Novel vitamin E derivative with 4-substituted resorcinol moiety has both antioxidant and tyrosinase inhibitory properties.
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.
Shimizu
K
K
Department of Forest Products, Faculty of Agriculture, Kyushu University Graduate School, Fukuoka, Japan.
Kondo
R
R
Sakai
K
K
Takeda
N
N
Nagahata
T
T
Oniki
T
T
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*
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