Gamma-irradiation of individual cholesterol oxidation products

Cholesterol and seven of its oxidation products in aqueous suspensions of multilamellar vesicles or sonicated aqueous suspensions were subjected individually to γ-radiation (10 KGy) at 0–4°C in air, N₂ or N₂O. All compounds underwent some changes under the influence of radiation. β-Epoxide (cholesterol 5β,6β-epoxide) and, to a much lesser extent, α-epoxide (cholesterol 5α,6α-epoxide) were converted in low yield to 6-ketocholestanol (5α-cholestan-3β-ol-6-one). 7β-Hydroxycholesterol (cholest-5-ene-3β,7β-diol) and, to a lesser extent, 7α-hydroxycholesterol (cholest-5-ene-3β,7α-diol) gave low yields of 7-ketocholestanol (5α-cholestan-3β-ol-7-one). The latter compound also was obtained by irradiation of 7-ketocholesterol (cholest-5-ene-3β-ol-7-one). 6-Ketocholestanol and 7-ketocholestanol are potential biomarkers for irradiated meat and poultry.     

Cholesterol oxidation in some processed fish products

Numerous foods of animal origin are reported to contain considerable levels of cholesterol oxidation products (COP); however, very few reports are available on fish products. Levels of COP were assessed in samples of fish roe, fish oil, and fish meal. Among the fish roe samples, the smoked cod roe had the highest amount of COP, 93 μg/g lipids. Refined and bleached menhaden oil had 8 μg/g, and two experimental alkali-refined, bleached, and deodorized herring fish oil samples contained similar amounts of COP. The range of total COP in the three fish meal samples ranged from 50 to 78 μg/g fish meal. Generally, processed fish roe contained high amounts of COP compared with refined fish oils, which had very low amounts of COP. Fish meal samples had very high amounts of COP.     

Antioxidant efficiency of oregano in frying and storage of fried products

The effect of oregano on the oxidative stability of cottonseed oil during frying of potato chips and on the storage stability of the products was studied. The ground spice or an ethanol‐derived extract was added to the oil before frying. The results showed that both additives decreased the rates of accumulation of conjugated dienes, polar compounds, polymerized triacylglycerols, dimeric triacylglycerols and the p‐anisidine value of the frying oil, while the hydrolytic compounds were not affected. The major decrease was observed in the accumulation of polymerized and dimeric triacylglycerols. The storage stability of the produced chips was estimated by the rate of increase of the peroxide value and of the conjugated dienes in the oil absorbed by them. Both rates were depressed when oregano was added to the frying oil, with the protective action of oregano extract being considerably greater than that of ground oregano. The protective action of oregano extracts obtained by successive extractions with petroleum ether (PE), diethyl ether (EE) and ethanol (EtOH) and added to the chips after frying was also examined. The results showed that the EE and EtOH extracts were very effective against oxidative deterioration.     

Volatile compounds in oils after deep frying or stir frying and subsequent storage

Soybean oil (900 g) was heated by deep frying at 200°C for 1 h with the addition of 0, 50, 100, 150 and 200 mL water, and then stored at 55°C for 26 weeks. Soybean oil, corn oil and lard were heated by stir frying and then stored at 55°C for 30 weeks. The volatiles and peroxide values of these samples were monitored. All samples contained aldehydes as major volatiles. During heating and storage, total volatiles increased 260-1100-fold. However, aldehyde content decreased from 62–87% to 47–67%, while volatile acid content increased from 1–6% to 12–33%; especially hexanoic acid which increased to 26–350 ppm in the oils after the storage period was completed. Water addition to the oils heated by deep frying tended to retard the formation of volatile compounds. The total amount of volatile constituents of lard heated by stir frying increased more during storage than that of corn oil or soybean oil. Peroxide values did not reflect the changes of volatile content in the samples.     

可得然胶功能特性及在肉及肉制品中的应用进展

可得然胶是一种微生物胞外多糖,因其良好的增稠、持水、凝胶以及成膜等性能,近些年在肉类加工及保鲜领域得到了广泛的应用。该文综述了可得然胶的功能特性,重点阐述了可得然胶对肉及肉制品品质特性的影响及其对肉品的品质提升机制,最后总结了由可得然胶制备的不同类型可食性复合膜在肉类保鲜中的应用效果,以期为可得然胶在肉类加工和保鲜领域的广泛应用提供理论参考。     

A-ring oxidation products from γ-irradiation of cholesterol in liposomes

γ-Irradiation of cholesterol in multilamellar vesicles (MLV) at 0–4°C causes oxidation of the A-ring. Two A-ring oxides formed in considerable amounts are cholest-4-en-3-one (10) and cholest-4-ene-3,6-dione (12) in addition to the usual B-ring oxides. Lesser amounts of cholesta-4,6-dien-3-one (11) are also generated. Compounds 10 and 12 were detected and measured in cholesterol irradiated at less than 0.5 kGy in liposomes containing saturated or unsaturated phospholipids. Lesser amounts of 10 and 12, as well as lesser amounts of other cholesterol oxides, were formed when a major constituent of the MLV was dilinoleoylphosphatidylcholine. Autoxidation of cholesterol in MLV also gave rise to small amounts of 10, 11 and 12.     

ICS-90测定肉制品中亚硝酸盐

介绍了用离子色谱测定肉制品中亚硝酸盐的方法。实验证明,该方法在0．00mg/L-0．20mg／n呈现良好的线性关系,相关系数为0．9998,回收率为94．3％,保留时间和峰面积的相对标准偏差（RSD）分别为0．38％和2．90％。     

Cholesterol oxides content in selected animal products determined by GC‐MS

The aim of this study was to evaluate the effect of heat treatment of selected animal products on formation of cholesterol oxidation products (COP) and also to determine their content in selected pates and fermented pork sausage which are available on the Polish market. COP content in pates was significantly lower as compared to fermented sausages, and ranged from 39.5 to 43.1 µg/100 g; COP in sausages ranged from 195.8 to 263.4 µg/100 g of product. COP content in pan fried meats, chops, and fish fillets varied from 6.2 to 991.2 µg/100 g products. This paper demonstrates the method for determining the content of COP by the use of selected ion technique with the aid of MS. Practical applications: The method described is useful for the investigation of oxysterols in food matrices. The method is used for the investigation of the presence and content of COP, such as: 7β‐hydroxycholesterol, 5α,6α‐epoxycholesterol, 5β,6β‐epoxycholesterol, 5α‐cholestane‐3β,5β,6β‐triol, 7‐ketocholesterol, and 25‐hydroxycholesterol. The obtained data about COP content in selected animal products and their formation during heat treatment are crucial for creating a reliable database to assess their daily intakes and biological effects in humans.     

Long storage stability of biodiesel made from rapeseed and used frying oil

The degree of physical and chemical deterioration of biodiesel produced from rapeseed and used frying oil was studied under different storage conditions. These produced drastic effects when the fuel was exposed to daylight and air. However, there were no significant differences between undistilled biodiesel made from fresh rapeseed oil and used frying oil. The viscosity and neutralization numbers rose during storage owing to the formation of dimers and polymers and to hydrolytic cleavage of methyl esters into fatty acids. However, even for samples studied under different storage conditions for over 150 d the specified limits for viscosity and neutralization numbers had not been reached. In European biodiesel specifications there will be a mandatory limit for oxidative stability, because it may be a crucial parameter for injection pump performance. The value for the induction period of the distilled product was very low. The induction period values for the undistilled samples decreased very rapidly during storage, especially with exposure to light and air.     

Oxidative decomposition of cholesterol in fish products

Cholesterol oxides in fish products popular in Japan, including salted and dried, boiled and dried and smoked products, were qualitatively and quantitatively determined as trimethylsilyl ether derivatives by gas-liquid chromatography and mass spectrometry. The level of total cholesterol oxides ranged widely between 8.3 ppm in boiled and dried shrimp and 188.0 ppm in boiled and dried anchovy. 7β-Hydroxycholesterol and 7-ketocholesterol were the most prominent oxidative decomposition products of cholesterol. The levels of epimeric epoxides, cholestane triol and 25-hydroxycholesterol were relatively low. To elucidate a mechanism of cholesterol oxidation proceeding during fish processing and subsequent preservation, four model systems, consisting of a mixture of purified cod liver triglycerides plus cholesterol, of a mixture of authentic triolein plus cholesterol, of triolein alone and of cholesterol alone, were stored separately at 25°C in dry air for up to 104 d. The residual fatty acids of the triglycerides, and the cholesterol oxides produced, were recovered and determined. Oxygen uptake remained almost unchanged for the mixture of triolein plus cholesterol. No detectable amount of cholesterol oxides was produced, and the fatty acid content of the residual oleic acid, measured by an internal standard, remained almost unchanged. For the mixture of cod liver triglycerides plus cholesterol, a remarkable increase in oxygen uptake was observed. A continuous increase in the amount of cholesterol oxides was observed, accompanied by a remarkable concurrent decrease in polyunsaturated fatty acid residues, as well as of the oleic acid naturally present. These results strongly suggest that cholesterol oxidation in fish products proceeds in conjunction with oxidative decomposition of the coexisting polyunsaturated fatty acids of fish oils.     

Iron accumulation in oil during the deep-fat frying of meat

Iron accumulation in oil is a potential problem when frying food containing substantial amounts of iron. Selected meat products (skinless chicken breast, beef liver, and lean beef) were ground and fried (ca. 2-cm spheres, ca. 10 g/sphere) in partially hydrogenated soybean oil (PHSBO). Samples (450 g) of ground meat were fried 3 times/h for 8 h/d for 3 d. Oil samples were collected for analysis for iron (every 8 h) and oil degradation (every 4 h) and replaced with fresh oil. The iron contents of oil samples after 3 d of frying were approximately 0.11, 0.48, and 4.01 mg of iron/kg of PHSBO for the oil used to fry chicken, beef, and liver, respectively. There was a notable darkening in color and an increased tendency to foam for the beef liver oil sample compared with the other samples. After frying, the acid values were 0.9, 1.1, and 1.4 for the oil samples for chicken, beef, and liver, respectively. After frying, the p-anisidine values were 11.5, 12.8, and 32.6 for the oil samples for chicken, beef, and liver, respectively; the food oil sensor values were 0.96, 0.96, and 0.83 for the oil samples for chicken, beef, and liver, respectively.     

Oxidative effects of animal-originated porphyrins and riboflavin on cholesterol oxidation in an aqueous model system

This study was executed to investigate effects of animal-originated porphyrins and riboflavin on cholesterol oxidation in aqueous model systems. Changes of headspace oxygen contents, cholesterol, and cholesterol oxide products (COP) in the model systems were measured by gas chromatography during storage under light. As concentration of protoporphyrin increased, contents of headspace oxygen decreased and COP increased. The same trend as that of protoporphyrin occurred with riboflavin in terms of contents of headspace oxygen, but production of COP was the highest at 5 ppm riboflavin. As concentrations of hemoglobin and myoglobin increased, headspace oxygen content and COP production were not changed significantly. Consequently, protoporphyrin could be the most active catalyst on the cholesterol oxidation in the aqueous system, but myoglobin and hemoglobin did not accelerate cholesterol oxidation.     

Long storage stability of biodiesel from vegetable and used frying oils

Biodiesel is defined as the mono-alkyl esters of vegetable oils. Production of biodiesel has grown tremendously in European Union in the last years. Though the commercial prospects for biodiesel have also grown, there remains some concern with respect to its resistance to oxidative degradation during storage. Due to the chemical structure of biodiesel the presence of the double bond in the molecule produce a high level of reactivity with the oxygen, especially when it placed in contact with air. Consequently, storage of biodiesel over extended periods may lead to degradation of fuel properties that can compromise fuel quality.This study used samples of biodiesel prepared by the process of transesterification from different vegetable oils: high oleic sunflower oil (HOSO), high and low erucic Brassica carinata oil (HEBO and LEBO) respectively and used frying oil (UFO). These biodiesels, produced from different sources, were used to determine the effects of long storage under different conditions on oxidation stability. Samples were stored in white (exposed) and amber (not exposed) glass containers at room temperature.The study was conducted for a period of 30-months. At regular intervals, samples were taken to measure the following physicochemical quality parameters: acid value (AV), peroxide value (PV), viscosity (ν), iodine value (IV) and insoluble impurities (II). Results showed that AV, PV, ν and II increased, while IV decreased with increasing storage time of biodiesel samples. However, slight differences were found between biodiesel samples exposed and not exposed to daylight before a storage time of 12 months. But after this period the differences were significant.     

Studies on phytosterol oxides. I: Effect of storage on the content in potato chips prepared in different vegetable oils

Potato chips fried in palm oil, sunflower oil, and high-oleic sunflower oil were studied for the content of different phytosterol oxides during 0 to 25 weeks of storage in the dark. Oxidation products of sitosterol (24α-ethyl-5-cholesten-3β-ol) and campesterol (24α-methyl-t-cholesten-3β-ol) were synthesized to help identify the phytosterol oxides. The oxides of phytosterols were analyzed by preparative thin-layer chromatography, solid-phase extraction, capillary column gas chromatography (GC), and GC-mass spectrometry. Epimers of 7-hydroxysitosterol and 7-hydroxycampesterol; 7-ketositosterol and 7-ketocampesterol; epimers of 5,6-epoxy-sitosterol and 5,6-epoxy-campesterol; 24α-ethylcholestane-3β,5,6β-triol (dihydroxysitosterol) and 24α-methylcholestane-3β,5,6β-triol (dihydroxycampesterol) were detected and quantitated in the samples of chips fried in different vegetable oils. Potato chips fried in palm oil had the lowest level of total sterol oxides, ranging from 5 to ca. 9 ppm in the lipids from time 0 to 25 wk of storage. The level of total sterol oxides in chip samples fried in sunflower oil ranged from 46 to 47 ppm, and the lipids in samples fried in high-oleic sunflower oil ranged from 35 to 58 ppm from 0 time to 25 wk of storage. During 25 wk of storage no considerable increase in sterol oxides was observed in the samples of chips fried in palm oil and sunflower oil. The chip samples fried in high-oleic sunflower oil had slightly higher levels of sterol oxides after 10 and 25 weeks of storage. In addition to the levels of individual sterol oxides, a new method for enrichment of phytosterol oxides from the unsaponifiables and full-scan mass spectra of various oxidation products of sitosterol and campesterol are reported in this paper. Part of the results were presented at the 86th Annual Meeting of the AOCS, May 7–11, 1995, San Antonio, TX.     

Effect of synthetic antioxidants on cholesterol stability during the thermal-induced oxidation of a polyunsaturated vegetable oil

As a molecule with an unsaturated bond, cholesterol is prone to oxidation. Cholesterol oxidation products (COP) are found in many common foods and have been shown to be atherogenic, cytotoxic, mutagenic, and possibly carcinogenic. Efforts to reduce the formation of oxidation products are considered important during the manufacture and processing of foods. The effect of synthetic antioxidants on cholesterol oxidation has not been extensively studied. We assayed the effect of five commonly used antioxidants—BHT, BHA, the n-propyl ester of 3,4,5-trihydroxy benzoic acid (PG), TBHQ, and 6-ethoxy-1,2-dihydro-2,4-trimethylquinoline (EQ)—on cholesterol stability when oxidation is induced in a Rancimat 679 instrument by bubbling air through the sample at 150°C. The sample consisted of 200 mg cholesterol dispersed in 100 g of a polyunsaturated vegetable oil (soybean oil). Formation of six COP was measured at the induction period, and at the 50 and 100 μS conductivity values. Under the experimental conditions, BHT and TBHQ were the most effective inhibitors of cholesterol oxidation. BHA and EQ were less effective, and PG was unable to prevent cholesterol oxidation. Synthetic antioxidants were more effective in preventing COP formation at the nucleus of the cholesterol structure than at the lateral chain.     

Formation of short‐chain glycerol‐bound oxidation products and oxidised monomeric triacylglycerols during deep‐frying and occurrence in used frying fats

Heating fats and oils at high temperature in the presence of air, a common procedure in culinary practices such as frying, results in a complex mixture of oxidation products. These compounds may impair the nutritional value of the food. Among them, there is a growing interest in the group of oxidised triacylglycerol monomers because of their high absorbability. The main structures in this group include triacylglycerols (TG) containing short‐chain acyl groups formed by homolytic β‐scission of the alkoxy radicals coming from allylic hydroperoxides. In addition there are TG containing oxidised fatty acyl groups of molecular weight similar to that of their parent TG, i.e., epoxy, keto and hydroxy fatty acyl groups. In this review, the main routes of formation of oxidised TG monomers are detailed. Also, the most relevant advances in the analysis of intact TG molecules by high‐performance liquid chromatography coupled with mass spectrometry are discussed. Special attention is paid to the present analytical possibilities for accurate quantification of the most important oxidised compounds formed at high temperature. Both the need to convert fats and oils into simpler derivatives, thus concentrating the compounds bearing the oxidised structure, and the methylation procedure selected to avoid artefact formation are justified. Typical concentrations of short‐chain fatty acids, short‐chain aldehydic acids, short‐chain diacids, and monoepoxy fatty acids, ketoacids and hydroxyacids in frying oils from restaurants and fried‐food outlets, with polar lipids levels at the limit of rejection for human consumption, are given.     

反相高效液相色谱法测定肉制品中残留的盐酸克伦特罗

建立了快速简便测定肉类产品中盐酸克伦特罗含量的反相高效液相色谱法。简化了样品前处理方法,优化了色谱分析条件。结果表明,以Inertil/WondaSil C18(5μm,4.6 mm×150 mm)为分离柱,流动相V(0.1%磷酸)∶V(甲醇)=6∶4,流速1.0 mL/min,进样量10μL,柱温40℃,检测波长244 nm时,可以获得良好的色谱峰。绞碎的样品经饱和硼砂和硫酸锌处理除去脂肪和蛋白质,用水定容。样品加标回收率在95%¹03%之间,保留时间的相对标准偏差为0.14%,峰面积的相对标准偏差为6.73%。此方法前处理简单,分析时间短,测定结果准确可靠,适于肉类产品中盐酸克伦特罗的测定。     

Ultrasonically enhanced low-temperature microwave-assisted vacuum frying of edamame: Effects on dehydration kinetics and improved quality attributes

Abstract

Using ultrasound (US) at microwave-assisted vacuum Frying (MVF) program was investigated to acquire better process efficacy and bodily high-quality attributes of fried edamame. Different power degrees of US (0, 150, 300, 600 W) and temperature (80, 90, and 100?°C) were utilized in a constant microwave power and frequency of 1000 W and 28?kHz during ultrasound and microwave-assisted vacuum frying (USMVF) process. Ten different mathematical models were employed to describe dehydration kinetics of the fried edamame, and nonlinear regression analysis was used to determine model parameters. Concerning fitting performance, the most suitable model was the two-term model. Drying kinetics, effective moisture diffusivity (D_e), activation energy (E_a), and physical properties of fried samples were evaluated in this newly designed USMVF equipment using different ultrasound power to the studied temperature range. By increasing the US power level, the calculated D_e increased from 1.947?×?10^?9 to 4.742?×?10^?9 m²/s. The results have revealed that the E_a of this fried edamame decreased significantly with increasing the US power level. The USMVF process at every frying temperature increased the drying kinetics and D_e when compared to the non-USMVF process. The USMVF samples always gave lower oil content and water activity in contrast to the non-USMVF samples. The color and texture properties of fried edamame were significantly improved and higher the US power level in the USMVF produced a better progress. Vitamin C and chlorophyll retention of fried edamame was highest in US600MVF process.     

Use of rosemary extract in preventing oxidation during deep-fat frying of potato chips

The effect of using a rosemary extract on the stability of oil used for frying potato chips has been evaluated. Sliced potatoes were fried intermittently in soybean oil containing a natural extract from rosemary. The conditions used for frying were 185°C for 90 s. Two separate experiments, with and without replenishment of oil, were carried out. Oil samples were taken each day, not only from the frying pans but also by extraction with hexane from the chips. Changes in the induction period of the oil samples (Rancimat method) were determined. The induction period decreased as frying progressed. The reduction in the induction period was higher in the oil free of rosemary extract, and the chips were much darker in color. The oil containing the extract showed greater antioxidant activity, and reduced darkening and rancidity of the oil. Potato chips fried in the oil with added rosemary extract were more acceptable than chips fried in oil containing no extract until the last frying. The free radical scavenging activity of rosemary extract in comparison to other natural antioxidants was also determined by the reduction of O₂ ^.- in a hypoxanthine/xanthine oxidase system.