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Rebaudiosides R and S, Minor Diterpene Glycosides from the Leaves of Stevia rebaudiana. 2016

Mohamed A Ibrahim, and Douglas L Rodenburg, and Kamilla Alves, and Wilmer H Perera, and Frank R Fronczek, and John Bowling, and James D McChesney
Ironstone Separations, Inc. , Etta, Mississippi 38627, United States.

Two new diterpene glycosides have been isolated from a commercial extract of the leaves of Stevia rebaudiana. Compound 1 was shown to be 13-[(2-O-β-d-glucopyranosyl-3-O-β-d-glucopyranosyl-β-d-xylopyranosyl)oxy]ent-kaur-16-en-19-oic acid β-d-glucopyranosyl ester (rebaudioside R), while compound 2 was determined to be 13-[(2-O-α-d-glucopyranosyl-β-d-glucopyranosyl)oxy]ent-kaur-16-en-19-oic acid 2-O-α-l-rhamnopyranosyl-β-d-glucopyranosyl ester (rebaudioside S). Six additional known compounds were identified, dulcoside B, 13-[(2-O-β-d-xylopyranosyl-β-d-glucopyranosyl)oxy]ent-kaur-16-en-19-oic acid β-d-glucopyranosyl ester, eugenol diglucoside, rebaudioside G, 13-[(2-O-6-deoxy-β-d-glucopyranosyl-3-O-β-d-glucopyranosyl-β-d-glucopyranosyl)oxy]ent-kaur-16-en-19-oic acid β-d-glucopyranosyl ester, and rebaudioside D (3), respectively. The structures of 1 and 2 were determined based on comprehensive 1D and 2D NMR (COSY, HSQC, and HMBC) studies. A high-quality crystal of compound 3 allowed confirmation of its structure by X-ray diffraction.

UI MeSH Term Description Entries
D004224 Diterpenes Twenty-carbon compounds derived from MEVALONIC ACID or deoxyxylulose phosphate. Diterpene,Diterpenes, Cembrane,Diterpenes, Labdane,Diterpenoid,Labdane Diterpene,Norditerpene,Norditerpenes,Norditerpenoid,Cembranes,Diterpenoids,Labdanes,Norditerpenoids,Cembrane Diterpenes,Diterpene, Labdane,Labdane Diterpenes
D006027 Glycosides Any compound that contains a constituent sugar, in which the hydroxyl group attached to the first carbon is substituted by an alcoholic, phenolic, or other group. They are named specifically for the sugar contained, such as glucoside (glucose), pentoside (pentose), fructoside (fructose), etc. Upon hydrolysis, a sugar and nonsugar component (aglycone) are formed. (From Dorland, 28th ed; From Miall's Dictionary of Chemistry, 5th ed) Glycoside
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular
D045786 Diterpenes, Kaurane A group of DITERPENES cyclized into four rings. Ent-Kaurane,Ent-Kaurene,Kaurane,Kaurane Diterpenoid,Kaurane Diterpenoids,Ent-Kauranes,Ent-Kaurenes,Kauranes,Diterpenoid, Kaurane,Diterpenoids, Kaurane,Ent Kaurane,Ent Kaurene,Kaurane Diterpenes
D018515 Plant Leaves Expanded structures, usually green, of vascular plants, characteristically consisting of a bladelike expansion attached to a stem, and functioning as the principal organ of photosynthesis and transpiration. (American Heritage Dictionary, 2d ed) Plant Leaf,Leaf, Plant,Leave, Plant,Leaves, Plant,Plant Leave
D019906 Nuclear Magnetic Resonance, Biomolecular NMR spectroscopy on small- to medium-size biological macromolecules. This is often used for structural investigation of proteins and nucleic acids, and often involves more than one isotope. Biomolecular Nuclear Magnetic Resonance,Heteronuclear Nuclear Magnetic Resonance,NMR Spectroscopy, Protein,NMR, Biomolecular,NMR, Heteronuclear,NMR, Multinuclear,Nuclear Magnetic Resonance, Heteronuclear,Protein NMR Spectroscopy,Biomolecular NMR,Heteronuclear NMR,Multinuclear NMR,NMR Spectroscopies, Protein,Protein NMR Spectroscopies,Spectroscopies, Protein NMR,Spectroscopy, Protein NMR
D036625 Stevia A plant genus of the family ASTERACEAE. Members contain stevioside and other sweet diterpene glycosides. The leaf is used for sweetening (SWEETENING AGENTS). Eupatorium rebaudianum,Sweetleaf,Stevia rebaudiana,Eupatorium rebaudianums,Stevia rebaudianas,Stevias,Sweetleafs,rebaudianas, Stevia,rebaudianums, Eupatorium

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