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Oxylipins

Oxylipins are a diverse group of oxygenated lipid mediators derived from polyunsaturated fatty acids.
They play crucial roles in regulating inflammation, immune function, and various physiological processes.
Oxylipins include prostanoids, leukotrienes, and other oxidized fatty acid derivatives that act as potent signaling molecules.
Understanding the complex biology of oxylipins is essential for researchers studying areas such as cardiovascular health, neurodegeneration, and metabolic disorders.
This MeSH term provides a comprehensive overview of the structural diversity, biosynthetic pathways, and functional significance of this important class of lipid-derived mediators.

Most cited protocols related to «Oxylipins»

1
Oxylipin Quantification Protocol
Two different types of compounds (Table S-6) were used as internal standards. Type I internal standards were added to samples before extraction to mimic the extraction of prostaglandins, diols, epoxides and other oxylipins. The type I internal standards include 6-keto-PGF1α-d4, PGE2-d4, 10,11 DHHep, 20 HETE-d6, 9 (S) HODE-d4, 5 HETE-d8, 11,12 EET-d8 and non-endogenous odd chain length monounsaturated fatty acids, 10,11 dihydroxynondecanoic acid 10,11-DHN. Type II internal standard was added at the last step before analysis to account for changes in volume and instrument variability. A synthetic acid, 1-cyclohexyl-dodecanoic acid urea (CUDA), was selected as type II internal standard.
The analytes were linked to their corresponding Type I internal standards for the purpose of quantification.
Yang J., Schmelzer K., Georgi K, & Hammock B.D. (2009). Quantitative Profiling Method for Oxylipin Metabolome by Liquid Chromatography Electrospray Ionization Tandem Mass Spectrometry. Analytical Chemistry, 81(19), 8085-8093.
Publication 2009
5-hydroxy-6,8,11,14-eicosatetraenoic acid 6-Ketoprostaglandin F1 alpha 20-hydroxy-5,8,11,14-eicosatetraenoic acid Acids Dinoprostone Epoxy Compounds Fatty Acids, Monounsaturated lauric acid Oxylipins Prostaglandins Urea
2
Quantifying Oxylipins by LC-MS/MS
Samples were analyzed by liquid chromatography (Agilent 1260, San Jose, CA, USA) coupled to electrospray ionization on a triple quadrupole mass spectrometer (Agilent 6460, San Jose, CA, USA). For analysis 5 μL of the extract was injected. The auto sampler was cooled at 10 °C. Chromatographic separation was achieved on an Ascentis Express (2.1 × 150 mm, 2.7 μm particles; Sigma-Aldrich Supelco) column using a flow rate of 0.35 mL/min at 40 °C during a 26 min gradient (0–3.5 min from 15 % B to 33 % B, 3.5–5.5 min B to 38 %, 5–7 min to 42 % B, 7–9 min to 48 % B, 9–15 min to 65 % B, 15–17 min to 75 % B, 17–18.5 min to 85 % B, 18.5–19.5 min to 95 % B, from 19.5 to 21 min to 15 % B, 21–26 min 15 % B), while using the solvents A, 0.1 % acetic acid, and B, 90:10 v/v acetonitril/isopropanol. Electrospray ionization was performed in the negative ion mode using N2 at a pressure of 35 psi for the nebulizer with a flow of 10 L/min and a temperature of 300 °C, respectively. The sheath gas temperature was 350 °C with a flow rate of 11 L/min. The capillary was set at 3,500 V and the nozzle voltage was 1,000 V.
To detect the individual oxylipins, MRM in negative ion mode was performed with individually optimized fragmentor voltage and collision energies (Optimizer application, MassHunter, Agilent). MRM transitions were achieved by flow injection of pure standards and the optimizer application and were compared to literature when available for the certain compounds. The detailed list of MRM transitions can be found in the Electronic Supplementary Material Table S-1. Instead of defining certain time segments, with fixed dwell times per compound, dynamic MRM was used, assuring optimal dwell time and sufficient data points per peak.
Strassburg K., Huijbrechts A.M., Kortekaas K.A., Lindeman J.H., Pedersen T.L., Dane A., Berger R., Brenkman A., Hankemeier T., van Duynhoven J., Kalkhoven E., Newman J.W, & Vreeken R.J. (2012). Quantitative profiling of oxylipins through comprehensive LC-MS/MS analysis: application in cardiac surgery. Analytical and Bioanalytical Chemistry, 404(5), 1413-1426.
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Publication 2012
A 300 Acetic Acid Capillaries Chromatography Isopropyl Alcohol Liquid Chromatography Nebulizers Oxylipins Pressure Solvents
3
Oxylipin Synthesis and Procurement
Oxylipins were either synthesized or purchased from Cayman Chemical (Ann Arbor, MI), Larodan Fine Lipids (Malmo, Sweden) and Biomol Research laboratories, Inc. (Plymouth Meeting, PA). Cayman Chemicals provided: (±)-12(13)-epoxy-9Z-octadecenoic acid (12, 13 EpOME), (±) 9,10 EpOME, 9, 10 DHOME, (±)13-hydroxy-9Z,11E-octadecadienoic acid (13 HODE), (±)9-hydroxy-10E,12Z-octadecadienoic acid (9 HODE), 13-keto-9Z,11E-octadecadienoic acid (13 oxo ODE), 9-oxo-10E,12Z-octadecadienoic acid (9 oxo ODE), 6-oxo-9S,11R,15S-trihydroxy-13E-prostenoic acid (6-keto PGF1α) , thromboxane B2 (TXB2), prostaglandin B2 (PGB2), prostaglandin D2 (PGD2), prostaglandin E2 (PGE2); 9S,11R,15S-trihydroxy-5Z,13E-prostadienoic acid (PGF2α); 11-oxo-5Z,9,12E,14E-prostatetraenoic acid (15 deoxy-PGJ2) ; 5-hydroxyeicosatetraenoic acid (5 HETE); 8 HETE; 9 HETE, 11 HETE; 12 HETE; 15 HETE; 20 HETE; 15-oxo--eicosatetraenoic acid (15 oxo-ETE), 5-oxo-ETE, 14,15-epoxy-5Z,8Z,11Z-eicosatrienoic acid (14, 15 EET), 11,12-epoxy-5Z,8Z,14Z-eicosatrienoic acid (11,12 EET), 8,9-epoxy-5Z,11Z,14Z-eicosatrienoic acid (8, 9 EET), 5,6-epoxy-8Z,11Z,14Z-eicosatrienoic acid (5,6 EET), 14,15-dihydroxy-5Z,8Z,11Z-eicosatrienoic acid (14, 15 DHET), 11,12-dihydroxy-5Z,8Z,14Z-eicosatrienoic acid (11, 12 DHET), 8,9-dihydroxy-5Z,11Z,14Z-eicosatrienoic acid (8, 9 DHET), 5,6-dihydroxy-8Z,11Z,14Z-eicosatrienoic acid (5, 6 DHET), leukotriene- B4 (LTB4); Larodan Fine Lipids provided: 9,10,13-tri-hydroxyoctadecenoic acid (9,10,13 TriHOME); 9,12,13 TriHOME. 5S,6R,15S-trihydroxy-7E,9E,11Z,13E-eicosatetraenoic acid (lipoxin A4) was purchased from Biomol.
The following compounds were synthesized in house: 1-cyclohexyl-dodecanoic acid urea (CUDA);10,11 dihydroxyheptadecanoid acid (10,11DHHep); and 10,11 dihydroxynondecanoic acid (10,11-DHN), 11,12, 15 trihydroxy eicosatrieneoic (11,12,15 THET), 19 HETE34 (link), 38 (link), 39 (link). Oasis HLB 60 mg SPE cartridges were purchased from Waters Co. (Milford, MA). Acetonitrile, methanol, ethyl acetate, phosphoric acid, and glacial acetic acid of HPLC Grade or better were purchased from Fisher Scientific (Pittsburgh, PA, USA). All other chemical reagents were purchase from Sigma (St. Louis, MO, USA).
Yang J., Schmelzer K., Georgi K, & Hammock B.D. (2009). Quantitative Profiling Method for Oxylipin Metabolome by Liquid Chromatography Electrospray Ionization Tandem Mass Spectrometry. Analytical Chemistry, 81(19), 8085-8093.
Publication 2009
5-hydroxy-6,8,11,14-eicosatetraenoic acid 5-octadecenoic acid 5-oxo-eicosatetraenoic acid 6-Ketoprostaglandin F1 alpha 8-hydroxyeicosatetraenoic acid 9-deoxy-delta-9-prostaglandin D2 9-hydroxy-10,12-octadecadienoic acid 11-hydroxy-5,8,12,14-eicosatetraenoic acid 12-Hydroxy-5,8,10,14-eicosatetraenoic Acid 13-hydroxy-9,11-octadecadienoic acid 13-oxo-9,11-octadecadienoic acid 15-hydroxy-5,8,11,13-eicosatetraenoic acid 15-oxo-5,8,11,13-eicosatetraenoic acid 20-hydroxy-5,8,11,14-eicosatetraenoic acid Acetic Acid acetonitrile Acids Caimans CREB3L1 protein, human Dinoprost Dinoprostone Eicosatetraenoic Acids Epoxy Resins ethyl acetate High-Performance Liquid Chromatographies Hydroxyeicosatetraenoic Acids Ketogenic Diet lauric acid Leukotriene B4 Lipids lipoxin A4 Methanol octadecadienoic acid Oxylipins oxytocin, 1-desamino-(O-Et-Tyr)(2)- phosphoric acid prostaglandin B2 Prostaglandin D2 Thromboxane B2 Urea
4
Oxylipins Profiling in Plasma Samples
Oxylipins were analyzed in accordance with protocols described elsewhere (Yang et al. 2009 (link)). Briefly, the plasma samples underwent solid phase extraction (SPE) on 60 mg Waters Oasis-HLB cartridges (Milford, MA). The elutions from the SPE cartridges were evaporated using a Speedvac (Jouan, St-Herblain, France) and reconstituted in a 200 nM 1-cyclohexyl ureido, 3-dodecanoic acid (CUDA) in a methanol solution. The LC system used for analysis was an Agilent 1200 SL (Agilent Corporation, Palo Alto, CA) equipped with a 2.1 × 150 mm Eclipse Plus C18 column with a 1.8 μm particle size (Agilent Corporation, Palo Alto, CA). The autosampler was kept at 4 °C. Mobile phase A was water with 0.1% glacial acetic acid. Mobile phase B consisted of acetonitrile/methanol (84:16) with 0.1% glacial acetic acid. Gradient elution was performed at a flow rate of 250 μL/min. Chromatography was optimized to separate all analytes in 21.5 min according to their polarity with the most polar analytes, prostaglandins and leukotrienes eluting first, followed by the hydroxy and epoxy fatty acids. The column was connected to a 4000 QTrap tandem mass spectrometer (Applied Biosystems Instrument Corporation, Foster City, CA) equipped with an electrospray source (Turbo V). The instrument was operated in negative multiple reaction monitor (MRM) mode. The optimized conditions and the MRM transitions, as well as extraction efficiencies were reported previously (Yang et al. 2009 (link)). Quality control samples were analyzed at a minimum frequency of 10 hours to ensure stability of the analytical calibration throughout the analysis. Analyst software 1.4.2 was used to quantify the peaks according to the standard curves.
Zivkovic A.M., Yang J., Georgi K., Hegedus C., Nording M.L., O’Sullivan A., German J.B., Hogg R.J., Weiss R.H., Bay C, & Hammock B.D. (2012). Serum oxylipin profiles in IgA nephropathy patients reflect kidney functional alterations. Metabolomics : Official journal of the Metabolomic Society, 8(6), 1102-1113.
Publication 2012
Acetic Acid acetonitrile Chromatography CREB3L1 protein, human Epoxy Resins Fatty Acids lauric acid Leukotrienes Methanol Oxylipins Plasma Prostaglandins Solid Phase Extraction
5
Solid Phase Extraction of Oxylipins
SPMs were extracted from plasma or serum samples and effluents from peritoneal dialysis (PD) using solid phase extraction (SPE) (Rund et al., 2017 (link)). In the first step a mixture of 20 deuterated IS (20 nM each, including 2H5-RvD1, 2H5-RvD2, 2H5-LXA4, 2H4-LTB4, and 2H4-9,10-DiHOME), antioxidant mixture (0.2 mg/mL BHT, 100 μM indomethacin, 100 μM soluble epoxide hydrolase inhibitor trans-4-[4-(3-adamantan-1-yl-ureido)-cyclohexyloxy]-benzoic acid (t-AUCB) in MeOH) were added to 500 μL of plasma/serum or 1,200 μL of PD exudates. Then 1,400 μL ice-cold MeOH (3,360 μL for PD exudates) were added for protein precipitation (at least 30 min at −80°C). Following centrifugation, the supernatant was evaporated under a gentle nitrogen stream to <50% MeOH, diluted with 0.1 M disodium hydrogen phosphate buffer (pH 5.5) and loaded onto the preconditioned SPE column (Bond Elut Certify II, 200 mg, 3 mL; Agilent, Waldbronn, Germany). Oxylipins were eluted with ethyl acetate/n-hexane (75/25, v/v) containing 1% acetic acid. After evaporation to dryness in a vacuum concentrator (30°C, 1 mbar, ca. 60 min; Christ, Osterode, Germany) sample extracts were reconstituted in 50 μL MeOH containing 40 nM 1-(1-(ethylsulfonyl)piperidin-4-yl)-3-(4-(trifluoromethoxy)phenyl)urea as IS 2. Injection volume was 5 μL; for samples with low SPM content a second (10 μL) injection was used for SPM quantification.
Kutzner L., Rund K.M., Ostermann A.I., Hartung N.M., Galano J.M., Balas L., Durand T., Balzer M.S., David S, & Schebb N.H. (2019). Development of an Optimized LC-MS Method for the Detection of Specialized Pro-Resolving Mediators in Biological Samples. Frontiers in Pharmacology, 10, 169.
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Publication 2019
4-(4-(3-adamantan-1-ylureido)cyclohexyloxy)benzoic acid Acetic Acid Antioxidants Benzoic Acid Buffers Centrifugation Cold Temperature Epoxide hydrolase ethyl acetate Exudate Indomethacin Leukotriene B4 lipoxin A4 n-hexane Nitrogen Oxylipins Peritoneal Dialysis Plasma Proteins Serum sodium phosphate, dibasic Solid Phase Extraction Urea Vacuum

Most recents protocols related to «Oxylipins»

1
Metabolomic Profiling Stability Analysis

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Publication 2023
Chromatography Diglycerides Endocannabinoids ethanolamine oleoyl ethanolamine Fatty Acids Glycerin Isomerism Oxylipins prisma Sphingolipids Triglycerides Tryptophan vaccenic acid
2
Comprehensive Analytical Reagents for Metabolomic Studies

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Publication 2023
Acetic Acid Acetone acetonitrile Alabaster Anabolism Butanols Caimans Chloroform Citric Acid Endocannabinoids ethyl acetate formic acid Hexanes Hydrochloric acid Isopropyl Alcohol Isotopes Lipids Methanol Oxylipins sodium phosphate, dibasic Sphingolipids Tryptophan
3
Comprehensive Metabolomic Analysis of Serum Samples
Blood samples were collected by a physician in the fasting state before and after the 12-week intervention. Serum samples were used to blindly analyze serum metabolites at the Gustave Roussy Cancer Campus facility (Villejuif, France) using mass spectrometers coupled to multiple different liquid or gas phase chromatography methods. Bile acids metabolomics were obtained using a UHPLC/MS—RRLC 1260 system (Agilent Technologies, Waldbronn, Germany) coupled to a Triple Quadrupole 6410 (Agilent Technologies). Short chain fatty acids, oxylipin, and lipids metabolomics were assessed by a UHPLC/QUAD+—RRLC 1260 system (Agilent Technologies, Waldbronn, Germany) coupled to a 6500+ QTRAP (Sciex, Darmstadt, Germany). Polyamines metabolomics were quantified using a UHPLC/QQQ—RRLC 1260 system (Agilent Technologies, Waldbronn, Germany) coupled to a Triple Quadrupole 6410 (Agilent Technologies). Concerning the level of identification, for the targeted metabolomics it is identified (level 1, validated by standards injections on the Orbitrap, and multiple reaction monitoring MRM developments for the LCQQQ and GCQQQ), and for the metabolomic profiling it is putative. Intra batch correction was performed based on quality control pool and processed on R software. The details of each method were previously described [26 (link),27 (link)].
Youssef L., Bourgin M., Durand S., Aprahamian F., Lefevre D., Maiuri M.C., Marcangeli V., Dulac M., Hajj-Boutros G., Buckinx F., Peyrusqué E., Gaudreau P., Morais J.A., Gouspillou G., Kroemer G., Aubertin-Leheudre M, & Noirez P. (2023). Serum Metabolome Adaptations Following 12 Weeks of High-Intensity Interval Training or Moderate-Intensity Continuous Training in Obese Older Adults. Metabolites, 13(2), 198.
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Publication 2023
Bile Acids BLOOD Fatty Acids, Volatile Gas Chromatography Lipids Oxylipins Physicians Polyamines Serous Cystadenocarcinoma Serum
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Quantification of n3 and n6 Oxylipins
Oxylipins were quantified as described by Pedersen et al. [31 (link)]. The extracted oxylipins were separated and quantified using a Waters i-Class Acquity UHPLC system coupled with a Sciex 6500+ QTRAP mass spectrometer operated in a negative ionization mode. Oxylipins were quantified by targeted, retention-time specific, multiple reaction monitoring (MRM) ion transitions. There were quantified values for 24 n6-related oxylipins, including 14 ARA-derived and 10 LA-derived oxylipins. There were 12 measured n3-related oxylipins, which included six ALA-derived, four Docosahexaenoic acid (DHA)-derived and two Eicosapentaenoic acid (EPA)-derived oxylipins. The oxylipins were Box-Cox transformed [32 (link)] using the forecast package in R (v8.1, R package version 8.12 [33 ]) and considered normally distributed for further analyses [34 (link)].
Buckner T., Johnson R.K., Vanderlinden L.A., Carry P.M., Romero A., Onengut-Gumuscu S., Chen W.M., Fiehn O., Frohnert B.I., Crume T., Perng W., Kechris K., Rewers M, & Norris J.M. (2023). An Oxylipin-Related Nutrient Pattern and Risk of Type 1 Diabetes in the Diabetes Autoimmunity Study in the Young (DAISY). Nutrients, 15(4), 945.
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Publication 2023
Docosahexaenoic Acids Eicosapentaenoic Acid Oxylipins Retention (Psychology)
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Targeted Metabolomic Analysis of Signaling Metabolites
Metabolomic studies were performed using directed, non-targeted liquid chromatography-mass spectrometry (LC-MS) approaches to specifically capture and assay small polar “bioactive” metabolites. These were deemed to have a higher likelihood of interacting with cell surface receptors involved in signaling. These include free fatty acids, eicosanoids and oxylipins, bile acids, and fatty acid esters of hydroxy fatty acids, among hundreds of unidentified related metabolites [34 (link),35 (link)]. Metabolite levels are used as continuous traits with a mean of 0 and standard deviation of 1. Identified metabolites were confirmed through internal standards.
Granados J.C., Watrous J.D., Long T., Rosenthal S.B., Cheng S., Jain M, & Nigam S.K. (2023). Regulation of Human Endogenous Metabolites by Drug Transporters and Drug Metabolizing Enzymes: An Analysis of Targeted SNP-Metabolite Associations. Metabolites, 13(2), 171.
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Publication 2023
Bile Acids Biological Assay Eicosanoids Esters Fatty Acids Hydroxy Acids Liquid Chromatography Mass Spectrometry Nonesterified Fatty Acids Oxylipins Receptors, Cell Surface

Top products related to «Oxylipins»

1
Qtrap 6500 by AB Sciex
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The QTRAP 6500 is a high-performance liquid chromatography-tandem mass spectrometry (LC-MS/MS) system. It is designed to provide sensitive and selective detection and quantification of a wide range of analytes in complex matrices. The QTRAP 6500 combines a triple quadrupole mass analyzer with a linear ion trap, enabling both quantitative and qualitative analysis capabilities.
2
Oxylipin standards by Cayman Chemical
Oxylipin standards are reference materials used for the identification and quantification of oxylipins in samples. Oxylipins are a class of bioactive lipid mediators derived from the oxidation of polyunsaturated fatty acids. These standards provide a reliable and consistent way to analyze oxylipin levels in biological and chemical samples.
3
Beh c18 column by Waters Corporation
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The BEH C18 column is a high-performance liquid chromatography (HPLC) column designed for the separation and analysis of a wide range of compounds. It features a Waters Ethylene Bridged Hybrid (BEH) stationary phase, which provides excellent peak shape and resolution for various types of analytes.
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Qtrap 5500 by AB Sciex
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The QTRAP 5500 is a high-performance hybrid triple quadrupole linear ion trap mass spectrometer. It combines the quantitative capabilities of triple quadrupole technology with the qualitative power of a linear ion trap, enabling both quantitative and qualitative analysis in a single platform.
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Api 4000 qtrap by AB Sciex
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The API 4000 QTrap is a high-performance liquid chromatography-tandem mass spectrometry (LC-MS/MS) system. It is designed to perform sensitive and selective quantitative and qualitative analyses of a wide range of analytes in complex matrices. The system features a quadrupole-linear ion trap mass analyzer that provides enhanced sensitivity, resolution, and scan speed for improved data acquisition and analysis.
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The Acquity UPLC is a high-performance liquid chromatography (HPLC) system developed by Waters Corporation. It is designed to deliver rapid and efficient separation of complex samples, providing high-resolution and sensitivity for various analytical applications.
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Multiquant software by AB Sciex
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MultiQuant software is a data processing application designed for quantitative analysis of mass spectrometry data. It provides a comprehensive suite of tools for data review, peak detection, and quantification of target analytes in complex biological samples.
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Acetic acid is a clear, colorless liquid chemical compound with a pungent odor. It is the main component of vinegar and is used as a reagent in various laboratory applications.
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GraphPad Prism 7 is a data analysis and graphing software. It provides tools for data organization, curve fitting, statistical analysis, and visualization. Prism 7 supports a variety of data types and file formats, enabling users to create high-quality scientific graphs and publications.
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Oxylipin by Cayman Chemical
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Oxylipin is a class of lipid-derived signaling molecules that play important roles in various physiological and pathological processes. These molecules are derived from the oxidation of polyunsaturated fatty acids and serve as mediators in diverse biological functions.

More about "Oxylipins"

Oxylipins, a diverse group of oxygenated lipid mediators derived from polyunsaturated fatty acids, play crucial roles in regulating inflammation, immune function, and various physiological processes.
These bioactive lipids include prostanoids, leukotrienes, and other oxidized fatty acid derivatives that act as potent signalling molecules.
Understanding the complex biology of this important class of lipid-derived mediators is essential for researchers studying areas such as cardiovascular health, neurodegeneration, and metabolic disorders.
Leveraging the power of advanced analytical techniques like the QTRAP 6500, QTRAP 5500, and API 4000 QTrap systems, researchers can accurately quantify and profile oxylipin levels using Oxylipin standards and BEH C18 columns on Acquity UPLC systems.
The MultiQuant software provides a user-friendly platform to analyze and visualize oxylipin data, while GraphPad Prism 7 can be used for statistical analysis and data interpretation.
Acetic acid is a common component in oxylipin extraction and separation procedures.
By optimizing research workflows and utilizing AI-driven insights from tools like PubCompare.ai, researchers can identify the most accurate and reproducible protocols from literature, preprints, and patents, streamlining their oxylipin studies and advancing our understanding of this dynamic lipid signalling network.