alexa Assigning glucose or galactose as the primary glycosidic sugar in 3-O-mono-, di- and triglycosides of kaempferol using negative ion electrospray and serial mass spectrometry.


Journal of Chemical Biology & Therapeutics

Author(s): Kite GC, Veitch NC

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Kaempferol 3-O-beta-glucopyranoside, kaempferol 3-O-beta-galactopyranoside and higher glycosides of these two flavonoids with alpha-rhamnose at C-2 and/or C-6 of the primary sugar were studied by negative ion electrospray ionisation and serial mass spectrometry in a three-dimensional (3D) ion trap mass spectrometer. Kaempferol 3-O-beta-glucopyranoside and kaempferol 3-O-alpha-rhamnopyranosyl(1-->6)-beta-glucopyranoside could be distinguished from their respective galactose analogues by differences in the ratio of the radical aglycone ion [Y(0) - H](*-) to the rearrangement aglycone ion Y(0) (-) following MS/MS of the deprotonated molecules. Kaempferol 3-O-rhamnopyranosyl(1-->2)-beta-glucopyranoside and kaempferol 3-O-alpha-rhamnopyranosyl(1-->2)[alpha-rhamnopyranosyl(1-->6)]-beta-glucopyranoside could be distinguished from their respective galactose analogues by differences in the product ion spectra of the [(M - H) - rhamnose](-) ion following serial mass spectrometry. In the triglycoside, it was deduced that this ion resulted from the loss of the rhamnose substituted at 2-OH of the primary sugar by observing that MS/MS of deprotonated kaempferol 3-O-beta-glucopyranosyl(1-->2)[alpha-rhamnopyranosyl(1-->6)]-beta-glucopyranoside showed the loss of glucose and not rhamnose. Thus the class of sugar (hexose, deoxyhexose, pentose) at C-2 and C-6 of the primary sugar can be determined. These observations aid the assignment of kaempferol 3-O-glycosides, having glucose or galactose as the primary glycosidic sugar, in LC/MS analyses of plant extracts, and this can be done with reference to only a few standards.

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This article was published in Rapid Commun Mass Spectrom and referenced in Journal of Chemical Biology & Therapeutics

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