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

  • J Nat Prod. 2016 May 27;79(5):1468-72. doi: 10.1021/acs.jnatprod.6b00048.
Mohamed A Ibrahim  1  2 ,  Douglas L Rodenburg  1 ,  Kamilla Alves  1 ,  Wilmer H Perera  1 ,  Frank R Fronczek  3 ,  John Bowling  4 ,  James D McChesney  1
Affiliations
  • 1. Ironstone Separations, Inc. , Etta, Mississippi 38627, United States.
  • 2. Department of Chemistry of Natural Compounds, National Research Center , Dokki 12622, Cairo, Egypt.
  • 3. Department of Chemistry, Louisiana State University , Baton Rouge, Louisiana 70803, United States.
  • 4. Department of Chemical Biology and Therapeutics, St. Jude Children's Research Hospital , Memphis, Tennessee 38105, United States.
PMID: 27119206 DOI: 10.1021/acs.jnatprod.6b00048
Abstract

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.

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