scholarly journals Isolation of a new phospholipid, phosphatidyl-N-(2-hydroxyethyl)alanine, from rumen protozoa

1969 ◽  
Vol 113 (3) ◽  
pp. 555-558 ◽  
Author(s):  
P Kemp ◽  
R. M. C. Dawson
Keyword(s):  
Fatty Acids ◽  
Linoleic Acid ◽  
Linolenic Acid ◽  
Octadecenoic Acid ◽  
Rumen Protozoa

1. Phosphatidyl-N-(2-hydroxyethyl)alanine was isolated from the mixed protozoal fraction of rumen and characterized. 2. Of the fatty acids 31% was octadecenoic acid, 91% of which was the trans-Δ11-isomer, an intermediary in the ruminal hydrogenation of linolenic acid and linoleic acid.

scholarly journals Production of Novel Tetrahydroxyfuranyl Fatty Acids from α-Linolenic Acid by Clavibacter sp. Strain ALA2

2003 ◽  
Vol 69 (7) ◽  
pp. 3868-3873 ◽  
Author(s):  
Masashi Hosokawa ◽  
Ching T. Hou ◽  
David Weisleder
Keyword(s):  
Fatty Acids ◽  
Linoleic Acid ◽  
Linolenic Acid ◽  
Unsaturated Fatty Acids ◽  
Incubation Temperature ◽  
Total Yield ◽  
Octadecenoic Acid ◽  
Gas Chromatography Mass Spectrometry ◽  
Microbial Culture ◽  
Chemical Structures

ABSTRACT Previously, it was reported that a newly isolated microbial culture, Clavibacter sp. strain ALA2, produced trihydroxy unsaturated fatty acids, diepxoy bicyclic fatty acids, and tetrahydroxyfuranyl fatty acids (THFAs) from linoleic acid (C. T. Hou, J. Am. Oil Chem. Soc. 73:1359-1362, 1996; C. T. Hou and R. J. Forman III, J. Ind. Microbiol. Biotechnol. 24:275-276, 2000; C. T. Hou, H. Gardner, and W. Brown, J. Am. Oil Chem. Soc. 75:1483-1487, 1998; C. T. Hou, H. W. Gardner, and W. Brown, J. Am. Oil Chem. Soc. 78:1167-1169, 2001). In this study, we found that Clavibacter sp. strain ALA2 produced novel THFAs, including 13,16-dihydroxy-12-THFA, 15-epoxy-9(Z)-octadecenoic acid (13,16-dihydroxy-THFA), and 7,13,16-trihydroxy-12, 15-epoxy-9(Z)-octadecenoic acid (7,13,16-trihydroxy-THFA), from α-linolenic acid (9,12,15-octadecatrienoic acid). The chemical structures of these products were determined by gas chromatography-mass spectrometry and proton and 13C nuclear magnetic resonance analyses. The optimum incubation temperature was 30°C for production of both hydroxy-THFAs. 13,16-Dihydroxy-THFA was detected after 2 days of incubation, and the concentration reached 45 mg/50 ml after 7 days of incubation; 7,13,16-trihydroxy-THFA was not detected after 2 days of incubation, but the concentration reached 9 mg/50 ml after 7 days of incubation. The total yield of both 13,16-dihydroxy-THFA and 7,13,16-trihydroxy-THFA was 67% (wt/wt) after 7 days of incubation at 30°C and 200 rpm. In previous studies, it was reported that Clavibacter sp. strain ALA2 oxidized the C-7, C-12, C-13, C-16, and C-17 positions of linoleic acid (n-6) into hydroxy groups. In this case, the bond between the C-16 and C-17 carbon atoms is saturated. In α-linolenic acid (n-3), however, the bond between the C-16 and C-17 carbon atoms is unsaturated. It seems that enzymes of strain ALA2 oxidized the C-12-C-13 and C-16-C-17 double bonds into dihydroxy groups first and then converted them to hydroxy-THFAs.

scholarly journals Explore the gene network regulating the composition of fatty acids in cottonseed

2021 ◽  
Vol 21 (1) ◽  
Author(s):  
Lihong Ma ◽  
Xinqi Cheng ◽  
Chuan Wang ◽  
Xinyu Zhang ◽  
Fei Xue ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Linoleic Acid ◽  
Linolenic Acid ◽  
Gene Network ◽  
Unsaturated Fatty Acids ◽  
Saturated Fatty Acids ◽  
Accumulation Pattern ◽  
Time Points ◽  
Expression Characteristics

Abstract Background Cottonseed is one of the major sources of vegetable oil. Analysis of the dynamic changes of fatty acid components and the genes regulating the composition of fatty acids of cottonseed oil is of great significance for understanding the biological processes underlying biosynthesis of fatty acids and for genetic improving the oil nutritional qualities. Results In this study, we investigated the dynamic relationship of 13 fatty acid components at 12 developmental time points of cottonseed (Gossypium hirsutum L.) and generated cottonseed transcriptome of the 12 time points. At 5–15 day post anthesis (DPA), the contents of polyunsaturated linolenic acid (C18:3n-3) and saturated stearic acid (C18:0) were higher, while linoleic acid (C18:2n-6) was mainly synthesized after 15 DPA. Using 5 DPA as a reference, 15,647 non-redundant differentially expressed genes were identified in 10–60 DPA cottonseed. Co-expression gene network analysis identified six modules containing 3275 genes significantly associated with middle-late seed developmental stages and enriched with genes related to the linoleic acid metabolic pathway and α-linolenic acid metabolism. Genes (Gh_D03G0588 and Gh_A02G1788) encoding stearoyl-ACP desaturase were identified as hub genes and significantly up-regulated at 25 DPA. They seemed to play a decisive role in determining the ratio of saturated fatty acids to unsaturated fatty acids. FAD2 genes (Gh_A13G1850 and Gh_D13G2238) were highly expressed at 25–50 DPA, eventually leading to the high content of C18:2n-6 in cottonseed. The content of C18:3n-3 was significantly decreased from 5 DPA (7.44%) to 25 DPA (0.11%) and correlated with the expression characteristics of Gh_A09G0848 and Gh_D09G0870. Conclusions These results contribute to our understanding on the relationship between the accumulation pattern of fatty acid components and the expression characteristics of key genes involved in fatty acid biosynthesis during the entire period of cottonseed development.

Saccharomyces kluyveri FAD3 encodes an ω3 fatty acid desaturase

Microbiology ◽  
2004 ◽  
Vol 150 (6) ◽  
pp. 1983-1990 ◽  
Author(s):  
Takahiro Oura ◽  
Susumu Kajiwara
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Linoleic Acid ◽  
Linolenic Acid ◽  
Functional Characterization ◽  
Fatty Acid Desaturase ◽  
Fatty Acid Desaturases ◽  
Desaturase Gene ◽  
Saccharomyces Kluyveri ◽  
Fatty Acid Desaturase Gene

Fungi, like plants, are capable of producing the 18-carbon polyunsaturated fatty acids linoleic acid and α-linolenic acid. These fatty acids are synthesized by catalytic reactions of Δ12 and ω3 fatty acid desaturases. This paper describes the first cloning and functional characterization of a yeast ω3 fatty acid desaturase gene. The deduced protein encoded by the Saccharomyces kluyveri FAD3 gene (Sk-FAD3) consists of 419 amino acids, and shows 30–60 % identity with Δ12 fatty acid desaturases of several eukaryotic organisms and 29–31 % identity with ω3 fatty acid desaturases of animals and plants. During Sk-FAD3 expression in Saccharomyces cerevisiae, α-linolenic acid accumulated only when linoleic acid was added to the culture medium. The disruption of Sk-FAD3 led to the disappearance of α-linolenic acid in S. kluyveri. These findings suggest that Sk-FAD3 is the only ω3 fatty acid desaturase gene in this yeast. Furthermore, transcriptional expression of Sk-FAD3 appears to be regulated by low-temperature stress in a manner different from the other fatty acid desaturase genes in S. kluyveri.

FLAVOUR REVERSION IN HYDROGENATED LINSEED OIL: I. THE PRODUCTION OF AN ISOMER OF LINOLEIC ACID FROM LINOLENIC ACID

1944 ◽  
Vol 22f (6) ◽  
pp. 191-198 ◽  
Author(s):  
H. W. Lemon
Keyword(s):  
Fatty Acids ◽  
Linoleic Acid ◽  
High Temperature ◽  
Iodine Number ◽  
Spectral Method ◽  
Linolenic Acid ◽  
Linseed Oil ◽  
Naturally Occurring ◽  
Total Fatty Acids ◽  
Isomeric Acid

Linseed oil that has been hydrogenated to a plastic consistency is subject to a type of deterioration termed "flavour reversion" when heated to temperatures used in baking or frying. Investigation of the course of hydrogenation of linseed oil by the spectral method of Mitchell, Kraybill, and Zscheile (11) has indicated that linolenic acid is converted to an isomeric linoleic acid; this acid differs from naturally occurring linoleic acid in that the double bonds are in such positions that diene conjugation is not produced by high-temperature saponification. In a typical hydrogenation, the concentration of the isomeric acid increased to a maximum, at about iodine number 120, of 18% of the total fatty acids, and at iodine number 80, at which point the plasticity was similar to that of a commercial shortening, the concentration of the isomer was 13%. Evidence is presented that the isomeric linoleic acid in partially hydrogenated linseed oil is responsible for the unpleasant flavour that develops when the oil is heated.

scholarly journals Inhibition of steroid 5α-reductase by specific aliphatic unsaturated fatty acids

1992 ◽  
Vol 285 (2) ◽  
pp. 557-562 ◽  
Author(s):  
T Liang ◽  
S Liao
Keyword(s):  
Fatty Acids ◽  
Oleic Acid ◽  
Linoleic Acid ◽  
Linolenic Acid ◽  
Unsaturated Fatty Acids ◽  
Binding Assay ◽  
Reductase Activity ◽  
Undecylenic Acid ◽  
Gamma Linolenic Acid ◽  
Enzymic Assay

Human or rat microsomal 5 alpha-reductase activity, as measured by enzymic conversion of testosterone into 5 alpha-dihydrotestosterone or by binding of a competitive inhibitor, [3H]17 beta-NN-diethulcarbamoyl-4-methyl-4-aza-5 alpha-androstan-3-one ([3H]4-MA) to the reductase, is inhibited by low concentrations (less than 10 microM) of certain polyunsaturated fatty acids. The relative inhibitory potencies of unsaturated fatty acids are, in decreasing order: gamma-linolenic acid greater than cis-4,7,10,13,16,19-docosahexaenoic acid = cis-6,9,12,15-octatetraenoic acid = arachidonic acid = alpha-linolenic acid greater than linoleic acid greater than palmitoleic acid greater than oleic acid greater than myristoleic acid. Other unsaturated fatty acids such as undecylenic acid, erucic acid and nervonic acid, are inactive. The methyl esters and alcohol analogues of these compounds, glycerols, phospholipids, saturated fatty acids, retinoids and carotenes were inactive even at 0.2 mM. The results of the binding assay and the enzymic assay correlated well except for elaidic acid and linolelaidic acid, the trans isomers of oleic acid and linoleic acid respectively, which were much less active than their cis isomers in the binding assay but were as potent in the enzymic assay. gamma-Linolenic acid had no effect on the activities of two other rat liver microsomal enzymes: NADH:menadione reductase and glucuronosyl transferase. gamma-Linolenic acid, the most potent inhibitor tested, decreased the Vmax. and increased Km values of substrates, NADPH and testosterone, and promoted dissociation of [3H]4-MA from the microsomal reductase. gamma-Linolenic acid, but not the corresponding saturated fatty acid (stearic acid), inhibited the 5 alpha-reductase activity, but not the 17 beta-dehydrogenase activity, of human prostate cancer cells in culture. These results suggest that unsaturated fatty acids may play an important role in regulating androgen action in target cells.

scholarly journals Fatty acid chemistry of Atrichum undulatum and Hypnum andoi

2012 ◽  
Vol 66 (2) ◽  
pp. 207-209 ◽  
Author(s):  
Boris Pejin ◽  
Ljubodrag Vujisic ◽  
Marko Sabovljevic ◽  
Vele Tesevic ◽  
Vlatka Vajs
Keyword(s):  
Fatty Acids ◽  
Gas Chromatography ◽  
Fatty Acid ◽  
Linoleic Acid ◽  
Stearic Acid ◽  
Palmitic Acid ◽  
Linolenic Acid ◽  
Essential Fatty Acids ◽  
Behenic Acid ◽  
Moss Species

The fatty acid composition of the moss species Atrichum undulatum (Hedw.) P. Beauv. (Polytrichaceae) and Hypnum andoi A.J.E. Sm. (Hypnaceae) collected in winter time were analyzed by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS) as a contribution to their chemistry. Eight fatty acids were identified in the chloroform/methanol extract 1:1 of A. undulatum (linoleic acid 26.80%, palmitic acid 22.17%, ?-linolenic acid 20.50%, oleic acid 18.49%, arachidonic acid 6.21%, stearic acid 3.34%, cis-5,8,11,14,17-eicosapentaenoic acid 1.52% and behenic acid 1.01%), while six fatty acids were found in the same type of extract of H. andoi (palmitic acid 63.48%, erucic acid 12.38%, stearic acid 8.08%, behenic acid 6.26%, lignoceric acid 5.16% and arachidic acid 4.64%). According to this study, the moss A. undulatum can be considered as a good source of both essential fatty acids for humans (linoleic acid and ?-linolenic acid) during the winter.

Independent effects of dietary linoleic and linolenic fatty acids on the conjugated linoleic acid content of cows’ milk

2002 ◽  
Vol 74 (1) ◽  
pp. 163-176 ◽  
Author(s):  
A.L. Lock ◽  
P.C. Garnsworthy
Keyword(s):  
Fatty Acids ◽  
Mammary Gland ◽  
Linoleic Acid ◽  
Conjugated Linoleic Acid ◽  
Linolenic Acid ◽  
Milk Fat ◽  
Latin Square ◽  
Health Benefit ◽  
Low Linolenic Acid ◽  
Low Linolenic

AbstractIt may be desirable to increase the level of conjugated linoleic acid (CLA) in milk as a health benefit in human nutrition. The purpose of this work was to separate the effects of linoleic and linolenic acids on CLA production in dairy cows and to determine to what extent endogenous synthesis contributes to cis-9, trans-11 CLA concentration in milk fat. Eight lactating cows and four non-lactating duodenal fistulated cows were used in a 4 ✕ 4 Latin-square design. All cows received a basal diet of grass silage that was supplemented with one of four concentrates, which were designed to differ in their linoleic and linolenic acid contents. The oil components of the concentrates were produced from mixtures of olive, linseed, rape, soya and sunflower oils to produce the four treatments: low linoleic/ low linolenic acid (LL), low linoleic/high linolenic acid (LH), high linoleic/low linolenic acid (HL) and high linoleic/ high linolenic acid (HH). Milk cis-9, trans-11 CLA contents were 0·8, 0·9, 0·9 and 1·1 g/100 g fatty acid methyl esters (P < 0·05) and yields were 5, 7, 7 and 8 g/day (P < 0·05) for the LL, LH, HL and HH treatments, respectively. The yields of trans-C18:1 fatty acids in milk were 19, 22, 21 and 23 g/day (P < 0·05), respectively. Taking the data for the cis-9, trans-11 CLA content and flow of duodenal fluid from the fistulated cows and representing this in terms of dietary intake by the lactating animals, the amounts of cis-9, trans-11 CLA produced in the rumen were calculated to be 0·8, 0·9, 1·2 and 1·1 g/day (P < 0·05) and for trans-C18:1 fatty acids 58, 58, 66 and 69 g/day (P < 0·05). Increasing linoleic and/or linolenic acids in the diet can increase the cis-9, trans-11 CLA content of cows’ milk. Only diets high in linoleic acid increased cis-9, trans-11 CLA production in the rumen. On all four diets, more than 80% of cis-9, trans-11 CLA in milk was produced endogenously by Δ9-desaturase from trans-11 C18:1 in the mammary gland. Cows on the same diet have different milk fat cis-9, trans-11 CLA concentrations that may be partially explained by differences in Δ9-desaturase activity between cows. Increasing the activity of Δ9-desaturase in the mammary gland may offer greater potential for enhancing the cis-9, trans-11 CLA content of milk fat than increasing cis-9, trans-11 CLA production in the rumen.

scholarly journals The Decrease of n-3 Fatty Acid Energy Percentage in an Equicaloric Diet Fed to B6C3Fe Mice for Three Generations Elicits Obesity

2009 ◽  
Vol 2009 ◽  
pp. 1-7 ◽  
Author(s):  
Ingeborg Hanbauer ◽  
Ignacio Rivero-Covelo ◽  
Ekrem Maloku ◽  
Adam Baca ◽  
Qiaoyan Hu ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Linoleic Acid ◽  
Polyunsaturated Fatty Acids ◽  
Linolenic Acid ◽  
Liver Lipid ◽  
Liver Steatosis ◽  
Docosapentaenoic Acid ◽  
Carbon Chain ◽  
Standard Diet

Feeding mice, over 3 generations, an equicaloric diet in which α-linolenic acid, the dietary precursor of n-3 polyunsaturated fatty acids, was substituted by linoleic acid, the dietary precursor of n-6 polyunsaturated fatty acids, significantly increased body weight throughout life when compared with standard diet-fed mice. Adipogenesis observed in the low n-3 fatty acid mice was accompanied by a 6-fold upregulation of stearyl-coenzyme A desaturase 1 (Scd1), whose activity is correlated to plasma triglyceride levels. In total liver lipid and phospholipid extracts, the sum of n-3 fatty acids and the individual longer carbon chain acids, eicosapentaenoic acid (20:5n3), docosapentaenoic acid (22:5n3), and docosahexaenoic acid (22:6n3) were significantly decreased whereas arachidonic acid (20:4n6) was significantly increased. In addition, low n-3 fatty acid-fed mice had liver steatosis, heart, and kidney hypertrophy. Hence, reducing dietary α-linolenic acid, from 1.02 energy% to 0.16 energy% combined with raising linoleic acid intake resulted in obesity and had detrimental consequences on organ function.

scholarly journals FATTY ACIDS COMPOSITION OF TOCTE (JUGLANS NEOTROPICA DIELS) WALNUT FROM ECUADOR

2018 ◽  
Vol 11 (2) ◽  
pp. 395 ◽  
Author(s):  
Vilcacundo E ◽  
Alvarez M ◽  
Silva M ◽  
Carpio C ◽  
Morales D ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Oleic Acid ◽  
Linoleic Acid ◽  
Stearic Acid ◽  
Palmitic Acid ◽  
Linolenic Acid ◽  
Lipid Content ◽  
Methyl Esters ◽  
Total Lipid Content ◽  
Fatty Acids Composition

 Objective: The aim of this study was to determine the fatty acids composition in a tocte seeds oil (Juglans neotropica Diels) sample cultivated in Ecuador.Methods: Tocte oil was obtained from tocte seeds using the cold pressing method. Fatty acids analysis was carried out using the gas chromatography method with a mass selective detector (GC/MSD) and using the database Library NIST14.L to identify the compounds.Results: Methyl esters fatty acids were identified from tocte (J. neotropica Diels) walnut using the GC–MS analytical method. The total lipid content of tocte walnuts seeds of plants cultivated in Ecuador was of 49.01% of the total lipid content on fresh weight. Fatty acids were analyzed as methyl esters on a capillary column DB-WAX 122-7062 with a good separation of palmitic acid, stearic acid, oleic acid, linoleic acid, and linolenic acid. The structure of methyl esters fatty acids was determined using the GC–MS. Tocte walnut presents 5.05% of palmitic acid, 2.26% of stearic acid, 19.50% of oleic acid, 65.81% of linoleic acid, and 2.79% linolenic acid of the total content of fatty acids in tocte oil. Fatty acids content reported in this study were similar to the data reported for other walnuts seeds.Conclusions: Tocte seeds are a good source of monounsaturated and polyunsaturated fatty acids. Tocte oil content oleic acid and with a good content of ɷ6 α-linoleic and ɷ3 α-linolenic. Tocte walnut can help reduce risk cardiovascular diseases in Ecuador for their good composition of fatty acids.

scholarly journals Poultry meat production as a functional food with a voluntary n-6 and n-3 polyunsaturated fatty acids ratio

2008 ◽  
Vol 52 (No. 7) ◽  
pp. 203-213 ◽  
Author(s):  
D. Schneideroá ◽  
J. Zelenka ◽  
E. Mrkvicová
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Linoleic Acid ◽  
Polyunsaturated Fatty Acids ◽  
Linolenic Acid ◽  
Functional Food ◽  
The Other ◽  
Poultry Meat ◽  
Meat Production ◽  
Alpha Linolenic Acid

We studied the effect of different levels of linseed oils made either of the flax cultivar Atalante with a high content of &alpha;-linolenic acid (612 g/kg) or of the cultivar Lola with a predominating content of linoleic acid (708 g/kg) in a chicken diet upon the fatty acid pattern in meat. Cockerels Ross 308 were fed the diets containing 1, 3, 5 or 7 per cent of oil in the last 15 days of fattening. Breast meat (BM) and thigh meat (TM) without skin of 8 chickens from each dietary group were used for analyses. The relative proportions of fatty acids were expressed as percentages of total determined fatty acids. When feeding Atalante oil, the proportions of n-6 fatty acids were highly significantly lower while those of n-3 fatty acids were higher; the ratio of n-6/n-3 polyunsaturated fatty acids in meat was narrower (<i>P</i> < 0.001) than in chickens fed oil with a low content of &alpha;-linolenic acid. In BM and TM, the relative proportions of &alpha;-linolenic and &gamma;-linolenic acids were nearly the same, the proportion of linoleic acid in BM was lower, and the proportions of the other polyunsaturated fatty acids in BM were higher than in TM. In BM, the ratio of n-6/n-3 polyunsaturated fatty acids was significantly (<i>P</i> < 0.001) more favourable than that found in TM. The relative proportions of total saturated and monounsaturated fatty acids in meat decreased and those of polyunsaturated fatty acids increased significantly (<i>P</i> < 0.01) in dependence on the increasing level of dietary oils. When feeding Atalante oil, a significant increase in the proportion of linoleic acid in BM but not in TM was observed. The proportions of the other n-6 fatty acids decreased and those of all determined n-3 fatty acids, with the exception of docosahexaenoic acid, significantly increased with the increasing level of oil in the diet. When feeding Lola oil, its increasing content in the diet increased the relative proportion of linoleic acid as well as its elongation to &gamma;-linolenic acid; however, the proportions of arachidonic and adrenic acid did not change significantly (<i>P</i> > 0.05). The proportion of &alpha;-linolenic acid increased in both BM and TM. The proportion of eicosapentaenoic and clupanodonic acids in BM significantly decreased. The ratio of n-6 to n-3 polyunsaturated fatty acids ranged from 0.9 to 13.6 and from 1.0 to 17.2 in BM and TM, respectively. An increase in the level of Lola oil in the diet by 1% caused that the n-6/n-3 polyunsaturated fatty acid ratio extended by 1.00 and 1.19 units in BM and TM, respectively. Dependences of n-6/n-3 ratio on the level of Atalante oil were expressed by equations of convex parabolas with minima at the level of oil 5.8 and 5.9% for BM and TM, respectively. By means of the inclusion of linseed oil with a high content of &alpha;-linolenic acid in the feed mixture it would be possible to produce poultry meat as a functional food with a very narrow ratio of n-6/n-3 polyunsaturated fatty acids.

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