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Fereidoon Shahidi - One of the best experts on this subject based on the ideXlab platform.
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Food and Health Applications of Marine Nutraceuticals: a Review
Seafoods — Quality Technology and Nutraceutical Applications, 2020Co-Authors: Cesarettin Alasalvar, Fereidoon Shahidi, Peter C. QuantickAbstract:With the growing public awareness of the nutritional, diet and health benefits of Seafoods, the stage is now to set for the development of mainstream nutraceutical products. Application of marine-based nutraceuticals includes fish Oil (mainly omega-3 polyunsaturated fatty acids), seal Blubber Oil, algal Oil, shark liver Oil and squalene, shark cartilage, chitin, chitosan as well as their monomers and oligomers, enzymes, peptides and related compounds, vitamins (A, particularly its precursor β-carotene, D and E), seaweed (macroalgae) and its components, protein hydrolysates and other products has become a topic of great interest for both pharmaceutical and health food industries. This review provides an account of marine nutraceuticals and their application. Where available, the health benefits of nutraceuticals of interest are also discussed.
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Two step-production of acylglycerols containing a high proportion of docosapentaenoic acid from marine omega-3 Oil and their oxidative stability
Journal of Food Bioactives, 2018Co-Authors: Zhongshui Yu, Jiankang Wang, Fereidoon ShahidiAbstract:The objective of this study was to concentrate polyunsaturated fatty acid (PUFA) from seal Blubber Oil in an innovative manner to produce a high content of docosapentaenoic acid (DPA) in the resultant product. It also aimed at investigating the use of lipases as catalysts for synthesizing acylglycerols from glycerol and polyunsaturated fatty acid concentrates. Additionally, study of the oxidative stability of acylglycerols synthesized by lipases was intended. A two-stage urea complexation process was used to concentrate PUFA from seal Blubber Oil, giving rise to a DPA content of up to 24.0% in the product. Enzymatic synthesis of acyglycerols directly from glycerol and fatty acid concentrate was studied. Three lipases were used as biocatalysts for esterification. Lipase SP435 from Candida antarctica showed the highest activity for esterification. Effects of reaction parameters, namely temperature, time course and mole ratio of glycerol to fatty acid were followed with all three lipases. The optimal reaction time was 24 hr at 30 °C at a mole ratio of glycerol to fatty acid of 14:1. The maximum degree of acylglycerol synthesis was > 90%. The effect of time course and mole ratio of glycerol to fatty acid on acylglycerols distribution was also determined. The oxidative stability of different samples under Schaal-oven conditions at 60 °C showed that the oxidative stability of acylglycerols was better than that of the corresponding fatty acid esters.
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Acidolysis of p-coumaric acid with omega-3 Oils and antioxidant activity of phenolipid products in in vitro and biological model systems.
Journal of Agricultural and Food Chemistry, 2013Co-Authors: Jiankang Wang, Fereidoon ShahidiAbstract:Lipase-catalyzed acidolysis of p-coumaric acid with seal Blubber Oil (SBO) and menhaden Oil (MHO) was carried out, followed by identification of major phenolipids in the resultant acidolysis mixture using high-performance liquid chromatography/mass spectrometry. Separation of phenolipid components from the resultant acidolysis mixture was achieved using flash column chromatography. The antioxidant activities of the phenolipids were examined in in vitro assays and biological model systems. The major phenolipids identified from acidolysis mixtures with both SBO and MHO included eight phenolic monoacylglycerols and eight phenolic diacylglycerols. Phenolipids derived from SBO and MHO generally showed good antioxidant potential in the systems tested. The prepared phenolipids exhibited high scavenging capacity toward 1,1-diphenyl-2-picrylhydrazyl (DPPH) and peroxyl radicals and displayed reducing power, strong inhibitory effect on bleaching of β-carotene, human low-density lipoprotein (LDL) cholesterol oxidatio...
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Effect of enzymatic randomization on positional distribution and stability of seal Blubber and menhaden Oils.
Journal of Agricultural and Food Chemistry, 2011Co-Authors: Jiankang Wang, Fereidoon ShahidiAbstract:In an effort to investigate the effect of positional distribution on oxidative stability of menhaden and seal Blubber Oils, Novozyme 435 was used as a random biocatalyst. Positional distribution of fatty acids was determined using gas chromatography. As some of the α-tocopherol was lost during randomization, its content was adjusted to the level prior to the process to eliminate this effect on oxidative stability of Oils tested. Conjugated dienes (CD) and thiobarbituric acid reactive substances (TBARS) were used as indicators of oxidative stability. The results showed that the polyunsaturated fatty acids were distributed predominantly at terminal positions in randomized menhaden Oil, whereas they were distributed more evenly among all positions in enzymatically randomized seal Blubber Oil, compared to their unrandomized counterparts. Results of CD and TBARS values indicated that randomized menhaden Oil was more stable than the original Oil, whereas randomized seal Blubber Oil was more vulnerable to oxidat...
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Effect of chemical randomization on positional distribution and stability of omega-3 Oil triacylglycerols.
Journal of Agricultural and Food Chemistry, 2010Co-Authors: Jiankang Wang, Jaroslav Kralovec, Erick Reyes Suárez, Fereidoon ShahidiAbstract:Randomization has been commonly used to modify the chemical and physical properties of natural fats and Oils. In this study, seal Blubber Oil (SBO) and menhaden Oil (MHO) were modified through chemical randomization using sodium methoxide, and the effect on positional distribution of fatty acids was investigated using gas chromatography (GC) and 13C nuclear magnetic resonance (NMR) spectroscopy. The effect of randomization on the stability of the original Oils and their randomized counterparts was analyzed by comparing conjugated dienes and thiobarbituric acid reactive substances (TBARS) values after accelerated oxidation at 60 °C for 4 days. The omega-3 polyunsaturated fatty acids (PUFA) were distributed more evenly among the terminal sn-1,3 positions and the middle sn-2 position in chemically randomized Oils when compared to the starting Oils. The effect was more pronounced for SBO with omega-3 PUFA attached preferentially to sn-1,3 positions of triacylglycerols before randomization, and it was less pro...
Udaya N Wanasundara - One of the best experts on this subject based on the ideXlab platform.
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Lipolytic activity of enzymes from germinating seeds of sesame (Sesamum indicum L.).
Journal of Food Lipids, 2001Co-Authors: P K J P D Wanasundara, Udaya N Wanasundara, Fereidoon ShahidiAbstract:Sesame (Sesumum indicum) seeds were germinated for seven days under laboratory conditions and the lipolytic activity of the defatted, dried seedlings was determined. Germination increased the lipolytic activity of sesame seeds and the highest activity was observed on day-4. The lipases of four days germinated sesame seeds were able to hydrolyze mainly the saturated fatty acids from seal Blubber Oil (SBO). Reaction temperature, incubation period and Oil-to-seedling powder ratio had a significant effect on the hydrolysis of saturated fatty acids, thereby concentrating unsaturated (mono- and polyunsaturated) fatty acids of seal Blubber Oil.
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effects of processing and squalene on composition and oxidative stability of seal Blubber Oil
Journal of Food Lipids, 1999Co-Authors: Fereidoon Shahidi, Udaya N WanasundaraAbstract:Effects of processing on constituents of seal Blubber Oil and that of squalene on oxidative stability of several Oils were monitored. The content of α-tocopherol in Oil decreased during processing, especially at the bleaching and deodorization steps. There was also a concurrent reduction in the contents of squalene and free fatty acids, especially during deodorization. Oils treated with squalene did not show any improved oxidative stability and in some cases were even less stable.
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concentration of omega 3 polyunsaturated fatty acids of seal Blubber Oil by urea complexation optimization of reaction conditions
Food Chemistry, 1999Co-Authors: Udaya N Wanasundara, Fereidoon ShahidiAbstract:Abstract Production of omega-3 fatty acid concentrates from seal Blubber Oil (SBO) was optimized. In this process, the content of total ω3-fatty acids, Y1; eicosapentaenoic acid (EPA), Y2; and docosahexaenoic acid (DHA), Y3 in the final product was maximized. A three-factor central composite rotatable design (CCRD) was used to study the effect of urea-to-fatty acid ratio (X1), crystallization time (X2), and crystallization temperature (X3). Second-order polynomial regression models for Y1, Y2 and Y3 were employed to generate response surfaces. Under optimum conditions the maximum amount of total ω3 fatty acids (88.2%) from SBO was obtained at a urea-to-fatty acid ratio of 4.5, a crystallization time of 24 h, and a crystallization temperature of −10°C. ©
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concentration of ω 3 polyunsaturated fatty acids of marine Oils using candida cylindracea lipase optimization of reaction conditions
Journal of the American Oil Chemists' Society, 1998Co-Authors: Udaya N Wanasundara, Fereidoon ShahidiAbstract:Production of ω-3 fatty acid concentrates from seal Blubber Oil (SBO) and menhaden Oil (MHO) upon enzymatic hydrolysis by Candida cylindracea lipase was optimized. In this process, the content of total ω-3 fatty acids, Y1; eicosapentaenoic acid, Y2; and docosahexaenoic acid, Y3, in the final product was maximized. A three-factor central composite rotatable design was used to study the effect of enzyme concentration (X1), reaction time (X2), and reaction temperature (X3). Second-order polynomial regression models for Y1, Y2, and Y3 were employed to generate response surfaces. After hydrolysis, a maximum of 54.3% total ω-3 fatty acids was obtained from SBO at an enzyme concentration of 308 U/g Oil, a reaction time of 40 h, and a reaction temperature of 37°C. Similarly, a maximum of 54.5% total ω-3 fatty acids was obtained from MHO at an enzyme concentration of 340 U/g Oil, a reaction time of 45 h, and a reaction temperature of 38°C.
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Concentration of ω‐3 polyunsaturated fatty acids of marine Oils using Candida cylindracea lipase: Optimization of reaction conditions
Journal of the American Oil Chemists' Society, 1998Co-Authors: Udaya N Wanasundara, Fereidoon ShahidiAbstract:Production of ω-3 fatty acid concentrates from seal Blubber Oil (SBO) and menhaden Oil (MHO) upon enzymatic hydrolysis by Candida cylindracea lipase was optimized. In this process, the content of total ω-3 fatty acids, Y1; eicosapentaenoic acid, Y2; and docosahexaenoic acid, Y3, in the final product was maximized. A three-factor central composite rotatable design was used to study the effect of enzyme concentration (X1), reaction time (X2), and reaction temperature (X3). Second-order polynomial regression models for Y1, Y2, and Y3 were employed to generate response surfaces. After hydrolysis, a maximum of 54.3% total ω-3 fatty acids was obtained from SBO at an enzyme concentration of 308 U/g Oil, a reaction time of 40 h, and a reaction temperature of 37°C. Similarly, a maximum of 54.5% total ω-3 fatty acids was obtained from MHO at an enzyme concentration of 340 U/g Oil, a reaction time of 45 h, and a reaction temperature of 38°C.
Natale G Frega - One of the best experts on this subject based on the ideXlab platform.
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Characterization of Phospholipid Molecular Species by Means of HPLC-Tandem Mass Spectrometry
Tandem Mass Spectrometry - Applications and Principles, 2012Co-Authors: Natale G Frega, Deborah Pacetti, Emmanuel BoselliAbstract:Phospholipids are the main constituents of the permeability barrier of cells and subcellular organelles. The phospholipid bilayer is the environment in which isolated proteins or dynamic nanoassemblies of sterols, sphingolipids, and proteins, called lipid rafts, act their vital functions, such as energy transduction, signal transduction, solute transport, DNA replication, protein targeting and trafficking, cell-cell recognition, secretion and many others (Lingwood et al., 2010). Christie et al. (2011) reported a detailed description of the general structure of phospholipids. According to Sud et al., 2007, phoshopholipids represent the category of lipids with the highest variety of structures (7775), followed in descending order, by polyketides (6713), fatty acyls (3942), sphingolipids (3936), glycerolipids (3044), sterol lipids (2196) and others. The positive effects of dietary phospholipids (PL) on hepatic lipid metabolism, atherosclerosis, obesity-related disorders and cardiovascular disease is a consistent experimental evidence (Shirouchi et al., 2007). The daily intake of PL can vary from 2 to 8 g per day and represents 1-10% of total daily fat intake (Cohn et al., 2008). The main natural phospholipid is phosphatidylcholine (lecithin) which is completely absorbed in humans. Natural or synthetic PLs are extracted from eggs and soybean and used as drug delivery systems since decades (Papahadjopoulos, 1978). During brain development, one of the most efficient forms of supplying 3-fatty acids such as DHA (docosahexaenoic acid) are phospholipids (Bourre & Dumont, 2002). In animal studies, it was reported that krill Oil (rich in 3-containing PLs) had stronger effects with respect to fish Oil (rich in 3-containing triacylglycerols) in increasing the DHA level in rat brain (Di Marzo et al., 2010). Although 3 are predominantly linked in the position Sn-1,3 of triacylglycerols (TG) in seal Blubber Oil, they are esterified in the Sn-2 position of the TGs and PLs of eggs obtained after feeding laying hens with enriched diets. Moreover, more 3 fatty acids are incorporated in phosphatidylethanolamine (PE) and phosphatidylcholine (PC) than in TGs (Pacetti et al., 2005). Apoptotic events and age-related diseases are strictly related to oxidized phospholipids. Much research remains to be done for the PL characterization by Liquid chromatography (LC) – tandem mass spectrometry (MS) aimed to understand their biological and
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Characterization of Phospholipid Molecular Species by Means of HPLC-Tandem Mass Spectrometry
Tandem Mass Spectrometry – Applications and Principles, 2011Co-Authors: Natale G Frega, Deborah Pacetti, Emmanuel BoselliAbstract:Phospholipids are the main constituents of the permeability barrier of cells and subcellular organelles. The phospholipid bilayer is the environment in which isolated proteins or dynamic nanoassemblies of sterols, sphingolipids, and proteins, called lipid rafts, act their vital functions, such as energy transduction, signal transduction, solute transport, DNA replication, protein targeting and trafficking, cell-cell recognition, secretion and many others (Lingwood et al., 2010). Christie et al. (2011) reported a detailed description of the general structure of phospholipids. According to Sud et al., 2007, phoshopholipids represent the category of lipids with the highest variety of structures (7775), followed in descending order, by polyketides (6713), fatty acyls (3942), sphingolipids (3936), glycerolipids (3044), sterol lipids (2196) and others. The positive effects of dietary phospholipids (PL) on hepatic lipid metabolism, atherosclerosis, obesity-related disorders and cardiovascular disease is a consistent experimental evidence (Shirouchi et al., 2007). The daily intake of PL can vary from 2 to 8 g per day and represents 1-10% of total daily fat intake (Cohn et al., 2008). The main natural phospholipid is phosphatidylcholine (lecithin) which is completely absorbed in humans. Natural or synthetic PLs are extracted from eggs and soybean and used as drug delivery systems since decades (Papahadjopoulos, 1978). During brain development, one of the most efficient forms of supplying 3-fatty acids such as DHA (docosahexaenoic acid) are phospholipids (Bourre & Dumont, 2002). In animal studies, it was reported that krill Oil (rich in 3-containing PLs) had stronger effects with respect to fish Oil (rich in 3-containing triacylglycerols) in increasing the DHA level in rat brain (Di Marzo et al., 2010). Although 3 are predominantly linked in the position Sn-1,3 of triacylglycerols (TG) in seal Blubber Oil, they are esterified in the Sn-2 position of the TGs and PLs of eggs obtained after feeding laying hens with enriched diets. Moreover, more 3 fatty acids are incorporated in phosphatidylethanolamine (PE) and phosphatidylcholine (PC) than in TGs (Pacetti et al., 2005). Apoptotic events and age-related diseases are strictly related to oxidized phospholipids. Much research remains to be done for the PL characterization by Liquid chromatography (LC) – tandem mass spectrometry (MS) aimed to understand their biological and 656 Tandem Mass Spectrometry – Applications and Principles physiopathological activity (Domingues et al., 2008). In the food industry, phospholipids are considered among the best emulsifying agents. Commercial preparations derived from soybean and corn Oils (commercial lecithins) are used extensively in manufactured foods such as bakery items, frostings, non-dairy creamers, confectionery products and ice creams. Staling and off-flavors are often related to the deterioration of the functional lipids in foods (Weihrauch et al., 1983). PLs extracts from eggs and/or fish products can play a pivotal role as an innovative food ingredient (Dumay et al., 2009; Commission Decision, 2000). Recently, a lipid extract rich of 3-containing PLs from krill (Euphausia superba) has been authorised by the EC as novel food/food ingredient (Commission Decision, 2009). Species, geographical origin, and production method of fish (i.e. wild/farmed) are the information which must be labelled in fishery and aquaculture products according to EU labelling regulations (Commission Regulation (EC) No 2065/2001). TGs are considered as markers for wild and farmed fish since their profile reflects the diet lipids (Standal et al., 2010), whereas the phospholipid profile is less affected by the diet and can be related to other variables, such as the species and stock (Joensen et al., 2000).
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high performance liquid chromatography tandem mass spectrometry of phospholipid molecular species in eggs from hens fed diets enriched in seal Blubber Oil
Journal of Chromatography A, 2005Co-Authors: Deborah Pacetti, Emmanuel Boselli, Howard W Hulan, Natale G FregaAbstract:Abstract The total lipid fraction of eggs from hens fed diets enriched in seal Blubber Oil (1.25–5.0% SBO) was directly analysed with normal-phase high performance liquid chromatography coupled on-line with electrospray ionization ion-trap tandem mass spectrometry (HPLC-ESI-MS–MS) for the identification of the molecular species of phospholipids (PLs). The species of phosphatidylethanolamine (PE) and phosphatidylinositol (PI) were all detected as the [M − H]− ions. The phosphatidylcholine (PC), sphingomyelin (Sph) and lysophosphatidylcholine (LPC) classes, were detected as formate adducts [M + HCOO]−. Tandem MS of PE and PI showed the loss of the carboxylate anions, and, for PI, also the loss of water and inositol. Product ion spectrum of PC, LPC and Sph contained only the [M − CH3]− ion fragment. Feeding different levels of SBO for 5 weeks resulted in a significant increase of PE, PC and PI molecular species carrying eicosapentaenoic acid (C20:5 ω3, EPA), docosapentaenoic acid (C22:5 ω3, DPA) and docosahexaenoic acid (C22:6 ω3, DHA), but not Sph nor LPC. The highest increase of the ω3/ω6 ratio occurred for PE and PC. On the contrary, PI was less affected by the increase of SBO in the diet.
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high performance liquid chromatography tandem mass spectrometry of phospholipid molecular species in eggs from hens fed diets enriched in seal Blubber Oil
Journal of Chromatography A, 2005Co-Authors: Deborah Pacetti, Emmanuel Boselli, Howard W Hulan, Natale G FregaAbstract:The total lipid fraction of eggs from hens fed diets enriched in seal Blubber Oil (1.25-5.0% SBO) was directly analysed with normal-phase high performance liquid chromatography coupled on-line with electrospray ionization ion-trap tandem mass spectrometry (HPLC-ESI-MS-MS) for the identification of the molecular species of phospholipids (PLs). The species of phosphatidylethanolamine (PE) and phosphatidylinositol (PI) were all detected as the [M-H](-) ions. The phosphatidylcholine (PC), sphingomyelin (Sph) and lysophosphatidylcholine (LPC) classes, were detected as formate adducts [M+HCOO](-). Tandem MS of PE and PI showed the loss of the carboxylate anions, and, for PI, also the loss of water and inositol. Product ion spectrum of PC, LPC and Sph contained only the [M-CH(3)](-) ion fragment. Feeding different levels of SBO for 5 weeks resulted in a significant increase of PE, PC and PI molecular species carrying eicosapentaenoic acid (C(20:5 omega3), EPA), docosapentaenoic acid (C(22:5 omega3), DPA) and docosahexaenoic acid (C(22:6 omega3), DHA), but not Sph nor LPC. The highest increase of the omega3/omega6 ratio occurred for PE and PC. On the contrary, PI was less affected by the increase of SBO in the diet.
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positional analysis of egg triacylglycerols and phospholipids from hens fed diets enriched with refined seal Blubber Oil
Journal of the Science of Food and Agriculture, 2005Co-Authors: Deborah Pacetti, Emmanuel Boselli, Howard W Hulan, Matthias Schreiner, Natale G FregaAbstract:The effect of feeding laying hens with refined seal Blubber Oil (SBO, containing 22.2% ω3 polyunsaturated fatty acids) on the fatty acids composition and regiospecific distribution of fatty acids in triacylglycerols (TAG) and phospholipids (PL) of egg produced was investigated. The hens were fed four diets containing 0 (control), 1.25, 2.5 or 5% SBO for 5 and 9 weeks. Comparison of the total fatty acids composition indicated that a 5 week feeding period was sufficient to obtain the highest amount of total polyunsaturated fatty acids in the eggs. The fatty acids composition of the egg lipids reflected the fatty acids composition of the diet. The substantial reduction in the ω6/ω3 ratio (ie 8.5 to 2.6) is of interest, and is in line with the recommendations of health authorities in several countries, where it has been suggested that the human diet should contain a ω6/ω3 ratio of 3–4. The greatest reduction of the ω6/ω3 ratio occurred for diet A (control) and diet B (1.25% SBO). Principal component analysis analysis of the fatty acids composition of egg lipid showed four clusters representing: (i) the control diet; (ii) the diet containing 1.25% SBO as well as samples obtained from feeding 2.5% SBO for 9 weeks; (iii) the diet with 5% SBO; and (iv) samples obtained from hens fed 2.5% SBO for 5 weeks. More ω-3 polyunsaturated fatty acids (ω3 PUFA) were incorporated in phosphatidylethanolamine and phosphatidylcholine than in TAG. Although ω3 were predominantly linked in the position Sn-1,3 of TAG in SBO, they were esterified in the Sn-2 position of the TAG and PL of eggs obtained after feeding laying hens with enriched diets. Copyright © 2005 Society of Chemical Industry
Deborah Pacetti - One of the best experts on this subject based on the ideXlab platform.
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Characterization of Phospholipid Molecular Species by Means of HPLC-Tandem Mass Spectrometry
Tandem Mass Spectrometry - Applications and Principles, 2012Co-Authors: Natale G Frega, Deborah Pacetti, Emmanuel BoselliAbstract:Phospholipids are the main constituents of the permeability barrier of cells and subcellular organelles. The phospholipid bilayer is the environment in which isolated proteins or dynamic nanoassemblies of sterols, sphingolipids, and proteins, called lipid rafts, act their vital functions, such as energy transduction, signal transduction, solute transport, DNA replication, protein targeting and trafficking, cell-cell recognition, secretion and many others (Lingwood et al., 2010). Christie et al. (2011) reported a detailed description of the general structure of phospholipids. According to Sud et al., 2007, phoshopholipids represent the category of lipids with the highest variety of structures (7775), followed in descending order, by polyketides (6713), fatty acyls (3942), sphingolipids (3936), glycerolipids (3044), sterol lipids (2196) and others. The positive effects of dietary phospholipids (PL) on hepatic lipid metabolism, atherosclerosis, obesity-related disorders and cardiovascular disease is a consistent experimental evidence (Shirouchi et al., 2007). The daily intake of PL can vary from 2 to 8 g per day and represents 1-10% of total daily fat intake (Cohn et al., 2008). The main natural phospholipid is phosphatidylcholine (lecithin) which is completely absorbed in humans. Natural or synthetic PLs are extracted from eggs and soybean and used as drug delivery systems since decades (Papahadjopoulos, 1978). During brain development, one of the most efficient forms of supplying 3-fatty acids such as DHA (docosahexaenoic acid) are phospholipids (Bourre & Dumont, 2002). In animal studies, it was reported that krill Oil (rich in 3-containing PLs) had stronger effects with respect to fish Oil (rich in 3-containing triacylglycerols) in increasing the DHA level in rat brain (Di Marzo et al., 2010). Although 3 are predominantly linked in the position Sn-1,3 of triacylglycerols (TG) in seal Blubber Oil, they are esterified in the Sn-2 position of the TGs and PLs of eggs obtained after feeding laying hens with enriched diets. Moreover, more 3 fatty acids are incorporated in phosphatidylethanolamine (PE) and phosphatidylcholine (PC) than in TGs (Pacetti et al., 2005). Apoptotic events and age-related diseases are strictly related to oxidized phospholipids. Much research remains to be done for the PL characterization by Liquid chromatography (LC) – tandem mass spectrometry (MS) aimed to understand their biological and
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Characterization of Phospholipid Molecular Species by Means of HPLC-Tandem Mass Spectrometry
Tandem Mass Spectrometry – Applications and Principles, 2011Co-Authors: Natale G Frega, Deborah Pacetti, Emmanuel BoselliAbstract:Phospholipids are the main constituents of the permeability barrier of cells and subcellular organelles. The phospholipid bilayer is the environment in which isolated proteins or dynamic nanoassemblies of sterols, sphingolipids, and proteins, called lipid rafts, act their vital functions, such as energy transduction, signal transduction, solute transport, DNA replication, protein targeting and trafficking, cell-cell recognition, secretion and many others (Lingwood et al., 2010). Christie et al. (2011) reported a detailed description of the general structure of phospholipids. According to Sud et al., 2007, phoshopholipids represent the category of lipids with the highest variety of structures (7775), followed in descending order, by polyketides (6713), fatty acyls (3942), sphingolipids (3936), glycerolipids (3044), sterol lipids (2196) and others. The positive effects of dietary phospholipids (PL) on hepatic lipid metabolism, atherosclerosis, obesity-related disorders and cardiovascular disease is a consistent experimental evidence (Shirouchi et al., 2007). The daily intake of PL can vary from 2 to 8 g per day and represents 1-10% of total daily fat intake (Cohn et al., 2008). The main natural phospholipid is phosphatidylcholine (lecithin) which is completely absorbed in humans. Natural or synthetic PLs are extracted from eggs and soybean and used as drug delivery systems since decades (Papahadjopoulos, 1978). During brain development, one of the most efficient forms of supplying 3-fatty acids such as DHA (docosahexaenoic acid) are phospholipids (Bourre & Dumont, 2002). In animal studies, it was reported that krill Oil (rich in 3-containing PLs) had stronger effects with respect to fish Oil (rich in 3-containing triacylglycerols) in increasing the DHA level in rat brain (Di Marzo et al., 2010). Although 3 are predominantly linked in the position Sn-1,3 of triacylglycerols (TG) in seal Blubber Oil, they are esterified in the Sn-2 position of the TGs and PLs of eggs obtained after feeding laying hens with enriched diets. Moreover, more 3 fatty acids are incorporated in phosphatidylethanolamine (PE) and phosphatidylcholine (PC) than in TGs (Pacetti et al., 2005). Apoptotic events and age-related diseases are strictly related to oxidized phospholipids. Much research remains to be done for the PL characterization by Liquid chromatography (LC) – tandem mass spectrometry (MS) aimed to understand their biological and 656 Tandem Mass Spectrometry – Applications and Principles physiopathological activity (Domingues et al., 2008). In the food industry, phospholipids are considered among the best emulsifying agents. Commercial preparations derived from soybean and corn Oils (commercial lecithins) are used extensively in manufactured foods such as bakery items, frostings, non-dairy creamers, confectionery products and ice creams. Staling and off-flavors are often related to the deterioration of the functional lipids in foods (Weihrauch et al., 1983). PLs extracts from eggs and/or fish products can play a pivotal role as an innovative food ingredient (Dumay et al., 2009; Commission Decision, 2000). Recently, a lipid extract rich of 3-containing PLs from krill (Euphausia superba) has been authorised by the EC as novel food/food ingredient (Commission Decision, 2009). Species, geographical origin, and production method of fish (i.e. wild/farmed) are the information which must be labelled in fishery and aquaculture products according to EU labelling regulations (Commission Regulation (EC) No 2065/2001). TGs are considered as markers for wild and farmed fish since their profile reflects the diet lipids (Standal et al., 2010), whereas the phospholipid profile is less affected by the diet and can be related to other variables, such as the species and stock (Joensen et al., 2000).
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high performance liquid chromatography tandem mass spectrometry of phospholipid molecular species in eggs from hens fed diets enriched in seal Blubber Oil
Journal of Chromatography A, 2005Co-Authors: Deborah Pacetti, Emmanuel Boselli, Howard W Hulan, Natale G FregaAbstract:Abstract The total lipid fraction of eggs from hens fed diets enriched in seal Blubber Oil (1.25–5.0% SBO) was directly analysed with normal-phase high performance liquid chromatography coupled on-line with electrospray ionization ion-trap tandem mass spectrometry (HPLC-ESI-MS–MS) for the identification of the molecular species of phospholipids (PLs). The species of phosphatidylethanolamine (PE) and phosphatidylinositol (PI) were all detected as the [M − H]− ions. The phosphatidylcholine (PC), sphingomyelin (Sph) and lysophosphatidylcholine (LPC) classes, were detected as formate adducts [M + HCOO]−. Tandem MS of PE and PI showed the loss of the carboxylate anions, and, for PI, also the loss of water and inositol. Product ion spectrum of PC, LPC and Sph contained only the [M − CH3]− ion fragment. Feeding different levels of SBO for 5 weeks resulted in a significant increase of PE, PC and PI molecular species carrying eicosapentaenoic acid (C20:5 ω3, EPA), docosapentaenoic acid (C22:5 ω3, DPA) and docosahexaenoic acid (C22:6 ω3, DHA), but not Sph nor LPC. The highest increase of the ω3/ω6 ratio occurred for PE and PC. On the contrary, PI was less affected by the increase of SBO in the diet.
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high performance liquid chromatography tandem mass spectrometry of phospholipid molecular species in eggs from hens fed diets enriched in seal Blubber Oil
Journal of Chromatography A, 2005Co-Authors: Deborah Pacetti, Emmanuel Boselli, Howard W Hulan, Natale G FregaAbstract:The total lipid fraction of eggs from hens fed diets enriched in seal Blubber Oil (1.25-5.0% SBO) was directly analysed with normal-phase high performance liquid chromatography coupled on-line with electrospray ionization ion-trap tandem mass spectrometry (HPLC-ESI-MS-MS) for the identification of the molecular species of phospholipids (PLs). The species of phosphatidylethanolamine (PE) and phosphatidylinositol (PI) were all detected as the [M-H](-) ions. The phosphatidylcholine (PC), sphingomyelin (Sph) and lysophosphatidylcholine (LPC) classes, were detected as formate adducts [M+HCOO](-). Tandem MS of PE and PI showed the loss of the carboxylate anions, and, for PI, also the loss of water and inositol. Product ion spectrum of PC, LPC and Sph contained only the [M-CH(3)](-) ion fragment. Feeding different levels of SBO for 5 weeks resulted in a significant increase of PE, PC and PI molecular species carrying eicosapentaenoic acid (C(20:5 omega3), EPA), docosapentaenoic acid (C(22:5 omega3), DPA) and docosahexaenoic acid (C(22:6 omega3), DHA), but not Sph nor LPC. The highest increase of the omega3/omega6 ratio occurred for PE and PC. On the contrary, PI was less affected by the increase of SBO in the diet.
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positional analysis of egg triacylglycerols and phospholipids from hens fed diets enriched with refined seal Blubber Oil
Journal of the Science of Food and Agriculture, 2005Co-Authors: Deborah Pacetti, Emmanuel Boselli, Howard W Hulan, Matthias Schreiner, Natale G FregaAbstract:The effect of feeding laying hens with refined seal Blubber Oil (SBO, containing 22.2% ω3 polyunsaturated fatty acids) on the fatty acids composition and regiospecific distribution of fatty acids in triacylglycerols (TAG) and phospholipids (PL) of egg produced was investigated. The hens were fed four diets containing 0 (control), 1.25, 2.5 or 5% SBO for 5 and 9 weeks. Comparison of the total fatty acids composition indicated that a 5 week feeding period was sufficient to obtain the highest amount of total polyunsaturated fatty acids in the eggs. The fatty acids composition of the egg lipids reflected the fatty acids composition of the diet. The substantial reduction in the ω6/ω3 ratio (ie 8.5 to 2.6) is of interest, and is in line with the recommendations of health authorities in several countries, where it has been suggested that the human diet should contain a ω6/ω3 ratio of 3–4. The greatest reduction of the ω6/ω3 ratio occurred for diet A (control) and diet B (1.25% SBO). Principal component analysis analysis of the fatty acids composition of egg lipid showed four clusters representing: (i) the control diet; (ii) the diet containing 1.25% SBO as well as samples obtained from feeding 2.5% SBO for 9 weeks; (iii) the diet with 5% SBO; and (iv) samples obtained from hens fed 2.5% SBO for 5 weeks. More ω-3 polyunsaturated fatty acids (ω3 PUFA) were incorporated in phosphatidylethanolamine and phosphatidylcholine than in TAG. Although ω3 were predominantly linked in the position Sn-1,3 of TAG in SBO, they were esterified in the Sn-2 position of the TAG and PL of eggs obtained after feeding laying hens with enriched diets. Copyright © 2005 Society of Chemical Industry
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Two step-production of acylglycerols containing a high proportion of docosapentaenoic acid from marine omega-3 Oil and their oxidative stability
Journal of Food Bioactives, 2018Co-Authors: Zhongshui Yu, Jiankang Wang, Fereidoon ShahidiAbstract:The objective of this study was to concentrate polyunsaturated fatty acid (PUFA) from seal Blubber Oil in an innovative manner to produce a high content of docosapentaenoic acid (DPA) in the resultant product. It also aimed at investigating the use of lipases as catalysts for synthesizing acylglycerols from glycerol and polyunsaturated fatty acid concentrates. Additionally, study of the oxidative stability of acylglycerols synthesized by lipases was intended. A two-stage urea complexation process was used to concentrate PUFA from seal Blubber Oil, giving rise to a DPA content of up to 24.0% in the product. Enzymatic synthesis of acyglycerols directly from glycerol and fatty acid concentrate was studied. Three lipases were used as biocatalysts for esterification. Lipase SP435 from Candida antarctica showed the highest activity for esterification. Effects of reaction parameters, namely temperature, time course and mole ratio of glycerol to fatty acid were followed with all three lipases. The optimal reaction time was 24 hr at 30 °C at a mole ratio of glycerol to fatty acid of 14:1. The maximum degree of acylglycerol synthesis was > 90%. The effect of time course and mole ratio of glycerol to fatty acid on acylglycerols distribution was also determined. The oxidative stability of different samples under Schaal-oven conditions at 60 °C showed that the oxidative stability of acylglycerols was better than that of the corresponding fatty acid esters.
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Acidolysis of p-coumaric acid with omega-3 Oils and antioxidant activity of phenolipid products in in vitro and biological model systems.
Journal of Agricultural and Food Chemistry, 2013Co-Authors: Jiankang Wang, Fereidoon ShahidiAbstract:Lipase-catalyzed acidolysis of p-coumaric acid with seal Blubber Oil (SBO) and menhaden Oil (MHO) was carried out, followed by identification of major phenolipids in the resultant acidolysis mixture using high-performance liquid chromatography/mass spectrometry. Separation of phenolipid components from the resultant acidolysis mixture was achieved using flash column chromatography. The antioxidant activities of the phenolipids were examined in in vitro assays and biological model systems. The major phenolipids identified from acidolysis mixtures with both SBO and MHO included eight phenolic monoacylglycerols and eight phenolic diacylglycerols. Phenolipids derived from SBO and MHO generally showed good antioxidant potential in the systems tested. The prepared phenolipids exhibited high scavenging capacity toward 1,1-diphenyl-2-picrylhydrazyl (DPPH) and peroxyl radicals and displayed reducing power, strong inhibitory effect on bleaching of β-carotene, human low-density lipoprotein (LDL) cholesterol oxidatio...
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Modification of marine Oils and their biological significance
2012Co-Authors: Jiankang WangAbstract:Marine Oils, such as seal Blubber and menhaden Oils offer a wide range of health benefits and play a critical role in many functions in the human body. Their effects in alleviating cancer cardiovascular disease, psychiatric disorders, Parkinson's disease and inflammatory ailments have been well demonstrated in a large body of literature. However, these Oils are highly vulnerable to oxidation due to their high content of polyunsaturated fatty acids (PUFA). There are a number of means to modify these marine omega-3 Oils in order to change their chemical and physical properties including randomization, blending and acidolysis. In this study, the effect of randomization using both chemical and enzymatic catalysts, as well as blending with antioxidant rich-wheat germ Oil on the oxidative stability of seal Blubber and menhaden Oils was investigated. Meanwhile, lipase-catalysed acidolysis of p-coumaric acid with triolein, seal Blubber and menhaden Oils was carried out in this work, followed by examination of the antioxidant activities of the synthesized phenolic lipids in in vitro assays, food and biological systems. The results indicated that both chemical and enzymatic randomization lead to the redistribution of fatty acids among the stereoisomeric sn-1 ,3 and sn-2 positions of the glycerol moiety of triaclyglycerols of seal Blubber and menhaden Oils. The changes in oxidative stability were due to the loss of tocopherol and positional redistribution of fatty acids, especially the unsaturated fatty acids. Blending with wheat germ Oil modified fatty acid composition and increased the tocopherol content of seal Blubber and menhaden Oils, hence improving the oxidative stability of blended seal Blubber and menhaden Oils, mainly due to the increased content of tocopherols, especially gamma- and deltatocopheols as the total content of unsaturated fatty acids before and after blending was similar. Therefore, wheat germ Oil served as a good stabilizer for marine Oils tested. Phenolic lipids derived from triolein, seal Blubber Oil and menhaden Oil showed good antioxidant potential in systems tested. The prepared phenolic lipids exhibited high scavenging capacity towards 1, 1-diphenyl-2-picrylhydrazyl (DPPH) and peroxyl radicals, and displayed reducing power, strong inhibitory effect in bleaching ~-carotene, human low-density lipoprotein (LDL) cholesterol oxidation as well as radical-induced DNA cleavage, which suggests that phenolic lipids derived from seal Blubber and menhaden Oils may be used as potential stable marine Oils for health promotion and disease risk reduction.
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Effect of enzymatic randomization on positional distribution and stability of seal Blubber and menhaden Oils.
Journal of Agricultural and Food Chemistry, 2011Co-Authors: Jiankang Wang, Fereidoon ShahidiAbstract:In an effort to investigate the effect of positional distribution on oxidative stability of menhaden and seal Blubber Oils, Novozyme 435 was used as a random biocatalyst. Positional distribution of fatty acids was determined using gas chromatography. As some of the α-tocopherol was lost during randomization, its content was adjusted to the level prior to the process to eliminate this effect on oxidative stability of Oils tested. Conjugated dienes (CD) and thiobarbituric acid reactive substances (TBARS) were used as indicators of oxidative stability. The results showed that the polyunsaturated fatty acids were distributed predominantly at terminal positions in randomized menhaden Oil, whereas they were distributed more evenly among all positions in enzymatically randomized seal Blubber Oil, compared to their unrandomized counterparts. Results of CD and TBARS values indicated that randomized menhaden Oil was more stable than the original Oil, whereas randomized seal Blubber Oil was more vulnerable to oxidat...
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Effect of chemical randomization on positional distribution and stability of omega-3 Oil triacylglycerols.
Journal of Agricultural and Food Chemistry, 2010Co-Authors: Jiankang Wang, Jaroslav Kralovec, Erick Reyes Suárez, Fereidoon ShahidiAbstract:Randomization has been commonly used to modify the chemical and physical properties of natural fats and Oils. In this study, seal Blubber Oil (SBO) and menhaden Oil (MHO) were modified through chemical randomization using sodium methoxide, and the effect on positional distribution of fatty acids was investigated using gas chromatography (GC) and 13C nuclear magnetic resonance (NMR) spectroscopy. The effect of randomization on the stability of the original Oils and their randomized counterparts was analyzed by comparing conjugated dienes and thiobarbituric acid reactive substances (TBARS) values after accelerated oxidation at 60 °C for 4 days. The omega-3 polyunsaturated fatty acids (PUFA) were distributed more evenly among the terminal sn-1,3 positions and the middle sn-2 position in chemically randomized Oils when compared to the starting Oils. The effect was more pronounced for SBO with omega-3 PUFA attached preferentially to sn-1,3 positions of triacylglycerols before randomization, and it was less pro...
