Tyrosinase, Hyaluronidase Inhibitory Effect and Antioxidant Activity of Medicinal Plants

약용식물의 Tyrosinase, Hyaluronidase 저해효과 및 항산화 활성

  • Cha, Bae-Cheon (Department of Pharmaceutical Engineering, College of Health Sciences, Sangji University)
  • 차배천 (상지대학교 보건과학대학 제약공학과)
  • Received : 2011.02.11
  • Accepted : 2011.03.21
  • Published : 2011.03.31

Abstract

This study was conducted to investigate tyrosinase inhibitory effect, hyaluronidase inhibitory effect and antioxidant activity by DPPH radical scavenging method on the MeOH extract of 50 species medicinal plant for screening of functional properties. As a result, Chaenomeles sinensis Koehne extract among 50 species medicinal plant turned out to be having tyrosinase, hyaluronidase inhibitory effect and antioxidant activity. The major component of tyrosinase and hyaluronidase inhibitory effect was isolated from EtOAc extract of Chaenomeles sinensis Koehne. And the component of antioxidant activity was isolated from n-BuOH extract of Chaenomeles sinensis Koehne. Their structure of compounds were identified as oleanolic acid and (-)-epicatechin by spectroscopic evidence, respectively.

Keywords

References

  1. Masaki, H. (2010) Role of antioxidants in the skin: Antiaging effects. J. Dermatol. Sci. 58: 85-90. https://doi.org/10.1016/j.jdermsci.2010.03.003
  2. Halliwell, B. (1991) Drug antioxidant effects. Drugs 42: 569-605. https://doi.org/10.2165/00003495-199142040-00003
  3. Korner, A. and Pawelek, J. (1982) Mammalian tyrosinase catalases three reactions in the biosynthesis of melanin. Science 217: 1163-1165. https://doi.org/10.1126/science.6810464
  4. Meyer, K. (1947) The biological significance of hyaluronic acid and hyaluronidase. Physiol. Rev. 27: 335-359.
  5. Ghosh, P. (1994) The role of hyaluronic acid(hyaluronan) in health and disease: interactions with cells, cartilage and components of synovial fluids. Clin. Exp. Rheumatol. 12: 75-82.
  6. Yang, S. W., Park, S. R., Ahn, D. R., Yang, J. H., Cho, C. H., Hwang, Y. H., Park, J. H. and Kim, D. K. (2010) DPPH free radical scavenging effect of the aerial parts of Desmodium oldhami. Kor. J. Pharmacogn. 41: 180-184.
  7. Choi, S. S., Yim, D. S. and Lee, S. Y. (2009) Radical scavenging activities and protective effects against oxidative damage to DNA of extracts from medicinal plants with known osteoprotective effects. Kor. J. Pharmacogn. 40: 143-149.
  8. Uchiyama, M., Suzuki, Y. and Fukuzawa, K. (1968) Biochemical studies of physiological function of tocopheronolactone. 1. Yakugaku Zasshi 88: 678-683.
  9. Hearing, J. R. and Hearing, V. J. (1987) Mammalian monophenol monooxygenase(Tyrosinase) : Purification, properties and reaction catalyzed. Method on Enzymology 142: 154-165.
  10. Lee, N. H., Lee, S. J., Jung, D. S., Bu, H. J., Yang, H. C. and Riu, K. Z. (2001) Screening of the tyrosinase inhibition and hyaluronidase inhibition activities, and radical scavenging effects using plants in Cheju. Kor. J. Pharmacogn. 32: 175-180.
  11. Yoshikawa, M., Harada, E., Miki, A., Tsukamoto, K., Liang, S. Q., Yamahara, J. and Murakami, N. (1994) Antioxidant constituents from the fruit hulls of Mangosteen(Garcinia mangostana L.) originating in Vetnam. Yakugaku Zasshi 114: 129-133.
  12. Park, S. R., Yang, S. W., Ahn, D. R., Yang, J. H., Cho, C. H., Kim, H. Y., Lee, J. H., Park, J. S. and Kim, D. K. (2010) Antioxidant Constituents of the heartwood of Cedrela sinsesis A. Juss. Kor. J. Pharmacogn. 41: 245-249.
  13. Jeong, S. I., Cho, J. K., Mok, J. Y., Kim, S. J., Park, J. M., Jeon, I. H., Kim, H. S. and Jang, S. I. (2010) Antioxidant activity of Persimmon leaves during growth. Kor. J. Pharmacogn. 41: 255-263.
  14. Koo, U., Lee, H. J., Lee, D. H., Lee, H. J., Ham, A. R., Cho, E. Y. and Mar, W. C. (2008) Anti-oxidative effect of some plant extracts against nitric oxide-induced oxidative stress on neuronal cell. Kor. J. Pharmacogn. 39: 290-294.
  15. Miliauskas, G., Venskutonis, P. R. and Van-Beek, T. A. (2004) Screening of radical scavenging activity of some medicinal and aromatic plant extracts. Food Chem. 85: 231-237. https://doi.org/10.1016/j.foodchem.2003.05.007
  16. Han, W. and Wang, M. H. (2010) Radical scavenging and anti- inflammation activities from different extracts of Zanthoxylum schnifolium fruits. Kor. J. Pharmacogn. 41: 250-254.
  17. Jeong, S. J., Ko, Y. S., Ahn, N. H. and Kim, Y. C. (1998) Hyaluronidase inhibitor from Uncariae ramulus et Uncus. Kor. J. Pharmacogn. 29: 169-172.
  18. Kim, Y. S., Noh, Y. K., Lee, G. I., Kim, Y. K., Lee, K. S. and Min, K. R. (1995) Inhibitory effects of herbal medicines on hyaluronidase activity. Kor. J. Pharmacogn. 26: 265-272.
  19. Cha, B. C. and Lee, E. H. (2004) Antioxidant and antiinflammation activities of Prunus persica tree extracts. Korean J. Medicinal Crop Sci. 12: 289-294.
  20. Marquina, M. A., Corao, G. M., Araujo, L., Buitrago, D. and Sosa, M. (2002) Hyaluronidase inhibitory activity from the polyphenols in the fruit of blackberry (Rubus fruticosus B.). Fitoterapia 73: 727-729. https://doi.org/10.1016/S0367-326X(02)00222-8
  21. Hanninen, O., Kaartinen, K., Rauma, A. L., Nenonen, M., Torronen, R., Hakkinen, S., Adlercreutz, H. and Laakso, J. (2000) Antioxidants in vegan diet and rheumatic disorders. Toxicology 155: 45-53. https://doi.org/10.1016/S0300-483X(00)00276-6
  22. Jeong, H. S., Han, J. G., Ha, J. H., Kim, Y., Oh, S. H., Kim, S. S., Jeong, M. H., Choi, G. P, Park, U. Y. and Lee, H. Y. (2009) Antioxidant activities and skin-whitening effect of nano-encapsuled water extract from Rubus coreanus Miquel. Korean J. Medicinal Crop Sci. 17: 83-89.
  23. Chan, E. W. C., Lim, Y. Y., Wong, L. F., Lianto, F. S., Wong, S. K., Lim, K. K., Joe, C. E. and Lim, T. Y. (2008) Antioxidant and tyrosinase inhibition properties of leaves and rhizomes of ginger species. Food Chem. 109: 477-483. https://doi.org/10.1016/j.foodchem.2008.02.016
  24. Karioti, A., Protopappa, A., Megoulas, N. and Skaltsa, H. (2007) Identification of tyrosinase inhibitors from Marrubium velutium and Marrubium cylleneum. Bioorg. Med. Chem. 15: 2708-2714. https://doi.org/10.1016/j.bmc.2007.01.035
  25. Likhitwitayawuid, K., Sornsute, A., Sritularak, B. and Ploypradith, P. (2006) Chemical transformations of oxyresveratrol (trans-2,4,3',5'-tetra hydroxystilbene) into a potent tyrosinase inhibitor and strong cytotoxic agent. Bioorg. Med. Chem. Lett. 16: 5650-5653. https://doi.org/10.1016/j.bmcl.2006.08.018
  26. Maeda, K. and Fukuda, M. (1991) In vitro effectiveness of several whitening cosmetic components in human melanocytes. J. Soc. Cosmet. Chem. 42: 361-368.
  27. Lee, C. B. (1982) Forest Economics-mokchogangmok. Korean plant map. 29, Hyangmunsa, Seoul, Korea.
  28. Lee, D. H., Kim, J. H., Kim, N. M., Choi, J. S. and Lee, J. S. (2002) Physiological functionality of chinese quince wine and liquors. Kor. J. Biotechnol. Bioeng. 17: 266-270.
  29. Lee, Y. M., Shin, H. D., Lee, J. J. and Lee, M. Y. (2007) Antioxidative effect of Chaenomelis Fructus ethanol extract. Korean J. Food Preserv. 14: 177-182.
  30. Baek, M. Y., Cho, J. G., Lee, D. Y., Ahn, E. M., Jeong, T. S. and Baek, N. I. (2010) Isolation of triterpenoids from the stem bark of Albizia julibrissin and their inhibition activity on ACAT-1 and ACAT-2. J. Korean Soc. Appl. Biol. Chem. 53: 310-315. https://doi.org/10.3839/jksabc.2010.048
  31. Kim, J. S., Kim, Y. J., Lee, S. Y. and Kang, S. S. (2008) Phytochemical studies on Paeoniae radix (3)-Triterpenoids. Kor. J. Pharmacogn. 39: 37-42.
  32. Park, J. C., Lee, J. I. and Ahn, S. D. (1989) Study on the constituents in the fruit of Chaenomeles sinensis Koehne. Kor. J. Pharmacogn. 20: 10-12.
  33. Bae, J. H., Lee, W. W., Suh, K. S. and Kim, S. T. (2000) The effect of oleanolic acid and ursodeoxycholic acid on the pigmentation in the mouse by ultraviolet-B(UVB) irradiation. Korean J. Innvestigative dermatology 7: 223-229.
  34. Liu, J. (1995) Pharmacology of oleanolic acid and ursolic acid. J. Ethnopharmacol. 49: 57-68. https://doi.org/10.1016/0378-8741(95)90032-2
  35. Natsume, M., Osakabe, N., Oyama, M., Sasaki, M., Baba, S., Nakamura, Y., Osawa, T. and Terao, J. (2003) Structure of (-)-epicatechin glucuronide identified from plasma and urine after oral ingestion of (-)-epicatechin : differences between human and rat. Free Radical Biol. Med. 34: 840-849. https://doi.org/10.1016/S0891-5849(02)01434-X
  36. Berregi, I., Santos, J. I., Campo, G. and Miranda, J. I. (2003) Quantitative determination of (-)-epicatechin in cider apple juices by $^1H$ NMR. Talanta, 61: 139-145. https://doi.org/10.1016/S0039-9140(03)00236-4
  37. Cren-Olive, C., Wieruszeski, J. M., Maes, E. and Rolando, C. (2002) Catechin and epicatechin deprotonation followed by $^{13}C$ NMR. Tetrahedron Lett. 43: 4545-4549. https://doi.org/10.1016/S0040-4039(02)00745-1
  38. Cha, B. C., Lee, E. H. and Noh, M. A. (2005) Antioxidant activity of Spatholobus suberectus Dunn. Kor. J. Pharmacogn. 36: 50-55.