2. Academic Validation
  3. 1,3-Dioxepine and spiropyran derivatives of viomellein and other dimeric naphthopyranones from cultures of Aspergillus elegans KUFA0015 and their antibacterial activity

1,3-Dioxepine and spiropyran derivatives of viomellein and other dimeric naphthopyranones from cultures of Aspergillus elegans KUFA0015 and their antibacterial activity

  • Phytochemistry. 2021 Jan:181:112575. doi: 10.1016/j.phytochem.2020.112575.
Decha Kumla 1,  Emilia Sousa 2,  Alessia Marengo 3,  Tida Dethoup 4,  José A Pereira 5,  Luís Gales 6,  Joana Freitas-Silva 7,  Paulo M Costa 8,  Sharad Mistry 9,  Artur M S Silva 10,  Anake Kijjoa 11
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: Decha1987@hotmail.com.
  • 2 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.
  • 3 Department of Drug Sciences, Università di Pávia, C. So strada Nuova 65, 27100, Pavia, Italy. Electronic address: alessia.marengo01@universitadipavia.it.
  • 4 Department of Plant Pathology, Faculty of Agriculture, Kasetsart University, Bangkok, 10240, Thailand. Electronic address: tdethoup@yahoo.com.
  • 5 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.
  • 6 ICBAS-Instituto de Ciências Biomédicas Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, 4050-313, Porto, Portugal; Instituto de Biologia Molecular e Celular (i3S-IBMC), Universidade do Porto, Rua de Jorge Viterbo Ferreira, 228, 4050-313, Porto, Portugal. Electronic address: lgales@ibmc.up.pt.
  • 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: joanafreitasdasilva@gmail.com.
  • 8 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.p.
  • 9 Department of Chemistry, University of Leicester, University Road, Leicester, LE 7 RH, UK. Electronic address: scm11@leicester.ac.th.
  • 10 Departamento de Química & QOPNA, Universidade de Aveiro, 3810-193, Aveiro, Portugal. Electronic address: artur.silva@ua.pt.
  • 11 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: 33166747 DOI: 10.1016/j.phytochem.2020.112575
Abstract

Two undescribed viomellein derivatives, xanthoelegansin and spiroxanthoelegansin, were isolated together with clavatol, sitosteanone, vioxanthin, xanthomegnin, viomellein, rubrosulphin, rubrosulphin diacetate, viopurpurin , ochratoxin A, ochratoxin A methyl ester, ochratoxin B and ochratoxin β, from cultures of the marine sponge-associated fungus Aspergillus elegans KUFA0015. The structures of the undescribed compounds were established based on an extensive analysis of 1D and 2D NMR spectra as well as HRMS data. The structure of xanthoelegansin and the absolute configuration of its stereogenic carbons were confirmed by X-ray analysis. The change in conformation of xanthoelegansin was interpreted using quantum mechanical theoretical calculation data in combination with the observation of the change of the proton signals of the 1,3-dioxepine ring in 1HNMR spectra at varying temperatures. The mechanisms of the formation of xanthoelegansin and spiroxanthoelegansin from viomellein were proposed. Clavatol, sitosteanone, vioxanthin, xanthomegnin, viomellein, xanthoelegansin, rubrosulphin, rubrosulphin diacetate, ochratoxin A, ochratoxin A methyl ester, ochratoxin B and ochratoxin β were assayed for their Antibacterial activity against reference strains and multidrug-resistant isolates from the environment. The tested compounds were also evaluated for their capacity to inhibit biofilm formation in the reference strains.

Keywords

Antibacterial activity; Aspergillus elegans KUFA0015; Marine sponge-associated fungus; Monanchora unguiculata; Naphthopyranone derivatives; Ochratoxins.

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