Antibacterial Spirotetronate Polyketides from an <i>Actinomadura</i> sp. Strain A30804
Large scale cultivation and chemical investigation of an extract obtained from <i>Actimonadura</i> sp. resulted in the identification of six previously undescribed spirotetronates (pyrrolosporin B and decatromicins C–G; <b>7</b>–<b>12</b>), along with six known co...
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MDPI AG
2022-11-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/23/8196 |
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| author | Kuan-Chieh Ching Elaine J. Chin Mario Wibowo Zann Y. Tan Lay-Kien Yang Deborah C. Seow Chung-Yan Leong Veronica W. Ng Siew-Bee Ng Yoganathan Kanagasundaram |
| author_facet | Kuan-Chieh Ching Elaine J. Chin Mario Wibowo Zann Y. Tan Lay-Kien Yang Deborah C. Seow Chung-Yan Leong Veronica W. Ng Siew-Bee Ng Yoganathan Kanagasundaram |
| author_sort | Kuan-Chieh Ching |
| collection | DOAJ |
| description | Large scale cultivation and chemical investigation of an extract obtained from <i>Actimonadura</i> sp. resulted in the identification of six previously undescribed spirotetronates (pyrrolosporin B and decatromicins C–G; <b>7</b>–<b>12</b>), along with six known congeners, namely decatromicins A–B (<b>1</b>–<b>2</b>), BE-45722B–D (<b>3</b>–<b>5</b>), and pyrrolosporin A (<b>6</b>). The chemical structures of compounds <b>1</b>–<b>12</b> were characterized via comparison with previously reported data and analysis of 1D/2D NMR and MS data. The structures of all new compounds were highly related to the spirotetronate type compounds, decatromicin and pyrrolosporin, with variations in the substituents on the pyrrole and aglycone moieties. All compounds were evaluated for antibacterial activity against the Gram-negative bacteria, <i>Acinetobacter baumannii</i> and Gram-positive bacteria, <i>Staphylococcus aureus</i> and were investigated for their cytotoxicity against the human cancer cell line A549. Of these, decatromicin B (<b>2</b>), BE-45722B (<b>3</b>), and pyrrolosporin B (<b>7</b>) exhibited potent antibacterial activities against both Gram-positive (MIC<sub>90</sub> between 1–3 μM) and Gram-negative bacteria (MIC<sub>90</sub> values ranging from 12–36 μM) with weak or no cytotoxic activity against A549 cells. |
| first_indexed | 2024-03-09T17:39:35Z |
| format | Article |
| id | doaj.art-5a75cf5e4bda47d5a23d26f56116776e |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T17:39:35Z |
| publishDate | 2022-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-5a75cf5e4bda47d5a23d26f56116776e2023-11-24T11:38:13ZengMDPI AGMolecules1420-30492022-11-012723819610.3390/molecules27238196Antibacterial Spirotetronate Polyketides from an <i>Actinomadura</i> sp. Strain A30804Kuan-Chieh Ching0Elaine J. Chin1Mario Wibowo2Zann Y. Tan3Lay-Kien Yang4Deborah C. Seow5Chung-Yan Leong6Veronica W. Ng7Siew-Bee Ng8Yoganathan Kanagasundaram9Singapore Institute of Food and Biotechnology Innovation (SIFBI), Agency for Science, Technology and Research (A*STAR), Singapore 138673, SingaporeSingapore Institute of Food and Biotechnology Innovation (SIFBI), Agency for Science, Technology and Research (A*STAR), Singapore 138673, SingaporeSingapore Institute of Food and Biotechnology Innovation (SIFBI), Agency for Science, Technology and Research (A*STAR), Singapore 138673, SingaporeSingapore Institute of Food and Biotechnology Innovation (SIFBI), Agency for Science, Technology and Research (A*STAR), Singapore 138673, SingaporeSingapore Institute of Food and Biotechnology Innovation (SIFBI), Agency for Science, Technology and Research (A*STAR), Singapore 138673, SingaporeSingapore Institute of Food and Biotechnology Innovation (SIFBI), Agency for Science, Technology and Research (A*STAR), Singapore 138673, SingaporeSingapore Institute of Food and Biotechnology Innovation (SIFBI), Agency for Science, Technology and Research (A*STAR), Singapore 138673, SingaporeSingapore Institute of Food and Biotechnology Innovation (SIFBI), Agency for Science, Technology and Research (A*STAR), Singapore 138673, SingaporeSingapore Institute of Food and Biotechnology Innovation (SIFBI), Agency for Science, Technology and Research (A*STAR), Singapore 138673, SingaporeSingapore Institute of Food and Biotechnology Innovation (SIFBI), Agency for Science, Technology and Research (A*STAR), Singapore 138673, SingaporeLarge scale cultivation and chemical investigation of an extract obtained from <i>Actimonadura</i> sp. resulted in the identification of six previously undescribed spirotetronates (pyrrolosporin B and decatromicins C–G; <b>7</b>–<b>12</b>), along with six known congeners, namely decatromicins A–B (<b>1</b>–<b>2</b>), BE-45722B–D (<b>3</b>–<b>5</b>), and pyrrolosporin A (<b>6</b>). The chemical structures of compounds <b>1</b>–<b>12</b> were characterized via comparison with previously reported data and analysis of 1D/2D NMR and MS data. The structures of all new compounds were highly related to the spirotetronate type compounds, decatromicin and pyrrolosporin, with variations in the substituents on the pyrrole and aglycone moieties. All compounds were evaluated for antibacterial activity against the Gram-negative bacteria, <i>Acinetobacter baumannii</i> and Gram-positive bacteria, <i>Staphylococcus aureus</i> and were investigated for their cytotoxicity against the human cancer cell line A549. Of these, decatromicin B (<b>2</b>), BE-45722B (<b>3</b>), and pyrrolosporin B (<b>7</b>) exhibited potent antibacterial activities against both Gram-positive (MIC<sub>90</sub> between 1–3 μM) and Gram-negative bacteria (MIC<sub>90</sub> values ranging from 12–36 μM) with weak or no cytotoxic activity against A549 cells.https://www.mdpi.com/1420-3049/27/23/8196spirotetronatedecatromicinpyrrolosporinantibacterialnatural productsstructure elucidation |
| spellingShingle | Kuan-Chieh Ching Elaine J. Chin Mario Wibowo Zann Y. Tan Lay-Kien Yang Deborah C. Seow Chung-Yan Leong Veronica W. Ng Siew-Bee Ng Yoganathan Kanagasundaram Antibacterial Spirotetronate Polyketides from an <i>Actinomadura</i> sp. Strain A30804 Molecules spirotetronate decatromicin pyrrolosporin antibacterial natural products structure elucidation |
| title | Antibacterial Spirotetronate Polyketides from an <i>Actinomadura</i> sp. Strain A30804 |
| title_full | Antibacterial Spirotetronate Polyketides from an <i>Actinomadura</i> sp. Strain A30804 |
| title_fullStr | Antibacterial Spirotetronate Polyketides from an <i>Actinomadura</i> sp. Strain A30804 |
| title_full_unstemmed | Antibacterial Spirotetronate Polyketides from an <i>Actinomadura</i> sp. Strain A30804 |
| title_short | Antibacterial Spirotetronate Polyketides from an <i>Actinomadura</i> sp. Strain A30804 |
| title_sort | antibacterial spirotetronate polyketides from an i actinomadura i sp strain a30804 |
| topic | spirotetronate decatromicin pyrrolosporin antibacterial natural products structure elucidation |
| url | https://www.mdpi.com/1420-3049/27/23/8196 |
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