Minor Diterpene Glycosides from the Leaves of <i>Stevia rebaudiana</i>

Ibrahim, Mohamed A.; Rodenburg, Douglas L.; Alves, Kamilla; Fronczek, Frank R.; McChesney, James D.; Wu, Chongming; Nettles, Brian; Venkataraman, Sylesh K.; Jaksch, Frank

doi:10.1021/np4009656

Cited by 32 publications

(31 citation statements)

References 23 publications

(30 reference statements)

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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%

“…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: 98%

“…Steviol is produced by enzymatic hydrolysis with gastric juices of the snail Helix pomatia , pectinase or hesperidinase . In our experience, steviol has only been obtained with H. pomatia snail gastric juices . Both aglycones are easily differentiated using the above mentioned HPLC method 2.8.2 : steviol elutes faster (earlier) than isosteviol.…”

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confidence: 95%

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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%

Section: Introductionmentioning

confidence: 98%

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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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“…More than 30 steviol glycosides have been discovered in S. rebaudiana, of which stevioside and rebaudioside A are the predominant sweetening agents. 1,2) Their concentrations vary widely depending on the genotype, cultivation conditions, and harvesting time of the plant. 3) The typical proportion of stevioside and rebaudioside A in dry leaf matter of wild stevia plants is 9.1 and 3.8%, respectively.…”

Section: Efficient Enzymatic Production Of Rebaudioside a From Steviomentioning

confidence: 99%

Efficient enzymatic production of rebaudioside A from stevioside

Chen

et al. 2016

Bioscience, Biotechnology, and Biochemistry

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Stevioside and rebaudioside A are the chief diterpene glycosides present in the leaves of Stevia rebaudiana. Rebaudioside A imparts a desirable sweet taste, while stevioside produces a residual bitter aftertaste. Enzymatic synthesis of rebaudioside A from stevioside can increase the ratio of rebaudioside A to stevioside in steviol glycoside products, providing a conceivable strategy to improve the organoleptic properties of steviol glycoside products. Here, we demonstrate the efficient conversion of stevioside to rebaudioside A by coupling the activities of recombinant UDP-glucosyltransferase UGT76G1 from S. rebaudiana and sucrose synthase AtSUS1 from Arabidopsis thaliana. The conversion occurred via regeneration of UDP-glucose by AtSUS1. UDP was applicable as the initial material instead of UDP-glucose for UDP-glucose recycling. The amount of UDP could be greatly reduced in the reaction mixture. Rebaudioside A yield in 30 h with 2.4 mM stevioside, 7.2 mM sucrose, and 0.006 mM UDP was 78%.

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“…Steviolbioside 13-[(2-O-β-d-glucopyranosyl-β-d-glucopyranosyl)oxyl]kaur-16-en-18oic acid] is a natural sweetener found in S. rebaudiana leaves in rare amounts (Ibrahim et al, 2014). Synthetic methods for steviolbioside such as alkaline and enzymatic hydrolysis of Ste have been investigated (Ko et al, 2013;Chen et al, 2016).…”

Section: Production Of Steviolbiosidementioning

confidence: 99%