Epoxide hydrolase hydrolyses 13,14-epoxy-DPAn-3 to MaR1n-3 DPA or MaR2n-3 DPA

Stable Identifier
R-HSA-9025998
Type
Reaction [transition]
Species
Homo sapiens
Compartment
cytosol
ReviewStatus
5/5
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Epoxide hydrolase hydrolyses 13,14-epoxy-DPAn-3 to MaR1n-3 DPA or MaR2n-3 DPA
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In a reaction scheme similar to the one for DHA-derived maresins, 13,14(S)-epoxy-docosapentaenoic acid (13,14(S)-epoxy-DPAn-3) can be hydrolysed by an epoxide hydrolase to form either 7(R),14(S)-dihydroxy-docosapentaenoic acid (MaR1n-3 DPA) or 13,14(S)-dihydroxy-docosapentaenoic acid (MaR2n-3 DPA) (Dalli et al. 2013). MaR1n-3 DPA and MaR2n-3 DPA are named after maresin-1 (derived from DHA) as they share an alcohol group at C14 and are proposed to possess similar anti-inflammatory and proresolving potency and activity as maresin-1. With human leukocytes these n-3 DPA-SPMs reduced neutrophil chemotaxis, adhesion and enhanced macrophage phagocytosis (Dalli et al. 2013, Vik et al. 2017). The total chemical synthesis of MaR1n-3 DPA had been reported for the first time in 2014 (Tungen et al. 2014).
Literature References
PubMed ID Title Journal Year
23736886 Novel n-3 immunoresolvents: structures and actions

Serhan, CN, Colas, RA, Dalli, J

Sci Rep 2013
25225129 Total synthesis of the anti-inflammatory and pro-resolving lipid mediator MaR1n-3 DPA utilizing an sp(3) -sp(3) Negishi cross-coupling reaction

Serhan, CN, Hansen, TV, Tungen, JE, Aursnes, M, Arnardottir, H, Dalli, J

Chemistry 2014
Participants
Input
Output
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as an event of
Catalyst Activity

epoxide hydrolase activity of Epoxide hydrolase [cytosol]

Physical Entity
Epoxide hydrolase [cytosol] (Homo sapiens)
Activity
epoxide hydrolase activity (GO:0004301)
Authored
Jassal, B  (2017-10-16)
Reviewed
Hansen, TV  (2018-02-21)
Created
Jassal, B  (2017-10-16)
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