A New Ergosterol Analog, a New Bis-Anthraquinone and Anti-Obesity Activity of Anthraquinones from the Marine Sponge-Associated Fungus Talaromyces stipitatus KUFA 0207
Jidapa Noinart,
Suradet Buttachon,
Tida Dethoup,
Luís Gales,
José A. Pereira,
Ralph Urbatzka,
Sara Freitas,
Michael Lee,
Artur M. S. Silva,
Madalena M. M. Pinto,
Vítor Vasconcelos,
Anake Kijjoa
Affiliations
Jidapa Noinart
ICBAS-Instituto de Ciências Biomédicas Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal
Suradet Buttachon
ICBAS-Instituto de Ciências Biomédicas Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal
Tida Dethoup
Department of Plant Pathology, Faculty of Agriculture, Kasetsart University, Bangkok 10240, Thailand
Luís Gales
ICBAS-Instituto de Ciências Biomédicas Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal
José A. Pereira
ICBAS-Instituto de Ciências Biomédicas Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal
Ralph Urbatzka
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
Sara Freitas
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
Michael Lee
Department of Chemistry, University of Leicester, University Road, Leicester LE 7 RH, UK
Artur M. S. Silva
Departamento de Química & QOPNA, Universidade de Aveiro, 3810-193 Aveiro, Portugal
Madalena M. M. Pinto
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
Vítor Vasconcelos
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
Anake Kijjoa
ICBAS-Instituto de Ciências Biomédicas Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal
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.
