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oxylipin biosynthetic process

Definition

Target type: biologicalprocess

The chemical reactions and pathways resulting in the formation of any oxylipin, any of a group of biologically active compounds formed by oxidative metabolism of polyunsaturated fatty acids. [GOC:mah, PMID:11960741]

Oxylipin biosynthesis is a crucial metabolic pathway involved in the production of bioactive lipid signaling molecules known as oxylipins. These molecules play diverse roles in plant and animal physiology, contributing to processes like stress responses, defense mechanisms, inflammation, and development. The process starts with the enzymatic oxygenation of polyunsaturated fatty acids (PUFAs), typically linoleic acid (18:2) or α-linolenic acid (18:3), by a family of enzymes known as lipoxygenases (LOXs). LOXs catalyze the insertion of molecular oxygen into the PUFA molecule, forming hydroperoxides. These hydroperoxides serve as substrates for a variety of downstream enzymes, including hydroperoxide lyases, allene oxide synthases, and epoxide hydrolases. These enzymes further modify the hydroperoxides, generating a diverse array of oxylipins with distinct biological activities. The diversity of oxylipins stems from the varying regio- and stereochemistry of oxygen insertion, as well as the different enzymatic transformations that occur during their biosynthesis. For example, the LOX enzyme can catalyze the oxygenation of the PUFA at different carbon positions, leading to the formation of distinct hydroperoxides. These hydroperoxides are further metabolized through various enzymatic pathways, resulting in a vast array of oxylipins, including jasmonates, prostaglandins, leukotrienes, and lipoxins. These oxylipins have diverse biological activities, including regulation of plant growth and development, modulation of immune responses, and the control of inflammation and pain. In plants, oxylipins are involved in defense against pathogens and herbivores, as well as in the regulation of growth and development. For instance, jasmonates, a class of oxylipins, play crucial roles in plant defense against insect herbivores and microbial pathogens. In animals, oxylipins are involved in a wide range of physiological processes, including inflammation, pain, and blood pressure regulation. For example, prostaglandins, another class of oxylipins, are involved in inflammation and pain perception. Leukotrienes and lipoxins are key mediators of the immune response, contributing to the recruitment of immune cells and the resolution of inflammation. The intricate interplay of these diverse oxylipins highlights their significance in maintaining homeostasis and regulating various physiological processes in both plants and animals. Their complex biosynthetic pathway and diverse biological activities make them important targets for drug development and therapeutic interventions.'
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Proteins (1)

ProteinDefinitionTaxonomy
Cytochrome P450 4A11A cytochrome P450 4A11 that is encoded in the genome of human. [PRO:DNx, UniProtKB:Q02928]Homo sapiens (human)

Compounds (5)

CompoundDefinitionClassesRoles
tranylcypromine(1R,2S)-tranylcypromine : A 2-phenylcyclopropan-1-amine that is the (1R,2S)-enantiomer of tranylcypromine.

tranylcypromine : A racemate comprising equal amounts of (1R,2S)- and (1S,2R)-2-phenylcyclopropan-1-amine. An irreversible monoamine oxidase inhibitor that is used as an antidepressant (INN tranylcypromine).

Tranylcypromine: A propylamine formed from the cyclization of the side chain of amphetamine. This monoamine oxidase inhibitor is effective in the treatment of major depression, dysthymic disorder, and atypical depression. It also is useful in panic and phobic disorders. (From AMA Drug Evaluations Annual, 1994, p311)
2-phenylcyclopropan-1-amine
proadifen hydrochloride
pirlindolepirlindole: RN given refers to parent cpd; synonym pyrazidol refers to mono-HCl; structure in Negwer, 5th ed, #2812carbazoles
17-dihydroexemestane
kaf156ganaplacide: antimalarial