Regulation of unsaturated fatty acids biosynthesis 1. Effect of unsaturated fatty acid of 18 carbons on the microsomal desaturation of linoleic acid into γ-linolenic acid

1969 ◽  
Vol 176 (3) ◽  
pp. 471-479 ◽  
Author(s):  
Rodolfo R. Brenner ◽  
Raúl O. Peluffo
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Linoleic Acid ◽  
Linolenic Acid ◽  
Unsaturated Fatty Acid ◽  
Unsaturated Fatty Acids

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.

Degradative Effects of Guayule Resin on Natural Rubber

1981 ◽  
Vol 54 (1) ◽  
pp. 115-123 ◽  
Author(s):  
R. W. Keller ◽  
D. S. Winkler ◽  
H. L. Stephens
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Linoleic Acid ◽  
Natural Rubber ◽  
Unsaturated Fatty Acid ◽  
Unsaturated Fatty Acids ◽  
Oxidation Mechanism ◽  
Hydrocarbon Polymers ◽  
Rubber Degradation

Abstract This study indicates that the degradative effects of guayule resin on natural rubber are due to the presence of unsaturated fatty acids in the resin. Since linoleic acid is, by far, the most abundant unsaturated fatty acid in guayule resin, it appears that linoleic acid is primarily responsible for the degradative effects of guayule resin on natural rubber. A possible mechanism to explain the acceleration of natural rubber degradation caused by linoleic acid can be developed by fitting linoleic acid into the Bolland oxidation mechanism for hydrocarbon polymers.

AGGRAVATION OF CHOLESTEROL ATHEROSCLEROSIS IN RABBITS BY FREE UNSATURATED FATTY ACIDS

1959 ◽  
Vol 37 (3) ◽  
pp. 479-483 ◽  
Author(s):  
George Rona ◽  
Clifford I. Chappel ◽  
Roger Gaudry
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Linoleic Acid ◽  
Olive Oil ◽  
Unsaturated Fatty Acid ◽  
Unsaturated Fatty Acids

An unsaturated fatty acid preparation containing 90 to 95% linoleic acid was tested on cholesterol-induced hypercholesterolemia and atherosclerosis in the rabbit. The rabbits, treated with cholesterol dissolved in the unsaturated fatty acid, revealed a significantly higher hypercholesterolemia and more marked atherosclerosis than the rabbits that were treated with cholesterol dissolved in the same amount of olive oil.

AGGRAVATION OF CHOLESTEROL ATHEROSCLEROSIS IN RABBITS BY FREE UNSATURATED FATTY ACIDS

1959 ◽  
Vol 37 (1) ◽  
pp. 479-483 ◽  
Author(s):  
George Rona ◽  
Clifford I. Chappel ◽  
Roger Gaudry
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Linoleic Acid ◽  
Olive Oil ◽  
Unsaturated Fatty Acid ◽  
Unsaturated Fatty Acids

An unsaturated fatty acid preparation containing 90 to 95% linoleic acid was tested on cholesterol-induced hypercholesterolemia and atherosclerosis in the rabbit. The rabbits, treated with cholesterol dissolved in the unsaturated fatty acid, revealed a significantly higher hypercholesterolemia and more marked atherosclerosis than the rabbits that were treated with cholesterol dissolved in the same amount of olive oil.

The Use of Argentation Chromatography for the Analysis of Fatty Acid Esters of Polyenes: The Structure of Carotenoid Esters of Aglais urticae (Lepidoptera, Insecta)

1975 ◽  
Vol 30 (5-6) ◽  
pp. 369-378 ◽  
Author(s):  
Hartmut Kayser
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Linoleic Acid ◽  
Linolenic Acid ◽  
Unsaturated Fatty Acids ◽  
Reversed Phase ◽  
Fatty Acid Esters ◽  
Preparative Scale ◽  
Argentation Chromatography ◽  
Acid Esters

Abstract Argentation Thin-layer systems for argentation chromatography of fatty-acid esters of carotenoids have been developed. As two-dimensional reversed-phase partition system on paraffine impregnated cellulose this method permits a clear discrimination between saturated and unsaturated fatty acids. By adsorption on silver nitrate containing silica gel-G separation of carotenoid esters according to the degree of unsaturation of their fatty acids was established. With the use of known esters for comparison the fatty acids of whole carotenoid esters can be successfully analysed from minute amounts. Using these methods the carotenoid esters of pupae of Aglais urticae have been studied. The pupae contain 5.3% β-carotene, 46% lutein diester, 7.8% lutein 3-monoester, 11.7% lutein 3′-mono-ester, and 29.2% unesterified lutein. The fatty acids of the esters are linoleic acid (18:2) and linolenic acid (18:3) only. The diester fraction was composed of 70% dilinolenate, 25% linolenate-linoleate, and 5% dilinoleate. The combined monoesters consisted of 81% linolenate and 19% linoleate. The two main diesters could be isolated in a preparative scale and their structure verified by mass spectrometry. On the whole, in Aglais pupae 6.2 μg linolenic acid and 1.4 μg linoleic acid are bound to lutein. Since polyunsaturated fatty acids are of dietary origin, and represent essential factors for insect development, it is concluded, that their esterification with carotenoids may be a mode of storage comparable to the formation of glycerides.

scholarly journals Changes in Soybean (Glycine max L.) Flour Fatty-Acid Content Based on Storage Temperature and Duration

Molecules ◽  
2018 ◽  
Vol 23 (10) ◽  
pp. 2713 ◽  
Author(s):  
Mayakrishnan Prabakaran ◽  
Kyoung-Jin Lee ◽  
Yeonju An ◽  
Chang Kwon ◽  
Soyeon Kim ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Oleic Acid ◽  
Fatty Acid ◽  
Linoleic Acid ◽  
Linolenic Acid ◽  
Acid Content ◽  
Unsaturated Fatty Acids ◽  
Storage Temperature ◽  
Fatty Acid Content ◽  
Soybean Flour

Soybeans are low in saturated fat and a rich source of protein, dietary fiber, and isoflavone; however, their nutritional shelf life is yet to be established. This study evaluated the change in the stability and quality of fatty acids in raw and roasted soybean flour under different storage temperatures and durations. In both types of soybean flour, the fatty-acid content was the highest in the order of linoleic acid (18-carbon chain with two double bonds; C18:2), oleic acid (C18:1), palmitic acid (C16:0), linolenic acid (18:3), and stearic acid (C18:0), which represented 47%, 26%, 12%, 9%, and 4% of the total fatty-acid content, respectively. The major unsaturated fatty acids of raw soybean flour—oleic acid, linoleic acid, and linolenic acid—decreased by 30.0%, 94.4%, and 97.7%, and 38.0%, 94.8%, and 98.0% when stored in polyethylene and polypropylene film, respectively, after 48 weeks of storage under high-temperature conditions. These values were later increased due to hydrolysis. This study presents the changes in composition and content of two soybean flour types and the changes in quality and stability of fatty acids in response to storage temperature and duration. This study shows the influence of storage conditions and temperature on the nutritional quality which is least affected by packing material.

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.

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

2018 ◽  
Vol 121 (1) ◽  
pp. 65-73 ◽  
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.

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.

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