Isolation and characterization of a novel rebaudioside M isomer from a bioconversion reaction of rebaudioside A and NMR comparison studies of rebaudioside M isolated from Stevia rebaudiana Bertoni and Stevia rebaudiana Morita

A minor product, rebaudioside M2 (2), from the bioconversion reaction of rebaudioside A (4) to rebaudioside D (3), was isolated and the complete structure of the novel steviol glycoside was determined. Rebaudioside M2 (2) is considered an isomer of rebaudioside M (1) and contains a relatively rare 1...

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Bibliographic Details
Published in:Biomolecules (Basel, Switzerland) Switzerland), 2014-03, Vol.4 (2), p.374-389
Main Authors: Prakash, Indra, Bunders, Cynthia, Devkota, Krishna P, Charan, Romila D, Ramirez, Catherine, Priedemann, Christopher, Markosyan, Avetik
Format: Article
Language:English
Subjects:
bioconversion
Biotransformation
Diterpenes, Kaurane - chemistry
Diterpenes, Kaurane - isolation & purification
Diterpenes, Kaurane - metabolism
Isomerism
Magnetic Resonance Spectroscopy
nuclear magnetic resonance (NMR)
rebaudioside D
rebaudioside M
rebaudioside M2
Species Specificity
Stevia - chemistry
Stevia rebaudiana
Stevia rebaudiana Bertoni
Stevia rebaudiana Morita
steviol glycosides
structure characterization
Trisaccharides - chemistry
Trisaccharides - isolation & purification
Trisaccharides - metabolism
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Summary:A minor product, rebaudioside M2 (2), from the bioconversion reaction of rebaudioside A (4) to rebaudioside D (3), was isolated and the complete structure of the novel steviol glycoside was determined. Rebaudioside M2 (2) is considered an isomer of rebaudioside M (1) and contains a relatively rare 1→6 sugar linkage. It was isolated and characterized with NMR (1H, 13C, COSY, HSQC-DEPT, HMBC, 1D-TOCSY, and NOESY) and mass spectral data. Additionally, we emphasize the importance of 1D and 2D NMR techniques when identifying complex steviol glycosides. Numerous NMR spectroscopy studies of rebaudioside M (1), rebaudioside D (3), and mixture of 1 and 3 led to the discovery that SG17 which was previously reported in literature, is a mixture of rebaudioside D (3), rebaudioside M (1), and possibly other related steviol glycosides.
ISSN:2218-273X
2218-273X
DOI:10.3390/biom4020374