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New Octadecanoid Enantiomers from the Whole Plants of Plantago depressa

In this study, 19 octadecanoid derivatives—four pairs of enantiomers (1–8), two racemic/scalemic mixtures (9–10), and nine biosynthetically related analogues—were obtained from the ethanolic extract of a Chinese medicinal plant, Plantago depressa Willd. Their structures were elucidated on the basis...

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Autores principales: Song, Xiu-Qing, Zhu, Kongkai, Yu, Jin-Hai, Zhang, Qianqian, Zhang, Yuying, He, Fei, Cheng, Zhi-Qiang, Jiang, Cheng-Shi, Bao, Jie, Zhang, Hua
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6099667/
https://www.ncbi.nlm.nih.gov/pubmed/30011919
http://dx.doi.org/10.3390/molecules23071723
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author Song, Xiu-Qing
Zhu, Kongkai
Yu, Jin-Hai
Zhang, Qianqian
Zhang, Yuying
He, Fei
Cheng, Zhi-Qiang
Jiang, Cheng-Shi
Bao, Jie
Zhang, Hua
author_facet Song, Xiu-Qing
Zhu, Kongkai
Yu, Jin-Hai
Zhang, Qianqian
Zhang, Yuying
He, Fei
Cheng, Zhi-Qiang
Jiang, Cheng-Shi
Bao, Jie
Zhang, Hua
author_sort Song, Xiu-Qing
collection PubMed
description In this study, 19 octadecanoid derivatives—four pairs of enantiomers (1–8), two racemic/scalemic mixtures (9–10), and nine biosynthetically related analogues—were obtained from the ethanolic extract of a Chinese medicinal plant, Plantago depressa Willd. Their structures were elucidated on the basis of detailed spectroscopic analyses, with the absolute configurations of the new compounds assigned by time-dependent density functional theory (TD-DFT)-based electronic circular dichroism (ECD) calculations. Six of them (1, 3–6, and 9) were reported for the first time, while 2, 7, and 8 have been previously described as derivatives and are currently obtained as natural products. Our bioassays have established that selective compounds show in vitro anti-inflammatory activity by inhibiting lipopolysaccharide-induced nitric oxide (NO) production in mouse macrophage RAW 264.7 cells.
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spelling pubmed-60996672018-11-13 New Octadecanoid Enantiomers from the Whole Plants of Plantago depressa Song, Xiu-Qing Zhu, Kongkai Yu, Jin-Hai Zhang, Qianqian Zhang, Yuying He, Fei Cheng, Zhi-Qiang Jiang, Cheng-Shi Bao, Jie Zhang, Hua Molecules Article In this study, 19 octadecanoid derivatives—four pairs of enantiomers (1–8), two racemic/scalemic mixtures (9–10), and nine biosynthetically related analogues—were obtained from the ethanolic extract of a Chinese medicinal plant, Plantago depressa Willd. Their structures were elucidated on the basis of detailed spectroscopic analyses, with the absolute configurations of the new compounds assigned by time-dependent density functional theory (TD-DFT)-based electronic circular dichroism (ECD) calculations. Six of them (1, 3–6, and 9) were reported for the first time, while 2, 7, and 8 have been previously described as derivatives and are currently obtained as natural products. Our bioassays have established that selective compounds show in vitro anti-inflammatory activity by inhibiting lipopolysaccharide-induced nitric oxide (NO) production in mouse macrophage RAW 264.7 cells. MDPI 2018-07-14 /pmc/articles/PMC6099667/ /pubmed/30011919 http://dx.doi.org/10.3390/molecules23071723 Text en © 2018 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
Song, Xiu-Qing
Zhu, Kongkai
Yu, Jin-Hai
Zhang, Qianqian
Zhang, Yuying
He, Fei
Cheng, Zhi-Qiang
Jiang, Cheng-Shi
Bao, Jie
Zhang, Hua
New Octadecanoid Enantiomers from the Whole Plants of Plantago depressa
title New Octadecanoid Enantiomers from the Whole Plants of Plantago depressa
title_full New Octadecanoid Enantiomers from the Whole Plants of Plantago depressa
title_fullStr New Octadecanoid Enantiomers from the Whole Plants of Plantago depressa
title_full_unstemmed New Octadecanoid Enantiomers from the Whole Plants of Plantago depressa
title_short New Octadecanoid Enantiomers from the Whole Plants of Plantago depressa
title_sort new octadecanoid enantiomers from the whole plants of plantago depressa
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6099667/
https://www.ncbi.nlm.nih.gov/pubmed/30011919
http://dx.doi.org/10.3390/molecules23071723
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