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Chemical Compound Review

Shikimol     5-prop-2-enylbenzo[1,3]dioxole

Synonyms: Shikomol, Safrene, Sassafras, Shikimole, safrole, ...
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Disease relevance of safrole


Psychiatry related information on safrole


High impact information on safrole

  • At 24 weeks after initiation of safrole treatment, foci of enzyme-altered hepatocytes were noted [2].
  • In both maternal and fetal tissues, safrole exhibited preferential binding to liver DNA [4].
  • As safrole-DNA adducts have been detected in 77% (23/30) of the OSCC tissues from Taiwanese oral cancer patients with a BQ chewing history, we cannot rule out the possibility that safrole or other carcinogens present in the BQ may cause a similar pattern of mutagenesis [6].
  • Determination of the role of safrole and other carcinogens present in BQ on the pattern of p53 gene mutation in OSCC will require further study [6].
  • These results show that safrole is a genotoxic carcinogen in the rat liver in vivo and suggest that the cytogenetic effects of this compound may result from covalent DNA modification in the rat liver [7].

Chemical compound and disease context of safrole


Biological context of safrole


Anatomical context of safrole

  • These findings indicate that the functional pineal gland plays an important role in oncostatic actions of carcinogens such as safrole [16].
  • The 1'-hydroxylation of safrole was characterized in a variety of in vitro test systems, including Supersomes, expressing individual human P450 enzymes to a high level, and microsomes derived from cell lines expressing individual human P450 enzymes to a lower, average human liver level [5].
  • Additionally, a correlation study was performed, in which safrole was incubated with a series of 15 human liver microsomes, and the 1'-hydroxylation rates obtained were correlated with the activities of these microsomes toward specific substrates for nine different isoenzymes [5].
  • To identify the main cytochrome P450 (P450) involved in human hepatic safrole 1'-hydroxylation (SOH), we determined the SOH activities of human liver microsomes and Escherichia coli membranes expressing bicistronic human P450s [17].
  • Collectively, the data suggest that in PC3 cells, safrole induced a [Ca2+]i increase by causing Ca2+ release from the endoplasmic reticulum in a phospholipase C- and protein kinase C-independent fashion, and by inducing Ca2+ influx [18].

Associations of safrole with other chemical compounds


Gene context of safrole


Analytical, diagnostic and therapeutic context of safrole


  1. Biology of hepatocellular neoplasia in the mouse. I. Histogenesis of safrole-induced hepatocellular carcinoma. Lipsky, M.M., Hinton, D.E., Klaunig, J.E., Trump, B.F. J. Natl. Cancer Inst. (1981) [Pubmed]
  2. Biology of hepatocellular neoplasia in the mouse. II. Sequential enzyme histochemical analysis of BALB/c mouse liver during safrole-induced carcinogenesis. Lipsky, M.M., Hinton, D.E., Klaunig, J.E., Goldblatt, P.J., Trump, B.F. J. Natl. Cancer Inst. (1981) [Pubmed]
  3. In vitro assays for recombinogenic activity of chemical carcinogens and related compounds with Saccharomyces cerevisiae D3. Simmon, V.F. J. Natl. Cancer Inst. (1979) [Pubmed]
  4. 32P-postlabeling assay in mice of transplacental DNA damage induced by the environmental carcinogens safrole, 4-aminobiphenyl, and benzo(a)pyrene. Lu, L.J., Disher, R.M., Reddy, M.V., Randerath, K. Cancer Res. (1986) [Pubmed]
  5. Human cytochrome p450 enzyme specificity for bioactivation of safrole to the proximate carcinogen 1'-hydroxysafrole. Jeurissen, S.M., Bogaards, J.J., Awad, H.M., Boersma, M.G., Brand, W., Fiamegos, Y.C., van Beek, T.A., Alink, G.M., Sudhölter, E.J., Cnubben, N.H., Rietjens, I.M. Chem. Res. Toxicol. (2004) [Pubmed]
  6. Characteristics of mutations in the p53 gene in oral squamous cell carcinoma associated with betel quid chewing and cigarette smoking in Taiwanese. Hsieh, L.L., Wang, P.F., Chen, I.H., Liao, C.T., Wang, H.M., Chen, M.C., Chang, J.T., Cheng, A.J. Carcinogenesis (2001) [Pubmed]
  7. In vivo genotoxicity and DNA adduct levels in the liver of rats treated with safrole. Daimon, H., Sawada, S., Asakura, S., Sagami, F. Carcinogenesis (1998) [Pubmed]
  8. Independent [Ca2+]i increases and cell proliferation induced by the carcinogen safrole in human oral cancer cells. Huang, J.K., Huang, C.J., Chen, W.C., Liu, S.I., Hsu, S.S., Chang, H.T., Tseng, L.L., Chou, C.T., Chang, C.H., Jan, C.R. Naunyn Schmiedebergs Arch. Pharmacol. (2005) [Pubmed]
  9. Comparative evaluation of different pairs of DNA repair-deficient and DNA repair-proficient bacterial tester strains for rapid detection of chemical mutagens and carcinogens. Suter, W., Jaeger, I. Mutat. Res. (1982) [Pubmed]
  10. Risks associated with consumption of herbal teas. Manteiga, R., Park, D.L., Ali, S.S. Reviews of environmental contamination and toxicology. (1997) [Pubmed]
  11. Manganese toxicity in soil for Eisenia fetida, Enchytraeus crypticus (Oligochaeta), and Folsomia candida (Collembola). Kuperman, R.G., Checkai, R.T., Simini, M., Phillips, C.T. Ecotoxicol. Environ. Saf. (2004) [Pubmed]
  12. Altered fidelity of a nucleic acid modifying enzyme, T4 polynucleotide kinase, by safrole-induced DNA damage. Randerath, K., Gupta, K.P., van Golen, K.L. Carcinogenesis (1993) [Pubmed]
  13. Induction of three histochemically distinct populations of hepatic foci in C57BL/6J mice. Hanigan, M.H., Winkler, M.L., Drinkwater, N.R. Carcinogenesis (1993) [Pubmed]
  14. Upregulating of Fas, integrin beta4 and P53 and depressing of PC-PLC activity and ROS level in VEC apoptosis by safrole oxide. Zhao, J., Miao, J., Zhao, B., Zhang, S. FEBS Lett. (2005) [Pubmed]
  15. Evidence that 4-allyl-o-quinones spontaneously rearrange to their more electrophilic quinone methides: potential bioactivation mechanism for the hepatocarcinogen safrole. Bolton, J.L., Acay, N.M., Vukomanovic, V. Chem. Res. Toxicol. (1994) [Pubmed]
  16. Both physiological and pharmacological levels of melatonin reduce DNA adduct formation induced by the carcinogen safrole. Tan, D., Reiter, R.J., Chen, L.D., Poeggeler, B., Manchester, L.C., Barlow-Walden, L.R. Carcinogenesis (1994) [Pubmed]
  17. Identification of the main human cytochrome P450 enzymes involved in safrole 1'-hydroxylation. Ueng, Y.F., Hsieh, C.H., Don, M.J., Chi, C.W., Ho, L.K. Chem. Res. Toxicol. (2004) [Pubmed]
  18. Safrole-induced Ca2+ mobilization and cytotoxicity in human PC3 prostate cancer cells. Chang, H.C., Cheng, H.H., Huang, C.J., Chen, W.C., Chen, I.S., Liu, S.I., Hsu, S.S., Chang, H.T., Wang, J.K., Lu, Y.C., Chou, C.T., Jan, C.R. J. Recept. Signal Transduct. Res. (2006) [Pubmed]
  19. Multiplicity of induction patterns of rat liver microsomal mono-oxygenases and other polypeptides produced by administration of various xenobiotics. Sharma, R.N., Cameron, R.G., Farber, E., Griffin, M.J., Joly, J.G., Murray, R.K. Biochem. J. (1979) [Pubmed]
  20. The role of the neurohormone melatonin as a buffer against macromolecular oxidative damage. Reiter, R.J. Neurochem. Int. (1995) [Pubmed]
  21. Genotoxic effects of eugenol, isoeugenol and safrole in the wing spot test of Drosophila melanogaster. Munerato, M.C., Sinigaglia, M., Reguly, M.L., de Andrade, H.H. Mutat. Res. (2005) [Pubmed]
  22. Inhibition of human cytochrome P450 enzymes by the natural hepatotoxin safrole. Ueng, Y.F., Hsieh, C.H., Don, M.J. Food Chem. Toxicol. (2005) [Pubmed]
  23. Suppressing Akt phosphorylation and activating Fas by safrole oxide inhibited angiogenesis and induced vascular endothelial cell apoptosis in the presence of fibroblast growth factor-2 and serum. Zhao, J., Miao, J., Zhao, B., Zhang, S., Yin, D. Int. J. Biochem. Cell Biol. (2006) [Pubmed]
  24. Biology of hepatocellular neoplasia in the mouse. III. Electron microscopy of safrole-induced hepatocellular adenomas and hepatocellular carcinomas. Lipsky, M.M., Hinton, D.E., Klaunig, J.E., Trump, B.F. J. Natl. Cancer Inst. (1981) [Pubmed]
  25. 32P-post-labelling analysis of DNA adducts formed in the livers of animals treated with safrole, estragole and other naturally-occurring alkenylbenzenes. I. Adult female CD-1 mice. Randerath, K., Haglund, R.E., Phillips, D.H., Reddy, M.V. Carcinogenesis (1984) [Pubmed]
  26. Abuse of nutmeg (Myristica fragrans Houtt.): studies on the metabolism and the toxicologic detection of its ingredients elemicin, myristicin, and safrole in rat and human urine using gas chromatography/mass spectrometry. Beyer, J., Ehlers, D., Maurer, H.H. Therapeutic drug monitoring. (2006) [Pubmed]
  27. Determination of safrole, dihydrosafrole, and chloromethyldihydrosafrole in piperonyl butoxide by high-performance liquid chromatography. Schreiber-Deturmeny, E.M., Pauli, A.M., Pastor, J.L. Journal of pharmaceutical sciences. (1993) [Pubmed]
  28. Antimycobacterial compounds from Piper sanctum. Mata, R., Morales, I., Pérez, O., Rivero-Cruz, I., Acevedo, L., Enriquez-Mendoza, I., Bye, R., Franzblau, S., Timmermann, B. J. Nat. Prod. (2004) [Pubmed]
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