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Journal of Biomedicine and Biotechnology
Volume 2012 (2012), Article ID 952452, 9 pages
http://dx.doi.org/10.1155/2012/952452
Research Article

Depigmenting Effect of Kojic Acid Esters in Hyperpigmented B16F1 Melanoma Cells

1Department of Bioprocess Technology, Faculty of Biotechnology and Biomolecular Sciences, Universiti Putra Malaysia, 43400 Serdang, Malaysia
2Department of Microbiology, Faculty of Biotechnology and Biomolecular Sciences, Universiti Putra Malaysia, 43400 Serdang, Malaysia
3Institute of Bioscience, Universiti Putra Malaysia, 43400 Serdang, Malaysia

Received 14 May 2012; Revised 21 June 2012; Accepted 22 June 2012

Academic Editor: Kapil Mehta

Copyright © 2012 Ahmad Firdaus B. Lajis et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. E. A. Hurst, J. W. Harbour, and L. A. Cornelius, “Ocular melanoma: a review and the relationship to cutaneous melanoma,” Archives of Dermatology, vol. 139, no. 8, pp. 1067–1073, 2003. View at Publisher · View at Google Scholar · View at Scopus
  2. H. P. Huang, Y. W. Shih, Y. C. Chang, C. N. Hung, and C. J. Wang, “Chemoinhibitory effect of mulberry anthocyanins on melanoma metastasis involved in the Ras/PI3K pathway,” Journal of Agricultural and Food Chemistry, vol. 56, no. 19, pp. 9286–9293, 2008. View at Publisher · View at Google Scholar · View at Scopus
  3. V. J. Hearing, “The expanding role and presence of neuromelanins in the human brain—why gray matter is gray,” Pigment Cell and Melanoma Research, vol. 22, no. 1, pp. 10–11, 2009. View at Publisher · View at Google Scholar · View at Scopus
  4. J. P. Ortonne and D. L. Bissett, “Latest insights into skin hyperpigmentation,” Journal of Investigative Dermatology Symposium Proceedings, vol. 13, no. 1, pp. 10–14, 2008. View at Publisher · View at Google Scholar · View at Scopus
  5. G. Eisenhofer, H. Tian, C. Holmes, J. Matsunaga, S. Roffler-Tarlov, and V. J. Hearing, “Tyrosinase: a developmentally specific major determinant of peripheral dopamine,” The FASEB Journal, vol. 17, no. 10, pp. 1248–1255, 2003. View at Publisher · View at Google Scholar · View at Scopus
  6. S. J. Heo, S. C. Ko, S. M. Kang et al., “Inhibitory effect of diphlorethohydroxycarmalol on melanogenesis and its protective effect against UV-B radiation-induced cell damage,” Food and Chemical Toxicology, vol. 48, no. 5, pp. 1355–1361, 2010. View at Publisher · View at Google Scholar · View at Scopus
  7. U. Panich, K. Kongtaphan, T. Onkoksoong et al., “Modulation of antioxidant defense by Alpinia galanga and Curcuma aromatica extracts correlates with their inhibition of UVA-induced melanogenesis,” Cell Biology and Toxicology, vol. 26, no. 2, pp. 103–116, 2010. View at Publisher · View at Google Scholar · View at Scopus
  8. L. Novellino, A. Napolitano, and G. Prota, “5,6-Dihydroxyindoles in the fenton reaction: a model study of the role of melanin precursors in oxidative stress and hyperpigmentary processes,” Chemical Research in Toxicology, vol. 12, no. 10, pp. 985–992, 1999. View at Publisher · View at Google Scholar · View at Scopus
  9. Y. Niwa and H. Akamatsu, “Kojic acid scavenges free radicals while potentiating leukocyte functions including free radical generation,” Inflammation, vol. 15, no. 4, pp. 303–315, 1991. View at Google Scholar · View at Scopus
  10. M. Springer, K. Engelhart, and H. K. Biesalski, “Effects of 3-isobutyl-1-methylxanthine and kojic acid on cocultures and skin equivalents composed of HaCat cells and human melanocytes,” Archives of Dermatological Research, vol. 295, no. 2, pp. 88–91, 2003. View at Publisher · View at Google Scholar · View at Scopus
  11. R. Mohamad, M. S. Mohamad, N. Suhaili, M. M. Salleh, and A. B. Ariff, “Kojic acid: applications and development of fermention process for production,” Biological and Molecular Biology Reviews, vol. 5, no. 2, pp. 24–37, 2010. View at Google Scholar
  12. S. E. Ashari, R. Mohamad, A. Ariff, M. Basri, and A. B. Salleh, “Optimization of enzymatic synthesis of palm-based kojic acid ester using response surface methodology,” Journal of Oleo Science, vol. 58, no. 10, pp. 501–510, 2009. View at Google Scholar · View at Scopus
  13. K. J. Liu and J. F. Shaw, “Lipase-catalyzed synthesis of kojic acid esters in organic solvents,” Journal of the American Oil Chemists' Society, vol. 75, no. 11, pp. 1507–1511, 1998. View at Google Scholar · View at Scopus
  14. T. Raku and Y. Tokiwa, “Regioselective synthesis of kojic acid esters by Bacillus subtilis protease,” Biotechnology Letters, vol. 25, no. 12, pp. 969–974, 2003. View at Publisher · View at Google Scholar · View at Scopus
  15. H. S. Rho, H. S. Baek, S. M. Ann, D. H. Kim, and I. S. Chang, “Synthesis of new anti-melanogenic compounds containing two molecules of kojic acid,” Bulletin of the Korean Chemical Society, vol. 29, no. 8, pp. 1569–1571, 2008. View at Google Scholar · View at Scopus
  16. R. Mohamad and A. B. Ariff, “Biotransformation of various carbon sources to kojic acid by cell-bound enzyme system of A. flavus Link 44-1,” Biochemical Engineering Journal, vol. 35, no. 2, pp. 203–209, 2007. View at Publisher · View at Google Scholar · View at Scopus
  17. N. H. Khamaruddin, M. Basri, G. E. C. Lian et al., “Enzymatic synthesis and characterization of palm-based kojic acid Ester,” Journal of Oil Palm Research, vol. 20, pp. 461–469, 2009. View at Google Scholar · View at Scopus
  18. S. Momtaz, B. M. Mapunya, P. J. Houghton et al., “Tyrosinase inhibition by extracts and constituents of Sideroxylon inerme L. stem bark, used in South Africa for skin lightening,” Journal of Ethnopharmacology, vol. 119, no. 3, pp. 507–512, 2008. View at Publisher · View at Google Scholar · View at Scopus
  19. S. Shibata, S. Okano, Y. Yonemitsu et al., “Induction of efficient antitumor immunity using dendritic cells activated by recombinant Sendai virus and its modulation by exogenous IFN-β gene,” Journal of Immunology, vol. 177, no. 6, pp. 3564–3576, 2006. View at Google Scholar · View at Scopus
  20. X. G. Cao, X. X. Li, Y. Z. Bao, N. Z. Xing, and Y. Chen, “Responses of human lens epithelial cells to quercetin and DMSO,” Investigative Ophthalmology and Visual Science, vol. 48, no. 8, pp. 3714–3718, 2007. View at Publisher · View at Google Scholar · View at Scopus
  21. S. Makpol, N. N. M. Arifin, Z. Ismail, K. H. Chua, Y. A. M. Yusof, and W. Z. W. Ngah, “Modulation of melanin synthesis and its gene expression in skin melanocytes by palm tocotrienol rich fraction,” African Journal of Biochemistry Research, vol. 3, no. 12, pp. 385–392, 2009. View at Google Scholar
  22. S. W. Choi, S. K. Lee, E. O. Kim et al., “Antioxidant and antimelanogenic activities of polyamine conjugates from corn bran and related hydroxycinnamic acids,” Journal of Agricultural and Food Chemistry, vol. 55, no. 10, pp. 3920–3925, 2007. View at Publisher · View at Google Scholar · View at Scopus
  23. Y. J. Shin, C. S. Han, C. S. Lee et al., “Zeolite 4A, a synthetic silicate, suppresses melanogenesis through the degradation of microphthalmia-associated transcription factor by extracellular signal-regulated kinase activation in B16F10 melanoma cells,” Biological and Pharmaceutical Bulletin, vol. 33, no. 1, pp. 72–76, 2010. View at Publisher · View at Google Scholar · View at Scopus
  24. Y. Aoki, T. Tanigawa, H. Abe, and Y. Fujiwara, “Melanogenesis inhibition by an oolong tea extract in B16 mouse melanoma cells and UV-induced skin pigmentation in brownish guinea pigs,” Bioscience, Biotechnology and Biochemistry, vol. 71, no. 8, pp. 1879–1885, 2007. View at Publisher · View at Google Scholar · View at Scopus
  25. J. S. Yu and A. K. Kim, “Effect of combination of taurine and azelaic acid on antimelanogenesis in murine melanoma cells,” Journal of Biomedical Science, vol. 17, supplement 1, article S45, 2010. View at Publisher · View at Google Scholar · View at Scopus
  26. D. S. Kim, S. H. Park, S. B. Kwon, K. Li, S. W. Youn, and K. C. Park, “(-)-Epigallocatechin-3-gallate and hinokitiol reduce melanin synthesis via decreased MITF production,” Archives of Pharmacal Research, vol. 27, no. 3, pp. 334–339, 2004. View at Google Scholar · View at Scopus
  27. S. K. Ha, M. Koketsu, K. Lee et al., “Inhibition of tyrosinase activity by N,N-unsubstituted selenourea derivatives,” Biological and Pharmaceutical Bulletin, vol. 28, no. 5, pp. 838–840, 2005. View at Publisher · View at Google Scholar · View at Scopus
  28. Y. J. Kim, “Antimelanogenic and antioxidant properties of gallic acid,” Biological and Pharmaceutical Bulletin, vol. 30, no. 6, pp. 1052–1055, 2007. View at Publisher · View at Google Scholar · View at Scopus
  29. K. D. Kim, M. H. Song, E. K. Yum, O. S. Jeon, Y. W. Ju, and M. S. Chang, “Melanogenesis inhibition by mono-hydroxycinnamic ester derivatives in B16 melanoma cells,” Bulletin of the Korean Chemical Society, vol. 31, no. 1, pp. 181–184, 2010. View at Publisher · View at Google Scholar · View at Scopus
  30. M. Kinoshita, N. Hori, K. Aida, T. Sugawara, and M. Ohnishi, “Prevention of melanin formation by yeast cerebroside in B16 mouse melanoma cells,” Journal of Oleo Science, vol. 56, no. 12, pp. 645–648, 2007. View at Google Scholar · View at Scopus
  31. K. Sato, H. Takahashi, R. Iraha, and M. Toriyama, “Down-regulation of tyrosinase expression by acetylsalicylic acid in murine B16 melanoma,” Biological and Pharmaceutical Bulletin, vol. 31, no. 1, pp. 33–37, 2008. View at Publisher · View at Google Scholar · View at Scopus
  32. S. A. Burchill, D. C. Bennett, A. Holmes, and A. J. Thody, “Tyrosinase expression and melanogenesis in melanotic and amelanotic B16 mouse melanoma cells,” Pathobiology, vol. 59, no. 5, pp. 335–339, 1991. View at Google Scholar · View at Scopus
  33. T. Shioda, M. H. Fenner, and K. J. Isselbacher, “msg1, a novel melanocyte-specific gene, encodes a nuclear protein and is associated with pigmentation,” Proceedings of the National Academy of Sciences of the United States of America, vol. 93, no. 22, pp. 12298–12303, 1996. View at Publisher · View at Google Scholar · View at Scopus
  34. K. Sato and M. Toriyama, “Depigmenting effect of catechins,” Molecules, vol. 14, no. 11, pp. 4425–4432, 2009. View at Publisher · View at Google Scholar · View at Scopus
  35. C. Bertolotto, K. Bille, J. P. Ortonne, and R. Ballotti, “Regulation of tyrosinase gene expression by cAMP in B16 melanoma cells involves two CATGTG motifs surrounding the TATA box: implication of the microphthalmia gene product,” Journal of Cell Biology, vol. 134, no. 3, pp. 747–755, 1996. View at Google Scholar · View at Scopus
  36. D. Rusciano, P. Lorenzoni, and M. M. Burger, “Regulation of c-met expression in B16 murine melanoma cells by melanocyte stimulating hormone,” Journal of Cell Science, vol. 112, no. 5, pp. 623–630, 1999. View at Google Scholar · View at Scopus
  37. K. Ohguchi, Y. Banno, Y. Akao, and Y. Nozawa, “Involvement of phospholipase D1 in melanogenesis of mouse B16 melanoma cells,” Journal of Biological Chemistry, vol. 279, no. 5, pp. 3408–3412, 2004. View at Publisher · View at Google Scholar · View at Scopus
  38. S. E. Hill, J. Buffey, A. J. Thody, I. Oliver, S. S. Bleehen, and S. MacNeil, “Investigation of the regulation of pigmentation in alpha-melanocyte-stimulating hormone responsive and unresponsive cultured B16 melanoma cells,” Pigment Cell Research, vol. 2, no. 3, pp. 161–166, 1989. View at Google Scholar · View at Scopus
  39. U. D. P. Lam, D. N. Hoang, H. B. Lee et al., “Depigmenting effect of Sterculia lynchnophera on B16F10 melanoma and C57BL/6 melan-a cells,” Korean Journal of Chemical Engineering, vol. 28, no. 4, pp. 1074–1077, 2011. View at Publisher · View at Google Scholar · View at Scopus
  40. Y. K. Choi, Y. K. Rho, K. H. Yoo et al., “Effects of vitamin C vs. multivitamin on melanogenesis: comparative study in vitro and in vivo,” International Journal of Dermatology, vol. 49, no. 2, pp. 218–226, 2010. View at Publisher · View at Google Scholar · View at Scopus
  41. I. Gülçin, “The antioxidant and radical scavenging activities of black pepper (Piper nigrum) seeds,” International Journal of Food Sciences and Nutrition, vol. 56, no. 7, pp. 491–499, 2005. View at Publisher · View at Google Scholar · View at Scopus
  42. N. M. Vad, P. K. Kandala, S. K. Srivastava, and M. Y. Moridani, “Structure-toxicity relationship of phenolic analogs as anti-melanoma agents: an enzyme directed prodrug approach,” Chemico-Biological Interactions, vol. 183, no. 3, pp. 462–471, 2010. View at Publisher · View at Google Scholar · View at Scopus
  43. H. L. Ma, M. J. Whitters, R. F. Konz et al., “IL-21 activates both innate and adaptive immunity to generate potent antitumor responses that require perforin but are independent of IFN-γ,” Journal of Immunology, vol. 171, no. 2, pp. 608–615, 2003. View at Google Scholar · View at Scopus
  44. J. H. Lee, H. Park, H. Chung et al., “Syndecan-2 regulates the migratory potential of melanoma cells,” Journal of Biological Chemistry, vol. 284, no. 40, pp. 27167–27175, 2009. View at Publisher · View at Google Scholar · View at Scopus
  45. Z. M. Hu, Q. Zhou, T. C. Lei, S. F. Ding, and S. Z. Xu, “Effects of hydroquinone and its glucoside derivatives on melanogenesis and antioxidation: biosafety as skin whitening agents,” Journal of Dermatological Science, vol. 55, no. 3, pp. 179–184, 2009. View at Publisher · View at Google Scholar · View at Scopus
  46. S. H. Lee, S. Y. Choi, H. Kim et al., “Mulberroside F isolated from the leaves of Morus alba inhibits melanin biosynthesis,” Biological and Pharmaceutical Bulletin, vol. 25, no. 8, pp. 1045–1048, 2002. View at Publisher · View at Google Scholar · View at Scopus