Inhibitory Effect of Dalbergioidin Isolated from the Trunk of Lespedeza cyrtobotrya on Melanin Biosynthesis

  • Baek, Seung-Hwa (Korea Research Institute of Bioscience and Biotechnology) ;
  • Kim, Jin-Hee (Korea Research Institute of Bioscience and Biotechnology) ;
  • Kim, Dong-Hyun (Korea Research Institute of Bioscience and Biotechnology) ;
  • Lee, Chan-Yong (Department of Microbiology and Biotechnology, Daejeon University) ;
  • Kim, Ji-Young (Division of Bioscience and Biotechnology, Konkuk University) ;
  • Chung, Dae-Kyun (Skin Biotechnology Center, Graduate School of Biotechnology and Institute of Life Science and Resources, Kyung Hee University) ;
  • Lee, Choong-Hwan (Division of Bioscience and Biotechnology, Konkuk University)
  • Published : 2008.05.31

Abstract

Tyrosinase is a key enzyme for melanin biosynthesis, and hyperpigmentation disorders are associated with abnormal accumulation of melanin pigments, which can be reduced by treatment with depigmenting agents. The methanol extract of Lespedeza cyrtobotrya $M_{IQ}$ showed inhibitory activity against mushroom tyrosinase. The active compound was purified from the methanol extract of L. cyrtobotrya, followed by several chromatographic methods, and identified as dalbergioidin (DBG) by spectroscopic methods. The results showed that DBG exhibited tyrosinase inhibitory activity with an $IC_{50}$ of $20\;{\mu}M$. The kinetic analysis of tyrosinase inhibition revealed that DBG acted as a noncompetitive inhibitor. In addition, DBG showed a melanin biosynthesis inhibition zone in the culture plate of Streptomyces bikiniensis that has commonly been used as an indicator organism. Furthermore, $27\;{\mu}M$ DBG decreased more than 50% of melanin contents on the pigmentation using the immortalized mouse melanocyte, melan-a cell.

Keywords

References

  1. Ahn, S. J., M. Koketsu, H. Ishihara, S. M. Lee, S. K. Ha, K. H. Lee, T. H. Kang, and S. Y. Kim. 2006. Regulation of melanin synthesis by selenium-containing carbohydrates. Chem. Pharm. Bull. 54: 281-286 https://doi.org/10.1248/cpb.54.281
  2. Baek, S. H., D. H. Kim, C. Y. Lee, Y. H. Kho, and C. H. Lee. 2006. Idescarpin isolated from the fruits of Idesia polycarpa inhibits melanin biosynthesis. J. Microbiol. Biotechnol. 16: 667-672
  3. Bennett, D. C., F. J. Cooper, and I. R. Hart. 1987. A line of non-tumorigenic mouse melanocytes, syngeneic with the B16 melanoma and requiring a tumor promoter for growth. Int. J. Cancer 39: 414-418 https://doi.org/10.1002/ijc.2910390324
  4. Choi, J. Y., K. D. Kim, J. K. Park, and N. I. Kim. 2002. Effects of green tea (-)-epigallocatechin-3-gallate and polyphenol on the proliferation and apoptosis of cultured human keratinocytes, melanocytes, fibroblasts, endothelial cells, and human epidermal carcinoma cells. Kor. J. Dermatol. 40: 375-385
  5. Chun, H. J., S. G. Hwang, J. S. Lee, S. H. Baek, B. H. Jeon, and W. H. Woo. 2002. Inhibitory effects of butyl alcohol extract from Caesalpinia sappan L. on melanogenesis in Melan-a cells. Kor. J. Pharmcogn. 33: 130-136
  6. Chun, H. J., W. H. Choi, S. H. Baek, and W. H. Woo. 2002. Effect of quercetin on melanogenesis in Melan-a melanocyte cells. Kor. J. Pharmcogn. 33: 245-251
  7. Dooley, T. P. 1997. Topical skin depigmentation agents: Current products and discovery of novel inhibitors of melanogenesis. J. Dematol. Treat. 7: 188-200
  8. Dubios, J. L. and A. T. Sneden. 1995. Dihydrolicoisoflavone, a new isoflavanone from Swartzia polyphylla. J. Antibiot. 58: 629-632
  9. Enos, T. A., K. Shimizu, and R. Kondo. 2006. Inhibitory effect of isoprenoid-substituted flavonoids isolated from Artocarpus heterophylus on melanin biosynthesis. Planta Med. 72: 847-850 https://doi.org/10.1055/s-2006-931606
  10. Gao, L., H. K. Ju, H. W. Chang, Y. Jahng, S. H. Lee, and J. K. Son. 2003. Melanin biosynthesis inhibitors from the bark of Machilus thunbergii. Biol. Pharm. Bull. 26: 1039-1041 https://doi.org/10.1248/bpb.26.1039
  11. Hearing, V. J. and K. Tsukamoto. 1991. Enzymatic control of pigmentation in mammals. FASEB J. 5: 2902-2909 https://doi.org/10.1096/fasebj.5.14.1752358
  12. Hearing, V. J. and M. Jimenez. 1989. Analysis of mammalian pigmentation at the molecular level. Pigment Cell Res. 2: 75-85 https://doi.org/10.1111/j.1600-0749.1989.tb00166.x
  13. Ingham, J. L. and P. M. Dewick. 1984. The structure of desmocarpin, a pterocarpan phytoalexin from Desmodium gangeticum. J. Biosci. 39: 531-534
  14. Iozumi, K., G. E. Hoganson, R. Pennella, M. A. Everett, and B. B. Fuller. 1993. Role of tyrosinase as the determinant of pigmentation in cultured human melanocytes. J. Invest. Dermatol. 100: 806-811 https://doi.org/10.1111/1523-1747.ep12476630
  15. Kim, C. T., W. C. Kim, M. H. Jin, H. J. Kim, S. J. Kang, H. H. Kang, M. H. Jung, and Y. H. Lim. 2002. Inhibitors of melanogenesis from the roots of Peucedanum praeruprorum. Kor. J. Pharmcogn. 33: 395-398
  16. Kim, D. H., J. Y. Park, J. H. Kim, C. K. Han, J. Y. Yoon, N. D. Kim, J. H. Seo, and C. H. Lee. 2006. Flavonoids as mushroom tyronase inhibitors: A fluorescence quenching study. J. Agric. Food Chem. 54: 935-941 https://doi.org/10.1021/jf0521855
  17. Kim, D. S., S. H. Park, S. B. Kwon, E. S. Park, C. H. Huh, S. W. Youn, and K. C. Park. 2005. Sphingosylphosphorylcholineinduced ERK activation inhibits melanin synthesis in human melanocytes. Pigment Cell Res. 19: 146-153
  18. Kim, J. H., S. H. Baek, D. H. Kim, T. Y. Choi, T. J. Yoon, J. S. Hwang, M. R. Kim, H. J. Kwon, and C. H. Lee. 2008. Downregulation of melanin synthesis by haginin A and its application to in vivo lightening model. J. Invest. Dermatol. [In Press]
  19. Kim, W. G., I. J. Ryoo, S. H. Park, D. S. Kim, S. G. Lee, K. C. Park, and I. D. Yoo. 2005. Terrein, a melanin biosynthesis inhibitor, from Penicillium sp. 20135. J. Microbiol. Biotechnol. 15: 891-894
  20. Kobayashi, T., K. Vrabe, A. Winder, C. Jimenz-Cervantes, G. Imokawa, T. Brewinton, F. Solano, J. C. Garcia-Borron, and V. J. Hearing. 1994. Tyrosinase related protein 1 (TRP1) functions as DHICA oxidase in melanin biosynthesis. EMBO J. 13: 5818-5825
  21. Maeda, K. and M. Fukuda. 1996. Arbutin: Mechanism of its depigmenting action in human melanocyte culture. J. Pharmacol. Exp. Ther. 276: 765-769
  22. Nguyen, D., D. Nguyen, L. Hwa-La, H. B. Lee, H. B. Lee, and E. K. Kim. 2007. Inhibition of melanogenesis by dioctyl phthalate isolated from Nigella glandulifera freyn. J. Microbiol. Biotechnol. 17: 1585-1590
  23. Ohira, T. 1933. Eriodictyol in the leaves of Lespedeza. Nippon Nogei Kagaku Kaishi 9: 448-452 https://doi.org/10.1271/nogeikagaku1924.9.448
  24. Penny, K. B., C. J. Smith, and J. C. Allen. 1984. Depigmenting action of hydroquinone depends on disruption of fundamental cell processes. J. Invest. Dermatol. 82: 308-310 https://doi.org/10.1111/1523-1747.ep12260588
  25. Prota, G. 1988. Some new aspects of eumelanin chemistry. Prog. Clin. Biol. Res. 256: 101-124
  26. Shimizu, K., S. Yasutake, and R. Kondo. 2003. A new stilbene with tyrosinase inhibitory activity from Chlorophora excelsa. Chem. Pharm. Bull. 51: 318-319 https://doi.org/10.1248/cpb.51.318
  27. Smith, C. J., K. B. O'Hare, and J. C. Allen. 1988. Selective cytotoxicity of hydroquinone for melanocyte-derived cells is mediated by tyrosinase activity but independent of melanin content. Pigmet. Cell Res. 1: 386-389 https://doi.org/10.1111/j.1600-0749.1988.tb00140.x
  28. Stryer, L. 1995. Biochemistry, pp. 197-198, 4th Ed. W. H. Freeman and Co., New York. U.S.A
  29. Tamotsu, T., T. Imai, J. I. Onose, M. Ueda, T. Tamura, K. Mitsumori, K. Izumi, and M. Hirose. 2004. Enhancement of hepatocarcinogenesis by kojic acid in rat two-stage models after initiation with N-bis(2-hydroxypropyl) nitrosamine or Ndiethylnitrosamine. Toxicol. Sci. 81: 43-49 https://doi.org/10.1093/toxsci/kfh195
  30. Teruhisa, M., S. Toshiyuki, K. Tomoko, K. Yoshie, N. Tsutomu, N. Kohshi, F. Takuya, K. Fumio, Y. Akira, and O. Katsuhiko. 2003. Intradermal concentration of hydroquinone after application of hydroquinone ointments is higher than its cytotoxic concentration. Biol. Pharm. Bull. 26: 1365-1367 https://doi.org/10.1248/bpb.26.1365
  31. Tomita, K., N. Oda, M. Ohbayashi, H. Kamei, T. Miyaki, and T. Oki. 1990. A new screening method for melanin biosynthesis inhibitors using Streptomyces bikiniensis. J. Antibiot. 43: 1601-1605 https://doi.org/10.7164/antibiotics.43.1601
  32. Toshio, M., U. Akira, N. Tadataka, and F. Seigo. 1980. Studies on the constituents of Lespedeza cyrtobotrya MIQ. I. The structures of a new chalcone and two new isoflav-3-ens. Chem. Pharm. Bull. 28: 1172-1177 https://doi.org/10.1248/cpb.28.1172
  33. Toshio, M., U. Akira, N. Tadataka, and F. Seigo. 1981. Studies on the constituents of Lespedeza cyrtobotrya MIQ. II. The structures of haginin C, haginin D, and lespedeol C. Chem. Pharm. Bull. 29: 2205-2209
  34. Yeo, S. H., H. J. Kim, J. H. Yoon, H. S. Kim, Y. I. Hwang, and S. C. Lee. 2006. Characterization of antioxidant-producing Alteromonas macleodii HJ-14 isolated from seawater. J. Microbiol. Biotechnol. 16: 731-739
  35. Yokoyana, K., H. Suzuki, K. Yasumoto, Y. Yomita, and S. Shibahara. 1994. Molecular cloning and functional analysis of a cDNA coding for human DOPAchrome tautonerase/tyrosinaserelated protein-2. Biochim. Biophys. Acta 1217: 317-321 https://doi.org/10.1016/0167-4781(94)90292-5
  36. Zhong, S., Y. Wu, S. M. Ahn, J. Zhao, K. Wang, S. Yang, J. H. Yeon, and X. Zhu. 2006. Depigmentation of melanocytes by the treatment of extracts from traditional Chinese herbs: A cell culture assay. Biol. Pharm. Bull. 29: 1947-1951 https://doi.org/10.1248/bpb.29.1947
  37. Zhu, Y. Y., L. K. Feng, T. W. En, H. W. Ge, and X. C. Wen. 2002. Characterization of rhizobia that nodulate legume species of the genus Lespedeza and description of Bradyrhizobium yuanmingense sp. nov. Int. J. System. Evol. Microbiol. 52: 2219-2230 https://doi.org/10.1099/ijs.0.01408-0