A New Cyclic Hexapeptide and a New Isocoumarin Derivative from the Marine Sponge-Associated Fungus Aspergillus similanensis KUFA 0013
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 structur...
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| Format: | Article |
| Language: | English |
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MDPI AG
2015-03-01
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| Series: | Marine Drugs |
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| Online Access: | http://www.mdpi.com/1660-3397/13/3/1432 |
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| author | Chadaporn Prompanya Carla Fernandes Sara Cravo Madalena M. M. Pinto Tida Dethoup Artur M. S. Silva Anake Kijjoa |
| author_facet | Chadaporn Prompanya Carla Fernandes Sara Cravo Madalena M. M. Pinto Tida Dethoup Artur M. S. Silva Anake Kijjoa |
| author_sort | Chadaporn Prompanya |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-04-14T01:33:17Z |
| format | Article |
| id | doaj.art-dc84a2c56bdf4a8a98149d0f3a27d0a9 |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-04-14T01:33:17Z |
| publishDate | 2015-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-dc84a2c56bdf4a8a98149d0f3a27d0a92022-12-22T02:20:05ZengMDPI AGMarine Drugs1660-33972015-03-011331432145010.3390/md13031432md13031432A New Cyclic Hexapeptide and a New Isocoumarin Derivative from the Marine Sponge-Associated Fungus Aspergillus similanensis KUFA 0013Chadaporn Prompanya0Carla Fernandes1Sara Cravo2Madalena M. M. Pinto3Tida Dethoup4Artur M. S. Silva5Anake Kijjoa6ICBAS-Instituto de Ciências Biomédicas Abel Salazar, Universidade do Porto, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, PortugalInterdisciplinary Centre of Marine and Environmental Research (CIIMAR), Rua dos Bragas 289, 4050-123 Porto, PortugalInterdisciplinary Centre of Marine and Environmental Research (CIIMAR), Rua dos Bragas 289, 4050-123 Porto, PortugalInterdisciplinary Centre of Marine and Environmental Research (CIIMAR), Rua dos Bragas 289, 4050-123 Porto, PortugalDepartment of Plant Pathology, Faculty of Agriculture, Kasetsart University, Bangkok 10240, ThailandDepartamento de Química & QOPNA, Universidade de Aveiro, 3810-193 Aveiro, PortugalICBAS-Instituto de Ciências Biomédicas Abel Salazar, Universidade do Porto, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, PortugalA 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.http://www.mdpi.com/1660-3397/13/3/1432Aspergillus similanensiscyclic hexapeptidesimilanamideisocoumarinsimilanpyrone Cpyripyropene T |
| spellingShingle | Chadaporn Prompanya Carla Fernandes Sara Cravo Madalena M. M. Pinto Tida Dethoup Artur M. S. Silva Anake Kijjoa A New Cyclic Hexapeptide and a New Isocoumarin Derivative from the Marine Sponge-Associated Fungus Aspergillus similanensis KUFA 0013 Marine Drugs Aspergillus similanensis cyclic hexapeptide similanamide isocoumarin similanpyrone C pyripyropene T |
| title | A New Cyclic Hexapeptide and a New Isocoumarin Derivative from the Marine Sponge-Associated Fungus Aspergillus similanensis KUFA 0013 |
| title_full | A New Cyclic Hexapeptide and a New Isocoumarin Derivative from the Marine Sponge-Associated Fungus Aspergillus similanensis KUFA 0013 |
| title_fullStr | A New Cyclic Hexapeptide and a New Isocoumarin Derivative from the Marine Sponge-Associated Fungus Aspergillus similanensis KUFA 0013 |
| title_full_unstemmed | A New Cyclic Hexapeptide and a New Isocoumarin Derivative from the Marine Sponge-Associated Fungus Aspergillus similanensis KUFA 0013 |
| title_short | A New Cyclic Hexapeptide and a New Isocoumarin Derivative from the Marine Sponge-Associated Fungus Aspergillus similanensis KUFA 0013 |
| title_sort | new cyclic hexapeptide and a new isocoumarin derivative from the marine sponge associated fungus aspergillus similanensis kufa 0013 |
| topic | Aspergillus similanensis cyclic hexapeptide similanamide isocoumarin similanpyrone C pyripyropene T |
| url | http://www.mdpi.com/1660-3397/13/3/1432 |
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