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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

by
Indra Prakash
1,*,
Cynthia Bunders
1,
Krishna P. Devkota
2,
Romila D. Charan
2,
Catherine Ramirez
2,
Christopher Priedemann
2 and
Avetik Markosyan
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.
Biomolecules 2014, 4(2), 374-389; https://doi.org/10.3390/biom4020374
Submission 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 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.
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)

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MDPI and ACS Style

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. https://doi.org/10.3390/biom4020374

AMA Style

Prakash I, Bunders C, Devkota KP, Charan RD, 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(2):374-389. https://doi.org/10.3390/biom4020374

Chicago/Turabian Style

Prakash, Indra, Cynthia Bunders, Krishna P. Devkota, Romila D. Charan, Catherine Ramirez, Christopher Priedemann, and Avetik Markosyan. 2014. "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 4, no. 2: 374-389. https://doi.org/10.3390/biom4020374

APA Style

Prakash, I., Bunders, C., Devkota, K. P., Charan, R. D., Ramirez, C., Priedemann, C., & Markosyan, A. (2014). 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, 4(2), 374-389. https://doi.org/10.3390/biom4020374

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