Abstract
The chemical synthesis of new lipophilic polyphenols with improved properties presents technical difficulties. Here we describe the selection, isolation and identification of lipolytic bacteria from food-processing industrial wastes, and their use for tailoring a new set of compounds with great interest in the food industry. These bacteria were employed to produce lipolytic supernatants, which were applied without further purification as biocatalysts in the chemoselective and regioselective synthesis of lipophilic partially acetylated phenolic compounds derived from olive polyphenols. The chemoselectivity of polyphenols acylation/deacylation was analyzed, revealing the preference of the lipases for phenolic hydroxyl groups and phenolic esters. In addition, the alcoholysis of peracetylated 3,4-dihydroxyphenylglycol resulted in a series of lipophilic 2-alkoxy-2-(3,4-dihydroxyphenyl)ethyl acetate through an unexpected lipase-mediated etherification at the benzylic position. These new compounds are more lipophilic and retained their antioxidant properties. This approach can provide access to unprecedented derivatives of 3,4-dihydroxyphenylglycol with improved properties.
Highlights
The beneficial effects of the Mediterranean diet are partly due to its high content in antioxidant compounds [1]
In order to obtain lipophilic phenolic esters it is essential to achieve the esterification of primary alcoholic groups without affecting the catechol moiety, which is known to be essential for the antioxidant effects
Previous reports have shown that the lipophilic derivatives and analogs of one of the olive phenols, HT, with esters or ethers functionalities display a better hydrophilic/lipophilic balance [28], an increased bioavailability compared with their unprotected analogs [29] and stability to oxygen compared with the underivatized HT, which make these molecules more attractive for the food industry [30]
Summary
The beneficial effects of the Mediterranean diet are partly due to its high content in antioxidant compounds [1]. The polyphenols present in the virgin olive oil display a strong antioxidant activity in vitro [2] and in vivo [3,4], which has impelled a growing interest in these compounds, especially those that can be obtained from by-products of the food industry [5]. Several epidemiological studies have shown the beneficial health effects arising from consumption of foods rich in antioxidants, preventing the damage caused by prolonged oxidative stress in certain biomolecules (nucleic acids, lipids, proteins), which is associated with an increased risk of chronic diseases [6]. The acylated polyphenols display improved properties as PLOS ONE | DOI:10.1371/journal.pone.0166561. The acylated polyphenols display improved properties as PLOS ONE | DOI:10.1371/journal.pone.0166561 November 17, 2016
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Free) 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a call
