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Synthesis and in vitro evaluation of antifungal and cytotoxic activities of eugenol glycosides

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Abstract

Six eugenol glycosides were prepared in order to assess their antifungal activity against Candida species. They were synthesized by glycosylation of eugenol with the appropriate glycosyl bromides followed by deacetylation with sodium methoxide in methanol and were evaluated in vitro for their antifungal activity through a Mueller–Hinton broth microdilution method. The peracetyl glycoside (derivative 4) was the most promising one since it was able to inhibit growth of C. albicans, C. tropicalis and C. glabrata with IC50 values much lower than that of the prototype eugenol. Derivative 4 showed to be 160.0 and 3.4 times more potent than eugenol and fluconazole, respectively, against C. glabrata with low cytotoxity (selectivity index of 45). Moreover, it was possible to verify the positive effect of gluco configuration and lipophilicity on antifungal activity, since glucose peracetyl derivatives were more active than the free sugars of galacto configuration.

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Authors and Affiliations

  1. Centro Universitário de Lavras, Rua Padre José Poggel, 506, Lavras, MG, Brazil

    Thiago Belarmino de Souza & Marina Orlandi

  2. Instituto de Ciências Biomédicas, Universidade Federal de Alfenas, Rua Gabriel Monteiro da Silva, 700, Alfenas, Brazil

    Luiz Felipe Leomil Coelho, Luiz Cosme Cotta Malaquias, Amanda Latercia Tranches Dias, Roberta Ribeiro de Carvalho & Naiara Chaves Silva

  3. Faculdade de Ciências Farmacêuticas, Universidade Federal de Alfenas, Rua Gabriel Monteiro da Silva, 700, Alfenas, MG, Brazil

    Diogo Teixeira Carvalho

Authors
  1. Thiago Belarmino de Souza
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  2. Marina Orlandi
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  3. Luiz Felipe Leomil Coelho
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  4. Luiz Cosme Cotta Malaquias
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  5. Amanda Latercia Tranches Dias
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  6. Roberta Ribeiro de Carvalho
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  7. Naiara Chaves Silva
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  8. Diogo Teixeira Carvalho
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Correspondence to Diogo Teixeira Carvalho.

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de Souza, T.B., Orlandi, M., Coelho, L.F.L. et al. Synthesis and in vitro evaluation of antifungal and cytotoxic activities of eugenol glycosides. Med Chem Res 23, 496–502 (2014). https://doi.org/10.1007/s00044-013-0669-2

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  • DOI: https://doi.org/10.1007/s00044-013-0669-2

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