engleski

A comparative study on the antioxidant and biological activities of carvacrol, thymol and eugenol derivatives

Four derivatives of thymol, carvacrol, and eugenol were synthesized: 4-(hydroxymethyl)-5-isopropyl- 2-methylphenol, 4, 4′ -methylenebis(5-isopropyl-2-methyl)phenol, 4-allyl-6-(hydroxymethyl)-2-methox- yphenol, and 4-(hydroxymethyl)-2-isopropyl-5-methylphenol. The obtained derivatives showed remarkably better antioxidative properties according to 1, 1-diphenyl-2-picrylhydrazyl assay (50% inhibitory concentrations ) 4– 156 µ ; g/mL) and Rancimat assay (protection factors ) 1.55– 5.84) when compared with parent compounds and values similar to or better than those of butylated hydroxy- toluene and vitamin C. At concentrations of 10 mM carvacrol derivatives had no toxic effect on viability of Escherichia coli K-12 (determined by minimum inhibitory concentrations). Other phenol derivatives showed reduced cytotoxic effect on E. coli K-12 at concentrations of 2– 5 mM on the basis of 50% lethal dose measurements. In comparison with the parent compounds, phenol derivatives showed reduced cytotoxic effect for Saccharomyces cerevisiae cells (determined by yeast colony reduction). On the other hand, the majority of synthesized compounds had dose-dependent antiproliferative effects on human uterine carcinoma cells (HeLa), which makes them potentially interesting for the adjuvant experimental cancer treatments. The 4, 4′ -methylenebis(5-isopropyl-2-methyl)phenol derivative of carvacrol showed lower inhibiting capacity also for the HeLa cells, which makes this particular derivative attractive as an effi cient antioxidant with negligible cytotoxic effects.

Carvacrol; eugenol; thymol; hydroxymethyl derivatives; diarylmethane derivative; antioxidant activity; antiproliferative activity; antimicrobial activity; antiyeast activity

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