The aerobic oxidation of unsaturated fatty acids and their esters: cobalt stearate-catalyzed oxidation of linoleic acid

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.

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Fatty acid positional distribution (sn-2 fatty acids) and phospholipid composition in Chinese breast milk from colostrum to mature stage

British Journal Of Nutrition ◽

10.1017/s0007114518002994 ◽

2018 ◽

Vol 121 (1) ◽

pp. 65-73 ◽

Cited By ~ 9

Author(s):

Ke Wu ◽

Runying Gao ◽

Fang Tian ◽

Yingyi Mao ◽

Bei Wang ◽

...

Keyword(s):

Fatty Acids ◽

Fatty Acid ◽

Linoleic Acid ◽

Fatty Acid Profile ◽

Unsaturated Fatty Acids ◽

Fatty Acid Content ◽

Positional Distribution ◽

Phospholipid Composition ◽

Mature Stage ◽

Feeding Time

AbstractThis study quantified the fatty acid profile with emphasis on the stereo-specifically numbered (sn) 2 positional distribution in TAG and the composition of main phospholipids at different lactation stages. Colostrum milk (n 70), transitional milk (n 96) and mature milk (n 82) were obtained longitudinally from healthy lactating women in Shanghai. During lactation, total fatty acid content increased, with SFA dominating in fatty acid profile. A high ratio of n-6:n-3 PUFA was observed as 11:1 over lactation due to the abundance of linoleic acid in Chinese human milk. As the main SFA, palmitic acid showed absolute sn-2 selectivity, while oleic acid, linoleic acid and α-linolenic acid, the main unsaturated fatty acids, were primarily esterified at the sn-1 and sn-3 positions. Nervonic acid and C22 PUFA including DHA were more enriched in colostrum with an sn-2 positional preference. A total of three dominant phospholipids (phosphatidylethanolamine (PE), phosphatidylcholine (PC) and sphingomyelin (SM)) were analysed in the collected samples, and each showed a decline in amount over lactation. PC was the dominant compound followed by SM and PE. With prolonged breast-feeding time, percentage of PE in total phospholipids remained constant, but PC decreased, and SM increased. Results from this study indicated a lipid profile different from Western reports and may aid the development of future infant formula more suitable for Chinese babies.

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

Biochemical Journal ◽

10.1042/bj2850557 ◽

1992 ◽

Vol 285 (2) ◽

pp. 557-562 ◽

Cited By ~ 126

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.

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Profile of ingested fatty acids and in the duodenal digest of steers fed different diets

Revista Brasileira de Zootecnia ◽

10.1590/s1516-35982010001100025 ◽

2010 ◽

Vol 39 (11) ◽

pp. 2502-2511 ◽

Cited By ~ 4

Author(s):

Luís Fernando Glasenapp de Menezes ◽

Gilberto Vilmar Kozloski ◽

João Restle ◽

Ivan Luiz Brondani ◽

Raul Dirceu Pazdiora ◽

...

Keyword(s):

Fatty Acids ◽

Linoleic Acid ◽

Conjugated Linoleic Acid ◽

Unsaturated Fatty Acids ◽

Saturated Fatty Acids ◽

Latin Square ◽

Tropical Pasture ◽

Ruminal Fermentation ◽

Omega 3 ◽

Conventional Diet

It was evaluated in this study the effect of the type of the diet on duodenal flow of long-chain fatty acids in steers. The tested diets were the following: conventional (feedlot diet composed of 60% corn silage and 40% of concentrate); winter forage silage - rye grass (Lolium multiflorum, Lam); or tropical forage silage - association of millet (Pennisetum americanum, Leeke + alexander grass, Brachiaria plantaginea). Six Charolais × Nellore crossbred steers with cannulas in duodenum were used in a 3 × 3 double Latin square. Dry material intake was similar among the groups (mean of 4,037 g/day), but the intake of total fatty acids and saturated fatty acids were higher in the group fed tropical pasture silage. On the other hand, the animals which received the conventional diet consumed higher quantity of unsaturated fatty acids. Tropical pasture silage provided higher consumption of vacenic acid (C18:1 t-11) and the winter forage silage offered higher consumption of conjugated linoleic acid. The intake of omega-6 fatty acids was higher in the group fed conventional diet and for omega-3, intake was higher in the group fed tropical pasture diet. The total fatty acid flow in the duodenum was not affected by the diets, but in all treatments it was higher than the consumed one. The animals fed diet with concentrate show the greatest changes on the profile of fatty acids during the ruminal fermentation. Conventional diets provide the highest intake of unsaturated fatty acids and the highest availability of vacenic acid in the small intestine, but they do not increase the supply of intestinal conjugated linoleic acid.

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FATTY ACID COMPOSITION OF SERUM LIPIDS IN HYPER- AND HYPOTHYROIDISM

Acta Endocrinologica ◽

10.1530/acta.0.0710062 ◽

1972 ◽

Vol 71 (1) ◽

pp. 62-72 ◽

Cited By ~ 19

Author(s):

Knut Kirkeby

Keyword(s):

Fatty Acids ◽

Fatty Acid Composition ◽

Fatty Acid ◽

Linoleic Acid ◽

Acid Composition ◽

Serum Lipids ◽

Unsaturated Fatty Acids ◽

Eicosatrienoic Acid ◽

High Linoleic Acid ◽

Absolute Concentrations

ABSTRACT The fatty acid composition of cholesterol esters, phospholipids, and triglycerides of the serum has been studied in groups of hyperthyroid and hypothyroid women and also in control material matched for age. In hyperthyroidism, a decrease in the proportions of linoleic acid and an increase in the proportions of some saturated and mono-unsaturated fatty acids were observed. When absolute concentrations were considered, it appeared that the decrease in linoleic acid was almost equivalent to the entire decrease in total fatty acids in the serum of the hyperthyroid patients. In hypothyroidism no changes were noted in the proportions of linoleic, saturated and mono-unsaturated fatty acids, and the absolute concentrations reflected the general increase in serum lipids. It is believed that these findings may be explained by the changes in lipid turnover which are known to occur in disturbances of thyroid function. In hyperthyroidism, they lead to a linoleic acid deficiency, while a sparing effect must be operating in hypothyroidism. The finding of relatively high linoleic acid values combined with hyperlipaemia in hypothyroidism seems to be characteristic of the condition, since other types of hyperlipaemia are almost invariably combined with low percentages of linoleic acid. Results regarding arachidonic and eicosatrienoic acid are consistent with increased synthesis in hyperthyroidism, and decreased synthesis in hypothyroidism.

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Effect of dietary fat supplements on levels of n-3 poly-unsaturated fatty acids,transacids and conjugated linoleic acid in bovine milk

Animal Science ◽

10.1017/s135772980005147x ◽

1999 ◽

Vol 69 (3) ◽

pp. 613-625 ◽

Cited By ~ 97

Author(s):

N. W. Offer ◽

M. Marsden ◽

J. Dixon ◽

B. K. Speake ◽

F. E. Thacker

Keyword(s):

Fatty Acids ◽

Linoleic Acid ◽

Conjugated Linoleic Acid ◽

Milk Yield ◽

Milk Fat ◽

Trans Fatty Acids ◽

Unsaturated Fatty Acids ◽

Linseed Oil ◽

The Other ◽

Fat Supplements

AbstractThe effects of three fat supplements on milk yield and composition were measured using 12 mid-lactation in-calf Hoistein-Friesian cows in a balanced incomplete change-over design over three periods each of 3 weeks. All cows received a basal diet consisting of 36 kg/day grass silage (dry matter (DM) 270 g/kg, metabolizable energy (ME) 11·6 MJ/kg DM) and 7 kg/day o f a concentrate mixture containing (g/kg) rolled barley (501), molassed sugar-beet pulp shreds (277), soya-bean meal (208) and a standard cow mineral supplement (14). Treatments were CON (control-no supplement); LIN and FISH (250 gl day of either linseed oil or marine oil, providing approximately 0·046 of ME intake) or TOA (95 glday of tuna orbital oil, providing 0·018 of total ME intake).There were no significant effects on silage DM intake or milk yield (means 9·25 and 17·2 kg/day respectively). The FISH and TOA treatments depressed (F < 0·05) milk fat concentration (45·4, 44·6, 34·5 and 41·6 (s.e.d. 1·08) g/kg for CON, LIN, FISH and TOA respectively; note — the same treatment order is used for all results quoted). Compared with values for CON, yield of f at (glday) was significantly (F < 0·05) greater for LIN and significantly lower for FISH (739, 808, 572 and 732, s.e.d. 28·7). All three oil supplements reduced (F < 0·05) milk protein content (33·6, 32·5, 30·6 and 32·4 (s.e.d. 0·43) g/kg) but, apart from a small increase for LIN, protein yield (glday) was unaffected (545, 586, 510 and 574, s.e.d. 20·2).The concentrations (g/100 g) of short-chain fatty acids (< C14) and C16 : 0 in milk f at were lower (F < 0·05) for LIN than for the other treatments. All supplements increased the concentrations ofC18:1 (F < 0·05), the value for LIN being greater (F < 0·05) than for the other treatments (21·0, 27·2, 25·3 and 23·7, s.e.d. 0·74). The FISH and TOA treatments increased (F < 0·05) the concentrations of long chain (< C2O) (n-3) poly-unsaturated fatty acids (PUFA), (0·19, 0·17, 0·49 and 0·27, s.e.d. 0·026) but less than proportionately 0·03 of dietary intake of these acids was transferred to milk, probably because they were found to be mostly in the phospholipid and cholesterol ester fractions of plasma. The FISH and TOA treatments increased (F < 0·05) the percentages of total trans fatty acids in milk fat (1·13, 2·19, 10·26 and 3·62, s.e.d. 0·728) whilst a significant (F < 0·05) increase in conjugated linoleic acid (CLA) was observed only for FISH (0·16, 0·28, 1·55, and 0·52, s.e.d. 0·154). Concentrations of CLA and total trans acids in milk were highly correlated (r = 0·91, no. =36, F < 0·001) whilst trans acids in milk were inversely correlated with milk fat content (r = -0·63, no. = 36, F < 0·001) supporting the theory that milk fat depression may be caused by increased supply of trans fatty acids to the mammary gland. The health implications of these changes in milk fat composition are discussed.

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Production of Palmitoleic and Linoleic Acid in Oleaginous and Nonoleaginous Yeast Biomass

International Journal of Analytical Chemistry ◽

10.1155/2016/7583684 ◽

2016 ◽

Vol 2016 ◽

pp. 1-9 ◽

Cited By ~ 15

Author(s):

Irena Kolouchová ◽

Olga Maťátková ◽

Karel Sigler ◽

Jan Masák ◽

Tomáš Řezanka

Keyword(s):

Fatty Acids ◽

Linoleic Acid ◽

Nitrogen Source ◽

Ammonium Sulfate ◽

Lipid Accumulation ◽

Unsaturated Fatty Acids ◽

Potassium Nitrate ◽

High Ratio ◽

Dietary Fatty Acids ◽

Dry Cell Weight

We investigated the possibility of utilizing both oleaginous yeast species accumulating large amounts of lipids (Yarrowia lipolytica, Rhodotorula glutinis, Trichosporon cutaneum,andCandidasp.) and traditional biotechnological nonoleaginous ones (Kluyveromyces polysporus, Torulaspora delbrueckii,andSaccharomyces cerevisiae) as potential producers of dietetically important major fatty acids. The main objective was to examine the cultivation conditions that would induce a high ratio of dietary fatty acids and biomass. Though genus-dependent, the type of nitrogen source had a higher influence on biomass yield than the C/N ratio. The nitrogen source leading to the highest lipid accumulation was potassium nitrate, followed by ammonium sulfate, which is an ideal nitrogen source supporting, in both oleaginous and nonoleaginous species, sufficient biomass growth with concomitantly increased lipid accumulation. All yeast strains displayed high (70–90%) content of unsaturated fatty acids in total cell lipids. The content of dietary fatty acids of interest, namely, palmitoleic acid and linoleic acid, reached inKluyveromycesandTrichosporonstrains over 50% of total fatty acids and the highest yield, over 280 mg per g of dry cell weight of these fatty acids, was observed inTrichosporonwith ammonium sulfate as nitrogen source at C/N ratio 70.

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UNSATURATED FATTY ACIDS IN THE DIETARY DESTRUCTION OF N,N-DIMETHYLAMINOAZOBENZENE (BUTTER YELLOW) AND IN THE PRODUCTION OF ANEMIA IN RATS

Journal of Experimental Medicine ◽

10.1084/jem.76.5.413 ◽

1942 ◽

Vol 76 (5) ◽

pp. 413-420 ◽

Cited By ~ 6

Author(s):

Paul György ◽

Rudolph Tomarelli ◽

Robert P. Ostergard ◽

J. B. Brown

Keyword(s):

Fatty Acids ◽

Linoleic Acid ◽

Room Temperature ◽

Unsaturated Fatty Acids ◽

Destructive Effect ◽

Butter Fat ◽

Loss Of Weight ◽

Secondary Type ◽

Progressive Anemia

Crude linoleic acid incorporated with or without butter yellow in a synthetic diet proved to be toxic for rats. The toxic effect manifested itself in loss of weight, progressive anemia of the secondary type, leucopenia, and pediculosis. It could be neutralized preventively and therapeutically by administration of yeast. The toxicity of the diet containing linoleic acid appears to be due to oxidative break-down products of the unsaturated fatty acid. The color of the same diet when it contained crude linoleic acid supplemented with butter yellow faded progressively in the presence of air (O2), even at room temperature. Purified preparations of linoleic acid and, to a less degree, purified preparations of arachidonic and oleic acids have shown the same destructive effect on butter yellow in vitro. Brown (unpolished) or white rice contains a stabilizer (antioxidant) for the preservation of butter yellow. In experiments on the production of hepatoma in rats following the ingestion of butter yellow, rice on one hand and crisco or butter fat on the other hand have proved to be procarcinogenic. These results would seem to be correlated with the preservation of butter yellow in the diet and in the intestine, because of the antioxidant in rice and the low supply of unsaturated fatty acids,respectively.

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Influence of fish oil on ruminal biohydrogenation of C18 unsaturated fatty acids

British Journal Of Nutrition ◽

10.1079/bjn20061783 ◽

2006 ◽

Vol 95 (6) ◽

pp. 1199-1211 ◽

Cited By ~ 86

Author(s):

I. Wąsowska ◽

M. R. G. Maia ◽

K. M. Niedźwiedzka ◽

M. Czauderna ◽

J. M. C. Ramalho Ribeiro ◽

...

Keyword(s):

Fatty Acids ◽

Linoleic Acid ◽

Fish Oil ◽

Unsaturated Fatty Acids ◽

Butyrivibrio Fibrisolvens ◽

Isomerase Activity ◽

Epa And Dha ◽

Pure Cultures ◽

Ruminal Biohydrogenation

Dietarycis-9,trans-11-conjugated linoleic acid (CLA) is generally thought to be beneficial for human health. Fish oil added to ruminant diets increases the CLA concentration of milk and meat, an increase thought to arise from alterations in ruminal biohydrogenation of unsaturated fatty acids. To investigate the mechanism for this effect,in vitroincubations were carried out with ruminal digesta and the main biohydrogenating ruminal bacterium,Butyrivibrio fibrisolvens. Linoleic acid (LA) or α-linolenic acid (LNA) was incubated (1·67g/l) with strained ruminal digesta from sheep receiving a 50:50 grass hay–concentrate ration. Adding fish oil (up to 4·17g/l) tended to decrease the initial rate of LA (P=0·025) and LNA (P=0·137) disappearance, decreased (P<0·05) the transient accumulation of conjugated isomers of both fatty acids, and increased (P<0·05) the accumulation oftrans-11-18:1. Concentrations of EPA (20:5n-3) or DHA (22:6n-3), the major fatty acids in fish oil, were low (100mg/l or less) after incubation of fish oil with ruminal digesta. Addition of EPA or DHA (50mg/l) to pure cultures inhibited the growth and isomerase activity ofB. fibrisolvens, while fish oil had no effect. In contrast, similar concentrations of EPA and DHA had no effect on biohydrogenation of LA by mixed digesta, while the addition of LA prevented metabolism of EPA and DHA. Neither EPA nor DHA was metabolised byB. fibrisolvensin pure culture. Thus, fish oil inhibits ruminal biohydrogenation by a mechanism which can be interpreted partly, but not entirely, in terms of its effects onB. fibrisolvens.

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L'induction chez Ceratocystis de fructifications de types Graphium et Leptographium par des acides gras insaturés

Canadian Journal of Botany ◽

10.1139/b77-244 ◽

1977 ◽

Vol 55 (16) ◽

pp. 2159-2167 ◽

Cited By ~ 3

Author(s):

Yolande Dalpé ◽

Peterjürgen Neumann

Keyword(s):

Fatty Acids ◽

Linoleic Acid ◽

Linolenic Acid ◽

Unsaturated Fatty Acids ◽

Optimal Concentration ◽

Natural Substrate ◽

Acides Gras ◽

Imperfect State ◽

Intraspecific Difference

The unsaturated fatty acids oleic, linoleic, and linolenic induce the formation of the imperfect state of fructification of the Graphium type (coremia) with Ceratocystis ulmi and C. piceae and the Leptographium type with C. penicillata. Intraspecific difference between several strains of C. ulmi show that linoleic acid is the best inducer with an optimal concentration from 0.05 to 0.20 g/ml of methanol between the 10th and 25th day of culture. Linoleic and linolenic acid extend the capacity of sporulation of C. penicillata, conserving the strains capability of differentiation of Leptographium structures when ordinarily only the natural substrate can reinduce it. Ceratocystis dryocoetidis cultivated in the same conditions remains insensible to the lipid treatments.

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