Identification of carbohydrate isomers in flavonoid glycosides after hydrolysis by hydrophilic interaction chromatography

Chemical Papers

Volumn 67, Issue 4, 2013, Pages 357-364

  Špačková, Věra ^a   Pazourek, Jiří ^a  

^a UNIVERSITY OF VETERINARY AND PHARMACEUTICAL SCIENCES   (Czech Republic)

Author keywords

acidic hydrolysis; enzymatic hydrolysis; glycosides; HILIC; identification of isomers

Indexed keywords

EID: 84873410944     PISSN: 03666352     EISSN: 13369075     Source Type: Journal    
DOI: 10.2478/s11696-012-0302-8     Document Type: Article

References (36)

1. Abrankó, L., García-Reyes, J. F., & Molina-Díaz, A. (2012). Systematic bottom-up approach for flavonoid derivative screening in plant material using liquid chromatography high-resolution mass spectrometry. Analytical and Bioanalytical Chemistry, 403, 995-1006. DOI: 10.1007/s00216-012- 5865-2.
2. Brito-Arias, M. (2007). Synthesis and characterization of glycosides. New York, NY, USA: Springer.
3. Chandler, B. V., & Harper, K. A. (1961). Identification of saccharides in anthocyanins and other flavonoids. Australian Journal of Chemistry, 14, 586-595. DOI: 10.1071/ch9610586.
4. Chassagne, D., Crouzet, J., Bayonove, C. L., & Baumes, R. L. (1998). Identification of passion fruit glycosides by gas chromatography/mass spectrometry. Journal of Agricultural and Food Chemistry, 46, 4352-4357. DOI: 10.1021/jf980416k.
5. Chen, H., & Zuo, Y. (2007). Identification of flavonol glycosides in American cranberry fruit. Food Chemistry, 101, 1357-1364. DOI:10.1016/j. foodchem.2006.03.041.
6. n methods for saccharide characterization of monoglycosyl flavonoids using postcolumn manganese complexation. Analytical Chemistry, 77, 1883-1890. DOI: 10.1021/ac048374o.
7. Eom, H. Y., Park, S. Y., Kim, M. K., Suh, J. H., Yeom, H., Min, J. W., Kim, U., Lee, J., Youm, J. R., & Han, S. B. (2010). Comparison between evaporative light scattering detection and charged aerosol detection for the analysis of saikosaponins. Journal of Chromatography A, 1217, 4347-4354. DOI:10.1016/j.chroma.2010.04.047.
8. Fan, P., Terrier, L., Hay, A. E., Marston, A., & Hostettmann, K. (2010). Antioxidant and enzyme inhibition activities and chemical profiles of Polygonum sachalinensis F.Schmidt ex Maxim (Polygonaceae). Fitoterapia, 81, 124-131. DOI:10.1016/j.fitote.2009.08.019.
9. Garegg, P. J. (2004). Synthesis and reactions of glycosides. Advances in Carbohydrate Chemistry and Biochemistry, 59, 69-134. DOI: 10.1016/s0065-2318(04) 59003-0.
10. Godin, B., Agneessens, R., Gerin, P. A., & Delcarte, J. (2011). Composition of structural carbohydrates in biomass: Precision of a liquid chromatography method using a neutral detergent extraction and a charged aerosol detector. Talanta, 85, 2014-2026. DOI:10.1016/j.talanta.2011.07.044.
11. Harborne, J. B. (1965). Plant polyphenols - XIV.: Characterization of flavonoid glycosides by acidic and enzymic hydrolyses. Phytochemistry, 4, 107-120. DOI: 10.1016/s0031-9422(00)86152-x.
12. Hernández-Hernández, O., Calvillo, I., Lebrón- Aguilar, R., Moreno, F. J., & Sanz, M. L. (2012). Hydrophilic interaction liquid chromatography coupled to mass spectrometry for the characterization of prebiotic galactooligosaccharides. Journal of Chromatography A, 1220, 57-67. DOI:10.1016/j.chroma.2011.11.047.
13. Ikegami, T., Horie, K., Saad, N., Hosoya, K., Fiehn, O., & Tanaka, N. (2008). Highly efficient analysis of underivatized carbohydrates using monolithic-silica-based capillary hydrophilic interaction (HILIC) HPLC. Analytical and Bioanalytical Chemistry, 391, 2533-2542. DOI: 10.1007/s00216-008-2060-6.
14. Inoue, K., Yamazaki, K., Kitahara, K. I., Aikawa, Y., Arai, S., & Masuda-Hanada, T. (2012). Erratum: Synthesis of new di-cation type stationary phases for high performance anion-exchange chromatographic separation of carbohydrates. Bunseki Kagaku, 61, 133. DOI: 10.2116/bunsekikagaku. 61.133.
15. Kadumi, K., Yamazaki, K., Kitahara, K. I., Aikawa, Y., Arai, S., & Masuda-Hanada, T. (2011). Synthesis of new di-cation type stationary phases for high performance anion-exchange chromatographic separation of carbohydrates. Bunseki Kagaku, 60, 959-964. DOI: 10.2116/bunsekikagaku.60.959.
16. Kawai, Y., Kumagai, H., Kurihara, H., Yamazaki, K., Sawano, R., & Inoue, N. (2006). β-Glucosidase inhibitory activities of phenylpropanoid glycosides, vanicoside A and B from Polygonum sachalinense rhizome. Fitoterapia, 77, 456-459. DOI:10.1016/j.fitote.2006.05.008.
17. Kim, Y. S., Yeom, S. J., & Oh, D. K. (2011). Characterization of a GH3 family β-glucosidase from Dictyoglomus turgidum and its application to the hydrolysis of isoflavone glycosides in spent coffee grounds. Journal of Agricultural and Food Chemistry, 59, 11812-11818. DOI:10.1021/jf2025192.
18. Lin, L. Z., & Harnly, J. M. (2007). A screening method for the identification of glycosylated flavonoids and other phenolic compounds using a standard analytical approach for all plant materials. Journal of Agricultural and Food Chemistry, 55, 1084-1096. DOI: 10.1021/jf062431s.
19. Litvinenko, V. I., & Makarov, V. A. (1969). The alkaline hydrolysis of flavonoid glycosides. Chemistry of Natural Compounds, 5, 305-306. DOI: 10.1007/bf00595062.
20. Lommen, A., Godejohann, M., Venema, D. P., Hollman, P. C. H., & Spraul, M. (2000). Application of directly coupled HPLC-NMR-MS to the identification and confirmation of quercetin glycosides and phloretin glycosides in apple peel. Analytical Chemistry, 72, 1793-1797. DOI: 10.1021/ac9912303.
21. Lundborg, M., Fontana, C., & Widmalm, G. (2011). Automatic structure determination of regular polysaccharides based solely on NMR spectroscopy. Biomacromolecules, 12, 3851-3855. DOI: 10.1021/bm201169y.
22. Ma, X. X., Wang, D., Zhang, Y. J., & Yang, C. R. (2011). Identification of new qingyangshengenin and caudatin glycosides from the roots of Cynanchum otophyllum. Steroids, 76, 1003-1009. DOI:10.1016/j.steroids.2011. 03.019.
23. Molnár-Perl, I., & Füzfai, Z. (2005). Chromatographic, capillary electrophoretic and capillary electrochromatographic techniques in the analysis of flavonoids. Journal of Chromatography A, 1073, 201-227. DOI:10.1016/j.chroma.2004.10.068.
24. Nehme, C. J., Bastos, W. L., de Araújo, A. J., & Cavalheiro, A. J. (2005). An HPLC-PAD method to analyse flavonoid glycosides and styrylpyrones from Cryptocarya species (lauraceae). Phytochemical Analysis, 16, 93-97. DOI: 10.1002/pca.818.
25. Pazourek, J. (2010). Monitoring of mutarotation of monosaccharides by hydrophilic interaction chromatography. Journal of Separation Science, 33, 974-981. DOI:10.1002/jssc.20090 0880.
26. Pieretti, G., Carillo, S., Lanzetta, R., Parrilli, M., Merino, S., Tomás, J. M., & Corsaro, M. M. (2011). Structural determination of the O-specific polysaccharide from Aeromonas hydrophila strain A19 (serogroup O:14) with S-layer. Carbohydrate Research, 346, 2519-2522. DOI:10.1016/j.carres. 2011. 08.003.
27. Qiu, H., Loukotková, L., Sun, P., Tesařová, E., Bosáková, Z., & Armstrong, D. W. (2011). Cyclofructan 6 based stationary phases for hydrophilic interaction liquid chromatography. Journal of Chromatography A, 1218, 270-279. DOI:10.1016/j.chroma.2010.11.027.
28. Quintin, J., & Lewin, G. (2005). Mild alkaline hydrolysis of some 7-O-flavone glycosides. Application to a novel access to rutinose heptaacetate. Tetrahedron Letters, 46, 4341-4343. DOI:10.1016/j.tetlet.2005.04.085.
29. Rassi, Z. E. (1995). Carbohydrate analysis: High performance liquid chromatography and capillary electrophoresis. Amsterdam, The Netherlands: Elsevier.
30. Ricochon, G., Paris, C., Girardin, M., & Muniglia, L. (2011). Highly sensitive, quick and simple quantification method for mono and disaccharides in aqueous media using liquid chromatography-atmospheric pressure chemical ionization-mass spectrometry (LC-APCI-MS). Journal of Chromatography B, 879, 1529-1536. DOI:10.1016/j.jchromb.2011.03. 044.
31. Rotrekl, V. (1998). Rostlinné β-glukosidasy. Chemické Listy, 92, 883-893. (in Czech)
32. Stalikas, C. D. (2007). Extraction, separation, and detection methods for phenolic acids and flavonoids. Journal of Separation Science, 30, 3268-3295. DOI:10.1002/jssc.200700261.
33. Thabti, I., Elfalleh, W., Hannachi, H., Ferchichi, A., & Campos, M. D. G. (2012). Identification and quantification of phenolic acids and flavonol glycosides in Tunisian Morus species by HPLC-DAD and HPLC-MS. Journal of Functional Foods, 4, 367-374. DOI:10.1016/j.jff.2012.01.006.
34. Zahid, M., Ishrud, O., Pan, Y., Asim, M., Riaz, M., & Ahmad, U. V. (2002). Flavonoid glycosides from Salvia moorcroftiana Wall. Carbohydrate Research, 337, 403-407. DOI: 10.1016/s0008-6215(02)00008-3.
35. Zhang, J. M., Wang, J., & Brodbelt, J. S. (2005). Characterization of flavonoids by aluminum complexation and collisionally activated dissociation. Journal of Mass Spectrometry, 40, 350-363. DOI: 10.1002/jms.793.
36. Zhang, H., Yang, H., Zhang, M., Wang, Y., Wang, J., Yau, L., Jiang, Z., & Hu, P. (2012). Identification of flavonol and triterpene glycosides in Luo-Han-Guo extract using ultrahigh performance liquid chromatography/quadrupole time-of-flight mass spectrometry. Journal of Food Composition and Analysis, 25, 142-148. DOI:10.1016/j.jfca.2011.09.004.