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 c...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1988-06, Vol.31 (6), p.1250-1253
Main Authors: DHAMMIKA NANAYAKKARA, N. P, HUSSAIN, R. A, PEZZUTO, J. M, SOEJARTO, D. D, KINGHORN, A. D
Format: Article
Language:English
Subjects:
Biological and medical sciences
Flavonoids - pharmacology
Flavonols
General pharmacology
Humans
Medical sciences
Molecular Conformation
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
Quercetin - analogs & derivatives
Quercetin - pharmacology
Structure-Activity Relationship
Sweetening Agents - chemical synthesis
Sweetening Agents - pharmacology
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Summary: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.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00401a030