{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,1]],"date-time":"2026-09-01T18:28:06Z","timestamp":1788287286242,"version":"build-2803163510"},"reference-count":30,"publisher":"MDPI AG","issue":"1","license":[{"start":{"date-parts":[[2024,1,18]],"date-time":"2024-01-18T00:00:00Z","timestamp":1705536000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"University of Queensland (UQ)","award":["LE210100148"],"award-info":[{"award-number":["LE210100148"]}]},{"DOI":"10.13039\/501100000923","name":"UQ Institute for Molecular Bioscience and Australian Research Council","doi-asserted-by":"publisher","award":["LE210100148"],"award-info":[{"award-number":["LE210100148"]}],"id":[{"id":"10.13039\/501100000923","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Antibiotics"],"abstract":"<jats:p>The Australian roadside soil-derived fungus Penicillium shearii CMB-STF067 was prioritized for chemical investigation based on an SDA cultivation extract exhibiting both antibacterial properties and natural products with unprecedented molecular formulae (GNPS). Subsequent miniaturized 24-well plate cultivation profiling (MATRIX) identified red rice as optimal for the production of the target chemistry, with scaled-up cultivation, extraction and fractionation yielding four new xanthone\u2013anthraquinone heterodimers, jugiones A\u2013D (1\u20134), whose structures were assigned by detailed spectroscopic analysis and biosynthetic considerations. Of note, where 1\u20132 and 4 were active against the Gram-positive bacteria vancomycin-resistant Enterococcus faecalis (IC50 2.6\u20133.9 \u03bcM) and multiple-drug-resistant clinical isolates of Staphylococcus aureus (IC50 1.8\u20136.4 \u03bcM), and inactive against the Gram-negative bacteria Escherichia coli (IC50 &gt; 30 \u03bcM), the closely related analog 3 exhibited no antibacterial properties (IC50 &gt; 30 \u03bcM). Furthermore, where 1 was cytotoxic to human carcinoma (IC50 9.0\u20139.8 \u03bcM) and fungal (IC50 4.1 \u03bcM) cells, 2 and 4 displayed no such cytotoxicity (IC50 &gt; 30 \u03bcM), revealing an informative structure activity relationship (SAR). We also extended the SAR study to other known compounds of this heterodimer class, which showed that the modification of ring G can reduce or eliminate the cytotoxicity while retaining the antibacterial activity.<\/jats:p>","DOI":"10.3390\/antibiotics13010097","type":"journal-article","created":{"date-parts":[[2024,1,19]],"date-time":"2024-01-19T05:46:44Z","timestamp":1705643204000},"page":"97","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Jugiones A\u2013D: Antibacterial Xanthone\u2013Anthraquinone Heterodimers from Australian Soil-Derived Penicillium shearii CMB-STF067"],"prefix":"10.3390","volume":"13","author":[{"given":"Thulasi","family":"Sritharan","sequence":"first","affiliation":[{"name":"Institute for Molecular Bioscience, The University of Queensland, St. Lucia, QLD 4072, Australia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8177-5689","authenticated-orcid":false,"given":"Angela A.","family":"Salim","sequence":"additional","affiliation":[{"name":"Institute for Molecular Bioscience, The University of Queensland, St. Lucia, QLD 4072, Australia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9285-1720","authenticated-orcid":false,"given":"Zeinab G.","family":"Khalil","sequence":"additional","affiliation":[{"name":"Institute for Molecular Bioscience, The University of Queensland, St. Lucia, QLD 4072, Australia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8341-7754","authenticated-orcid":false,"given":"Robert J.","family":"Capon","sequence":"additional","affiliation":[{"name":"Institute for Molecular Bioscience, The University of Queensland, St. Lucia, QLD 4072, Australia"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2024,1,18]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1954","DOI":"10.1038\/s41596-020-0317-5","article-title":"Reproducible Molecular Networking of Untargeted Mass Spectrometry Data Using GNPS","volume":"15","author":"Aron","year":"2020","journal-title":"Nat. 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