Abstract
The following three new analogs of naringin (I) were synthesized. Naringein-7-[6'-Omethyl-O-α-L-mannopyranosyl-(1→2)-β-D-glucopyranoside] (II), naringenin-7-[6'-Omethyl-O-α-D-mannopyranosyl-(1→2)-β-D-glucopyranoside] (III) and naringenin-7-[O-α-L-rhamnopyranosyl-(1→6)-β-D-galactopyranoside] (XVI).
Compounds II, III, narirutin (naringenin-7-[O-α-L-rhamnopyranosyl-(1→6)-β-n-glucopyranoside] (XV) and XVI are 0.10, 0.13, 0.05 and 0.08 times as bitter as I, respectively. From the above organoleptic result it was concluded that the methyl group of L-rhamnose in I is one of the essential factors for intense bitterness. Attachment of α-L-rhamnose to the_??_-position of D-glucoside or D-galactoside of naringenin does not abolish the taste of the resulting glycosides but elicits a moderate bitter taste.
