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New Hybrid Phenalenone Dimer, Highly Conjugated Dihydroxylated C(28) Steroid and Azaphilone from the Culture Extract of a Marine Sponge-Associated Fungus, Talaromyces pinophilus KUFA 1767
An undescribed hybrid phenalenone dimer, talaropinophilone (3), an unreported azaphilone, 7-epi-pinazaphilone B (4), an unreported phthalide dimer, talaropinophilide (6), and an undescribed 9R,15S-dihydroxy-ergosta-4,6,8 (14)-tetraen-3-one (7) were isolated together with the previously reported baci...
Autores principales: | , , , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2023
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10051590/ https://www.ncbi.nlm.nih.gov/pubmed/36976243 http://dx.doi.org/10.3390/md21030194 |
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author | Machado, Fátima P. Rodrigues, Inês C. Georgopolou, Aikaterini Gales, Luís Pereira, José A. Costa, Paulo M. Mistry, Sharad Hafez Ghoran, Salar Silva, Artur M. S. Dethoup, Tida Sousa, Emília Kijjoa, Anake |
author_facet | Machado, Fátima P. Rodrigues, Inês C. Georgopolou, Aikaterini Gales, Luís Pereira, José A. Costa, Paulo M. Mistry, Sharad Hafez Ghoran, Salar Silva, Artur M. S. Dethoup, Tida Sousa, Emília Kijjoa, Anake |
author_sort | Machado, Fátima P. |
collection | PubMed |
description | An undescribed hybrid phenalenone dimer, talaropinophilone (3), an unreported azaphilone, 7-epi-pinazaphilone B (4), an unreported phthalide dimer, talaropinophilide (6), and an undescribed 9R,15S-dihydroxy-ergosta-4,6,8 (14)-tetraen-3-one (7) were isolated together with the previously reported bacillisporins A (1) and B (2), an azaphilone derivative, Sch 1385568 (5), 1-deoxyrubralactone (8), acetylquestinol (9), piniterpenoid D (10) and 3,5-dihydroxy-4-methylphthalaldehydic acid (11) from the ethyl acetate extract of the culture of a marine sponge-derived fungus, Talaromyces pinophilus 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 1 and 2 was revised to be 9′S using the coupling constant value between C-8′ and C-9′ and was confirmed by ROESY correlations in the case of 2. The absolute configurations of the stereogenic carbons in 7 and 8 were established by X-ray crystallographic analysis. Compounds 1,2, 4–8, 10 and 11 were tested for antibacterial activity against four reference strains, viz. two Gram-positive (Staphylococcus aureus ATCC 29213, Enterococcus faecalis ATCC 29212) and two Gram-negative (Escherichia coli ATCC 25922, Pseudomonas aeruginosa ATCC 27853), as well as three multidrug-resistant strains, viz. an extended-spectrum β-lactamase (ESBL)-producing E. coli, a methicillin-resistant S. aureus (MRSA) and a vancomycin-resistant E. faecalis (VRE). However, only 1 and 2 exhibited significant antibacterial activity against both S. aureus ATCC 29213 and MRSA. Moreover, 1 and 2 also significantly inhibited biofilm formation in S. aureus ATCC 29213 at both MIC and 2xMIC concentrations. |
format | Online Article Text |
id | pubmed-10051590 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-100515902023-03-30 New Hybrid Phenalenone Dimer, Highly Conjugated Dihydroxylated C(28) Steroid and Azaphilone from the Culture Extract of a Marine Sponge-Associated Fungus, Talaromyces pinophilus KUFA 1767 Machado, Fátima P. Rodrigues, Inês C. Georgopolou, Aikaterini Gales, Luís Pereira, José A. Costa, Paulo M. Mistry, Sharad Hafez Ghoran, Salar Silva, Artur M. S. Dethoup, Tida Sousa, Emília Kijjoa, Anake Mar Drugs Article An undescribed hybrid phenalenone dimer, talaropinophilone (3), an unreported azaphilone, 7-epi-pinazaphilone B (4), an unreported phthalide dimer, talaropinophilide (6), and an undescribed 9R,15S-dihydroxy-ergosta-4,6,8 (14)-tetraen-3-one (7) were isolated together with the previously reported bacillisporins A (1) and B (2), an azaphilone derivative, Sch 1385568 (5), 1-deoxyrubralactone (8), acetylquestinol (9), piniterpenoid D (10) and 3,5-dihydroxy-4-methylphthalaldehydic acid (11) from the ethyl acetate extract of the culture of a marine sponge-derived fungus, Talaromyces pinophilus 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 1 and 2 was revised to be 9′S using the coupling constant value between C-8′ and C-9′ and was confirmed by ROESY correlations in the case of 2. The absolute configurations of the stereogenic carbons in 7 and 8 were established by X-ray crystallographic analysis. Compounds 1,2, 4–8, 10 and 11 were tested for antibacterial activity against four reference strains, viz. two Gram-positive (Staphylococcus aureus ATCC 29213, Enterococcus faecalis ATCC 29212) and two Gram-negative (Escherichia coli ATCC 25922, Pseudomonas aeruginosa ATCC 27853), as well as three multidrug-resistant strains, viz. an extended-spectrum β-lactamase (ESBL)-producing E. coli, a methicillin-resistant S. aureus (MRSA) and a vancomycin-resistant E. faecalis (VRE). However, only 1 and 2 exhibited significant antibacterial activity against both S. aureus ATCC 29213 and MRSA. Moreover, 1 and 2 also significantly inhibited biofilm formation in S. aureus ATCC 29213 at both MIC and 2xMIC concentrations. MDPI 2023-03-21 /pmc/articles/PMC10051590/ /pubmed/36976243 http://dx.doi.org/10.3390/md21030194 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Machado, Fátima P. Rodrigues, Inês C. Georgopolou, Aikaterini Gales, Luís Pereira, José A. Costa, Paulo M. Mistry, Sharad Hafez Ghoran, Salar Silva, Artur M. S. Dethoup, Tida Sousa, Emília Kijjoa, Anake New Hybrid Phenalenone Dimer, Highly Conjugated Dihydroxylated C(28) Steroid and Azaphilone from the Culture Extract of a Marine Sponge-Associated Fungus, Talaromyces pinophilus KUFA 1767 |
title | New Hybrid Phenalenone Dimer, Highly Conjugated Dihydroxylated C(28) Steroid and Azaphilone from the Culture Extract of a Marine Sponge-Associated Fungus, Talaromyces pinophilus KUFA 1767 |
title_full | New Hybrid Phenalenone Dimer, Highly Conjugated Dihydroxylated C(28) Steroid and Azaphilone from the Culture Extract of a Marine Sponge-Associated Fungus, Talaromyces pinophilus KUFA 1767 |
title_fullStr | New Hybrid Phenalenone Dimer, Highly Conjugated Dihydroxylated C(28) Steroid and Azaphilone from the Culture Extract of a Marine Sponge-Associated Fungus, Talaromyces pinophilus KUFA 1767 |
title_full_unstemmed | New Hybrid Phenalenone Dimer, Highly Conjugated Dihydroxylated C(28) Steroid and Azaphilone from the Culture Extract of a Marine Sponge-Associated Fungus, Talaromyces pinophilus KUFA 1767 |
title_short | New Hybrid Phenalenone Dimer, Highly Conjugated Dihydroxylated C(28) Steroid and Azaphilone from the Culture Extract of a Marine Sponge-Associated Fungus, Talaromyces pinophilus KUFA 1767 |
title_sort | new hybrid phenalenone dimer, highly conjugated dihydroxylated c(28) steroid and azaphilone from the culture extract of a marine sponge-associated fungus, talaromyces pinophilus kufa 1767 |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10051590/ https://www.ncbi.nlm.nih.gov/pubmed/36976243 http://dx.doi.org/10.3390/md21030194 |
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