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Int. J. Mol. Sci. 2013, 14(8), 15669-15680; doi:10.3390/ijms140815669
Article

Hydrogenation of the Exocyclic Olefinic Bond at C-16/C-17 Position of ent-Kaurane Diterpene Glycosides of Stevia rebaudiana Using Various Catalysts

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Received: 18 April 2013 / Revised: 8 July 2013 / Accepted: 17 July 2013 / Published: 26 July 2013
(This article belongs to the Section Biochemistry, Molecular Biology and Biophysics)
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Abstract

Catalytic hydrogenation of the exocyclic double bond present between C16 and C17 carbons of the four ent-kaurane diterpene glycosides namely rebaudioside A, rebaudioside B, rebaudioside C, and rebaudioside D isolated from Stevia rebaudiana has been carried out using Pt/C, Pd(OH)2, Rh/C, Raney Ni, PtO2, and 5% Pd/BaCO3 to their corresponding dihydro derivatives with 17α and 17β methyl group isomers. Reactions were performed using the above-mentioned catalysts with the solvents methanol, water, and ethanol/water (8:2) under various conditions. Synthesis of reduced steviol glycosides was performed using straightforward chemistry and their structures were characterized on the basis of 1D and 2D NMR spectral data, including a comparison with reported spectral data.
Keywords: ent-Kaurane diterpene glycosides; Stevia rebaudiana; catalytic hydrogenation; Pt/C; Pd(OH)2; Rh/C; Raney Ni; PtO2; 5% Pd/BaCO3; structure characterization ent-Kaurane diterpene glycosides; Stevia rebaudiana; catalytic hydrogenation; Pt/C; Pd(OH)2; Rh/C; Raney Ni; PtO2; 5% Pd/BaCO3; structure characterization
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Chaturvedula, V.S.P.; Prakash, I. Hydrogenation of the Exocyclic Olefinic Bond at C-16/C-17 Position of ent-Kaurane Diterpene Glycosides of Stevia rebaudiana Using Various Catalysts. Int. J. Mol. Sci. 2013, 14, 15669-15680.

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