Chemical Compositional Changes in Over-Oxidized Fish Oils
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Non-Cyclooxygenase-Derived Prostanoids (F2-Isoprostanes) Are Formed in Situ on Phospholipids (Eicosanoids/Lipids/Oxidative Stress/Peroxidation/Free Radicals) JASON D
Proc. Nail. Acad. Sci. USA Vol. 89, pp. 10721-10725, November 1992 Pharmacology Non-cyclooxygenase-derived prostanoids (F2-isoprostanes) are formed in situ on phospholipids (eicosanoids/lipids/oxidative stress/peroxidation/free radicals) JASON D. MORROW, JOSEPH A. AWAD, HOLLIS J. BOSS, IAN A. BLAIR, AND L. JACKSON ROBERTS II* Departments of Pharmacology and Medicine, Vanderbilt University, Nashville, TN 37232.6602 Communicated by Philip Needleman, July 21, 1992 (receivedfor review March 11, 1992) ABSTRACT We recently reported the discovery ofa series the formation ofthese prostanoids occurs independent ofthe of bioactive prostaglandin F2-like compounds (F2-isoprostanes) catalytic activity of the cyclooxygenase enzyme, which had that are produced in vivo by free radical-catalyzed peroxidation been considered obligatory for endogenous prostanoid bio- ofarachidonic acid independent ofthe cyclooxygenase enzyme. synthesis. Circulating levels ofthese compounds were shown Inasmuch as phospholipids readily undergo peroxidation, we to increase dramatically in animal models of free radical examined the possibility that F2-isoprostanes may be formed in injury (8). Interestingly, the levels of these prostanoids in situ on phospholipids. Initial support for this hypothesis was normal human plasma and urine are one or two orders of obtained by the rmding that levels of free F2-isoprostanes magnitude higher than those of prostaglandins produced by measured after hydrolysis oflipids extracted from livers ofrats the cyclooxygenase enzyme. Formation ofthese compounds treated with CCI4 to induce lipid peroxidation were more than proceeds through intermediates composed of four positional 100-fold higher than levels in untreated animal. Further, peroxyl radical isomers of arachidonic acid which undergo increased levels of lipid-associated F2-isoprostanes in livers of endocyclization to yield bicyclic endoperoxide PGG2-like CCI4-treated rats preceded the appearance of free compounds compounds. -
Therapeutic Effects of Specialized Pro-Resolving Lipids Mediators On
antioxidants Review Therapeutic Effects of Specialized Pro-Resolving Lipids Mediators on Cardiac Fibrosis via NRF2 Activation 1, 1,2, 2, Gyeoung Jin Kang y, Eun Ji Kim y and Chang Hoon Lee * 1 Lillehei Heart Institute, University of Minnesota, Minneapolis, MN 55455, USA; [email protected] (G.J.K.); [email protected] (E.J.K.) 2 College of Pharmacy, Dongguk University, Seoul 04620, Korea * Correspondence: [email protected]; Tel.: +82-31-961-5213 Equally contributed. y Received: 11 November 2020; Accepted: 9 December 2020; Published: 10 December 2020 Abstract: Heart disease is the number one mortality disease in the world. In particular, cardiac fibrosis is considered as a major factor causing myocardial infarction and heart failure. In particular, oxidative stress is a major cause of heart fibrosis. In order to control such oxidative stress, the importance of nuclear factor erythropoietin 2 related factor 2 (NRF2) has recently been highlighted. In this review, we will discuss the activation of NRF2 by docosahexanoic acid (DHA), eicosapentaenoic acid (EPA), and the specialized pro-resolving lipid mediators (SPMs) derived from polyunsaturated lipids, including DHA and EPA. Additionally, we will discuss their effects on cardiac fibrosis via NRF2 activation. Keywords: cardiac fibrosis; NRF2; lipoxins; resolvins; maresins; neuroprotectins 1. Introduction Cardiovascular disease is the leading cause of death worldwide [1]. Cardiac fibrosis is a major factor leading to the progression of myocardial infarction and heart failure [2]. Cardiac fibrosis is characterized by the net accumulation of extracellular matrix proteins in the cardiac stroma and ultimately impairs cardiac function [3]. Therefore, interest in substances with cardioprotective activity continues. -
Detection of F2-Isoprostanes and F4-Neuroprostanes in Clinical Studies
Mini Review Detection of F2-isoprostanes and F4-neuroprostanes in Clinical Studies Hsiu-Chuan Yen Graduate Institute of Medical Biotechnology Department of Medical Biotechnology and Laboratory Science Chang Gung University, Taoyuan, Taiwan Detecting stable products of oxidative damage is the most reliable approach to access oxidative stress in vivo. F2-isoprostanes (F2-IsoPs) and F4-neuroprostanes (F4-NPs) are the most specific markers of lipid peroxidation, which is superior to other markers of oxidative damage for clinical studies in many ways. F2-IsoPs is formed from peroxidation of arachidonic acid that is abundant in all kind of cells, while F4-NPs is derived from docosahexaenoic acid enriched in neurons. Moreover, F2-IsoPs is known to exhibit biological activities, such as vasoconstriction and platelet aggregation. Gas chromatography/negative-ion chemical-ionization mass spectrometry (GC/NICI-MS) is the reference method and the method with highest sensitivity to quantify F2-IsoPs and F4-NPs. F2-IsoPs is not only a widely used gold marker of lipid peroxidation detectable in all types of body fluids, but also a cause of diseases due to its biological activities, a marker to evaluate severity or predict out- come of diseases, or a tool to monitor the effectiveness of antioxidant therapy. Clinical studies de- tecting F4-NPs are little because cerebrospinal fluid or brain tissues are needed, but it is more useful than F2-IsoPs in selectively evaluating neuronal oxidative damage. This paper will discuss the above issues with emphasis on the advantages and considerations in clinical studies. Key words: Lipid peroxidation, Gas chromatography/negative-ion chemical-ionization mass spectrometry, Body fluid, Neuron The best way to access oxidative stress in humans is to detect specific and stable markers of oxidative dam- Introduction age using reliable methods. -
A Comprehensive Review Article on Isoprostanes As Biological Markers
mac har olo P gy Jadoon and Malik, Biochem Pharmacol (Los Angel) 2018, 7:2 : & O y r p t e s DOI: 10.4172/2167-0501.1000246 i n A m c e c h e c s Open Access o i s Biochemistry & Pharmacology: B ISSN: 2167-0501 Review Article Open Access A Comprehensive Review Article on Isoprostanes as Biological Markers Saima Jadoon* and Arif Malik Institute of Molecular Biology and Biotechnology, University of Lahore, Lahore, Pakistan Abstract Various obsessive procedures include free radical intervened oxidative anxiety. The elaboration of solid and non- intrusive strategies for the assessment of oxidative worry in human body is a standout amongst the most critical strides towards perceiving the assortment of oxidative disorders apparently created by Reactive Oxygen Species (ROS). Lipid peroxidation is a standout amongst the most well-known components related with oxidative anxiety, and the estimation of lipid peroxidation items has been utilized to assess oxidative worry in vivo conditions. The estimation of conjugated dienes and lipid hydro peroxide, while the evaluation of optional final results incorporates thiobarbituric acid reactive substances, vaporous alkanes and prostaglandin F2-like items, named F2-isoprostanes (F2-iPs). As of late, F2-iPs have been viewed as the most significant, precise and solid marker of oxidative worry in vivo and their evaluation is suggested for surveying oxidant wounds in people. The motivation behind this paper is to give some data on organic chemistry of isoprostanes and their use as a marker of oxidative anxiety. Keywords: Lipid peroxidation; Prostaglandin F2; Conjugated undifferentiated from prostaglandins PGF2 to recognize upgraded rates products; Arachidonic acid metabolites of lipid peroxidation. -
Functional Metabolomics Reveals Novel Active Products in the DHA Metabolome
Functional Metabolomics Reveals Novel Active Products in the DHA Metabolome The Harvard community has made this article openly available. Please share how this access benefits you. Your story matters. Citation Shinohara, Masakazu, Valbona Mirakaj, and Charles N. Serhan. 2012. Functional metabolomics reveals novel active products in the DHA metabolome. Frontiers in Immunology 3:81. Published Version doi:10.3389/fimmu.2012.00081 Accessed February 19, 2015 10:33:44 AM EST Citable Link http://nrs.harvard.edu/urn-3:HUL.InstRepos:10366358 Terms of Use This article was downloaded from Harvard University's DASH repository, and is made available under the terms and conditions applicable to Other Posted Material, as set forth at http://nrs.harvard.edu/urn-3:HUL.InstRepos:dash.current.terms-of- use#LAA (Article begins on next page) REVIEW ARTICLE published: 17 April 2012 doi: 10.3389/fimmu.2012.00081 Functional metabolomics reveals novel active products in the DHA metabolome Masakazu Shinohara,Valbona Mirakaj and Charles N. Serhan* Center for Experimental Therapeutics and Reperfusion Injury, Department of Anesthesiology, Perioperative and Pain Medicine, Brigham and Women’s Hospital, Harvard Medical School, Boston, MA, USA Edited by: Endogenous mechanisms for successful resolution of an acute inflammatory response and Masaaki Murakami, Osaka University, the local return to homeostasis are of interest because excessive inflammation underlies Japan many human diseases. In this review, we provide an update and overview of functional Reviewed by: Takayuki Yoshimoto,Tokyo Medical metabolomics that identified a new bioactive metabolome of docosahexaenoic acid (DHA). University, Japan Systematic studies revealed that DHA was converted to DHEA-derived novel bioactive Hiroki Yoshida, Saga University products as well as aspirin-triggered forms of protectins (AT-PD1). -
Cysteinyl Leukotrienes and 8-Isoprostane in Exhaled Breath
505 ASTHMA Thorax: first published as 10.1136/thorax.58.6.509 on 1 June 2003. Downloaded from Cysteinyl leukotrienes and 8-isoprostane in exhaled breath condensate of children with asthma exacerbations E Baraldi, S Carraro, R Alinovi, A Pesci, L Ghiro, A Bodini, G Piacentini, F Zacchello, S Zanconato ............................................................................................................................. Thorax 2003;58:505–509 Background: Cysteinyl leukotrienes (Cys-LTs) and isoprostanes are inflammatory metabolites derived from arachidonic acid whose levels are increased in the airways of asthmatic patients. Isoprostanes are relatively stable and specific for lipid peroxidation, which makes them potentially reliable biomarkers for oxidative stress. A study was undertaken to evaluate the effect of a course of oral steroids on Cys-LT and 8-isoprostane levels in exhaled breath condensate of children with an asthma exacerbation. Methods: Exhaled breath condensate was collected and fractional exhaled nitric oxide (FENO) and spirometric parameters were measured before and after a 5 day course of oral prednisone (1 mg/kg/ day) in 15 asthmatic children with an asthma exacerbation. Cys-LT and 8-isoprostane concentrations were measured using an enzyme immunoassay. FENO was measured using a chemiluminescence ana- lyser. Exhaled breath condensate was also collected from 10 healthy children. Results: Before prednisone treatment both Cys-LT and 8-isoprostane concentrations were higher in See end of article for asthmatic subjects (Cys-LTs, 12.7 pg/ml (IQR 5.4–15.6); 8-isoprostane, 12.0 pg/ml (9.4–29.5)) than authors’ affiliations ....................... in healthy children (Cys-LTs, 4.3 pg/ml (2.0–5.7), p=0.002; 8-isoprostane, 2.6 pg/ml (2.1–3.0), p<0.001). -
Oxylipin Response to Acute and Chronic Exercise: a Systematic Review
H OH metabolites OH Review Oxylipin Response to Acute and Chronic Exercise: A Systematic Review Étore F. Signini 1,* , David C. Nieman 2 , Claudio D. Silva 1 , Camila A. Sakaguchi 1 and Aparecida M. Catai 1 1 Physical Therapy Department, Federal University of São Carlos, São Carlos, SP 13565-905, Brazil; [email protected] (C.D.S.); [email protected] (C.A.S.); [email protected] (A.M.C.) 2 North Carolina Research Campus, Appalachian State University, Kannapolis, NC 28081, USA; [email protected] * Correspondence: [email protected] Received: 28 May 2020; Accepted: 19 June 2020; Published: 25 June 2020 Abstract: Oxylipins are oxidized compounds of polyunsaturated fatty acids that play important roles in the body. Recently, metabololipidomic-based studies using advanced mass spectrometry have measured the oxylipins generated during acute and chronic physical exercise and described the related physiological effects. The objective of this systematic review was to provide a panel of the primary exercise-related oxylipins and their respective functions in healthy individuals. Searches were performed in five databases (Cochrane, PubMed, Science Direct, Scopus and Web of Science) using combinations of the Medical Subject Headings (MeSH) terms: “Humans”, “Exercise”, “Physical Activity”, “Sports”, “Oxylipins”, and “Lipid Mediators”. An adapted scoring system created in a previous study from our group was used to rate the quality of the studies. Nine studies were included after examining 1749 documents. Seven studies focused on the acute effect of physical exercise while two studies determined the effects of exercise training on the oxylipin profile. Numerous oxylipins are mobilized during intensive and prolonged exercise, with most related to the inflammatory process, immune function, tissue repair, cardiovascular and renal functions, and oxidative stress. -
Oxidation of Polyunsaturated Fatty Acids to Produce Lipid Mediators
Essays in Biochemistry (2020) 64 401–421 https://doi.org/10.1042/EBC20190082 Review Article Oxidation of polyunsaturated fatty acids to produce lipid mediators William W. Christie1 and John L. Harwood2 1James Hutton Institute, Invergowrie, Dundee, Scotland DD2 5DA, U.K.; 2School of Biosciences, Cardiff University, Cardiff CF10 3AX, Wales, U.K. Correspondence: John L. Harwood ([email protected]) Downloaded from http://portlandpress.com/essaysbiochem/article-pdf/64/3/401/893636/ebc-2019-0082c.pdf by guest on 29 September 2021 The chemistry, biochemistry, pharmacology and molecular biology of oxylipins (defined as a family of oxygenated natural products that are formed from unsaturated fatty acids by pathways involving at least one step of dioxygen-dependent oxidation) are complex and occasionally contradictory subjects that continue to develop at an extraordinarily rapid rate. The term includes docosanoids (e.g. protectins, resolvins and maresins, or special- ized pro-resolving mediators), eicosanoids and octadecanoids and plant oxylipins, which are derived from either the omega-6 (n-6) or the omega-3 (n-3) families of polyunsaturated fatty acids. For example, the term eicosanoid is used to embrace those biologically active lipid mediators that are derived from C20 fatty acids, and include prostaglandins, thrombox- anes, leukotrienes, hydroxyeicosatetraenoic acids and related oxygenated derivatives. The key enzymes for the production of prostanoids are prostaglandin endoperoxide H synthases (cyclo-oxygenases), while lipoxygenases and oxidases of the cytochrome P450 family pro- duce numerous other metabolites. In plants, the lipoxygenase pathway from C18 polyunsat- urated fatty acids yields a variety of important products, especially the jasmonates, which have some comparable structural features and functions. -
Leukotriene B and 8-Isoprostane in Exhaled Breath Condensate
ORIGINAL ARTICLE Leukotriene B4 and 8-Isoprostane in Exhaled Breath Condensate of Children With Episodic and Persistent Asthma S Caballero Balanzá,1 A Martorell Aragonés,1 JC Cerdá Mir,1 JB Ramírez,2 R Navarro Iváñez,3 A Navarro Soriano,4 R Félix Toledo,1 A Escribano Montaner5 1Unidad de Alergología, Hospital General Universitario, Valencia, Spain 2Laboratorio de Función Pulmonar, Instituto Nacional de Silicosis, Área de Gestión del Pulmón. H. Central Universitario de Asturias, Oviedo, Spain 3Servicio de Neumología. Hospital General Universitario, Valencia, Spain 4Fundación de Investigación. Hospital General Universitario Valencia, Spain ■ Abstract Background: Leukotrienes and isoprostanes are biomarkers of airway infl ammation and oxidative stress that can be detected in exhaled breath condensate (EBC). The aim of this study was to evaluate leukotriene B4 (LTB4) and 8-isoprostane levels in EBC of healthy and asthmatic children with episodic and moderate persistent asthma. Methods: EBC was collected from 62 children aged 6 to 14 years: 22 healthy children, 30 patients with episodic asthma, and 10 patients with moderate persistent asthma, without preventive treatment at the time of enrolment. Results: LTB 4 concentrations were higher in children with asthma than in healthy controls (50.7 pg/mL vs 13.68 pg/mL, P<.011). The same was true for children with moderate persistent asthma compared to children with episodic asthma (146.9 pg/mL vs 18.85 pg/mL, P<.0001), children with moderate persistent asthma compared to healthy controls (146.9 pg/mL vs 13.68 pg/mL, P<.0001), and children with episodic asthma compared to healthy controls (P, nonsignifi cant). -
Thromboxane Receptor Activation Mediates Isoprostane- Induced Increases in Amyloid Pathology in Tg2576 Mice
The Journal of Neuroscience, April 30, 2008 • 28(18):4785–4794 • 4785 Neurobiology of Disease Thromboxane Receptor Activation Mediates Isoprostane- Induced Increases in Amyloid Pathology in Tg2576 Mice Diana W. Shineman,1 Bin Zhang,1 Susan N. Leight,1 Domenico Pratico,2 and Virginia M.-Y. Lee1 1Department of Pathology and Laboratory Medicine, Center for Neurodegenerative Disease Research, University of Pennsylvania School of Medicine, Philadelphia, Pennsylvania 19104, and 2Department of Pharmacology, Temple University School of Medicine, Philadelphia, Pennsylvania 19122 Alzheimer’s disease (AD) amyloid plaques are composed of amyloid- (A) peptides produced from proteolytic cleavage of amyloid precursor protein (APP). Isoprostanes, markers of in vivo oxidative stress, are elevated in AD patients and in the Tg2576 mouse model of   AD-like A brain pathology. To determine whether isoprostanes increase A production, we delivered isoprostane iPF2␣-III into the brains of Tg2576 mice. Although treated mice showed increased brain A levels and plaque-like deposits, this was blocked by a throm-  boxane (TP) receptor antagonist, suggesting that TP receptor activation mediates the effects of iPF2␣-III on A . This hypothesis was supported by cell culture studies that showed that TP receptor activation increased A and secreted APP ectodomains. This increase was a result of increased APP mRNA stability leading to elevated APP mRNA and protein levels. The increased APP provides more substrate for ␣ and  secretase proteolytic cleavages, thereby increasing A generation and amyloid plaque deposition. To test the effectiveness of targeting the TP receptor for AD therapy, Tg2576 mice underwent long-term treatment with S18886, an orally available TP receptor antagonist. -
Cysteinyl Leukotriene Correlated with 8-Isoprostane Levels As Predictive
Qasem et al. Lipids in Health and Disease (2016) 15:130 DOI 10.1186/s12944-016-0298-0 RESEARCH Open Access Cysteinyl leukotriene correlated with 8- isoprostane levels as predictive biomarkers for sensory dysfunction in autism Hanan Qasem2, Laila Al-Ayadhi3,4,5 and Afaf El-Ansary1,3,4,6* Abstract Background: Autism is a neurodevelopmental disorder that clinically presented as cognitive deficits, social impairments and sensory dysfunction. An increasing body of evidence has shown that oxidative stress and inflammation are involved in the pathophysiology of autism. Recording biomarkers as measure of the severity of autistic features might help in understanding the pathophysiology of autism. Methods: This study investigates the plasma levels of 8-isoprostane and Cysteinyl leukotrienes (CysLTs) in 44 autistic children and 40 healthy controls. The recruited autistic patients were assessed for behavior, cognitive and sensory deficits by using different autism severity rating scales, including the Childhood Autism Rating Scales (CARS), Social responsiveness scale (SRS) and Short Sensory Profile (SSP). Receiver Operating Characteristics analysis (ROC) of the obtained data was performed to measure the predictive value of 8-isoprostane and Cysteinyl leukotrienes (CysLTs) as oxidative stress- related parameters. Pearson’s correlations between the measured parameters was also performed. Results: The concentrations of 8-isoprostane and CysLTs in autistic patients were significantly higher than those in controls. While cognitive and social impairments did not show any significant differences, the SSP results were strongly correlated with the levels of both of the biomarkers assessed. However, autistic children showed improvements in oxidative stress status (as determined by 8-isoprostane levels) at increasing ages. -
The Effect of Agility Exercise on Eicosanoid Excretion, Oxidant Status, and Plasma Lactate in Dogs
Baltzer et al. BMC Veterinary Research 2012, 8:249 http://www.biomedcentral.com/1746-6148/8/249 RESEARCH ARTICLE Open Access The effect of agility exercise on eicosanoid excretion, oxidant status, and plasma lactate in dogs Wendy I Baltzer1*, Anna M Firshman2, Bernadette Stang1, Jennifer J Warnock1, Elena Gorman1 and Erica C McKenzie1 Abstract Background: The objective was to determine the effects of agility exercise on dogs of different skill levels with respect to urinary eicosanoids, urinary 15F2t-isoprostane (lipid peroxidation marker) and hematological/biochemical changes in plasma. Fifteen adult dogs had blood and urine samples obtained prior to, immediately and 4-hours following an agility exercise. Results: Hematocrit, red blood cells (RBC), albumin, and hemoglobin increased following exercise, with greatest increases correlating to increased skill group (novice, intermediate, masters); at 4-hours post-exercise, hematocrit, RBC, and hemoglobin were decreased. Phosphorus increased following exercise with the greatest increase in novice and intermediates. Plasma lactate increased 3.6-fold in masters, 3.2-fold in intermediates, and 1.2-fold in novice dogs. Urine thromboxane B2 (TXB2) more than tripled 4-hours post-exercise while 6-keto prostaglandin F1α (PGF1α, prostacyclin metabolite), prostaglandin E2 metabolites (13,14-dihydro-15-keto-prostaglandin A2 and 13, 14-dihydro-15-keto-prostaglandin E2), and 13,14-dihydro-15-keto prostaglandin F2α were unaffected as determined by a competitive enzyme immunoassay and standardized by division with urine creatinine. Urine 15F2t-isoprostane increased insignificantly. Conclusions: Alterations in the plasma post-exercise were likely due to hemoconcentration from insensible water loss, splenic contraction and sympathetic stimulation while 4-hours later autohemodilution reduced RBC parameters.