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

Volumn 40, Issue 3, 2005, Pages 364-372

  Cuyckens, Filip ^a   Claeys, Magda ^a  

^a UNIVERSITY OF ANTWERP   (Belgium)

Author keywords

Collision induced dissociation; Electrospray ionization; Flavonoid glycosides; Glycosylation position; Sodium adduct ions

Indexed keywords

DISSOCIATION; IONIZATION; IONS; ISOMERS; MASS SPECTROMETRY;

COLLISION ENERGY; COLLISION-INDUCED DISSOCIATION SPECTRA; ELECTROSPRAY IONIZATION; GLYCOSYLATION;

CARBOHYDRATES;

APIGENIN 7 O NEOHESPERIDOSIDE; APIGENIN 7 O RUTINOSIDE; FLAVANONE DERIVATIVE; FLAVONE DERIVATIVE; FLAVONOID GLYCOSIDE; FLAVONOL 3 O GLYCOSIDE; FLAVONOL DERIVATIVE; HESPERETIN 7 O RUTINOSIDE; HYPERIN; ISOQUERCITRIN; KAEMPFEROL 7 O NEOHESPERIDOSIDE; LUTEOLIN 4' O GLUCOSIDE; LUTEOLIN 7 GLUCOSIDE; NARINGENIN 7 O NEOHESPERIDOSIDE; NARINGENIN 7 O RUTINOSIDE; NICOTIFLORIN; QUERCETIN 3 O ARABINOGLUCOSIDE; QUERCETIN 3 O RUTINOSIDE; QUERCETIN 4' O GLUCOSIDE; SODIUM; SYRINGETIN 3 O GALACTOSIDE; SYRINGETIN 3 O GLUCOSIDE; UNCLASSIFIED DRUG;

ARTICLE; COLLISIONALLY ACTIVATED DISSOCIATION; ELECTROSPRAY; ENERGY; FRAGMENTATION REACTION; GLYCOSYLATION; NEGATIVE ION ELECTROSPRAY; PRIORITY JOURNAL; PROTON TRANSPORT; REACTION ANALYSIS; STANDARD; TANDEM MASS SPECTROMETRY;

FLAVONOIDS; GLYCOSIDES; GLYCOSYLATION; MOLECULAR STRUCTURE; PROTONS; SODIUM; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 15344346915     PISSN: 10765174     EISSN: None     Source Type: Journal    
DOI: 10.1002/jms.794     Document Type: Article

References (32)

1. Di Carlo G, Mascolo N, Izzo AA, Capasso F. Flavonoids: old and new aspects of a class of natural therapeutic drugs. Life Sci. 1999; 65: 337.
2. Nijveldt RJ, van Nood E, van Hoorn DEC, Boelens PG, van Norren K, van Leeuwen PAM. Flavonoids: a review of probable mechanisms of actions and potential applications. Am. J. Clin. Nutr. 2001; 74: 418.
3. Hollman PCH, Katan MB. Absorption, metabolism and health effects of dietary flavonoids in man. Biomed. Pharmacother. 1997; 51: 305.
4. Hollman PCH. Evidence for health benefits of plant phenols: local or systemic effects? J. Sci. Food Agric. 2001; 81: 842.
5. Iwashina T. The structure and distribution of the flavonoids in plants. J. Plant Res. 2000; 113: 287.
6. Cuyckens F, Claeys M. Mass spectrometry in the structural analysis of flavonoids. J. Mass Spectrom. 2004; 39: 1; erratum, 2004; 39: 461.
7. Ma YL, Li QM, Van den Heuvel H, Claeys M. Characterization of flavone and flavonol aglycones by collision-induced dissociation tandem mass spectrometry. Rapid Commun. Mass Spectrom. 1997; 11: 1357.
8. n for the dereplication of flavonoids and related compounds in crude plant extracts. Analusis 2000; 28: 895.
9. Fabre N, Rustan I, de Hoffmann E, Quetin-Leclercq J. Determination of flavone, flavonol and flavanone aglycones by negative ion LC-ES ion trap mass spectrometry. J. Am. Soc. Mass Spectrom. 2001; 12: 707.
10. Wolfender JL, Maillard M, Marston A, Hostettmann K, Review paper: mass spectrometry of underivatized naturally occurring glycosides. Phytochem. Anal. 1992; 3: 193.
11. Cuyckens F, Shahat AA, Pieters L, Claeys M. Direct stereochemical assignment of hexose and pentose residues in flavonoid O-glycosides by fast atom bombardment and electrospray ionization mass spectrometry. J. Mass Spectrom. 2002; 12: 1272.
12. Häkkinen S, Auriola S. High-performance liquid chromatography with electrospray ionization mass spectrometry and diode array ultraviolet detection in the identification of flavonol aglycones and glycosides in berries. J. Chromatogr. A 1998; 829: 91.
13. Cuyckens F, Shahat AA, Van den Heuvel H, Abdel-Shafeek KA, El-Messiry MM, Seif-El Nasr MM, Pieters L, Vlietinck AJ, Claeys M. The application of liquid chromatography-electrospray ionization mass spectrometry and collision-induced dissociation in the structural characterization of acylated flavonol O-glycosides from the seeds of Carrichtera annua. Eur. J. Mass Spectrom. 2003; 9: 409.
14. Ma YL, Cuyckens F, Van den Heuvel H, Claeys M. Mass spectrometric methods for the characterisation and differentiation of isomeric O-diglycosyl flavonoids. Phytochem. Anal. 2001; 12: 159.
15. Satterfield M, Brodbelt JS. Structural characterization of flavonoid glycosides by collisionally activated dissociation of metal complexes. J. Am. Soc. Mass Spectrom. 2001; 12: 537.
16. Pikulski M, Brodbelt JS. Differentiation of flavonoid glycoside isomers by using metal complexation and electrospray ionization mass spectrometry. J. Am. Soc. Mass Spectrom. 2003; 14: 1437.
17. Zhang J, Brodbelt JS. Gas-phase hydrogen/deuterium exchange and conformations of deprotonated flavonoids and gas-phase acidities of flavonoids. J. Am. Chem. Soc. 2004; 126: 5906.
18. Ferreres F, Llorach R, Gil-Izquierdo A. 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. J. Mass Spectrom. 2004; 39: 312.
19. Li QM, Van den Heuvel H, Dillen L, Claeys M. Differentiation of 6-C and 8-C-glycosidic flavonoids by positive ion fast atom bombardment and tandem mass spectrometry. Biol. Mass Spectrom. 1992; 21: 213.
20. Becchi M, Fraisse D. Fast atom bombardment and fast atom bombardment collision-activated dissociation/mass-analysed ion kinetic energy analysis of C-glycosidic flavonoids. Biomed. Mass Spectrom. 1989; 18: 122.
21. Waridel P, Wolfender JL, Ndjoko K, Hobby KR, Major HJ, Hostettmann K. Evaluation of quadrupole time-of-flight tandem mass spectrometry and ion-trap multiple-stage mass spectrometry for the differentiation of C-glycosidic flavonoid isomers. J. Chromatogr. A 2001; 926: 29.
22. Rath R, Touŕ A, Nianga M, Wolfender JL, Hostettmann K. Characterization of C-glycosylflavones from Dossotis rotundifolia by liquid chromatography-UV diode array detection-tandem mass spectrometry. Chromatographia 1995; 41: 332.
23. Davis BD, Brodbelt JS. Determination of the glycosylation site of flavonoid monoglucosides by metal complexation and tandem mass spectrometry. J. Am. Soc. Mass Spectrom. 2004; 15: 1287.
24. Li QM, Van den Heuvel H, Delorenzo O, Corthout J, Pieters LAC, Vlietinck AJ, Claeys M. Mass spectral characterization of C-glycosidic flavonoids isolated from a medicinal plant (Passiflora incarnata). J. Chromatogr. B 1991; 562: 435.
25. Domon B, Costello CE. A systematic nomenclature for carbohydrate fragmentations in FAB-MS/MS spectra of glycoconjugates. Glycoconj. J. 1988; 5: 397.
26. Constant HL, Slowing K, Graham JG, Pezzuto JM, Cordell GA, Beecher CWW. A general method for the dereplication of flavonoid glycosides utilizing high performance liquid chromatography/mass spectrometric analysis. Phytochem. Anal. 1997; 8: 176.
27. Hvattum E. Determination of phenolic compounds in rose hip (Rosa canina) using liquid chromatography coupled to electrospray ionisation tandem mass spectrometry and diode array detection. Rapid Commun. Mass Spectrom. 2002; 16: 655.
28. Hvattum E, Ekeberg D. Study of the collision-induced radical cleavage of flavonoid glycosides using negative electrospray ionization tandem quadrupole mass spectrometry. J. Mass Spectrom. 2003; 38: 43.
29. March RE, Miao XS, Metcalfe CD, Stobiecki M, Marczak L. A fragmentation study of an isoflavone glycoside, genistein-7-O-glucoside, using electrospray quadrupole time-of-flight mass spectrometry at high mass resolution. Int. J. Mass Spectrom. 2004; 232: 171.
30. Sakushima A, Nishibe S, Takeda T, Ogihara Y. Positive and negative ion mass spectra of flavonoid glycosides by fast atom bombardment. Mass Spectrosc. 1988; 36: 71.
31. Karlsson KE. Cationization in electrospray microcolumn liquid chromatography-mass spectrometry. J. Chromatogr. A 1998; 794: 359.
32. Li QM, Claeys M. Characterization and differentiation of diglycosyl flavonoids by positive ion fast atom bombardment and tandem mass spectrometry. Biol. Mass Spectrom. 1994; 23: 406.