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Rebaudiosides T and U, minor C-19 xylopyranosyl and arabinopyranosyl steviol glycoside derivatives from Stevia rebaudiana (Bertoni) Bertoni.
Phytochemistry. 2017 Mar; 135:106-114.P

Abstract

Two diterpene glycosides were isolated from a commercial Stevia rebaudiana leaf extract. One was found to be 13-[(2-O-β-d-glucopyranosyl-3-O-β-d-glucopyranosyl-β-d-glucopyranosyl)oxy]ent-kaur-16-en-19-oic acid-(2-O-β-d-xylopyranosyl-3-O-β-d-glucopyranosyl- β-d-glucopyranosyl) ester (rebaudioside T), whereas the other was determined to be 13-[(2-O-β-d-glucopyranosyl-3-O-β-d-glucopyranosyl-β-d-glucopyranosyl)oxy]ent-kaur-16-en-19-oic acid-(6-O-α-l-arabinopyranosyl-β-d-glucopyranosyl) ester (rebaudioside U). In addition, five C-19 sugar free derivatives were prepared and identified as follows: 13-[(2-O-α-l-rhamnopyranosyl-β-d-glucopyranosyl)]oxy]kaur-16-en-19-oic acid (dulcoside A1); 13-[(2-O-β-d-xylopyranosy-3-O-β-d-glucopyranosyl-β-d-glucopyranosyl)oxy]kaur-16-en-19-oic acid; 13-[(2-O-β-d-xylopyranosyl-β-d-glucopyranosyl-)oxy]kaur-16-en-19-oic acid; 13-[(2-O-β-d-glucopyranosyl-3-O-β-d-glucopyranosyl-β-d-xylopyranosyl-)oxy]kaur-16-en-19-oic acid (rebaudioside R1) and 13-[(2-O-6-deoxy-β-d-glucopyranosyl-3-O-β-d-glucopyranosyl-β-d-glucopyranosyl)oxy]kaur-16-en-19-oic acid, respectively. Chemical structures were determined by NMR experiments. HPLC analyses were also useful to differentiate different steviol-C13 sugar substituent patterns by elution position.

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Authors+Show Affiliations

Perera WH
Ironstone Separations, Inc., Etta, Oxford, MS 38627, USA.
Ghiviriga I
Department of Chemistry, University of Florida, Gainesville, FL 32611, USA.
Rodenburg DL
Ironstone Separations, Inc., Etta, Oxford, MS 38627, USA.
Alves K
Ironstone Separations, Inc., Etta, Oxford, MS 38627, USA.
Bowling JJ
Department of Chemical Biology and Therapeutics, St. Jude Children's Research Hospital, Memphis, TN 38105, USA.
Avula B
National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, University of Mississippi, University, MS 38677, USA.
Khan IA
National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, University of Mississippi, University, MS 38677, USA; Division of Pharmacognosy, Department of BioMolecular Sciences, School of Pharmacy, University of Mississippi, University, MS 38677, USA.
McChesney JD
Ironstone Separations, Inc., Etta, Oxford, MS 38627, USA. Electronic address: jdmcchesney@yahoo.com.

MeSH

DiterpenesDiterpenes, KauraneGlycosidesMolecular StructureSaponinsSteviaTriterpenes

Pub Type(s)

Journal Article

Language

eng

PubMed ID

27979591

Citation

Perera, Wilmer H., et al. "Rebaudiosides T and U, Minor C-19 Xylopyranosyl and Arabinopyranosyl Steviol Glycoside Derivatives From Stevia Rebaudiana (Bertoni) Bertoni." Phytochemistry, vol. 135, 2017, pp. 106-114.
Perera WH, Ghiviriga I, Rodenburg DL, et al. Rebaudiosides T and U, minor C-19 xylopyranosyl and arabinopyranosyl steviol glycoside derivatives from Stevia rebaudiana (Bertoni) Bertoni. Phytochemistry. 2017;135:106-114.
Perera, W. H., Ghiviriga, I., Rodenburg, D. L., Alves, K., Bowling, J. J., Avula, B., Khan, I. A., & McChesney, J. D. (2017). Rebaudiosides T and U, minor C-19 xylopyranosyl and arabinopyranosyl steviol glycoside derivatives from Stevia rebaudiana (Bertoni) Bertoni. Phytochemistry, 135, 106-114. https://doi.org/10.1016/j.phytochem.2016.12.001
Perera WH, et al. Rebaudiosides T and U, Minor C-19 Xylopyranosyl and Arabinopyranosyl Steviol Glycoside Derivatives From Stevia Rebaudiana (Bertoni) Bertoni. Phytochemistry. 2017;135:106-114. PubMed PMID: 27979591.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Rebaudiosides T and U, minor C-19 xylopyranosyl and arabinopyranosyl steviol glycoside derivatives from Stevia rebaudiana (Bertoni) Bertoni. AU - Perera,Wilmer H, AU - Ghiviriga,Ion, AU - Rodenburg,Douglas L, AU - Alves,Kamilla, AU - Bowling,John J, AU - Avula,Bharathi, AU - Khan,Ikhlas A, AU - McChesney,James D, Y1 - 2016/12/12/ PY - 2016/07/04/received PY - 2016/10/11/revised PY - 2016/12/02/accepted PY - 2016/12/17/pubmed PY - 2017/3/17/medline PY - 2016/12/17/entrez KW - Asteraceae KW - Stevia rebaudiana KW - Steviol glycosides SP - 106 EP - 114 JF - Phytochemistry JO - Phytochemistry VL - 135 N2 - Two diterpene glycosides were isolated from a commercial Stevia rebaudiana leaf extract. One was found to be 13-[(2-O-β-d-glucopyranosyl-3-O-β-d-glucopyranosyl-β-d-glucopyranosyl)oxy]ent-kaur-16-en-19-oic acid-(2-O-β-d-xylopyranosyl-3-O-β-d-glucopyranosyl- β-d-glucopyranosyl) ester (rebaudioside T), whereas the other was determined to be 13-[(2-O-β-d-glucopyranosyl-3-O-β-d-glucopyranosyl-β-d-glucopyranosyl)oxy]ent-kaur-16-en-19-oic acid-(6-O-α-l-arabinopyranosyl-β-d-glucopyranosyl) ester (rebaudioside U). In addition, five C-19 sugar free derivatives were prepared and identified as follows: 13-[(2-O-α-l-rhamnopyranosyl-β-d-glucopyranosyl)]oxy]kaur-16-en-19-oic acid (dulcoside A1); 13-[(2-O-β-d-xylopyranosy-3-O-β-d-glucopyranosyl-β-d-glucopyranosyl)oxy]kaur-16-en-19-oic acid; 13-[(2-O-β-d-xylopyranosyl-β-d-glucopyranosyl-)oxy]kaur-16-en-19-oic acid; 13-[(2-O-β-d-glucopyranosyl-3-O-β-d-glucopyranosyl-β-d-xylopyranosyl-)oxy]kaur-16-en-19-oic acid (rebaudioside R1) and 13-[(2-O-6-deoxy-β-d-glucopyranosyl-3-O-β-d-glucopyranosyl-β-d-glucopyranosyl)oxy]kaur-16-en-19-oic acid, respectively. Chemical structures were determined by NMR experiments. HPLC analyses were also useful to differentiate different steviol-C13 sugar substituent patterns by elution position. SN - 1873-3700 UR - https://www.unboundmedicine.com/medline/citation/27979591/Rebaudiosides_T_and_U_minor_C_19_xylopyranosyl_and_arabinopyranosyl_steviol_glycoside_derivatives_from_Stevia_rebaudiana__Bertoni__Bertoni_ DB - PRIME DP - Unbound Medicine ER -