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Molecules 2012, 17(4), 4186-4196; doi:10.3390/molecules17044186
Article

Synthetic Study on the Relationship Between Structure and Sweet Taste Properties of Steviol Glycosides

* ,
 and
Organic Chemistry Department, Global Research and Development, the Coca-Cola Company, One Coca-Cola Plaza, Atlanta, GA 30313, USA
* Author to whom correspondence should be addressed.
Received: 2 March 2012 / Revised: 24 March 2012 / Accepted: 30 March 2012 / Published: 5 April 2012
(This article belongs to the Section Metabolites)
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Abstract

The structure activity relationship between the C16-C17 methylene double bond on the aglycone of steviol glycosides and the corresponding impact on their sweet taste has been reported here for the first time. It has been observed that converting stevioside and rebaudioside A to their corresponding ketones by switching the doubly bonded methylene on C-17 for a ketone group actually removes the sweet taste properties of these molecules completely. Regenerating the original molecules tends to restore the sweet taste of both the steviol glycosides. Thus this C16-C17 methylene double bond in rebaudioside A and stevioside can be regarded as a pharmacophore essential for the sweetness property of these molecules.
Keywords: reb A; stevioside; steviol; reb A ketone; stevioside ketone and steviol nor ketone, methylenation reb A; stevioside; steviol; reb A ketone; stevioside ketone and steviol nor ketone, methylenation
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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MDPI and ACS Style

Upreti, M.; Dubois, G.; Prakash, I. Synthetic Study on the Relationship Between Structure and Sweet Taste Properties of Steviol Glycosides. Molecules 2012, 17, 4186-4196.

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