13-(S)-Hydroxyoctadecadienoic acid (13-HODE) incorporation and conversion to novel products by endothelial cells

Xiang Fang, Terry L. Kaduce, Arthur A. Spector

Research output: Contribution to journalArticle

20 Scopus citations

Abstract

13(S)-Hydroxy-[12,13-3H]octadecadienoic acid (13-HODE), a linoleic acid oxidation product that has vasoactive properties, was rapidly taken up by bovine aortic endothelial cells. Most of the 13-HODE was incorporated into phosphatidylcholine, and 80% was present in the sn-2 position. The amount of 13-HODE retained in the cells gradually decreased, and radiolabeled metabolites with shorter reverse-phase high-performance liquid chromatography retention times (RT) than 13-HODE accumulated in the extracellular fluid. The three major metabolites were identified by gas chromatography combined with mass spectrometry as 11-hydroxyhexadecadienoic acid (11-OH-16:2), 9- hydroxytetradecadienoic acid (9-OH-14:2), and 7-hydroxydodecadienoic acid (7- OH-12:2). Most of the radioactivity contained in the cell lipids remained as 13-HODE. However, some 11-OH-16:2 and several unidentified products with longer RT than 13-HODE were detected in the cell lipids. Normal human skin fibroblasts also converted 13-HODE to the three major chain-shortened metabolites, but Zellweger syndrome fibroblasts produced only a very small amount of 11-OH-16:2. Therefore, the chain-shortened products probably are formed primarily by peroxisomal β-oxidation. These findings suggest that peroxisomal β-oxidation may constitute a mechanism for the inactivation and removal of 13-HODE from the vascular wall. Because this is a gradual process, some 13-HODE that is initially incorporated remains in endothelial phospholipids, especially phosphatidylcholine. This may be the cause of some of the functional perturbations produced by 13-HODE in the vascular wall.

Original languageEnglish (US)
Pages (from-to)699-707
Number of pages9
JournalJournal of Lipid Research
Volume40
Issue number4
StatePublished - Apr 1 1999
Externally publishedYes

Keywords

  • Fibroblasts
  • Linoleic acid
  • Lipoxygenase
  • Oxidation
  • Peroxisomes
  • Phosphatidylcholine
  • Zellweger syndrome

ASJC Scopus subject areas

  • Biochemistry
  • Endocrinology
  • Cell Biology

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