Archives of Pharmacal Research

  • 제27권3호
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  • Pages.278-282
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  • 2004
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  • 0253-6269(pISSN)
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  • 1976-3786(eISSN)
대한약학회 (The Pharmaceutical Society of Korea)
권호 표지

Synthesis and Biological Activities of 8-Arylflavones

  • 발행 : 2004.03.01
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초록

A number of 8-arylflavones have been synthesized as congeners of wogonin and evaluated for their inhibitory activities of $PGE_2$ production. 8-Arylflavones were obtained from commercially available chrysin via two different synthetic pathways. Most 8-arylflavones exhibited much reduced inhibitory activities against COX-2 catalyzed $PGE_2$ production compared to that of wogonin. Functional group replacement at the 8-position of wogonin from methoxy to aryl group caused loss of inhibitory activity. Our present results imply that the functional group at the 8-position of flavones seems to play very important roles for bioactivity.

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참고문헌

  1. Chen, Y. C., Shen, S. C., Chen, L. G., Lee, T. J., and Yang, L. L. Wogonin, baicalin, and baicalein inhibition of inducible nitric oxide synthase and cyclooxygenase-2 gene expression induced by nitric oxide synthase inhibitors and lipopolysaccharide. Biochem. Pharmacol., 61, 1417-1427 (2001) https://doi.org/10.1016/S0006-2952(01)00594-9
  2. Chi, Y. S., Cheon, B. S., and Kim, H. P. Effect of wogonin, a plant flavone from Scutellaria radix, on the suppression of cyclooxygenase-2 and the induction of inducible nitric oxide synthase in lopopolysaccharide-treated RAW 264.7 cells. Biochem. Pharmacol., 61, 1195-1203 (2001) https://doi.org/10.1016/S0006-2952(01)00597-4
  3. Chi, Y. S., Lim, H., Park, H., and Kim, H. P. Effects of woqonin., a plant flavone from Scutellaria radix, on skin inflammation: in vivo regulation of inflammation-associated gene expression. Biochem. Pharmacol., 66, 1271-1278 (2003) https://doi.org/10.1016/S0006-2952(03)00463-5
  4. Dao, T. T., Chi, Y. S., Kim, J., Kim, H. P., Kim, S., and Park, H. Synthesis and inhibitory activity against COX-2 catalyzed prostaglandin production of chrysin derivatives. BioOrg. Med. Chem. Lett., 14, 1165-1167 (2004) https://doi.org/10.1016/j.bmcl.2003.12.087
  5. Harbome, J. B., and Williams, C. A. Advances in f1avonoids research since 1992. Phytochemistry, 55, 481-504 (2000) https://doi.org/10.1016/S0031-9422(00)00235-1
  6. Kim, H., Kim, Y. S., Kim, S. Y., and Suk, K. The plant flavonoid wogonin suppresses death of activated C6 rat glial cell inhibiting nitric oxide production. Neurosci. Lett., 309(1), 67-71 (2001) https://doi.org/10.1016/S0304-3940(01)02028-6
  7. Lee, H., Kim, Y. O., Kim, H., Kim, S. Y., Noh, H. S., Kang, S. S., Cho, G. J., Choi, W. S., and Suk, K. Flavonoid wogonin from medicinal herb is neuroprotective by inhibiting inflammatory activation of microglia. FASEB J., 17, 1943-1944 (2003)
  8. Mossman, T. Rapid colorimetric asay 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
  9. Read, M. A. Flavonoids: naturally occurring anti-inflammatory agents. Am. J. Pathol., 147, 235-237 (1995)
  10. de Rossi, R. H., Veglia, A. V. On the product distribution in the iodination of phenol. Tetrahedron Lett., 27, 5963-5966 (1986) https://doi.org/10.1016/S0040-4039(00)85373-3
  11. Shieh, D. E., Liu, L. T., and Lin, C. C. Antioxidant and free radical scavenging effects of baicalein, baicalin and wogonin. Anticancer Res., 20(5A), 2861-2865 (2000)
  12. Suzuki, A. Recent advances in the cross-coupling reactions of organoboron derivatives with organic electrophiles, 1995-1998. J. Organometal Chem., 576, 147-168 (1999) https://doi.org/10.1016/S0022-328X(98)01055-9
  13. Wakabayashi, I. Inhibitory effects of baicalein and wogonin on lipopolysaccharide-induced nitric oxide production in macro-phages. Pharmacol. Toxicol., 84, 288-291 (1999) https://doi.org/10.1111/j.1600-0773.1999.tb01496.x
  14. Wakabayashi, I., and Yasui, K. Wogonin inhibits inducible prostaglandin $E_{2}$ production in marophages. Eur. J. Pharmacol., 406, 477-481 (2000) https://doi.org/10.1016/S0014-2999(00)00695-6