Analysis of structural features responsible for the sweetness of the sesquiterpene, hernandulcin
- 1 May 1988
- journal article
- research article
- Published by Springer Nature in Cellular and Molecular Life Sciences
- Vol. 44 (5) , 447-449
- https://doi.org/10.1007/bf01940543
Abstract
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.This publication has 16 references indexed in Scilit:
- A quantitative structure-activity relationship analysis of some 4-aminodiphenyl sulfone antibacterial agents using linear free energy and molecular modeling methodsJournal of Medicinal Chemistry, 1987
- The intensely sweet sesquiterpene hernandulcin: isolation, synthesis, characterization, and preliminary safety evaluationJournal of Agricultural and Food Chemistry, 1987
- Sweetness and bitterness contributions of structural units of aspartame and some analogsJournal of Agricultural and Food Chemistry, 1985
- Hernandulcin: An Intensely Sweet Compound Discovered by Review of Ancient LiteratureScience, 1985
- Naturally occurring carbonyl compounds are mutagens Salmonella tester strain TA104Mutation Research - Fundamental and Molecular Mechanisms of Mutagenesis, 1985
- Soft agonist receptor interactions: Theoretical and experimental simulation of the active site of the receptor of sweet moleculesInternational Journal of Quantum Chemistry, 1984
- Interaction of conformationally flexible agonists with the active site of sweet taste. A study of arylureasJournal of Medicinal Chemistry, 1983
- Structure-mutagenicity relationship in α,β-unsaturated carbonylic compounds and their corresponding allylic alcoholsMutation Research - Fundamental and Molecular Mechanisms of Mutagenesis, 1982
- A Molecular Theory of Sweet TasteJournal of Pharmaceutical Sciences, 1972
- Dependence of Relative Sweetness on Hydrophobic BondingNature, 1966