Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Alkamides from Piper longum and Piper nigrum as Inhibitors of IL-6 action

  • Lee, Seung-Woong (Eco-friendly Biomaterial Research Center, Korea Research Institute of Bioscience and Biotechnology) ;
  • Kim, Myo-Sun (Eco-friendly Biomaterial Research Center, Korea Research Institute of Bioscience and Biotechnology) ;
  • Park, Mi-Hye (Eco-friendly Biomaterial Research Center, Korea Research Institute of Bioscience and Biotechnology) ;
  • Park, Su-Jin (Eco-friendly Biomaterial Research Center, Korea Research Institute of Bioscience and Biotechnology) ;
  • Lee, Woo-Song (Eco-friendly Biomaterial Research Center, Korea Research Institute of Bioscience and Biotechnology) ;
  • Chang, Jong-Sun (Eco-friendly Biomaterial Research Center, Korea Research Institute of Bioscience and Biotechnology) ;
  • Rho, Mun-Chual (Eco-friendly Biomaterial Research Center, Korea Research Institute of Bioscience and Biotechnology)
  • Published : 2010.04.20
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Abstract

Blocking of IL-6 has been postulated to be an effective therapy in the pathogenesis of several inflammatory diseases. The current study was performed to examine the potential effects of alkamides isolated from P. longum and P. nigrum on IL-6 induced Stat3 activation and identify the structure-activity relationship of these alkamides in human hepatoma cells. Among 10 alkamides isolated from P. longum and P. nigrum, compounds 6, 7 and 9 were identified as strong inhibitors of IL-6 action, which inhibit IL-6 induced Stat3-dependent luciferase activities. These inhibitory activities were positively influenced by the presence of piperidine moiety.

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References

  1. Strassmann, G.; Masui, Y.; Chizzonite, R.; Fong, M. J. Immunol.1993, 150, 2341.
  2. Yoshizaki, K.; Matsuda, T.; Nishimoto, N.; Kuritani, T.; Taeho, L.;Aozasa, K.; Nakahata, T.; Kawai, H.; Tagoh, H.; Komori, T.; Kishimoto,S.; Hirano, T.; Kishimoto, T. Blood 1989, 74, 1360.
  3. Takagi, N.; Mihara, M.; Moriya, Y.; Nishimoto, N.; Yoshizaki, K.;Kishimoto, T.; Takeda, Y.; Ohsugi, Y. Arthritis. Rheum. 1998, 41,2117. https://doi.org/10.1002/1529-0131(199812)41:12<2117::AID-ART6>3.0.CO;2-P
  4. De la Mata, J.; Uy, H. L.; Guise, T. A.; Story, B.; Boyce, B. F.;Mundy, G. R.; Roodman, G. D. J. Clin. Invest. 1995, 95, 2846. https://doi.org/10.1172/JCI117990
  5. Zhang, X. G.; Bataille, R.; Jourdan, M.; Saeland, S.; Banchereau,J.; Mannoni, P.; Klein, B. Blood 1990, 76, 2599.
  6. Bhagat, K.; Valance, P. Circulation 1997, 96, 3042. https://doi.org/10.1161/01.CIR.96.9.3042
  7. Hayashi, M.; Rho, M. C.; Enomoto, A.; Fukami, A.; Kim, Y. P.;Kikuchi, Y.; Sunazuka, T.; Hirose, T.; Komiyama, K.; Omura, S.Proc. Natl. Acad. Sci. USA 2002, 99, 14728. https://doi.org/10.1073/pnas.232562799
  8. Lutticken, C.; Wegenka, U.; Yuan, J.; Buschmann, J.; Schindler,C.; Ziemiecki, A.; Harpur, A.; Wilks, A.; Yasukawa, K.; Taga, T.;Kishimoto, T.; Barbieri, G.; Pellegrini, S.; Sendtner, M.; Heinrich,P. C.; Horn, F. Science 1994, 263, 89. https://doi.org/10.1126/science.8272872
  9. Ihle, J. Cell 1996, 84, 331. https://doi.org/10.1016/S0092-8674(00)81277-5
  10. Sebti, S.; Der, C. Nat. Rev. Cancer 2003, 3, 945. https://doi.org/10.1038/nrc1234
  11. Darnell, J., Jr. Science 1997, 277, 1630. https://doi.org/10.1126/science.277.5332.1630
  12. Aaronson, D.; Horvath, C. Science 2002, 296, 1653. https://doi.org/10.1126/science.1071545
  13. Jung, B. S.; Shin, M. K. Encyclopedia of Illustrated Gorean Natural Drugs; Young Lim Sa: Seoul, 1998; p 439.
  14. Kiuchi, F.; Nakamura, N.; Tsuda, Y.; Kondo, K.; Yoshimura, H.Chem. Pharm. Bull. 1988, 36, 2452. https://doi.org/10.1248/cpb.36.2452
  15. Mujumdar, A. M.; Dhuley, J. N.; Deshmukh, V. K.; Raman, P. H.;Naik, S. R. Jpn. J. Med. Sci. Biol. 1990, 43, 95. https://doi.org/10.7883/yoken1952.43.95
  16. Park, I. K.; Lee, S. G.; Shin, S. C.; Park, J. D.; Ahn, Y. J. J. Agric. Food Chem. 2002, 50, 1866. https://doi.org/10.1021/jf011457a
  17. Reddy, S. V.; Srinivas, P. V.; Praveen, B.; Kishore, K. H.; Raju,B. C.; Murthy, U. S.; Rao, J. M. Phytomedicine 2004, 11, 697. https://doi.org/10.1016/j.phymed.2003.04.004
  18. Lee, S. W.; Rho, M. C.; Nam, J. Y.; Lim, E. H.; Kwon, O. E.; Kim,Y. H.; Lee, H. S.; Kim, Y. K. Planta Med. 2004, 70, 678. https://doi.org/10.1055/s-2004-827193
  19. Rho, M. C.; Lee, S. W.; Park, H. R.; Choi, J. H.; Kang, J. Y.; Kim,K.; Lee, H. S.; Kim, Y. K. Phytochemistry 2007, 68, 899. https://doi.org/10.1016/j.phytochem.2006.11.025
  20. Lee, S. W.; Rho, M. C.; Park, H. R.; Choi, J. H.; Kang, J. Y.; Lee,J. W.; Kim, K.; Lee, H. S.; Kim, Y. K. J. Agric. Food Chem.2006, 54, 9759. https://doi.org/10.1021/jf061402e
  21. Lee, S. W.; Kim, Y. K.; Kim, K.; Lee, H. S.; Choi, J. H.; Lee, W. S.;Jun, C. D.; Park, J. H.; Lee, J. M.; Rho, M. C. Bioorg. Med. Chem. Lett. 2008, 18, 4544. https://doi.org/10.1016/j.bmcl.2008.07.045
  22. Yan, S. F.; Zou, Y. S.; Gao, Y.; Zhai, C.; Mackman, N.; Lee, S. L.;Milbrandt, J.; Pinsky, D.; Kisiel, W.; Stern, D. Proc. Natl. Acad. Sci. USA 1998, 95, 8298. https://doi.org/10.1073/pnas.95.14.8298
  23. Tenhumberg, S.; Schuster, B.; Zhu, L.; Kovaleva, M.; Scheller, J.;Kallen, K. J.; Rose-John, S. Biochem. Biophys. Res. Commun.2006, 346, 649. https://doi.org/10.1016/j.bbrc.2006.05.173

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