New Sesterterpenes from the Antarctic Sponge <i>Suberites</i> sp.
Chemical investigation of the Antarctic sponge <i>Suberites</i> sp. has previously led to the identification of new suberitane derivatives, some of which show bioactivity toward respiratory syncytial virus (RSV). Our ongoing NMR-guided investigation of new specimens of the sponge resulte...
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MDPI AG
2024-12-01
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| Series: | Marine Drugs |
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| Online Access: | https://www.mdpi.com/1660-3397/22/12/551 |
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| author | Stine S. H. Olsen Sydney K. Morrow Julia L. Szabo Michael N. Teng Kim C. Tran Charles D. Amsler James B. McClintock Bill. J. Baker |
| author_facet | Stine S. H. Olsen Sydney K. Morrow Julia L. Szabo Michael N. Teng Kim C. Tran Charles D. Amsler James B. McClintock Bill. J. Baker |
| author_sort | Stine S. H. Olsen |
| collection | DOAJ |
| description | Chemical investigation of the Antarctic sponge <i>Suberites</i> sp. has previously led to the identification of new suberitane derivatives, some of which show bioactivity toward respiratory syncytial virus (RSV). Our ongoing NMR-guided investigation of new specimens of the sponge resulted in the isolation of five new analogs (<b>1</b>–<b>5</b>), previously reported suberitenones A–D (<b>6</b>–<b>9</b>), and oxaspirosuberitenone (<b>10</b>). Suberitenone K (<b>1</b>) was characterized as the 8-keto derivative of <b>6</b>, while three new phenols, suberitandiol (<b>2</b>), abeosuberitandiol (<b>3</b>), and furanosuberitandiol (<b>4</b>), and the degraded sesterterpene norsuberitenone B (<b>5</b>) were also found. Compound <b>3</b> displays a ring contraction while <b>4</b> has a new dihydrofuran ring. Structural characterization was achieved by a combination of NMR, HR-MS, and X-ray diffraction (XRD). Moderate activity towards RSV was reported for <b>9</b> and the new metabolite <b>1</b>, with IC<sub>50</sub> values of 15.0 μM and 39.8 μM, respectively. |
| format | Article |
| id | doaj-art-0d521bac005f4e0fbf0b7a5b97107223 |
| institution | DOAJ |
| issn | 1660-3397 |
| language | English |
| publishDate | 2024-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj-art-0d521bac005f4e0fbf0b7a5b971072232025-08-20T02:50:41ZengMDPI AGMarine Drugs1660-33972024-12-01221255110.3390/md22120551New Sesterterpenes from the Antarctic Sponge <i>Suberites</i> sp.Stine S. H. Olsen0Sydney K. Morrow1Julia L. Szabo2Michael N. Teng3Kim C. Tran4Charles D. Amsler5James B. McClintock6Bill. J. Baker7Department of Chemistry, University of South Florida, 4202 E. Fowler Avenue, CHE205, Tampa, FL 33620, USADepartment of Chemistry, University of South Florida, 4202 E. Fowler Avenue, CHE205, Tampa, FL 33620, USADepartment of Chemistry, University of South Florida, 4202 E. Fowler Avenue, CHE205, Tampa, FL 33620, USADepartment of Internal Medicine, University of South Florida, Tampa, FL 33612, USADepartment of Internal Medicine, University of South Florida, Tampa, FL 33612, USADepartment of Biology, University of Alabama at Birmingham, 1300 University Blvd, Birmingham, AL 35233, USADepartment of Biology, University of Alabama at Birmingham, 1300 University Blvd, Birmingham, AL 35233, USADepartment of Chemistry, University of South Florida, 4202 E. Fowler Avenue, CHE205, Tampa, FL 33620, USAChemical investigation of the Antarctic sponge <i>Suberites</i> sp. has previously led to the identification of new suberitane derivatives, some of which show bioactivity toward respiratory syncytial virus (RSV). Our ongoing NMR-guided investigation of new specimens of the sponge resulted in the isolation of five new analogs (<b>1</b>–<b>5</b>), previously reported suberitenones A–D (<b>6</b>–<b>9</b>), and oxaspirosuberitenone (<b>10</b>). Suberitenone K (<b>1</b>) was characterized as the 8-keto derivative of <b>6</b>, while three new phenols, suberitandiol (<b>2</b>), abeosuberitandiol (<b>3</b>), and furanosuberitandiol (<b>4</b>), and the degraded sesterterpene norsuberitenone B (<b>5</b>) were also found. Compound <b>3</b> displays a ring contraction while <b>4</b> has a new dihydrofuran ring. Structural characterization was achieved by a combination of NMR, HR-MS, and X-ray diffraction (XRD). Moderate activity towards RSV was reported for <b>9</b> and the new metabolite <b>1</b>, with IC<sub>50</sub> values of 15.0 μM and 39.8 μM, respectively.https://www.mdpi.com/1660-3397/22/12/551<i>Suberites</i> sp.sesterterpenessuberitaneporiferaAntarcticaRSV |
| spellingShingle | Stine S. H. Olsen Sydney K. Morrow Julia L. Szabo Michael N. Teng Kim C. Tran Charles D. Amsler James B. McClintock Bill. J. Baker New Sesterterpenes from the Antarctic Sponge <i>Suberites</i> sp. Marine Drugs <i>Suberites</i> sp. sesterterpenes suberitane porifera Antarctica RSV |
| title | New Sesterterpenes from the Antarctic Sponge <i>Suberites</i> sp. |
| title_full | New Sesterterpenes from the Antarctic Sponge <i>Suberites</i> sp. |
| title_fullStr | New Sesterterpenes from the Antarctic Sponge <i>Suberites</i> sp. |
| title_full_unstemmed | New Sesterterpenes from the Antarctic Sponge <i>Suberites</i> sp. |
| title_short | New Sesterterpenes from the Antarctic Sponge <i>Suberites</i> sp. |
| title_sort | new sesterterpenes from the antarctic sponge i suberites i sp |
| topic | <i>Suberites</i> sp. sesterterpenes suberitane porifera Antarctica RSV |
| url | https://www.mdpi.com/1660-3397/22/12/551 |
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