Gas-Phase Intramolecular Elimination Reaction Studies of Steviol Glycosides in Positive Electrospray and Tandem Mass Spectrometry

This paper reports the first study of the gas-phase intramolecular elimination reaction of steviol glycosides in positive electrospray mass spectrometry. The observed glycosylated product ions are proposed to be formed via an intramolecular elimination of sugar units from the parent molecule ion. It...

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Bibliographic Details
Published in:European journal of mass spectrometry (Chichester, England) England), 2009-01, Vol.15 (1), p.11-21
Main Authors: Upreti, Mani, Clos, John F., Somayajula, Kasi V., Milanowski, Dennis J., Mocek, Ulla, DuBois, Grant E., Prakash, Indra
Format: Article
Language:English
Subjects:
Carbohydrate Sequence
Deuterium
Diterpenes, Kaurane - chemistry
Gases
Glycosides - chemistry
Glycosylation
Molecular Sequence Data
Molecular Structure
Spectrometry, Mass, Electrospray Ionization
Stevia - chemistry
Sweetening Agents - chemistry
Tandem Mass Spectrometry
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Summary:This paper reports the first study of the gas-phase intramolecular elimination reaction of steviol glycosides in positive electrospray mass spectrometry. The observed glycosylated product ions are proposed to be formed via an intramolecular elimination of sugar units from the parent molecule ion. It was further proven by MS/MS studies and deuterium labeling experiments with one of the steviol glycosides, rebaudioside A. These mass spectrometric results confirmed that the new glycosylated product ions observed are most likely formed by the combination of glucose moieties (Glu) II–IV and Glu I via a gas-phase intramolecular elimination reaction.
ISSN:1469-0667
1751-6838
DOI:10.1255/ejms.981