An investigation of the hemolytic saccharide cleavage of deprotonated flavonol 3-O-glycosides in a quadrupole ion trap mass spectrometer

Journal of Mass Spectrometry

Volumn 43, Issue 8, 2008, Pages 1045-1052

  Davis, Barry D ^a,b   Brodbelt, Jennifer S ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

^b ARIAD PHARMACEUTICALS INC   (United States)

Author keywords

Collision induced dissociation; Flavonoid; Heterolytic cleavage; Homolytic cleavage; Radical

Indexed keywords

IONS; MASS SPECTROMETRY; SPECTROMETERS; SPECTROMETRY; SUGARS;

3-O-GLYCOSIDES; COLLISION-INDUCED DISSOCIATION; FLAVONOID; HETEROLYTIC CLEAVAGE; HOMOLYTIC CLEAVAGE; PRODUCT IONS; QUADRUPOLE ION TRAPS; RADICAL;

MASS SPECTROMETERS;

AGLYCONE; CARBOHYDRATE; FLAVONOID; FLAVONOL DERIVATIVE; HYDROGEN; DRUG DERIVATIVE; GLYCOSIDE; KAEMPFEROL; KAEMPFEROL DERIVATIVE; MYRICETIN; PROTON; QUERCETIN;

ARTICLE; DISSOCIATION; HYDROXYLATION; ION TRAP MASS SPECTROMETRY; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; TANDEM MASS SPECTROMETRY; CHEMICAL STRUCTURE; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; GLYCOSYLATION; INSTRUMENTATION; METHODOLOGY;

FLAVONOIDS; FLAVONOLS; GLYCOSIDES; GLYCOSYLATION; KAEMPFEROLS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PROTONS; QUERCETIN; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 49549113625     PISSN: 10765174     EISSN: 10969888     Source Type: Journal    
DOI: 10.1002/jms.1381     Document Type: Article

References (26)

1. Cuyckens F, Claeys M. Mass spectrometry in the structural analysis of flavonoids. Journal of Mass Spectrometry 2004; 39: 1. DOI: 10.1002/jms.585.
2. de Rijke E, Out P, Niessen WMA, Ariese F, Gooijer C, Brinkman UAT. Analytical separation and detection methods for flavonoids. Journal of Chromatography A 2006; 1112: 31. DOI: 10.1016/j.chroma.2006.01.019.
3. Prasain JK, Wang CC, Barnes S. Mass spectrometric methods for the determination of flavonoids in biological samples. Free Radical Biology and Medicine 2004; 37: 1324. DOI: 10.1016/j.freeradbiomed.2004.07.026.
4. Cuyckens F, Ma YL, Pocsfalvi G, Claeys M. Tandem mass spectral strategies for the structural characterization of flavonoid glycosides. Analysis 2000; 28: 888.
5. Stobiecki M. Application of mass spectrometry for identification and structural studies of flavonoid glycosides. Phytochemistry 2000; 54: 237. DOI: 10.1016/S0031-9422(00)00091-1.
6. Wolfender JL, Maillard M, Marston A, Hostettmann K. Mass spectrometry of underivatized naturally occurring glycosides. Phytochemical Analysis 1992; 3: 193. DOI: 10.1002/pca.2800030502.
7. Mabry TJ, Ulubelen A. Flavonoids and related plant phenolics. In Biochemical Applications of Mass Spectrometry, 1st Supplemental Volume, Waller GR Dermer OC (eds). John Wiley: New York, 1980; 1131.
8. 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. International Journal of Mass Spectrometry 2004; 232: 171. DOI: 10.1016/j.ijms.2004.01.001.
9. Cuyckens F, Rozenberg R, de Hoffmann E, Claeys M. Structure characterization of flavonoid O-diglycosides by positive and negative nano-electrospray ionization ion trap mass spectrometry. Journal of Mass Spectrometry 2001; 36: 1203. DOI: 10.1002/jms.224.
10. Hvattum E, Ekeberg D. 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. DOI: 10.1002/jms.398.
11. Petasaloa JJ, Tolonen A. Identification of flavonoids of Rhodiola rosea by liquid chromatography-tandem mass spectrometry. Journal of Chromatography A 2006; 1112: 224. DOI: 10.1016/j.chroma.2005.11.056.
12. Ablajan K, Abliz Z, Shang X-Y, He J-M, Zhang RP, Shi J-G. 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. DOI: 10.1002/jms.995.
13. Cuyckens F, Claeys M. 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. DOI: 10.1002/jms.794.
14. Davis BD, Brodbelt JS. Determination of the glycosylation site of flavonoid monoglucosides by metal complexation and tandem mass spectrometry. Journal of The American Society for Mass Spectrometry 2004; 15: 1287. DOI: 10.1016/j.jasms.2004.06.003.
15. n Methods for Saccharide Characterization of Monoglycosyl Flavonoids Using Postcolumn Manganese Complexation. Analytical Chemistry 2005; 77: 1883. DOI: 10.1021/ac048374o.
16. Davis BD, Needs PW, Kroon PA, Brodbelt JS. Identification of isomeric flavonoid glucuronides in urine and plasma by metal complexation and LC-ESI-MS/MS. Journal of Mass Spectrometry 2006; 41: 911. DOI: 10.1002/jms.1050.
17. Wojcinska M, Williams J, Mabry TJ, Ahmed AA, Davis BD, Toth G, El-Sayed NH, Matlawska I, Clevinger J. Flavonol triglycosides from the leaves of Silphium albiflorum. Natural Product Communications 2006; 1: 941.
18. Lopez LL, Tiller PR, Senko MW, Schwartz JC. Automated strategies for obtaining standardized collisionally induced dissociation spectra on a benchtop ion trap mass spectrometer. Rapid Communications in Mass Spectrometry 1999; 13: 663. DOI: 10.1002/(SICI)1097-0231(19990430)13:8¡663::AID- RCM538¿3.0.CO;2-H.
19. Domon B, Costello CE. A systematic nomenclature for carbohydrate fragmentations in FAB-MS/MS spectra of glycoconjugates. Glycoconjugate Journal 1988; 5: 397. DOI: 10.1007/BF01049915.
20. HyperChem(TM) Professional 7.51. Hypercube, Inc: Florida, USA.
21. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui QA, Baboul G, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA. Gaussian 03, Revision C.02. Gaussian: Wallingford, 2004.
22. Flükiger P, Lüthi HP, Portmann S, Weber J. MOLEKEL 4.0. Swiss National Supercomputing Centre CSCS: Manno, 2000.
23. Hughes RJ, Croley TR, Metcalfe CD, March RE. A tandem mass spectrometric study of selected characteristic flavonoids. International Journal of Mass Spectrometry 2001; 210/211: 371. DOI: 10.1016/S1387-3806(01)00451-1.
24. Fabre N, Rustan I, de Hoffmann E, Quetin-Leclercq J. Determination of flavone, flavonol, and flavanone aglycones by negative ion liquid chromatography electrospray ion trap mass spectrometry. Journal of The American Society for Mass Spectrometry 2001; 12: 707. DOI: 10.1016/S1044-0305(01)00226-4.
25. Hvattum E, Stenstrom Y, Ekeberg D. Study of the reaction products of flavonols with 2,2-diphenyl-1-picrylhydrazyl using liquid chromatography coupled with negative electrospray ionization tandem mass spectrometry. Journal of Mass Spectrometry 2004; 39: 1570. DOI: 10.1002/jms.756.
26. March RE, Miao XS. A fragmentation study of kaempferol using electrospray quadrupole time-of-flight mass spectrometry at high mass resolution. International Journal of Mass Spectrometry 2004; 231: 157. DOI: 10.1016/j.ijms.2003.10.008.