The Inhibitory Effect of Hydroxycinnamic Acid Derivatives from Corn (Zea may L.) Bran on Melanogenesis

옥수수겨 유래 하이드록시신나믹애씨드 유도체의 멜라닌 생성 저해 효과

  • 김미진 ((주)사임당화장품 기술연구소) ;
  • 임경란 ((주)사임당화장품 기술연구소) ;
  • 정택규 ((주)사임당화장품 기술연구소) ;
  • 윤경섭 ((주)사임당화장품 기술연구소) ;
  • 최상원 (대구가톨릭대학교 식품영양학과)
  • Published : 2009.06.30

Abstract

Several hydroxycinnamic acid derivatives, p-coumaric acid, ferulic acid, N,N'-dicoumaroylputrescine (DCP), N-p-coumaroyl-N'-feruloyl-putrescine (CFP), and N,N'-diferuloylputrescine (DFP) were isolated and purified from corn bran. To develop the skin whitening agent, we investigated the effects of hydroxycinnamic acid derivatives from corn bran, on melanogenesis. CFP and DFP inhibited melanin synthesis in a dose dependent manner up to 44.7 ${\pm}$ 6.0 %, and 58.5 ${\pm}$ 3.1 % at a concentration of 50 ${\mu}g/mL$, respectively. The intracellular tyrosinase activity decreased about 42.5 ${\pm}$ 14.6 %, and 9.0 ${\pm}$ 4.4 % at a concentration of 50 ${\mu}g/mL$ of CFP and DFP, respectively. Our results suggest that inhibitory effects of hydroxycinnamic acid derivatives on melanogenesis are due to the inhibition of the intracellular tyrosinase activity. These results indicate that these hydroxycinnamic acid derivatives from corn bran may be potential natural skin whitening agents.

옥수수겨로부터 분리 정제한 하이드록시신나믹애씨드 유도체(hydroxycinnamic acid derivatives)는 p-coumaric acid, ferulic acid, N,N'-dicoumaroylputrescine (DCP), N-p-coumaroyl-N'-feruloylputrescine (CFP), N,N'-diferuloylputrescine (DFP) 등으로 분석이 되었으며, 옥수수겨추출물은 이들을 각각 함유하고 있었다. 본 연구는 천연 미백 소재 개발을 위하여 옥수수겨에서 유래한 화합물인, 하이드록시신나믹애씨드유도체의 멜라닌 생성에 연관된 생리활성을 알아보았다. 하이드록시신나믹애씨드유도체들의 B16-F1 melanoma cells에서의 멜라닌 생합성 저해효과는 농도 의존적으로 저해하여 CFP, DFP 50 ${\mu}g/$ mL에서 각각 44.7 ${\pm}$ 6.0 %, 58.5 ${\pm}$ 3.1 %의 저해율을 보였다. 그리고 세포 내 tyrosinase의 활성은 각각 42.5 ${\pm}$ 14.6 %, 9.0 ${\pm}$ 4.4 %의 저해효과를 보였다. 이러한 결과를 볼 때, 옥수수겨 유래 하이드록시신나믹애씨드 유도체들은 세포 내 tyrosinase의 활성을 억제함으로써 멜라닌 생성을 감소시키는 것으로 사료되며, 미백 효능을 갖는 천연 화장품 소재로서의 개발 가능성이 클 것으로 기대된다.

Keywords

References

  1. H. Z. Hill, W. Li, P. Xin, and D. L. Michell, Melanin: a two edged swords, Pigment Cell Res., 10, 158 (1997) https://doi.org/10.1111/j.1600-0749.1997.tb00478.x
  2. S. Briganti, E. Camera, and M. Picardo, Chemical and instrumental approaches to treat hyperpigmentation, Pigment Cell Res., 16, 101 (2003) https://doi.org/10.1034/j.1600-0749.2003.00029.x
  3. L. P. Zhang and Z. Z. Ji, Synthesis, antiinflammatory and anticancer activity of cinnamic acids, their derivatives and analogues, Yao Xue Xue Bao, 27, 817 (1992)
  4. L. R. Ferguson, I. F. Lim, A. E. Pearson, J. Ralph, and P. J. Harris, Bacterial antimutagenesis by hydroxycinnamic acids from plant cell walls, Mutat. Res., 542, 49 (2003) https://doi.org/10.1016/j.mrgentox.2003.08.005
  5. F. Natella, M. Nardini, M. D. Felice, and C. Scaccini, Benzoic and cinnamic acid derivatives as antioxidants: structure-activity relation, J. Agric. Food Chem., 47, 1453 (1999) https://doi.org/10.1021/jf980737w
  6. K. Iwai, N. Kishimoto, Y. Kakino, K. Mochida, and T. Fujita, In vitro antioxidative effects and tyrosinase inhibitory activities of seven hydroxycinnamoyl derivatives in green coffee beans, J. Agric. Food Chem., 52(15), 4893 (2004) https://doi.org/10.1021/jf040048m
  7. S. W. Choi, S. K. Lee, E. O. Kim, J. H. Oh, K. S. Yoon, N. Parris, K. B. Hicks, and R. A. Moreau, Antioxidant and antimelanogenic activities of polyamine conjugates from corn bran and related hydroxycinnamic acids, J. Agric. Food Chem., 55, 3920 (2007) https://doi.org/10.1021/jf0635154
  8. R. A. Moreau, A. Nunez, and V. Singh, Diferuloylputrescine and p-coumaroyl-feruloyputrescine, abundant polyamine conjugates in lipid extracts of maize kernels, Lipids, 36, 839 (2002)
  9. T. Niwa, U. Doi, and T. Osawa, Inhibitory activity of corn-derived bisamide compounds against α -glucosidase, J. Agric. Food Chem., 51, 90 (2003) https://doi.org/10.1021/jf020758x
  10. J. E. Mellon and R. A. Moreau, Inhibition of aflatoxin biosynthesis in Aspergillus flavus by diferuloylputrescine and p-coumaroylferuloylputrescine, J. Agric. Food Chem., 52, 6660 (2004) https://doi.org/10.1021/jf040226b
  11. M. S. Blois, Antioxidant determinations by the use of a stable free radical, Nature, 181, 1199 (1958) https://doi.org/10.1038/1811199a0
  12. T. Noro, O. Yasushi, M. Toshio, U. Akira, and S. ukushima, Inhibition of xanthine oxidase from the flowers and buds of Daphne genkwa, Chem. Pharm. Bull., 31, 3984 (1983) https://doi.org/10.1248/cpb.31.3984
  13. P. R. Gordon, C. P. Mansur, and B. A. Gilchrest, Regulation of human melanocyte growth, dendricity and melanization by keratinicyte derived factors. J. Invest. Dermatol., 92(4), 565 (1989) https://doi.org/10.1111/1523-1747.ep12709595
  14. J. Pawelek, Melanoma cells in culture, Methods Enzymol., 58, 564 (1978) https://doi.org/10.1016/S0076-6879(79)58172-5