Effects of NSAIDs on liver microsomal mono-oxygenase system and products of oxidative metabolism of arachidonic acid

1992 ◽  
pp. 204-210 ◽  
Author(s):  
M. E. Fracasso ◽  
L. Franco ◽  
R. Gasperini ◽  
G. P. Velo
Keyword(s):  
Arachidonic Acid ◽  
Oxidative Metabolism

Lyso(bis)phosphatidic acid: A novel source of arachidonic acid for oxidative metabolism by rabbit alveolar macrophages

1985 ◽  
Vol 130 (2) ◽  
pp. 800-806 ◽  
Author(s):  
Felicia R. Cochran ◽  
Janice R. Connor ◽  
Vicki L. Roddick ◽  
B.Moseley Waite
Keyword(s):  
Arachidonic Acid ◽  
Phosphatidic Acid ◽  
Alveolar Macrophages ◽  
Oxidative Metabolism

The oxidative metabolism of arachidonic acid by purified cytochromes P-450

1981 ◽  
Vol 101 (4) ◽  
pp. 1357-1363 ◽  
Author(s):  
Jorge Capdevila ◽  
Linda Parkhill ◽  
Nicholas Chacos ◽  
Richard Okita ◽  
Bettie Sue S. Masters ◽  
...  
Keyword(s):  
Arachidonic Acid ◽  
Oxidative Metabolism

scholarly journals Cytochrome P450/NADPH-dependent biosynthesis of 5,6-trans-epoxyeicosatrienoic acid from 5,6-trans-arachidonic acid

2005 ◽  
Vol 390 (3) ◽  
pp. 719-727 ◽  
Author(s):  
Uzzal Roy ◽  
Robert Joshua ◽  
Russell L. Stark ◽  
Michael Balazy
Keyword(s):  
Arachidonic Acid ◽  
Cytochrome P450 ◽  
Fatty Acid ◽  
Trans Fatty Acid ◽  
Oxidative Metabolism ◽  
Liver Microsomes ◽  
Complex Mixture ◽  
Metabolic Activation ◽  
Lipid Mediator ◽  
Epoxyeicosatrienoic Acid

5,6-trans-AA (5,6-TAA, where TAA stands for trans-arachidonic acid) is a recently identified trans fatty acid that originates from the cis–trans isomerization of AA initiated by the NO2 radical. This trans fatty acid has been detected in blood circulation and we suggested that it functions as a lipid mediator of the toxic effects of NO2. To understand its role as a lipid mediator, we studied the metabolism of 5,6-TAA by liver microsomes stimulated with NADPH. Profiling of metabolites by liquid chromatography/MS revealed a complex mixture of oxidized products among which were four epoxides, their respective hydrolysis products (dihydroxyeicosatrienoic acids), and several HETEs (hydroxyeicosatetraenoic acids) resulting from allylic, bis-allylic and (ω−1)/(ω−2) hydroxylations. We found that the C5–C6 trans bond competed with the three cis bonds for oxidative metabolism mediated by CYP (cytochrome P450) epoxygenase and hydroxylase. This was evidenced by the detection of 5,6-trans-EET (where EET stands for epoxyeicosatrienoic acid), 5,6-erythro-dihydroxyeicosatrienoic acid and an isomer of 5-HETE. A standard of 5,6-trans-EET obtained by iodolactonization of 5,6-TAA was used for the unequivocal identification of the unique microsomal epoxide in which the oxirane ring was of trans configuration. Additional lipid products originated from the metabolism involving the cis bonds and thus these metabolites had the trans C5–C6 bond. The 5,6-trans-isomers of 18- and 19-HETE were likely to be products of the CYP2E1, because a neutralizing antibody partially inhibited their formation without having an effect on the formation of the epoxides. Our study revealed a novel pathway of microsomal oxidative metabolism of a trans fatty acid in which both cis and trans bonds participated. Of particular significance is the detection of the trans-epoxide of AA, which may be involved in the metabolic activation of such trans fatty acids and probably contribute to their biological activity. Unlike its cis-isomer, 5,6-trans-EET was significantly more stable and resisted microsomal hydrolysis and conjugation with glutathione catalysed by hepatic glutathione S-transferase.

scholarly journals Eicosanoid turnover in GtoPdb v.2021.3

2021 ◽  
Vol 2021 (3) ◽  
Author(s):  
Angelo A. Izzo ◽  
Jane A. Mitchell
Keyword(s):  
Oxidative Stress ◽  
Fatty Acids ◽  
Arachidonic Acid ◽  
Cytochrome P450 ◽  
Free Radicals ◽  
Phospholipase A2 ◽  
Oxidative Metabolism ◽  
Molecular Targets ◽  
Structural Analogues ◽  
Biomarkers Of Oxidative Stress

Eicosanoids are 20-carbon fatty acids, where the usual focus is the polyunsaturated analogue arachidonic acid and its metabolites. Arachidonic acid is thought primarily to derive from phospholipase A2 action on membrane phosphatidylcholine, and may be re-cycled to form phospholipid through conjugation with coenzyme A and subsequently glycerol derivatives. Oxidative metabolism of arachidonic acid is conducted through three major enzymatic routes: cyclooxygenases; lipoxygenases and cytochrome P450-like epoxygenases, particularly CYP2J2. Isoprostanes are structural analogues of the prostanoids (hence the nomenclature D-, E-, F-isoprostanes and isothromboxanes), which are produced in the presence of elevated free radicals in a non-enzymatic manner, leading to suggestions for their use as biomarkers of oxidative stress. Molecular targets for their action have yet to be defined.

scholarly journals Lipoxygenase Pathway in Islet Endocrine Cells. OXIDATIVE METABOLISM OF ARACHIDONIC ACID PROMOTES INSULIN RELEASE

1983 ◽  
Vol 71 (5) ◽  
pp. 1191-1205 ◽  
Author(s):  
Stewart Metz ◽  
Michael VanRollins ◽  
Robert Strife ◽  
Wilfred Fujimoto ◽  
R. Paul Robertson
Keyword(s):  
Arachidonic Acid ◽  
Insulin Release ◽  
Oxidative Metabolism ◽  
Endocrine Cells ◽  
Lipoxygenase Pathway

scholarly journals Eicosanoid turnover (version 2019.5) in the IUPHAR/BPS Guide to Pharmacology Database

2019 ◽  
Vol 2019 (5) ◽  
Author(s):  
Angelo A. Izzo ◽  
Jane A. Mitchell
Keyword(s):  
Oxidative Stress ◽  
Fatty Acids ◽  
Arachidonic Acid ◽  
Cytochrome P450 ◽  
Free Radicals ◽  
Phospholipase A2 ◽  
Oxidative Metabolism ◽  
Molecular Targets ◽  
Structural Analogues ◽  
Biomarkers Of Oxidative Stress

Eicosanoids are 20-carbon fatty acids, where the usual focus is the polyunsaturated analogue arachidonic acid and its metabolites. Arachidonic acid is thought primarily to derive from phospholipase A2 action on membrane phosphatidylcholine, and may be re-cycled to form phospholipid through conjugation with coenzyme A and subsequently glycerol derivatives. Oxidative metabolism of arachidonic acid is conducted through three major enzymatic routes: cyclooxygenases; lipoxygenases and cytochrome P450-like epoxygenases, particularly CYP2J2. Isoprostanes are structural analogues of the prostanoids (hence the nomenclature D-, E-, F-isoprostanes and isothromboxanes), which are produced in the presence of elevated free radicals in a non-enzymatic manner, leading to suggestions for their use as biomarkers of oxidative stress. Molecular targets for their action have yet to be defined.

scholarly journals Bradykinin stimulation of oxidative metabolism in renal cortical tubules from rabbit. Possible role of arachidonic acid.

1985 ◽  
Vol 76 (5) ◽  
pp. 1812-1818 ◽  
Author(s):  
P C Brazy ◽  
D R Trellis ◽  
P E Klotman
Keyword(s):  
Arachidonic Acid ◽  
Oxidative Metabolism ◽  
Stimulation Of

Effect of GSH depletion by 1-chloro-2,4-dinitrobenzene on human platelet aggregation, arachidonic acid oxidative metabolism and cytoskeletal proteins

1985 ◽  
Vol 37 (3) ◽  
pp. 423-434 ◽  
Author(s):  
A. Bosia ◽  
P. Spangenberg ◽  
D. Ghigo ◽  
R. Heller ◽  
W. Lösche ◽  
...  
Keyword(s):  
Arachidonic Acid ◽  
Platelet Aggregation ◽  
Oxidative Metabolism ◽  
Human Platelet ◽  
Cytoskeletal Proteins ◽  
Human Platelet Aggregation
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