Modified phosphatidylcholine with different alkyl chain length and covalently attached caffeic acid affects the physical and oxidative stability of omega-3 delivery 70% oil-in-water emulsions

Yeşiltaş, Betül; Sørensen, Ann‐Dorit Moltke; Moreno, Pedro J.; Anankanbil, Sampson; Guo, Zheng; Jacobsen, Charlotte

doi:10.1016/j.foodchem.2019.03.087

Cited by 30 publications

(31 citation statements)

References 34 publications

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“…Interfacial tension -pendant drop method. The dynamic interfacial tension of the peptides at the oil-water interface was determined using an automated drop tensiometer OCA20 (DataPhysics Instruments GmbH, Filderstadt, Germany) at 25 °C 38 . Peptide solutions (0.2 wt.%) in 10 mM sodium acetate − 10 mM imidazole buffer (pH 7) were prepared.…”

Section: Methodsmentioning

confidence: 99%

Identification of emulsifier potato peptides by bioinformatics: application to omega-3 delivery emulsions and release from potato industry side streams

Moreno

Gregersen

Nedamani

et al. 2020

Sci Rep

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In this work, we developed a novel approach combining bioinformatics, testing of functionality and bottom-up proteomics to obtain peptide emulsifiers from potato side-streams. This is a significant advancement in the process to obtain emulsifier peptides and it is applicable to any type of protein.Our results indicated that structure at the interface is the major determining factor of the emulsifying activity of peptide emulsifiers. Fish oil-in-water emulsions with high physical stability were stabilized with peptides to be predicted to have facial amphiphilicity: (i) peptides with predominantly α-helix conformation at the interface and having 18-29 amino acids, and (ii) peptides with predominantly β-strand conformation at the interface and having 13-15 amino acids. In addition, high physically stable emulsions were obtained with peptides that were predicted to have axial hydrophobic/hydrophilic regions. Peptides containing the sequence FCLKVGV showed high in vitro antioxidant activity and led to emulsions with high oxidative stability. Peptide-level proteomics data and sequence analysis revealed the feasibility to obtain the potent emulsifier peptides found in this study (e.g. γ-1) by trypsin-based hydrolysis of different side streams in the potato industry.A considerable number of commercial products are oil-in-water emulsions (e.g. food, pharmaceutical, cosmetics) 1 . In addition, aqueous-based food products are enriched with hydrophobic bioactives (i.e., omega-3, vitamins A, D, E, carotenoids, flavonoids or curcumin) by using oil-in-water emulsions as delivery systems 2 . Nevertheless, oil-in-water emulsions are thermodynamically unstable systems. They tend to separate over time into their components (oil and water) due to several physical destabilization mechanisms such as creaming, flocculation, coalescence, and Ostwald ripening 3 . Emulsifiers are the most common stabilizers used in emulsions production since: (i) they facilitate emulsion formation (e.g., by reducing interfacial tension at the oil-water interface), and (ii) they provide physical stability to the emulsion (i.e., by strong steric and/or electrostatic repulsive forces) 4 . Moreover, emulsifiers also have an influence on the chemical stability of emulsions (e.g. oxidative stability) by determining the properties of the oil-water interface (i.e., thickness, porosity, charge, antioxidant activity). Indeed, these interfacial properties play a critical role on the interaction between oil and prooxidants such as radicals, oxygen and trace metals 5 .Milk proteins such as casein and whey protein are common emulsifiers used for food oil-in-water emulsions due to their excellent functional and antioxidant properties, which lead to physically and oxidatively stable emulsions 6 . Nonetheless, there is an increasing trend to replace animal proteins by plant or microbial proteins in vegetarian or vegan products, as well as to enhance food sustainability 7 . Different approaches have been suggested

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Section: Methodsmentioning

confidence: 99%

Identification of emulsifier potato peptides by bioinformatics: application to omega-3 delivery emulsions and release from potato industry side streams

Moreno

Gregersen

Nedamani

et al. 2020

Sci Rep

Self Cite

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“…Natural antioxidants are preferred as being safer (Kiokias & Varzakas, 2014). The use of hydrolysed proteins (Li et al ., 2019), polysaccharides (Shi et al ., 2020) and modified phosphatidylcholine (Yesiltas et al ., 2019) as natural antioxidants to restrain lipid oxidation in O/W emulsions has been well evaluated. Within the natural antioxidants category, phenolic compounds have emerged as a group of natural antioxidants potentially useful in the food industry, due to their remarkable radical scavenging capability.…”

Section: Introductionmentioning

confidence: 99%

Effect of proanthocyanidin‐rich extracts from Chinese quince (Chaenomeles sinensis) fruit on the physical and oxidative stability of sunflower oil‐in‐water emulsions

Qin

Wang

et al. 2021

Int J of Food Sci Tech

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Summary To evaluate the effect of Chinese quince proanthocyanidins (PAs) on the physical and oxidative stability of sunflower oil‐in‐water (O/W) emulsions during storage, three proanthocyanidin (PA)‐rich extracts, namely water extract (WE), ethanol extract (EE), and acetone extract (AE), were prepared. When added to O/W emulsions, all the three extracts inhibited the increase in droplet size and the absolute zeta‐potential value during storage (55 °C, 24 days). All three extracts also exhibited superior antioxidative activity in the O/W emulsions. WE showed the highest efficacy in retarding lipid oxidation as proved by its lower conjugated dienes (8.18 ± 0.49 mmol L−1) and thiobarbituric substances values (0.68 ± 0.0025 mg MDA L−1), and such efficacy was similar to that of BHA at the same level. Lower molecular weight and degree of polymerisation have a positive effect on antioxidant activity of PA‐rich extracts. According to these results, all three PA‐rich extracts are potential natural antioxidants for improving the stability of food‐grade emulsions.

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“…The conjugation and resonance effects in caffeic acid occur due to the presence of the CH=CH bridge between the aromatic ring and the carboxyl group. Thus it may act as a chain-breaking antioxidant via donating an H-atom to free radicals or metal chelator to reduce the activity of prooxidant (Conde et al, 2011;Yesiltas et al, 2019) The antioxidative effectiveness of caffeic acid in oilin-water emulsions is mainly attributed to the retardation of initiation and propagation stages of lipid oxidation reactions by scavenging lipid radicals and forming a low-energy phenoxyl radical that does not readily stimulate oxidation of unsaturated fatty acids (Conde et al, 2011;Maqsood & Benjakul, 2010;Sorensen et al, 2008). Gulcin (2006) found that caffeic acid containing a catechol group with an α,β-unsaturated carboxylic acid chain efficiently F I G U R E 4 Chemical structures of different types of phenolic antioxidants quenched the reactive oxygen species, that is, superoxide anion radicals ( • O 2 − ) and singlet oxygen ( 1 O 2 ), and thus showed 75.8% inhibition of lipid peroxidation in linoleic acid oil-in-water emulsions.…”

Section: Caffeic Acidmentioning

confidence: 99%

A comprehensive review on polarity, partitioning, and interactions of phenolic antioxidants at oil–water interface of food emulsions

Farooq

Khan

Zhang

et al. 2021

Comp Rev Food Sci Food Safe

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There has been a growing interest in developing effective strategies to inhibit lipid oxidation in emulsified food products by utilization of natural phenolic antioxidants owing to their growing popularity over the past decades. However, due to the complexity of emulsified systems, the inhibition mechanism of phenolic antioxidants against lipid oxidation is rather complicated and not yet fully understood. In order to highlight the importance of polarity of phenolic antioxidants in emulsified systems according to the polar paradox, this review covers the recent progress on chemical, enzymatic, and chemoenzymatic lipophilization techniques used to modify the polarity of antioxidants. The partitioning behavior of phenolic antioxidants at the oil-water interface, which can be influenced by the presence of synthetic surfactants and/or antioxidant emulsifiers (e.g., polysaccharides, proteins, and phospholipids), is discussed. In addition, the emerging phenolic antioxidants among phenolic acids, flavonoids, tocopherols, and stilbenes applied in food emulsions are elaborated. As well, the interactions of polar-nonpolar antioxidants are stressed as a promising strategy to induce synergistic interactions at oil-water interface for improved oxidative stability of emulsions.

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Modified phosphatidylcholine with different alkyl chain length and covalently attached caffeic acid affects the physical and oxidative stability of omega-3 delivery 70% oil-in-water emulsions

Abstract: Modified phosphatidylcholine with different alkyl chain length and covalently attached caffeic acid affects the physical and oxidative stability of omega-3 delivery 70% oil-in-water emulsions. Food Chemistry, 289,[490][491][492][493][494][495][496][497][498][499]

Cited by 30 publications

References 34 publications

Identification of emulsifier potato peptides by bioinformatics: application to omega-3 delivery emulsions and release from potato industry side streams

Identification of emulsifier potato peptides by bioinformatics: application to omega-3 delivery emulsions and release from potato industry side streams

Effect of proanthocyanidin‐rich extracts from Chinese quince (Chaenomeles sinensis) fruit on the physical and oxidative stability of sunflower oil‐in‐water emulsions

A comprehensive review on polarity, partitioning, and interactions of phenolic antioxidants at oil–water interface of food emulsions

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