METHODS AND RESULTS: A novel vitamin E derivative, (6"-hydroxy-2",5",7",8"-tetramethylchroman-2"-yl)Methyl 3-(2,4-dihydroxyphenyl)propionate (TM4R), which has a chromanoxyl ring and 4-substituted resorcinol moieties, was synthesized; and its inhibitory effects on tyrosinase, antioxidant ability, and lightening effect of ultraviolet B (UVB)-induced hyperpigmentation were estimated.Methyl 3-(2,4-dihydroxyphenyl)propionate showed potent inhibitory activity on tyrosinase, which is the rate-limiting enzyme in melanogenesis. The scavenging activities of Methyl 3-(2,4-dihydroxyphenyl)propionate on 1,1-diphenyl-2-picrylhydrazyl and hydroxyl radicals were found to be nearly the same as those of alpha-tocopherol. Furthermore, an efficient lightening effect was observed following topical application of Methyl 3-(2,4-dihydroxyphenyl)propionate to UVB-stimulated hyperpigmented dorsal skin of brownish guinea pigs.
CONCLUSIONS:
These results suggest that Methyl 3-(2,4-dihydroxyphenyl)propionate may be a candidate for an efficient whitening agent, possibly by inhibiting tyrosinase activity and biological reactions caused by reactive oxygen species. |