Novel vitamin E derivative with 4-substituted resorcinol moiety has both antioxidant and tyrosinase inhibitory properties

Lipids. 2001 Dec;36(12):1321-6. doi: 10.1007/s11745-001-0847-9.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antioxidants / chemical synthesis
  • Antioxidants / chemistry*
  • Antioxidants / pharmacology*
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / pharmacology*
  • Guinea Pigs
  • Kinetics
  • Monophenol Monooxygenase / antagonists & inhibitors*
  • Skin Pigmentation / drug effects
  • Skin Pigmentation / radiation effects
  • Ultraviolet Rays
  • Vitamin E / analogs & derivatives*
  • Vitamin E / chemical synthesis
  • Vitamin E / chemistry*
  • Vitamin E / pharmacology*

Substances

  • (6''-hydroxy-2'',5'',7'',8''-tetramethylchroman-2''-yl)methyl 3-(2',4'-dihydroxyphenyl)propionate
  • Antioxidants
  • Enzyme Inhibitors
  • Vitamin E
  • Monophenol Monooxygenase