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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.
Mar. Drugs 2014, 12(10), 5160-5173; https://doi.org/10.3390/md12105160
Received: 28 July 2014 / Revised: 24 September 2014 / Accepted: 25 September 2014 / Published: 14 October 2014
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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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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