Phenolic Compounds and Plant Phenolic Extracts as Natural Antioxidants in Prevention of Lipid Oxidation in Seafood: A Detailed Review

Lipid oxidation is the principal cause of quality loss in seafood, which is known to contain high amounts of polyunsaturated fatty acids. Such quality deterioration, associated with the development of off‐flavor as well as lowering of nutritive value, can be retarded by incorporation of additives having antioxidative properties. The use of synthetic antioxidants has long been practiced in retarding lipid oxidation. However, due to the potential health concerns of synthetic antioxidants, polyphenolic compounds, which are found in different plants and their manufactured by‐products, have been used as an alternative natural antioxidants to retard lipid oxidation in different seafood systems. Both pure phenolic compounds and crude plant phenolic extracts have been successfully used in delaying oxidation in fish muscle, fish oil, and fish oil‐in‐water emulsions. This article reviews in detail the phenolic antioxidants and their natural sources as well as focuses on the role of pure phenolic compounds and crude plant phenolic extracts on the prevention of lipid oxidation in different seafood systems.     

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     

Compositional characteristics of muscle and visceral oil from steelhead trout and their oxidative stability

The quality of lipid from steelhead trout viscera, a byproduct of steelhead trout industry, was evaluated and compared with that of the muscle. Steelhead trout viscera had a higher lipid content than muscle and the visceral oil differed from muscle oil in its lipid class composition. Neutral lipids, mainly triacylglycerols (TAG), comprised the major lipid class in both muscle and visceral lipid. However, as expected, muscle contained a remarkably higher level of phospholipids (PL) than viscera, and the ratio of total neutral lipids to polar lipids was lower in muscle than in viscera. Visceral and muscle lipid had similar fatty acid compositions, with the concentration of muscle polyunsaturated fatty acids (PUFA) slightly higher than that of visceral PUFA. Docosahexaenoic acid (DHA) and eicosapentaenoic acid (EPA) were the major n-3 PUFA present in both muscle and visceral lipid; docosapentaenoic acid (DPA) was present at about 1.61–1.76%. With respect to minor components, muscle lipid had higher α-tocopherol and total carotenoids contents than visceral lipid. Oxidative stability of visceral and muscle lipid, as determined by conjugated dienes (CD) and thiobarbituric acid reactive substances (TBARS), showed that visceral lipid was more stable against oxidation than muscle lipid, probably due to their different lipid profiles. Besides, carotenoids, which were present more abundantly in muscle, might have acted as prooxidants and therefore, decreased the oxidative stability of muscle lipid. These results suggest that steelhead trout viscera may serve as a good source of lipid and could be utilized for production of omega-3 oils.     

Effect of dietary lipid sources on odour‐active compounds in muscle of turbot (Psetta maxima)

Odour‐active compounds in muscle of turbot (Psetta maxima) fed experimental diets containing fish oil (FO), soybean oil (SO) or linseed oil (LO) were investigated by a gas chromatography/olfactometry technique. Thirty‐one areas associated with odours were detected in muscle extracts. Among the compounds responsible for these odours, 23 were formed by oxidation of unsaturated fatty acids. Independently of diet, (E)‐2‐penten‐1‐ol and (E)‐3‐hexen‐1‐ol contribute strongly to the odour of turbot. (E,Z)‐2,6‐Nonadienal, (E)‐2‐pentenal and (E,E)‐1,3‐(Z)‐5‐octatriene seem to contribute strongly to the odour of turbot fed diets containing high levels of n‐3 PUFA (FO and LO groups). Hexanal and decanal show a high detection frequency in turbot fed diets containing vegetable oils. Odorous compounds which are not formed by lipid oxidation (methional, 1‐acetyl pyrazine, 4‐ethyl benzaldehyde and 2‐acetyl‐2‐thiazoline) were not affected by dietary lipid sources. © 2001 Society of Chemical Industry     

Impacts of natural antioxidants on the fatty acid profiles of vacuum-packaged tuna-like muscles

The impacts of natural preservatives such as olive leaf (Olea europaea L.) and sweet marjoram (Origanum majorana L.) extracts (OLE and SME) and cold storage on the fatty acid profiles of vacuum-packaged tuna-like muscles were evaluated. At the end of the storage time, the lowest content of the total saturated fatty acids (SFA) was observed in both ordinary and dark muscles of the treated samples (OLE and SME) whereas the highest content was found in their counterparts from the untreated samples (control). The total polyunsaturated fatty acid (PUFA) and total monounsaturated fatty acid (MUFA) contents decreased markedly in both ordinary and dark muscles of the control samples. In contrast, treated samples remained relatively stable throughout the storage time since the employment of plant extracts had protective effects against lipid oxidation and help maintain MUFA and PUFA levels in frigate tuna muscles. In addition, the PUFA/SFA ratio and polyene index which are considered important dietetic parameters showed that the used plant extracts (OLE and SME) did not result in a reduction in the PUFA/SFA ratio and prevented PUFA damage in both frigate tuna muscles during storage. Thus, the use of plant extracts such as OLE and SME can be recommended as natural preservatives for the fish processing industry.     

Inhibition of oxidation of omega-3 polyunsaturated fatty acids and fish oil by quercetin glycosides

The antioxidant properties of naturally occurring flavonols, quercetin glycosides, were examined and compared with common food antioxidants butylated hydroxytoluene (BHT) and α-tocopherol. Antioxidants were incorporated into selected polyunsaturated fatty acids (PUFA) or fish oil in aqueous emulsions and bulk oil systems. The effectiveness of quercetin was similar to or greater than quercetin glycosides in inhibiting lipid oxidation in the oil-in-water emulsion systems when oxidation was induced by heat, light, peroxyl radical or ferrous ion. In bulk fish oil, C-3 glycosylation enhanced the antioxidant activity of quercetin. The effectiveness of quercetin and its glycosides was greater than that of α-tocopherol in the emulsions. Quercetin and quercetin-3-O-glucoside exhibited a better antioxidant activity than BHT in bulk fish oil; however, the reverse was observed in the emulsions of omega-3 PUFA and fish oil systems in agreement with the polar paradox theory. Quercetin and its glycosides were more effective than α-tocopherol in emulsion systems.     

Wax Esters of n -3 Polyunsaturated Fatty Acids: A New Stable Formulation as a Potential Food Supplement. 1 — Digestion and Absorption in Rats

Fish oils (FO) and their ethyl ester derivatives (EE) are proposed as rich sources of n -3 polyunsaturated fatty acids (PUFA), in view of their nutritional and therapeutic effects. However, they have drawbacks due to their high degree of susceptibility to oxidation, both during manufacturing and in living organisms. We prepared wax esters (WE) by transesterification of stoichiometric amounts of ethyl esters enriched with n -3 PUFA and long-chain alcohols (18-22 carbon atoms). They are waxy solids, with melting points from 30 to 52 °C, depending on the degree of unsaturation in the acidic and alcoholic moieties of the molecules. We studied their bioavailability in comparison with commercially available products, namely EE and FO, using an animal model (rat). WE have a low degree of susceptibility to oxidation and a high degree of enzymatic hydrolysis in vitro. After an oral load, rats hydrolyse and absorb WE to a greater extent than EE, resulting in significant enrichment of n -3 PUFA in plasma triglycerides. After dietary supplementation with WE (0.15 g/d/rat) for 4 weeks, n -3 PUFA in plasma phospholipid were comparable to those of rats receiving diets supplemented with FO and EE in equimolar concentrations of n -3 PUFA. Body weight, lipid profile and intestinal transit were not affected by 4 weeks' treatment with WE. These formulations offer a potential advantage as food supplements over products in current use, on account of their greater stability.     

Importance of instrumental and sensory analysis in the assessment of oxidative deterioration of omega‐3 long‐chain polyunsaturated fatty acid‐rich foods

Omega‐3 long‐chain polyunsaturated fatty acids (LC PUFA) positively influence human health. Their main dietary source is fish, especially fish oil. Owing to low fish consumption in many Western countries the average intake of omega‐3 LC PUFA is below the recommended level. This raises interest in diet supplementation and food enrichment with fish oil. However, due to a high degree of unsaturation fish oil is extremely susceptible to oxidation. Oxidation of fish oil increases when added to food products, which may be enhanced by some antioxidants, under certain conditions. For quality control of omega‐3 LC PUFA‐containing foods adequate and combined methods of oxidation assessment should be used, beginning from the raw material and continuing during processing, storage and distribution. To achieve this goal correlation of instrumental and sensory methods with multivariate data analysis may give the best results. In this paper problems of oxidation of fish oil and fish oil‐containing foods, as well as methods for its assessment, are reviewed. Copyright © 2006 Society of Chemical Industry     

Fatty acids distribution in different tissues of wild and reared Seriola dumerili

In this study, we compared the lipid and fatty acids content, between cultured and wild Seriola dumerili, in different edible portions. Results showed that cultured fish contained a higher level of lipids than wild fish. The fatty acids profiles revealed that, among all the split‐fish side, palmitic (C16:0) and oleic (C18:1n‐9) acid were the principal saturated and monounsaturated fatty acids, in cultured and wild S. dumerili. On the other hand, wild S. dumerili contained a higher level of saturated (38.12 ± 0.54% vs. 33.66 ± 0.15% in cultured fish), monounsaturated (33.13 ± 1.07% vs. 26.49 ± 0.17%), n‐3 polyunsaturated fatty acids (PUFA) (23.90 ± 1.02% vs. 19.77 ± 0.51%) particularly docosahexaenoic acid (DHA) (18.83 ± 0.48% vs. 11.77 ± 0.42%). However, the cultured fish showed a higher level of n‐6 PUFA due principally to the higher value of linoleic acid (C18:2n‐6). In fact, changes in fatty acids content between anatomical areas marked differences in the muscle quality of wild and cultured S. dumerili. According to this study, both groups of wild and farmed S. dumerili have nutritional benefits for human health. Cultured fish were characterised by higher hypocholesterolaemic and hypercholesterolaemic fatty acids ratio for all samples studied and a lower n‐3/n‐6 ratio due to the abundance of n‐3 PUFA particularly DHA in wild fish.     

Lipid distribution and composition of commercially farmed atlantic salmon (salmosalar)

Skin, red and white muscle, belly flap, dorsal fat depot, backbone, head, visceral tissue and liver of commercially farmed Atlantic salmon (Salmo salar) were analysed for total lipid content, lipid classes and fatty acid composition. The fat is deposited in a number of tissues and organs with the highest level in the dorsal fat depot (38.4% of wet weight), red muscle (27.2%) and belly flap (28.1%). The fat content in white muscle is 9.6% of wet weight. The lipid class distribution is nearly uniform throughout the fish body. The belly flap contains the highest amount of triacylglycerols (98.8% of total lipid) and white muscle and visceral tissue have the lowest levels, 93.3% and 93.1%, respectively. The variation in total saturates, monoenes, polyenes, n-6 and n-3 fatty acids was much less between tissues than the variation in total lipid content. In the edible part, the belly flap (16.7%) contained significantly lower levels of n-3 fatty acids than red (18.4%) and white muscle (19.7%) mainly due to lower level of 22: 6n-3 and 20: 5n-3 fatty acids.     

Influence of fatty acids compositions and manufacturing type on the formation of 4-hydroxy-2-alkenals in food lipids

Correlations between 4-hydroxy-2-hexenal (HHE) or 4-hydroxy-2-nonenal (HNE) and fatty acids were statistically investigated in 73 kinds of commercially available food sources of n-3 or n-6 polyunsaturated fatty acids (PUFA). The analysis revealed that the level of HNE was obviously correlated with the contents of PUFA (r=0.462), n-6 PUFA (r=0.512), and saturated fatty acids (r=0.535). Significant correlation was also observed between HHE and HNE (r=0.486) although whose source fatty acids were different. Regarding the sesame oils and perilla oils currently available on the Korean markets, no appreciable difference in the levels of HHE or HNE was found depending on their manufacturing types.     

How do n-3 fatty acid (short-time restricted vs unrestricted) and n-6 fatty acid enriched diets affect the fatty acid profile in different tissues of German Simmental bulls?

This study investigated the effect of n-6 (control group) and n-3 polyunsaturated fatty acids (PUFA) supply (treatment group unrestricted) and a short-time feed restriction for n-3 PUFA supply (treatment group restricted) on intramuscular fat content and the total fatty acid composition in different tissues (muscle, subcutaneous fat, liver, serum and erythrocytes) and lipid classes of intramuscular fat of German Simmental bulls (n = 25). Exogenous n-3 PUFA caused a higher concentration of the sum of all single n-3 and n-3 long-chain polyunsaturated fatty acids (LC PUFA) in all analysed tissues. Feed restriction compared to control feeding induced a significant decrease of C18:1cis-9 in the phospholipid fraction of longissimus muscle and in subcutaneous fat. The concentration of C18:3n-3 in liver of treatment groups was between 34 and 44% higher compared to control. PUFA in serum and the sum of n-3 PUFA in erythrocytes were significantly higher in both treatment groups compared to control. The synthesis and deposition of n-3 LC PUFA seems to be tissue dependent according to different relative amounts.     

Effects of dietary fats on meat quality and sensory characteristics of heavy pig loins

Forty-eight crossbred growing-finishing pigs were used to study the effects of polyunsaturated fatty acids (PUFA 31%= low and 50%= high) and fish oil (0, 0.2, and 0.4% capelin) diets on fatty acid composition, chemical traits, and sensory properties of the longissimus muscle, fat, and sausages. High levels of PUFA, independent of the level of fish oil, increased oxidation and rancidity for whole muscle (stored at 1 and 8 months at -23?°C) and sausages (TBARS 0.6-1.3). Fish oil at 0.4% in the diet increased TBA values of loin, but did not affect sensory evaluation scores. An interaction between PUFA and fish oil occurred for TBARS values and rancid odour in sausage, where the 0.4% fish oil and high PUFA level showed highest oxidation (TBARS 1.9). Although fish oil and high PUFA levels might contribute to a more healthy meat, their undesirable affects on palatability would limit their use.     

Alkylresorcinols as antioxidants: hydrogen donation and peroxyl radical‐scavenging effects

Alkylresorcinols, resorcinol derivatives with a long hydrocarbon chain at position 5 of the phenolic ring, have been reported to act as antioxidants and protect polyunsaturated fatty acids against peroxidation. Their structures with meta‐dihydroxy substitutions do not, however, support active hydrogen donation and scavenging of peroxyl radicals responsible for propagation of lipid oxidation. This study compares the antioxidant properties of 5‐n‐pentadecylresorcinol and α‐tocopherol using two model systems: (i) the DPPH· model to test their ability for hydrogen atom donation; and (ii) a triacylglycerol oxidation model to test their ability for scavenging peroxyl radicals. In agreement with theoretical expectations, results from both models showed 5‐n‐pentadecylresorcinol to have very low hydrogen donation and peroxyl radical‐scavenging potency. © 2000 Society of Chemical Industry     

杀菌温度对乳化肠中脂肪酸组成和脂肪氧化的影响

通过氯仿-甲醇法提取乳化肠中的脂肪,并进行皂化和甲酯化,采用气相色谱-质谱联用技术系统对比研究 不同杀菌温度对乳化肠中脂肪酸组成和脂肪氧化的影响。结果表明：乳化肠经不同杀菌温度处理后,脂肪酸含量和 脂肪氧化都会发生一定程度的变化。杀菌温度超过100 ℃时,饱和脂肪酸（saturated fatty acids,SFA）含量显著增 加（P＜0.05）,而不饱和脂肪酸（unsaturated fatty acids,UFA）含量显著降低（P＜0.05）,其中多不饱和脂肪酸 （polyunsaturated fatty acid,PUFA）的含量呈极显著降低（P＜0.01）,而单不饱和脂肪酸（monounsaturated fatty acid,MUFA）含量差异不显著（P＞0.05）;n-6 PUFA/n-3 PUFA比值显著增加,PUFA/SFA比值显著降低,同时 100～110 ℃杀菌温度显著提高了产品的过氧化值（peroxide value,POV）和硫代巴比妥酸反应物（thiobarbituric acid reactive substances,TBARS）含量。100 ℃以上的杀菌温度使C14:0、C16:0、C18:0和C20:0的含量显著提高,同时 C18:2n6、C18:3n3、C20:3n6和C20:4n6的含量显著降低,而C20:5n3和C22:6n3未检出。结论：低于100 ℃的杀菌条件可以最大程度 保持产品原有的脂肪酸组成,而高于100 ℃的杀菌温度对产品的脂肪酸比例破坏明显,且可显著促进脂肪氧化,这 为杀菌条件在肉制品中的精细化调控提供技术支持。     

Effects of differences in diet and seasonal changes on the fatty acid composition in fillets from farmed and wild sea bream (Sparus aurata L.) and sea bass (Dicentrarchus labrax L.)

The effects of dietary fatty acids and seasonal variation on the fatty acid profiles of farmed and wild sea bream (Sparus aurata) and sea bass (Dicentrarchus labrax) were determined by analysis of their fillets. Farmed sea bream and sea bass were fed on the same commercial feeds all year. Fatty acid profiles in the fillets reflected the fatty acid profiles of the commercial feeds. The predominant fatty acids in the trial feeds, fillets of farmed and wild sea bream and sea bass were 16:0, 18:1n‐9, 18:2n‐6, 20:5n‐3 and 22:6n‐3. The fatty acid profiles in the fillets of farmed sea bream and sea bass did not differ (P > 0.05) except in the winter season compared with those of their wild counterparts. However, the content of eicosapentaenoic acid (20:5n‐3), docosahexaenoic acid (22:6n‐3) in the fillets of the farmed and wild sea bass were significantly (P < 0.05) higher than the farmed and wild sea bream. The wild sea bream had significantly (P < 0.05) higher total saturated fatty acid and monounsaturated fatty acid (MUFA) levels, and lower total n‐6 and n‐3 polyunsaturated fatty acid (PUFA) levels in winter than in the summer and spring seasons. Similarly, in the fillets of wild sea bass, total n‐3 PUFA levels were significantly (P < 0.05) lower, and the MUFA levels were higher in winter than in the other seasons. These results indicate that the farmed fish fillets were good sources of n‐3 PUFA in each of the three seasons. However, wild fish were good sources of n‐3 PUFA in the spring and summer.     

Nutritional and sensory aspects of light lamb meat enriched in n−3 fatty acids during refrigerated storage

Fatty acid content and sensory characteristics of meat from light lambs fed three diets supplemented with different sources of n−3 fatty acids (fish oil, extruded linseed and extruded linseed plus microalgae) and a control diet during refrigerated storage have been studied. The meat from lambs fed linseed diets had the highest levels of C18:3 n−3, while animals fed fish oil had the highest long-chain n−3 polyunsaturated fatty acids (PUFA). Thus, 100 g of meat from lamb fed the fish oil diet provided 183 mg of long-chain n−3 PUFA, representing 40% of the daily recommended intake. The levels of n−3, n−6 and long-chain n−3 PUFA decreased during a 7-day storage period. The meat from lambs fed the fish oil diet had high scores of fish odour and flavour and rancid odour and flavour and the lowest overall liking. Rancid odour and flavour increased after storage, mainly in supplemented groups.     

Lipolytic and oxidative changes in Iberian dry-cured loin

This study was conducted using 61 Iberian pigs from four different genetic lines fattened under two different rearing systems. Fatty acid composition of neutral lipids (NL), polar lipids (PL) and free fatty acids (FFA) of the 61 fresh loins and their corresponding dry-cured loins and indices of lipid oxidation (hexanal, TBARS and rancid flavour) of the dry-cured loins were analyzed. Although the total amount of fatty acids from PL decreased most (89.77%), the fatty acid profile of FFA from dry-cured loin was more similar to that of NL from fresh loins. Monounsaturated fatty acids (MUFA) were the most abundant FFA type (260mg/100g muscle dry matter) followed by saturated fatty acid (SFA) (256mg/100g muscle dry matter) and polyunsaturated fatty acids (PUFA) (148mg/100g muscle dry matter). Neither genetic line nor rearing system showed any significant (P>0.05) effect on the decrease of fatty acids in the lipid fractions studied. The important decrease in PUFA from NL (43.70%) and PL (89%) was not reflected in higher oxidative indices in dry-cured loin. Neither PCA nor Pearson's correlation showed any clear relationships between lipolytic changes and oxidative indices.     

中国大鲵肌内脂肪酸组成及其抗氧化研究

分析中国大鲵肌内脂肪酸的组成,并研究肌内脂肪酸抗氧化,提供肌内脂肪酸开发利用的基础理论。通过气相色谱/质谱联用技术分析肌内脂肪酸的组成;通过Schaal烘箱法(63±1℃)研究肌内脂肪酸的抗氧化特性。GC-MS分析结果表明:肌内脂肪主要含13种脂肪酸,其含量由高到低依次为,C18∶124.2%,C16∶015.4%,C16∶113.7%,C18∶28.2%,C20∶56.7%,C18∶34.5%,C22∶64.3%,C14∶13.0%,C18∶02.8%,C22∶52.6%,C20∶42.2%,C17∶02.0%,C17∶11.9%。饱和脂肪酸(SFA)为20.2%,不饱和脂肪酸(UFA)达71.3%。单不饱和脂肪酸(MUFA)为42.8%,多不饱和脂肪酸(PUFA)为28.5%,具有保健功能性作用的ω-6型PUFA为13.0%,ω-3型PUFA为15.5%。ω-6型与ω-3型PUFA比为0.8。Schaal烘箱法研究结果表明:抗氧化剂二丁基对甲苯酚(BHT)、没食子酸丙酯(PG)、特丁基对苯二酚(TBHQ)对肌内脂肪酸有明显的抗氧化作用,其中特丁基对苯二酚抗氧化效果较佳。中国大鲵肌内脂肪富含ω-3和ω-6型...     

Oxidative stability of palm‐ and soybean‐based medium‐ and long‐chain triacylglycerol (MLCT) oil blends

BACKGROUND: Medium‐ and long‐chain triacylglyerols (MLCT) enzymatically esterified using Lipozyme RM IM lipase has very low oxidative stability as it does not contain any antioxidants. The aim of this work was to study the ability of various antioxidants to increase the oxidative stability of palm‐ and soybean‐based MLCT blends which assist to bring up the oxidative stability of both MLCT blends. In this study, the effectiveness of rosemary extracts, sage extracts, tert‐butylhydroquinone (TBHQ) and mixtures of tert‐butyl‐4‐hydroxyanisole (BHA) and tert‐butyl‐p‐hydroxytoluene (BHT) in protecting against oxidation of various MLCT blends was investigated. RESULTS: Blending of MLCT oil with either palm olein or soybean oil improved its smoke point values and oxidative stability. TBHQ addition to both palm‐ and soybean‐based MLCT blends increased oxidative stability. Combination of BHA and BHT showed no significant improvement (P > 0.05) in ability to protect blends from oxidation compared to natural antioxidants such as sage or rosemary extracts. CONCLUSION: Blended oils with 500 g kg^?1 MLCT and 500 g kg^?1 palm olein (MP5) were the most suitable for use at high temperature based on the fatty acid composition of the MLCT blends, which subsequently had an effect on thermal oxidative stability. In general, addition of either natural or synthetic antioxidant assisted in improving the antioxidative strength of both MLCT blends. MLCT blends with added TBHQ showed the highest thermal oxidative stability among the antioxidants used. Copyright © 2008 Society of Chemical Industry