• CYP2C11 produced epoxyeicosatrienoic acids (EETs) as 61.3%, and CYP2C6 produced midchain HETEs and EETs as 48.3 and 29.4%, respectively, of the total metabolites formed. (aspetjournals.org)
  • In isolated retinas, vasodilations dependent on astrocyte metabolism of arachidonic acid by cytochrome (CYP) P450 2C11 (epoxygenase) to epoxyeicosatrienoic acids (EETs) became less likely as NO levels increased and directly inhibited epoxygenase activity [ 5 ]. (biomedcentral.com)
  • Metabolism of the released arachidonic acid by the cytochrome P450 enzyme system (cP450) generates biologically active compounds, including epoxyeicosatrienoic acids (EETs) and hydroxyeicosatetraenoic acids. (elsevierpure.com)
  • Impairment of endothelial function is typically associated with a reduction in the biosynthesis of vasodilatory epoxyeicosatrienoic acids (e.g., 14,15-EET) identified as an endothelium-derived hyperpolarising element [10]. (lrrk2inhibitor.com)
  • Unlike hormones which are secreted by cells, travel in the circulation to alter the behavior of distant cells, and thereby act as Endocrine signalling agents, these arachidonic acid metabolites act locally as Autocrine signalling and/or Paracrine signaling agents to regulate the behavior of their cells of origin or of nearby cells, respectively. (wikipedia.org)
  • Cytochrome P450 (P450) enzymes mediate arachidonic acid (AA) oxidation to several biologically active metabolites. (aspetjournals.org)
  • CYP1A1 and CYP1A2 produced ω -1→4 hydroxyeicosatetraenoic acids (HETEs) as 88.7 and 62.7%, respectively, of the total metabolites formed. (aspetjournals.org)
  • Synthesis of leukotriene C and other arachidonic acid metabolites by mouse pulmonary macrophages. (silverchair.com)
  • Direct fatty acid analysis of [3H]20:4-labeled PTM cultured in the presence or absence of zymosan indicated that the specific activity of the [3H]20:4 in cell phospholipid provided an accurate measure of 20:4 released by the cells, and could therefore be used to quantitate the synthesis of 20:4 metabolites by PTM in vitro. (silverchair.com)
  • The identified differential metabolites included arachidonic acid derivatives, omega-3 fatty acids, omega-6 fatty acids, and omega-9 fatty acids that were related to unsaturated fatty acid metabolism, which plays a role in the inflammatory responses. (biomedcentral.com)
  • The potential roles of filarial parasite-derived arachidonic acid metabolites as mediators of pathogenicity and as modulators of host immunity will be examined. (grantome.com)
  • By UPLC-Q-Exactive-MS method and multivariate statistical analysis, a total of 15 differential metabolites were identified, including 4 up-regulated and 11 down-regulated biomarkers, of which l -tryptophan, l -leucine, uric acid, 12-HETE, arachidonic acid, PC(20:1(11Z)/14:1(9Z)) and SM(d18:0/24:1(15Z)) were exhibited an important variation, as the potential biomarkers in diabetes. (biomedcentral.com)
  • Hepoxilins (HXs) and trioxilins (TrXs) which are involved in physiological processes such as inflammation, insulin secretion and pain perception in human are metabolites of polyunsaturated fatty acids (PUFAs), including arachidonic acid, eicosapentaenoic acid and docosahexaenoic acid, formed by 12-lipoxygenase (LOX) and epoxide hydrolase (EH) expressed by mammalian cells. (konkuk.ac.kr)
  • 12-Hydroxyeicosatetraenoic acid (12-HETE) is a derivative of the 20 carbon polyunsaturated fatty acid, arachidonic acid, containing a hydroxyl residue at carbon 12 and a 5Z,8Z,10E,14Z Cis-trans isomerism configuration (Z=cis, E=trans) in its four double bonds. (wikipedia.org)
  • Therefore, COX - also known as prostaglandin-endoperoxide synthase (PTGS), fatty acid COX, prostaglandin H (PGH) synthase, and EC 1.14.99.1 - is implicated in the production of fever, inflammation, and pain. (medscape.com)
  • Twenty-carbon polyunsaturated fatty acid with cyclopentane ring. (medscape.com)
  • Their distinct biosynthetic activity includes an endoperoxidase synthase reaction that oxygenates and cyclizes polyunsaturated fatty acid precursors (eg, arachidonic acid) to form prostaglandin G 2 (PGG2), and a peroxidase reaction that converts PGG2 to prostaglandin H 2 (PGH2), as shown below. (medscape.com)
  • Membrane proteins implicated in long-chain fatty acid uptake by mammalian cells: CD36, FATP and FABPm. (springer.com)
  • Airway epithelial cells carry out their physiologic role in part by activating phospholipase-fatty acid oxygenation pathways. (wustl.edu)
  • CYP4F11 is a fatty acid w-hydroxylase and catalyzes the production of the lipid mediator 20-hydroxyeicosatetraenoic acid (20-HETE) from arachidonic acid. (qxmd.com)
  • This trial suggests fish-oil supplementation could mitigate the PM 2.5 -induced inflammatory responses via modulating fatty acid metabolism, providing biological plausibility for the health benefits of fish-oil supplementation against PM 2.5 exposure. (biomedcentral.com)
  • A review of fatty acid 2-hydroxylation in sphingolipid biology in connection with the nervous system and various cell types may be consulted ( Hama H , Biochim Biophys Acta 2010, 1801, 405 ). (gerli.com)
  • Arachidonic acid (AA) is a key polyunsaturated fatty acid (PUFA), which derives a great number of bioactive mediators that are involved in many physiological and pathological processes. (biomedcentral.com)
  • Retinol is commonly esterified to a fatty acid and kept in the liver. (pressbooks.pub)
  • More importantly, this finding shattered a dogma of the time that held that fatty acids played only structural roles in cells, thus opening the way for discovery of the many other important bioactive fatty acid-derived products. (jci.org)
  • [ 6 ] This situation leads to an essential fatty acid deficiency, which is associated with the development of ichthyosis. (medscape.com)
  • In macrophages, 15-LOX-1 converts AA to 15-hydroperoxyeicosatetraenoic acids (15-HpETEs), which is soon reduced by peroxidase to 15-hydroxyeicosatetraenoic acids (15-HETEs). (biomedcentral.com)
  • He localized the biologic activity to a fraction of lipid soluble acids that he termed "prostaglandin," hypothesizing that these substances originate in the prostate gland. (medscape.com)
  • Knowledge of the mechanisms by which fatty acids control specific gene expression may identify important risk factors for cancer and provide insight into the development of new therapeutic strategies for a better management of whole body lipid metabolism. (springer.com)
  • Uptake of long chain fatty acids is regulated by dynamic interaction of FAT/CD36 with cholesterol/sphingolipid enriched microdomains (lipid rafts). (springer.com)
  • KT109 perturbs a lipid network involved in macrophage inflammatory responses and lowers 2-arachidonoylglycerol (2-AG), arachidonic acid and eicosanoids in mouse peritoneal macrophages. (medchemexpress.com)
  • The chemical composition of lipid inclusions in Bacillus megaterium was identifed in 1926 as poly(3-hydroxybutyric acid) ( Lemoigne M, Bull Soc Chim Biol 1926, 8, 770 ). (gerli.com)
  • In lipid science , Eicosanoids are a subclass of organic compounds in the fatty acyl class [FA class] of the lipids superclass generally derived from unsaturated C20 fatty acids or skeletally related compounds, that have hormone-like effects ( autacoid effects , mediated by specialized eicosanoid receptors ). (wellnessadvantage.com)
  • I. Launch Eicosanoids are lipid mediators produced from the hydrolysis of membrane phospholipids by phospholipase A2 (PLA21) into arachidonic acidity (AA), the main element molecule in eicosanoid biosynthesis. (mdm2-inhibitors.com)
  • Phytanic acid replaces other fatty acids, including such essential ones as linoleic and arachidonic acids, in lipid moieties of various tissues. (medscape.com)
  • Fish oil is one of the common dietary supplements, with an abundance of long-chain omega-3 polyunsaturated fatty acids as the active ingredients, including eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) [ 7 , 8 ]. (biomedcentral.com)
  • Among these, arachidonic acid (AA, 20:4n-6) and docosahexaenoic acid (DHA, 22:6n-3) are the principal forms of the long chain (LC) polyunsaturated fatty acids, omega-6 and omega-3 (referred to as n-6 or n-3 PUFAs) of the grey matter. (nature.com)
  • A phytanic acid-restricted diet and combination docosahexaenoic acid and cholic acid therapy may inhibit disease progression. (medscape.com)
  • Although the pathways and products of arachidonic acid metabolism in mammalian cells have been intensely studied, the presence and function of pathways of arachidonic acid metabolism in helminthic parasites are largely undefined. (grantome.com)
  • Utilizing adults and microfilariae of the human lymphatic filarial parasite Brugia malayi, this project will investigate the biochemical pathways of arachidonic acid metabolism in these filarial nematodes. (grantome.com)
  • Possible actions of the antifilarial agent, diethylcarbamazine, on the pathways of parasite arachidonic acid metabolism will be determined. (grantome.com)
  • Two decades later, the prostaglandins were deduced to be a family of related compounds that contain 20-carbon polyunsaturated fatty acids with a cyclopentane ring, as depicted below. (medscape.com)
  • By 1964, after recognition of this basic structure, Bergstrom and colleagues successfully synthesized series 2 prostaglandins from arachidonic acid using sheep seminal fluid. (medscape.com)
  • Bergström stated in his 1982 Nobel lecture that, following the structural assignments of the six PGs, "These 20-carbon prostaglandins have cis -double bonds located as in certain essential fatty acids, when counting from the carboxyl. (jci.org)
  • Acts as a polyunsaturated omega-3 fatty acids hydroxylase: mediates conversion of docosahexaenoate (DHA) to 22-hydroxydocosahexaenoate (PubMed:16820285). (nih.gov)
  • Omega-3 fatty acids (n-3 PUFAs) are essential for the functional maturation of the brain. (nature.com)
  • A research team led by Professor Deok-kun Oh of the Department of Integrative Bioscience and Biotechnology, KU Institute of Technology, has identified the possibility of development of anti-diabetic drugs through biotransformation of polyunsaturated fatty acids to bioactive hepoxilins and trioxilins by microbial enzymes. (konkuk.ac.kr)
  • On January 9, 2018, the research, named "Biotransformation of polyunsaturated fatty acids to bioactive hepoxilins and trioxilins by microbial enzymes" funded by the Mid-Career Researcher Program, through the National Research Foundation grant funded by the Ministry of Science, ICT and Future Planning, Republic of Korea, was published in Nature Communications, a peer-reviewed open access scientific journal published by the Nature Publishing Group since 2010. (konkuk.ac.kr)
  • Cytochrome p450-dependent metabolism of ω-6 and ω-3 long-chain polyunsaturated fatty acids. (springer.com)
  • constriction was attributed to PLA2-mediated arachidonic acid production by astrocytes, followed by diffusion of the arachidonic acid to smooth muscle and subsequent metabolism by cytochrome P450 4A (ω-hydroxylase) to 20-hydroxyeicosatetraenoic acid (20-HETE). (biomedcentral.com)
  • AA and DHA are either biosynthesized from their respective dietary precursors, linoleic acid (LA, 18:2n-6), and α-linolenic acid (ALA, 18:3n-3), or directly sourced from the diet (mainly meat and dairy products for AA, fatty fish for DHA) 2 . (nature.com)
  • This made us suspect that these naturally occurring acids might be precursors" (see ref. 5 and references within). (jci.org)
  • An infantile form of Refsum disease also exists and is an autosomal recessive disorder of peroxisomal biogenesis, leading to many biochemical abnormalities, including elevated plasma concentration of phytanic acid, pristanic acid, very long chain fatty acids, and C27 bile acids. (medscape.com)
  • Mice also express an epidermal type 15-lipoxygenase (e-12LO) which has 50.8% amino acid sequence identity to human 15-LOX-2 and 49.3% sequence identity to mouse Arachidonate 8-lipoxygenase. (wikipedia.org)
  • AACOCF3 blocks production of arachidonate and 12-hydroxyeicosatetraenoic acid by calcium ionophore-challenged platelets. (medchemexpress.com)
  • Therefore, determining te factors that regulate arachidonic acid metabolismin airway epithelial cells is still a fundamental goal for unraveling the role of arachidonate products in airway function and for altering eicosanoid production in the airway. (wustl.edu)
  • Mechanisms of parasite incorporation of arachidonate will be further evaluated and compared with those for other saturated and unsaturated fatty acids. (grantome.com)
  • This article reviews the current knowledge and experimental research about the mechanisms by which fatty acids and their derivatives control specific gene expression involved during carcinogenesis. (springer.com)
  • Pathway analysis indicated that phenylalanine, tyrosine and tryptophan biosynthesis and arachidonic acid metabolism were prone to interference in diabetes. (biomedcentral.com)
  • Arachidonic acid is an essential constituent of cell membranes that is esterified to the sn-2 position of glycerophospholipids and is released from selected phospholipid pools by tightly regulated phospholipase cleavage. (elsevierpure.com)
  • 12(R)-HpETE also spontaneously decomposes to a mixture of hepoxilins and trihydroxy-eicosatetraenoic acids that possess R or S hydroxy and epoxy residues at various sites while 8R-hydroxy-11R,12R-epoxy-hepoxilin A3 spontaneously decomposes to 8R,11R,12R-trihydroxy-5Z,9E,14Z-eicosatetraenoic acid. (wikipedia.org)
  • a -Hydroxy acids or 2-hydroxy acids are found in plants (chain from 12 up to 24 carbon atoms) and in animal wool waxes, skin lipids and specialized tissues, mainly in brain. (gerli.com)
  • Refsum disease (RD) is a neurocutaneous syndrome that is characterized biochemically by the accumulation of phytanic acid in plasma and tissues. (medscape.com)
  • Isoform CYP4F3A: Catalyzes the omega-hydroxylation of leukotriene-B(4), a potent chemoattractant for polymorphonuclear leukocytes, it has low activity for arachidonic acid. (nih.gov)
  • Several studies have uncovered potent biological activities of 2-hydroxyoleic acid (Minerval). (gerli.com)
  • Cleavage of sn-2 fatty acids by PLA2 results in the production of free thiols, which react with chromogenic reagents such as DTNB (Ellman's reagent) and DTP, allowing quantification of PLA2 activity. (medchemexpress.com)
  • Patients with RD are unable to degrade phytanic acid because of a deficient activity of phytanoyl-CoA hydroxylase (PhyH), a peroxisomal enzyme catalyzing the first step of phytanic acid alpha-oxidation. (medscape.com)
  • Skeletal defects (noticed in some patients) are not related directly to phytanic acid levels. (medscape.com)
  • In Refsum disease (RD), the phytanic acid level in the blood is increased. (medscape.com)
  • however, phytanic acid levels are 10-50 mg/dL or even higher in patients with RD. (medscape.com)
  • [ 8 ] A minor indication is failure of dietary management to reduce a high plasma phytanic acid level. (medscape.com)
  • Pharmacological up-regulation of the omega-oxidation of phytanic acid may form the basis of the new treatment strategy for adult RD in the near future. (medscape.com)
  • Patients with Refsum disease are unable to degrade phytanic acid because of a deficient activity of phytanoyl-CoA hydroxylase (PhyH), a peroxisomal enzyme catalyzing the first step of phytanic acid alpha-oxidation. (medscape.com)
  • Refsum disease is a recessive disorder characterized by defective peroxisomal alpha-oxidation of phytanic acid. (medscape.com)
  • Blood levels of phytanic acid are increased in patients with Refsum disease. (medscape.com)
  • Mouse resident pulmonary macrophages were subdivided into alveolar (PAM) and interstitial (PTM) populations on the basis of accessibility to pulmonary lavage, and zymosan-induced arachidonic acid (20:4) metabolism was examined in both populations labeled with [3H]20:4. (silverchair.com)
  • The ability of adults or microfilariae to incorporate 3H-arachidonic acid in vitro into parasite neutral and phospholipids has been assessed utilizing thin layer chromatography and reverse phase high performance liquid chromatography (HPLC). (grantome.com)
  • It was first found as a product of arachidonic acid metabolism made by human and bovine platelets through their 12S-lipoxygenase (i.e. (wikipedia.org)
  • 15-oxo-5,8,11,13-(Z,Z,Z,E)-eicosatetraenoic acid (15-oxo-ETE) was formed from 15-hydroxyprostaglandin dehydrogenase (PGDH)-mediated oxidation of 15(S)-HETE. (biomedcentral.com)
  • MUFAs, palmitoleic acid (16:1 n9), and oleic acid (18:1 n9) in NASH compared to control group. (wjgnet.com)
  • Furthermore, using sequence analysis of human genomic DNA, researchers concluded that the amino acids important for catalysis by COX-1 are conserved and are equally important for catalysis by COX-2. (medscape.com)
  • Further investigations are required to explore the diverse chemical natures of distinct PBPs from different cyanobacteria and red algae because their amino acid sequences vary among different algal species. (m0b1le.net)
  • The overactivation of RAS in hypertension is connected with the excessive generation of arachidonic acid-derived 20-hydroxyeicosatetraenoic acid (20-HETE), a robust vasoconstrictor, which potentiates systemic vascular bed responses to angiotensin II (Ang II), and additionally impairs endothelial function [8,9]. (lrrk2inhibitor.com)
  • Digalloyl-resveratrol (di-GA) is a synthetic compound aimed to combine the biological effects of the plant polyhydroxy phenols gallic acid and resveratrol, which are both radical scavengers and cyclooxygenase inhibitors exhibiting anticancer activity. (nature.com)
  • Some polyhydroxy fatty acids are also known, which are most frequently produced by lipoxygenase activities, as for several mono-hydroxylated fatty acids. (gerli.com)
  • ALOX12 metabolizes arachidonic acid almost exclusively to 12(S)-hydroperoxy-5Z,8Z,10E,14Z-eicosatetraenoic acid (12(S)-HpETE or 12S-HpETE). (wikipedia.org)
  • Vitamin A comes in three primary chemical forms, retinol (storage in liver - Figure 2.225), retinal (role in vision - Figure 2.226), and retinoic acid (roles in growth and development). (pressbooks.pub)
  • The remaining 98 to 99% of an oral dose will reach the colon, where each molecule is rapidly converted into two molecules of 5-aminosalicylic acid (5-ASA) by colonic bacteria and the low prevailing redox potential found in this environment. (nih.gov)
  • Each phospholipid molecule contains two fatty acids. (wellnessadvantage.com)
  • Indeed, evidence obtained with isotopically labeled 20-carbon fatty acids incubated with sheep vesicular glands, an abundant source of PGs, confirmed this assumption. (jci.org)
  • It acts in differentiation of stem cells through a specific cellular retinoic acid receptor. (pressbooks.pub)
  • Fatty acids specifically related to the anisotropic properties of plasma membrane from rat urothelium. (springer.com)
  • Gallic acid is also present at high concentrations in gallnuts (name), which are proliferations of plant leaves that become elicited by gall wasp exudates to build up a hatchery for their larvae. (nature.com)
  • Artemisinin, rosmarinic and chlorogenic acids tested at plausible intestinal concentrations had no effect on the CYP3A4 activity. (iwerliewen.org)