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Chemistry and Tumor Cell Growth Inhibitory Activity of 11,20-Epoxy-3Z,5(6)E-diene Briaranes from the South China Sea Gorgonian Dichotella gemmacea

Eighteen new 11,20-epoxy-3Z,5E-dien briaranes, gemmacolides AA–AR (1–18), were isolated together with three known analogs, dichotellides F (19) and I (20), and juncenolide C (21), from the South China Sea gorgonian Dichotella gemmacea. The structures of the compounds were elucidated by detailed spec...

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Autores principales: Li, Cui, Jiang, Mei, La, Ming-Ping, Li, Tie-Jun, Tang, Hua, Sun, Peng, Liu, Bao-Shu, Yi, Yang-Hua, Liu, Zhiyong, Zhang, Wen
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2013
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3707162/
https://www.ncbi.nlm.nih.gov/pubmed/23697947
http://dx.doi.org/10.3390/md11051565
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author Li, Cui
Jiang, Mei
La, Ming-Ping
Li, Tie-Jun
Tang, Hua
Sun, Peng
Liu, Bao-Shu
Yi, Yang-Hua
Liu, Zhiyong
Zhang, Wen
author_facet Li, Cui
Jiang, Mei
La, Ming-Ping
Li, Tie-Jun
Tang, Hua
Sun, Peng
Liu, Bao-Shu
Yi, Yang-Hua
Liu, Zhiyong
Zhang, Wen
author_sort Li, Cui
collection PubMed
description Eighteen new 11,20-epoxy-3Z,5E-dien briaranes, gemmacolides AA–AR (1–18), were isolated together with three known analogs, dichotellides F (19) and I (20), and juncenolide C (21), from the South China Sea gorgonian Dichotella gemmacea. The structures of the compounds were elucidated by detailed spectroscopic analysis and comparison with reported data. The absolute configuration was determined based on the ECD experiment. In the in vitro bioassay, compounds 1–3, 5, 6, 8–12, and 14–19 exhibited different levels of growth inhibition activity against A549 and MG63 cell lines. Preliminary structure-activity analysis suggests that 12-O-isovalerate may increase the activity whereas 13- or 14-O-isovalerate may decrease the activity. Contribution of substitutions at C-2 and C-16 remains uncertain.
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spelling pubmed-37071622013-07-10 Chemistry and Tumor Cell Growth Inhibitory Activity of 11,20-Epoxy-3Z,5(6)E-diene Briaranes from the South China Sea Gorgonian Dichotella gemmacea Li, Cui Jiang, Mei La, Ming-Ping Li, Tie-Jun Tang, Hua Sun, Peng Liu, Bao-Shu Yi, Yang-Hua Liu, Zhiyong Zhang, Wen Mar Drugs Article Eighteen new 11,20-epoxy-3Z,5E-dien briaranes, gemmacolides AA–AR (1–18), were isolated together with three known analogs, dichotellides F (19) and I (20), and juncenolide C (21), from the South China Sea gorgonian Dichotella gemmacea. The structures of the compounds were elucidated by detailed spectroscopic analysis and comparison with reported data. The absolute configuration was determined based on the ECD experiment. In the in vitro bioassay, compounds 1–3, 5, 6, 8–12, and 14–19 exhibited different levels of growth inhibition activity against A549 and MG63 cell lines. Preliminary structure-activity analysis suggests that 12-O-isovalerate may increase the activity whereas 13- or 14-O-isovalerate may decrease the activity. Contribution of substitutions at C-2 and C-16 remains uncertain. MDPI 2013-05-15 /pmc/articles/PMC3707162/ /pubmed/23697947 http://dx.doi.org/10.3390/md11051565 Text en © 2013 by the authors; licensee MDPI, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0/ This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Li, Cui
Jiang, Mei
La, Ming-Ping
Li, Tie-Jun
Tang, Hua
Sun, Peng
Liu, Bao-Shu
Yi, Yang-Hua
Liu, Zhiyong
Zhang, Wen
Chemistry and Tumor Cell Growth Inhibitory Activity of 11,20-Epoxy-3Z,5(6)E-diene Briaranes from the South China Sea Gorgonian Dichotella gemmacea
title Chemistry and Tumor Cell Growth Inhibitory Activity of 11,20-Epoxy-3Z,5(6)E-diene Briaranes from the South China Sea Gorgonian Dichotella gemmacea
title_full Chemistry and Tumor Cell Growth Inhibitory Activity of 11,20-Epoxy-3Z,5(6)E-diene Briaranes from the South China Sea Gorgonian Dichotella gemmacea
title_fullStr Chemistry and Tumor Cell Growth Inhibitory Activity of 11,20-Epoxy-3Z,5(6)E-diene Briaranes from the South China Sea Gorgonian Dichotella gemmacea
title_full_unstemmed Chemistry and Tumor Cell Growth Inhibitory Activity of 11,20-Epoxy-3Z,5(6)E-diene Briaranes from the South China Sea Gorgonian Dichotella gemmacea
title_short Chemistry and Tumor Cell Growth Inhibitory Activity of 11,20-Epoxy-3Z,5(6)E-diene Briaranes from the South China Sea Gorgonian Dichotella gemmacea
title_sort chemistry and tumor cell growth inhibitory activity of 11,20-epoxy-3z,5(6)e-diene briaranes from the south china sea gorgonian dichotella gemmacea
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3707162/
https://www.ncbi.nlm.nih.gov/pubmed/23697947
http://dx.doi.org/10.3390/md11051565
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