Anticholinesterase and Antityrosinase Secondary Metabolites from the Fungus Xylobolus subpileatus
Xylobolus subpileatus is a widely distributed crust fungus reported from all continents except Antarctica, although considered a rare species in several European countries. Profound mycochemical analysis of the methanol extract of X. subpileatus resulted in the isolation of seven compounds ( 1 – 7 )...
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2023
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ftdoajarticles:oai:doaj.org/article:b3769ac657d3456abe403e294618b86e 2024-02-11T09:56:53+01:00 Anticholinesterase and Antityrosinase Secondary Metabolites from the Fungus Xylobolus subpileatus Kristóf Felegyi Zsófia Garádi Elżbieta Studzińska-Sroka Viktor Papp Imre Boldizsár András Dancsó Szabolcs Béni Przemysław Zalewski Attila Ványolós 2023-12-01T00:00:00Z https://doi.org/10.3390/molecules29010213 https://doaj.org/article/b3769ac657d3456abe403e294618b86e EN eng MDPI AG https://www.mdpi.com/1420-3049/29/1/213 https://doaj.org/toc/1420-3049 doi:10.3390/molecules29010213 1420-3049 https://doaj.org/article/b3769ac657d3456abe403e294618b86e Molecules, Vol 29, Iss 1, p 213 (2023) medicinal mushroom anticholinesterase antityrosinase fomannoxin triterpenes Basidiomycota Organic chemistry QD241-441 article 2023 ftdoajarticles https://doi.org/10.3390/molecules29010213 2024-01-14T01:38:54Z Xylobolus subpileatus is a widely distributed crust fungus reported from all continents except Antarctica, although considered a rare species in several European countries. Profound mycochemical analysis of the methanol extract of X. subpileatus resulted in the isolation of seven compounds ( 1 – 7 ). Among them, (3β,22E)-3-methoxy-ergosta-4,6,8 14 ,22-tetraene ( 1 ) is a new natural product, while the NMR assignment of its already known epimer ( 2 ) has been revised. In addition to a benzohydrofuran derivative fomannoxin ( 3 ), four ergostane-type triterpenes 4 – 7 were identified. The structure elucidation of the isolated metabolites was performed by one- and two-dimensional NMR and MS analysis. Compounds 2 – 7 as well as the chloroform, n -hexane, and methanol extracts of X. subpileatus were evaluated for their tyrosinase, acetylcholinesterase, and butyrylcholinesterase inhibitory properties. Among the examined compounds, only fomannoxin ( 3 ) displayed the antityrosinase property with 51% of inhibition, and the fungal steroids proved to be inactive. Regarding the potential acetylcholinesterase (AChE) inhibitory activity of the fungal extracts and metabolites, it was demonstrated that the chloroform extract and compounds 3 – 4 exerted noteworthy inhibitory activity, with 83.86 and 32.99%, respectively. The butyrylcholinesterase (BChE) inhibitory assay revealed that methanol and chloroform extracts, as well as compounds 3 and 4, exerted notable activity, while the rest of the compounds proved to be only weak enzyme inhibitors. Our study represents the first report on the chemical profile of basidiome of the wild-growing X. subpileatus , offering a thorough study on the isolation and structure determination of the most characteristic biologically active constituents of this species. Article in Journal/Newspaper Antarc* Antarctica Directory of Open Access Journals: DOAJ Articles Molecules 29 1 213 |
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Directory of Open Access Journals: DOAJ Articles |
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ftdoajarticles |
language |
English |
topic |
medicinal mushroom anticholinesterase antityrosinase fomannoxin triterpenes Basidiomycota Organic chemistry QD241-441 |
spellingShingle |
medicinal mushroom anticholinesterase antityrosinase fomannoxin triterpenes Basidiomycota Organic chemistry QD241-441 Kristóf Felegyi Zsófia Garádi Elżbieta Studzińska-Sroka Viktor Papp Imre Boldizsár András Dancsó Szabolcs Béni Przemysław Zalewski Attila Ványolós Anticholinesterase and Antityrosinase Secondary Metabolites from the Fungus Xylobolus subpileatus |
topic_facet |
medicinal mushroom anticholinesterase antityrosinase fomannoxin triterpenes Basidiomycota Organic chemistry QD241-441 |
description |
Xylobolus subpileatus is a widely distributed crust fungus reported from all continents except Antarctica, although considered a rare species in several European countries. Profound mycochemical analysis of the methanol extract of X. subpileatus resulted in the isolation of seven compounds ( 1 – 7 ). Among them, (3β,22E)-3-methoxy-ergosta-4,6,8 14 ,22-tetraene ( 1 ) is a new natural product, while the NMR assignment of its already known epimer ( 2 ) has been revised. In addition to a benzohydrofuran derivative fomannoxin ( 3 ), four ergostane-type triterpenes 4 – 7 were identified. The structure elucidation of the isolated metabolites was performed by one- and two-dimensional NMR and MS analysis. Compounds 2 – 7 as well as the chloroform, n -hexane, and methanol extracts of X. subpileatus were evaluated for their tyrosinase, acetylcholinesterase, and butyrylcholinesterase inhibitory properties. Among the examined compounds, only fomannoxin ( 3 ) displayed the antityrosinase property with 51% of inhibition, and the fungal steroids proved to be inactive. Regarding the potential acetylcholinesterase (AChE) inhibitory activity of the fungal extracts and metabolites, it was demonstrated that the chloroform extract and compounds 3 – 4 exerted noteworthy inhibitory activity, with 83.86 and 32.99%, respectively. The butyrylcholinesterase (BChE) inhibitory assay revealed that methanol and chloroform extracts, as well as compounds 3 and 4, exerted notable activity, while the rest of the compounds proved to be only weak enzyme inhibitors. Our study represents the first report on the chemical profile of basidiome of the wild-growing X. subpileatus , offering a thorough study on the isolation and structure determination of the most characteristic biologically active constituents of this species. |
format |
Article in Journal/Newspaper |
author |
Kristóf Felegyi Zsófia Garádi Elżbieta Studzińska-Sroka Viktor Papp Imre Boldizsár András Dancsó Szabolcs Béni Przemysław Zalewski Attila Ványolós |
author_facet |
Kristóf Felegyi Zsófia Garádi Elżbieta Studzińska-Sroka Viktor Papp Imre Boldizsár András Dancsó Szabolcs Béni Przemysław Zalewski Attila Ványolós |
author_sort |
Kristóf Felegyi |
title |
Anticholinesterase and Antityrosinase Secondary Metabolites from the Fungus Xylobolus subpileatus |
title_short |
Anticholinesterase and Antityrosinase Secondary Metabolites from the Fungus Xylobolus subpileatus |
title_full |
Anticholinesterase and Antityrosinase Secondary Metabolites from the Fungus Xylobolus subpileatus |
title_fullStr |
Anticholinesterase and Antityrosinase Secondary Metabolites from the Fungus Xylobolus subpileatus |
title_full_unstemmed |
Anticholinesterase and Antityrosinase Secondary Metabolites from the Fungus Xylobolus subpileatus |
title_sort |
anticholinesterase and antityrosinase secondary metabolites from the fungus xylobolus subpileatus |
publisher |
MDPI AG |
publishDate |
2023 |
url |
https://doi.org/10.3390/molecules29010213 https://doaj.org/article/b3769ac657d3456abe403e294618b86e |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Molecules, Vol 29, Iss 1, p 213 (2023) |
op_relation |
https://www.mdpi.com/1420-3049/29/1/213 https://doaj.org/toc/1420-3049 doi:10.3390/molecules29010213 1420-3049 https://doaj.org/article/b3769ac657d3456abe403e294618b86e |
op_doi |
https://doi.org/10.3390/molecules29010213 |
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Molecules |
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29 |
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1 |
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213 |
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1790606678749609984 |