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Isolation, Structure Elucidation, and Absolute Configuration of Germacrane Isomers from Carpesium divaricatum

Five sets of germacrane isomers (1/8/17, 2/7/10/11/13/16/18, 3/4/5/14/20, 6/12/15, and 9/19) with different skeletal types, including seven new ones (1–3, 8–9, and 15–16) were isolated from the whole plant of Carpesium divaricatum. Among them, there are six pairs of stereoisomers (1/8, 2/13, 4/14, 6...

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Autores principales: Zhang, Tao, Chen, Jia-Huan, Si, Jin-Guang, Ding, Gang, Zhang, Qiu-Bo, Zhang, Hong-Wu, Jia, Hong-Mei, Zou, Zhong-Mei
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6102216/
https://www.ncbi.nlm.nih.gov/pubmed/30127485
http://dx.doi.org/10.1038/s41598-018-30782-2
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author Zhang, Tao
Chen, Jia-Huan
Si, Jin-Guang
Ding, Gang
Zhang, Qiu-Bo
Zhang, Hong-Wu
Jia, Hong-Mei
Zou, Zhong-Mei
author_facet Zhang, Tao
Chen, Jia-Huan
Si, Jin-Guang
Ding, Gang
Zhang, Qiu-Bo
Zhang, Hong-Wu
Jia, Hong-Mei
Zou, Zhong-Mei
author_sort Zhang, Tao
collection PubMed
description Five sets of germacrane isomers (1/8/17, 2/7/10/11/13/16/18, 3/4/5/14/20, 6/12/15, and 9/19) with different skeletal types, including seven new ones (1–3, 8–9, and 15–16) were isolated from the whole plant of Carpesium divaricatum. Among them, there are six pairs of stereoisomers (1/8, 2/13, 4/14, 6/12, 7/11 and 10/11). The planar structures and relative configurations of the new compounds were elucidated by detailed spectroscopic analysis. The absolute configurations of 4, 10, 11, and 17 were established by circular dichroism (CD) spectra and X-ray crystallographic analyses, and the stereochemistry of the new compounds 1–3, 8–9, and 15–16 were determined by similar CD spectra with 4, 10, 11, and 17, respectively. The confusion in the literature about subtypes I and II of germacranolides was clarified in this paper. The NMR data of 10–11, and the absolute configurations of the known compounds 4–6, 13–14, and 17–20 were reported for the first time. Compounds 13, 17, and 18 showed cytotoxicity against human cervical (HeLa), colon (LoVo) and stomach cancer (BGC-823) cell lines with IC(50) values in the range 4.72–13.68 μM compared with the control cis-platin (7.90–15.34 μM).
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spelling pubmed-61022162018-08-27 Isolation, Structure Elucidation, and Absolute Configuration of Germacrane Isomers from Carpesium divaricatum Zhang, Tao Chen, Jia-Huan Si, Jin-Guang Ding, Gang Zhang, Qiu-Bo Zhang, Hong-Wu Jia, Hong-Mei Zou, Zhong-Mei Sci Rep Article Five sets of germacrane isomers (1/8/17, 2/7/10/11/13/16/18, 3/4/5/14/20, 6/12/15, and 9/19) with different skeletal types, including seven new ones (1–3, 8–9, and 15–16) were isolated from the whole plant of Carpesium divaricatum. Among them, there are six pairs of stereoisomers (1/8, 2/13, 4/14, 6/12, 7/11 and 10/11). The planar structures and relative configurations of the new compounds were elucidated by detailed spectroscopic analysis. The absolute configurations of 4, 10, 11, and 17 were established by circular dichroism (CD) spectra and X-ray crystallographic analyses, and the stereochemistry of the new compounds 1–3, 8–9, and 15–16 were determined by similar CD spectra with 4, 10, 11, and 17, respectively. The confusion in the literature about subtypes I and II of germacranolides was clarified in this paper. The NMR data of 10–11, and the absolute configurations of the known compounds 4–6, 13–14, and 17–20 were reported for the first time. Compounds 13, 17, and 18 showed cytotoxicity against human cervical (HeLa), colon (LoVo) and stomach cancer (BGC-823) cell lines with IC(50) values in the range 4.72–13.68 μM compared with the control cis-platin (7.90–15.34 μM). Nature Publishing Group UK 2018-08-20 /pmc/articles/PMC6102216/ /pubmed/30127485 http://dx.doi.org/10.1038/s41598-018-30782-2 Text en © The Author(s) 2018 Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.
spellingShingle Article
Zhang, Tao
Chen, Jia-Huan
Si, Jin-Guang
Ding, Gang
Zhang, Qiu-Bo
Zhang, Hong-Wu
Jia, Hong-Mei
Zou, Zhong-Mei
Isolation, Structure Elucidation, and Absolute Configuration of Germacrane Isomers from Carpesium divaricatum
title Isolation, Structure Elucidation, and Absolute Configuration of Germacrane Isomers from Carpesium divaricatum
title_full Isolation, Structure Elucidation, and Absolute Configuration of Germacrane Isomers from Carpesium divaricatum
title_fullStr Isolation, Structure Elucidation, and Absolute Configuration of Germacrane Isomers from Carpesium divaricatum
title_full_unstemmed Isolation, Structure Elucidation, and Absolute Configuration of Germacrane Isomers from Carpesium divaricatum
title_short Isolation, Structure Elucidation, and Absolute Configuration of Germacrane Isomers from Carpesium divaricatum
title_sort isolation, structure elucidation, and absolute configuration of germacrane isomers from carpesium divaricatum
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6102216/
https://www.ncbi.nlm.nih.gov/pubmed/30127485
http://dx.doi.org/10.1038/s41598-018-30782-2
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