Plasma Phospholipid Fatty Acid and Ex Vivo Neutrophil Responses are Differentially Altered in Dogs Fed Fish- and Linseed-Oil Containing Diets at the Same n-6:n-3 Fatty Acid Ratio

The effect of diets containing either 18-carbon n-3 fatty acids (FA) or 20/22-carbon n-3 FA on canine plasma and neutrophil membrane fatty acid composition, superoxide and leukotriene B₄ and B₅ production when fed at the same n-6:n-3 fatty acid ratio was investigated. Four groups of ten dogs each were fed a low fat basal diet supplemented with safflower oil (SFO), beef tallow (BTO), linseed oil (LSO), or Menhaden fish oil (MHO) for 28 days. Dietary fat provided 40.8% of energy and the n-6:n-3 of the diets were ~100:1, 9.7:1, 0.38:1, and 0.34:1 for the SFO, BTO, LSO and MHO groups, respectively. The MHO and LSO groups had increased incorporation of EPA and DPA in both the plasma and neutrophil membranes compared to the BTO and SFO groups. DHA was observed in the MHO but not in the LSO group. Neutrophils from the MHO diet fed dogs had less LTB₄ and greater LTB₅ than the other three groups. The LSO group also showed a reduction in LTB₄ and greater LTB₅ production compared to the SFO and BTO groups. Both LSO and MHO groups had lower superoxide production compared to the SFO and BTO groups. Diets containing 18 or 20/22 carbon n-3 FA fed at the same n-6:n-3 resulted in differential incorporation of long chain n-3 FA into neutrophil membranes. Thus, fatty acid type and chain length individually affect neutrophil membrane structure and function and these effects exist independent of dietary total n-6:total n-3 FA ratios.     

Low n-6/n-3 PUFA Ratio Improves Lipid Metabolism,Inflammation, Oxidative Stress and Endothelial Function in Rats Using Plant Oils as n-3 Fatty Acid Source

Lipid metabolism, inflammation, oxidative stress and endothelial function play important roles in the pathogenesis of cardiovascular disease (CVD), which may be affected by an imbalance in the n‐6/n‐3 polyunsaturated fatty acid (PUFA) ratio. This study aimed to investigate the effects of the n‐6/n‐3 PUFA ratio on these cardiovascular risk factors in rats fed a high‐fat diet using plant oils as the main n‐3 PUFA source. The 1:1 and 5:1 ratio groups had significantly decreased serum levels of total cholesterol, low‐density lipoprotein cholesterol, and proinflammatory cytokines compared with the 20:1 group (p < 0.05). Additionally, the 20:1 group had significantly increased serum levels of E‐Selectin, von Willebrand factor (vWF), and numerous markers of oxidative stress compared with the other groups (p < 0.05). The 1:1 group had a significantly decreased lipid peroxide level compared with the other groups (p < 0.05). Serum levels of malondialdehyde, reactive oxygen species and vWF tended to increase with n‐6/n‐3 PUFA ratios increasing from 5:1 to 20:1. We demonstrated that low n‐6/n‐3 PUFA ratio (1:1 and 5:1) had a beneficial effect on cardiovascular risk factors by enhancing favorable lipid profiles, having anti‐inflammatory and anti‐oxidative stress effects, and improving endothelial function. A high n‐6/n‐3 PUFA ratio (20:1) had adverse effects. Our results indicated that low n‐6/n‐3 PUFA ratios exerted beneficial cardiovascular effects, suggesting that plant oils could be used as a source of n‐3 fatty acids to prevent CVD. They also suggested that we should be aware of possible adverse effects from excessive n‐3 PUFA.     

Estradiol Favors the Formation of Eicosapentaenoic Acid (20:5n-3) and n-3 Docosapentaenoic Acid (22:5n-3) from Alpha-Linolenic Acid (18:3n-3) in SH-SY5Y Neuroblastoma Cells

Whether neurosteroids regulate the synthesis of long chain polyunsaturated fatty acids in brain cells is unknown. We examined the influence of 17-β-estradiol (E2) on the capacity of SH-SY5Y cells supplemented with α-linolenic acid (ALA), to produce eicosapentaenoic acid (EPA), docosapentaenoic acid (DPA) and docosahexaenoic acid (DHA). Cells were incubated for 24 or 72 h with ALA added alone or in combination with E2 (ALA + E2). Fatty acids were analyzed by gas chromatography of ethanolamine glycerophospholipids (EtnGpl) and phosphatidylcholine (PtdCho). Incubation for 24 h with ALA alone increased EPA and DPA in EtnGpl, by 330 and 430% compared to controls (P < 0.001) and DHA by only 10% (P < 0.05). Although DHA increased by 30% (P < 0.001) in ALA + E2-treated cells, the difference between the ALA and ALA + E2 treatments were not significant after 24 h (Anova-1, Fisher’s test). After 72 h, EPA, DPA and DHA further increased in EtnGpl and PtdCho of cells supplemented with ALA or ALA + E2. Incubation for 72 h with ALA + E2 specifically increased EPA (+34% in EtnGpl, P < 0.001) and DPA (+15%, P < 0.001) compared to ALA alone. Thus, SH-SY5Y cells produced membrane EPA, DPA and DHA from supplemental ALA. The formation of DHA was limited, even in the presence of E2. E2 significantly favored EPA and DPA production in cells grown for 72 h. Enhanced synthesis of ALA-elongation products in neuroblastoma cells treated with E2 supports the hypothesis that neurosteroids could modulate the metabolism of PUFA.     

Enzymatic Modification of Anhydrous Milkfat with n-3 and n-6 Fatty Acids for Potential Use in Infant Formula: Comparison of Methods

A structured lipid (SL) with a high amount of sn‐2 palmitic acid was synthesized from anhydrous milkfat and was then enriched with docosahexaenoic (DHA) and arachidonic (ARA) acids using an immobilized lipase. Three different methods were compared including physical blending, enzymatic interesterification, and enzymatic acidolysis. Products were compared with respect to differences in fatty acid profiles, reaction times, antioxidant contents, oxidative stability, melting and crystallization profiles, and reaction yields. The acidolysis method was the least suitable for the synthesis of desired product because of a low reaction yield, low incorporation of DHA, low oxidative stability, and the extra processing steps required. The physical blending and interesterification methods were suitable, but the interesterification product (IE‐SL) had higher amounts of ARA at the sn‐2 position. The IE‐SL contained total ARA and DHA of 0.63 and 0.50 mol%, and 0.55 and 0.46 mol% at the sn‐2 position, respectively. The IE‐SL also contained 44.97 mol% sn‐2 palmitic acid. The reaction yield for the IE‐SL was 91.84 %, and its melting completion and crystallization onset temperatures were 43.1 and 27.1 °C, respectively. This SL might be totally or partially used in commercial fat blends for infant formula.     

Efficient Synthesis of the Very-Long-Chain n-3 Fatty Acids,Tetracosahexaenoic Acid (C<Subscript>24</Subscript>:6n-3) and Tricosahexaenoic Acid (C<Subscript>23</Subscript>:6n-3)

Tetracosahexaenoic acid (C₂₄:6n-3, THA, 3) is an essential biosynthetic precursor in mammals of docosahexaenoic acid (C₂₂:6n-3, DHA, 1), the end-product of the metabolism of n-3 fatty acids. THA 3 is present in commercially valuable fishes, such as flathead flounder. Tricosahexaenoic acid (C₂₃:6n-3, TrHA, 2), an odd-numbered-chain fatty acid, has been identified from marine organisms such as the dinoflagellate, Amphidinium carterae. To date, few studies have examined THA 3 and TrHA 2 due to difficulties in detecting and identifying these compounds, so their chemical and biological properties remain poorly characterized. Only one methodology for the chemical synthesis of THA 3 has been presented, and no method for the synthesis of TrHA 2 has been reported. We report here the efficient synthesis of THA 3 in four steps in 56% overall yield, and the synthesis of TrHA 2 in six steps in 48% overall yield. We also present the synthesis of Δ²-THA 4, an intermediate of β-oxidation of THA 3 to DHA 1, in three steps in 73% overall yield.     

Alteration of Serum Phospholipid n-6 Polyunsaturated Fatty Acid Compositions in Nonalcoholic Fatty Liver Disease in the Japanese Population: A Cross-Sectional Study

We performed a cross-sectional study on 215 Japanese employees aged 20–68 years to investigate the association between NAFLD and serum phospholipid fatty acid composition. NAFLD was diagnosed by ultrasonography. The fatty acid composition between the control and NAFLD groups was compared, and the inverse probability of treatment weighting (IPTW) was performed to eliminate each confounding effect of sex, smoking status, BMI, insulin resistance, dietary cholesterol, and salt intake. A receiver operating characteristic (ROC) curve analysis was performed to evaluate the NAFLD prediction accuracy of fatty acids. Seventy-one subjects were diagnosed with NAFLD. Their serum phospholipid dihomo-γ-linolenic acid (DGLA) level was significantly higher after adjusting for each variable using IPTW. In the ROC analysis, the ratio of ARA to DGLA had an area under the curve (AUC) of 0.763. By combining the ratio of ARA to DGLA with the ratio of AST to ALT, AUC increased to 0.871. In conclusion, NAFLD subjects in a Japanese working population have higher serum phospholipid DGLA. Results of the IPTW and ROC analysis indicated that serum PL DGLA and the ratio of ARA to DGLA provide diagnosis information on the fatty liver that is different to AST and ALT and improve the accuracy of fatty liver prediction, owning potential value as serum biomarkers.     

Dietary Fish Oil Supplements Increase Tissue n-3 Fatty Acid Composition and Expression of Delta-6 Desaturase and Elongase-2 in Jade Tiger Hybrid Abalone

This study was conducted to investigate the effects of fish oil (FO) supplements on fatty acid composition and the expression of ∆6 desaturase and elongase 2 genes in Jade Tiger abalone. Five test diets were formulated to contain 0.5, 1.0, 1.5, 2.0 and 2.5% of FO respectively, and the control diet was the normal commercial abalone diet with no additional FO supplement. The muscle, gonad and digestive glands (DG) of abalone fed with all of the five test diets showed significantly high levels of total n-3 polyunsaturated fatty acid (PUFA), eicosapentaenoic acid (EPA), docosapentaenoic acid n-3 (DPAn-3), and docosahexaenoic acid (DHA) than the control group. In all three types of tissue, abalone fed diet supplemented with 1.5% FO showed the highest level of these fatty acids (P < 0.05). For DPAn-3 the higher level was also found in muscle and gonad of abalone fed diet supplemented with 2% FO (P < 0.05). Elongase 2 expression was markedly higher in the muscle of abalone fed diet supplemented with 1.5% FO (P < 0.05), followed by the diet containing 2% FO supplement. For ∆6 desaturase, significantly higher expression was observed in muscle of abalone fed with diet containing 0.5% FO supplement (P < 0.05). Supplementation with FO in the normal commercial diet can significantly improve long chain n-3 PUFA level in cultured abalone, with 1.5% being the most effective supplementation level.     

Fatty Acids of Abyssal Echinodermata,the Sea Star Eremicaster vicinus and the Sea Urchin Kamptosoma abyssale: A New Polyunsaturated Fatty Acid Detected, 22:6(n-2)

Fatty acids (FA) of two species of abyssal Echinodermata—the sea star (Asteroidea) Eremicaster vicinus and the sea urchin (Echinoidea) Kamptosoma abyssale—from the Kuril–Kamchatka Trench, collected at depths of 5210 and 6183 m, were analyzed. Lipids of these deposit-feeding animals showed similar FA compositions: 20.05–16.08% saturated, 42.20–39.50% monoenoic, and 37.75–44.42% polyunsaturated FA, respectively. The contents of odd- and branched-chain FA were 17.35% and 8.80%, respectively. A significant part of FA was represented by uncommon FA such as 21:4(n-7), 22:4(n-8), 22:5(n-5), and 23:4(n-9), earlier discovered in deep-sea foraminifera. Also, the newly found acid, related to the ω2 family, Δ5,8,11,14,17,20–22:6(n-2), amounted 1.60% and 0.33% of total FA, respectively, for the two species. Such unusual FA composition of these abyssal species can be explained by the transfer and modification of FA from consumed foraminifera, which in turn, feed on bacteria.     

Plasma Levels of 14:0, 16:0, 16:1n-7, and 20:3n-6 are Positively Associated,but 18:0 and 18:2n-6 are Inversely Associated with Markers of Inflammation in Young Healthy Adults

Inflammation is a recognized risk factor for the development of chronic diseases, such as type 2 diabetes and atherosclerosis. Evidence suggests that individual fatty acids (FA) may have distinct influences on inflammatory processes. The goal of this study was to conduct a cross-sectional analysis to examine the associations between circulating FA and markers of inflammation in a population of young healthy Canadian adults. FA, high-sensitivity C-reactive protein (hsCRP), and cytokines were measured in fasted plasma samples from 965 young adults (22.6 ± 0.1 years). Gas chromatography was used to measure FA. The following cytokines were analyzed with a multiplex assay: regulated upon activation normal T cell expressed and secreted (RANTES/CCL5), interleukin 1-receptor antagonist (IL-1Ra), interferon-γ (IFN-γ), interferon-γ inducible protein 10 (IP-10), and platelet-derived growth factor β (PDGF-ββ). Numerous statistically significant associations (p < 0.05, corrected for multiple testing) were identified between individual FA and markers of inflammation using linear regression. Myristic (14:0), palmitic (16:0), palmitoleic (16:1n-7), and dihomo-γ-linolenic (20:3n-6) acids were positively associated with all markers of inflammation. In contrast, stearic acid (18:0) was inversely associated with hsCRP and RANTES, and linoleic acid (18:2n-6) was inversely associated with hsCRP, RANTES and PDGF-ββ. In conclusion, our results indicate that specific FA are distinctly correlated with various markers of inflammation. Moreover, the findings of this study suggest that FA profiles in young adults may serve as an early indicator for the development of future complications comprising an inflammatory component.     

The Determination of n-3 Fatty Acid Levels in Food Products Containing Microencapsulated Fish Oil Using the One-Step Extraction Method. Part 1: Measurement in the Raw Ingredient and in Dry Powdered Foods

An optimized one-step extraction and methylation method (OSE) for the determination of n-3 fatty acid levels in microencapsulated fish oil products has been described. Validation of the method for the food ingredient powder MEG-3^® (a commercial microencapsulated fish oil product manufactured by Ocean Nutrition Canada Ltd, with a gelatin shell matrix) has been demonstrated and compared to a method that combines enzymatic digestion of the shell material, gravimetric determination of released oil payload and an official method of fish oil analysis. Excellent agreement between the two methods was also achieved using a microencapsulated standard of pure ethyl palmitate. The OSE method was applied to an infant formula containing microencapsulated fish oil powder and is shown to be a valid method for such dry powdered foods.     

A Unique Amino Transfer Mechanism for Constructing the β‐Amino Fatty Acid Starter Unit in the Biosynthesis of the Macrolactam Antibiotic Cremimycin

Cremimycin is a 19‐membered macrolactam glycoside antibiotic based on three distinctive substructures: 1) a β‐amino fatty acid starter moiety, 2) a bicyclic macrolactam ring, and 3) a cymarose unit. To elucidate the biosynthetic machineries responsible for these three structures, the cremimycin biosynthetic gene cluster was identified. The cmi gene cluster consists of 33 open reading frames encoding eight polyketide synthases, six deoxysugar biosynthetic enzymes, and a characteristic group of five β‐amino‐acid‐transfer enzymes. Involvement of the gene cluster in cremimycin production was confirmed by a gene knockout experiment. Further, a feeding experiment demonstrated that 3‐aminononanoate is a direct precursor of cremimycin. Two characteristic enzymes of the cremimycin‐type biosynthesis were functionally characterized in vitro. The results showed that a putative thioesterase homologue, CmiS1, catalyzes the Michael addition of glycine to the β‐position of a non‐2‐enoic acid thioester, followed by hydrolysis of the thioester to give N‐carboxymethyl‐3‐aminononanoate. Subsequently, the resultant amino acid was oxidized by a putative FAD‐dependent glycine oxidase homologue, CmiS2, to produce 3‐aminononanoate and glyoxylate. This represents a unique amino transfer mechanism for β‐amino acid biosynthesis.     

Diets with Higher ω-6/ω-3 Ratios Show Differences in Ceramides and Fatty Acid Levels Accompanied by Increased Amyloid-Beta in the Brains of Male APP/PS1 Transgenic Mice

Senile plaque formation as a consequence of amyloid-β peptide (Aβ) aggregation constitutes one of the main hallmarks of Alzheimer’s disease (AD). This pathology is characterized by synaptic alterations and cognitive impairment. In order to either prevent or revert it, different therapeutic approaches have been proposed, and some of them are focused on diet modification. Modification of the ω-6/ω-3 fatty acids (FA) ratio in diets has been proven to affect Aβ production and senile plaque formation in the hippocampus and cortex of female transgenic (TG) mice. In these diets, linoleic acid is the main contribution of ω-6 FA, whereas alpha-linoleic acid (ALA), eicosapentaenoic acid (EPA), docosahexaenoic acid (DHA) and docosapentaenoic acid (DPA) are the contributors of ω-3 FA. In the present work, we have explored the effect of ω-6/ω-3 ratio modifications in the diets of male double-transgenic APPswe/PS1ΔE9 (AD model) and wild-type mice (WT). Amyloid burden in the hippocampus increased in parallel with the increase in dietary ω-6/ω-3 ratio in TG male mice. In addition, there was a modification in the brain lipid profile proportional to the ω-6/ω-3 ratio of the diet. In particular, the higher the ω-6/ω-3 ratio, the lower the ceramides and higher the FAs, particularly docosatetraenoic acid. Modifications to the cortex lipid profile was mostly similar between TG and WT mice, except for gangliosides (higher levels in TG mice) and some ceramide species (lower levels in TG mice).     

草酸沉淀法制备纳米晶Y2O3:Eu3+及粉体评价

报道了草酸作为沉淀剂并添加表面活性剂合成了纳米晶Y2O3Eu3+的方法,其一次粒径为20～30 nm,团聚尺寸D50=0.53μm.粉体细且分布均匀.与微米晶比较,该纳米晶的发射光谱发生明显蓝移,色座标符合荧光粉要求.     

Heavy metals in cement phases: on the solubility of Mg, Cd, Pb and Ba in Ca3Al2O6

The compounds formed when the divalent cations Mg²⁺, Cd²⁺, Ba²⁺ and Pb²⁺ are present during the preparation of Ca₃Al₂O₆ have been studied using X-ray microanalysis and diffraction methods. The smaller Mg cations are found to partially substitute for Ca²⁺, and structural refinements show that Mg preferentially occupies the smaller six-coordinate sites in Ca_3−xMg_xAl₂O₆. When Ba is present, it preferentially occupies the larger eight- and nine-coordinate sites. X-ray microanalysis suggests that Pb and Cd are lost from the samples during the preparation process. The diffraction patterns show a small decrease in the lattice parameters, suggesting that a defect structure of the type Ca_3−x(vac)_xAl₂O₆ is formed. The distribution of products formed on hydration of the doped Ca_3−xM_xAl₂O₆ is found to be very different than that observed for the undoped material.