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

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Lipids

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 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.

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Abbreviations

COSY:

correlation spectroscopy

DCC:

N,N′-dicyclohexyl-carbodiimide

DMAP:

4-dimethylaminopyridine

DMSO:

dimethylsulfoxide

DOPA:

dihydroxyphenylalanine

DPPacid:

3-(2′,4′-dihydroxyphenyl)propionic acid

DPPH:

1,1-diphenyl-2-picrylhydrazyl

ESR:

electron spin resonance

HMBC:

heteronuclear multiple bond connectivity

HR-FAB-MS:

high resolution-fast atom bombardment-mass spectrometry

IC50 :

concentration at which 50% inhibition occurs

NBA:

3-nitrobenzyl alcohol

NMR:

nuclear magnetic resonance

TM:

2-hydroxymethyl-2,5,7,8-tetramethylchroman-6-ol

TM4R:

(6″-hydroxy-2″,5″,7″,8″-tetramethylchroman-2″-yl)methyl 3-(2′,4′-dihydroxyphenyl)propionate

Trolox:

2-carboxy-2,5,7,8-tetramethylchroman-6-ol

UV:

ultraviolet

UVB:

ultraviolet B

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Authors and Affiliations

  1. Kansai Koso Co. Ltd., 816-0921, Ohnojo, Japan

    Norio Takeda & Tetsuji Nagahata

  2. Kyushu Dental College, 803-8580, Kitakyushu, Japan

    Takayuki Oniki

  3. Laboratory of Forest Chemistry and Biochemistry, Department of Forest Products, Faculty of Agriculture, Kyushu University Graduate School, 6-10-1 Hakozaki, Higashiku, 812-8581, Fukuoka, Japan

    Kuniyoshi Shimizu, Ryuichiro Kondo & Kokki Sakai

Authors
  1. Kuniyoshi Shimizu
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  2. Ryuichiro Kondo
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  3. Kokki Sakai
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  4. Norio Takeda
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  5. Tetsuji Nagahata
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  6. Takayuki Oniki
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Correspondence to Ryuichiro Kondo.

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Shimizu, K., Kondo, R., Sakai, K. et al. Novel vitamin E derivative with 4-substituted resorcinol moiety has both antioxidant and tyrosinase inhibitory properties. Lipids 36, 1321–1326 (2001). https://doi.org/10.1007/s11745-001-0847-9

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  • DOI: https://doi.org/10.1007/s11745-001-0847-9

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