Cargando…

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...

Descripción completa

Detalles Bibliográficos
Autores principales: Welsch, Joshua T., Smalley, Tracess B., Matlack, Jenet K., Avalon, Nicole E., Binning, Jennifer M., Johnson, Mark P., Allcock, A. Louise, Baker, Bill J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society and American Society of Pharmacognosy 2022
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
_version_ 1784880374033154048
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
work_keys_str_mv AT welschjoshuat tuaimenalsbhmerosesquiterpenesfromtheirishdeepseasoftcoralduvafloridawithbioactivityagainstcervicalcancercelllines
AT smalleytracessb tuaimenalsbhmerosesquiterpenesfromtheirishdeepseasoftcoralduvafloridawithbioactivityagainstcervicalcancercelllines
AT matlackjenetk tuaimenalsbhmerosesquiterpenesfromtheirishdeepseasoftcoralduvafloridawithbioactivityagainstcervicalcancercelllines
AT avalonnicolee tuaimenalsbhmerosesquiterpenesfromtheirishdeepseasoftcoralduvafloridawithbioactivityagainstcervicalcancercelllines
AT binningjenniferm tuaimenalsbhmerosesquiterpenesfromtheirishdeepseasoftcoralduvafloridawithbioactivityagainstcervicalcancercelllines
AT johnsonmarkp tuaimenalsbhmerosesquiterpenesfromtheirishdeepseasoftcoralduvafloridawithbioactivityagainstcervicalcancercelllines
AT allcockalouise tuaimenalsbhmerosesquiterpenesfromtheirishdeepseasoftcoralduvafloridawithbioactivityagainstcervicalcancercelllines
AT bakerbillj tuaimenalsbhmerosesquiterpenesfromtheirishdeepseasoftcoralduvafloridawithbioactivityagainstcervicalcancercelllines