Biotransformation of polyunsaturated fatty acids to bioactive hepoxilins and trioxilins by microbial enzymes

Jung-Ung An, Yong-Seok Song, Kyoung-Rok Kim, Yoon-Joo Ko, Do-Young Yoon and Deok-Kun Oh ()
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Jung-Ung An: Konkuk University
Yong-Seok Song: Konkuk University
Kyoung-Rok Kim: Konkuk University
Yoon-Joo Ko: Seoul National University
Do-Young Yoon: Konkuk University
Deok-Kun Oh: Konkuk University

Nature Communications, 2018, vol. 9, issue 1, 1-9

Abstract: Abstract Hepoxilins (HXs) and trioxilins (TrXs) are involved in physiological processes such as inflammation, insulin secretion and pain perception in human. They are metabolites of polyunsaturated fatty acids (PUFAs), including arachidonic acid, eicosapentaenoic acid and docosahexaenoic acid, formed by 12-lipoxygenase (LOX) and epoxide hydrolase (EH) expressed by mammalian cells. Here, we identify ten types of HXs and TrXs, produced by the prokaryote Myxococcus xanthus, of which six types are new, namely, HXB5, HXD3, HXE3, TrXB5, TrXD3 and TrXE3. We succeed in the biotransformation of PUFAs into eight types of HXs (>35% conversion) and TrXs (>10% conversion) by expressing M. xanthus 12-LOX or 11-LOX with or without EH in Escherichia coli. We determine 11-hydroxy-eicosatetraenoic acid, HXB3, HXB4, HXD3, TrXB3 and TrXD3 as potential peroxisome proliferator-activated receptor-γ partial agonists. These findings may facilitate physiological studies and drug development based on lipid mediators.

Date: 2018
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DOI: 10.1038/s41467-017-02543-8

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