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https://www.readbyqxmd.com/read/29339254/design-synthesis-biological-evaluation-and-docking-studies-of-new-3-4-5-dihydro-1h-pyrazol-isoxazol-5-yl-2-phenyl-1h-indole-derivatives-as-potent-antioxidants-and-15-lipoxygenase-inhibitors
#1
Haydi Saher ElBordiny, Mostafa Mahmoud El-Miligy, Shaymaa Emam Kassab, Hoda Daabees, Soad Abdelhamid Mohamed El-Hawash, Waleed Ali Mohamed Ali
New candidates of 3-(4,5-dihydro-1H-pyrazol/isoxazol-5-yl)-2-phenyl-1H-indole derivatives (4-7) were designed combining the pyrazoline/isoxazoline heterocycles and 2-phenylindole to explore its potential as 15-lipoxygenase (15-LOX) inhibitors. The design of the new derivatives was based on utilizing the antioxidant properties of pyrazoline, 2-phenylindole and the good 15-LOX inhibition properties of indolylpyrazoline. The derivatives were synthesized adopting simple and laboratory friendly reaction conditions to give the target compounds in quantitative yields...
January 10, 2018: European Journal of Medicinal Chemistry
https://www.readbyqxmd.com/read/29302056/human-macrophages-differentially-produce-specific-resolvin-or-leukotriene-signals-that-depend-on-bacterial-pathogenicity
#2
Oliver Werz, Jana Gerstmeier, Stephania Libreros, Xavier De la Rosa, Markus Werner, Paul C Norris, Nan Chiang, Charles N Serhan
Proinflammatory eicosanoids (prostaglandins and leukotrienes) and specialized pro-resolving mediators (SPM) are temporally regulated during infections. Here we show that human macrophage phenotypes biosynthesize unique lipid mediator signatures when exposed to pathogenic bacteria. E. coli and S. aureus each stimulate predominantly proinflammatory 5-lipoxygenase (LOX) and cyclooxygenase pathways (i.e., leukotriene B4 and prostaglandin E2) in M1 macrophages. These pathogens stimulate M2 macrophages to produce SPMs including resolvin D2 (RvD2), RvD5, and maresin-1...
January 4, 2018: Nature Communications
https://www.readbyqxmd.com/read/29301865/analysis-of-hydroxyeicosatetraenoic-acids-hetes-in-human-whole-blood-by-chiral-ultrahigh-performance-liquid-chromatgraphy-uhplc-electron-capture-atmospheric-pressure-chemical-ionization-high-resolution-mass-spectrometry-ecapci-hrms
#3
Liudmila L Mazaleuskaya, Ashkan Salamatipour, Dimitra Sarantopoulou, Liwei Weng, Garret A FitzGerald, Ian A Blair, Clementina Mesaros
The biosynthesis of eicosanoids occurs enzymatically via lipoxygenases (LOXs), cyclooxygenases (COXs), and cytochrome P450, or through non-enzymatic free radical reactions. The enzymatic routes are highly enantiospecific. Chiral separation and high sensitivity detection methods are required to differentiate and quantify enantioselective HETEs (hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoic acids) in complex biological fluids. We report here a targeted chiral lipidomics analysis of human blood using ultrahigh performance liquid chromatgraphy (UHPLC)-electron capture atmospheric pressure chemical ionization/high resolution mass spectrometry (ECAPCI/HRMS)...
January 4, 2018: Journal of Lipid Research
https://www.readbyqxmd.com/read/29288756/is-comfrey-root-more-than-toxic-pyrrolizidine-alkaloids-salvianolic-acids-among-antioxidant-polyphenols-in-comfrey-symphytum-officinale-l-roots
#4
Adriana Trifan, Sebastian E W Opitz, Roland Josuran, Andreas Grubelnik, Nils Esslinger, Samuel Peter, Sarah Bräm, Nadja Meier, Evelyn Wolfram
Comfrey root preparations are used for the external treatment of joint distortions and myalgia, due to its analgesic and anti-inflammatory properties. Up to date, key activity-determining constituents of comfrey root extracts have not been completely elucidated. Therefore, we applied different approaches to further characterize a comfrey root extract (65% ethanol). The phenolic profile of comfrey root sample was characterized by HPLC-DAD-QTOF-MS/MS. Rosmarinic acid was identified as main phenolic constituent (7...
December 27, 2017: Food and Chemical Toxicology
https://www.readbyqxmd.com/read/29280942/the-occurrence-of-flavonoids-and-related-compounds-in-cedrus-brevifolia-a-henry-ex-elwes-a-henry-needles-inhibitory-potencies-on-lipoxygenase-linoleic-acid-lipid-peroxidation-and-antioxidant-activity
#5
Andreas Douros, Dimitra Hadjipavlou-Litina, Konstantinos Nikolaou, Helen Skaltsa
The phytochemical analysis of the polar extracts of Cedrus brevifolia needles yielded 20 compounds, namely from the methanol extract we isolated three flavonoids (1-3), one hydrolysable tannin (4), eleven phenolic derivatives (5-15) and one apocarotenoid (16), while from the methanol: water (5:1) extract we isolated four flavonoids (17-20). Chemical structures of all isolated compounds were determined by 1D, 2D-NMR (1 Dimension, 2 Dimensions Nuclear Magnetic Resonance) and UV-Vis (Ultraviolet-Visible) spectroscopy...
December 27, 2017: Plants (Basel, Switzerland)
https://www.readbyqxmd.com/read/29275696/potential-of-rare-actinomycetes-in-the-production-of-metabolites-against-multiple-oxidant-agents
#6
Fatemeh Mohammadipanah, Mana Momenilandi
CONTEXT: Actinobacteria are a precious source of novel bioactive metabolites with potential pharmaceutical applications. OBJECTIVES: Representatives of 11 genera of rare Actinobacteria were selected for the evaluation of antioxidant activity. MATERIAL AND METHODS: Fermentation broths of the Actinobacteria were extracted and dosage of 10 to 2000 µg/mL were applied for in vitro antioxidant-related bioassays. Cytotoxicity was assessed at the concentration of 2...
December 2018: Pharmaceutical Biology
https://www.readbyqxmd.com/read/29235036/expression-of-dha-metabolizing-enzyme-alox15-is-regulated-by-selective-histone-acetylation-in-neuroblastoma-cells
#7
Christabel Fung-Yih Ho, Claire Poh-Ee Bon, Yee-Kong Ng, Deron R Herr, Jui-Sheng Wu, Teng-Nan Lin, Wei-Yi Ong
The omega-3 polyunsaturated fatty acid, docosahexaenoic acid (DHA) is enriched in neural membranes of the CNS, and recent studies have shown a role of DHA metabolism by 15-lipoxygenase-1 (Alox15) in prefrontal cortex resolvin D1 formation, hippocampo-prefrontal cortical long-term-potentiation, spatial working memory, and anti-nociception/anxiety. In this study, we elucidated epigenetic regulation of Alox15 via histone modifications in neuron-like cells. Treatment of undifferentiated SH-SY5Y human neuroblastoma cells with the histone deacetylase (HDAC) inhibitors trichostatin A (TSA) and sodium butyrate significantly increased Alox15 mRNA expression...
December 12, 2017: Neurochemical Research
https://www.readbyqxmd.com/read/29228980/lipoxin-a4-reverses-mesenchymal-phenotypes-to-attenuate-invasion-and-metastasis-via-the-inhibition-of-autocrine-tgf-%C3%AE-1-signaling-in-pancreatic-cancer
#8
Liang Zong, Ke Chen, Zhengdong Jiang, Xin Chen, Liankang Sun, Jiguang Ma, Cancan Zhou, Qinhong Xu, Wanxing Duan, Liang Han, Jianjun Lei, Xuqi Li, Qingyong Ma, Zheng Wang
BACKGROUND: Pancreatic cancer is a lethal disease in part because of its potential for aggressive invasion and metastasis. Lipoxin A4 (LXA4) is one of the metabolites that is derived from arachidonic acid and that is catalyzed by 15-lipoxygenase (15-LOX), and it has recently been reported to exhibit anti-cancer effects. However, the role of LXA4 in pancreatic cancer remains to be elucidated. METHODS: Pancreatic cell lines were treated with vehicle or LXA4, and the invasive capacity was then assessed by Transwell assays...
December 11, 2017: Journal of Experimental & Clinical Cancer Research: CR
https://www.readbyqxmd.com/read/29197557/soy-flour-as-an-alternative-to-purified-lipoxygenase-for-the-enzymatic-synthesis-of-resolvin-analogues
#9
Hoang-Anh T Tu, Eleanor P Dobson, Luke C Henderson, Colin J Barrow, Jacqui L Adcock
Specialized pro-resolving mediators are lipid signaling molecules synthesized from omega-3 and -6 polyunsaturated fatty acids, which promote the resolution of the inflammatory response. They are potential drug targets for the treatment of numerous conditions linked with uncontrolled inflammation. Many of these mediators can be effectively synthesized using enzymes, such as lipoxygenases. However, these enzymes are expensive to purchase and can be difficult to isolate. In this work, we show that commercial soy flour can be used directly as a source of lipoxygenase for the biosynthesis of specialized pro-resolving mediators from DHA and other biologically important fatty acids...
November 29, 2017: New Biotechnology
https://www.readbyqxmd.com/read/29190851/oxidized-low-density-lipoprotein-and-cell-adhesion-molecules-following-exercise-training
#10
Yunsuk Koh, Jin Park, Rick Carter
Elevated oxidized low-density lipoprotein (ox-LDL) and cell adhesion molecules are associated with inflammation and atherosclerosis. The role of exercise in circulating ox-LDL, enzyme mediators, and cell adhesion molecules are not clearly understood in obesity. As a randomized controlled design, 27 obese (BMI>30 kg/m2) sedentary men (N=13) and women (N=14) were randomly assigned to either an exercise (N=15) or a control (N=12) group. The exercise group performed a 60-min supervised treadmill exercise at moderate intensity (70% of HRmax) for 3 days per week for 4 weeks, while the control group did not exercise...
November 30, 2017: International Journal of Sports Medicine
https://www.readbyqxmd.com/read/29184033/networks-of-enzymatically-oxidized-membrane-lipids-support-calcium-dependent-coagulation-factor-binding-to-maintain-hemostasis
#11
Sarah N Lauder, Keith Allen-Redpath, David A Slatter, Maceler Aldrovandi, Anne O'Connor, Daniel Farewell, Charles L Percy, Jessica E Molhoek, Sirpa Rannikko, Victoria J Tyrrell, Salvatore Ferla, Ginger L Milne, Alastair W Poole, Christopher P Thomas, Samya Obaji, Philip R Taylor, Simon A Jones, Phillip G de Groot, Rolf T Urbanus, Sohvi Hörkkö, Stefan Uderhardt, Jochen Ackermann, P Vince Jenkins, Andrea Brancale, Gerhard Krönke, Peter W Collins, Valerie B O'Donnell
Blood coagulation functions as part of the innate immune system by preventing bacterial invasion, and it is critical to stopping blood loss (hemostasis). Coagulation involves the external membrane surface of activated platelets and leukocytes. Using lipidomic, genetic, biochemical, and mathematical modeling approaches, we found that enzymatically oxidized phospholipids (eoxPLs) generated by the activity of leukocyte or platelet lipoxygenases (LOXs) were required for normal hemostasis and promoted coagulation factor activities in a Ca2+- and phosphatidylserine (PS)-dependent manner...
November 28, 2017: Science Signaling
https://www.readbyqxmd.com/read/29182862/on-the-inhibition-of-mammalian-15-lipoxygenase-by-three-ebselen-like-drugs-a-qm-mm-and-mm-pbsa-comparative-study
#12
Anna Cebrián-Prats, Tiffani Rovira, Patricia Saura, Àngels González-Lafont, José M Lluch
Ebselen is a potent competitive inhibitor of the active form of rabbit 15-lipoxygenase, an enzyme involved in many inflammatory diseases. Light induced Z-to-E isomerization of the ebselen-like 2-(3-benzylidene)-3-oxo-2,3-dihydrobenzo[b]thiophene-7-carboxylic acid methyl ester (BODTCM) molecule was used to convert the weak (Z)-BOTDCM inhibitor into the (E)-isomer with much higher inhibitory capacity. In this study, the binding modes of ebselen, (E)-BOTDCM and (Z)-BOTDCM have been analyzed to provide molecular insights on the inhibitory potency of ebselen and on the geometric-isomer specificity of (E)- and (Z)-BOTDCM inhibitors...
November 28, 2017: Journal of Physical Chemistry. A
https://www.readbyqxmd.com/read/29177613/retinal-pigment-epithelium-and-photoreceptor-preconditioning-protection-requires-docosanoid-signaling
#13
Eric J Knott, William C Gordon, Bokkyoo Jun, Khanh Do, Nicolas G Bazan
Omega-3 and omega-6 polyunsaturated fatty acids (PUFAs) are necessary for functional cell integrity. Preconditioning (PC), as we define it, is an acquired protection or resilience by a cell, tissue, or organ to a lethal stimulus enabled by a previous sublethal stressor or stimulus. In this study, we provide evidence that the omega-3 fatty acid docosahexaenoic acid (DHA) and its derivatives, the docosanoids 17-hydroxy docosahexaenoic acid (17-HDHA) and neuroprotectin D1 (NPD1), facilitate cell survival in both in vitro and in vivo models of retinal PC...
November 24, 2017: Cellular and Molecular Neurobiology
https://www.readbyqxmd.com/read/29154477/mutagenesis-of-sequence-determinants-of-truncated-porcine-alox15-induces-changes-in-the-reaction-specificity-by-altering-the-catalytic-mechanism-of-initial-hydrogen-abstraction
#14
Àngels González-Lafont, Patricia Saura, Ilya Kaganer, Dagmar Heydeck, José M Lluch, Hartmut Kühn
The reaction specificity of lipoxygenases is of physiological relevance since the various oxygenation products exhibit different biological activities. Among mammalian ALOX15 orthologs there are arachidonic acid 12- and 15-lipoxygenating enzymes and recent studies suggested an evolutionary switch in that reaction specificity during late primate development. Previous reports showed that 12-lipoxygenating ALOX15 orthologs can be converted to 15-lipoxygenating enzymes by site-directed mutagenesis of some sequence determinants...
November 20, 2017: Chemistry: a European Journal
https://www.readbyqxmd.com/read/29097313/isomer-distribution-of-hydroxyoctadecadienoates-hode-and-hydroxyeicosatetraenoates-hete-produced-in-the-plasma-oxidation-mediated-by-peroxyl-radical-peroxynitrite-hypochlorite-15-lipoxygenase-and-singlet-oxygen
#15
Aya Umeno, Mayuko Morita, Yasukazu Yoshida, Yuji Naito, Etsuo Niki
Free and ester forms of unsaturated fatty acids and cholesterol are oxidized in vivo by multiple oxidants to give diverse products. Some lipid oxidation is mediated by enzymes to selectively give specific products, while others proceed randomly to produce mixtures of many kinds of regioisomers and stereoisomers. The efficacy of antioxidants against lipid oxidation depends on the nature of the oxidants and therefore the identification of oxidant is important for understanding the roles and effects of lipid oxidation and antioxidants in vivo...
December 1, 2017: Archives of Biochemistry and Biophysics
https://www.readbyqxmd.com/read/29095817/a-regulatory-role-for-%C3%AE-adrenergic-receptors-regarding-the-resolvin-d1-rvd1-pathway-in-the-diabetic-retina
#16
Haoshen Shi, Thomas W Carion, Youde Jiang, Adam Chahine, Jena J Steinle, Elizabeth A Berger
Diabetic retinopathy is a visually debilitating disease with limited treatment options available. Compound 49b, a β-adrenergic receptor agonist, has been demonstrated to effectively reduce disease pathogenesis associated with diabetic retinopathy. While the exact mechanisms are not fully understood, previous studies have determined that it reduces the pro-inflammatory cytokine, TNF-α, and inhibits apoptosis of the retinal microvasculture. As inflammation becomes more recognized in driving disease pathogenesis, so does the regulation by pro-resolving pathways as therapeutic points of intervention...
2017: PloS One
https://www.readbyqxmd.com/read/29079502/inhibiting-12-15-lipoxygenase-to-treat-acute-stroke-in-permanent-and-tpa-induced-thrombolysis-models
#17
H Karatas, Joo Eun Jung, E H Lo, K van Leyen
12/15-Lipoxygenase (12/15-LOX) contributes to the brain damage after middle cerebral artery occlusion (MCAO) in the acute phase of stroke. The aim of this study was to investigate the effects of a 12/15-LOX inhibitor, LOXBlock-1(LB1), in mice using a FeCl3-induced permanent distal MCAO model and FeCl3-induced ischemia/thrombolysis with tPA. In order to induce permanent distal MCAO, 30% FeCl3 was used in C57BL6 mice. LB1 or DMSO treatments were applied intraperitoneally 2hrs following MCAO. For FeCl3-induced ischemia/thrombolysis experiments, 10% FeCl3 was preferred so as to obtain reperfusion with tPA in CD1 mice...
October 24, 2017: Brain Research
https://www.readbyqxmd.com/read/29068244/interaction-between-alox15-polymorphisms-and-coronary-artery-disease-in-north-indian-population
#18
Naindeep Kaur, Jagtar Singh, Sreenivas Reddy
BACKGROUND: Coronary artery disease (CAD) is major cause of death and morbidity worldwide. Arachidonate 12/15-lipoxygenase (ALOX) is a member of the lipid peroxidizing enzyme family and implicated in the pathogenesis of atherosclerosis, but with contradicting results. AIM: The present study aimed to investigate the association of two polymorphisms in ALOX15 (rs2619112 and rs7217186) and the risk of CAD in North Indian population. METHODS: A total of 500 angiographically confirmed CAD patients and 500 control subjects of North Indian population were recruited in the case-control study and genotyped by PCR-RFLP...
October 25, 2017: Clinical and Experimental Hypertension: CHE
https://www.readbyqxmd.com/read/29064442/enhanced-glucose-uptake-in-human-liver-cells-and-inhibition-of-carbohydrate-hydrolyzing-enzymes-by-nordic-berry-extracts
#19
Giang Thanh Thi Ho, Thi Kim Yen Nguyen, Eili Tranheim Kase, Margey Tadesse, Hilde Barsett, Helle Wangensteen
A Western lifestyle with low physical activity and a diet rich in sugar, fat and processed food contribute to higher incidences of diabetes and obesity. Enhanced glucose uptake in human liver cells was observed after treatment with phenolic extracts from different Nordic berries. All berry extracts showed higher inhibition against α-amylase and α-glucosidase than the anti-diabetic agent acarbose. Total phenolic content and phenolic profiles in addition to antioxidant activities, were also investigated. The berries were extracted with 80% methanol on an accelerated solvent extraction system (ASE) and then purified by C-18 solid phase extraction (SPE)...
October 24, 2017: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
https://www.readbyqxmd.com/read/29053969/pebp1-wardens-ferroptosis-by-enabling-lipoxygenase-generation-of-lipid-death-signals
#20
Sally E Wenzel, Yulia Y Tyurina, Jinming Zhao, Claudette M St Croix, Haider H Dar, Gaowei Mao, Vladimir A Tyurin, Tamil S Anthonymuthu, Alexandr A Kapralov, Andrew A Amoscato, Karolina Mikulska-Ruminska, Indira H Shrivastava, Elizabeth M Kenny, Qin Yang, Joel C Rosenbaum, Louis J Sparvero, David R Emlet, Xiaoyan Wen, Yoshinori Minami, Feng Qu, Simon C Watkins, Theodore R Holman, Andrew P VanDemark, John A Kellum, Ivet Bahar, Hülya Bayır, Valerian E Kagan
Ferroptosis is a form of programmed cell death that is pathogenic to several acute and chronic diseases and executed via oxygenation of polyunsaturated phosphatidylethanolamines (PE) by 15-lipoxygenases (15-LO) that normally use free polyunsaturated fatty acids as substrates. Mechanisms of the altered 15-LO substrate specificity are enigmatic. We sought a common ferroptosis regulator for 15LO. We discovered that PEBP1, a scaffold protein inhibitor of protein kinase cascades, complexes with two 15LO isoforms, 15LO1 and 15LO2, and changes their substrate competence to generate hydroperoxy-PE...
October 19, 2017: Cell
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