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Mar. Drugs 2018, 16(8), 289; https://doi.org/10.3390/md16080289

Chromone Derivatives and Other Constituents from Cultures of the Marine Sponge-Associated Fungus Penicillium erubescens KUFA0220 and Their Antibacterial Activity

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), Universidade do Porto, Terminal de Cruzeiros do Porto de Lexões, Av. General Norton de Matos s/n, 4450-208 Matosinhos, Portugal
3
Department of Plant Pathology, Faculty of Agriculture, Kasetsart University, Bangkok 10240, Thailand
4
Instituto de Biologia Molecular e Celular (i3S-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
Department of Food Engineering, Faculty of Engineering and Architecture, Kilis 7 Aralık University, 79000 Kilis, Turkey
8
Laboratório de Química Orgânica, Departamento de Ciências Químicas, Faculdade de Farmácia, Universidade do Porto, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal
*
Authors to whom correspondence should be addressed.
Received: 2 August 2018 / Revised: 15 August 2018 / Accepted: 18 August 2018 / Published: 20 August 2018
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Abstract

A previously unreported chromene derivative, 1-hydroxy-12-methoxycitromycin (1c), and four previously undescribed chromone derivatives, including pyanochromone (3b), spirofuranochromone (4), 7-hydroxy-6-methoxy-4-oxo-3-[(1E)-3-oxobut-1-en-1-yl]-4H-chromene-5-carboxylic acid (5), a pyranochromone dimer (6) were isolated, together with thirteen known compounds: β-sitostenone, ergosterol 5,8-endoperoxide, citromycin (1a), 12-methoxycitromycin (1b), myxotrichin D (1d), 12-methoxycitromycetin (1e), anhydrofulvic acid (2a), myxotrichin C (2b), penialidin D (2c), penialidin F (3a), SPF-3059-30 (7), GKK1032B (8) and secalonic acid A (9), from cultures of the marine sponge- associated fungus Penicillium erubescens KUFA0220. Compounds 1ae, 2a, 3a, 4, 79, were tested for their antibacterial activity against Gram-positive and Gram-negative reference and multidrug-resistant strains isolated from the environment. Only 8 exhibited an in vitro growth inhibition of all Gram-positive bacteria whereas 9 showed growth inhibition of methicillin-resistant Staphyllococus aureus (MRSA). None of the compounds were active against Gram-negative bacteria tested. View Full-Text
Keywords: Penicillium erubescens; Aspergillaceae; marine sponge-associated fungus; Neopetrosia sp.; chromone derivatives; GKK 1032B; pyranochromone; spirofuranochromone; antibacterial activity Penicillium erubescens; Aspergillaceae; marine sponge-associated fungus; Neopetrosia sp.; chromone derivatives; GKK 1032B; pyranochromone; spirofuranochromone; antibacterial activity
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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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Kumla, D.; Pereira, J.A.; Dethoup, T.; Gales, L.; Freitas-Silva, J.; Costa, P.M.; Lee, M.; Silva, A.M.S.; Sekeroglu, N.; Pinto, M.M.M.; Kijjoa, A. Chromone Derivatives and Other Constituents from Cultures of the Marine Sponge-Associated Fungus Penicillium erubescens KUFA0220 and Their Antibacterial Activity. Mar. Drugs 2018, 16, 289.

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