Tyrosinase Inhibitor from the Flowers of Impatiens balsamina

  • Lim, Young-Hee (Department of Clinical Laboratory Science, College of Health Sciences, Korea University) ;
  • Kim, In-Hwan (Department of Food and Nutrition, College of Health Sciences, Korea University) ;
  • Seo, Jung-Ju (Hazardous Substance Research Team, Korea Basic Science Institute) ;
  • Kim, Jeong-Keun (Department of Chemical Engineering and Biotechnology, Korea Polytechnic University)
  • Published : 2006.12.30

Abstract

Kaempferol was isolated and identified from the methanol extract of the flowers of Impatiens balsamina. Kaempferol showed inhibitory activity against mushroom tyrosinase with an $ID_{50}$ of 0.042 mM. Inhibition kinetics, as determined using a Lineweaver-Burk plot, showed kaempferol to be a competitive inhibitor of mushroom tyrosinase with a $K_i$ value of 0.011 mM. The lag phase of tyrosine hydroxylation catalyzed by mushroom tyrosinase clearly increased on increasing the concentration of kaempferol. In addition to its tyrosinase inhibiting activity, kaempferol strongly inhibited melanin production by Streptomyces bikiniensis, in a dose-dependent manner, without inhibiting cell growth. For comparative purposes, the tyrosinase inhibitory activity of kaempferol was also assayed versus quercetin, a positive standard.

Keywords

References

  1. Bouchilloux, S., P. McMahill, and H. S. Mason. 1963. The multiple form of mushroom tyrosinase. Purification and molecular properties of the enzymes. J. Biol. Chem. 238: 1699-1707
  2. Cabanes, J., F. G. Canovas, J. A. Lozano, and F. G. Carmona. 1987. A kinetic study of the melanization pathway between $_L$-tyrosine and dopachrome. Biochim. Biophys. Acta 923: 187-195 https://doi.org/10.1016/0304-4165(87)90003-1
  3. Canovas, F. G., F. G. Carmona, J. V. Sanchez, J. L. I. Pastor, and J. A. L. Teruel. 1982. The role of pH in the melanin biosynthesis pathway. J. Biol. Chem. 257: 8738-8744
  4. Carmona, F. G., E. Pedreno, J. D. Galindo, and F. G. Canovas. 1979. A new spectrophotometric method for the determination of cresolase activity of epidermis tyrosinase. Anal. Biochem. 95: 433-435 https://doi.org/10.1016/0003-2697(79)90751-6
  5. Chen, J. S., C. I. Wei, and M. R. Marshall. 1991. Inhibition mechanism of kojic acid on polyphenol oxidase. J. Agric. Food Chem. 39: 1897-1901 https://doi.org/10.1021/jf00011a001
  6. Cooksey, C. J., P. J. Garratt, E. J. Land, S. Pavel, C. A. Ramsden, P. A. Riley, and N. P. M. Smit. 1997. Evidence of the indirect formation of the catecholic intermediate substrate responsible for the autoactivation kinetics of tyrosinase. J. Biol. Chem. 272: 26226-26235 https://doi.org/10.1074/jbc.272.42.26226
  7. Friedman, M. 1996. Food browning and its prevention: An overview. J. Agric. Food Chem. 44: 631-653 https://doi.org/10.1021/jf950394r
  8. Fukumoto, H., K. Ishiguro, T. Murashima, and M. Isoi. 1994. Structure determination of a kaempferol 3-rhamnosyldiglucoside from Impatiens balsamina. Phytochemistry 37: 1486-1488 https://doi.org/10.1016/S0031-9422(00)90440-0
  9. Hearing, V. J. and M. Jimenez. 1987. Mammalian tyrosinase - The critical regulatory control point in melanocyte pigmentation. Int. J. Biochem. 19: 1141-1147 https://doi.org/10.1016/0020-711X(87)90095-4
  10. Kang, S. C. and Y. Moon. 1992. Isolation and antimicrobial activity of a naphthoquinone from Impatiens balsamina. Saengyak Hakhoechi 23: 240-247
  11. Khan, M. T. H., M. I. Choudhary, K. M. Khan, M. Rani, and A. Rahman. 2005. Structure-activity relationships of tyrosinase inhibitory combinatorial library of 2,5-disubstituted-1,3,4- oxadiazole analogues. Bioorg. Med. Chem. 13: 3385-3395 https://doi.org/10.1016/j.bmc.2005.03.012
  12. Khan, M. T. H., S. B. Khan, and A. Ather. 2006. Tyrosinase inhibitory cycloartane type triterpenoids from the methanol extract of the whole plant of Amberboa ramosa Jafri and their structure-activity relationship. Bioorg. Med. Chem. 14: 938-943 https://doi.org/10.1016/j.bmc.2005.09.010
  13. Kim, J.-H., J. J. Song, B.-G. Kim, M.-H. Sung, and S. C. Lee. 2004. Enhanced stability of tyrosine phenol-lyase from Symbiobacterium toebii by DNA shuffling. J. Microbiol. Biotechnol. 14: 153-157 https://doi.org/10.1159/000079436
  14. Kim, W.-G., I.-J. Ryoo, S.-H. Park, D.-S. Kim, S. Lee, K.-C. Park, and I.-D. Yoo. 2005. Terrein, a melanin biosynthesis inhibitor, from Penicillium sp. 20135. J. Microbiol. Biotechnol. 15: 891-894
  15. Korner, A. M. and J. Pawelek. 1982. Mammalian tyrosinase catalyzes three reactions in the biosynthesis of melanin. Science 217: 1163-1165 https://doi.org/10.1126/science.6810464
  16. Kubo, I. and I. K. Hori. 1999. Flavonols from Saffron flower: Tyrosinase inhibitory activity and inhibition mechanism. J. Agric. Food Chem. 47: 4121-4125 https://doi.org/10.1021/jf990201q
  17. Kubo, I., I. K. Hori, S. K. Chaudhuri, Y. Kubo, Y. Sánchez, and T. Ogura. 2000. Flavonols from Heterotheca inuloides: Tyrosinase inhibitory activity and structural criteria. Bioorg. Med. Chem. 8: 1749-1755 https://doi.org/10.1016/S0968-0896(00)00102-4
  18. Kupper, U., D. M. Niedermann, G. Travaglini, and K. Lerch. 1989. Isolation and characterization of the tyrosinase gene from Neurospora crassa. J. Biol. Chem. 264: 17250-17258
  19. Kwon, B. S., A. K. Haq, S. H. Pomerantz, and R. Halaban. 1987. Isolation and sequence of a cDNA clone for human tyrosinase that maps at the mouse c-albino locus. Proc. Natl. Acad. Sci. USA 84: 7473-7477
  20. Lerch, K. and L. Ettlinger. 1972. Purification and characterization of a tyrosinase from Streptomyces glaucescens. Eur. J. Biochem. 31: 427-437 https://doi.org/10.1111/j.1432-1033.1972.tb02549.x
  21. Lopez, J. N. R., M. B. Arnao, F. M. Ortiz, J. Tudela, M. Acosta, R. Varón, and F. G. Canovas. 1992. Catalytic oxidation of 2,4,5-trihydroxyphenylalanine by tyrosinase: Identification and evolution of intermediates. Biochim. Biophys. Acta 1160: 221-228 https://doi.org/10.1016/0167-4838(92)90011-2
  22. Maeda, K. and M. Fukuda. 1991. In vitro effectiveness of several whitening cosmetic components in human melanocytes. J. Soc. Cosmet. Chem. 42: 361-368
  23. Malmstrom, B., L. Andreasson, and B. Reinhammar. 1975. Copper-containing oxidases and superoxide dismutase, pp 507-579. In Boyer, P. (ed.), The Enzymes, 3rd Ed. Vol. 12. Academic Press, New York
  24. Martinez, J. R. R., J. N. R. Lopez, R. V. Castellanos, and F. G. Cánovas. 1993. Discrimination between two kinetic mechanisms for the monophenolase activity of tyrosinase. Biochem. J. 294: 621-623 https://doi.org/10.1042/bj2940621
  25. Martinez, M. V. and J. R. Whitaker. 1995. The biochemistry and control of enzymatic browning. Trends Food Sci. Technol. 6: 195-200 https://doi.org/10.1016/S0924-2244(00)89054-8
  26. Mayer, A. M. 1987. Polyphenol oxidases in plants: Recent progress. Phytochemistry 26: 11-20 https://doi.org/10.1016/S0031-9422(00)81472-7
  27. Nihei, K., Y. Yamagiwa, T. Kamikawa, and I. Kubo. 2004. 2- Hydroxy-4-isopropylbenzaldehyde, a potent partial tyrosinase inhibitor. Bioorg. Med. Chem. Lett. 14: 681-683 https://doi.org/10.1016/j.bmcl.2003.11.033
  28. Nishioka, K. 1978. Particulate tyrosinase of human malignant melanoma. Solubilization, purification following trypsin treatment and characterization. Eur. J. Biochem. 85: 137- 146 https://doi.org/10.1111/j.1432-1033.1978.tb12221.x
  29. No, J. K., D. Y. Soung, Y. J. Kim, K. H. Shim, Y. S. Jun, and S. H. Rhee. 1999. Inhibition of tyrosinase by green tea components. Life Sci. 65: 241-246 https://doi.org/10.1016/S0024-3205(99)00492-0
  30. Park, K. J. and H. H. Lee. 2005. In Vitro antiviral activity of aqueous extracts from korean medicinal plants against influenza virus type A. J. Microbiol. Biotechnol. 15: 924- 929
  31. Tomita, K., N. Oda, M. Ohbayashi, and H. Kamei. 1990. A new screening method for melanin biosynthesis inhibitors using Streptomyces bikiniensis. J. Antibiotics 43: 1601- 1605 https://doi.org/10.7164/antibiotics.43.1601
  32. Wang, X.-L., K.-T. Kim, J.-H. Lee, H.-G. Hur, and S.-I. Kim. 2004. C-Ring cleavage of isoflavones daidzein and genistein by a newly-isolated human intestinal bacterium Eubacterium ramulus Julong 601. J. Microbiol. Biotechnol. 14: 766-771
  33. Whittaker, J. R. 1995. Phenol oxidase, pp. 271-307. In Wong, D. (ed.), Food Enzymes, Structure and Mechanism. Chapman and Hall, New York
  34. Yang, X., D. K. Summerhurst, S. F. Koval, C. Ficker, M. L. Smith, and M. A. Bernards. 2001. Isolation of an antimicrobial compound from Impatiens balsamina L. using bioassay-guided fractionation. Phytother. Res. 15: 676-680 https://doi.org/10.1002/ptr.906