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http://dx.doi.org/10.3839/jabc.2022.038

Antimelanogenic and antioxidant effects of trimethoxybenzene derivatives: methyl 3,4,5-trimethoxybenzoate, ethyl 3,4,5-trimethoxybenzoate, methyl 3,4,5-trimethoxycinnamate, and ethyl 3,4,5-trimethoxycinnamate  

Jaewon Shin (Division of Applied Chemistry and Cosmetic Science, Dongduk Women's University)
Harim Lee (Division of Applied Chemistry and Cosmetic Science, Dongduk Women's University)
Seunghyun Ahn (Department of Applied Chemistry, Dongduk Women's University)
Won Seok Jeong (RNS Inc. R&D Center)
CheongTaek Kim (RNS Inc. R&D Center)
Seyeon Park (Division of Applied Chemistry and Cosmetic Science, Dongduk Women's University)
Publication Information
Journal of Applied Biological Chemistry / v.65, no.4, 2022 , pp. 299-306 More about this Journal
Abstract
In this study, derivatives of trimethoxybenzene were investigated as inhibitors of melanogenesis. We examined the effects of methyl 3,4,5-trimethoxybenzoate (MTB), ethyl 3,4,5-trimethoxybenzoate (ETB), methyl 3,4,5-trimethoxycinnamate (MTC), and ethyl 3,4,5-trimethoxycinnamate (ETC). First, the inhibitory effects of these agents on melanin production were evaluated using α-melanocyte-stimulating hormone (α-MSH)-stimulated B16F10 melanoma cells. We found that all derivatives decreased α-MSH-induced melanin production in B16F10 melanoma cells; ETC showed a strong inhibitory effect at half of the concentration of the other derivatives. As tyrosinase is considered a key enzyme of melanogenesis, we also examined whether the derivatives inhibited tyrosinase activity. MTC and ETC reduced mushroom tyrosinase activity and expression levels of α-MSH-induced B16F10 cellular tyrosinase protein. Inhibitory effects of all derivatives on α-MSH-induced B16F10 cellular tyrosinase activity were shown in a dose-dependent manner. Additionally, the derivatives were exposed to diphenylpicrylhydrazyl free radical to examine their antioxidant characteristics. All derivatives showed considerable antioxidant activity, which was 2-fold higher than that of arbutin. In conclusion, the trimethoxybenzene derivatives, including MTB, ETB, MTC, and ETC exerted anti-melanogenic and antioxidant effects on α-MSH-stimulated melanogenesis, demonstrating their potential for use as novel hypopigmenting agents and antioxidants.
Keywords
Alpha-MSH; Antioxidants; Benzoates; Cinnamates; Melanocytes; Skin pigmentation;
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Times Cited By KSCI : 3  (Citation Analysis)
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