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Chemical Compound Review

Scoparon     6,7-dimethoxychromen-2-one

Synonyms: Scoparone, Escoparone, PubChem13307, CHEMBL325864, Bio-0192, ...
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Disease relevance of Esculetin dimethyl ether


High impact information on Esculetin dimethyl ether


Chemical compound and disease context of Esculetin dimethyl ether


Biological context of Esculetin dimethyl ether


Anatomical context of Esculetin dimethyl ether


Associations of Esculetin dimethyl ether with other chemical compounds

  • The oxidative removal of two different methyl groups from scoparone by a cytochrome P-450-mediated reaction proceeds with greater velocity for the 6-methyl group than for the 7-methyl group [15].
  • Regioselective 7-demethylation of scoparone is regularly employed as an indicator of phenobarbital-like induction of rat liver cytochrome P450 isoform CYP2B1, e.g., by the antiepileptic drug phenytoin [9].
  • Emodin (3 x 10(-7)-10(-4) M) and scoparone (10(-6)-3 x 10(-4) M) also dose dependently suppressed the responses of human mononuclear cells to phytohemagglutinin and mixed lymphocyte reaction [16].
  • We compared the effect of scoparone on the mononuclear cell response to genistein, a specific inhibitor of protein tyrosine kinase and demonstrated the non-additivity and cross-desensitization of the two compounds [17].
  • No changes in the level of IP3 were detected in response to the treatment with the G-protein activators cholera toxin or mastoparan, although the HR was observed in response to these compounds as determined by the scoparone synthesis [18].

Gene context of Esculetin dimethyl ether

  • Moreover, scoparone also attenuated the production of tumor necrosis factor (TNF)-alpha, interleukin (IL)-1beta and IL-6 in LPS-stimulated RAW264.7 cells [19].
  • Scoparone from Artemisia capillaris inhibits the release of inflammatory mediators in RAW 264.7 cells upon stimulation cells by interferon-gamma Plus LPS [19].
  • These results suggest that scoparone decreases the production of the inflammatory mediators such as NO and PGE2 in macrophages by inhibiting iNOS and COX-2 expression [19].
  • Cyp2c29-dependent 6-demethylation of scoparone resulted in the formation of isoscopoletin, an intermediate which is susceptible to further oxidation [9].
  • The molecular mechanism by which scoparone inhibited iNOS gene expression appeared to involve the inhibition of NF-kappaB activation [4].

Analytical, diagnostic and therapeutic context of Esculetin dimethyl ether


  1. Transcriptional activation of cytochrome P450 CYP2C45 by drugs is mediated by the chicken xenobiotic receptor (CXR) interacting with a phenobarbital response enhancer unit. Baader, M., Gnerre, C., Stegeman, J.J., Meyer, U.A. J. Biol. Chem. (2002) [Pubmed]
  2. Identification of Mycobacterium tuberculosis and M. avium complex directly from smear-positive sputum specimens and BACTEC 12B cultures by high-performance liquid chromatography with fluorescence detection and computer-driven pattern recognition models. Jost, K.C., Dunbar, D.F., Barth, S.S., Headley, V.L., Elliott, L.B. J. Clin. Microbiol. (1995) [Pubmed]
  3. Scoparone inhibits PMA-induced IL-8 and MCP-1 production through suppression of NF-kappaB activation in U937 cells. Jang, S.I., Kim, Y.J., Kim, H.J., Lee, J.C., Kim, H.Y., Kim, Y.C., Yun, Y.G., Yu, H.H., You, Y.O. Life Sci. (2006) [Pubmed]
  4. Inhibition of cytokine-mediated nitric oxide synthase expression in rat insulinoma cells by scoparone. Kim, E.K., Kwon, K.B., Lee, J.H., Park, B.H., Park, J.W., Lee, H.K., Jhee, E.C., Yang, J.Y. Biol. Pharm. Bull. (2007) [Pubmed]
  5. Stimulation of melanogenesis by scoparone in B16 melanoma cells. Yang, J.Y., Koo, J.H., Song, Y.G., Kwon, K.B., Lee, J.H., Sohn, H.S., Park, B.H., Jhee, E.C., Park, J.W. Acta Pharmacol. Sin. (2006) [Pubmed]
  6. Morphological evidence for the antiatherogenic effect of scoparone in hyperlipidaemic diabetic rabbits. Chen, Y.L., Huang, H.C., Weng, Y.I., Yu, Y.J., Lee, Y.T. Cardiovasc. Res. (1994) [Pubmed]
  7. Biotransformation of scoparone used to monitor changes in cytochrome P450 activities in primary hepatocyte cultures derived from rats, hamsters and monkeys. Mennes, W.C., van Holsteijn, C.W., Timmerman, A., Noordhoek, J., Blaauboer, B.J. Biochem. Pharmacol. (1991) [Pubmed]
  8. Production of three O-methhylated esculetins with Escherichia coli expressing O-methyltransferase from poplar. Kim, B.G., Lee, Y., Hur, H.G., Lim, Y., Ahn, J.H. Biosci. Biotechnol. Biochem. (2006) [Pubmed]
  9. Oxidative hydrolysis of scoparone by cytochrome p450 CYP2C29 reveals a novel metabolite. Meyer, R.P., Hagemeyer, C.E., Knoth, R., Kurz, G., Volk, B. Biochem. Biophys. Res. Commun. (2001) [Pubmed]
  10. Scoparone inhibits tissue factor expression in lipopolysaccharide-activated human umbilical vein endothelial cells. Lee, Y.M., Hsiao, G., Chang, J.W., Sheu, J.R., Yen, M.H. J. Biomed. Sci. (2003) [Pubmed]
  11. Effects of various medium formulations and attachment substrata on the performance of cultured ruminant hepatocytes in biotransformation studies. van 't Klooster, G.A., Woutersen-van Nijnanten, F.M., Klein, W.R., Blaauboer, B.J., Noordhoek, J., van Miert, A.S. Xenobiotica (1992) [Pubmed]
  12. The effect of scoparone, a coumarin derivative isolated from the Chinese crude drug Artemisiae capillaris flos, on the heart. Yamahara, J., Kobayashi, G., Matsuda, H., Katayama, T., Fujimura, H. Chem. Pharm. Bull. (1989) [Pubmed]
  13. Biocontrol of aflatoxins B1, B2, G1, G2, and fumonisin B1 with 6,7-dimethoxycoumarin, a phytoalexin from Citrus sinensis. Mohanlall, V., Odhav, B. J. Food Prot. (2006) [Pubmed]
  14. Differences in the effects of model inducers of cytochrome P450 on the biotransformation of scoparone in rat and hamster liver. Mennes, W.C., Luijckx, N.B., Wortelboer, H.M., Noordhoek, J., Blaauboer, B.J. Arch. Toxicol. (1993) [Pubmed]
  15. Radioisomers of scoparone (6,7-dimethoxycoumarin) as a tool for in vivo differentiation of various hepatic monooxygenase inducers in mice using the breath test technique. Legrum, W., Kling, L., Funke, E. J. Pharmacol. Exp. Ther. (1984) [Pubmed]
  16. Vasorelaxants from Chinese herbs, emodin and scoparone, possess immunosuppressive properties. Huang, H.C., Chu, S.H., Chao, P.D. Eur. J. Pharmacol. (1991) [Pubmed]
  17. Possible mechanism of immunosuppressive effect of scoparone (6,7-dimethoxycoumarin). Huang, H.C., Huang, Y.L., Chang, J.H., Chen, C.C., Lee, Y.T. Eur. J. Pharmacol. (1992) [Pubmed]
  18. IP3 production in the hypersensitive response of lemon seedlings against Alternaria alternata involves active protein tyrosine kinases but not a G-protein. Ortega, X., Velásquez, J.C., Pérez, L.M. Biol. Res. (2005) [Pubmed]
  19. Scoparone from Artemisia capillaris inhibits the release of inflammatory mediators in RAW 264.7 cells upon stimulation cells by interferon-gamma Plus LPS. Jang, S., Kim, Y.J., Lee, W.Y., Kwak, K.C., Baek, S.H., Kwak, G.B., Yun, Y.G., Kwon, T.O., Chung, H.T., Chai, K.Y. Arch. Pharm. Res. (2005) [Pubmed]
  20. Mode of action of hot-water dip in reducing decay of lemon fruit. Nafussi, B., Ben-Yehoshua, S., Rodov, V., Peretz, J., Ozer, B.K., D'hallewin, G. J. Agric. Food Chem. (2001) [Pubmed]
  21. Pharmacokinetics of a novel anti-asthmatic, scoparone, in the rabbit serum assessed by a simple HPLC method. Fang, Y., Li, Z., Watanabe, Y. Journal of ethnopharmacology. (2003) [Pubmed]
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