Epoxide hydrolase hydrolyses 13(S),14(S)-epoxy-DHA to MaR1

Stable Identifier
R-HSA-9024973
Type
Reaction [transition]
Species
Homo sapiens
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Maresin 1 (MaR1, 7(R),14(S)-dihydroxy-docosahexaenoic acid) is the first identified maresin. It is formed by hydrolysis of 13(R),14(S)-epoxy-docosahexaenoic acid (13(R),14(S)-epoxy-DHA) by an unknown epoxide hydrolase (Serhan et al. 2009). MaR1 displays potent anti-inflammatory and pro-resolving actions (Serhan et al. 2012, Chatterjee et al. 2014). MaR1 was found to inhibit proinflammatory mediator production by inhibiting LTA4 hydrolase, thereby shifting macrophage phenotype from proinflammatory mediator to proresolving mediator production (Dalli et al. 2013).

A novel double dioxygenation product can also be formed by non-enzymatic hydrolysis of 13(R),154(S)-epoxy-DHA, namely 7(S),14(S)-dihydroxy-docosahexaenoic acid (7-epi-MaR1). Although 7-epi-MaR1 possesses some bioactivity, it displays lower anti-inflammatory and pro-resolving actions than MaR1 (Serhan et al. 2009).

Literature References
PubMed ID Title Journal Year
23504711 The novel 13S,14S-epoxy-maresin is converted by human macrophages to maresin 1 (MaR1), inhibits leukotriene A4 hydrolase (LTA4H), and shifts macrophage phenotype

Dalli, J, Zhu, M, Vlasenko, NA, Deng, B, Haeggström, JZ, Petasis, NA, Serhan, CN

FASEB J. 2013
25036362 Maresin biosynthesis and identification of maresin 2, a new anti-inflammatory and pro-resolving mediator from human macrophages

Deng, B, Wang, CW, Arnardottir, HH, Li, Y, Cheng, CY, Dalli, J, Serhan, CN

PLoS ONE 2014
25409514 The pro-resolving lipid mediator maresin 1 (MaR1) attenuates inflammatory signaling pathways in vascular smooth muscle and endothelial cells

Chatterjee, A, Sharma, A, Chen, M, Toy, R, Mottola, G, Conte, MS

PLoS ONE 2014
19103881 Maresins: novel macrophage mediators with potent antiinflammatory and proresolving actions

Serhan, CN, Yang, R, Martinod, K, Kasuga, K, Pillai, PS, Porter, TF, Oh, SF, Spite, M

J. Exp. Med. 2009
22253477 Macrophage proresolving mediator maresin 1 stimulates tissue regeneration and controls pain

Serhan, CN, Dalli, J, Karamnov, S, Choi, A, Park, CK, Xu, ZZ, Ji, RR, Zhu, M, Petasis, NA

FASEB J. 2012
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Catalyst Activity
Title
epoxide hydrolase activity of Epoxide hydrolase [cytosol]
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