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Biomolecules 2014, 4(2), 374-389; doi:10.3390/biom4020374
Article

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

1,* , 1
,
2
,
2
,
2
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2
 and
3
1 The Coca-Cola Company, Atlanta, GA 30313, USA 2 AMRI-Albany, Analytical Development, Albany, NY 12212, USA 3 PureCircle Limited, Lengkuk Teknologi, Bandar Enstek, Negeri Sembilan 71760, Malaysia
* Author to whom correspondence should be addressed.
Received: 30 January 2014 / Revised: 12 March 2014 / Accepted: 13 March 2014 / Published: 31 March 2014
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Abstract

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 16 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.
Keywords: Stevia rebaudiana Bertoni; Stevia rebaudiana Morita; rebaudioside M; rebaudioside D; rebaudioside M2; bioconversion; steviol glycosides; structure characterization; nuclear magnetic resonance (NMR) Stevia rebaudiana Bertoni; Stevia rebaudiana Morita; rebaudioside M; rebaudioside D; rebaudioside M2; bioconversion; steviol glycosides; structure characterization; nuclear magnetic resonance (NMR)
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Prakash, I.; Bunders, C.; Devkota, K.P.; Charan, R.D.; Ramirez, C.; Priedemann, C.; Markosyan, A. 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. Biomolecules 2014, 4, 374-389.

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