Reaction Process: WikiPathways:WP5324
Octadecanoid formation from linoleic acid related metabolites
find 26 related metabolites which is associated with chemical reaction(pathway) Octadecanoid formation from linoleic acid
10-HODA ⟶ 9(Z)-OME Oleic Acid
Oleic acid
Oleic acid (or 9Z)-Octadecenoic acid) is an unsaturated C-18 or an omega-9 fatty acid that is the most widely distributed and abundant fatty acid in nature. It occurs naturally in various animal and vegetable fats and oils. It is an odorless, colorless oil, although commercial samples may be yellowish. The name derives from the Latin word oleum, which means oil. Oleic acid is the most abundant fatty acid in human adipose tissue, and the second most abundant in human tissues overall, following palmitic acid. Oleic acid is a component of the normal human diet, being a part of animal fats and vegetable oils. Triglycerides of oleic acid represent the majority of olive oil (about 70\\\\%). Oleic acid triglycerides also make up 59–75\\\\% of pecan oil, 61\\\\% of canola oil, 36–67\\\\% of peanut oil, 60\\\\% of macadamia oil, 20–80\\\\% of sunflower oil, 15–20\\\\% of grape seed oil, sea buckthorn oil, 40\\\\% of sesame oil, and 14\\\\% of poppyseed oil. High oleic variants of plant sources such as sunflower (~80\\\\%) and canola oil (70\\\\%) also have been developed. consumption has been associated with decreased low-density lipoprotein (LDL) cholesterol, and possibly with increased high-density lipoprotein (HDL) cholesterol, however, the ability of oleic acid to raise HDL is still debated. Oleic acid may be responsible for the hypotensive (blood pressure reducing) effects of olive oil that is considered a health benefit. Oleic acid is used in manufacturing of surfactants, soaps, plasticizers. It is also used as an emulsifying agent in foods and pharmaceuticals. Oleic acid is used commercially in the preparation of oleates and lotions, and as a pharmaceutical solvent. Major constituent of plant oils e.g. olive oil (ca. 80\\\\%), almond oil (ca. 80\\\\%) and many others, mainly as glyceride. Constituent of tall oiland is also present in apple, melon, raspberry oil, tomato, banana, roasted peanuts, black tea, rice bran, cardamon, plum brandy, peated malt, dairy products and various animal fats. Component of citrus fruit coatings. Emulsifying agent in foods CONFIDENCE standard compound; INTERNAL_ID 290 COVID info from WikiPathways Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Oleic acid (9-cis-Octadecenoic acid) is an abundant monounsaturated fatty acid[1]. Oleic acid is a Na+/K+ ATPase activator[2]. Oleic acid (9-cis-Octadecenoic acid) is an abundant monounsaturated fatty acid[1]. Oleic acid is a Na+/K+ ATPase activator[2].
Linoleic acid
Linoleic acid is a doubly unsaturated fatty acid, also known as an omega-6 fatty acid, occurring widely in plant glycosides. In this particular polyunsaturated fatty acid (PUFA), the first double bond is located between the sixth and seventh carbon atom from the methyl end of the fatty acid (n-6). Linoleic acid is an essential fatty acid in human nutrition because it cannot be synthesized by humans. It is used in the biosynthesis of prostaglandins (via arachidonic acid) and cell membranes (From Stedman, 26th ed). Linoleic acid is found to be associated with isovaleric acidemia, which is an inborn error of metabolism. Linoleic acid (LA) is an organic compound with the formula HOOC(CH2)7CH=CHCH2CH=CH(CH2)4CH3. Both alkene groups (−CH=CH−) are cis. It is a fatty acid sometimes denoted 18:2 (n-6) or 18:2 cis-9,12. A linoleate is a salt or ester of this acid.[5] Linoleic acid is a polyunsaturated, omega-6 fatty acid. It is a colorless liquid that is virtually insoluble in water but soluble in many organic solvents.[2] It typically occurs in nature as a triglyceride (ester of glycerin) rather than as a free fatty acid.[6] It is one of two essential fatty acids for humans, who must obtain it through their diet,[7] and the most essential, because the body uses it as a base to make the others. The word "linoleic" derives from Latin linum 'flax', and oleum 'oil', reflecting the fact that it was first isolated from linseed oil.
12,13-DiHOME
12,13-DHOME (CAS: 263399-35-5), also known as 12,13-dihydroxy-9-octadecenoic acid or 12,13-DiHOME, is the epoxide hydrolase metabolite of the leukotoxin 12,13-EpOME. 12,13-EpOME acts as a protoxin, with the corresponding epoxide hydrolase 12,13-DHOME specifically exerting toxicity. Both the EpOME and the DHOME are shown to have neutrophil chemotactic activity. 12,13-DHOME suppress the neutrophil respiratory burst by a mechanism distinct from that of respiratory burst inhibitors such as cyclosporin H or lipoxin A4, which inhibit multiple aspects of neutrophil activation. 12,13-DHOME is a derivative of the linoleic acid diol that has been reported to be toxic in human tissue preparations. 12,13-DHOME is a naturally occurring proliferator-activated receptor (PPAR) gamma2 ligand, which stimulates adipocytes and inhibits osteoblast differentiation (PMID: 17435320, 12021203, 12127265). 12,13-DHOME is the epoxide hydrolase metabolite of the leukotoxin12,13-EpOME. 12,13-EpOMEs act as a protoxin, with the corresponding epoxide hydrolase 12,13-DiHOME specifically exerting toxicity. Both the EpOME and the DiHOME are shown to have neutrophil chemotactic activity. 12,13-DiHOME suppress the neutrophil respiratory burst by a mechanism distinct from that of respiratory burst inhibitors such as cyclosporin H or lipoxin A4,which inhibit multiple aspects of neutrophil activation. 12,13-DHOME is a derivative of linoleic acid diol that have been reported to be toxic in humans tissue preparations. 12,13-DHOME is a naturally occurring proliferator-activated receptor (PPAR) gamma2 ligand, which stimulates adipocytes and inhibits osteoblast differentiation. (PMID: 17435320, 12021203, 12127265) [HMDB]
9-Oxo-ODE
9-OxoODE results from oxidation of the allylic hydroxyl of either 9(S)- or 9(R)-HODE. Rabbit reticulocyte plasma and mitochondrial membranes contain both 9- and 13-oxoODEs, representing about 2\\% of the total linoleate residues in the membranes. Most of these oxidized linoleate residues are esterified to membrane lipids. [HMDB] 9-OxoODE results from oxidation of the allylic hydroxyl of either 9(S)- or 9(R)-HODE. Rabbit reticulocyte plasma and mitochondrial membranes contain both 9- and 13-oxoODEs, representing about 2\\% of the total linoleate residues in the membranes. Most of these oxidized linoleate residues are esterified to membrane lipids.
3-HODE + 9-HODE
13-Hydroxyoctadecadienoic acid (13-HODE) (CAS: 18104-45-5), also known as 13(S)-hydroxy-9Z,11E-octadecadienoic acid or 13(S)-HODE, is the major lipoxygenation product synthesized in the body from linoleic acid. 13-HODE prevents cell adhesion to endothelial cells and can inhibit cancer metastasis. 13-HODE synthesis is enhanced by cyclic AMP. gamma-Linolenic acid, a desaturated metabolite of linoleic acid, causes substantial stimulation of 13-HODE synthesis. A fall in gamma-linolenic acid synthesis with age may be related to the age-related fall in 13-HODE formation (PMID: 9561154). 13-HODE is considered an intermediate in linoleic acid metabolism. It is generated from 13(S)-HPODE via the enzyme lipoxygenase (EC 1.13.11.12). 13-HODE has been shown to be involved in cell proliferation and differentiation in a number of systems. 13-HODE is found to be produced by prostate tumours and cell lines and researchers believe that there is a link between linoleic acid metabolism and the development or progression of prostate cancer (PMID: 9367845).
13-L-Hydroperoxylinoleic acid
(9z,11e)-(13s)-13-hydroperoxyoctadeca-9,11-dienoate, also known as 13s-hydroperoxy-9z,11e-octadecadienoic acid or 13(S)-hpode, belongs to lineolic acids and derivatives class of compounds. Those are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. Thus, (9z,11e)-(13s)-13-hydroperoxyoctadeca-9,11-dienoate is considered to be an octadecanoid lipid molecule (9z,11e)-(13s)-13-hydroperoxyoctadeca-9,11-dienoate is practically insoluble (in water) and a weakly acidic compound (based on its pKa). (9z,11e)-(13s)-13-hydroperoxyoctadeca-9,11-dienoate can be synthesized from octadeca-9,11-dienoic acid (9z,11e)-(13s)-13-hydroperoxyoctadeca-9,11-dienoate can also be synthesized into pinellic acid and 13(S)-HPODE methyl ester (9z,11e)-(13s)-13-hydroperoxyoctadeca-9,11-dienoate can be found in a number of food items such as lingonberry, lemon thyme, watermelon, and agave, which makes (9z,11e)-(13s)-13-hydroperoxyoctadeca-9,11-dienoate a potential biomarker for the consumption of these food products (9z,11e)-(13s)-13-hydroperoxyoctadeca-9,11-dienoate can be found primarily in blood. 13-L-Hydroperoxylinoleic acid (13(S)-HPODE) is one of the primary products of the major polyunsaturated fatty acids (linoleic acid and arachidonic acid) from the 15-lipoxygenase pathway (EC 1.13.11.31). 13(S)-HPODE is a rather unstable metabolite and is rapidly metabolized to more stable secondary products such as diverse forms of hydroxy fatty acids (via reduction of the hydroperoxy group), alkoxy radicals (via homolytic cleavage of the peroxy group), forms of dihydro(pero)xy fatty acids (via lipoxygenase-catalysed double and triple oxygenation), or epoxy leukotrienes (via a hydrogen abstraction from a doubly allylic methylene group and a homolytic cleavage of the hydroperoxy group) (PMID: 9082450). D009676 - Noxae > D016877 - Oxidants > D010545 - Peroxides
13-OxoODE
13-oxoODE is produced from 13-HODE by a NAD+-dependent dehydrogenase present in rat colonic mucosa. 13-OxoODE has been shown to stimulate cell proliferation when instilled intrarectally in rats. 13-OxoODE has also been detected in preparations of rabbit reticulocyte plasma and mitochondrial membranes, mostly esterified to phospholipids. Production of 13-oxoODE is putatively linked to the maturation of reticulocytes to erythrocytes through the activity of 15-LO. [HMDB] 13-oxoODE is produced from 13-HODE by a NAD+-dependent dehydrogenase present in rat colonic mucosa. 13-OxoODE has been shown to stimulate cell proliferation when instilled intrarectally in rats. 13-OxoODE has also been detected in preparations of rabbit reticulocyte plasma and mitochondrial membranes, mostly esterified to phospholipids. Production of 13-oxoODE is putatively linked to the maturation of reticulocytes to erythrocytes through the activity of 15-LO.
9,10-DiHOME
9,10-Dihydroxy-12-octadecenoic acid (CAS: 263399-34-4), also known as 9,10-DHOME, is a derivative of linoleic acid diol and has been reported to be toxic in humans tissue preparations. 9,10-DHOME is a naturally occurring proliferator-activated receptor (PPAR) gamma2 ligand, which stimulates adipocytes and inhibits osteoblast differentiation. 9,10-DHOME is the epoxide hydrolase metabolite of the leukotoxin 9,10-EpOME. 9,10-EpOME act as a protoxin, with the corresponding epoxide hydrolase metabolite 9,10-DHOME, specifically exerting toxicity. Both 9,10-EpOME and 9,10-DHOME are shown to have neutrophil chemotactic activity. 9,10-DHOME suppresses the neutrophil respiratory burst by a mechanism distinct from that of respiratory burst inhibitors such as cyclosporin H or lipoxin A4, which inhibit multiple aspects of neutrophil activation (PMID: 12021203, 12127265, 17435320). 9,10-DHOME is found in fruits and can be isolated from the seeds of Cucurbita pepo. 9,10-DHOME is a derivative of linoleic acid diol that have been reported to be toxic in humans tissue preparations. 9,10-DHOME is a naturally occurring proliferator-activated receptor (PPAR) gamma2 ligand, which stimulates adipocytes and inhibits osteoblast differentiation. 9,10-DHOME is the epoxide hydrolase metabolite of the leukotoxin 9,10--EpOME. 9,10-EpOMEs act as a protoxin, with the corresponding epoxide hydrolase 9,10-DiHOME specifically exerting toxicity. Both the 9,10-EpOME and the 9,10-DiHOME are shown to have neutrophil chemotactic activity. 9,10-DiHOME suppress the neutrophil respiratory burst by a mechanism distinct from that of respiratory burst inhibitors such as cyclosporin H or lipoxin A4,which inhibit multiple aspects of neutrophil activation. (PMID: 12021203, 12127265, 17435320) [HMDB]
9,10-Epoxyoctadecenoic acid
9,10-Epoxyoctadecenoic acid (9,10-EOA) is a peroxidation product of linoleic acid (LA). 9,10-EOA is a naturally occurring component of oxidized low density lipoprotein (LDL), the level of which increases with aging, atherosclerosis, and rheumatoid arthritis, perhaps due to an increase in 15-lipoxygenase and free oxygen radicals. 9,10-EOA is a proliferator-activated receptors (PPAR) gamma2 ligand, that is antiosteogenic without stimulating adipocyte differentiation. Studies in dogs suggest that 9,10-EOA has toxic cardiovascular effects. (PMID: 12665667, 12021203, 10667371).
alpha-Dimorphecolic acid
alpha-Dimorphecolic acid or 9(S)-HODE is an endogenous fatty acid (PPAR)gamma agonist synthesized in the body from linoleic acid. alpha-Dimorphecolic acid activates peroxisomal proliferator-activated receptor-gamma (PPAR)gamma in human endothelial cells increasing plasminogen activator inhibitor type-1 expression. Plasminogen activator inhibitor type-1 (PAI-1) is a major physiological inhibitor of fibrinolysis, with its plasma levels correlating with the risk for myocardial infarction and venous thrombosis. The regulation of PAI-1 transcription by endothelial cells (ECs), a major source of PAI-1, remains incompletely understood. Adipocytes also produce PAI-1, suggesting possible common regulatory pathways between adipocytes and ECs. Peroxisomal proliferator-activated receptor-gamma (PPAR)gamma is a ligand-activated transcription factor that regulates gene expression in response to various mediators such as 15-deoxy-delta12, 14-prostaglandin J2 (15d-PGJ2) and oxidized linoleic acid (9- and 13-HODE). alpha-Dimorphecolic acid is a ligand of the G protein-coupled receptor G2A (PMID: 10073956, 16647253, 16236715). alpha-Dimorphecolic acid inhibits the proliferation of NHEK cells by suppressing DNA synthesis and arresting the cell cycle in the G0/1-phase. alpha-Dimorphecolic acid-G2A signalling plays proinflammatory roles in the skin under oxidative conditions (PMID: 18034171). Present in plant and animal lipids as autoxidn. or lipoxygenase oxidn. production of linoleic acid.
9,10,13-TriHOME
9,10,13-TriHOME is a trihydroxyoctadecenoic acid metabolite of linoleic acid, one of the major fatty acids found in lipids. Vascular tissue converts various polyunsaturated fatty acids to monohydroxy and trihydroxy metabolites derived from hydroperoxides which may be involved in regulating prostaglandin synthesis. [HMDB] 9,10,13-TriHOME is a trihydroxyoctadecenoic acid metabolite of linoleic acid, one of the major fatty acids found in lipids. Vascular tissue converts various polyunsaturated fatty acids to monohydroxy and trihydroxy metabolites derived from hydroperoxides which may be involved in regulating prostaglandin synthesis.
xi-10-Hydroxyoctadecanoic acid
xi-10-Hydroxyoctadecanoic acid is found in herbs and spices. xi-10-Hydroxyoctadecanoic acid is a constituent of leaf cutins of rosemary. Constituent of leaf cutins of rosemary. xi-10-Hydroxyoctadecanoic acid is found in herbs and spices.
FA 18:1
trans-Vaccenic acid is a precursor for the synthesis of saturated fatty acid in the rumen and of conjugated linoleic acid (CLA) at the tissue level. trans-Vaccenic acid is a precursor for the synthesis of saturated fatty acid in the rumen and of conjugated linoleic acid (CLA) at the tissue level.
12,13-EpOME
12,13-EpOME is the 12,13-cis epoxide of linoleic acid, generated by neutrophils during the oxidative burst. The toxicity and biosynthesis of 12,13-EpOME has not been well differentiated from 9,10-EpOME, but has been presumed to be essentially the same.P [HMDB]. Vernolic acid is found in rice. 12,13-EpOME is the 12,13-cis epoxide of linoleic acid, generated by neutrophils during the oxidative burst. The toxicity and biosynthesis of 12,13-EpOME has not been well differentiated from 9,10-EpOME, but has been presumed to be essentially the same.P.
12(13)Ep-9-KODE
trans-12,13-epoxy-11-oxo-trans-9-octadecenoic acid is a novel product from 13-L (S)-hydroperoxy-cis-9,trans-11-octadecadienoic acid under degradation of linoleic acid hydroperoxides by a cysteine . FeCl3 catalyst as a model for similar biochemical reactions. III. [HMDB] trans-12,13-epoxy-11-oxo-trans-9-octadecenoic acid is formed from 13-L (S)-hydroperoxy-cis-9,trans-11-octadecadienoic acid by a cysteine • FeCl3 redox couple in the presence of O2 (PMID: 7284410).
10-Oxooctadecanoic acid
10-Oxooctadecanoic acid is found in milk and milk products. 10-Oxooctadecanoic acid is a trace constituent of milk fa Trace constituent of milk fat. 10-Oxooctadecanoic acid is found in milk and milk products.
(9E,11E)-Octadecadienoic acid
Conjugated linoleic acid is an integral term for the mixture of positional and geometrical isomers of the octadecadienoic acids, whose two double-bonds are separated with one single-bond. The most common isomers are cis-9, trans-11, and trans-10, cis-12. Conjugated linoleic acid is present in the food namely in the red meat and dairy products which the contemporary dietary recommendations tend to limit. Those limitations should be compensated with dietary supplements. Much attention has focused on the therapeutic potential of conjugated linoleic acid. Initial animal studies associated conjugated linoleic acid with beneficial health properties, such as reducing the risk of cancer, diabetes, atherosclerosis, inflammation and obesity. More recent human conjugated linoleic acid supplementation studies have often shown conflicting and less convincing health benefits. The marked variation between studies may reflect the isomer-specific effect of the individual conjugated linoleic acid isomers, which can often have opposing effects. Detrimental effects have been observed in some studies, in particular after supplementation with the trans-10,cis-12 conjugated linoleic acid isomer. Diet composition may modulate CLA effects on body fat accumulation. As far as human studies are concerned, a specific dietary pattern has not been established. As a result differences among studies and also among subjects in the same study are likely. In rodents, the effects of CLA vary with genotype, suggesting that genetic predisposition to fat accumulation can play an important role in the effectiveness of CLA. Human volunteers with different body mass index have participated in the published studies and even in the same experiment. So, differences in lipid metabolism among subjects could help to explain the discrepancies observed in the literature. Age and maturity may also be crucial. (PMID: 17053429, 17217167, 17554969, 16477173). Conjugated linoleic acid (CLA) is a collective term for a mixture of positional and geometric isomers of linoleic acid (18:2) in which the two double bonds are conjugated. CLA has been suggested to have effects on human health, including effects on body composition, blood lipids, liver metabolism, insulin sensitivity and immune function, with mixed results.
(10E,12Z)-Octadecadienoic acid
Conjugated linoleic acid (CLA) is a collective term for a mixture of positional and geometric isomers of linoleic acid (18:2) in which the two double bonds are conjugated. CLA has been suggested to have effects on human health, including effects on body composition, blood lipids, liver metabolism, insulin sensitivity and immune function, with mixed results. Some reported data suggest that the effects of the substance may be isomer dependent and that cis-9,trans-11 and trans-10,cis-12 conjugated linoleic acids have opposing effects, the later (trans-10,cis-12 CLA) having a relative detrimental effect on blood lipids. (PMID 16477173). (10E,12Z)-Octadeca-10,12-dienoic acidactivates PPAR α and inhibits adipocyte differentiation[1]. (10E,12Z)-Octadeca-10,12-dienoic acid and its downstream metabolites have various antioxidant and antitumor activities. (10E,12Z)-Octadeca-10,12-dienoic acid is effective orally[2][3].
(9S,10E,12S,13S)-9,12,13-Trihydroxy-10-octadecenoic acid
Pinellic acid is found in cereals and cereal products. Pinellic acid is isolated from a rice cultivar. Confers resistance to rice blast disease. Found in beer and blast-resistant rice
(10E,12Z)-9-HODE
(10E,12Z)-9-HODE, also known as 9-Hydroxy-10E,12Z-octadecadienoic acid or 9-Hydroxylinoleic acid, is classified as a lineolic acid or a Lineolic acid derivative. Lineolic acids are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. (10E,12Z)-9-HODE is considered to be practically insoluble (in water) and acidic. (10E,12Z)-9-HODE is an octadecanoid lipid molecule