Bartłomiej Zieniuk1, Małgorzata Wołoszynowska2, Ewa Białecka-Florjańczyk3, Agata Fabiszewska3. 1. Department of Chemistry, Institute of Food Sciences, Warsaw University of Life Sciences, 159c Nowoursynowska St., 02-776, Warsaw, Poland. bartlomiej_zieniuk@sggw.pl. 2. Analytical Department, Łukasiewicz Research Network - Institute of Industrial Organic Chemistry, 6 Annopol St., 03-236, Warsaw, Poland. 3. Department of Chemistry, Institute of Food Sciences, Warsaw University of Life Sciences, 159c Nowoursynowska St., 02-776, Warsaw, Poland.
Abstract
OBJECTIVE: The aim of the study was to evaluate the possibility of using Y. lipolytica biomass as a whole-cell catalyst in the synthesis of lipophilic antioxidants, with the example of esterification of five phenolic acids with 1-butanol. RESULTS: Freeze-dried Y. lipolytica biomass was successfully applied as a biocatalyst in the synthesis of esters of phenylpropanoic acid derivatives with 75-98% conversion. However, in the case of phenylacetic acid derivatives, results below 10% were obtained. The biological activity of phenolic acid esters was strongly associated with their chemical structures. Butyl 3-(4-hydroxyphenyl)propanoate showed an IC50 value of 19 mg/ml (95 mM) and TEAC value of 0.427. Among the compounds tested, butyl esters of 3-(4-hydroxyphenyl)propanoic and 4-hydroxyphenylacetic acids exhibited the highest antifungal activity. CONCLUSIONS: Lipophilization of phenolic acids achieved by enzymatic esterification creates prospects for using these compounds as food additives with antioxidant properties in lipid-rich food matrices.
OBJECTIVE: The aim of the study was to evaluate the possibility of using Y. lipolytica biomass as a whole-cell catalyst in the synthesis of lipophilic antioxidants, with the example of esterification of five phenolic acids with 1-butanol. RESULTS: Freeze-dried Y. lipolytica biomass was successfully applied as a biocatalyst in the synthesis of esters of phenylpropanoic acid derivatives with 75-98% conversion. However, in the case of phenylacetic acid derivatives, results below 10% were obtained. The biological activity of phenolic acid esters was strongly associated with their chemical structures. Butyl 3-(4-hydroxyphenyl)propanoate showed an IC50 value of 19 mg/ml (95 mM) and TEAC value of 0.427. Among the compounds tested, butyl esters of 3-(4-hydroxyphenyl)propanoic and 4-hydroxyphenylacetic acids exhibited the highest antifungal activity. CONCLUSIONS: Lipophilization of phenolic acids achieved by enzymatic esterification creates prospects for using these compounds as food additives with antioxidant properties in lipid-rich food matrices.
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