Table 3.

Metabolism of linoleic acid produces several oxylipins with a diverse set of putative functions.

Oxylipin	CAS Number	CYPs/Enzymes	References	Effects	References
9,10-EpOME	6814-52-4	1A2, 2B6, 2C9	[8,84]	Activate NF-kB and AP-1 in endothelial cells resulting in oxidative stress Inhibit osteoblast differentiation through PPARγ2 Obesity	[2,76,85]
9,10-DiHOME	263399-34-4	sEH		Promotes adipogenesis and inhibits osteogenesis through PPARγ2	[76]
12,13-EpOME	Not found	1A2, 2C9, 2E1, 2J2,	[68,84]	Activate NF-kB and AP-1 in endothelial cells resulting in oxidative stress Obesity	[2,85]
12,13-DiHOME	263399-35-5	sEH		Stimulates brown adipose tissue activity in response to cold exposure Stimulates cell proliferation in MCF-7 breast cancer cells Cause mitochondrial dysfunction through activation of the permeability transition Increases exercise-mediated fatty acid uptake Increases sensitivity to thermal pain Cardiac/ischemic injury	[7,16,52,86,87,88]
9-HpODE	63121-49-3	1A2, 2S1	[68,69]	Increases GSH oxidation	[70]
9-HODE	98524-19-7	1A2, 2B6, 2C9, 2C19, 2E1, 2J2 Peroxidase	[8,73,75]	Stimulates fat accumulation through PPARγ2 Associated with reduced obesity, greater glucose sensitivity, but also liver steatosis Decreased in response to ischemia	[8,76,83]
9-oxoODE	54232-59-6	Dehydrogenase		May contribute to pain and hyperalgesia through TRVP1	[89]
13-HpODE	23017-93-8	1A2, 2S1	[68,69]	Can induce smooth muscle cytotoxicity by activating NAD(P)H oxidase Induce TNFα, MCP1, and GZMB in Natural Killer (NK) cells	[71,72]
13-HODE	18104-45-5	1A2, 2B6, 2C9, 2C19, 2E1, 2J2 Peroxidase	[8,75,90]	Stimulates prostacyclin production by increasing arachidonic acid release Decreased in response to ischemia Can inhibit platelet adhesion to endothelial cells Ligand for PPARγ Inhibit LtB4 secretion from stimulated leukocytes	[79,80,82,83,91]
13-oxoODE	29623-29-8	Dehydrogenase		Regulates gene expression in macrophages through PPARγ Reduces IL-8 secretion and has anti-inflammatory effects in colonic epithelial cells Associated with reduced obesity in females; greater glucose sensitivity and liver steatosis in male hCYP2B6-Tg mice	[8,92,93]