Structure–Taste Relationships of Flavanone and Dihydrochalcone Glycosides Containing (l→2) Linked Disaccharides

Abstract

To clarify the structure-taste relationships of flavanone and dihydrochalcone (DHC) glycosides, the new glycosides, naringenin 7-O-(2-O-α-d-fucopyranosyl-β-d-galactoside) (I), -7-O-(2-O-β-d-fucopyranosyl-β-d-galactoside) (II), -7-O-(2-O-α-l-fucopyranosyl-β-d-galactoside) (III), -7-O-(2-O-α-l-fucopyranosyl-β-d-galactoside) (V), -7-O-(2-O-α-l-rhamnopyranosyl-β-d-mannoside) (VI), -7-O-α-d-galactoside) (XII), hesperetin 7-O-(2-O-β-l-fucopyranosyl-β-d-galactoside) (IV), naringenin DHC 4′-O-(2-O-β-d-fucopyranosyl-β-d-galactoside) (VII), -4′-(2-O-β-d-fucopyranosyl-β-d-galactoside) (VIII), -4′-O-(2-O-β-l-fucopyranosyl-β-d-galactoside) (IX), -4′-O-(2-O-β-l-fucopyranosyl-β-d-galactoside) (XI), -4′-O-β-d-galactoside) (XIII) and hesperetin DHC 4′-O-(2-O-β-l-fucopyranosyl-β-d-galactoside) (X) were synthesized. The flavanones I, IV and XII had no taste but II, III, V and VI respectively tasted 0.05, 0.58, 0.39 and 0.75 times more bitter than naringin. Compounds VII and VIII were tasteless but IX, X, XI and XIII were found to be 1.46, 4.80, 1.04, and 0.90 times sweeter than saccharin, respectively, on a molar basis.