13-Hydroxyoctadecadienoic acid: Difference between revisions

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{{Short description|A hydroxylated fatty acid derived from linoleic acid}}
{{DISPLAYTITLE:13-Hydroxyoctadecadienoic acid}}
{{DISPLAYTITLE:13-Hydroxyoctadecadienoic acid}}


'''13-Hydroxyoctadecadienoic acid''' (13-HODE) is a [[hydroxyl]]ated [[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.
== 13-Hydroxyoctadecadienoic acid ==
[[File:13-HODE.svg|thumb|right|Chemical structure of 13-Hydroxyoctadecadienoic acid]]
13-Hydroxyoctadecadienoic acid, commonly abbreviated as 13-HODE, is a type of [[hydroxy fatty acid]] derived from the oxidation of [[linoleic acid]]. It is one of the primary products formed during the enzymatic and non-enzymatic oxidation of linoleic acid, a common polyunsaturated fatty acid found in many vegetable oils.


==Structure and Formation==
== Formation ==
13-Hydroxyoctadecadienoic acid is a [[monohydroxy fatty acid]] with the chemical formula C<sub>18</sub>H<sub>32</sub>O<sub>3</sub>. 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.
13-HODE is formed through the action of [[lipoxygenase]] enzymes, which catalyze the oxidation of linoleic acid. This process involves the insertion of molecular oxygen into the fatty acid chain, resulting in the formation of a hydroperoxide intermediate. The hydroperoxide is then reduced to form 13-HODE. Non-enzymatic pathways, such as free radical oxidation, can also produce 13-HODE.


==Biological Functions==
== 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]].
13-HODE plays a role in various biological processes. It is involved in the regulation of [[inflammation]] and has been shown to have anti-inflammatory properties. Additionally, 13-HODE can influence [[cell signaling]] pathways and modulate the activity of [[nuclear receptors]] such as [[PPAR gamma]].


===Role in Inflammation===
== Clinical Significance ==
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.
The levels of 13-HODE in the body can be indicative of oxidative stress and inflammation. Elevated levels of 13-HODE have been associated with various pathological conditions, including [[atherosclerosis]], [[diabetes]], and certain types of [[cancer]]. As a result, 13-HODE is often studied as a potential biomarker for these diseases.


===Cell Proliferation and Apoptosis===
== Related Compounds ==
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.
13-HODE is part of a larger family of oxidized fatty acids known as [[oxylipins]]. Other related compounds include 9-Hydroxyoctadecadienoic acid (9-HODE) and various [[prostaglandins]] and [[leukotrienes]]. These compounds collectively play important roles in the regulation of inflammation and immune responses.


==Clinical Significance==
== Related Pages ==
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]]
* [[Linoleic acid]]
* [[Lipoxygenase]]
* [[Lipoxygenase]]
* [[Fatty acid metabolism]]
* [[Oxidative stress]]
* [[Eicosanoids]]
* [[Atherosclerosis]]
 
* [[PPAR gamma]]
==Gallery==
<gallery>
File:13-HODE.svg|Chemical structure of 13-Hydroxyoctadecadienoic acid
</gallery>


[[Category:Fatty acids]]
[[Category:Fatty acids]]
[[Category:Biochemistry]]
[[Category:Biochemistry]]
[[Category:Hydroxy acids]]
[[Category:Oxylipins]]

Latest revision as of 11:11, 15 February 2025


13-Hydroxyoctadecadienoic acid[edit]

Chemical structure of 13-Hydroxyoctadecadienoic acid

13-Hydroxyoctadecadienoic acid, commonly abbreviated as 13-HODE, is a type of hydroxy fatty acid derived from the oxidation of linoleic acid. It is one of the primary products formed during the enzymatic and non-enzymatic oxidation of linoleic acid, a common polyunsaturated fatty acid found in many vegetable oils.

Formation[edit]

13-HODE is formed through the action of lipoxygenase enzymes, which catalyze the oxidation of linoleic acid. This process involves the insertion of molecular oxygen into the fatty acid chain, resulting in the formation of a hydroperoxide intermediate. The hydroperoxide is then reduced to form 13-HODE. Non-enzymatic pathways, such as free radical oxidation, can also produce 13-HODE.

Biological Functions[edit]

13-HODE plays a role in various biological processes. It is involved in the regulation of inflammation and has been shown to have anti-inflammatory properties. Additionally, 13-HODE can influence cell signaling pathways and modulate the activity of nuclear receptors such as PPAR gamma.

Clinical Significance[edit]

The levels of 13-HODE in the body can be indicative of oxidative stress and inflammation. Elevated levels of 13-HODE have been associated with various pathological conditions, including atherosclerosis, diabetes, and certain types of cancer. As a result, 13-HODE is often studied as a potential biomarker for these diseases.

Related Compounds[edit]

13-HODE is part of a larger family of oxidized fatty acids known as oxylipins. Other related compounds include 9-Hydroxyoctadecadienoic acid (9-HODE) and various prostaglandins and leukotrienes. These compounds collectively play important roles in the regulation of inflammation and immune responses.

Related Pages[edit]