Synthesis of Industrially Useful Phenolic Compounds Esters by Means of Biocatalysts Obtained Along with Waste Fish Oil Utilization

Abstract

The purpose of the study was to utilize the waste fish oil after fish smoking process in Y. lipolytica yeast batch cultures in order to assess its valorization to whole-cell biocatalysts with lipolytic properties. Almost 90% of the waste carbon source in medium was used and batch cultures of Y. lipolytica W29 were characterized with biomass yield of 18.59 g/dm3 and lipolytic activity of 53.41 U/g. The yeast biomass was used as a whole-cell biocatalyst in the synthesis of esters of selected phenolic compounds (acetates of 2-phenylethanol, tyrosol (2-(4-hydroxyphenyl) ethanol) and 3-phenyl-1-propanol, and ethyl esters of phenylacetic, 4-hydroxyphenylacetic, 3-phenylpropanoic, and 3-(4-hydroxyphenyl) propanoic acids). Y. lipolytica biomass was able to catalyze esterification of 3-phenylpropanoic acid (conversion of 95% after 24 h), but conversion of other acids to their esters was very weak, and in the case of transesterification of aromatic alcohols with vinyl acetate, conversions were 27%–63% after 24 h. Synthesized esters were tested prior potential activities as food additives. Esters of hydroxylated phenolic compounds showed activity of 2.5 mg/mL against Klebsiella pneumoniae and Citrobacter freundii, exhibited similar antioxidant properties to their precursors, and were better soluble in lipids, which increases the possibility of their use in the food industry.

Use of Non-Conventional Yeast Yarrowia lipolytica in Treatment or Upgradation of Hydrophobic Industry Wastes

“…Zieniuk et al [19] compared four strains of Y. lipolytica in growth and intracellular lipases production in medium containing waste fish oil. Two of them, KKP 379 and W29 were able to grow and produce lipases at a satisfactory level, and the latter was used in bioreactor culture to obtain wholecell biocatalyst with lipolytic properties.…”

“…Some perspective processes have been developed to obtain a variety of products through biosynthesis with these microorganisms including erythritol, aromatic compounds e.g. γ-decalactone [19], carotenoidse.g. β-carotene [20], organic acids-α-ketoglutaric, succinic, citric and pyruvic acids [21], lipases-enzymes used in food production, for water purification or as an ingredient in detergents [22], SCP (Single Cell Protein)-proteins of microbiological origin that can be used as feed additives [23], SCO (Single Cell Oil)-microbiological oil which is a source of essential unsaturated fatty acids (EFA) with valuable properties for both humans and farm animals [5,24].…”

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.…”

“…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 ]. The approach has been presented in the current study that aimed to evaluate the effect of the substituent and its position in the aromatic ring on the antioxidant activity of hexanoic acid esters synthesized in reactions catalyzed by immobilized lipase B from Candida antarctica (CALB).…”

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

“…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 ).…”