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New Abietane and Kaurane Type Diterpenoids from the Stems of Tripterygium regelii

Eleven new abietane type (1‒11), and one new kaurane (12), diterpenes, together with eleven known compounds (13–23), were isolated and identified from the stems of Tripterygium regelii, which has been used as a traditional folk Chinese medicine for the treatment of rheumatoid arthritis in China. The...

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Autores principales: Fan, Dongsheng, Zhou, Shuangyan, Zheng, Zhiyuan, Zhu, Guo-Yuan, Yao, Xiaojun, Yang, Ming-Rong, Jiang, Zhi-Hong, Bai, Li-Ping
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5297780/
https://www.ncbi.nlm.nih.gov/pubmed/28098763
http://dx.doi.org/10.3390/ijms18010147
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author Fan, Dongsheng
Zhou, Shuangyan
Zheng, Zhiyuan
Zhu, Guo-Yuan
Yao, Xiaojun
Yang, Ming-Rong
Jiang, Zhi-Hong
Bai, Li-Ping
author_facet Fan, Dongsheng
Zhou, Shuangyan
Zheng, Zhiyuan
Zhu, Guo-Yuan
Yao, Xiaojun
Yang, Ming-Rong
Jiang, Zhi-Hong
Bai, Li-Ping
author_sort Fan, Dongsheng
collection PubMed
description Eleven new abietane type (1‒11), and one new kaurane (12), diterpenes, together with eleven known compounds (13–23), were isolated and identified from the stems of Tripterygium regelii, which has been used as a traditional folk Chinese medicine for the treatment of rheumatoid arthritis in China. The structures of new compounds were characterized by means of the interpretation of high-resolution electrospray ionization mass spectrometry (HRESIMS), extensive nuclear magnetic resonance (NMR) spectroscopic data and comparisons of their experimental CD spectra with calculated electronic circular dichroism (ECD) spectra. Compound 1 is the first abietane type diterpene with an 18→1 lactone ring. Compound 19 was isolated from the plants of the Tripterygium genus for the first time, and compounds 14–17 were isolated from T. regelii for the first time. Triregelin I (9) showed significant cytotoxicity against A2780 and HepG2 with IC(50) values of 5.88 and 11.74 µM, respectively. It was found that this compound was inactive against MCF-7 cells. The discovery of these twelve new diterpenes not only provided information on chemical substances of T. regelii, but also contributed to the chemical diversity of natural terpenoids.
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spelling pubmed-52977802017-02-10 New Abietane and Kaurane Type Diterpenoids from the Stems of Tripterygium regelii Fan, Dongsheng Zhou, Shuangyan Zheng, Zhiyuan Zhu, Guo-Yuan Yao, Xiaojun Yang, Ming-Rong Jiang, Zhi-Hong Bai, Li-Ping Int J Mol Sci Article Eleven new abietane type (1‒11), and one new kaurane (12), diterpenes, together with eleven known compounds (13–23), were isolated and identified from the stems of Tripterygium regelii, which has been used as a traditional folk Chinese medicine for the treatment of rheumatoid arthritis in China. The structures of new compounds were characterized by means of the interpretation of high-resolution electrospray ionization mass spectrometry (HRESIMS), extensive nuclear magnetic resonance (NMR) spectroscopic data and comparisons of their experimental CD spectra with calculated electronic circular dichroism (ECD) spectra. Compound 1 is the first abietane type diterpene with an 18→1 lactone ring. Compound 19 was isolated from the plants of the Tripterygium genus for the first time, and compounds 14–17 were isolated from T. regelii for the first time. Triregelin I (9) showed significant cytotoxicity against A2780 and HepG2 with IC(50) values of 5.88 and 11.74 µM, respectively. It was found that this compound was inactive against MCF-7 cells. The discovery of these twelve new diterpenes not only provided information on chemical substances of T. regelii, but also contributed to the chemical diversity of natural terpenoids. MDPI 2017-01-13 /pmc/articles/PMC5297780/ /pubmed/28098763 http://dx.doi.org/10.3390/ijms18010147 Text en © 2017 by the authors; licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC-BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Fan, Dongsheng
Zhou, Shuangyan
Zheng, Zhiyuan
Zhu, Guo-Yuan
Yao, Xiaojun
Yang, Ming-Rong
Jiang, Zhi-Hong
Bai, Li-Ping
New Abietane and Kaurane Type Diterpenoids from the Stems of Tripterygium regelii
title New Abietane and Kaurane Type Diterpenoids from the Stems of Tripterygium regelii
title_full New Abietane and Kaurane Type Diterpenoids from the Stems of Tripterygium regelii
title_fullStr New Abietane and Kaurane Type Diterpenoids from the Stems of Tripterygium regelii
title_full_unstemmed New Abietane and Kaurane Type Diterpenoids from the Stems of Tripterygium regelii
title_short New Abietane and Kaurane Type Diterpenoids from the Stems of Tripterygium regelii
title_sort new abietane and kaurane type diterpenoids from the stems of tripterygium regelii
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5297780/
https://www.ncbi.nlm.nih.gov/pubmed/28098763
http://dx.doi.org/10.3390/ijms18010147
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