8-iso prostaglandin F2α

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  • Name: 8-iso prostaglandin F2α
  • Description: 8-Isoprostaglandin F2a is an isoprostane and a potent renal vasoconstrictor. Isoprostanes are prostaglandin-like compounds that are produced in vivo in humans by a noncyclooxygenase mechanism invol... ving free radical-catalyzed peroxidation of arachidonic acid. The formation of these prostanoids proceeds through bicyclic endoperoxide intermediates that are then reduced to form ring isoprostanes. Of considerable interest is that, in contradistinction to cyclooxygenase-derived prostaglandins, isoprostanes have been shown to be initially formed in situ, esterified to phospholipids, and subsequently released preformed, presumably by phospholipases. The fact that prostanoids are produced in vivo by a noncyclooxygenase mechanism is of considerable interest from a biochemical perspective. However, this may also be associated with biological ramifications since it has been shown that these compounds are capable of exerting potent biological activity. (PMID: 7825845, 17012140). 8-iso-prostaglandin F2A is a biomarker for the consumption of offal meat. 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 signaling pathways (HMDB0005083)
Overview of age-variations
Age group comparisons
PMID Age/Age interval, Gender Value (unit of measurement) Method Sample
25147595 Age 21 ± 4.3, Gender ⚥ 15.0 (pg/ml EBC) HPLC/MS body fluid
25147595 Age 39 ± 8.4, Gender ⚥ 26.8 (pg/ml EBC) HPLC/MS body fluid
25147595 Age 62 ± 9.1, Gender ⚥ 44.5 (pg/ml EBC) HPLC/MS body fluid
Linear regression
PMID Age/Age interval, Gender Value (unit of measurement) Method Sample
log2 ratio/log2(FC)
PMID Age/Age interval, Gender Value (unit of measurement) Method Sample
Summary
  • Synonym:
    8-iso prostaglandin F2 alpha
  • Chemical Formula:
    C20H34O5
  • Exact Mass g/mol:
    356.0000000
  • Systematic name:
    (Z)-7-[(1S,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoic acid
  • SMILES:
    CCCCCC(C=CC1C(CC(C1CC=CCCCC(=O)O)O)O)O
  • InChI:
    InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16-,17+,18-,19+/m0/s1
  • InChI Key:
    PXGPLTODNUVGFL-NAPLMKITSA-N
Related resources
Pathway info P = product of S = substrate of
Metabolite sources and localization
  • Metabolite location:
    Human organism, Body part, Extracellular, Human body biofluids, Biofluid tissues, Blood, Cerebrospinal fluid, Urine, Tissue, Cellular (general class), Subcellular, Cell membrane, Cytoplasm, Excreta material
  • Metabolite source:
    Homo sapiens, endogenous metabolite
Age-variations
Age group comparisons
Method: HPLC/MS
Sample: body fluid
PubMed PMID: 25147595
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