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Chemical Compound Review

Allylveratrol     1,2-dimethoxy-4-prop-2-enyl- benzene

Synonyms: METHYLEUGENOL, LS-15, CCRIS 746, CHEMBL108861, SureCN113794, ...
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Disease relevance of Eugenol methyl ether


High impact information on Eugenol methyl ether


Chemical compound and disease context of Eugenol methyl ether

  • Methyleugenol (MEG) was tested for toxicity/carcinogenicity in a 2-yr carcinogenesis bioassay because of its widespread use in a variety of foods, beverages, and cosmetics as well as its structural resemblance to the known carcinogen safrole [2].
  • Three allylbenzenes from Asiasarum heterotropoides, methyleugenol (1), elemicin (2) and gamma-asaron (3) showed suppressive effects on umu gene expression of the SOS response in the Salmonella typhimurium OY1001/1A2 umu test against the mutagen 2-amino-3,4-dimethylimidazo[4,5-f ]quinoline (MeIQ) [8].

Biological context of Eugenol methyl ether


Anatomical context of Eugenol methyl ether

  • The rate of 1'-hydroxylation of methyleugenol in vitro in 13 human liver samples varied markedly (by 37-fold), with the highest activities being similar to the activity evident in control rat liver microsomes [7].
  • These findings imply that generation of protein adducts in livers of rats given methyleugenol in vivo proceeds via the 1'-hydroxy metabolite and requires crucial cofactors, and/or structural features, which are present in intact hepatocytes but not in broken cell preparations and which remain to be defined [11].
  • An additional experiment with Gentest microsomes, expressing the same individual enzymes to roughly average liver levels, indicated that P450 1A2, 2C9, 2C19, and 2D6 contribute to methyleugenol 1'-hydroxylation in the human liver [12].
  • The effects of methyleugenol (ME) on guinea-pig isolated ileum were studied [13].
  • We conclude that methyleugenol directly affect histamine release and HDC gene over-expression in mast cells [1].

Associations of Eugenol methyl ether with other chemical compounds


Gene context of Eugenol methyl ether


Analytical, diagnostic and therapeutic context of Eugenol methyl ether


  1. Suppression of L-histidine decarboxylase mRNA expression by methyleugenol. Shin, B.K., Lee, E.H., Kim, H.M. Biochem. Biophys. Res. Commun. (1997) [Pubmed]
  2. Two-year toxicity and carcinogenicity study of methyleugenol in F344/N rats and B6C3F(1) mice. Johnson, J.D., Ryan, M.J., Toft JD, I.I., Graves, S.W., Hejtmancik, M.R., Cunningham, M.L., Herbert, R., Abdo, K.M. J. Agric. Food Chem. (2000) [Pubmed]
  3. 14-Week toxicity and cell proliferation of methyleugenol administered by gavage to F344 rats and B6C3F1 mice. Abdo, K.M., Cunningham, M.L., Snell, M.L., Herbert, R.A., Travlos, G.S., Eldridge, S.R., Bucher, J.R. Food Chem. Toxicol. (2001) [Pubmed]
  4. Mutation of beta-catenin is an early event in chemically induced mouse hepatocellular carcinogenesis. Devereux, T.R., Anna, C.H., Foley, J.F., White, C.M., Sills, R.C., Barrett, J.C. Oncogene (1999) [Pubmed]
  5. Floral scent production in Clarkia breweri (Onagraceae). II. Localization and developmental modulation of the enzyme S-adenosyl-L-methionine:(iso)eugenol O-methyltransferase and phenylpropanoid emission. Wang, J., Dudareva, N., Bhakta, S., Raguso, R.A., Pichersky, E. Plant Physiol. (1997) [Pubmed]
  6. Unique patterns of gene expression changes in liver after treatment of mice for 2 weeks with different known carcinogens and non-carcinogens. Iida, M., Anna, C.H., Holliday, W.M., Collins, J.B., Cunningham, M.L., Sills, R.C., Devereux, T.R. Carcinogenesis (2005) [Pubmed]
  7. Cytochrome P450 mediated bioactivation of methyleugenol to 1'-hydroxymethyleugenol in Fischer 344 rat and human liver microsomes. Gardner, I., Wakazono, H., Bergin, P., de Waziers, I., Beaune, P., Kenna, J.G., Caldwell, J. Carcinogenesis (1997) [Pubmed]
  8. Suppression of MeIQ-induced SOS response by allylbenzenes from Asiasarum heterotropoides in the Salmonella typhimurium OY1001/1A2 umu test. Miyazawa, M., Kohno, G., Okuno, Y., Oda, Y. Nat. Prod. Res. (2006) [Pubmed]
  9. Cytotoxicity and genotoxicity of methyleugenol and related congeners-- a mechanism of activation for methyleugenol. Burkey, J.L., Sauer, J.M., McQueen, C.A., Sipes, I.G. Mutat. Res. (2000) [Pubmed]
  10. Determination of Final Steps in Biosyntheses of Essential Oil Components in Perilla frutescens. Nishizawa, A., Honda, G., Tabata, M. Planta Med. (1989) [Pubmed]
  11. Immunochemical detection of covalently modified protein adducts in livers of rats treated with methyleugenol. Gardner, I., Bergin, P., Stening, P., Kenna, J.G., Caldwell, J. Chem. Res. Toxicol. (1996) [Pubmed]
  12. Human cytochrome p450 enzymes of importance for the bioactivation of methyleugenol to the proximate carcinogen 1'-hydroxymethyleugenol. Jeurissen, S.M., Bogaards, J.J., Boersma, M.G., ter Horst, J.P., Awad, H.M., Fiamegos, Y.C., van Beek, T.A., Alink, G.M., Sudhölter, E.J., Cnubben, N.H., Rietjens, I.M. Chem. Res. Toxicol. (2006) [Pubmed]
  13. Relaxant and antispasmodic actions of methyleugenol on guinea-pig isolated ileum. Lima, C.C., Criddle, D.N., Coelho-de-Souza, A.N., Monte, F.J., Jaffar, M., Leal-Cardoso, J.H. Planta Med. (2000) [Pubmed]
  14. Phylogenetic relationships among Bactrocera species (Diptera: Tephritidae) inferred from mitochondrial DNA sequences. Smith, P.T., Kambhampati, S., Armstrong, K.A. Mol. Phylogenet. Evol. (2003) [Pubmed]
  15. Human consumption of methyleugenol and its elimination from serum. Schecter, A., Lucier, G.W., Cunningham, M.L., Abdo, K.M., Blumenthal, G., Silver, A.G., Melnick, R., Portier, C., Barr, D.B., Barr, J.R., Stanfill, S.B., Patterson, D.G., Needham, L.L., Stopford, W., Masten, S., Mignogna, J., Tung, K.C. Environ. Health Perspect. (2004) [Pubmed]
  16. Determination of methyleugenol in rodent plasma by high-performance liquid chromatography. Graves, S.W., Runyon, S. J. Chromatogr. B, Biomed. Appl. (1995) [Pubmed]
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