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The Pharmaceutical Society of Korea (대한약학회)
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Nitric Oxide and Prostaglandin $E_2$ Synthesis Inhibitory Activities of Diarylheptanoids from the Barks of Alnus japonica Steudel

  • Published : 2005.02.01
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Abstract

Nine known diarylheptanoids (1-9) isolated from the barks of Alnus japonica were evaluated for their inhibitory activities on nitric oxide (NO) and prostagrandin $E_2$ (COX-2) production in interferon-${\gamma}$ (INF-${\gamma}$) and lipopolysaccharide (LPS)-activated RAW 264.7 cells in vitro. The NO and COX-2 levels were moderately reduced by the addition of compounds (1-9). Among these compounds, compounds 6 and 8 inhibited NO production in a dose dependent manner with an $IC_{50}$ of 16.7 and $27.2\;{\mu}g/mL$, respectively (positive control, L-NMMA; $22.8\;{\mu}g/mL$), and compounds 6, 7, 8, and 9 reduced the COX-2 level in a dose dependent manner with an $IC_{50}$ of 20.7, 25.7, 25.0, and $27.3\;{\mu}g/mL$, respectively (positive control, indomethacin; $26.2\;{\mu}g/mL$). An analysis of the structural activity relationship among these diarylheptanoids suggests that the presence of a keto-enol group in the heptane moiety or a caffeoyl group in the aromatic ring were important for the efficacy on the inhibitory activities of NO and COX-2 production.

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References

  1. Jang D. S., Muriel C., Alison D. P., Leonardus B. S. K., Kazuko K., Norman R. F., Harry H. S. F., John M. P., and A. Douglas K., Potential cancer chemopreventive constituents of the leaves of Macaranga triloba. Phytochemistry, 65, 345-350 (2004) https://doi.org/10.1016/j.phytochem.2003.10.026
  2. Je K. H., Jan A. R., Lee H. T., Mar W. C., and Seo E. K., The inhibitory Principle of lipopolysaccharide-Induced Nitric Oxide Production from Inula britannica var. chinensis. Arch. Pharm.Res., 27, 83-85 (2004) https://doi.org/10.1007/BF02980051
  3. Kim, H. J., Kim, K. H., Yeom, S. H., Kim, M. K., Shim, J. G., and Lee M. W., New Diarylheptanoid from the Barks of Alnus japonica steudel. Chinese Chem. Lett., submitted (2004)
  4. Lee, M. W., Kim N. Y., Park. M. S., Ahn, K. H., Toh, S. H., Hahn, D. R., Kim, Y. C., and Chung, J. T., Diarylheptanoids with In vitro inducible nitric oxide synthesis inhibitory activity from Alnus hirsuta. Planta Med., 66, 551-553 (2000) https://doi.org/10.1055/s-2000-8606
  5. Lee, M. W., Kim J. H., Jeong, D. W., Ahn, K. H., Toh, S. H., and Surh, Y. J., Inhibition of Cyclooxygenase-2 Expression by Diarylheptanoids from the Bark of Alnus hirsuta var. sibirica. Biol. Pharm. Bull., 23, 517-518 (2000) https://doi.org/10.1248/bpb.23.517
  6. Moncada S., Palmer R. M., and Higgs E. A., Nitric oxide: physiology, pathophysiology, and pharmacology. Pharmacol. Rev., 43, 1091-1042 (1991)
  7. Mosmann, T., Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxic assays. J. Iimmunol. Methods., 65, 55-63 (1983) https://doi.org/10.1016/0022-1759(83)90303-4
  8. Rie I., Koichi S., Masakazu H., Takeshi S., Susumu K., and Fumio A., Inhibitory Effects of Hydrolyzable Tannins from Melastoma dodecandrum Lour. On Nitric Oxide Production by a Murine Macrophage-Like cell Line, RAW 264.7, Activated with Lipopolysaccharide and Interferon-$\gamma$. Biol. Pharm. Bull., 22, 647-653 (1999) https://doi.org/10.1248/bpb.22.647
  9. Subbaramiah K., Telang N., Ramonetti J. T., Araki T., DeVito B., Weksler B. B., and Dannenberg A. J., Transcription of cyclooxygenase-2 is enhanced in transformed mammary epithelial cells. Cancer Res., 56, 4424-4429 (1996)