Lipophilization of phenolic compounds: optimization of synthesis conditions, antioxidant properties, and identification by LC-MS/MS

• Grant number: 18/21638-7
• Support type: Scholarships abroad - Research Internship - Post-doctor
• Effective date (Start): January 15, 2019
• Effective date (End): November 01, 2019
• Field of knowledge: Agronomical Sciences - Food Science and Technology - Food Science
• Principal researcher: Inar Castro Erger
• Grantee: Tayse Ferreira Ferreira da Silveira
• Supervisor abroad: Pierre Villeneuve
• Home Institution: Faculdade de Ciências Farmacêuticas (FCF). Universidade de São Paulo (USP). São Paulo , SP, Brazil
• Research place: Ingénierie des Agro-polymères et Technologies Émergentes (IATE), France
• Associated to the scholarship: 17/08066-1 - Application of phenolipids to increase oxidative stability of n-3 polyunsaturated fatty acids emulsions, BP.PD

Abstract

Addition of antioxidants is one main strategy to hamper oxidation in oil-in-water (O/W) emulsions. Among the factors governing antioxidant efficacy, polarity was found to play a key role, with nonpolar antioxidants working better in O/W emulsions than polar ones, as stated by the Polar Paradox. In this context, phenolic compounds are recognized as potent antioxidants, but due to their high polarity, they would have limited action in O/W emulsions. Therefore, recently, lipophilization was proposed to decrease their polarity and thus increase their effectiveness in lipid dispersions. Lipophilization, which consists of grafting a lipid moiety to the phenolic compounds to give phenolipids, is a promising and cutting-edge technology for production of antioxidants and may be a good alternative for food manufacturers seeking for replacing traditionally used synthetic antioxidants. Thus, the present proposal aims to evaluate the potential of rutin, quercetin, resveratrol, caffeic acid and cinnamic acid to be enzymatically synthesized. Among these, the most promising phenolipids will have their synthesis conditions optimized, in terms of yield and antioxidant activity (ApoCat assay), using a factorial design. The produced phenolipids will also be purified and characterized by LC-MS/MS. The study will take place at a renowned French research institution (CIRAD), under the supervision of the currently main investigator in this field around the world. Results and materials produced during the internship will be of paramount importance for the progress of the research project to which it is attached (2017/08066-1) and will enable to deeper the study of the effect of phenolipids on the oxidative stability of model emulsions and real food emulsions containing polyunsaturated fatty acids.

Scientific publications

(References retrieved automatically from Web of Science and SciELO through information on FAPESP grants and their corresponding numbers as mentioned in the publications by the authors)

FERREIRA DA SILVEIRA, TAYSE FERREIRA; CAJAIBA, LETICIA MAEDA; VALENTIN, LEONARDO; BAREA, BRUNO; VILLENEUVE, PIERRE; CASTRO, INAR ALVES. Effect of sinapic acid ester derivatives on the oxidative stability of omega-3 fatty acids rich oil-in-water emulsions. Food Chemistry, v. 309, MAR 20 2020. (18/10411-1, 18/21638-7)

FERREIRA DA SILVEIRA, TAYSE FERREIRA; LAGUERRE, MICKAEL; BOURLIEU-LACANAL, CLAIRE; LECOMTE, JEROME; DURAND, ERWANN; FIGUEROA-ESPINOZA, MARIA CRUZ; BAREA, BRUNO; BAROUH, NATHALIE; CASTRO, INAR ALVES; VILLENEUVE, PIERRE. Impact of surfactant concentration and antioxidant mode of incorporation on the oxidative stability of oil-in-water nanoemulsions. LWT-FOOD SCIENCE AND TECHNOLOGY, v. 141, APR 2021. (17/08066-1, 18/21638-7)