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

Abstract

Due to the increase in the consumption of highly processed food in developed countries, as well as, a growing number of foodborne diseases, exploration of new food additives is an issue focusing on scientific attention and industrial interest. Functional compounds with lipophilic properties are remarkably desirable due to the high susceptibility to the deterioration of lipid-rich food products. This paper in a comprehensive manner provides the current knowledge about the enzymatic synthesis of lipophilic components that could act as multifunctional food additives. The main goal of enzymatic lipophilization of compounds intentionally added to food is to make these substances soluble in lipids and/or to obtain environmentally friendly surfactants. Moreover, lipase-catalyzed syntheses could result in changes in the antioxidant and antimicrobial activities of phenolic compounds, carbohydrates, amino acids (oligopeptides), and carboxylic acids. The review describes also the implementation of a new trend in green chemistry, where apart from simple and uncomplicated chemical compounds, the modifications of multi-compound mixtures, such as phenolic extracts or essential oils have been carried out.

Keywords: Antimicrobial compounds; Food additives; Lipase; Lipase-catalyzed ester synthesis; Lipophilic antioxidants; Lipophilization.

Fig. 1

Examples of sugar esters obtained in lipase-catalyzed reactions: a trehalose laurate, b fructose laurate, c sucrose monolaurate

Fig. 2

The possibilities of lipase-catalyzed functionalization of the amino acids

Fig. 3

Chemical structure of bixin

Fig. 4

Chemical structures of enzymatically obtained ferulic acid derivatives: a hexyl ferulate, b L-arabinose ferulate, and c 1,3-diferuloyl-sn-glycerol

Fig. 5

Chemical structures of a erythorbyl laurate and b erythorbyl myristate

Fig. 6

Chemical structure of dilauryl azelate

Fig. 7

Chemical structures of a β-sitosteryl 4-hydroxybenzoate, b β-sitosteryl vanillate, and c β-sitosteryl ferulate

Fig. 8

Chemical structures of a andrographolide-14-propionate and b andrographolide-14-butanoate