{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,27]],"date-time":"2026-09-27T02:36:19Z","timestamp":1790476579419,"version":"4.1.0"},"reference-count":83,"publisher":"Wiley","issue":"20","license":[{"start":{"date-parts":[[2020,3,17]],"date-time":"2020-03-17T00:00:00Z","timestamp":1584403200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"},{"start":{"date-parts":[[2020,3,17]],"date-time":"2020-03-17T00:00:00Z","timestamp":1584403200000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"funder":[{"DOI":"10.13039\/100000002","name":"National Institutes of Health","doi-asserted-by":"publisher","award":["R00-GM097096"],"award-info":[{"award-number":["R00-GM097096"]}],"id":[{"id":"10.13039\/100000002","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000002","name":"National Institutes of Health","doi-asserted-by":"publisher","award":["1DP2-CA186575"],"award-info":[{"award-number":["1DP2-CA186575"]}],"id":[{"id":"10.13039\/100000002","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000002","name":"National Institutes of Health","doi-asserted-by":"publisher","award":["5T32GM06754 3-12"],"award-info":[{"award-number":["5T32GM06754 3-12"]}],"id":[{"id":"10.13039\/100000002","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000861","name":"Burroughs Wellcome Fund","doi-asserted-by":"publisher","award":["1016720"],"award-info":[{"award-number":["1016720"]}],"id":[{"id":"10.13039\/100000861","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100001082","name":"Camille and Henry Dreyfus Foundation","doi-asserted-by":"publisher","award":["TC-17-011"],"award-info":[{"award-number":["TC-17-011"]}],"id":[{"id":"10.13039\/100001082","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000011","name":"Howard Hughes Medical Institute","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100000011","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2020,5,11]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    Tapinarof is a stilbene drug that is used to treat psoriasis and atopic dermatitis, and is thought to function through regulation of the AhR and Nrf2 signaling pathways, which have also been linked to inflammatory bowel diseases. It is produced by the gammaproteobacterial\n                    <jats:italic>Photorhabdus<\/jats:italic>\n                    genus, which thus represents a model to probe tapinarof structural and functional transformations. We show that\n                    <jats:italic>Photorhabdus<\/jats:italic>\n                    transforms tapinarof into novel drug metabolism products that kill inflammatory bacteria, and that a cupin enzyme contributes to the conversion of tapinarof and related dietary stilbenes into novel dimers. One dimer has activity against methicillin\u2010resistant\n                    <jats:italic>Staphylococcus aureus<\/jats:italic>\n                    (MRSA) and vancomycin\u2010resistant\n                    <jats:italic>Enterococcus faecalis<\/jats:italic>\n                    (VRE), and another undergoes spontaneous cyclizations to a cyclopropane\u2010bridge\u2010containing hexacyclic framework that exhibits activity against\n                    <jats:italic>Mycobacterium<\/jats:italic>\n                    . These dimers lack efficacy in a colitis mouse model, whereas the monomer reduces disease symptoms.\n                  <\/jats:p>","DOI":"10.1002\/anie.201916204","type":"journal-article","created":{"date-parts":[[2020,2,25]],"date-time":"2020-02-25T15:05:16Z","timestamp":1582643116000},"page":"7871-7880","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":26,"title":["Bacterial Autoimmune Drug Metabolism Transforms an Immunomodulator into Structurally and Functionally Divergent Antibiotics"],"prefix":"10.1002","volume":"59","author":[{"given":"Hyun Bong","family":"Park","sequence":"first","affiliation":[{"name":"Department of Chemistry Yale University  New Haven CT 06520 USA"},{"name":"Chemical Biology Institute Yale University  West Haven CT 06516 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tyler N.","family":"Goddard","sequence":"additional","affiliation":[{"name":"Department of Chemistry Yale University  New Haven CT 06520 USA"},{"name":"Chemical Biology Institute Yale University  West Haven CT 06516 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Joonseok","family":"Oh","sequence":"additional","affiliation":[{"name":"Department of Chemistry Yale University  New Haven CT 06520 USA"},{"name":"Chemical Biology Institute Yale University  West Haven CT 06516 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jaymin","family":"Patel","sequence":"additional","affiliation":[{"name":"Chemical Biology Institute Yale University  West Haven CT 06516 USA"},{"name":"Department of Molecular, Cellular, and Developmental Biology Yale University  New Haven CT 06520 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zheng","family":"Wei","sequence":"additional","affiliation":[{"name":"Chemical Biology Institute Yale University  West Haven CT 06516 USA"},{"name":"Department of Immunobiology Yale University School of Medicine  New Haven CT 06520 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Corey E.","family":"Perez","sequence":"additional","affiliation":[{"name":"Department of Chemistry Yale University  New Haven CT 06520 USA"},{"name":"Chemical Biology Institute Yale University  West Haven CT 06516 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Brandon Q.","family":"Mercado","sequence":"additional","affiliation":[{"name":"Department of Chemistry Yale University  New Haven CT 06520 USA"},{"name":"Chemical and Biophysical Instrumentation Center Yale University  New Haven CT 06520 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Rurun","family":"Wang","sequence":"additional","affiliation":[{"name":"Exploratory Science Center Merck &amp; Co., Inc.  Cambridge MA USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Thomas P.","family":"Wyche","sequence":"additional","affiliation":[{"name":"Exploratory Science Center Merck &amp; Co., Inc.  Cambridge MA USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Grazia","family":"Piizzi","sequence":"additional","affiliation":[{"name":"Exploratory Science Center Merck &amp; Co., Inc.  Cambridge MA USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Richard A.","family":"Flavell","sequence":"additional","affiliation":[{"name":"Department of Immunobiology Yale University School of Medicine  New Haven CT 06520 USA"},{"name":"Howard Hughes Medical Institute Yale University School of Medicine  New Haven CT 06520 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7583-1242","authenticated-orcid":false,"given":"Jason M.","family":"Crawford","sequence":"additional","affiliation":[{"name":"Department of Chemistry Yale University  New Haven CT 06520 USA"},{"name":"Chemical Biology Institute Yale University  West Haven CT 06516 USA"},{"name":"Department of Microbial Pathogenesis Yale School of Medicine  New Haven CT 06536 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2020,3,17]]},"reference":[{"key":"e_1_2_6_1_1","unstructured":"\u00a0"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1038\/nrendo.2013.161"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1038\/nrdp.2016.82"},{"key":"e_1_2_6_4_1","unstructured":"\u00a0"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1056\/NEJMra1505557"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1001\/jamadermatol.2018.3631"},{"key":"e_1_2_6_7_1","unstructured":"\u00a0"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1038\/nri1689"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1111\/exd.13336"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1146\/annurev-immunol-032713-120225"},{"key":"e_1_2_6_11_1","doi-asserted-by":"publisher","DOI":"10.1046\/j.1365-2672.2000.01017.x"},{"key":"e_1_2_6_12_1","doi-asserted-by":"publisher","DOI":"10.3390\/ijms20215424"},{"key":"e_1_2_6_13_1","unstructured":"\u00a0"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1468-3083.2011.04332.x"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1001\/archdermatol.2010.34"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1365-2133.2011.10775.x"},{"key":"e_1_2_6_17_1","unstructured":"\u00a0"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.1007\/BF00987707"},{"key":"e_1_2_6_19_2","doi-asserted-by":"publisher","DOI":"10.1128\/AEM.54.6.1602-1605.1988"},{"key":"e_1_2_6_20_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jid.2017.05.004"},{"key":"e_1_2_6_21_1","doi-asserted-by":"publisher","DOI":"10.1146\/annurev.pharmtox.43.100901.135828"},{"key":"e_1_2_6_22_1","unstructured":"\u00a0"},{"key":"e_1_2_6_23_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.immuni.2014.04.019"},{"key":"e_1_2_6_24_2","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.R116.767723"},{"key":"e_1_2_6_25_1","doi-asserted-by":"publisher","DOI":"10.1128\/MCB.26.1.221-229.2006"},{"key":"e_1_2_6_26_1","doi-asserted-by":"publisher","DOI":"10.1002\/cbic.200800840"},{"key":"e_1_2_6_27_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5FO00202H"},{"key":"e_1_2_6_28_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41698-017-0038-6"},{"key":"e_1_2_6_29_1","doi-asserted-by":"publisher","DOI":"10.1093\/ajcn\/81.1.268S"},{"key":"e_1_2_6_30_1","doi-asserted-by":"publisher","DOI":"10.1039\/b905960a"},{"key":"e_1_2_6_31_1","unstructured":"\u00a0"},{"key":"e_1_2_6_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/cb100117k"},{"key":"e_1_2_6_33_2","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.M116.762542"},{"key":"e_1_2_6_34_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jafc.6b04303"},{"key":"e_1_2_6_35_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7NP00054E"},{"key":"e_1_2_6_36_1","unstructured":"\u00a0"},{"key":"e_1_2_6_37_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201210116"},{"key":"e_1_2_6_37_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201210116"},{"key":"e_1_2_6_38_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200705148"},{"key":"e_1_2_6_38_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200705148"},{"key":"e_1_2_6_39_2","doi-asserted-by":"publisher","DOI":"10.1099\/mic.0.28136-0"},{"key":"e_1_2_6_40_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.chembiol.2016.10.010"},{"key":"e_1_2_6_41_1","unstructured":"\u00a0"},{"key":"e_1_2_6_42_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1462-5822.2008.01209.x"},{"key":"e_1_2_6_43_2","doi-asserted-by":"publisher","DOI":"10.1146\/annurev.micro.091208.073507"},{"key":"e_1_2_6_44_1","unstructured":"\u00a0"},{"key":"e_1_2_6_45_2","doi-asserted-by":"publisher","DOI":"10.1128\/JCM.37.11.3647-3653.1999"},{"key":"e_1_2_6_46_2","doi-asserted-by":"publisher","DOI":"10.1128\/JCM.43.8.4152-4155.2005"},{"key":"e_1_2_6_47_1","unstructured":"\u00a0"},{"key":"e_1_2_6_48_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.micinf.2003.10.018"},{"key":"e_1_2_6_49_2","doi-asserted-by":"publisher","DOI":"10.3201\/eid0902.020222"},{"key":"e_1_2_6_50_1","first-page":"159","volume-title":"The Molecular Biology of Photorhabdus Bacteria","author":"Hapeshi A.","year":"2017"},{"key":"e_1_2_6_51_1","unstructured":"\u00a0"},{"key":"e_1_2_6_52_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1365-2958.2010.07270.x"},{"key":"e_1_2_6_53_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1216641"},{"key":"e_1_2_6_54_2","doi-asserted-by":"publisher","DOI":"10.1007\/s10295-013-1356-5"},{"key":"e_1_2_6_55_1","doi-asserted-by":"publisher","DOI":"10.1021\/np500974f"},{"key":"e_1_2_6_56_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2006.01.025"},{"key":"e_1_2_6_57_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.0610525104"},{"key":"e_1_2_6_58_1","unstructured":"\u00a0"},{"key":"e_1_2_6_59_2","doi-asserted-by":"publisher","DOI":"10.1146\/annurev.arplant.55.031903.141701"},{"key":"e_1_2_6_60_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.febslet.2006.06.006"},{"key":"e_1_2_6_61_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.chom.2016.07.009"},{"key":"e_1_2_6_62_1","unstructured":"\u00a0"},{"key":"e_1_2_6_63_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.cub.2009.10.059"},{"key":"e_1_2_6_64_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jmb.2019.04.042"},{"key":"e_1_2_6_65_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo500333u"},{"key":"e_1_2_6_66_1","unstructured":"\u00a0"},{"key":"e_1_2_6_67_2","doi-asserted-by":"publisher","DOI":"10.1002\/1099-0690(200209)2002:18<3162::AID-EJOC3162>3.0.CO;2-H"},{"key":"e_1_2_6_68_2","doi-asserted-by":"publisher","DOI":"10.1002\/1099-0690(200109)2001:17<3307::AID-EJOC3307>3.0.CO;2-T"},{"key":"e_1_2_6_69_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jmr.2006.06.009"},{"key":"e_1_2_6_70_1","unstructured":"\u00a0"},{"key":"e_1_2_6_71_2","doi-asserted-by":"publisher","DOI":"10.1128\/AEM.61.3.907-912.1995"},{"key":"e_1_2_6_72_2","doi-asserted-by":"publisher","DOI":"10.1002\/biof.108"},{"key":"e_1_2_6_73_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(97)10622-0"},{"key":"e_1_2_6_74_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.phytochem.2003.08.016"},{"key":"e_1_2_6_75_1","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.M500190200"},{"key":"e_1_2_6_76_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b07588"},{"key":"e_1_2_6_77_1","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.2336"},{"key":"e_1_2_6_78_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.mib.2017.12.002"},{"key":"e_1_2_6_79_1","unstructured":"\u00a0"},{"key":"e_1_2_6_80_2","doi-asserted-by":"publisher","DOI":"10.1038\/srep26585"},{"key":"e_1_2_6_81_2","first-page":"868","volume":"41","author":"Wang Q.","year":"2018","journal-title":"Int. J. Mol. Med."}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fanie.201916204","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.201916204","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.201916204","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.201916204","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,5,1]],"date-time":"2026-05-01T12:03:22Z","timestamp":1777637002000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.201916204"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,3,17]]},"references-count":83,"journal-issue":{"issue":"20","published-print":{"date-parts":[[2020,5,11]]}},"alternative-id":["10.1002\/anie.201916204"],"URL":"https:\/\/doi.org\/10.1002\/anie.201916204","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2020,3,17]]},"assertion":[{"value":"2019-12-20","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2020-03-17","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}