Abstract
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.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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8,11,14-Eicosatrienoic Acid / analogs & derivatives
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8,11,14-Eicosatrienoic Acid / biosynthesis*
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8,11,14-Eicosatrienoic Acid / metabolism*
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Animals
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Arachidonic Acid
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Arachidonic Acids / metabolism*
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Carbon Radioisotopes
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Chromatography, High Pressure Liquid
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Epoxy Compounds / isolation & purification*
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Ethers, Cyclic / isolation & purification*
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Fatty Acids, Unsaturated / biosynthesis*
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Fatty Acids, Unsaturated / metabolism*
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Isomerism
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Lung / metabolism*
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Male
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Mass Spectrometry
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Rats
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Rats, Inbred Strains
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Tritium
Substances
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Arachidonic Acids
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Carbon Radioisotopes
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Epoxy Compounds
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Ethers, Cyclic
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Fatty Acids, Unsaturated
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Tritium
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Arachidonic Acid
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8,11,12-trihydroxy-5,9,14-eicosatrienoic acid
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10-hydroxy-11,12-epoxyeicosa-5,8,14-trienoic acid
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8-hydroxy-11,12-epoxyeicosa-5,9,14-trienoic acid
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10,11,12-trihydroxyeicosatrienoic acid
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8,11,14-Eicosatrienoic Acid