2. Academic Validation
  3. Prenylated phenylbutyrolactones from cultures of a marine sponge-associated fungus Aspergillus flavipes KUFA1152

Prenylated phenylbutyrolactones from cultures of a marine sponge-associated fungus Aspergillus flavipes KUFA1152

  • Phytochemistry. 2021 May:185:112709. doi: 10.1016/j.phytochem.2021.112709.
Fátima P Machado 1,  Decha Kumla 2,  José A Pereira 3,  Emilia Sousa 4,  Tida Dethoup 5,  Joana Freitas-Silva 6,  Paulo M Costa 7,  Sharad Mistry 8,  Artur M S Silva 9,  Anake Kijjoa 10
Affiliations

Affiliations

  • 1 ICBAS-Instituto de Ciências Biomédicas Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, 4050-313, Porto, Portugal; Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), Terminal de Cruzeiros do Porto de Leixões, Av. General Norton de Matos s/n, 4450-208, Matosinhos, Portugal. Electronic address: maria.mfpm@hotmail.com.
  • 2 ICBAS-Instituto de Ciências Biomédicas Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, 4050-313, Porto, Portugal; Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), Terminal de Cruzeiros do Porto de Leixões, Av. General Norton de Matos s/n, 4450-208, Matosinhos, Portugal. Electronic address: Decha1987@hotmail.com.
  • 3 ICBAS-Instituto de Ciências Biomédicas Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, 4050-313, Porto, Portugal; Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), Terminal de Cruzeiros do Porto de Leixões, Av. General Norton de Matos s/n, 4450-208, Matosinhos, Portugal. Electronic address: jpereira@icbas.up.pt.
  • 4 Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), Terminal de Cruzeiros do Porto de Leixões, Av. General Norton de Matos s/n, 4450-208, Matosinhos, Portugal; Laboratório de Química Orgânica, Departamento de Ciências Químicas, Faculdade de Farmácia, Universidade do Porto, Rua de Jorge Viterbo Ferreira, 228, 4050-313, Porto, Portugal. Electronic address: esousa@ff.up.pt.
  • 5 Department of Plant Pathology, Faculty of Agriculture, Kasetsart University, Bangkok, 10240, Thailand. Electronic address: tdethoup@yahoo.com.
  • 6 ICBAS-Instituto de Ciências Biomédicas Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, 4050-313, Porto, Portugal; Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), Terminal de Cruzeiros do Porto de Leixões, Av. General Norton de Matos s/n, 4450-208, Matosinhos, Portugal. Electronic address: joanafreitasdasilva@gmail.com.
  • 7 ICBAS-Instituto de Ciências Biomédicas Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, 4050-313, Porto, Portugal; Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), Terminal de Cruzeiros do Porto de Leixões, Av. General Norton de Matos s/n, 4450-208, Matosinhos, Portugal. Electronic address: pmcosta@icbas.up.pt.
  • 8 Department of Chemistry, University of Leicester, University Road, Leicester, LE 7 RH, UK. Electronic address: scm11@leicester.ac.uk.
  • 9 Departamento de Química & QOPNA, Universidade de Aveiro, 3810-193, Aveiro, Portugal. Electronic address: artur.silva@ua.pt.
  • 10 ICBAS-Instituto de Ciências Biomédicas Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, 4050-313, Porto, Portugal; Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), Terminal de Cruzeiros do Porto de Leixões, Av. General Norton de Matos s/n, 4450-208, Matosinhos, Portugal. Electronic address: ankijjoa@icbas.up.pt.
PMID: 33636575 DOI: 10.1016/j.phytochem.2021.112709
Abstract

Four undescribed prenylated phenylbutyrolactones, aspulvinones R, S, T and U, were isolated together with the previously reported aspulvinones A, B', H and 4-hydroxy-3,5-bis(3-methylbut-2-en-1-yl)benzaldehyde, from cultures of the marine sponge-derived fungus Aspergillus flavipes KUFA1152. The structures of the undescribed compounds were established on the basis of extensive analysis of 1D and 2D NMR and HRMS spectra. In the case of aspulvinone T, the absolute configuration of its stereogenic carbon was established by comparison of the experimental and calculated electronic circular dichroism (ECD) spectra. The structure of the previously reported compounds were elucidated by 1D and 2D NMR analysis as well as comparison of their 1H or/and 13C NMR data with those reported in the literature. Aspulvinones B', H, R, S, T and a mixture of aspulvinones A and U exhibited Antibacterial activity against reference strains and multidrug-resistant isolates from the environment as well as capacity to inhibit biofilm formation in the reference strains. However, none of the tested compounds showed potential synergy with clinically relevant Antibiotics on multidrug-resistant isolates.

Keywords

Antibacterial activity; Antibiofilm activity; Aspergillus flavipes KUFA1152; Aspulvinones; Marine sponge-associated fungus; Mycale sp.; Prenylated phenylbutyrolactones; Trichocomaceae.

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