Inhibitory Effects of Coumarin Derivatives on Tyrosinase

Eon-Joo Roh

doi:10.3390/molecules26082346

Abstract

In this study, a series of coumarin derivatives were synthesized and their inhibitory effects on the activity of mushroom tyrosinase were evaluated. As a result of measuring the inhibition of tyrosinase activity of these derivatives, the compounds 3e (1.05 μM), 3f (0.83 μM), 3h (0.85 μM), 3i (1.05 μM), and 3k (0.67 μM) of the geranyloxycoumarin derivatives were highly active at a concentration of 0.8%. The geranyloxycoumarin derivatives exhibited better activity than the hydroxycoumarin derivatives. Among the geranyloxycoumarin derivatives, compound 3k was two times more active than arbutin, a positive control, at a concentration of 0.4%. The above results suggest that geranyloxycoumarin derivatives have great potential for application as functional cosmetic ingredients with tyrosinase-inhibiting activity.

Highlights

Tyrosinase is known to be a multifunctional copper-containing enzyme from the oxidase superfamily, and it is the key protein involved in the biosynthesis of the large biological pigment, melanin [1]
These excessive melanin expressions can be suppressed by effective tyrosinase inhibitors
Geranyloxycoumarin derivatives were effectively synthesized using coumarin, which affects a number of physiological activities, as a lead compound

Summary

Introduction

Tyrosinase is known to be a multifunctional copper-containing enzyme from the oxidase superfamily, and it is the key protein involved in the biosynthesis of the large biological pigment, melanin [1]. Tyrosinase promotes hydroxylation of L-Tyrosine to L-DOPA (L-3,4dihydroxyphenylalanine) in the process of melanin biosynthesis, promotes oxidation from L-DOPA to dopaquinone. Dopaquinone forms melanin through several stages [3]. Melanin plays an important role in human skin, but excessive melanin formation caused by abnormal melanin production can cause pigmentation disorders, such as freckles, blemishes, and age spots [4]. These excessive melanin expressions can be suppressed by effective tyrosinase inhibitors

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