EUROPEAN JOURNAL OF LIPID SCIENCE AND TECHNOLOGY

Detection and Semi-quantification of Lipids on High-Performance Thin-Layer Chromatography Plate using Ceric Ammonium Molybdate Staining
Asressu KH and Zhang Q
It is desirable to quickly check the composition of lipids in small size samples, but achieving this is challenging using the existing staining methods. Herein, we developed a highly sensitive and semi-quantitative method for analysis of lipid samples with ceric ammonium molybdate (CAM) staining. The CAM detection method was systematically evaluated with a wide range of lipid classes including phospholipids, sphingolipids, glycerolipids, fatty acids (FA) and sterols, demonstrating high sensitivity, stability, and overall efficiency. Additionally, CAM staining provides a clean yellow background in high performance thin-layer chromatography (HPTLC) which facilitates quantification of lipids using image processing software. Lipids can be stained with CAM reagent regardless of their head group types, position of the carbon-carbon double bonds, geometric isomerism and the variation in the length of FA chain, but staining is mostly affected by the degree of unsaturation of the FA backbone. The mechanism of the CAM staining of lipids was proposed on principles of the reduction-oxidation reaction, in which Mo(VI) oxidizes the unsaturated lipids into carbonyl compounds on the HPTLC plate upon heating, while itself being reduced to Mo(IV). This method was applied for the separation, identification, and quantification of lipid extracts from porcine brain.
Phytosterol oxidation products (POP) in foods with added phytosterols and estimation of their daily intake: A literature review
Lin Y, Knol D and Trautwein EA
1To evaluate the content of phytosterol oxidation products (POP) of foods with added phytosterols, in total 14 studies measuring POP contents of foods with added phytosterols were systematically reviewed. In non-heated or stored foods, POP contents were low, ranging from (medians) 0.03-3.6 mg/100 g with corresponding oxidation rates of phytosterols (ORP) of 0.03-0.06%. In fat-based foods with 8% of added free plant sterols (FPS), plant sterol esters (PSE) or plant stanol esters (PAE) pan-fried at 160-200°C for 5-10 min, median POP contents were 72.0, 38.1, and 4.9 mg/100 g, respectively, with a median ORP of 0.90, 0.48, and 0.06%. Hence resistance to thermal oxidation was in the order of PAE > PSE > FPS. POP formation was highest in enriched butter followed by margarine and rapeseed oil. In margarines with 7.5-10.5% added PSE oven-heated at 140-200°C for 5-30 min, median POP content was 0.3 mg/100 g. Further heating under same temperature conditions but for 60-120 min markedly increased POP formation to 384.3 mg/100 g. Estimated daily upper POP intake was 47.7 mg/d (equivalent to 0.69 mg/kg BW/d) for foods with added PSE and 78.3 mg/d (equivalent to 1.12 mg/kg BW/d) for foods with added FPS as calculated by multiplying the advised upper daily phytosterol intake of 3 g/d with the 90% quantile values of ORP. In conclusion, heating temperature and time, chemical form of phytosterols added and the food matrix are determinants of POP formation in foods with added phytosterols, leading to an increase in POP contents. Phytosterol oxidation products (POP) are formed in foods containing phytosterols especially when exposed to heat treatment. This review summarising POP contents in foods with added phytosterols in their free and esterified forms reveals that heating temperature and time, the chemical form of phytosterols added and the food matrix itself are determinants of POP formation with heating temperature and time having the biggest impact. The estimated upper daily intakes of POP is 78.3 mg/d for fat-based products with added free plant sterols and 47.7 mg/d for fat-based products with added plant sterol esters. Phytosterols in foods are susceptible to oxidation to form phytosterol oxidation products (POP). This review summarizes literature data regarding POP contents of foods with added phytosterols that were exposed to storage and heat treatments.
Optimized extraction of 2-arachidonyl glycerol and anandamide from aortic tissue and plasma for quantification by LC-MS/MS
Garst C, Fulmer M, Thewke D and Brown S
Atherosclerosis is a disease characterized by plaque formation due to an accumulation of fat, cholesterol, and immune cells in the walls of arteries. If a plaque ruptures, an occlusive thrombosis may form that causes either a heart attack or stroke. Macrophages express CB-2 receptors, and are one type of immune cell that plays a role in plaque destabilization and rupture. Endocannabinoids anandamide (AEA) and 2-arachidonyl glycerol (2-AG) have been found to have activity on CB-1 and CB-2 receptors throughout the body and immune system. In this study, we investigated several sample preparation options for the LC-MS quantification of AEA and 2-AG from plasma and aortic tissue. The extractions considered included liquid-liquid (LLE), solid-phase (SPE), and supported liquid (SLE). Some extraction protocols yielded high analyte recovery and prevention of 1-AG/2-AG isomerization. Our results indicate that a liquid-liquid extraction using toluene yields the highest recovery for both analytes, coupled with low ionization suppression in the mass spectrometer. This extraction and corresponding LC-MS/MS assay provides a simple, high throughput mechanism for the quantification of 2-AG and AEA in matrices relevant to the study of endocannabinoids' role in atherosclerosis.
Functional self-assembled lipidic systems derived from renewable resources
Silverman JR, Samateh M and John G
Self-assembled lipidic amphiphile systems can create a variety of multi-functional soft materials with value-added properties. When employing natural reagents and following biocatalytic syntheses, self-assembling monomers may be inherently designed for degradation, making them potential alternatives to conventional and persistent polymers. By using non-covalent forces, self-assembled amphiphiles can form nanotubes, fibers, and other stimuli responsive architectures prime for further applied research and incorporation into commercial products. By viewing these lipid derivatives under a lens of green principles, there is the hope that in developing a structure-function relationship and functional smart materials that research may remain safe, economic, and efficient.
Comparative evaluation of structured oil systems: Shellac oleogel, HPMC oleogel, and HIPE gel
Patel AR and Dewettinck K
In lipid-based food products, fat crystals are used as building blocks for creating a crystalline network that can trap liquid oil into a 3D gel-like structure which in turn is responsible for the desirable mouth feel and texture properties of the food products. However, the recent ban on the use of trans-fat in the US, coupled with the increasing concerns about the negative health effects of saturated fat consumption, has resulted in an increased interest in the area of identifying alternative ways of structuring edible oils using non-fat-based building blocks. In this paper, we give a brief account of three alternative approaches where oil structuring was carried out using wax crystals (shellac), polymer strands (hydrophilic cellulose derivative), and emulsion droplets as structurants. These building blocks resulted in three different types of oleogels that showed distinct rheological properties and temperature functionalities. The three approaches are compared in terms of the preparation process (ease of processing), properties of the formed systems (microstructure, rheological gel strength, temperature response, effect of water incorporation, and thixotropic recovery), functionality, and associated limitations of the structured systems. The comparative evaluation is made such that the new researchers starting their work in the area of oil structuring can use this discussion as a general guideline.
An automated shotgun lipidomics platform for high throughput, comprehensive, and quantitative analysis of blood plasma intact lipids
Surma MA, Herzog R, Vasilj A, Klose C, Christinat N, Morin-Rivron D, Simons K, Masoodi M and Sampaio JL
Blood plasma has gained protagonism in lipidomics studies due to its availability, uncomplicated collection and preparation, and informative readout of physiological status. At the same time, it is also technically challenging to analyze due to its complex lipid composition affected by many factors, which can hamper the throughput and/or lipidomics coverage. To tackle these issues, we developed a comprehensive, high throughput, and quantitative mass spectrometry-based shotgun lipidomics platform for blood plasma lipid analyses. The main hallmarks of this technology are (i) it is comprehensive, covering 22 quantifiable different lipid classes encompassing more than 200 lipid species; (ii) it is amenable to high-throughput, with less than 5 min acquisition time allowing the complete analysis of 200 plasma samples per day; (iii) it achieves absolute quantification, by inclusion of internal standards for every lipid class measured; (iv) it is highly reproducible, achieving an average coefficient of variation of <10% (intra-day), approx. 10% (inter-day), and approx. 15% (inter-site) for most lipid species; (v) it is easily transferable allowing the direct comparison of data acquired in different sites. Moreover, we thoroughly assessed the influence of blood stabilization with different anticoagulants and freeze-thaw cycles to exclude artifacts generated by sample preparation. This shotgun lipidomics platform can be implemented in different laboratories without compromising reproducibility, allowing multi-site studies and inter-laboratory comparisons. This possibility combined with the high-throughput, broad lipidomic coverage and absolute quantification are important aspects for clinical applications and biomarker research.
Intake and sources of dietary fatty acids in Europe: Are current population intakes of fats aligned with dietary recommendations?
Eilander A, Harika RK and Zock PL
1The development of food-based dietary guidelines for prevention of cardiovascular diseases requires knowledge of the contribution of common foods to SFA and PUFA intake. We systematically reviewed available data from European countries on population intakes and dietary sources of total fat, SFA, and PUFA. Data from national dietary surveys or population studies published >1995 were searched through Medline, Web of Science, and websites of national public health institutes. Mean population intakes were compared with FAO/WHO dietary recommendations, and contributions of major food groups to overall intakes of fat and fatty acids were calculated. Fatty acid intake data from 24 European countries were included. Reported mean intakes ranged from 28.5 to 46.2% of total energy (%E) for total fat, from 8.9 to 15.5%E for SFA, from 3.9 to 11.3%E for PUFA. The mean intakes met the recommendation for total fat (20-35%E) in 15 countries, and for SFA (<10%E) in two countries, and for PUFA (6-11%E) in 15 of the 24 countries. The main three dietary sources of total fat and SFA were dairy, added fats and oils, and meat and meat products. The majority of PUFA in the diet was provided by added fats and oils, followed by cereals and cereal products, and meat and meat products. While many European countries meet the recommended intake levels for total fat and PUFA, a large majority of European population exceeds the widely recommended maximum 10%E for SFA. In particular animal based products, such as dairy, animal fats, and fatty meat contribute to SFA intake. Adhering to food-based dietary guidelines for prevention of CHD and other chronic diseases in Europe, including eating less fatty meats, low-fat instead of full-fat dairy, and more vegetable fats and oils will help to reduce SFA intake and at the same time increase PUFA intake. In European countries, SFA intakes are generally higher than the recommended <10%E and PUFA intakes lower than the recommended 6-11%E. Adhering to food-based dietary guidelines for prevention of CHD and other chronic diseases including eating leaner variants of meat and dairy, and more vegetable fats and oils will help to decrease SFA intake and increase PUFA intake.
Transgenic plants as a sustainable, terrestrial source of fish oils
Napier JA, Usher S, Haslam RP, Ruiz-Lopez N and Sayanova O
1An alternative, sustainable source of omega-3 long chain polyunsaturated fatty acids is widely recognized as desirable, helping to reduce pressure on current sources (wild capture fisheries) and providing a de novo source of these health beneficial fatty acids. This review will consider the efforts and progress to develop transgenic plants as terrestrial sources of omega-3 fish oils, focusing on recent developments and the possible explanations for advances in the field. We also consider the utility of such a source for use in aquaculture, since this industry is the major consumer of oceanic supplies of omega-3 fish oils. Given the importance of the aquaculture industry in meeting global requirements for healthy foodstuffs, an alternative source of omega-3 fish oils represents a potentially significant breakthrough for this production system. Transgenic Camelina seeds engineered to accumulate the omega-3 fatty acids EPA and DHA, represent a sustainable alternative to fish oils.
The supramolecular chemistry of lipid oxidation and antioxidation in bulk oils
Budilarto ES and Kamal-Eldin A
The microenvironment formed by surface active compounds is being recognized as the active site of lipid oxidation. Trace amounts of water occupy the core of micro micelles and several amphiphilic minor components (e.g., phospholipids, monoacylglycerols, free fatty acids, etc.) act as surfactants and affect lipid oxidation in a complex fashion dependent on the structure and stability of the microemulsions in a continuous lipid phase such as bulk oil. The structures of the triacylglycerols and other lipid-soluble molecules affect their organization and play important roles during the course of the oxidation reactions. Antioxidant head groups, variably located near the water-oil colloidal interfaces, trap and scavenge radicals according to their location and concentration. According to this scenario, antioxidants inhibit lipid oxidation not only by scavenging radicals via hydrogen donation but also by physically stabilizing the micelles at the microenvironments of the reaction sites. There is a cut-off effect (optimum value) governing the inhibitory effects of antioxidants depending inter alias on their hydrophilic/lipophilic balance and their concentrations. These complex effects, previously considered as paradoxes in antioxidants research, are now better explained by the supramolecular chemistry of lipid oxidation and antioxidants, which is discussed in this review.
Comprehensive and quantitative profiling of lipid species in human milk, cow milk and a phospholipid-enriched milk formula by GC and MS/MS
Sokol E, Ulven T, Færgeman NJ and Ejsing CS
Here we present a workflow for in-depth analysis of milk lipids that combines gas chromatography (GC) for fatty acid (FA) profiling and a shotgun lipidomics routine termed MS/MS for structural characterization of molecular lipid species. To evaluate the performance of the workflow we performed a comparative lipid analysis of human milk, cow milk, and Lacprodan® PL-20, a phospholipid-enriched milk protein concentrate for infant formula. The GC analysis showed that human milk and Lacprodan have a similar FA profile with higher levels of unsaturated FAs as compared to cow milk. In-depth lipidomic analysis by MS/MS revealed that each type of milk sample comprised distinct composition of molecular lipid species. Lipid class composition showed that the human and cow milk contain a higher proportion of triacylglycerols (TAGs) as compared to Lacprodan. Notably, the MS/MS analysis demonstrated that the similar FA profile of human milk and Lacprodan determined by GC analysis is attributed to the composition of individual TAG species in human milk and glycerophospholipid species in Lacprodan. Moreover, the analysis of TAG molecules in Lacprodan and cow milk showed a high proportion of short-chain FAs that could not be monitored by GC analysis. The results presented here show that complementary GC and MS/MS analysis is a powerful approach for characterization of molecular lipid species in milk and milk products.
Tocopherol and tocotrienol homologs in parenteral lipid emulsions
Xu Z, Harvey KA, Pavlina TM, Zaloga GP and Siddiqui RA
Parenteral lipid emulsions, which are made of oils from plant and fish sources, contain different types of tocopherols and tocotrienols (vitamin E homologs). The amount and types of vitamin E homologs in various lipid emulsions vary considerably and are not completely known. The objective of this analysis was to develop a quantitative method to determine levels of all vitamin E homologs in various lipid emulsions. An HPLC system was used to measure vitamin E homologs using a Pinnacle DB Silica normal phase column and an isocratic, n-hexane:1,4 dioxane (98:2) mobile phase. An optimized protocol was used to report vitamin E homolog concentrations in soybean oil-based (Intralipid®, Ivelip®, Lipofundin® N, Liposyn® III, and Liposyn® II), medium- and long-chain fatty acid-based (Lipofundin®, MCT and Structolipid®), olive oil-based (ClinOleic® and fish oil-based (Omegaven®) and mixture of these oils-based (SMOFlipid®, Lipidem®) commercial parenteral lipid emulsions. Total content of all vitamin E homologs varied greatly between different emulsions, ranging from 57.9 to 383.9 µg/mL. Tocopherols (α, β, γ, δ) were the predominant vitamin E homologs for all emulsions, with tocotrienol content < 0.3%. In all of the soybean emulsions, except for Lipofundin® N, the predominant vitamin E homolog was γ-tocopherol, which ranged from 57-156 µg/mL. ClinOleic® predominantly contained α-tocopherol (32 µg/mL), whereas α-tocopherol content in Omegaven® was higher than most of the other lipid emulsions (230 µg/mL).
Shotgun lipidomic analysis of chemically sulfated sterols compromises analytical sensitivity: Recommendation for large-scale global lipidome analysis
Casanovas A, Hannibal-Bach HK, Jensen ON and Ejsing CS
Research advancements in palm oil nutrition
May CY and Nesaretnam K
Palm oil is the major oil produced, with annual world production in excess of 50 million tonnes. About 85% of global palm oil produced is used in food applications. Over the past three decades, research on nutritional benefits of palm oil have demonstrated the nutritional adequacy of palm oil and its products, and have resulted in transitions in the understanding these attributes. Numerous studies have demonstrated that palm oil was similar to unsaturated oils with regards to effects on blood lipids. Palm oil provides a healthy alternative to trans-fatty acid containing hydrogenated fats that have been demonstrated to have serious deleterious effects on health. The similar effects of palm oil on blood lipids, comparable to other vegetable oils could very well be due to the structure of the major triglycerides in palm oil, which has an unsaturated fatty acid in the stereospecific numbers (-2 position of the glycerol backbone. In addition, palm oil is well endowed with a bouquet of phytonutrients beneficial to health, such as tocotrienols, carotenoids, and phytosterols. This review will provide an overview of studies that have established palm oil as a balanced and nutritious oil.
The use of natural and synthetic phospholipids as pharmaceutical excipients
van Hoogevest P and Wendel A
In pharmaceutical formulations, phospholipids obtained from plant or animal sources and synthetic phospholipids are used. Natural phospholipids are purified from, e.g., soybeans or egg yolk using non-toxic solvent extraction and chromatographic procedures with low consumption of energy and minimum possible waste. Because of the use of validated purification procedures and sourcing of raw materials with consistent quality, the resulting products differing in phosphatidylcholine content possess an excellent batch to batch reproducibility with respect to phospholipid and fatty acid composition. The natural phospholipids are described in pharmacopeias and relevant regulatory guidance documentation of the Food and Drug Administration (FDA) and European Medicines Agency (EMA). Synthetic phospholipids with specific polar head group, fatty acid composition can be manufactured using various synthesis routes. Synthetic phospholipids with the natural stereochemical configuration are preferably synthesized from glycerophosphocholine (GPC), which is obtained from natural phospholipids, using acylation and enzyme catalyzed reactions. Synthetic phospholipids play compared to natural phospholipid (including hydrogenated phospholipids), as derived from the number of drug products containing synthetic phospholipids, a minor role. Only in a few pharmaceutical products synthetic phospholipids are used. Natural phospholipids are used in oral, dermal, and parenteral products including liposomes. Natural phospholipids instead of synthetic phospholipids should be selected as phospholipid excipients for formulation development, whenever possible, because natural phospholipids are derived from renewable sources and produced with more ecologically friendly processes and are available in larger scale at relatively low costs compared to synthetic phospholipids. For selection of phospholipid excipients for pharmaceutical formulations, natural phospholipids are preferred compared to synthetic phospholipids because they are available at large scale with reproducible quality at lower costs of goods. They are well accepted by regulatory authorities and are produced using less chemicals and solvents at higher yields. In order to avoid scale up problems during pharmaceutical development and production, natural phospholipid excipients instead of synthetic phospholipids should be selected whenever possible.
Polyunsaturated fatty acids modify expression of TGF-β in a co-culture model ultilising human colorectal cells and human peripheral blood mononuclear cells exposed to , and
Bentley-Hewitt KL, De Guzman CE, Ansell J, Mandimika T, Narbad A and Lund EK
Commensal bacteria and polyunsaturated fatty acids (PUFAs) have both been shown independently to modulate immune responses. This study tested the hypothesis that the different colonic immunomodulatory responses to commensal () and pathogenic bacteria ( and ) may be modified by PUFAs. Experiments used a Transwell system combining the colorectal cell line HT29, or its mucous secreting sub-clone HT29-MTX, with peripheral blood mononuclear cells to analyse immunomodulatory signalling in response to bacteria, with and without prior treatment with arachidonic acid, eicosapentaenoic acid or docosahexaenoic acid. increased transforming growth factor β1 (TGF-β1) mRNA and protein secretion in colonic cell lines when compared with controls, an effect that was enhanced by pre-treatment with eicosapentaenoic acid. In contrast, the Gram-negative pathogen LF82 had no significant effect on TGF-β1 protein. also increased IL-8 mRNA but not protein while increased both; although differences between PUFA treatments were detected, none were significantly different to controls. Colonic epithelial cells show different immunomodulatory signalling patterns in response to the commensal compared to and and pre-treatment of these cells with PUFAs can modify responses. We have demonstrated an interaction between dietary PUFAs and epithelial cell response to both commensal and pathogenic bacteria found in the gastrointestinal tract by utilising in vitro co-culture models. The data suggest that n-3 PUFAs may provide some protection against the potentially damaging effects of pathogens. Furthermore, the beneficial effects of combining n-3 PUFAs and the commensal bacteria, and potential probiotic, are illustrated by the increased expression of immunoregulatory TGF-β1.
Antioxidant effect of mono- and dihydroxyphenols in sunflower oil with different levels of naturally present tocopherols
Hrádková I, Merkl R, Smidrkal J, Kyselka J and Filip V
Antioxidant properties of mono- and dihydroxyphenolic acids and their alkyl esters were examined, with emphasis on the relationship between their molecular structure and antioxidant activity. Test media with different tocopherol level were used for determining the oxidative stability: original refined sunflower oil (total tocopherols 149.0 mg/kg), partially tocopherol-stripped sunflower oil (total tocopherols 8.7 mg/kg) and distilled fatty acid methyl esters (FAME) as a tocopherol-free medium. The chemical reaction of tocopherols with diazomethane tested for the purpose to eliminate their antioxidant activity failed due to the negligible degree of methylation of hydroxyl group in the tocopherol molecule. Caffeic acid and protocatechuic acid (3,4-dihydroxyphenolic acids) and their alkyl esters were found to be more active antioxidants than monohydroxyphenolic acid (-hydroxybenzoic acid), 2,5-dihydroxyphenolic acid (gentisic acid), 3-methoxy-4-hydroxyphenolic acids (vanillic and ferulic acids) and their corresponding alkyl esters. Naturally present tocopherols in refined sunflower oil proved to have a synergistic effect on gentisic acid but not on its alkyl esters. In contrast, tocopherols showed an antagonistic effect on alkyl esters of caffeic acid, because their protection factors decreased with increasing level of tocopherols in the test medium. Moreover, the antioxidant activity of these alkyl esters decreased with increasing length of their alkyl chain in conformity with the polar paradox hypothesis.
Beta-Cell Injury in Ncb5or-null Mice is Exacerbated by Consumption of a High-Fat Diet
Guo Y, Xu M, Deng B, Frontera JR, Kover KL, Aires D, Ding H, Carlson SE, Turk J, Wang W and Zhu H
NADH-cytochrome b5 oxidoreductase (Ncb5or) in endoplasmic reticulum (ER) is involved in fatty acid metabolism, and Ncb5or(-/-) mice fed standard chow (SC) are insulin-sensitive but weigh less than wild type (WT) littermates. Ncb5or(-/-) mice develop hyperglycemia at about age 7 weeks due to β-cell dysfunction and loss associated with saturated fatty acid accumulation and manifestations of ER and oxidative stress. Here we report that when Ncb5or(-/-) mice born to heterozygous mothers fed a high fat (HF) diet continue to ingest HF, they weigh as much as SC-fed WT at age 5 weeks. By age 7 weeks, diabetes mellitus develops in all HF-fed vs. 68% of SC-fed Ncb5or(-/-) mice. Islet β-cell content in age 5-week Ncb5or(-/-) mice fed HF for 7 days is lower (53%) than for those fed SC (63%), and both are lower than for WT (75%, SC, vs. 69%, HF). Islet transcript levels for markers of mitochondrial biogenesis (PGC-1α) and ER stress (ATF6α) are higher in Ncb5or(-/-) than WT mice but not significantly affected by diet. Consuming a HF diet exacerbates Ncb5or(-/-) β-cell accumulation of intracellular saturated fatty acids and increases the frequency of ER distention from 11% (SC) to 47% (HF), thus accelerates β-cell injury in Ncb5or(-/-) mice.
Searching for health beneficial n-3 and n-6 fatty acids in plant seeds
Kuhnt K, Degen C, Jaudszus A and Jahreis G
Various plant seeds have received little attention in fatty acid research. Seeds from 30 species mainly of Boraginaceae and Primulaceae were analysed in order to identify potential new sources of the n-3 PUFA α-linolenic acid (ALA) and stearidonic acid (SDA) and of the n-6 PUFA γ-linolenic acid (GLA). The fatty acid distribution differed enormously between genera of the same family. Echium species (Boraginaceae) contained the highest amount of total n-3 PUFA (47.1%), predominantly ALA (36.6%) and SDA (10.5%) combined with high GLA (10.2%). Further species of Boraginaceae rich in both SDA and GLA were Omphalodes linifolia (8.4, 17.2%, resp.), Cerinthe minor (7.5, 9.9%, resp.) and Buglossoides purpureocaerulea (6.1, 16.6%, resp.). Alkanna species belonging to Boraginaceae had comparable amounts of ALA (37.3%) and GLA (11.4%) like Echium but lower SDA contents (3.7%). Different genera of Primulaceae (Dodecatheon and Primula) had varying ALA (14.8, 28.8%, resp.) and GLA portions (4.1, 1.5%, resp.), but similar amounts of SDA (4.9, 4.5%, resp.). Cannabis sativa cultivars (Cannabaceae) were rich in linoleic acid (57.1%), but poor in SDA and GLA (0.8, 2.7%, resp.). In conclusion, several of the presented plant seeds contain considerable amounts of n-3 PUFA and GLA, which could be relevant for nutritional purposes due to their biological function as precursors for eicosanoid synthesis. PRACTICAL APPLICATIONS: N-3 PUFA are important for human health and nutrition. Unfortunately, due to the increasing world population, overfishing of the seas and generally low amounts of n-3 PUFA in major oil crops, there is a demand for new sources of n-3 PUFA. One approach involves searching for potential vegetable sources of n-3 PUFA; especially those rich in ALA and SDA. The conversion of ALA to SDA in humans is dependent on the rate-limiting Δ6-desaturation. Plant-derived SDA is therefore a promising precursor regarding the endogenous synthesis of n-3 long-chain PUFA in humans. The present study shows that, in addition to seed oil of Echium, other species of Boraginaceae (Cerinthe, Omphalodes, Lithospermum, Buglossoides) and Primulaceae (Dodecatheon, Primula), generally high in n-3 PUFA (30-50%), contain considerable amounts of SDA (5-10%). Therefore, these seed oils could be important for nutrition.
Subcritical co-solvents extraction of lipid from wet microalgae pastes of Nannochloropsis sp
Chen M, Liu T, Chen X, Chen L, Zhang W, Wang J, Gao L, Chen Y and Peng X
In this paper subcritical co-solvents extraction (SCE) of algal lipid from wet pastes of Nannochloropsis sp. is examined. The influences of five operating parameters including the ratio between ethanol to hexane, the ratio of mixed solvents to algal biomass (dry weight), extraction temperature, pressure, and time were investigated. The determined optimum extraction conditions were 3:1 (hexane to ethanol ratio), 10:1 ratio (co-solvents to microalgae (dry weight) ratio), 90°C, 1.4 MPa, and 50 min, which could produce 88% recovery rate of the total lipids. In addition, electron micrographs of transmission electron microscopy (TEM) and scanning electron microscopy (SEM) were conducted to show that the algal cell presented shrunken, collapsed with some wrinkles and microholes after SCE extraction. The main composition of total lipids extracted under the optimum conditions was TAG which represented more than 80%. And the fatty acid profile of triglycerides revealed that C16:0 (35.67 ± 0.2%), C18:1 (26.84 ± 0.044%) and C16:1 (25.96 ± 0.011%) were dominant. PRACTICAL APPLICATIONS: The reported method could save energy consumption significantly through avoiding deep dewatering (for example drying). The composition of the extracted lipid is suitable for the production of high quality biodiesel.
Regulation of polyisoprenylated methylated protein methyl esterase by polyunsaturated fatty acids and prostaglandins
Amissah F, Taylor S, Duverna R, Ayuk-Takem LT and Lamango NS
Polyisoprenylation is a set of secondary modifications involving proteins whose aberrant activities are implicated in cancers and degenerative disorders. The last step of the pathway involves an ester-forming polyisoprenylated protein methyl transferase- and hydrolytic polyisoprenylated methylated protein methyl esterase (PMPMEase)-catalyzed reactions. Omega-3 and omega-6 polyunsaturated fatty acids (PUFAs) have been linked with antitumorigeneis and tumorigenesis, respectively. PUFAs are structurally similar to the polyisoprenyl groups and may interfere with polyisoprenylated protein metabolism. It was hypothesized that PUFAs may be more potent inhibitors of PMPMEase than their more polar oxidative metabolites, the prostaglandins. As such, the relative effects of PUFAs and prostaglandins on PMPMEase could explain the association between cyclooxygenase-2 (COX-2) expression in tumors, the chemopreventive effects of the non-steroidal anti-inflammatory (NSAIDs) COX-2 inhibitors and PUFAs. PUFAs such as arachidonic (AA), eicosapentaenoic (EPA) and docosahexaenoic (DHA) acids inhibited PMPMEase activity with Ki values of 0.12 to 3.7 μM. The most potent prostaglandin was 63-fold less potent than AA. The PUFAs were also more effective at inducing neuroblastoma cell death at physiologically equivalent concentrations. The lost PMPMEase activity in AA-treated degenerating cells was restored by incubating the lysates with COX-1 or COX-2. PUFAs may thus be physiological regulators of cell growth and could owe these effects to PMPMEase inhibition.
Trans fatty acid isomers and the trans-9/trans-11 index in fat containing foods
Kuhnt K, Baehr M, Rohrer C and Jahreis G
To determine trans fatty acid (TFA) distribution of contemporary foods, especially regarding individual trans octadecenoic acids (trans C18:1), 339 German foods of six categories (semi-solid fats, deep-fried potato products, bakery products, confectioneries, instant products and butter) were analysed using two GC methods. Results showed a high variation of TFA content between and within the categories containing between 0 and 40.5% of FAME except in butter, which is a source of natural TFA. The mean TFA values were below 2.0% of FAME, however, bakery products contained 4.5% and butter fat 3.2%, respectively. In addition, the distribution of individual trans C18:1 differed. In samples containing ruminant fat (butter and various confectioneries), vaccenic acid (t11-C18:1, t11) predominated, while in foods containing industrially hydrogenated fats, elaidic acid (trans-9, t9-) and t10-C18:1 were the major trans isomers.. This was reflected by a low t9/t11 index of 0.3 and 0.5 in butter and ruminant fat containing confectioneries, respectively, whilst the highest index was observed in shortenings and deep-fried potato products at 5.2 and 6.8, respectively. In conclusion, the TFA content of foods available on the German market is generally declining, but substantial variations are present. The t9/t11 index could be used as an indicator to determine ruminant fat.Practical applications: A number of studies provide evidence that a high TFA intake, particularly of industrial origin, adversely affects human health. The TFA content of foods could be reduced due to the introduction of several mandatory regulations and modifications regarding the hydrogenation process of oils. The most abundant dietary TFA are the isomers of trans C18:1. Unfortunately, the differentiation of these isomers is not yet very common, though the trans C18:1 profile differs depending on its origin (bacterial hydrogenation in the rumen or industrial hydrogenation). To date, data for TFA content including the trans C18:1 profile of different food categories are limited. The present study confirmed that the TFA contents in German foods are declining. However, TFA are still elevated, especially in bakery products and confectioneries, which are produced using mainly industrial but also ruminant fats. Therefore, the t9/t11 index imparts important information on the source of TFA in processed foods.