Reactome | Biosynthesis of DPA-derived SPMs

Biosynthesis of DPA-derived SPMs

Stable Identifier

R-HSA-9018683

Type

Pathway

Species

Homo sapiens

ReviewStatus

5/5

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Docosapentaenoic acid (DPA), a C22:5 long-chain ω3 or ω6 polyunsaturated fatty acid (PUFA), is found in algal and fish oils, created via linoleic acid metabolism and is a metabolite in DHA metabolism. It can be acted upon by lipoxygenases to produce mono-, di- and tri-hydroxy derivatives in neutrophils and macrophages. These DPA derivatives are another branch of the specialised proresolving mediators (SPMs) produced from long-chain fatty acids which have anti-inflammatory properties, even though mechanisms of their anti-inflammatory action have not been fully elucidated (Bannenberg & Serhan 2010, Dangi et al. 2010, Vik et al. 2017, Hansen et al. 2017).

The biosynthesis of SPMs derived from the two isomers of DPA, DPAn-6 (cis-4,7,10,13,16-docosapentaenoic acid) and DPAn-3 (cis-7,10,13,16,19-docosapentaenoic acid), is described here. The only difference between the two isomers is the position of the first double bond; ω-3 for DPAn-3 and ω-6 for DPAn-6. The products of these isomers were characterised by analogy in structure and action to docosahexaenoic acid (DHA)-derived and eicosapentaenoic acid (EPA)-derived resolvins, protectins and maresins (Serhan et al. 2002, Bannenberg & Serhan 2010, Serhan et al. 2015).

Literature References

PubMed ID	Title	Journal	Year
20708099	Specialized pro-resolving lipid mediators in the inflammatory response: An update Serhan, CN, Bannenberg, G	Biochim. Biophys. Acta	2010
28602942	The novel lipid mediator PD1n-3 DPA: An overview of the structural elucidation, synthesis, biosynthesis and bioactions Serhan, CN, Hansen, TV, Dalli, J	Prostaglandins Other Lipid Mediat.	2017
28408222	Recent advances in the chemistry and biology of anti-inflammatory and specialized pro-resolving mediators biosynthesized from n-3 docosapentaenoic acid Hansen, TV, Vik, A, Dalli, J	Bioorg. Med. Chem. Lett.	2017
19679107	Metabolism and biological production of resolvins derived from docosapentaenoic acid (DPAn-6) Arterburn, LM, Hallenbeck, T, Chung, G, Nauroth, JM, Obeng, M, Dangi, B, Bailey-Hall, E	Biochem. Pharmacol.	2010