Medicinal Chemistry Research p. 496 - 502 (2014)
Update date:2022-08-04
Topics: Synthesis Antifungal Cytotoxic In vitro Glycosides Eugenol
De Souza, Thiago Belarmino
Orlandi, Marina
Coelho, Luiz Felipe Leomil
Malaquias, Luiz Cosme Cotta
Dias, Amanda Latercia Tranches
De Carvalho, Roberta Ribeiro
Silva, Naiara Chaves
Carvalho, Diogo Teixeira
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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