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Mar. Drugs 2016, 14(7), 134; doi:10.3390/md14070134

New Polyketides and New Benzoic Acid Derivatives from the Marine Sponge-Associated Fungus Neosartorya quadricincta KUFA 0081

1
ICBAS—Instituto de Ciências Biomédicas 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, 4050-313 Porto, Portugal
3
Department of Plant Pathology, Faculty of Agriculture, Kasetsart University, 10900 Bangkok, Thailand
4
Instituto de Biologia Molecular e Celular (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
Laboratório de Química Orgânica, Departamento de Ciências Químicas, Faculdade de Farmácia Universidade do Porto, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal
*
Author to whom correspondence should be addressed.
Academic Editor: Russell Kerr
Received: 30 June 2016 / Revised: 8 July 2016 / Accepted: 12 July 2016 / Published: 16 July 2016
(This article belongs to the Special Issue Marine Fungal Natural Products)

Abstract

Two new pentaketides, including a new benzofuran-1-one derivative (1) and a new isochromen-1-one (5), and seven new benzoic acid derivatives, including two new benzopyran derivatives (2a, b), a new benzoxepine derivative (3), two new chromen-4-one derivatives (4b, 7) and two new benzofuran derivatives (6a, b), were isolated, together with the previously reported 2,3-dihydro-6-hydroxy-2,2-dimethyl-4H-1-benzopyran-4-one (4a), from the culture of the marine sponge-associated fungus Neosartorya quadricincta KUFA 0081. The structures of the new compounds were established based on 1D and 2D NMR spectral analysis, and in the case of compounds 1, 2a, 4b, 5, 6a and 7, the absolute configurations of their stereogenic carbons were determined by an X-ray crystallographic analysis. None of the isolated compounds were active in the tests for antibacterial activity against Gram-positive and Gram-negative bacteria, as well as multidrug-resistant isolates from the environment (MIC > 256 μg/mL), antifungal activity against yeast (Candida albicans ATTC 10231), filamentous fungus (Aspergillus fumigatus ATTC 46645) and dermatophyte (Trichophyton rubrum FF5) (MIC > 512 µg/mL) and in vitro growth inhibitory activity against the MCF-7 (breast adenocarcinoma), NCI-H460 (non-small cell lung cancer) and A375-C5 (melanoma) cell lines (GI50 > 150 µM) by the protein binding dye SRB method. View Full-Text
Keywords: Neosartorya quadricincta KUFA 0081; marine-derived fungus; polyketides; pentaketides; benzoic acid derivatives; Clathria reinwardti Neosartorya quadricincta KUFA 0081; marine-derived fungus; polyketides; pentaketides; benzoic acid derivatives; Clathria reinwardti
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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.; Gales, L.; Lee, M.; Pereira, J.A.C.; Silva, A.M.S.; Pinto, M.M.M.; Kijjoa, A. New Polyketides and New Benzoic Acid Derivatives from the Marine Sponge-Associated Fungus Neosartorya quadricincta KUFA 0081. Mar. Drugs 2016, 14, 134.

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