title: An intensely sweet dihydroflavonol derivative based on a natural product lead compound.
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.
authors: Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois, Chicago 60612.
authors: N P
authors: NP
authors: Nanayakkara
authors: R A
authors: RA
authors: Hussain
authors: J M
authors: JM
authors: Pezzuto
authors: D D
authors: DD
authors: Soejarto
authors: A D
authors: AD
authors: Kinghorn
mesh_terms: 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*
chemical_list: D005419:Flavonoids; D044948:Flavonols; D013549:Sweetening Agents; D011794:Quercetin; C003377:taxifolin