Specific markers of lipid peroxidation issued from n−3 and n−6 fatty acids

2004 ◽  
Vol 32 (1) ◽  
pp. 139-140 ◽  
Author(s):  
M. Guichardant ◽  
B. Chantegrel ◽  
C. Deshayes ◽  
A. Doutheau ◽  
P. Moliere ◽  
...  
Keyword(s):  
Lipid Peroxidation ◽  
Fatty Acids ◽  
Arachidonic Acid ◽  
Fatty Acid ◽  
Eicosatetraenoic Acid ◽  
Breakdown Product ◽  
High Enrichment ◽  
Urinary Sample ◽  
12 Lipoxygenase ◽  
Fatty Acid Hydroperoxides

Several markers of lipid peroxidation are available with different degrees of specificity, from malondialdehyde as a global marker, to F2-isoprostane, which is specifically produced from arachidonic acid. Among these, 4-hydroxynonenal is recognized as a breakdown product of fatty acid hydroperoxides, such as 15-hydroperoxy-eicosatetraenoic acid and 13-hydroperoxy-octade cadienoic acid from the n−6 fatty acids. Furthermore, 4-hydroxyhexenal (4-HHE) derives from n−3 fatty acid hydroperoxides. We have recently described the occurrence of 4-hydroxydodecadienal (4-HDDE) from the 12-lipoxygenase product of arachidonic acid 12-hydroperoxy-eicosatetraenoic acid. These three hydroxy-alkenals may be measured in human plasma by GC–MS, but they may partly be generated in the course of sampling, and the relative volatility of 4-HHE makes its measurement quite unreliable. We have successfully characterized and measured the stable oxidized carboxylic acid products from the hydroxy-alkenals 4-HNA, 4-HHA and 4-HDDA in urine. The ratio between 4-HHA and 4-HNA found in the same urinary sample might provide useful information on the location of lipid peroxidation, accounting for the high enrichment of the cerebrovascular system with docosahexaenoic acid, the main n−3 fatty acid in humans.

Muscle-stimulating fatty acid isolated from placenta

1960 ◽  
Vol 198 (5) ◽  
pp. 1094-1098 ◽  
Author(s):  
Shigetaka Ichikawa
Keyword(s):  
Blood Pressure ◽  
Fatty Acids ◽  
Arachidonic Acid ◽  
Smooth Muscle ◽  
Fatty Acid ◽  
Biological Properties ◽  
Eicosatetraenoic Acid ◽  
Alkali Isomerization ◽  
Active Fraction ◽  
Hypotensive Action

A smooth-muscle-stimulating fatty acid has been isolated from the human placenta. The neutralization value, iodine value and results obtained from alkali-isomerization, biological assay and paper chromatography provided evidence indicating that the active substance is eicosatetraenoic acid (arachidonic acid). The active fraction manifested the following biological properties: a) delayed-slow-contracting action on the isolated intestine and uterus, which seemed to be a direct one on muscle fibers; b) hypotensive action on rabbit blood pressure in a dose of 5 µEq. The evidence considered in relation to the literature on smooth-muscle-activating, lipid-soluble acids, strongly indicates that eicosatetraenoic acid is more active than the previously studied fatty acids, and among the most active lipid-soluble smooth-muscle-activating substances.

scholarly journals Palmitic acid and long-chain polyunsaturated fatty acids dominate in mycelia of mangrove Halophytophthora and Salispina species in Taiwan

2021 ◽  
Vol 0 (0) ◽  
Author(s):  
Chun-Jui Su ◽  
Wen-Ting Ju ◽  
Yi-Min Chen ◽  
Michael W.L. Chiang ◽  
Sung-Yuan Hsieh ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Arachidonic Acid ◽  
Fatty Acid ◽  
Eicosapentaenoic Acid ◽  
Palmitic Acid ◽  
Unsaturated Fatty Acids ◽  
Essential Fatty Acids ◽  
Eicosatetraenoic Acid ◽  
Fatty Acid Profiles ◽  
High Production

Abstract Marine oomycetous species produce, among other fatty acids, omega-6 arachidonic acid (ARA) and omega-3 eicosapentaenoic acid (EPA), with implications for the industrial potential of this group of organisms and the need to find an isolate with high production. This study screened 14 isolates of marine oomycetous species: Halophytophthora avicenniae, H. batemanensis, H. exoprolifera, H. polymorphica and Salispina spinosa cultured from fallen mangrove leaves in Taiwan for 24 saturated and unsaturated fatty acids in their mycelia. This paper is the first to report C18:1n-7 vaccenic acid, C20:1 eicosenoic acid, C24:1 nervonic acid, C20:2n-6 eicosadienoic acid, C22:4n-6 adrenic acid, C20:4n-3 eicosatetraenoic acid and C22:5n-3 docosapentaenoic acid in mycelia of Halophytophthora and Salispina species, and the fatty acid profiles of H. batemanensis and H. exoprolifera. Five fatty acids were dominant in the mycelia of the isolates, i.e. C16:0 palmitic acid, C18:1n-9 oleic acid, C18:2n-6 linoleic acid, C20:4n-6 arachidonic acid and C20:5n-3 eicosapentaenoic acid. For the essential fatty acids, S. spinosa produced the highest level of arachidonic acid (27–31% of total fatty acid (TFA), 141–188 mg l−1 yield) while H. avicenniae IMB212 produced the highest percentage of EPA (15% of TFA) while H. polymorphica IMB227 produced the highest yield (96 mg l−1). Different species and isolates of the same species produced different fatty acid profiles, and further research effort may yield a high production isolate of industrial significance and also important fatty acids from the marine environment.

scholarly journals Changes in fatty acid levels (saturated, monounsaturated and polyunsaturated) during pregnancy

2021 ◽  
Vol 21 (1) ◽  
Author(s):  
Estefania Aparicio ◽  
Carla Martín-Grau ◽  
Carmen Hernández-Martinez ◽  
Nuria Voltas ◽  
Josefa Canals ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Arachidonic Acid ◽  
Fatty Acid ◽  
Docosahexaenoic Acid ◽  
Serum Concentration ◽  
Eicosapentaenoic Acid ◽  
Pregnant Women ◽  
First Trimester ◽  
Third Trimester ◽  
Total N

Abstract Background During pregnancy a high amount of fatty acids (FA) is necessary to meet foetus demands, which vary during gestation. The present study describes the changes in maternal fatty acid concentrations during pregnancy in a sample of pregnant women. Methods This is a longitudinal study of 479 pregnant women who were monitored from the first trimester to third trimester of pregnancy. Data on maternal characteristics were recorded and a serum sample was collected in each trimester. The fatty acid profile (saturated (SFA: total, lauric acid, myristic acid, palmitic acid, stearic acid), monounsaturated (MUFA: total, palmitoleic acid, oleic acid) and polyunsaturated fatty acids (PUFA: total omega-6 (n-6), linoleic acid, dihomo-γ-linolenic acid, arachidonic acid (AA), total omega-3 (n-3), eicosapentaenoic acid (EPA), docosahexaenoic acid (DHA)) was analysed with a gas chromatography-mass spectrometry combination. Results From the first trimester to third trimester of pregnancy, a significant increase in total SFA, total MUFA and total n-6 PUFA was found. (p < 0.001). Nevertheless, the serum concentration of arachidonic acid (AA), eicosapentaenoic acid (EPA) and total n-3 PUFA decreased during gestation (p < 0.001). A statistically non-significant result was observed for the docosahexaenoic acid (DHA) serum concentration between the first and third trimesters of pregnancy. Significant correlations were observed between each total fatty acid concentrations of the first and third trimesters. Conclusion The circulating serum concentration of SFA, MUFA and n-6 PUFA increases during pregnancy, whereas essential fatty acids such as AA and EPA decrease, and DHA remains unchanged. Further research is necessary to understand the role played by FA throughout gestation.

scholarly journals Dietary fat and the diabetic state alter insulin binding and the fatty acyl composition of the adipocyte plasma membrane

1988 ◽  
Vol 253 (2) ◽  
pp. 417-424 ◽  
Author(s):  
C J Field ◽  
E A Ryan ◽  
A B Thomson ◽  
M T Clandinin
Keyword(s):  
Fatty Acids ◽  
Arachidonic Acid ◽  
Plasma Membrane ◽  
Fatty Acid ◽  
Polyunsaturated Fatty Acids ◽  
Insulin Binding ◽  
Fatty Acyl ◽  
Membrane Composition ◽  
Membrane Phospholipids ◽  
Diabetic State

Control and diabetic rats were fed on semi-purified high-fat diets providing a polyunsaturated/saturated fatty acid ratio (P/S) of 1.0 or 0.25, to examine the effect of diet on the fatty acid composition of major phospholipids of the adipocyte plasma membrane. Feeding the high-P/S diet (P/S = 1.0) compared with the low-P/S diet (P/S = 0.25) increased the content of polyunsaturated fatty acids in membrane phospholipids in both control and diabetic animals. The diabetic state decreased the content of polyunsaturated fatty acids, particularly arachidonic acid, in adipocyte membrane phospholipids. The decrease in arachidonic acid in membrane phospholipids of diabetic animals tended to be normalized to within the control values when high-P/S diets were given. For control animals, altered plasma-membrane composition was associated with change in insulin binding, suggesting that change in plasma-membrane composition may have physiological consequences for insulin-stimulated functions in the adipocyte.

scholarly journals Incorporation of platelet and leukocyte lipoxygenase metabolites by cultured vascular cells

Blood ◽  
1986 ◽  
Vol 67 (2) ◽  
pp. 373-378 ◽  
Author(s):  
AI Schafer ◽  
H Takayama ◽  
S Farrell ◽  
MA Jr Gimbrone
Keyword(s):  
Endothelial Cells ◽  
Arachidonic Acid ◽  
Smooth Muscle ◽  
Fatty Acid ◽  
Smooth Muscle Cells ◽  
Vascular Function ◽  
Muscle Cells ◽  
Arachidonic Acid Metabolism ◽  
Eicosatetraenoic Acid

Abstract When arachidonic acid metabolism is studied during platelet-endothelial interactions in vitro, the predominant cyclooxygenase end products of each cell type (thromboxane B2 and 6-keto-prostaglandin-F1 alpha, respectively) are essentially completely recovered in the cell-free supernatants of these reactions. In contrast, 50% of 12-hydroxy- 5,8,10,14-eicosatetraenoic acid (12-HETE), the major lipoxygenase metabolite from platelets, is released into the cell-free supernatant. In investigating the basis of this observation, we have found that platelet lipoxygenase metabolites were generated to the same extent during these coincubations but became rapidly incorporated into the endothelial cells. The endothelial cell-associated 12-HETE was present not only as free fatty acid, but was also incorporated into cellular phospholipids and triglycerides. When purified 3H-12-HETE, 3H-5-HETE (the major hydroxy acid lipoxygenase product of leukocytes), and 3H- arachidonic acid (the common precursor of these metabolites) were individually incubated with suspensions of cultured bovine aortic endothelial cells or smooth muscle cells, different patterns of intracellular lipid distribution were found. In endothelial cells, 12- HETE was incorporated equally into phospholipids and triglycerides, whereas 5-HETE was incorporated preferentially into triglycerides, and arachidonic acid was incorporated into phospholipids. In smooth muscle cells, both 12-HETE and 5-HETE showed more extensive incorporation into triglycerides. The rapid and characteristic incorporation and esterification of platelet and leukocyte monohydroxy fatty acid lipoxygenase products by endothelial and smooth muscle cells suggests a possible physiologic role for these processes in regulating vascular function.

scholarly journals The role of lipid components of the diet in the regulation of the fatty acid composition of the rat liver endoplasmic reticulum and lipid peroxidation

1978 ◽  
Vol 174 (2) ◽  
pp. 585-593 ◽  
Author(s):  
Catherine T. Hammer ◽  
Eric D. Wills
Keyword(s):  
Lipid Peroxidation ◽  
Fatty Acids ◽  
Endoplasmic Reticulum ◽  
Fatty Acid Composition ◽  
Fatty Acid ◽  
Polyunsaturated Fatty Acids ◽  
Acid Composition ◽  
Corn Oil ◽  
Lipid Peroxide

The fatty acid compositions of the lipids and the lipid peroxide concentrations and rates of lipid peroxidation were determined in suspensions of liver endoplasmic reticulum isolated from rats fed on synthetic diets in which the fatty acid composition had been varied but the remaining constituents (protein, carbohydrate, vitamins and minerals) kept constant. Stock diet and synthetic diets containing no fat, 10% corn oil, herring oil, coconut oil or lard were used. The fatty acid composition of the liver endoplasmic reticulum lipid was markedly dependent on the fatty acid composition of the dietary lipid. Feeding a herring-oil diet caused incorporation of 8.7% eicosapentaenoic acid (C20:5) and 17% docosahexaenoic acid (C22:6), but only 5.1% linoleic acid (C18:2) and 6.4% arachidonic acid (C20:4), feeding a corn-oil diet caused incorporation of 25.1% C18:2, 17.8% C20:4 and 2.5% C22:6 fatty acids, and feeding a lard diet caused incorporation of 10.3% C18:2, 13.5% C20:4 and 4.3% C22:6 fatty acids into the liver endoplasmic-reticulum lipids. Phenobarbitone injection (100mg/kg) decreased the incorporation of C20:4 and C22:6 fatty acids into the liver endoplasmic reticulum of rats fed on a lard, corn-oil or herring-oil diet. Microsomal lipid peroxide concentrations and rates of peroxidation in the presence of ascorbate depended on the nature and quantity of the polyunsaturated fatty acids in the diet. The lipid peroxide content was 1.82±0.30nmol of malonaldehyde/mg of protein and the rate of peroxidation was 0.60±0.08nmol of malonaldehyde/min per mg of protein after feeding a fat-free diet, and the values were increased to 20.80nmol of malonaldehyde/mg of protein and 3.73nmol of malonaldehyde/min per mg of protein after feeding a 10% herring-oil diet in which polyunsaturated fatty acids formed 24% of the total fatty acids. Addition of α-tocopherol to the diets (120mg/kg of diet) caused a very large decrease in the lipid peroxide concentration and rate of lipid peroxidation in the endoplasmic reticulum, but addition of the synthetic anti-oxidant 2,6-di-t-butyl-4-methylphenol to the diet (100mg/kg of diet) was ineffective. Treatment of the animals with phenobarbitone (1mg/ml of drinking water) caused a sharp fall in the rate of lipid peroxidation. It is concluded that the polyunsaturated fatty acid composition of the diet regulates the fatty acid composition of the liver endoplasmic reticulum, and this in turn is an important factor controlling the rate and extent of lipid peroxidation in vitro and possibly in vivo.

Antioxidant Behaviour of Thia Fatty Acids

2002 ◽  
Vol 55 (10) ◽  
pp. 647 ◽  
Author(s):  
C. J. Easton ◽  
A. Ferrante ◽  
T. A. Robertson ◽  
L. Xia
Keyword(s):  
Fatty Acids ◽  
Antioxidant Activity ◽  
Arachidonic Acid ◽  
Oxidation Process ◽  
Free Radical Oxidation ◽  
Lag Phase ◽  
Carboxyl Group ◽  
Radical Oxidation ◽  
Fatty Acid Hydroperoxides ◽  
Thia Fatty Acids

Eight thia fatty acids and other sulfides have been studied as inhibitors of autoxidation of arachidonic acid. The inhibitors extend the lag phase of the oxidation, to varying degrees. A carboxyl group in the vicinity of the sulfur reduces the antioxidant activity, while unsaturated sulfides are more effective than their saturated analogues. The results are consistent with the sulfides acting to reduce fatty acid hydroperoxides, which otherwise accumulate during the early stages of reaction and propagate the free-radical oxidation process.

scholarly journals Exposure to a Farm Environment During Pregnancy Increases the Proportion of Arachidonic Acid in the Cord Sera of Offspring

Nutrients ◽  
2019 ◽  
Vol 11 (2) ◽  
pp. 238 ◽  
Author(s):  
Malin Barman ◽  
Karin Jonsson ◽  
Agnes E. Wold ◽  
Ann-Sofie Sandberg
Keyword(s):  
Fatty Acids ◽  
Arachidonic Acid ◽  
Fatty Acid Composition ◽  
Fatty Acid ◽  
Breast Milk ◽  
Acid Composition ◽  
Post Partum ◽  
Maternal Diet ◽  
Circulation System ◽  
Adrenic Acid

Growing up in a farm environment is protective against allergy development. Various explanations have been put forward to explain this association. Fatty acids are regulators of immune function and the composition of fatty acids in the circulation system may affect immune development. Here, we investigate whether the fatty acid composition of cord serum differs for infants born to Farm (n = 26) or non-Farm mothers (n =29) in the FARMFLORA birth-cohort. For comparison, the levels of fatty acids in the maternal diet, serum and breast milk around 1 month post-partum were recorded. The fatty acids in the cord sera from infants born to Farm mothers had higher proportions of arachidonic acid (20:4 n-6) and adrenic acid (22:4 n-6) than those from infants born to non-Farm mothers. No differences were found for either arachidonic acid or adrenic acid in the diet, samples of the serum, or breast milk from Farm and non-Farm mothers obtained around 1 month post-partum. The arachidonic and adrenic acid levels in the cord blood were unrelated to allergy outcome for the infants. The results suggest that a farm environment may be associated with the fatty acid composition to which the fetus is exposed during pregnancy.

scholarly journals Some Biogenetic Considerations Regarding the Marine Natural Product (−)-Mucosin

Molecules ◽  
2019 ◽  
Vol 24 (22) ◽  
pp. 4147 ◽  
Author(s):  
Jens M. J. Nolsøe ◽  
Marius Aursnes ◽  
Yngve H. Stenstrøm ◽  
Trond V. Hansen
Keyword(s):  
Fatty Acids ◽  
Natural Products ◽  
Arachidonic Acid ◽  
Fatty Acid ◽  
Polyunsaturated Fatty Acids ◽  
Natural Product ◽  
Polyunsaturated Fatty Acid ◽  
Marine Natural Product ◽  
Structural Pattern ◽  
Different Origin

Recently, the identity of the marine hydrindane natural product (−)-mucosin was revised to the trans-fused structure 6, thereby providing a biogenetic puzzle that remains to be solved. We are now disseminating some of our insights with regard to the possible machinery delivering the established architecture. Aspects with regard to various modes of cyclization in terms of concerted versus stepwise processes are held up against the enzymatic apparatus known to be working on arachidonic acid (8). To provide a contrast to the tentative polyunsaturated fatty acid biogenesis, the structural pattern featured in (−)-mucosin (6) is compared to some marine hydrinane natural products of professed polyketide descent. Our appraisal points to a different origin and strengthens the hypothesis of a polyunsaturated fatty acids (PUFA) as the progenitor of (−)-mucosin (6).

Telomere Length in Healthy Adults Is Positively Associated With Polyunsaturated Fatty Acids, Including Arachidonic Acid, and Negatively With Saturated Fatty Acids

2020 ◽  
Vol 76 (1) ◽  
pp. 3-6
Author(s):  
Varinderpal S Dhillon ◽  
Permal Deo ◽  
Ann Chua ◽  
Phil Thomas ◽  
Michael Fenech
Keyword(s):  
Fatty Acids ◽  
Arachidonic Acid ◽  
Fatty Acid ◽  
Blood Cell ◽  
Telomere Length ◽  
Red Blood Cell ◽  
Blood Cells ◽  
Saturated Fatty Acids ◽  
Fatty Acid Status ◽  
Acid Status

Abstract Lymphocyte telomere length (LTL) is a biomarker of aging that may be modified by dietary factors including fat. Red blood cell fatty acid status is a well-validated indicator of long-term dietary intake of fat from various sources. Recent findings from epidemiological studies of LTL in relation to fatty acids in red blood cells are not conclusive. The present study was carried out to investigate if red blood cell fatty acid status in 174 healthy older South Australians is associated with LTL. Lymphocyte telomere length was measured by real-time qPCR and fatty acid content in red blood cells was measured by gas chromatography. Our results indicate that the majority of saturated fatty acids and monounsaturated fatty acids are negatively associated with LTL, whereas polyunsaturated fatty acids are positively associated with LTL. Multiple regression analysis revealed that arachidonic acid (C20:4n-6) is significantly, independently, positively correlated with LTL (β = 0.262; p = .000). The significant association of fatty acids, particularly C20:4n-6, with telomere length warrants further research.

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