Classification Term: 168155

Levuglandins [FA0310] (ontology term: 9e0d167f29b375e334d467430d1725d4)

Levuglandins [FA0310]

found 11 associated metabolites at sub_class metabolite taxonomy ontology rank level.

Ancestor: Eicosanoids [FA03]

Child Taxonomies: There is no child term of current ontology term.

Levuglandin E2

(5Z,8S,9R,10E,12S)-8-acetyl-9-formyl-12-hydroxyheptadeca-5,10-dienoic acid

C20H32O5 (352.2249622)


Levuglandin E2 is a levuglandin generated in the cyclooxygenase (COX) pathway. Levuglandins (LGs) and their stereo and structural isomers are extraordinarily reactive γ-ketoaldehydes that are generated by rearrangements of prostanoid endoperoxide intermediates of polyene cyclooxygenation. Their rapid adduction with biological nucleophiles results, inter alia, in pathological modifications of proteins and DNA. It also complicates their detection. Cyclooxygenase-promoted lipid oxidation is a pivotal step in the biosynthesis of an array of physiologically active metabolites. COX fosters a highly regio and stereoselective cyclooxygenation of arachidonic acid (AA) to deliver a single, enantiomerically pure endoperoxide, PGH2, that is a branch point in the biosynthesis of numerous hormone-like mediators of cellular activities. Spontaneous rearrangements of PGH2 were known to generate prostaglandins (PG) PGD2 and PGE2. (PMID: 15752459) [HMDB] Levuglandin E2 is a levuglandin generated in the cyclooxygenase (COX) pathway. Levuglandins (LGs) and their stereo and structural isomers are extraordinarily reactive γ-ketoaldehydes that are generated by rearrangements of prostanoid endoperoxide intermediates of polyene cyclooxygenation. Their rapid adduction with biological nucleophiles results, inter alia, in pathological modifications of proteins and DNA. It also complicates their detection. Cyclooxygenase-promoted lipid oxidation is a pivotal step in the biosynthesis of an array of physiologically active metabolites. COX fosters a highly regio and stereoselective cyclooxygenation of arachidonic acid (AA) to deliver a single, enantiomerically pure endoperoxide, PGH2, that is a branch point in the biosynthesis of numerous hormone-like mediators of cellular activities. Spontaneous rearrangements of PGH2 were known to generate prostaglandins (PG) PGD2 and PGE2. (PMID: 15752459).

   

Levuglandin D2

(5Z,8R,9R,10E,12S)-9-acetyl-8-formyl-12-hydroxyheptadeca-5,10-dienoic acid

C20H32O5 (352.2249622)


Levuglandin D2 is one of the products of a non-enzymatically rearrangement of prostaglandin H2 (PGH2) to this highly reactive gamma-keto aldehyde. PGH2 markedly accelerates the formation of dimers and higher oligomers of amyloid beta1-42. This evidence implicates cyclooxygenase activity in the pathogenesis of Alzheimers disease, and is associated with the formation of levuglandin adducts of the peptide. Levuglandins (LGs) and their stereo and structural isomers are extraordinarily reactive γ-ketoaldehydes that are generated by rearrangements of prostanoid endoperoxide intermediates of polyene cyclooxygenation. Their rapid adduction with biological nucleophiles results, inter alia, in pathological modifications of proteins and DNA. It also complicates their detection. Cyclooxygenase-promoted lipid oxidation is a pivotal step in the biosynthesis of an array of physiologically active metabolites. COX fosters a highly regio and stereoselective cyclooxygenation of arachidonic acid (AA) to deliver a single, enantiomerically pure endoperoxide, PGH2, that is a branch point in the biosynthesis of numerous hormone-like mediators of cellular activities. Spontaneous rearrangements of PGH2 were known to generate prostaglandins (PG) PGD2 and PGE2. (PMID: 12358806, 15752459, 3317517, 10224068) [HMDB] Levuglandin D2 is one of the products of a non-enzymatically rearrangement of prostaglandin H2 (PGH2) to this highly reactive gamma-keto aldehyde. PGH2 markedly accelerates the formation of dimers and higher oligomers of amyloid beta1-42. This evidence implicates cyclooxygenase activity in the pathogenesis of Alzheimers disease, and is associated with the formation of levuglandin adducts of the peptide. Levuglandins (LGs) and their stereo and structural isomers are extraordinarily reactive γ-ketoaldehydes that are generated by rearrangements of prostanoid endoperoxide intermediates of polyene cyclooxygenation. Their rapid adduction with biological nucleophiles results, inter alia, in pathological modifications of proteins and DNA. It also complicates their detection. Cyclooxygenase-promoted lipid oxidation is a pivotal step in the biosynthesis of an array of physiologically active metabolites. COX fosters a highly regio and stereoselective cyclooxygenation of arachidonic acid (AA) to deliver a single, enantiomerically pure endoperoxide, PGH2, that is a branch point in the biosynthesis of numerous hormone-like mediators of cellular activities. Spontaneous rearrangements of PGH2 were known to generate prostaglandins (PG) PGD2 and PGE2. (PMID: 12358806, 15752459, 3317517, 10224068).

   

isoLGD2

9,10-seco-9,11-dioxo-15-hydroxy-5Z,13E-prostadienoic acid

C20H32O5 (352.2249622)


   

isoLGE2

10,11-seco-9,11-dioxo-15-hydroxy-5Z,13E-prostadienoic acid

C20H32O5 (352.2249622)


   

8-iso-LGE2

(5Z,8S,9E,11S,12R)-11-acetyl-12-formyl-8-hydroxyheptadeca-5,9-dienoic acid

C20H32O5 (352.2249622)


   

5-iso-LGE2

(5S,6E,8S,9R,11Z)-8-acetyl-9-formyl-5-hydroxyheptadeca-6,11-dienoic acid

C20H32O5 (352.2249622)


   

ox-LGD2

9,10-seco-9-carboxy-11,11,15S-trihydroxy-5Z,8(12),13E-prostatrienoic acid 9,11-lactone

C20H30O6 (366.204228)


   

FA 20:4;O3

4-((1S,2S,5R)-5-hydroxy-2-((S,1E,5Z)-3-hydroxyundeca-1,5-dien-1-yl)-3-oxocyclopentyl)butanoic acid

C20H32O5 (352.2249622)


D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D002491 - Central Nervous System Agents > D000700 - Analgesics D000893 - Anti-Inflammatory Agents D018501 - Antirheumatic Agents

   

IsoLG-Etn

15-isoLG hydroxylactam-ethanolamine

C22H35NO6 (409.24642500000004)


   

Levuglandin D2

(8R,12R)-9,10-seco-9,11-dioxo-15S-hydroxy-5Z,13E-prostadienoic acid

C20H32O5 (352.2249622)


   

Levuglandin E2

(8R,12R)-10,11-seco-9,11-dioxo-15S-hydroxy-5Z,13E-prostadienoic acid

C20H32O5 (352.2249622)