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Rebaudiosides R and S, Minor Diterpene Glycosides from the Leaves of Stevia rebaudiana.
J Nat Prod. 2016 05 27; 79(5):1468-72.JN

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.

Authors+Show Affiliations

Ironstone Separations, Inc. , Etta, Mississippi 38627, United States. Department of Chemistry of Natural Compounds, National Research Center , Dokki 12622, Cairo, Egypt.Ironstone Separations, Inc. , Etta, Mississippi 38627, United States.Ironstone Separations, Inc. , Etta, Mississippi 38627, United States.Ironstone Separations, Inc. , Etta, Mississippi 38627, United States.Department of Chemistry, Louisiana State University , Baton Rouge, Louisiana 70803, United States.Department of Chemical Biology and Therapeutics, St. Jude Children's Research Hospital , Memphis, Tennessee 38105, United States.Ironstone Separations, Inc. , Etta, Mississippi 38627, United States.

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

27119206

Citation

Ibrahim, Mohamed A., et al. "Rebaudiosides R and S, Minor Diterpene Glycosides From the Leaves of Stevia Rebaudiana." Journal of Natural Products, vol. 79, no. 5, 2016, pp. 1468-72.
Ibrahim MA, Rodenburg DL, Alves K, et al. Rebaudiosides R and S, Minor Diterpene Glycosides from the Leaves of Stevia rebaudiana. J Nat Prod. 2016;79(5):1468-72.
Ibrahim, M. A., Rodenburg, D. L., Alves, K., Perera, W. H., Fronczek, F. R., Bowling, J., & McChesney, J. D. (2016). Rebaudiosides R and S, Minor Diterpene Glycosides from the Leaves of Stevia rebaudiana. Journal of Natural Products, 79(5), 1468-72. https://doi.org/10.1021/acs.jnatprod.6b00048
Ibrahim MA, et al. Rebaudiosides R and S, Minor Diterpene Glycosides From the Leaves of Stevia Rebaudiana. J Nat Prod. 2016 05 27;79(5):1468-72. PubMed PMID: 27119206.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Rebaudiosides R and S, Minor Diterpene Glycosides from the Leaves of Stevia rebaudiana. AU - Ibrahim,Mohamed A, AU - Rodenburg,Douglas L, AU - Alves,Kamilla, AU - Perera,Wilmer H, AU - Fronczek,Frank R, AU - Bowling,John, AU - McChesney,James D, Y1 - 2016/04/27/ PY - 2016/4/28/entrez PY - 2016/4/28/pubmed PY - 2017/6/6/medline SP - 1468 EP - 72 JF - Journal of natural products JO - J Nat Prod VL - 79 IS - 5 N2 - 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. SN - 1520-6025 UR - https://www.unboundmedicine.com/medline/citation/27119206/Rebaudiosides_R_and_S_Minor_Diterpene_Glycosides_from_the_Leaves_of_Stevia_rebaudiana_ DB - PRIME DP - Unbound Medicine ER -