Synthesis and Taste of Some Flavanone and Dihydrochalcone Glycosides in which Carbohydrate Moieties are Located at differing Positions of the Aglycones

Abstract

To clarify the influence upon taste of the sugar position in the aglycone of dihydrochalcone (DHC), new nine DHC glycosides were synthesized: naringin DHC 4-O-β-d-glucopyrano-side (I), naringin DHC 4-O-β-d-galactopyranoside (II), naringin DHC 4-O-β-d-xylopyranoside (III), 3,2′,3′,-trihydroxy-4-methoxy DHC 3′-O-β-d-galactopyranoside (XII), 3,2′,4′-trihydroxy-4-methoxy DHC 4′-O-β-d-galactopyranoside (XIII), 3,2′,5′-trihydroxy-4-methoxy DHC 5′-O-β-d-galactopyranoside (XIV), 3,2′,6′-trihydroxy-4-methoxy DHC 6′-O-β-d-glactopyranoside (XV), 3,2′,4′,6′-tetrahydroxy-4-methoxy DHC 2″4′-O-β-digalactopyranoside (XVI) and 3,2′,4′-trihydroxy-4-methoxy DHC 4′-O-[2-O-α-l-quinovopyranosyl-β-d-glucopyranoside] (XL). Such compounds as I, II and III which carry the sugars in both the A and B rings of the DHC′s were completely tasteless. Between XII, XIII, XIV, XV, XVI and XL, XIII and XL were 140 and 400 times sweeter than sucrose and the remainder were either slightly sweet, tasteless or bitter.