{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,30]],"date-time":"2026-06-30T05:41:34Z","timestamp":1782798094911,"version":"3.54.5"},"reference-count":41,"publisher":"Beilstein Institut","license":[{"start":{"date-parts":[[2020,5,25]],"date-time":"2020-05-25T00:00:00Z","timestamp":1590364800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0"},{"start":{"date-parts":[[2020,5,25]],"date-time":"2020-05-25T00:00:00Z","timestamp":1590364800000},"content-version":"am","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0"},{"start":{"date-parts":[[2020,5,25]],"date-time":"2020-05-25T00:00:00Z","timestamp":1590364800000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Beilstein J. Org. Chem."],"accepted":{"date-parts":[[2020,5,5]]},"abstract":"<jats:p>Aside from the well-studied conventional actinomycetes such as <jats:italic>Streptomyces<\/jats:italic>, the less investigated genera of actinomycetes also represent a promising source of natural products. Genome mining indicated that members of the underexplored genus <jats:italic>Pseudosporangium<\/jats:italic>, from which no secondary metabolites have been reported to date, may harbor the biosynthetic machinery for the formation of novel natural products. The strain RD062863, that is available at a public culture collection, was obtained and subjected to metabolite analysis, which resulted in the discovery of a novel cyclopeptide, pseudosporamide (<jats:bold>1<\/jats:bold>), along with three new oligomycin-class polyketides, pseudosporamicins A\u2013C (<jats:bold>2<\/jats:bold>\u2013<jats:bold>4<\/jats:bold>). The unusual structure of compound <jats:bold>1<\/jats:bold>, featured by a biaryl-bond bridging across a tripeptide scaffold, <jats:italic>N<\/jats:italic>-acetyl-\u029f-Tyr-\u029f-Pro-\u029f-Trp, was determined by a combination of spectroscopic analyses, chemical derivatization, ECD calculation, and DFT-based theoretical chemical shift calculation, revealing the presence of an (<jats:italic>S<\/jats:italic><jats:sub>a<\/jats:sub>)-axial chirality around the biaryl bond. Compounds <jats:bold>2<\/jats:bold>\u2013<jats:bold>4<\/jats:bold> lacked hydroxylation on the side chain of the spiroacetal rings, which showed clear contrast to other oligomycin congeners and related polyketides with ring-truncation or expansion. The new macrolides <jats:bold>2<\/jats:bold>\u2013<jats:bold>4<\/jats:bold> displayed potent antimicrobial activity against the Gram-positive bacterium <jats:italic>Kocuria rhizohpila<\/jats:italic> and the plant pathogenic fungus <jats:italic>Glomerella cingulata<\/jats:italic>. All compounds showed moderate cytotoxicity against P388 murine leukemia cells with IC<jats:sub>50<\/jats:sub> values in the micromolar to submicromolar ranges. These results exemplified the validity of phylogeny-focused strain selection combined with biosynthetic gene-directed genome mining for the efficient discovery of new natural products.<\/jats:p>","DOI":"10.3762\/bjoc.16.97","type":"journal-article","created":{"date-parts":[[2020,5,25]],"date-time":"2020-05-25T09:25:51Z","timestamp":1590398751000},"page":"1100-1110","source":"Crossref","is-referenced-by-count":40,"title":["A cyclopeptide and three oligomycin-class polyketides produced by an underexplored actinomycete of the genus <i>Pseudosporangium<\/i>"],"prefix":"10.3762","volume":"16","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-8628-5614","authenticated-orcid":false,"given":"Shun","family":"Saito","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kota","family":"Atsumi","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tao","family":"Zhou","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7148-4714","authenticated-orcid":false,"given":"Keisuke","family":"Fukaya","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1999-9374","authenticated-orcid":false,"given":"Daisuke","family":"Urabe","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Naoya","family":"Oku","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Md Rokon Ul","family":"Karim","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hisayuki","family":"Komaki","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5114-1389","authenticated-orcid":false,"given":"Yasuhiro","family":"Igarashi","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"2086","published-online":{"date-parts":[[2020,5,25]]},"reference":[{"key":"ref1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jnatprod.5b01055"},{"key":"ref2","doi-asserted-by":"publisher","DOI":"10.1016\/j.foodcont.2016.03.001"},{"key":"ref3","doi-asserted-by":"publisher","DOI":"10.1038\/ja.2008.16"},{"key":"ref4","doi-asserted-by":"publisher","DOI":"10.1016\/b978-0-12-817190-5.00004-5"},{"key":"ref5","first-page":"1","volume":"21","author":"Srianta","year":"2014","journal-title":"International Food Research Journal"},{"key":"ref6","volume-title":"Difco & BBL Manual. Manual of Microbiological Culture Media","author":"Zimbro","year":"2009","edition":"2"},{"key":"ref7","doi-asserted-by":"publisher","DOI":"10.1038\/s41598-017-07757-w"},{"key":"ref9","doi-asserted-by":"publisher","DOI":"10.1201\/9781315184289"},{"key":"ref10","doi-asserted-by":"publisher","DOI":"10.1039\/c6np00025h"},{"key":"ref11","doi-asserted-by":"publisher","DOI":"10.1038\/s41598-018-24921-y"},{"key":"ref12","doi-asserted-by":"publisher","DOI":"10.1016\/0385-6380(88)90001-5"},{"key":"ref13","doi-asserted-by":"publisher","DOI":"10.1038\/ja.2012.27"},{"key":"ref16","doi-asserted-by":"publisher","DOI":"10.1099\/ijs.0.65680-0"},{"key":"ref17","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/gkz310"},{"key":"ref19","doi-asserted-by":"publisher","DOI":"10.1007\/s00726-004-0118-0"},{"key":"ref20","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jnatprod.5b00540"},{"key":"ref21","doi-asserted-by":"publisher","DOI":"10.1021\/jo991218a"},{"key":"ref22","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200901255"},{"key":"ref23","doi-asserted-by":"publisher","DOI":"10.1021\/cr200106v"},{"key":"ref24","doi-asserted-by":"publisher","DOI":"10.1039\/c3np70028c"},{"key":"ref25","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.5b02396"},{"key":"ref26","doi-asserted-by":"publisher","DOI":"10.1007\/s11418-013-0768-x"},{"key":"ref27","doi-asserted-by":"publisher","DOI":"10.1002\/chir.22600"},{"key":"ref28","first-page":"151","volume":"3","author":"Salzet","year":"2000","journal-title":"Current Trends in Immunology"},{"key":"ref29","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.46.1812"},{"key":"ref30","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-019-10384-w"},{"key":"ref31","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.53.105"},{"key":"ref32","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4039(95)00676-4"},{"key":"ref33","first-page":"962","volume":"4","author":"Smith","year":"1954","journal-title":"Antibiotics and Chemotherapy"},{"key":"ref34","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.44.1318"},{"key":"ref35","first-page":"474","author":"Thompson","year":"1961","journal-title":"Antimicrobial Agents and Chemotherapy"},{"key":"ref36","first-page":"82","volume":"18","author":"Schmitz","year":"1965","journal-title":"Journal of Antibiotics"},{"key":"ref37","doi-asserted-by":"publisher","DOI":"10.1021\/np300719g"},{"key":"ref38","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.53.474"},{"key":"ref39","doi-asserted-by":"publisher","DOI":"10.1038\/ja.2005.55"},{"key":"ref40","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.54.573"},{"key":"ref41","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.m300299200"},{"key":"ref43","doi-asserted-by":"publisher","DOI":"10.1038\/ja.2014.168"},{"key":"ref44","doi-asserted-by":"publisher","DOI":"10.1016\/s0040-4020(98)00838-2"},{"key":"ref45","doi-asserted-by":"publisher","DOI":"10.1038\/ja.2011.137"},{"key":"ref49","doi-asserted-by":"publisher","DOI":"10.3762\/bjoc.16.29"}],"container-title":["Beilstein Journal of Organic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.beilstein-journals.org\/bjoc\/articles\/16\/97","content-type":"text\/html","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/www.beilstein-journals.org\/bjoc\/content\/pdf\/1860-5397-16-97.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/www.beilstein-journals.org\/bjoc\/articles\/16\/97","content-type":"text\/html","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2021,6,24]],"date-time":"2021-06-24T08:41:46Z","timestamp":1624524106000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.beilstein-journals.org\/bjoc\/articles\/16\/97"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,5,25]]},"references-count":41,"URL":"https:\/\/doi.org\/10.3762\/bjoc.16.97","archive":["Portico"],"relation":{},"ISSN":["1860-5397"],"issn-type":[{"value":"1860-5397","type":"electronic"}],"subject":[],"published":{"date-parts":[[2020,5,25]]}}}