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http://dx.doi.org/10.5352/JLS.2015.25.11.1298

Tyrosinase Inhibitory Activities of Meso-dihydroguaiaretic Acid from Machilus thunbergii  

Kwon, Hyun Sook (Korea Promotion Institute for Traditional Medicine Industry)
Lee, Kyung Dong (Department of Oriental Medicine Materials, Dongshin University)
Kim, Su Cheol (Amicogen Inc.)
Cho, Soo Jeong (Department of Pharmaceutical Engineering, Gyeongnam National University of Science and Technology)
Publication Information
Journal of Life Science / v.25, no.11, 2015 , pp. 1298-1303 More about this Journal
Abstract
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.
Keywords
Dibenzylbutane lignans; macelignan; Machilus thunbergii; meso-dihydroguaiaretic acid;
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1 Forrest, J. E., Heacock, R. A. and Forrest, T. P. 1974. Diarylpropanoids from nutmeg and mace (Myristica fragrans Houtt.). J. Chem. Soc. Perkin 1 2, 205-209.
2 Cho, J. Y., Choi, G. J., Son, S. W., Jang, K. S., Lim, H. K., Lee, S. O., Sung, N. D., Cho, K. Y. and Kim, J. C. 2007. Isolation and antifungal activity of lignans from Myristica fragrans against various plant pathogenic fungi. Pest Manag. Sci. 63, 935-940.   DOI
3 Friedman, M. 1996. Food browning and it’s prevent; an overview. J. Agric. Food Chem. 44, 631-653.   DOI
4 Ha, T. J., Tamura, S. and Kubo, I. 2005. Effects of mushroom tyrosinase on anisaldehyde. J. Agric. Food Chem. 53, 7024-7028.   DOI
5 Jin , D. Q., Lim, C. S., Hwang, J. K., Ha, I. and Han, J. S. 2005. Biochem. Biophys. Res. Commun. 331, 1264-1269.   DOI
6 Kahn, V. and Andrawis, A. 1985. Inhibition of mushroom tyrosinase by tropolone. Phytochemistry 24, 905-908.   DOI
7 Karikome, H., Mimaki, Y. and Sashida, Y. 1991. A butanolide and phenolics from Machilus thunbergii. Phytochemistry 30, 315-319.   DOI
8 Kawaguchi, Y., Yamauchi, S., Masuda, K., Nishiwaki, H., Akiyama, K., Maruyama, M., Sugahara, T., Kishida, T. and Koba, Y. 2009. Antimicrobial activity of stereoisomers of butane-type lignans. Biosci. Biotechnol. Biochem. 73, 1806-1810.   DOI
9 Kim, N. Y. and Ryu, J. H. 2003. Butanoilds from Machilus thunbergii and their inhibitory activity on nitric oxide synthesis in activated macrophages. Phytother. Res. 17, 372-375.   DOI
10 Kim, W., Lyu, H. N., Kwon, H. S., Kim, Y. S., Lee, K. H., Kim, D. Y., Chakraborty, G., Choi, K. Y., Yoon, H. S. and Kim, K. T. 2013. Obtusilactone B from Machilus Thunbergii targets barrier-to-autointegration factor to treat cancer. Mol. Pharmacol. 83, 367-376.   DOI
11 Komae, H. and Hayashi, N. 1972. Terpenes from Actinodaphne, Machilus and Neolitsea species. Phytochemistry 11, 1181-1182.   DOI
12 Kubo, I. and Kinst-Hori, I. 1999. Flavonols from saffron flower. J. Agric. Food Chem. 47, 4121-4125.   DOI
13 Lee, H. S. 2002. Tyrosinase inhibitors of Pulsatilla cernua root-derived materials. J. Agric. Food Chem. 50, 1400-1403.   DOI
14 Lee, J. Y., Han, Y. B., Woo, W. S. and Shin, K. H. 1990. Antioxidant activity of Diarylbutanes. Kor. J. Pharmacogn. 21, 270-273.
15 Li, G., Lee, C. S., Woo, M. H., Lee, S. H., Chang, H. W. and Son, J. K. 2004. Lignans from the bark of Machilus thunbergii and their DNA topoisomerases I and II inhibition and cytotoxicity. Biol. Pharm. Bull. 27, 1147-1150.   DOI
16 Ma, C. J., Sung, S. H. and Kim, Y. C. 2004. Neuroprotective lignans from the bark of Machilus thunbergii. Planta Med. 70, 79-80.   DOI
17 Maeda, K. and Fukuda, M. 1991. In vitro effectiveness of several whitening cosmetic components in human melanocytes. J. Soc. Cosmet. Chem. 42, 361-368.
18 Moon, T. C., Seo, C. S., Ha, K., Kim, J. C., Hwang, N. K., Hong, T. G., Kim, J. H., Kim, D. H., Son, J. K. and Chang, H. W. 2008. meso-Dihydroguaiaretic acid isolated from Saururus chinensis inhibits cyclooxygenase-2 and 5-lipoxygenase in mouse bone marrow-derived mast cells. Arch. Pharm. Res. 31, 606-610.   DOI
19 Park, E. Y., Shin, S. M., Ma, C. J., Kim, Y. C. and Kim, S. G. 2005. meso-Dihydroguaiaretic acid from Machilus thunbergii down-regulates TGF-β1 gene expression in activated hepatic stellate cells via inhibition of AP-1 activity. Planta Med. 71, 393-398.   DOI
20 Park, B. Y., Min, B. S., Kwon, O. K., Oh, S. R., Aha, K. S., Kim, J. T., Kim, D. Y., Bae, K. and Lee, H. K. 2004. Increase of caspase-3 activity by lignans from Machilus thunbergii in HL-60 cells. Biol. Pharm. Bull. 27, 1305-1307.   DOI
21 Paul, S., Hwang, J. K., Kim, H. Y., Jeon, W. K., Chung, C. and Han, J. S. 2013. Multiple biological properties of macelignan and its pharmacological implications. Arch. Pharm. Res. 36, 264-272.   DOI
22 Seo, S. Y., Sharma, V. K. and Sharma, N. 2003. Mushroom tyrosinase: recent prospects. J. Agric. Food Chem. 51, 2837-2853.   DOI
23 Parvez, S., Kang, M. K., Chung, H. S. and Bae, H. S. 2007. Naturally occurring tyrosinase inhibitors: mechanism and applications in skin health, cosmetics and agriculture industries. Phytother. Res. 21, 805-816.   DOI
24 Shin, K. H. and Woo, W. S. 1986. Hepatic Drug metabolism modifier from arils of Myristica fragrans. Kor. J. Pharmacogn. 17, 91-99.
25 Son, S. M., Moon, K. D. and Lee, C. Y. 2000. Rhubarb juice as a natural antibrowing agent. J. Food Sci. 65, 1288-1289.   DOI
26 Woo, W. S., Shin, K. H., Wagner, H. and Lotter, H. 1987. The structure of macelignan from Myristica fragrans. Phytochemistry 26, 1542-1543.   DOI
27 Yu, Y. U., Kang, S. Y., Park, H. Y., Sung, S. H., Lee, E. J., Kim, S. Y. and Kim, Y. C. 2000. Antioxidant lignans from Machilus thunbergii protect CCl4-injured primary cultures of rat hepatocytes. J. Pharm. Pharmacol. 52, 1163-1169.   DOI