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Genomic analysis identified two type III polyketide synthase genes, designated cspks and cupks. Heterologous expression of both genes in Aspergillus oryzae NSAR1 yielded a variety of acylphloroglucinols derived from different starter units. Among these were cavenderic acids A\u2212E (1\u22125) and two related ester derivatives (6\u22127). Compounds 1 and 2 are reported here for the first time as natural products, whereas compounds 3\u22127 are new compounds. Structural analysis suggested that compounds 1\u22127 are biosynthetically derived from C4\u2212C10 \u03b1,\u03c9-dicarboxylic acid CoA thioesters, representing a putative and unprecedented starter-unit class for type III PKSs. Additionally, four known acylphloroglucinols (8\u221210 and 12) and one new derivative (11), derived from saturated and unsaturated fatty acid starter units, were identified. These findings demonstrate the broad starter-unit promiscuity of Cavenderia type III PKSs and their ability to generate structurally diverse acylphloroglucinols when expressed in a heterologous host. Compounds 1, 3\u22124, and 8\u221211 were evaluated for antimicrobial activity. Compound 8 (jambone C) exhibited the strongest antibacterial activity against several Gram-positive bacteria. Comparison of the tested compounds further suggested that terminal polar functional groups reduced antibacterial activity, providing preliminary structure\u2212activity relationship insights for acylphloroglucinols.<\/jats:p>","DOI":"10.1021\/acs.jnatprod.6c00631","type":"journal-article","created":{"date-parts":[[2026,8,7]],"date-time":"2026-08-07T14:01:38Z","timestamp":1786111298000},"page":"2486-2501","source":"Crossref","is-referenced-by-count":0,"title":["Starter Unit Promiscuity of Dictyostelid Type III Polyketide Synthases Generates Diverse Acylphloroglucinols with Antimicrobial Activity"],"prefix":"10.1021","volume":"89","author":[{"ORCID":"https:\/\/orcid.org\/0009-0009-3502-6271","authenticated-orcid":true,"given":"Nattapong","family":"Dedkad","sequence":"first","affiliation":[{"name":"Kasetsart University , , ,","place":["Bangkok, Thailand, 10900"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sukhita","family":"Sathitnaitham","sequence":"additional","affiliation":[{"name":"Kasetsart University , , ,","place":["Bangkok, Thailand, 10900"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kamonchat","family":"Prommarit","sequence":"additional","affiliation":[{"name":"Kasetsart University , , ,","place":["Bangkok, Thailand, 10900"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Thanyaporn","family":"Chittavichai","sequence":"additional","affiliation":[{"name":"Kasetsart University , , ,","place":["Bangkok, Thailand, 10900"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Supanut","family":"Utthiya","sequence":"additional","affiliation":[{"name":"Kasetsart University , , ,","place":["Bangkok, Thailand, 10900"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9290-0238","authenticated-orcid":true,"given":"Wanchat","family":"Sirisarn","sequence":"additional","affiliation":[{"name":"Kasetsart University , , ,","place":["Bangkok, Thailand, 10900"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1362-2971","authenticated-orcid":true,"given":"Piyangkun","family":"Lueangjaroenkit","sequence":"additional","affiliation":[{"name":"Kasetsart University , , ,","place":["Bangkok, Thailand, 10900"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1194-3552","authenticated-orcid":true,"given":"Supachai","family":"Vuttipongchaikij","sequence":"additional","affiliation":[{"name":"Kasetsart University , , ,","place":["Bangkok, Thailand, 10900"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6224-0275","authenticated-orcid":true,"given":"Passorn","family":"Wonnapinij","sequence":"additional","affiliation":[{"name":"Kasetsart University , , ,","place":["Bangkok, Thailand, 10900"]},{"name":"Kasetsart University (OmiKU) , , ,","place":["Bangkok, Thailand, 10900"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4780-7122","authenticated-orcid":true,"given":"Pakorn","family":"Wattana-Amorn","sequence":"additional","affiliation":[{"name":"Kasetsart University , , ,","place":["Bangkok, Thailand, 10900"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,8,7]]},"reference":[{"issue":"7","key":"2026100909070935600_cit1","doi-asserted-by":"publisher","first-page":"531","DOI":"10.1038\/nrm1427","article-title":"Insights into morphogenesis from a simple developmental system","volume":"5","author":"Chisholm","year":"2004","journal-title":"Nat. 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