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

Abstract

13(S)-Hydroxy-[12,13-3 H]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 ␤ -oxidation. These findings suggest that peroxisomal ␤ -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. -Fang, X., T. L. Kaduce, and A. A. Spector. 13-(S)-Hydroxyoctadecadienoic acid (13-HODE) incorporation and conversion to novel products by endothelial cells.

Integrative analysis of transcriptomics and metabolomics to reveal the melanogenesis pathway of muscle and related meat characters in Wuliangshan black-boned chickens

“…WLS black-boned chickens showed higher levels of linoleic acid oxidation product, 13-HODE and lower levels of phosphatidylcholine in breast muscle compared with the two white muscled chicken breeds. Fang et al [ 19 ] indicated that 13- HODE has vasoactive properties, was rapidly taken up by bovine aortic endothelial cells. 13-HODE prevents cell adhesion to endothelial cells and can inhibit cancer metastasis.…”

Omega-6 and Omega-3 Fatty Acid-Derived Oxylipins from the Lipoxygenase Pathway in Maternal and Umbilical Cord Plasma at Delivery and Their Relationship with Infant Growth

“…HODEs, as with HETEs, are generally present in healthy pregnancies [ 21 ]; they function as PPAR ligands and have atherogenic properties. HODE activity is modulated by Th1 and Th2 lymphocytes with cytokine and chemokine participation, either pro- or anti-inflammatory, depending on the type of lymphocytes present [ 31 ]. Best et al demonstrated that maternal 13-HODE significantly decreases throughout normal pregnancy, suggesting that less metabolite is transferred to the developing fetus [ 24 ].…”

Targeted Lipidomics for Characterization of PUFAs and Eicosanoids in Extracellular Vesicles

“…As these eicosanoids are associated with pro-inflammatory effects, this finding seems contradictory at first. However, this finding is explainable by LOX pathway activation by IL4 [ 49 , 65 , 66 , 67 , 68 ], which we used to polarize M2 macrophages. In the future, other M1/M2 macrophage differentiation approaches as well as the analysis of primary M1/M2 macrophages will allow confirmation of these findings.…”