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Experientia

, Volume 44, Issue 5, pp 447–449 | Cite as

Analysis of structural features responsible for the sweetness of the sesquiterpene, hernandulcin

  • C. M. Compadre
  • R. A. Hussain
  • R. L. de Compadre Lopez
  • J. M. Pezzuto
  • A. D. Kinghorn
Short Communications

Summary

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 words

Hernandulcin intense sweetener synthetic analogues taste attributes conformational analysis structure-activity relationships safety assessment 

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Copyright information

© Birkhäuser Verlag 1988

Authors and Affiliations

  • C. M. Compadre
    • 1
  • R. A. Hussain
    • 1
  • R. L. de Compadre Lopez
    • 1
  • J. M. Pezzuto
    • 1
  • A. D. Kinghorn
    • 1
  1. 1.Department of Medicinal Chemistry and Pharmacognosy, and Program for Collaborative Research in the Pharmaceutical Science, College of PharmacyUniversity of Illinois at ChicagoChicagoUSA

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