Chemical Formula: C20H30O5
Chemical Formula C20H30O5
Found 343 metabolite its formula value is C20H30O5
Andrographolide
Andrographolide is a labdane diterpenoid isolated from the leaves and roots of Andrographis paniculata that exhibits anti-HIV, anti-inflammatory and antineoplastic properties. It has a role as a metabolite, an anti-inflammatory drug, an anti-HIV agent and an antineoplastic agent. It is a gamma-lactone, a primary alcohol, a secondary alcohol, a labdane diterpenoid and a carbobicyclic compound. Andrographolide (HMPL-004) is a botanical product extracted from a herb that occurs naturally in China. The herb has an extensive history of use in TCM for the treatment of upper respiratory tract infections and other inflammatory and infectious diseases. Andrographolide is a natural product found in Andrographis paniculata, Ginkgo biloba, and Cymbopogon schoenanthus with data available. Andrographolide is a labdane diterpenoid that is produced by the Andrographis paniculata plant, which has a broad range of therapeutic applications including anti-inflammatory and anti-platelet aggregation activities and potential antineoplastic properties. Since andrographolide has multiple therapeutic activities there are several proposed mechanisms of action for this agent. The anti-inflammatory effects of this agent appear to be related to the inhibition of nitric oxide (NO) production by macrophages. This agent may activate the NO/cyclic GMP pathway and inhibit both the phospholipase C gamma 2 (PLC gamma2)/protein kinase C (PKC) and PI3K/AKT-MAPK signaling pathways in activated platelets to inhibit platelet aggregation. In activated platelets, these three signaling pathways are downstream of integrin activation mediated by collagen binding and influence the association of fibrinogen with its receptors. Additionally, andrographolide may exert its anti-cancer activity through the induction of cell cycle arrest at G0/G1 phase and the stimulation of lymphocyte proliferation and activation. These processes could result in decreased proliferation of and increased immunocytotoxicity against tumor cells. A labdane diterpenoid isolated from the leaves and roots of Andrographis paniculata that exhibits anti-HIV, anti-inflammatory and antineoplastic properties. D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000981 - Antiprotozoal Agents D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents C78275 - Agent Affecting Blood or Body Fluid > C1327 - Antiplatelet Agent D006401 - Hematologic Agents > D010975 - Platelet Aggregation Inhibitors D002491 - Central Nervous System Agents > D000700 - Analgesics D000890 - Anti-Infective Agents > D000998 - Antiviral Agents D000893 - Anti-Inflammatory Agents D018501 - Antirheumatic Agents Origin: Plant; SubCategory_DNP: Diterpenoids, Andrographolide diterpenoids relative retention time with respect to 9-anthracene Carboxylic Acid is 0.941 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.939 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.936 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.938 Andrographolide is a NF-κB inhibitor, which inhibits NF-κB activation through covalent modification of a cysteine residue on p50 in endothelial cells without affecting IκBα degradation or p50/p65 nuclear translocation. Andrographolide has antiviral effects. Andrographolide is a NF-κB inhibitor, which inhibits NF-κB activation through covalent modification of a cysteine residue on p50 in endothelial cells without affecting IκBα degradation or p50/p65 nuclear translocation. Andrographolide has antiviral effects.
15-Keto-prostaglandin E2
15-keto-PGE2 is one of the prostaglandin E2 metabolites. (PMID 7190512). It is a degradation product produced by 15-hydroxy prostaglandin dehydrogenase (PGDH or 15-PGDH). Dinoprostone is a naturally occurring prostaglandin E2 (PGE2) and the most common and most biologically active of the mammalian prostaglandins. It has important effects in labour and also stimulates osteoblasts to release factors which stimulate bone resorption by osteoclasts (a type of bone cell that removes bone tissue by removing the bones mineralized matrix). PGE2 has been shown to increase vasodilation and cAMP production, to enhance the effects of bradykinin and histamine, to induce uterine contractions and to activate platelet aggregation. PGE2 is also responsible for maintaining the open passageway of the fetal ductus arteriosus; decreasing T-cell proliferation and lymphocyte migration and activating the secretion of IL-1alpha and IL-2. PGE2 exhibits both pro- and anti-inflammatory effects, particularly on dendritic cells (DC). Depending on the nature of maturation signals, PGE2 has different and sometimes opposite effects on DC biology. PGE2 exerts an inhibitory action, reducing the maturation of DC and their ability to present antigen. PGE2 has also been shown to stimulate DC and promote IL-12 production when given in combination with TNF-alpha. PGE2 is an environmentally bioactive substance. Its action is prolonged and sustained by other factors especially IL-10. It modulates the activities of professional DC by acting on their differentiation, maturation and their ability to secrete cytokines. PGE2 is a potent inducer of IL-10 in bone marrow-derived DC (BM-DC), and PGE2-induced IL-10 is a key regulator of the BM-DC pro-inflammatory phenotype. (PMID: 16978535). Prostaglandins are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs), and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes), and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signalling pathways. 15-keto-PGE2 is one of the prostaglandin E2 metabolites. (PMID 7190512). It is a degradation product produced by 15-hydroxy prostaglandin dehydrogenase (PGDH or 15-PGDH)
9S-hydroxy-11,15-dioxo-5Z,13E-prostadienoic acid
9S-hydroxy-11,15-dioxo-5Z,13E-prostadienoic acid is also known as 15-Deoxy-15-oxo-prostaglandin D2. 9S-hydroxy-11,15-dioxo-5Z,13E-prostadienoic acid is considered to be practically insoluble (in water) and acidic. 9S-hydroxy-11,15-dioxo-5Z,13E-prostadienoic acid is an eicosanoid lipid molecule
Prostaglandin E3
Prostaglandin E3 is from the cyclooxygenase metabolism of eicosapentaenoic acid.Prostaglandins are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs), and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes), and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signalling pathways. Prostaglandin E3 is from the cyclooxygenase metabolism of eicosapentaenoic acid.
Prostaglandin D3
Prostaglandin D3 (PGD3) is a prostanoid that has been identified as an inhibitor of human platelet aggregation and as a modulator of autonomic nerve transmission. Prostanoids are a subclass of the lipid mediator group known as eicosanoids. They derive from C-20 polyunsaturated fatty acids, mainly dihomo-gamma-linoleic (20:3n-6), arachidonic (20:4n-6), and eicosapentaenoic (20:5n-3) acids, through the action of cyclooxygenases-1 and -2 (COX-1 and COX-2). The reaction product of COX is the unstable endoperoxide prostaglandin H (PGH) that is further transformed into the individual prostanoids by a series of specific prostanoid synthases. Prostanoids are local-acting mediators formed and inactivated within the same or neighbouring cells prior to their release into circulation as inactive metabolites (15-keto- and 13,14-dihydroketo metabolites). Non-enzymatic peroxidation of arachidonic acid and other fatty acids in vivo can result in prostaglandin-like substances isomeric to the COX-derived prostaglandins that are termed isoprostanes. Prostanoids take part in many physiological and pathophysiological processes in practically every organ, tissue and cell, including the vascular, renal, gastrointestinal and reproductive systems. Their activities are mediated through prostanoid-specific receptors and intracellular signalling pathways, whilst their biosynthesis and action are blocked by nonsteroidal antiinflammatory drugs (NSAID). Isoprostanes are considered to be reliable markers of oxidant stress status and have been linked to inflammation, ischaemia-reperfusion, diabetes, cardiovascular disease, reproductive disorders and diabetes. (PMID: 16986207, 6252026, 6952267, 4019112, 6945633Prostaglandins are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs), and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes), and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signalling pathways. Prostaglandin D3 (PGD3) is a prostanoid that has been identified as an inhibitor of human platelet aggregation and as a modulator of autonomic nerve transmission. Prostanoids are a subclass of the lipid mediator group known as eicosanoids. They derive from C-20 polyunsaturated fatty acids, mainly dihomo-gamma-linoleic (20:3n-6), arachidonic (20:4n-6), and eicosapentaenoic (20:5n-3) acids, through the action of cyclooxygenases-1 and -2 (COX-1 and COX-2). The reaction product of COX is the unstable endoperoxide prostaglandin H (PGH) that is further transformed into the individual prostanoids by a series of specific prostanoid synthases. Prostanoids are local-acting mediators formed and inactivated within the same or neighbouring cells prior to their release into circulation as inactive metabolites (15-keto- and 13,14-dihydroketo metabolites). Non-enzymatic peroxidation of arachidonic acid and other fatty acids in vivo can result in prostaglandin-like substances isomeric to the COX-derived prostaglandins that are termed isoprostanes. Prostanoids take part in many physiological and pathophysiological processes in practically every organ, tissue and cell, including the vascular, renal, gastrointestinal and reproductive systems. Their activities are mediated through prostanoid-specific receptors and intracellular signalling pathways, whilst their biosynthesis and action are blocked by nonsteroidal antiinflammatory drugs (NSAID). Isoprostanes are considered to be reliable markers of oxidant stress status and have been linked to inflammation, ischaemia-reperfusion, diabetes, cardiovascular disease, reproductive disorders and diabetes. (PMID: 16986207, 6252026, 6952267, 4019112, 6945633
Resolvin E1
Resolvin E1 is a resolvin, a bioactive oxygenated product of EPA (eicosapentaenoic acid). It is a inflammation-resolving lipid mediator. RvE1 reduces neutrophil hyper-function, it also prevents the initiation and progression of tissue destruction (PMID: 16373400). RvE1, can also act as a host response modulator in the control of the inflammatory diseases that also involve bone loss such as periodontitis and arthritis. RvE1 has been shown to display specific binding sites on human neutrophils with an apparent Kd of 47 nM (PMID: 15753205; 16373400). RvE1 is a potent modulator of leukocytes as well as selective platelet responses in blood and platelet-rich plasma (PMID: 18480426). [HMDB] Resolvin E1 is a resolvin, a bioactive oxygenated product of EPA (eicosapentaenoic acid). It is a inflammation-resolving lipid mediator. RvE1 reduces neutrophil hyper-function, it also prevents the initiation and progression of tissue destruction (PMID: 16373400). RvE1, can also act as a host response modulator in the control of the inflammatory diseases that also involve bone loss such as periodontitis and arthritis. RvE1 has been shown to display specific binding sites on human neutrophils with an apparent Kd of 47 nM (PMID: 15753205; 16373400). RvE1 is a potent modulator of leukocytes as well as selective platelet responses in blood and platelet-rich plasma (PMID: 18480426).
(5S)-hydroperoxy-18-hydroxy-EPE
(5S)-hydroperoxy-18-hydroxy-EPE is also known as (5S)-Hydroperoxy-18-hepe or 5(S)-HP-18-HEPE. (5S)-hydroperoxy-18-hydroxy-EPE is considered to be practically insoluble (in water) and acidic
8-iso-15-keto-PGE2
8-iso-15-keto-PGE2 is an isoprostane. Isoprostanes are arachidonic acid metabolites produced by peroxidative attack of membrane lipids. These accumulate to substantial levels in many clinical conditions characterized in part by accumulation of free radicals and reactive oxygen species, including asthma, hypertension and ischemia reperfusion injury. For this reason, they are frequently used as markers of oxidative stress; however, many are now finding that these molecules are not inert, but in fact evoke powerful biological responses in an increasing array of cell types. In many cases, these biological effects can account in part for the various features and manifestations of those clinical conditions. Thus, it may be possible that the isoprostanes are playing somewhat of a causal role in those disease states (PMID: 14504139). Dinoprostone is a naturally occurring prostaglandin E2 (PGE2) and the most common and most biologically active of the mammalian prostaglandins. It has important effects in labour and also stimulates osteoblasts to release factors which stimulate bone resorption by osteoclasts (a type of bone cell that removes bone tissue by removing the bones mineralized matrix). PGE2 has been shown to increase vasodilation and cAMP production, to enhance the effects of bradykinin and histamine, to induce uterine contractions and to activate platelet aggregation. PGE2 is also responsible for maintaining the open passageway of the fetal ductus arteriosus; decreasing T-cell proliferation and lymphocyte migration and activating the secretion of IL-1alpha and IL-2. PGE2 exhibits both pro- and anti-inflammatory effects, particularly on dendritic cells (DC). Depending on the nature of maturation signals, PGE2 has different and sometimes opposite effects on DC biology. PGE2 exerts an inhibitory action, reducing the maturation of DC and their ability to present antigen. PGE2 has also been shown to stimulate DC and promote IL-12 production when given in combination with TNF-alpha. PGE2 is an environmentally bioactive substance. Its action is prolonged and sustained by other factors especially IL-10. It modulates the activities of professional DC by acting on their differentiation, maturation and their ability to secrete cytokines. PGE2 is a potent inducer of IL-10 in bone marrow-derived DC (BM-DC), and PGE2-induced IL-10 is a key regulator of the BM-DC pro-inflammatory phenotype (PMID: 16978535). Prostaglandins are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs), and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes), and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signalling pathways. 8-iso-15-keto-PGE2 is an isoprostane. Isoprostanes are arachidonic acid metabolites produced by peroxidative attack of membrane lipids. These accumulate to substantial levels in many clinical conditions characterized in part by accumulation of free radicals and reactive oxygen species, including asthma, hypertension and ischemia reperfusion injury. For this reason, they are frequently used as markers of oxidative stress; however, many are now finding that these molecules are not inert, but in fact evoke powerful biological responses in an increasing array of cell types. In many cases, these biological effects can account in part for the various features and manifestations of those clinical conditions. Thus, it may be possible that the isoprostanes are playing somewhat of a causal role in those disease states. (PMID: 14504139)
15-Epi-lipoxin B5
15-epi-lipoxin B5 is a lipoxin derivative. Lipoxins (LXs) and aspirin-triggered Lipoxin (ATL) are trihydroxytetraene-containing eicosanoids generated from arachidonic acid that are distinct in structure, formation, and function from the many other proinflammatory lipid-derived mediators. These endogenous eicosanoids have now emerged as founding members of the first class of lipid/chemical mediators involved in the resolution of the inflammatory response. Lipoxin A4 (LXA4), ATL, and their metabolic stable analogs elicit cellular responses and regulate leukocyte trafficking in vivo by activating the specific receptor, ALX. Many of the eicosanoids derived from arachidonic acid (AA2), including prostaglandins (PGs) and leukotrienes (LTs), play important roles as local mediators exerting a wide range of actions relevant in immune hypersensitivity and inflammation. However, recent observations indicate that other agents derived from the lipoxygenase (LO) pathways are formed and play a key role in initiating the resolution of acute inflammation. This phenomenon is an active process that is governed by specific lipid mediators and involves a series of well-orchestrated temporal events. Thus, potent locally released mediators serve as checkpoint controllers of inflammation. In addition to the well-appreciated ability of aspirin to inhibit PGs, aspirin also acetylates cyclooxygenase (COX)-2, triggering the formation of a 15-epimeric form of lipoxins, termed aspirin-triggered LXA4 (ATL). These eicosanoids (i.e., LXA4 and ATL) with a unique trihydroxytetraene structure function as stop signals in inflammation and actively participate in dampening host responses to bring the inflammation to a close, namely, resolution. LXA4 and ATL elicit the multicellular responses via a specific G protein-coupled receptor (GPCR) termed ALX that has been identified in human. (PMID: 16968948, 11478982). 15-epi-lipoxin B5 is a lipoxin derivative
Oryzalic acid B
Oryzalic acid B is found in cereals and cereal products. Oryzalic acid B is isolated from leaves of a blight-resistant rice cultivar. Isolated from leaves of a blight-resistant rice cultivariety Oryzalic acid B is found in cereals and cereal products.
(ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid
(ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid is found in fruits. (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid is a constituent of Cucurbita maxima. Constituent of Cucurbita maxima. 6alpha,7alpha,12alpha-Trihydroxykaurenoic acid is found in fruits and japanese pumpkin.
Prostaglandin H3
Prostaglandin H3 (PGH3) can be enzymatically converted by platelets into thromboxane A3 (TXA3). Both prostaglandin H2 (PGH2) and thromboxane A2 (TXA2) aggregate human platelet-rich plasma. In contrast, PGH3 and TXA3 do not. PGH3 and TXA3 increase platelet cyclic AMP in platelet-rich plasma and thereby (1) inhibit aggregation by other agonists, (2) block the ADP-induced release reaction, and (3) suppress platelet phospholipase-A2 activity or events leading to its activation. PGI3 (A7-prostacyclin; synthesized from PGH3 by blood vessel enzyme) and PGI2 (prostacyclin) exert similar effects. Both compounds are potent coronary relaxants that also inhibit aggregation in human platelet-rich plasma and increase platelet adenylate cyclase activity. Prostaglandins are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs), and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes), and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent and are able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis through receptor-mediated G-protein linked signalling pathways. Prostaglandin H3 (PGH3)can be enzymatically converted by platelets into thromboxane A3. Both PGH2 and thromboxane A2 aggregate human platelet-rich plasma. In contrast, PGH3 and thromboxane A3 do not. PGH3 and thromboxane A3 increase platelet cyclic AMP in platelet-rich plasma and thereby: (i) inhibit
Oryzalic acid A
Oryzalic acid A is found in cereals and cereal products. Oryzalic acid A is isolated from rice leaves. Isolated from rice leaves. Oryzalic acid A is found in cereals and cereal products.
12-Oxo-20-hydroxy-leukotriene B4
12-oxo-20-hydroxy-leukotriene B4 is the metabolite of lipid omega-oxidation of leukotriene B4 (LTB4). LTB4 is the major metabolite in neutrophil polymorphonuclear leukocytes. Omega-oxidation is the major pathway for the catabolism of leukotriene B4 in human polymorphonuclear leukocytes. Leukotrienes are metabolites of arachidonic acid derived from the action of 5-LO (5-lipoxygenase). The immediate product of 5-LO is LTA4 (leukotriene A4), which is enzymatically converted into either LTB4 (leukotriene B4) by LTA4 hydrolase or LTC4 (leukotriene C4) by LTC4 synthase. The regulation of leukotriene production occurs at various levels, including expression of 5-LO, translocation of 5-LO to the perinuclear region, and phosphorylation to either enhance or inhibit the activity of 5-LO. Biologically active LTB4 is metabolized by omega-oxidation carried out by specific cytochrome P450s (CYP4F) followed by beta-oxidation from the omega-carboxy position and after CoA ester formation (PMID: 7649996, 17623009, 2853166, 6088485). Leukotrienes are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs), and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes), and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signalling pathways. 12-oxo-20-hydroxy-leukotriene B4 is the metabolite of lipid omega-oxidation of leukotriene B4 (LTB4). LTB4 is the major metabolite in neutrophil polymorphonuclear leukocytes. Omega-oxidation is the major pathway for the catabolism of leukotriene B4 in human polymorphonuclear leukocytes. Leukotrienes are metabolites of arachidonic acid derived from the action of 5-LO (5-lipoxygenase). The immediate product of 5-LO is LTA4 (leukotriene A4), which is enzymatically converted into either LTB4 (leukotriene B4) by LTA4 hydrolase or LTC4 (leukotriene C4) by LTC4 synthase. The regulation of leukotriene production occurs at various levels, including expression of 5-LO, translocation of 5-LO to the perinuclear region and phosphorylation to either enhance or inhibit the activity of 5-LO. Biologically active LTB4 is metabolized by w-oxidation carried out by specific cytochrome P450s (CYP4F) followed by beta-oxidation from the w-carboxy position and after CoA ester formation. (PMID: 7649996, 17623009, 2853166, 6088485)
15-Oxo-lipoxin A4
15-oxo-lipoxin A4 is a lipoxin derivative. Lipoxins (LXs) and aspirin-triggered Lipoxin (ATL) are trihydroxytetraene-containing eicosanoids generated from arachidonic acid that are distinct in structure, formation, and function from the many other proinflammatory lipid-derived mediators. These endogenous eicosanoids have now emerged as founding members of the first class of lipid/chemical mediators involved in the resolution of the inflammatory response. Lipoxin A4 (LXA4), ATL, and their metabolic stable analogs elicit cellular responses and regulate leukocyte trafficking in vivo by activating the specific receptor, ALX. Many of the eicosanoids derived from arachidonic acid (AA2), including prostaglandins (PGs) and leukotrienes (LTs), play important roles as local mediators exerting a wide range of actions relevant in immune hypersensitivity and inflammation. However, recent observations indicate that other agents derived from the lipoxygenase (LO) pathways are formed and play a key role in initiating the resolution of acute inflammation. This phenomenon is an active process that is governed by specific lipid mediators and involves a series of well-orchestrated temporal events. Thus, potent locally released mediators serve as checkpoint controllers of inflammation. In addition to the well-appreciated ability of aspirin to inhibit PGs, aspirin also acetylates cyclooxygenase (COX)-2, triggering the formation of a 15-epimeric form of lipoxins, termed aspirin-triggered LXA4 (ATL). These eicosanoids (i.e., LXA4 and ATL) with a unique trihydroxytetraene structure function as stop signals in inflammation and actively participate in dampening host responses to bring the inflammation to a close, namely, resolution. LXA4 and ATL elicit the multicellular responses via a specific G protein-coupled receptor (GPCR) termed ALX that has been identified in human. (PMID: 16968948, 11478982). 15-oxo-lipoxin A4 is a lipoxin derivative
20-oxo-leukotriene B4
20-oxo-leukotriene B4 is the metabolite of lipid omega-oxidation of leukotriene B4 (LTB4). LTB4 is the major metabolite in neutrophil polymorphonuclear leukocytes. Omega-oxidation is the major pathway for the catabolism of leukotriene B4 in human polymorphonuclear leukocytes. Leukotrienes are metabolites of arachidonic acid derived from the action of 5-LO (5-lipoxygenase). The immediate product of 5-LO is LTA4 (leukotriene A4), which is enzymatically converted into either LTB4 (leukotriene B4) by LTA4 hydrolase or LTC4 (leukotriene C4) by LTC4 synthase. The regulation of leukotriene production occurs at various levels, including expression of 5-LO, translocation of 5-LO to the perinuclear region, and phosphorylation to either enhance or inhibit the activity of 5-LO. Biologically active LTB4 is metabolized by omega-oxidation carried out by specific cytochrome P450s (CYP4F) followed by beta-oxidation from the omega-carboxy position and after CoA ester formation (PMID: 7649996, 17623009, 2853166, 6088485). Leukotrienes are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs), and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes), and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signalling pathways. 20-oxo-leukotriene B4 is the metabolite of lipid omega-oxidation of leukotriene B4 (LTB4). LTB4 is the major metabolite in neutrophil polymorphonuclear leukocytes. Omega-oxidation is the major pathway for the catabolism of leukotriene B4 in human polymorphonuclear leukocytes. Leukotrienes are metabolites of arachidonic acid derived from the action of 5-LO (5-lipoxygenase). The immediate product of 5-LO is LTA4 (leukotriene A4), which is enzymatically converted into either LTB4 (leukotriene B4) by LTA4 hydrolase or LTC4 (leukotriene C4) by LTC4 synthase. The regulation of leukotriene production occurs at various levels, including expression of 5-LO, translocation of 5-LO to the perinuclear region and phosphorylation to either enhance or inhibit the activity of 5-LO. Biologically active LTB4 is metabolized by w-oxidation carried out by specific cytochrome P450s (CYP4F) followed by beta-oxidation from the w-carboxy position and after CoA ester formation. (PMID: 7649996, 17623009, 2853166, 6088485)
5,12,18R-TriHEPE
This compound belongs to the family of Leukotrienes. These are eicosanoids containing an hydroxyl group attached to the aliphati chain of an arachidonic acid.
15-oxo-5S,6R-dihydroxy-7E,9E,11Z,13E-eicosatetraenoic acid
15-oxo-5S,6R-dihydroxy-7E,9E,11Z,13E-eicosatetraenoic acid is also known as 15-keto-Lipoxin a4 or 15-oxo-LXA4. 15-oxo-5S,6R-dihydroxy-7E,9E,11Z,13E-eicosatetraenoic acid is considered to be practically insoluble (in water) and acidic. 15-oxo-5S,6R-dihydroxy-7E,9E,11Z,13E-eicosatetraenoic acid is an eicosanoid lipid molecule
(5S)-hydroperoxy-18-hydroxy-EPE(1-)
(5S)-hydroperoxy-18-hydroxy-EPE(1-) is considered to be practically insoluble (in water) and acidic
(Z)-7-[(1R,3R)-3-Hydroxy-2-[(1E,3S,5Z)-3-hydroxyocta-1,5-dienyl]-5-oxocyclopentyl]hept-5-enoic acid
Andrographolide
Prostaglandin I3
(5S,12R,18R)-5,12,18-Trihydroxyicosa-6,8,10,14,16-pentaenoic acid
Thromboxane A3
7β-Hydroxylathyrol
7beta-Hydroxylathyrol is a natural product. 7beta-Hydroxylathyrol is a natural product.
17-Hydroxyisolathyrol
17-Hydroxyisolathyrol is a macrocychc lathyrol derivative isolated from seeds of Euphorbla luthyrrs[1].
[1R-(1alpha,4beta,4abeta,6alpha,8aalpha)]-6-(Acetyloxy)-4-ethoxy-1,2,3,4,4a,5,6,8a-octahydro-4,7-dimethyl-a-methylene-1-naphthaleneacetic acid methyl ester
16,17,18-Trihydroxy-2,6,10,14-phytatetraen-1,20-olide
(E,Z,E,Z)-2-(9-Hydroxy-4,8-dimethyl-3,7-nonadienyl)-6-methyl-2,6-octadienedioic acid
8beta,17-Epoxy-3beta,7beta-Dihydroxy-12(E)-labden-16,15-olide
(ent-6alpha,13E)-6,16-Dihydroxy-17-oxo-7,13-labdadien-15-oic acid
(E,Z,Z,Z)-2-(9-Hydroxy-4,8-dimethyl-3,7-nonadienyl)-6-methyl-2,6-octadienedioic acid
16,17,18,20-Tetrahydroxynerylgeran-1-oic acid lactone
13,16alpha,17-trihydroxy-ent-9(11)-kauren-19-oic acid
7beta,18,19-trihydroxy-ent-clerodan-3,13-dien-16,15-diolide
2beta-hydroxy-ent-clerod-3-en-15-oic acid-18,19-olide
3alpha-angeloyloxy-4alpha,11-dihydroxy-eudesm-6-en-8-one|3alpha-angeloyloxy-4alpha,11-hihydroxyeudesm-6-en-8-one
11,12,15-Trihydroxy-16-kauren-19-oic acid|ent-11alpha,12alpha,15alpha-trihydroxykaur-16-en-19-oic acid
3-desoxy-8-epi-hymenoxon(2-methylbutyrate)|3-desoxy-8-epi-hymenoxon<2-methylbutyrate>
3alpha,8beta,14beta-trihydroxyabiet-13,15-en-16,12-olide|suremulide
1-deoxyrabdoserrin B|7alpha,12alpha,14beta,20-tetrahydroxy-ent-kaur-16-en-15-one|excisanin I
7beta,16beta,17-trihydroxy-ent-kauran-6beta,19-olide
3beta-hydroxy-abieta-8(14)-en-18-oic acid 9alpha,13alpha-endoperoxide
(+)-miliusane XX|[4alpha-methoxy-7alpha-(2,6-dimethyl-hepta-1,5-dienyl)-2-oxo-6beta-oxa-bicyclo[3.2.1]oct-1-yl]acetic acid methyl ester
2beta,3beta,17,19-tetrahydroxyspongia-13(16),14-diene
7alpha,14beta,18,20-tetrahydroxy-ent-kaur-16-en-15-one|excisanin J
7alpha-13alpha,14beta,18-tetrahydroxy-ent-atis-16-en-15-one|alboatisin A
pulchellin-2-O-isovalerate|pulchellin-2alpha-O-isovalerate
(ent-7alpha,15beta)-7,9,15-Trihydroxy-16-kauren-19-oic acid|ent-7alpha,9alpha,15beta-trihydroxy-kaurenic acidz
6alpha-isovaleryloxy-1-hydroxy-4alphaH-1,10-secoeudesma-5(10),11(13)-dien-12,8beta-olide
4,5-Dihydro-4alpha-hydroxyivangustin-2-methylbutyrat
(1beta,2alpha,3betaH,6E,10E)-1,2-Dihydroxy-13-oxo-6,10,14-phytatrien-20,1-olide
3alpha,5alpha,8beta-trihydroxycleistanth-13(17),15-dien-18-oic acid
7-oxo-13beta,15-dihydroxyabiet-8(14)-en-18-oic acid
(1RS,2SR,5RS,6SR,9RS,10SR,12RS)-10-hydroxy-1,5,9-trimethyl-13-methylidene-15,18,19-trioxatetracyclo[10.3.2.1(2,5).1(6,9)]nonadecan-14-one|sinulaparvalide B
3alpha,15-dihydroxy-14-oxo-labd-8(17),13(16)-dien-19-oic acid
6alpha-(2-methybutyryloxy)-1-hydroxy-4alphaH-1,10-secoeudesma-5(10),11(13)-dien-12,8beta-olide
(2alpha,6alpha)-2,6,19-Trihydroxy-8,13-labdadien-15,16-olide
7-oxo-8,14beta-dihydroxy-15-isopimaren-18-oic acid|8,14beta-dihydroxy-7-oxo-15-isopimaren-18-oic acid
3,18,19-trihydroxy-ent-labda-8(17),13-dien-16,15-olide
7alpha-hydroxy-ent-clerod-3-en-15-oic acid-18,19-olide
ent-13-epi-8,13-epoxy-2-oxa-3-oxolabd-14-ene-1R-carboxylic acid
5-(1-isovalerianoyloxy)ethyl-2-O-isopentenyl-1,3-di-O-methylpyrogallol
(ent-4alpha,13xi)-4-Hydroxy-2-cleroden-18,19-olid-15-oic acid|4beta-hydroxy-ent-clerod-2-en-15-oic acid-18,19-olide
(2E,6E)-8-{[ (2E,6E)-8-hydroxy-2,6-dimethylocta-2,6-dienoyl]oxy}-2,6-dimethylocta-2,6-dienoic acid
7-oxo-12alpha,13beta-dihydroxyabiet-8(14)-en-18-oic acid
14,15-Dihydro,13,14-didehydro,15-hydroxy-Ichthyouleolide|14-peroxy-15,17-dehydro-14,15-dihydroichthyouleolide
(+)-(1S*,4R*,8S*,10R*)-1,4,8-trihydroxycembra-2E,6E,11Z-trien-20,10-olide
(+)-(1S*,4S*,7R*,10R*)-1,4,7-trihydroxycembra-2E,8(19),11Z-trien-20,10-olide
13beta-dihydroxy-14-oxo-3,4-secoatis-16-en-3-oic acid
(8beta,12alphaH,16R)-8,12-Epoxy-16,17-dihydroxy-13-labden-15,16-olide
16alpha,17-Dihydroxy-7-oxo-(-)-kauran-19-saeure|ent-7-oxo-16alpha,17-dihydroxykauran-19-oic acid
(E)-3-hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)dodecan-6-en-5-one
6,9:15,16-diepoxy-6-hydroxy-6,7-seco-13(16),14-labdadien-7-oic acid|leosibiric acid B
(7alpha,17beta)-15,17-Epoxy-7,17-dihydroxy-16-spongianone|7alpha,17beta-dihydroxy-15,17-oxidospongian-16-one
15,16-epoxy-3alpha,6beta,9alpha-trihydroxylabda-13(16),14-dien-7-one
4R*-hydroxy-6S*-tigloyloxyeudesma-7S*-11(13)-en-12-oic acid
(1aS,3aS,4E,7S,7aR,10R)-dodecahydro-4-[(2E)-4-hydroxy-4-methylpent-2-en-1-ylidene]-1a-methyl-8-methylideneoxireno[5,6]cyclonona[1,2-c]pyran-7,10-diol|asterolaurin L
(4E,10E)-9beta-hydroxy-3-(2-methylbutyroyloxy)-germacra-4,10(1)-diene-12,6alpha-olide|3beta-[2-methylbutyryloxy]-9beta-hydroxy-germacra-1(10),4-dienolide
(ent-1alpha,15alpha)-1,9,15-Trihydroxy-16-kauren-19-oci acid|ent-1alpha,9alpha,15alpha-trihydroxykaur-16-en-19-oic acid
17-Hydroxy-(2alpha,6alpha)-2,6-Dihydroxy-8,13-labdadien-15,16-olide
(3R,9S)-3-(9-hydroxyundecyl)-6,8-dihydroxy-3,4-dihydroisocoumarin
3alpha-senecioyloxy-4alpha,11-dihydroxy-eudesm-6-en-8-one
(ent-2alpha,3beta)-2,3,18-Trihydroxy-8(17),13-labdadien-15,16-olide
acetylajugarin II|deacetyl ajugarin II|deacetylajugarin II|deacetylajugarin-II
(8alpha,12alpha)-form-8,12-Epidioxy-15-hydroxy-13-abieten-18-oic acid
(-)-Kromycin|(3R)-14t-Aethyl-13c-hydroxy-3r,5,7t,9t,13t-pentamethyl-oxacyclotetradeca-5t,11t-dien-2,4,10-trion|(3R)-14t-ethyl-13c-hydroxy-3r,5,7t,9t,13t-pentamethyl-oxacyclotetradeca-5t,11t-diene-2,4,10-trione|Kromycin
5b,6-epoxydecahydro-4,7,8-trihydroxy-3-isopropyl-3a,5a,8-trimethyl-1H-pentaleno[1,6a-a]pentalen-5(5aH)-one|crinipellin D|rel-(1aR,2R,3S,3aR,4aR,7R,7aR,8R,9aS,9bR)-octahydro-2,3,8-trihydroxy-3,7a,9a-trimethyl-7-(1-methylethyl)-3H,5H-pentaleno[6a,1: 5,6]pentaleno[1,6a-b]oxiren-9(9aH)-one
(1R*,2E,4S*,6E,8R*,11E)-1-isopropyl-4-hydroxy-8-hydroperoxy-4,8-dimethyl-21-oxabicyclo[10.2.2]hexadeca-2,6,11-trien-20-one|laevigatlactone F
(4S,5alpha,12beta)-8beta,14beta-epoxy-12-hydroxy-11-oxototaran-19-oic acid|pedunculatic acid B
minheryin G
An ent-kaurane diterpenoid isolated from Isodon henryi and has been shown to exhibit cytotoxic activity.
15,16-epoxy-8beta-hydroxy-16-ketolabd-13-en-19-oic acid|leonotinic acid
16alpha,17-dihydroxy-15-oxo-ent-kaur-19-oic acid|16??,17-Dihydroxy-15-oxo-ent-kaur-19-oic acid|ent-17-hydroxy-15-oxokauran-19-oic acid
3-alpha,7alpha,14beta,15-beta-tetrahydroxy-ent-kaur-16-en-12-one|pharicunin F
3,4-Dihydro-6,8-dihydroxy-3-(6-hydroxyundecyl)-1H-2-benzopyran-1-one
Bis-((4aR)-4c,7c-dimethyl-1-oxo-(4ar,7ac)-octahydro-cyclopenta[c]pyran-3xi-yl)-aether|bis-((4aR)-4c,7c-dimethyl-1-oxo-(4ar,7ac)-octahydro-cyclopenta[c]pyran-3xi-yl)-ether
7beta-hydroxy-abieta-8(14)-en-18-oic acid, 9alpha,13alpha-endoperoxide
13,14-seco-13-oxoabiet-7-ene-14,18-dioic acid|13-Oxo-13-isopropyl-13,14-seco-podocarpen-(7)-disaeure-(14,15)|13-oxo-13-isopropyl-13,14-seco-podocarpene-(7)-dioic acid-(14,15)
Epoxylathyrol
Epoxylathyrol is a natural product found in Euphorbia lathyris with data available.
Yuexiandajisu E
(4Ar,6aR,7R,10aS,11R,11aR,11bR)-6a,7,11-trihydroxy-4,4,8,11b-tetramethyl-1,2,3,4a,5,6,7,10a,11,11a-decahydronaphtho[2,1-f][1]benzofuran-9-one is a natural product found in Euphorbia ebracteolata with data available.
7beta-Hydroxylathyrol
7beta-Hydroxylathyrol is a natural product. 7beta-Hydroxylathyrol is a natural product.
Andropanolide
Andropanolide is a natural product found in Andrographis paniculata with data available.
5-(4-carboxy-3-methylbutyl)-5,6,8a-trimethyl-3-oxo-4a,6,7,8-tetrahydro-4H-naphthalene-1-carboxylic acid
6,8-dihydroxy-3-(10-hydroxyundecyl)-3,4-dihydroisochromen-1-one
C20H30O5_(1S,2R,4aR)-1-Hydroxy-7-isopropylidene-1,4a-dimethyl-6-oxodecahydro-2-naphthalenyl 2,3-dimethyl-2-oxiranecarboxylate
C20H30O5_2(3H)-Furanone, 3-[2-[(1R,4aS,5R,6R,8aS)-decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl]ethylidene]dihydro-4-hydroxy-, (3E,4R)
C20H30O5_Oxacyclotetradeca-7,11-diene-2,6,10-trione, 14-ethyl-13-hydroxy-3,5,7,9,13-pentamethyl-, (7E,11E)
C20H30O5_1-Cyclopentene-1-octanoic acid, gamma-(acetyloxy)-3-oxo-2-(2-penten-1-yl)
C20H30O5_2-Cyclopentene-1-octanoic acid, 1-(acetyloxy)-4-oxo-5-[(2Z)-2-penten-1-yl]
C20H30O5_2(5H)-Furanone, 3-[2-[(1R,4aS,5R,6R,8aS)-decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl]-1-hydroxyethyl]
C20H30O5_6,10a-Dihydroxy-4-(hydroxymethyl)-4,7,11b-trimethyl-2,3,4,4a,5,6,6a,7,10a,11,11a,11b-dodecahydrophenanthro[3,2-b]furan-9(1H)-one
C20H30O5_1-Naphthalenecarboxylic acid, 5-[(3E)-4-carboxy-3-methyl-3-buten-1-yl]decahydro-3-hydroxy-1,4a-dimethyl-6-methylene
4-acetyloxy-8-(3-oxo-2-pent-2-enylcyclopenten-1-yl)octanoic acid
4-[2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-1-hydroxyethyl]-2H-furan-5-one
6,10a-dihydroxy-4-(hydroxymethyl)-4,7,11b-trimethyl-1,2,3,4a,5,6,6a,7,11,11a-decahydronaphtho[2,1-f][1]benzofuran-9-one
(3E,4R)-3-[2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]-4-hydroxyoxolan-2-one
5-(4-carboxy-3-methylbutyl)-5,6,8a-trimethyl-3-oxo-4a,6,7,8-tetrahydro-4H-naphthalene-1-carboxylic acid
6,8-dihydroxy-3-(10-hydroxyundecyl)-3,4-dihydroisochromen-1-one
5-(4-carboxy-3-methylbutyl)-5,6,8a-trimethyl-3-oxo-4a,6,7,8-tetrahydro-4H-naphthalene-1-carboxylic acid [IIN-based: Match]
6,8-dihydroxy-3-(10-hydroxyundecyl)-3,4-dihydroisochromen-1-one [IIN-based on: CCMSLIB00000846799]
5-(4-carboxy-3-methylbutyl)-5,6,8a-trimethyl-3-oxo-4a,6,7,8-tetrahydro-4H-naphthalene-1-carboxylic acid [IIN-based on: CCMSLIB00000847901]
5-(4-carboxy-3-methylbutyl)-5,6,8a-trimethyl-3-oxo-4a,6,7,8-tetrahydro-4H-naphthalene-1-carboxylic acid [IIN-based on: CCMSLIB00000847900]
6,8-dihydroxy-3-(10-hydroxyundecyl)-3,4-dihydroisochromen-1-one [IIN-based: Match]
(3E,4R)-3-[2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]-4-hydroxyoxolan-2-one_major
6,8-dihydroxy-3-(10-hydroxyundecyl)-3,4-dihydroisochromen-1-one_major
8-(3-((1-Ethoxy-2-methyl-1-oxopropan-2-yl)oxy)phenyl)octanoic acid
5,6,15-trihydroxy-7,9,13-Eicosatrien-11-ynoic acid
Prostaglandin K2
Resolvin E1
A resolvin that is (6Z,8E,10E,14Z,16E)-icosa-6,8,10,14,16-pentaenoic acid which is substituted at positions 5, 12 and 18 by hydroxy groups (the 5S,12R,18R stereoisomer).
(ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid
Oryzalic acid A
Oryzalic acid B
6,8-Dihydroxy-3-(10-hydroxyundecyl)-3,4-dihydro-1H-isochromen-1-one
(E)-4-acetoxy-8-(3-oxo-2-(pent-2-en-1-yl)cyclopent-1-en-1-yl)octanoic acid
6,10a-Dihydroxy-4-(hydroxymethyl)-4,7,11b-trimethyl-2,3,4,4a,5,6,6a,7,10a,11,11a,11b-dodecahydrophenanthro[3,2-b]furan-9(1H)-one
5-(4-Carboxy-3-methylbutyl)-5,6,8a-trimethyl-3-oxo-3,4,4a,5,6,7,8,8a-octahydro-1-naphthalenecarboxylic acid
3,4-Dihydro-6,8-dihydroxy-3-(10-hydroxyundecyl)isocoumarin
(5E,13E)-11-Hydroxy-9,15-dioxoprosta-5,13-dien-1-oic acid
(5S)-hydroperoxy-(18S)-hydroxy-(6E,8Z,11Z,14Z,16E)-icosapentaenoic acid
A polyunsaturated fatty acid that is (6E,8Z,11Z,14Z,16E)-icosapentaenoic acid substituted at positions 5 and 18 by hydroperoxy and hydroxy groups respectively (the 5S, 18S-stereoisomer).
8-iso-15-keto-PGE2
8-iso-15-keto-PGE2 is an isoprostane. Isoprostanes are arachidonic acid metabolites produced by peroxidative attack of membrane lipids. These accumulate to substantial levels in many clinical conditions characterized in part by accumulation of free radicals and reactive oxygen species, including asthma, hypertension and ischemia reperfusion injury. For this reason, they are frequently used as markers of oxidative stress; however, many are now finding that these molecules are not inert, but in fact evoke powerful biological responses in an increasing array of cell types. In many cases, these biological effects can account in part for the various features and manifestations of those clinical conditions. Thus, it may be possible that the isoprostanes are playing somewhat of a causal role in those disease states (PMID: 14504139). Dinoprostone is a naturally occurring prostaglandin E2 (PGE2) and the most common and most biologically active of the mammalian prostaglandins. It has important effects in labour and also stimulates osteoblasts to release factors which stimulate bone resorption by osteoclasts (a type of bone cell that removes bone tissue by removing the bones mineralized matrix). PGE2 has been shown to increase vasodilation and cAMP production, to enhance the effects of bradykinin and histamine, to induce uterine contractions and to activate platelet aggregation. PGE2 is also responsible for maintaining the open passageway of the fetal ductus arteriosus; decreasing T-cell proliferation and lymphocyte migration and activating the secretion of IL-1alpha and IL-2. PGE2 exhibits both pro- and anti-inflammatory effects, particularly on dendritic cells (DC). Depending on the nature of maturation signals, PGE2 has different and sometimes opposite effects on DC biology. PGE2 exerts an inhibitory action, reducing the maturation of DC and their ability to present antigen. PGE2 has also been shown to stimulate DC and promote IL-12 production when given in combination with TNF-alpha. PGE2 is an environmentally bioactive substance. Its action is prolonged and sustained by other factors especially IL-10. It modulates the activities of professional DC by acting on their differentiation, maturation and their ability to secrete cytokines. PGE2 is a potent inducer of IL-10 in bone marrow-derived DC (BM-DC), and PGE2-induced IL-10 is a key regulator of the BM-DC pro-inflammatory phenotype (PMID: 16978535). Prostaglandins are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs), and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes), and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signalling pathways. 8-iso-15-keto-PGE2 is an isoprostane. Isoprostanes are arachidonic acid metabolites produced by peroxidative attack of membrane lipids. These accumulate to substantial levels in many clinical conditions characterized in part by accumulation of free radicals and reactive oxygen species, including asthma, hypertension and ischemia reperfusion injury. For this reason, they are frequently used as markers of oxidative stress; however, many are now finding that these molecules are not inert, but in fact evoke powerful biological responses in an increasing array of cell types. In many cases, these biological effects can account in part for the various features and manifestations of those clinical conditions. Thus, it may be possible that the isoprostanes are playing somewhat of a causal role in those disease states. (PMID: 14504139)
(3E)-3-[2-[(8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]-4-hydroxyoxolan-2-one
(5S)-hydroperoxy-18-hydroxy-EPE
An icosanoid that is (6E,8Z,11Z,14Z,16E)-icosa-6,8,11,14,16-pentaenoic acid substituted at positions 5S and 18 by hydroperoxy and hydroxy groups respectively.
2(3H)-Furanone, 3-[2-[decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl]ethylidene]dihydro-4-hydroxy-
(E)-7-[3-[(1E,5E)-3-hydroxyocta-1,5-dienyl]-2,6-dioxabicyclo[3.1.1]heptan-4-yl]hept-5-enoic acid
(5S)-Hydroperoxy-18-hydroxy-(7E,9E,11Z,14Z,16E)-eicosapentaenoate
(Z)-7-[(1R,3R)-3-Hydroxy-2-[(1E,3S,5Z)-3-hydroxyocta-1,5-dienyl]-5-oxocyclopentyl]hept-5-enoic acid
(5Z)-5-[5-hydroxy-4-[(1E,5E)-3-hydroxyocta-1,5-dienyl]-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-ylidene]pentanoic acid
(2E,6E)-8-{[(2E,6E)-8-hydroxy-2,6-dimethylocta-2,6-dienoyl]oxy}-2,6-dimethylocta-2,6-dienoic acid
A natural product found in Anarrhinum orientale.
rel-(-)-(1S,4S,7S,10R)-1,4,7-trihydroxycembra-2E,8-(19),11Z-trien-20,10-olide
A cembrane diterpenoid that is cembra-2E,8-(19),11Z-trien-20,10-olide substituted by hydroxy groups at positions 1, 4 and 7. It has been isolated from the leaves of Croton gratissimus.
rel-(+)-(1S,4S,7R,10R)-1,4,7-trihydroxycembra-2E,8-(19),11Z-trien-20,10-olide
A cembrane diterpenoid that is cembra-2E,8-(19),11Z-trien-20,10-olide substituted by hydroxy groups at positions 1, 4 and 7. It has been isolated from the leaves of Croton gratissimus.
(7E,11E)-14-Ethyl-13-hydroxy-3,5,7,9,13-pentamethyl-1-oxacyclotetradeca-7,11-diene-2,6,10-trione
rel-(+)-(1S,4R,8S,10R)-1,4,8-trihydroxycembra-2E,6E,11Z-trien-20,10-olide
A cembrane diterpenoid that is cembra-2E,8-(19),11Z-trien-20,10-olide substituted by hydroxy groups at positions 1, 4 and 8. It has been isolated from the leaves of Croton gratissimus.
(5S,6Z,8E,10E,14Z)-5,20-dihydroxy-12-oxoicosa-6,8,10,14-tetraenoic acid
(7E,9E,11Z,13E,15R,17Z)-5,6,15-trihydroxyicosa-7,9,11,13,17-pentaenoic acid
(6Z,8E,10E,14Z,16E,18R)-5,12,18-trihydroxyicosa-6,8,10,14,16-pentaenoic acid
(3E)-4-hydroxy-3-[2-[6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]oxolan-2-one
15-dehydro-prostaglandin D2
The 15-dehydro derivative of prostaglandin D2.
5S-hydroperoxy-18R-hydroxy-6E,8Z,11Z,14Z,16E-eicosapentaenoic acid
Prostaglandin D3
A member of the class of prostaglandins D that is prosta-5,13,17-trien-1-oic acid substituted by hydroxy groups at positions 9 and 15 and an oxo group at position 11 (the 5Z,13E,15S,17Z-stereoisomer).
(5S,6Z,8E,10E,12R,14Z)-5,12-dihydroxy-20-oxoicosa-6,8,10,14-tetraenoic acid
Prostaglandin H3
A member of the class of prostaglandins H that is 9,11-epidioxyprosta-5,13,17-trienoic acid carrying an additional hydroxy substituent at the 15S-position.
15-oxolipoxin A4
A C20 hydroxy fatty acid having (5S)- and (6R)- -hydroxy groups as well as a 15-oxo group and (7E)- (9E)-, (11Z)- and (13E)-double bonds.
5(S)-hydroperoxy-18(R)-hydroxy-(6E,8Z,11Z,14Z,16E)-icosapentaenoic acid
A polyunsaturated fatty acid that is (6E,8Z,11Z,14Z,16E)-icosapentaenoic acid substituted at positions 5 and 18 by hydroperoxy and hydroxy groups respectively (the 5S, 18R-stereoisomer).
20-Oxoleukotriene b4
A leukotriene that is leukotriene B4 bearing an additional oxo substituent at position 20.
(18S)-resolvin E1
A resolvin that is (6Z,8E,10E,14Z,16E)-icosa-6,8,10,14,16-pentaenoic acid which is substituted at positions 5, 12 and 18 by hydroxy groups (the 5S,12R,18S stereoisomer).
DG(17:4)
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