Composition and distribution of fatty acids in triglycerides from goat infant formulas with milk fat

Most infant formulas use vegetable oils in place of milk fat to provide an overall fatty acid profile similar to that of breast milk. Vegetable oils have 5 to 20% saturated fatty acids in the sn-2 position of triglycerides unless they are modified by interesterification. Interesterification is increasingly used for the fat for infant formulas to raise the level of saturated fatty acids in the sn-2 position to 40 to 60%. The objective of this study was to verify an alternative approach to providing the appropriate fatty acid profile, including in the sn-2 position, for a goat infant formula. In this method, 55% of total fat was made from goat milk fat and 45% from a mixture of unmodified high oleic sunflower, canola, and sunflower oils in a ratio of 44:30:26. The fatty acid profile was measured by gas-liquid chromatography and the relative percentage of fatty acids in the sn-2 position of triglycerides was measured via partial deacylation with Grignard reagent using trimethylsilyl derivatives of monoacylglycerols. Mixing goat milk fat with vegetable oils produced a formula with a profile of essential fatty acids and a ratio of linoleic:α-linolenic fatty acids within the required interval of 5 to 15:1 recommended for infant formula. The proportion of palmitic acid in the sn-2 position was 31%.     

Enzymatic production of human milk fat substitutes containing palmitic and docosahexaenoic acids at sn-2 position and oleic acid at sn-1,3 positions

This paper studies the synthesis of structured triacylglycerols (STAGs) rich in palmitic and docosahexaenoic acids (PA and DHA) at sn-2 position and oleic acid (OA) at sn-1,3 positions by a four step process. First, triacylglycerols (TAGs) were obtained with 63–66 mol PA/100 mol total fatty acids and 10 mol DHA/100 mol by acidolysis of tuna oil and commercial PA, catalyzed by the non-positionally specific lipase Novozym 435. Then these TAGs were purified neutralizing the free fatty acids (FFAs) by KOH hydroethanolic solutions and extracting TAGs with hexane; these TAGs were completely recovered as pure TAGs (without FFAs). The third step involved the displacement of fatty acids located at sn-1,3 positions by acidolysis of PA and DHA enriched TAGs with OA rich FFAs, catalyzed by the sn-1,3 specific lipase DF from Rhizopus oryzae, immobilized on Accurel MP-1000; TAGs with 67 mol OA/100 mol at sn-1,3 positions and 52.1 and 15.4 mol PA and DHA, respectively, per 100 mol at sn-2 position were obtained. Both acidolysis reactions were carried out in stirred tank reactors (STRs) with lipase both dispersed in the reaction medium and contained in a cartridge filter attached to the stirrer rod. Finally STAGs were purified and obtained with yields of over 80 mol STAGs/100 mol STAGs in the reaction product (no FFAs were detected).     

POSITIONAL DISTRIBUTION OF FATTY ACIDS IN TRIACYLGLYCEROLS OF SEAL BLUBBER OIL

The positional distribution of long-chain ω3 polyunsaturated fatty acids namely eicosapentaenoic acid (EPA), docosapentaenoic acid (DPA), and docosahexaenoic acid (DHA) in the triacylglycerol (TAG) molecules of seal blubber oil was determined and compared with that of commercially available menhaden oil via stereospecific analysis. In seal blubber oil, EPA, DPA and DHA occurred mainly in the sn-1 and sn-3 positions of the TAG molecules. The amounts were EPA, 8.36 and 11.2; DPA, 3.99 and 8.21; and DHA, 10.5 and 17.9%, respectively. In menhaden oil, DPA and DHA occurred mainly in the sn-2 position of the TAG at 3.11 and 17.2%, respectively. However, EPA was equally distributed in the sn-2 and sn-3 positions and was present only in minute amounts in the sn-1 position.     

褐点石斑鱼鱼肉及其副产物的脂肪酸分析

为了评估褐点石斑鱼的脂肪酸组成特点,采用固相萃取和气相色谱技术对鱼肉、头、皮和内脏的脂质含量、总脂及各脂类脂肪酸组成,甘油三酯(triacylglycerols, TAG)和磷脂(phospholipids, PL)中脂肪酸的位置分布进行了较全面的分析。石斑鱼鱼头和内脏中含有丰富的糖脂(saccharolipids, SL)和PL。在各组织总脂中,必需脂肪酸的含量占总脂肪酸的24.17%～24.51%,二十二碳六烯酸(docosahexaenoic acid, DHA)及二十碳五烯酸(eicosapentaenoic acid, EPA)的含量为12.42%～13.73%,动脉粥状硬化指数、血栓形成指数和n-6/n-3的比例处于较低水平。多不饱和脂肪酸(polyunsaturated fatty acids, PUFA),尤其是DHA+EPA(28.43%～37.37%)在PL中的比例要远高于在其它脂类中的占比。饱和脂肪酸主要分布在TAG和PL的sn-2位,单不饱和脂肪酸主要分布在TAG的sn-1,3位和PL的sn-2位,PUFA倾向于分布在TAG的sn-1,3位和PL的sn-1位;T...     

Enzymatic Synthesis of Refined Olive Oil‐Based Structured Lipid Containing Omega ‐3 and ‐6 Fatty Acids for Potential Application in Infant Formula

Structured lipids (SLs) containing palmitic, docosahexaenoic (DHA), and gamma‐linolenic (GLA) acids were produced using refined olive oil, tripalmitin, and ethyl esters of DHA single cell oil and GLA ethyl esters. Immobilized Lipozyme TL IM lipase was used as the biocatalyst. The SLs were characterized for fatty acid profile, triacylglycerol (TAG) molecular species, solid fat content, oxidative stability index, and melting and crystallization profiles and compared to physical blend of substrates, extracted fat from commercial infant formula (IFF), and milk fat. 49.28 mol% of palmitic acid was found at the sn‐2 position of SL TAG and total DHA and GLA composition were 0.73 and 5.00 mol%, respectively. The total oleic acid content was 36.13 mol% which was very close to the 30.49% present in commercial IFF. Comparable solid fat content profiles were also found between SLs and IFF. The SLs produced have potential for use in infant formulas.     

Evaluating nutritional quality of pacific fish species from fatty acid signatures

Eight fish species common to the Pacific Northwest coastal waters were categorised according to total lipids in a ranking from lean fish (e.g. walleye pollock) to oily fish (e.g. herring) species. Comprehensive fatty acid signatures were compared on both the relative proportion of total fatty acids and the proportion of total carcass lipid content. Generally, fish species from the Pacific coast had a relatively high proportion of n-3 highly polyunsaturated fatty acids (n-3 HUFAs), of which more than 80% was accounted for by C20:5n-3 (EPA) and C22:6n-3 (DHA), with species-specific and lower proportions of oleic acid (C18:1n-9) and palmitic acid (C16:0) also dominating. The MUFA contents of fish were lower (P < 0.05) in the lipids of lean and low-fat fish compared to those of fattier species. In contrast, higher (P < 0.05) proportions of polyunsaturated fatty acids (PUFAs) existed in the low-fat species with DHA contents ranging from 18% to 29% in the low-fat fish and from 8% to 10% in the fattier fish, such as herring and capelin. Expressing the same fatty acid content data in terms of absolute amount of fatty acids (e.g. gFA/100 g wet tissue) showed that both EPA and DHA contents in the flesh of pollock and hake were indeed many fold lower than those found in fatty fish, such as herring. The findings confirm that it is important that both the total lipid content and the fatty acid composition of these Pacific fish food sources be considered when making evaluations on the nutritional quality.     

Fatty acid distribution in triacylglycerols and phospholipids of broad beans (Vicia faba)

Fatty acid distribution of triacylglycerols (TAG) and phospholipids (PL) obtained from the four cultivars of broad beans (Vicia faba) was investigated. Total lipids extracted from the beans were separated by thin-layer chromatography into eight fractions. The major lipid components were TAG (47.7–50.1%) and PL (47.5–50.5%), while hydrocarbons, steryl esters, free fatty acids, diacylglycerols (1,3-DAG and 1,2-DAG) and monoacylglycerols were present in minor proportions (1.8–2.4%). The major PL components were phosphatidylcholine (56.4–58.4%), phosphatidylethanolamine (20.3–21.7%) and phosphatidylinositol (16.6–18.6%). Phosphatidylinositol was unique in that it had the highest saturated fatty acid content among the three PL. No significant differences (P > 0.05) in fatty acid distribution existed when the different cultivars were compared. The fatty acid distributions in the TAG were evident among the four cultivars: unsaturated fatty acids were predominantly concentrated in the sn−2 position, and saturated fatty acids primarily occupied the sn−1 or sn−3 position in the oils. These results could be useful to both consumers and producers for manufacture of traditional foods in Japan and elsewhere.     

Compositional Information Useful for Authentication of Krill Oil and the Detection of Adulterants

Nuclear magnetic resonance (NMR) spectroscopy and chromatography, particularly thin layer chromatography with flame ionisation detector (TLC-FID), were used to investigate fish oil adulteration of krill oil with ethyl esters and triacylglycerol. Natural krill oil has higher levels of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) in phospholipid than in triacylglycerol and so high levels of these omega-3 fatty acids in krill oil triacylglycerol was indicative of adulteration. Carbon (¹³C) NMR detected adulteration of krill oil with 10% or more anchovy oil, while TLC-FID detected levels as low as 1% adulteration with EPA ethyl esters. However, positional distribution of EPA and DHA, as determined using ¹³C NMR, was similar for both fish oil and krill oil, indicating that positional distribution cannot be used to show adulteration. Phosphorous (³¹P) NMR spectroscopy can show adulteration with low cost sources of phospholipid but was not useful for determining adulteration of krill oil with fish oil.     

Structural analysis of triacylglycerol fraction and some its sub-fractions from an eicosapentaenoic acid/docosahexaenoic acid dietary supplement

 Ag⁺- and RP-HPLC have been used to study the triacylglycerol fraction of a dietary supplement containing fish oil. The fatty acid (FA) distribution in the glycerol backbone of the triacylglycerol fraction was determined by stereospecific analysis. Eicosapentaenoic acid, the most abundant poly unsaturated FA, was predominantly located in the sn-3 position, while docosahexaenoic and docosapentaenoic acids were generally located in the sn-2 position. The nutritional significance of these findings is briefly discussed. Received: 18 February 1998 / Revised version: 25 June 1998     

Total lipid content and fatty acid composition of commercially important fish species from the Mediterranean, Mar Grande Sea

The fatty acid (FA) profiles of 11 commercially important fish species from the sea of Southern Italy (Mar Grande Sea) were investigated.The results showed significant differences among the fatty acid profiles of the examined fish (p < 0.05). A relatively high proportion of n − 3 polyunsaturated fatty acids (PUFAs), of which more than 70% were accounted by docoesahexaenoic acid (DHA) and eicoesapentaenoic acid (EPA) in salema, bogue, common two-banded seabream and sand smelt, and lower proportions of oleic acid (C18:1n − 9) and palmitic acid (C16:0) also dominating. The percentages of EPA and DHA were between 5.03-8.61% and 9.85-17.39% of total lipid, respectively.The results showed that the fish examined are a good source of n − 3 PUFAs, resulting in a very favourable n3 - n6 ratio, especially in salema, sand smelt, common two-banded seabream and picarel.     

海洋鱼油深加工技术研究进展

海洋鱼油深加工技术可以更加合理、有效地利用其中的EPA和DHA等多不饱和脂肪酸,提升鱼油的利用价值.介绍了以海洋鱼油为原料的EPA/DHA产品的深加工技术,主要包括鱼油脱腥、多不饱和脂肪酸的富集纯化,新型EPA/DHA产品的开发与应用以及产品稳定性的研究.对海洋鱼油多不饱和脂肪酸深加工技术进行了分析与展望,认为含有高纯度EPA、DHA等多不饱和脂肪酸的鱼油产品仍是市场的主流需要.     

Distribution of fatty acids in triacylglycerols and phospholipids from peas (Pisum sativum L.)

BACKGROUND: The fatty acid distribution of triacylglycerols (TAG) and major phospholipids (PL) obtained from four varieties of peas (Pisum sativum) was investigated. The total lipids extracted from the peas were separated by thin layer chromatography into seven fractions. RESULTS: The major lipid components were PL (52.2–61.3%) and TAG (31.2–40.3%), while hydrocarbons, steryl esters, free fatty acids and diacylglycerols (sn‐1,3 and sn‐1,2) were also present in minor proportions (5.6–9.2%). The main PL components isolated from the four varieties were phosphatidylcholine (42.3–49.2%), phosphatidylinositol (23.3–25.2%) and phosphatidylethanolamine (17.7–20.5%). Significant differences (P < 0.05) in fatty acid distribution were found for different pea varieties. Phosphatidylinositol was unique in that it had the highest saturated fatty acid content among the three PL. However, the principal characteristics of the fatty acid distribution in the TAG and three PL were evident among the four varieties: unsaturated fatty acids were predominantly located in the sn‐2 position while saturated fatty acids primarily occupied the sn‐1 or sn‐3 position in the oils of the peas. CONCLUSION: These results should be useful to both producers and consumers for the manufacture of pea foods in Japan. Copyright © 2007 Society of Chemical Industry     

Long-chain n-3 fatty acids and classical cardiovascular disease risk factors among the Catalan population

The protective cardiovascular effect of long-chain n-3 fatty acids has been firmly established in populations with high fish consumption, like those from Mediterranean countries. The current fish consumption in a representative sample from Catalonia, a Mediterranean region, and its relationship with plasma concentrations of eicosapentaenoic (EPA) and docosahexaenoic (DHA) and some classical cardiovascular disease risk factors was evaluated. Mean fish and seafood intake was 78.5 ± 51.4 g/day. Mean plasma concentrations of EPA and DHA were respectively 0.48% and 1.99% of total fatty acids. Consumption of marine foods among the Catalan population, the main source of n-3 fatty acids, appears to beneficially affect some cardiovascular disease risk factors. Our results show that both EPA and DHA are negatively associated with triacylglycerol (TG) concentrations and the ratio of total cholesterol (TC) to HDL-cholesterol. Furthermore, EPA but not DHA has a beneficial effect on plasma HDL-cholesterol among the Catalan population. There were no significant associations between long-chain n-3 fatty acids and LDL-cholesterol, TC, glucose, insulin or blood pressure. Oily fish intake, which is richest in EPA and DHA, is currently at an order of only 1 serving per week in the Catalan population and its increase should therefore be promoted.     

Selective concentration of EPA and DHA using Thermomyces lanuginosus lipase is due to fatty acid selectivity and not regioselectivity

The selectivity of anchovy oil hydrolysis was optimised for Thermomyces lanuginosus lipase, so that docosahexaenoic acid (DHA) and eicosapentaenoic acid (EPA) were concentrated and partially separated from each other. Enzyme concentration and pH control were important factors for effective hydrolysis. Monitoring percent hydrolysis using capillary chromatography with flame ionisation detector (Iatroscan) and fatty acid selectivity using gas chromatography (GC) indicated that during hydrolysis DHA primarily remained on the glycerol backbone, while EPA was progressively removed. ¹³C nuclear magnetic resonance (NMR) data showed that selectivity of hydrolysis was primarily due to fatty acid selectivity and not regioselectivity, with hydrolysis from both sn-1,3 and sn-2 sites being equally favoured.     

Stereospecific analysis of triacylglycerol and phospholipid fractions of four freshwater fish species: Salmo trutta, Ictalurus punctatus, Ictalurus melas and Micropterus salmoides

The fatty acid compositions and the positional distributions of fatty acid in triacylglycerol (TAGs) and phospholipid (PLs) fractions of four cultured freshwater fish species (Salmo trutta, Ictalurus punctatus, Ictalurus melas and Micropterus salmoides) were investigated. As regards the TAGs fraction, the S. trutta (trout) and I. punctatus (channel catfish) species had the highest % content in n3 polyunsaturated fatty acids (PUFAs) and the lowest n6/n3 ratio; this ratio resulted always lower than 1 in all the considered fish species. The PLs fraction of the considered fish was very interesting because of the high percentage of PUFAs, both in phosphatidylcholines and in phosphatidylethanolamines. The fatty acid distribution among the three sn-positions of the glycerol backbone was non-random; generally, both n6 and n3 PUFAs were mainly distributed between sn-2- and sn-3-positions of TAGs while the contents in sn-1-position were generally lower; in PLs fraction these fatty acids preferred the sn-2-position.     

Changes in fatty acid composition in muscle of three farmed carp fish species (Labeo rohita,Cirrhinus mrigala,Catla catla) raised under the same conditions

This study was carried out to determine the proximate composition, fatty acid profile and biometric data for farm fish species Labeo rohita, Cirrhinus mrigala, Catla catla raised under identical conditions. The analysed fish species were found as source of high polyunsaturated fatty acids with low fat high protein. Fat content of the fish fillets was in range 2.57–3.11 g/100 g. Whereas fat content for feed was 14.90 g/100 g. The protein level for the three fish ranged from 20.00–23.57 g/100 g and in feed it was estimated in the range of 67.70 g/100 g. The palmitic acid and stearic acid were the main saturated fatty acids (SFA), oleic acid was the predominant MUFA while the docosahexanoic acid and eicopentanoic acid were the major PUFA. The percentage of DHA exceeded that of EPA in all fish species analysed. The n−3/n−6 ratio ranged from 1.69–1.91. PUFA/SFA ratio was much higher in L. rohita (1.40) due to abundance of n−3 PUFA, particularly DHA.     

Stereospecific analysis of triacylglycerols in camel (Camelus dromedarius) milk fat

In the lipid fraction of camel (Camelus dromedarius) milk the percentage of saturated fatty acids (SFAs) was 62.8% with a content of palmitic acid of 28.5%. The unsaturated fatty acid (UFA) fraction was dominated by oleic and palmitoleic acids. Enzyme digestion and chemical degradation methods were used to determine the intramolecular fatty acid (FA) composition and then the intermolecular FA distribution in the three sn-positions of the triacylglycerols of the camel milk. FAs showed a specific preference for a particular position: in all samples studied, SFAs were prevalently esterified in the sn-2 position, while UFAs occupied mainly the sn-1 and sn-3 position. As the carbon chain lengthened from 8 to 16 the percentages of SFAs decreased in the sn-2 position and increased in the outer positions. Such data indicated that the length of the carbon chain could be a discriminating factor in the acylation process of SFAs.     

Roasting effects on fatty acid distributions of triacylglycerols and phospholipids in sesame (Sesamum indicum) seeds

Sesame seeds were roasted at different temperatures (180–220 °C) using a domestic electric oven. The positional distribution of fatty acids in triacylglycerols (TAGs) and phosphatidylcholine (PC) isolated from total lipids in these seeds was investigated as well as the naturally occurring antioxidants that are present. Major lipid components were TAGs and phospholipids (PLs), while steryl esters (SEs), free fatty acids (FFAs) and sn‐1,3‐ and sn‐1,2‐diacylglycerols (DAGs) were minor ones. Following roasting, a significant increase (P < 0.05) was observed in FFAs and in both forms of DAG (primarily sn‐1,3‐DAG). The greatest PL losses (P < 0.05) were observed in phosphatidylethanolamine (PE), followed by PC and phosphatidylinositol (PI). On the other hand, the amounts of γ‐tocopherol and sesamin remained at over 80 and 90% respectively of the original levels after roasting at 220 °C. The principal characteristics of the positional distribution of fatty acids were still retained after 25 min of roasting: unsaturated fatty acids, especially linoleic and/or oleic, were predominantly concentrated in the sn‐2‐position, and saturated fatty acids, especially stearic and/or palmitic, primarily occupied the sn‐1‐ or sn‐3‐position. The results suggest that unsaturated fatty acids located in the sn‐2‐position are significantly protected from oxidation during roasting at elevated temperatures. © 2001 Society of Chemical Industry     

Seasonal changes of fatty acids of cuttlefish Sepia officinalis L. (Mollusca: Cephalopoda) in the north eastern Mediterranean sea

The total lipids and seasonal variations in the fatty acids of the mantle of cuttlefish (Sepia officinalis) captured in the north eastern Mediterranean were investigated and the mantle was found to be a good source of polyunsaturated fatty acids (ω3 PUFAs, in particular). In all seasons, the major fatty acids in the cuttlefish mantle were observed to be palmitic acid (16:0), stearic acid (18:0), eicosapentaenoic acid (EPA, 20:5ω3) and docosahexaenoic acid (DHA, 22:6ω3). A comparison of the saturated fatty acid (29.5–36.8%), monounsaturated fatty acids (7.81–9.84%) and polyunsaturated fatty acids (43.7–49.6%) of the cuttlefish mantle revealed that polyunsaturated fatty acids (PUFA) constituted the highest proportion. The levels of DHA in the cuttlefish mantle in autumn, winter, spring and summer were 27.6%, 28.5%, 29.5% and 23.9%, while those of EPA were 16.8%, 15.4%, 14.7% and 13.9%, respectively.     

Comparison of Polyunsaturated Fatty Acids Content in Filets of Anadromous and Landlocked Sockeye Salmon Oncorhynchus Nerka

Abstract: Fatty acid composition and content of 2 forms of sockeye salmon Oncorhynchus nerka from lakes in Kamchatka Peninsula (Russia) were compared. One form of sockeye salmon was anadromous (“marine”), that is, adult fish migrated in ocean to feed and grow and than return in the lake to breed. Fish of another form, kokanee, never migrate in the ocean. Per cent levels of the main indicators of nutritive value, eicosapentaenoic acid (EPA, 20:5n‐3), and docosahexaenoic acid (DHA, 22:6n‐3), were significantly higher in the landlocked O. nerka. However, concentrations of EPA and DHA per wet weight of filets were higher in the marine form, because of the relatively higher content of sum of fatty acids in their muscle tissue. As concluded, fish fed in marine environment had higher contents of long‐chain n‐3 fatty acids per wet weight than fish of the same species, fed in fresh waters. In general, both the anadromous sockeye salmon and the landlocked kokanee salmon can be recommended for human diet as a valuable product concerning contents of EPA and DHA. Practical Application: The long‐chain polyunsaturated acids (PUFA) have been specifically recommended for humans to prevent cardiovascular disease and psychiatric disorders. Fish are known to be the main source of PUFA in human diet. Data on PUFA content in diverse food fish is essential to compare the benefits they offer for consumers’ health. We compared PUFA contents in 2 forms of popular food fish Oncorhynchus nerka, migrating sockeye salmon and landlocked kokanee salmon, and found that both forms are valuable product concerning PUFA content.