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eicosapentaenoic acid and docosahexaenoic acid is beneficial for health control. We recently identified 17,18\u2010epoxyeicosatetraenoic acid (17,18\u2010EpETE) as a lipid metabolite endogenously generated from eicosapentaenoic acid that exhibits potent anti\u2010allergic and anti\u2010inflammatory properties. However, chemically synthesized 17,18\u2010EpETE is enantiomeric due to its epoxy group\u201417(\n                    <jats:italic>S<\/jats:italic>\n                    ),18(\n                    <jats:italic>R<\/jats:italic>\n                    )\u2010EpETE and 17(\n                    <jats:italic>R<\/jats:italic>\n                    ),18(\n                    <jats:italic>S<\/jats:italic>\n                    )\u2010EpETE. In this study, we demonstrated stereoselective differences of 17(\n                    <jats:italic>S<\/jats:italic>\n                    ),18(\n                    <jats:italic>R<\/jats:italic>\n                    )\u2010EpETE and 17(\n                    <jats:italic>R<\/jats:italic>\n                    ),18(\n                    <jats:italic>S<\/jats:italic>\n                    )\u2010EpETE in amelioration of skin contact hypersensitivity and found that anti\u2010inflammatory activity was detected in 17(\n                    <jats:italic>S<\/jats:italic>\n                    ),18(\n                    <jats:italic>R<\/jats:italic>\n                    )\u2010EpETE, but not in 17(\n                    <jats:italic>R<\/jats:italic>\n                    ),18(\n                    <jats:italic>S<\/jats:italic>\n                    )\u2010EpETE. In addition, we found that cytochrome P450 BM\u20103 derived from\n                    <jats:italic>Bacillus megaterium<\/jats:italic>\n                    stereoselectively converts EPA into 17(\n                    <jats:italic>S<\/jats:italic>\n                    ),18(\n                    <jats:italic>R<\/jats:italic>\n                    )\u2010EpETE, which effectively inhibited the development of skin contact hypersensitivity by inhibiting neutrophil migration in a G protein\u2010coupled receptor 40\u2010dependent manner. These results suggest the new availability of a bacterial enzyme to produce a beneficial lipid mediator, 17(\n                    <jats:italic>S<\/jats:italic>\n                    ),18(\n                    <jats:italic>R<\/jats:italic>\n                    )\u2010EpETE, in a stereoselective manner. Our findings highlight that bacterial enzymatic conversion of fatty acid is a promising strategy for mass production of bioactive lipid metabolites.\n                  <\/jats:p>","DOI":"10.1096\/fba.2019-00061","type":"journal-article","created":{"date-parts":[[2019,12,12]],"date-time":"2019-12-12T01:51:20Z","timestamp":1576115480000},"page":"59-71","source":"Crossref","is-referenced-by-count":18,"title":["17(\n                    <i>S<\/i>\n                    ),18(\n                    <i>R<\/i>\n                    )\u2010epoxyeicosatetraenoic acid generated by cytochrome P450 BM\u20103 from\n                    <i>Bacillus megaterium<\/i>\n                    inhibits the development of contact hypersensitivity via G\u2010protein\u2010coupled receptor 40\u2010mediated neutrophil suppression"],"prefix":"10.1096","volume":"2","author":[{"given":"Azusa","family":"Saika","sequence":"first","affiliation":[{"name":"Laboratory of Vaccine Materials Center for Vaccine and Adjuvant Research 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