Cargando…
Butenolide derivatives from Aspergillus terreus selectively inhibit butyrylcholinesterase
Two undescribed butenolide derivatives, asperteretal J (1) and K (2), together with 13 known ones (3–15) were isolated from an endophytic fungus Aspergillus terreus SGP-1, the fermentation product of which exhibited selective inhibitory activity toward butyrylcholinesterase. The structures of the ne...
Autores principales: | , , , , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Frontiers Media S.A.
2022
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9811682/ https://www.ncbi.nlm.nih.gov/pubmed/36618870 http://dx.doi.org/10.3389/fchem.2022.1063284 |
_version_ | 1784863577106022400 |
---|---|
author | Cui, Xiang Deng, Shanshan Li, Guoyin Zhang, Yunxia Wang, Lining Wu, Changjing Deng, Yanru |
author_facet | Cui, Xiang Deng, Shanshan Li, Guoyin Zhang, Yunxia Wang, Lining Wu, Changjing Deng, Yanru |
author_sort | Cui, Xiang |
collection | PubMed |
description | Two undescribed butenolide derivatives, asperteretal J (1) and K (2), together with 13 known ones (3–15) were isolated from an endophytic fungus Aspergillus terreus SGP-1, the fermentation product of which exhibited selective inhibitory activity toward butyrylcholinesterase. The structures of the new compounds were elucidated based on HRMS and NMR data, and the absolute configurations were determined by specific optical rotation comparison. All compounds were evaluated for cholinesterase inhibitory effects with galantamine as a positive control. Compounds 4–8 selectively inhibited butyrylcholinesterase with IC(50) values of 18.4–45.8 µM in a competitive manner, with Ki values of 12.3–38.2 µM. The structure-activity relationship was discussed. Molecular docking and dynamic simulation of the inhibitor-enzyme complex were performed to better understand the interactions. |
format | Online Article Text |
id | pubmed-9811682 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | Frontiers Media S.A. |
record_format | MEDLINE/PubMed |
spelling | pubmed-98116822023-01-05 Butenolide derivatives from Aspergillus terreus selectively inhibit butyrylcholinesterase Cui, Xiang Deng, Shanshan Li, Guoyin Zhang, Yunxia Wang, Lining Wu, Changjing Deng, Yanru Front Chem Chemistry Two undescribed butenolide derivatives, asperteretal J (1) and K (2), together with 13 known ones (3–15) were isolated from an endophytic fungus Aspergillus terreus SGP-1, the fermentation product of which exhibited selective inhibitory activity toward butyrylcholinesterase. The structures of the new compounds were elucidated based on HRMS and NMR data, and the absolute configurations were determined by specific optical rotation comparison. All compounds were evaluated for cholinesterase inhibitory effects with galantamine as a positive control. Compounds 4–8 selectively inhibited butyrylcholinesterase with IC(50) values of 18.4–45.8 µM in a competitive manner, with Ki values of 12.3–38.2 µM. The structure-activity relationship was discussed. Molecular docking and dynamic simulation of the inhibitor-enzyme complex were performed to better understand the interactions. Frontiers Media S.A. 2022-12-21 /pmc/articles/PMC9811682/ /pubmed/36618870 http://dx.doi.org/10.3389/fchem.2022.1063284 Text en Copyright © 2022 Cui, Deng, Li, Zhang, Wang, Wu and Deng. 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 Cui, Xiang Deng, Shanshan Li, Guoyin Zhang, Yunxia Wang, Lining Wu, Changjing Deng, Yanru Butenolide derivatives from Aspergillus terreus selectively inhibit butyrylcholinesterase |
title | Butenolide derivatives from Aspergillus terreus selectively inhibit butyrylcholinesterase |
title_full | Butenolide derivatives from Aspergillus terreus selectively inhibit butyrylcholinesterase |
title_fullStr | Butenolide derivatives from Aspergillus terreus selectively inhibit butyrylcholinesterase |
title_full_unstemmed | Butenolide derivatives from Aspergillus terreus selectively inhibit butyrylcholinesterase |
title_short | Butenolide derivatives from Aspergillus terreus selectively inhibit butyrylcholinesterase |
title_sort | butenolide derivatives from aspergillus terreus selectively inhibit butyrylcholinesterase |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9811682/ https://www.ncbi.nlm.nih.gov/pubmed/36618870 http://dx.doi.org/10.3389/fchem.2022.1063284 |
work_keys_str_mv | AT cuixiang butenolidederivativesfromaspergillusterreusselectivelyinhibitbutyrylcholinesterase AT dengshanshan butenolidederivativesfromaspergillusterreusselectivelyinhibitbutyrylcholinesterase AT liguoyin butenolidederivativesfromaspergillusterreusselectivelyinhibitbutyrylcholinesterase AT zhangyunxia butenolidederivativesfromaspergillusterreusselectivelyinhibitbutyrylcholinesterase AT wanglining butenolidederivativesfromaspergillusterreusselectivelyinhibitbutyrylcholinesterase AT wuchangjing butenolidederivativesfromaspergillusterreusselectivelyinhibitbutyrylcholinesterase AT dengyanru butenolidederivativesfromaspergillusterreusselectivelyinhibitbutyrylcholinesterase |