Resorcinol alkyl glucosides as potent tyrosinase inhibitors.


Department of Applied Biological Chemistry, School of Agriculture, Utsunomiya University, Tochigi 321-0943, Japan; Department of Applied Life Science, United Graduate School of Agricultural Science, Tokyo University of Agriculture and Technology, Tokyo 183-8509, Japan. Electronic address: [Email]


Resorcinol alkyl glucosides 7-12 were developed as novel tyrosinase inhibitors based on the structure of rhododendrin. These were synthesized from 2,4-dibenzyloxybenzaldehyde using either the Wittig or the Horner-Wadsworth-Emmons reaction with Koenigs-Knorr glycosylation as key steps. The tyrosinase inhibitory activity of 7-12 increased with the length of the alkyl spacer between resorcinol and glucose. The 50% inhibitory concentration (IC50) of tetradecyl derivative 12 was 0.39 μM, making it the most potent of the compounds synthesized. The IC50 of 8 (3.62 μM) with a propyl spacer was ca 10 times that of 7 (35.9 μM) with an ethyl spacer. This significant activity difference suggests that an interaction between resorcinol alkyl glucoside and tyrosinase may increase remarkably if the length of the alkyl spacer exceeds C3.


Alkyl spacer,Glycosylation,Resorcinol alkyl glucoside,Tyrosinase inhibitor,