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Journal of Experimental Botany Nov 2016Abiotic and biotic stresses are often characterized by an induction of reactive electrophile species (RES) such as the jasmonate 12-oxo-phytodienoic acid (OPDA) or the...
Abiotic and biotic stresses are often characterized by an induction of reactive electrophile species (RES) such as the jasmonate 12-oxo-phytodienoic acid (OPDA) or the structurally related phytoprostanes. Previously, RES oxylipins have been shown massively to induce heat-shock-response (HSR) genes including HSP101 chaperones. Moreover, jasmonates have been reported to play a role in basal thermotolerance. We show that representative HSR marker genes are strongly induced by RES oxylipins through the four master regulator transcription factors HSFA1a, b, d, and e essential for short-term adaptation to heat stress in Arabidopsis. When compared with Arabidopsis seedlings treated at the optimal acclimation temperature of 37 °C, the exogenous application of RES oxylipins at 20 °C induced a much weaker induction of HSP101 at both the gene and protein expression levels which, however, was not sufficient to confer short-term acquired thermotolerance. Moreover, jasmonate-deficient mutant lines displayed a wild-type-like HSR and were not compromised in acquiring thermotolerance. Hence, the OPDA- and RES oxylipin-induced HSR is not sufficient to protect seedlings from severe heat stress but may help plants to cope better with stresses associated with protein unfolding by inducing a battery of chaperones in the absence of heat.
Topics: Arabidopsis Proteins; Cyclopentanes; DNA-Binding Proteins; Heat Shock Transcription Factors; Heat-Shock Proteins; Heat-Shock Response; Hot Temperature; Oxylipins; Plant Growth Regulators; Plant Proteins; Seedlings; Transcription Factors; Transcriptome
PubMed: 27811081
DOI: 10.1093/jxb/erw376 -
Journal of Lipid Research Nov 2020Oxylipins are potent lipid mediators involved in a variety of physiological processes. Their profiling has the potential to provide a wealth of information regarding...
Oxylipins are potent lipid mediators involved in a variety of physiological processes. Their profiling has the potential to provide a wealth of information regarding human health and disease and is a promising technology for translation into clinical applications. However, results generated by independent groups are rarely comparable, which increases the need for the implementation of internationally agreed upon protocols. We performed an interlaboratory comparison for the MS-based quantitative analysis of total oxylipins. Five independent laboratories assessed the technical variability and comparability of 133 oxylipins using a harmonized and standardized protocol, common biological materials (i.e., seven quality control plasmas), standard calibration series, and analytical methods. The quantitative analysis was based on a standard calibration series with isotopically labeled internal standards. Using the standardized protocol, the technical variance was within ±15% for 73% of oxylipins; however, most epoxy fatty acids were identified as critical analytes due to high variabilities in concentrations. The comparability of concentrations determined by the laboratories was examined using consensus value estimates and unsupervised/supervised multivariate analysis (i.e., principal component analysis and partial least squares discriminant analysis). Interlaboratory variability was limited and did not interfere with our ability to distinguish the different plasmas. Moreover, all laboratories were able to identify similar differences between plasmas. In summary, we show that by using a standardized protocol for sample preparation, low technical variability can be achieved. Harmonization of all oxylipin extraction and analysis steps led to reliable, reproducible, and comparable oxylipin concentrations in independent laboratories, allowing the generation of biologically meaningful oxylipin patterns.
Topics: Calibration; Chromatography, Liquid; Humans; Oxylipins; Quality Control; Tandem Mass Spectrometry
PubMed: 32848050
DOI: 10.1194/jlr.RA120000991 -
The Journal of Antibiotics May 2017
Topics: Anti-Infective Agents; Cyanobacteria; Oxylipins; Secondary Metabolism
PubMed: 28270686
DOI: 10.1038/ja.2017.32 -
Environment International Dec 2021Exposure to consumer product chemicals during pregnancy may increase susceptibility to pregnancy disorders by influencing maternal inflammation. However, effects on...
BACKGROUND
Exposure to consumer product chemicals during pregnancy may increase susceptibility to pregnancy disorders by influencing maternal inflammation. However, effects on specific inflammatory pathways have not been well characterized. Oxylipins are a diverse class of lipids that act as important mediators and biomarkers of several biological pathways that regulate inflammation. Adverse pregnancy outcomes have been associated with circulating oxylipin levels in pregnancy. In this study, we aimed to determine the longitudinal associations between plasma oxylipins and urinary biomarkers of three classes of consumer product chemicals among pregnant women.
METHODS
Data come from a study of 90 pregnant women nested within the LIFECODES cohort. Maternal plasma and urine were collected at three prenatal visits. Plasma was analyzed for 61 oxylipins, which were grouped according to biosynthetic pathways that we defined by upstream: 1) fatty acid precursor, including linoleic, arachidonic, docosahexaenoic, or eicosapentaenoic acid; and 2) enzyme pathway, including cyclooxygenase (COX), lipoxygenase (LOX), or cytochrome P450 (CYP). Urine was analyzed for 12 phenol, 12 phthalate, and 9 organophosphate ester (OPE) biomarkers. Linear mixed effect models were used for single-pollutant analyses. We implemented a novel extension of quantile g-computation for longitudinal data to examine the joint effect of class-specific chemical mixtures on individual plasma oxylipin concentrations.
RESULTS
We found that urinary biomarkers of consumer product chemicals were positively associated with pro-inflammatory oxylipins from several biosynthetic pathways. Importantly, these associations depended upon the chemical class of exposure biomarker. We estimated positive associations between urinary phenol biomarkers and oxylipins produced from arachidonic acid by LOX enzymes, including several important pro-inflammatory hydroxyeicosatetraenoic acids (HETEs). On average, mean concentrations of oxylipin produced from the arachidonic acid/LOX pathway were 48%-71% higher per quartile increase in the phenol biomarker mixture. For example, a simultaneous quartile increase in all urinary phenols was associated with 53% higher (95% confidence interval [CI]: 11%, 111%) concentrations of 12-HETE. The positive associations among phenols were primarily driven by methyl paraben, 2,5-dichlorophenol, and triclosan. Additionally, we observed that phthalate and OPE metabolites were associated with higher concentrations of oxylipins produced from linoleic acid by CYP enzymes, including the pro-inflammatory dihydroxy-octadecenoic acids (DiHOMEs). Associations among DiHOME oxylipins were driven by metabolites of benzylbutyl and di-isodecyl phthalate, and by the metabolite of tris(1,3-dichloro-2-propyl) phosphate among OPEs. We also observed inverse associations between phthalate and OPE metabolites and oxylipins produced from other pathways; however, adjusting for a plasma indicator of dietary fatty acid intake attenuated those results.
CONCLUSIONS
Our findings support the hypothesis that consumer product chemicals may have diverse impacts on inflammation processes in pregnancy. Certain pro-inflammatory oxylipins were generally higher among participants with higher urinary chemical biomarker concentrations. Associations varied by class of chemical and by the biosynthetic pathway of oxylipin production, indicating potential specificity in the inflammatory effects of these environmental chemicals during pregnancy that warrant investigation in larger studies.
Topics: Cohort Studies; Female; Humans; Oxylipins; Phenols; Pregnancy; Pregnancy Outcome; Pregnant Women
PubMed: 34314981
DOI: 10.1016/j.envint.2021.106787 -
STAR Protocols Sep 2023Polyunsaturated fatty acids (PUFAs) and their oxidized products (oxylipins) are important mediators in intra- and extra-cellular signaling. We describe here the...
Polyunsaturated fatty acids (PUFAs) and their oxidized products (oxylipins) are important mediators in intra- and extra-cellular signaling. We describe here the simultaneous quantification of 163 PUFAs and oxylipins using liquid chromatography-mass spectrometry (LC-MS). The protocol details steps for PUFA purification from various biological materials, the conditions for LC-MS analysis, as well as quantitative approaches for data evaluation. We provide an example of PUFA quantification in animal tissue along with the bioinformatic protocol, enabling efficient inter-sample comparison and statistical analysis. For complete details on the use and execution of this protocol, please refer to Vila et al., Costanza et al., Blomme et al., and Blomme et al..
Topics: Animals; Oxylipins; Tandem Mass Spectrometry; Fatty Acids, Unsaturated; Chromatography, Liquid; Liquid Chromatography-Mass Spectrometry
PubMed: 37597187
DOI: 10.1016/j.xpro.2023.102226 -
Comparative Biochemistry and... May 2024Chemical cues play important roles in mediating ecological interactions. Oxylipins, oxygenated metabolites of fatty acids, are one signalling molecule type that...
Chemical cues play important roles in mediating ecological interactions. Oxylipins, oxygenated metabolites of fatty acids, are one signalling molecule type that influences the physiology and function of species, suggesting their broader significance in chemical communication within aquatic systems. Yet, our current understanding of their function is restricted taxonomically and contextually making it difficult to infer their ecological significance. Snails and leeches are ubiquitous in freshwater ecosystems worldwide, yet little is known about their oxylipin profiles and the factors that cause their profiles to change. As snails and leeches differ taxonomically and represent different trophic groups, we postulated oxylipin profile differences. For snails, we hypothesized that ontogeny (non-reproductive vs reproductive) and predation (non-infested vs leech-infested) would affect oxylipin profiles. Oxylipins were characterized from water conditioned with the snail Planorbella duryi and leech Helobdella lineata, and included three treatment types (snails, leeches, and leech-infested snails) with the snails consisting of three size classes: small (5-6 mm, non-reproductive) and medium and large (13-14 and 19-20 mm, reproductive). The two species differed in the composition of their oxylipin profiles both in diversity and amounts. Further, ontogeny and predation affected the diversity of oxylipins emitted by snails. Our experimental profiles of oxylipins show that chemical cues within freshwater systems vary depending upon the species emitting the signals, the developmental stage of the species, as well as from ecological interactions such as predation. We also identified some candidates, like 9-HETE and PGE, that could be explored more directly for their physiological and ecological roles in freshwater systems.
Topics: Animals; Oxylipins; Ecosystem; Predatory Behavior; Snails; Fresh Water; Leeches
PubMed: 38360203
DOI: 10.1016/j.cbpa.2024.111607 -
Science Signaling Feb 2010Plants possess a family of potent fatty acid-derived wound-response and developmental regulators: the jasmonates. These compounds are derived from the tri-unsaturated... (Review)
Review
Plants possess a family of potent fatty acid-derived wound-response and developmental regulators: the jasmonates. These compounds are derived from the tri-unsaturated fatty acids alpha-linolenic acid (18:3) and, in plants such as Arabidopsis thaliana and tomato, 7(Z)-, 10(Z)-, and 13(Z)-hexadecatrienoic acid (16:3). The lipoxygenase-catalyzed addition of molecular oxygen to alpha-linolenic acid initiates jasmonate synthesis by providing a 13-hydroperoxide substrate for formation of an unstable allene oxide by allene oxide synthase (AOS). This allene oxide then undergoes enzyme-guided cyclization to produce 12-oxophytodienoic acid (OPDA). These first steps take place in plastids, but further OPDA metabolism occurs in peroxisomes. OPDA has several fates, including esterification into plastid lipids and transformation into the 12-carbon prohormone jasmonic acid (JA). JA is itself a substrate for further diverse modifications, including the production of jasmonoyl-isoleucine (JA-Ile), which is a major biologically active jasmonate among a growing number of jasmonate derivatives. Each new jasmonate family member that is discovered provides another key to understanding the fine control of gene expression in immune responses; in the initiation and maintenance of long-distance signal transfer in response to wounding; in the regulation of fertility; and in the turnover, inactivation, and sequestration of jasmonates, among other processes.
Topics: Biocatalysis; Cyclization; Cyclopentanes; Oxylipins; Plants
PubMed: 20159849
DOI: 10.1126/scisignal.3109cm3 -
Psychoneuroendocrinology Apr 2021People with type 2 diabetes mellitus (T2DM) are at increased risk for depression. Both conditions are associated with disturbances in polyunsaturated fatty acids....
BACKGROUND
People with type 2 diabetes mellitus (T2DM) are at increased risk for depression. Both conditions are associated with disturbances in polyunsaturated fatty acids. Omega-3 and omega-6 fatty acids can be converted into bioactive epoxides by cytochrome P450s (CYP450), which play pro-resolving roles in the inflammatory response; however, soluble epoxide hydrolase (sEH) metabolizes epoxides into diols, which lack pro-resolving functions and can be cytotoxic. Here, we survey serum CYP450- and sEH-derived metabolite concentrations in people with T2DM with and without a major depressive episode.
METHODS
Sunnybrook Type 2 Diabetes Study (NCT04455867) participants experiencing a major depressive episode (research version of the Structured Clinical Interview for DSM-5 criteria) were matched 1:1 for gender, glycosylated hemoglobin A1c and body mass index to participants without a current depressive episode. Depression severity was assessed using the Beck Depression Inventory 2nd Edition (BDI-II). From fasting morning blood, unesterified serum oxylipins were quantified by ultra-high-performance liquid chromatography tandem mass spectrometry following solid phase extraction, and interleukin-6 (IL-6) by enzyme-linked immunosorbent assay.
RESULTS
Between 20 depressed and 20 non-depressed participants (mean age 58.9 ± 8.5 years, 65% women) with T2DM, several sEH-derived fatty acid diols, but not IL-6, were higher among those with a depressive episode (effect sizes up to d = 0.796 for 17,18-DiHETE, a metabolite of eicosapentaenoic acid [EPA]; t = 2.516, p = 0.016). Among people with a depressive episode, two epoxides were correlated with lower BDI-II scores: 12(13)-EpOME (ρ = -0.541, p = 0.014) and 10(11)-EpDPE (ρ = -0.444, p = 0.049), metabolites of linoleic acid and docosahexaenoic acid (DHA), respectively, while the ratio of 12,13-DiHOME/12(13)-EpOME was correlated with higher BDI-II scores (ρ = 0.513, p = 0.021).
CONCLUSIONS
In people with T2DM, major depressive episodes and depressive symptom severity were associated with an oxylipin profile consistent with elimination of pro-resolving lipid mediators by sEH.
Topics: Aged; Depressive Disorder, Major; Diabetes Mellitus, Type 2; Epoxide Hydrolases; Female; Humans; Male; Middle Aged; Oxylipins
PubMed: 33503568
DOI: 10.1016/j.psyneuen.2021.105149 -
Journal of Food Science May 2021The oxidation of polyunsaturated fatty acids produces bioactive primary oxidation products known as oxylipins. In many biological matrices, the majority of oxylipins are...
The oxidation of polyunsaturated fatty acids produces bioactive primary oxidation products known as oxylipins. In many biological matrices, the majority of oxylipins are bound (i.e. esterified), and a relatively small proportion (<10%) exists in the free form. The present study tested whether this extends to bovine milk following method evaluation of various extraction and base hydrolysis protocols for measuring bound oxylipins. Free (unbound) oxylipins were also measured. Folch extraction followed by sodium carbonate hydrolysis in the presence of methanol containing 0.1% of acetic acid and 0.1% of butylated hydroxytoluene resulted in greater oxylipin concentrations and better surrogate standard recoveries compared to other methods that did not involve Folch extraction or the addition of methanol with hydrolysis base. Sodium hydroxide was better than sodium carbonate in hydrolyzing bound oxylipins under the same conditions. Milk analysis of oxylipins with mass-spectrometry following Folch extraction and sodium hydroxide hydrolysis revealed that 95% of oxylipins in bovine milk were esterified. Most of the detected oxylipins were derived from linoleic acid, which accounted for 92 and 88% of oxylipins in the free and esterified pools, respectively. These results demonstrate that the majority of bovine milk oxylipins are bound, and that linoleic-acid derived metabolites are the most abundant oxylipin species in free and bound lipid pools. Additional studies are needed to understand the role of different oxylipin pools in both calf and human nutrition. PRACTICAL APPLICATION: A method involving Folch lipid extraction and sodium hydroxide hydrolysis was validated for esterified oxylipin measurements in bovine milk. Application of the method revealed that the majority (∼95%) of oxylipins in bovine milk were bound. Linoleic-acid derived oxylipins were the most abundant species in both bound and free milk fractions (88-92%). The results highlight the presence of a new pool of oxidized lipids in milk, potentially involved in modifying its sensory and nutritional properties.
Topics: Animals; Cattle; Esterification; Fatty Acids, Unsaturated; Humans; Hydrolysis; Linoleic Acid; Milk; Oxidation-Reduction; Oxylipins; Sodium Hydroxide
PubMed: 33864645
DOI: 10.1111/1750-3841.15697 -
Marine Drugs Dec 2020The bioactivity-guided purification of the culture broth of the shipworm endosymbiont strain 991H.S.0a.06 yielded a new fatty acid, turneroic acid (), and two...
The bioactivity-guided purification of the culture broth of the shipworm endosymbiont strain 991H.S.0a.06 yielded a new fatty acid, turneroic acid (), and two previously described oxylipins (-). Turneroic acid () is an 18-carbon fatty acid decorated by a hydroxy group and an epoxide ring. Compounds - inhibited bacterial biofilm formation in , while only showed antimicrobial activity against planktonic . . Comparison of the bioactivity of - with structurally related compounds indicated the importance of the epoxide moiety for selective and potent biofilm inhibition.
Topics: Animals; Biofilms; Bivalvia; Gammaproteobacteria; Microbial Sensitivity Tests; Oxylipins; Symbiosis
PubMed: 33419303
DOI: 10.3390/md18120656