scholarly journals Mass Spectrometric Analysis of Oxidized Eicosapentaenoic Acid Sodium Salt

2013 ◽  
Vol 6 ◽  
pp. LPI.S10862 ◽  
Author(s):  
Kelsey D. Jordan ◽  
Rita K. Upmacis

Eicosapentaenoic acid (EPA) is an omega-3 polyunsaturated fatty acid (PUFA) with 20 carbon atoms and 5 carbon-carbon double bonds. Mammalian cells cannot synthesize long chain PUFAs such as EPA de novo, and, thus, the most effective way to enrich cells in EPA is by dietary intake of fish oils. EPA supplementation causes an increase in its concentration in plasma lipids and in cell membrane phospholipids. Many beneficial effects of EPA supplementation have been noted, including (1) the potential to sensitize cancerous tumors towards chemotherapy, (2) the promotion of cardiovascular health, and (3) the alleviation of some mental disorders, but results from clinical trials have sometimes been disparate. In this study, we report the use of mass spectrometry to investigate the autoxidation of EPA, thereby demonstrating the formation of a variety of oxidized products. The oxidative stress of the patient may affect the response to EPA and may, in part, explain divergent results from clinical trials.

Nutrients ◽  
2020 ◽  
Vol 12 (3) ◽  
pp. 749 ◽  
Author(s):  
Zhi-Hong Yang ◽  
Marcelo Amar ◽  
Maureen Sampson ◽  
Amber B. Courville ◽  
Alexander V. Sorokin ◽  
...  

Background: Eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) have both shared and different cardiovascular effects, and commonly used fish oil supplements have considerably varied EPA/DHA ratios. Aims: We compared the effects of fish oil supplements with different EPA/DHA ratios on lipoprotein metabolism. Methods: In a double-blind, randomized cross-over study, normolipidemic adults (n = 30) consumed 12 g/day of EPA-rich (EPA/DHA: 2.3) or DHA-rich (EPA/DHA: 0.3) fish oil for 8-weeks, separated by an 8-week washout period. Results: Both fish oil supplements similarly lowered plasma TG levels and TG-related NMR parameters versus baseline (p < 0.05). There were no changes in plasma cholesterol-related parameters due to either fish oil, although on-treatment levels for LDL particle number were slightly higher for DHA-rich oil compared with EPA-rich oil (p < 0.05). Both fish oil supplements similarly altered HDL subclass profile and proteome, and down regulated HDL proteins related to inflammation, with EPA-rich oil to a greater extent. Furthermore, EPA-rich oil increased apoM abundance versus DHA-rich oil (p < 0.05). Conclusions: Overall, fish oil supplements with varied EPA/DHA ratios had similar effects on total lipids/lipoproteins, but differences were observed in lipoprotein subfraction composition and distribution, which could impact on the use of EPA versus DHA for improving cardiovascular health.


BMJ ◽  
2018 ◽  
pp. k4067 ◽  
Author(s):  
Heidi TM Lai ◽  
Marcia C de Oliveira Otto ◽  
Rozenn N Lemaitre ◽  
Barbara McKnight ◽  
Xiaoling Song ◽  
...  

AbstractObjectiveTo determine the longitudinal association between serial biomarker measures of circulating omega 3 polyunsaturated fatty acid (n3-PUFA) levels and healthy ageing.DesignProspective cohort study.SettingFour communities in the United States (Cardiovascular Health Study) from 1992 to 2015.Participants2622 adults with a mean (SD) age of 74.4 (4.8) and with successful healthy ageing at baseline in 1992-93.ExposureCumulative levels of plasma phospholipid n3-PUFAs were measured using gas chromatography in 1992-93, 1998-99, and 2005-06, expressed as percentage of total fatty acids, including α-linolenic acid from plants and eicosapentaenoic acid, docosapentaenoic acid, and docosahexaenoic acid from seafoood.Main outcome measureHealthy ageing defined as survival without chronic diseases (ie, cardiovascular disease, cancer, lung disease, and severe chronic kidney disease), the absence of cognitive and physical dysfunction, or death from other causes not part of the healthy ageing outcome after age 65. Events were centrally adjudicated or determined from medical records and diagnostic tests.ResultsHigher levels of long chain n3-PUFAs were associated with an 18% lower risk (95% confidence interval 7% to 28%) of unhealthy ageing per interquintile range after multivariable adjustments with time-varying exposure and covariates. Individually, higher eicosapentaenoic acid and docosapentaenoic acid (but not docosahexaenoic acid) levels were associated with a lower risk: 15% (6% to 23%) and 16% (6% to 25%), respectively. α-linolenic acid from plants was not noticeably associated with unhealthy ageing (hazard ratio 0.92, 95% confidence interval 0.83 to 1.02).ConclusionsIn older adults, a higher cumulative level of serially measured circulating n3-PUFAs from seafood (eicosapentaenoic acid, docosapentaenoic acid, and docosahexaenoic acid), eicosapentaenoic acid, and docosapentaenoic acid (but not docosahexaenoic acid from seafood or α-linolenic acid from plants) was associated with a higher likelihood of healthy ageing. These findings support guidelines for increased dietary consumption of n3-PUFAs in older adults.


2019 ◽  
Vol 105 (4) ◽  
pp. 1030-1045 ◽  
Author(s):  
Huaizhu Wu ◽  
Lu Xu ◽  
Christie M Ballantyne

Abstract Context The effects of dietary intake of different fatty acids and pharmacological use of fatty acids, specifically long-chain n-3 polyunsaturated fatty acids (LC n-3 PUFAs), on cardiovascular health and atherosclerotic cardiovascular disease (ASCVD) prevention have been examined in a large number of observational studies and clinical trials. This review summarizes recent data and discusses potential mechanisms. Evidence acquisition The review is based on the authors’ knowledge of the field supplemented by a PubMed search using the terms seafood, fish oil, saturated fatty acids, omega-3 fatty acids, eicosapentaenoic acid, docosahexaenoic acid, polyunsaturated fatty acids, monounsaturated fatty acids, and ASCVD. Evidence synthesis We mainly discuss the recent clinical trials that examine the effects of different types of dietary fatty acids and pharmacological use of n-3 PUFA products on ASCVD prevention and the potential mechanisms. Conclusions While replacement of dietary saturated fat with unsaturated fat, polyunsaturated fat in particular, or intake of LC n-3 PUFA–rich seafood has generally shown benefit for ASCVD prevention and is recommended for cardiovascular benefits, data on effects of n-3 PUFA products on ASCVD health are inconsistent. However, recent clinical trials support benefits of prescription EPA in ASCVD prevention. n-3 PUFAs may contribute to ASCVD prevention through multiple mechanisms, including lowering plasma triglyceride levels, anti-inflammatory effects, antithrombotic effects, and effects on endothelial function.


2008 ◽  
Vol 2 ◽  
pp. LPI.S1013 ◽  
Author(s):  
Brian M. Ross

Omega-3 polyunsaturated fatty acids play important roles in both the structure and communication processes of cells. Dietary deficiences of these fatty acids have been implicated in cardiac dysfunction, cancer and mood disorders. In the latter, clinical trials have strongly suggested that not all types of omega-3 PUFA are equally efficacious. In particular eicosapentaenoic acid (EPA) appears to be the most useful in ameliorating the symptoms of major depressive disorder. The mechanism by which omega-3 PUFA have these effects, and why EPA is apparently more effective in this role than the much more abundant brain lipid docosahexaenoic acid, is unclear. The available data do suggest various biologically plausible mechanisms all of which are amenable to study using straightforward experimental approaches. To progress further, a better understanding of how EPA and other omega-3 PUFA effect neurophysiological and neurosignalling processes is required.


Author(s):  
Rossella Avallone ◽  
Giovanni Vitale ◽  
Marco Bertolotti

A nutritional approach could be a promising strategy to prevent or slow the progression of neurodegenerative diseases such as Parkinson&rsquo;s and Alzheimer&rsquo;s disease, since there is no effective therapy for these diseases so far. The beneficial effects of omega-3 fatty acids are now well established by a plethora of studies through their involvement in multiple biochemical functions, including synthesis of antinflammatory mediators, cell membrane fluidity, intracellular signalling and gene expression. This systematic review will consider epidemiological studies and clinical trials that assessed the impact of supplementation or dietary intake of omega-3 polyunsaturated fatty acids on neurodegenerative diseases such as Parkinson&rsquo;s and Alzheimer&rsquo;s diseases. Indeed, treatment with omega-3 fatty acids, being safe and well tolerated, represent a valuable and biologically plausible tool in the management of neurodegenerative diseases in their early stages.


2019 ◽  
Vol 20 (17) ◽  
pp. 4256 ◽  
Author(s):  
Rossella Avallone ◽  
Giovanni Vitale ◽  
Marco Bertolotti

A nutritional approach could be a promising strategy to prevent or slow the progression of neurodegenerative diseases such as Parkinson’s and Alzheimer’s disease, since there is no effective therapy for these diseases so far. The beneficial effects of omega-3 fatty acids are now well established by a plethora of studies through their involvement in multiple biochemical functions, including synthesis of anti-inflammatory mediators, cell membrane fluidity, intracellular signaling, and gene expression. This systematic review will consider epidemiological studies and clinical trials that assessed the impact of supplementation or dietary intake of omega-3 polyunsaturated fatty acids on neurodegenerative diseases such as Parkinson’s and Alzheimer’s diseases. Indeed, treatment with omega-3 fatty acids, being safe and well tolerated, represents a valuable and biologically plausible tool in the management of neurodegenerative diseases in their early stages.


Nutrients ◽  
2020 ◽  
Vol 12 (12) ◽  
pp. 3718
Author(s):  
Anandita Pal ◽  
Adam H. Metherel ◽  
Lauren Fiabane ◽  
Nicole Buddenbaum ◽  
Richard P. Bazinet ◽  
...  

Eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) are n-3 polyunsaturated fatty acids (PUFAs) consumed in low abundance in the Western diet. Increased consumption of n-3 PUFAs may have beneficial effects for a wide range of physiological outcomes including chronic inflammation. However, considerable mechanistic gaps in knowledge exist about EPA versus DHA, which are often studied as a mixture. We suggest the novel hypothesis that EPA and DHA may compete against each other through overlapping mechanisms. First, EPA and DHA may compete for residency in membrane phospholipids and thereby differentially displace n-6 PUFAs, which are highly prevalent in the Western diet. This would influence biosynthesis of downstream metabolites of inflammation initiation and resolution. Second, EPA and DHA exert different effects on plasma membrane biophysical structure, creating an additional layer of competition between the fatty acids in controlling signaling. Third, DHA regulates membrane EPA levels by lowering its rate of conversion to EPA’s elongation product n-3 docosapentaenoic acid. Collectively, we propose the critical need to investigate molecular competition between EPA and DHA in health and disease, which would ultimately impact dietary recommendations and precision nutrition trials.


Cells ◽  
2020 ◽  
Vol 9 (12) ◽  
pp. 2605
Author(s):  
Sabina Cisa-Wieczorek ◽  
María Isabel Hernández-Alvarez

Lipids are important molecules for human health. The quantity and quality of fats consumed in the diet have important effects on the modulation of both the natural biosynthesis and degradation of lipids. There is an important number of lipid-failed associated metabolic diseases and an increasing number of studies suggesting that certain types of lipids might be beneficial to the treatment of many metabolic diseases. The aim of the present work is to expose an overview of de novo biosynthesis, storage, and degradation of lipids in mammalian cells, as well as, to review the published data describing the beneficial effects of these processes and the potential of some dietary lipids to improve metabolic diseases.


2013 ◽  
Vol 2013 ◽  
pp. 1-8 ◽  
Author(s):  
Benjamin B. Albert ◽  
David Cameron-Smith ◽  
Paul L. Hofman ◽  
Wayne S. Cutfield

Marine omega-3 rich oils are used by more than a third of American adults for a wide range of purported benefits including prevention of cardiovascular disease. These oils are highly prone to oxidation to lipid peroxides and other secondary oxidation products. Oxidized oils may have altered biological activity making them ineffective or harmful, though there is also evidence that some beneficial effects of marine oils could be mediated through lipid peroxides. To date, human clinical trials have not reported the oxidative status of the trial oil. This makes it impossible to understand the importance of oxidation to efficacy or harm. However, animal studies show that oxidized lipid products can cause harm. Oxidation of trial oils may be responsible for the conflicting omega-3 trial literature, including the prevention of cardiovascular disease. The oxidative state of an oil can be simply determined by the peroxide value and anisidine value assays. We recommend that all clinical trials investigating omega-3 harms or benefits report the results of these assays; this will enable better understanding of the benefits and harms of omega-3 and the clinical importance of oxidized supplements.


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