Medicinal Chemistry Research

, Volume 23, Issue 1, pp 496–502

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

  • Thiago Belarmino de Souza
  • Marina Orlandi
  • Luiz Felipe Leomil Coelho
  • Luiz Cosme Cotta Malaquias
  • Amanda Latercia Tranches Dias
  • Roberta Ribeiro de Carvalho
  • Naiara Chaves Silva
  • Diogo Teixeira Carvalho
Original Research

DOI: 10.1007/s00044-013-0669-2

Cite this article as:
de Souza, T.B., Orlandi, M., Coelho, L.F.L. et al. Med Chem Res (2014) 23: 496. doi:10.1007/s00044-013-0669-2

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.

Keywords

Eugenol derivativesGlycosidesAnti-Candida activity

Supplementary material

44_2013_669_MOESM1_ESM.pdf (382 kb)
Supplementary material 1 (PDF 381 kb)

Copyright information

© Springer Science+Business Media New York 2013

Authors and Affiliations

  • Thiago Belarmino de Souza
    • 1
  • Marina Orlandi
    • 1
  • Luiz Felipe Leomil Coelho
    • 2
  • Luiz Cosme Cotta Malaquias
    • 2
  • Amanda Latercia Tranches Dias
    • 2
  • Roberta Ribeiro de Carvalho
    • 2
  • Naiara Chaves Silva
    • 2
  • Diogo Teixeira Carvalho
    • 3
  1. 1.Centro Universitário de LavrasLavrasBrazil
  2. 2.Instituto de Ciências BiomédicasUniversidade Federal de AlfenasAlfenasBrazil
  3. 3.Faculdade de Ciências FarmacêuticasUniversidade Federal de AlfenasAlfenasBrazil