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. Epub 2016 Apr 27.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Diterpenes / chemistry
  • Diterpenes / isolation & purification
  • Diterpenes, Kaurane / chemistry
  • Diterpenes, Kaurane / isolation & purification*
  • Glycosides / chemistry
  • Glycosides / isolation & purification*
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Leaves / chemistry
  • Stereoisomerism
  • Stevia / chemistry*

Substances

  • Diterpenes
  • Diterpenes, Kaurane
  • Glycosides
  • rebaudioside R
  • rebaudioside S
  • argyrophilic acid