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KMID : 0613820150250111298
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Journal of Life Science
2015 Volume.25 No. 11 p.1298 ~ p.1303
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Tyrosinase Inhibitory Activities of Meso-dihydroguaiaretic Acid from Machilus thunbergii
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Kwon Hyun-Sook
Lee Kyung-Dong
Kim Su-Cheol
Cho Soo-Jeong
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Abstract
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Machilus thunbergii (Lauraceae) is an evergreen tree cultivated in Korea and Japan. M. thunbergii has long been used as a traditional medicine in Korea, China, and Japan to treat various diseases, including edema, abdominal pain, and abdominal distension. In this study, dried stem bark of M. thunbergii extracted in methanol and extract was partitioned into n-hexane, CHCl3, and BuOH. The CHCl3-soluble extracts chromatographed on silica gel column using a CHCl3/acetone and n-hexane/EtOAc mixture to afford Compound 1 and 2. Two dibenzylbutane lignans, macelignan (1) and meso-dihydroguaiaretic acid (2), were isolated from the CHCl3-soluble extract of M. thunbergii stem bark. The structures of 1 and 2 were determined by 1H- and 13C-NMR spectroscopic data analyses and a comparison with literature data. The tyrosinase inhibitory activity of the isolated compounds was evaluated. Among these compounds, Compound 2 strongly inhibited the monophenolase (IC50=10.2 μM) activity of tyrosinase. A kinetic analysis showed that Compound 2 was a competitive inhibitor. The apparent inhibition constant (Ki) for Compound 2 binding to free enzyme was 4.8 μM. Based on these results, it can be concluded that meso-dihydroguaiaretic acid (2) is a potential candidate for the treatment of melanin biosynthesis-related skin diseases.
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KEYWORD
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Dibenzylbutane lignans, macelignan, Machilus thunbergii, meso-dihydroguaiaretic acid
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