Archives of Pharmacal Research

The Pharmaceutical Society of Korea (대한약학회)
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Anti-Inflammatory Principles from the Fruits of Evodia rutaecarpa and Their Cellular Action Mechanisms

  • Choi Yong-Hwan (College of Pharmacy, Kangwon National University) ;
  • Shin Eun-Myoung (Natural Products Research Institute and College of Pharmacy, Seoul National University) ;
  • Kim Yeong-Shik (Natural Products Research Institute and College of Pharmacy, Seoul National University) ;
  • Cai Xing-Fu (Korea Research Institute of Bioscience and Biotechnology) ;
  • Lee Jung-Joon (Korea Research Institute of Bioscience and Biotechnology) ;
  • Kim Hyun-Pyo (College of Pharmacy, Kangwon National University)
  • Published : 2006.04.01
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Abstract

The fruits of Evodia rutaecarpa Benth (Rutaceae) has long been used for inflammatory disorders and some anti-inflammatory actions of its constituents such as dehydroevodiamine, evodiamine and rutaecarpine were previously reported. Since the pharmacological data is not sufficient to clearly establish the scientific rationale of anti-inflammatory medicinal use of this plant material and the search for its active principles is limited so far, three major constituents (evodiamine, rutaecarpine, goshuyuamide II) were evaluated for their anti-inflammatory cellular action mechanisms in the present study. From the results, evodiamine and rutaecarpine were found to strongly inhibit prostaglandin $E_2$ synthesis from lipopolysaccharide-treated RAW 264.7 cells at $1-10{\mu}M$. Evodiamine inhibited cyclooxygenase-2 induction and NF-kB activation, while rutaecarpine did not. On the other hand, goshuyuamide II inhibited 5-lipoxygenase from RBL-1 cells $(IC_{50}=6.6{\mu}M)$, resulting in the reduced synthesis of leukotrienes. However, these three compounds were not inhibitory against inducible nitric oxide synthase-mediated nitric oxide production from RAW cells up to $50{\mu}M$. These pharmacological properties may provide the additional scientific rationale for anti-inflammatory use of the fruits of E. rutaecarpa.

Keywords

References

  1. Adams, M., Kunert, O., Haslinger, E., and Bauer, R., Inhibition of leukotriene biosynthesis by quinolone alkaloids from the fruits of Evodia rutaecarpa. Planta Med., 70, 904-908 (2004) https://doi.org/10.1055/s-2004-832614
  2. Ahn, K. S., Moon, K. Y., and Kim, Y. S., Downregulation of NF- ${\kappa}B$ activation in human keratinocytes by melanogenic inhibitors. J. Dermatol. Sci., 31, 193-201 (2003) https://doi.org/10.1016/S0923-1811(03)00039-2
  3. Ahn, K. S., Noh, E. J., Zhao, H. L., Jung, S. H., Kang, S. S., and Kim, Y. S., Inhibition of inducible nitric oxide synthase and cyclooxygenase II by Platycodon grandiflorum saponins via suppression of $NF-{\kappa}B$ activation in RAW 264.7 cells. Life Sci., 76, 2315-2328 (2005) https://doi.org/10.1016/j.lfs.2004.10.042
  4. Bae, K., The medicinal plants of Korea, Kyo-Hak Publishing Co., Seoul, (2000) pp. 287
  5. Bergman, J. and Bergman, S., Studies of rutaecarpine and related quinazolinocarboline alkaloids. J. Org. Chem., 50, 1246-1255 (1985) https://doi.org/10.1021/jo00208a018
  6. Chi, Y. S., Cheon, B. S., and Kim, H. P., Effect of wogonin, a plant flavone from Scutellaria radix, on the suppression of cyclooxygenase and the induction of inducible nitric oxide synthase in lipopolysaccharide-treated RAW 264.7 cells. Biochem. Pharmacol., 61, 1195-1203 (2001) https://doi.org/10.1016/S0006-2952(01)00597-4
  7. Chiou, W. F., Sung, Y. J., Liao, J. F., Shum, A. Y., and Chen, C. F., Inhibitory effect of dehydroevodiamine and evodiamine on nitric oxide production in cultured murine macrophages. J. Nat. Prod., 60, 708-711 (1997) https://doi.org/10.1021/np960495z
  8. Hwang, S. Y., Hwang, B. Y., Ju, H. K., Park, J. H., Son, K. H., Lee, S. H., Chang, S. Y., Kang, S. J., Ro, J. S., and Lee, K. S., Isolation and quantitative analysis of evodiamine from Evodiae Fructus. Kor. J. Pharmacogn., 32, 98-102 (2001)
  9. Jin, H. Z., Lee, J. H., Lee, D., Lee, H. S., Hong, Y. S., Kim, Y. H., and Lee, J. J., Quinolone alkaloids with inhibitory activity against nuclear factor of activated T cells from the fruits of Evodia rutaecarpa. Biol. Pharm. Bull., 27, 926-928 (2004) https://doi.org/10.1248/bpb.27.926
  10. Gallin, J. I. and Snyderman, R., Overview, In Gallin, J. I. and Snyderman, R. (Eds.). Inflammaton: Basic principles and clinical correlates, 3rd ed. Lippincott Williams & Wilkins, Philadelphia, pp. 1-4 (1999)
  11. Moon, T. C., Murakami, M., Kudo, I., Son, K. H., Kim, H. P., Kang, S. S., and Chang, H. W., A new class of COX-2 inhibitor, rutaecarpine from Evodia rutaecarpa. Inflammation Res., 48, 621-625 (1999) https://doi.org/10.1007/s000110050512
  12. Mossman, T., Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxic assays. J Immunol. Methods., 65, 55-63 (1983) https://doi.org/10.1016/0022-1759(83)90303-4
  13. Noboru, S., Akemi, U., Akio, I., Nobuaki, S., and Shigenobu, A., Two novel alkaloids from Evodia rutaecarpa. J. Nat. Prod., 52, 1160-1162 (1989) https://doi.org/10.1021/np50065a043
  14. Takara, Y., Kobayashi, Y., and Aggarwal, B. B., Evodiamine abolishes constitutive and inducible $NF-{\kappa}B$ activation by inhibiting $IkB-{\alpha}$ kinase activation, thereby suppressing $NF-{\kappa}B$-regulated antiapoptotic and metastatic gene expression, up-regulating apoptosis and inhibiting invasion. J. Biol. Chem., 280, 17203-17212 (2005) https://doi.org/10.1074/jbc.M500077200
  15. Tang, W. and Eisenbrand, G., Chinese drugs of plant origin, Springer-Verlag, New York, pp. 509-514 (1992)
  16. Woo, H. G., Lee, C. H., Noh, M. S., Lee, J. J., Jung, Y. S., Baik, E. J., Moon, C. H., and Lee, S. H., Rutaecarpine, a quinazolinocarboline alkaloid, inhibits prostaglandin production in RAW 264.7 macrophages. Planta Med., 67, 505-509 (2001) https://doi.org/10.1055/s-2001-16479