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Mar. Drugs 2018, 16(4), 119; https://doi.org/10.3390/md16040119

Bis-Indolyl Benzenoids, Hydroxypyrrolidine Derivatives and Other Constituents from Cultures of the Marine Sponge-Associated Fungus Aspergillus candidus KUFA0062

1
ICBAS-Instituto de Ciências Biomédicas Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal
2
Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), Terminal de Cruzeiros do Porto de Lexões, Av. General Norton de Matos s/n, 4450-208 Matosinhos, Portugal
3
Department of Plant Pathology, Faculty of Agriculture, Kasetsart University, Bangkok 10240, Thailand
4
Instituto de Biologia Molecular e Celular (i3S-IBMC), Universidade do Porto, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal
5
Department of Chemistry, University of Leicester, University Road, Leicester LE 7 RH, UK
6
Departamento de Química & QOPNA, Universidade de Aveiro, 3810-193 Aveiro, Portugal
7
Medicinal and Aromatic Plant Programme, Plant and Animal Sciences Department, Vocational School, Kilis 7 Aralık University, 79000 Kilis, Turkey
8
Laboratório de Química Orgânica, Departamento de Ciências Químicas, Faculdade de Farmácia, Universidade do Porto, Rua de Jorge Viterbo Ferreira, 228, 4050-3 13 Porto, Portugal
*
Authors to whom correspondence should be addressed.
Received: 14 March 2018 / Revised: 27 March 2018 / Accepted: 5 April 2018 / Published: 6 April 2018
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Abstract

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. View Full-Text
Keywords: Aspergillus candidus; Aspergillaceae; sponge-associated fungus; bis-indolyl benzenoids; hydroxypyrrolidine; antibacterial activity; cytotoxicity Aspergillus candidus; Aspergillaceae; sponge-associated fungus; bis-indolyl benzenoids; hydroxypyrrolidine; antibacterial activity; cytotoxicity
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Buttachon, S.; Ramos, A.A.; Inácio, Â.; Dethoup, T.; Gales, L.; Lee, M.; Costa, P.M.; Silva, A.M.S.; Sekeroglu, N.; Rocha, E.; Pinto, M.M.M.; Pereira, J.A.; Kijjoa, A. Bis-Indolyl Benzenoids, Hydroxypyrrolidine Derivatives and Other Constituents from Cultures of the Marine Sponge-Associated Fungus Aspergillus candidus KUFA0062. Mar. Drugs 2018, 16, 119.

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