Analysis of structural features responsible for the sweetness of the sesquiterpene, hernandulcin
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The relationship between sweetness and structure was studied for several analogues of the intensely sweet sesquiterpene, hernandulcin. These derivatives were prepared synthetically, and were subjected to spectroscopic and conformational analysis. With the exception of the parent substance, none of the derivatives tested proved to be sweet. Evidence gathered in this study suggests that hernandulcin binds to its putative receptor through a three-point interaction, involving the C-1 carbonyl and C-1′ hydroxyl groups, and the double bond between C-4′ and C-5′. In the course of a preliminary safety assessment, the 3-desmethyl derivative of hernandulcin was found to be mutagenic towardSalmonella typhimurium strain TM677.
Key wordsHernandulcin intense sweetener synthetic analogues taste attributes conformational analysis structure-activity relationships safety assessment
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- 3.Kinghorn, A. D. and Compadre, C. M., Pharm. Int.6 (1985) 201.Google Scholar
- 4.O'Brien Nabors, L., and Gelardi, R. C. (Eds), Alternative Sweeteners. Marcel Dekker, New York and Basel 1986.Google Scholar
- 5.Birch, G. G., Endeavour, New Series11 (1987) 21.Google Scholar
- 7.DuBois, G. E., A. Rep. Med. Chem.17 (1982) 323.Google Scholar
- 17.Lutz, D., Eder, E., Neudecker, T., and Henschler, D., Mutation Res.93 (1982) 305.Google Scholar