Metabolism of 15-hydroxy-5,8,11,13-eicosatetraenoic acid by MOLT-4 cells and blood T-lymphocytes

Christos Hadjiagapiou, Jeffrey Travers, Richard H. Fertel, Howard Sprecher

Research output: Contribution to journalArticle

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Abstract

MOLT-4 lymphocytes metabolize 15-hydroxy-5,8,11,13-eicosatetraenoic acid (15-HETE) via β-oxidation with retention of the hydroxyl group at the ω6-carbon atom. 15-HETE oxidation is accompanied by the time-dependent accumulation of both β-hydroxy acids and metabolites produced by repetitive cycles of the β-oxidation spiral. Detection of 7-hydroxy-5-dodecenoic acid shows that these cells continue to β-oxidize the substrate when the conjugated diene is allylic to a hydroxyl group. When 15-HETE was the substrate, it was also possible to detect 12-hydroxy-5,8,10-heptadecatrien-1-al and 3,15-dihydroxy-8,11, 13-eicosatrienoic acid. The former product may be produced by α-oxidation of 13-hydroxy-6,9,11-octadecatrienoic acid followed by its decarboxylation. Detection of a 20-carbon metabolite, lacking a double bond at position 5, suggests that an intermediate of β-oxidation was used as a substrate for chain elongation. When 13-hydroxy-6,9,11-octadecatrienoic acid was used as a substrate, it was indeed possible to detect 3,15-dihydroxy-8,11,13-eicosatrienoic acid as well as 15-hydroxy-8,11,13-eicosatrienoic acid. In addition, 13-hydroxy-6,9,11-octadecatrienoic acid was a precursor for the biosynthesis of both 14-hydroxy-7,10,12-nonadecatrien-1-al and 1,14-dihydroxy-7,10,12-nonadecatriene. These studies with MOLT-4 cells as well as with T-lymphocytes isolated from blood show that products of the 15-lipoxygenase pathway are metabolized with the accumulation of a variety of compounds. Since 15-HETE has been implicated as a modulator of T-cell function, these findings raise the possibility that the newly described metabolites may be involved in regulating lymphocyte function.

Original languageEnglish (US)
Pages (from-to)4369-4371
Number of pages3
JournalJournal of Biological Chemistry
Volume265
Issue number8
StatePublished - Mar 15 1990
Externally publishedYes

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T-cells
Metabolism
Blood Cells
Blood
T-Lymphocytes
Oxidation
Metabolites
Hydroxyl Radical
Lymphocytes
Substrates
Carbon
Arachidonate 15-Lipoxygenase
Hydroxy Acids
Decarboxylation
Acids
Biosynthesis
Modulators
Elongation
15-hydroxy-5,8,11,13-eicosatetraenoic acid
Atoms

ASJC Scopus subject areas

  • Biochemistry

Cite this

Metabolism of 15-hydroxy-5,8,11,13-eicosatetraenoic acid by MOLT-4 cells and blood T-lymphocytes. / Hadjiagapiou, Christos; Travers, Jeffrey; Fertel, Richard H.; Sprecher, Howard.

In: Journal of Biological Chemistry, Vol. 265, No. 8, 15.03.1990, p. 4369-4371.

Research output: Contribution to journalArticle

Hadjiagapiou, Christos ; Travers, Jeffrey ; Fertel, Richard H. ; Sprecher, Howard. / Metabolism of 15-hydroxy-5,8,11,13-eicosatetraenoic acid by MOLT-4 cells and blood T-lymphocytes. In: Journal of Biological Chemistry. 1990 ; Vol. 265, No. 8. pp. 4369-4371.
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abstract = "MOLT-4 lymphocytes metabolize 15-hydroxy-5,8,11,13-eicosatetraenoic acid (15-HETE) via β-oxidation with retention of the hydroxyl group at the ω6-carbon atom. 15-HETE oxidation is accompanied by the time-dependent accumulation of both β-hydroxy acids and metabolites produced by repetitive cycles of the β-oxidation spiral. Detection of 7-hydroxy-5-dodecenoic acid shows that these cells continue to β-oxidize the substrate when the conjugated diene is allylic to a hydroxyl group. When 15-HETE was the substrate, it was also possible to detect 12-hydroxy-5,8,10-heptadecatrien-1-al and 3,15-dihydroxy-8,11, 13-eicosatrienoic acid. The former product may be produced by α-oxidation of 13-hydroxy-6,9,11-octadecatrienoic acid followed by its decarboxylation. Detection of a 20-carbon metabolite, lacking a double bond at position 5, suggests that an intermediate of β-oxidation was used as a substrate for chain elongation. When 13-hydroxy-6,9,11-octadecatrienoic acid was used as a substrate, it was indeed possible to detect 3,15-dihydroxy-8,11,13-eicosatrienoic acid as well as 15-hydroxy-8,11,13-eicosatrienoic acid. In addition, 13-hydroxy-6,9,11-octadecatrienoic acid was a precursor for the biosynthesis of both 14-hydroxy-7,10,12-nonadecatrien-1-al and 1,14-dihydroxy-7,10,12-nonadecatriene. These studies with MOLT-4 cells as well as with T-lymphocytes isolated from blood show that products of the 15-lipoxygenase pathway are metabolized with the accumulation of a variety of compounds. Since 15-HETE has been implicated as a modulator of T-cell function, these findings raise the possibility that the newly described metabolites may be involved in regulating lymphocyte function.",
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