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Isolation and identification of two pairs of cytotoxic diterpene tautomers and their tautomerization mechanisms
Discovering anticancer drugs that do not have adverse side effects has been a developing research field worldwide in recent decades. In this work, four previously undescribed cytotoxic diterpenoids were isolated from the aerial parts of Isodon excisoides. Interestingly, these four diterpenoids were...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Nature Publishing Group UK
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6989466/ https://www.ncbi.nlm.nih.gov/pubmed/31996737 http://dx.doi.org/10.1038/s41598-020-58260-8 |
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author | Dai, Li-Ping Li, Xiao-Fei Feng, Qing-Mei Zhang, Ling-Xia Liu, Qiu-Yan Xu, Er-Ping Wu, Hong Wang, Zhi-Min |
author_facet | Dai, Li-Ping Li, Xiao-Fei Feng, Qing-Mei Zhang, Ling-Xia Liu, Qiu-Yan Xu, Er-Ping Wu, Hong Wang, Zhi-Min |
author_sort | Dai, Li-Ping |
collection | PubMed |
description | Discovering anticancer drugs that do not have adverse side effects has been a developing research field worldwide in recent decades. In this work, four previously undescribed cytotoxic diterpenoids were isolated from the aerial parts of Isodon excisoides. Interestingly, these four diterpenoids were two pairs of tautomers that were first reported in plants. Their structures were further elucidated using various spectroscopic methods. The tautomerization phenomenon and mechanism for these two pairs of tautomers were emphatically described. The theoretical simulation results indicated that the diterpene tautomerization is greatly related to certain factors, including the existence of a transition state, the change of bond length and the level of conversion energy; the tautomerization for the two pairs of tautomers is mainly caused by proton transfer. For bioassays, the cytotoxicities of the tautomers against five human cancer cell lines were also investigated. The results indicated that each of the four diterpenoids showed significant cytotoxicity in at least three cell lines and could serve as potential anticancer agents for further investigation. |
format | Online Article Text |
id | pubmed-6989466 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | Nature Publishing Group UK |
record_format | MEDLINE/PubMed |
spelling | pubmed-69894662020-02-03 Isolation and identification of two pairs of cytotoxic diterpene tautomers and their tautomerization mechanisms Dai, Li-Ping Li, Xiao-Fei Feng, Qing-Mei Zhang, Ling-Xia Liu, Qiu-Yan Xu, Er-Ping Wu, Hong Wang, Zhi-Min Sci Rep Article Discovering anticancer drugs that do not have adverse side effects has been a developing research field worldwide in recent decades. In this work, four previously undescribed cytotoxic diterpenoids were isolated from the aerial parts of Isodon excisoides. Interestingly, these four diterpenoids were two pairs of tautomers that were first reported in plants. Their structures were further elucidated using various spectroscopic methods. The tautomerization phenomenon and mechanism for these two pairs of tautomers were emphatically described. The theoretical simulation results indicated that the diterpene tautomerization is greatly related to certain factors, including the existence of a transition state, the change of bond length and the level of conversion energy; the tautomerization for the two pairs of tautomers is mainly caused by proton transfer. For bioassays, the cytotoxicities of the tautomers against five human cancer cell lines were also investigated. The results indicated that each of the four diterpenoids showed significant cytotoxicity in at least three cell lines and could serve as potential anticancer agents for further investigation. Nature Publishing Group UK 2020-01-29 /pmc/articles/PMC6989466/ /pubmed/31996737 http://dx.doi.org/10.1038/s41598-020-58260-8 Text en © The Author(s) 2020 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 Dai, Li-Ping Li, Xiao-Fei Feng, Qing-Mei Zhang, Ling-Xia Liu, Qiu-Yan Xu, Er-Ping Wu, Hong Wang, Zhi-Min Isolation and identification of two pairs of cytotoxic diterpene tautomers and their tautomerization mechanisms |
title | Isolation and identification of two pairs of cytotoxic diterpene tautomers and their tautomerization mechanisms |
title_full | Isolation and identification of two pairs of cytotoxic diterpene tautomers and their tautomerization mechanisms |
title_fullStr | Isolation and identification of two pairs of cytotoxic diterpene tautomers and their tautomerization mechanisms |
title_full_unstemmed | Isolation and identification of two pairs of cytotoxic diterpene tautomers and their tautomerization mechanisms |
title_short | Isolation and identification of two pairs of cytotoxic diterpene tautomers and their tautomerization mechanisms |
title_sort | isolation and identification of two pairs of cytotoxic diterpene tautomers and their tautomerization mechanisms |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6989466/ https://www.ncbi.nlm.nih.gov/pubmed/31996737 http://dx.doi.org/10.1038/s41598-020-58260-8 |
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