Neosuberitenone, a New Sesterterpenoid Carbon Skeleton; New Suberitenones; and Bioactivity against Respiratory Syncytial Virus, from the Antarctic Sponge Suberites sp.
Respiratory syncytial virus (RSV) is a highly contagious human pathogen that poses a significant threat to children under the age of two, and there is a current need for new small molecule treatments. The Antarctic sponge Suberites sp. is a known source of sesterterpenes, and following an NMR-guided...
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2023
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Online Access: | https://doi.org/10.3390/md21020107 https://doaj.org/article/a2b6acfd7f154c71bca8e2aa09a2fb9a |
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ftdoajarticles:oai:doaj.org/article:a2b6acfd7f154c71bca8e2aa09a2fb9a 2023-05-15T13:44:48+02:00 Neosuberitenone, a New Sesterterpenoid Carbon Skeleton; New Suberitenones; and Bioactivity against Respiratory Syncytial Virus, from the Antarctic Sponge Suberites sp. Joe Bracegirdle Stine S. H. Olsen Michael N. Teng Kim C. Tran Charles D. Amsler James B. McClintock Bill J. Baker 2023-02-01T00:00:00Z https://doi.org/10.3390/md21020107 https://doaj.org/article/a2b6acfd7f154c71bca8e2aa09a2fb9a EN eng MDPI AG https://www.mdpi.com/1660-3397/21/2/107 https://doaj.org/toc/1660-3397 doi:10.3390/md21020107 1660-3397 https://doaj.org/article/a2b6acfd7f154c71bca8e2aa09a2fb9a Marine Drugs, Vol 21, Iss 107, p 107 (2023) antiviral RSV porifera sesquiterpene suberitane ansellane Biology (General) QH301-705.5 article 2023 ftdoajarticles https://doi.org/10.3390/md21020107 2023-02-26T01:29:24Z Respiratory syncytial virus (RSV) is a highly contagious human pathogen that poses a significant threat to children under the age of two, and there is a current need for new small molecule treatments. The Antarctic sponge Suberites sp. is a known source of sesterterpenes, and following an NMR-guided fractionation procedure, it was found to produce several previously unreported metabolites. Neosuberitenone ( 1 ), with a new carbon scaffold herein termed the ‘neosuberitane’ backbone, six suberitenone derivatives ( 2 – 7 ), an ansellane-type terpenoid ( 8 ), and a highly degraded sesterterpene ( 9 ), as well as previously reported suberitenones A ( 10 ) and B ( 11 ), were characterized. The structures of all of the isolated metabolites including absolute configurations are proposed on the basis of NMR, HRESIMS, optical rotation, and XRD data. The biological activities of the metabolites were evaluated in a range of infectious disease assays. Suberitenones A, B, and F ( 3 ) were found to be active against RSV, though, along with other Suberites sp. metabolites, they were inactive in bacterial and fungal screens. None of the metabolites were cytotoxic for J774 macrophages or A549 adenocarcinoma cells. The selectivity of suberitenones A, B, and F for RSV among other infectious agents is noteworthy. Article in Journal/Newspaper Antarc* Antarctic Directory of Open Access Journals: DOAJ Articles Antarctic The Antarctic Marine Drugs 21 2 107 |
institution |
Open Polar |
collection |
Directory of Open Access Journals: DOAJ Articles |
op_collection_id |
ftdoajarticles |
language |
English |
topic |
antiviral RSV porifera sesquiterpene suberitane ansellane Biology (General) QH301-705.5 |
spellingShingle |
antiviral RSV porifera sesquiterpene suberitane ansellane Biology (General) QH301-705.5 Joe Bracegirdle Stine S. H. Olsen Michael N. Teng Kim C. Tran Charles D. Amsler James B. McClintock Bill J. Baker Neosuberitenone, a New Sesterterpenoid Carbon Skeleton; New Suberitenones; and Bioactivity against Respiratory Syncytial Virus, from the Antarctic Sponge Suberites sp. |
topic_facet |
antiviral RSV porifera sesquiterpene suberitane ansellane Biology (General) QH301-705.5 |
description |
Respiratory syncytial virus (RSV) is a highly contagious human pathogen that poses a significant threat to children under the age of two, and there is a current need for new small molecule treatments. The Antarctic sponge Suberites sp. is a known source of sesterterpenes, and following an NMR-guided fractionation procedure, it was found to produce several previously unreported metabolites. Neosuberitenone ( 1 ), with a new carbon scaffold herein termed the ‘neosuberitane’ backbone, six suberitenone derivatives ( 2 – 7 ), an ansellane-type terpenoid ( 8 ), and a highly degraded sesterterpene ( 9 ), as well as previously reported suberitenones A ( 10 ) and B ( 11 ), were characterized. The structures of all of the isolated metabolites including absolute configurations are proposed on the basis of NMR, HRESIMS, optical rotation, and XRD data. The biological activities of the metabolites were evaluated in a range of infectious disease assays. Suberitenones A, B, and F ( 3 ) were found to be active against RSV, though, along with other Suberites sp. metabolites, they were inactive in bacterial and fungal screens. None of the metabolites were cytotoxic for J774 macrophages or A549 adenocarcinoma cells. The selectivity of suberitenones A, B, and F for RSV among other infectious agents is noteworthy. |
format |
Article in Journal/Newspaper |
author |
Joe Bracegirdle Stine S. H. Olsen Michael N. Teng Kim C. Tran Charles D. Amsler James B. McClintock Bill J. Baker |
author_facet |
Joe Bracegirdle Stine S. H. Olsen Michael N. Teng Kim C. Tran Charles D. Amsler James B. McClintock Bill J. Baker |
author_sort |
Joe Bracegirdle |
title |
Neosuberitenone, a New Sesterterpenoid Carbon Skeleton; New Suberitenones; and Bioactivity against Respiratory Syncytial Virus, from the Antarctic Sponge Suberites sp. |
title_short |
Neosuberitenone, a New Sesterterpenoid Carbon Skeleton; New Suberitenones; and Bioactivity against Respiratory Syncytial Virus, from the Antarctic Sponge Suberites sp. |
title_full |
Neosuberitenone, a New Sesterterpenoid Carbon Skeleton; New Suberitenones; and Bioactivity against Respiratory Syncytial Virus, from the Antarctic Sponge Suberites sp. |
title_fullStr |
Neosuberitenone, a New Sesterterpenoid Carbon Skeleton; New Suberitenones; and Bioactivity against Respiratory Syncytial Virus, from the Antarctic Sponge Suberites sp. |
title_full_unstemmed |
Neosuberitenone, a New Sesterterpenoid Carbon Skeleton; New Suberitenones; and Bioactivity against Respiratory Syncytial Virus, from the Antarctic Sponge Suberites sp. |
title_sort |
neosuberitenone, a new sesterterpenoid carbon skeleton; new suberitenones; and bioactivity against respiratory syncytial virus, from the antarctic sponge suberites sp. |
publisher |
MDPI AG |
publishDate |
2023 |
url |
https://doi.org/10.3390/md21020107 https://doaj.org/article/a2b6acfd7f154c71bca8e2aa09a2fb9a |
geographic |
Antarctic The Antarctic |
geographic_facet |
Antarctic The Antarctic |
genre |
Antarc* Antarctic |
genre_facet |
Antarc* Antarctic |
op_source |
Marine Drugs, Vol 21, Iss 107, p 107 (2023) |
op_relation |
https://www.mdpi.com/1660-3397/21/2/107 https://doaj.org/toc/1660-3397 doi:10.3390/md21020107 1660-3397 https://doaj.org/article/a2b6acfd7f154c71bca8e2aa09a2fb9a |
op_doi |
https://doi.org/10.3390/md21020107 |
container_title |
Marine Drugs |
container_volume |
21 |
container_issue |
2 |
container_start_page |
107 |
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1766207115863523328 |