Arachidonic acid epoxides. Isolation and structure of two hydroxy epoxide intermediates in the formation of 8,11,12- and 10,11,12-trihydroxyeicosatrienoic acids.
Arachidonic acid and 12-hydroperoxyeicosa-5,8, 10, 14-tetraenoic acid are converted by a 0-30% ammonium sulfate fraction (Fraction A) of the high speed supernatant of rat lung into two hydroxy epoxides (EH-1 and EH-2) which have been purified by high performance liquid chromatography. These hydroxy epoxides are converted quantitatively into two triols (10,11,12- from EH-1 and 8,11,12- from EH-2) by a 30-50% ammonium sulfate fraction (Fraction B) of the high speed supernatant. We propose the structures, 8-hydroxy-11,12-epoxyeicosa-5,9,14-trienoic acid (EH-2) and 10-hydroxy-11,12-epoxyeicosa-5,8,14-trienoic acids (EH-1) for these intermediates on the basis of mass spectral interpretation of several derivatives including the lithium aluminum hydride reduction product of both natural and 18Oxygenated derivatives.
D015126:8,11,14-Eicosatrienoic Acid / Q000031:analogs & derivatives / Q000096:biosynthesis* / Q000378:metabolism*; D000818:Animals; D016718:Arachidonic Acid; D001095:Arachidonic Acids / Q000378:metabolism*; D002250:Carbon Radioisotopes; D002851:Chromatography, High Pressure Liquid; D004852:Epoxy Compounds / Q000302:isolation & purification*; D004988:Ethers, Cyclic / Q000302:isolation & purification*; D005231:Fatty Acids, Unsaturated / Q000096:biosynthesis* / Q000378:metabolism*; D007536:Isomerism; D008168:Lung / Q000378:metabolism*; D008297:Male; D013058:Mass Spectrometry; D051381:Rats; D011919:Rats, Inbred Strains; D014316:Tritium
D001095:Arachidonic Acids; D002250:Carbon Radioisotopes; D004852:Epoxy Compounds; D004988:Ethers, Cyclic; D005231:Fatty Acids, Unsaturated; D014316:Tritium; D016718:Arachidonic Acid; C019121:8,11,12-trihydroxy-5,9,14-eicosatrienoic acid; C022948:10-hydroxy-11,12-epoxyeicosa-5,8,14-trienoic acid; C038243:8-hydroxy-11,12-epoxyeicosa-5,9,14-trienoic acid; C037854:10,11,12-trihydroxyeicosatrienoic acid; D015126:8,11,14-Eicosatrienoic Acid