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Chemical Compound Review

Brevifolin     1-(2-hydroxy-4,6-dimethoxy- phenyl)ethanone

Synonyms: Xanthoxylin, Xanthoxyline, SPECTRUM200441, SureCN44708, CHEMBL450288, ...
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High impact information on NSC17392


Biological context of NSC17392


Anatomical context of NSC17392

  • Xanthoxyline (30 to 300 microM) inhibited contractions of the rat uterus, guinea-pig ileum, and urinary bladder induced by several agonists in a non-competitive, non-selective, concentration-related manner, with the IC50's ranging between 47 and 190 microM [2].
  • Therefore, it appears that xanthoxyline induces a direct and non-selective inhibition of contractions triggered by agonists or electrical stimulation of smooth and cardiac muscle preparations [2].
  • Successive purification of the extract from Canarium album and Euphorbia nematocypha, guided by antihepatotoxic activity in primary cultured rat hepatocytes, led to the isolation of brevifolin (1), hyperin (2), ellagic acid (3) and 3,3'-di-O-methylellagic acid (4) as hepatoprotective compounds [4].

Associations of NSC17392 with other chemical compounds

  • Four new megastigmane glucosides, named macarangiosides A-D (2-5), together with mallophenol B, lauroside E, methyl brevifolin carboxylate, and hyperin and isoquercitrin as a mixture were isolated from the leaves of Macaranga tanarius (L.) MULL.-ARG [5].
  • Chalcones and chalcone-like compounds, most of them new ones, prepared by base-catalyzed condensation of appropriate aldehydes and xanthoxyline, were tested for antifungal properties against a panel of yeasts, hialohyphomycetes as well as dermatophytes with the agar dilution assay [6].

Gene context of NSC17392

  • Aldose reductase (AR) inhibitory activity-directed fractionation of the 70% ethanolic extract of Para-parai mí, Phyllanthus niruri, has led to the isolation of three active components, ellagic acid (1), brevifolin carboxylic acid (4) and ethyl brevifolin carboxylate (5) [7].


  1. Antispasmodic activity of xanthoxyline derivatives: structure-activity relationships. Cechinel Filho, V., Miguel, O.G., Nunes, R.J., Calixto, J.B., Yunes, R.A. Journal of pharmaceutical sciences. (1995) [Pubmed]
  2. Action of 2-hydroxy-4,6-dimethoxyacetophenone isolated from Sebastiania schottiana. Calixto, J.B., Miguel, O.G., Yunes, R.A., Rae, G.A. Planta Med. (1990) [Pubmed]
  3. Molecular structure and QSAR study on antispasmodic activity of some xanthoxyline derivatives. dos Santos, R., Kuhnen, C.A., Yunes, R.A. Arch. Pharm. (Weinheim) (2006) [Pubmed]
  4. Hepatoprotective compounds from Canarium album and Euphorbia nematocypha. Ito, M., Shimura, H., Watanabe, N., Tamai, M., Hanada, K., Takahashi, A., Tanaka, Y., Arai, K., Zhang, P.L., Chang, R. Chem. Pharm. Bull. (1990) [Pubmed]
  5. Radical-Scavenging Activities of New Megastigmane Glucosides from Macaranga tanarius (L.) MULL.-ARG. Matsunami, K., Takamori, I., Shinzato, T., Aramoto, M., Kondo, K., Otsuka, H., Takeda, Y. Chem. Pharm. Bull. (2006) [Pubmed]
  6. Antifungal activity and studies on mode of action of novel xanthoxyline-derived chalcones. Boeck, P., Leal, P.C., Yunes, R.A., Filho, V.C., López, S., Sortino, M., Escalante, A., Furlán, R.L., Zacchino, S. Arch. Pharm. (Weinheim) (2005) [Pubmed]
  7. Studies on aldose reductase inhibitors from natural products. II. Active components of a Paraguayan crude drug "Para-parai mí," Phyllanthus niruri. Shimizu, M., Horie, S., Terashima, S., Ueno, H., Hayashi, T., Arisawa, M., Suzuki, S., Yoshizaki, M., Morita, N. Chem. Pharm. Bull. (1989) [Pubmed]
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