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: K Shimizu, R Kondo, K Sakai, N Takeda, T Nagahata, T Oniki
• Journal: Lipids (Lipids) Vol. 36 Issue 12 Pg. 1321-6 (Dec 2001) ISSN: 0024-4201 [Print] United States
• PMID: 11834083 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

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

Topics

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