Abstract
ObjectiveThe 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.ResultsFreeze-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.ConclusionsLipophilization of phenolic acids achieved by enzymatic esterification creates prospects for using these compounds as food additives with antioxidant properties in lipid-rich food matrices.
Highlights
Free radicals are atoms, ions, or molecules with one or more unpaired electrons capable of independent existence
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
Antioxidant food additives permitted for use within the European Union are ascorbic acid, and its salts, esters, and tocopherols, as well as propyl gallate, tert-butylhydroquinone (TBHQ), butylated hydroxyanisole (BHA), and butylated hydroxytoluene (BHT) (Silva and Lidon 2016) (Fig. 1)
Summary
Ions, or molecules with one or more unpaired electrons capable of independent existence. Lipophilic antioxidants synthesized by biotechnological methods are gaining popularity This method usually involves enzymatic esterification of suitable compounds with high antioxidant activity and a lipophilic moiety (fatty acid or long-chain alcohol), resulting in lipid-soluble esters that inhibit oxidation of food components, as in the case of fatty acid esters of ascorbic acid (Viklund et al 2003) or alkyl esters of phenolic acids (BiałeckaFlorjanczyk et al 2018). Yarrowia lipolytica yeast is capable of producing many metabolites of application importance, especially hydrolytic enzymes such as lipases, proteases, phosphatases, or RNases (Zieniuk and Fabiszewska 2019). It produces many other valuable compounds with high biological activity. Enzymatic synthesis methods open new ways of producing valuable products under mild conditions in contrast to traditional chemical methods (Pradima et al 2017)
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