Enzymatic synthesis of lipophilic rutin and vanillyl esters from fish byproducts

Lipase-catalyzed synthesis of lipophilic phenolic antioxidants was carried out with a concentrate of n-3 polyunsaturated fatty acids (PUFAs), recovered from oil extracted from salmon ( Salmon salar ) byproduct. Vanillyl alcohol and rutin were selected for the esterification reaction, and obtained esters yields were 60 and 30%, respectively. The antioxidant activities of the esters were compared with those of commercial butylated hydroxytoluene (BHT) and α-tocopherol using DPPH radical scavenging and thiobarbituric acid assays. In the DPPH assay, rutin esters showed better activity than vanillyl esters, and on the contrary in lipophilic medium, vanillyl esters were found to be superior to rutin esters. In bulk oil system, the antioxidant activities of rutin and vanillyl derivatives were lower than that of BHT and α-tocopherol, but in emulsion, they showed better activity than α-tocopherol. By attaching to natural phenolics, the PUFAs are protected against oxidation, and PUFA improves the hydrophobicity of the phenolic, which could enhance its function in lipid systems.     

Antioxidant activity of capsaicinoid in canola oil

Interest in replacing synthetic antioxidants, namely, butylated hydroxytoluene (BHT) and butylated hydroxyanisole (BHA), with natural antioxidants is increasing. The present study examined the antioxidant activity of capsaicinoid from chili pepper in heated canola oil. The oxidation was conducted at 60, 90, 120, and 180 °C by monitoring oxygen consumption and the decrease in linoleic acid and α-linolenic acid in canola oil. At 60 °C, capsaicinoid was more effective against oxidation of canola oil compared with BHT. At higher temperatures of 90, 120, and 180 °C, capsaicinoid possessed an antioxidant activity similar to or slightly weaker that that of BHT. It was found that capsaicinoid prevented canola oil from oxidation in a dose-dependent manner. To study the structure-antioxidant relationship, it was found that the trimethylsiloxy (TMS) derivatives of capsaicinoid did not exhibit any antioxidant activity, suggesting the hydroxyl moiety was the functional group responsible for the antioxidant activity of capsaicinoid. It was concluded that capsaicinoid had the potential to be further explored as a natural antioxidant in foods, particularly spicy foods.     

Potato peel extract-a natural antioxidant for retarding lipid peroxidation in radiation processed lamb meat

The effective utilization of potato peel, a waste generated in large quantities by the food industry, as an antioxidant was investigated. Potato peel extract (PPE) exhibited high phenolic content (70.82 mg of catechin equivalent/100 g), chlorogenic acid (27.56 mg/100 g of sample) being the major component. The yield of total phenolics and chlorogenic acid increased by 26 and 60%, respectively, when the extract was prepared from gamma irradiated (150 Gy) potatoes. PPE showed excellent antioxidant activity as determined by beta-carotene bleaching and radical scavenging activity of 1,1-diphenyl-2-picrylhydrazyl (DPPH). The suitability of PPE for controlling lipid oxidation of radiation processed lamb meat was also investigated. PPE (0.04%) when added to meat before radiation processing was found to retard lipid peroxidation of irradiated meat as measured by TBA number and carbonyl content. The antioxidant activity of PPE was found to be comparable to butylated hydroxytoluene (BHT).     

Oxidative stability of tree nut oils

The oxidative stability of selected tree nut oils was examined. The oils of almond, Brazil nut, hazelnut, pecan, pine nut, pistachio, and walnut were extracted using two solvent extraction systems, namely, hexane and chloroform/methanol. The chloroform/methanol system afforded a higher oil yield for each tree nut type examined (pine nut had the highest oil content, whereas almond had the lowest). The fatty acid compositions of tree nut oils were analyzed using gas chromatography, showing that oleic acid was the predominant fatty acid in all samples except pine nut and walnut oils, which contained high amounts of linoleic acid. The tocopherol compositions were analyzed using high-performance liquid chromatography, showing that alpha- and gamma-tocopherols were the predominant tocopherol homologues present; however delta- and beta-tocopherols were also detected in some samples. The oxidative stability of nonstripped and stripped tree nut oils was examined under two conditions, namely, accelerated autoxidation and photooxidation. Progression of oxidation was monitored using tests for conjugated dienes, peroxide value, p-anisidine value, and headspace volatiles. Primary products of oxidation persisted in the earlier stages of oxidation, whereas secondary oxidation product levels increased dramatically during the later stages of oxidation. Hexanal was the major headspace aldehyde formed in all oxidized samples except walnut oil, which contained primarily propanal. Results showed that chloroform/methanol-extracted oils were more stable than hexane-extracted oils in both the accelerated autoxidation and photooxidation studies. Oils of pecan and pistachio were the most stable, whereas oils of pine nut and walnut were the least stable.     

Effect of a low-density polyethylene film containing butylated hydroxytoluene on lipid oxidation and protein quality of Sierra fish (Scomberomorus sierra) muscle during frozen storage

Fresh sierra fish (Scomberomorus sierra) fillets were packed in low-density polyethylene films with butylated hydroxytoluene (BHT-LDPE) added. Fillets packed in LDPE with no BHT were used as controls (LDPE). The packed fillets were stored at -25 degrees C for 120 days in which the film released 66.5% of the antioxidant. The influence of the antioxidant on lipid and protein quality, lipid oxidation, muscle structure changes, and shear-force resistance was recorded. As compared to LDPE films, fillets packed in BHT-LDPE films showed lower lipid oxidation, thiobarbituric acid values (4.20 +/- 0.52 vs 11.95 +/- 1.06 mg malonaldehyde/kg), peroxide values (7.20 +/- 1.38 vs 15.15 +/- 1.48 meq/kg), and free fatty acids (7.98 +/- 0.43 vs 11.83 +/- 1.26% of oleic acid). Fillets packed in BHT-LDPE films showed less tissue damage and lost less firmness than fillets packed in LDPE. A significant relationship between lipid oxidation and texture was detected (R2 adjusted, 0.70-0.73). BHT-LDPE films may be used not only to prevent lipid oxidation but also to minimize protein damage to prolong the shelf life of sierra fish.     

Evaluation of extracts from Gevuina avellana hulls as antioxidants

The antioxidant activity of the extracts from Gevuina avellana hulls was evaluated and compared with that of BHT (butylated hydroxytoluene) and BHA (butylated hydroxyanisole), using the beta-carotene bleaching assay, the accelerated oxidation of crude soybean oil, and the 2,2-diphenyl-beta-picrylhydrazyl (DPPH) radical scavenging method. Solvents of different polarity were used to obtain the extracts. Both the extraction yield and the antioxidant activity were strongly dependent on the solvent. The ethanol and diethyl ether soluble fractions were the most active with the beta-carotene assay. Ethanol and methanol extracts were the most active in hydrogen radical scavenging activity. Water and methanol inhibited more efficiently the oxidation of soybean oil at 70 and 80 degrees C, respectively. As a general trend, increased antioxidant activity was observed for increased extract concentration. Except the acetone extracts, all were stable after 6 months storage at 4 degrees C. The ethanol solubles from G. avellana hulls present antioxidant activity similar to that of synthetic antioxidants and to other reported residual agroindustrial materials.     

Chemical composition and antioxidant properties of clove leaf essential oil

The antioxidant activity of a commercial rectified clove leaf essential oil (Eugenia caryophyllus) and its main constituent eugenol was tested. This essential oil comprises in total 23 identified constituents, among them eugenol (76.8%), followed by beta-caryophyllene (17.4%), alpha-humulene (2.1%), and eugenyl acetate (1.2%) as the main components. The essential oil from clove demonstrated scavenging activity against the 2,2-diphenyl-1-picryl hydracyl (DPPH) radical at concentrations lower than the concentrations of eugenol, butylated hydroxytoluene (BHT), and butylated hydroxyanisole (BHA). This essential oil also showed a significant inhibitory effect against hydroxyl radicals and acted as an iron chelator. With respect to the lipid peroxidation, the inhibitory activity of clove oil determined using a linoleic acid emulsion system indicated a higher antioxidant activity than the standard BHT.     

Physical and Chemical Attributes and Consumer Acceptance of Sugar-Snap Cookies Containing Naturally Occurring Antioxidants

The antioxidant compounds, ascorbate (ascorbyl-2-phosphate), α-tocopherol, a combination of ascorbate and α-tocopherol, sodium phytate, and ferulic acid were tested as replacements for butylated hydroxyanisole (BHA) in preserving sugar-snap cookies. The cookies were compared with regard to shelf life, moisture content, width, stacking height, surface score, color, and texture. Following storage at 60°C, the Schaal oven test and gas-liquid chromatographic analysis of headspace gases indicated that ferulic acid and sodium phytate were suitable antioxidants for sugarsnap cookies. At present, sodium phytate is a GRAS substance, whereas ferulic acid is not. Consumer testing showed that cookies containing phytate were as acceptable as those containing BHA.     

Evaluation of antioxidant activity of Australian tea tree (Melaleuca alternifolia) oil and its components

Antioxidant activity of Australian tea tree (Melaleuca alternifolia) oil (TTO) was determined using two different assays. In the 2,2-diphenyl-1-picrylhydrazyl assay, 10 microL/mL crude TTO in methanol had approximately 80% free radical scavenging activity, and in the hexanal/hexanoic acid assay, 200 microL/mL crude TTO exhibited 60% inhibitory activity against the oxidation of hexanal to hexanoic acid over 30 days. These results were equivalent to the antioxidant activities of 30 mM butylated hydroxytoluene in both tests at the same experimental conditions. This indicated that the TTO could be a good alternative antioxidant. Inherent antioxidants, i.e., alpha-terpinene, alpha-terpinolene, and gamma-terpinene, in the crude TTO were separated and identified chromatographically using silica gel open chromatography, C(18)-high-pressure liquid chromatography, and gas chromatography-mass spectrometry. Their antioxidant activities decreased in the following order in both assays: alpha-terpinene > alpha-terpinolene > gamma-terpinene.     

Effect of antioxidants on soy oil conjugated linoleic acid production and its oxidative stability

Conjugated linoleic acid (CLA)-rich soy oil can be produced by photoisomerization of soy oil linoleic acid to produce a soy oil with up to 20% CLA. Recent studies indicate that mixed soy tocopherols added to refined bleached deodorized (RBD) oil produced significant increase in soy CLA yield during soy oil linoleic acid photoisomerization. However, the effect of common synthetic free radical scavenging antioxidants and specific tocopherols on CLA yield and its oxidative stability is not known. Therefore, this investigation evaluated the effects of various antioxidant systems on soy oil CLA yield and oxidative stability. Soy oil with added antioxidants consisting of combinations of mixed tocopherols (MT), ascorbyl palmitate (AP), butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT) and tert-butylhydroquinone (TBHQ) was photoisomerized to produce CLA- rich soy oil. The CLA content was determined by GC-FID analysis and oxidative stability by peroxide value (PV). The soy oil in the presence of TBHQ, MT alone and MT with 500 ppm of AP produced significantly greater CLA yields and improved oxidative stability compared to a control without added antioxidants (p < 0.05). However, added mixed tocopherols produced the greatest CLA yield and also reduced PV relative to the control. Tocopherols in the form of α-, γ- and δ-tocopherols were then each examined as to their relative effect on CLA yields and PV. The largest increase in CLA yield was obtained with 1800 ppm of γ-tocopherols with reduced PV. Mixed tocopherols, TBHQ and γ-tocopherols can be used to increase CLA yield and reduce PV of soy oil during linoleic acid photoisomerization.     

Effect of antioxidants on oxidative stability of edible fats and oils: thermogravimetric analysis

Thermogravimetric analysis was used to determine the oxidative stability of various edible oils (olive oil, milkfat) and triacylglycerides (triolein, trilinolein), while the effect of natural (alpha-tocopherol, ascorbic acid) and synthetic antioxidants (butylated hydroxytoluene (BHT), butylated hydroxyanisole (BHA), and tertiary butyl hydroquinone were evaluated by addition to trilinolein. Oil resistance to oxidation was obtained by measuring the increase in sample weight due to the uptake of molecular oxygen, the temperature at maximum sample weight, and the temperature at the onset of oxidation. When comparing sample weight increase, trilinolein proved to be oxidatively less stable than triolein, olive oil, and milk fat, while triolein was less stable than olive oil and milk fat. Olive oil showed significantly higher stability than milkfat when comparing the temperature at the onset of oxidation. When comparing effectiveness of antioxidants, a combination of 0.01% BHA and 0.01% BHT increased trilinolein stability the most.     

Antioxidant and biocidal activities of Carum nigrum (seed) essential oil, oleoresin, and their selected components

In the present study, chemical constituents of the essential oil and oleoresin of the seed from Carum nigrum obtained by hydrodistillation and Soxhlet extraction using acetone, respectively, have been studied by GC and GC-MS techniques. The major component was dillapiole (29.9%) followed by germacrene B (21.4%), beta-caryophyllene (7.8%), beta-selinene (7.1%), and nothoapiole (5.8%) along with many other components in minor amounts. Seventeen components were identified in the oleoresin (Table 2) with dillapiole as a major component (30.7%). It also contains thymol (19.1%), nothoapiole (15.2.3%), and gamma-elemene (8.0%). The antioxidant activity of both the essential oil and oleoresin was evaluated in mustard oil by monitoring peroxide, thiobarbituric acid, and total carbonyl and p-anisidine values of the oil substrate. The results showed that both the essential oil and oleoresin were able to reduce the oxidation rate of the mustard oil in the accelerated condition at 60 degrees C in comparison with synthetic antioxidants such as butylated hydroxyanisole and butylated hydroxytoluene at 0.02%. In addition, individual antioxidant assays such as linoleic acid assay, DPPH scavenging activity, reducing power, hydroxyl radical scavenging, and chelating effects have been used. The C. nigrum seed essential oil exhibited complete inhibition against Bacillus cereus and Pseudomonas aeruginosa at 2000 and 3000 ppm, respectively, by agar well diffusion method. Antifungal activity was determined against a panel of foodborne fungi such as Aspergillus niger, Penicillium purpurogenum, Penicillium madriti, Acrophialophora fusispora, Penicillium viridicatum, and Aspergillus flavus. The fruit essential oil showed 100% mycelial zone inhibition against P. purpurogenum and A. fusispora at 3000 ppm in the poison food method. Hence, both oil and oleoresin could be used as an additive in food and pharmaceutical preparations after screening.     

Update on the healthful lipid constituents of commercially important tree nuts

Uncharacteristic of most whole foods, the major component of tree nuts is lipid; surprisingly, information on the lipid constituents in tree nuts has been sporadic and, for the most part, not well reported. Most published papers focus on only one nut type, or those that report a cultivar lack a quality control program, thus making data comparisons difficult. The present study was designed to quantify the healthful lipid constituents of 10 different types of commercially important tree nuts (i.e., almonds, black walnuts, Brazil nuts, cashews, English walnuts, hazelnuts, macadamias, pecans, pine nuts, and pistachios) according to standardized, validated methods. The total lipid content of each nut type ranged from 44.4 ± 1.9% for cashews to 77.1 ± 1.7% for macadamias. As expected, the major fatty acids present in the tree nuts were unsaturated: oleic (18:1 ω9) and linoleic (18:2 ω6) acids. A majority of the lipid extracts contained <10% saturated fatty acids with the exceptions of Brazil nuts (24.5%), cashews (20.9%), macadamias (17.1%), and pistachios (13.3%). The total tocopherol (T) content ranged from 1.60 ± 1.27 mg/100 g nutmeat in macadamias to 32.99 ± 0.78 in black walnuts. The predominant T isomers in the nut types were α- and γ-T. Tocotrienols were also detected, but only in 6 of the 10 nut types (i.e., Brazil nut, cashews, English walnuts, macadamias, pine nuts, and pistachios). In most cases, total phytosterol contents were greater in the present study than reported in peer-reviewed journal papers and the USDA National Nutrient Database for Standard Reference, which is attributed to total lipid extraction and the inclusion of steryl glucosides in the analysis; the levels were highest for pistachios (301.8 ± 15.4 mg/100 g nutmeat) and pine nuts (271.7 ± 9.1 mg/100 g nutmeat). Minor sterols were also quantified and identified using GC-FID and GC-MS techniques.     

Characterization of medium-chain triacylglycerol (MCT)-enriched seed oil from Cinnamomum camphora (Lauraceae) and its oxidative stability

Medium-chain triacylglycerol (MCT)-enriched oil was extracted by supercritical fluid extraction of carbon dioxide (SFE-CO(2)) from Cinnamomum camphora seeds. The SFE-CO(2) process was optimized using the Box-Behnken design (BBD). The maximum oil yield (42.82%) was obtained under the optimal SFE-CO(2) conditions: extraction pressure, 21.16 MPa; extraction temperature, 45.67 °C; and extraction time, 2.38 h. Subsequently, the physicochemical characteristics, fatty acid composition, triacylglycerol (TAG) composition, tocopherol content, and DSC profile as well as oxidative stabilities of C. camphora seed oil (CCSO) were studied. Results showed that CCSO contained two major medium-chain fatty acids, capric acid (53.27%) and lauric acid (39.93%). The predominant TAG species in CCSO was LaCC/CLaC (ECN 32, 79.29%). Meanwhile, it can be found that CCSO had much higher oxidative stabilities than coconut oil due to the higher content of tocopherols in CCSO (α-tocopherol, 8.67 ± 0.51 mg/100 g; γ-tocopherol, 22.6 ± 1.02 mg/100 g; δ-tocopherol, 8.38 ± 0.47 mg/100 g). Conclusively, CCSO with such a high level of MCTs and high oxidative stabilities could be potentially applied in special food for specific persons such as weak patients and overweight persons because oils enriched in MCTs can be rapidly absorbed into body to provide energy without fat accumulation.     

Effect of added caffeic acid and tyrosol on the fatty acid and volatile profiles of camellia oil following heating

Camellia oil is widely used in some parts of the world partly because of its high oxidative stability. The effect of heating a refined camellia oil for 1 h at 120 degrees C or 2 h at 170 degrees C with exogenous antioxidant, namely, caffeic acid and tyrosol, was studied. Parameters used to assess the effect of heating were peroxide and K values, volatile formation, and fatty acid profile. Of these, volatile formation was the most sensitive index of change as seen in the number of volatiles and the total area count of volatiles in gas chromatograms. Hexanal was generally the dominant volatile in treated and untreated samples with a concentration of 2.13 and 5.34 mg kg(-1) in untreated oils heated at 120 and 170 degrees C, respectively. The hexanal content was significantly reduced in heated oils to which tyrosol and/or caffeic acid had been added. Using volatile formation as an index of oxidation, tyrosol was the more effective antioxidant of these compounds. This is contradictory to generally accepted antioxidant structure-activity relationships. Changes in fatty acid profiles after heating for up to 24 h at 180 degrees C were not significant.     

Antioxidant properties of evening primrose seed extracts

The antioxidant activity of extracts of evening primrose seeds (SE) and a commercially extracted filter cake (FC) were determined. The SE and FC were extracted with methanol/water (9:1) followed by evaporation and concentration. Extracts were tested in a bulk oil system and an oil-in-water emulsion using safflower oil as the major source of lipids. The antioxidant activity of the extracts was compared to that of a control and to that of butylated hydroxytoluene (BHT), singly, and in combination. Antioxidant activity was measured by the co-oxidation of beta-carotene, an oxidative stability instrument, conjugated dienes, and headspace analysis of hexanal. The SE extract had greater antioxidant activity than the FC extract. The SE extract was more effective in controlling the oxidation in the oil-in-water model system than in the bulk oil system. The activity of SE was concentration dependent, and at higher concentrations the SE was as effective as BHT, but it required higher concentrations because of its lack of purity. Synergism between SE and BHT was demonstrated in both model systems.     

Model system for testing the efficacy of antioxidants in muscle foods

The objective of this research was to study the effect of the antioxidants, delta-tocopherol, butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), tertiary butylhydroquinone (TBHQ), and propyl gallate in a model system of lean muscle and canola oil and to compare the effects with those in minced herring. Two carrier solvents with different dielectric constants (epsilon), ethanol (epsilon = 24) and oil (epsilon= 2), were used. Oxidation was measured using thiobarbituric acid reactive substances (TBARS) and sensory analysis. In both the lean muscle-canola oil model system and in herring muscle, the hydrophilic antioxidants, propyl gallate and TBHQ, were more effective in providing oxidative stability than the lipophilic antioxidants, delta-tocopherol and BHT. The oxidative stability of a cod muscle-canola oil system in the presence of propyl gallate, and delta-tocopherol was not affected by the dielectric constant of the carrier solvent, while BHA was more effective as an antioxidant when added in the polar solvent ethanol.     

气调包装对松籽常温贮藏生理和品质变化的影响

以朝鲜红松带壳松籽和去壳松仁为试材,将其分别放在30 μm紫色聚氯乙烯袋、30 μm白色聚氯乙烯袋和40 μm白色聚乙烯袋中进行自发气调贮藏,研究了常温下（20～30℃）贮藏180 d期间松籽种仁的生理、品质和脂肪酸氧化变化。结果表明：与40 μm聚乙烯袋相比,30 μm紫色聚氯乙烯袋与30 μm白色聚氯乙烯袋可以形成相对低O2高CO2的贮藏条件,能有效降低带壳松籽和去壳松仁的呼吸速率和可溶性总糖的损耗,提高种仁的贮藏优品率;同时可以较好地防止总脂肪的降解,抑制酸价、过氧化值的升高和碘价的降低。综上所述,30 μm聚氯乙烯袋可以较好地保持松籽品质,相同气调包装贮藏下带壳松籽的贮藏品质优于去壳松仁。     

Tocopherol concentration in almond oil: genetic variation and environmental effects under warm conditions

The concentration of the different tocopherol homologues in almond kernel oil was determined in 17 almond cultivars grown in two different experimental orchards, in Spain and Morocco. The three main homologues showed a large variability, ranging from 210.9 to 553.4 mg/kg of oil for α-tocopherol, from 4.64 to 14.92 mg/kg for γ-tocopherol, and from 0.2 to 1.02 mg/kg for δ-tocopherol. The year effect was significant, independent of the experimental site, for all homologues and total tocopherol, the values of α-tocopherol, γ-tocopherol, and total tocopherol being higher in 2009 than in 2008, whereas the value of δ-tocopherol was higher in 2008. The location effect was also significant, the values of γ- and δ-tocopherol being higher in Spain than in Morocco, whereas for α-tocopherol the location effect was dependent on the genotype. These effects could not be explained by the temperature differences between sites, but probably other undetermined environmental factors might explain the effect of the location, such as rainfall and irrigation supplementation during fruit growing and ripening.     

High content of dopamine, a strong antioxidant, in Cavendish banana

A strong water-soluble antioxidant was identified in the popular commercial banana Musa cavendishii. It is dopamine, one of the catecholamines. For suppressing the oxygen uptake of linoleic acid in an emulsion and scavenging a diphenylpicrylhydrazyl radical, dopamine had greater antioxidative potency than glutathione, food additives such as butylated hydroxyanisole and hydroxytoluene, flavone luteolin, flavonol quercetin, and catechin, and similar potency to the strongest antioxidants gallocatechin gallate and ascorbic acid. Banana contained dopamine at high levels in both the peel and pulp. Dopamine levels ranged from 80-560 mg per 100 g in peel and 2.5-10 mg in pulp, even in ripened bananas ready to eat. Banana is thus one of the antioxidative foods.