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...
Ausführliche Beschreibung
Autor*in: |
Xiang Cui [verfasserIn] Shanshan Deng [verfasserIn] Guoyin Li [verfasserIn] Yunxia Zhang [verfasserIn] Lining Wang [verfasserIn] Changjing Wu [verfasserIn] Yanru Deng [verfasserIn] |
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E-Artikel |
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Englisch |
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2022 |
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In: Frontiers in Chemistry - Frontiers Media S.A., 2014, 10(2022) |
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Übergeordnetes Werk: |
volume:10 ; year:2022 |
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DOI / URN: |
10.3389/fchem.2022.1063284 |
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Katalog-ID: |
DOAJ083287094 |
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10.3389/fchem.2022.1063284 doi (DE-627)DOAJ083287094 (DE-599)DOAJ2146690aba5e480a8c5f58d66df66d16 DE-627 ger DE-627 rakwb eng QD1-999 Xiang Cui verfasserin aut Butenolide derivatives from Aspergillus terreus selectively inhibit butyrylcholinesterase 2022 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier 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 IC50 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. Aspergillus terreus secondary metabolites butenolide derivatives structure elucidation butyrylcholinesterase inhibitor Chemistry Xiang Cui verfasserin aut Shanshan Deng verfasserin aut Guoyin Li verfasserin aut Yunxia Zhang verfasserin aut Lining Wang verfasserin aut Changjing Wu verfasserin aut Yanru Deng verfasserin aut In Frontiers in Chemistry Frontiers Media S.A., 2014 10(2022) (DE-627)742224538 (DE-600)2711776-5 22962646 nnns volume:10 year:2022 https://doi.org/10.3389/fchem.2022.1063284 kostenfrei https://doaj.org/article/2146690aba5e480a8c5f58d66df66d16 kostenfrei https://www.frontiersin.org/articles/10.3389/fchem.2022.1063284/full kostenfrei https://doaj.org/toc/2296-2646 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_213 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2003 GBV_ILN_2014 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 10 2022 |
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10.3389/fchem.2022.1063284 doi (DE-627)DOAJ083287094 (DE-599)DOAJ2146690aba5e480a8c5f58d66df66d16 DE-627 ger DE-627 rakwb eng QD1-999 Xiang Cui verfasserin aut Butenolide derivatives from Aspergillus terreus selectively inhibit butyrylcholinesterase 2022 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier 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 IC50 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. Aspergillus terreus secondary metabolites butenolide derivatives structure elucidation butyrylcholinesterase inhibitor Chemistry Xiang Cui verfasserin aut Shanshan Deng verfasserin aut Guoyin Li verfasserin aut Yunxia Zhang verfasserin aut Lining Wang verfasserin aut Changjing Wu verfasserin aut Yanru Deng verfasserin aut In Frontiers in Chemistry Frontiers Media S.A., 2014 10(2022) (DE-627)742224538 (DE-600)2711776-5 22962646 nnns volume:10 year:2022 https://doi.org/10.3389/fchem.2022.1063284 kostenfrei https://doaj.org/article/2146690aba5e480a8c5f58d66df66d16 kostenfrei https://www.frontiersin.org/articles/10.3389/fchem.2022.1063284/full kostenfrei https://doaj.org/toc/2296-2646 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_213 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2003 GBV_ILN_2014 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 10 2022 |
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10.3389/fchem.2022.1063284 doi (DE-627)DOAJ083287094 (DE-599)DOAJ2146690aba5e480a8c5f58d66df66d16 DE-627 ger DE-627 rakwb eng QD1-999 Xiang Cui verfasserin aut Butenolide derivatives from Aspergillus terreus selectively inhibit butyrylcholinesterase 2022 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier 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 IC50 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. Aspergillus terreus secondary metabolites butenolide derivatives structure elucidation butyrylcholinesterase inhibitor Chemistry Xiang Cui verfasserin aut Shanshan Deng verfasserin aut Guoyin Li verfasserin aut Yunxia Zhang verfasserin aut Lining Wang verfasserin aut Changjing Wu verfasserin aut Yanru Deng verfasserin aut In Frontiers in Chemistry Frontiers Media S.A., 2014 10(2022) (DE-627)742224538 (DE-600)2711776-5 22962646 nnns volume:10 year:2022 https://doi.org/10.3389/fchem.2022.1063284 kostenfrei https://doaj.org/article/2146690aba5e480a8c5f58d66df66d16 kostenfrei https://www.frontiersin.org/articles/10.3389/fchem.2022.1063284/full kostenfrei https://doaj.org/toc/2296-2646 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_213 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2003 GBV_ILN_2014 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 10 2022 |
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10.3389/fchem.2022.1063284 doi (DE-627)DOAJ083287094 (DE-599)DOAJ2146690aba5e480a8c5f58d66df66d16 DE-627 ger DE-627 rakwb eng QD1-999 Xiang Cui verfasserin aut Butenolide derivatives from Aspergillus terreus selectively inhibit butyrylcholinesterase 2022 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier 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 IC50 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. Aspergillus terreus secondary metabolites butenolide derivatives structure elucidation butyrylcholinesterase inhibitor Chemistry Xiang Cui verfasserin aut Shanshan Deng verfasserin aut Guoyin Li verfasserin aut Yunxia Zhang verfasserin aut Lining Wang verfasserin aut Changjing Wu verfasserin aut Yanru Deng verfasserin aut In Frontiers in Chemistry Frontiers Media S.A., 2014 10(2022) (DE-627)742224538 (DE-600)2711776-5 22962646 nnns volume:10 year:2022 https://doi.org/10.3389/fchem.2022.1063284 kostenfrei https://doaj.org/article/2146690aba5e480a8c5f58d66df66d16 kostenfrei https://www.frontiersin.org/articles/10.3389/fchem.2022.1063284/full kostenfrei https://doaj.org/toc/2296-2646 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_213 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2003 GBV_ILN_2014 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 10 2022 |
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Butenolide derivatives from Aspergillus terreus selectively inhibit butyrylcholinesterase |
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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 IC50 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. |
abstractGer |
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 IC50 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. |
abstract_unstemmed |
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 IC50 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. |
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