Skip to main content
Log in

Antibacterial and mutagenic activities of new isothiocyanate derivatives

  • Papers
  • Published:
Folia Microbiologica Aims and scope Submit manuscript

Abstract

Nine newly synthetized isothiocyanate derivatives were demonstrated to posses antibacterial and genotoxic activitiesin vitro. 4-Hydroxybutyl isothiocyanate exhibited a broad antibacterial effect, with MIC values of 762 μmol/L forStaphylococcus aureus andEscherichia coli. Ethyl 4-methylsulfoxidobutanoate had the highest antibacterial activity in Gram-positive bacteria, the MIC value being 425 μmol/L forS. aureus. The highest tested concentrations of ethyl 4-isothiocyanatobutanoate and 4-hydroxybutyl isothiocyanate produced a bacteriocidal effect in Gram-positive bacteria. The compounds showed no mutagenic effects onSalmonella typhimurium tester strains TA 98 and TA 100, either in the absence or in the presence of a metabolically active microsomal S9 fraction from rat liver using standard Ames test.

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

  • Drobnica L'., Zemanová M., Nemec P., Antoš K., Kristián P., Stullerová A., Knoppová V., Nemec P. Jr.: Antifungal activity of isothiocyanates and related compounds. 1. Naturally occuring isothiocyanates and their analogues.Appl. Microbiol. 15, 701–709 (1967).

    PubMed  CAS  Google Scholar 

  • Fenwick G.R., Heaney R.K., Mullin W.J.: Glucosinolates and their breakdown products in food and food plants.Crit. Rev. Food Sci. Nutr. 18, 123–201 (1983).

    Article  PubMed  CAS  Google Scholar 

  • Floch L',will be published (2001).

  • Floch L'., Kováč S.: Synthesis and properties of alkyl isothiocyanatocarboxylates.Collect. Czechosl. Chem. Commun. 40, 2845–2854 (1975).

    CAS  Google Scholar 

  • Hecht S.S.: Chemoprevention by isothiocyanates.J. Cell Biochem. 22 (Suppl.), 195–209 (1995).

    Article  CAS  Google Scholar 

  • Horáková K., Drobnica L'., Nemec P.: Cytotoxic and cancerostatic effect of isothiocyanates and related compounds. VII. Effect of isothiocyanate chalkones on HeLa cells.Neoplasma 18, 355–359 (1971).

    PubMed  Google Scholar 

  • Horáková K., Straková Z., Jantová S., Múčková M., Floch L'.: Biological effects of 2-isothiocyanate carboxylic acid esters. 1. Cytotoxic, antimicrobial and genotoxic screening of amino acid isothiocyanate derivatives.Biologia 44, 637–646 (1989).

    Google Scholar 

  • Jantová S., Hudecová D., Stankovský S., Špirková K., Ružeková L'.: Antibacterial effect of substituted 4-quinazolylhydrazines and their arylhydrazones determined by modified microdilution method.Folia Microbiol. 40, 611–614 (1995).

    Article  Google Scholar 

  • Kawazoe Y., Kato M.: Antimutagenic effect of isocyanates and related compounds inEscherichia coli.Gann 73, 255–263 (1982).

    PubMed  CAS  Google Scholar 

  • Maron D.M., Ames B.N.: Revised methods for theSalmonella mutagenicity test.Mutat. Res. 112, 173–215 (1983).

    Google Scholar 

  • Neudecker T., Henschler D.: Allyl isothiocyanate is mutagenic inSalmonella typhimurium.Mutat. Res. 156, 33–37 (1985).

    Article  PubMed  CAS  Google Scholar 

  • Ono H., Tesaki S., Tanabe S., Watanabe M.: 6-Methylsulfinylhexyl isothiocyanate and its homologues as food-originated compounds with antibacterial activity againstEscherichia coli andStaphylococcus aureus.Biosci. Biotechnol. Biochem. 62, 363–365 (1998).

    Article  PubMed  CAS  Google Scholar 

  • Říhová E.: Mutagenic effects of allylisothiocyanate inEscherichia coli WP 67.Folia Microbiol. 27, 25–31 (1982).

    Google Scholar 

  • Saksena N.K.: Fungicidal action and structure correlation of monosubstituted phenyl isothiocyanates.Folia Microbiol. 30, 359–362 (1985).

    Article  CAS  Google Scholar 

  • Tajima H., Li G.: Synthesis of hydroxyallyl isothiocyanates.Synlett 7, 773–774 (1997).

    Article  Google Scholar 

  • Tajima H., Kimoto H., Taketo Y., Taketo A.: Effects of synthetic hydroxy isothiocyanates on microbial systems.Biosci. Biotechnol. Biochem. 62, 491–495 (1998).

    Article  PubMed  CAS  Google Scholar 

  • Talalay P., Zhang Y.: Chemoprotection against cancer by isothiocyanates and glucosinolates.Biochem. Soc. Trans. 24, 806–810 (1996).

    PubMed  CAS  Google Scholar 

  • Verhoeven D.T., Goldbohm R.A., Van Poppel G., Verhagen H., Van Den Brandt P.A.: Epidemiological studies on brassica vegetables and cancer risk.Cancer Epidemiol. Biomark Prev. 5, 733–748 (1996).

    CAS  Google Scholar 

  • Zhang Y., Talalay P.: Mechanism of differential potencies of isothiocyanates as inducers of anticarcinogenic Phase 2 enzymes.Cancer Res. 58, 4632–4639 (1998).

    PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Šovčíková, A., Mikulášová, M., Horáková, K. et al. Antibacterial and mutagenic activities of new isothiocyanate derivatives. Folia Microbiol 46, 113–117 (2001). https://doi.org/10.1007/BF02873587

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02873587

Keywords

Navigation