Bis-Indolyl Benzenoids, Hydroxypyrrolidine Derivatives and Other Constituents from Cultures of the Marine Sponge-Associated Fungus Aspergillus candidus KUFA0062
A previously unreported bis-indolyl benzenoid, candidusin D (2e) and a new hydroxypyrrolidine alkaloid, preussin C (5b) were isolated together with fourteen previously described compounds: palmitic acid, clionasterol, ergosterol 5,8-endoperoxides, chrysophanic acid (1a), emodin (1b), six bis-indolyl...
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| Format: | Article |
| Language: | English |
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MDPI AG
2018-04-01
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| Series: | Marine Drugs |
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| Online Access: | http://www.mdpi.com/1660-3397/16/4/119 |
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| author | Suradet Buttachon Alice A. Ramos Ângela Inácio Tida Dethoup Luís Gales Michael Lee Paulo M. Costa Artur M. S. Silva Nazim Sekeroglu Eduardo Rocha Madalena M. M. Pinto José A. Pereira Anake Kijjoa |
| author_facet | Suradet Buttachon Alice A. Ramos Ângela Inácio Tida Dethoup Luís Gales Michael Lee Paulo M. Costa Artur M. S. Silva Nazim Sekeroglu Eduardo Rocha Madalena M. M. Pinto José A. Pereira Anake Kijjoa |
| author_sort | Suradet Buttachon |
| collection | DOAJ |
| description | A previously unreported bis-indolyl benzenoid, candidusin D (2e) and a new hydroxypyrrolidine alkaloid, preussin C (5b) were isolated together with fourteen previously described compounds: palmitic acid, clionasterol, ergosterol 5,8-endoperoxides, chrysophanic acid (1a), emodin (1b), six bis-indolyl benzenoids including asterriquinol D dimethyl ether (2a), petromurin C (2b), kumbicin B (2c), kumbicin A (2d), 2″-oxoasterriquinol D methyl ether (3), kumbicin D (4), the hydroxypyrrolidine alkaloid preussin (5a), (3S, 6S)-3,6-dibenzylpiperazine-2,5-dione (6) and 4-(acetylamino) benzoic acid (7), from the cultures of the marine sponge-associated fungus Aspergillus candidus KUFA 0062. Compounds 1a, 2a–e, 3, 4, 5a–b, and 6 were tested for their antibacterial activity against Gram-positive and Gram-negative reference and multidrug-resistant strains isolated from the environment. Only 5a exhibited an inhibitory effect against S. aureus ATCC 29213 and E. faecalis ATCC29212 as well as both methicillin-resistant S. aureus (MRSA) and vancomycin-resistant enterococci (VRE) strains. Both 1a and 5a also reduced significant biofilm formation in E. coli ATCC 25922. Moreover, 2b and 5a revealed a synergistic effect with oxacillin against MRSA S. aureus 66/1 while 5a exhibited a strong synergistic effect with the antibiotic colistin against E. coli 1410/1. Compound 1a, 2a–e, 3, 4, 5a–b, and 6 were also tested, together with the crude extract, for cytotoxic effect against eight cancer cell lines: HepG2, HT29, HCT116, A549, A 375, MCF-7, U-251, and T98G. Except for 1a, 2a, 2d, 4, and 6, all the compounds showed cytotoxicity against all the cancer cell lines tested. |
| first_indexed | 2024-04-14T05:16:23Z |
| format | Article |
| id | doaj.art-373789cc2ee348d59b71f9911d48cc0e |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-04-14T05:16:23Z |
| publishDate | 2018-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-373789cc2ee348d59b71f9911d48cc0e2022-12-22T02:10:21ZengMDPI AGMarine Drugs1660-33972018-04-0116411910.3390/md16040119md16040119Bis-Indolyl Benzenoids, Hydroxypyrrolidine Derivatives and Other Constituents from Cultures of the Marine Sponge-Associated Fungus Aspergillus candidus KUFA0062Suradet Buttachon0Alice A. Ramos1Ângela Inácio2Tida Dethoup3Luís Gales4Michael Lee5Paulo M. Costa6Artur M. S. Silva7Nazim Sekeroglu8Eduardo Rocha9Madalena M. M. Pinto10José A. Pereira11Anake Kijjoa12ICBAS-Instituto de Ciências Biomédicas Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, PortugalICBAS-Instituto de Ciências Biomédicas Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, PortugalICBAS-Instituto de Ciências Biomédicas Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, PortugalDepartment of Plant Pathology, Faculty of Agriculture, Kasetsart University, Bangkok 10240, ThailandICBAS-Instituto de Ciências Biomédicas Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, PortugalDepartment of Chemistry, University of Leicester, University Road, Leicester LE 7 RH, UKICBAS-Instituto de Ciências Biomédicas Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, PortugalDepartamento de Química & QOPNA, Universidade de Aveiro, 3810-193 Aveiro, PortugalMedicinal and Aromatic Plant Programme, Plant and Animal Sciences Department, Vocational School, Kilis 7 Aralık University, 79000 Kilis, TurkeyICBAS-Instituto de Ciências Biomédicas Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, PortugalInterdisciplinary Centre of Marine and Environmental Research (CIIMAR), Terminal de Cruzeiros do Porto de Lexões, Av. General Norton de Matos s/n, 4450-208 Matosinhos, PortugalICBAS-Instituto de Ciências Biomédicas Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, PortugalICBAS-Instituto de Ciências Biomédicas Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, PortugalA previously unreported bis-indolyl benzenoid, candidusin D (2e) and a new hydroxypyrrolidine alkaloid, preussin C (5b) were isolated together with fourteen previously described compounds: palmitic acid, clionasterol, ergosterol 5,8-endoperoxides, chrysophanic acid (1a), emodin (1b), six bis-indolyl benzenoids including asterriquinol D dimethyl ether (2a), petromurin C (2b), kumbicin B (2c), kumbicin A (2d), 2″-oxoasterriquinol D methyl ether (3), kumbicin D (4), the hydroxypyrrolidine alkaloid preussin (5a), (3S, 6S)-3,6-dibenzylpiperazine-2,5-dione (6) and 4-(acetylamino) benzoic acid (7), from the cultures of the marine sponge-associated fungus Aspergillus candidus KUFA 0062. Compounds 1a, 2a–e, 3, 4, 5a–b, and 6 were tested for their antibacterial activity against Gram-positive and Gram-negative reference and multidrug-resistant strains isolated from the environment. Only 5a exhibited an inhibitory effect against S. aureus ATCC 29213 and E. faecalis ATCC29212 as well as both methicillin-resistant S. aureus (MRSA) and vancomycin-resistant enterococci (VRE) strains. Both 1a and 5a also reduced significant biofilm formation in E. coli ATCC 25922. Moreover, 2b and 5a revealed a synergistic effect with oxacillin against MRSA S. aureus 66/1 while 5a exhibited a strong synergistic effect with the antibiotic colistin against E. coli 1410/1. Compound 1a, 2a–e, 3, 4, 5a–b, and 6 were also tested, together with the crude extract, for cytotoxic effect against eight cancer cell lines: HepG2, HT29, HCT116, A549, A 375, MCF-7, U-251, and T98G. Except for 1a, 2a, 2d, 4, and 6, all the compounds showed cytotoxicity against all the cancer cell lines tested.http://www.mdpi.com/1660-3397/16/4/119Aspergillus candidusAspergillaceaesponge-associated fungusbis-indolyl benzenoidshydroxypyrrolidineantibacterial activitycytotoxicity |
| spellingShingle | Suradet Buttachon Alice A. Ramos Ângela Inácio Tida Dethoup Luís Gales Michael Lee Paulo M. Costa Artur M. S. Silva Nazim Sekeroglu Eduardo Rocha Madalena M. M. Pinto José A. Pereira Anake Kijjoa Bis-Indolyl Benzenoids, Hydroxypyrrolidine Derivatives and Other Constituents from Cultures of the Marine Sponge-Associated Fungus Aspergillus candidus KUFA0062 Marine Drugs Aspergillus candidus Aspergillaceae sponge-associated fungus bis-indolyl benzenoids hydroxypyrrolidine antibacterial activity cytotoxicity |
| title | Bis-Indolyl Benzenoids, Hydroxypyrrolidine Derivatives and Other Constituents from Cultures of the Marine Sponge-Associated Fungus Aspergillus candidus KUFA0062 |
| title_full | Bis-Indolyl Benzenoids, Hydroxypyrrolidine Derivatives and Other Constituents from Cultures of the Marine Sponge-Associated Fungus Aspergillus candidus KUFA0062 |
| title_fullStr | Bis-Indolyl Benzenoids, Hydroxypyrrolidine Derivatives and Other Constituents from Cultures of the Marine Sponge-Associated Fungus Aspergillus candidus KUFA0062 |
| title_full_unstemmed | Bis-Indolyl Benzenoids, Hydroxypyrrolidine Derivatives and Other Constituents from Cultures of the Marine Sponge-Associated Fungus Aspergillus candidus KUFA0062 |
| title_short | Bis-Indolyl Benzenoids, Hydroxypyrrolidine Derivatives and Other Constituents from Cultures of the Marine Sponge-Associated Fungus Aspergillus candidus KUFA0062 |
| title_sort | bis indolyl benzenoids hydroxypyrrolidine derivatives and other constituents from cultures of the marine sponge associated fungus aspergillus candidus kufa0062 |
| topic | Aspergillus candidus Aspergillaceae sponge-associated fungus bis-indolyl benzenoids hydroxypyrrolidine antibacterial activity cytotoxicity |
| url | http://www.mdpi.com/1660-3397/16/4/119 |
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