A Novel Diterpene Glycoside with Nine Glucose Units from Stevia rebaudiana Bertoni.
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.
The Coca-Cola Company, One Coca-Cola Plaza, Atlanta, GA 30313, USA. cynbun@gmail.com.
Indra
I
Prakash
The Coca-Cola Company, One Coca-Cola Plaza, Atlanta, GA 30313, USA. cynbun@gmail.com.
Gil
G
Ma
The Coca-Cola Company, One Coca-Cola Plaza, Atlanta, GA 30313, USA. cynbun@gmail.com.
Cynthia
C
Bunders
AMRI-Albany, Analytical Development, Albany, NY 12212, USA. Romila.Charan@amriglobal.com.
Romila D
RD
Charan
AMRI-Albany, Analytical Development, Albany, NY 12212, USA. Catherine.Ramirez@amriglobal.com.
Catherine
C
Ramirez
AMRI-Albany, Analytical Development, Albany, NY 12212, USA. Krishna.Devkota@amriglobal.com.
Krishna P
KP
Devkota
AMRI-Albany, Analytical Development, Albany, NY 12212, USA. Tara.Snyder@amriglobal.com.
Tara M
TM
Snyder
D004224:Diterpenes / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry; D036625:Stevia / Q000737:chemistry*
D004224:Diterpenes; D006027:Glycosides; D010936:Plant Extracts
16 glycoside linkage; Diterpene glycosides; NMR; Stevia rebaudiana Bertoni; nine sugar steviol glycoside; structure elucidation