title: New Cyclotetrapeptides and a New Diketopiperzine Derivative from the Marine Sponge-Associated Fungus Neosartorya glabra KUFA 0702.
abstract: Two new cyclotetrapeptides, sartoryglabramides A (5) and B (6), and a new analog of fellutanine A (8) were isolated, together with six known compounds including ergosta-4, 6, 8 (14), 22-tetraen-3-one, ergosterol 5, 8-endoperoxide, helvolic acid, aszonalenin (1), (3R)-3-(1H-indol-3-ylmethyl)-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione (2), takakiamide (3), (11aR)-2,3-dihydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H,11aH)-dione (4), and fellutanine A (7), from the ethyl acetate extract of the culture of the marine sponge-associated fungus Neosartorya glabra KUFA 0702. The structures of the new compounds were established based on extensive 1D and 2D spectral analysis. X-ray analysis was also used to confirm the relative configuration of the amino acid constituents of sartoryglabramide A (5), and the absolute stereochemistry of the amino acid constituents of sartoryglabramide A (5) and sartoryglabramides B (6) was determined by chiral HPLC analysis of their hydrolysates by co-injection with the d- and l- amino acids standards. Compounds 1-8 were tested for their antibacterial activity against Gram-positive (Escherichia coli ATCC 25922) and Gram-negative (Staphyllococus aureus ATCC 25923) bacteria, as well as for their antifungal activity against filamentous (Aspergillus fumigatus ATCC 46645), dermatophyte (Trichophyton rubrum ATCC FF5) and yeast (Candida albicans ATCC 10231). None of the tested compounds exhibited either antibacterial (MIC > 256 μg/mL) or antifungal activities (MIC > 512 μg/mL).
authors.affiliation: <i>ICBAS</i>-Instituto de Ci&#234;ncias Biom&#233;dicas Abel Salazar, Universidade do Porto, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal. wwmzin.chem.yu@gmail.com.|Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), Rua dos Bragas 289, 4050-313 Porto, Portugal. wwmzin.chem.yu@gmail.com.
authors.forename: War War
authors.initials: WW
authors.lastname: May Zin
authors.affiliation: <i>ICBAS</i>-Instituto de Ci&#234;ncias Biom&#233;dicas Abel Salazar, Universidade do Porto, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal. nokrari_209@hotmail.com.|Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), Rua dos Bragas 289, 4050-313 Porto, Portugal. nokrari_209@hotmail.com.
authors.forename: Suradet
authors.initials: S
authors.lastname: Buttachon
authors.affiliation: Department of Plant Pathology, Faculty of Agriculture, Kasetsart University, 10240 Bangkok, Thailand. agrtdd@ku.ac.th.
authors.forename: Tida
authors.initials: T
authors.lastname: Dethoup
authors.affiliation: Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), Rua dos Bragas 289, 4050-313 Porto, Portugal. cfernandes@ff.up.pt.|Laborat&#243;rio de Qu&#237;mica Org&#226;nica, Departamento de Ci&#234;ncias Qu&#237;micas, Faculdade de Farm&#225;cia, Universidade do Porto, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal. cfernandes@ff.up.pt.
authors.forename: Carla
authors.initials: C
authors.lastname: Fernandes
authors.affiliation: Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), Rua dos Bragas 289, 4050-313 Porto, Portugal. scravo@ff.up.pt.|Laborat&#243;rio de Qu&#237;mica Org&#226;nica, Departamento de Ci&#234;ncias Qu&#237;micas, Faculdade de Farm&#225;cia, Universidade do Porto, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal. scravo@ff.up.pt.
authors.forename: Sara
authors.initials: S
authors.lastname: Cravo
authors.affiliation: Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), Rua dos Bragas 289, 4050-313 Porto, Portugal. madalena@ff.up.pt.|Laborat&#243;rio de Qu&#237;mica Org&#226;nica, Departamento de Ci&#234;ncias Qu&#237;micas, Faculdade de Farm&#225;cia, Universidade do Porto, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal. madalena@ff.up.pt.
authors.forename: Madalena M M
authors.initials: MM
authors.lastname: Pinto
authors.affiliation: <i>ICBAS</i>-Instituto de Ci&#234;ncias Biom&#233;dicas Abel Salazar, Universidade do Porto, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal. lgales@ibmc.up.pt.|Instituto de Biologia Molecular e Celular (IBMC), Universidade do Porto, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal. lgales@ibmc.up.pt.
authors.forename: Luís
authors.initials: L
authors.lastname: Gales
authors.affiliation: <i>ICBAS</i>-Instituto de Ci&#234;ncias Biom&#233;dicas Abel Salazar, Universidade do Porto, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal. jpereira@icbas.up.pt.
authors.forename: José A
authors.initials: JA
authors.lastname: Pereira
authors.affiliation: Departamento de Qu&#237;mica &amp; QOPNA, Universidade de Aveiro, 3810-193 Aveiro, Portugal. artur.silva@ua.pt.
authors.forename: Artur M S
authors.initials: AM
authors.lastname: Silva
authors.affiliation: Medicinal and Aromatic Plant Programme, Plant and Animal Sciences Department, Vocational School, Kilis Aralık University, 79000 Kilis, Turkey. nsekeroglu@gmail.com.
authors.forename: Nazim
authors.initials: N
authors.lastname: Sekeroglu
authors.affiliation: <i>ICBAS</i>-Instituto de Ci&#234;ncias Biom&#233;dicas Abel Salazar, Universidade do Porto, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal. ankijjoa@icbas.up.pt.|Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), Rua dos Bragas 289, 4050-313 Porto, Portugal. ankijjoa@icbas.up.pt.
authors.forename: Anake
authors.initials: A
authors.lastname: Kijjoa
mesh_terms: D000596:Amino Acids / Q000737:chemistry; D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000494:pharmacology; D000935:Antifungal Agents / Q000737:chemistry / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D001569:Benzodiazepines / Q000737:chemistry / Q000494:pharmacology; D002176:Candida albicans / Q000187:drug effects; D054659:Diketopiperazines / Q000737:chemistry* / Q000494:pharmacology; D004875:Ergosterol / Q000737:chemistry / Q000494:pharmacology; D005658:Fungi / Q000737:chemistry*; D005672:Fusidic Acid / Q000031:analogs & derivatives / Q000737:chemistry / Q000494:pharmacology; D026121:Indole Alkaloids / Q000737:chemistry / Q000494:pharmacology; D008826:Microbial Sensitivity Tests / Q000379:methods; D055326:Neosartorya / Q000737:chemistry*; D009842:Oligopeptides / Q000737:chemistry* / Q000494:pharmacology; D011161:Porifera / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D054659:Diketopiperazines; D026121:Indole Alkaloids; D009842:Oligopeptides; C000602356:aszonalenin; D001569:Benzodiazepines; D005672:Fusidic Acid; C011267:helvolic acid; D004875:Ergosterol
keywords: Mycale sp.; Neosartorya glabra; cyclotetrapeptides; diketopiperazines; fellutanine A epoxide; marine-derived fungus; sartoryglabramides A and B