Rebaudiosides T and U, minor C-19 xylopyranosyl and arabinopyranosyl steviol glycoside derivatives from Stevia rebaudiana (Bertoni) Bertoni

Perera, Wilmer H.; Ghiviriga, Ion; Rodenburg, Douglas L.; Alves, Kamilla; Bowling, John J.; Avula, Bharathi; Khan, Ikhlas A.; McChesney, James D.

doi:10.1016/j.phytochem.2016.12.001

Cited by 19 publications

(17 citation statements)

References 13 publications

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“…Melting points were recorded using an OptiMelt automated Melting Point System from Standford Research Systems using open capillary. High resolution electrospray ionization tandem mass spectrometry (HRESI–MS/MS) were acquired by direct infusion using an Agilent Model G6530A QTOF mass detector equipped as previously reported . NMR spectra were acquired on a Varian Inova spectrometer, operating at 500 MHz for proton, equipped with a 5 mm indirect detection probe, and with z ‐axis pulsed‐field gradients.…”

Section: Methodsmentioning

confidence: 99%

“…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%

“…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%

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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: Methodsmentioning

confidence: 99%

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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“…Some minor compounds were identified prior to studies reported by Ohta et al ., where several new steviol glycosides were discovered, followed by other important advances made by Chaturvedula et al . Our group has also been working extensively in recent years on the isolation of new steviol glycosides with some recent contributions in the area . Therefore, many of the minor components of Stevia rebaudiana are better known today but many more of them remain uncharacterized.…”

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confidence: 92%

Assignment of sugar arrangement in branched steviol glycosides using electrospray ionization quadrupole time‐of‐flight tandem mass spectrometry

Perera

Avula

Khan

et al. 2017

Rapid Comm Mass Spectrometry

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Those steviol glycosides with a monosaccharide or less hindered disaccharides at position C-19 are cleaved at low collision energy (10 eV) while highly hindered disaccharides and trisaccharides are cleaved at 40 eV. However, sugars attached at C-13 cleave at highest collision energies in the following order: the C-3 sugar, followed by the C-2 sugar and finally the sugar directly linked at C-13. Copyright © 2016 John Wiley & Sons, Ltd.

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“…The COSY and 1D-TOCSY data allowed the assignments of . The glycosylation pattern is similar to that for rebaudioside T. 6 We have termed this compound stevatisene T.…”

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confidence: 79%

Five New Ent-Atisene Glycosides From Stevia rebaudiana

Devkota

Charan

Priedemann

et al. 2019

Natural Product Communications

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Five new ent-atisene diterpene glycosides (1-5) have been isolated from Stevia rebaudiana Bertoni. This adds to a list of only 2 new ent-atisene diterpene glycosides isolated previously from S. rebaudiana. Diterpene glycosides isolated from S. rebaudiana, such as the rebaudiosides, are typically associated with the ent-kaurene core and glycosylation at the C-13 and C-19 positions. Extensive application of nuclear magnetic resonance spectroscopy techniques (1H, 13C, 1D-TOCSY, COSY, HSQC-DEPT, HMBC, and ROESY) as well as high-resolution mass spectrometry demonstrated that the ent-atisenes 1 to 5 had glycosylation patterns identical to rebaudiosides J, N, O, K, and T, respectively. We have named these compounds stevatisene J, N, O, K, and T, respectively.

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Rebaudiosides T and U, minor C-19 xylopyranosyl and arabinopyranosyl steviol glycoside derivatives from Stevia rebaudiana (Bertoni) Bertoni

Cited by 19 publications

References 13 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

Assignment of sugar arrangement in branched steviol glycosides using electrospray ionization quadrupole time‐of‐flight tandem mass spectrometry

Five New Ent-Atisene Glycosides From Stevia rebaudiana

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