{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,26]],"date-time":"2026-01-26T10:37:48Z","timestamp":1769423868689,"version":"3.49.0"},"reference-count":24,"publisher":"MDPI AG","issue":"5","license":[{"start":{"date-parts":[[2017,5,16]],"date-time":"2017-05-16T00:00:00Z","timestamp":1494892800000},"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>A new ergosterol analog, talarosterone (1) and a new bis-anthraquinone derivative (3) were isolated, together with ten known compounds including palmitic acid, ergosta-4,6,8(14),22-tetraen-3-one, ergosterol-5,8-endoperoxide, cyathisterone (2), emodin (4a), questinol (4b), citreorosein (4c), fallacinol (4d), rheoemodin (4e) and secalonic acid A (5), from the ethyl acetate extract of the culture of the marine sponge-associated fungus Talaromyces stipitatus KUFA 0207. The structures of the new compounds were established based on extensive 1D and 2D spectral analysis, and in the case of talarosterone (1), the absolute configurations of its stereogenic carbons were determined by X-ray crystallographic analysis. The structure and stereochemistry of cyathisterone (2) was also confirmed by X-ray analysis. The anthraquinones 4a\u2013e and secalonic acid A (5) were tested for their anti-obesity activity using the zebrafish Nile red assay. Only citreorosein (4c) and questinol (4b) exhibited significant anti-obesity activity, while emodin (4a) and secalonic acid A (5) caused toxicity (death) for all exposed zebrafish larvae after 24 h.<\/jats:p>","DOI":"10.3390\/md15050139","type":"journal-article","created":{"date-parts":[[2017,5,16]],"date-time":"2017-05-16T11:42:11Z","timestamp":1494934931000},"page":"139","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":54,"title":["A New Ergosterol Analog, a New Bis-Anthraquinone and Anti-Obesity Activity of Anthraquinones from the Marine Sponge-Associated Fungus Talaromyces stipitatus KUFA 0207"],"prefix":"10.3390","volume":"15","author":[{"given":"Jidapa","family":"Noinart","sequence":"first","affiliation":[{"name":"ICBAS-Instituto de Ci\u00eancias Biom\u00e9dicas Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5134-0115","authenticated-orcid":false,"given":"Suradet","family":"Buttachon","sequence":"additional","affiliation":[{"name":"ICBAS-Instituto de Ci\u00eancias Biom\u00e9dicas Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal"},{"name":"Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), Terminal de Cruzeiros do Porto de Lex\u00f5es, Av. General Norton de Matos s\/n, 4450-208 Matosinhos, Portugal"}]},{"given":"Tida","family":"Dethoup","sequence":"additional","affiliation":[{"name":"Department of Plant Pathology, Faculty of Agriculture, Kasetsart University, Bangkok 10240, Thailand"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8352-6539","authenticated-orcid":false,"given":"Lu\u00eds","family":"Gales","sequence":"additional","affiliation":[{"name":"ICBAS-Instituto de Ci\u00eancias Biom\u00e9dicas Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal"},{"name":"Instituto de Biologia Molecular e Celular (IBMC), Universidade do Porto, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2604-2375","authenticated-orcid":false,"given":"Jos\u00e9","family":"Pereira","sequence":"additional","affiliation":[{"name":"ICBAS-Instituto de Ci\u00eancias Biom\u00e9dicas Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal"},{"name":"Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), Terminal de Cruzeiros do Porto de Lex\u00f5es, Av. General Norton de Matos s\/n, 4450-208 Matosinhos, Portugal"}]},{"given":"Ralph","family":"Urbatzka","sequence":"additional","affiliation":[{"name":"Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), Terminal de Cruzeiros do Porto de Lex\u00f5es, Av. General Norton de Matos s\/n, 4450-208 Matosinhos, Portugal"}]},{"given":"Sara","family":"Freitas","sequence":"additional","affiliation":[{"name":"Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), Terminal de Cruzeiros do Porto de Lex\u00f5es, Av. General Norton de Matos s\/n, 4450-208 Matosinhos, Portugal"}]},{"given":"Michael","family":"Lee","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University of Leicester, University Road, Leicester LE 7 RH, UK"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2861-8286","authenticated-orcid":false,"given":"Artur","family":"Silva","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica &amp; QOPNA, Universidade de Aveiro, 3810-193 Aveiro, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4676-1409","authenticated-orcid":false,"given":"Madalena","family":"Pinto","sequence":"additional","affiliation":[{"name":"Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), Terminal de Cruzeiros do Porto de Lex\u00f5es, Av. General Norton de Matos s\/n, 4450-208 Matosinhos, Portugal"},{"name":"Laborat\u00f3rio de Qu\u00edmica Org\u00e2nica, Departamento de Ci\u00eancias Qu\u00edmicas, Faculdade de Farm\u00e1cia, Universidade do Porto, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3585-2417","authenticated-orcid":false,"given":"V\u00edtor","family":"Vasconcelos","sequence":"additional","affiliation":[{"name":"Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), Terminal de Cruzeiros do Porto de Lex\u00f5es, Av. General Norton de Matos s\/n, 4450-208 Matosinhos, Portugal"},{"name":"Departamento de Biologia, Faculdade de Ci\u00eancias, Universidade do Porto, Rua do Campo Alegre, s\/n, 4169-007 Porto, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3321-1061","authenticated-orcid":false,"given":"Anake","family":"Kijjoa","sequence":"additional","affiliation":[{"name":"ICBAS-Instituto de Ci\u00eancias Biom\u00e9dicas Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal"},{"name":"Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), Terminal de Cruzeiros do Porto de Lex\u00f5es, Av. General Norton de Matos s\/n, 4450-208 Matosinhos, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2017,5,16]]},"reference":[{"key":"ref_1","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_2","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_3","doi-asserted-by":"crossref","first-page":"888","DOI":"10.1055\/s-0042-103687","article-title":"Secondary Metabolites from the Culture of the Marine Sponge-Associated Fungi Talaromyces tratensis and Sporidesmium circinophorum","volume":"82","author":"Buttachon","year":"2016","journal-title":"Planta Med."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"72","DOI":"10.1248\/cpb.40.72","article-title":"Marine sterols. XXII. Occurrence of 3-oxo-4, 6, 8(14)-triunsaturated steroids in the sponge Dysidea herbacea","volume":"40","author":"Kobayashi","year":"1992","journal-title":"Chem. Pharm. Bull."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"685","DOI":"10.1055\/s-2001-18365","article-title":"Antimycobacterial plant terpenoids","volume":"67","author":"Cantrell","year":"2001","journal-title":"Planta Med."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"213","DOI":"10.1016\/0031-9422(94)85028-3","article-title":"Steroids from Calvatia cyathiformis","volume":"37","author":"Kawahara","year":"1994","journal-title":"Phytochemistry"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"219","DOI":"10.1038\/ja.2012.110","article-title":"Antifouling and antibacterial polyketides from marine gorgonian coral-associated fungus Penicillium sp. SCSGAF 0023","volume":"66","author":"Bao","year":"2013","journal-title":"J. Antibiot."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"1346","DOI":"10.4014\/jmb.1405.05035","article-title":"Anti-inflammatory activity of questinol isolated from marine-derived fungus Eurotium amstelodami in lipopolysaccharide-stimulated RAW 264.7 macrophages","volume":"24","author":"Yang","year":"2014","journal-title":"J. Microbiol. Biotechnol."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"298","DOI":"10.1248\/cpb1953.4.298","article-title":"The coloring matters of Xanthoria fallax (Hepp.) Arn. Fallacinal and fallacinol","volume":"4","author":"Murakami","year":"1956","journal-title":"Pharm. Bull."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"179","DOI":"10.1007\/s12223-009-0028-3","article-title":"Hydroxylated anthraquinones produced by Geosmithia species","volume":"54","author":"Kuzma","year":"2009","journal-title":"Folia Microbiol."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"199","DOI":"10.1248\/cpb.19.199","article-title":"The isolation of secalonic acid A from Aspergillus ochraceus cultured on rice","volume":"19","author":"Yamazaki","year":"1971","journal-title":"Chem. Pharm. Bull."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"3107","DOI":"10.1002\/anie.201311260","article-title":"Total syntheses of secalonic acids A and D","volume":"53","author":"Qin","year":"2014","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"879","DOI":"10.1016\/j.drudis.2007.07.024","article-title":"Pancreatic lipase inhibitors from natural sources: Unexplored potential","volume":"12","author":"Birari","year":"2007","journal-title":"Drug Discov. Today"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"2577","DOI":"10.2174\/1568026616666160415155644","article-title":"Obesity: The metabolic disease, advances on drug discovery and natural product research","volume":"16","author":"Castro","year":"2016","journal-title":"Curr. Top. Med. Chem."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"1625","DOI":"10.1016\/j.phytochem.2010.07.011","article-title":"Possible anti-obesity therapeutics from nature\u2014A review","volume":"71","author":"Yun","year":"2010","journal-title":"Phytochemistry"},{"key":"ref_16","unstructured":"(1970, January 01). Anti-obesity Product and Its Method of Preparation. Available online: http:\/\/www.google.com\/patents\/US8247001."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"781812","DOI":"10.1155\/2012\/781812","article-title":"Emodin, a naturally occurring anthraquinone derivative, ameliorates dyslipidemia by activating AMP-activated protein kinase in high-fat-diet-fed rats","volume":"2012","author":"Tzeng","year":"2012","journal-title":"Evid.-Based Complement. Altern. Med."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"204","DOI":"10.1111\/j.1476-5381.2010.00725.x","article-title":"High-throughput screening and small animal models, where are we?","volume":"160","author":"Giacomotto","year":"2010","journal-title":"Br. J. Pharmacol."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"23","DOI":"10.1186\/1743-7075-5-23","article-title":"A high throughput live transparent animal bioassay to identify non-toxic small molecules or genes that regulate vertebrate fat metabolism for obesity drug development","volume":"5","author":"Jones","year":"2008","journal-title":"Nutr. Metab."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"607","DOI":"10.1080\/10286020802133167","article-title":"A new hTopo I isomerase inhibitor produced by a mangrove endophytic fungus no. 2240","volume":"10","author":"Tan","year":"2008","journal-title":"J. Asian Nat. Prod. Res."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"1764","DOI":"10.1248\/cpb.25.1764","article-title":"Studies on the constituents of Aloe saponaria Haw. II. The structures of tetrahydroanthracene derivatives aloesaponol III and IV","volume":"25","author":"Yagi","year":"1977","journal-title":"Chem. Pharm. Bull."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"1248","DOI":"10.1248\/cpb.56.1248","article-title":"Anthraquinone-benzisochromanquinone dimers from the roots of Berchemia floribunda","volume":"56","author":"Wei","year":"2008","journal-title":"Chem. Pharm. Bull."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"3776","DOI":"10.3390\/md13063776","article-title":"A New Meroditerpene and a New Tryptoquivaline from the Algicolous Fungus Neosartorya takakii KUFC 7898","volume":"13","author":"Buttachon","year":"2015","journal-title":"Mar. Drugs"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"112","DOI":"10.1107\/S0108767307043930","article-title":"A short history of SHELX","volume":"64","author":"Sheldrick","year":"2008","journal-title":"Acta Cryst."}],"container-title":["Marine Drugs"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1660-3397\/15\/5\/139\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T18:35:57Z","timestamp":1760207757000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1660-3397\/15\/5\/139"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2017,5,16]]},"references-count":24,"journal-issue":{"issue":"5","published-online":{"date-parts":[[2017,5]]}},"alternative-id":["md15050139"],"URL":"https:\/\/doi.org\/10.3390\/md15050139","relation":{},"ISSN":["1660-3397"],"issn-type":[{"value":"1660-3397","type":"electronic"}],"subject":[],"published":{"date-parts":[[2017,5,16]]}}}