{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,13]],"date-time":"2026-07-13T21:47:22Z","timestamp":1783979242519,"version":"3.55.0"},"reference-count":40,"publisher":"MDPI AG","issue":"11","license":[{"start":{"date-parts":[[2017,11,14]],"date-time":"2017-11-14T00:00:00Z","timestamp":1510617600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Marine Drugs"],"abstract":"<jats:p>The marine-derived fungus Talaromyces rugulosus isolated from the Mediterranean sponge Axinella cannabina and cultured on solid rice medium yielded seventeen lactone derivatives including five butenolides (1\u20135), seven (3S)-resorcylide derivatives (6\u201312), two butenolide-resorcylide dimers (13 and 14), and three dihydroisocoumarins (15\u201317). Among them, fourteen compounds (1\u20133, 6\u201316) are new natural products. The structures of the isolated compounds were elucidated by 1D and 2D NMR (Nuclear Magnetic Resonance) spectroscopy as well as by ESI-HRMS (ElectroSpray Ionization-High Resolution Mass Spectrometry). TDDFT-ECD (Time-Dependent Density Functional Theory-Electronic Circular Dichroism) calculations were performed to determine the absolute configurations of chiral compounds. The butenolide-resorcylide dimers talarodilactones A and B (13 and 14) exhibited potent cytotoxicity against the L5178Y murine lymphoma cell line with IC50 values of 3.9 and 1.3 \u00b5M, respectively.<\/jats:p>","DOI":"10.3390\/md15110359","type":"journal-article","created":{"date-parts":[[2017,11,14]],"date-time":"2017-11-14T10:58:32Z","timestamp":1510657112000},"page":"359","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":42,"title":["Lactones from the Sponge-Derived Fungus Talaromyces rugulosus"],"prefix":"10.3390","volume":"15","author":[{"given":"Lisa","family":"K\u00fcppers","sequence":"first","affiliation":[{"name":"Institute of Pharmaceutical Biology and Biotechnology, Heinrich-Heine-Universit\u00e4t D\u00fcsseldorf, 40225 D\u00fcsseldorf, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3725-9481","authenticated-orcid":false,"given":"Weaam","family":"Ebrahim","sequence":"additional","affiliation":[{"name":"Institute of Pharmaceutical Biology and Biotechnology, Heinrich-Heine-Universit\u00e4t D\u00fcsseldorf, 40225 D\u00fcsseldorf, Germany"},{"name":"Department of Pharmacognosy, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mona","family":"El-Neketi","sequence":"additional","affiliation":[{"name":"Department of Pharmacognosy, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2499-8480","authenticated-orcid":false,"given":"Ferhat","family":"\u00d6zkaya","sequence":"additional","affiliation":[{"name":"Institute of Pharmaceutical Biology and Biotechnology, Heinrich-Heine-Universit\u00e4t D\u00fcsseldorf, 40225 D\u00fcsseldorf, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7867-7084","authenticated-orcid":false,"given":"Attila","family":"M\u00e1ndi","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry, University of Debrecen, 4032 Debrecen, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tibor","family":"Kurt\u00e1n","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry, University of Debrecen, 4032 Debrecen, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Raha","family":"Orfali","sequence":"additional","affiliation":[{"name":"Department of Pharmacognosy, Faculty of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Werner","family":"M\u00fcller","sequence":"additional","affiliation":[{"name":"Institute of Physiological Chemistry, Universit\u00e4tsmedizin der Johannes Gutenberg-Universit\u00e4t Mainz, 55128 Mainz, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7807-6273","authenticated-orcid":false,"given":"Rudolf","family":"Hartmann","sequence":"additional","affiliation":[{"name":"Institute of Complex Systems: Strukturbiochemie, ForschungszentrumJuelich, 52428 Juelich, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4978-4083","authenticated-orcid":false,"given":"Wenhan","family":"Lin","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing 100191, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Weiguo","family":"Song","sequence":"additional","affiliation":[{"name":"FukangPharma, North-East of Dongwaihuan Road, Dongcheng Industrial Area, Shouguang City 262700, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3314-7853","authenticated-orcid":false,"given":"Zhen","family":"Liu","sequence":"additional","affiliation":[{"name":"Institute of Pharmaceutical Biology and Biotechnology, Heinrich-Heine-Universit\u00e4t D\u00fcsseldorf, 40225 D\u00fcsseldorf, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Peter","family":"Proksch","sequence":"additional","affiliation":[{"name":"Institute of Pharmaceutical Biology and Biotechnology, Heinrich-Heine-Universit\u00e4t D\u00fcsseldorf, 40225 D\u00fcsseldorf, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2017,11,14]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"4137","DOI":"10.3390\/md13074137","article-title":"Investigation of marine-derived fungal diversity and their exploitable biological activities","volume":"13","author":"Hong","year":"2015","journal-title":"Mar. Drugs"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"255","DOI":"10.1016\/j.tips.2010.02.005","article-title":"The odyssey of marine pharmaceuticals: A current pipeline perspective","volume":"31","author":"Mayer","year":"2010","journal-title":"Trends Pharmacol. Sci."},{"key":"ref_3","doi-asserted-by":"crossref","unstructured":"Ebada, S., and Proksch, P. (2015). Marine-Derived Fungal Metabolites. Springer Handbook of Marine Biotechnology, Springer.","DOI":"10.1007\/978-3-642-53971-8_32"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"914","DOI":"10.1021\/acs.jnatprod.5b00975","article-title":"Metabolites from the fungal endophyte Aspergillus austroafricanus in axenic culture and in fungal-bacterial mixed cultures","volume":"79","author":"Ebrahim","year":"2016","journal-title":"J. Nat. Prod."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"2332","DOI":"10.1021\/acs.jnatprod.6b00473","article-title":"Cytotoxic 14-membered macrolides from a mangrove-derived endophytic fungus, Pestalotiopsis microspora","volume":"79","author":"Liu","year":"2016","journal-title":"J. Nat. Prod."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"2411","DOI":"10.1016\/j.tet.2016.03.073","article-title":"Xanthones and sesquiterpene derivatives from a marine-derived fungus Scopulariopsis sp.","volume":"72","author":"Elnaggar","year":"2016","journal-title":"Tetrahedron"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"126","DOI":"10.1016\/j.fitote.2016.12.003","article-title":"Two new triterpenoids and a new naphthoquinone derivative isolated from a hard coral-derived fungus Scopulariopsis sp.","volume":"116","author":"Elnaggar","year":"2017","journal-title":"Fitoterapia"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"567","DOI":"10.1002\/hlca.200800333","article-title":"Cathepsin B inhibitory tetraene lactones from the fungus Talaromyces wortmannii","volume":"92","author":"Dong","year":"2009","journal-title":"Helv. Chim. Acta"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"185","DOI":"10.1055\/s-0029-1186047","article-title":"The bioactive metabolites of the mangrove endophytic fungus Talaromyces sp. ZH-154 isolated from Kandelia candel (L.) Druce","volume":"76","author":"Liu","year":"2010","journal-title":"Planta Med."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"491","DOI":"10.1038\/ja.2013.28","article-title":"Antibiotically active metabolites from Talaromyces wortmannii, an endophyte of Aloe vera","volume":"66","author":"Bara","year":"2013","journal-title":"J. Antibiot."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1007\/s13659-015-0081-3","article-title":"The bioactive secondary metabolites from Talaromyces species","volume":"6","author":"Zhai","year":"2016","journal-title":"Nat. Prod. Bioprospect."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"175","DOI":"10.1016\/j.simyco.2014.08.001","article-title":"Polyphasic taxonomy of the genus Talaromyces","volume":"78","author":"Yilmaz","year":"2014","journal-title":"Stud. Mycol."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"105","DOI":"10.1080\/1478641032000101714","article-title":"Butenolides from a cultured microfungus, Acremonium sp.","volume":"18","author":"Ghisalberti","year":"2004","journal-title":"Nat. Prod. Res."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"3256","DOI":"10.1002\/ejoc.201700288","article-title":"Expanding the metabolic profile of the fungus Chaetomium sp. through co-culture with autoclaved Pseudomonas aeruginosa","volume":"2017","author":"Ancheeva","year":"2017","journal-title":"Eur. J. Org. Chem."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"466","DOI":"10.1002\/chir.22600","article-title":"Good computational practice in the assignment of absolute configurations by TDDFT calculations of ECD spectra","volume":"28","author":"Pescitelli","year":"2016","journal-title":"Chirality"},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"2051","DOI":"10.1021\/acs.jnatprod.5b00369","article-title":"Absolute configuration and conformational study of psammaplysins A and B from the Balinese marine sponge Aplysinella strongylata","volume":"78","author":"Mudianta","year":"2015","journal-title":"J. Nat. Prod."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"1023","DOI":"10.1021\/np970200x","article-title":"New macrocyclic lactones from a Penicillium species","volume":"60","author":"Barrow","year":"1997","journal-title":"J. Nat. Prod."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"1119","DOI":"10.1021\/cb500043g","article-title":"Insights into the biosynthesis of 12-membered resorcylic acid lactones from heterologous production in Saccharomyces cerevisiae","volume":"9","author":"Xu","year":"2014","journal-title":"ACS Chem. Biol."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"39870","DOI":"10.1039\/C5RA02203G","article-title":"Structure, absolute configuration, and conformational study of resorcylic acid derivatives and related congeners from the fungus Penicillium brocae","volume":"5","author":"Zhang","year":"2015","journal-title":"RSC Adv."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"27396","DOI":"10.1038\/srep27396","article-title":"Penicimenolides A\u2013F, resorcylic acid lactones from Penicillium sp., isolated from the rhizosphere soil of Panax notoginseng","volume":"6","author":"An","year":"2016","journal-title":"Sci. Rep."},{"key":"ref_21","doi-asserted-by":"crossref","unstructured":"Kerti, G., Kurt\u00e1n, T., Illy\u00e9s, T.Z., K\u00f6v\u00e9r, K.E., S\u00f3lyom, S., Pescitelli, G., Fujioka, N., Berova, N., and Antus, S. (2007). Enantioselective synthesis of 3-methylisochromans and determination of their absolute configurations by circular dichroism. Eur. J. Org. Chem., 296\u2013305.","DOI":"10.1002\/ejoc.200600678"},{"key":"ref_22","doi-asserted-by":"crossref","unstructured":"Krohn, K., Kock, I., Els\u00e4sser, B., Fl\u00f6rke, U., Schulz, B., Dr\u00e4ger, S., Pescitelli, G., Antus, S., and Kurt\u00e1n, T. (2007). Bioactive natural products from the endophytic fungus Ascochyta sp. from meliotus dentatus\u2014Configurational assignment by solid-state CD and TDDFT calculations. Eur. J. Org. Chem., 1123\u20131129.","DOI":"10.1002\/ejoc.200600907"},{"key":"ref_23","doi-asserted-by":"crossref","unstructured":"Hussain, H., Akhtar, N., Dr\u00e4ger, S., Schulz, B., Pescitelli, G., Salvadori, P., Antus, S., Kurt\u00e1n, T., and Krohn, K. (2009). New bioactive 2,3-epoxycyclohexenes and isocoumarins from the endophytic fungus Phomopsis sp. from Laurus azorica. Eur. J. Org. Chem., 749\u2013756.","DOI":"10.1002\/ejoc.200801052"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"371","DOI":"10.1007\/s10600-012-0254-9","article-title":"Two new dihydroisocoumarins from the endophytic fungus Aspergillus sp. collected from the South China Sea","volume":"48","author":"Li","year":"2012","journal-title":"Chem. Nat. Compd."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"2921","DOI":"10.1016\/j.tetlet.2014.03.067","article-title":"First enantioselective total synthesis of penicimarin B, aspergillumarins A and B","volume":"55","author":"Yadav","year":"2014","journal-title":"Tetrahedron Lett."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"6721","DOI":"10.1016\/j.tetlet.2012.10.011","article-title":"Farinomalein derivatives from an unidentified endophytic fungus isolated from the mangrove plant Avicennia marina","volume":"53","author":"Debbab","year":"2012","journal-title":"Tetrahedron Lett."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"3476","DOI":"10.1002\/ejoc.201200245","article-title":"Decalactone derivatives from Corynespora cassiicola, an endophytic fungus of the mangrove plant Laguncularia racemosa","volume":"2012","author":"Ebrahim","year":"2012","journal-title":"Eur. J. Org. Chem."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"1390","DOI":"10.1021\/np500151b","article-title":"Meroterpenoids from the alga-derived fungi Penicillium thomii Maire and Penicillium lividum Westling","volume":"77","author":"Zhuravleva","year":"2014","journal-title":"J. Nat. Prod."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"485","DOI":"10.1055\/s-0030-1250570","article-title":"Labdanediterpenoids and shikimic acid derivatives from Araucaria cunninghamii","volume":"77","author":"Chen","year":"2011","journal-title":"Planta Med."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"102","DOI":"10.1016\/j.phytochem.2016.10.002","article-title":"Biologically active xanthones from Codonopsis ovate","volume":"132","author":"Dar","year":"2016","journal-title":"Phytochemistry"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"479","DOI":"10.1038\/nprot.2009.233","article-title":"Methods for isolation of marine-derived endophytic fungi and their bioactive secondary products","volume":"5","author":"Kjer","year":"2010","journal-title":"Nat. Protoc."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"1787","DOI":"10.1002\/jcc.20495","article-title":"Semiempirical GGA-type density functional constructed with a long-range dispersion correction","volume":"27","author":"Grimme","year":"2006","journal-title":"J. Comput. Chem."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"7030","DOI":"10.1021\/jo400861j","article-title":"Structure, absolute configuration, and conformational study of 12-membered macrolides from the fungus Dendrodochium sp. associated with the sea cucumber Holothuria nobilis Selenka","volume":"78","author":"Sun","year":"2013","journal-title":"J. Org. Chem."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"51","DOI":"10.1016\/j.cplett.2004.06.011","article-title":"A new hybrid exchange\u2013correlation functional using the Coulomb-attenuating method (CAM-B3LYP)","volume":"393","author":"Yanai","year":"2004","journal-title":"Chem. Phys. Lett."},{"key":"ref_35","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. (Gaussian 09, 2010). Gaussian 09, revision B.01."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"229","DOI":"10.1002\/chir.20733","article-title":"ECD cotton effect approximated by the Gaussian curve and other methods","volume":"22","author":"Stephens","year":"2010","journal-title":"Chirality"},{"key":"ref_37","unstructured":"MacroModel (2013, December 31). Schro\u0308dinger, LLC, 2015. Available online: http:\/\/www.schrodinger.com\/."},{"key":"ref_38","unstructured":"Varetto, U. (MOLEKEL, 2009). MOLEKEL, version 5.4."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"1547","DOI":"10.1021\/np060172v","article-title":"Kahalalide derivatives from the Indian sacoglossan mollusk Elysia grandifolia","volume":"69","author":"Ashour","year":"2006","journal-title":"J. Nat. Prod."},{"key":"ref_40","unstructured":"Clinical and Laboratory Standards Institute (CLSI) (2012). Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria That Grow Aerobically: Approved Standard, Clinical and Laboratory Standards Institute. [9th ed.]."}],"container-title":["Marine Drugs"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1660-3397\/15\/11\/359\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T18:49:21Z","timestamp":1760208561000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1660-3397\/15\/11\/359"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2017,11,14]]},"references-count":40,"journal-issue":{"issue":"11","published-online":{"date-parts":[[2017,11]]}},"alternative-id":["md15110359"],"URL":"https:\/\/doi.org\/10.3390\/md15110359","relation":{},"ISSN":["1660-3397"],"issn-type":[{"value":"1660-3397","type":"electronic"}],"subject":[],"published":{"date-parts":[[2017,11,14]]}}}