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Open AccessArticle

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

1
Ironstone Separations, Inc., Etta, Oxford, MS 38627, USA
2
ORISE Fellow-Agricultural Research Service, Natural Product Utilization Research Unit, U.S. Department of Agriculture, University of Mississippi, Oxford, MS 38677, USA
3
Department of Chemistry, University of Florida, Gainesville, FL 32611, USA
4
National Center for Natural Products Research, University of Mississippi, Oxford, MS 38677, USA
5
Department of Chemistry, Louisiana State University, Baton Rouge, LA 70803, USA
6
Chemistry of Natural Compounds Department, Pharmaceutical and Drug Industries Division, National Research Centre, Dokki, Giza 12622, Egypt
*
Author to whom correspondence should be addressed.
Charles D. Hufford deceased on 15 May 2017.
Academic Editors: Muhammad Ilias and Charles L. Cantrell
Molecules 2018, 23(12), 3328; https://doi.org/10.3390/molecules23123328
Received: 29 November 2018 / Revised: 13 December 2018 / Accepted: 14 December 2018 / Published: 15 December 2018
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. View Full-Text
Keywords: Stevia rebaudiana; diterpene glycosides; rebaudioside A isomers; 13(S)-hydroxyatisenoic acid derivative; iso-stevioside X-ray structure Stevia rebaudiana; diterpene glycosides; rebaudioside A isomers; 13(S)-hydroxyatisenoic acid derivative; iso-stevioside X-ray structure
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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. 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, 3328.

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