EMAIL THIS PAGE TO A FRIEND

Journal of dermatological science

A convenient screening method to differentiate phenolic skin whitening tyrosinase inhibitors from leukoderma-inducing phenols.


PMID 26228294

Abstract

Tyrosinase is able to oxidize a great number of phenols and catechols to form ortho-quinones. Ortho-quinones are highly reactive compounds that exert cytotoxicity through binding with thiol enzymes and the production of reactive oxygen species. Certain phenolic (and catecholic) compounds are known to induce contact/occupational leukoderma through activation to ortho-quinones. We report a convenient screening method to follow the oxidation of those leukoderma-inducing phenols by mushroom tyrosinase. Oxidation of phenolic compounds by mushroom tyrosinase was followed periodically by UV-vis spectrophotometry. The production of ortho-quinones were confirmed by their absorptions around 400-420 nm. HPLC analysis after reduction with NaBH4 detected the corresponding catechols. Leukoderma-inducing phenols, rhododendrol, raspberry ketone, 4-methoxyphenol, 4-benzyloxyphenol, 4-tert-butylphenol, and 4-tert-butylcatechol, were readily oxidized by mushroom tyrosinase to form ortho-quinones. On the other hand, phenolic skin whitening tyrosinase inhibitors, ellagic acid, 4-n-butylresorcinol, potassium 4-methoxysalicylate, and 2,2'-dihydroxy-5,5'-di-n-propylbiphenyl, were not oxidized by mushroom tyrosinase, while arbutin was only slowly oxidized. This study has provided a convenient screening method to differentiate phenolic skin whitening tyrosinase inhibitors from leukoderma-inducing phenols. A common chemical feature of the latter group of compounds is that they are readily oxidized by tyrosinase to form reactive ortho-quinone species. The present results point out the necessity that tyrosinase inhibitors should also be examined as substrates if they are phenolic compounds.

Related Materials

Product #

Image

Description

Molecular Formula

Add to Cart

173401
1,2,4-Benzenetriol, ReagentPlus®, 99%
C6H6O3
178519
4-(4-Hydroxyphenyl)-2-butanone, 99%
C10H12O2
W258806
4-(4-Hydroxyphenyl)-2-butanone, ≥98%, FCC, FG
C10H12O2
W258814
4-(4-Hydroxyphenyl)-2-butanone, natural, ≥98%, FCC, FG
C10H12O2
P53802
4-Propylphenol, 99%
C9H12O
W364908
4-Propylphenol, ≥97%, FG
C9H12O
425761
4-tert-Butylphenol, purified by sublimation, 99%
C10H14O
W391808
4-tert-Butylphenol, ≥99%, FG
C10H14O
B99901
4-tert-Butylphenol, 99%
C10H14O
506761
4-tert-Butylphenol, analytical standard
C10H14O
E2250
Ellagic acid, ≥95% (HPLC), powder, from tree bark
C14H6O8
27002
Formic acid, purum, ≥85%
CH2O2
W248703
Formic acid, ≥95%, FCC, FG
CH2O2
71320
Sodium borohydride, purum p.a., ≥96% (gas-volumetric)
H4BNa
452890
Sodium borohydride, caplets (18 × 10 × 8 mm), 98%
H4BNa
452165
Sodium borohydride, caplets
H4BNa
480886
Sodium borohydride, granular, 99.99% trace metals basis
H4BNa
452874
Sodium borohydride, granular, 10-40 mesh, 98%
H4BNa
452882
Sodium borohydride, powder, ≥98.0%
H4BNa
247677
Sodium borohydride, 90% NaBH4 basis, pellets, diam. 8 mm, Cobalt (Doped)
H4BNa
71318
Sodium borohydride, purum, ≥97.0% (gas-volumetric), tablet
H4BNa
213462
Sodium borohydride, ReagentPlus®, 99%
H4BNa
686018
Sodium borohydride, hydrogen-storage grade, 98%
H4BNa
200972
Sodium borohydride solution, 0.5 M in 2-methoxyethyl ether
H4BNa
452904
Sodium borohydride solution, SWS, ~12 wt. % in 14 M NaOH
H4BNa
215511
Sodium borohydride solution, 2.0 M in triethylene glycol dimethyl ether
H4BNa
632287
VenPure® SF, powder
H4BNa