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, 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), fallacin...
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| Format: | Article |
| Language: | English |
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MDPI AG
2017-05-01
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| Series: | Marine Drugs |
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| Online Access: | http://www.mdpi.com/1660-3397/15/5/139 |
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| author | 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 |
| author_facet | 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 |
| author_sort | Jidapa Noinart |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-04-13T09:00:41Z |
| format | Article |
| id | doaj.art-14d79a50bda14a41931fd6051c3c8407 |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-04-13T09:00:41Z |
| publishDate | 2017-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-14d79a50bda14a41931fd6051c3c84072022-12-22T02:53:09ZengMDPI AGMarine Drugs1660-33972017-05-0115513910.3390/md15050139md15050139A New Ergosterol Analog, a New Bis-Anthraquinone and Anti-Obesity Activity of Anthraquinones from the Marine Sponge-Associated Fungus Talaromyces stipitatus KUFA 0207Jidapa Noinart0Suradet Buttachon1Tida Dethoup2Luís Gales3José A. Pereira4Ralph Urbatzka5Sara Freitas6Michael Lee7Artur M. S. Silva8Madalena M. M. Pinto9Vítor Vasconcelos10Anake Kijjoa11ICBAS-Instituto de Ciências Biomédicas Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, PortugalICBAS-Instituto de Ciências Biomédicas Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, PortugalDepartment of Plant Pathology, Faculty of Agriculture, Kasetsart University, Bangkok 10240, ThailandICBAS-Instituto de Ciências Biomédicas Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, PortugalICBAS-Instituto de Ciências Biomédicas Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, PortugalInterdisciplinary Centre of Marine and Environmental Research (CIIMAR), Terminal de Cruzeiros do Porto de Lexões, Av. General Norton de Matos s/n, 4450-208 Matosinhos, PortugalInterdisciplinary Centre of Marine and Environmental Research (CIIMAR), Terminal de Cruzeiros do Porto de Lexões, Av. General Norton de Matos s/n, 4450-208 Matosinhos, PortugalDepartment of Chemistry, University of Leicester, University Road, Leicester LE 7 RH, UKDepartamento de Química & QOPNA, Universidade de Aveiro, 3810-193 Aveiro, PortugalInterdisciplinary Centre of Marine and Environmental Research (CIIMAR), Terminal de Cruzeiros do Porto de Lexões, Av. General Norton de Matos s/n, 4450-208 Matosinhos, PortugalInterdisciplinary Centre of Marine and Environmental Research (CIIMAR), Terminal de Cruzeiros do Porto de Lexões, Av. General Norton de Matos s/n, 4450-208 Matosinhos, PortugalICBAS-Instituto de Ciências Biomédicas Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, PortugalA 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.http://www.mdpi.com/1660-3397/15/5/139Talaromyces stipitatusTrichocomaceaeanthraquinonesbis-anthraquinoneergosterol derivativessecalonic acid Aanti-obesityzebrafish Nile red assay |
| spellingShingle | 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 A New Ergosterol Analog, a New Bis-Anthraquinone and Anti-Obesity Activity of Anthraquinones from the Marine Sponge-Associated Fungus Talaromyces stipitatus KUFA 0207 Marine Drugs Talaromyces stipitatus Trichocomaceae anthraquinones bis-anthraquinone ergosterol derivatives secalonic acid A anti-obesity zebrafish Nile red assay |
| title | A New Ergosterol Analog, a New Bis-Anthraquinone and Anti-Obesity Activity of Anthraquinones from the Marine Sponge-Associated Fungus Talaromyces stipitatus KUFA 0207 |
| title_full | A New Ergosterol Analog, a New Bis-Anthraquinone and Anti-Obesity Activity of Anthraquinones from the Marine Sponge-Associated Fungus Talaromyces stipitatus KUFA 0207 |
| title_fullStr | A New Ergosterol Analog, a New Bis-Anthraquinone and Anti-Obesity Activity of Anthraquinones from the Marine Sponge-Associated Fungus Talaromyces stipitatus KUFA 0207 |
| title_full_unstemmed | A New Ergosterol Analog, a New Bis-Anthraquinone and Anti-Obesity Activity of Anthraquinones from the Marine Sponge-Associated Fungus Talaromyces stipitatus KUFA 0207 |
| title_short | A New Ergosterol Analog, a New Bis-Anthraquinone and Anti-Obesity Activity of Anthraquinones from the Marine Sponge-Associated Fungus Talaromyces stipitatus KUFA 0207 |
| title_sort | new ergosterol analog a new bis anthraquinone and anti obesity activity of anthraquinones from the marine sponge associated fungus talaromyces stipitatus kufa 0207 |
| topic | Talaromyces stipitatus Trichocomaceae anthraquinones bis-anthraquinone ergosterol derivatives secalonic acid A anti-obesity zebrafish Nile red assay |
| url | http://www.mdpi.com/1660-3397/15/5/139 |
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