To investigate the inhibitory potency of phloretin 2'-O-β-L-glycodides, phloretin 2'-O-(6-deoxy-β-L-galactoside) (1), -2'-O-(6-deoxy-β-L-galactoside) (2) and -2'-O-β-L-glucoside (3) were synthesized. The appropriate phloracetophenone 4'-O-β-L-glycosides were coupled with p-hydroxybenzaldehyde in aq. alkali to yield the respective chalcone glycosides, which were catalytically hydrogenated to give 1-3.
Compounds 1-3 as well as phloretin 2'-O-(6-deoxy-a-L-mannopyranoside) (glycyphyllin) each exhibited dose-dependent inhibition of 3-O-methyl-D-glucose-evoked ΔPD (transmural potential difference), using the everted jejunal segment of rats. A kinetic study revealed that the mode of action of 1-3 was non-conpetitive and that their Ki values were more than 400 times smaller than the Km value, indicating that they possess strong inhibitory potency toward the Na⁺ co-transporter.

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