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Active compounds from Schisandra chinensis exhibiting tyrosinase activity and melanin content inhibition in B16 melanoma cells

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Abstract

Schisandra chinensis has been used as traditional medicine. The structures of isolate active compounds (schisandrin B, deoxyschisandrin, schisandrin C) from S. chinensis were characterized by physical and spectroscopic analyses. Active compounds were tested for their potential to act as anti-melanogenesis or skin-whitening agents by their abilities to inhibit tyrosinase activity in the cell-free mushroom tyrosinase assay and cellular tyrosinase derived from B16 melanoma cells. The tyrosinase inhibitory activity was correlated to the inhibition of melanin productions in a-MSH-stimulated and unstimulated B16 cells. Cellular tyrosinase kinetics were analyzed and showed by Lineweaver- Burk plot. Schisandrin B was minimally cytotoxic (cell viability: 88.99% at 0.75 µM) and the IC50 value for suppression of mushroom tyrosinase activity was estimated as 0.6 µM. Zymography analysis demonstrated schisandrin B’s concentration-dependent effects and the kinetic analysis indicated schisandrin B’s noncompetitive-inhibitory action.

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References

  1. Ip, S. P., C. T. Chen, Y. C. Kong, and K. M. Ko (2001) Effects of schisandrin B pretreatment on tumor necrosis factor-α induced apoptosis and Hsp70 expression in mouse liver. Cell Stress Chaperones. 6: 44–46.

    Article  CAS  Google Scholar 

  2. Chen, Q. X., K. K. Song, Q. Wang, and H. Huang (2003) Inhibitory effects on mushroom tyrosinase by some alkylbenzaldehydes. J. Enz. Inhib. Med. Chem. 18: 491–496.

    Article  CAS  Google Scholar 

  3. Chiu, P. Y. and K. M. Ko (2003) Time-dependent enhancement in mitochondrial glutathione status and ATP generation capacity by schisandrin B treatment decreases the susceptibility of rat hearts to ischemia-reperfusion injury. Biofactors. 19: 43–51.

    Article  CAS  Google Scholar 

  4. Chiu, P. Y. and K. M. Ko (2004) Schisandrin B protects myocardial ischemia-reperfusion injury partly by inducing Hsp25 and Hsp70 expression in rats. Mol. Cell. Biochem. 266: 139–144.

    Article  CAS  Google Scholar 

  5. Giridharan, V. V., R. A. Thandavarayan, H. N. Bhilwade, K. M. Ko, K. Watanabe, and T. Konishi (2012) Schisandrin B, attenuates cisplatin-induced oxidative stress, genotoxicity and neurotoxicity through modulating NF-κB pathway in mice. Free Radic Res. 46: 50–60.

    Article  Google Scholar 

  6. Hearing, V. J. (2005) Biogenesis of pigment granules: A sensitive way to regulate melanocyte function. J. Dermatol. Sci. 37: 3–14.

    Article  CAS  Google Scholar 

  7. Tsatmali, M., J. Ancans, and A. J. Thody (2002) Melanocyte function and its control by melanocortin peptides. J. Histochem. Cytochem. 50: 125–133.

    Article  CAS  Google Scholar 

  8. Kameyama, K., C. Sakai, S. Kuge, S. Nishiyama, Y. Tomita, S. Ito, K. Wakamatsu, and V. J. Hearing (1995) The Expression of Tyrosinase, Tyrosinase-Related Proteins 1 and 2 (TRP1 and RP2), the Silver Protein, and a melanogenic inhibitor in human melanoma cells of differing melanogenic activities. Pigment Cell Res. 8: 97–104.

    Article  CAS  Google Scholar 

  9. Solano, F., S. Briganti, M. Picardo, and G. Ghanem (2006) Hypopigmenting agents: An updated review on biological, chemical and clinical aspects. Pigment Cell Res. 19: 550–571.

    Article  CAS  Google Scholar 

  10. Chiu, P. Y., P. Y. Lam, C. W. Yan, and K. M. Ko (2011) Schisandrin B protects against solar irradiation-induced oxidative injury in BJ human fibroblasts. Fitoterapia. 82: 682–691.

    Article  CAS  Google Scholar 

  11. Lam, P. Y., C. W. Yan, P. Y. Chiu, H. Y. Leung, and K. M. Ko (2011) Schisandrin B protects against solar irradiation-induced oxidative stress in rat skin tissue. Fitoterapia. 82: 393–400.

    Article  CAS  Google Scholar 

  12. Sugimoto, K., K. Nomura, T. Nishimura, T. Kiso, K. Sugimoto, and T. Kuriki (2005) Syntheses of α-arbutin-α-glycosides and their inhibitory effects on human tyrosinase. J. Biosci. Bioeng. 99: 272–276.

    Article  CAS  Google Scholar 

  13. Pérez, G. M. and C. F. García (2001) Dimethyl sulfide, a volatile flavor constituent, is a slow-binding inhibitor of tyrosinase. Biochem. Biophys. Res. Commun. 285: 257–261.

    Article  Google Scholar 

  14. Ma, W., M. Wlaschek, I. Tantcheva-Poór, L. Schneider, L. Naderi, Z. Razi-Wolf, J. Schüller, and K. Scharffetter-Kochanek (2001) Chronological ageing and photoageing of the fibroblasts and the dermal connective tissue. Clin. Exp. Dermatol. 26: 592–599.

    Article  CAS  Google Scholar 

  15. Kim, S. H., M. Joo, and S. H. Yoo (2009) Structural identification and antioxidant properties of major anthocyanin extracted from Omija (Schizandra chinensis) fruit. J. Food Sci. 74: C134–C140.

    Article  CAS  Google Scholar 

  16. Garcia, A. and J. E. Fulton (1996) The combination of glycolic acid and hydroquinone or kojic acid for the treatment of melasma and related conditions. Dermatol. Surg. 22: 443–447.

    CAS  Google Scholar 

  17. Schmidt, M., R. Kusche, W. Kronmüller, B. von Issendorff, and H. Haberland (1997) Experimental determination of the melting point and heat capacity for a free cluster of 139 sodium atoms. Physical Rev. Lett. 79: 99–102.

    Article  CAS  Google Scholar 

  18. Rasenack, N. and B. W. Müller (2002) Crystal habit and tableting behavior. Internat. J. Pharm. 244: 45–57.

    Article  CAS  Google Scholar 

  19. Li, C. T., Z. F. Yan, F. H. Tian, X. X. Mao, and Y. Li (2014) Chemical fingerprinting of Tussilago farara by RP-HPLC and hierarchical clustering analysis. Asian J. Chem. 26: 4003–4006.

    Article  CAS  Google Scholar 

  20. Tipper, E. T., P. Louvat, F. Capmas, A. Galy, and J. Gaillardet (2008) Accuracy of stable Mg and Ca isotope data obtained by MC-ICP-MS using the standard addition method. Chem. Geol. 257: 65–75.

    Article  CAS  Google Scholar 

  21. Lee, M. H., Y. P. Lin, F. L. Hsu, G. R. Zhan, and K. Y. Yen (2006) Bioactive constituents of Spatholobus suberectus in regulating tyrosinase-related proteins and mRNA in HEMn cells. Phytochem. 67: 1262–1270.

    Article  CAS  Google Scholar 

  22. Takahashi, H. and P. G. Parsons (1992) Rapid and reversible inhibition of tyrosinase activity by glucosidase inhibitors in human melanoma cells. J. Invest. Dermatol. 98: 481–487.

    Article  CAS  Google Scholar 

  23. Hunt, G., C. Todd, J. E. Cresswell, and A. J. Thody (1994) Alphamelanocyte stimulating hormone and its analogue Nle4DPhe7 α-MSH affect morphology, tyrosinase activity and melanogenesis in cultured human melanocytes. J. Cell Sci. 107: 205–211.

    CAS  Google Scholar 

  24. Chan, Y., K. Kim, and S. Cheah (2011) Inhibitory effects of Sargassum polycystum on tyrosinase activity and melanin formation in B16F10 murine melanoma cells. J. Ethnopharmacol. 137: 1183–1188.

    Article  CAS  Google Scholar 

  25. Chen, Q. X., K. K. Song, L. Qiu, X. D. Liu, H. Huang, and H. Y. Guo (2005) Inhibitory effects on mushroom tyrosinase by palkoxybenzoic acids. Food Chem. 91: 269–274.

    Article  CAS  Google Scholar 

  26. Greco, W. R. and M. T. Hakala (1979) Evaluation of methods for estimating the dissociation constant of tight binding enzyme inhibitors. J. Biol. Chem. 254: 12104–12109.

    CAS  Google Scholar 

  27. Lineweaver, H. and D. Burk (1934) The determination of enzyme dissociation constants. J. Am. Chem. Soc. 56: 658–666.

    Article  CAS  Google Scholar 

  28. Zhang, Q., J. Wu, Z. Hu, and D. Li (2004) Induction of HL-60 apoptosis by ethyl acetate extract of Cordyceps sinensis fungal mycelium. Life Sci. 75: 2911–2919.

    Article  CAS  Google Scholar 

  29. He, X. G., L. Z. Lian, and L. Z. Lin (1997) Analysis of lignan constituents from Schisandra chinensis by liquid chromatography-electrospray mass spectrometry. J. Chromatogr. A. 757: 81–87.

    Article  CAS  Google Scholar 

  30. Huang, X., F. Song, Z. Liu, and S. Liu (2007) Studies on lignan constituents from Schisandra chinensis (Turcz.) Baill. fruits using high-performance liquid chromatography/electrospray ionization multiple-stage tandem mass spectrometry. J. Mass Spectrom. 42: 1148–1161.

    Article  CAS  Google Scholar 

  31. Yukinobu, I. and K. Hiroshi (1979) The constituents of Schizandra chinensis Baill. I. Isolation and structure determination of five new lignans, gomisin A, B, C, F and G, and the absolute structure of schizandrin. Chem. Pharm. Bull. 27: 1383–1394.

    Article  Google Scholar 

  32. Yukinobu, I. (1982) The constituents of Schizandra chinensis Baill. XII. Isolation and structure of a new lignan, gomisin R, the absolute structure of wuweizisu C and isolation of schisantherin D. Chem. Pharm. Bull. 30: 3207–3211.

    Article  Google Scholar 

  33. Lo, Y. H., R. D. Lin, Y. P. Lin, Y. L. Liu, and M. H. Lee (2009) Active constituents from Sophora japonica exhibiting cellular tyrosinase inhibition in human epidermal melanocytes. J. Ethnopharmacol. 124: 625–629.

    Article  CAS  Google Scholar 

  34. Mu, F. Y., M. Jin, and R. Liu (2005) Analysis of content of the Schisandra chimensis Baill fruit, rattan and fruit handles. J. Med. Sci. Yanbian Univ. 28: 28–30.

    CAS  Google Scholar 

  35. Yin, F. Z., T. L. Lu, and L. Li (2005) Comparison of γ-schisandrin contents of Fructus schisandrae of different origins in Heilongjiang province. Acta Universitatis Traditionis Medicalis Sinensis Pharmacologiaeque Shanghai 19: 42–43.

    Google Scholar 

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Yan, ZF., Guo, J., Tian, FH. et al. Active compounds from Schisandra chinensis exhibiting tyrosinase activity and melanin content inhibition in B16 melanoma cells. Biotechnol Bioproc E 20, 814–823 (2015). https://doi.org/10.1007/s12257-014-0867-x

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