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Coumarin derivatives from Ainsliaea fragrans and their anticoagulant activity

Coumarin derivatives are an important class of C(6)–C(3) plant metabolites that show a variety of bioactivities. Currently, most clinical anticoagulant agents are coumarins, such as warfarin, dicoumarol and acenocoumarol, and patients taking these drugs must be monitored for adverse reactions. In a...

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Autores principales: Lei, Liang, Xue, Yong-bo, Liu, Zhong, Peng, Si-si, He, Yan, Zhang, Yang, Fang, Rong, Wang, Jian-ping, Luo, Zeng-wei, Yao, Guang-min, Zhang, Jin-wen, Zhang, Geng, Song, Hong-ping, Zhang, Yong-hui
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4551958/
https://www.ncbi.nlm.nih.gov/pubmed/26315062
http://dx.doi.org/10.1038/srep13544
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author Lei, Liang
Xue, Yong-bo
Liu, Zhong
Peng, Si-si
He, Yan
Zhang, Yang
Fang, Rong
Wang, Jian-ping
Luo, Zeng-wei
Yao, Guang-min
Zhang, Jin-wen
Zhang, Geng
Song, Hong-ping
Zhang, Yong-hui
author_facet Lei, Liang
Xue, Yong-bo
Liu, Zhong
Peng, Si-si
He, Yan
Zhang, Yang
Fang, Rong
Wang, Jian-ping
Luo, Zeng-wei
Yao, Guang-min
Zhang, Jin-wen
Zhang, Geng
Song, Hong-ping
Zhang, Yong-hui
author_sort Lei, Liang
collection PubMed
description Coumarin derivatives are an important class of C(6)–C(3) plant metabolites that show a variety of bioactivities. Currently, most clinical anticoagulant agents are coumarins, such as warfarin, dicoumarol and acenocoumarol, and patients taking these drugs must be monitored for adverse reactions. In a search for safe and effective anticoagulant compounds from Chinese herbal medicine, a screening procedure on the whole plant of Ainsliaea fragrans was performed. The phytochemical investigation of this plant afforded five new coumarin derivatives, including a pair of natural 4-hydroxycoumarin enantiomers (1), a pair of coumarin enantiomers with a rare polycyclic pyrano[3-2c] carbon skeleton (2) and a 7-hydroxycoumarin derivative (3), together with 5 known biogenetically related compounds (4–8). Enantioseparation of 1 and 2 produced optically pure compounds 1a, 1b, 2a and 2b. The absolute configurations of the new compounds were confirmed by single-crystal X-ray diffraction analysis. In addition, we evaluated the anticoagulant activity of all isolates via activated partial thromboplastin time (APTT), thrombin time (TT) and prothrombin time (PT) assays in vitro and in vivo. Of note, compound 3 displayed potent anticoagulant activity and no significant hepatic or renal toxicity, which could make it a promising agent for further preclinical evaluation for preventing abnormal blood clotting.
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spelling pubmed-45519582015-09-04 Coumarin derivatives from Ainsliaea fragrans and their anticoagulant activity Lei, Liang Xue, Yong-bo Liu, Zhong Peng, Si-si He, Yan Zhang, Yang Fang, Rong Wang, Jian-ping Luo, Zeng-wei Yao, Guang-min Zhang, Jin-wen Zhang, Geng Song, Hong-ping Zhang, Yong-hui Sci Rep Article Coumarin derivatives are an important class of C(6)–C(3) plant metabolites that show a variety of bioactivities. Currently, most clinical anticoagulant agents are coumarins, such as warfarin, dicoumarol and acenocoumarol, and patients taking these drugs must be monitored for adverse reactions. In a search for safe and effective anticoagulant compounds from Chinese herbal medicine, a screening procedure on the whole plant of Ainsliaea fragrans was performed. The phytochemical investigation of this plant afforded five new coumarin derivatives, including a pair of natural 4-hydroxycoumarin enantiomers (1), a pair of coumarin enantiomers with a rare polycyclic pyrano[3-2c] carbon skeleton (2) and a 7-hydroxycoumarin derivative (3), together with 5 known biogenetically related compounds (4–8). Enantioseparation of 1 and 2 produced optically pure compounds 1a, 1b, 2a and 2b. The absolute configurations of the new compounds were confirmed by single-crystal X-ray diffraction analysis. In addition, we evaluated the anticoagulant activity of all isolates via activated partial thromboplastin time (APTT), thrombin time (TT) and prothrombin time (PT) assays in vitro and in vivo. Of note, compound 3 displayed potent anticoagulant activity and no significant hepatic or renal toxicity, which could make it a promising agent for further preclinical evaluation for preventing abnormal blood clotting. Nature Publishing Group 2015-08-28 /pmc/articles/PMC4551958/ /pubmed/26315062 http://dx.doi.org/10.1038/srep13544 Text en Copyright © 2015, 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
Lei, Liang
Xue, Yong-bo
Liu, Zhong
Peng, Si-si
He, Yan
Zhang, Yang
Fang, Rong
Wang, Jian-ping
Luo, Zeng-wei
Yao, Guang-min
Zhang, Jin-wen
Zhang, Geng
Song, Hong-ping
Zhang, Yong-hui
Coumarin derivatives from Ainsliaea fragrans and their anticoagulant activity
title Coumarin derivatives from Ainsliaea fragrans and their anticoagulant activity
title_full Coumarin derivatives from Ainsliaea fragrans and their anticoagulant activity
title_fullStr Coumarin derivatives from Ainsliaea fragrans and their anticoagulant activity
title_full_unstemmed Coumarin derivatives from Ainsliaea fragrans and their anticoagulant activity
title_short Coumarin derivatives from Ainsliaea fragrans and their anticoagulant activity
title_sort coumarin derivatives from ainsliaea fragrans and their anticoagulant activity
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4551958/
https://www.ncbi.nlm.nih.gov/pubmed/26315062
http://dx.doi.org/10.1038/srep13544
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