Dihydroresveratrol cellobioside and xylobioside as effective melanogenesis activators

Dihydroresveratrol cellobioside and xylobioside, whose structures were designed based on that of the naturally occurring melanogenesis-controlling agent dihydroresveratrol glucoside, were synthesized via Schmidt glycosylation as the key step. Both analogues stimulated melanogenesis with efficacies comparable to that of 8-methoxypsoralen, a well-known melanogenesis activator. This suggests that diglycosyl modification of the 4’-OH on the dihydroresveratrol skeleton leads to the activation of melanogenesis, both with and without hydroxymethyl groups in the sugar moieties. [Display omitted] •Dihydroresveratrol cellobioside 3 was synthesized via the Schmidt glycosylation.•Xylobioside 4 was prepared from the corresponding xylooligosaccharides.•Both derivatives are potent melanogenesis activators of B16F0 melanoma cells.