Application of freeze-dried Yarrowia lipolytica biomass in the synthesis of lipophilic antioxidants

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.

Yarrowia lipolytica Yeast: A Treasure Trove of Enzymes for Biocatalytic Applications—A Review

“…Over the last 30 years, Y. lipolytica yeast has been utilized for various applications, including the production of biodiesel [42], oils and fats processing [43], biosynthesis of aromas, antimicrobial or antioxidant esters [32,[44][45][46][47][48][49], as well as polymer degradation [50,51].…”

Recent advances in the enzymatic synthesis of lipophilic antioxidant and antimicrobial compounds

“…Elongation of the alkyl chain resulted in a decrease in the scavenging activity in the DPPH assay, and the opposite results were achieved in the β-carotene bleaching test. Zieniuk et al ( 2020 , 2021a , 2021c ) studied the synthesis, antioxidant and antimicrobial properties of different esters of phenolic compounds—phenylacetic and phenylpropanoic acids, their derivatives and analogues. Besides using CALB, Yarrowia lipolytica biomass was used as biocatalyst.…”

“…This approach is described as a strong trend in food of the future (Sun et al 2021 ). The commercialization of compounds acting as food additives is also facilitated via biocatalysis and processes such as esterification or general enzymatic reactions occurring under milder conditions, with the generation of fewer by-products (Zieniuk et al 2020 , 2021c ).…”

Enzymatic Synthesis of Lipophilic Esters of Phenolic Compounds, Evaluation of Their Antioxidant Activity and Effect on the Oxidative Stability of Selected Oils

“…Biocatalysis provides opportunities for the sustainable production of chemical compounds with interesting features, which can possibly be commercialized as food additives [9,10]. Esterification of phenolic compounds is the primary method of their modification; moreover, the use of enzymes to catalyze these reactions has many advantages in comparison with conventional chemical synthesis.…”

“…Esterification of phenolic compounds is the primary method of their modification; moreover, the use of enzymes to catalyze these reactions has many advantages in comparison with conventional chemical synthesis. Enzyme-catalyzed reactions are carried out in milder conditions; fewer by-products are generated and they are environmental-friendly [10]. Different esters of phenolic compounds are used in the food or cosmetic industry and esterification improves their biological activity [4,9].…”