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New Highly Oxygenated Germacranolides from Carpesium divaricatum and their Cytotoxic Activity

Eight highly oxygenated germacranolides (1–8) including four new ones (2–5) were isolated from the whole plant of Carpesium divaricatum. The planar structures and relative configurations of the new compounds were determined by NMR experiment and HRESIMS data. The absolute configuration of 1 was esta...

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Autores principales: Zhang, Tao, Si, Jin-Guang, Zhang, Qiu-Bo, Ding, Gang, Zou, Zhong-Mei
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4893730/
https://www.ncbi.nlm.nih.gov/pubmed/27265755
http://dx.doi.org/10.1038/srep27237
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author Zhang, Tao
Si, Jin-Guang
Zhang, Qiu-Bo
Ding, Gang
Zou, Zhong-Mei
author_facet Zhang, Tao
Si, Jin-Guang
Zhang, Qiu-Bo
Ding, Gang
Zou, Zhong-Mei
author_sort Zhang, Tao
collection PubMed
description Eight highly oxygenated germacranolides (1–8) including four new ones (2–5) were isolated from the whole plant of Carpesium divaricatum. The planar structures and relative configurations of the new compounds were determined by NMR experiment and HRESIMS data. The absolute configuration of 1 was established by circular dichroism (CD) method and X-ray diffraction, and the stereochemistry of the new compounds 2–5 were determined by similar CD spectra with 1. Compound 2 is the first hydroperoxyl germacrane from the genus Carpesium. The (13)C NMR data of 1, NMR data of 6–7, and their absolute configurations were reported for the first time. Two new compounds (2 and 4) and two known compounds (6 and 8) exhibited potent cytotoxicity against human cervical cancer (HeLa) cells, superior to that of the positive control doxorubicin.
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spelling pubmed-48937302016-06-10 New Highly Oxygenated Germacranolides from Carpesium divaricatum and their Cytotoxic Activity Zhang, Tao Si, Jin-Guang Zhang, Qiu-Bo Ding, Gang Zou, Zhong-Mei Sci Rep Article Eight highly oxygenated germacranolides (1–8) including four new ones (2–5) were isolated from the whole plant of Carpesium divaricatum. The planar structures and relative configurations of the new compounds were determined by NMR experiment and HRESIMS data. The absolute configuration of 1 was established by circular dichroism (CD) method and X-ray diffraction, and the stereochemistry of the new compounds 2–5 were determined by similar CD spectra with 1. Compound 2 is the first hydroperoxyl germacrane from the genus Carpesium. The (13)C NMR data of 1, NMR data of 6–7, and their absolute configurations were reported for the first time. Two new compounds (2 and 4) and two known compounds (6 and 8) exhibited potent cytotoxicity against human cervical cancer (HeLa) cells, superior to that of the positive control doxorubicin. Nature Publishing Group 2016-06-06 /pmc/articles/PMC4893730/ /pubmed/27265755 http://dx.doi.org/10.1038/srep27237 Text en Copyright © 2016, Macmillan Publishers Limited http://creativecommons.org/licenses/by/4.0/ This work is licensed under a Creative Commons Attribution 4.0 International License. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in the credit line; if the material is not included under the Creative Commons license, users will need to obtain permission from the license holder to reproduce the material. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/
spellingShingle Article
Zhang, Tao
Si, Jin-Guang
Zhang, Qiu-Bo
Ding, Gang
Zou, Zhong-Mei
New Highly Oxygenated Germacranolides from Carpesium divaricatum and their Cytotoxic Activity
title New Highly Oxygenated Germacranolides from Carpesium divaricatum and their Cytotoxic Activity
title_full New Highly Oxygenated Germacranolides from Carpesium divaricatum and their Cytotoxic Activity
title_fullStr New Highly Oxygenated Germacranolides from Carpesium divaricatum and their Cytotoxic Activity
title_full_unstemmed New Highly Oxygenated Germacranolides from Carpesium divaricatum and their Cytotoxic Activity
title_short New Highly Oxygenated Germacranolides from Carpesium divaricatum and their Cytotoxic Activity
title_sort new highly oxygenated germacranolides from carpesium divaricatum and their cytotoxic activity
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4893730/
https://www.ncbi.nlm.nih.gov/pubmed/27265755
http://dx.doi.org/10.1038/srep27237
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