Chemoenzymatically synthesized policosanyl phenolates as autoxidation inhibitors

Abstract

In this study, ten policosanyl phenolates were synthesized via a two‐step chemoenzymatic route. The intermediate vinyl esters were first chemically produced and subsequently esterified with policosanols catalyzed by Novozyme 435 (Candida antarctica lipase B). The conversion yields of the policosanyl phenolates were in the range of 4.20–37.14%. Their antioxidant activities were evaluated. Results showed that, compared with the corresponding phenolic acids, all synthesized policosanyl phenolates had better activities for peroxide value, but worse for 2,2'‐azinobis(3‐ethylbenzothiazoline‐6‐sulfonic acid) assay; policosanyl p‐coumarate and policosanyl 5‐phenylvalerate showed a moderate and durable inhibition effect on lipid oxidation both in a linoleic acid system and a cooked pork system. Practical applications: It is important to develop antioxidants from natural sources. The lipophilization of phenolic acids with fatty alcohols can improve the hydrophobicity and change the antioxidant capacity of phenols. This study focuses on policosanol, which is a food‐grade mixture of long‐chain aliphatic primary alcohols, having development and application potential as a cost‐effective food additive. According to our results, policosanyl phenolates, which are a new range of amphiphilic antioxidant molecules, have the potential for use as alternative food antioxidants in the food industry. The policosanyl phenolates were synthesized via a two‐step route as shown in the figure. The intermediate vinyl esters were first chemically produced and subsequently esterified with policosanols catalyzed by Novozyme 435 (Candida antarctica lipase B).

Comprehensive evaluation of the antioxidant capacity of Perilla frutescens leaves extract and isolation of free radical scavengers using step-wise HSCCC guided by DPPH-HPLC

“…The ABTS assay was performed according to Wang et al [39] with slight modification. In brief, 10 µL of the diluted sample was mixed with 290 µL ABTS solution (2 mM ABTS diammonium salt, 3.5 mM potassium persulfate) and then completed with methanol to a final volume of 300 µL.…”

Lipophilization of phenolic acids with phytosterols by a chemoenzymatic method to improve their antioxidant activities

“…To enhance their hydrophobicity and improve their antioxidant properties, lipophilization of phenolic acids were carried out . But most researchers focused on esterification of phenolic acids with fatty alcohols , steroid compounds have not yet been well studied. Phytosterols (PSs), as bioactive compounds with the ability to lower cholesterol, are steroid compounds that can be found in all vegetable foods.…”

Effect of novel synthesised policosanyl phenolates on lipid oxidation

“…They can be obtained from sugarcane, wheat, and beeswax and are used to treat diabetes and hypercholesterolaemia diseases (Berttner et al 2006;Irmak et al 2006;Berthold et al 2014). In a previous study, several esters of policosanols and phenolic acids were synthesised; the resulting policosanyl p-coumarate and policosanyl 5-phenylvalerate showed a potential for use as lipid antioxidants (Wang et al 2015b). Hence, in this study, the antioxidant capacities of another eight synthesised policosanyl phenolates were assessed and compared in different systems in order to develop novel more effective food antioxidants.…”