Geometric and positional fatty acid isomers interact differently with desaturation and elongation of linoleic and linolenic acids in cultured glioma cells

1990 ◽  
Vol 68 (3) ◽  
pp. 653-660 ◽  
Author(s):  
H. W. Cook ◽  
E. A. Emken
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Essential Fatty Acid ◽  
Essential Fatty Acids ◽  
Glioma Cells ◽  
Dienoic Acid ◽  
Chain Elongation ◽  
Positional Isomers ◽  
Trans Isomers ◽  
Trans Bond

A range of geometrical and positional isomers of 18-carbon acyl chains are potential components of diets containing fats from processed vegetable oils or ruminant animals. We have examined seventeen 18-carbon fatty acids, with cis or trans double bonds in positions 8–15, for their effects on desaturation and chain elongation of [1-14C]18:2(n − 6) or [1-14C]18:3(n − 3), primarily to 20:4(n − 6) or 20:5(n − 3) respectively, in cultured glioma cells. All trans monoenoic positional isomers inhibited Δ5 desaturation by approximately 60% when 18:2(n − 6) was the substrate, with no positional discrimination evident; with 18:3(n − 3) as substrate, only the 11- and 12-trans isomers were effective inhibitors of formation of 20:5(n − 3). All cis positional monoene isomers, except for 12-cis 18:1, produced 25–30% inhibition of conversion of 18:2(n − 6) to 20:4(n − 6), but had little effect on the conversion of 18:3(n − 3) to 20:5(n − 3). For dienoic isomers, the presence of a 12-trans bond inhibited formation of both 20:4(n − 6) and 20:5(n − 3) and this was enhanced markedly when the other bond in the dienoic acid was 9-trans. Presence of a 9-trans or 15-trans bond with 12-cis gave little effect except for a slight inhibition of 20:4(n − 6) formation by the 12-cis,15-trans 18:2 isomer. All-cis 20:3(n − 9) blocked Δ5 desaturation, increasing 20:3(n − 6) accumulation from 18:2(n − 6) and suggesting that formation of 20:3(n − 9) from 18:1(n − 9) during essential fatty acid deficiency may further exacerbate the already compromised formation of 20:4(n − 6). Further, the differential effects of various cis and trans isomers on the metabolism of 18:2(n − 6) and 18:3(n − 3) suggest that either Δ5 desaturation is not common in both pathways of conversion of 18:2(n − 6) or 18:3(n − 3) to their primary products or that selective interactions of trans and cis isomers occur when the essential fatty acid substrates are different.Key words: trans isomers, essential fatty acids, desaturation, glioma cells, fatty acid metabolism.

Lipids of the intestinal mucosa of normal and essential fatty acid deficient rats

1970 ◽  
Vol 48 (9) ◽  
pp. 631-639 ◽  
Author(s):  
M. Yurkowski ◽  
B. L. Walker
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Free Fatty Acids ◽  
Essential Fatty Acid ◽  
Corn Oil ◽  
Essential Fatty Acids ◽  
Coconut Oil ◽  
Fatty Acid Deficiency ◽  
Arachidonic Acids ◽  
Layer Chromatography

Mucosal lipids were isolated from the proximal, middle, and distal intestinal sections of rats fed diets containing either 10% corn oil or 10% hydrogenated coconut oil, the latter diet being deficient in essential fatty acids. By a combination of column and thin-layer chromatography, the lipids were fractionated and the major components found to consist of triglycerides, free fatty acids, cholesterol, phosphatidylcholine, and phosphatidylethanolamine. Several minor constituents were present. Triglycerides and free fatty acids were generally present in higher concentrations in animals fed corn oil, and the concentration of mucosal triglycerides decreased towards the distal end of the intestine whereas free fatty acids increased in this group. Essential fatty acid deficiency resulted in lower levels of linoleic and arachidonic acids and higher levels of palmitoleic, oleic, and eicosatrienoic acids in the mucosal lipids. Mono- and di-enoic fatty acids tended to decrease in concentration from the proximal to the distal end of the intestine; the polyunsaturated acids and, to some extent, the saturated acids, were lowest in the proximal section of the intestine.

Effects of Non-essential Fatty Acids on Essential Fatty Acid Deficiency

1965 ◽  
Vol 87 (2) ◽  
pp. 168-172 ◽  
Author(s):  
R. B. Alfin-Slater ◽  
R. S. Morris ◽  
H. Hansen ◽  
J. F. Proctor
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Essential Fatty Acid ◽  
Essential Fatty Acid Deficiency ◽  
Essential Fatty Acids ◽  
Acid Deficiency ◽  
Fatty Acid Deficiency

scholarly journals The effect of dihomo-γ-linolenic acid (20: 3, n-6) on the composition of phospholipid fatty acids in the liver of rats deficient in essential fatty acids

1978 ◽  
Vol 40 (1) ◽  
pp. 155-157 ◽  
Author(s):  
A. G. Hassam ◽  
M. A. Crawford
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Linoleic Acid ◽  
Linolenic Acid ◽  
Essential Fatty Acid ◽  
Essential Fatty Acids ◽  
Phospholipid Fatty Acids ◽  
Phospholipid Fraction ◽  
Liver Phospholipid ◽  
Dietary Energy

1. Rats were fed on either a diet deficient in essential fatty acid (EFA) or one supplemented with dihomo-γ-linolenic acid (20:3,n-6) at levels that represented 0.25, 0.5, 1.0 and 2.0% of the dietary energy.2. Supplementation of the diet of EFA-deficient animals with 20:3,n-6 reversed most of the fatty acid changes induced in the liver phospholipid fraction.3. The EFA potency of 20:3,n-6 was found to be similar to that of γ-linolenic acid (18:3,n-6) which has been shown to be higher than that of linoleic acid (18:2,n-6).

Modulation of Cytokine Production In Vivo by Dietary Essential Fatty Acids in Patients with Colorectal Cancer

1994 ◽  
Vol 87 (6) ◽  
pp. 711-717 ◽  
Author(s):  
P. Purasiri ◽  
A. Murray ◽  
S. Richardson ◽  
S. D. Heys ◽  
D. Horrobin ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Essential Fatty Acid ◽  
Cytokine Production ◽  
Essential Fatty Acids ◽  
Interferon Γ ◽  
Total Serum ◽  
Serum Cytokines ◽  
Factor Α ◽  
Necrosis Factor

1. The effects of essential fatty acids (γ-linolenic acid, eicosapentaenoic acid, docosahexaenoic acid), at a dose of 4.8 g/day, given in combination as dietary supplements, on cytokine production were investigated in patients with colorectal cancer. 2. Total serum cytokines - interleukin (interleukin-1β, 2, 4 and 6), tumour necrosis factor-α and interferon-γ - were analysed using the enzyme-linked immunosorbent assay technique at different time intervals during the course of essential fatty acid supplementation. 3. Fatty acid uptake and patient compliance were confirmed by a significant increase in serum levels of γ-linolenic acid, eicosapentaenoic acid and docosahexaenoic acid in all three fractions: triacylglycerol, cholesterol and phospholipid. 4. There was no significant alteration in total serum cytokine concentration/levels in the first 2 months of essential fatty acid ingestion, but the levels of serum cytokines steadily declined thereafter, reaching minimum levels after 6 months of essential fatty acid supplementation. 5. Essential fatty acids, at the dose and duration (6 months) used in this study, reduced total serum interleukin-1β levels by 61% (P = 0.044), interleukin-2 by 63% (P = 0.05), interleukin-4 by 69% (P = 0.025), interleukin-6 by 83% (P = 0.030), tumour necrosis factor-α by 73% (P = 0.040) and interferon-γ by 67% (P = 0.050). 6. Three months after cessation of essential fatty acid intake, however, these cytokine levels returned to presupplementation values. 7. This present study has shown that long-term n-3 and n-6 EFA ingestion results in a significant reduction in circulating key cytokines. The precise mechanism of this reduction is unclear.

Effects of essential fatty acid deficiency on rat adrenal composition and secretory activity

1959 ◽  
Vol 197 (4) ◽  
pp. 893-896 ◽  
Author(s):  
Takuya Hayashida ◽  
Oscar W. Portman
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Essential Fatty Acid ◽  
Corn Oil ◽  
Essential Fatty Acids ◽  
Secretory Activity ◽  
Monounsaturated Fatty Acids ◽  
Essential Fatty Acid Deficient ◽  
Fatty Acid Deficiency

The effect of feeding diets deficient in essential fatty acids on the composition of adrenal lipids and on the secretory activity of adrenocortical hormones was studied. Rats which were fed diets devoid of fat had lower levels of tetraenoic and pentaenoic acids and higher levels of trienoic acids in both the total lipid and cholesterol ester fraction than did rats receiving a supplement of corn oil. There was a greater accumulation of cholesterol esterified with saturated and monounsaturated fatty acids in the adrenals of the rats fed essential fatty acid-deficient diets. The adrenals of the essential fatty acid-deficient rats secreted smaller quantities of steroid hormones in vitro under the stimulation of ACTH.

Fish Oils.: IX. Certain Fish Oils as Sources of Nutritionally Essential Fatty Acids.

1943 ◽  
Vol 6b (2) ◽  
pp. 109-112 ◽  
Author(s):  
B. E. Bailey
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Methyl Linoleate ◽  
Essential Fatty Acid ◽  
Essential Fatty Acid Deficiency ◽  
Essential Fatty Acids ◽  
Fish Oils ◽  
Acid Deficiency ◽  
Fatty Acid Deficiency

Pilchard oil and two fractions of salmon egg oil, despite their greater unsaturation, proved less effective than methyl linoleate in curing rats suffering from essential fatty acid deficiency. Herring oil, less unsaturated, was even less effective.

Fatty Acids: Evolution in Relation to Neurobiology

1993 ◽  
Vol 71 (9) ◽  
pp. 683-683 ◽  
Author(s):  
M. T. Clandinin
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Polyunsaturated Fatty Acids ◽  
Acid Content ◽  
Essential Fatty Acids ◽  
Fatty Acid Content ◽  
Chain Elongation ◽  
Brain Membrane ◽  
The Impact ◽  
Long Chain

Metabolism of long-chain polyunsaturated fatty acids derived from 18:2ω−6 and 18:3ω−3 by chain elongation – desaturation is essential for synthesis of complex structural lipids, leukotrienes, thromboxanes, and prostaglandins. These essential fatty acids are required for normal function in developing tissues and appropriate maturation of a wide variety of physiological processes. During development, fetal accretion of long-chain metabolites of ω−6 and ω−3 fatty acids may result from maternal or placental synthesis and transfer or, alternatively, from the metabolism of 18:2ω−6 and 18:3ω−3 to longer chain homologues by the fetus. After birth the infant must synthesize or be fed the very long chain polyunsaturated fatty acids of C20 and C22 type derived from 18:2ω−6 and 18:3ω−3.Metabolism of ω−6 and ω−3 fatty acids utilizes the same enzyme system and is competitive. When levels of dietary ω−3 and ω−6 C18 fatty acids are altered, the levels of metabolites of these precursor fatty acids change in specific brain membranes, influencing membrane lipid dependent functions. For example, a diet unbalanced in very long chain ω−3 and ω−6 fatty acids may increase brain membrane ω−3 fatty acid content when 20:5ω−3 is fed, while decreasing membrane fatty acid content of the ω−6 series of competing fatty acids. As 20:4ω−6 is quantitatively and qualitatively important to brain phospholipid, significant reduction in brain levels of 20:4ω−6 may be less than optimal. The impact of these compositional changes on brain function is not yet clear.The authors in this symposium address how this general area of essential fatty acid metabolism is relevant to the evolution of man, growth and development of fish, function of the retina and neural tissue, cognitive development of infants, and infant nutrition.

Essential Fatty Acid Status in Premature Newborns Fed by Nasoduodenal Technique

PEDIATRICS ◽  
1981 ◽  
Vol 67 (1) ◽  
pp. 73-78
Author(s):  
Iolanda Minoli ◽  
Bernardo Coppalini ◽  
Claudio Galli ◽  
Guido Moro
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Essential Fatty Acid ◽  
Essential Fatty Acids ◽  
Lipid Fraction ◽  
Fatty Acid Status ◽  
Premature Newborns ◽  
Nutritional Conditions ◽  
Acid Status ◽  
Essential Fatty Acid Status

The fatty acid composition of plasma phospholipids and the triene (20:3, n=9) to tetraene (20:4, n=6) ratio in the same lipid fraction have been determined, as indices of the essential fatty acid status, in a group of 22 healthy premature newborns fed by the nasoduodenal technique. Determinations have been carried out on the first and fifth day of life for all 22 newborns, and also on the tenth and 30th day of life for 12 of them. The normal plasma levels of essential fatty acids obtained indicate a satisfactory utilization of dietary essential fatty acids under these unusual nutritional conditions.

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