Mono Fatty Acids Research Articles

3배체 참전복, Haliotis discus hannai의 식품 성분에 대한 연구

This study analyzed the proximate compositions, total amino acids, and fatty acid compositions in muscle and viscera of 51-month-old triploid and diploid Pacific abalone, Haliotis discus hannai. Proximate composition analysis showed that the muscle of diploid abalones had a higher protein and ash ratio than that of triploid abalones, while there was no significant difference in the ratios of moisture and fat (P>0.05). The triploid abalones had a significantly higher ratio of carbohydrate in muscle than the diploid abalones (P<0.05), which suggests that the transference of carbohydrates from muscle to gonad is decreased in sterile triploid organisms. Amino-acid analysis indicated that the total content was 133.42 mg/g in diploid muscle and 151.46 mg/g in triploid muscle. Taurine, arginine, glutamine, glycine, glutamic acid, alanine, and leucine, which are the major amino acids in abalone, were measured as 84.64 mg/g in triploid muscle and as 73.92 mg/g in diploid muscle. The essential amino acid content of triploid muscle (38.83 mg/g) was significantly higher than that of diploid muscle (31.94 mg/g) (P<0.05). Saturated fatty acids and monoene fatty acids were abundant in triploid muscle and polyene fatty acids were abundant in diploid muscle. Therefore, triploid Pacific abalone appears to be a good nutritional food source.

Preparation of pure vaterite by simple mechanical mixing of two aqueous salt solutions

Vaterite-type calcium carbonate particles have some unique properties such as high hydrophilicity, large surface areas, and hierarchical structures consisting of primary vaterite particles in comparison with calcite- or aragonite-type polymorphs. In this paper, preparation conditions of vaterite by mixing treatment of two salt solutions, CaCl 2 and K 2CO 3, were studied in terms of the presence of surfactant, agitation method of the solutions and other conditions. A double-cylinder-type homogenizer or ultrasonic homogenizer was used for agitation of the solutions. When suitable mixing conditions were adopted, pure vaterite was obtained as fine powders quantitatively by mixing the two salt solutions at room temperature without any surfactant using any types of homogenizers. When a polyoxyethylene sorbitan monofatty acid ester was present as a surfactant in the mixing solutions, pure vaterite but different morphologies or particle sizes were obtained, depending on the chemical structure of the surfactant used. The obtained results revealed that homogeneous, high-shear and constant agitation of the mixing solutions around 1 M salt concentration was necessary to prepare pure vaterite under the conditions used in this study.

Time‐ and media‐dependent secondary carotenoid accumulation in Haematococcus pluvialis

The green microalgae Haematococcus pluvialis synthesizes secondary carotenoids after exposure to environmental stress, a process that is used for the biotechnological production of astaxanthin (Ax). This study reports, for the first time, the medium-dependent changes in the carotenoid pattern throughout the cultivation process as well as the exact composition of carotenoids and their fatty acid mono- and diesters using LC-MS. Secondary carotenoid formation started immediately upon exposure to nutrient depletion and high light conditions. Ax and its corresponding mono- and diesters were detected simultaneously. After 15 days of cultivation, no significant changes were detected in carotenoid composition; however, the ratio between carotenoid mono- and diesters still varied. Main carotenoids were identified as Ax linolenate and Ax oleate, but also five adonirubin and one lutein monoester were detected. The influence of three different autotroph media was studied on carotenoid content, which reached a maximum 16.1 mg/g dry weight. The results indicate that media composition has an influence on the ratio of Ax mono- to diester but not on the qualitative composition of secondary carotenoids in H. pluvialis. Beside the pathway via echinenone, canthaxanthin and adonirubin the results indicate that Ax biosynthesis takes place via another route: from beta-carotene via beta-cryptoxanthin, zeaxanthin and adonixanthin.

The ultrasound-assisted oxidative scission of monoenic fatty acids by ruthenium tetroxide catalysis: Influence of the mixture of solvents

Carboxylic acids and diacids were synthesized from monoenic fatty acids by using RuO 4 catalysis, under ultrasonic irradiation, in various mixtures of solvents. Ultrasound associated with Aliquat ® 336 have promoted in water, the quantitative oxidative cleavage of the CH CH bond of oleic acid. A design of experiment (DOE) shows that the optimal mixture of solvents (H 2O/MeCN, ratio 1/1, 2.2% RuCl 3/4.1 eq. NaIO 4) gives 81% azelaic acid and 97% pelargonic acid. With the binary heterogeneous mixture H 2O/AcOEt, the oxidation of the oleic acid leads to a third product, the α-dione 9,10-dioxostearic acid.

Higher Content of C18:1 Trans Fatty Acids in Early Human Milk Fat of Roma Breast-Feeding Women

Aim: The purpose of our study was to determine the content of trans fatty acids in early human breast milk as an indicator of dietary exposure in a sample of Roma breast-feeding women and in a sample of women from the general Czech population. Methods: We collected samples of early human milk from 43 Prague women from the general population and 21 Roma women. After lipid extraction, the fatty acids were converted into methyl esters (FAMEs). Finally, gas chromatography with flame ionization detector (GC-FID) analysis on a CP-Sil 88 column was used to determine C18:1 trans monoenic fatty acid levels and total trans isomers fatty acid levels in human milk. Results: A significantly higher content of C18:1 trans fatty acid isomers was detected in human milk fat from Roma mothers than in women of the general population (2.73 vs. 2.09%, p < 0.05). Both groups monitored did not differ in the representation of total fatty acid trans isomers. Differences in the frequency of consumption of certain TFA sources (butter, fried crisps) were established. Conclusions: The study proved a higher fatty acid trans isomers content in Roma breast-feeding mothers in the Czech Republic, and this is probably related to their bad eating habits.

Partial hydrogenation of sunflower oil in a membrane reactor

Partial hydrogenation of sunflower oil was carried out in a membrane reactor in pore-flow-through mode in n-heptane as solvent. The membrane reactor consisted of a porous α-Al 2O 3 membrane impregnated with Pd or Pt as the active catalyst and was constructed as a loop of saturation vessel and membrane module. Hydrogenation experiments were performed at different temperatures, hydrogen pressures and noble metals as catalysts. The experiments in the membrane reactor were compared with experiments in a slurry reactor with a powder catalyst for benchmarking. The stearic acid content at an iodine value (IV) of about 80 was 10–15% in the membrane reactor and 45% in the slurry reactor, respectively. The selectivity for the monoene fatty acids could be improved with decreasing hydrogen pressures. The content of trans fatty acids at IV ≈ 80 was 30–45% in the membrane reactor, whereas in the slurry reactor 12% were obtained. For the trans-isomer formation, the influence of hydrogen pressure and temperature in the membrane reactor was rather low. Pd showed a higher activity and selectivity compared to Pt, but promoted the trans-isomerization to a greater extent.

Oil‐Induced Structural Change of Wormlike Micelles in Sugar Surfactant Systems

Sucrose monofatty acid esters form spherical or short‐rod micelles in water. By combining the sugar surfactant with lipophilic monoglyceride or short‐EO‐chain, poly (oxyethylene) alkyl ether (CmEOn) one‐dimensional growth of micelles takes place, and the viscosity of the aqueous mixed nonionic surfactant solution dramatically increases due to the entanglement of elongated wormlike micelles. Upon addition of oil (decane or m‐xylene), the viscosity changes in the opposite way. With a slightly polar m‐xylene, the viscosity increases, but the viscosity is sharply decreased upon addition of the saturated hydrocarbon decane. It was confirmed by SAXS results that long wormlike micelles are more extended by m‐xylene because the m‐xylene molecules are solubilized in the surfactant palisade layer, whereas decane is solubilized in the core of micelles and makes an oil pool inside. Consequently, upon addition of decane, wormlike micelles become shortened and change to short fat micelles. The oil‐induced structural change in the micellar shape is highly related to the solubilized site of oil in the aggregates.

Targeted mutagenesis of a fatty acid Δ 6-desaturase from Mucor rouxii: Role of amino acid residues adjacent to histidine-rich motif II

The amino acid residues serine at position 213 (S213) and lysine at position 218 (K218), which are present in close proximity to the histidine-rich motif II of Mucor rouxii fatty acid Δ 6-desaturase isoform II, were targeted for studying structure–function relationships using site-directed mutagenesis. The mutants were functionally characterized in a heterologous host, Saccharomyces cerevisiae. Substrate specificity and preference studies revealed that S213 and K218 are involved in substrate recognition. K218 plays a role in substrate preference by involvement in the binding of substrates, particularly C15–C18 monoene fatty acids. Modification of the M. rouxii Δ 6-desaturase therefore has potential in specifically altering substrate utilization for production of desired fatty acids.

Synthesis and Stability Studies of the Glutathione and N-Acetylcysteine Adducts of an Iminoquinone Reactive Intermediate Generated in the Biotransformation of 3-(N-Phenylamino)propane-1,2-diol: Implications for Toxic Oil Syndrome

Epidemiological studies have pointed to fatty acid mono- and diesters of 3-(N-phenylamino)propane-1,2-diol (PAP) as the biomarkers of the toxic oil batches that caused toxic oil syndrome (TOS), an intoxication episode that occurred in Spain in 1981, causing over 400 deaths and affecting more than 20000 people. The biotransformation of PAP administered intraperitoneally to two mouse strains produced potentially toxic metabolites. The identification of 3-(4'-hydroxyphenylamino)propane-1,2-diol among those metabolites was important because the compound can generate the quinoneimine intermediate 2. The potential toxicity of quinoneimines has been attributed primarily to their electrophilic character. Accordingly, the reactions of 2 with N-acetylcysteine, N-acetylcysteine methyl ester, and GSH were investigated. Quinoneimine 2 reacts with the N-acetylcysteine methyl ester to give the expected conjugate as a major product, accompanied by the corresponding bis and tris adducts. The monoadduct, when isolated in pure form, undergoes spontaneous oxidation to generate a new quinoneimine intermediate, which in turn rearranges and undergoes hydrolysis to afford the thiol adduct formally derived from the quinoneimine generated from p-aminophenol. The same overall pathway was observed for the reaction of 2 with N-acetylcysteine and GSH. Both thiol reagents reacted with the quinoneimine to give the corresponding adducts in which the addition took place at the ortho position with respect to the amino group. These conjugates were also unstable and ultimately afforded the corresponding adduct derived from p-aminophenol. The relevancy of these results to TOS, as well as their potential generalization for quinoneimines derived from other xenobiotics, is discussed herein.

Ruthenium‐Catalyzed Oxidation Without CCl4 of Oleic Acid, Other Monoenic Fatty Acids and Alkenes.

AbstractFor Abstract see ChemInform Abstract in Full Text.

Kinetics of Fatty Acid Oxidation in Low Density Lipoproteins Evaluated by Registration of the Oxidizer Consumption and Reaction Product Yield

Oxidation of arachidonic acid by ROS in vitro can be evaluated by the formation of reaction products (conjugated dienes); this is preceded by a lag period caused by the action of antioxidants (alpha-tocopherol, beta-carotene, and ascorbic acid). In case of ozone titration the oxidizer is consumed even during the lag period, when conjugated dienes are not yet forming. Comparison of the oxidation rate constants for antioxidants, arachidonic and oleic monoenic fatty acids suggests that during the lag period Cu(2+)-initiated forms of O(2) oxidize primarily oleic acid, whose reaction rate constant is much higher than those of antioxidants. Presumably, the duration of lag period during oxidation of arachidonic acid and formation of conjugated dienes is determined also by the content of triglycerides and oleic fatty acid in low density lipoproteins.

Environmentally friendly properties of vegetable oil methyl esters

Measurements were carried out on Vegetable Oil Methyl Esters (VOME or FAME) answering the most recent specifications. The products tested are RME (Rapeseed oil Methyl Ester), ERME (Erucic Rapeseed oil Methyl Esters), SME (Sunflower oil Methyl Esters), and HOSME (High Oleic Sunflower oil Methyl Esters). They contain more than 99.5% of fatty acid mono esters. The compositions are given. VOME are not volatile and they are not easily flammable. They are not soluble in water and they are biodegradable. According to the methods implemented for the determination of the German classification of substances hazardous to waters WGK, they are not toxic on mammals and unlike diesel fuel they are not toxic on fish, daphnia, algae and bacteria. The RME is not either toxic for shrimps. According to tests on rabbits, RME and SME are not irritating for the skin and the eyes. VOME display particularly attractive environmental properties.

Ruthenium catalysed oxidation without CCl 4 of oleic acid, other monoenic fatty acids and alkenes

Ruthenium catalysed oxidation of alkenes and monoenic fatty acids is reported. The study of the influence of cosolvents (H 2O/MeCN/X) shows that toxic CCl 4 initially used in the Sharpless system (H 2O/MeCN/CCl 4) can be avoided and demonstrates that the oxidative cleavage of C C bond could be accomplished in good yields with H 2O/MeCN/AcOEt solvent system in a ratio 3/2/2, respectively.

Effect of mono and polyunsaturated fatty acids on muscle cholesterol level in fattening pigs

The effect of supplementing fattening pigs with oils differing in MUFA (monounusaturated fatty acids) and PUFA (polyunsaturated fatty acids) level addition for fatteners diets on the cholesterol content of m. longissimus was investigated. In a feeding trial with 48 crossbred pigs [? ($ White Polish Large x S Polish Landrace) x &lt;$ Pietrain] randomly assigned to four treatments groups of 12 animals each (6 gilts and 6 barrows), dietary supplements of 3% maize, sunflower or linseed oil in the experimental groups and of 3% lard in the control group were applied. Total cholesterol in the longissimus muscle of linseed oil supplemented pigs was found to decrease significantly (PO.01) compared to the lard-fed pigs (60.75 vs. 71.37 mg/100 g of fresh tissue). Similar tendencies for reduced cholesterol level in longissimus muscle of sunflower and maize oil supplemented pigs were also noted. The production of pork with reduced total cholesterol seems to be important in terms of consumer health and culinary value.

Application of Polyglycerol Mono-Fatty Acid Esters to Improve Breadmaking

The effects of polyglycerol mono-fatty acid esters (PGMFEs) on dough properties and baking were investigated using six PGMFEs with saturated fatty acid moieties (octanoic, decanoic, lauric, myristic, palmitic, and stearic acids). The addition of the PGMFEs (0.5% w/w of flour) to dough significantly increased its resistance, retention of the generated gas, and the volume of bread compared to loaves baked with the addition of monoglycerides and the control. These effects increased with a decrease in the chain length of the fatty acid moiety of the PGMFEs. Microscopic observation of the fermented dough with the PGMFEs showed that the gluten matrix became thick and that most of the starch granules were sufficiently covered with the gluten matrix as compared with the control. Also, addition of the PGMFEs with palmitic or stearic acid moieties retarded firmness in bread like that of bread baked with monoglycerides. These results indicated that the addition of PGMFEs as dough-conditioners promoted gluten formation and retarded the firming of bread by acting as a softener.

Studies on Toxic Oil Syndrome: Stereoselective Hydrolysis of 3-(Phenylamino)propane-1,2-diol Esters by Human Pancreatic Lipase

The ingestion of rapeseed oil batches denatured with aniline and illegally refined and distributed by street vendors was responsible for toxic oil syndrome (TOS), an intoxication episode that took place in Spain in 1981, causing over 400 deaths and affecting more than 20,000 people. Despite the intense research efforts carried out to date, the compounds responsible for that intoxication have not been elucidated. Nevertheless, epidemiological studies have pointed to fatty acid mono- and diesters of 3-phenylamino-1,2-propanediol (PAP) as the biomarkers of those toxic oil batches. The structure of these esters bears common features with that of triglycerides, which suggested that PAP esters could follow the route of lipids metabolism up to a certain extent. The incubation of racemic PAP dioleyl ester with human pancreatic lipase (hPL) led to the formation of the corresponding stereoisomeric monoesters bearing the oleyl residue at C-2, although a kinetic resolution in favor of the (S)-enantiomer was observed. These monoesters are unstable and in equilibrium with their corresponding regioisomers with the acyl residue at C-1, apparently without the intervention of the lipase. Finally, incubations of these latter monoesters with hPL led to the formation of the respective PAP enantiomers. Again, the kinetic resolution of this hydrolytic process favored the formation of the enantiomer with the (S)-configuration. Taken together, these results showed that PAP esters are substrates of hPL and that the two hydrolytic steps exhibit kinetic resolution in favor of the (S)-enantiomers.

Replacing dietary fish oil with increasing levels of rapeseed oil and olive oil - effects on Atlantic salmon (Salmo salar L.) tissue and lipoprotein lipid composition and lipogenic enzyme activities

Six groups of Atlantic salmon, initial weight 142 ± 1 g, were fed increasing dietary inclusion of rapeseed oil (RO) in a regression design and one group was fed a 50% olive oil/50% capelin oil diet. Fatty acid composition was measured in red and white muscle, liver, and fatty acid and lipid class composition was measured in plasma and in the lipoproteins; very low density lipoprotein, low density lipoprotein, high density lipoprotein and nonlipoprotein fraction after 22 and 42 weeks of feeding. Further, the activities of liver NADH-isocitrate dehydrogenase (ICDH), malic enzyme, glucose-6-phosphate dehydrogenase (G6PDH) and 6-phosphogluconate dehydrogenase were measured at each sampling point. After 42 weeks of feeding the experimental diets, the tissue and lipoprotein fatty acid composition was highly affected by dietary fatty acid composition. Regressions showed that 22:1n − 11, 18:1n − 9, 18:3n − 3 and 18:2n − 6 are readily metabolized in all tissues analysed. Further, 20:5n − 3 seems to be metabolized in muscle and retained in liver. 22:6n − 3 was selectively retained in all the analysed tissues, and with higher retention in liver and plasma with higher polar lipid/neutral lipid ratio compared to white and red muscle. Liver from salmon fed 100% RO showed decreased G6PDH and increased ICDH activities compared to the other dietary groups; however, no linear relationship related to increased RO inclusion was detected. The amount of plasma lipoproteins, liver monoene fatty acid level and lipogenic enzyme activity decreased from the autumn to the winter sampling with concomitant decrease in temperature.

Use of White Fat as a Replacement for Squid Liver Oil in Practical Diets for Surubim Pseudoplatystoma coruscans

AbstractThe effect of dietary lipid on culture performance, fatty acid composition of carcass, and the liver polar lipid of surubim fingerlings Pseudoplatystoma coruscans was investigated. Five isonitrogenous (46.5% crude protein) and isolipidic (19% crude lipid) diets were formulated with squid liver oil (SLO) and white fat (pig lard‐PL) as lipid sources. Diet 1 was supplemented with 12% SLO, diet 2 with 8% SLO and 4% PL, diet 3 with 6% SLO and 6% PL, diet 4 with 4% SLO and 8% PL, and diet 5 with 12% PL. Fish were fed to apparent satiation over a 64‐d feeding trial. No statistically significant difference (P &gt;0.05) was observed in growth performance of fish. In contrast, fatty acid profile of fish carcass and liver polar lipid fraction was affected (P 0.05) by dietary fatty acid composition. Palmitic (16:O) and the oleic (18:1n‐9) acids were the major saturated and monoene fatty acids respectively found in fish carcass, independent of the lipid source in the diets. The total amount of saturated and monoene fatty acids was significantly higher (P 0.05) in the carcass of the fish fed diets 4 and 5, than in the other fish. The concentration (P 0.05) of eicosapentaenoic and docosahexaenoic acids and the n‐3/n‐6 ratio in fish carcass and in polar lipid fraction of liver increased in direct proportion to the level of squid liver oil in diet. Results of this experiment clearly demonstrated that both squid liver oil and pig lard have a positive nutritive value for surubim and that it is possible to increase the n‐3 to n‐6 ratio in favor of n‐3, without loss in the growth performance, feeding fish with a diet containing a lipid source rich in this fatty acid.

The Reduction of Oxidation of Food Products Using Dioxygenases

A novel way of deoxygenating food products by oxygen scavenging enzymes has been developed, especially suitable for food products comprising mono or polyunsaturated fatty acids or both which are very sensitive to oxidation. It has been found that dioxygenases, which are enzymes capable of oxidising substrates by inserting one or two oxygen atoms into the substrate using molecular oxygen, are very effective in oxygen removal in food products. Moreover, no reactive species are formed during this reaction. Furthermore, the substrates for dioxygenases are antioxidants, which have the advantage that a combination-effect can be achieved, particularly because the substrate retains its antioxidant activity after being oxidised. The use of quercetinase and catechinase, both dioxygenases, as oxygen-scavenging enzymes for off-flavour prevention in oil-in-water (o/w) emulsions was found to be highly efficient, and the oxygen concentration could be reduced to zero. The enzymes quercetinase and catechinase were able to...

What limits production of unusual monoenoic fatty acids in transgenic plants?

Unusual monounsaturated fatty acids are major constituents (greater than 80%) in seeds of Coriandrum sativum L. (coriander) and Thunbergia alata Bojer, as well as in glandular trichomes (greater than 80% derived products) of Pelargonium x hortorum (geranium). These diverged fatty acid structures are produced via distinct plastidial acyl-acyl carrier protein (ACP) desaturases. When expressed in Arabidopsis thaliana (L.) Heynh. under strong seed-specific promoters the unusual acyl-ACP desaturases resulted in accumulation of unusual monoene fatty acids at 1-15% of seed fatty acid mass. In this study, we have examined several factors that potentially limit higher production of unusual monoenes in transgenic oilseeds. (i) Immunoblots indicated that the introduced desaturases were expressed at levels equivalent to or higher than the endogenous delta9 18:0-ACP desaturase. However, the level of unusual fatty acid produced in transgenic plants was not correlated with the level of desaturase expression. (ii) The unusual desaturases were expressed in several backgrounds, including antisense 18:0-ACP desaturase plants, in fab1 mutants, and co-expressed with specialized ACP or ferredoxin isoforms. None of these experiments led to high production of expected products. (iii) No evidence was found for degradation of the unusual fatty acids during seed development. (iv) Petroselinic acid added to developing seeds was incorporated into triacylglycerol as readily as oleic acid, suggesting no major barriers to its metabolism by enzymes of glycerolipid assembly. (v) In vitro and in situ assay of acyl-ACP desaturases revealed a large discrepancy of activity when comparing unusual acyl-ACP desaturases with the endogenous delta9 18:0-ACP desaturase. The combined results, coupled with the sensitivity of acyl-ACP desaturase activity to centrifugation and low salt or detergent suggests low production of unusual monoenes in transgenic plants may be due to the lack of, or incorrect assemble of, a necessary multi-component enzyme association.