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Tetra-glucopyranosyl Diterpene ent-Kaur-16-en-19-oic Acid and ent-13(S)-Hydroxyatisenoic Acid Derivatives from a Commercial Extract of Stevia rebaudiana (Bertoni) Bertoni.
Molecules. 2018 Dec 15; 23(12)M

Abstract

Stevia rebaudiana and its diterpene glycosides are one of the main focuses of food companies interested in developing novel zero calorie sugar substitutes since the recognition of steviol glycosides as Generally Recognized as Safe (GRAS) by the United States Food and Drug Administration. Rebaudioside A, one of the major steviol glycosides of the leaves is more than 200 times sweeter than sucrose. However, its lingering aftertaste makes it less attractive as a table-top sweetener, despite its human health benefits. Herein, we report the purification of two novel tetra-glucopyranosyl diterpene glycosides 1 and 3 (rebaudioside A isomers) from a commercial Stevia rebaudiana leaf extract compounds, their saponification products compounds 2 and 4, together with three known compounds isolated in gram quantities. Compound 1 was determined to be 13-[(2-O-β-d-glucopyranosyl-6-O-β-d-glucopyranosyl-β-d-glucopyranosyl) oxy]ent-kaur-16-en-19-oic acid-β-d-glucopyranosy ester (rebaudioside Z), whereas compound 3 was found to be 13-[(2-O-β-d-glucopyranosyl-3-O-β-d-glucopyranosyl-β-d-glucopyranosyl) oxy]ent-hydroxyatis-16-en-19-oic acid -β-d-glucopyranosy ester. Two new tetracyclic derivatives with no sugar at position C-19 were prepared from rebaudiosides 1 and 3 under mild alkaline hydrolysis to afford compounds 2 13-[(2-O-β-d-glucopyranosyl-6-O-β-d-glucopyranosyl-β-d-glucopyranosyl) oxy]ent-kaur-16-en-19-oic acid (rebaudioside Z₁) and 4 13-[(2-O-β-d-glucopyranosyl-3-O-β-d-glucopyranosyl-β-d-glucopyranosyl) oxy]ent-hydroxyatis-16-en-19-oic acid. Three known compounds were purified in gram quantities and identified as rebaudiosides A (5), H (6) and J (7). Chemical structures were unambiguously elucidated using different approaches, namely HRESIMS, HRESI-MS/MS, and 1D-and 2D-NMR spectroscopic data. Additionally, a high-quality crystal of iso-stevioside was grown in methanol and its structure confirmed by X-ray diffraction.

Authors+Show Affiliations

Ironstone Separations, Inc., Etta, Oxford, MS 38627, USA. wilmer.perera@gmail.com. ORISE Fellow-Agricultural Research Service, Natural Product Utilization Research Unit, U.S. Department of Agriculture, University of Mississippi, Oxford, MS 38677, USA. wilmer.perera@gmail.com.Department of Chemistry, University of Florida, Gainesville, FL 32611, USA. ion@chem.ufl.edu.Ironstone Separations, Inc., Etta, Oxford, MS 38627, USA. douglasrodenburg@yahoo.com.Ironstone Separations, Inc., Etta, Oxford, MS 38627, USA. Kamilla_07@yahoo.com.National Center for Natural Products Research, University of Mississippi, Oxford, MS 38677, USA. fwiggers@olemiss.edu.National Center for Natural Products Research, University of Mississippi, Oxford, MS 38677, USA.Department of Chemistry, Louisiana State University, Baton Rouge, LA 70803, USA. ffroncz@lsu.edu.National Center for Natural Products Research, University of Mississippi, Oxford, MS 38677, USA. mmibrahi@olemiss.edu. Chemistry of Natural Compounds Department, Pharmaceutical and Drug Industries Division, National Research Centre, Dokki, Giza 12622, Egypt. mmibrahi@olemiss.edu.National Center for Natural Products Research, University of Mississippi, Oxford, MS 38677, USA. milias@olemiss.edu.National Center for Natural Products Research, University of Mississippi, Oxford, MS 38677, USA. bavula@olemiss.edu.National Center for Natural Products Research, University of Mississippi, Oxford, MS 38677, USA. ikhan@olemiss.edu.Ironstone Separations, Inc., Etta, Oxford, MS 38627, USA. jdmcchesney@yahoo.com.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

30558268

Citation

Perera, Wilmer H., et al. "Tetra-glucopyranosyl Diterpene ent-Kaur-16-en-19-oic Acid and ent-13(S)-Hydroxyatisenoic Acid Derivatives From a Commercial Extract of Stevia Rebaudiana (Bertoni) Bertoni." Molecules (Basel, Switzerland), vol. 23, no. 12, 2018.
Perera WH, Ghiviriga I, Rodenburg DL, et al. Tetra-glucopyranosyl Diterpene ent-Kaur-16-en-19-oic Acid and ent-13(S)-Hydroxyatisenoic Acid Derivatives from a Commercial Extract of Stevia rebaudiana (Bertoni) Bertoni. Molecules. 2018;23(12).
Perera, W. H., Ghiviriga, I., Rodenburg, D. L., Alves, K., Wiggers, F. T., Hufford, C. D., Fronczek, F. R., Ibrahim, M. A., Muhammad, I., Avula, B., Khan, I. A., & McChesney, J. D. (2018). Tetra-glucopyranosyl Diterpene ent-Kaur-16-en-19-oic Acid and ent-13(S)-Hydroxyatisenoic Acid Derivatives from a Commercial Extract of Stevia rebaudiana (Bertoni) Bertoni. Molecules (Basel, Switzerland), 23(12). https://doi.org/10.3390/molecules23123328
Perera WH, et al. Tetra-glucopyranosyl Diterpene ent-Kaur-16-en-19-oic Acid and ent-13(S)-Hydroxyatisenoic Acid Derivatives From a Commercial Extract of Stevia Rebaudiana (Bertoni) Bertoni. Molecules. 2018 Dec 15;23(12) PubMed PMID: 30558268.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Tetra-glucopyranosyl Diterpene ent-Kaur-16-en-19-oic Acid and ent-13(S)-Hydroxyatisenoic Acid Derivatives from a Commercial Extract of Stevia rebaudiana (Bertoni) Bertoni. AU - Perera,Wilmer H, AU - Ghiviriga,Ion, AU - Rodenburg,Douglas L, AU - Alves,Kamilla, AU - Wiggers,Frank T, AU - Hufford,Charles D, AU - Fronczek,Frank R, AU - Ibrahim,Mohamed A, AU - Muhammad,Ilias, AU - Avula,Bharathi, AU - Khan,Ikhlas A, AU - McChesney,James D, Y1 - 2018/12/15/ PY - 2018/11/29/received PY - 2018/12/13/revised PY - 2018/12/14/accepted PY - 2018/12/19/entrez PY - 2018/12/19/pubmed PY - 2019/3/6/medline KW - 13(S)-hydroxyatisenoic acid derivative KW - Stevia rebaudiana KW - diterpene glycosides KW - iso-stevioside X-ray structure KW - rebaudioside A isomers JF - Molecules (Basel, Switzerland) JO - Molecules VL - 23 IS - 12 N2 - Stevia rebaudiana and its diterpene glycosides are one of the main focuses of food companies interested in developing novel zero calorie sugar substitutes since the recognition of steviol glycosides as Generally Recognized as Safe (GRAS) by the United States Food and Drug Administration. Rebaudioside A, one of the major steviol glycosides of the leaves is more than 200 times sweeter than sucrose. However, its lingering aftertaste makes it less attractive as a table-top sweetener, despite its human health benefits. Herein, we report the purification of two novel tetra-glucopyranosyl diterpene glycosides 1 and 3 (rebaudioside A isomers) from a commercial Stevia rebaudiana leaf extract compounds, their saponification products compounds 2 and 4, together with three known compounds isolated in gram quantities. Compound 1 was determined to be 13-[(2-O-β-d-glucopyranosyl-6-O-β-d-glucopyranosyl-β-d-glucopyranosyl) oxy]ent-kaur-16-en-19-oic acid-β-d-glucopyranosy ester (rebaudioside Z), whereas compound 3 was found to be 13-[(2-O-β-d-glucopyranosyl-3-O-β-d-glucopyranosyl-β-d-glucopyranosyl) oxy]ent-hydroxyatis-16-en-19-oic acid -β-d-glucopyranosy ester. Two new tetracyclic derivatives with no sugar at position C-19 were prepared from rebaudiosides 1 and 3 under mild alkaline hydrolysis to afford compounds 2 13-[(2-O-β-d-glucopyranosyl-6-O-β-d-glucopyranosyl-β-d-glucopyranosyl) oxy]ent-kaur-16-en-19-oic acid (rebaudioside Z₁) and 4 13-[(2-O-β-d-glucopyranosyl-3-O-β-d-glucopyranosyl-β-d-glucopyranosyl) oxy]ent-hydroxyatis-16-en-19-oic acid. Three known compounds were purified in gram quantities and identified as rebaudiosides A (5), H (6) and J (7). Chemical structures were unambiguously elucidated using different approaches, namely HRESIMS, HRESI-MS/MS, and 1D-and 2D-NMR spectroscopic data. Additionally, a high-quality crystal of iso-stevioside was grown in methanol and its structure confirmed by X-ray diffraction. SN - 1420-3049 UR - https://www.unboundmedicine.com/medline/citation/30558268/Tetra_glucopyranosyl_Diterpene_ent_Kaur_16_en_19_oic_Acid_and_ent_13_S__Hydroxyatisenoic_Acid_Derivatives_from_a_Commercial_Extract_of_Stevia_rebaudiana__Bertoni__Bertoni_ DB - PRIME DP - Unbound Medicine ER -