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

Journal of Chromatography A

Volumn 1402, Issue , 2015, Pages 36-45

  Qiao, Xue ^a   Song, Wei ^a   Ji, Shuai ^a   Wang, Qi ^a   Guo, De an ^a,b   Ye, Min ^a,b  

^a PEKING UNIVERSITY HEALTH SCIENCE CENTER   (China)

^b SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

2DLC; Glycyrrhiza uralensis; Licorice; Phenolic compounds; Triterpenoid saponins

Indexed keywords

MASS SPECTROMETRY; PHENOLS; PLANT EXTRACTS; SEPARATION;

2DLC; GLYCYRRHIZA URALENSIS; LICORICE; PHENOLIC COMPOUNDS; TRITERPENOID SAPONINS;

LIQUID CHROMATOGRAPHY;

22 ACETOXYLGLYCYRRHIZIN; 5,7,4' TRIHYDROXY 3'(3 METHYLBUT 2 ENYL) 3 METHOXYFLAVONE; ALLOLICOISOFLAVONE B; ANGUSTONE A; GANCAONIN I; GLYCYROL; GLYCYRRHIZA URALENSIS EXTRACT; GLYCYRRHIZIC ACID; ISOANGUSTONE A; ISOGLYCYROL; ISOLIQUIRITIN; ISOLIQUIRITIN APIOSIDE; LICOFLAVONOL; LICOISOFLAVONE A; LICORICE SAPONIN A3; LICORICE SAPONIN E2; LICORICE SAPONIN G2; LICORICE SAPONIN H2; LICORICE SAPONIN J2; LICORICONE; LIQUIRITIN; LIQUIRITIN APIOSIDE; PHENOL DERIVATIVE; SAPONIN; SEMILICOISOFLAVONE B; TOPAZOLIN; TRITERPENOID; UNCLASSIFIED DRUG; UNINDEXED DRUG; URALSAPONIN B; WIGHTEONE; ACETONITRILE; ACETONITRILE DERIVATIVE; COUMARIN DERIVATIVE; FLAVONOID;

ARTICLE; CHEMICAL STRUCTURE; CONTROLLED STUDY; MASS SPECTROMETRY; MOBILE PHASE DEPENDENT REVERSED PHASE X REVERSED PHASECOMPREHENSIVE TWO DIMENSIONAL LIQUID CHROMATOGRAPHY; NONHUMAN; PLANT ROOT; PRIORITY JOURNAL; PROCESS OPTIMIZATION; REVERSED PHASE LIQUID CHROMATOGRAPHY; SEPARATION TECHNIQUE; CHEMICAL ANALYSIS; CHEMISTRY; GLYCYRRHIZA; GLYCYRRHIZA URALENSIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

GLYCYRRHIZA; GLYCYRRHIZA URALENSIS;

ACETONITRILES; CHEMISTRY TECHNIQUES, ANALYTICAL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CHROMATOGRAPHY, REVERSE-PHASE; COUMARINS; FLAVONOIDS; GLYCYRRHIZA; GLYCYRRHIZA URALENSIS; MASS SPECTROMETRY; PHENOLS; PLANT ROOTS; SAPONINS;

EID: 84930572588     PISSN: 00219673     EISSN: 18733778     Source Type: Journal    
DOI: 10.1016/j.chroma.2015.05.006     Document Type: Article

References (39)

1. Zhang Q., Ye M. Chemical analysis of the Chinese herbal medicine Gan-Cao (licorice). J. Chromatogr. A 2009, 1216:1954-1969.
2. Xiang C., Qiao X., Ye M., Guo D.A. Classification and distribution analysis of components in Glycyrrhiza using licorice compounds database. Acta Pharm. Sin. 2012, 47:1023-1030.
3. Song W., Si L., Ji S., Wang H., Fang X., Yu L., Li R., Liang L., Zhou D., Ye M. Uralsaponins M-Y, antiviral triterpenoid saponins from the roots of Glycyrrhiza uralensis. J. Nat. Prod. 2014, 77:1632-1643.
4. Cuendet M., Guo J., Luo Y., Chen S., Oteham C.P., Moon R.C., van Breemen R.B., Marler L.E., Pezzuto J.M. Cancer chemopreventive activity and metabolism of isoliquiritigenin, a compound found in licorice. Cancer Prev. Res. 2010, 3:221-232.
5. Chen L., Chen W., Qian X., Fang Y., Zhu N. Liquiritigenin alleviates mechanical and cold hyperalgesia in a rat neuropathic pain model. Sci. Rep. 2014, 4:5676. Article ID.
6. Huang W., Tang S., Qiao X., Ma W., Ji S., Wang K., Ye M., Yu S. Isoangustone A induces apoptosis in SW480 human colorectal adenocarcinoma cells by disrupting mitochondrial functions. Fitoterapia 2014, 94:36-47.
7. Adianti M., Aoki C., Komoto M., Deng L., Shoji I., Wahyuni T.S., Lusida M.I., Soetjipto H., Fuchino N., Kawahara H.Hotta Anti-hepatitis C virus compounds obtained from Glycyrrhiza uralensis and other Glycyrrhiza species. Microbiol. Immunol. 2014, 58:180-187.
8. Qiao X., Ji S., Yu S.W., Lin X.H., Jin H.W., Duan Y.K., Zhang L.R., Guo D.A., Ye M. Identification of key licorice constituents which interact with cytochrome P450: evaluation by LC/MS/MS cocktail assay and metabolic profiling. AAPS J. 2014, 16:101-113.
9. Zhang Y., Cao J., Wang Y., Xiao S. Simultaneous determination of glycyrrhizin and 15 flavonoids in licorice and blood by high performance liquid chromatography with ultraviolet detector. ISRN Anal. Chem. 2013, Article ID 786151.
10. Kong W., Wen J., Yang Y., Qiu F., Sheng P., Yang M. Simultaneous targeted analysis of five active compounds in licorice by ultra-fast liquid chromatography coupled to hybrid linear-ion trap tandem mass spectrometry. Analyst 2014, 139:1883-1894.
11. Farag M.A., Porzel A., Wessjohann L.A. Comparative metabolite profiling and fingerprinting of medicinal licorice roots using a multiplex approach of GC-MS, LC-MS and 1D NMR techniques. Phytochemistry 2012, 76:60-72.
12. Simons R., Vincken J.P., Bakx E.J., Verbruggen M.A., Gruppen H. A rapid screening method for prenylated flavonoids with ultra-high-performance liquid chromatography/electrospray ionisation mass spectrometry in licorice root extracts. Rapid Commun. Mass Spectrom. 2009, 23:3083-3093.
13. Li Y.J., Chen J., Li Y., Li Q., Zheng Y.F., Fu Y., Li P. Screening and characterization of natural antioxidants in four Glycyrrhiza species by liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry. J. Chromatogr. A 2011, 1218:8181-8191.
14. Xu T., Yang M., Li Y., Chen X., Wang Q., Deng W., Pang X., Yu K., Jiang B., Guan S., Guo D. An integrated exact mass spectrometric strategy for comprehensive and rapid characterization of phenolic compounds in licorice. Rapid Commun. Mass Spectrom. 2013, 27:2297-2309.
15. Qiao X., Liu C., Ji S., Lin X.H., Guo D.A., Ye M. Simultaneous determination of five minor coumarins and flavonoids in Glycyrrhiza uralensis by solid-phase extraction and high-performance liquid chromatography/electrospray ionization tandem mass spectrometry. Planta Med. 2014, 80:237-242.
16. Dugo P., Cacciola F., Kumm T., Dugo G., Mondello L. Comprehensive multidimensional liquid chromatography: theory and applications. J. Chromatogr. A 2008, 1184:353-368.
17. Cao J.L., Wei J.C., Chen M.W., Su H.X., Wan J.B., Wang Y.T., Li P. Application of two-dimensional chromatography in the analysis of Chinese herbal medicines. J. Chromatogr. A 2014, 1371:1-14.
18. Qiao X., Song W., Ji S., Li Y., Wang Y., Li R., An R., Guo D., Ye M. Separation and detection of minor constituents in herbal medicines using a combination of heart-cutting and comprehensive two-dimensional liquid chromatography. J. Chromatogr. A 2014, 1362:157-167.
19. Le Masle A., Angot D., Gouin C., D'Attoma A., Ponthus J., Quignard A., Heinisch S. Development of on-line comprehensive two-dimensional liquid chromatography method for the separation of biomass compounds. J. Chromatogr. A 2014, 1340:90-98.
20. Cong J., Lin B. Study of separation conditions of active components in licorice with two-dimensional liquid chromatography. J. Liq. Chromatogr. Relat. Technol. 2008, 31:891-911.
21. Cong J., Wang S., Gao H. Separation of liquiritin by two-dimensional liquid chromatography. Adv. Mater. Res. 2012, 455-456:1232-1238.
22. Ikegami T., Hara T., Kimura H., Kobayashi H., Hosoya K., Cabrera K., Tanaka N. Two-dimensional reversed-phase liquid chromatography using two monolithic silica C18 columns and different mobile phase modifiers in the two dimensions. J. Chromatogr. A 2006, 1106:112-117.
23. Wang Q., Miao W.J., Xiang C., Guo D.A., Ye M. Chemical constituents from Glycyrrhiza uralensis. Chin. Trad. Herbal Med. 2012, 43:1886-1890.
24. Wang Q., Miao W.J., Xiang C., Guo D.A., Ye M. Chemical constituents in flavonoids from roots of Glycyrrhiza uralensis. Chin. Trad. Herbal Med. 2014, 45:31-36.
25. Cohen S.A., Schure M.R. Multidimensional Liquid Chromatography: Theory and Applications in Industrial Chemistry and the Life Sciences 2008, 171. John Wiley & Sons, New Jersey.
26. Li X., Stoll D.R., Carr P.W. Equation for peak capacity estimation in two-dimensional liquid chromatography. Anal. Chem. 2009, 81:845-850.
27. Gilar M., Olivova P., Daly A.E., Gebler J.C. Orthogonality of separation in two-dimensional liquid chromatography. Anal. Chem. 2005, 77:6426-6434.
28. Snyder L.R., Kirkland J.J., Dolan J.W. Introduction to Modern Liquid Chromatography 2010, 34. John Wiley & Sons, Inc., New Jersey. third ed.
29. Li D., Schmit O.J. Use of shift gradient in the second dimension to improve the separation space in comprehensive two-dimensional liquid chromatography. Anal. Bioanal. Chem. 2013, 405:6511-6517.
30. Leme G.M., Cacciola F., Donato P., Cavalheiro A.J., Dugo P., Mondello L. Continuous vs. segmented second-dimension system gradients for comprehensive two-dimensional liquid chromatography of sugarcane (Saccharum spp.). Anal. Bioanal. Chem. 2014, 406:4315-4324.
31. Brinda B.J., Hao-Jie Zhu, John S.Markowitz A sensitive LC-MS/MS assay for the simultaneous analysis of the major active components of silymarin in human plasma. J. Chromatogr. B 2012, 902:1-9.
32. Fukai T., Wang Q.H., Nomura T. Phenolic constituents of Glycyrrhiza. Part 2. Four new prenylated flavonoids from aerial parts of Glycyrrhiza uralensis. Heterocycles 1989, 29:1369-1378.
33. Jia S.S., Ma C.M., Wang J.M. Studies on flavonoid constituents isolated from the leaves of Glycyrrhiza uralensis Fish. Acta Pharm. Sin. 1990, 25:758-762.
34. Kiuchi F., Chen X., Tsuda Y. Four new phenolic constituents from licorice (root of Glycyrrhiza sp.). Heterocycles 1990, 31:629-636.
35. Hatano T., Shintani Y., Aga Y., Shiota S., Tisuchiya T., Yoshida T. Phenolic constituents of licorice. VIII. Structures of glicophenone and glicoisoflavanone, and effects of licorice phenolics on methicillin-resistant Staphylococcus aureus. Chem. Pharm. Bull. 2000, 48:1286-1292.
36. Hatano T., Fukuda T., Miyase T., Noro T., Okuda T. Phenolic constituents of licorice. III. Structures of glicoricone and licofuranone, and inhibitory effects of licorice constituents on monoamine oxidase. Chem. Pharm. Bull. 1991, 39:1238-1243.
37. Mitscher L.A., Park Y.H., Clark D., Beal J.L. Antimicrobial agents from higher plants. Antimicrobial isoflavanoids and related substances from Glycyrrhiza glabra L. var. typica. J. Nat. Prod. 1980, 43:259-269.
38. Zeng L., Fukai T., Kaneki T., Nomura T., Zhang R., Lou Z. Four new isoprenoid- substituted dibenzoylmethane derivatives, glyinflanins A, B, C, and D from the roots of Glycyrrhiza inflata. Heterocycles 1992, 34:85-97.
39. Fukai T., Tantai L., Nomura T. Isoprenoid-substituted flavonoids from Glycyrrhiza glabra. Phytochemistry 1996, 43:531-532.