{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,30]],"date-time":"2026-09-30T11:06:58Z","timestamp":1790766418335,"version":"4.1.0"},"reference-count":35,"publisher":"Wiley","issue":"10","license":[{"start":{"date-parts":[[2012,6,14]],"date-time":"2012-06-14T00:00:00Z","timestamp":1339632000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemBioChem"],"published-print":{"date-parts":[[2012,7,9]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>New signaling molecules that induce lankacidin and lankamycin production in <jats:italic>Streptomyces rochei<\/jats:italic> were extracted from the culture filtrate and purified by Sephadex LH20 and silica gel chromatography with the help of bioassay. Chiral HPLC and ESI\u2010MS analyses indicated the presence of two active components\u2014SRB1 and SRB2\u2014and their molecular formulas were established to be C<jats:sub>15<\/jats:sub>H<jats:sub>24<\/jats:sub>O<jats:sub>5<\/jats:sub> and C<jats:sub>16<\/jats:sub>H<jats:sub>26<\/jats:sub>O<jats:sub>5<\/jats:sub>, respectively. By extensive NMR analysis, SRB1 and SRB2 were determined to be 2\u2010(1\u2032\u2010hydroxy\u20106\u2032\u2010oxo\u20108\u2032\u2010methylnonyl)\u20103\u2010methyl\u20104\u2010hydroxybut\u20102\u2010en\u20101,4\u2010olide and 2\u2010(1\u2032\u2010hydroxy\u20106\u2032\u2010oxo\u20108\u2032\u2010methyldecyl)\u20103\u2010methyl\u20104\u2010hydroxybut\u20102\u2010en\u20101,4\u2010olide, respectively. These structures were finally confirmed by chemical synthesis and the absolute configuration at C\u20101\u2032 was determined to be <jats:italic>R<\/jats:italic> in each case. The synthetic 1\u2032<jats:italic>R<\/jats:italic> isomers induced production of lankacidin and lankamycin at around 40 n<jats:sc>M<\/jats:sc> concentrations. SRB1 and SRB2 are therefore distinct from the well\u2010known 2,3\u2010disubstituted \u03b3\u2010butyrolactone molecules such as A\u2010factor, virginia butanolide, and SCB1 and and belong, like avenolide, recently isolated from <jats:italic>Streptomyces avermitilis<\/jats:italic>, to the \u03b3\u2010butenolide family.<\/jats:p>","DOI":"10.1002\/cbic.201200149","type":"journal-article","created":{"date-parts":[[2012,6,14]],"date-time":"2012-06-14T10:20:07Z","timestamp":1339669207000},"page":"1447-1457","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":72,"title":["The Butenolide Signaling Molecules SRB1 and SRB2 Induce Lankacidin and Lankamycin Production in <i>Streptomyces rochei<\/i>"],"prefix":"10.1002","volume":"13","author":[{"given":"Kenji","family":"Arakawa","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Naoto","family":"Tsuda","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Akihiro","family":"Taniguchi","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Haruyasu","family":"Kinashi","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2012,6,14]]},"reference":[{"key":"e_1_2_6_1_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.mib.2005.02.016"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.2183\/pjab.83.277"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.mib.2006.04.003"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1046\/j.1365-2958.1999.01579.x"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1271\/bbb.69.431"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.35.349"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.0607472104"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1365-2958.2005.04543.x"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1046\/j.1365-2958.2000.01819.x"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1128\/JB.183.14.4357-4363.2001"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.0805530105"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.1113908108"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.47.1447"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.0914100107"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1046\/j.1365-2958.2003.03523.x"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.chembiol.2005.01.009"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1128\/AAC.00016-06"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.1099\/mic.0.2006\/002170-0"},{"key":"e_1_2_6_19_2","doi-asserted-by":"publisher","DOI":"10.1128\/JB.01383-07"},{"key":"e_1_2_6_20_2","doi-asserted-by":"publisher","DOI":"10.1271\/bbb.90927"},{"key":"e_1_2_6_21_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.chembiol.2009.08.010"},{"key":"e_1_2_6_22_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1574-6968.1995.tb07387.x"},{"key":"e_1_2_6_23_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(00)00904-2"},{"key":"e_1_2_6_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00337a013"},{"key":"e_1_2_6_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00271a050"},{"key":"e_1_2_6_26_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-2001-10760"},{"key":"e_1_2_6_27_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00011a006"},{"key":"e_1_2_6_28_2","first-page":"2242","author":"Schreiber J.","year":"1965","journal-title":"Bull. 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