Isolation of Melanin Biosynthesis Inhibitory Compounds from the Roots of Asarum sieboldii

세신으로부터 멜라닌 생성 억제 성분의 분리

  • Published : 2007.12.31

Abstract

Eight compounds were isolated from the roots of Asarum sieboldii and their structures were identified as $({\pm})$-car-3-ene-2,5-dione (1), (-)-asarinin (2), (-)-sesamin (3), eucarvone (4), methyleugenol (5), ${\gamma}-asarone$ (6), pellitorine (7) and asarinol A (8) by analysis of spectral data. Among them, (-)-asarinin (2) showed the most potent inhibitory effect on melanogenesis, with inhibition rate of 66%.

Keywords

References

  1. 생약학교재편찬위원회 (2006) 생약학, 151-153 동명사
  2. Lee, J. Y., Moon, S. S., Hwang, B. K. (2005) Isolation and antifungal activity of kakuol, a propiophenone derivative from Asarum sieboldii rhizome, Pest management science, 61: 821-825 https://doi.org/10.1002/ps.1050
  3. Hashimoto Kazunori et al. (2004) Studies on anti-allergic components in the roots of Asiasarum sieboldii, Planta Med., 60: 124-127 https://doi.org/10.1055/s-2006-959432
  4. Mishima, Y., Hatta, S., Ohyama, Y. (1988) Induction of melanogenesis suppression cellular pharmacology and mode of differential action, Pigment Cell Res., 1: 367 https://doi.org/10.1111/j.1600-0749.1988.tb00136.x
  5. Matubara, H. (1998) Inhibitory effect of Iichen metabolites and their synthetic analogues on malanin biosynthesis in cultured B-16 mouse melanoma cells, Natural Product Sciences., 4: 3
  6. Ortonne, J. P., Nordlund, J. J. (1998) Mechanism that cause abnormal skin color, In Physiology and Pathophysiology, New York, Oxford University Press, 489-502
  7. Hearin, V. J., Jimenez, M. (1987) Mammalian tyrosinase the critical regulatory control point in melanocyte pigment, Int. J. Biochem., 19: 1141 https://doi.org/10.1016/0020-711X(87)90095-4
  8. Prota, G. (1980) Recent advances in the chemistry of melanogenesis in mammals, J. Invest. Dermatol., 75: 122 https://doi.org/10.1111/1523-1747.ep12521344
  9. Pavel, S., Muskiet, F. (1983) Eumelanin (precursor) metabolites as markers for pigmented malignant melanoma, a preliminary report, Cancer Detection and Prevention, 6: 311
  10. Kusano, G., Shibano, M. (1994) Food & Food Ingredients J. Jnp 161: 73
  11. Cabanes, J., Chazarra, S. (1994) Kojic acid, a cosmetin skin whitening agent, is a slow-binding inhibitor of catecholase activity of tyrosinase, J. Pharm. Pharnacol. 46: 982-985 https://doi.org/10.1111/j.2042-7158.1994.tb03253.x
  12. Chakrabotry, A. K., Funasaka, Y., Komoto, M., Ichihashi, M. (1998) Effect of arbutin on melanigenic proteins in human melanocytes. Pigment Cell Res. 11: 206-212 https://doi.org/10.1111/j.1600-0749.1998.tb00731.x
  13. Shin N. H. et al (1998) Oxyresveratrol as the potent inhibitor on dopa oxidase activity of mushroom tyrosinase. Biochemical and Biophysical Research Communication, 243: 801- 803 https://doi.org/10.1006/bbrc.1998.8169
  14. Korner, A. M., Pawelek, J. (1980) Dopachrome conversion : a possible control point in melanin biosynthesis. J. Invest. Dermatol., 75: 192 https://doi.org/10.1111/1523-1747.ep12522650
  15. Kreiner, P. W., Gold, C. J., Keirns, J. J., Brock, W. A., Bitensky, M. W. (1973) Hormonal control of melanocytes : MSHsensitive adenyl cyclase in the Cloudman melanoma. Yale J. Biol. Med., 46: 583
  16. Giacomini, P. L. et al(1985) Immunochemical analysis of the modulation of human melanoma-associated antigens by DNA recombinant immune interferon. Immunol., 135: 288
  17. Sawyer, T. K. et al (1983) $\alpha$-Melanocyte stimulating hormone. Amer. Zool., 23: 529 https://doi.org/10.1093/icb/23.3.529
  18. Pilar, A., Urabe K., Kobayashi T., Tsukamoto K., and Vincent J. H., (1993) Melanin biosynthesis patterns following hormonal stimulation. J. Biol. Chem., 34: 25650
  19. Fukushima, T. M., Tagami, H. (1986) Stimulation of melanogenesis by cholecalciferol in cultured human melanocytes. melanocytes. Tohoku J. Exp. Med., 451
  20. Ando, S., Ando, O., Suemoto, Y., Mishima, Y. (1993) Tyrosinase gene transcription and its control by melanogenic inhibitors. J. Invest. Dermatol., 100: 150s https://doi.org/10.1111/1523-1747.ep12465056
  21. Hashimoto, K., Katsuhara, T., Itoh, H., Ikeya, Y., Okada, M. (1990) Mitsuhashi, H., Monoterpenes from asiasari radix from Asiasarum sp., Phytochemistry, 29: 3571-3574 https://doi.org/10.1016/0031-9422(90)85278-N
  22. Pelter, A., Ward, R. S., Nishino, C. (1977) Revised structures for epiaschantin and epimagnolin, Tetrahedron letters: the international organ for the rapid publication of preliminary communications in organic chemistry, 18: 4137-4140 https://doi.org/10.1016/S0040-4039(01)83447-X
  23. Zhang, F. et al (2005) A new amide from Asarum forbesii Maxim., Journal of Asian natural products research, 7: 1-5 https://doi.org/10.1080/10286020310001596015
  24. Ronald F., Childs, Yee-chee Hor (1977) Comparison of the charge distributions and barriers to ring inversion of protonated eucarvone and its boron trihalide adducts., Canadian Journal of Chemistry, 55: 3495-3500 https://doi.org/10.1139/v77-489
  25. Meepagala, K. M., Sturtz, G., Wedge, D. E. (2002) Antifungal Constituents of the Essential Oil Fraction of Artemisia dracunculus L. Var. dracunculus, J. Agric. Food Chem., 50: 6989-6992 https://doi.org/10.1021/jf020466w
  26. Ruchi Acharya et al (2002) A mild and convenient procedure for the conversion of toxic $\beta$-asarone into rare phenylpropanoids: 2,4,5-trimethoxycinnamaldehyde and $\gamma$-asarone, J. Nat. Prod., 65: 764-765 https://doi.org/10.1021/np010559s
  27. Park, I. K., Lee, S. G., Shin, S. C., Park, J. D., Ahn, Y. J., (2002) Larvicidal activity of isobutylamides identified in Piper nigrum Fruits against three mosquito species, J. Agric. Food Chem., 50: 1866-1870 https://doi.org/10.1021/jf011457a
  28. Ley, Jakob P. et al (2004) Stereoselective Enzymatic Synthesis of cis-Pellitorine, a Taste Active Alkamide Naturally Occurring in Tarragon, Eur. J. Org. Chem., 2004: 5135-5140 https://doi.org/10.1002/ejoc.200400403