{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,25]],"date-time":"2026-03-25T18:58:17Z","timestamp":1774465097821,"version":"3.50.1"},"reference-count":30,"publisher":"MDPI AG","issue":"10","license":[{"start":{"date-parts":[[2018,10,1]],"date-time":"2018-10-01T00:00:00Z","timestamp":1538352000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100019018","name":"CAMS Initiative for Innovative Medicine","doi-asserted-by":"publisher","award":["2017-I2M-4-004"],"award-info":[{"award-number":["2017-I2M-4-004"]}],"id":[{"id":"10.13039\/501100019018","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Marine Drugs"],"abstract":"<jats:p>By treating with histone-deacetylase inhibitor valproate sodium, three new heterdimeric tetrahydroxanthone\u2013chromanone lactones chrysoxanthones A\u2013C (1\u20133), along with 17 known compounds were isolated from a sponge-associated Penicillium chrysogenum HLS111. The planar structures of chrysoxanthones A\u2013C were elucidated by means of spectroscopic analyses, including MS, 1D, and 2D NMR. Their absolute configurations were established by electronic circular dichroism (ECD) calculations. Chrysoxanthones A\u2013C exhibited moderate antibacterial activities against Bacillus subtilis with minimum inhibitory concentration (MIC) values of 5\u201310 \u03bcg\/mL.<\/jats:p>","DOI":"10.3390\/md16100357","type":"journal-article","created":{"date-parts":[[2018,10,2]],"date-time":"2018-10-02T08:23:50Z","timestamp":1538468630000},"page":"357","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":25,"title":["Chrysoxanthones A\u2013C, Three New Xanthone\u2013Chromanone Heterdimers from Sponge-Associated Penicillium chrysogenum HLS111 Treated with Histone Deacetylase Inhibitor"],"prefix":"10.3390","volume":"16","author":[{"given":"Xin","family":"Zhen","sequence":"first","affiliation":[{"name":"State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Key Laboratory of Biosynthesis of Natural Products of National Health Committee, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, 1 Xian Nong Tan Street, Beijing 100050, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ting","family":"Gong","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Key Laboratory of Biosynthesis of Natural Products of National Health Committee, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, 1 Xian Nong Tan Street, Beijing 100050, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yan-Hua","family":"Wen","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Key Laboratory of Biosynthesis of Natural Products of National Health Committee, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, 1 Xian Nong Tan Street, Beijing 100050, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Dao-Jiang","family":"Yan","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Key Laboratory of Biosynthesis of Natural Products of National Health Committee, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, 1 Xian Nong Tan Street, Beijing 100050, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jing-Jing","family":"Chen","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Key Laboratory of Biosynthesis of Natural Products of National Health Committee, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, 1 Xian Nong Tan Street, Beijing 100050, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8537-2169","authenticated-orcid":false,"given":"Ping","family":"Zhu","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Key Laboratory of Biosynthesis of Natural Products of National Health Committee, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, 1 Xian Nong Tan Street, Beijing 100050, China"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2018,10,1]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1161","DOI":"10.1038\/nbt.1498","article-title":"Genome sequencing and analysis of the filamentous fungus Penicillium chrysogenum","volume":"26","author":"Albang","year":"2008","journal-title":"Nat. Biotechnol."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"513","DOI":"10.1021\/ol203097b","article-title":"Tenuipyrone, a novel skeletal polyketide from the entomopathogenic fungus, Isaria tenuipes, cultivated in the presence of epigenetic modifiers","volume":"14","author":"Asai","year":"2011","journal-title":"Org. Lett."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"5456","DOI":"10.1021\/ol302539s","article-title":"Structural diversity of new C13-polyketides produced by Chaetomium mollipilium cultivated in the presence of a NAD+-dependent histone deacetylase Inhibitor","volume":"14","author":"Asai","year":"2012","journal-title":"Org. Lett."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"687","DOI":"10.1016\/j.apsb.2017.12.012","article-title":"Epigenetic modification in histone deacetylase deletion strain of Calcarisporium arbuscula leads to diverse diterpenoids","volume":"8","author":"Bai","year":"2018","journal-title":"Acta Pharm. Sin. B"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"7592","DOI":"10.1002\/anie.201502452","article-title":"Epigenetic genome mining of an endophytic fungus leads to the pleiotropic biosynthesis of natural products","volume":"54","author":"Mao","year":"2015","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"109","DOI":"10.1002\/ejoc.201402984","article-title":"Biosynthetically distinct cytotoxic polyketides from Setophoma terrestris","volume":"2015","author":"Figueroa","year":"2015","journal-title":"Eur. J. Org. Chem."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"604","DOI":"10.1016\/j.phytol.2012.06.004","article-title":"A dimeric chromanone and a phthalide: Metabolites from the seagrass-derived fungus Bipolaris sp. PSU-ES64","volume":"5","author":"Arunpanichlert","year":"2012","journal-title":"Phytochem. Lett."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"2691","DOI":"10.1021\/acs.jnatprod.5b00636","article-title":"Versixanthones A\u2013F, cytotoxic xanthone-chromanone dimers from the marine-derived fungus Aspergillus versicolor HDN1009","volume":"78","author":"Wu","year":"2015","journal-title":"J. Nat. Prod."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"418","DOI":"10.7164\/antibiotics.49.418","article-title":"Andrastins A\u2013C, new protein farnesyltransferase inhibitors produced by Penidllium sp. FO-3929","volume":"49","author":"Uchida","year":"1996","journal-title":"J. Antibiot."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"414","DOI":"10.7164\/antibiotics.49.414","article-title":"Andrastins A\u2013C, new protein farnesyltransferase inhibitors produced by Penicillium sp. FO-3929. I. Producing strain, fermentation, isolation, and biological activities","volume":"49","author":"Omura","year":"1996","journal-title":"J. Antibiot."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"51","DOI":"10.1016\/0040-4020(70)85006-2","article-title":"The isolation, structure and absolute configuration of secalonic acid D, the toxic metabolite of Penicillium oxalicum","volume":"26","author":"Steyn","year":"1970","journal-title":"Tetrahedron"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"352","DOI":"10.1021\/jo00422a042","article-title":"Secalonic acids D and F are toxic metabolites of Aspergillus aculeatus","volume":"42","author":"Andersen","year":"1977","journal-title":"J. Org. Chem."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"1256","DOI":"10.7164\/antibiotics.32.1256","article-title":"Biosynthetic relationships among the secalonic acids","volume":"32","author":"Kurobane","year":"1979","journal-title":"J. Antibiot."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"4563","DOI":"10.1002\/ejoc.200500265","article-title":"X-ray structure determination, absolute configuration and biological activity of phomoxanthone A","volume":"2005","author":"Krohn","year":"2005","journal-title":"Eur. J. Org. Chem."},{"key":"ref_15","first-page":"174","article-title":"Bioactive metabolites isolated from the fungus Penicillium chrysogenum HLS111 associated with the marine sponge Gelliodes carnosa","volume":"9","author":"Gong","year":"2014","journal-title":"Chin. Med. Biotechnol."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"797","DOI":"10.1016\/S0031-9422(02)00622-2","article-title":"Homoisoflavonoids and xanthones from the tubers of wild and in vitro regenerated Ledebouria graminifolia and cytotoxic activities of some of the homoisoflavonoids","volume":"62","author":"Mutanyatta","year":"2003","journal-title":"Phytochemistry"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"209","DOI":"10.1016\/j.fitote.2011.10.013","article-title":"Polyketides with antimicrobial activity from the solid culture of an endolichenic fungus Ulocladium sp.","volume":"83","author":"Wang","year":"2012","journal-title":"Fitoterapia"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"114","DOI":"10.1016\/j.phytol.2016.07.003","article-title":"Penicisimpins A\u2013C, three new dihydroisocoumarins from Penicillium simplicissimum MA-332, a marine fungus derived from the rhizosphere of the mangrove plant Bruguiera sexangula var","volume":"17","author":"Xu","year":"2016","journal-title":"rhynchopetala. Phytochem. Lett."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"374","DOI":"10.1021\/np50004a004","article-title":"Isolation of radicicol from Penicillium luteo-aurantium, and meleagrin, a new metabolite from Penicillium meleagrinum","volume":"42","author":"Nozawa","year":"1979","journal-title":"J. Nat. Prod."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"2625","DOI":"10.1016\/0040-4020(76)88040-4","article-title":"The chemistry and 13C NMR assignments of oxaline, a novel alkaloid from Penicillium oxalicum","volume":"32","author":"Nagel","year":"1976","journal-title":"Tetrahedron"},{"key":"ref_21","first-page":"2097","article-title":"Identification of roquefortine C produced by Penicillium roqueforti","volume":"41","author":"Ohmomo","year":"1977","journal-title":"Agric. Biol. Chem."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"3851","DOI":"10.1016\/j.tetlet.2016.07.049","article-title":"Structure revision of the penicillium alkaloids haenamindole and citreoindole","volume":"57","author":"Song","year":"2016","journal-title":"Tetrahedron Lett."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"1033","DOI":"10.1016\/j.tet.2008.11.078","article-title":"New alkaloids and diterpenes from a deep ocean sediment derived fungus Penicillium sp.","volume":"65","author":"Du","year":"2009","journal-title":"Tetrahedron"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"2","DOI":"10.1186\/s40694-016-0020-z","article-title":"Identification and characterization of the ergochrome gene cluster in the plant pathogenic fungus Claviceps purpurea","volume":"3","author":"Neubauer","year":"2016","journal-title":"Fungal Biol. Biotechnol."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1007\/s13225-010-0022-8","article-title":"Phylogenetic diversity of culturable fungi associated with two marine sponges: Haliclona simulans and Gelliodes carnosa, collected from the Hainan Island coastal waters of the South China Sea","volume":"42","author":"Liu","year":"2010","journal-title":"Fungal Divers."},{"key":"ref_26","unstructured":"Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Mennucci, B., and Petersson, G.A. (Gaussian09, R.A. 1, 2009). Gaussian09, R.A. 1."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"P32","DOI":"10.1186\/1758-2946-3-S1-P32","article-title":"Confab\u2014Generation of diverse low energy conformers","volume":"3","author":"Vandermeersch","year":"2011","journal-title":"J Cheminform."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"243","DOI":"10.1002\/chir.22138","article-title":"SpecDis: Quantifying the comparison of calculated and experimental electronic circular dichroism spectra","volume":"25","author":"Bruhn","year":"2013","journal-title":"Chirality"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"1366","DOI":"10.1039\/C6CC08292K","article-title":"Aminoglycoside-based novel probes for bacterial diagnostic and therapeutic applications","volume":"53","author":"Zhang","year":"2017","journal-title":"Chem. Commun."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"6947","DOI":"10.3390\/md13116947","article-title":"A new analogue ofechinomycin and a new cyclic dipeptide from a marine-derived Streptomyces sp. LS298","volume":"13","author":"Zhen","year":"2015","journal-title":"Mar. Drugs"}],"container-title":["Marine Drugs"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1660-3397\/16\/10\/357\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T15:23:28Z","timestamp":1760196208000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1660-3397\/16\/10\/357"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2018,10,1]]},"references-count":30,"journal-issue":{"issue":"10","published-online":{"date-parts":[[2018,10]]}},"alternative-id":["md16100357"],"URL":"https:\/\/doi.org\/10.3390\/md16100357","relation":{},"ISSN":["1660-3397"],"issn-type":[{"value":"1660-3397","type":"electronic"}],"subject":[],"published":{"date-parts":[[2018,10,1]]}}}