Bioconversion of arachidonic acid into human 14,15-hepoxilin B 3 and 13,14,15-trioxilin B 3 by recombinant cells express
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ORIGINAL RESEARCH PAPER
Bioconversion of arachidonic acid into human 14,15hepoxilin B3 and 13,14,15-trioxilin B3 by recombinant cells expressing microbial 15-lipoxygenase without and with epoxide hydrolase J. Lee . T.-H. Kim . D.-K. Oh
Received: 20 March 2020 / Accepted: 29 May 2020 Ó Springer Nature B.V. 2020
Abstract Objective To produce high concentrations of 13-hydroxy-14,15-epoxy-eicosatrienoic acid (14,15-hepoxilin B3, 14,15-HXB3) and 13,14,15-trihydroxyeicosatrienoic acid (13,14,15-trioxilin B3, 13,14,15TrXB3) from arachidonic acid (ARA) using microbial 15-lipoxygenase (15-LOX) without and with epoxide hydrolase (EH), respectively. Results The products obtained from the bioconversion of ARA by recombinant Escherichia coli cells containing Archangium violaceum 15-LOX without and with Myxococcus xanthus EH were identified as 14,15-HXB3 and 13,14,15-TrXB3, respectively. Under the optimal conditions of 30 g cells L-1, 200 mM ARA, 25 °C, and initial pH 7.5, the cells converted 200 mM ARA into 192 mM 14,15-HXB3 and 100 mM 13,14,15-TrXB3 for 150 min, with conversion yields of 96 and 51% and productivities of 77 and 40 mM h-1, respectively.
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s10529-020-02932-y) contains supplementary material, which is available to authorized users. J. Lee T.-H. Kim D.-K. Oh (&) Department of Bioscience and Biotechnology, Konkuk University, 120 Neungdong-ro, Gwangjin-gu, Seoul 05029, Republic of Korea e-mail: [email protected]
Conclusion These are the highest concentrations, productivities, and yields of hepoxilin and trioxilin from ARA reported thus far. Keywords Archangium violaceum 15lipoxygenase Epoxide hydrolase 14,15-hepoxilin B3 13,14,15-trioxilin B3
Introduction Lipid mediators (LMs) such as leukotrienes, hepoxilins (HXs), lipoxins, protectins, resolvins, and trioxilins (TrXs) are endogenous essential oxylipins in humans and are lipoxygenase (LOX)-derived products produced from polyunsaturated fatty acids (PUFAs) (Arita 2012). HXs and TrXs at trace amounts are involved in human physiological functions such as insulin secretion regulation, calcium regulation, cell volume regulation, and neutrophil stimulation (Anton et al. 1998; Arita 2012; Dho et al. 1990). LOXs catalyze the oxidation and epoxidation of PUFAs with one or more cis,cis-1.4-pentadienes into hydroperoxy fatty acids (HpFAs) that are converted to hydroxy fatty acids (HFAs) by reduction (Hansen et al. 2013). They also catalyze the epoxidation of HpFAs to hydroxy epoxide and epoxide fatty acids such as HXs. Depending on the carbon position of the hydroxyl group on arachidonic acid (ARA), LOXs are classified
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as 5-, 8-, 11-, 12-, and 15-LOX and have been found in various organisms (Berger et al. 1998; Brodhun et al. 2013; Joo and Oh 2012; Lee et al. 2019; Lu et al. 2013). PUFAs are converted into HXs by oxidation and epoxidation via 12-LOXs and 15-LOXs, and the formed HXs are converted
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