Skip to main content
Log in

Synthesis and PGE2 inhibitory activity of vinylated and allylated chrysin analogues

  • Published:
Archives of Pharmacal Research Aims and scope Submit manuscript

Abstract

Vinylated and allylated chrysin analogues were prepared as congeners of prenylated flavonoids and evaluated their anti-inflammatory activity. 8-Substituted chrysin analogues were prepared from 2’-hydroxy-3’-iodo-4’,6’-dimethoxyacetophenone in 3 steps. 3-Allylated chrysin analogues were prepared from chrysin in 3 steps. Synthesized chrysin analogues (4, 5 and8) showed moderate inhibitory activities of PGE2 production from LPS-induced RAW 264.7 cells.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  • Cheon, B.-S., Kim, Y. H., Son, K. H., Chang, H. W., Kang, S. S., and Kim, H. P., Effects of prenylated flavonoids and biflavonoids on lipopolysaccharide-induced nitric oxide production from the mouse macrophage cell line RAW 264.7.Planta Medica, 66, 596–600 (2000).

    Article  PubMed  CAS  Google Scholar 

  • 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).

    Article  PubMed  CAS  Google Scholar 

  • Gabor, M., Anti-inflammatory and antiallergy properties of flavonoids. InPlant Flavonoids in Biology and Medicine: Biochemical, Pharmacological, and Structure-Activity Relationships; Alan R. Liss: New York, 1986; p 471–480.

    Google Scholar 

  • Kim, H. K., Cheon, B. S. Kim, Y. H., Kim, S. Y., and Kim, H. P., Effects of naturally occurring flavonoids on nitric oxide production in the macrophage cell line RAW 264.7 and their structural-activity relationships.Biochem. Pharmacol., 58, 759–765 (1999).

    Article  PubMed  CAS  Google Scholar 

  • Kim, H. P., Son, K. H., Chang, H. W., and Kang, S. S. Effects of naturally occurring flavonoids on inflammatory responses and their action mechanism.Nat. Prod. Sci., 6, 170–178 (2000).

    Google Scholar 

  • Kosmeder, J. W., Moriarty, R. M., Pezzuto, J. M., Song, L. L., and Moon, R. C., Use of 4-bromoflavone in a cancer chemopreventative composition and method. US Patent 6, 046,231, 2000.

  • Lewis, D. A., Anti-inflammatory drugs from plant and marine sources. Inflavonoids; Berkhauser Verlag: Basel, Suppl. 27, p. 137–165, 1989.

    Google Scholar 

  • Nakazawa, K., Syntheses of nuclear-substituted flavonoids and allied compounds. IX. Syntheses of tetramethyl ether and dimethyl ether of Ginkgetin.Chem. Pharm. Bull., 10, 1032–1038 (1962).

    CAS  Google Scholar 

  • Needleman, P. and Isakson, P., The discovery and function of COX-2.J. Rhematol., 24 (Suppl. 49), 6–8 (1997).

    Google Scholar 

  • Strichtenoth, D. O. and Frolich, J. C., Nitric oxide and inflammatory joint diseases.Br. J. Rheumatol., 37, 246–257 (1998).

    Article  Google Scholar 

  • Reddy, G. R., Ueda, N., Hada, T., Sackeyfio, A. C., Yamamoto, S., and Hano, Y. et al., A prenylflavone, artonin E, as arachidonate 5-lipoxygenase inhibitor.Biochem. Pharmacol., 41, 115–118 (1991).

    Article  PubMed  CAS  Google Scholar 

  • Stille, J. K., The palladium-catalyzed cross-coupling reactions of organotin reagents with organic electrophiles.Angew. Chem. Int. Ed. Engl., 25, 508–524 (1986).

    Article  Google Scholar 

  • Yasukawa, K., Takido, M., Takeuchi, M., and Nakagawa, S., Effect of chemical constituents from plants on 12-O-tertra-decanoylphorbol-13-acetatate-induced inflammation in mice.Chem. Pharm. Bull., 37, 1071–1073 (1989).

    PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Haeil Park.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Dao, T.T., Oh, J.W., Chi, Y.S. et al. Synthesis and PGE2 inhibitory activity of vinylated and allylated chrysin analogues. Arch Pharm Res 26, 581–584 (2003). https://doi.org/10.1007/BF02976703

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02976703

Key words

Navigation