Fatty Acids In Sn-2 Position Research Articles

Ultrasound-assisted extraction of cranberry seed oil: food waste valorization approach

Cranberry pomace considered as a by-product of fruit industry contains seeds which may be processed to highly nutritive oil. Conventional extraction methods may be, however, harmful to natural environment, thus alternative, ultrasound-assisted extraction method may be useful tool to reduce environmental impact. In the following study, sonication was applied to extract oil from cranberry seeds. The aim of the study was to determine the most efficient conditions of ultrasound-assisted extraction of oil and to investigate sonication influence on the properties of final product. Ultrasound amplitude and extraction time were independent variables; yield and maximum induction time of oils were responses. The most efficient conditions were amplitude of 95% and extraction time of 11.38 min. Model predicted extraction yield of 22.55 ± 0.36% (vs. actual 21.98 ± 0.08%) and induction time of 52.60 ± 0.95 min (vs. actual 61.95 ± 3.06 min). Detailed analyses of oil extracted in the most efficient conditions and the control sample were performed. Kinetic parameters of oil oxidation, fatty acid profile and distribution, melting characteristics studies were carried out. Sonication influenced activation energy of oxidation reaction, contribution of chosen fatty acids (oleic, α-linolenic and eicosenoic fatty acids) and distribution of oleic and α-linolenic fatty acids in sn-2 position of triacylglycerols. Slight changes in melting profile of oils were also recorded. Scanning electron microscopy of cranberry seeds revealed that ultrasound treatment resulted in pore enlargement and fat agglomeration damage. Additional studies of thermal properties of cranberry seeds: differential scanning calorimetry and modulated differential scanning calorimetry were performed, which confirmed that cranberry seeds may be a new source of oil with unique properties.

Palmitic Acid is Absorbed as sn-2 Monopalmitin from Milk and Formula with Rearranged Triacylglycerols and Results in Increased Plasma Triglyceride sn-2 and Cholesteryl Ester Palmitate in Piglets

Milk fatty acids contain 20–30% palmitic acid (16:0), with -70% of the 16:0 esterified to the sn-2 position of the milk triacylglycerol. Formulae containing vegetable and oleo oils contain different amounts of 16:0, but all have unsaturated fatty acids esterified to the triacylglycerol sn-2 position. Intraluminal triacylglycerol hydrolysis by endogenous lipases produces sn-2 monoacylglycerols and free fatty acids, which are absorbed and re-esterified in the enterocyte for secretion to plasma. The extent of absorption and re-esterification of sn-2 monoacylglycerols from milk or formula fats in infants is unknown. This was studied by feeding piglets sow milk or formulae containing similar total saturated fat, 18:1, 18:2(n-6) and 18:3(n-3) with unsaturated fatty acids at the sn-2 position or with rearranged triacylglycerols containing -30% 16:0, with 70% 16:0 in fatty acids at the sn-2 position. Feeding milk or 16:0 on the sn-2 position of formula with rearranged triacylglycerols resulted in higher 16:0 esterified to the plasma triacylglycerol sn-2 position and in cholesteryl esters than feeding formulae with 0.4 to 4.4% 16:0 in the sn-2 position fatty acids. The absorption of 16:0 as monopalmitin from milk and any metabolic importance in human infants has yet to be determined.

Fatty Acids, Triacylglycerol and Sn -2 Fatty Acids Distributions Variations in Seed Oil from Camellia Cultivars

Camellia seed oil is widely used in the food, health, cosmetics and medicine industries in China. The present study aimed to investigate fatty acids, triacylglycerols (TGAs) and sn-2 fatty acids distributions variations in seed oil from 46 kinds of Camellia cultivars. The predominant fatty acids was oleic acid (18:1ω9) with 71.30% (average). The sn-2 position was mainly occupied by oleic acid, linoleic acid and palmitic acid. Fifteen TAGs species were found and the main TAGs were OOO + SLO, OOP and OOL+SLL. The trisaturated TAGs species were not detected. These results indicated significant changes in the profiles of fatty acids, sn-2 position fatty acids and TGAs, and in contents of these in seed oils from different Camellia cultivars (P< 0.05). Saturated fatty acids is not positively related to its distribution in sn-2 position. The data in present paper may be important as a reference for adulteration of camellia seed oil with other oils.

Phosphatidylcholine and phosphatidylethanolamine plasmalogens in lipid loaded human macrophages.

BackgroundPlasmalogens are either phosphatidylcholine (PC P) or phosphatidylethanolamine (PE P) glycerophospholipids containing a vinyl ether moiety in sn-1-position and an esterified fatty acid in sn-2 position. Multiple functions have been proposed, including reservoir of precursors for inflammatory mediators, modulation of membrane fluidity, and anti-oxidative properties. They could therefore play a role under conditions of metabolic stress. Especially enzymatically modified LDL (eLDL) and oxidatively modified LDL (oxLDL) represent modifications of LDL that are taken up by macrophages in atherosclerotic plaques. The aim of this study was to analyze plasmalogen related effects of eLDL and oxLDL in human monocyte derived macrophages, as well as the effects of HDL3 mediated deloading.MethodsElutriated monocytes from nine healthy donors were differentiated in vitro for four days. Macrophages were then loaded with native LDL, eLDL and oxLDL for 24h and subsequently deloaded with HDL3 for another 24h. Lipidomic and transcriptomic profiles were obtained.ResultsLoading of macrophages with eLDL and oxLDL led to a transient but strong elevation of lysophosphatidylcholine (LPC) most likely through direct uptake. Only eLDL induced increased levels of total PC, presumably through an induction of PC synthesis. On the other hand treatment with oxLDL led to a significant increase in PC P. Analysis of individual lipid species showed lipoprotein and saturation specific effects for LPC, PC P and PE P species. Membrane fluidity was decreased by the large amount of FC contained in the lipoproteins, as indicated by a lower PC to FC ratio after lipoprotein loading. In contrast the observed changes in the saturated to mono-unsaturated fatty acid (SFA to MUFA) and saturated to poly-unsaturated fatty acid (SFA to PUFA) ratios in PE P could represent a cellular reaction to counteract this effect by producing more fluid membranes. Transcriptomic analysis showed considerable differences between eLDL and oxLDL treated macrophages. As a common feature of both lipoproteins we detected a strong downregulation of pathways for endogenous lipid synthesis as well as for exogenous lipid uptake. Deloading with HDL3 had only minor effects on total lipid class as well as on individual lipid species levels, most of the time not reaching significance. Interestingly treatment with HDL3 had no effect on membrane fluidity under these conditions, although incubation with HDL3 was partially able to counteract the oxLDL induced transcriptomic effects. To investigate the functional effect of lipoprotein treatment on macrophage polarization we performed surface marker flow cytometry. Under our experimental conditions oxLDL was able to partially shift the surface marker pattern towards a pro-inflammatory M1-like phenotype. This is consistent with the consumption of arachidonic acid containing PE P species in oxLDL treated cells, presumably for the synthesis of inflammatory mediators.SummaryOur findings provide novel data on the lipoprotein induced, lipidomic and transcriptomic changes in macrophages. This can help us better understand the development of metabolic, inflammatory diseases as well as improve our background knowledge on lipid biomarkers in serum.

Characterization of Phospholipase A2 Enzyme Activity in Serum of the Komodo Dragon (Varanus komodoensis)Soluble phospholipase A2 (sPLA2) is an enzyme found in the peripheral circulation of vertebrates which has significant immunological activity. This en

Soluble phospholipase A2 (sPLA2) is an enzyme found in the peripheral circulation of vertebrates which has significant immunological activity. This enzyme exerts immune activity by the hydrolysis of fatty acids from the sn-2 position of membrane glycerophospholipids of microbes, thus compromising membrane integrity and casing eventual lysis. We utilized membrane fatty acids labeled with a fluorescent probe (BODIPY) at the sn-2 position fatty acid to label the membranes. Incubation of different volumes of serum from Komodo dragons with BODIPY-labeled bacteria resulted in liberation of labeled fatty acid in a serum volume-dependent manner. This cleavage of fatty acid occurred rapidly, with a biphasic production of fluorescent product. An immediate accumulation of product was noted, which increased steadily for a 30-minute period, followed by a slower hydrolysis between 30 and 180 min. The activity was temperature-dependent, with low activities observed at 5oC and a linear increase up to 40oC. The liberation for fatty acid was inhibited by p-bromophenacyl bromide, a specific phospholipase A2 (PLA2) inhibitor, in a concentration-dependent manner, indicating that the activity was due to the presence of sPLA2.

Determination of sn-2 position fatty acid in oils by SPE method with Florisil extraction cartridge coupled with gas chromatography

Determination of sn-2 position fatty acid in oils by SPE method with Florisil extraction cartridge coupled with gas chromatography

The Effectiveness of Immobilized Lipase Thermomyces lanuginosa in Catalyzing Interesterification of Palm Olein in Batch Reaction

Lipase Thermomyces lanuginosa has shown potential in modifying oils and fats through interesterification. Analyzing the physicochemical properties of the modified oils is important to determine the effectiveness of lipase in catalyzing interesterification. In this study, the effectiveness of the immobilized lipase (Lipozyme(®) TL IM) in catalyzing interesterification of palm olein in pilot-scale batch reactor was determined. The evaluation was done by analyzing the changes of triacylglycerol (TAGs) composition, sn-2 position fatty acids composition and the physical properties of the palm olein after the interesterifications. The pilot-scale batch reaction was conducted for 8 hours with 5 %w/w enzyme dosage based on the results of TAGs composition of the laboratory-scale interesterified products. The pilot-scale results showed that Lipozyme(®) TL IM act as an effective enzyme in converting TAGs, in which 4.5% of trisaturated TAGs (PPP and PPS) were produced in the batch reaction. The formation of these new TAGs had also altered the thermal and physical properties of the palm olein. These interesterified products showed a broad peak and shoulder at high temperature, ranging from 10°C to 40°C, indicating the formation of some new TAGs with high melting points. However, the enzyme did not perform perfectly as a 1,3-specific enzyme in the reaction as a significant reduction of oleic acid and an increment of palmitic acid at the sn-2 position was observed.

국내 시장에서 유통되는 국내·외 초콜릿의 지방산 조성 및 triacylglycerol 조성 분석

The fat content, fatty acid composition, trans fatty acid content and triacylglycerol (TAG) composition of 22 chocolates (domestics 8, foreigns 14) collected from the Korea distribution markets were investigated. The crude fat was extracted by acid hydrolysis method and analyzed by gas chromatography (GC) and reversed-phase HPLC for fatty acid and TAG compositions, respectively. The crude fat content of all chocolates varied between 30.11% and 49.59%. The major fatty acids in most of the chocolates were palmitic acid (19.36~31.15 wt%), stearic acid (5.11~36.32 wt%) and oleic acid (18.77~36.68 wt%). Whereas lauric acid (approximately 35.43 wt%) was detected in chocolate fat of sample No. 18. High oleic acid content was observed for the sn-2 position fatty acid with a range from 64.91% to 86.93%. Trans fatty acid contents in domestic chocolates (sample No. 1~8) and foreign chocolates (sample No. 9~22) were 0.03~0.59 wt% (0.01~0.19 g/100g chocolate) and 0.05~6.32 wt% (0.02~1.99 g/100g chocolate), respectively. In TAG composition, TAGs such as POP/PPO(1,3(2)-palmitoyl-2(3)-oleoyl glycerol, PN=48), POS/PSO(palmitoyl-oleoyl-stearoyl glycerol or palmitoyl-stearoyl-oleoyl glycerol, PN=50), SOS/SSO(1,3(2)-stearoyl-2(3)-oleoyl glycerol, PN=50) were mainly detected in most of the chocolates. The peaks of TAG with low PN (ex, 32-34, 36-38, and 40-42) were detected in No. 18 chocolate fat because of containing short chain fatty acid such as lauric acid.

Activation of the Chloroplast Monogalactosyldiacylglycerol Synthase MGD1 by Phosphatidic Acid and Phosphatidylglycerol

One of the major characteristics of chloroplast membranes is their enrichment in galactoglycerolipids, monogalactosyldiacylglycerol (MGDG), and digalactosyldiacylglycerol (DGDG), whereas phospholipids are poorly represented, mainly as phosphatidylglycerol (PG). All these lipids are synthesized in the chloroplast envelope, but galactolipid synthesis is also partially dependent on phospholipid synthesis localized in non-plastidial membranes. MGDG synthesis was previously shown essential for chloroplast development. In this report, we analyze the regulation of MGDG synthesis by phosphatidic acid (PA), which is a general precursor in the synthesis of all glycerolipids and is also a signaling molecule in plants. We demonstrate that under physiological conditions, MGDG synthesis is not active when the MGDG synthase enzyme is supplied with its substrates only, i.e. diacylglycerol and UDP-gal. In contrast, PA activates the enzyme when supplied. This is shown in leaf homogenates, in the chloroplast envelope, as well as on the recombinant MGDG synthase, MGD1. PG can also activate the enzyme, but comparison of PA and PG effects on MGD1 activity indicates that PA and PG proceed through different mechanisms, which are further differentiated by enzymatic analysis of point-mutated recombinant MGD1s. Activation of MGD1 by PA and PG is proposed as an important mechanism coupling phospholipid and galactolipid syntheses in plants.

Effects of increasing dietary concentrations of specific structured triacylglycerides on performance and nitrogen and energy metabolism in broiler chickens

1. Specific structured triacylglycerides (STG) containing medium chain fatty acids in sn-1,3 positions and a long chain fatty acid in sn-2 position were prepared from rapeseed oil and capric acid (C10:0). 2. A total of 80 female broiler chickens (Ross 208) were randomly allocated into five dietary treatments as two series of 40 chicks: a basal diet with graded levels of STG of 0, 20, 40, 60 and 80 g/kg diet at the expense of rapeseed oil were fed to the chickens in groups of four. At 12 d of age the chickens were placed pair-wise in metabolism cages. The grower period (d 13–36) was divided into four consecutive balance periods each of 6 d. Two 24 h measurements of gas exchange in two open-air circuit respiration chambers were performed during the second and third day of each balance period. 3. During the whole experiment there was a negative effect of the inclusion of STG on average feed intake. However, this only slightly affected average daily weight gain. Feed conversion efficiency improved linearly with the inclusion level of STG. Daily gain adjusted to mean daily feed intake increased linearly with inclusion rate of STG, indicating that the weight gain was affected by both feed intake and the enhancing effect on digestibility of STG. Weight of small intestine and colon decreased with increasing inclusion of STG. 4. Utilisation of dietary protein relative to intake increased while that of retained fat tended to decrease resulting in a decreased utilisation of metabolisable energy (RE/ME) in birds receiving STG. Heat production (HE) was slightly lower in the STG groups. 5. More of the dietary fat was oxidised when more STG was added, although the total amount of fat in the diets was kept constant.

Metabolism of defined structured triglyceride particles compared to mixtures of medium and long chain triglycerides intravenously infused in dogs

The present study aimed to determine whether including medium-chain fatty acids (MCFA) in specifically designed structured triglycerides (STG) with a MCFA in sn-1 and sn-3 positions and a long-chain (LC) FA in sn-2 position (MLM) would lead to different effects on plasma lipids and FA distribution into plasma and tissue lipids by comparison to a mixture of separate MCT and LCT molecules (MMM/LLL). The fatty acid (FA) composition was comparable in both lipid emulsions. Lipids were infused over 9 h daily, in 2 groups of dogs ( n=6 each), for 28 days as a major component (55% of the non-protein energy intake) of total parenteral nutrition (TPN). Blood samples were obtained on specific days, before starting and just before stopping TPN. The concentration of plasma lipids was measured before starting and before stopping TPN on days 1, 2, 3, 4, 5, 8, 10, 12, 16 and 28. Biopsies were obtained from liver, muscle and adipose tissue 15 days before starting, and again on the day following cessation of TPN. In addition, the spleen was removed after the TPN period. FA composition in plasma and tissue lipids was analysed by gas liquid chromatography in different lipid components of plasma and tissues. No differences in either safety or tolerance parameters were detected between both lipid preparations. A lower rise of plasma TG ( P<0.05) was observed during MLM infusion, indicating a faster elimination rate of MLM vs MMM/LLL emulsion. In spite of the differences of TG molecules which would be assumed to affect the site of FA delivery and metabolic fate, FA distribution in phospholipids (PL) of hepatic and extrahepatic tissues did not substantially differ between both emulsions.

Triglyceride, total and 2-position fatty acid composition of Cornicabra virgin olive oil: Comparison with other Spanish cultivars

The main triglycerides (TG) found in the Cornicabra virgin olive oil variety samples analyzed ( n=224, from 1995/96 to 1999/2000 crop seasons) were OOO, SOL + POO, OLO + LnPP and OLA + SOO, as expected from the high oleic acid and low linoleic and linolenic acid contents observed for both the total and sn-2 position fatty acids (FA); these accounted for more than 85% of the total HPLC chromatogram peak area. Concentrations of most of the TGs and FAs presented highly significant statistical differences ( p⩽0.001) among the four Spanish varieties studied. Principal component analysis and discriminant analysis (PCA and DA) suggested that the TG variables are more suitable than total and 2-position FAs for optimum classification of the commercial samples analyzed. Finally, PCA and DA showed that there are several combinations of TGs and total FA variables (from 3 to 5) which can be selected for satisfactory classification of the four Spanish virgin olive oil varieties studied, guaranteeing 90%-plus correct classification.

The efficient synthesis of mixed diacyl phospholipids with polyunsaturated fatty acid in sn-2 position of glycerol

A convenient method for synthesis of the mixed-diacyl phospholipid using boron trichloride as an efficient reagent for the removal of benzyl protecting group from polyunsaturated diacylglycerols without affecting the double bond and acyl migration is described.

Dietary Triacylglycerols with Palmitic Acid (16:0) in the 2-Position Increase 16:0 in the 2-Position of Plasma and Chylomicron Triacylglycerols, but Reduce Phospholipid Arachidonic and Docosahexaenoic Acids, and Alter Cholesteryl Ester Metabolism in Formula-Fed Piglets ,

Milk triacylglycerols have an unusual fatty acid distribution, with palmitic acid (16:0) esterified predominately at the center (sn-2) position. Other dietary triacylglycerols contain 16:0 predominantly at the sn-1,3 positions. This study was designed to evaluate the effect of formula triacylglycerol fatty acid distribution on the composition and distribution of plasma lipoprotein fatty acids in piglets fed formula containing synthesized triacylglycerols or palm olein oil with about 32 or 4.2% 16:0, respectively, in fatty acids at the sn-2 position, with comparison to piglets fed sow’s milk. Feeding formula with 16:0 at the triglyceride sn-2 position or sow’s milk resulted in higher chylomicron triacylglycerol sn-2 16:0 than when palm olein was fed. This suggests that dietary triacylglycerol sn-2 position fatty acids are conserved during digestion, absorption and reassembly to chylomicron triacylglycerols. The increased chylomicron triacylglycerol sn-2 position 16:0 in piglets fed synthesized triacylglycerols was accompanied by lower chylomicron triacylglycerol arachidonic and docosahexaenoic acid than in piglets fed formula with palm olein, suggesting an interaction between dietary triacylglycerol saturated fatty acid distribution and (n-6) and (n-3) fatty acid transport.

Regulation of membrane lipid bilayer structure during seasonal variation: a study on the brain membranes of Clarias batrachus

(1) A significant seasonal variation in the membrane fluidity (as sensed by DPH-fluorescence polarization), membrane lipid components (phospholipid and neutral lipid), fatty acid composition of membrane phospholipid (phosphatidylcholine, phosphatidylethanolamine and sphingomyelin), positional distribution of fatty acids at Sn-1 and Sn-2 position of phosphatidyl-choline and -ethanolamine is noticed in the brain membranes (myelin, synaptosomes, and mitochondria) of a tropical air breathing teleost, Clarias batrachus. (2) A `partial compensation' of membrane fluidity during seasonal adaptation is observed in myelin and mitochondria membrane fractions. Synaptosomes membrane fraction exhibits a different response. Depletion (about 15–70%) of membrane lipid components (phospholipid, cholesterol, diacylglycerol and triacylglycerol) per unit of membrane protein is the characteristic feature of summer adaptation. An increase (about 20–100%) in the level of oleic acid and decrease (about 20–60%) in the level of stearic acid are almost common features in membrane phospholipid fractions of winter-adapted Clarias. (3) From the tissue slice experiment it is evident that there is an activation of cellular phopholipase A 2 at lower growth temperature and of cellular phosphalipase A 1 at higher growth temperature and this suggests the reorganization of molecular architecture of the membrane during seasonal adaptation. (4) Accumulation of oleic acid in Sn-1 position and polyunsaturated fatty acids in Sn-2 position of phophatidyl-choline and -ethanolamine during winter indicates an increase in the concentration of 1-monoenoic, 2-polyenoic molecular species of phospholipid in order to maintain the stability of membrane lipid bilayer.

The effect of alteration of fatty acids in SN-2 position of lecithin on cholesterol carriers, nucleation and crystal growth: [formula omitted] Department of Gastroenterology, Souraski Medical Center, Ichilov Hospital and Sackler Medical School, Tel-Aviv University, Israel

The effect of alteration of fatty acids in SN-2 position of lecithin on cholesterol carriers, nucleation and crystal growth: [formula omitted] Department of Gastroenterology, Souraski Medical Center, Ichilov Hospital and Sackler Medical School, Tel-Aviv University, Israel