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Todd R Harris, Sean Kodani, Jun Yang, Denise M Imai, Bruce D Hammock
Exposure to the halogenated hydrocarbon carbon tetrachloride (CCl4) leads to hepatic lipid peroxidation, inflammation and fibrosis. Dietary supplementation of ω-3 fatty acids has been increasingly advocated as being generally anti-inflammatory, though its effect in models of liver fibrosis is mixed. This raises the question of whether diets high in ω-3 fatty acids will result in a greater sensitivity or resistance to liver fibrosis as a result of environmental toxicants like CCl4. In this study, we fed CCl4-treated mice a high ω-3 diet (using a mix of docosahexaenoic acid and eicosapentaenoic acid ethyl esters)...
September 14, 2016: Journal of Nutritional Biochemistry
Mohammed Sherif, Eva-Maria Becker, Cornelia Herrfurth, Ivo Feussner, Petr Karlovsky, Richard Splivallo
Along with barley and rice, maize provides staple food for more than half of the world population. Maize ears are regularly infected with fungal pathogens of the Fusarium genus, which, besides reducing yield, also taint grains with toxic metabolites. In an earlier work, we have shown that maize ears infection with single Fusarium strains was detectable through volatile sensing. In nature, infection most commonly occurs with more than a single fungal strain; hence we tested how the interactions of two strains would modulate volatile emission from infected ears...
2016: Frontiers in Plant Science
Souvik Mitra, Barend V Burger, Mousumi Poddar-Sarkar
Mosses have an inherent adaptability against different biotic and abiotic stresses. Oxylipins, the volatile metabolites derived from polyunsaturated fatty acids (PUFAs), play a key role in the chemical defence strategy of mosses. In the present study, a comparative survey of these compounds, including an investigation into their precursor fatty acids (FAs), was carried out for the first time on the mosses Brachymenium capitulatum (Mitt.) Paris, Hydrogonium consanguineum (Thwaites & Mitt.) Hilp., Barbula hastata Mitt...
October 5, 2016: Protoplasma
Jessay Gopuran Devassy, Shan Leng, Melissa Gabbs, Md Monirujjaman, Harold M Aukema
Alzheimer disease (AD) is becoming one of the most prevalent neurodegenerative conditions worldwide. Although the disease progression is becoming better understood, current medical interventions can only ameliorate some of the symptoms but cannot slow disease progression. Neuroinflammation plays an important role in the advancement of this disorder, and n-3 (ω-3) polyunsaturated fatty acids (PUFAs) are involved in both the reduction in and resolution of inflammation. These effects may be mediated by the anti-inflammatory and proresolving effects of bioactive lipid mediators (oxylipins) derived from n-3 PUFAs [eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA)] in fish oil...
September 2016: Advances in Nutrition
Bart V J Cuppen, Junzeng Fu, Herman A van Wietmarschen, Amy C Harms, Slavik Koval, Anne C A Marijnissen, Judith J W Peeters, Johannes W J Bijlsma, Janneke Tekstra, Jacob M van Laar, Thomas Hankemeier, Floris P J G Lafeber, Jan van der Greef
In clinical practice, approximately one-third of patients with rheumatoid arthritis (RA) respond insufficiently to TNF-α inhibitors (TNFis). The aim of the study was to explore the use of a metabolomics to identify predictors for the outcome of TNFi therapy, and study the metabolomic fingerprint in active RA irrespective of patients' response. In the metabolomic profiling, lipids, oxylipins, and amines were measured in serum samples of RA patients from the observational BiOCURA cohort, before start of biological treatment...
2016: PloS One
Monika D Arnold, Cornelia Gruber, Kristýna Floková, Otto Miersch, Miroslav Strnad, Ondřej Novák, Claus Wasternack, Bettina Hause
Oxylipins of the jasmonate family are active as signals in plant responses to biotic and abiotic stresses as well as in development. Jasmonic acid (JA), its precursor cis-12-oxo-phytodienoic acid (OPDA) and the isoleucine conjugate of JA (JA-Ile) are the most prominent members. OPDA and JA-Ile have individual signalling properties in several processes and differ in their pattern of gene expression. JA-Ile, but not OPDA, is perceived by the SCFCOI1-JAZ co-receptor complex. There are, however, numerous processes and genes specifically induced by OPDA...
2016: PloS One
Ahmad Hanif, Matthew L Edin, Darryl C Zeldin, Christophe Morisseau, Mohammed A Nayeem
Coronary reactive hyperemia (CRH) is a physiological response to ischemic insult that prevents the potential harm associated with an interruption of blood supply. The relationship between the pharmacologic inhibition of soluble epoxide hydrolase (sEH) and CRH response to a brief ischemia is not known. sEH is involved in the main catabolic pathway of epoxyeicosatrienoic acids (EETs), which are converted into dihydroxyeicosatrienoic acids (DHETs). EETs protect against ischemia/reperfusion injury and have numerous beneficial physiological effects...
2016: PloS One
Aleix Sala-Vila, Andrés Díaz-López, Cinta Valls-Pedret, Montserrat Cofán, Alfredo García-Layana, Rosa-María Lamuela-Raventós, Olga Castañer, Vicente Zanon-Moreno, Miguel A Martinez-Gonzalez, Estefanía Toledo, Josep Basora, Jordi Salas-Salvadó, Dolores Corella, Enrique Gómez-Gracia, Miquel Fiol, Ramón Estruch, José Lapetra, Montserrat Fitó, Fernando Arós, Luis Serra-Majem, Xavier Pintó, Emilio Ros
Importance: Diabetic retinopathy (DR) is a devastating complication of individuals with type 2 diabetes mellitus. The retina is rich in long-chain ω-3 polyunsaturated fatty acids (LCω3PUFAs), which are substrate for oxylipins with anti-inflammatory and antiangiogenic properties. Experimental models support dietary LCω3PUFA protection against DR, but clinical data are lacking. Objective: To determine whether LCω3PUFA intake relates to a decreased incidence of sight-threatening DR in individuals with type 2 diabetes older than 55 years...
October 1, 2016: JAMA Ophthalmology
Seungkyu Lee, Eugene A Kapustin, Omar M Yaghi
A chiral metal-organic framework, MOF-520, was used to coordinatively bind and align molecules of varying size, complexity, and functionality. The reduced motional degrees of freedom obtained with this coordinative alignment method allowed the structures of molecules to be determined by single-crystal x-ray diffraction techniques. The chirality of the MOF backbone also served as a reference in the structure solution for an unambiguous assignment of the absolute configuration of bound molecules. Sixteen molecules representing four common functional groups (primary alcohol, phenol, vicinal diol, and carboxylic acid), ranging in complexity from methanol to plant hormones (gibberellins, containing eight stereocenters), were crystallized and had their precise structure determined...
August 19, 2016: Science
Stephanie P B Caligiuri, Delfin Rodriguez-Leyva, Harold M Aukema, Amir Ravandi, Wendy Weighell, Randolph Guzman, Grant N Pierce
UNLABELLED: In the year-long FlaxPAD clinical trial (Flaxseed for Peripheral Artery Disease), dietary flaxseed generated a powerful reduction in brachial systolic and diastolic blood pressure in patients with peripheral artery disease. Oxylipins were implicated as potential mechanistic mediators. However, the ability of flaxseed to impact central aortic hypertension, arterial stiffness, or cardiac performance was not investigated. Additionally, the relationship between central blood pressure (cBP) and oxylipins was not elucidated...
October 2016: Hypertension
Amanda Lo Van, Nobuyuki Sakayori, Mayssa Hachem, Mounir Belkouch, Madeleine Picq, Michel Lagarde, Noriko Osumi, Nathalie Bernoud-Hubac
Docosahexaenoic acid (DHA; 22:6 ω-3) is highly enriched in the brain and is required for proper brain development and function. Its deficiency has been shown to be linked with the emergence of neurological diseases. Dietary ω-3 fatty acid supplements including DHA have been suggested to improve neuronal development and enhance cognitive functions. However, mechanisms of DHA incorporation in the brain remain to be fully understood. Findings suggested that DHA is better incorporated when esterified within lysophospholipid rather than under its non-esterified form...
August 2, 2016: Biochimie
Ahmad Hanif, Matthew L Edin, Darryl C Zeldin, Christophe Morisseau, Mohammed A Nayeem
The relationship between soluble epoxide hydrolase (sEH) and coronary reactive hyperemia (CRH) response to a brief ischemic insult is not known. Epoxyeicosatrienoic acids (EETs) exert cardioprotective effects in ischemia/reperfusion injury. sEH converts EETs into dihydroxyeicosatrienoic-acids (DHETs). Therefore, we hypothesized that knocking out sEH enhances CRH through modulation of oxylipin profiles, including an increase in EET/DHET ratio. Compared with sEH(+/+), sEH(-/-) mice showed enhanced CRH, including greater repayment volume (RV; 28% higher, P < 0...
October 1, 2016: American Journal of Physiology. Regulatory, Integrative and Comparative Physiology
Chetna Tyagi, Archana Singh, Indrakant Kumar Singh
Various types of oxygenated fatty acids termed 'oxylipins' are involved in plant response to herbivory. Oxylipins like jasmonic acid (JA) and green leafy volatiles (GLVs) are formed by the action of enzymes like allene oxide synthase (AOS) and hydroxyperoxide lyase (HPL) respectively. In this study, we focus on AOS of Oryza sativa sb. Japonica, that interact with 9- and 13- hydroxyperoxides to produce intermediates of jasmonate pathway and compare it with rice HPL that yields GLVs. We attempt to elucidate the interaction pattern by computational docking protocols keeping the Arabidopsis AOS system as the reference model system...
July 2, 2016: Computational Biology and Chemistry
Jennifer Yeung, Benjamin E Tourdot, Reheman Adili, Abigail R Green, Cody J Freedman, Pilar Fernandez-Perez, Johnny Yu, Theodore R Holman, Michael Holinstat
OBJECTIVE: Dietary supplementation with polyunsaturated fatty acids has been widely used for primary and secondary prevention of cardiovascular disease in individuals at risk; however, the cardioprotective benefits of polyunsaturated fatty acids remain controversial because of lack of mechanistic and in vivo evidence. We present direct evidence that an omega-6 polyunsaturated fatty acid, dihomo-γ-linolenic acid (DGLA), exhibits in vivo cardioprotection through 12-lipoxygenase (12-LOX) oxidation of DGLA to its reduced oxidized lipid form, 12(S)-hydroxy-8Z,10E,14Z-eicosatrienoic acid (12(S)-HETrE), inhibiting platelet activation and thrombosis...
October 2016: Arteriosclerosis, Thrombosis, and Vascular Biology
Bruce A Watkins, Jeffrey Kim, Anne Kenny, Theresa L Pedersen, Kirk L Pappan, John W Newman
Postmenopausal women (PMW) report marginal n-3 PUFA intakes and are at risk of chronic diseases associated with the skeletal, muscular, neuroendocrine, and cardiovascular systems. How n-3 PUFA affect the amounts of endocannabinoids (ECs) and oxylipins (OLs) of metabolic and physiologic importance in PMW is not clear. Based on our recent findings that dietary n-3 PUFA alter gene targets of the EC system and lower pro-inflammatory OL we proceeded to characterize these actions in blood of PMW. Our aim was to determine levels of the ECs, OLs, and global metabolites (GM) in white PMW (75±7y), randomized in a double-masked manner, from baseline to 6mo after receiving a fish oil supplement of n-3 PUFA (720mg 20:5n3+480mg 22:6n3/d, n=20) or placebo (1...
November 2016: Biochimica et Biophysica Acta
Iván Antonio García-Montalvo, Gabriel Mayoral Andrade, Laura Perez-Campos Mayoral, Socorro Pina Canseco, Ruth Martinez Cruz, Margarito Martínez-Cruz, Edgar Zenteno, Eduardo Perez-Campos Mayoral, Itandehui Velasco Gallegos, Maria Teresa Hernandez-Huerta, Diana Matias-Perez, Eduardo Pérez-Campos
Prostaglandins present in seminal fluid are actively involved in vascular and non-vascular smooth muscle maintenance, reproduction, and inflammatory processes. Seminal plasma contains molecules, such as oxylipins, which possess cell signaling functions. Several studies have shown that specific molecules in seminal fluid can increase passive diffusion, and cause interactions in the female reproductive tract. This may provoke a cascade of cellular and molecular changes in general health and certain diseases. This study examines the hypothesis that the molecules in seminal fluid are involved in platelet activity...
August 2016: Medical Hypotheses
Ye Sun, Hiromi W L Koh, Hyungwon Choi, Woon-Puay Koh, Jian-Min Yuan, John W Newman, Jin Su, Jinling Fang, Choon Nam Ong, Rob M van Dam
We aimed to examine the prospective association between plasma FAs, oxylipins, and risk of acute myocardial infarction (AMI) in a Singapore Chinese population. A nested case-control study with 744 incident AMI cases and 744 matched controls aged 47-83 years was conducted within the Singapore Chinese Health Study. Nineteen plasma FAs and 12 oxylipins were quantified using MS. These were grouped into 12 FA clusters and 5 oxylipin clusters using hierarchical clustering, and their associations with AMI risk were assessed...
July 2016: Journal of Lipid Research
James R Collins, Bethanie R Edwards, Helen F Fredricks, Benjamin A S Van Mooy
Discovery and identification of molecular biomarkers in large LC/MS data sets requires significant automation without loss of accuracy in the compound screening and annotation process. Here, we describe a lipidomics workflow and open-source software package for high-throughput annotation and putative identification of lipid, oxidized lipid, and oxylipin biomarkers in high-mass-accuracy HPLC-MS data. Lipid and oxylipin biomarker screening through adduct hierarchy sequences, or LOBSTAHS, uses orthogonal screening criteria based on adduct ion formation patterns and other properties to identify thousands of compounds while providing the user with a confidence score for each assignment...
July 19, 2016: Analytical Chemistry
Ameer Y Taha, Marie Hennebelle, Jun Yang, Daisy Zamora, Stanley I Rapoport, Bruce D Hammock, Christopher E Ramsden
Linoleic acid (LA, 18:2n-6) is the most abundant polyunsaturated fatty acid in the North American diet and is a precursor to circulating bioactive fatty acid metabolites implicated in brain disorders. This exploratory study tested the effects of increasing dietary LA on plasma and cerebral cortex metabolites derived from LA, its elongation-desaturation products dihomo-gamma linolenic (DGLA, 20:3n-6) acid and arachidonic acid (AA, 20:4n-6), as well as omega-3 alpha-linolenic (α-LNA, 18:3n-3), eicosapentaenoic (EPA, 20:5n-3) and docosahexaenoic acid (DHA, 22:6n-3)...
May 11, 2016: Prostaglandins, Leukotrienes, and Essential Fatty Acids
Yiyi Zhang, Eliseo Guallar, Elena Blasco-Colmenares, Amy C Harms, Rob J Vreeken, Thomas Hankemeier, Gordon F Tomaselli, Alan Cheng
INTRODUCTION: Individuals with systolic heart failure are at risk of ventricular arrhythmias and all-cause mortality. Little is known regarding the mechanisms underlying these events. We sought to better understand if oxylipins, a diverse class of lipid metabolites derived from the oxidation of polyunsaturated fatty acids, were associated with these outcomes in recipients of primary prevention implantable cardioverter defibrillators (ICDs). METHODS: Among 479 individuals from the PROSE-ICD study, baseline serum were analyzed and quantitatively profiled for 35 known biologically relevant oxylipin metabolites...
2016: PloS One
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