13-Hydroxyoctadecadienoic acid

A hydroxylated fatty acid derived from linoleic acid

13-Hydroxyoctadecadienoic acid (13-HODE) is a hydroxylated fatty acid derived from linoleic acid. It is one of the primary products of the lipoxygenase pathway and plays a significant role in various biological processes.

Structure and Formation

13-Hydroxyoctadecadienoic acid is a monohydroxy fatty acid with the chemical formula C₁₈H₃₂O₃. It is formed by the enzymatic oxidation of linoleic acid, a common polyunsaturated fatty acid found in dietary sources. The enzyme 15-lipoxygenase catalyzes the addition of molecular oxygen to linoleic acid, resulting in the formation of 13-HODE.

Biological Functions

13-HODE is involved in various physiological and pathological processes. It acts as a signaling molecule and has been implicated in the regulation of inflammation, cell proliferation, and apoptosis.

Role in Inflammation

In the context of inflammation, 13-HODE can modulate the activity of immune cells and influence the production of cytokines. It has been shown to have both pro-inflammatory and anti-inflammatory effects, depending on the cellular context and concentration.

Cell Proliferation and Apoptosis

13-HODE can affect cell proliferation and apoptosis, making it relevant in the study of cancer and other diseases characterized by abnormal cell growth. It may promote or inhibit cell proliferation depending on the type of cells and the presence of other signaling molecules.

Clinical Significance

The levels of 13-HODE in biological fluids and tissues can serve as biomarkers for certain diseases. Elevated levels have been associated with conditions such as atherosclerosis, diabetes, and cancer.

Metabolism

After its formation, 13-HODE can undergo further metabolism. It can be converted into other bioactive lipids or be incorporated into phospholipids within cell membranes, influencing membrane properties and cell signaling.

Related Compounds

13-HODE is part of a larger family of hydroxylated fatty acids, including 9-HODE, which is also derived from linoleic acid. These compounds share similar pathways of formation and biological activities.

Related pages

• Linoleic acid
• Lipoxygenase
• Fatty acid metabolism
• Eicosanoids

Gallery

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  Chemical structure of 13-Hydroxyoctadecadienoic acid