Bingcan Chen

Minor Components in Food Oils: A Critical Review of their Roles on Lipid Oxidation Chemistry in Bulk Oils and Emulsions

Food oils are primarily composed of triacylglycerols (TAG), but they may also contain a variety of other minor constituents that influence their physical and chemical properties, including diacylglycerols (DAG), monoacylglycerols (MAG), free fatty acids (FFA), phospholipids (PLs), water, and minerals. This article reviews recent research on the impact of these minor components on lipid oxidation in bulk oils and oil-in-water emulsions. In particular, it highlights the origin of these minor components, the influence of oil refining on the type and concentration of minor components present, and potential physicochemical mechanisms by which these minor components impact lipid oxidation in bulk oils and emulsions. This knowledge is crucial for designing food, pharmaceutical, personal care, and other products with improved stability to lipid oxidation.

Role of continuous phase anionic polysaccharides on the oxidative stability of Menhaden oil-in-water emulsions

The antioxidant role of selected polysaccharides was studied in the continuous phase of a Menhaden oil-in-water emulsion coated by polyoxyethylene(23) lauryl ether (Brij 35) at neutral pH. The addition of low-methoxyl (LM) and high-methoxyl (HM) pectin (0.02-0.1 wt %) reduced the formation of lipid hydroperoxides and thiobarbituric acid reactive substances with an inhibition that increased with increasing polysaccharide concentration in the continuous phase. alpha-Carrageenan and sodium alginate were less effective antioxidants than pectin and were prooxidative under certain conditions. None of the polysaccharides impacted the physical properties of the emulsions as determined by droplet particle size (d(43) approximately 0.32 microm) and creaming index. LM and HM pectins had higher iron-binding capacities as compared to alpha-carrageenan and sodium alginate, which may relate to their higher antioxidant activities. These results suggest that the addition of anionic polysaccharides to the continuous phase of oil-in-water emulsions could be used to increase the oxidative stability of oil-in-water emulsions and thus prolong shelf life.

Physical structures in soybean oil and their impact on lipid oxidation.

The oxidation of edible oil yields both primary and secondary oxidation products (e.g., hydroperoxides, carbonyls, hydrocarbons, and epoxides), which produce undesirable sensory and biological effects. Consequently, the suppression of lipid oxidation in food matrices is of great importance. The rate and extent of lipid oxidation in many heterogeneous foods are strongly affected by the physicochemical characteristics of water-oil interfaces. This study examined the ability of dioleoylphosphatidylcholine (DOPC) and water to form association colloids within bulk oil, as well as their impact on lipid oxidation kinetics. Attenuation was used to show the DOPC and water concentrations at which association colloids existed without altering the optical properties of the oil. Interfacial tension and fluorescence spectrometry showed the critical micelle concentration (CMC) of DOPC in stripped soybean oil was around 650 μM at room temperature. Small-angle X-ray scattering (SAXS) and fluorescence probes showed that water had a very strong impact on the properties of the association colloids formed by DOPC. Measurement of primary and secondary lipid oxidation products revealed that the association colloids formed by DOPC had a pro-oxidant effect. The characterization of association colloids could provide a better understanding of the mechanisms of lipid oxidation in bulk oils and provide insights into new antioxidant technologies.

Design of foods with bioactive lipids for improved health.

Numerous studies have found an association between the consumption of certain bioactive lipids and improved human health, e.g., the prevention, delay, or treatment of chronic and acute diseases, such as cancer, cardiovascular disease (CVD), osteoporosis, and immune disorders. In this review, we discuss food-based sources and potential beneficial attributes of major dietary bioactive lipids: polyunsaturated fatty acids; carotenoids; phytosterols and phytostanols; and fat-soluble vitamins. We summarize the various challenges associated with incorporating these bioactive lipids into foods and beverages, such as poor water solubility, high melting point, and low chemical stability. Finally, we propose several techniques that have been used to solve the challenges and integrate dietary bioactive lipids into foods for improved health.

New Insights into the Role of Iron in the Promotion of Lipid Oxidation in Bulk Oils Containing Reverse Micelles

Formation of physical structures, known as association colloids, in bulk oils can promote lipid oxidation. However, the cause of this accelerated lipid oxidation is unknown. Therefore, the aim of this study was to investigate whether transition metals were important prooxidants in bulk oils containing reverse micelles produced from 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC) and water. The Fe(III) chelator deferoxamine (DFO) increased the oxidative stability of stripped soybean oil (SSO) containing reverse micelles from 2 to 7 days. Because phosphatidylcholine (1,2-dibutyl-sn-glycero-3-phosphocholine) that does not form reverse micelles is not prooxidative, these results suggest that the prooxidant activity of DOPC reverse micelles could be due to their ability to concentrate both endogenous iron and lipid hydroperoxides at the water-lipid interface, thereby increasing the ability of iron to decompose lipid hydroperoxides. DFO was also able to improve the activity of α-tocopherol and Trolox in SSO containing DOPC reverse micelles increasing the lag phase from 2 to 11 and 13 days, respectively. DOPC reverse micelles decreased iron-promoted α-tocopherol and Trolox decomposition and decreased the ability of α-tocopherol and Trolox to decrease Fe(III) concentrations. Overall, these results suggest that iron is an important prooxidant in bulk oils containing reverse micelles; therefore, finding ways to control iron reactivity in association colloids could provide new technologies to increase the oxidative stability of oils.

Physical and oxidative stability of pre-emulsified oil bodies extracted from soybeans

Soybeans contain oil bodies that are coated by a layer of oleosin proteins. In nature, this protein coating protects the oil bodies from environmental stresses and might be utilised by food manufacturers for the same purpose. In this study, an aqueous extraction method was developed to increase the yield of oil bodies extracted from soybean. This method involved a two-step procedure: (i) blending, dispersion, and filtration of soybeans; (ii) homogenisation, suspension, and centrifugation of the filter cake. Using this extraction method about 65% of the oil bodies could be obtained. The mean particle diameter (d43) and sedimentation of the resulting oil bodies increased during storage, suggesting they were prone to aggregation. Heat treatment (90°C, 30min) of the oil body suspensions immediately after extraction improved their storage stability, which was attributed to deactivation of endogenous enzymes such as lipase and lipoxygenase. Heat treatment did not adversely affect the oxidative stability of the oil body suspensions at pH 3 or 7 during storage at 37°C. These results suggest that this aqueous extraction method can be used to prepare oil body suspensions with improved long-term stability.

Stabilization of Soybean Oil Bodies by Enzyme (Laccase) Cross-Linking of Adsorbed Beet Pectin Coatings

Soybean oil bodies are naturally coated by a layer of phospholipids and oleosin proteins, which protect them from in vivo environmental stresses. When oil bodies are incorporated into food products, they encounter new environmental stresses such as changes in pH, ionic strength, and temperature. Consequently, additional protection mechanisms are often needed to stabilize them. The purpose of this study was to determine whether soybean oil bodies could be stabilized by coating them with a layer of cross-linked anionic polysaccharide (beet pectin). The beet pectin layer was cross-linked via its ferulic acid groups using laccase (an enzyme that catalyzes the oxidation of phenolic groups). Oil body suspensions were prepared that contained 1 wt % oil and 0.06 wt % beet pectin at pH 7 and were then adjusted to pH 4.5 to promote electrostatic deposition of the beet pectin molecules onto the surfaces of the oil bodies. Laccase was then added to promote cross-linking of the adsorbed beet pectin layer. Cross-linked pectin-coated oil bodies had similar or better stability than uncoated oil bodies to pH changes (3 to 7), NaCl addition (0 to 500 mM), and freeze-thaw cycling (-20 °C for 22 h; +40 °C for 2 h). These pectin-coated oil bodies may provide a convenient means of incorporating soybean oil into food and other products.

Antioxidant Properties of Chlorogenic Acid and Its Alkyl Esters in Stripped Corn Oil in Combination with Phospholipids and/or Water

In bulk oil, it is generally thought that hydrophilic antioxidants are more active than lipophilic antioxidants. To test this hypothesis, the antioxidant activity of phenolics with increasing hydrophobicity was evaluated in stripped corn oil using both conjugated diene and hexanal measurements. Chlorogenic acid and its butyl, dodecyl, and hexadecyl esters were used as model phenolic antioxidants with various hydrophobicities. Results showed that hydrophobicity did not correlate well with antioxidant capacity. The combination of chlorogenic acid derivatives with dioleoylphosphatidylcholine (DOPC) and/or water was also studied to determine if the physical structure in the oil affected antioxidant activity. DOPC alone made hexadecyl chlorogenate a less effective antioxidant, but it did not change the antioxidant capacity of chlorogenic acid. In contrast, the combination of DOPC and water (∼400 ppm) renders chlorogenic acid a less active antioxidant, whereas it does not change the activity of hexadecyl chlorogenate. These results show, in bulk oil, that intrinsic parameters such as the hydrophobicity of lipophilized phenolics do not exert a strong influence on antioxidant capacity, but they can be highly influential if potentialized by extrinsic factors such as physical structures in the oil.

Chemical and Antioxidant Properties of Casein Peptide and Its Glucose Maillard Reaction Products in Fish Oil-in-Water Emulsions

Maillard reaction products (MRPs) were prepared by reacting casein peptides with different concentrations of glucose at 80 °C for up to 12 h. The chemical properties of MRPs and their effects on lipid oxidation in fish oil-in-water emulsions were investigated. Increasing browning development and absorbance in 294 nm in the MRPs caused an increase in DPPH radical scavenging, but a decrease in iron chelation, which could be related to the loss of free amino groups in the peptides. The MRPs produced with longer reaction time or higher glucose concentrations were less effective in inhibiting lipid oxidation in emulsions at pH 7.0 compared to casein peptides alone. However, the antioxidant activity of MRPs in emulsions at pH 3.0 was not decreased by prolonged heating. The bitterness of MRPs was less than that of the original casein peptides, and bitterness decreased with increasing heating time and glucose concentrations. Therefore, the Maillard reaction was a potential method to reduce the bitterness of casein peptides while not strongly decreasing their antioxidant activity.

Understanding antioxidant mechanisms in preventing oxidation in foods.

Abstract: Many foods are becoming more susceptible to oxidative rancidity due to attempts to make foods healthier by increasing polyunsaturated fatty acids, and more sustainable by introducing light weight oxygen-permeable and light-penetrating packaging. Unfortunately, very few new food antioxidants have been made available over the past several decades and the use of synthetic antioxidants is disfavored by many consumers. Thus, in order to make natural, more sustainable and healthier foods, the food technologist must find ways to use existing antioxidants more effectively. This requires a strong understanding of antioxidant chemistry. This chapter reviews the chemistry of free radical scavengers, metal chelators, singlet oxygen quenchers and antioxidant enzymes. Interactions between antioxidants to enhance activity are also discussed.