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Molecules 2019, 24(1), 208; https://doi.org/10.3390/molecules24010208

Erubescensoic Acid, a New Polyketide and a Xanthonopyrone SPF-3059-26 from the Culture of the Marine Sponge-Associated Fungus Penicillium erubescens KUFA 0220 and Antibacterial Activity Evaluation of Some of Its Constituents

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), 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
Departamento de Química & QOPNA, Universidade de Aveiro, 3810-193 Aveiro, Portugal
6
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.
Academic Editor: Isabel C.F.R. Ferreira
Received: 4 December 2018 / Revised: 2 January 2019 / Accepted: 3 January 2019 / Published: 8 January 2019
(This article belongs to the Collection Bioactive Compounds)
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Abstract

A new polyketide erubescensoic acid (1), and the previously reported xanthonopyrone, SPF-3059-26 (2), were isolated from the uninvestigated fractions of the ethyl acetate crude extract of the marine sponge-associated fungus Penicillium erubescens KUFA0220. The structures of the new compound, erubescensoic acid (1), and the previously reported SPF-3059-26 (2), were elucidated by extensive analysis of 1D and 2D-NMR spectra as well as HRMS. The absolute configuration of the stereogenic carbon of erubescensoic acid (1) was determined by X-ray analysis. Erubescensoic acid (1) and SPF-3059-26 (2), together with erubescenschromone B (3), penialidin D (4), and 7-hydroxy-6-methoxy-4-oxo-3-[(1E)-3-oxobut-1-en-1-yl]-4H-chromen-5-carboxylic acid (5), recently isolated from this fungus, were assayed for their antibacterial activity against gram-positive and gram-negative reference strains and the multidrug-resistant (MDR) strains from the environment. The capacity of these compounds to interfere with the bacterial biofilm formation and their potential synergism with clinically relevant antibiotics for the MDR strains were also investigated. View Full-Text
Keywords: Penicillium erubescens; marine sponge-associated fungus; polyketides; erubescensoic acid; SPF-3059-267; antibacterial activity; antibiofilm activity; antibiotic synergy Penicillium erubescens; marine sponge-associated fungus; polyketides; erubescensoic acid; SPF-3059-267; antibacterial activity; antibiofilm activity; antibiotic synergy
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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.; Dethoup, T.; Gales, L.; Pereira, J.A.; Freitas-Silva, J.; Costa, P.M.; Silva, A.M.S.; Pinto, M.M.M.; Kijjoa, A. Erubescensoic Acid, a New Polyketide and a Xanthonopyrone SPF-3059-26 from the Culture of the Marine Sponge-Associated Fungus Penicillium erubescens KUFA 0220 and Antibacterial Activity Evaluation of Some of Its Constituents. Molecules 2019, 24, 208.

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