{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,2,1]],"date-time":"2026-02-01T13:42:39Z","timestamp":1769953359771,"version":"3.49.0"},"reference-count":31,"publisher":"Oxford University Press (OUP)","issue":"1","license":[{"start":{"date-parts":[[2023,12,14]],"date-time":"2023-12-14T00:00:00Z","timestamp":1702512000000},"content-version":"vor","delay-in-days":347,"URL":"https:\/\/creativecommons.org\/licenses\/by-nc-nd\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100003725","name":"National Research Foundation of Korea","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100003725","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100014188","name":"Ministry of Science and ICT, South Korea","doi-asserted-by":"publisher","award":["2021R1A4A2001251"],"award-info":[{"award-number":["2021R1A4A2001251"]}],"id":[{"id":"10.13039\/501100014188","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003710","name":"Korea Health Industry Development Institute","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100003710","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100008903","name":"Ministry of Health and Welfare","doi-asserted-by":"publisher","award":["HI22C1361"],"award-info":[{"award-number":["HI22C1361"]}],"id":[{"id":"10.13039\/100008903","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2023,2,17]]},"abstract":"<jats:title>Abstract<\/jats:title>\n               <jats:sec>\n                  <jats:title>\u00a0<\/jats:title>\n                  <jats:p>Two new macrocyclic secondary metabolites, glycosyl-migrastatin (1) and 5-hydroxy-migrastatin (2), were isolated from a gut bacterium Kitasatospora sp. JL24 in dung beetle Onthophagus lenzii. Based on a comprehensive analysis of the nuclear magnetic resonance (NMR), MS, and UV spectroscopic data, the planar structures of 1 and 2 were successfully identified as new derivatives of migrastatin. Compound 1 was the first glycosylated member of the migrastatin family. The absolute configuration of the sugar moiety was determined to be d-glucose through the analysis of coupling constants and ROESY correlations, followed by chemical derivatization and chromatographic comparison with authentic d- and l-glucose. Compound 2, identified as 5-hydroxy-migrastatin possessing an additional hydroxy group with a previously unreported chiral center, was assigned using Mosher's method through 19F NMR chemical shifts and confirmed with the modified Mosher's method. Genomic analysis of Kitasatospora sp. strain JL24 revealed a putative biosynthetic pathway involving an acyltransferase-less type I polyketide synthase biosynthetic gene cluster.<\/jats:p>\n               <\/jats:sec>\n               <jats:sec>\n                  <jats:title>One-Sentence Summary<\/jats:title>\n                  <jats:p>Two secondary metabolites, glycosyl-migrastatin (1) and 5-hydroxy-migrastatin (2), were discovered from the gut bacterium Kitasatospora sp. JL24 in the dung beetle Onthophagus lenzii.<\/jats:p>\n               <\/jats:sec>","DOI":"10.1093\/jimb\/kuad046","type":"journal-article","created":{"date-parts":[[2023,12,14]],"date-time":"2023-12-14T05:34:09Z","timestamp":1702532049000},"source":"Crossref","is-referenced-by-count":2,"title":["Discovery and structure elucidation of glycosyl and 5-hydroxy migrastatins from dung beetle gut <i>Kitasatospora<\/i> sp."],"prefix":"10.1093","volume":"50","author":[{"given":"Ji Hyeon","family":"Im","sequence":"first","affiliation":[{"name":"N , Seoul 08826 , Republic of Korea"},{"name":"atural Products Research Institute, College of Pharmacy, Seoul National University , Seoul 08826 , Republic of Korea"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Seoyoung","family":"Oh","sequence":"additional","affiliation":[{"name":"N , Seoul 08826 , Republic of Korea"},{"name":"atural Products Research Institute, College of Pharmacy, Seoul National University , Seoul 08826 , Republic of Korea"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Eun Seo","family":"Bae","sequence":"additional","affiliation":[{"name":"N , Seoul 08826 , Republic of Korea"},{"name":"atural Products Research Institute, College of Pharmacy, Seoul National University , Seoul 08826 , Republic of Korea"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Soohyun","family":"Um","sequence":"additional","affiliation":[{"name":"N , Seoul 08826 , Republic of Korea"},{"name":"atural Products Research Institute, College of Pharmacy, Seoul National University , Seoul 08826 , Republic of Korea"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Sang Kook","family":"Lee","sequence":"additional","affiliation":[{"name":"N , Seoul 08826 , Republic of Korea"},{"name":"atural Products Research Institute, College of Pharmacy, Seoul National University , Seoul 08826 , Republic of Korea"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yeon Hee","family":"Ban","sequence":"additional","affiliation":[{"name":"Department of Molecular Bioscience, College of Biomedical Science, Kangwon National University , Chuncheon 24341 , Republic of Korea"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6405-5535","authenticated-orcid":false,"given":"Dong-Chan","family":"Oh","sequence":"additional","affiliation":[{"name":"N , Seoul 08826 , Republic of Korea"},{"name":"atural Products Research Institute, College of Pharmacy, Seoul National University , Seoul 08826 , Republic of Korea"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"286","published-online":{"date-parts":[[2023,12,13]]},"reference":[{"issue":"W1","key":"2023122618031456500_bib1","doi-asserted-by":"crossref","first-page":"W46","DOI":"10.1093\/nar\/gkad344","article-title":"antiSMASH 7.0: New and improved predictions for detection, regulation, chemical structures and visualisation","volume":"51","author":"Blin","year":"2023","journal-title":"Nucleic Acids Research"},{"issue":"5386","key":"2023122618031456500_bib2","doi-asserted-by":"crossref","first-page":"63","DOI":"10.1126\/science.282.5386.63","article-title":"Harnessing the biosynthetic code: Combinations, permutations, and mutations","volume":"282","author":"Cane","year":"1998","journal-title":"Science"},{"issue":"6","key":"2023122618031456500_bib3","doi-asserted-by":"crossref","first-page":"563","DOI":"10.1038\/nmeth.2474","article-title":"Nonhybrid, finished microbial genome assemblies from long-read SMRT sequencing data","volume":"10","author":"Chin","year":"2013","journal-title":"Nature Methods"},{"issue":"36","key":"2023122618031456500_bib4","doi-asserted-by":"crossref","first-page":"11326","DOI":"10.1021\/ja048779q","article-title":"The migrastatin family: Discovery of potent cell migration inhibitors by chemical synthesis","volume":"126","author":"Gaul","year":"2004","journal-title":"Journal of the American Chemical Society"},{"issue":"8","key":"2023122618031456500_bib5","doi-asserted-by":"crossref","first-page":"870","DOI":"10.7164\/antibiotics.47.870","article-title":"Dorrigocins: Novel antifungal antibiotics that change the morphology of ras-transformed NIH\/3T3 cells to that of normal cells II. 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