Rebaudiosides R and S, Minor Diterpene Glycosides from the Leaves of <i>Stevia rebaudiana</i>

Ibrahim, Mohamed A.; Rodenburg, Douglas L.; Alves, Kamilla; Perera, Wilmer H.; Fronczek, Frank R.; Bowling, John J.; McChesney, James D.

doi:10.1021/acs.jnatprod.6b00048

Cited by 30 publications

(26 citation statements)

References 19 publications

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“…The saponification products (SPs) were prepared from pure DGs previously isolated and purified by ironstone using high efficiency silica gel and RP-C18 chromatographies [20]. All the DGs were previously characterized by NMR and/or MS/MS [12][13][14]16].…”

Section: Preparation Of the Saponification Productsmentioning

confidence: 99%

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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

Perera

Ghiviriga

Rodenburg

et al. 2017

J of Separation Science

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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 H . 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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Section: Preparation Of the Saponification Productsmentioning

confidence: 99%

“…Numerous DGs have been isolated from S. rebaudiana [10] and well summarized in the review published by Ceunen and Geuns [11]. Additionally, reports of new natural DGs have appeared recently [12][13][14].…”

Section: Introductionmentioning

confidence: 99%

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

Perera

Ghiviriga

Rodenburg

et al. 2017

J of Separation Science

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“…rebaudioside-N and rebaudioside-O. Similarly, Rebaudioside-R and S have been isolated by Ibrahim et al (2016). Chaturvedula (2014) recognised a minor penta β-D glucopyranosyl diterpene from S. rebaudiana leaves.…”

Section: Chemical Constituentsmentioning

confidence: 92%

Chemistry and analytical techniques for ent-kaurene-glycosides of Stevia rebaudiana Bertoni - A review

Kumari

Kumar

2017

JANS

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Abstract:The Stevia genus encompasses about 200 herbs and shrubs species. Stevia rebaudiana, one of the members has gained commercial importance as a natural low-calorie sweetener, due to the presence of high concentration of stevioside and rebaudioside -A (25% to 45% of stevioside content) in the leaves. The major processes involved in the production and quantification of steviol glycosides are extraction, purification and estimation. Various extraction methods have been used for extraction of steviol glycosides in the world. The extraction methods of steviol glycosides mostly differed at the stage of clarification of extracts. The present study is an attempt to summarize the scattered literature and reports on a single podium. Moreover, it also depicts upto date literature regarding numerous extraction, purification and quantitative estimation methods for steviol glycosides

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“…Recent studies reported identification and structural characterization of several minor diterpene glycoside compounds from various commercial stevia extracts [9] [10]. In this paper, we are reporting a new compound, rebaudioside D3, obtained by the enzymatic conversion of rebaudioside E. The same compound was identified from the crude extract of Stevia rebaudiana using comparative HPLC and LC-MS.…”

Section: Introductionmentioning

confidence: 90%

Enzymatic Synthesis and Structural Characterization of Rebaudioside D3, a Minor Steviol Glycoside of <i>Stevia rebaudiana</i> Bertoni

Mao¹,

Chaturvedula²,

Vick³

et al. 2017

AJPS

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Rebaudioside D3, a novel steviol glycoside, is produced by specific UDP-glycosyltransferase of rebaudioside E, a minor steviol glycoside of Stevia rebaudiana Bertoni. The complete proton and carbon NMR spectral assignments ofglucopyranosyl) ester, was achieved by the extensive 1D and 2D NMR ( 1 H and 13 C, TOCSY, HMQC, HMBC) as well as mass spectral data. Further, hydrolysis studies were performed on rebaudioside D3 using acid and enzymatic studies to identify aglycone and sugar residues in its structure. Rebaudioside D3 is detected in the commercial extract of the leaves of Stevia rebaudiana by LC-MS analysis, suggesting rebaudioside D3 is a natural steviol glycoside.

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

Cited by 30 publications

References 19 publications

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

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

Chemistry and analytical techniques for ent-kaurene-glycosides of Stevia rebaudiana Bertoni - A review

Enzymatic Synthesis and Structural Characterization of Rebaudioside D3, a Minor Steviol Glycoside of <i>Stevia rebaudiana</i> Bertoni

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

Cited by 30 publications

References 19 publications

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

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

Chemistry and analytical techniques for ent-kaurene-glycosides of Stevia rebaudiana Bertoni - A review

Enzymatic Synthesis and Structural Characterization of Rebaudioside D3, a Minor Steviol Glycoside of &lt;i&gt;Stevia rebaudiana&lt;/i&gt; Bertoni

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Enzymatic Synthesis and Structural Characterization of Rebaudioside D3, a Minor Steviol Glycoside of <i>Stevia rebaudiana</i> Bertoni