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Development of a high-performance liquid chromatography procedure to identify known and detect novel C-13 oligosaccharide moieties in diterpene glycosides from Stevia rebaudiana (Bertoni) Bertoni (Asteraceae): Structure elucidation of rebaudiosides V and W.
J Sep Sci. 2017 Oct; 40(19):3771-3781.JS

Abstract

As an aid for structure elucidation of new steviol glycosides, reversed-phase C18 high-performance liquid chromatography method was developed with several previously characterized diterpene glycosides, to identify known and detect novel aglycone-C13 oligosaccharide moieties and indirectly identify C-19 interlinkages. Elution order of several diterpene glycosides and their aglycone-C13 oligosaccharide substituted with different sugar arrangements were also summarized. Comparison of the retention time of a product obtained after alkaline hydrolysis with the aglycone-C-13 portions of known compounds reported herein allowed us to deduce the exact positions of the sugars in the C-13 oligosaccharide portion. The elution position of several steviol glycosides with an ent-kaurene skeleton was helpful to describe an identification key. Two previously uncharacterized diterpene glycosides together with two known compounds were isolated from a commercial Stevia rebaudiana leaf extract. One was found to be 13-[(2-O-β-d-xylopyranosyl-3-O-β-d-glucopyranosyl-β-d-glucopyranosyl)oxy]ent-kaur-16-en-19-oic acid-(2-O-β-d-glucopyranosyl-β-d-glucopyranosyl) ester (rebaudioside V), whereas the other was determined to be 13-[(2-O-β-d-xylopyranosyl-3-O-β-d-glucopyranosyl-β-d-glucopyranosyl)oxy]ent-kaur-16-en-19-oic acid-(2-O-α-l-rhamnopyranosyl-3-O-β-d-glucopyranosyl-β-d-glucopyranosyl) ester (rebaudioside W). Previously reported compounds were isolated in gram quantities and identified as rebaudioside J and rebaudioside H. In addition, a C-19 sugar-free derivative was also prepared from rebaudioside H to afford rebaudioside H1 . Chemical structures were partially determined by the high-performance liquid chromatography method and unambiguously characterized by using one-dimensional and two-dimensional nuclear magnetic resonance experiments.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Perera WH
Ironstone Separations, Inc., Etta, MS, USA.
Ghiviriga I
Department of Chemistry, University of Florida, Gainesville, FL, USA.
Rodenburg DL
Ironstone Separations, Inc., Etta, MS, USA.
Carvalho R
Universidade Federal de Mato Grosso do Sul, Campo Grande, MS, Brazil.
Alves K
Ironstone Separations, Inc., Etta, MS, USA.
McChesney JD
Ironstone Separations, Inc., Etta, MS, USA.

MeSH

Chromatography, High Pressure LiquidDiterpenesGlycosidesOligosaccharidesStevia

Pub Type(s)

Journal Article

Language

eng

PubMed ID

28762654

Citation

Perera, Wilmer H., et al. "Development of a High-performance Liquid Chromatography Procedure to Identify Known and Detect Novel C-13 Oligosaccharide Moieties in Diterpene Glycosides From Stevia Rebaudiana (Bertoni) Bertoni (Asteraceae): Structure Elucidation of Rebaudiosides V and W." Journal of Separation Science, vol. 40, no. 19, 2017, pp. 3771-3781.
Perera WH, Ghiviriga I, Rodenburg DL, et al. Development of a high-performance liquid chromatography procedure to identify known and detect novel C-13 oligosaccharide moieties in diterpene glycosides from Stevia rebaudiana (Bertoni) Bertoni (Asteraceae): Structure elucidation of rebaudiosides V and W. J Sep Sci. 2017;40(19):3771-3781.
Perera, W. H., Ghiviriga, I., Rodenburg, D. L., Carvalho, R., Alves, K., & McChesney, J. D. (2017). Development of a high-performance liquid chromatography procedure to identify known and detect novel C-13 oligosaccharide moieties in diterpene glycosides from Stevia rebaudiana (Bertoni) Bertoni (Asteraceae): Structure elucidation of rebaudiosides V and W. Journal of Separation Science, 40(19), 3771-3781. https://doi.org/10.1002/jssc.201700435
Perera WH, et al. Development of a High-performance Liquid Chromatography Procedure to Identify Known and Detect Novel C-13 Oligosaccharide Moieties in Diterpene Glycosides From Stevia Rebaudiana (Bertoni) Bertoni (Asteraceae): Structure Elucidation of Rebaudiosides V and W. J Sep Sci. 2017;40(19):3771-3781. PubMed PMID: 28762654.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Development of a high-performance liquid chromatography procedure to identify known and detect novel C-13 oligosaccharide moieties in diterpene glycosides from Stevia rebaudiana (Bertoni) Bertoni (Asteraceae): Structure elucidation of rebaudiosides V and W. AU - Perera,Wilmer H, AU - Ghiviriga,Ion, AU - Rodenburg,Douglas L, AU - Carvalho,Raquel, AU - Alves,Kamilla, AU - McChesney,James D, Y1 - 2017/09/01/ PY - 2017/04/19/received PY - 2017/06/19/revised PY - 2017/07/19/accepted PY - 2017/8/2/pubmed PY - 2018/6/21/medline PY - 2017/8/2/entrez KW - Stevia rebaudiana KW - diterpene glycosides KW - ent-kaurene core KW - saponification products SP - 3771 EP - 3781 JF - Journal of separation science JO - J Sep Sci VL - 40 IS - 19 N2 - As an aid for structure elucidation of new steviol glycosides, reversed-phase C18 high-performance liquid chromatography method was developed with several previously characterized diterpene glycosides, to identify known and detect novel aglycone-C13 oligosaccharide moieties and indirectly identify C-19 interlinkages. Elution order of several diterpene glycosides and their aglycone-C13 oligosaccharide substituted with different sugar arrangements were also summarized. Comparison of the retention time of a product obtained after alkaline hydrolysis with the aglycone-C-13 portions of known compounds reported herein allowed us to deduce the exact positions of the sugars in the C-13 oligosaccharide portion. The elution position of several steviol glycosides with an ent-kaurene skeleton was helpful to describe an identification key. Two previously uncharacterized diterpene glycosides together with two known compounds were isolated from a commercial Stevia rebaudiana leaf extract. One was found to be 13-[(2-O-β-d-xylopyranosyl-3-O-β-d-glucopyranosyl-β-d-glucopyranosyl)oxy]ent-kaur-16-en-19-oic acid-(2-O-β-d-glucopyranosyl-β-d-glucopyranosyl) ester (rebaudioside V), whereas the other was determined to be 13-[(2-O-β-d-xylopyranosyl-3-O-β-d-glucopyranosyl-β-d-glucopyranosyl)oxy]ent-kaur-16-en-19-oic acid-(2-O-α-l-rhamnopyranosyl-3-O-β-d-glucopyranosyl-β-d-glucopyranosyl) ester (rebaudioside W). Previously reported compounds were isolated in gram quantities and identified as rebaudioside J and rebaudioside H. In addition, a C-19 sugar-free derivative was also prepared from rebaudioside H to afford rebaudioside H1 . Chemical structures were partially determined by the high-performance liquid chromatography method and unambiguously characterized by using one-dimensional and two-dimensional nuclear magnetic resonance experiments. SN - 1615-9314 UR - https://www.unboundmedicine.com/medline/citation/28762654/Development_of_a_high_performance_liquid_chromatography_procedure_to_identify_known_and_detect_novel_C_13_oligosaccharide_moieties_in_diterpene_glycosides_from_Stevia_rebaudiana__Bertoni__Bertoni__Asteraceae_:_Structure_elucidation_of_rebaudiosides_V_and_W_ L2 - https://doi.org/10.1002/jssc.201700435 DB - PRIME DP - Unbound Medicine ER -