{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,26]],"date-time":"2026-09-26T01:59:29Z","timestamp":1790387969199,"version":"4.1.0"},"reference-count":35,"publisher":"Wiley","license":[{"start":{"date-parts":[[2026,9,25]],"date-time":"2026-09-25T00:00:00Z","timestamp":1790294400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"},{"start":{"date-parts":[[2026,9,25]],"date-time":"2026-09-25T00:00:00Z","timestamp":1790294400000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"funder":[{"DOI":"10.13039\/501100004359","name":"Vetenskapsr\u00e5det","doi-asserted-by":"publisher","award":["2022\u201000796"],"award-info":[{"award-number":["2022\u201000796"]}],"id":[{"id":"10.13039\/501100004359","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["aocs.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Lipids"],"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:p>\n                    Gut bacteria can convert dietary fatty acids into oxygenated metabolites called oxylipins, which can exert potent lipid mediator functions. The oxylipins derived from C\u201018 fatty acids are termed octadecanoids and associate with multiple disorders including allergy and metabolic dysregulation. This study presents the synthesis of 17 octadecanoids possessing a hydroxy group (\n                    <jats:italic>n<\/jats:italic>\n                    \u2009=\u20099) or a ketone (\n                    <jats:italic>n<\/jats:italic>\n                    \u2009=\u20098) on the 10\u2010 or 13\u2010positions. The products of these two series were prepared for the linoleic acid (LA), \u03b1\u2010linolenic acid (ALA) and \u03b3\u2010linolenic acid (GLA) pathways. The synthetic strategies provided 17 putative microbial metabolites of C\u201018 polyunsaturated fatty acids (PUFAs) with high purities, in 5\u201313 steps and overall yields from 1.5%\u201337%. To study the biological formation of these compounds, the parent PUFAs (LA, ALA, GLA) were fed to cultures of\n                    <jats:styled-content style=\"fixed-case\">\n                      <jats:italic>Enterococcus faecalis<\/jats:italic>\n                    <\/jats:styled-content>\n                    U150 and\n                    <jats:styled-content style=\"fixed-case\">\n                      <jats:italic>Lactobacillus acidophilus<\/jats:italic>\n                    <\/jats:styled-content>\n                    CCUG 5917, and the octadecanoid products were measured by chiral supercritical fluid chromatography coupled to tandem mass spectrometry (SFC\u2010MS\/MS). The compounds containing a hydroxy group on the 10\u2010 or 13\u2010position are racemic, forming 9 enantiomeric pairs. Accordingly, of the 17 compounds synthesized, 9 were chiral and 8 were achiral resulting in 26 compounds. An additional 7 commercial bacteria\u2010derived octadecanoids were measured to provide a screen of 33 compounds. Generally, PUFA supplementation resulted in selective formation of the associated octadecanoids. Of the 33 studied compounds, 16 were observed to be formed by\n                    <jats:styled-content style=\"fixed-case\">\n                      <jats:italic>E. faecalis<\/jats:italic>\n                    <\/jats:styled-content>\n                    and 13 by\n                    <jats:styled-content style=\"fixed-case\">\n                      <jats:italic>L. acidophilus<\/jats:italic>\n                    <\/jats:styled-content>\n                    . These findings demonstrate the bacteria species\u2010specific formation of octadecanoids, which may have ramifications for associated biological response in the host.\n                  <\/jats:p>","DOI":"10.1002\/lipd.70067","type":"journal-article","created":{"date-parts":[[2026,9,26]],"date-time":"2026-09-26T01:21:08Z","timestamp":1790385668000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Synthesis of Microbial\u2010Derived Octadecanoids"],"prefix":"10.1002","author":[{"given":"Johanna","family":"Revol\u2010Cavalier","sequence":"first","affiliation":[{"name":"Unit of Integrative Metabolomics Institute of Environmental Medicine, Karolinska Institute  Stockholm Sweden"},{"name":"Larodan Research Laboratory Karolinska Institutet  Stockholm Sweden"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Katar\u00edna","family":"Bank\u00f3ov\u00e1","sequence":"additional","affiliation":[{"name":"Centre for Translational Microbiome Research (CTMR), Department of Microbiology, Tumor and Cell Biology Karolinska Institute  Stockholm Sweden"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0388-1352","authenticated-orcid":false,"given":"Olivier","family":"Salamin","sequence":"additional","affiliation":[{"name":"Unit of Integrative Metabolomics Institute of Environmental Medicine, Karolinska Institute  Stockholm Sweden"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alessandro","family":"Quaranta","sequence":"additional","affiliation":[{"name":"Unit of Integrative Metabolomics Institute of Environmental Medicine, Karolinska Institute  Stockholm Sweden"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Juan","family":"Du","sequence":"additional","affiliation":[{"name":"Centre for Translational Microbiome Research (CTMR), Department of Microbiology, Tumor and Cell Biology Karolinska Institute  Stockholm Sweden"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8910-7810","authenticated-orcid":false,"given":"Mats","family":"Hamberg","sequence":"additional","affiliation":[{"name":"Unit of Integrative Metabolomics Institute of Environmental Medicine, Karolinska Institute  Stockholm Sweden"},{"name":"Larodan Research Laboratory Karolinska Institutet  Stockholm Sweden"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8113-0653","authenticated-orcid":false,"given":"Craig E.","family":"Wheelock","sequence":"additional","affiliation":[{"name":"Unit of Integrative Metabolomics Institute of Environmental Medicine, Karolinska Institute  Stockholm Sweden"},{"name":"Department of Respiratory Medicine and Allergy Karolinska University Hospital  Stockholm Sweden"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,9,25]]},"reference":[{"key":"e_1_2_10_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.2c00431"},{"key":"e_1_2_10_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.0c02726"},{"key":"e_1_2_10_4_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.2120691119"},{"key":"e_1_2_10_5_1","unstructured":"Bioquest A.2023.\u201cPotassium Phosphate (pH 5.8 to 8.0) Preparation and Recipe | AAT Bioquest.\u201dhttps:\/\/www.aatbio.com\/resources\/buffer\u2010preparations\u2010and\u2010recipes\/potassium\u2010phosphate\u2010ph\u20105\u20108\u2010to\u20108\u20100."},{"key":"e_1_2_10_6_1","doi-asserted-by":"publisher","DOI":"10.1038\/nrmicro.2016.142"},{"key":"e_1_2_10_7_1","doi-asserted-by":"publisher","DOI":"10.3389\/fimmu.2022.840245"},{"key":"e_1_2_10_8_1","unstructured":"Diazald and Diazomethane Generators.Sigma\u2010Aldrich. Technical Bulletin."},{"key":"e_1_2_10_9_1","doi-asserted-by":"publisher","DOI":"10.1136\/gut.2006.093484"},{"key":"e_1_2_10_10_1","doi-asserted-by":"publisher","DOI":"10.1039\/d3fo05288e"},{"key":"e_1_2_10_11_1","doi-asserted-by":"publisher","DOI":"10.1038\/nm.4176"},{"key":"e_1_2_10_12_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bbrc.2015.02.154"},{"key":"e_1_2_10_13_1","doi-asserted-by":"publisher","DOI":"10.1002\/mnfr.201800146"},{"key":"e_1_2_10_14_1","doi-asserted-by":"publisher","DOI":"10.1194\/jlr.M059444"},{"key":"e_1_2_10_15_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41392\u2010022\u201000974\u20104"},{"key":"e_1_2_10_16_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1574\u20106968.1998.tb13329.x"},{"key":"e_1_2_10_17_1","doi-asserted-by":"publisher","DOI":"10.1038\/nrcardio.2016.183"},{"key":"e_1_2_10_18_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11745\u2010003\u20101188\u20104"},{"key":"e_1_2_10_19_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00253\u2010009\u20101949\u20100"},{"key":"e_1_2_10_20_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.1312937110"},{"key":"e_1_2_10_21_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41579\u2010020\u20100438\u20104"},{"key":"e_1_2_10_22_1","doi-asserted-by":"publisher","DOI":"10.1038\/srep31649"},{"key":"e_1_2_10_23_1","doi-asserted-by":"publisher","DOI":"10.1055\/s\u20101993\u201025795"},{"key":"e_1_2_10_24_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41564\u2010019\u20100498\u20102"},{"key":"e_1_2_10_25_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41564\u2010026\u201002321\u20107"},{"key":"e_1_2_10_26_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467\u2010019\u201011978\u20100"},{"key":"e_1_2_10_27_1","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.M114.610733"},{"key":"e_1_2_10_28_1","doi-asserted-by":"publisher","DOI":"10.1096\/fj.201700273R"},{"key":"e_1_2_10_29_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41579\u2010024\u201001048\u20108"},{"key":"e_1_2_10_30_1","doi-asserted-by":"publisher","DOI":"10.1128\/jb.88.4.1056\u20101064.1964"},{"key":"e_1_2_10_31_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.analchem.2c02601"},{"key":"e_1_2_10_32_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.3c00520"},{"key":"e_1_2_10_33_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.micpath.2025.107381"},{"key":"e_1_2_10_34_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.plipres.2022.101209"},{"key":"e_1_2_10_35_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040\u20104039(98)00987\u20103"},{"key":"e_1_2_10_36_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bbalip.2018.03.012"}],"container-title":["Lipids"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/aocs.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/lipd.70067","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/aocs.onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/lipd.70067","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/aocs.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/lipd.70067","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,26]],"date-time":"2026-09-26T01:21:10Z","timestamp":1790385670000},"score":1,"resource":{"primary":{"URL":"https:\/\/aocs.onlinelibrary.wiley.com\/doi\/10.1002\/lipd.70067"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,9,25]]},"references-count":35,"alternative-id":["10.1002\/lipd.70067"],"URL":"https:\/\/doi.org\/10.1002\/lipd.70067","archive":["Portico"],"relation":{},"ISSN":["0024-4201","1558-9307"],"issn-type":[{"value":"0024-4201","type":"print"},{"value":"1558-9307","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,9,25]]},"assertion":[{"value":"2026-01-30","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-06-03","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-09-25","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"lipd.70067"}}