{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,11,28]],"date-time":"2025-11-28T12:18:25Z","timestamp":1764332305519,"version":"build-2065373602"},"reference-count":40,"publisher":"MDPI AG","issue":"3","license":[{"start":{"date-parts":[[2015,3,17]],"date-time":"2015-03-17T00:00:00Z","timestamp":1426550400000},"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 isocoumarin derivative, similanpyrone C (1), a new cyclohexapeptide, similanamide (2), and a new pyripyropene derivative, named pyripyropene T (3) were isolated from the ethyl acetate extract of the culture of the marine sponge-associated fungus Aspergillus similanensis KUFA 0013. The structures of the compounds were established based on 1D and 2D NMR spectral analysis, and in the case of compound 2 the stereochemistry of its amino acid constituents was determined by chiral HPLC analysis of the hydrolysate by co-injection with the d and l amino acids standards. Compounds 2 and 3 were evaluated for their in vitro growth inhibitory activity against MCF-7 (breast adenocarcinoma), NCI-H460 (non-small cell lung cancer) and A373 (melanoma) cell lines, as well as antibacterial activity against reference strains and the environmental  multidrug-resistant isolates (MRS and VRE). Only compound 2 exhibited weak activity against the three cancer cell lines, and neither of them showed antibacterial activity.<\/jats:p>","DOI":"10.3390\/md13031432","type":"journal-article","created":{"date-parts":[[2015,3,17]],"date-time":"2015-03-17T11:04:24Z","timestamp":1426590264000},"page":"1432-1450","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":66,"title":["A New Cyclic Hexapeptide and a New Isocoumarin  Derivative from the Marine Sponge-Associated Fungus Aspergillus similanensis KUFA 0013"],"prefix":"10.3390","volume":"13","author":[{"given":"Chadaporn","family":"Prompanya","sequence":"first","affiliation":[{"name":"ICBAS-Instituto de Ci\u00eancias Biom\u00e9dicas Abel Salazar, Universidade do Porto,  Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal"},{"name":"Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), Rua dos Bragas 289, 4050-123 Porto, Portugal"}]},{"given":"Carla","family":"Fernandes","sequence":"additional","affiliation":[{"name":"Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), Rua dos Bragas 289, 4050-123 Porto, Portugal"},{"name":"Centro de Qu\u00edmica Medicinal da Universidade do Porto (CEQUIMED-UP), Laborat\u00f3rio de Qu\u00edmica Org\u00e2nica, Departamento de Ci\u00eancias Qu\u00edmicas, Faculdade de Farm\u00e1cia, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal"}]},{"given":"Sara","family":"Cravo","sequence":"additional","affiliation":[{"name":"Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), Rua dos Bragas 289, 4050-123 Porto, Portugal"},{"name":"Centro de Qu\u00edmica Medicinal da Universidade do Porto (CEQUIMED-UP), Laborat\u00f3rio de Qu\u00edmica Org\u00e2nica, Departamento de Ci\u00eancias Qu\u00edmicas, Faculdade de Farm\u00e1cia, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, 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), Rua dos Bragas 289, 4050-123 Porto, Portugal"},{"name":"Centro de Qu\u00edmica Medicinal da Universidade do Porto (CEQUIMED-UP), Laborat\u00f3rio de Qu\u00edmica Org\u00e2nica, Departamento de Ci\u00eancias Qu\u00edmicas, Faculdade de Farm\u00e1cia, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9079-3010","authenticated-orcid":false,"given":"Tida","family":"Dethoup","sequence":"additional","affiliation":[{"name":"Department of Plant Pathology, Faculty of Agriculture, Kasetsart University, Bangkok 10240, Thailand"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2861-8286","authenticated-orcid":false,"given":"Artur","family":"Silva","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica & QOPNA, Universidade de Aveiro, 3810-193 Aveiro, 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, Universidade do Porto,  Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal"},{"name":"Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), Rua dos Bragas 289, 4050-123 Porto, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2015,3,17]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"143","DOI":"10.1039\/b301926h","article-title":"Marine-derived fungi: A chemically and biologically diverse group of microorganisms","volume":"21","author":"Bugni","year":"2004","journal-title":"Nat. Prod. Rep."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"1142","DOI":"10.1039\/b607254m","article-title":"Marine natural products of fungal origin","volume":"24","author":"Saleem","year":"2007","journal-title":"Nat. Prod. Rep."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"290","DOI":"10.1039\/c0np00061b","article-title":"Secondary metabolites of fungi from marine habitats","volume":"28","author":"Rateb","year":"2011","journal-title":"Nat. Prod. Rep."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"1182","DOI":"10.1080\/14786419.2014.923996","article-title":"Ergosteroid derivatives from an algicolous strain of Aspergillus ustus","volume":"28","author":"Liu","year":"2014","journal-title":"Nat. Prod. Res."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"1174","DOI":"10.1248\/cpb.59.1174","article-title":"Flavusides A and B, antibacterial cerebrosides from the marine-derived fungus Aspergillus flavus","volume":"59","author":"Yang","year":"2011","journal-title":"Chem. Pharm. Bull."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"1326","DOI":"10.1016\/j.bmcl.2011.12.083","article-title":"New bisabolane sesquiterpenoids from a marine-derived fungus Aspergillus sp. isolated from the sponge Xestospongia testudinaria","volume":"22","author":"Sun","year":"2012","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"4192","DOI":"10.1016\/j.tetlet.2012.05.144","article-title":"Novel pyridino-\u03b1-pyrone sesquiterpene type pileotin prduced by a sea urchin-derived Aspergillus sp","volume":"53","author":"Kitano","year":"2012","journal-title":"Tetrahedron Lett."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"623","DOI":"10.1002\/hlca.201000283","article-title":"Ophiobolin sesterterpenoids and pyrrolidine alkaloids from the sponge-derived fungus Aspergillus ustus","volume":"94","author":"Liu","year":"2011","journal-title":"Helv. Chim. Acta"},{"key":"ref_9","first-page":"1411","article-title":"Ophiobolin O and 6-epi-ophiobolin O, two new cytotoxic sesterterpenes from the marine-derived fungus Aspergillus sp","volume":"7","author":"Zhang","year":"2012","journal-title":"Nat. Prod. Commun."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"148","DOI":"10.1021\/np2006742","article-title":"Asperolides A\u2013C, tetranorlabdane diterpenoids from the marine alga-derived endophytic fungus Aspergillus wentii EN-48","volume":"75","author":"Sun","year":"2012","journal-title":"J. Nat. Prod."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"2789","DOI":"10.1016\/j.tetlet.2014.02.062","article-title":"Marine bacterial inhibitors from the sponge-derived fungus Aspergillus sp","volume":"55","author":"Zhou","year":"2014","journal-title":"Tetrahedron Lett."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"1774","DOI":"10.1271\/bbb.120047","article-title":"Anthraquinone derivatives produced by marine-derived fungus Aspergillus versicolor EN-7","volume":"76","author":"Zhang","year":"2012","journal-title":"Biosci. Biotechnol. Biochem."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"1346","DOI":"10.1021\/np3002699","article-title":"Halogenated anthraquinones from the marine-derived fungus Aspergillus sp","volume":"75","author":"Huang","year":"2012","journal-title":"SCSIO F063. J. Nat. Prod."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"895","DOI":"10.1080\/14786419.2014.891114","article-title":"Nucleoside derivatives from the marine-derived fungus Aspergillus versicolor","volume":"28","author":"Chen","year":"2014","journal-title":"Nat. Prod. Res."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"2615","DOI":"10.1016\/j.tetlet.2012.03.043","article-title":"Aspergilazine A, a diketopiperazine d\u00edmer with a rare N-1 to C-6 linkage, from a marine-derived fungus Aspergillus taichungensis","volume":"53","author":"Cai","year":"2012","journal-title":"Tetrahedron Lett."},{"key":"ref_16","first-page":"329","article-title":"Antifouling indole alkaloids from two marine-derived fungi","volume":"8","author":"He","year":"2013","journal-title":"Nat. Prod. Commun."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"2327","DOI":"10.1021\/ol4009624","article-title":"Aspeverin, a new alkaloid from algicolous strain of Aspergillus versicolor","volume":"15","author":"Ji","year":"2013","journal-title":"Org. Lett."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"1438","DOI":"10.1021\/np1002498","article-title":"Notoamide O, a structurally unprecedented prenylated \u00edndole alkaloid, and notamides P-R from a marine-derived fungus, Aspergillus sp","volume":"73","author":"Tsukamoto","year":"2010","journal-title":"J. Nat. Prod."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"385","DOI":"10.1002\/cbdv.201100061","article-title":"2,5-Diketopiperazines from the marine-derived fungus Aspergillus fumigatus YK-7","volume":"9","author":"Wang","year":"2012","journal-title":"Chem. Biodivers."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"4770","DOI":"10.1021\/ol302051x","article-title":"Brevianamides with antitubercular potential from a marine-derived isolate of Aspergillus versicolor","volume":"14","author":"Song","year":"2012","journal-title":"Org. Lett."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"547","DOI":"10.1021\/np300707x","article-title":"Bioactive indole alkaloids and phenyl ether derivatives from a marine-derived Aspergillus sp. fungus","volume":"76","author":"Chen","year":"2013","journal-title":"J. Nat. Prod."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"983","DOI":"10.1021\/np400132m","article-title":"Alkaloids from the deep-sea-derived fungus Aspergillus westerdijkiae DFFSCS013","volume":"76","author":"Peng","year":"2013","journal-title":"J. Nat. Prod."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"1182","DOI":"10.1021\/np300897v","article-title":"Asperterrestide A, a cytotoxic tetrapeptide from the marine-derived fungus Aspergillus terreus SCSGAF0162","volume":"76","author":"He","year":"2013","journal-title":"J. Nat. Prod."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"1065","DOI":"10.1002\/hlca.201000408","article-title":"Two new cyclic pentapeptides from the marine-derived fungus Aspergillus versicolor","volume":"96","author":"Zhou","year":"2011","journal-title":"Hel. Chim. Acta"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"7085","DOI":"10.1016\/j.tet.2011.07.003","article-title":"Cyclopeptides and polyketides from coral-associated fungus, Aspergillus versicolor LCJ-5-4","volume":"67","author":"Zhuang","year":"2011","journal-title":"Tetrahedron"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"786","DOI":"10.1007\/s10600-011-0059-2","article-title":"A new cyclic peptide from the marine fungal strain Aspergillus sp. AF119","volume":"47","author":"Liu","year":"2011","journal-title":"Chem. Nat. Compd (Engl. Transl.)"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"2113","DOI":"10.1016\/j.tet.2013.01.021","article-title":"New cyclic tripeptides and asteltoxins from gorgonian-derived fungus Aspergillus sp. SCSGAF0076","volume":"69","author":"Bao","year":"2013","journal-title":"Tetrahedron"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"776","DOI":"10.1080\/14786419.2014.880911","article-title":"Psychrophilin E, a new cyclopeptide, from co-fermentation of two marine alga-derived fungi of the genus Aspergillus","volume":"28","author":"Ebada","year":"2014","journal-title":"Nat. Prod. Res."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"5160","DOI":"10.3390\/md12105160","article-title":"New isocoumarin derivatives and meroterpenoids from the marine sponge-associated fungus Aspergillus similanensis sp. nov. KUFA 0013","volume":"12","author":"Prompanya","year":"2014","journal-title":"Mar. Drugs"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"1309","DOI":"10.1271\/bbb.100098","article-title":"Determination of absolute structure of cyclic peptides, PF1171A and PF1171C, from unidentified ascomycete OK-128","volume":"74","author":"Kai","year":"2010","journal-title":"Biosci. Biotechnol. Biochem."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"7844","DOI":"10.1021\/jo500861k","article-title":"Total synthesis and biological evaluation of PF1171A, C, F and G, cyclic hxapeptides with insecticidal activity","volume":"79","author":"Masuda","year":"2014","journal-title":"J. Org. Chem."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"1696","DOI":"10.1021\/np0605891","article-title":"Cyclic peptide from an endophytic fungus obtained from a mangrove leaf (Kandelia candel)","volume":"70","author":"Huang","year":"2007","journal-title":"J. Nat. Prod."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"123","DOI":"10.1016\/0021-9673(95)01198-6","article-title":"Facile liquid chromatographic enantioresolution of native amino acids and peptides using a teicoplanin chiral stationary phase","volume":"731","author":"Berthod","year":"1996","journal-title":"J. Chromatogr. A"},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"283","DOI":"10.1016\/S0021-9673(97)00938-2","article-title":"High-performance liquid chromatographic separation of enantiomers of unusual amino acids on a teicoplanin chiral stationary phase","volume":"793","author":"Armstrong","year":"1998","journal-title":"J. Chromatogr. A"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"123","DOI":"10.1016\/j.seppur.2013.09.010","article-title":"Enantioselective separation of unusual amino acids by high performance liquid chromatography","volume":"119","author":"Vozka","year":"2013","journal-title":"Sep. Purif. Technol."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"694","DOI":"10.1021\/np400009a","article-title":"Nocardiamides A and B, two cyclohexapeptides from the marine-derived Actinomycete nocardiopsis sp. CNX037","volume":"76","author":"Wu","year":"2013","journal-title":"J. Nat. Prod."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"2009","DOI":"10.1021\/np400145u","article-title":"Hytramycins V and I, Anti-mycobacterium tuberculosis hexapeptides from a Streptomyces hygroscopicus strain","volume":"76","author":"Cai","year":"2013","journal-title":"J. Nat. Prod."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"1937","DOI":"10.1021\/np500399v","article-title":"Cyclic hexapeptides from the deep South China Sea-derived Streptomyces scopuliridis SCSIO ZJ46 active against pathogenic Gram-positive bacteria","volume":"77","author":"Song","year":"2014","journal-title":"J. Nat. Prod."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"6","DOI":"10.3390\/md502006","article-title":"Anticancer activity evaluation of kuanoniamines A and C isolated from the marine sponge Oceanapia sagittaria, collected from the Gulf of Thailand","volume":"5","author":"Kijjoa","year":"2007","journal-title":"Mar. Drugs"},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"822","DOI":"10.3390\/md12020822","article-title":"Antibacterial and antibiofilm activities of tryptoquivalines and meroditerpenes isolated from the marine-derived fungi Neosartorya paulistensis, N. laciniosa, N. tsunodae, and the soil fungi N. fischeri and N. siamensis","volume":"12","author":"Gomes","year":"2014","journal-title":"Mar. 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