Isofuran

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Isofurans are nonclassic eicosanoids formed nonenzymatically by free radical mediated peroxidation of arachidonic acid. The isofurans are similar to the isoprostanes and are formed under similar conditions, but contain a substituted tetrahydrofuran ring. The concentration of oxygen affects this process; at elevated oxygen concentrations, the formation of isofurans is favored whereas the formation of isoprostanes is disfavored. [1] [2]

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Phosphatidylethanolamine group of chemical compounds

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9-Hydroxyoctadecadienoic acid chemical compound

9-Hydroxyoctadecadienoic acid has been used in the literature to designate either or both of two stereoisomer metabolites of the essential fatty acid, linoleic acid: 9(S)-hydroxy-10(E),12(Z)-octadecadienoic acid and 9(R)-hydroxy-10(E),12(Z)-octadecadienoic acid ; these two metabolites differ in having their hydroxy residues in the S or R configurations, respectively. The accompanying figure gives the structure for 9(S)-HETE. Two other 9-hydroxy linoleic acid derivatives occur in nature, the 10E,12E isomers of 9(S)-HODE and 9(R)-HODE viz., 9(S)-hydroxy-10E,12E-octadecadienoic acid and 9(R)-hydroxy-10E,12E-octadecadienoic acid ; these two derivatives have their double bond at carbon 12 in the E or trans configuration as opposed to the Z or cis configuration. The four 9-HODE isomers, particularly under conditions of oxidative stress, may form together in cells and tissues; they have overlapping but not identical biological activities and significances. Because many studies have not distinguished between the S and R stereoisomers and, particularly in identifying tissue levels, the two EE isomers, 9-HODE is used here when the isomer studied is unclear.

The neuroprostanes are prostaglandin-like compounds formed in vivo from the free radical-catalyzed peroxidation of essential fatty acids without the direct action of cyclooxygenase (COX) enzymes. The result is the formation of isoprostane-like compounds F4-, D4-, E4-, A4-, and J4-neuroprostanes which have been shown to be produced in vivo. These oxygenated essential fatty acids possess potent biological activity as anti-inflammatory mediators inhibiting the response of human macrophages that augment the perception of pain.

References

  1. Roberts, L. Jackson; Fessel, Joshua P.; Davies, Sean S. (2006-04-05). "The Biochemistry of the Isoprostane, Neuroprostane, and Isofuran Pathways of Lipid Peroxidation". Brain Pathology. 15 (2): 143–148. doi:10.1111/j.1750-3639.2005.tb00511.x. ISSN   1015-6305.
  2. Roberts, LJ 2nd and Fessel, JP (Mar 2004). "The biochemistry of the isoprostane, neuroprostane, and isofuran pathways of lipid peroxidation". Chem Phys Lipids. 128 (1–2): 173–86. doi:10.1016/j.chemphyslip.2003.09.016. PMID   15037162.CS1 maint: multiple names: authors list (link)