Showing papers in "Journal of the American Oil Chemists' Society in 2014"

Structure and Physical Properties of Plant Wax Crystal Networks and Their Relationship to Oil Binding Capacity

Abstract: The microstructure, melting and crystallization behavior, rheological properties and oil binding capacity of crystalline networks of plant-derived waxes in edible oil were studied and then compared amongst different wax types. The critical concentrations for oleogelation of canola oil by rice bran wax (RBX), sunflower wax, candelilla wax, and carnauba wax were 1, 1, 2, and 4 %, respectively, suggesting RBX and sunflower wax are more efficient structurants. A phenomenological two-phase exponential decay model was implemented to quantify the oil-binding capacity of these oleogels. Parameters obtained from this empirical model were then evaluated against microscale structural attributes such as crystal size, mass distribution and porosity to determine the structural dependence of oil-binding capacity. Gels containing candelilla wax exhibited the greatest oil-binding capacity, as they retained nearly 90 % of their oil. This is due to the small crystal size as well as the spatial distribution of these crystals. Using a microscopic to macroscopic approach, this study examines how the structural characteristics unique to each wax and resulting oleogel system affect functionality and macroscopic behavior.

Recovery and Removal of Phenolic Compounds from Olive Mill Wastewater

Abstract: Food wastes are today considered as a cheap source of valuable components since the existent technologies allow the recovery of target compounds and their recycling inside the food chain as functional additives in different products. Olive mill wastewater (OMW) is generated from olive oil extraction systems. It has high added-value compounds namely phenolics, recalcitrants, pectin, and some important enzymes. It causes a certain amount of toxicity/phytotoxicity because of its phenolic compounds. OMW also has significant impacts when discharged directly into surface waters. Therefore, the treatment of olive mill wastewater is very much needed. Several types of techniques have been investigated for OMW treatment along with recovery and removal of its phenolic compounds. Among these techniques, physical ones are utilized for extraction purposes, while chemical and biological methods are applied in order to diminish organic load. In this review, current status and recent developments in the recovery and removal of phenolic compounds from OMW have been critically examined.

Current Knowledge in Soybean Composition

Abstract: The soybean [Glycine max (L.) Merr.] is grown worldwide for its high protein and oil contents. Characterization of soybean seed components lends itself to understanding how soybean production can meet the needs of a growing world population. For this article, literature was reviewed and condensed to create a well-rounded picture of the current understanding of structural, functional, and nutritional properties of soybean components. Natural variation in soybean protein, lipid, and carbohydrate components, as well as the minor constituents phytic acid and isoflavones, are mentioned. Environment- or genetic-induced shifts in natural variation are described with respect to nutrition and functional improvements in soybean.

Properties and Stability of Hazelnut Oil Organogels with Beeswax and Monoglyceride

Abstract: The objectives of this study were to produce and characterize hazelnut oil (HO) organogels with beeswax (BW) and monoglyceride (MG) organogelators. Oil binding capacities of most samples were over 99 %. As the organogelator level increased, crystal formation time decreased, but solid fat content (SFC %) was enhanced. Although the highest SFC was 8.52 % among the organogel samples, it was 30.35 % in the commercial shortening (CS) at 20 °C. The peak melting temperature of CS was 41.86 °C, and almost all organogels had very close values to it. Melting enthalpies of the samples ranged from 0.48 to 13.40 J/g. Firmness and stickiness values of all samples were measured each month during 90 days of storage. There was no important change during storage. The organogels were texturally very stable, and were very homogenous and smooth in structure. Polarized light microscopy pictures revealed needle-like crystals for BW and rosette-like aggregates for MG organogels. The X-ray diffraction measurements of the crystals also showed the difference of the two types. There would be some hydrogen bonding in only MG organogels as predicted from the infrared spectra. The organogels were very stable against oxidation during storage. HO organogels can be used as shortening or margarine-like fat stock.

The Antioxidant Activity and Oxidative Stability of Cold-Pressed Oils.

Abstract: In our study, we characterized the antioxidant activity and oxidative stability of cold-pressed macadamia, avocado, sesame, safflower, pumpkin, rose hip, Linola, flaxseed, walnut, hempseed, poppy, and milk thistle oils The radical scavenging activity of the non-fractionated fresh oil, as well as the lipophilic and hydrophilic fractions of the oil was determined using a 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay The fatty acid composition of the fresh and stored oils was analyzed by gas chromatography The acid value, peroxide value, p-anisidine value and conjugated diene and triene contents in the fresh oils, as well as in those stored throughout the whole period of their shelf life, were measured by CEN ISO methods The antioxidant activity of the oils expressed as Trolox equivalent antioxidant capacity (TEAC), ranged from 017 to 232 mM The lipophilic fractions of the oils were characterized by much higher antioxidant activity than the hydrophilic ones There were no significant changes in fatty acid composition and only slight changes in the oxidative stability parameters of the oils during their shelf life Through the assessment of the relationship between antiradical activity and the oxidative stability of oils, it is proposed that a DPPH assay predicts the formation of oxidation products in cold-pressed oils—however, the correlations differ in fractionated and nonfractionated oils

Composition of Coconut Testa, Coconut Kernel and its Oil

Abstract: Testa, a by-product from the coconut processing industry is getting wasted. A study was carried out to utilize testa as a source of edible oil. The composition of the oils from testa of wet coconut (WCT) and copra (CT) were evaluated and compared with wet coconut whole, copra whole, wet coconut white kernel and copra white kernel. The samples had fat as a major component ranging from 34 to 63 %. Oils had 90–98.2 % triacylglycerols, 1–8 % diacylglycerols and 0.4–2 % monoacylglycerols. The triacylglycerol composition of oil from WCT had decreased trilaurin and increased triolein. Lauric acid content of CT was 40.9 % and WCT was 32.4 % whereas other oils were 50–53 %. Oils from testa were richer in monounsaturates and polyunsaturates than other coconut oil samples. The phenolics and phytosterols content were 0.2–1.9 % and 31–51 mg%, respectively. The total phenolic acids and tocopherol content of oils from CT (313.9 μg%, 22.3 mg%) and WCT (389.0 μg%, 100.1 mg%) were higher than other samples (94.8–291.4 μg%, 2.5–6.7 mg%). These studies indicated that the oil from coconut testa contained more of natural antioxidants such as tocopherols, tocotrienols and phenolics compared to coconut kernel oil and may confer health benefits.

Comparison of Fatty Acid Methyl and Ethyl Esters as Biodiesel Base Stock: a Review on Processing and Production Requirements

Abstract: Fatty acid methyl esters (FAME) were the first fatty acid esters to be introduced for use as biodiesel. However, there is a growing interest in the use of fatty acid ethyl esters (FAEE) in biodiesel. Both FAME and FAEE have their own unique advantages and disadvantages. These differences are ultimately attributable to the structural differences imparted by the alcohols used in their production. Sources of reactants as well as their safety issues, are a focus of this review. Also reviewed are the comparative characteristics and properties of both biodiesel types in terms of physicochemical features and performance. Processing requirements, reaction times and molar ratios of alcohol to oil, together with problems and drawbacks, are discussed. Recent developments on improving the yield of biodiesel, include mixing methanol and ethanol in the same reaction with ethanol acting as a co-solvent, and enzymatic methanolysis and ethanolysis are also highlighted.

Physico-chemical, Sensory and Aromatic Properties of Cold Press Produced Safflower Oil

Abstract: In this study, seeds from the safflower variety called “Dincer” were roasted and microwaved before oil extraction by cold pressing. Some physico-chemical analyses (moisture, ash, oil content and color) were performed in safflower meals. Physico-chemical properties (refractive index, viscosity, turbidity, specific gravity, color, free acidity, peroxide value, iodine number), nutritional components (total phenolics, antioxidant capacity, tocopherol content), sterol composition and fatty acid composition of produced oils were also determined. Volatile components of the oils were detected by solid-phase microextraction/gas chromatography–mass spectrometry technique. Quantitative descriptive analysis was accomplished with trained panelists by 11 definition terms. Cold pressing yielded less oil than solvent extraction, but oil quality was superior and a refining process was not required. There was no significant difference between samples for fatty acid composition and some physico-chemical parameters. Whereas, microwave treatment caused a decrease in oil turbidity, free acidity, α-tocopherol and some sterol contents and an enhancement in total phenolic content, antioxidant capacity and peroxide value. Moreover, microwave treatment led to an increased nutty aroma in the oil. In contrast, isot pepper aroma was decreased by microwave treatment. This study provides very important information about the safflower oils for the first time in the literature.

The use of FTIR spectroscopy and chemometrics for rapid authentication of extra virgin olive oil

Abstract: The authenticity of high value edible fats and oils including extra virgin olive oil (EVOO) is an emerging issue, currently. The potential employment of Fourier transform infrared (FTIR) spectroscopy in combination with chemometrics of multivariate calibration and discriminant analysis has been exploited for rapid authentication of EVOO from canola oil (Ca-O). The optimization of two calibration models of partial least square (PLS) and principle component regression was performed in order to quantify the level of Ca-O in EVOO. The chemometrics of discriminant analysis (DA) was used for making the classification between pure EVOO and EVOO adulterated with Ca-O. The individual oils and their blends were scanned on good contact with ZnSe crystals in horizontal attenuated total reflectance, as a sampling technique. The wavenumbers of 3,028–2,985 and 1,200–987 cm−1 were used for quantification and classification of EVOO adulterated with Ca-O. The results showed that PLS with normal FTIR spectra was well suited for quantitative analysis of Ca-O with a value of the coefficient of determination (R2) > 0.99. The error, expressed as root mean square error of calibration obtained was relatively low, i.e. 0.108 % (v/v). DA can make the classification between pure EVOO and that adulterated with Ca-O with one misclassified reported.

Study of Formulation and Stability of Co-surfactant Free Water-in-Olive Oil Nano- and Submicron Emulsions with Food Grade Non-ionic Surfactants

Abstract: Nanoemulsions are of great interest in food industry finding various food applications. However, oil-in-water (o/w) nanoemulsions have been intensively investigated, but there are few studies on w/o nanoemulsions. In the present work the preparation of nanoemulsions with olive oil using non-ionic surfactants (Tween 20, 40, 60, 80, Span 20, 80) without the addition of a co-surfactant was studied and their emulsion properties and stability were examined. The stable nanoemulsions were presented in ternary phase diagrams (oil–water-surfactant) for each surfactant and the emulsifying ability of the efficient surfactants was determined. The nanoemulsions properties were evaluated in relationship to compositional components. From the results of this study it can be concluded that stable olive oil nanoemulsions without use of a co-surfactant were obtained and moreover the most efficient type of emulsifier and its ratio of addition in the system were determined.

Profile of Bioactive Compounds in Avocado Pulp Oil: Influence of the Drying Processes and Extraction Methods

Abstract: The influence of different procedures of pulp drying and oil extraction methods on the concentrations of α-tocopherol, squalene and several phytosterols in avocado oil was evaluated. Pulp portions of Fortune variety avocados were dried either by lyophilization or under circulating air at 40 or 70 °C. For lyophilization and for each air drying temperature, the oil was obtained either by cold pressing or with Soxhlet extraction using petroleum ether. The dehydrated pulp (73 % of the pulp weight) yielded 25–33 % oil by cold pressing, and 45–57 % oil by Soxhlet extraction. Infrared spectroscopy and gas chromatography with FID and mass spectrometry detection were used to analyze the oils. α-Tocopherol, squalene, cycloartenol acetate, β-sitosterol, campesterol and stigmasterol were present in all the oil samples. In comparison to lyophilization, hot air drying resulted in smaller concentrations of α-tocopherol, squalene and β-sitosterol, and larger relative concentrations of campesterol and cycloartenol acetate. On the other hand, extraction by cold pressing produced a smaller amount of oil, with greater concentrations of α-tocopherol and squalene, and lower contents of campesterol and cycloartenol acetate, than Soxhlet extraction. Thus, the oil yield was maximal with lyophilization and Soxhlet extraction, but lyophilization and cold pressing produced oils which had greater concentrations of antioxidants and other bioactive compounds.

GC-FID/MS Analysis of Fatty Acids in Indian Cultivars of Moringa oleifera: Potential Sources of PUFA

Abstract: In the present investigation, the fatty acid profile was analysed in vegetative and reproductive parts of eight commercially cultivated Indian cultivars of Moringa oleifera and verified by gas chromatography mass spectra. In leaves, α-linolenic acid (C18:3, cis-9,12,15) was found in the highest quantity (49–59 %) followed by palmitic acid (C16:0) (16–18 %), and linoleic acid (C18:2, cis-9,12) (6–13 %). The total content of saturated fatty acids and unsaturated fatty acids showed a ratio of 0.33 (cv. DHANRAJ) to 0.39 (cv. PKM-2) in leaves, 0.53 in flowers and 0.56 in tender pods. Similarly, polyunsaturated fatty acids and total monounsaturated fatty acids were found in a ratio of 5.68 (cv. DHANRAJ) to 9.71 (cv. CO-1) in leaves, 1.11 in flowers and 2.79 in tender pods. The total lipid content was recorded in the range of 1.92 % (flowers) to 4.82 % (leaves, cv. CO-1). When considering health benefits, M. oleifera leaves contain low amounts of saturated fatty acids, a high mono- and polyunsaturated fatty acid content, which can enhance the health benefits of Moringa-based products.

Evolution of Oxidative Values during Kinetic Studies on Olive Oil Oxidation in the Rancimat Test

Abstract: A comparative study was carried out in order to evaluate the kinetics of the formation of a number of primary and secondary oxidation products during oxidation of olive oil in the Rancimat test at 100–130 °C. There were good correlations between the Rancimat index (OSI) and stability indices (IP) measured in the Rancimat test with no significant differences in kinetic parameters calculated from them. Mean values of the temperature coefficient, Q 10 number, activation energy (E a), frequency factor (A), and free energy of activation (ΔG ++) for olive oil oxidation were calculated to be −3.44 × 10−2 °C−1, 2.21, 98.91 kJ/mol, 12.17 × 1012 h−1, and 128.25 kJ/mol, respectively. Each unit change in E a was accompanied by an average 1.43 × 1012 change in A, indicating a higher contribution for factor A than for E a to the olive oil stability. The E a and A correlated well with the values of enthalpy and entropy, respectively. The values of OSI or IP could be described well by the ΔG ++ values. Kinetic data indicated that olive oil stability is more affected by the indigenous antioxidants than by the fatty acid composition.

Sequential Fractionation of Cottonseed Meal to Improve Its Wood Adhesive Properties

Abstract: For better understanding of the adhesive properties of different fractions of cottonseed protein, cottonseed meals from both glanded and glandless cotton varieties were separated into several fractions. Each meal was sequentially extracted with water and 1 M NaCl solution, or with phosphate buffer and NaCl solution. Adhesives were prepared from the recovered fractions and hot-pressed onto maple veneer strips and tested for their properties. The adhesive strength of the water- and buffer-washed solid fractions (i.e., the un-extractable residues of the meals) from the glanded seed ranged from 1.32 to 1.62 MPa and were unchanged or increased compared with the adhesive strength of the original meal that varied from 0.98 and 1.49 MPa. Soaking the wood specimens bonded at 80 °C revealed that the water resistance of these water- and buffer-washed adhesives was significantly improved in that they exhibited no delamination during soaking compared with the meal adhesive that showed some delamination (20–30 % of the samples). Furthermore, the water resistance of these fractions with wet shear strength around 1.5 MPa was comparable to that of cottonseed protein isolate (>90 % protein) when the joints were bonded at 100 °C. The preparations from glandless cottonseed meals showed similar adhesive performances. Additional extraction of the meals with NaCl solution reduced adhesive performance. The results suggest that water- or buffer-washed cottonseed meal fractions can be used as wood adhesives and would be less costly to prepare than cottonseed protein isolates.

Structure and Physical Properties of Organogels Developed by Sitosterol and Lecithin with Sunflower Oil

Abstract: High linoleic acid sunflower oil (HLSO) with various sitosterol (Sit) to lecithin (Lec) mass ratios (i.e., 0:100–100:0) were used to develop organogels at two storage temperatures (T s: 5 and 25 °C). The results showed that, at 25 °C, the hardness value of organogels obtained from HLSO with both Sit and Lec was higher than that of organogels developed from HLSO with only Sit or Lec. Microscopy revealed that the shapes of the crystals in the organogels varied significantly with the composition of the structurant and the T s. At both T s used, the Sit:Lec (80:20) system had a lower degree of supersaturation compared with the (100:0) system. X-ray diffraction (XRD) revealed that Sit:Lec mass ratio of 70:30, 80:20 and 100:0 had similar short spacings, and the presence of Lec might be adverse to the formation of Sit crystal in oil. Small-angel X-ray scattering (SAXS) showed that the layer thickness of Sit/Lec/HLSO organogel was larger than that of Sit/HLSO organogel. It was found that the presence of Lec induced the change of self-assembly structure of Sit in HLSO and caused the changes of physical properties of organogels obtained.

Isoflavone Content of Soybean Cultivars from Maturity Group 0 to VI Grown in Northern and Southern China.

Abstract: Soybean isoflavone content has long been considered to be a desirable trait to target in selection programs for their contribution to human health and plant defense systems. The objective of this study was to determine isoflavone concentrations of various soybean cultivars from maturity groups 0 to VI grown in various environments and to analyze their relationship to other important seed characters. Forty soybean cultivars were grown in replicated trials at Wuhan and Beijing of China in 2009/2010 and their individual and total isoflavone concentrations were determined by HPLC. Their yield and quality traits were also concurrently analyzed. The isoflavone components had abundant genetic variation in soybean seed, with a range of coefficient variation from 45.01% to 69.61%. Moreover, individual and total isoflavone concentrations were significantly affected by cultivar, maturity group, site and year. Total isoflavone concentration ranged from 551.15 to 7584.07 μg g−1, and averaged 2972.64 μg g−1 across environments and cultivars. There was a similar trend regarding the isoflavone contents, in which a lower isoflavone concentration was generally presented in early rather than late maturing soybean cultivars. In spite of significant cultivar × year × site interactions, cultivars with consistently high or low isoflavone concentrations across environments were identified, indicating that a genetic factor plays the most important role for isoflavone accumulation. The total isoflavone concentration had significant positive correlations with plant height, effective branches, pods per plant, seeds per plant, linoleic acid and linolenic acid, while significant negative correlations with oleic acid and oil content, indicating that isoflavone concentration can be predicted as being associated with other desirable seed characteristics.

Antioxidant Property, Thymoquinone Content and Chemical Characteristics of Different Extracts from Nigella sativa L. Seeds

Abstract: In this study, Nigella sativa L. seeds were extracted using supercritical carbon dioxide (SC-CO2) and Soxhlet. Chemical characteristics, fatty acid composition, antioxidant activity and thymoquinone content of N. sativa L. extracts obtained through different methods were investigated and compared. It was revealed that antioxidant activity and thymoquinone content could be significantly different for SC-CO2 and Soxhlet extracts. The results for fatty acid composition indicated that linoleic acid, palmitic acid and oleic acid were the main fatty acids in both extracts. The SC-CO2 extraction could provide an extract with higher quality and antioxidant activity compared to Soxhlet extraction method and can be considered a more appropriate method for attaining a high-quality extract.

Optimization of Mixing Parameters for α-Tocopherol Nanodispersions Prepared Using Solvent Displacement Method

Abstract: A bottom-up approach based on a solvent displacement technique was used for the production of α-tocopherol nanodispersions. Response surface methodology was utilized to study the effect of the mixing conditions of organic and aqueous phases, namely, mixing speed (1 × 100–6 × 100 rpm) and mixing time (30–150 s) on the average particle size (nm), polydispersity index and α-tocopherol concentration (mg/L) of the nanodispersions. Second order regression models, with high coefficient of determination values (R 2 > 0.94 and adjusted R 2 > 0.79), were significantly (p < 0.05) fitted for predicting the α-tocopherol nanodispersion characteristics as functions of mixing parameters. A multiple optimization procedure presented the optimum mixing speed and time as 3.8 × 100 rpm and 70 s, respectively. The statistically insignificant differences between experimental and predicted values of studied responses, verified the satisfactoriness of the models found for explaining the variation of produced nanodispersions, as a function of mixing conditions.

Antioxidant Activity of Sesame (Sesamum indicum L.) Cake Extract for the Stabilization of Olein Based Butter

Abstract: This study investigated the effect of ethanolic sesame cake extract on oxidative stabilization of olein based butter. Fractionation of cream was performed by the dry fractionation technique at 10 °C, ethanolic sesame cake extract (SCE) was incorporated into olein butter at three different concentrations; 50, 100, 150 ppm (T1, T2, T3) and compared with a control. The total phenolic content of SCE was 1.72 (mg gallic acid equivalent g−1 dry weight). The HPLC characterization of ethanolic sesame cake revealed the presence of antioxidant substances viz. sesamol, sesamin and sesamolin in higher extents. The DPPH free radical scavenging activity of SCE was 83 % as compared to 64 and 75 % in BHA and BHT. Fractionation of milk fat at 10 °C significantly (p 0.05). Ethanolic SCE can be used for the long-term preservation of olein butter, with acceptable sensory characteristics.

Evaluation of the Phenolic Content and Antioxidant Activity of Different Seed and Nut Cakes from the Edible Oil Industry

Abstract: The objective of this work was to extract water-soluble compounds from different seed and nut cakes under the same conditions and compare the phenolic content and antioxidant activity of the cake extracts. Seed cakes of sunflower, pumpkin, flaxseed and defatted sesame, and nut cakes of almond, pecan, macadamia and hazelnut were used in the experiments. Extracts were obtained by solid–liquid extraction with a water/ethanol solution (20:80, v/v). Total phenolic content, flavonoids, flavan-3-ols and condensed tannins in the extracts were determined using spectrophotometric analysis. Antioxidant properties of the extracts were determined by the DPPH and ABTS radical scavenging methods, and by determination of the reducing power and chelating activity. The extract from pecan nut cake presented the highest amounts of all compounds analyzed, followed by sunflower seed and hazelnut cake extracts. These samples also had the highest effects on the ABTS and DPPH radicals, as well as the uppermost reducing powers. The extracts from pecan nut and sunflower and sesame seeds were analyzed using HPLC and individual phenolics were further characterized.

Evaluation of Oxygen-Limitation on Lipid Oxidation and Moisture Content in Corn Oil at Elevated Temperature

Abstract: The role of oxygen-limitation on lipid oxidation and moisture content were tested in corn oil heated to 60, 100, and 140 °C. The degree of oxidation was determined by analyzing headspace oxygen content, conjugated dienoic acids (CDA), and p-anisidine value (p-AV). The moisture content in bulk oil was analyzed by the Karl Fischer method. Oxygen-limited samples heated to 100 and 140 °C had significantly more lipid oxidation than oxygen-unlimited samples at early timepoints (p < 0.05). After this period, the oxygen-unlimited samples had more lipid oxidation based on CDA and p-AV assays. During those initial periods, oxygen-limited samples had significantly higher moisture content than oxygen-unlimited samples (p < 0.05), which implies that moisture content in oils plays an important role in the rate of lipid oxidation. The increased moisture content in bulk oil under oxygen-limited conditions is due to headspace moisture rather than moisture inside the oil. However, the effects of oxygen-limitation on lipid oxidation were less clear at 60 °C than at 100 or 140 °C.

Polyphenols of Pistachio (Pistacia vera L.) Oil Samples and Geographical Differentiation by Principal Component Analysis

Abstract: The phenolic compounds of Italian and Turkish pistachio oil samples were investigated by gas chromatography–mass spectrometry (GC–MS) with the aim of identifying substances also present in very low concentration; 21 compounds were identified by means of the mass spectra of the trimethylsilyl (TMS) derivatives. Benzoic acid derivatives (protocatechuic acid, gallic acid, 4-hydroxybenzoic acid) were the main components; 14 polyphenols were detected in pistachios for the first time. The concentrations of the compounds found were in the range 0.02–5.64 μg/g of fresh pistachio. No appreciable qualitative differences were found between samples of different origin; a multivariate approach was successfully tried to differentiate the samples according to their geographical origin, using Principal Component Analysis (PCA). Finally, Canonical Discriminant Analysis (CDA) was further conducted to classify different pistachio samples.

Selective Ethanolysis of Fish Oil Catalyzed by Immobilized Lipases

Abstract: Selective ethanolysis of fish oil was catalyzed by immobilized lipases and their derivatives in organic media. Lipases from Candida antarctica B (CALB), Thermomyces lanuginosa (TLL) and Rhizomucor miehei (RML) were studied. The three lipases were immobilized by anion exchange and hydrophobic adsorption. The discrimination between the ethyl ester of eicosapentaenoic acid (EE-EPA) and the ethyl ester of docosahexaenoic acid (EE-DHA) depends on the lipase, the immobilization support, the physico-chemical modifications of the immobilized lipase derivatives and on the solvents used. TLL and RML were much more selective than CALB. EE-EPA is released 20-fold faster than EE-DHA when ethanolysis was catalyzed, in cyclohexane, by TLL hydrophobically adsorbed on Sepabeads C18. The selectivity and stability of the different derivatives in these polar organic solvents were further improved after physico-chemical modification. The best results for activity-selectivity-stability were obtained in cyclohexane for TLL adsorbed on Sepabeads C18 and further modified via solid-phase physical modification with a polyethylenimine polymer. In this case, the initial selectivity was higher than 20, and a 80 % of EPA was released as ethyl ester after 3 h at 25 °C. At this conversion, mixtures of ethyl esters highly enriched in the ethyl ester of EPA with less than 5 % of the EE-DHA were obtained. TLL derivatives remained fully active after incubation for 24 h in anhydrous solvents.

Association Colloids Formed by Multiple Surface Active Minor Components and Their Effect on Lipid Oxidation in Bulk Oil

Abstract: Association colloids formed by surface active minor components play an important role in the oxidative stability of bulk oils. To imitate the formation of nanostructures in refined oils, multiple surface active minor components including phospholipids, free fatty acids, diacylglycerols and sterols were added to stripped corn oil. The critical micelle concentration (CMC) of the mixed components was determined. The impact of mixed minor components at below and above their CMC on oxidative stability of bulk oil and on antioxidant activity of α-tocopherol and Trolox was investigated. The CMC of the mixed surface active components in bulk oil was 20 µmol/kg oil in the presence of 383 ± 2 ppm of water. 1,2-Dioleoyl-sn-glycero-3-phosphocholine (DOPC) played an important role on the formation of association colloids since it was the most important component in forming the association colloids as confirmed by CMC and fluorescence probe studies. The association colloids formed by the mixed components showed prooxidative activity in bulk oil as determined by monitoring the formation of lipid hydroperoxide and hexanal. The activity of α-tocopherol or Trolox was not changed by mixed components association colloids. These results suggest that association colloids both physically and chemically impacted the oxidative stability and activity of antioxidants in bulk oil.

Biodiesel Synthesis in a Solvent-Free System by Recombinant Rhizopus oryzae Lipase. Study of the Catalytic Reaction Progress

Abstract: The recombinant 1,3-positional selective Rhizopus oryzae lipase (rROL) was used to synthesize biodiesel and monoacylglycerols simultaneously. The reaction was carried out in a solvent-free system with the enzyme immobilized on octadecyl-Sepabeads. Using response surface methodology, the methyl ester yield was optimized by means of the study of the effect of water, substrate molar ratio (methanol:olive oil) and methanol stepwise addition. It was concluded that in order to prevent enzyme inactivation by methanol, alcohol should be added slowly; otherwise a large amount of water would be present. Taking the best conditions, a 50.3 % yield was achieved in 3 h, which corresponds to 75.4 % of the acyl groups at the 1,3-position undergoing transesterification. It was also concluded that methyl esters result from the esterification of the free fatty acid hydrolyzed by the enzyme and also from a direct transesterification of oil. In addition, the fatty acid selectivity of rROL was found not to favor one fatty acid in olive oil over another.

Production of Canolol from Canola Meal Phenolics via Hydrolysis and Microwave-Induced Decarboxylation

Abstract: A potent antioxidant, anti-inflammatory and anti-mutagenic agent; 4-vinyl-2,6-dimethoxyphenol (canolol) was obtained from canola meal in a significant yield via alkaline (NaOH)/enzymatic (ferulic acid esterase) hydrolysis followed by microwave-assisted decarboxylation. The hydrolysis was carried out either through using canola meal directly as a substrate or by using the 70 % aqueous methanolic extract filtrates. The hydrolyzed extracts underwent RP-HPLC analysis which showed that 81.0 and 94.8 % of the total phenolics were hydrolyzed to sinapic acid after the alkaline hydrolysis of the meal and the methanolic extracts, respectively. The enzymatic hydrolysis showed lower conversion rates (49.5 and 58.3 %). The hydrolyzed extracts were consequently decarboxylated using 8-diazabicyclo[5.4.0]undec-7-ene under microwave irradiation at different conditions. The HPLC profiling of decarboxylated extracts showed that using microwave at 300 W of microwave power for 12 min brought the highest sinapic acid conversion to canolol (58.3 %) yielding 4.2 mg canolol from each gram of canola meal suggesting that the process could be commercially economical.

Lipid Content and Fatty Acid Profile of Muscle, Brain and Eyes of Seven Freshwater Fish: a Comparative Study

Abstract: The fatty acid and lipid content of the eyes, brain and muscle were determined for the following seven freshwater fish species in China: black carp, grass carp, silver carp, bighead carp, common carp, crucian carp, and Wuchang bream. Lipid contents of all seven freshwater fish were in the order of brain > eyes > muscle. Most of the freshwater fish demonstrated much lower n-3 PUFA than n-6 PUFA in all tissues with n-3/n-6 ratios varying between 0.07 and 0.40, while silver carp and bighead carp had much higher n-3 PUFA than n-6 PUFA. The percentage of PUFA in the muscle of all species are the highest compared to those of the eyes and brain, while no significant difference was observed in PUFA concentration between eyes and brain (p > 0.05). Multivariable analyses indicate that the fatty acid composition of the filter-feeder fish (silver carp and bighead carp) was distinct from the other four species.

Impact of Phosphoethanolamine Reverse Micelles on Lipid Oxidation in Bulk Oils

Abstract: Phospholipids are important minor components in edible oil that play a role in lipid oxidation. Surface active phospholipids have an intermediate hydrophilic–lipophilic balance value, which allows them to form association colloids such as reverse micelles in bulk oil. These association colloids can influence lipid oxidation since they create lipid–water interfaces where prooxidants and antioxidants can interact with triacylglycerols. In this study, we examined the formation of reverse micelles in a stripped oil system by dioleoyl phosphoethanolamine (DOPE) and the effect of these physical structures on lipid oxidation kinetics. The critical micelle concentration (CMC) of DOPE was approximately 200 µmol/kg oil at 45 °C. Oxidation kinetics studies showed that DOPE was prooxidative when it was above its CMC (400 and 1,000 µM), reducing the lag phase from 14 days (control) to 8 days. The addition of combinations of DOPE and dioleoyl phosphocholine (DOPC) resulted in formation of mixed micelles with a CMC of 80 µmol/kg oil at 45 °C. These mixed micelles were also prooxidative when concentrations (100 and 500 µM) were above the CMC, decreasing the lag phase from 14 to 8 days. These findings provide a better understanding of the role of phospholipids in lipid oxidation of edible oil and could contribute to better antioxidant solutions.

Phenolic Composition and Antioxidant Activity of Monovarietal and Commercial Portuguese Olive Oils

Abstract: Olive oil composition has been investigated using chemical approaches, since the composition has a direct impact on its quality and safety and it may be used for certification purposes. In this paper, eleven monovarietal and twelve commercial Portuguese olive oils were analyzed to determine spectrophotometrically their total polyphenol content, ortho-diphenols and antioxidant activity. The phenolic profiles of these olive oils were also studied by high performance liquid chromatography. The lowest phenolic content and antioxidant activity were observed for monovarietal olive oils, however, among these group, ‘Cobrancosa’ and ‘Redondil’ cultivars showed the highest values of these two chemical parameters. In commercial olive oils, the concentration of polyphenols, determined according to the Folin–Ciocalteu method, and the antioxidant activity (ABTS method) ranged from 97.37 ± 1.10 to 219.7 ± 1.50 mg GAE/kg of oil and from 387.2 ± 20.00 to 997.5 ± 30.90 µmol Trolox/kg, respectively. The study of the phenolic profile demonstrated that the highest concentrations of the most abundant compounds in olive oil (tyrosol, hydroxytyrosol and oleuropein) are present in commercial olive oils. The correlation coefficient between total phenolics and antioxidant activity was statistically significant (r = 0.95, p < 0.0001). The same was observed for ortho-diphenol content and antioxidant capacity (r = 0.94, p < 0.0001).

Content of Antioxidants, Antioxidant Capacity and Oxidative Stability of Grape Seed Oil Obtained by Ultra Sound Assisted Extraction

Abstract: The goal of this work was to investigate the relationship between antioxidants’ content and the oxidative stabilities of grape seed oils obtained from the Cabernet Sauvignon variety. The samples of grape seed oils were obtained by ultrasound assisted extraction. The time of extraction was varied, while the other relevant parameters: extraction temperature, solvent to solid ratio and sonication power were kept constant. For the sake of comparison, the extraction was also done using the conventional Soxhlet method. For all the oil samples obtained, the contents of total phenolic compounds (TPC), α-tocopherol and fatty acids were determined using relevant analytic methods. Importantly, in the present study, the modern analytical techniques for estimation of antioxidant capacity (measuring the chemiluminescence intensity of a luminol-hemin solution) and oxidative stability [differential scanning calorimetry (DSC), coupled with thermogravimetry (TG)] were proposed. The obtained results prove that ultrasonic irradiation enables effective extraction of grape seed oil. It was shown that the extractive yields and the amounts of total phenolic compounds and α-tocopherol increase with time of extraction; the optimum time was determined. Results obtained in this work show that, for both oxidative stability and antioxidant capacity, TPC have a more important role then α-tocopherol.