The New Paradigm for Lipid Oxidation and Insights to Microencapsulation of Omega‐3 Fatty Acids

The consumption of omega‐3 fatty acids provides a wide range of health benefits. However, the incorporation of these fatty acids in foods is limited because of their high oxidative instability. A new paradigm has emerged to better explain the oxidation mechanism of polyunsaturated fatty acids, which will be discussed here with reference to bulk lipids considered a special case of water in oil microemulsion. This paradigm suggests that lipid oxidation reactions are initiated by heterogeneous catalysis by metal oxides followed by the formation of micelles containing initial hydroperoxides, water, and other amphiphilic compounds. The induction period comes to the end when the formed micelles reach a critical micelle concentration and start to decompose opening the way to intense free radical reactions. Antioxidants and synergists extend the induction period not only by scavenging free radicals but also by stabilizing the micelles. With better understanding of the lipid oxidation mechanism, a tailored choice of antioxidants and synergistic combinations, and efficient encapsulation methods may be optimized to provide stable encapsulates containing highly n‐3 polyunsaturated fatty acids. Smart processing and encapsulation technologies utilizing properly stabilized oils as well as optimized packaging parameters aiming to enhance n‐3 fatty acid stability by smart selection/design of antioxidants, control of the interfacial physics and chemistry, and elimination of surface oil are needed for this purpose.     

Lipid Modification Strategies in the Production of Nutritionally Functional Fats and Oils

Rapid improvements in the understanding of the nutritional requirements of both infants and adults has led to new developments in the modification of fats and oils. Specific targets include the improvement in growth and development of infants, treatment of disease in adults, and disease prevention. Efforts have been focussed on the production of structured lipids using medium-chain acids and long-chain polyunsaturated fatty acids (PUFAs), as well as the concentration of long-chain PUFAs from new and existing sources. Short- and medium-chain fatty acids are metabolized differently than long-chain fatty acids and have been used as a source of rapid energy for preterm infants and patients with fat malabsorption-related diseases. Long-chain PUFAs, specifically docosahexaenoic acid and arachidonic acid, are important both in the growth and development of infants, while n-3 PUFAs have been associated with reduced risk of cardiovascular disease in adults. Based on the requirements for individual fat components by different segments of the population, including infants, adults, and patients, ideal fats can be formulated to meet their needs. By using specific novel fat sources and lipid modification techniques, the concentrations of medium-chain, long-chain saturated, and long-chain polyunsaturated fatty acids as well as cholesterol can be varied to meet the individual needs of each of these groups. While genetic modification of oilseeds and other novel sources of specific lipid components are still being developed, chemical and lipase-catalyzed interesterification reactions have moved to the forefront of lipid modification technology. Fractionation of fats and oils to provide fractions with different nutritional properties has potential, but little work has been performed on the nutritional applications of this method. The choice of suitable lipid modification technologies will depend on the target lipid structure, production costs, and consumer demand. A combination of some or all of the present lipid modification techniques may be required for this purpose.     

Effects of rosemary and green tea extracts on frozen surimi gels fortified with omega‐3 fatty acids

Two different sources of omega‐3 fatty acids (fish oil concentrate and menhaden oil) with or without the addition of natural antioxidants (rosemary and green tea) were incorporated into surimi gels at equivalent levels and examined for changes in sensory and physical properties and resistance to oxidation during 9 months of frozen storage. Gels with menhaden oil showed higher acceptance than gels with fish oil concentrate, which displayed a fishy taste that was partially masked by natural antioxidants. Formation of volatile compounds was similar in all samples. Upon heating to form the gel, there was a ca 20–25% decrease in the relative polyene index of the control containing no rosemary or green tea extract. Formulations with menhaden oil containing green tea and rosemary were more stable immediately after cooking; however, a slight pro‐oxidant effect occurred during storage. Omega‐3 fortified gels were whiter than gels with no added oil. Rosemary and green tea extracts increased yellowness (b*) and redness (a*), respectively. Strength increased in all formulations during frozen storage. Copyright © 2005 Society of Chemical Industry     

Effects of Trans and Conjugated LC N‐3 Polyunsaturated Fatty Acids on Lipid Composition and Abdominal Fat Weight in Rats

ABSTRACT: Trans and conjugated fatty acids may exhibit either beneficial or detrimental bioactive effects depending on their metabolic properties. This study was conducted to elucidate if isomerization and conjugation of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) demonstrate more favorable bioactivity on lipid metabolism compared to unmodified EPA and DHA. The effects of dietary intake of trans and conjugated forms of EPA and DHA on lipid metabolism were evaluated in animal trials and compared to a control group fed soybean oil. None of the experimental diets showed significant differences from the control in terms of body weight; however, the white adipose tissue weight of rodents fed trans DHA, conjugated EPA (CEPA), and conjugated DHA (CDHA) was significantly lower than the control. Triacylglycerol levels in plasma were significantly decreased in groups fed trans DHA (17.2 mg/dL) and CDHA (31.9 mg/dL) relative to the control (51.3 mg/dL). The total cholesterol concentrations were significantly lower than the control (68.0 mg/dL) in all experimental groups (47.3 to 53.7 mg/dL) except CEPA (58.3 mg/dL). Fatty acid compositions of lipids extracted from rodent livers were influenced by the dietary fatty acid profiles, with all groups showing higher concentrations of stearic acid and lower levels of linoleic acid compared to the control. Rodents fed trans DHA did not have detectable levels of these fatty acid isomers in their livers, suggesting either quick metabolism or a difficulty with bio‐absorption.     

大豆油和月桂酸制备MLM型结构脂质工艺优化及其性质分析

以大豆油和月桂酸作为反应底物,采用Lipozyme RM IM催化合成中长碳链（middle-long-middle,MLM）型结构脂质。通过响应面试验优化方法研究不同底物（月桂酸∶大豆油）物质的量比、反应温度、反应时间、脂肪酶添加量对合成结构脂质中月桂酸插入率的影响,并研究在最佳反应条件下MLM型结构脂质的理化性质。结果表明,最佳合成工艺条件下所得结构脂质的月桂酸插入率为29.26%,该条件为底物物质的量比6∶1、反应温度45?℃、反应时间24?h、脂肪酶添加量为底物质量的13%。理化性质研究表明,与原大豆油相比,MLM型结构脂质碘值（97.38?g/100?g）、黏度（70.39?cP）均降低,皂化值（以KOH计）（229.58?mg/g）、结晶开始温度（4.89?℃）和熔融开始温度（－19.87?℃）均显著提高（P＜0.05）,而烟点（231.24?℃）无显著差异（P＞0.05）。本研究合成的MLM型结构脂质,提高了原大豆油的营养价值,为开发抗肥胖、降血脂的优质油脂提供理论依据。     

Mechanisms of Docosahexaenoic and Eicosapentaenoic Acid Loss from Pacific Saury and Comparison of Their Retention Rates after Various Cooking Methods

The docosahexaenoic acid (DHA) and eicosapentaenoic acid (EPA) contents of Pacific saury (Cololabis saira), a fatty fish and staple of the Japanese diet, have been reported to decrease after cooking. This study compared the DHA and EPA contents remaining in saury after grilling, pan‐frying or deep‐frying to center temperatures of 75, 85, or 95 °C, and examined physical loss, lipid oxidation, and thermal degradation as mechanisms of DHA and EPA loss. Temperature changes inside the saury were monitored using thermocouples, while DHA and EPA contents, oxygen radical absorbance capacity, and measurements of lipid oxidation (that is, carbonyl value and thiobarbituric acid value) were determined chemically. Visualization of temperature distribution inside fish samples during cooking revealed large differences in heat transfer among cooking methods. True retention rates in grilled (DHA: 84 ± 15%; EPA: 87 ± 14%) and pan‐fried samples (DHA: 85 ± 16%; EPA: 77 ± 17%) were significantly higher than deep‐fried samples (DHA: 58 ± 17%; EPA: 51 ± 18%), but were not affected by final center temperatures despite differences in cooking times. Physical loss via cooking losses (grilling and pan‐frying) or migration into frying oil (deep‐frying) accounted for large quantities of DHA and EPA loss, while lipid oxidation and thermal degradation did not appear to be major mechanisms of loss. The antioxidant capacity of saury was not significantly affected by cooking treatments. The results of this study suggest that minimization of physical losses during cooking may increase DHA and EPA contents retained in cooked Pacific saury.     

Omega‐3 Fatty Acid Profile of Eggs from Laying Hens Fed Diets Supplemented with Chia,Fish Oil,and Flaxseed

The aim of this study was to investigate the effect of diets supplemented with fish oil, flaxseed, and chia seed on the omega‐3 fatty acid composition and sensory properties of hens’ eggs. No significant difference in yolk fat content was found between treatments. The fatty acid composition of egg yolk was significantly affected by the dietary treatments. Inclusion of chia at 300 g/kg into the diet produced eggs with the highest concentration of omega‐3 fatty acid. Eicosapentaenoic acid and docosahexaenoic acid were only detected in eggs from laying hens fed the diet supplemented with fish oil. Diet had a significant effect on color, flavor and overall acceptability of eggs. Types and levels of omega‐3 fatty acids in feed influence the level of yolk omega‐3 fatty acids in egg yolk. Inclusion of chia into the hens’ diet significantly increased the concentration of yolk omega‐3 fatty acid without significant change in sensory properties.     

n‐3 Omega fatty acids: a review of current knowledge

The very long chain polyunsaturated fatty acids (PUFAs) (C18–C22) and n‐3 Omega PUFAs are apparently widely accepted as a part of modern nutrition because of their beneficial effects on metabolism. Most significantly, the reported protective effect of the n‐3 omega fatty acids in relation to cardiovascular inflammatory diseases and cancer has led people to consider these fatty acids more beneficial than other dietary supplements. Unfortunately, there is a lack of studies relating to the physical performance increasing effect in sports diets, cholesterol‐reducing effect in meat technology, effects on human serum profile, the application dose and the side effects with/without omega‐6 PUFAs, which has left us with several crucial unanswered questions. We still do not know the correct dose of n‐3 omega and the correct ratio of n‐3 omega to n‐6 omega or their possible contraindications when combined with drugs, other foods and herbal supplements. Another reported aspect of n‐3 omega PUFAs is that they protect and even enhance the effect in medical treatment of important diseases such as Alzheimer’s, multiple sclerosis and cancer. These reports led to PUFAs becoming one of the most accepted and consumed food supplements. Despite this weight of evidence and the considerable current use, there is still a need for studies, which will determine whether the n‐3 omega fatty acids are in fact important functional supplements with no adverse effects. This review will attempt to outline the current position of n‐3 omega fatty acids in the field of clinical nutrition and healthcare and outline the studies needed to determine whether there are significant advantages in taking them as food supplement without any adverse effects.     

Comparative potential of white and red clover to modify the milk fatty acid profile of cows fed ryegrass‐based diets from zero‐grazing and silage systems

BACKGROUND: Two experiments were conducted to compare the effects of white and red clover on the fatty acid composition of milk fat from cows fed ryegrass‐based diets. In experiment 1, fresh ryegrass was mixed with white or red clover (60/40, on a dry matter (DM) basis). Experiment 2 involved similar mixed diets in ensiled form, and one ryegrass‐silage diet without the addition of clover. RESULTS: Total DM intake, milk yield and milk fat content were not affected by dietary treatments. Feeding freshly cut white versus red clover supplemented diets resulted in a higher proportion of n‐3 fatty acids, especially α‐linolenic acid, in milk fat. Addition of any clover silage to ryegrass silage increased the proportions of n‐3 fatty acids in milk fat, and reduced the proportions of conjugated linoleic acids (CLA), including C18:2 c9t11, and C18:1cis isomers. The n‐6/n‐3 ratio was elevated compared to the diet not supplemented with clover. CONCLUSION: White clover seemed to be slightly superior to red clover supplementation, but the effects of clover supplementation as such were generally larger than that of clover type. However, a higher concentration of n‐3 fatty acids with clover supplementation coincided with a lower concentration of CLA in the milk fat. Copyright © 2007 Society of Chemical Industry     

Fatty acid profile and proximate composition of Pacific mullet (Mugil so‐iuy) caught in the Black Sea

This study demonstrates proximate composition and fatty acid profile of Pacific mullet caught in Turkey. The highest moisture and protein contents were observed with muscle tissues as 83.74 and 10.52%, while the highest fat and ash contents were attributed to female gonads as 11.80 and 0.94%, respectively, with a significant variation amongst months (P < 0.05). Significant variation (P < 0.05) usually occurred amongst months within the same sex for total saturated fatty acids ( ∑ SFA), monosaturated fatty acids ( ∑ MUFA), polyunsaturated fatty acids ( ∑ PUFA), eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) in muscle, although overall mean values between sexes were not found significant. Except for EPA, no variation observed for gonads while significant changes occurred (P < 0.05) with liver samples amongst months. Overall total values of ∑ SFA, ∑ MUFA, ∑ PUFA, DHA and EPA in muscle samples were 29.59, 29.26, 18.06 and 4.48%, respectively, while in gonads ranged as 30.26–33.23%, 35.17–37.47%, 11.87–14.88%, 4.38–5.34% and 3.02–5.02%. These FAs were 21.57–33.11%, 32.89–50.96%, 14.78–20.08%, 0.89–9.94% and 5.85–9.54% for liver, respectively. The results of this study showed that muscle and gonads of Pacific mullet were rich in n‐3 PUFA, especially, EPA, DHA, increasing the value of this species for human consumption.     

Performance,carcass cut‐up and fatty acids deposition in broilers fed different levels of pellet‐processed flaxseed

The effects of flaxseed (FS) processing and inclusion levels on broiler performance and fatty acid deposition were examined. FS was provided as whole seed, ground or pellet‐then‐mashed at a dietary level of 0, 12 or 14% during days 1 to 21. These levels represented control, threshold and over‐threshold, respectively. During days 22 to 40, the threshold level was increased to 15%, while the over‐threshold level increased to 17%. After 21 days of feeding, the performance of birds fed a diet with 12% pellet‐then‐mashed FS were comparable (p > 0.05) with those fed mashed control diet, but superior to those fed a diet of whole FS (p < 0.05). There was interaction (p < 0.05) between diet processing and FS level on weight gain, with pellet‐then‐mash processing being more effective at the 12% FS inclusion level than at the 14% level in improving performance. The beneficial processing effect on performance diminished during days 22 to 40. Furthermore, carcass cut‐up percentage was not affected (p > 0.05) by the treatments, except that increased FS level resulted in smaller fat‐pad and larger liver (p < 0.05). Birds deposited omega‐3 (n‐3) fatty acids in breast and thigh muscle the most with higher FS inclusion and pellet‐then‐mash processing. On day 40, the total n‐3 fatty acids made up 22.1 and 24.4% in the muscle lipids of breast and thigh samples from birds fed pellet‐then‐mashed FS at the level of 12% during days 1 to 21 and at the level of 15% during days 22 to 40, respectively. These values were higher (p < 0.05) than those found in birds fed diets of similar FS levels but as whole seed or ground seed. Up to 12% pellet‐processed FS can be incorporated into broiler diets with satisfactory growth, while maximizing n‐3 fatty acid deposition in the tissues. Copyright © 2005 Society of Chemical Industry     

Effect of Dietary Partial Hydrolysate of Phospholipids,Rich in Docosahexaenoic Acid‐Bound Lysophospholipids,on Lipid and Fatty Acid Composition in Rat Serum and Liver

Lysophospholipids have been recognized as potent biologically active lipid mediators. However, attention has not been paid to the health benefits of dietary partial hydrolysate of phospholipids (PH‐PL), which is rich in docosahexaenoic acid (DHA)‐bound lysophospholipids. In this study, the effects of PH‐PL on serum and liver lipid profiles of rats upon administration of PH‐PL are demonstrated in comparison to those of fish oil (FO), which comprises eicosapentaenoic acid (EPA) and DHA‐bound triglyceride (TG). PH‐PL containing EPA and DHA was prepared via enzymatic modification of squid (Todarodes pacificus) meal that is rich in phospholipids. Male Wistar rats were fed a basal diet containing soybean oil alone (7%), FO, and PH‐PL. The FO and PH‐PL diets had similar EPA and DHA contents. After the rats had been fed their respective diets for 28 d, their serum and liver lipid contents, fecal lipid excretion, and hepatic gene expression level were measured. The results demonstrated that compared with the soybean oil diet alone, the PH‐PL diet decreased serum and liver TG contents partially because of the enhancement of liver acyl‐CoA oxidase activity and suppression of liver fatty acid synthase activity. In addition, compared with the soybean oil diet, the PH‐PL group exhibited lower serum cholesterol content at least in part because of the reduction of hepatic 3‐hydroxy‐3‐methylglutaryl‐CoA reductase mRNA expression level. We found that dietary administration of EPA and DHA containing PH‐PL has a hypolipidemic effect that may help prevent the development lifestyle‐related diseases.     

精制大豆油烟点与游离脂肪酸含量的关系模型

食用植物油脂是脂肪酸甘油三酯的混合物,精制大豆油是我国居民主要食用植物油脂之一,烟点与游离脂肪酸含量是精制大豆油的两项重要质量指标,其直接决定了大豆油的质量等级。一般情况下,精制大豆油游离脂肪酸含量高,则烟点低,本文利用回归分析法建立了两者的关系模型。     

Antioxidative Activities of Ginkgo biloba Extract on Oil/Water Emulsion System Prepared from an Enzymatically Modified Lipid Containing Alpha‐Linolenic Acid

Abstract: The desired mix of alpha‐linolenic acid (ALA)‐enriched structured lipid (SL) and physically blended lipid (PB) was prepared from grape seed oil and perilla oil at a weight ratio of 3:1. The major triacylglycerol species (LnLnL) in PB was drastically increased after interesterification (SL), from 0.5% to 16.8%. After the reaction, the total unsaturated fatty acid at the sn‐2 position was decreased from 98.83% in PB to 91.36% in SL. The reduction of vitamin E compounds was also observed. Compared with a PB‐based emulsion, SL‐based emulsions showed oxidative instability, as assessed by lipid hydroperoxide (LOOH) and 2‐thiobarbituric acid‐reactive substances (TBARS) values, which was mainly due to the SL which contained less LA, ALA, and ΣUSFA at the sn‐2 position and less γ‐tocopherol than did PB. PB‐, and SL‐based emulsions with Ginkgo biloba extract (GBE) which showed significantly lower values of LOOH and TBARS compared to a blank control. GBE was effective in retarding the oxidation of the emulsion by quenching the free radicals in the water phase of the emulsion and inhibiting the formation of primary and secondary oxidation products. These results indicate that GBE could be used as an antioxidant additive for stabilizing ALA‐enriched emulsions. Practical Application: The results suggest the possibility to supplement Ginkgo biloba extract in alpha linolenic acid‐enriched structured lipid‐based emulsions which would increase the therapeutic value and enhance the antioxidant potential of the emulsions.     

Sensory characteristics and storage quality indicators of surimi franks nutritionally enhanced with omega‐3 rich flaxseed oil and salmon oil

Surimi franks were fortified with flaxseed or salmon oil at 2 g/100 g sample, franks without added oil served as a control. Thiobarbituric acid reactive substances values were highest (P < 0.001) in salmon oil franks; however, these values did not change over the 21‐day storage period regardless of frank type (P > 0.05). Frank pH decreased over time (P = 0.011) for all frank types. There were differences in textural properties between frank types (P < 0.05), with the flaxseed franks being softer and less gummy, cohesive and chewy than the control franks. Participants (n = 79; age 18–35) evaluated visual appeal, colour, aroma, texture, flavour and acceptability on a hedonic scale; there were no differences (P > 0.05) between franks. Fifty‐four panellists reported consuming sausage on a weekly to monthly basis, and most (50/79) indicated interest in purchasing this type product. The surimi franks were accepted by young adult consumers, which may indicate market potential of these types of products.     

Effects of Green Tea Extract and α‐Tocopherol on the Lipid Oxidation Rate of Omega‐3 Oils,Incorporated into Table Spreads,Prepared using Multiple Emulsion Technology

Abstract: This study examined the effectiveness of fat and water soluble antioxidants on the oxidative stability of omega (ω)‐3 rich table spreads, produced using novel multiple emulsion technology. Table spreads were produced by dispersing an oil‐in‐water (O/W) emulsion (500 g/kg 85 camelina/15 fish oil blend) in a hardstock/rapeseed oil blend, using sodium caseinate and polyglycerol polyricinoleate as emulsifiers. The O/W and oil‐in‐water‐in‐oil (O/W/O) emulsions contained either a water soluble antioxidant (green tea extract [GTE]), an oil soluble antioxidant (α‐Tocopherol), or both. Spreads containing α‐Tocopherol had the highest lipid hydroperoxide values, whereas spreads containing GTE had the lowest (P < 0.05), during storage at 5 °C, while p‐Anisidine values did not differ significantly. Particle size was generally unaffected by antioxidant type (P < 0.05). Double emulsion (O/W/O) structures were clearly seen in confocal images of the spreads. By the end of storage, none of the spreads had significantly different G′ values. Firmness (Newtons) of all spreads generally increased during storage (P < 0.05). Practical Application: Lipid oxidation is a major problem in omega‐3 rich oils, and can cause off‐odors and off‐flavors. Double emulsion technology was used to produce omega‐3 enriched spreads (O/W/O emulsions), wherein the omega‐3 oil was incorporated into the inner oil phase, to protect it from lipid oxidation. Antioxidants were added to further protect the spreads by reducing lipid oxidation. Spreads produced had good oxidative stability and possessed functional (omega‐3 addition) properties.