γ‐ and δ‐tocopherols are more effective than α‐tocopherol on the autoxidation of a 10% rapeseed oil triacylglycerol‐in‐water emulsion with and without a radical initiator

The antioxidative effects of γ‐ and mainly δ‐tocopherol in a multiphase system were hardly considered up to now. The aim of this study was i) to assess the effects and ii) to follow the degradation of α‐, γ‐ and δ‐tocopherol in concentrations of 0.01%, 0.05%, 0.1% and 0.25% during the oxidation of a 10% purified rapeseed oil triacylglycerol‐in‐water emulsion at 40 °C in the dark for 15 wk in a system containing a low oxygen concentration. Oxidation experiments were performed weekly by assessing the formation of hydroperoxides and hexanal, and the stability of the tocopherols was determined using high‐performance liquid chromatography. Storage tests were conducted with and without the addition of 0.01% α, α′‐azoisobutyronitrile (AIBN), which is a known radical initiator. α‐Tocopherol increased the formation of hydroperoxides in both tests as well as the generation of hexanal when the radical initiator was added; furthermore it was the least stable. γ‐Tocopherol delayed the formation of hexanal and prolonged the stability of the emulsion in a dose‐dependant manner. δ‐Tocopherol was the most stable and also the most effective in delaying lipid oxidation in the emulsions. Each concentration that was tested reduced the rate of hydroperoxide and especially hexanal formation. Hexanal was only formed to a slight extent after 15 wk of oxidation in the test with AIBN and the lowest dose of 0.01% δ‐tocopherol. For all tocopherols, strong correlations were found between tocopherol stability and the extent of oxidation. Results suggest that i) mainly δ‐tocopherol, but also γ‐tocopherol even less pronounced, are very good antioxidants in order to stabilize and prolong the shelf life of oil‐in‐water emulsions, ii) the antioxidative effects were intensified with increasing amounts.     

Quantification of Antioxidant Ability Against Lipid Peroxidation with an ‘Area Under Curve’ Approach

When oxygen is passed through a linoleic acid (LA) emulsion containing copper(II), primary (hydroperoxides) and secondary oxidation products (aldehydes and ketones) are formed, monitored by ferric thiocyanate (Fe(III)‐SCN) and thiobarbituric acid reactive substances (TBARS) colorimetry, respectively. As total antioxidant capacity (TAC) against lipid peroxidation was not quantified before, both methods were adapted to an ‘area under curve (AUC)’ approach. LA peroxidation followed pseudo‐first order kinetics in aerated emulsions. Absorbance changes as a function of incubation time exhibited sigmoidal curves, enabling the calculation of ‘area under curve’ (AUC) and net AUC = AUC_blank?AUC_sample, standard calibration curve as net AUC versus concentration, and trolox‐equivalent antioxidant capacity of the tested compounds. Garlic extract showed an antioxidative effect on hydroperoxide formation, but a prooxidative effect on TBARS. Although inhibition of lipid peroxidation was described qualitatively before, it was not evaluated quantitatively, e.g., the trolox‐equivalent antioxidant capacities (TEAC values) of antioxidants with respect to their inhibitive effect against lipid peroxidation were not calculated and compared. Additionally, real‐time monitoring of lipid oxidation products requires highly sophisticated but costly instrumental techniques, but no single oxidation product is a direct measure of lipid oxidation or its antioxidative prevention. The AUC approach is the first quantitative method measuring antioxidant protection against lipid oxidation, with a slightly different order of antioxidative effectiveness from reductive assays because of interfacial effects.     

α‐, γ‐ and δ‐ Tocopherols as inhibitors of isomerization and decomposition of cis,trans methyl linoleate hydroperoxides

The effects of α‐, γ‐ and δ‐tocopherols on the stability and decomposition reactions of lipid hydroperoxides were studied. Isomerization and decomposition of cis,trans methyl linoleate hydroperoxides (cis,trans ML‐OOH) in hexadecane at 40 °C were followed by high‐performance liquid chromatography. Due to its higher hydrogen donating ability, α‐tocopherol was more efficient than γ‐ and δ‐tocopherols in inhibiting the isomerization of cis,trans ML‐OOH to trans,trans ML‐OOH. α‐Tocopherol stabilized hydroperoxides into the cis,trans configuration, whereas γ‐ and δ‐tocopherols allowed hydroperoxides to convert into trans,trans isomers. Thus, the biological importance of α‐tocopherol as compared to other tocopherols may be partly due to its better efficacy in protecting the cis,trans configuration of hydroperoxides formed, for example, in the enzymatic oxidation of polyunsaturated fatty acids. The isomeric configuration of hydroperoxides has an impact on biological activities of further oxidation products of polyunsaturated fatty acids. Paradoxically, the order of activity of tocopherols with regard to hydroperoxide decomposition was different from that obtained for hydroperoxide isomerization. γ‐ and δ‐tocopherols were more efficient inhibitors of ML‐OOH decomposition when compared to α‐tocopherol. A loss of antioxidant efficiency, observed as the tocopherol concentration increased from 2 to 20 mM, was highest for α‐tocopherol but was also evident for γ‐ and δ‐tocopherols. Thus, the differences in the relative effects of tocopherols at differing concentrations seem to result from a compromise between their radical scavenging efficiency and participation in side reactions of peroxidizing nature.     

Kinetics of antioxidant action of α‐ and γ‐toco‐pherols in sunflower and soybean triacylglycerols

A kinetic analysis was performed to evaluate the antioxidant behavior of α‐ and γ‐to‐copherols (5—2000 ppm) in purified triacylglycerols obtained from sunflower oil (TGSO) and soybean oil (TGSBO) at 100 °C. Different kinetic parameters were determined, viz. the stabilization factor as a measure of effectiveness, the oxidation rate ratio as a measure of strength, and the antioxidant activity which combines the other two parameters. In the low concentration range (up to 400 ppm in TGSBO and up to 700 ppm in TGSO) α‐tocopherol was a more active antioxidant than γ‐tocopherol whereas the latter was more active at higher concentrations. It has been found that the different activity of the tocopherols is not due to their participation in chain initiation reactions, but that the loss of antioxidant activity at high tocopherol concentrations is due to their consumption in side reactions. The rates of these reactions are higher in TGSBO than in TGSO. Both α‐tocopherol itself and its radicals participated more readily in side reactions than γ‐tocopherol and its radicals. Both α‐ and γ‐tocopherol reduce lipid hydroperoxides, thus generating alkoxyl radicals which are able to amplify the rate of lipid oxidation by participating in chain propagation reactions.     

Surfactant Concentration,Antioxidants, and Chelators Influencing Oxidative Stability of Water‐in‐Walnut Oil Emulsions

Effects of surfactant concentration, antioxidants with different polarities, and chelator type on the oxidative stability of water‐in‐stripped walnut oil (W/O) emulsions stabilized by polyglycerol polyricinoleate (PGPR) were evaluated. The formation of primary oxidation products (lipid hydroperoxides) and secondary oxidation products (hexanal) decreased with increasing PGPR concentrations (0.3–1.0 wt% of emulsions). Excess surfactant might solubilize lipid hydroperoxides out of the oil–water interface, resulting in the decreased lipid oxidation rates in W/O emulsions. At concentrations of 10–1000 μM, the polar Trolox demonstrated concentration‐dependent antioxidant activity according to both hydroperoxide and hexanal formation. The antioxidant efficiency of the non‐polar α‐tocopherol was slightly reduced at the higher range of 500–1000 μM based on hydroperoxide formation. Both ethylenediaminetetraacetic acid (EDTA) and deferoxamine (DFO) at concentrations of 5–100 μM reduced the rates of lipid oxidation at varying degrees, indicating that endogenous transition metals may promote lipid oxidation in W/O emulsions. EDTA was a stronger inhibitor of lipid oxidation than DFO. These results suggest that the oxidative stability of W/O emulsions could be improved by the appropriate choice of surfactant concentration, antioxidants, and chelators.     

Oxidation at elevated temperatures: competition between α‐tocopherol and unsaturated triacylglycerols

The competitive oxidation between α‐tocopherol and unsaturated fatty acyls at thermoxidation conditions (180 and 240 °C) was evaluated using purified triacylglycerols from nine fats and oils (refined coconut, palm, tallow, olive, high oleic sunflower, sunflower, corn, soybean, and flaxseed oil). α‐Tocopherol degraded faster in less unsaturated lipids and a linear correlation between the iodine value (x) and the residual tocopherol content (y) was obtained after 2 h of heating at 240 °C (y = 3.72x + 137.5, R² = 0.9463). The formation of polar oxidation products was established and the results were explained by a non‐selective oxidation of unsaturated fatty acyls and α‐tocopherol by highly reactive alkoxyl and hydroxyl radicals generated by decomposition of hydroperoxides.     

Process efficiency and long‐term performance of α‐tocopherol in film‐blown linear low‐density polyethylene

α‐Tocopherol was compared with a commercial phenolic antioxidant (Irganox 1076) as a long‐term and process antioxidant in film‐blown and compression‐molded linear low‐density polyethylene. The antioxidant function of α‐tocopherol was high in the film‐blown material, especially in the processing, according to oxygen induction time measurements with differential scanning calorimetry. The residual content of α‐tocopherol after processing, determined with chromatographic techniques, was less than that of the commercial phenolic antioxidant in both the film‐blown and compression‐molded materials. The process stabilizing efficiency was nevertheless higher for the material containing α‐tocopherol. During the long‐term stabilization, the efficiency of α‐tocopherol was less than that of the commercial phenolic stabilizer Irganox 1076 in the thin films, according to chemiluminescence and infrared measurements. The long‐term efficiency in the compression‐molded samples stabilized with α‐tocopherol or Irganox 1076 was equally good because of the low loss of both α‐tocopherol and Irganox 1076 from the thicker films. © 2005 Wiley Periodicals, Inc. J Appl Polym Sci 98: 2427–2439, 2005     

Iron‐Catalyzed Reaction of γ‐Tocopherol with Methyl Linoleate Hydroperoxides in Solutions

γ‐Tocopherol is one of the main constituents in vegetable oils and acts as an antioxidant by trapping lipid‐peroxyl radicals. This study reports reaction products of γ‐tocopherol with lipid‐peroxyl radicals formed by iron‐catalyzed decomposition of methyl linoleate hydroperoxides (MeLOOH) in toluene and methanol solutions. The products in toluene solution were tocored, methyl (8a‐dioxy‐γ‐tocopherone)‐epoxyoctadecenoates (γT‐OO‐epoxyMeL), methyl (8a‐dioxy‐γ‐tocopherone)‐octadecadienoates (γT‐OO‐MeL), γ‐tocopherol biphenyl dimer (γTBD), γ‐tocopherol diphenylether dimer (γTED), and adducts of γ‐tocopherol dimers with the MeLOOH‐derived peroxyl radicals (γTED‐OO‐epoxyMeL, γTBD‐OO‐MeL, and γTED‐OO‐MeL). The iron‐catalyzed reaction in toluene proceeded slowly, whereas the reaction in methanol was relatively fast. The reaction products in methanol were γT‐OO‐epoxyMeL and γTED‐OO‐epoxyMeL together with tocored, γTBD, and γTED. The results indicate that the iron‐catalyzed decomposition of MeLOOH in toluene produces both epoxyperoxyl and peroxyl radicals and that the decomposition in methanol yields only the epoxyperoxyl radicals. These peroxyl radicals could react with the 8a‐carbon‐centered radical of γ‐tocopherol or its dimers.     

Role of Water and Selected Minor Components on Association Colloid Formation and Lipid Oxidation in Bulk Oil

This study investigated the influence of water content in combination with selected minor components including oleic acid, stigmasterol, α‐tocopherol, and Trolox on their association colloid formation as well as their impact on lipid oxidation in bulk corn oil. First, surface activity of each minor component was evaluated by determining the ability of these components to lower the interfacial tension between bulk oil and water. All components but α‐tocopherol were able to decrease interfacial tension of stripped oil. Second, the critical micelle concentration (CMC) of each minor component was determined in bulk oil with no water added and in the presence of 1000 ppm of water. In the bulk oil without extraneous water, we could not determine the CMC of minor components in the range of concentrations studied. However, in the presence of 1000 ppm of water, only stigmasterol could form association colloids at the CMC of 20 mmol/kg oil. Last, the effect of water content (400 and 1000 ppm) and minor components on lipid oxidation in bulk oil was studied by following the lipid hydroperoxides and hexanal formation during storage at 55 °C. Different water content did not significantly impact the lag time of lipid oxidation compared with the control. Interestingly, water caused prooxidant by decreasing the lag time of lipid hydroperoxides and hexanal formation in bulk oil containing oleic acid, stigmasterol, and Trolox compared with the control of each system. On the other hand, there was not significant impact of water on the antioxidant activity of α‐tocopherol, a lipid soluble antioxidant in bulk oil. This study highlights the impact of water content on the surface activity of minor components as well as on the oxidative stability in bulk oil.     

Inhibition of Hydroperoxy-, Keto- and Hydroxy-FAME by Alpha- and Delta-Tocopherol at Rancimat Conditions

The effects of α‐ and δ‐tocopherol on inhibition of hydroperoxides, keto and hydroxy compounds under Rancimat conditions, i.e. 100 °C and air bubbling, were studied in samples of fatty acid methyl esters (FAME) obtained from high linoleic (HL) and high oleic (HO) sunflower oils. Primary hydroperoxides from methyl linoleate and methyl oleate and secondary keto and hydroxy compounds derived from methyl linoleate hydroperoxides were analyzed by HPLC–UV‐ELS. Different tocopherol concentrations, namely, 10, 50, 100, 500 and 1000 mg/kg, were tested. Irrespective of the lipid substrate and the initial concentration of tocopherol, results showed that the content of hydroperoxides accumulated during the induction period was remarkably higher in the samples containing δ‐tocopherol. The relative concentrations of oleate hydroperoxides in the HO samples were also higher in the presence of δ‐tocopherol. α‐Tocopherol was more effective in inhibiting hydroperoxides at low levels, with 100 mg/kg as optimal concentration, while δ‐tocopherol displayed optimal protection at 1000 mg/kg. Under the oxidation conditions applied, neither α‐ nor δ‐tocopherol showed a protective effect on hydroperoxide decomposition at any level assayed. Formation of keto‐ and hydroxy‐dienes was more related to the concentration of their hydroperoxide precursors. Furthermore, both tocopherols gave rise to increased concentrations of ketodienes at 500 and 1000 mg/kg compared to the controls. Such an effect was more pronounced for α‐tocopherol and in the HL samples.     

Antioxidant activity of phenolic compounds in sunflower oil‐in‐water emulsions containing sodium caseinate and lactose

The aim of this work was to study the evolution of oxidation and the efficiency of phenolic antioxidants in sunflower oil‐in‐water emulsions containing sodium caseinate and lactose (Cas‐Lac) or stabilized by Tween‐20 (T‐20). Two groups of phenolic antioxidants which are structurally similar were tested, i.e. (1) α‐tocopherol and its water‐soluble analogue, Trolox; and (2) gallic acid and its ester derivatives propyl gallate and dodecyl gallate. Emulsion samples were oxidized at 40 °C and the progress of oxidation was followed through quantitation of oxidized triacylglycerol monomers, dimers and oligomers. Results showed that Cas‐Lac emulsions were more stable to oxidation than T‐20 emulsions. In both types of emulsions, the most protective antioxidants were the compounds of lower polarity, namely, α‐tocopherol and dodecyl gallate. It was also found that substantial amounts of α‐tocopherol coexisted with significant polymerization, which was indicative of the heterogeneity of oxidation, i.e. differences of oxidation rate in oil droplets.     

Effect of different antioxidants on lycopene degradation in oil‐in‐water emulsions

There is interest in incorporating lycopene into foods because it is a natural pigment and can also play a role in preventing disease. Therefore, the effect of the addition of various antioxidants in lycopene containing oil‐in‐water emulsions stabilized with Tween 20 at acidic pH was studied in order to determine protection systems against lycopene oxidation. In this model, EDTA showed pro‐oxidant activity while other chelators like citric acid and tripolyphosphate showed no effect. The free radical scavengers, propyl gallate (PG), gallic acid (GA), and α‐tocopherol all had the ability to decrease lycopene oxidation with α‐tocopherol being the most effective. The combination of 1 µM α‐tocopherol and 10 µM GA was more effective than the individual antioxidants. Addition of ascorbic acid to the combination of α‐tocopherol and GA system accelerated lycopene loss. These results suggest that by the proper selection of free radical scavenging antioxidants, lycopene stability in oil‐in‐water emulsions could be significantly improved. Practical applications: Evidence that dietary lycopene decreases the risk for a number of health conditions has generated new opportunities for addition of lycopene to functional foods. A successful strategy to deliver lycopene into foods is by means of oil‐in‐water emulsions. However, lycopene may decompose thus causing nutritional loss and color fading. In order to prevent this, the effectiveness of various antioxidants and their combinations in Tween 20 stabilized oil‐in‐water emulsions was studied. Overall, lycopene oxidation in oil‐in‐water emulsions could be significantly reduced by the proper selection of free radical scavengers. This fact is of interest to food industry for increasing the shelf‐life of lycopene containing functional foods where the lycopene is dispersed in the food in the form of an oil‐in‐water emulsion.     

Effects of tocopherols and tocotrienols on the inhibition of autoxidation of conjugated linoleic acid

The effect of eight vitamin E homologues, i.e. α‐, β‐, γ‐, and δ‐tocopherol and α‐, β‐, γ, and δ‐tocotrienol, on the inhibition of autoxidation of conjugated linoleic acid (CLA) were investigated. The oxidation was carried out in the dark for 21 days at 50 °C and monitored by peroxide values (PV) and TBA values. The levels of the individual vitamin E homologues in CLA during storage were determined by HPLC. γ‐Tocopherol exhibited the highest antioxidant activity among the homologues tested in this study when the antioxidant activities of the individual homologues in CLA were compared by PV. The order of antioxidant activity of eight homologues was γ‐tocopherol > δ‐tocopherol = δ‐tocotrienol ≥ γ‐tocotrienol > β‐tocopherol = β‐tocotrienol > α‐tocopherol = α‐tocotrienol. The degradation rates of α‐tocopherol and α‐tocotrienol were faster than those of the other homologues, whereas δ‐tocopherol had the highest stability in CLA during storage. All homologues exhibited an antioxidant activity by inhibiting the formation of secondary oxidation products. It appears that α‐tocotrienol and β‐tocotrienol have significantly higher antioxidant activities for secondary oxidation in CLA than α‐tocopherol and β‐tocopherol. Meanwhile, the other homologues, namely γ‐tocopherol, γ‐tocotrienol, δ‐tocopherol, and δ‐tocotrienol, exhibited similar antioxidant activity for secondary oxidation in CLA.     

Effects of Phosphatidylcholine on Interaction of α-Tocopherol and β-Carotene in Photosensitized Oxidation of Emulsions

The interaction between α‐tocopherol (500 mg/kg) and β‐carotene (10 mg/kg) during chlorophyll‐photosensitized oxidation of a sunflower oil emulsion was studied in the presence or absence of phosphatidylcholine (PC, 250 mg/kg) by determining peroxide (POV) and conjugated dienoic acid (CDA) values. Chlorophyll, α‐tocopherol, β‐carotene, and PC contents in the emulsion were also monitored. α‐Tocopherol and β‐carotene individually and interactively decreased the POV and CDA values of oil in the emulsion by singlet oxygen quenching. PC decreased the POV and CDA values of oil, however, the values of the emulsion with added α‐tocopherol, β‐carotene, and PC were not significantly different from those of the emulsion with added α‐tocopherol and β‐carotene without PC. Contents of α‐tocopherol did not change during 24‐h oxidation, whereas co‐present PC significantly caused α‐tocopherol and chlorophyll degradation. β‐Carotene and PC contents significantly decreased to 45.5 and 51.3 %, respectively, after 24 h, and α‐tocopherol protected β‐carotene from degradation. The results suggest that PC had no net effects on the interactive antioxidant activity of α‐tocopherol and β‐carotene during chlorophyll‐photosensitized oxidation of the emulsion through free radical generation, chlorophyll degradation, and lessening the potency of α‐tocopherol as a singlet oxygen quencher.     

Mulberry Seed Oil: a Rich Source of δ‐Tocopherol

In the present study, mulberry seed oil (MSO) samples obtained from seeds of different mulberry varieties as well as concentrated mulberry juice production waste (mulberry pomace) were investigated. Radical scavenging capacity, tocopherol and total phenolic content of MSO were determined. It was observed that MSO contain unique amounts of δ‐tocopherol varying between 1645–2587 mg kg^?1 oil depending on the variety. The secondary tocopherol homologue was γ‐tocopherol within a concentration range of 299–854 mg kg^?1 oil. MSO exhibited a very high antioxidant capacity varying in the range of 1013–1743 and 2574–4522 mg α‐tocopherol equivalents (α‐TE) per kg of oil for 2,2‐diphenyl‐1‐picrylhydrazyl (DPPH) and freeze‐dried 2,2′‐azino‐bis (3‐ethylbenzothiazoline‐6‐sulfonic acid) (FD‐ABTS) radical cation assays, respectively. Both antioxidant capacity and total phenolic content were higher for mulberry pomace oil compared with the seed oils. Fatty acid composition of MSO was also determined, and linoleic acid was found to be the primary fatty acid (66–80 %).     

Low‐density lipoprotein is oxidized by phospholipase A2 and lipoxygenase in xanthoma lesions

Oxidized LDL has been obtained by incubation with copper ions (Cu‐LDL) or various kinds of cells. LDL incubated with xanthoma tissues (x‐LDL) is considered a model of in vivo oxidized LDL that has extravasated into xanthoma lesions. To investigate the mechanism of x‐LDL formation, we studied the effects of various enzyme inhibitors or antioxidants on the oxidation process of LDL. Thiobarbituric acid‐reactive substance (TBARS) levels, electrophoretic mobility and spectrophotometric pattern of the oxidized LDL were examined. Antioxidants suppressed TBARS formation in both x‐LDL and Cu‐LDL. Enzyme inhibitors inhibited TBARS levels in x‐LDL, but not in Cu‐LDL. All the enzyme inhibitors and antioxidants, except for the cyclooxygenase inhibitor, inhibited the anodic electrophoretic mobility of x‐LDL. The anodic electrophoretic mobility of Cu‐LDL was suppressed only with antioxidants. Spectrophotometry indicated that an increase in the absorbance at 240 nm was observed in Cu‐LDL, but not in x‐LDL. x‐LDL oxidation is primarily catalyzed by phospholipase A₂, and subsequently generated polyunsaturated free fatty acids propagate the peroxidation. Fatty acid hydroperoxides conjugated with dienes are not synthesized in x‐LDL. On the other hand, non‐enzymatic oxidants, such as superoxide anion and hydroxyl radicals generate Cu‐LDL with diene‐conjugated fatty acid hydroperoxides.     

3, 4‐Dihydroxymandelic acid amides of alkylamines as antioxidants for lipids

The antioxidative and radical scavenging activity of the 3, 4‐dihydroxymandelic acid (DHMA) amides of hexylamine, 2‐ethylhexylamine, octylamine, and cyclohexylamine was determined by several physicochemical test systems. The amides were synthesized by protecting group‐free coupling of in situ prepared N‐hydroxysuccinimidylester of DHMA and the amines. The radical scavenging activity was determined using the DPPH (2, 2‐diphenyl‐1‐picrylhydrazyl) method and by quenching superoxide anions generated using a horse radish peroxidase/H₂O₂ system. In the DPPH assay, all amides show higher radical scavenging activity (EC₅₀ 0.09‐0.12 mol/mol_DPPH) compared to the standard antioxidants ascorbic acid (EC₅₀ 0.27 mol/mol_DPPH) and tocopherol (EC₅₀ 0.25 mol/mol_DPPH). The amides are also more potent superoxide radical scavengers (IC₅₀ < 600 nm) than standard ascorbic acid (IC₅₀ 700 nm). Activity against lipid peroxidation was determined by accelerated autoxidation of highly unsaturated oils and squalene using the Rancimat. Again, the antioxidative potentials of the DHMA amides against lipid oxidation as determined by the Rancimat, are at least equal or higher compared to the standard lipid antioxidants tocopherol, BHT, BHA, and ascorbylpalmitate (concentration in soybean oil 0.05%, all other oils 0.025%, squalene 0.005%). In squalene, an equi‐amount mixture of DHMA octylamide and α‐tocopherol shows a synergistic effect. Last but not least, the amides are able to protect an emulsion of linoleic acid/β‐carotene against oxidation initiated by N, N‐azodiisobutyramidine dihydrochloride (IC₅₀ 0.19‐0.77 mmol/l, ascorbic acid > 0.9, tocopherol 0.08). The DHMA octylamide in combination with ascorbic acid shows a synergistic antioxidative effect in the emulsion model. In conclusion, the new alkylamides of DHMA are easy to synthesize, potent radical scavengers and protect lipids, in particular the highly unsaturated, both in bulk and in emulsions against autoxidation.     

2,2′‐Bis(monoacylglycero) PO4 (BMP), but Not 3,1′‐BMP,Increases Membrane Curvature Stress to Enhance α‐Tocopherol Transfer Protein Binding to Membranes

Previous work revealed that α‐tocopherol transfer protein (α‐TTP) co‐localizes with bis(monoacylglycero)phosphate (BMP) in late endosomes. BMP is a lipid unique to late endosomes and is believed to induce membrane curvature and support the multivesicular nature of this organelle. We examined the effect of BMP on α‐TTP binding to membranes using dual polarization interferometry and vesicle‐binding assay. α‐TTP binding to membranes is increased by the curvature‐inducing lipid BMP. α‐TTP binds to membranes with greater affinity when they contain the 2,2′‐BMP versus 3,1′‐BMP isomers.     

Antioxidant α‐tocopherol/γ‐cyclodextrin–inclusion complex encapsulated poly(lactic acid) electrospun nanofibrous web for food packaging

α‐Tocopherol (α‐TC) and α‐TC/cyclodextrin (CD)–inclusion complex (IC) incorporated electrospun poly(lactic acid) (PLA) nanofibers (NF) were developed via electrospinning (PLA/α‐TC–NF and PLA/α‐TC/γ‐CD–IC–NF). The release of α‐TC into 95% ethanol (fatty food simulant) was much greater from PLA/α‐TC/γ‐CD–IC–NF than from PLA/α‐TC–NF because of the solubility increase in α‐TC; this was confirmed by a phase‐solubility diagram. 2,2‐Diphenyl‐1‐picrylhydrazyl radical‐scavenging assay shows that PLA/α‐TC–NF and PLA/α‐TC/γ‐CD–IC–NF had 97% antioxidant activities; this value was expected to be high enough to inhibit lipid oxidation. PLA/α‐TC–NF and PLA/α‐TC/γ‐CD–IC–NF were tested directly on beef with the thiobarbituric acid reactive substance (TBARS) method, and the nanofibers displayed a lower TBARS content than the unpackaged meat sample. Thus, active packaging significantly enhanced the oxidative stability of the meat samples at 4 °C. In conclusion, PLA/α‐TC/γ‐CD–IC–NF was shown to be promising as an active food‐packaging material for prolonging the shelf life of foods. © 2017 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2017 , 134, 44858.     

Stability of the lipid fraction of milk‐based infant formulas during storage

A study is made of the effects of storage (time and temperature) on the lipid fraction of four milk‐based adapted infant formulas with basically the same composition, though differing in the iron salt added (lactate or sulfate) and/or the vitamin E source (α‐tocopherol or α‐tocopherol acetate). Peroxide value, hydroperoxide C₁₈ percentage and thiobarbituric acid‐reactive substance (TBARS) content were used as indicators of lipid peroxidation. Fat contents remained stable throughout storage. Peroxide values increased from the first storage month and were affected by storage time, although they exhibited irregular behavior. Storage time and temperature affected hydroperoxide percentage, which was seen to be the earliest indicator of lipid oxidation, being measurable in newly manufactured formulas. TBARS values were only affected by storage time. No statistically significant differences were found among the four infant formulas for any of the lipid oxidation indicators.