Diterpene glycosides from Stevia phlebophylla A. Gray

Ceunen, Stijn; Borggraeve, Wim M. De; Compernolle, Frans; Hung, Anh; Geuns, Jan

doi:10.1016/j.carres.2013.06.003

Cited by 10 publications

(10 citation statements)

References 16 publications

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“…It was suggested that glycosylation by UGT85C2 is a key regulatory step of steviol glycoside biosynthesis due to a linear correlation between UGT85C2 transcription and total steviol glycoside content observed in the upper leaves of plants growing under short-day conditions . A regulation of some kind might also explain the significantly linear correlations observed between the transcript levels of ent - kaurenoic acid 13-hydroxylase and the three UGTs during vegetative growth . One possible mode of regulation involves metabolon formation.…”

Section: Biosynthesis Of Steviol Glycosidesmentioning

confidence: 99%

“…For example, in a field study with 300 S. rebaudiana plants, total steviol glycoside content varied between 0.5 and 3.7% w/w at the seedling stage and between 6.7 and 18.6% w/w at harvest time . Even within a population of in vitro propagated plants, a significant variation in steviol glycoside levels remained, necessitating the pooling of large amounts of leaves to obtain reliable results. , Nevertheless, despite these issues, a few general observations can be made regarding steviol glycoside accumulation in S. rebaudiana .…”

Section: Accumulation Of Steviol Glycosides In Stevia Rebaudianamentioning

confidence: 99%

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Steviol Glycosides: Chemical Diversity, Metabolism, and Function

2013

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Steviol glycosides are a group of highly sweet diterpene glycosides discovered in only a few plant species, most notably the Paraguayan shrub Stevia rebaudiana. During the past few decades, the nutritional and pharmacological benefits of these secondary metabolites have become increasingly apparent. While these properties are now widely recognized, many aspects related to their in vivo biochemistry and metabolism and their relationship to the overall plant physiology of S. rebaudiana are not yet understood. Furthermore, the large size of the steviol glycoside pool commonly found within S. rebaudiana leaves implies a significant metabolic investment and poses questions regarding the benefits S. rebaudiana might gain from their accumulation. The current review intends to thoroughly discuss the available knowledge on these issues.

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Section: Biosynthesis Of Steviol Glycosidesmentioning

confidence: 99%

Section: Accumulation Of Steviol Glycosides In Stevia Rebaudianamentioning

confidence: 99%

Steviol Glycosides: Chemical Diversity, Metabolism, and Function

2013

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“…The genus Stevia belongs to the Eupatorieae tribe within the Asteraceae family. Among the ~230 species of the genus Stevia , S. rebaudiana is the only one that contains SGs 3 , 7 . SGs have a core diterpenoid steviol backbone (aglycone) decorated with different glycosylation patterns at the C-13 and C-19 positions 3 , 8 .…”

Section: Introductionmentioning

confidence: 99%

The chromosome-level Stevia genome provides insights into steviol glycoside biosynthesis

Yuan

et al. 2021

Hortic Res

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Stevia (Stevia rebaudiana Bertoni) is well known for its very sweet steviol glycosides (SGs) consisting of a common tetracyclic diterpenoid steviol backbone and a variable glycone. Steviol glycosides are 150–300 times sweeter than sucrose and are used as natural zero-calorie sweeteners. However, the most promising compounds are biosynthesized in small amounts. Based on Illumina, PacBio, and Hi-C sequencing, we constructed a chromosome-level assembly of Stevia covering 1416 Mb with a contig N50 value of 616.85 kb and a scaffold N50 value of 106.55 Mb. More than four-fifths of the Stevia genome consisted of repetitive elements. We annotated 44,143 high-confidence protein-coding genes in the high-quality genome. Genome evolution analysis suggested that Stevia and sunflower diverged ~29.4 million years ago (Mya), shortly after the whole-genome duplication (WGD) event (WGD-2, ~32.1 Mya) that occurred in their common ancestor. Comparative genomic analysis revealed that the expanded genes in Stevia were mainly enriched for biosynthesis of specialized metabolites, especially biosynthesis of terpenoid backbones, and for further oxidation and glycosylation of these compounds. We further identified all candidate genes involved in SG biosynthesis. Collectively, our current findings on the Stevia reference genome will be very helpful for dissecting the evolutionary history of Stevia and for discovering novel genes contributing to SG biosynthesis and other important agronomic traits in future breeding programs.

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“…These compounds have only been found in Stevia phlebophylla A. Gray and in Rubus suavissimus S. Lee (Rosaceae) . Numerous DGs have been isolated from S. rebaudiana and well summarized in the review published by Ceunen and Geuns .…”

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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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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Diterpene glycosides from Stevia phlebophylla A. Gray

Cited by 10 publications

References 16 publications

Steviol Glycosides: Chemical Diversity, Metabolism, and Function

Steviol Glycosides: Chemical Diversity, Metabolism, and Function

The chromosome-level Stevia genome provides insights into steviol glycoside biosynthesis

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

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