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. 2020 Nov 2;10:18849. doi: 10.1038/s41598-020-76005-5

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© The Author(s) 2020

Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/.

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Conversion pathways of DHA into lipid mediators by collaboration with biological and chemical reactions. Three products were converted from DHA by Osc-LOX, in which the conversion proceeds sequentially in a concentration-dependent manner of the enzyme. Osc-LOX converted DHA (1) into 17S-hydroperoxy-docosahexaenoic acid (2), 17S-hydroperoxy-docosahexaenoic acid into 7S,17S-dihydroperoxy-docosahexaenoic acid (3), and 7S,17S-dihydroperoxy-docosahexaenoic acid into 7S,15R-dihydroperoxy-16S,17S-epoxy-docosapenta-enoic acid as a precursor, respectively. And then, 17S-HDHA, RvD5, and 7S,15R-dihydroxy-16S,17S-epoxy-docosapentaenoic acid were converted by deoxygenation using sodium borohydride from each corresponded precursor. (4). Two products were generated by sodium hydroxide (NaOH): main product was 7S,15R,16S,17S-tetrahydroxy-docosapentaenoic acid (5) and minor product was RvD2 (6).