Synthesis and Characterization of Phenolic Lipids

Abstract

Omega-3 polyunsaturated faty acids (ω3 PUFAs) from ish oils promote well-established health and antiaging beneits that justify their use as functional ingredients in dietary supplements, healthy foods, and nutraceutical products. Dietary supply is needed because human metabolism exhibits limited to synthesize ω3 PUFAs. However, the practical use of such lipids as food ingredients is often limited due to their high susceptibility to oxidation, which is responsible for the undesirable of-lavor and odor of rancid oils, associated with the loss of nutritional value. Produced phenolic lipids were a good solution for all these problems. These phenolic lipids are preferentially produced by enzymatic bioprocesses that exhibit high selectivity toward polyfunctional substrates and mild reaction conditions compared with chemical synthesis pathways. This chapter presents the acylation of phenolic compounds and lipids using enzyme under various operating conditions. In conclusion, the acylation of lipids with natural phenolic compounds resulted in the formation of a lipophilic ester that should be able to stabilize the oil, fats, and emulsions against oxidation. Acylation of lipids to phenolic compounds that have antioxidant properties thus protects the lipids from oxidation, and the phenolic lipid derivatives carry the combined health beneicial properties of lipids and the phenolic molecules.

Green Synthesized Magnetic Nanoparticles as Effective Nanosupport for the Immobilization of Lipase: Application for the Synthesis of Lipophenols

“…For instance, lipophenols (or phenol lipids) are biologically active compounds, consisting of a lipidic and a phenolic moiety joined with an ester bond, which have attracted marked interest among nutraceutical and pharmaceutical industries due to their beneficial cumulative or synergistic activities. Lipase-mediated production of novel lipophilic derivatives of natural phenols and polyphenols with fatty acids has received great attention over the past few years [ 21 , 22 , 23 , 24 , 25 , 26 ]. Hydroxytyrosol is a naturally occurring phenolic compound that derives foremost from olive tree and displays significant health benefits, especially high antioxidant activity and cardiovascular protection [ 11 , 27 ].…”

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

“…Additionally, phenolic compounds exert anti-proliferative, anti-inflammatory, and several other properties [22,23], and their derivatives are being presently tested in clinical trials for the treatment of acute ischemic stroke (ozagrel-imidazole-substituted cinnamic acid), convulsions (cinromide-trans-3-bromo-N-ethylcinnamamide), or different types of cancers (piplartine-an alkaloid found in the roots of Piper tuberculatum) [24]. The primary methods of phenolic acids modifications are the esterification of the carboxyl group with aliphatic alcohols, or with polyphenols glycosides or lipids modification via incorporation of phenolic acids [21,25]. Different esters of gallic acid, such as propyl (E310), octyl (E311), and dodecyl (E312) esters, are used as food additives with antioxidant role.…”

“…Furthermore, esters of p-hydroxybenzoic acid, known as parabens, act as food preservatives, e.g., methyl or ethyl parabens, E214 and E218, respectively [26]. In many cases, the esterification of phenolic acids improves their properties-in this way, many functional and antioxidative properties are improved, and in the case of phenolic lipids, the oxidative stability and nutritional value of edible oils are increased, and also these compounds possessing ultraviolet adsorbing activity are valuable in the cosmetics industry [21,25].…”

Ethyl Butyrate Synthesis Catalyzed by Lipases A and B from Candida antarctica Immobilized onto Magnetic Nanoparticles. Improvement of Biocatalysts’ Performance under Ultrasonic Irradiation

“…If water is captured (e.g., using molecular sieves), the yields may be shifted towards the synthesis, and also this may permit preventing the formation of an aqueous phase on the biocatalyst beads (where the water is formed). This water layer can inhibit or inactivate the enzyme [60]. This has been solved using very hydrophobic supports and also using ultrasonic irradiation to stir inside the biocatalyst and to prevent this aqueous phase formation [61,62,63,64].…”