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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...
Autores principales: | , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2018
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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. |
format | Online Article Text |
id | pubmed-6099667 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
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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