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New Monoterpene Glycoside Paeoniflorin Derivatives as NO and IL-1β Inhibitors: Synthesis and Biological Evaluation
Several monoterpene glycoside compounds were extracted from Paeonia lactiflora Pall. Among them, paeoniflorin, a water-soluble monoterpene glycoside found in the root of Paeonia lactiflora Pall, exhibits excellent antioxidant pharmacological functions. Initially, Sc(CF(3)SO(3))(3) was employed as th...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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MDPI
2023
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10574144/ https://www.ncbi.nlm.nih.gov/pubmed/37836765 http://dx.doi.org/10.3390/molecules28196922 |
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author | Chen, Yongjie Zhang, Guoqing Cao, Dongyi Wang, Fei Zhang, Fan Shao, Huawu Jiao, Wei |
author_facet | Chen, Yongjie Zhang, Guoqing Cao, Dongyi Wang, Fei Zhang, Fan Shao, Huawu Jiao, Wei |
author_sort | Chen, Yongjie |
collection | PubMed |
description | Several monoterpene glycoside compounds were extracted from Paeonia lactiflora Pall. Among them, paeoniflorin, a water-soluble monoterpene glycoside found in the root of Paeonia lactiflora Pall, exhibits excellent antioxidant pharmacological functions. Initially, Sc(CF(3)SO(3))(3) was employed as the catalyst for paeoniflorin’s dehydration and rearrangement reactions with alcohols. Subsequently, structural modifications were performed on paeoniflorin through a series of responses, including acetylation, deacetylation, and debenzoylation, ultimately yielding 46 monoterpene glycoside derivatives. The potential inhibitory effects on the pro-inflammatory mediators interleukin-1 beta (IL-1β) and nitric oxide (NO) were assessed in vitro. The results revealed that compounds 29 and 31 demonstrated notable inhibition of NO production, while eight derivatives (3, 8, 18, 20, 21, 29, 34, and 40) displayed substantial inhibitory effects on the secretion of IL-1β. Computational research was also undertaken to investigate the binding affinity of the ligands with the target proteins. Interactions between the proteins and substrates were elucidated, and corresponding binding energies were calculated accordingly. The findings of this study could provide valuable insights into the design and development of novel anti-inflammatory agents with enhanced pharmacological properties. |
format | Online Article Text |
id | pubmed-10574144 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-105741442023-10-14 New Monoterpene Glycoside Paeoniflorin Derivatives as NO and IL-1β Inhibitors: Synthesis and Biological Evaluation Chen, Yongjie Zhang, Guoqing Cao, Dongyi Wang, Fei Zhang, Fan Shao, Huawu Jiao, Wei Molecules Article Several monoterpene glycoside compounds were extracted from Paeonia lactiflora Pall. Among them, paeoniflorin, a water-soluble monoterpene glycoside found in the root of Paeonia lactiflora Pall, exhibits excellent antioxidant pharmacological functions. Initially, Sc(CF(3)SO(3))(3) was employed as the catalyst for paeoniflorin’s dehydration and rearrangement reactions with alcohols. Subsequently, structural modifications were performed on paeoniflorin through a series of responses, including acetylation, deacetylation, and debenzoylation, ultimately yielding 46 monoterpene glycoside derivatives. The potential inhibitory effects on the pro-inflammatory mediators interleukin-1 beta (IL-1β) and nitric oxide (NO) were assessed in vitro. The results revealed that compounds 29 and 31 demonstrated notable inhibition of NO production, while eight derivatives (3, 8, 18, 20, 21, 29, 34, and 40) displayed substantial inhibitory effects on the secretion of IL-1β. Computational research was also undertaken to investigate the binding affinity of the ligands with the target proteins. Interactions between the proteins and substrates were elucidated, and corresponding binding energies were calculated accordingly. The findings of this study could provide valuable insights into the design and development of novel anti-inflammatory agents with enhanced pharmacological properties. MDPI 2023-10-03 /pmc/articles/PMC10574144/ /pubmed/37836765 http://dx.doi.org/10.3390/molecules28196922 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/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 (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Chen, Yongjie Zhang, Guoqing Cao, Dongyi Wang, Fei Zhang, Fan Shao, Huawu Jiao, Wei New Monoterpene Glycoside Paeoniflorin Derivatives as NO and IL-1β Inhibitors: Synthesis and Biological Evaluation |
title | New Monoterpene Glycoside Paeoniflorin Derivatives as NO and IL-1β Inhibitors: Synthesis and Biological Evaluation |
title_full | New Monoterpene Glycoside Paeoniflorin Derivatives as NO and IL-1β Inhibitors: Synthesis and Biological Evaluation |
title_fullStr | New Monoterpene Glycoside Paeoniflorin Derivatives as NO and IL-1β Inhibitors: Synthesis and Biological Evaluation |
title_full_unstemmed | New Monoterpene Glycoside Paeoniflorin Derivatives as NO and IL-1β Inhibitors: Synthesis and Biological Evaluation |
title_short | New Monoterpene Glycoside Paeoniflorin Derivatives as NO and IL-1β Inhibitors: Synthesis and Biological Evaluation |
title_sort | new monoterpene glycoside paeoniflorin derivatives as no and il-1β inhibitors: synthesis and biological evaluation |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10574144/ https://www.ncbi.nlm.nih.gov/pubmed/37836765 http://dx.doi.org/10.3390/molecules28196922 |
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