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

Stable Identifier
Reaction [transition]
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
25036362 Maresin biosynthesis and identification of maresin 2, a new anti-inflammatory and pro-resolving mediator from human macrophages

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

PLoS ONE 2014
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

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

FASEB J. 2013
25409514 The pro-resolving lipid mediator maresin 1 (MaR1) attenuates inflammatory signaling pathways in vascular smooth muscle and endothelial cells

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

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

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

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

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

FASEB J. 2012
Catalyst Activity

epoxide hydrolase activity of Epoxide hydrolase [cytosol]

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