{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,23]],"date-time":"2026-10-23T02:51:44Z","timestamp":1792723904706,"version":"4.5.0"},"reference-count":50,"publisher":"Wiley","issue":"68","license":[{"start":{"date-parts":[[2020,11,3]],"date-time":"2020-11-03T00:00:00Z","timestamp":1604361600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100002347","name":"Bundesministerium f\u00fcr Bildung und Forschung","doi-asserted-by":"publisher","award":["InfectControl"],"award-info":[{"award-number":["InfectControl"]}],"id":[{"id":"10.13039\/501100002347","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","award":["Leibniz Award"],"award-info":[{"award-number":["Leibniz Award"]}],"id":[{"id":"10.13039\/501100001659","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2020,12,4]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The anaerobe <jats:italic>Clostridium acetobutylicum<\/jats:italic> belongs to the most important industrially used bacteria. Whereas genome mining points to a high potential for secondary metabolism in <jats:italic>C. acetobutylicum<\/jats:italic>, the functions of most biosynthetic gene clusters are cryptic. We report that the addition of supra\u2010physiological concentrations of cysteine triggered the formation of a novel natural product, clostrisulfone (<jats:bold>1<\/jats:bold>). Its structure was fully elucidated by NMR, MS and the chemical synthesis of a reference compound. Clostrisulfone is the first reported natural product with a diphenylsulfone scaffold. A biomimetic synthesis suggests that pentamethylchromanol\u2010derived radicals capture sulfur dioxide to form <jats:bold>1<\/jats:bold>. In a cell\u2010based assay using murine macrophages a biphasic and dose\u2010dependent regulation of the LPS\u2010induced release of nitric oxide was observed in the presence of <jats:bold>1<\/jats:bold>.<\/jats:p>","DOI":"10.1002\/chem.202003500","type":"journal-article","created":{"date-parts":[[2020,9,30]],"date-time":"2020-09-30T08:25:39Z","timestamp":1601454339000},"page":"15855-15858","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":6,"title":["Induced Production, Synthesis, and Immunomodulatory Action of Clostrisulfone, a Diarylsulfone from <i>Clostridium acetobutylicum<\/i>"],"prefix":"10.1002","volume":"26","author":[{"given":"Toni","family":"Neuwirth","sequence":"first","affiliation":[{"name":"Department of Biomolecular Chemistry Leibniz Institute for Natural Product Chemistry and Infection Biology (HKI)  Beutenbergstr. 11a 07745 Jena Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Anne\u2010Catrin","family":"Letzel","sequence":"additional","affiliation":[{"name":"Department of Biomolecular Chemistry Leibniz Institute for Natural Product Chemistry and Infection Biology (HKI)  Beutenbergstr. 11a 07745 Jena Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Cedric","family":"Tank","sequence":"additional","affiliation":[{"name":"BioPilotPlant Leibniz Institute for Natural Product Chemistry and Infection Biology (HKI)  Beutenbergstr. 11a 07745 Jena Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Keishi","family":"Ishida","sequence":"additional","affiliation":[{"name":"Department of Biomolecular Chemistry Leibniz Institute for Natural Product Chemistry and Infection Biology (HKI)  Beutenbergstr. 11a 07745 Jena Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Michael","family":"Cyrulies","sequence":"additional","affiliation":[{"name":"BioPilotPlant Leibniz Institute for Natural Product Chemistry and Infection Biology (HKI)  Beutenbergstr. 11a 07745 Jena Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lisa","family":"Schm\u00f6lz","sequence":"additional","affiliation":[{"name":"Institute of Nutritional Sciences Friedrich Schiller University Jena  Dornburger Stra\u00dfe 25 07743 Jena Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Stefan","family":"Lorkowski","sequence":"additional","affiliation":[{"name":"Institute of Nutritional Sciences Friedrich Schiller University Jena  Dornburger Stra\u00dfe 25 07743 Jena Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0367-337X","authenticated-orcid":false,"given":"Christian","family":"Hertweck","sequence":"additional","affiliation":[{"name":"Department of Biomolecular Chemistry Leibniz Institute for Natural Product Chemistry and Infection Biology (HKI)  Beutenbergstr. 11a 07745 Jena Germany"},{"name":"Faculty of Biological Sciences Friedrich Schiller University Jena  07743 Jena Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2020,11,3]]},"reference":[{"key":"e_1_2_2_1_1","doi-asserted-by":"publisher","DOI":"10.1002\/3527600108"},{"key":"e_1_2_2_2_1","doi-asserted-by":"publisher","DOI":"10.1128\/mr.50.4.484-524.1986"},{"key":"e_1_2_2_3_1","unstructured":"\u00a0"},{"key":"e_1_2_2_4_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200906114"},{"key":"e_1_2_2_4_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200906114"},{"key":"e_1_2_2_5_2","doi-asserted-by":"publisher","DOI":"10.1007\/s00253-012-4285-8"},{"key":"e_1_2_2_6_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ijmm.2013.08.011"},{"key":"e_1_2_2_7_2","doi-asserted-by":"publisher","DOI":"10.1007\/s10295-018-2086-5"},{"key":"e_1_2_2_8_1","unstructured":"\u00a0"},{"key":"e_1_2_2_9_2","doi-asserted-by":"publisher","DOI":"10.1039\/C2NP20103H"},{"key":"e_1_2_2_10_2","doi-asserted-by":"publisher","DOI":"10.1186\/1471-2164-15-983"},{"key":"e_1_2_2_11_1","unstructured":"\u00a0"},{"key":"e_1_2_2_12_2","doi-asserted-by":"publisher","DOI":"10.1039\/b821578b"},{"key":"e_1_2_2_13_2","doi-asserted-by":"publisher","DOI":"10.1371\/journal.pone.0029609"},{"key":"e_1_2_2_14_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.synbio.2018.09.001"},{"key":"e_1_2_2_15_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.mib.2019.03.003"},{"key":"e_1_2_2_16_1","unstructured":"\u00a0"},{"key":"e_1_2_2_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201108214"},{"key":"e_1_2_2_17_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201108214"},{"key":"e_1_2_2_18_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201807970"},{"key":"e_1_2_2_18_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201807970"},{"key":"e_1_2_2_19_1","unstructured":"\u00a0"},{"key":"e_1_2_2_20_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201403836"},{"key":"e_1_2_2_21_2","doi-asserted-by":"publisher","DOI":"10.1093\/jac\/dkv161"},{"key":"e_1_2_2_22_1","unstructured":"\u00a0"},{"key":"e_1_2_2_23_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201402632"},{"key":"e_1_2_2_23_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201402632"},{"key":"e_1_2_2_24_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.aac9990"},{"key":"e_1_2_2_25_1","doi-asserted-by":"publisher","DOI":"10.1039\/C9OB00968J"},{"key":"e_1_2_2_26_1","doi-asserted-by":"publisher","DOI":"10.1021\/acschembio.9b00228"},{"key":"e_1_2_2_27_1","doi-asserted-by":"publisher","DOI":"10.1007\/s10295-020-02266-8"},{"key":"e_1_2_2_28_1","doi-asserted-by":"publisher","DOI":"10.1128\/JB.183.16.4823-4838.2001"},{"key":"e_1_2_2_29_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-017-01809-5"},{"key":"e_1_2_2_30_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)86564-9"},{"key":"e_1_2_2_31_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201506541"},{"key":"e_1_2_2_31_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201506541"},{"key":"e_1_2_2_32_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9258(18)89536-9"},{"key":"e_1_2_2_33_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.6b00697"},{"key":"e_1_2_2_34_1","unstructured":"\u00a0"},{"key":"e_1_2_2_35_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7SC01182B"},{"key":"e_1_2_2_36_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201303733"},{"key":"e_1_2_2_36_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201303733"},{"key":"e_1_2_2_37_1","doi-asserted-by":"publisher","DOI":"10.1128\/AEM.39.6.1096-1099.1980"},{"key":"e_1_2_2_38_1","unstructured":"\u00a0"},{"key":"e_1_2_2_39_2","doi-asserted-by":"publisher","DOI":"10.1186\/1471-2180-10-234"},{"key":"e_1_2_2_40_2","doi-asserted-by":"publisher","DOI":"10.1128\/IAI.00121-16"},{"key":"e_1_2_2_41_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.micres.2018.07.003"},{"key":"e_1_2_2_42_1","doi-asserted-by":"publisher","DOI":"10.1128\/AAC.37.4.754"},{"key":"e_1_2_2_43_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-2005-864107"},{"key":"e_1_2_2_44_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jim.2017.06.012"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202003500","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/chem.202003500","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202003500","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T19:57:28Z","timestamp":1760299048000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.202003500"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,11,3]]},"references-count":50,"journal-issue":{"issue":"68","published-print":{"date-parts":[[2020,12,4]]}},"alternative-id":["10.1002\/chem.202003500"],"URL":"https:\/\/doi.org\/10.1002\/chem.202003500","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2020,11,3]]},"assertion":[{"value":"2020-07-27","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2020-11-03","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}