Tunable Transition Metal-Ligand Complexation for Enhanced Elucidation of Flavonoid Diglycosides by Electrospray Ionization Mass Spectrometry

Journal of the American Society for Mass Spectrometry

Volumn 18, Issue 3, 2007, Pages 422-431

  Pikulski, Michael ^a   Aguilar, Apolonio ^a   Brodbelt, Jennifer S ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DISSOCIATION; IONIZATION; ISOMERS; MASS SPECTROMETRY; MOLECULAR STRUCTURE; TRANSITION METALS;

AUXILIARY LIGANDS; ELECTROSPRAY IONIZATION MASS SPECTROMETRY; FRAGMENTATION PATTERNS; METAL BINDING;

COMPLEXATION;

AURANTIIN; DIOSMIN; FLAVONOID; GLYCOSIDE; HESPERIDIN; LIGAND; LINARIN; METAL COMPLEX;

ARTICLE; BINDING AFFINITY; COMPLEX FORMATION; ELECTROSPRAY MASS SPECTROMETRY; ION TRAP MASS SPECTROMETRY; MASS SPECTROMETER; METAL BINDING; MOLECULAR MODEL; PROTON NUCLEAR MAGNETIC RESONANCE; QUADRUPOLE MASS SPECTROMETRY;

FLAVONOIDS; GLYCOSIDES; LIGANDS; METALS; MOLECULAR STRUCTURE; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STEREOISOMERISM; TANDEM MASS SPECTROMETRY;

EID: 33847073277     PISSN: 10440305     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jasms.2006.10.011     Document Type: Article

References (50)

1. Reddy P.N., Ramesh V., Srinivas R., Sharma G.V.M., Nagendar P., and Subash V. Differentiation of Some Positional and Diastereomeric Isomers of Boc-carbo-beta(3) Dipeptides Containing Galactose, Xylose and Mannose Sugars by Electrospray Ionization Tandem Mass Spectrometry (ESI MS/MS). Int. J. Mass Spectrom. 248 (2006) 115-123
2. Song F.R., Liu Z.Q., Liu S.Y., and Cai Z.W. Differentiation and Identification of Ginsenoside Isomers by Electrospray Ionization Tandem Mass Spectrometry. Anal. Chim. Acta 531 (2005) 69-77
3. Wu L.M., and Cooks G. Chiral and Isomeric Analysis by Electrospray Ionization and Sonic Spray Ionization Using the Fixed-ligand Kinetic Method. Eur. J. Mass Spectrom. 11 (2005) 231-242
4. Song F.R., Cui M., Liu Z.Q., Yu B., and Liu S.Y. Multiple-stage Tandem Mass Spectrometry for Differentiation of Isomeric Saponins. Rapid Commun. Mass Spectrom. 18 (2004) 2241-2248
5. Matamoros F.L.E., Obel N., Scheller H.C., and Roepstorff P. Differentiation of Isomeric Oligosaccharide Structures by ESI Tandem MS and GC-MS. Carbohydr. Res. 339 (2004) 655-664
6. Zhang J.H., Lindsay L.L., Hedrick J.L., and Lebrilla C.B. Strategy for Profiling and Structure Elucidation of Mucin-type Oligosaccharides by Mass Spectrometry. Anal. Chem. 76 (2004) 5990-6001
7. Cuyckens F., Rozenberg R., de Hoffmann E., and Claeys M. Structure Characterization of Flavonoid O-Diglycosides by Positive and Negative Nano-electrospray Ionization Ion Trap Mass Spectrometry. J. Mass Spectrom. 36 (2001) 1203-1210
8. Desaire H., and Leary J.A. Multicomponent Quantification of Diastereomeric Hexosamine Monosaccharides Using Ion Trap Tandem Mass Spectrometry. Anal. Chem. 71 (1999) 4142-4147
9. Waridel P., Wolfender J.L., Ndjoko K., Hobby K.R., Major H.J., and 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 926 (2001) 29-41
10. Gaucher S.P., and Leary J.A. Influence of Metal Ion and Coordination Geometry on the Gas Phase Dissociation and Stereochemical Differentiation of N-glycosides. Int. J. Mass Spectrom. 197 (2000) 139-148
11. Desaire H., and Leary J.A. Differentiation of Diastereomeric N-acetylhexosamine Monosaccharides Using Ion Trap Tandem Mass Spectrometry. Anal. Chem. 71 (1999) 1997-2002
12. Leavell M.D., Kruppa G.H., and Leary J.A. Determination of Phosphate Position in Hexose Monosaccharides Using an FTICR Mass sPectrometer: Ion/Molecule Reactions, Labeling Studies, and Dissociation Mechanisms. Int. J. Mass Spectrom. 222 (2003) 135-153
13. Hashii N., Kawasaki N., Itoh S., Harazono A., Matsuishi Y., Hayakawa T., and Kawanishi T. Specific Detection of Lewis x-Carbohydrates in Biological Samples Using Liquid Chromatography/Multiple-stage Tandem Mass Spectrometry. Rapid Commun. Mass Spectrom. 19 (2005) 3315-3321
14. Li R., Wu Z.J., Zhang F., and Ding L.S. Differentiation of Three Pairs of Aconite Alkaloid Isomers from Aconitum nagarum var. lasiandrum by Electrospray Ionization Tandem Mass Spectrometry. Rapid Commun. Mass Spectrom. 20 (2006) 157-170
15. Bandu M.L., and Desaire H. The STEP Method (Statistical Test of Equivalent Pathways): Application to Pharmaceuticals. Analyst 131 (2006) 268-274
16. Bandu M.L., Wilson J., Vachet R.W., Dalpathado D.S., and Desaire H. STEP (Statistical Test of Equivalent Pathways) Analysis: A Mass Spectrometric Method for Carbohydrates and Peptides. Anal. Chem. 77 (2005) 5886-5893
17. Satterfield M., and Brodbelt J.S. Enhanced Detection of Flavonoids by Metal Complexation and Electrospray Ionization Mass Spectrometry. Anal. Chem. 72 (2000) 5898-5906
18. Satterfield M., and Brodbelt J.S. Structural Characterization of Flavonoid Glycosides by Collisionally Activated Dissociation of Metal Complexes. J. Am. Soc. Mass Spectrom. 12 (2001) 537-549
19. Zhang J.M., and Brodbelt J.S. Silver Complexation and Tandem Mass Spectrometry for Differentiation of Isomeric Flavonoid Diglycosides. Anal. Chem. 77 (2005) 1761-1770
20. Zhang J.M., Wang J.M., and Brodbelt J.S. Characterization of Flavonoids by Aluminum Complexation and Collisionally Activated Dissociation. J. Mass Spectrom. 40 (2005) 350-363
21. Pikulski M., and Brodbelt J.S. Differentiation of Flavonoid Glycoside Isomers by Using Metal Complexation and Electrospray Ionization Mass Spectrometry. J. Am. Soc. Mass Spectrom. 14 (2003) 1437-1453
22. Davis B.D., and Brodbelt J.S. Determination of the Glycosylation Site of Flavonoid Monoglucosides by Metal Complexation and Tandem Mass Spectrometry. J. Am. Soc. Mass Spectrom. 15 (2004) 1287-1299
23. Davis B.D., and Brodbelt J.S. LC-MSn Methods for Saccharide Characterization of Monoglycosyl Flavonoids Using Postcolumn Manganese Complexation. Anal. Chem. 77 (2005) 1883-1890
24. vanAcker S.A.B.E., vandenBerg D.J., Tromp M.N.J.L., Griffioen D.H., VanBennekom W.P., VanderVijgh W.J.F., and Bast A. Structural Aspects of Antioxidant Activity of Flavonoids. Free. Radic. Biol. Med. 20 (1996) 331-342
25. Pietta P. Flavonoids in Medicinal Plants (1998), Marcel Dekker, New York
26. Paganga G., Miller N., and Rice-Evans C.A. The Polyphenolic Content of Fruit and Vegetables and Their Antioxidant Activities. What Does a Serving Constitute?. Free. Radic. Res. 30 (1999) 153-162
27. Jovanovic S.V., Steenken S., Tosic M., Marjanovic B., and Simic M.G. Flavonoids as Antioxidants. J. Am. Chem. Soc. 116 (1994) 4846-4851
28. RiceEvans C.A., and Miller N.J. Antioxidant Activities of Flavonoids as Bioactive Components of Food. Biochem. Soc. Trans. 24 (1996) 790-795
29. Hertog M.G.L. Flavonoid Intake and Long-Term Risk of Coronary Heart-Disease and Cancer in the 7 Countries Study. Arch. Intern. Med. 155 (1995) 11841184
30. Knekt P., Jarvinen R., Reunanen A., and Maatela J. Flavonoid Intake and Coronary Mortality in Finland: A Cohort Study. Br. Med. J. 312 (1996) 478-481
31. Hollman P.C.H., Feskens E.J.M., and Katan M.B. Tea Flavonols in Cardiovascular Disease and Cancer Epidemiology. Proc. Soc. Exp. Biol. Med. 220 (1999) 198-202
32. Mojzisova G., and Kuchta M. Dietary Flavonoids and Risk of Coronary Heart Disease. Physiol. Res. 50 (2001) 529-535
33. Amic D., Davidovic-Amic D., Beslo D., and Trinajstic N. Structure-Radical Scavenging Activity Relationships of Flavonoids. Croat. Chem. Acta 76 (2003) 55-61
34. Cao G.H., Sofic E., and Prior R.L. Antioxidant and Prooxidant Behavior of Flavonoids: Structure-Activity Relationships. Free. Radic. Biol. Med. 22 (1997) 749-760
35. Bors W.H.M.C. The Chemistry of Flavonoids. In: Rice-Evans C.A. (Ed). Flavonoids in Health and Disease (1998), Marcel Dekker, New York 111-136
36. RiceEvans C.A., Miller N.J., and Paganga G. Structure-Antioxidant Activity Relationships of Flavonoids and Phenolic Acids. Free Radic. Biol. Med. 21 (1996) 417417
37. Stobiecki M. Application of Mass Spectrometry for Identification and Structural Studies of Flavonoid Glycosides. Phytochemistry 54 (2000) 237-256
38. Cuyckens H., and Claeys M. Mass Spectrometry in the Structural Analysis of Flavonoids. J. Mass Spectrom. 39 (2004) 461461
39. Nord G. Some Properties of 2,2′-bipyridine, 1,10-Phenanthroline and Their Metal Complexes. Comments. Inorg. Chem. 4 (1985) 193-212
40. Constable E.C. The Reactions of Nucleophiles with Complexes of Chelating Heterocyclic Imines-A Critical Survey. Polyhedron 2 (1983) 551-572
41. Brandt W.W., Dwyer F.P., and Gyarfas E.C. Chelate complexes of 1,10-phenanthroline and related compounds. Chem. Rev. 54 (1954) 959-1017
42. McWhinnie W.R., and Miller J.D. Chemistry of Complexes Containing 2,2′-Bipyridyl, 1,10-Phenanthroline or 2,2′,6′,2″-Terpyridyl as Ligands. Adv. Inorg. Radiochem. 12 (1969) 135-173
43. Martell A.E., and Hancock R.D. Metal Complexes in Aqueous Solutions. 1st ed. (1996), Plenum Press, New York
44. Satterfield M., and Brodbelt J.S. Relative Binding Energies of Gas-phase Pyridyl Ligand/Metal Complexes by Energy-Variable Collisionally Activated Dissociation in a Quadrupole Ion Trap. Inorg. Chem. 40 (2001) 5393-5400
45. Wu H.F., and Brodbelt J.S. Gas-phase Chelation Reactions of Monopositive Cations with Heteroaromatic Ligands. Inorg. Chem. 34 (1995) 615-621
46. Maerker G.C. Synthesis of Some 4,4′-Disubstituted 2,2′-Bipyridines. J. Am. Chem. Soc. 80 (1958) 2745-2748
47. Carlson B., Phelan G.D., Kim J.H., Jen A.K.Y., and Dalton L.R. Organic Light Emitting Devices Based upon Divalent Osmium Complexes. Abstr. Pap. Am. Chem. Soc. 227 (2004) U1314-U1314
48. Ward R.S., Branciard D., Dignan R.A., and Pritchard M.C. Synthesis of C-2 Symmetric 2,2′-Bipyridyl Imidazolidinone and Oxazaborolidine Derivatives. Heterocycles 56 (2002) 157-170
49. Denes V., and Chira R. Poly-Halogenation of Nitrogen Containing Heterocyclic-Compounds. 3. Polybromo-1,10-Phenanthrolines. J. Fur. Prak. Chem. 320 (1978) 172-175
50. Zhang J.M., and Brodbelt J.S. Threshold Dissociation and Molecular Modeling of Transition Metal Complexes of Flavonoids. J. Am. Soc. Mass Spectrom. 16 (2005) 139-151