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. 2022 Dec 24;12(1):82. doi: 10.3390/cells12010082

Table 4.

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

Oxylipin CAS Number CYPs/Enzymes References Effects References
5-HETE 330796-62-8 1B1, 2B6 [139,140]

  • Activates Nrf2

  • Stimulate neutrophils to increase intracellular calcium

  • Induce airway contraction through induction of neutrophil migration

 [99,106,110]
9-HETE 79495-85-5 2B6 [140]

  • Marker for oxidative stress

 [114]
12-HETE 71030-37-0 1B1, 2B6 [8,139,140]

  • Contributes to platelet aggregation

 [112]
15-HETE 71030-36-9 1B1 [139]

  • Can increase pulmonary artery tension through PGH2/TXA2 receptors

 [107]
18-HETE 133268-58-3 2E1 [141]

  • Induces vasodilation in rabbit kidney

 [115]
19-HETE 79551-85-2 2E1, 2U1 [141,142]

  • Activates the prostacyclin (IP) receptor, inhibiting platelet aggregation and reducing vascular constriction

 [98]
20-HETE 79551-86-3 2U1 [142]

  • Acts as a participant in tubuloglomerular feedback response in the kidney

  • Promotes salt excretion through inhibition of the Na+-K+-ATPase and Na+-K+-2Cl− cotransporters

  • Constricts vascular smooth muscle through blocking activity of the calcium-activated potassium channel and enhancing the activity of voltage-gated L-type calcium channels

 [108,143,144]
5,6-EET 81246-84-6 2B6, 2D6, 2J2, 3A4 [8,138,145,146]

  • Can suppress cardiomyocyte shortening

  • Inhibits T-type calcium channels which may contribute to vascular tone

 [122,123]
8,9-EET 184488-44-6 1A2, 2B6, 2C9, 2D6, 2J2 3A4 [8,138,140,145,146,147,148]

  • Inhibits B-cell proliferation and survival, possibly through inhibition of Nf-κB

  • Stimulates pulmonary artery endothelial cells proliferation and angiogenesis through the JNK/c-Jun pathway

  • Decreases epithelial Na+ channel activity to reduce sodium reabsorption

 [116,118,149]
11,12-EET 200960-01-6 2C8, 2C9, 2D6, 2J2, 2S1, 3A4, 2B [104,138,145,148,150]

  • Stimulates pulmonary artery endothelial cells proliferation and angiogenesis through the JNK/c-Jun pathway

  • Decreases epithelial Na+ channel activity to reduce sodium reabsorption

  • Activates the α and β1 subunits of mitochondrial BK channels to promote pulmonary vasoconstriction

  • Increased following eschemia in endothelial CYP2J2-overexpressing mice

 [83,116,118,151]
14,15-EET 197508-62-6 2C8, 2C9, 2D6, 2J2, 2S1, 3A4 [138,145,148,150]

  • Stimulates pulmonary artery endothelial cells proliferation and angiogenesis through the JNK/c-Jun pathway

  • Decreases epithelial Na+ channel activity to reduce sodium reabsorption

  • Increased following eschemia in endothelial CYP2J2-overexpressing mice

  • Suppresses mitochondrial apoptosis through the PI3K/AKT/CREB/Bcl-2 signaling pathway in ischemia–reperfusion injury

 [83,116,118,120]
5,6-EET-EA * N/A 2D6, 2J2, 3A4 [152,153]

  • Potent agonist of CB1 and CB2

  • Weak agonist of GPR119 receptor

 [133,137]
8,9-EET-EA * N/A 2D6, 2J2, 3A4 [152,153]

  • Agonist of GPR119 receptor

 [137]
11,12-EET-EA * N/A 2D6, 2J2, 3A4 [152,153]

  • High-affinity agonist of CB2

 [134]
14,15-EET-EA * N/A 2D6, 2J2, 3A4 [152,153]

  • Weak agonist of GPR119 receptor

 [137]
19-HETE-EA * N/A 2D6, 3A4 [152,153]

  • Unknown
20-HETE-EA * 942069-11-6 2D6, 3A4 [34,152,153]

  • Low affinity binding of CB

 [135]

* denotes an oxylipin derived from anadamide (AEA).