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

The trend in the extent of homolytic saccharide cleavage is reported for a series of deprotonated flavonol 3-O-glycosides upon collision-induced dissociation (CID) in a quadrupole ion trap mass spectrometer. The second-generation product ions from the primary [Y₀]⁻ and [Y₀- H]⁻ product ions were als...

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Bibliographic Details
Published in:Journal of mass spectrometry. 2008-08, Vol.43 (8), p.1045-1052
Main Authors: Davis, Barry D, Brodbelt, Jennifer S
Format: Article
Language:English
Subjects:
collision-induced dissociation
flavonoid
Flavonoids - chemistry
Flavonols - chemistry
Glycosides - chemistry
Glycosylation
heterolytic cleavage
homolytic cleavage
Kaempferols - chemistry
Models, Molecular
Molecular Structure
Protons
Quercetin - analogs & derivatives
Quercetin - chemistry
radical
Spectrometry, Mass, Electrospray Ionization - instrumentation
Spectrometry, Mass, Electrospray Ionization - methods
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Summary:The trend in the extent of homolytic saccharide cleavage is reported for a series of deprotonated flavonol 3-O-glycosides upon collision-induced dissociation (CID) in a quadrupole ion trap mass spectrometer. The second-generation product ions from the primary [Y₀]⁻ and [Y₀- H]⁻ product ions were also identified. It was determined that the structure of both the aglycon and the saccharide portions of the flavonoid glycoside are pivotal in inducing radical cleavage. In contrast to earlier work on this subject reported for a smaller group of flavonols, the correlation between the degree of B-ring hydroxylation and the extent of radical saccharide cleavage showed several notable exceptions in the present work. Homolytic cleavage was also investigated in the context of using tandem mass spectrometry to identify the aglycon portions of flavonoid glycosides. Copyright © 2008 John Wiley & Sons, Ltd.
ISSN:1076-5174
1096-9888
DOI:10.1002/jms.1381