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Tuaimenals B–H, Merosesquiterpenes from the Irish Deep-Sea Soft Coral Duva florida with Bioactivity against Cervical Cancer Cell Lines
[Image: see text] Previous chemical investigation of the Irish deep-sea soft coral Duva florida led to the identification of tuaimenal A (10), a new merosesquiterpene containing a highly substituted chromene core and modest cytotoxicity against cervical cancer. Further MS/MS and NMR-guided investiga...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society and American Society of Pharmacognosy
2022
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9887596/ https://www.ncbi.nlm.nih.gov/pubmed/36580354 http://dx.doi.org/10.1021/acs.jnatprod.2c00898 |
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author | Welsch, Joshua T. Smalley, Tracess B. Matlack, Jenet K. Avalon, Nicole E. Binning, Jennifer M. Johnson, Mark P. Allcock, A. Louise Baker, Bill J. |
author_facet | Welsch, Joshua T. Smalley, Tracess B. Matlack, Jenet K. Avalon, Nicole E. Binning, Jennifer M. Johnson, Mark P. Allcock, A. Louise Baker, Bill J. |
author_sort | Welsch, Joshua T. |
collection | PubMed |
description | [Image: see text] Previous chemical investigation of the Irish deep-sea soft coral Duva florida led to the identification of tuaimenal A (10), a new merosesquiterpene containing a highly substituted chromene core and modest cytotoxicity against cervical cancer. Further MS/MS and NMR-guided investigation of this octocoral has resulted in the isolation and characterization of seven additional tuaimenal analogs, B–H (1–7), as well as two known A-ring aromatized steroids (8, 9), and additional tuaimenal A (10). Tuaimenals B, F, and G (1, 5, 6), bearing an oxygen at the C(5) position, as well as monocyclic tuaimenal H (7), show increased cervical cancer inhibition profiles in comparison to that of 10. Tuaimenal G further displayed potent, selective cytotoxicity with an EC(50) value of 0.04 μM against the C33A cell line compared to the CaSki cell line (EC(50) 20 μM). These data reveal the anticancer properties of tuaimenal analogs and suggest unique antiproliferation mechanisms across these secondary metabolites. |
format | Online Article Text |
id | pubmed-9887596 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | American Chemical Society and American Society of Pharmacognosy |
record_format | MEDLINE/PubMed |
spelling | pubmed-98875962023-02-01 Tuaimenals B–H, Merosesquiterpenes from the Irish Deep-Sea Soft Coral Duva florida with Bioactivity against Cervical Cancer Cell Lines Welsch, Joshua T. Smalley, Tracess B. Matlack, Jenet K. Avalon, Nicole E. Binning, Jennifer M. Johnson, Mark P. Allcock, A. Louise Baker, Bill J. J Nat Prod [Image: see text] Previous chemical investigation of the Irish deep-sea soft coral Duva florida led to the identification of tuaimenal A (10), a new merosesquiterpene containing a highly substituted chromene core and modest cytotoxicity against cervical cancer. Further MS/MS and NMR-guided investigation of this octocoral has resulted in the isolation and characterization of seven additional tuaimenal analogs, B–H (1–7), as well as two known A-ring aromatized steroids (8, 9), and additional tuaimenal A (10). Tuaimenals B, F, and G (1, 5, 6), bearing an oxygen at the C(5) position, as well as monocyclic tuaimenal H (7), show increased cervical cancer inhibition profiles in comparison to that of 10. Tuaimenal G further displayed potent, selective cytotoxicity with an EC(50) value of 0.04 μM against the C33A cell line compared to the CaSki cell line (EC(50) 20 μM). These data reveal the anticancer properties of tuaimenal analogs and suggest unique antiproliferation mechanisms across these secondary metabolites. American Chemical Society and American Society of Pharmacognosy 2022-12-29 /pmc/articles/PMC9887596/ /pubmed/36580354 http://dx.doi.org/10.1021/acs.jnatprod.2c00898 Text en © 2022 The Authors. Published by American Chemical Society and American Society of Pharmacognosy https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Welsch, Joshua T. Smalley, Tracess B. Matlack, Jenet K. Avalon, Nicole E. Binning, Jennifer M. Johnson, Mark P. Allcock, A. Louise Baker, Bill J. Tuaimenals B–H, Merosesquiterpenes from the Irish Deep-Sea Soft Coral Duva florida with Bioactivity against Cervical Cancer Cell Lines |
title | Tuaimenals
B–H, Merosesquiterpenes from the
Irish Deep-Sea Soft Coral Duva florida with Bioactivity
against Cervical Cancer Cell Lines |
title_full | Tuaimenals
B–H, Merosesquiterpenes from the
Irish Deep-Sea Soft Coral Duva florida with Bioactivity
against Cervical Cancer Cell Lines |
title_fullStr | Tuaimenals
B–H, Merosesquiterpenes from the
Irish Deep-Sea Soft Coral Duva florida with Bioactivity
against Cervical Cancer Cell Lines |
title_full_unstemmed | Tuaimenals
B–H, Merosesquiterpenes from the
Irish Deep-Sea Soft Coral Duva florida with Bioactivity
against Cervical Cancer Cell Lines |
title_short | Tuaimenals
B–H, Merosesquiterpenes from the
Irish Deep-Sea Soft Coral Duva florida with Bioactivity
against Cervical Cancer Cell Lines |
title_sort | tuaimenals
b–h, merosesquiterpenes from the
irish deep-sea soft coral duva florida with bioactivity
against cervical cancer cell lines |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9887596/ https://www.ncbi.nlm.nih.gov/pubmed/36580354 http://dx.doi.org/10.1021/acs.jnatprod.2c00898 |
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