An intensely sweet dihydroflavonol derivative based on a natural product lead compound.
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.
Nanayakkara
N P
NP
Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois, Chicago 60612.
Hussain
R A
RA
Pezzuto
J M
JM
Soejarto
D D
DD
Kinghorn
A D
AD
D005419:Flavonoids / Q000494:pharmacology*; D044948:Flavonols; D006801:Humans; D008968:Molecular Conformation; D011794:Quercetin / Q000031:analogs & derivatives / Q000494:pharmacology; D013329:Structure-Activity Relationship; D013549:Sweetening Agents / Q000138:chemical synthesis / Q000494:pharmacology*
D005419:Flavonoids; D044948:Flavonols; D013549:Sweetening Agents; D011794:Quercetin; C003377:taxifolin