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New antiproliferative germacranolides from Carpesium divaricatum

Six new highly oxygenated (2–7) and one known (1) germacranolides were isolated from the whole plant of Carpesium divaricatum. The planar structures and relative configurations of the new compounds were determined by detailed spectroscopic analysis. The absolute configurations of 1 and 3 were establ...

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Autores principales: Zhang, Tao, Zhang, Qiu-Bo, Fu, Lu, Li, Ling-Yu, Ma, Li-Yan, Si, Jin-Guang, Zhang, Hong-Wu, Wei, Jian-He, Yu, Shi-Shan, Zou, Zhong-Mei
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9063262/
https://www.ncbi.nlm.nih.gov/pubmed/35520265
http://dx.doi.org/10.1039/c9ra00478e
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author Zhang, Tao
Zhang, Qiu-Bo
Fu, Lu
Li, Ling-Yu
Ma, Li-Yan
Si, Jin-Guang
Zhang, Hong-Wu
Wei, Jian-He
Yu, Shi-Shan
Zou, Zhong-Mei
author_facet Zhang, Tao
Zhang, Qiu-Bo
Fu, Lu
Li, Ling-Yu
Ma, Li-Yan
Si, Jin-Guang
Zhang, Hong-Wu
Wei, Jian-He
Yu, Shi-Shan
Zou, Zhong-Mei
author_sort Zhang, Tao
collection PubMed
description Six new highly oxygenated (2–7) and one known (1) germacranolides were isolated from the whole plant of Carpesium divaricatum. The planar structures and relative configurations of the new compounds were determined by detailed spectroscopic analysis. The absolute configurations of 1 and 3 were established by circular dichroism (CD) and X-ray crystallographic analyses, and the stereochemistry of the new compounds 2 and 4–6 were determined by similar CD data to 1 and 3, respectively. All isolates were evaluated for their antiproliferative activities against three human tumor cell lines, and compounds 3 and 6 show antiproliferative activities against HeLa and Hep G2 cells with IC(50) values of 4.13–8.37 μM. Intensive mechanism study showed that 3 caused cell-cycle arrest at the S/G2 phase and induced apoptosis in Hep G2 cells through a mitochondria-related pathway.
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spelling pubmed-90632622022-05-04 New antiproliferative germacranolides from Carpesium divaricatum Zhang, Tao Zhang, Qiu-Bo Fu, Lu Li, Ling-Yu Ma, Li-Yan Si, Jin-Guang Zhang, Hong-Wu Wei, Jian-He Yu, Shi-Shan Zou, Zhong-Mei RSC Adv Chemistry Six new highly oxygenated (2–7) and one known (1) germacranolides were isolated from the whole plant of Carpesium divaricatum. The planar structures and relative configurations of the new compounds were determined by detailed spectroscopic analysis. The absolute configurations of 1 and 3 were established by circular dichroism (CD) and X-ray crystallographic analyses, and the stereochemistry of the new compounds 2 and 4–6 were determined by similar CD data to 1 and 3, respectively. All isolates were evaluated for their antiproliferative activities against three human tumor cell lines, and compounds 3 and 6 show antiproliferative activities against HeLa and Hep G2 cells with IC(50) values of 4.13–8.37 μM. Intensive mechanism study showed that 3 caused cell-cycle arrest at the S/G2 phase and induced apoptosis in Hep G2 cells through a mitochondria-related pathway. The Royal Society of Chemistry 2019-04-11 /pmc/articles/PMC9063262/ /pubmed/35520265 http://dx.doi.org/10.1039/c9ra00478e Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Zhang, Tao
Zhang, Qiu-Bo
Fu, Lu
Li, Ling-Yu
Ma, Li-Yan
Si, Jin-Guang
Zhang, Hong-Wu
Wei, Jian-He
Yu, Shi-Shan
Zou, Zhong-Mei
New antiproliferative germacranolides from Carpesium divaricatum
title New antiproliferative germacranolides from Carpesium divaricatum
title_full New antiproliferative germacranolides from Carpesium divaricatum
title_fullStr New antiproliferative germacranolides from Carpesium divaricatum
title_full_unstemmed New antiproliferative germacranolides from Carpesium divaricatum
title_short New antiproliferative germacranolides from Carpesium divaricatum
title_sort new antiproliferative germacranolides from carpesium divaricatum
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9063262/
https://www.ncbi.nlm.nih.gov/pubmed/35520265
http://dx.doi.org/10.1039/c9ra00478e
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