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. 2017 Jan 31;7(1):10.
doi: 10.3390/biom7010010.

A Novel Diterpene Glycoside with Nine Glucose Units from Stevia rebaudiana Bertoni

Indra Prakash  1 , Gil Ma  1 , Cynthia Bunders  1 , Romila D Charan  2 , Catherine Ramirez  3 , Krishna P Devkota  4 , Tara M Snyder  5
Affiliations

A Novel Diterpene Glycoside with Nine Glucose Units from Stevia rebaudiana Bertoni

Indra Prakash et al. Biomolecules. .

Abstract

Following our interest in new diterpene glycosides with better taste profiles than that of Rebaudioside M, we have recently isolated and characterized Rebaudioside IX-a novel steviol glycoside-from a commercially-supplied extract of Stevia rebaudiana Bertoni. This molecule contains a hexasaccharide group attached at C-13 of the central diterpene core, and contains three additional glucose units when compared with Rebaudioside M. Here we report the complete structure elucidation-based on extensive Nuclear Magnetic Resonance (NMR) analysis (1H, 13C, Correlation Spectroscopy (COSY), Heteronuclear Single Quantum Coherence-Distortionless Enhancement Polarization Transfer (HSQC-DEPT), Heteronuclear Multiple Bond Correlation (HMBC), 1D Total Correlation Spectroscopy (TOCSY), Nuclear Overhauser Effect Spectroscopy (NOESY)) and mass spectral data-of this novel diterpene glycoside with nine sugar moieties and containing a relatively rare 16 α-linked glycoside. A steviol glycoside bearing nine glucose units is unprecedented in the literature, and could have an impact on the natural sweetener catalog.

Keywords: 16 glycoside linkage; Diterpene glycosides; NMR; Stevia rebaudiana Bertoni; nine sugar steviol glycoside; structure elucidation.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Structures of Rebaudioside IX (1) and Rebaudioside M (2).
Figure 2
Figure 2
1H NMR spectrum of Rebaudioside IX (1) (500 MHz, 300 K) in pyridine-d5. ppm: parts per million.
Figure 3
Figure 3
Summary of key Heteronuclear Multiple Bond Correlation (HMBC) and Correlation Spectroscopy (COSY) correlations used to assign the C-13 and C-19 glycoside region of compound (1).
See this image and copyright information in PMC

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