New Hybrid Phenalenone Dimer, Highly Conjugated Dihydroxylated C<sub>28</sub> Steroid and Azaphilone from the Culture Extract of a Marine Sponge-Associated Fungus, <i>Talaromyces pinophilus</i> KUFA 1767
An undescribed hybrid phenalenone dimer, talaropinophilone (<b>3</b>), an unreported azaphilone, 7-<i>epi</i>-pinazaphilone B (<b>4</b>), an unreported phthalide dimer, talaropinophilide (<b>6</b>), and an undescribed 9<i>R</i>,15<i>S...
| Main Authors: | , , , , , , , , , , , |
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-03-01
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| Series: | Marine Drugs |
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| Online Access: | https://www.mdpi.com/1660-3397/21/3/194 |
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| author | Fátima P. Machado Inês C. Rodrigues Aikaterini Georgopolou Luís Gales José A. Pereira Paulo M. Costa Sharad Mistry Salar Hafez Ghoran Artur M. S. Silva Tida Dethoup Emília Sousa Anake Kijjoa |
| author_facet | Fátima P. Machado Inês C. Rodrigues Aikaterini Georgopolou Luís Gales José A. Pereira Paulo M. Costa Sharad Mistry Salar Hafez Ghoran Artur M. S. Silva Tida Dethoup Emília Sousa Anake Kijjoa |
| author_sort | Fátima P. Machado |
| collection | DOAJ |
| description | An undescribed hybrid phenalenone dimer, talaropinophilone (<b>3</b>), an unreported azaphilone, 7-<i>epi</i>-pinazaphilone B (<b>4</b>), an unreported phthalide dimer, talaropinophilide (<b>6</b>), and an undescribed 9<i>R</i>,15<i>S</i>-dihydroxy-ergosta-4,6,8 (14)-tetraen-3-one (<b>7</b>) were isolated together with the previously reported bacillisporins A (<b>1</b>) and B (<b>2</b>), an azaphilone derivative, Sch 1385568 (<b>5</b>), 1-deoxyrubralactone (<b>8</b>), acetylquestinol (<b>9</b>), piniterpenoid D (<b>10</b>) and 3,5-dihydroxy-4-methylphthalaldehydic acid (<b>11</b>) from the ethyl acetate extract of the culture of a marine sponge-derived fungus, <i>Talaromyces pinophilus</i> KUFA 1767. The structures of the undescribed compounds were elucidated by 1D and 2D NMR as well as high-resolution mass spectral analyses. The absolute configuration of C-9′ of <b>1</b> and <b>2</b> was revised to be 9′<i>S</i> using the coupling constant value between C-8′ and C-9′ and was confirmed by ROESY correlations in the case of <b>2</b>. The absolute configurations of the stereogenic carbons in <b>7</b> and <b>8</b> were established by X-ray crystallographic analysis. Compounds <b>1</b>,<b>2</b>, <b>4</b>–<b>8</b>, <b>10</b> and <b>11</b> were tested for antibacterial activity against four reference strains, viz. two Gram-positive (<i>Staphylococcus aureus</i> ATCC 29213, <i>Enterococcus faecalis</i> ATCC 29212) and two Gram-negative (<i>Escherichia coli</i> ATCC 25922, <i>Pseudomonas aeruginosa</i> ATCC 27853), as well as three multidrug-resistant strains, viz. an extended-spectrum β-lactamase (ESBL)-producing <i>E. coli</i>, a methicillin-resistant <i>S. aureus</i> (MRSA) and a vancomycin-resistant <i>E. faecalis</i> (VRE). However, only <b>1</b> and <b>2</b> exhibited significant antibacterial activity against both <i>S. aureus</i> ATCC 29213 and MRSA. Moreover, <b>1</b> and <b>2</b> also significantly inhibited biofilm formation in <i>S. aureus</i> ATCC 29213 at both MIC and 2xMIC concentrations. |
| first_indexed | 2024-03-11T06:16:46Z |
| format | Article |
| id | doaj.art-eba2cccf15af484b864372c28185fe7a |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-03-11T06:16:46Z |
| publishDate | 2023-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-eba2cccf15af484b864372c28185fe7a2023-11-17T12:17:52ZengMDPI AGMarine Drugs1660-33972023-03-0121319410.3390/md21030194New Hybrid Phenalenone Dimer, Highly Conjugated Dihydroxylated C<sub>28</sub> Steroid and Azaphilone from the Culture Extract of a Marine Sponge-Associated Fungus, <i>Talaromyces pinophilus</i> KUFA 1767Fátima P. Machado0Inês C. Rodrigues1Aikaterini Georgopolou2Luís Gales3José A. Pereira4Paulo M. Costa5Sharad Mistry6Salar Hafez Ghoran7Artur M. S. Silva8Tida Dethoup9Emília Sousa10Anake 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 Pharmacy, National and Kapodistrian University of Athens, 15771 Athens, GreeceICBAS—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, PortugalICBAS—Instituto de Ciências Biomédicas Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, PortugalDepartment of Chemistry, University of Leicester, University Road, Leicester LE1 7RH, UKHEJ Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, PakistanDepartamento de Química & QOPNA, Universidade de Aveiro, 3810-193 Aveiro, PortugalDepartment of Plant Pathology, Faculty of Agriculture, Kasetsart University, Bangkok 10240, ThailandInterdisciplinary Centre of Marine and Environmental Research (CIIMAR), Terminal de Cruzeiros do Porto de Leixões, 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, PortugalAn undescribed hybrid phenalenone dimer, talaropinophilone (<b>3</b>), an unreported azaphilone, 7-<i>epi</i>-pinazaphilone B (<b>4</b>), an unreported phthalide dimer, talaropinophilide (<b>6</b>), and an undescribed 9<i>R</i>,15<i>S</i>-dihydroxy-ergosta-4,6,8 (14)-tetraen-3-one (<b>7</b>) were isolated together with the previously reported bacillisporins A (<b>1</b>) and B (<b>2</b>), an azaphilone derivative, Sch 1385568 (<b>5</b>), 1-deoxyrubralactone (<b>8</b>), acetylquestinol (<b>9</b>), piniterpenoid D (<b>10</b>) and 3,5-dihydroxy-4-methylphthalaldehydic acid (<b>11</b>) from the ethyl acetate extract of the culture of a marine sponge-derived fungus, <i>Talaromyces pinophilus</i> KUFA 1767. The structures of the undescribed compounds were elucidated by 1D and 2D NMR as well as high-resolution mass spectral analyses. The absolute configuration of C-9′ of <b>1</b> and <b>2</b> was revised to be 9′<i>S</i> using the coupling constant value between C-8′ and C-9′ and was confirmed by ROESY correlations in the case of <b>2</b>. The absolute configurations of the stereogenic carbons in <b>7</b> and <b>8</b> were established by X-ray crystallographic analysis. Compounds <b>1</b>,<b>2</b>, <b>4</b>–<b>8</b>, <b>10</b> and <b>11</b> were tested for antibacterial activity against four reference strains, viz. two Gram-positive (<i>Staphylococcus aureus</i> ATCC 29213, <i>Enterococcus faecalis</i> ATCC 29212) and two Gram-negative (<i>Escherichia coli</i> ATCC 25922, <i>Pseudomonas aeruginosa</i> ATCC 27853), as well as three multidrug-resistant strains, viz. an extended-spectrum β-lactamase (ESBL)-producing <i>E. coli</i>, a methicillin-resistant <i>S. aureus</i> (MRSA) and a vancomycin-resistant <i>E. faecalis</i> (VRE). However, only <b>1</b> and <b>2</b> exhibited significant antibacterial activity against both <i>S. aureus</i> ATCC 29213 and MRSA. Moreover, <b>1</b> and <b>2</b> also significantly inhibited biofilm formation in <i>S. aureus</i> ATCC 29213 at both MIC and 2xMIC concentrations.https://www.mdpi.com/1660-3397/21/3/194<i>Talaromyces pinophilus</i>Trichocomaceaemarine sponge-associated fungushybrid oxyphenalenonehighly conjugated C<sub>28</sub> steroidazaphilone |
| spellingShingle | Fátima P. Machado Inês C. Rodrigues Aikaterini Georgopolou Luís Gales José A. Pereira Paulo M. Costa Sharad Mistry Salar Hafez Ghoran Artur M. S. Silva Tida Dethoup Emília Sousa Anake Kijjoa New Hybrid Phenalenone Dimer, Highly Conjugated Dihydroxylated C<sub>28</sub> Steroid and Azaphilone from the Culture Extract of a Marine Sponge-Associated Fungus, <i>Talaromyces pinophilus</i> KUFA 1767 Marine Drugs <i>Talaromyces pinophilus</i> Trichocomaceae marine sponge-associated fungus hybrid oxyphenalenone highly conjugated C<sub>28</sub> steroid azaphilone |
| title | New Hybrid Phenalenone Dimer, Highly Conjugated Dihydroxylated C<sub>28</sub> Steroid and Azaphilone from the Culture Extract of a Marine Sponge-Associated Fungus, <i>Talaromyces pinophilus</i> KUFA 1767 |
| title_full | New Hybrid Phenalenone Dimer, Highly Conjugated Dihydroxylated C<sub>28</sub> Steroid and Azaphilone from the Culture Extract of a Marine Sponge-Associated Fungus, <i>Talaromyces pinophilus</i> KUFA 1767 |
| title_fullStr | New Hybrid Phenalenone Dimer, Highly Conjugated Dihydroxylated C<sub>28</sub> Steroid and Azaphilone from the Culture Extract of a Marine Sponge-Associated Fungus, <i>Talaromyces pinophilus</i> KUFA 1767 |
| title_full_unstemmed | New Hybrid Phenalenone Dimer, Highly Conjugated Dihydroxylated C<sub>28</sub> Steroid and Azaphilone from the Culture Extract of a Marine Sponge-Associated Fungus, <i>Talaromyces pinophilus</i> KUFA 1767 |
| title_short | New Hybrid Phenalenone Dimer, Highly Conjugated Dihydroxylated C<sub>28</sub> Steroid and Azaphilone from the Culture Extract of a Marine Sponge-Associated Fungus, <i>Talaromyces pinophilus</i> KUFA 1767 |
| title_sort | new hybrid phenalenone dimer highly conjugated dihydroxylated c sub 28 sub steroid and azaphilone from the culture extract of a marine sponge associated fungus i talaromyces pinophilus i kufa 1767 |
| topic | <i>Talaromyces pinophilus</i> Trichocomaceae marine sponge-associated fungus hybrid oxyphenalenone highly conjugated C<sub>28</sub> steroid azaphilone |
| url | https://www.mdpi.com/1660-3397/21/3/194 |
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