Reactome | ALOX15 oxidises DPAn-6 to 17(S)-HDPAn-6 and 10(S),17(S)-diHDPAn-6

ALOX15 oxidises DPAn-6 to 17(S)-HDPAn-6 and 10(S),17(S)-diHDPAn-6

Stable Identifier

R-HSA-9025152

Type

Reaction [transition]

Species

Homo sapiens

Compartment

cytosol

ReviewStatus

5/5

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ALOX15 oxidises DPAn-6 to 17(S)-HDPAn-6 and 10(S),17(S)-diHDPAn-6

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Of the 5-, 12- and 15-lipoxygenases, 15-lipoxygenase is the most efficient enzyme in oxygenating docosapentaenoic acids DPAn-6 and DPAn-3 as well as docosahexaenoic acid (DHA) at efficiencies 100%, 85% and 50% respectively. The main products of DPAn-6 oxygenation were found to be 17(S)-hydroxy-DPAn-6 and (10(S),17(S)-dihydroxy-DPAn-6 (17(S)-HDPAn-6 and 10(S),17(S)-diHDPAn-6 respectively) (Dangi et al. 2009, 2010, Dobson et al. 2013, Dayaker et al. 2014). Tested in two animal models of acute inflammation (Dangi et al. 2010) and human peripheral mononuclear cells (Nauroth et al. 2010), both compounds possessed potent anti-inflammatory activity. These DPAn-6 products are analogous in structure and action to DHA (docosahexaenoic acid)-derived resolvins (Dangi et al. 2010).

Literature References

PubMed ID	Title	Journal	Year
24571431	Total synthesis of neuroprotectin D1 analogues derived from omega-6 docosapentaenoic acid (DPA) and adrenic acid (AdA) from a common pivotal, late-stage intermediate Dayaker, G, Durand, T, Balas, L	J. Org. Chem.	2014
20364438	Docosahexaenoic acid (DHA) and docosapentaenoic acid (DPAn-6) algal oils reduce inflammatory mediators in human peripheral mononuclear cells in vitro and paw edema in vivo Nauroth, JM, Liu, YC, Van Elswyk, M, Bell, R, Hall, EB, Chung, G, Arterburn, LM	Lipids	2010
23471029	Controlled formation of mono- and dihydroxy-resolvins from EPA and DHA using soybean 15-lipoxygenase Dobson, EP, Barrow, CJ, Kralovec, JA, Adcock, JL	J. Lipid Res.	2013
19679107	Metabolism and biological production of resolvins derived from docosapentaenoic acid (DPAn-6) Dangi, B, Obeng, M, Nauroth, JM, Chung, G, Bailey-Hall, E, Hallenbeck, T, Arterburn, LM	Biochem. Pharmacol.	2010
19324874	Biogenic synthesis, purification, and chemical characterization of anti-inflammatory resolvins derived from docosapentaenoic acid (DPAn-6) Dangi, B, Obeng, M, Nauroth, JM, Teymourlouei, M, Needham, M, Raman, K, Arterburn, LM	J. Biol. Chem.	2009