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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...
Autores principales: | , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2013
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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. |
format | Online Article Text |
id | pubmed-3707162 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2013 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
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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