,顾伟钢,闫永芳,等.HPLC示差折光法测定水产品中还原糖、磷酸化单糖和蔗糖[J].食品与生物技术学报,2011,30(4):576-582.
[35]LIN Chun-hua,LEI Zhi-wei,LIU De-yong,et al.Determination of four kinds of monosaccharides and disaccharides in honey by ultra performance convergence chromatography with evaporative light scattering detector[J].Chinese Journal of Analytical Chemistry,2016,44(12):1 912-1 918.
[36]王巧娥,丁明玉.蒸发光散射检测技术研究进展[J].分析测试学报,2006,25(6):126-132.
[37]姜辉,王斌,高家荣.高效液相色谱法-蒸发光散射检测器同时测定肝乐颗粒中黄芪甲苷和芍药苷的含量[J].安徽中医药大学学报,2015,34(3):86-89.
[38]杨俊,刘江生,蔡继宝,等.高效液相色谱-蒸发光散射检测法测定烟草中的水溶性糖[J].分析化学,2005,33(11):1 596-1 598.
[39]DING Hong-liu,LI Can,JIN Peng,et al.Simultaneous determination of monosaccharides,disaccharides,oligosaccharides and sugar alcohols in foods by high performance liquid chromatography with evaporative light-scattering detection[J].Chinese Journal of Chromatography,2013,31(8):804.
[40]沈少林,陆文琪,张惠雄.高效液相色谱-蒸发光散射法同时测定蜂蜜中果糖、葡萄糖、蔗糖和麦芽糖[J].理化检验:化学分册,2015,51(9):1 330-1 332.
[41]尚姝,冯有龙.高效液相色谱蒸发光散射检测器测定保健食品中果糖、葡萄糖、蔗糖、麦芽糖、乳糖和木糖[J].西北药学杂志,2014(1):27-31.
[42]LIU Qian,LUCIANA C Nogueira,FILIPE Silva,et al.Separation and quantification of carbohydrate compounds in beer using high performance liquid chromatography-evaporative light scattering detector[J].Bee Tech,2016(5):65-68.
[43]STEFANSSON M,WESTERLUND D.Ligand-exchange chromatography of carbohydrates andglycoconjugates[J].Journal of Chromatography A,1996,720(1/2):127-136.
[44]CHURMS S C.Recent progress in carbohydrate separation by high-performance liquid chromatography based on size exclusion[J].Journal of Chromatography A,1996,720(1/2):151-166.
[45]ALPERT A J,SHUKLA M,SHUKLA A K,et al.Hydrophilic-interaction chromatography of complex carbohydrates[J].Journal of Chromatography A,1994,676(1):191-122.
[46]KLEIN A,CARNOY C,LO-GUIDICE J M,et al.Separation of mucin oligosaccharide-alditols by high performance liquid chromatography on alkylamine-bonded silica columns.Effects of structural parameters[J].Carbohydr Res,1992,236(26):9-16.
[47]LIU Ying,URGAONKAR S,VERKADE J G,et al.Separation and characterization of underivatized oligosaccharides using liquid chromatography and liquid chromatography-electrospray ionization mass spectrometry[J].Journal of Chromatography A,2005,1 079(1/2):146.
[48]GHFAR A A,WABAIDUR S M,AHMED A Y,et al.Simultaneous determination of monosaccharides and oligosaccharides in dates using liquid chromatography-electrospray ionization mass spectrometry[J].Food Chemistry,2015,176:487-492.
[2]尤婷婷,姜燕,张海悦,等.蹄叶槖吾叶多糖提取工艺优化及单糖组成研究[J].天然产物研究与开发,2016(1):136-141.
[3]RUIZ-CALERO V,PUIGNOU L,GALCERAN M T.Determination of glycosaminoglycan monosaccharides by capillary electrophoresis using laser-induced fluorescence detection[J].JChromatogr B AnalytTechnol Biomed Life Sci,2003,791(1):193-202.
[4]ZOLLO F,IORIZZI M,FESTA C,et al.L-Cysteine(3-nitrophenyl)methyl ester hydrochloride:a new chiral reagent in the sugar analysis[J].Letters in Organic Chemistry,2017,14(2):69-73.
[5]RUMPEL C,DIGNAC M F.Gas chromatographic analysis of monosaccharides in a forest soil profile:Analysis by gas chromatography after trifluoroacetic acid hydrolysis and reduction-acetylation[J].Soil Biology&Biochemistry,2006,38(6):1 478-1 481.
[6]贾鹏禹,孙蕊,彭绪玲,等.配位体交换色谱法测定槐米废渣水解液单糖成分[J].天然产物研究与开发,2017(5):800-804.
[7]HAYES R,AHMED A,EDGE T,et al.Core-shell particles:preparation,fundamentals and applications in high performance liquid chromatography[J].Journal of Chromatography A,2014,1 357:36.
[8]YOU Lv,YANG Xing-bin,ZHAO Yan,et al.Separation and quantification of component monosaccharides of the tea polysaccharides from Gynostemma pentaphyllum by HPLC with indirect UV detection[J].Food Chemistry,2009,112(3):742-746.
[9]SINGH V,PANDA S,KAUR H,et al.Solvation behavior of monosaccharides in aqueous protic ionic liquid solutions:Volumetric,calorimetric and NMR spectroscopic studies[J].Fluid Phase Equilibria,2016,421:24-32.
[10]AKABANE M,YAMAMOTO A,AIZAWA S,et al.Simultaneous enantioseparation of monosaccharides derivatized with L-tryptophan by reversed phase HPLC[J].Analytical Sciences the International Journal of the Japan Society for Analytical Chemistry,2014,30(7):739.
[11]郭怀忠,李胜男,吴芳,等.单糖紫外衍生方法的改进与应用[J].中国实验方剂学杂志,2017(2):32-36.
[12]郝桂堂,陈尚卫,朱松,等.对氨基苯甲酸衍生化高效液相色谱法分析多糖中的单糖及糖醛酸组成[J].色谱,2007,25(1):75-79.
[13]梁军,夏永刚,杨炳友,等.基于氨基苯甲酸衍生化HPLC-FLD分析中药多糖单糖组成[J].中医药学报,2016,44(6):13-15.
[14]FANG Jing-jing,QIN Guo-chen,MA Jun,et al.Quantification of plant cell wall monosaccharides by reversed-phase liquid chromatography with 2-aminobenzamide pre-column derivatization and a non-toxic reducing reagent 2-picoline borane[J].Journal of Chromatography A,2015,1 414:122-128.
[15]张璐瑶,赵峡,陈欢欢.糖类化合物PMP衍生分析进展[J].分析测试学报,2016,35(3):367-372.
[16]DAI Jun,WU Yan,CHEN Shang-wei,et al.Sugar compositional determination of polysaccharides from Dunaliellasalina by modified RP-HPLC method of precolumnderivatization with 1-phenyl-3-methyl-5-pyrazolone[J].Carbohydrate Polymers,2010,82(3):629-635.
[17]BAI Wei-dong,FANG Xiao-di,ZHAO Wen-hong,et al.Determination of oligosaccharides and monosaccharides in Hakka rice wine by precolumn derivation high-performance liquid chromatography[J].Journal of Food&Drug Analysis,2015,23(4):645.
[18]李卫燕,李萍,曹蔚.柱前衍生化高效液相色谱法测定当归酸性多糖单糖组成的新方法[J].科学技术与工程,2015,15(10):151-154.
[19]王媛媛,张晖,杨俊松,等.柱前衍生化高效液相色谱法分析9种多糖中的单糖组成[J].济宁医学院学报,2016,39(4):241-244.
[20]汪名春,聂陈志鹏,朱培蕾,等.莴苣茎水溶性多糖的单糖组成及免疫调节活性研究[J].食品与机械,2016,34(5):148-151.
[21]宋叶涵,李冬梅,杨静峰,等.三种色谱法分析鲍鱼生殖腺多糖的单糖组成[J].食品与机械,2012,28(2):44-47.
[22]段月,刘敦华,李世瑶,等.不同生长期枸杞多糖变化规律及特性研究[J].食品与机械,2016,32(12):55-59.
[23]MARKUS Windwarder,RUDOLF Figl,ELISABETH Svehla,et al.“Hypermethylation”of anthranilic acid-labeled sugars confers the selectivity required for liquid chromatography-mass spectrometry[J].Analytical Biochemistry,2016,514:24-31.
[24]程宾,梁成罡,杨化新.柱前衍生化反相高效液相色谱法定量测定重组人促卵泡激素中的单糖[J].药物分析杂志,2008(9):1 454-1 458.
[25]赵鑫.1-萘硼酸柱后衍生高效液相色谱荧光法测定单糖的研究[D].石家庄:河北师范大学,2013:50-55.
[26]FANG Huo,ZHANG Zhi-mei,WANG Jian-jun,et al.Research advances in detection techniques of high performance liquid chromatography-refractive index detector[J].Animal Husbandry and Feed Science,2014(2):87-90.
[27]LAKKA N S,PRAVEEN B N V V D,REDDY C S.Simple and sensitive RP-HPLC/RID method for the determination of triclofos sodium[J].Journal of the Indian Chemical Society,2017,94:53-58.
[28]姜红,但晓梦,胡远华,等.HPLC-RID法测定氨基葡萄糖的含量[J].中国药品标准,2013,14(4):259-263.
[29]刘泰然,李洁,刘平,等.高效液相色谱-示差折光法测定保健食品中的低聚木糖[J].中国食品卫生杂志,2012,24(2):132-135.
[30]于雷,李晓坤,张华锋,等.RP-HPLC-RID法同时测定怀地黄中单糖、低聚糖的含量[J].药物分析杂志,2013(6):977-982.
[31]欧阳华学,黎源倩,肖全伟.高效液相色谱法同时测定枸杞中单糖和低聚糖的含量[J].四川大学学报:医学版,2007,38(6):1 040-1 042.
[32]刘潇潇,戴慧贤,刘学华,等.HPLC示差折光检测法同时测定参芪扶正注射液中单糖和寡糖的含量[J].中国药房,2012(12):1 139-1 141.
[33]郭秀春,郭小白,张苗苗,等.莱茵-埃农氏法和高效液相色谱-示差折光法检测奶粉中乳糖和蔗糖的比较研究[J].食品科学,2016,37(12):139-143.
[34]张进杰,顾伟钢,闫永芳,等.HPLC示差折光法测定水产品中还原糖、磷酸化单糖和蔗糖[J].食品与生物技术学报,2011,30(4):576-582.
[35]LIN Chun-hua,LEI Zhi-wei,LIU De-yong,et al.Determination of four kinds of monosaccharides and disaccharides in honey by ultra performance convergence chromatography with evaporative light scattering detector[J].Chinese Journal of Analytical Chemistry,2016,44(12):1 912-1 918.
[36]王巧娥,丁明玉.蒸发光散射检测技术研究进展[J].分析测试学报,2006,25(6):126-132.
[37]姜辉,王斌,高家荣.高效液相色谱法-蒸发光散射检测器同时测定肝乐颗粒中黄芪甲苷和芍药苷的含量[J].安徽中医药大学学报,2015,34(3):86-89.
[38]杨俊,刘江生,蔡继宝,等.高效液相色谱-蒸发光散射检测法测定烟草中的水溶性糖[J].分析化学,2005,33(11):1 596-1 598.
[39]DING Hong-liu,LI Can,JIN Peng,et al.Simultaneous determination of monosaccharides,disaccharides,oligosaccharides and sugar alcohols in foods by high performance liquid chromatography with evaporative light-scattering detection[J].Chinese Journal of Chromatography,2013,31(8):804.
[40]沈少林,陆文琪,张惠雄.高效液相色谱-蒸发光散射法同时测定蜂蜜中果糖、葡萄糖、蔗糖和麦芽糖[J].理化检验:化学分册,2015,51(9):1 330-1 332.
[41]尚姝,冯有龙.高效液相色谱蒸发光散射检测器测定保健食品中果糖、葡萄糖、蔗糖、麦芽糖、乳糖和木糖[J].西北药学杂志,2014(1):27-31.
[42]LIU Qian,LUCIANA C Nogueira,FILIPE Silva,et al.Separation and quantification of carbohydrate compounds in beer using high performance liquid chromatography-evaporative light scattering detector[J].Bee Tech,2016(5):65-68.
[43]STEFANSSON M,WESTERLUND D.Ligand-exchange chromatography of carbohydrates andglycoconjugates[J].Journal of Chromatography A,1996,720(1/2):127-136.
[44]CHURMS S C.Recent progress in carbohydrate separation by high-performance liquid chromatography based on size exclusion[J].Journal of Chromatography A,1996,720(1/2):151-166.
[45]ALPERT A J,SHUKLA M,SHUKLA A K,et al.Hydrophilic-interaction chromatography of complex carbohydrates[J].Journal of Chromatography A,1994,676(1):191-122.
[46]KLEIN A,CARNOY C,LO-GUIDICE J M,et al.Separation of mucin oligosaccharide-alditols by high performance liquid chromatography on alkylamine-bonded silica columns.Effects of structural parameters[J].Carbohydr Res,1992,236(26):9-16.
[47]LIU Ying,URGAONKAR S,VERKADE J G,et al.Separation and characterization of underivatized oligosaccharides using liquid chromatography and liquid chromatography-electrospray ionization mass spectrometry[J].Journal of Chromatography A,2005,1 079(1/2):146.
[48]GHFAR A A,WABAIDUR S M,AHMED A Y,et al.Simultaneous determination of monosaccharides and oligosaccharides in dates using liquid chromatography-electrospray ionization mass spectrometry[J].Food Chemistry,2015,176:487-492.