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

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 derivativ...

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Autores principales: Prompanya, Chadaporn, Dethoup, Tida, Gales, Luís, Lee, Michael, Pereira, José A. C., Silva, Artur M. S., Pinto, Madalena M. M., Kijjoa, Anake
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4962024/
https://www.ncbi.nlm.nih.gov/pubmed/27438842
http://dx.doi.org/10.3390/md14070134
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author Prompanya, Chadaporn
Dethoup, Tida
Gales, Luís
Lee, Michael
Pereira, José A. C.
Silva, Artur M. S.
Pinto, Madalena M. M.
Kijjoa, Anake
author_facet Prompanya, Chadaporn
Dethoup, Tida
Gales, Luís
Lee, Michael
Pereira, José A. C.
Silva, Artur M. S.
Pinto, Madalena M. M.
Kijjoa, Anake
author_sort Prompanya, Chadaporn
collection PubMed
description 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 (GI(50) > 150 µM) by the protein binding dye SRB method.
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spelling pubmed-49620242016-08-01 New Polyketides and New Benzoic Acid Derivatives from the Marine Sponge-Associated Fungus Neosartorya quadricincta KUFA 0081 Prompanya, Chadaporn Dethoup, Tida Gales, Luís Lee, Michael Pereira, José A. C. Silva, Artur M. S. Pinto, Madalena M. M. Kijjoa, Anake Mar Drugs Article 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 (GI(50) > 150 µM) by the protein binding dye SRB method. MDPI 2016-07-16 /pmc/articles/PMC4962024/ /pubmed/27438842 http://dx.doi.org/10.3390/md14070134 Text en © 2016 by the authors; licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC-BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Prompanya, Chadaporn
Dethoup, Tida
Gales, Luís
Lee, Michael
Pereira, José A. C.
Silva, Artur M. S.
Pinto, Madalena M. M.
Kijjoa, Anake
New Polyketides and New Benzoic Acid Derivatives from the Marine Sponge-Associated Fungus Neosartorya quadricincta KUFA 0081
title New Polyketides and New Benzoic Acid Derivatives from the Marine Sponge-Associated Fungus Neosartorya quadricincta KUFA 0081
title_full New Polyketides and New Benzoic Acid Derivatives from the Marine Sponge-Associated Fungus Neosartorya quadricincta KUFA 0081
title_fullStr New Polyketides and New Benzoic Acid Derivatives from the Marine Sponge-Associated Fungus Neosartorya quadricincta KUFA 0081
title_full_unstemmed New Polyketides and New Benzoic Acid Derivatives from the Marine Sponge-Associated Fungus Neosartorya quadricincta KUFA 0081
title_short New Polyketides and New Benzoic Acid Derivatives from the Marine Sponge-Associated Fungus Neosartorya quadricincta KUFA 0081
title_sort new polyketides and new benzoic acid derivatives from the marine sponge-associated fungus neosartorya quadricincta kufa 0081
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4962024/
https://www.ncbi.nlm.nih.gov/pubmed/27438842
http://dx.doi.org/10.3390/md14070134
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