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Mar. Drugs 2014, 12(10), 5160-5173; doi:10.3390/md12105160

New Isocoumarin Derivatives and Meroterpenoids from the Marine Sponge-Associated Fungus Aspergillus similanensis sp. nov. KUFA 0013

1
ICBAS—Instituto de Ciências Biomédicas de Abel Salazar, Universidade do Porto, Rua de Jorge Viterbo Ferreira 228, 4050-313 Porto, Portugal
2
Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), Rua dos Bragas 289, 4050-123 Porto, Portugal
3
Department of Plant Pathology, Faculty of Agriculture, Kasetsart University, Bangkok 10240, Thailand
4
Centro de Química Medicinal da Universidade do Porto (CEQUIMED-UP) and Laboratório de Química Orgânica e Farmacêutica, Departamento de Ciências Químicas, Faculdade de Farmácia, Universidade do Porto, Rua de Jorge Viterbo 228, 4050-313 Porto, Portugal
5
Instituto de Biologia Celular e Molecular (IBMC), Universidade do Porto, 4099-003 Porto, Portugal
6
Departamento de Química & QOPNA, Universidade de Aveiro, 4810-193 Aveiro, Portugal
*
Author to whom correspondence should be addressed.
Received: 28 July 2014 / Revised: 24 September 2014 / Accepted: 25 September 2014 / Published: 14 October 2014
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Abstract

Two new isocoumarin derivatives, including a new 5-hydroxy-8-methyl-2H, 6H-pyrano[3,4-g]chromen-2,6-dione (1) and 6,8-dihydroxy-3,7-dimethylisocoumarin (2b), a new chevalone derivative, named chevalone E (3), and a new natural product pyripyropene S (6) were isolated together with 6, 8-dihydroxy-3-methylisocoumarin (2a), reticulol (2c), p-hydroxybenzaldehyde, chevalone B, chevalone C, S14-95 (4), and pyripyropene E (5) from the ethyl acetate extract of the undescribed marine sponge-associated fungus Aspergillus similanensis KUFA 0013. The structures of the new compounds were established based on 1D and 2D NMR spectral analysis, and in the case of compound 3, X-ray analysis was used to confirm its structure and the absolute configuration of its stereogenic carbons. Compounds 1, 2ac and 36 were evaluated for their antimicrobial activity against Gram-positive and Gram-negative bacteria, Candida albicans ATCC 10231, and multidrug-resistant isolates from the environment. Chevalone E (3) was found to show synergism with the antibiotic oxacillin against methicillin-resistant Staphylococcus aureus (MRSA). View Full-Text
Keywords: Aspergillus similanensis; similanpyrones; isocoumarins; meroditerpenes; pyripyropenes; chevalones Aspergillus similanensis; similanpyrones; isocoumarins; meroditerpenes; pyripyropenes; chevalones
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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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MDPI and ACS Style

Prompanya, C.; Dethoup, T.; Bessa, L.J.; Pinto, M.M.M.; Gales, L.; Costa, P.M.; Silva, A.M.S.; Kijjoa, A. New Isocoumarin Derivatives and Meroterpenoids from the Marine Sponge-Associated Fungus Aspergillus similanensis sp. nov. KUFA 0013. Mar. Drugs 2014, 12, 5160-5173.

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