An intensely sweet dihydroflavonol derivative based on a natural product lead compound

J Med Chem. 1988 Jun;31(6):1250-3. doi: 10.1021/jm00401a030.

Abstract

The dihydroflavonol dihydroquercetin 3-acetate (1) was isolated as a sweet constituent of the young shoots of Tessaria dodoneifolia (Hook. & Arn.) Cabrera (Compositae). Compound 1 and dihydroquercetin 3-acetate 4'-(methyl ether) (2), a novel synthetic analogue of this natural product lead compound, were rated by a taste panel as being 80 and 400 times sweeter than a 2% w/v sucrose solution, respectively. Synthetic dihydroquercetin 4'-(methyl ether) (3) showed a reduced sweetness intensity when compared to 2, while (+)-dihydroquercetin (4) was devoid of sweetness. Dihydroflavonol derivatives 1-3 represent a new class of potentially noncaloric and noncariogenic intense sweeteners.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Flavonoids / pharmacology*
  • Flavonols
  • Humans
  • Molecular Conformation
  • Quercetin / analogs & derivatives
  • Quercetin / pharmacology
  • Structure-Activity Relationship
  • Sweetening Agents / chemical synthesis
  • Sweetening Agents / pharmacology*

Substances

  • Flavonoids
  • Flavonols
  • Sweetening Agents
  • Quercetin
  • taxifolin