Molecular design of potent tyrosinase inhibitors having the bibenzyl skeleton

In order to develop water soluble tyrosinase inhibitors, bibenzyl xyloside 1 isolated from Chlorophytum arundinaceum (liliaceae), and its derivatives 2 and 3 were synthesized by using Wittig reaction and trichloroimidate glycosylation procedure as key steps. Xylosides 1–3 showed potent tyrosinase inhibitory activity with IC50s of 1.6, 0.43, and 0.73 μM, respectively, although each NMR data of synthetic bibenzyls was not identical to that of naturally occurring xyloside 1.