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

Stable Identifier
Reaction [transition]
Homo sapiens
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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

Durand, T, Balas, L, Dayaker, G

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

Arterburn, LM, Liu, YC, Chung, G, Hall, EB, Nauroth, JM, Bell, R, Van Elswyk, M

Lipids 2010
23471029 Controlled formation of mono- and dihydroxy-resolvins from EPA and DHA using soybean 15-lipoxygenase

Kralovec, JA, Dobson, EP, Adcock, JL, Barrow, CJ

J. Lipid Res. 2013
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
19324874 Biogenic synthesis, purification, and chemical characterization of anti-inflammatory resolvins derived from docosapentaenoic acid (DPAn-6)

Needham, M, Arterburn, LM, Nauroth, JM, Teymourlouei, M, Obeng, M, Raman, K, Dangi, B

J. Biol. Chem. 2009
Catalyst Activity

arachidonate 15-lipoxygenase activity of ALOX15 [cytosol]

Orthologous Events
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