2. Academic Validation
  3. A New Ergosterol Analog, a New Bis-Anthraquinone and Anti-Obesity Activity of Anthraquinones from the Marine Sponge-Associated Fungus Talaromyces stipitatus KUFA 0207

A New Ergosterol Analog, a New Bis-Anthraquinone and Anti-Obesity Activity of Anthraquinones from the Marine Sponge-Associated Fungus Talaromyces stipitatus KUFA 0207

  • Mar Drugs. 2017 May 16;15(5):139. doi: 10.3390/md15050139.
Jidapa Noinart 1,  Suradet Buttachon 2 3,  Tida Dethoup 4,  Luís Gales 5 6,  José A Pereira 7 8,  Ralph Urbatzka 9,  Sara Freitas 10,  Michael Lee 11,  Artur M S Silva 12,  Madalena M M Pinto 13 14,  Vítor Vasconcelos 15 16,  Anake Kijjoa 17 18
Affiliations

Affiliations

  • 1 ICBAS-Instituto de Ciências Biomédicas Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal. jidanoinart@gmail.com.
  • 2 ICBAS-Instituto de Ciências Biomédicas Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal. nokrari_209@hotmail.com.
  • 3 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. nokrari_209@hotmail.com.
  • 4 Department of Plant Pathology, Faculty of Agriculture, Kasetsart University, Bangkok 10240, Thailand. tdethoup@yahoo.com.
  • 5 ICBAS-Instituto de Ciências Biomédicas Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal. lgales@ibmc.up.pt.
  • 6 Instituto de Biologia Molecular e Celular (IBMC), Universidade do Porto, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal. lgales@ibmc.up.pt.
  • 7 ICBAS-Instituto de Ciências Biomédicas Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal. jpereira@icbas.up.pt.
  • 8 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. jpereira@icbas.up.pt.
  • 9 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. rurbatzka@ciimar.up.pt.
  • 10 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. freitas.srf.09@gmail.com.
  • 11 Department of Chemistry, University of Leicester, University Road, Leicester LE 7 RH, UK. ml34@leicester.ac.uk.
  • 12 Departamento de Química & QOPNA, Universidade de Aveiro, 3810-193 Aveiro, Portugal. artur.silva@ua.pt.
  • 13 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. madalena@ff.up.pt.
  • 14 Laboratório de Química Orgânica, Departamento de Ciências Químicas, Faculdade de Farmácia, Universidade do Porto, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal. madalena@ff.up.pt.
  • 15 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. vmvascon@fc.up.pt.
  • 16 Departamento de Biologia, Faculdade de Ciências, Universidade do Porto, Rua do Campo Alegre, s/n, 4169-007 Porto, Portugal. vmvascon@fc.up.pt.
  • 17 ICBAS-Instituto de Ciências Biomédicas Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal. ankijjoa@icbas.up.pt.
  • 18 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. ankijjoa@icbas.up.pt.
PMID: 28509846 DOI: 10.3390/md15050139
Abstract

A new ergosterol analog, talarosterone (1) and a new bis-anthraquinone derivative (3) were isolated, together with ten known compounds including palmitic acid, ergosta-4,6,8(14),22-tetraen-3-one, ergosterol-5,8-endoperoxide, cyathisterone (2), emodin (4a), questinol (4b), citreorosein (4c), fallacinol (4d), rheoemodin (4e) and secalonic acid A (5), from the ethyl acetate extract of the culture of the marine sponge-associated fungus Talaromyces stipitatus KUFA 0207. The structures of the new compounds were established based on extensive 1D and 2D spectral analysis, and in the case of talarosterone (1), the absolute configurations of its stereogenic carbons were determined by X-ray crystallographic analysis. The structure and stereochemistry of cyathisterone (2) was also confirmed by X-ray analysis. The Anthraquinones 4a-e and secalonic acid A (5) were tested for their anti-obesity activity using the zebrafish Nile red assay. Only citreorosein (4c) and questinol (4b) exhibited significant anti-obesity activity, while emodin (4a) and secalonic acid A (5) caused toxicity (death) for all exposed zebrafish larvae after 24 h.

Keywords

Talaromyces stipitatus; Trichocomaceae; anthraquinones; anti-obesity; bis-anthraquinone; ergosterol derivatives; secalonic acid A; zebrafish Nile red assay.

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