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Synthesis and Evaluation of 11-Butyl Matrine Derivatives as Potential Anti-Virus Agents

Matrine derivatives were reported to have various biological activities, especially the ester, amide or sulfonamide derivatives of matrine deriving from the hydroxyl or carboxyl group at the end of the branch chain after the D ring of matrine is opened. In this work, to investigate whether moving aw...

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Autores principales: Ni, Wanjun, Wang, Lizhong, Song, Hongjian, Liu, Yuxiu, Wang, Qingmin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9658933/
https://www.ncbi.nlm.nih.gov/pubmed/36364389
http://dx.doi.org/10.3390/molecules27217563
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author Ni, Wanjun
Wang, Lizhong
Song, Hongjian
Liu, Yuxiu
Wang, Qingmin
author_facet Ni, Wanjun
Wang, Lizhong
Song, Hongjian
Liu, Yuxiu
Wang, Qingmin
author_sort Ni, Wanjun
collection PubMed
description Matrine derivatives were reported to have various biological activities, especially the ester, amide or sulfonamide derivatives of matrine deriving from the hydroxyl or carboxyl group at the end of the branch chain after the D ring of matrine is opened. In this work, to investigate whether moving away all functional groups from the C-11 branch chain could have an impact on the bioactivities, such as anti-tobacco mosaic virus (TMV), insecticidal and fungicidal activities, a variety of N-substituted-11-butyl matrine derivatives were synthesized. The obtained bioassay result showed that most N-substituted-11-butyl matrine derivatives had obviously enhanced anti-TMV activity compared with matrine, especially many compounds had good inhibitory activity close to that of commercialized virucide Ningnanmycin (inhibition rate 55.4, 57.8 ± 1.4, 55.3 ± 0.5 and 60.3 ± 1.2% at 500 μg/mL; 26.1, 29.7 ± 0.2, 24.2 ± 1.0 and 27.0 ± 0.3% at 100 μg/mL, for the in vitro activity, in vivo inactivation, curative and protection activities, respectively). Notably, N-benzoyl (7), N-benzyl (16), and N-cyclohexylmethyl-11-butyl (19) matrine derivatives had higher anti-TMV activity than Ningnanmycin at both 500 and 100 μg/mL for the four test modes, showing high potential as anti-TMV agent. Furthermore, some compounds also showed good fungicidal activity or insecticidal activity.
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spelling pubmed-96589332022-11-15 Synthesis and Evaluation of 11-Butyl Matrine Derivatives as Potential Anti-Virus Agents Ni, Wanjun Wang, Lizhong Song, Hongjian Liu, Yuxiu Wang, Qingmin Molecules Article Matrine derivatives were reported to have various biological activities, especially the ester, amide or sulfonamide derivatives of matrine deriving from the hydroxyl or carboxyl group at the end of the branch chain after the D ring of matrine is opened. In this work, to investigate whether moving away all functional groups from the C-11 branch chain could have an impact on the bioactivities, such as anti-tobacco mosaic virus (TMV), insecticidal and fungicidal activities, a variety of N-substituted-11-butyl matrine derivatives were synthesized. The obtained bioassay result showed that most N-substituted-11-butyl matrine derivatives had obviously enhanced anti-TMV activity compared with matrine, especially many compounds had good inhibitory activity close to that of commercialized virucide Ningnanmycin (inhibition rate 55.4, 57.8 ± 1.4, 55.3 ± 0.5 and 60.3 ± 1.2% at 500 μg/mL; 26.1, 29.7 ± 0.2, 24.2 ± 1.0 and 27.0 ± 0.3% at 100 μg/mL, for the in vitro activity, in vivo inactivation, curative and protection activities, respectively). Notably, N-benzoyl (7), N-benzyl (16), and N-cyclohexylmethyl-11-butyl (19) matrine derivatives had higher anti-TMV activity than Ningnanmycin at both 500 and 100 μg/mL for the four test modes, showing high potential as anti-TMV agent. Furthermore, some compounds also showed good fungicidal activity or insecticidal activity. MDPI 2022-11-04 /pmc/articles/PMC9658933/ /pubmed/36364389 http://dx.doi.org/10.3390/molecules27217563 Text en © 2022 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
Ni, Wanjun
Wang, Lizhong
Song, Hongjian
Liu, Yuxiu
Wang, Qingmin
Synthesis and Evaluation of 11-Butyl Matrine Derivatives as Potential Anti-Virus Agents
title Synthesis and Evaluation of 11-Butyl Matrine Derivatives as Potential Anti-Virus Agents
title_full Synthesis and Evaluation of 11-Butyl Matrine Derivatives as Potential Anti-Virus Agents
title_fullStr Synthesis and Evaluation of 11-Butyl Matrine Derivatives as Potential Anti-Virus Agents
title_full_unstemmed Synthesis and Evaluation of 11-Butyl Matrine Derivatives as Potential Anti-Virus Agents
title_short Synthesis and Evaluation of 11-Butyl Matrine Derivatives as Potential Anti-Virus Agents
title_sort synthesis and evaluation of 11-butyl matrine derivatives as potential anti-virus agents
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9658933/
https://www.ncbi.nlm.nih.gov/pubmed/36364389
http://dx.doi.org/10.3390/molecules27217563
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