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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

 and
*
Organic Chemistry Department, Global Research and Development, The Coca-Cola Company, One Coca-Cola Plaza, Atlanta, GA 30313, USA Current address: Natural Ingredient Development, Blue California, 30111 Tomas, Rancho Santa Margarita, CA 92688, USA
* Author to whom correspondence should be addressed.
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 (CC BY 3.0).
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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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