New isocoumarin derivatives and meroterpenoids from the marine sponge-associated fungus Aspergillus similanensis sp. nov. KUFA 0013

  • Mar Drugs. 2014 Oct 14;12(10):5160-73. doi: 10.3390/md12105160.
Chadaporn Prompanya  1 ,  Tida Dethoup  2 ,  Lucinda J Bessa  3 ,  Madalena M M Pinto  4 ,  Luís Gales  5 ,  Paulo M Costa  6 ,  Artur M S Silva  7 ,  Anake Kijjoa  8
Affiliations
  • 1. ICBAS-Instituto de Ciências Biomédicas de Abel Salazar, Universidade do Porto, Rua de Jorge Viterbo Ferreira 228, 4050-313 Porto, Portugal. [email protected].
  • 2. Department of Plant Pathology, Faculty of Agriculture, Kasetsart University, Bangkok 10240, Thailand. [email protected].
  • 3. ICBAS-Instituto de Ciências Biomédicas de Abel Salazar, Universidade do Porto, Rua de Jorge Viterbo Ferreira 228, 4050-313 Porto, Portugal. [email protected].
  • 4. Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), Rua dos Bragas 289, 4050-123 Porto, Portugal. [email protected].
  • 5. ICBAS-Instituto de Ciências Biomédicas de Abel Salazar, Universidade do Porto, Rua de Jorge Viterbo Ferreira 228, 4050-313 Porto, Portugal. [email protected].
  • 6. ICBAS-Instituto de Ciências Biomédicas de Abel Salazar, Universidade do Porto, Rua de Jorge Viterbo Ferreira 228, 4050-313 Porto, Portugal. [email protected].
  • 7. Departamento de Química & QOPNA, Universidade de Aveiro, 4810-193 Aveiro, Portugal. [email protected].
  • 8. ICBAS-Instituto de Ciências Biomédicas de Abel Salazar, Universidade do Porto, Rua de Jorge Viterbo Ferreira 228, 4050-313 Porto, Portugal. [email protected].
PMID: 25317534 DOI: 10.3390/md12105160
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, 2a-c and 3-6 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).

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