Protection of fish oil from oxidation with sesamol Fhaner, Matthew; Hwang, Hong-Sik; Winkler-Moser, Jill K. ...
European journal of lipid science and technology,
06/2016, Letnik:
118, Številka:
6
Journal Article
Recenzirano
The aim of this study was to determine whether sesamol may provide antioxidant protection for marine omega‐3 fatty acids. We tested the effectiveness of sesamol at two temperatures, 30 and 50°C and ...compared its antioxidant activity with butylated hydroxytoluene (BHT), a commercial rosemary extract, and gamma‐oryzanol. Each antioxidant system was tested at two concentrations, 0.84 and 8.4 mM except for BHT of which the concentration was fixed at 0.84 mM BHT (200 ppm, the regulatory limit allowed in oils). 0.84 mM phenolic diterpenes in the rosemary extract protected fish oil very well. 0.84 mM sesamol was not as good as the rosemary extract as indicated by peroxide values, conjugated diene values, eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) levels, and volatile compounds formation. However, 8.4 mM sesamol performed better than the rosemary extract containing 8.4 mM phenolic diterpenes in peroxide values and headspace volatiles compounds during storage of the stripped fish oil for 14 days at 30 and 50°C, while it showed similar results as the rosemary extract in conjugated diene values and EPA and DHA levels. Gamma‐oryzanol was also evaluated for protection of fish oil. However, it was found that gamma‐oryzanol was less effective than the other antioxidants tested in this study.
Practical applications: At 8.4 mM (0.13 wt%), sesamol, a natural antioxidant, showed better than or comparable antioxidant activity to a commercial rosemary extract toward fish oil during storage at 30 and 50°C. Considering problems of flavor, odor, and color associated with a rosemary extract and that a rosemary extract product is typically sold as a solution containing only a few percent of active ingredients for oil applications, such as omega‐3 oil supplements and frying oil due to the low solubility of active ingredients in oil, sesamol offers advantages over the rosemary extract as it can be used as a pure form without mixing with other ingredients.
8.4 mM sesamol protected fish oil from oxidation better than the leading commercial natural antioxidant, rosemary extract, containing 8.4 mM phenolic diterpenes at 30 and 50°C. Gamma‐oryzanol was less effective than the other antioxidants tested in this study.
8.4 mM sesamol protected fish oil from oxidation better than the leading commercial natural antioxidant, rosemary extract, containing 8.4 mM phenolic diterpenes at 30 and 50°C. Gamma‐oryzanol was less effective than the other antioxidants tested in this study.
Antioxidant activity of sesamol was investigated in soybean oil using a miniaturized frying experiment with potato cubes fried at 180 °C. Oxidation of soybean oil was determined by gel permeation ...chromatography for polymerized triacylglycerols and by ¹H-NMR spectroscopy for reactions at reactive sites of soybean oil molecules including olefinic, bisallylic and allylic protons during frying. Sesamol showed lower antioxidant activity than 0.02 % (w/w) tert-butylhydroquinone (TBHQ) at the same molar concentration. Higher concentrations of sesamol provided better antioxidant effects indicating that no prooxidant activity occurred. Sesamol in this frying test showed better results than 0.02 % TBHQ when the concentration was as high as 0.66 % by weight. An HPLC experiment showed that the concentration of sesamol decreased sharply during frying. Thermogravimetric analysis indicated that sesamol is highly volatile and easily oxidizes when exposed to air. To overcome this problem, two multiple addition methods were evaluated in which sesamol was added portion by portion every hour. The multiple additions of divided portions of 0.66 % (w/w) sesamol maintained the concentration of sesamol at the minimum of 0.04–0.06 % throughout the frying process and showed improved antioxidant activity compared to one single addition of 0.66 % sesamol at the beginning of frying. One of the multiple addition methods showed 28, 18, 59, and 27 % less polymerized triacylglycerols and losses of olefinic, bisallylic and allylic protons, respectively, than 0.02 % TBHQ after 8-h frying. This study shows that sesamol can be used as an alternative for synthetic antioxidants for frying oil.
The food industry is seeking natural antioxidants for edible oils that have comparable activity to synthetic counterparts. In this study, Osage orange extract (OOE) rich in osajin (42.9%) and ...pomiferin (30.0%) was obtained after hexane extraction of the fruit, and its antioxidant activity was examined in stripped soybean oil (SBO) and fish oil (FO), in which antioxidants and polar compounds were removed. The antioxidant activity of OOE was compared with commercial natural antioxidants (i.e., rosemary extract and mixed tocopherols) and a synthetic antioxidant, butylated hydroxytoluene (BHT), during storage at 25 and 40 °C. The 0.1% OOE had stronger antioxidant activity than 0.1% rosemary extract and 0.1% mixed tocopherols in both oils at 25 and 40 °C. Its activity was similar to 0.02% BHT in SBO and was similar or slightly stronger than 0.02% BHT in FO. When OOE was studied at 0.05, 0.1, and 0.2%, there was a weak dose–response in SBO but a stronger dose–response in FO. Headspace volatile analysis using solid phase micro‐extraction (SPME) combined with GC–MS indicated that 0.1% OOE was very effective in preventing the formation of volatile oxidation products in both oils. Although it should be further tested for safety before the actual use, this study shows that OOE can be developed as an antioxidant for edible oils.
The antipolymerization activity of the lignans including nordihydroguaiaretic acid, (+)-pinoresinol, (−)-secoisolariciresinol, enterodiol, and two sesame lignans (sesamol and sesamin), and four model ...compounds (4-ethylcatechol, 2-methoxy-4-propylphenol, 4-methyl-2,6-dimethoxyphenol, and piperonyl alcohol) were investigated for soybean oil at frying temperature (180 °C). The heated samples were analyzed by gel-permeation chromatography for polymerized triacylglycerols and by 1H NMR to monitor the decrease in peak intensities for bisallylic protons and olefinic protons. The heating test results were compared with ability to scavenge the radical 2,2′-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) to understand the relationship between radical-scavenging ability at room temperature and antipolymerization activity at 180 °C. It was found that the antipolymerization activity of a lignan at frying temperature cannot be predicted solely from the radical-scavenging ability at room temperature. The lignans tested in this research had antipolymerization activity, but it was not as strong as that of 200 ppm tert-butylhydroquinone (TBHQ) with equivalent of phenolic moiety (0.0012 meq/g). At higher concentrations, however, sesamol, nordihydroguaiaretic acid, and (+)-pinoresinol had better antipolymerization activity than the legal limit set for TBHQ (200 ppm, 0.0012 meq/g). Therefore, this research showed that by using an appropriate concentration, these natural antioxidants can replace synthetic antioxidants and provide better antioxidation activity.
Many types of plant-based materials have been investigated as fat replacers or meat extenders in beef patties and meatballs, including cereal and pulse flours as well as isolated plant proteins. ...Previously, excess steam jet cooking and drum drying of pulse flours were shown to impart potentially useful properties as food ingredients. In this study, pinto bean flour was jet-cooked and drum-dried (JC-DD) and compared with raw pinto bean flour when added to ground beef patties. The finely milled flours were mixed with ground beef at levels of 6, 12, and 18% along with equal amounts of water. The effects of jet cooking and drum drying on the flour included complete breakdown of starch granules, greatly reduced viscosity upon heating in water, and substantial reduction of several volatile beany flavor components. The highest level of JC-DD flour resulted in the highest cooked patty weight, moisture content, and diameter and the lowest cooking time, springiness, and fat content. There were significant color changes in both raw and cooked beef patties to which pinto bean flour was added, but they were not large due to the native color of bean seed coats. Texture analysis revealed that addition of JC-DD flour to the meat resulted in a greater degree of tenderizing compared to the raw flour. The experiments indicate that further investigation of different flour/water ratios and different pulse types might lead to higher substitution levels. Novelty Impact Statement. The use of pulse flour as a meat extender was investigated with the novel approach of processing the pulse flour by excess steam jet cooking and drum drying. Comparison of the effects of raw and jet-cooked flour on the properties of cooked ground beef patties revealed advantages of jet cooking the flour including higher cooked patty weight, moisture content, and diameter and a greater degree of tenderizing.
As consumers continue to become more interested in the health properties of the food ingredients they purchase, the market potential for new functional ingredients, such as structured lipids and ...spreadable products, continues to grow. Recently we reported a solvent fractionation procedure for the production of a spreadable product derived from rice bran oil. This material is enriched in phytosterols and rice bran wax relative to crude rice bran oil and has rheological properties that differ vastly from the constituent oil. Here we evaluate the suitability of such a spread for use as a functional ingredient. Two potential avenues are explored: the use of the material as an antioxidant source in frying oils, and the use of this material as a fat replacer in baked goods. As an additive, the material was shown to impart oxidative stability to the oil. This spread was also successfully incorporated into two baked goods with consistently high acceptability ratings for both baked goods tested. Practical applications: We have created a novel semisolid material from crude rice bran oil that can serve as a functional ingredient in a variety of capacities. In this work we incorporate the material into edible oils and baked goods to evaluate its suitability for continued development as an ingredient. In a frying oil, this material may extend the life of the oil by protecting the oil from oxidation during heating. We also show through sensory studies that this material can be successfully used in a bread or granola as a substitute for a portion of the butter or margarine. The high stability and positive sensory reception of this ingredient suggest that this spread might be suitable for further development into a functional food that is allergen‐free, trans‐fat free, and high in antioxidants.
Vegetable oil is extracted from oil rich seeds, such as soybeans. Genetic engineering of green plants to accumulate oil in vegetative tissue is a future source of oil that promises increased land ...productivity and the use of marginal lands. However, the low concentration of lipids in current engineered plant biomass samples makes the oil extraction process challenging and expensive. In this study, liquid hot water (LHW) pretreatment was investigated to enhance oil recovery from the solids and increase enzymatic hydrolysis efficiency of such feedstocks. Corn germ meal was chosen as a model feedstock representing lipid-producing energy crops. Germ meal was pretreated at 160 and 180 °C for 10 and 15 min at 20% w/w solids loading. Enzymatic hydrolysis on the pretreated solid was performed. After pretreatment, the oil concentration increased by 2.2 to 4.2 fold. The most severe pretreatment condition of LHW, at 180 °C for 15 min, gave the maximum oil concentration (9.7%, w/w), the highest triacylglycerol (TAG) content of the extracted oil (71.6%), and the highest conversions of glucose and xylose (99.0% and 32.8%, respectively). This study demonstrates that the optimal pretreatment condition for corn germ meal is 180 °C LHW for 15 min. Pretreatment improves lipids recovery from oil bearing biomass with little or no effect on the lipid profile.
The fatty acid profiles and tocopherol and phytosterol contents of crude oils of cress (
Lepidium sativum L.) and field pennycress (
Thlaspi arvense L.) are reported, along with yields from the ...corresponding seeds. The physical properties of these oils were also determined, which included oxidative stability, kinematic viscosity, viscosity index, low temperature fluidity, specific gravity, acid value, lubricity, and iodine value. The oil content of dried cress and field pennycress seeds was 22.7 and 29.0
wt%, respectively. The primary fatty acids found in cress oil were oleic (30.6
wt%) and linolenic acids (29.3
wt%), whereas field pennycress oil was principally composed of erucic (32.8
wt%) and linoleic (22.4
wt%) acids. Cress oil contained high concentrations of γ- (1422
ppm) and δ- (356
ppm) tocopherols, whereas α-tocopherol (714
ppm) was the primary tocopherol discovered in field pennycress oil. The overall tocopherol concentrations of cress and field pennycress oils were 1799 and 851
ppm, respectively. The primary phytosterols elucidated in cress and field pennycress oils were sitosterol and campesterol, with avenasterol also present in significant quantity in cress oil. The total phytosterol concentration in cress oil (14.41
mg/g) was greater than that in field pennycress (8.55
mg/g) oil. Field pennycress oil exhibited excellent low temperature fluidity, whereas cress oil was more stable to oxidation and over a range of temperatures displayed lower kinematic viscosities as well as a higher viscosity index. The acid and iodine values of field pennycress oil were lower than those for cress oil, but both oils had excellent lubrication properties.
In an effort to develop alternatives for harmful trans fats produced by partial hydrogenation of vegetable oils, oleogels of high‐stearic soybean (A6 and MM106) oils were prepared with sunflower wax ...(SW) as the oleogelator. Oleogels of high‐stearic oils did not have greater firmness when compared to regular soybean oil (SBO) at room temperature. However, the firmness of high‐stearic oil oleogels at 4 °C sharply increased due to the high content of stearic acid. High‐stearic acid SBO had more polar compounds than the regular SBO. Polar compounds in oil inversely affected the firmness of oleogels. Differential scanning calorimetry showed that wax crystals facilitated nucleation of solid fats of high‐stearic oils during cooling. Polar compounds did not affect the melting and crystallization behavior of wax. Solid fat content (SFC) showed that polar compounds in oil and wax interfered with crystallization of solid fats. Linear viscoelastic properties of 7% SW oleogels of three oils reflected well the SFC values while they did not correlate well with the firmness of oleogels. Phase‐contrast microscopy showed that the wax crystal morphology was slightly influenced by solid fats in the high‐steric SBO, A6.
•Synthesis procedures were improved for g scale synthesis of phytosteryl ferulates.•Radical scavenging activities of phytosteryl ferulates were lower than ferulic acid.•Antioxidant activity of ...phytosteryl ferulates was low in soybean OSI analysis.•Phytosterol structural features greatly affected antioxidant activity during frying.
Steryl ferulates synthesised from commercial sterols as well as commercial oryzanol were used to better understand how structural features affect antioxidant activity in vitro by the ABTS+ radical decolorization assay, by oxidative stability index (OSI) of soybean oil, and by analysis of antioxidant activity during frying. Steryl ferulates inhibited the ABTS+ radical by 6.5–56.6%, depending on their concentration, but were less effective, especially at lower concentrations, than ferulic acid. Ferulic acid and steryl ferulates had either no effect, or lowered the OSI of soybean oil by up to 25%, depending on the concentration. In their evaluation as frying oil antioxidants, steryl ferulates with a saturated sterol group had the best antioxidant activity, followed by sterols with one double bond in the C5 position. The results indicate that a dimethyl group at C4 as well as a C9,C19 cyclopropane group, as found in oryzanol, negatively affects antioxidant activity in frying oils.
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