Chemistry:Eicosatetraenoic acid
Eicosatetraenoic acid (ETA) designates any straight chain 20:4 fatty acid. Eicosatetraenoic acid belongs to the family of eicosanoids, molecules synthesized from oxidized polyunsaturated fatty acids (PUFAs) to mediate cell-cell communication. The eicosanoids, working in tandem, contribute to a lipid signaling complex widely responsible for inducing an inflammatory immune response.[1] Common signs of inflammation are both internal and external, with effects like visible redness, pain in the surrounding area, swelling, and the sensation of heat—many of these an effect of varying eicosanoid species.[2] These effects are associated with and have been observed in patients with cancers and various neurological/metabolic disorders.[3]
- See Essential Fatty Acid for nomenclature.
Two isomers, both of them essential fatty acids, are of particular interest:
- all-cis-5,8,11,14-eicosatetraenoic acid is an ω-6 fatty acid with the trivial name arachidonic acid. It is formed by a desaturation of dihomo-gamma-linolenic acid (DGLA, 20:3 ω-6).
- all-cis-8,11,14,17-eicosatetraenoic acid is an ω-3 fatty acid. It is an intermediate between stearidonic acid (18:4 ω-3) and eicosapentaenoic acid (EPA, 20:5 ω-3)
Some chemistry sources define 'arachadonic acid' to designate any of the eicosatetraenoic acids. However, almost all writings in biology, medicine and nutrition limit the use of the term 'arachidonic acid' to all-cis-5,8,11,14-eicosatetraenoic acid (ω-6).
Related studies
ETA is found in green-lipped mussel and appears to act as dual inhibitor of arachidonic acid oxygenation by both the cyclooxygenase (COX) and lipoxygenase pathway.[4]
Mutants of Mortierella alpina 1S-4 is a fungus employed for producing arachidonic acid. These mutants produce larger amounts of ETA due to the expression of an ω-3-desaturase gene, typically responsible for the significant production of the more abundant PUFAs.[5]
In addition to their inflammatory nature, eicosanoids such as ETA can also contribute to an anti-inflammatory response.[5]
See also
- Polyunsaturated fatty acid
- List of omega-3 fatty acids
- Omega-3 fatty acids
- Omega-6 fatty acids
References
- ↑ "Eicosanoid storm in infection and inflammation". Nature Reviews. Immunology 15 (8): 511–23. August 2015. doi:10.1038/nri3859. PMID 26139350.
- ↑ "Proinflammatory and immunoregulatory roles of eicosanoids in T cells" (in English). Frontiers in Immunology 4: 130. 2013. doi:10.3389/fimmu.2013.00130. PMID 23760108.
- ↑ "Monoacylglycerol lipase inhibitors: modulators for lipid metabolism in cancer malignancy, neurological and metabolic disorders". Acta Pharmaceutica Sinica B 10 (4): 582–602. April 2020. doi:10.1016/j.apsb.2019.10.006. PMID 32322464. PMC 7161712. https://www-ncbi-nlm-nih-gov.wexler.hunter.cuny.edu/pubmed/32322464.
- ↑ "Improvement of arthritic signs in dogs fed green-lipped mussel (Perna canaliculus)". The Journal of Nutrition 132 (6 Suppl 2): 1634S–6S. June 2002. doi:10.1093/jn/132.6.1634S. PMID 12042477.
- ↑ 5.0 5.1 "Omega-3 eicosatetraenoic acid production by molecular breeding of the mutant strain S14 derived from Mortierella alpina 1S-4". Journal of Bioscience and Bioengineering 120 (3): 299–304. September 2015. doi:10.1016/j.jbiosc.2015.01.014. PMID 25845716.
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