title: 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.
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.
authors: The Coca-Cola Company, Atlanta, GA 30313, USA. iprakash@coca-cola.com.
authors: Indra
authors: I
authors: Prakash
authors: The Coca-Cola Company, Atlanta, GA 30313, USA. cbunders@coca-cola.com.
authors: Cynthia
authors: C
authors: Bunders
authors: AMRI-Albany, Analytical Development, Albany, NY 12212, USA. Krishna.Devkota@amriglobal.com.
authors: Krishna P
authors: KP
authors: Devkota
authors: AMRI-Albany, Analytical Development, Albany, NY 12212, USA. Romila.Charan@amriglobal.com.
authors: Romila D
authors: RD
authors: Charan
authors: AMRI-Albany, Analytical Development, Albany, NY 12212, USA. Catherine.Ramirez@amriglobal.com.
authors: Catherine
authors: C
authors: Ramirez
authors: AMRI-Albany, Analytical Development, Albany, NY 12212, USA. Christopher.Priedemann@amriglobal.com.
authors: Christopher
authors: C
authors: Priedemann
authors: PureCircle Limited, Lengkuk Teknologi, Bandar Enstek, Negeri Sembilan 71760, Malaysia. avetik@purecircle.com.
authors: Avetik
authors: A
authors: Markosyan
mesh_terms: D001711:Biotransformation; D045786:Diterpenes, Kaurane / Q000737:chemistry* / Q000302:isolation & purification* / Q000378:metabolism*; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D013045:Species Specificity; D036625:Stevia / Q000737:chemistry*; D014312:Trisaccharides / Q000737:chemistry* / Q000302:isolation & purification* / Q000378:metabolism
chemical_list: D045786:Diterpenes, Kaurane; D014312:Trisaccharides; C025474:rebaudioside A; C000590692:rebaudioside M