Practical guidelines for characterization of O-diglycosyl flavonoid isomers by triple quadrupole MS and their applications for identification of some fruit juices flavonoids

Journal of Mass Spectrometry

Volumn 44, Issue 7, 2009, Pages 1017-1025

  Abad Garcia B ^a   Garmon Lobato S ^a   Berrueta, L A ^a   Gallo, B ^a   Vicente, F ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

Citrus juice; Diglycosides; Flavonoids characterization; LC MS; Mass spectrometry; Neohesperidosides; Rutinosides

Indexed keywords

CITRUS JUICE; DIGLYCOSIDES; FLAVONOIDS CHARACTERIZATION; LC/MS; NEOHESPERIDOSIDES; RUTINOSIDES;

CHROMATOGRAPHIC ANALYSIS; ELECTROSPRAY IONIZATION; ESTERIFICATION; FRUITS; GLYCOSYLATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMERS; MASS SPECTROMETERS; MASS SPECTROMETRY; SUGARS;

FRUIT JUICES;

ANTHOCYANIN; CITRIC ACID; FLAVONOID; GLYCOSIDE; O DIGLYCOSYL FLAVONOID; UNCLASSIFIED DRUG;

ARTICLE; CITRUS FRUIT; DIODE; ELECTROSPRAY; GLYCOSYLATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LEMON JUICE; MASS SPECTROMETRY; PRIORITY JOURNAL; TANDEM MASS SPECTROMETRY; ULTRAVIOLET SPECTROSCOPY;

BEVERAGES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CITRUS; FLAVANONES; FLAVONOIDS; FRUIT; GLYCOSYLATION; ISOMERISM; QUERCETIN; RUTIN; TANDEM MASS SPECTROMETRY;

CITRUS;

EID: 67650459992     PISSN: 10765174     EISSN: 10969888     Source Type: Journal    
DOI: 10.1002/jms.1573     Document Type: Article

References (37)

1. J. A. T. Pennington. Food composition databases for bioactive food components. Journal of Food Composition and Analysis 2002, 15, 419.
2. F. Shahidi, M. Naczk. Phenolics in Food and Nutraceuticals: Sources, Applications and Health Effects. CRC Press: Boca Raton, FL, 2004.
3. L. Yaoa, Y. M. Jiang, R. Singanusong, N. Datta, K. Raymont. Phenolic acids in Australian Melaleuca, Guioa, Lophostemon, Banksia and Helianthus honeys and their potential for floral authentication. Food Research International 2005, 38, 651.
4. R. M. Alonso-Salces, C. Herrero, A. Barranco, D. M. Lopez-Marquez, L. A. Berrueta, B. Gallo, F. Vicente. Polyphenolic compositions of Basque natural ciders: a chemometric study. Food Chemistry 2006, 97, 438.
5. M. Naczk, F. Shahidi. Phenolics in cereals, fruits and vegetables: occurrence, extraction and analysis. Journal of Pharmaceutical and Biomedical Analysis 2006, 41, 1523.
6. E. Hvattum, D. Ekeberg. Study of the collision-induced radical cleavage of flavonoid glycosides using negative electrospray ionization tandem quadrupole mass spectrometry. Journal of Mass Spectrometry 2003, 38, 43.
7. L. Kerhoas, D. Aouak, A. Cingoz, J. M. Routaboul, L. Lepiniec, J. Einhorn, N. Birlirakis. Structural characterization of the major flavonoid glycosides from Arabidopsis thaliana seeds. Journal of Agricultural and Food Chemistry 2006, 54, 6603.
8. F. Cuyckens, Y. L. Ma, G. Pocsfalvi, M. Claeys. Tandem mass spectral strategies for the structural characterization of flavonoid glycosides. Analusis 2000, 28, 888.
9. F. Cuyckens, M. Claeys. Determination of the glycosylation site in flavonoid mono-O-glycosides by collision-induced dissociation of electrospray-generated deprotonated and sodiated molecules. Journal of Mass Spectrometry 2005, 40, 364.
10. F. Cuyckens, A. A. Shahat, L. Pieters, M. Claeys. Direct stereochemical assignment of hexose and pentose residues in flavonoid O-glycosides by fast atom bombardment and electrospray ionization mass spectrometry. Journal of Mass Spectrometry 2002, 37, 1272.
11. J. B. Harbone. The Flavonoids. Chapman & Hall: London 1998.
12. K. Robards, X. Li, M. Antolovich, S. Boyd. Characterisation of citrus by chromatographic analysis of flavonoids. Journal of the Science of Food and Agriculture 1997, 75, 87.
13. Y. L. Ma, F. Cuyckens, H. Van den Heuvel, M. Claeys. Mass spectrometricmethods for the characterisation and differentiation of isomeric O-diglycosyl flavonoids. Phytochemical Analysis 2001, 12, 159.
14. Y. L. Ma, I. Vedernikova, H. Van den Heuvel, M. Claeys. Internal glucose residue loss in protonated O-diglycosyl flavonoids upon low-energy collision-induced dissociation. Journal of the American Society for Mass Spectrometry 2000, 11, 136.
15. F. Cuyckens, R. Rozenberg, E. de Hoffmann, M. Claeys. Structure characterization of flavonoid O-diglycosides by positive and negative nano-electrospray ionization ion trap mass spectrometry. Journal of Mass Spectrometry 2001, 36, 1203.
16. R. Franski, P. Bednarek, P. Wojtaszek, M. Stobiecki. Identification of flavonoid diglycosides in yellow lupin (Lupinus luteus L.) with mass spectrometric techniques. Journal of Mass Spectrometry 1999, 34, 486.
17. F. Ferreres, R. Llorach, A. Gil-Izquierdo. Characterization of the interglycosidic linkage in di-, tri-, tetra- and pentaglycosylated flavonoids and differentiation of positional isomers by liquid chromatography/electrospray ionization tandem mass spectrometry. Journal of Mass Spectrometry 2004, 39, 312.
18. J. M. Zhang, J. S. Brodbelt. Silver complexation and tandem mass spectrometry for differentiation of isomeric flavonoid diglycosides. Analytical Chemistry 2005, 77, 1761.
19. P. Kachlicki, J. Einhorn, D. Muth, L. Kerhoas, M. Stobiecki. Evaluation of glycosylation and malonylation patterns in flavonoid glycosides during LC/MS/MS metabolite profiling. Journal of Mass Spectrometry 2008, 43, 572.
20. B. H. Clowers, H. H. Hill. Influence of cation adduction on the separation characteristics of flavonoid diglycoside isomers using dual gate-ion mobility-quadrupole ion trap mass spectrometry. Journal of Mass Spectrometry 2006, 41, 339.
21. K. Ablajan, Z. Abliz, X. Y. Shang, J. M. He, R. P. Zhang, J. G. Shi. Structural characterization of flavonol 3,7-di-O-glycosides and determination of the glycosylation position by using negative ion electrospray ionization tandem mass spectrometry. Journal of Mass Spectrometry 2006, 41, 352.
22. P. Y. Shi, Q. He, Y. Song, H. B. Qu, Y. Y. Cheng. Characterization and identification of isomeric flavonoid O-diglycosides from genus Citrus in negative electrospray ionization by ion trap mass spectrometry and time-of-flight mass, spectrometry. Analytica Chimica Acta 2007, 598, 110.
23. D. Y. Zhou, Q. Xu, X. Y. Xue, F. F. Zhang, X. M. Liang. Identification of O-diglycosyl flavanones in Fructus aurantii by liquid chromatography with electrospray ionization and collision-induced dissociation mass spectrometry. Journal of Pharmaceutical and Biomedical Analysis 2006, 42, 441.
24. P. Waridel, J. L. Wolfender, K. Ndjoko, K. R. Hobby, H. J. Major, K. Hostettmann. Evaluation of quadrupole time-of-flight tandem mass spectrometry and ion-trap multiple-stage mass spectrometry for the differentiation of C-glycosidic flavonoid isomers. Journal of Chromatography A 2001, 926, 29.
25. B. Abad-Garcia, L. A. Berrueta, D. M. Lopez-Marquez, I. Crespo-Ferrer, B. Gallo, F. Vicente. Optimization and validation of a methodology based on solvent extraction and liquid chromatography for the simultaneous determination of several polyphenolic families in fruit juices. Journal of Chromatography A 2007, 1154, 87.
26. L. W. Wulf, C. W. Nagel. High-pressure liquid-chromatographic separation of anthocyanins of vitis-vinifera. American Journal of Enology and Viticulture 1978, 29, 42.
27. B. Domon, C. E. Costello. A systematic nomenclature for carbohydrate fragmentations in Fab-Ms Ms spectra of glycoconjugates. Glycoconjugate Journal 1988, 5, 397.
28. T. J. Mabry, K. R. Markham, M. B. Thomas. The Systematic Identification of Flavonoids. Springer-Verlag: New York 1970.
29. Q. M. Li, M. Claeys. Characterization and differentiation of diglycosyl flavonoids by positive-ion fast-atom-bombardment and tandem mass-spectrometry. Biological Mass Spectrometry 1994, 23, 406.
30. Y. L. Ma. Development and application of mass spectrometric methods for the structural characterisation of flavonoids glycosides and other biologically active natural products, Doctoral Thesis. University of Antwerp, Belgium 1999.
31. A. Sakushima, S. Nishibe, T. Takeda, M. Ohman. Positive and negative ion mass spectra of flavonoid glycosides by fast atom bombardment. Shitsuryo Bunseki 1988, 36, 71.
32. P. Dugo, M. Lo Presti, M. Ohman, A. Fazio, G. Dugo, L. Mondello. Determination of flavonoids in citrus juices by micro-HPLC-ESI/MS. Journal of Separation Science 2005, 28, 1149.
33. C. Caristi, E. Bellocco, V. Panzera, G. Toscano, R. Vadala, U. Leuzzi. Flavonoids detection by HPLC-DAD-MS-MS in lemon juices from sicilian cultivars. Journal of Agricultural and Food Chemistry 2003, 51, 3528.
34. A. Gil-Izquierdo, M. T. Riquelme, N. Porras, F. Ferreres. Effect of the rootstock and interstock grafted in lemon tree (Citrus limon (L.) Burm.) on the flavonoid content of lemon juice. Journal of Agricultural and Food Chemistry 2004, 52, 324.
35. G. Gattuso, C. Caristi, C. Gargiulli, E. Bellocco, G. Toscano, U. Leuzzi. Flavonoid glycosides in bergamot juice (Citrus bergamia risso). Journal of Agricultural and Food Chemistry 2006, 54, 3929.
36. B. Abad-Garcia, Búsqueda de Marcadores Químicos de tipo Polifenólico para la autentificación de Zumos de Frutas, Doctoral Thesis. UPV-EHU: Spain 2007.
37. R. H. Horowitz, B. Gentili. Flavonoid constituents of Citrus (Citrus Science and Technology). Avi Publisher: Wesport, CT 1977.