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Minor Diterpene Glycosides from the Leaves of Stevia rebaudiana

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    Minor Diterpene Glycosides from the Leaves of Stevia rebaudiana
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    † Ironstone Separations, Inc., Etta, Mississippi 38627, United States
    ‡ Department of Chemistry of Natural Compounds, National Research Center, Dokki 12622, Cairo, Egypt
    § Department of Chemistry, Louisiana State University, Baton Rouge, Louisiana 70803, United States
    ⊥ ChromaDex, Inc., Suite G, Irvine, California 92614, United States
    *Tel: 303-808-4104. E-mail: [email protected]
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    Journal of Natural Products

    Cite this: J. Nat. Prod. 2014, 77, 5, 1231–1235
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    https://doi.org/10.1021/np4009656
    Published April 23, 2014
    Copyright © 2014 The American Chemical Society and American Society of Pharmacognosy
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    Abstract

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    Two new diterpene glycosides in addition to five known glycosides have been isolated from a commercial extract of the leaves of Stevia rebaudiana. Compound 1 (rebaudioside KA) was shown to be 13-[(O-β-d-glucopyranosyl)oxy]ent-kaur-16-en-19-oic acid 2-O-β-d-glucopyranosyl-β-d-glucopyranosyl ester and compound 2, 12-α-[(2-O-β-d-glucopyranosyl-β-d-glucopyranosyl)oxy]ent-kaur-16-en-19-oic acid β-d-glucopyranosyl ester. Five additional known compounds were identified, rebaudioside E, rebaudioside M, rebaudioside N, rebaudioside O, and stevioside, respectively. Enzymatic hydrolysis of stevioside afforded the known ent-kaurane aglycone 13-hydroxy-ent-kaur-16-en-19-oic acid (steviol) (3). The isolated metabolite 1 possesses the ent-kaurane aglycone steviol (3), while compound 2 represents the first example of the isomeric diterpene 12-α-hydroxy-ent-kaur-16-en-19-oic acid existing as a glycoside in S. rebaudiana. The structures of the isolated metabolites 1 and 2 were determined based on comprehensive 1D- and 2D-NMR (COSY, HSQC, and HMBC) studies. A high-quality crystal of compound 3 has formed, which allowed the acquisition of X-ray diffraction data that confirmed its structure. The structural similarities between the new metabolites and the commercially available stevioside sweeteners suggest the newly isolated metabolites should be examined for their organoleptic properties. Accordingly rebaudiosides E, M, N, O, and KA have been isolated in greater than gram quantities.

    Copyright © 2014 The American Chemical Society and American Society of Pharmacognosy

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    Spectroscopic data and mass analysis of compounds 1 and 2, and the absolute configuration analysis of the carbohydrate units are available free of charge via the Internet at http://pubs.acs.org.

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    This article is cited by 30 publications.

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    5. Mohamed A. Ibrahim, Douglas L. Rodenburg, Kamilla Alves, Wilmer H. Perera, Frank R. Fronczek, John Bowling, and James D. McChesney . Rebaudiosides R and S, Minor Diterpene Glycosides from the Leaves of Stevia rebaudiana. Journal of Natural Products 2016, 79 (5) , 1468-1472. https://doi.org/10.1021/acs.jnatprod.6b00048
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    10. Yunyun Zhang, Shaohua Xu, Yue Jin, Yan Dai, Yijun Chen, Xuri Wu. Efficient Biocatalytic Preparation of Rebaudioside KA: Highly Selective Glycosylation Coupled with UDPG Regeneration. Scientific Reports 2020, 10 (1) https://doi.org/10.1038/s41598-020-63379-9
    11. Min Lin, Fei Wang, Yushan Zhu. Modeled structure-based computational redesign of a glycosyltransferase for the synthesis of rebaudioside D from rebaudioside A. Biochemical Engineering Journal 2020, 159 , 107626. https://doi.org/10.1016/j.bej.2020.107626
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    13. Anna Reale, Tiziana Di Renzo, Antonio Russo, Serena Niro, Antonio Ottombrino, Mario Paolo Pellicano. Production of low‐calorie apricot nectar sweetened with stevia: Impact on qualitative, sensory, and nutritional profiles. Food Science & Nutrition 2020, 8 (4) , 1837-1847. https://doi.org/10.1002/fsn3.1464
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    17. Venkata Sai Prakash Chaturvedula, Srinivasa Rao Meneni. Isolation, and Structural Characterization of a New Hexa β-D-Glucopyranosyl Diterpene from Stevia rebaudiana. Natural Product Communications 2018, 13 (4) https://doi.org/10.1177/1934578X1801300405
    18. Indra Prakash, Venkata Sai Prakash Chaturvedula. Steviol Glycosides: Natural Noncaloric Sweeteners. 2018, 101-128. https://doi.org/10.1007/978-3-319-27027-2_9
    19. Wilmer H. Perera, Ion Ghiviriga, Douglas L. Rodenburg, Raquel Carvalho, Kamilla Alves, James D. McChesney. 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 2017, 40 (19) , 3771-3781. https://doi.org/10.1002/jssc.201700435
    20. Wilmer H. Perera, Ion Ghiviriga, Douglas L. Rodenburg, Kamilla Alves, John J. Bowling, Bharathi Avula, Ikhlas A. Khan, James D. McChesney. Rebaudiosides T and U, minor C-19 xylopyranosyl and arabinopyranosyl steviol glycoside derivatives from Stevia rebaudiana (Bertoni) Bertoni. Phytochemistry 2017, 135 , 106-114. https://doi.org/10.1016/j.phytochem.2016.12.001
    21. Wilmer H. Perera, Bharathi Avula, Ikhlas A. Khan, James D. McChesney. Assignment of sugar arrangement in branched steviol glycosides using electrospray ionization quadrupole time‐of‐flight tandem mass spectrometry. Rapid Communications in Mass Spectrometry 2017, 31 (3) , 315-324. https://doi.org/10.1002/rcm.7784
    22. Jun-ming Chen, Li Ding, Xiao-chen Sui, Yong-mei Xia, Hui-da Wan, Tong Lu. Production of a bioactive sweetener steviolbioside via specific hydrolyzing ester linkage of stevioside with a β-galactosidase. Food Chemistry 2016, 196 , 155-160. https://doi.org/10.1016/j.foodchem.2015.09.035
    23. Yu Wang, Liangliang Chen, Yan Li, Yangyang Li, Ming Yan, Kequan Chen, Ning Hao, Lin Xu. Efficient enzymatic production of rebaudioside A from stevioside. Bioscience, Biotechnology, and Biochemistry 2016, 80 (1) , 67-73. https://doi.org/10.1080/09168451.2015.1072457
    24. Indra Prakash, Venkata Sai Prakash Chaturvedula. Steviol Glycosides: Natural Non-Caloric Sweeteners. 2016, 1-28. https://doi.org/10.1007/978-3-319-26478-3_9-1
    25. Gerrit J. Gerwig, Evelien M. te Poele, Lubbert Dijkhuizen, Johannis P. Kamerling. Stevia Glycosides. 2016, 1-72. https://doi.org/10.1016/bs.accb.2016.05.001
    26. Indra Prakash, Cynthia Bunders, Krishna P. Devkota, Romila D. Charan, Rachael M. Hartz, Tracy L. Sears, Tara M. Snyder, Catherine Ramirez. Degradation Products of Rubusoside under Acidic Conditions. Natural Product Communications 2015, 10 (4) https://doi.org/10.1177/1934578X1501000404
    27. James R. Hanson. Diterpenoids of terrestrial origin. Natural Product Reports 2015, 32 (12) , 1654-1663. https://doi.org/10.1039/C5NP00087D
    28. Venkata Sai Prakash Chaturvedula, Julian Zamora. Isolation and Structural Characterization of a New Minor Diterpene Glycoside from Stevia rebaudiana. Natural Product Communications 2014, 9 (12) https://doi.org/10.1177/1934578X1400901203
    29. Indra Prakash, Venkata Chaturvedula. Structures of Some Novel α-Glucosyl Diterpene Glycosides from the Glycosylation of Steviol Glycosides. Molecules 2014, 19 (12) , 20280-20294. https://doi.org/10.3390/molecules191220280
    30. Indra Prakash, Cynthia Bunders, Krishna Devkota, Romila Charan, Catherine Ramirez, Tara Snyder, Christopher Priedemann, Avetik Markosyan, Cyrille Jarrin, Robert Halle. Bioconversion of Rebaudioside I from Rebaudioside A. Molecules 2014, 19 (11) , 17345-17355. https://doi.org/10.3390/molecules191117345
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    Journal of Natural Products

    Cite this: J. Nat. Prod. 2014, 77, 5, 1231–1235
    Click to copy citationCitation copied!
    https://doi.org/10.1021/np4009656
    Published April 23, 2014
    Copyright © 2014 The American Chemical Society and American Society of Pharmacognosy
    Request reuse permissions

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