ALOX15 dehydrogenates 17(S)-Hp-DHA to 16S,17S-epoxy-DHA

Stable Identifier
Reaction [transition]
Homo sapiens
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Instead of undergoing a second oxygenation (to form PDX), the hydroperoxide intermediate 17(S)-Hp-DHA undergoes a hydrogen abstraction by 15-lipoxygenase (ALOX15) to form an intermediate epoxide, 16S,17S-epoxy-DHA (Hong et al. 2003, Serhan et al. 2006, Hong et al. 2007, Aursnes et al. 2015). This epoxide has now proved to be the precursor for the production of (neuro)protectin D1 ((N)PD1) as well as production of protectin conjugates in tissue regeneration (PCTRs) (Dalli et al. 2015, Ramon et al. 2016, Aursnes et al. 2015).
Literature References
PubMed ID Title Journal Year
26580578 Synthesis of the 16S,17S-Epoxyprotectin Intermediate in the Biosynthesis of Protectins by Human Macrophages

Serhan, CN, Colas, RA, Hansen, TV, Tungen, JE, Aursnes, M, Dalli, J, Vlasakov, I

J. Nat. Prod. 2015
26878209 The Protectin PCTR1 Is Produced by Human M2 Macrophages and Enhances Resolution of Infectious Inflammation

Serhan, CN, Winkler, JW, Sanger, JM, Hansen, TV, Tungen, JE, Aursnes, M, Dalli, J, Ramon, S

Am. J. Pathol. 2016
16424216 Anti-inflammatory actions of neuroprotectin D1/protectin D1 and its natural stereoisomers: assignments of dihydroxy-containing docosatrienes

Lu, Y, Serhan, CN, Colgan, SP, Petasis, NA, Hong, S, Baer, T, Yang, R, Gotlinger, K, Siegelman, J

J. Immunol. 2006
17055291 Resolvin D1, protectin D1, and related docosahexaenoic acid-derived products: Analysis via electrospray/low energy tandem mass spectrometry based on spectra and fragmentation mechanisms

Serhan, CN, Gotlinger, KH, Lu, Y, Petasis, NA, Hong, S, Yang, R

J. Am. Soc. Mass Spectrom. 2007
12590139 Novel docosatrienes and 17S-resolvins generated from docosahexaenoic acid in murine brain, human blood, and glial cells. Autacoids in anti-inflammation

Serhan, CN, Gronert, K, Devchand, PR, Hong, S, Moussignac, RL

J. Biol. Chem. 2003
Catalyst Activity

arachidonate 15-lipoxygenase activity of ALOX15 [cytosol]

Orthologous Events
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