Biomolecules & Therapeutics

  • 제14권1호
  • /
  • Pages.36-39
  • /
  • 2006
  • /
  • 1976-9148(pISSN)
  • /
  • 2005-4483(eISSN)
한국응용약물학회 (The Korean Society of Applied Pharmacology)
권호 표지

Inhibition of Collagenase by Anti-inflammatory Synthetic Flavones

  • Park Hae-Il (College of Pharmacy, Kangwon National University) ;
  • Sin Bo-Young (College of Pharmacy, Kangwon National University) ;
  • Kim Hyun-Pyo (College of Pharmacy, Kangwon National University)
  • 발행 : 2006.03.01
PDF 다운로드
⟨ 이전 논문 다음 논문 ⟩

초록

Some flavones/flavonols were previously found to inhibit collagenase. To establish a therapeutic potential for skin inflammation, twenty-three synthetic flavone derivatives were examined for their inhibitory potential against collagenase from Clostridium histolyticum. From the results, it was found that most of them having various hydroxyl, methoxyl, methylsulfuryl and/or chloro substitution(s) on A- and B-rings were not efficient collagenase inhibitors. Among the synthetic flavones tested, only two synthetic derivatives, 3',4'-dihydroxyflavone and 5-hydroxy-4'-methoxyflavone, weakly inhibited bacterial collagenase (13-29% inhibition at 50-100 ${\mu}M$).

키워드

참고문헌

  1. Choe, T., Lee, B., Park, I. and Hong, S. (2003). Inhibition of matrix metalloproteinase-1 and -2 expression using nitric oxide synthase inhibitors in UV-irradiated human dermal fibroblasts. J. Cosmet. Sci. 54, 229-238
  2. Dao, T. T., Chi, Y. S., Kim, J., Kim, H. P., Kim, S. and Park, H. (2003). Synthesis and $PGE_{2}$ inhibitory activity of 5,7-dihydroxyflavones and their O-methylated flavone analogues. Arch. Pharm. Res. 26, 345-350 https://doi.org/10.1007/BF02976690
  3. Ende, C. and Gebhardt, R. (2004). Inhibition of matrix metalloproteinase- 2 and -9 activities by selected flavonoids. Planta Med. 70, 1006-1008 https://doi.org/10.1055/s-2004-832630
  4. Fisher, G. J. and Voorhees, J. J. (1998). Molecular mechanism of photoaging and its prevention by retinoic acid: ultraviolet irradiation induces MAP kinase signaling transduction cascade that induce AP-I-regulated matrix metalloproteinases that degrade human skin in vivo. J. Investig. Dermatol. Symp. Proc. 3, 61-68
  5. Gabor, M. (1986). Anti-inflammatory and anti-allergic properties of flavonoids. In Plant flavonoids in biology and medicine: Biochemical, pharmacological, and structure-activity relationships (Cody et al., Eds.), pp. 471-480. Alan R. Liss, New York
  6. Kang, S., Chung, J. H., Lee, J. H., Fisher, G. J., Wan, Y. S., Duell, E. A. and Voorhees, J. J. (2003). Topical N-acetyl cysteine and genistein prevent ultraviolet-light-induced signaling that leads to photoaging in human skin in vivo. J. Invest. Dermatol. 120, 835-841 https://doi.org/10.1046/j.1523-1747.2003.12122.x
  7. Kim, H. P., Son, K. H., Chang, H. W. and Kang, S. S. (2004). Anti-inflammatory plant flavonoids and cellular action mechanisms. J. Pharmacol. Sci. 96, 229-245 https://doi.org/10.1254/jphs.CRJ04003X
  8. Lewis, D. A. (1989) Flavonoids. In Anti-inflammatory drugs from plant and marine sources (D. A. Lewis, Ed.), Agents and Actions, Suppl. Vol. 27, pp. 137-165. Berkhauser Verlag, Basel
  9. Lin, N., Sato, T., Takayama, Y., Mimaki, Y., Sashida, Y., Yano, M. and Ito, A. (2003). Novel anti-inflammatory actions of nobiletin, a citrus polymethoxy flavonoid, on human synovial fibroblasts and mouse macrophages. Biochem. Pharmacol. 65, 2065-2071 https://doi.org/10.1016/S0006-2952(03)00203-X
  10. Makimura, M., Hirasawa, M., Kobayashi, K., Indo, J., Sakanaka, S., Taguchi, T. and Otake, S. (1993). Inhibitory effect of tea catechins on collagenase activity. J. Periodontol. 64, 630-636 https://doi.org/10.1902/jop.1993.64.7.630
  11. Melzig, M. E, Loser, B. and Ciesielski, S. (2001). Inhibition of neutrophil elastase activity by phenolic compounds from plants. Pharmazie 56, 967-970
  12. Middleton, E., Kandaswami, C. and Theoharides, T. C. (2000). The effects of plant flavonoids on mammalian cells: Implications for inflammation. heart diseases. and cancer. Pharmacol.Rev. 52, 673-751
  13. Nagase, H., Sasaki, K., Kito, H., Haga, A. and Sato, T. (1998). Inhibitory effect of delphinidin from Solanum melongena on human fibrosarcoma HT-1080 invasiveness in vitro. Planta Med. 64, 216-219 https://doi.org/10.1055/s-2006-957412
  14. Park, H., Dao, T. T. and Kim, H. P. (2005). Synthesis and inhibition of $PGE_{2}$ production of 6,8-disubstituted chrysin derivatives. Eur. J. Med. Chem. 40, 943-948 https://doi.org/10.1016/j.ejmech.2005.04.013
  15. Sartor, L., Pezzato, E., Dell'Aica, I., Caniato, R., Biggin, S. and Garbisa, S. (2002). Inhibition of matrix-proteases by polyphenols: chemical insights for anti-inflammatory and anti-invasion drug design. Biochem. Phannacol. 64, 229-237 https://doi.org/10.1016/S0006-2952(02)01069-9
  16. Sawabe, Y., Yamasaki, K., Iwagarni, S., Kazimura, K. and Nakagommi, K. (1998). Inhibitory effects of natural medicines on the enzymes related to the skin. Yakugaku Zasshi 118, 423-429 https://doi.org/10.1248/yakushi1947.118.9_423
  17. Sin, B. Y. and Kim, H. P. (2005). Inhibition of collagenase by naturally-occurring flavonoids. Arch. Pharm. Res. 28, 1152-1155 https://doi.org/10.1007/BF02972978
  18. Song, L., Xu, M., Lopes-Virella, M. F. and Huang, Y. (2001). Quercetin inhibits matrix metalloproteinase-l expression in human vascular endothelial cells through extracellular signalregulated kinase. Arch. Biochem. Biophys. 391, 72-78 https://doi.org/10.1006/abbi.2001.2402