Uncommon Bis-Amide Matrine-type Alkaloids From Sophora alopecuroides With Anti-inflammatory Effects

Four new alkaloids (1–4) belonging to rare examples of bis-amide matrine-type were isolated from the seeds of sophora alopecuroides. Their structures including absolute configuration were determined by extensive spectroscopic analysis, electronic circular dichroism (ECD) interpretation, and X-ray di...

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Autores principales: Luo, Ding, Tu, Zhenchao, Yin, Wenjing, Fan, Chunlin, Chen, Nenghua, Wu, Zhongnan, Ding, Weilong, Li, Yaolan, Wang, Guocai, Zhang, Yubo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2021
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8479178/
https://www.ncbi.nlm.nih.gov/pubmed/34604173
http://dx.doi.org/10.3389/fchem.2021.740421
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author Luo, Ding
Tu, Zhenchao
Yin, Wenjing
Fan, Chunlin
Chen, Nenghua
Wu, Zhongnan
Ding, Weilong
Li, Yaolan
Wang, Guocai
Zhang, Yubo
author_facet Luo, Ding
Tu, Zhenchao
Yin, Wenjing
Fan, Chunlin
Chen, Nenghua
Wu, Zhongnan
Ding, Weilong
Li, Yaolan
Wang, Guocai
Zhang, Yubo
author_sort Luo, Ding
collection PubMed
description Four new alkaloids (1–4) belonging to rare examples of bis-amide matrine-type were isolated from the seeds of sophora alopecuroides. Their structures including absolute configuration were determined by extensive spectroscopic analysis, electronic circular dichroism (ECD) interpretation, and X-ray diffraction crystallography. Chemically, bis-amide matrine-type alkaloids can provide new molecular template for structural modification. Compounds 3–4 displayed obvious anti-inflammatory effects based on the inhibition of two key pro-inflammatory cytokines [tumor necrosis factor-α (TNF-α) and interleukin-6 (IL-6)] in a dose-dependent manner, with IC50 values from 35.6 to 45.8 μm.
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spelling pubmed-84791782021-09-30 Uncommon Bis-Amide Matrine-type Alkaloids From Sophora alopecuroides With Anti-inflammatory Effects Luo, Ding Tu, Zhenchao Yin, Wenjing Fan, Chunlin Chen, Nenghua Wu, Zhongnan Ding, Weilong Li, Yaolan Wang, Guocai Zhang, Yubo Front Chem Chemistry Four new alkaloids (1–4) belonging to rare examples of bis-amide matrine-type were isolated from the seeds of sophora alopecuroides. Their structures including absolute configuration were determined by extensive spectroscopic analysis, electronic circular dichroism (ECD) interpretation, and X-ray diffraction crystallography. Chemically, bis-amide matrine-type alkaloids can provide new molecular template for structural modification. Compounds 3–4 displayed obvious anti-inflammatory effects based on the inhibition of two key pro-inflammatory cytokines [tumor necrosis factor-α (TNF-α) and interleukin-6 (IL-6)] in a dose-dependent manner, with IC50 values from 35.6 to 45.8 μm. Frontiers Media S.A. 2021-09-15 /pmc/articles/PMC8479178/ /pubmed/34604173 http://dx.doi.org/10.3389/fchem.2021.740421 Text en Copyright © 2021 Luo, Tu, Yin, Fan, Chen, Wu, Ding, Li, Wang and Zhang. https://creativecommons.org/licenses/by/4.0/This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.
spellingShingle Chemistry
Luo, Ding
Tu, Zhenchao
Yin, Wenjing
Fan, Chunlin
Chen, Nenghua
Wu, Zhongnan
Ding, Weilong
Li, Yaolan
Wang, Guocai
Zhang, Yubo
Uncommon Bis-Amide Matrine-type Alkaloids From Sophora alopecuroides With Anti-inflammatory Effects
title Uncommon Bis-Amide Matrine-type Alkaloids From Sophora alopecuroides With Anti-inflammatory Effects
title_full Uncommon Bis-Amide Matrine-type Alkaloids From Sophora alopecuroides With Anti-inflammatory Effects
title_fullStr Uncommon Bis-Amide Matrine-type Alkaloids From Sophora alopecuroides With Anti-inflammatory Effects
title_full_unstemmed Uncommon Bis-Amide Matrine-type Alkaloids From Sophora alopecuroides With Anti-inflammatory Effects
title_short Uncommon Bis-Amide Matrine-type Alkaloids From Sophora alopecuroides With Anti-inflammatory Effects
title_sort uncommon bis-amide matrine-type alkaloids from sophora alopecuroides with anti-inflammatory effects
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8479178/
https://www.ncbi.nlm.nih.gov/pubmed/34604173
http://dx.doi.org/10.3389/fchem.2021.740421
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