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Novel vitamin E derivative with 4‐substituted resorcinol moiety has both antioxidant and tyrosinase inhibitory properties
Author(s) -
Shimizu Kuniyoshi,
Kondo Ryuichiro,
Sakai Kokki,
Takeda Norio,
Nagahata Tetsuji,
Oniki Takayuki
Publication year - 2001
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/s11745-001-0847-9
Subject(s) - tyrosinase , chemistry , resorcinol , antioxidant , moiety , skin whitening , stereochemistry , biochemistry , organic chemistry , enzyme , pharmacology , active ingredient , medicine
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 α‐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.