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

Author:

Upreti Mani1,Clos John F.1,Somayajula Kasi V.1,Milanowski Dennis J.2,Mocek Ulla2,DuBois Grant E.1,Prakash Indra1

Affiliation:

1. The Coca-Cola Company, PO Box 1734, Atlanta, GA 30301, USA

2. AMRI, Bothell Research Center, 18804 North Creek Parkway, Bothell, WA 98011, USA

Abstract

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.

Publisher

SAGE Publications

Subject

Spectroscopy,Atomic and Molecular Physics, and Optics,General Medicine

Reference27 articles.

1. Development of rebiana, a natural, non-caloric sweetener

2. New sweet diterpene glucosides from Stevia rebaudiana

3. Stevia rebaudiana: Its agricultural, biological, and chemical properties

4. Philipps K.C., in “Developments in Sweeteners”, Vol. 3, Ed by Grenby T.H., Elsevier, London, UK, pp. 1–43 (1989).

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