Application of two-dimensional liquid chromatography in the separation of traditional Chinese medicine.

Traditional Chinese medicines have been widely used to prevent and cure diseases for thousands of years. For the purpose of better understanding the extremely complicated traditional Chinese medicines, powerful separation techniques are essential. Two-dimensional liquid chromatography has been proven to be more powerful for the separation of complex traditional Chinese medicines due to its enhanced peak capacity and resolution compared with one-dimensional liquid chromatography. Enormous efforts have been made on the coupling of independent separation mechanisms to improve the resolving power for complex traditional Chinese medicine samples, including the development and introduction of novel stationary phases. This review aims to give an overview on the applications of two-dimensional liquid chromatography in traditional Chinese medicine research since 2008, including comprehensive two-dimensional liquid chromatography, heart-cutting two-dimensional liquid chromatography both in on-line and off-line mode. Different couplings of separation modes were respectively discussed based on specific studies, with emphasis on the the applications of novel stationary phases in the two-dimensional liquid chromatography. This article is protected by copyright. All rights reserved.

[1]  Xinmiao Liang,et al.  Offline preparative 2-D polar-copolymerized reversed-phase chromatography × zwitterionic hydrophilic interaction chromatography for effective purification of polar compounds from Caulis Polygoni Multiflori. , 2019, Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.

[2]  Yu Jin,et al.  "Click oligo(ethylene glycol)": an excellent orthogonal stationary phase to C18 for two-dimensional reversed-phase/reversed-phase liquid chromatography. , 2008, Journal of chromatography. A.

[3]  Qing Fu,et al.  The herbalome—an attempt to globalize Chinese herbal medicine , 2011, Analytical and Bioanalytical Chemistry.

[4]  Dan Wang,et al.  A novel two-dimensional preparative chromatography method designed for the separation of traditional animal Tibetan medicine Osteon Myospalacem Baileyi. , 2014, Journal of separation science.

[5]  Yifeng Chai,et al.  Comprehensive two-dimensional HepG2/cell membrane chromatography/monolithic column/time-of-flight mass spectrometry system for screening anti-tumor components from herbal medicines. , 2012, Journal of chromatography. A.

[6]  Min Yang,et al.  An enhanced targeted identification strategy for the selective identification of flavonoid O-glycosides from Carthamus tinctorius by integrating offline two-dimensional liquid chromatography/linear ion-trap-Orbitrap mass spectrometry, high-resolution diagnostic product ions/neutral loss filtering an , 2017, Journal of chromatography. A.

[7]  Ling Tong,et al.  Separation and analysis of phenolic acids from Salvia miltiorrhiza and its related preparations by off-line two-dimensional hydrophilic interaction chromatography×reversed-phase liquid chromatography coupled with ion trap time-of-flight mass spectrometry. , 2016, Journal of chromatography. A.

[8]  Dwight R Stoll,et al.  Active Solvent Modulation: A Valve-Based Approach To Improve Separation Compatibility in Two-Dimensional Liquid Chromatography. , 2017, Analytical chemistry.

[9]  Zhimou Guo,et al.  Two-dimensional strong cation exchange/positively charged reversed-phase liquid chromatography for alkaloid analysis and purification. , 2013, Journal of separation science.

[10]  Tao Zhang,et al.  Histamine H1 receptor cell membrane chromatography online high-performance liquid chromatography with mass spectrometry method reveals houttuyfonate as an activator of the histamine H1 receptor. , 2014, Journal of separation science.

[11]  Hua Yang,et al.  A strategy for screening antioxidants in Ginkgo biloba extract by comprehensive two-dimensional ultra high performance liquid chromatography. , 2015, Journal of chromatography. A.

[12]  Shuai Ji,et al.  Separation and characterization of phenolic compounds and triterpenoid saponins in licorice (Glycyrrhiza uralensis) using mobile phase-dependent reversed-phase×reversed-phase comprehensive two-dimensional liquid chromatography coupled with mass spectrometry. , 2015, Journal of chromatography. A.

[13]  Jian-Bo Wan,et al.  Qualitative and quantitative characterization of phenolic and diterpenoid constituents in Danshen (Salvia miltiorrhiza) by comprehensive two-dimensional liquid chromatography coupled with hybrid linear ion trap Orbitrap mass. , 2016, Journal of chromatography. A.

[14]  Shen Aijin,et al.  Development and Application of Hydrophilic Interaction Liquid Chromatographic Stationary Phases , 2014 .

[15]  G. Vivó-Truyols,et al.  Comprehensive study on the optimization of online two-dimensional liquid chromatographic systems considering losses in theoretical peak capacity in first- and second-dimensions: a Pareto-optimality approach. , 2010, Analytical chemistry.

[16]  Yu Jin,et al.  Evaluation and application of a mixed-mode chromatographic stationary phase in two-dimensional liquid chromatography for the separation of traditional Chinese medicine. , 2016, Journal of separation science.

[17]  Yafeng Guan,et al.  Multidimensional liquid chromatography system with an innovative solvent evaporation interface. , 2006, Journal of chromatography. A.

[18]  Jochen Vestner,et al.  Comprehensive Two-Dimensional Hydrophilic Interaction Chromatography (HILIC) × Reversed-Phase Liquid Chromatography Coupled to High-Resolution Mass Spectrometry (RP-LC-UV-MS) Analysis of Anthocyanins and Derived Pigments in Red Wine. , 2015, Analytical chemistry.

[19]  Ying Hu,et al.  Simultaneously targeted and untargeted multicomponent characterization of Erzhi Pill by offline two-dimensional liquid chromatography/quadrupole-Orbitrap mass spectrometry. , 2019, Journal of chromatography. A.

[20]  Yu Jin,et al.  Two-dimensional RPLC-RPLC system with different pH in two dimensions for separation of alkaloids from Corydalis yanhusuo W. T. Wang. , 2009, Journal of separation science.

[21]  Yu Jin,et al.  Purification of flavonoids from licorice using an off-line preparative two-dimensional normal-phase liquid chromatography/reversed-phase liquid chromatography method. , 2016, Journal of separation science.

[22]  Shuangyuan Wang,et al.  On-line stop-flow two-dimensional liquid chromatography–mass spectrometry method for the separation and identification of triterpenoid saponins from ginseng extract , 2014, Analytical and Bioanalytical Chemistry.

[23]  Zhimou Guo,et al.  Separation and characterization of bufadienolides in toad skin using two-dimensional normal-phase liquid chromatography×reversed-phase liquid chromatography coupled with mass spectrometry. , 2016, Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.

[24]  Yan Zhang,et al.  Discovery of N-methyltetrahydroprotoberberines with κ-opioid receptor agonists-opioid receptor agonist activities from corydalis yanhusuo W. T. Wang by using two-dimensional liquid chromatography. , 2014, Journal of ethnopharmacology.

[25]  Pavel Jandera,et al.  Column selectivity for two-dimensional liquid chromatography. , 2006, Journal of separation science.

[26]  Qing Fu,et al.  Comprehensive characterization of Stevia rebaudiana using two-dimensional reversed-phase liquid chromatography/hydrophilic interaction liquid chromatography. , 2012, Journal of separation science.

[27]  Davy Guillarme,et al.  Development of Comprehensive Online Two-Dimensional Liquid Chromatography/Mass Spectrometry Using Hydrophilic Interaction and Reversed-Phase Separations for Rapid and Deep Profiling of Therapeutic Antibodies. , 2018, Analytical chemistry.

[28]  Yanduo Tao,et al.  Antioxidative extracts and phenols isolated from Qinghai–Tibet Plateau medicinal plant Saxifraga tangutica Engl. , 2015 .

[29]  Yu Jin,et al.  Comprehensive HILIC × RPLC with mass spectrometry detection for the analysis of saponins in Panax notoginseng. , 2012, The Analyst.

[30]  O. Schmitz,et al.  Practical considerations in comprehensive two-dimensional liquid chromatography systems (LCxLC) with reversed-phases in both dimensions , 2014, Analytical and Bioanalytical Chemistry.

[31]  Shengli Han,et al.  Screening active compounds acting on the epidermal growth factor receptor from Radix scutellariae via cell membrane chromatography online coupled with HPLC/MS. , 2012, Journal of pharmaceutical and biomedical analysis.

[32]  Luigi Mondello,et al.  Employing ultra high pressure liquid chromatography as the second dimension in a comprehensive two-dimensional system for analysis of Stevia rebaudiana extracts. , 2011, Journal of chromatography. A.

[33]  Dwight R Stoll,et al.  Simulation of elution profiles in liquid chromatography - II: Investigation of injection volume overload under gradient elution conditions applied to second dimension separations in two-dimensional liquid chromatography. , 2017, Journal of chromatography. A.

[34]  Kai Chen,et al.  Two-dimensional liquid chromatography and its application in traditional Chinese medicine analysis and metabonomic investigation. , 2016, Journal of separation science.

[35]  Fan Yang,et al.  Preparative separation of a challenging anthocyanin from Lycium ruthenicum Murr. by two-dimensional reversed-phase liquid chromatography/hydrophilic interaction chromatography , 2015 .

[36]  Yanduo Tao,et al.  Two-dimensional hydrophilic interaction chromatography × reversed-phase liquid chromatography for the preparative isolation of potential anti-hepatitis phenylpropanoids from Salvia prattii. , 2016, Journal of separation science.

[37]  Tyge Greibrokk,et al.  Two-dimensional capillary liquid chromatography: pH gradient ion exchange and reversed phase chromatography for rapid separation of proteins. , 2006, Journal of chromatography. A.

[38]  Shuai Ji,et al.  Separation and detection of minor constituents in herbal medicines using a combination of heart-cutting and comprehensive two-dimensional liquid chromatography. , 2014, Journal of chromatography. A.

[39]  Xinmiao Liang,et al.  Two-dimensional LC-MS analysis of components in Swertia franchetiana Smith. , 2008, Journal of separation science.

[40]  Long Yu,et al.  A novel zwitterionic HILIC stationary phase based on "thiol-ene" click chemistry between cysteine and vinyl silica. , 2011, Chemical communications.

[41]  Li Zhang,et al.  Isolation and Identification of Water-Soluble Components of Lycium barbarum Leaves , 2019, Chemistry of Natural Compounds.

[42]  Qiang Wang,et al.  Comprehensive two-dimensional PC-3 prostate cancer cell membrane chromatography for screening anti-tumor components from Radix Sophorae flavescentis. , 2017, Journal of separation science.

[43]  Qinhua Chen,et al.  Screening active anti-breast cancer compounds from Cortex Magnolia officinalis by 2D LC-MS. , 2013, Journal of separation science.

[44]  Shuai Ji,et al.  Separation and characterization of chemical constituents in Ginkgo biloba extract by off‐line hydrophilic interaction × reversed‐phase two‐dimensional liquid chromatography coupled with quadrupole‐time of flight mass spectrometry , 2017, Journal of pharmaceutical and biomedical analysis.

[45]  Nicola Marchetti,et al.  Implementations of two-dimensional liquid chromatography. , 2008, Journal of chromatography. A.

[46]  Alejandro Cifuentes,et al.  Metabolite profiling of licorice (Glycyrrhiza glabra) from different locations using comprehensive two-dimensional liquid chromatography coupled to diode array and tandem mass spectrometry detection. , 2016, Analytica chimica acta.

[47]  Yafeng Guan,et al.  Comprehensive two-dimensional liquid chromatography (NPLCxRPLC) with vacuum-evaporation interface. , 2008, Journal of separation science.

[48]  Armando C. Duarte,et al.  Comprehensive multidimensional liquid chromatography for advancing environmental and natural products research , 2019, TrAC Trends in Analytical Chemistry.

[49]  Yanduo Tao,et al.  Preparative isolation of flavonoid glycosides from Sphaerophysa salsula using hydrophilic interaction solid-phase extraction coupled with two-dimensional preparative liquid chromatography. , 2017, Journal of separation science.

[50]  Zhen Wu,et al.  On-line comprehensive two-dimensional normal-phase liquid chromatography×reversed-phase liquid chromatography for preparative isolation of toad venom. , 2016, Journal of chromatography. A.

[51]  Caisheng Wu,et al.  Use of on-line stop-flow heart-cutting two-dimensional high performance liquid chromatography for simultaneous determination of 12 major constituents in tartary buckwheat (Fagopyrum tataricum Gaertn). , 2013, Journal of chromatography. A.

[52]  Hua Yang,et al.  An integrated evidence-based targeting strategy for determining combinatorial bioactive ingredients of a compound herbal medicine Qishen Yiqi dripping pills. , 2018, Journal of ethnopharmacology.

[53]  Yanduo Tao,et al.  Target separation of flavonoids from Saxifraga tangutica using two-dimensional hydrophilic interaction chromatography/reversed-phase liquid chromatography. , 2018, Journal of separation science.

[54]  Tyge Greibrokk,et al.  Recent advances in on-line multidimensional liquid chromatography , 2010 .

[55]  Xin Lu,et al.  Simultaneous separation of hydrophilic and hydrophobic compounds by using an online HILIC-RPLC system with two detectors. , 2008, Journal of separation science.

[56]  Yuzhi Fang,et al.  On-Line Two-Dimension Liquid Chromatography for the Analysis of Ingredients in the Medicinal Preparation of Coptis Chinensis Franch , 2011 .

[57]  Yu Jin,et al.  Combination of off-line two-dimensional hydrophilic interaction liquid chromatography for polar fraction and two-dimensional hydrophilic interaction liquid chromatography×reversed-phase liquid chromatography for medium-polar fraction in a traditional Chinese medicine. , 2012, Journal of chromatography. A.

[58]  Jingyu Yan,et al.  Orthogonal separation and identification of long-chain peptides from scorpion Buthus martensi Karsch venom by using two-dimensional mixed-mode reversed phase-reversed phase chromatography coupled to tandem mass spectrometry. , 2013, The Analyst.

[59]  Luigi Mondello,et al.  Comprehensive two-dimensional liquid chromatography , 2017 .

[60]  Zhe Wang,et al.  Comprehensive two-dimensional liquid chromatography coupled with quadrupole time-of-flight mass spectrometry for chemical constituents analysis of tripterygium glycosides tablets. , 2015, Journal of chromatography. A.

[61]  Rongji Dai,et al.  Offline Two-Dimensional RP/RPLC Method to Separate Components in Dracaena cochinchinensis (Lour.) S.C.Chen Xylem Containing Resin , 2011 .

[62]  Shilong Mao,et al.  Comprehensive two-dimensional high performance liquid chromatography system with immobilized liposome chromatography column and monolithic column for separation of the traditional Chinese medicine Schisandra chinensis. , 2012, Analytica chimica acta.

[63]  Oliver Fiehn,et al.  Analysis of highly polar compounds of plant origin: combination of hydrophilic interaction chromatography and electrospray ion trap mass spectrometry. , 2002, Analytical biochemistry.

[64]  O. Schmitz,et al.  Comprehensive two-dimensional liquid chromatography tandem diode array detector (DAD) and accurate mass QTOF-MS for the analysis of flavonoids and iridoid glycosides in Hedyotis diffusa , 2014, Analytical and Bioanalytical Chemistry.

[65]  Xiaoqian Zhang,et al.  Bioassay-Guided Separation and Identification of a New Anti-Lung Cancer Compound from Cordyceps militaris by Means of Off-Line Two-Dimensional Preparative Chromatography, Real-Time Cell Analysis, and X-ray Single-Crystal Diffraction , 2015, Chromatographia.

[66]  C. Venkatramani,et al.  Assessing stability-indicating methods for coelution by two-dimensional liquid chromatography with mass spectrometric detection. , 2014, Journal of separation science.

[67]  Wei Song,et al.  Separation and Characterization of Triterpenoid Saponins in Gleditsia sinensis by Comprehensive Two-Dimensional Liquid Chromatography Coupled with Mass Spectrometry , 2016, Planta Medica.

[68]  O. Schmitz,et al.  The advantage of mixed-mode separation in the first dimension of comprehensive two-dimensional liquid-chromatography. , 2014, Journal of chromatography. A.

[69]  L. Mondello,et al.  Comprehensive two-dimensional liquid chromatography with parallel gradients for separation of phenolic and flavone antioxidants. , 2007, Journal of chromatography. A.

[70]  Pat Sandra,et al.  Comprehensive liquid chromatography: fundamental aspects and practical considerations--a review. , 2009, Analytica chimica acta.

[71]  Hong MA,et al.  Bioassay-guided Separation of Anti-tumor Components from Euphorbia kansui by Means of Two-dimensional Preparative High Performance Liquid Chromatography and Real-time Cell Analysis. , 2016, Analytical sciences : the international journal of the Japan Society for Analytical Chemistry.

[72]  A. Alpert.  Hydrophilic-interaction chromatography for the separation of peptides, nucleic acids and other polar compounds. , 1990, Journal of chromatography.

[73]  J. Seeley,et al.  Theoretical study of incomplete sampling of the first dimension in comprehensive two-dimensional chromatography. , 2002, Journal of chromatography. A.

[74]  Zhimou Guo,et al.  Purification of polar compounds from Radix isatidis using conventional C18 column coupled with polar-copolymerized C18 column. , 2010, Journal of separation science.

[75]  Jing Ma,et al.  An online coupled breast cancer cell membrane chromatography with HPLC/MS for screening active compounds from Fructus evodiae , 2013 .

[76]  Na Shen,et al.  Anti-inflammatory bioactive equivalence of combinatorial components β-carboline alkaloids identified in Arenaria kansuensis by two-dimensional chromatography and solid-phase extraction coupled with liquid-liquid extraction enrichment technology. , 2017, Journal of separation science.

[77]  Jing Zhang,et al.  Purification of active bufadienolides from toad skin by preparative reversed-phase liquid chromatography coupled with hydrophilic interaction chromatography. , 2010, Journal of separation science.

[78]  Xin Lu,et al.  Development of a comprehensive two-dimensional hydrophilic interaction chromatography/quadrupole time-of-flight mass spectrometry system and its application in separation and identification of saponins from Quillaja saponaria. , 2008, Journal of chromatography. A.

[79]  Shengli Han,et al.  Overview of online two-dimensional liquid chromatography based on cell membrane chromatography for screening target components from traditional Chinese medicines. , 2017, Journal of separation science.

[80]  Liangliang Liu,et al.  Integration of magnetic solid phase fishing and off-line two-dimensional high-performance liquid chromatography-diode array detector-mass spectrometry for screening and identification of human serum albumin binders from Radix Astragali. , 2014, Food chemistry.

[81]  Shuai Ji,et al.  The application of on‐line two‐dimensional liquid chromatography (2DLC) in the chemical analysis of herbal medicines , 2018, Journal of pharmaceutical and biomedical analysis.

[82]  Zhimou Guo,et al.  Polar-copolymerized approach based on horizontal polymerization on silica surface for preparation of polar-modified stationary phases. , 2010, Journal of chromatography. A.

[83]  G. Sassaki,et al.  Analysis of Camellia sinensis green and black teas via ultra high performance liquid chromatography assisted by liquid-liquid partition and two-dimensional liquid chromatography (size exclusion × reversed phase). , 2012, Journal of chromatography. A.

[84]  Yu Jin,et al.  Orthogonal separation on one beta-cyclodextrin column by switching reversed-phase liquid chromatography and hydrophilic interaction chromatography. , 2010, Talanta.

[85]  Peter J Schoenmakers,et al.  Optimizing separations in online comprehensive two‐dimensional liquid chromatography , 2017, Journal of separation science.

[86]  Xinmiao Liang,et al.  2-D RP/RPLC method to separate components in Fructus schisandrae chinensis. , 2010, Journal of separation science.

[87]  S. Heinisch,et al.  On-line comprehensive two-dimensional separations of charged compounds using reversed-phase high performance liquid chromatography and hydrophilic interaction chromatography. Part I: orthogonality and practical peak capacity considerations. , 2012, Journal of chromatography. A.

[88]  Shengli Han,et al.  Screening epidermal growth factor receptor antagonists from Radix et Rhizoma Asari by two-dimensional liquid chromatography. , 2014, Journal of separation science.

[89]  Ye Fang,et al.  Discovery of β2- adrenoceptor agonists in Curcuma zedoaria Rosc using label-free cell phenotypic assay combined with two-dimensional liquid chromatography. , 2018, Journal of chromatography. A.

[90]  Zhimou Guo,et al.  Separation and identification of flavonoids from complex samples using off-line two-dimensional liquid chromatography tandem mass spectrometry. , 2012, Journal of chromatography. A.

[91]  Zhimou Guo,et al.  Recent development in liquid chromatography stationary phases for separation of Traditional Chinese Medicine components. , 2016, Journal of pharmaceutical and biomedical analysis.

[92]  Mei-Juan Fang,et al.  On-line comprehensive two-dimensional normal-phase liquid chromatography × reversed-phase liquid chromatography for preparative isolation of Peucedanum praeruptorum. , 2015, Journal of chromatography. A.

[93]  De-An Guo,et al.  Method development and application of offline two-dimensional liquid chromatography/quadrupole time-of-flight mass spectrometry-fast data directed analysis for comprehensive characterization of the saponins from Xueshuantong Injection. , 2016, Journal of pharmaceutical and biomedical analysis.

[94]  Min Yang,et al.  Simultaneous quantitation of five Panax notoginseng saponins by multi heart-cutting two-dimensional liquid chromatography: Method development and application to the quality control of eight Notoginseng containing Chinese patent medicines. , 2015, Journal of chromatography. A.

[95]  Shengli Han,et al.  A high expression Mas‐related G protein coupled receptor X2 cell membrane chromatography coupled with liquid chromatography and mass spectrometry method for screening potential anaphylactoid components in kudiezi injection , 2018, Journal of pharmaceutical and biomedical analysis.

[96]  Jian-Bo Wan,et al.  Application of two-dimensional chromatography in the analysis of Chinese herbal medicines. , 2014, Journal of chromatography. A.

[97]  M. Krauze-Baranowska,et al.  Application of one- and two-dimensional high-performance liquid chromatography methodologies for the analysis of C-glycosylflavones from fenugreek seeds. , 2014, Journal of chromatography. A.

[98]  Jingyu Yan,et al.  On-line comprehensive two-dimensional liquid chromatography tandem mass spectrometry for the analysis of Curcuma kwangsiensis. , 2018, Talanta.

[99]  Zhengtao Wang,et al.  Comprehensive two-dimensional high-performance liquid chromatography system with immobilized liposome chromatography column and reversed-phase column for separation of complex traditional Chinese medicine Longdan Xiegan Decoction. , 2009, Journal of chromatography. A.

[100]  Zhimou Guo,et al.  Development of orthogonal two-dimensional hydrophilic interaction chromatography systems with the introduction of novel stationary phases. , 2009, Journal of separation science.

[101]  Zhimou Guo,et al.  Purification of saponins from leaves of Panax notoginseng using preparative two-dimensional reversed-phase liquid chromatography/hydrophilic interaction chromatography , 2013, Analytical and Bioanalytical Chemistry.

[102]  Yu Jin,et al.  "Click dipeptide": a novel stationary phase applied in two-dimensional liquid chromatography. , 2009, Journal of chromatography. A.

[103]  Xinmiao Liang,et al.  Characterization of polymethoxylated flavones in Fructus aurantii by off-line two-dimensional liquid chromatography/electrospray ionization-ion trap mass spectrometry. , 2009, Journal of pharmaceutical and biomedical analysis.

[104]  Huaizhen He,et al.  Targeting Analysis of Gallic Acid and Bioactive Components in Xuebijing Injection with Loop-based Heart-cutting Two-dimensional Liquid Chromatography , 2018, Current Pharmaceutical Analysis.

[105]  Zhimou Guo,et al.  Efficient purification of high-purity compounds from the stem of Lonicera japonica Thunb using two-dimensional preparative chromatography. , 2013, Journal of separation science.

[106]  Qionglin Liang,et al.  A simple way to configure on-line two-dimensional liquid chromatography for complex sample analysis: acquisition of four-dimensional data. , 2012, Talanta.

[107]  Zhimou Guo,et al.  Novel two-dimensional reversed-phase liquid chromatography/hydrophilic interaction chromatography, an excellent orthogonal system for practical analysis. , 2008, Journal of chromatography. A.

[108]  Dwight R Stoll,et al.  Dependence of effective peak capacity in comprehensive two-dimensional separations on the distribution of peak capacity between the two dimensions. , 2008, Analytical chemistry.

[109]  Yu Jin,et al.  Purification of amide alkaloids from Piper longum L. using preparative two-dimensional normal-phase liquid chromatography × reversed-phase liquid chromatography. , 2013, The Analyst.

[110]  Mei-Juan Fang,et al.  Development of an on-line mixed-mode gel liquid chromatography×reversed phase liquid chromatography method for separation of water extract from Flos Carthami. , 2017, Journal of chromatography. A.