title: Novel vitamin E derivative with 4-substituted resorcinol moiety has both antioxidant and tyrosinase inhibitory properties.
abstract: 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. TM4R showed potent inhibitory activity on tyrosinase, which is the rate-limiting enzyme in melanogenesis. The scavenging activities of TM4R 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 TM4R to UVB-stimulated hyperpigmented dorsal skin of brownish guinea pigs. These results suggest that TM4R may be a candidate for an efficient whitening agent, possibly by inhibiting tyrosinase activity and biological reactions caused by reactive oxygen species.
authors.affiliation: Department of Forest Products, Faculty of Agriculture, Kyushu University Graduate School, Fukuoka, Japan.
authors.forename: K
authors.initials: K
authors.lastname: Shimizu
authors.forename: R
authors.initials: R
authors.lastname: Kondo
authors.forename: K
authors.initials: K
authors.lastname: Sakai
authors.forename: N
authors.initials: N
authors.lastname: Takeda
authors.forename: T
authors.initials: T
authors.lastname: Nagahata
authors.forename: T
authors.initials: T
authors.lastname: Oniki
mesh_terms: D000818:Animals; D000975:Antioxidants / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D006168:Guinea Pigs; D007700:Kinetics; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors*; D012880:Skin Pigmentation / Q000187:drug effects / Q000528:radiation effects; D014466:Ultraviolet Rays; D014810:Vitamin E / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*
chemical_list: C462380:(6''-hydroxy-2'',5'',7'',8''-tetramethylchroman-2''-yl)methyl 3-(2',4'-dihydroxyphenyl)propionate; D000975:Antioxidants; D004791:Enzyme Inhibitors; D014810:Vitamin E; D014442:Monophenol Monooxygenase