Synthetic Study on the Relationship Between Structure and Sweet Taste Properties of Steviol Glycosides
| Autor: | Mani Upreti, Indra Prakash, Grant E. Dubois |
|---|---|
| Rok vydání: | 2012 |
| Předmět: |
Ketone
Double bond Stereochemistry Pharmaceutical Science Steviol Article stevioside ketone and steviol nor ketone methylenation Analytical Chemistry lcsh:QD241-441 chemistry.chemical_compound rebAketone Glucosides lcsh:Organic chemistry Drug Discovery Organic chemistry Stevioside Physical and Theoretical Chemistry chemistry.chemical_classification reb A reb A ketone Organic Chemistry stevioside Glycoside Sweetness steviosideketone and steviol nor ketone methylenation Aglycone chemistry Chemistry (miscellaneous) Sweetening Agents steviol Molecular Medicine Diterpenes Kaurane Rebaudioside A |
| Zdroj: | Molecules, Vol 17, Iss 4, Pp 4186-4196 (2012) Molecules; Volume 17; Issue 4; Pages: 4186-4196 Molecules |
| ISSN: | 1420-3049 |
| DOI: | 10.3390/molecules17044186 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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