{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,3]],"date-time":"2026-06-03T16:29:51Z","timestamp":1780504191127,"version":"3.54.1"},"reference-count":32,"publisher":"MDPI AG","issue":"1","license":[{"start":{"date-parts":[[2023,12,30]],"date-time":"2023-12-30T00:00:00Z","timestamp":1703894400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"National Research, Development, and Innovation Fund","award":["KDP-1007075"],"award-info":[{"award-number":["KDP-1007075"]}]},{"name":"National Research, Development, and Innovation Fund","award":["STIA-OTKA-2022"],"award-info":[{"award-number":["STIA-OTKA-2022"]}]},{"name":"National Research, Development, and Innovation Fund","award":["OTKA NKFIH K-135712"],"award-info":[{"award-number":["OTKA NKFIH K-135712"]}]},{"name":"National Research, Development, and Innovation Fund","award":["OTKA NKFIH FK-146487"],"award-info":[{"award-number":["OTKA NKFIH FK-146487"]}]},{"name":"Semmelweis Fund for Science and Innovation","award":["KDP-1007075"],"award-info":[{"award-number":["KDP-1007075"]}]},{"name":"Semmelweis Fund for Science and Innovation","award":["STIA-OTKA-2022"],"award-info":[{"award-number":["STIA-OTKA-2022"]}]},{"name":"Semmelweis Fund for Science and Innovation","award":["OTKA NKFIH K-135712"],"award-info":[{"award-number":["OTKA NKFIH K-135712"]}]},{"name":"Semmelweis Fund for Science and Innovation","award":["OTKA NKFIH FK-146487"],"award-info":[{"award-number":["OTKA NKFIH FK-146487"]}]},{"DOI":"10.13039\/501100018818","name":"National Research, Development and Innovation Office","doi-asserted-by":"publisher","award":["KDP-1007075"],"award-info":[{"award-number":["KDP-1007075"]}],"id":[{"id":"10.13039\/501100018818","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100018818","name":"National Research, Development and Innovation Office","doi-asserted-by":"publisher","award":["STIA-OTKA-2022"],"award-info":[{"award-number":["STIA-OTKA-2022"]}],"id":[{"id":"10.13039\/501100018818","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100018818","name":"National Research, Development and Innovation Office","doi-asserted-by":"publisher","award":["OTKA NKFIH K-135712"],"award-info":[{"award-number":["OTKA NKFIH K-135712"]}],"id":[{"id":"10.13039\/501100018818","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100018818","name":"National Research, Development and Innovation Office","doi-asserted-by":"publisher","award":["OTKA NKFIH FK-146487"],"award-info":[{"award-number":["OTKA NKFIH FK-146487"]}],"id":[{"id":"10.13039\/501100018818","id-type":"DOI","asserted-by":"publisher"}]},{"name":"J\u00e1nos Bolyai Research Scholarship of the Hungarian Academy of Sciences","award":["KDP-1007075"],"award-info":[{"award-number":["KDP-1007075"]}]},{"name":"J\u00e1nos Bolyai Research Scholarship of the Hungarian Academy of Sciences","award":["STIA-OTKA-2022"],"award-info":[{"award-number":["STIA-OTKA-2022"]}]},{"name":"J\u00e1nos Bolyai Research Scholarship of the Hungarian Academy of Sciences","award":["OTKA NKFIH K-135712"],"award-info":[{"award-number":["OTKA NKFIH K-135712"]}]},{"name":"J\u00e1nos Bolyai Research Scholarship of the Hungarian Academy of Sciences","award":["OTKA NKFIH FK-146487"],"award-info":[{"award-number":["OTKA NKFIH FK-146487"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>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\u20137). Among them, (3\u03b2,22E)-3-methoxy-ergosta-4,6,814,22-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\u20137 were identified. The structure elucidation of the isolated metabolites was performed by one- and two-dimensional NMR and MS analysis. Compounds 2\u20137 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\u20134 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.<\/jats:p>","DOI":"10.3390\/molecules29010213","type":"journal-article","created":{"date-parts":[[2023,12,31]],"date-time":"2023-12-31T04:51:51Z","timestamp":1703998311000},"page":"213","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":8,"title":["Anticholinesterase and Antityrosinase Secondary Metabolites from the Fungus Xylobolus subpileatus"],"prefix":"10.3390","volume":"29","author":[{"given":"Krist\u00f3f","family":"Felegyi","sequence":"first","affiliation":[{"name":"Department of Pharmacognosy, Semmelweis University, 1085 Budapest, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0152-2746","authenticated-orcid":false,"given":"Zs\u00f3fia","family":"Gar\u00e1di","sequence":"additional","affiliation":[{"name":"Department of Pharmacognosy, Semmelweis University, 1085 Budapest, Hungary"},{"name":"Directorate of Drug Substance Development, Egis Pharmaceuticals Plc., 1475 Budapest, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0462-1766","authenticated-orcid":false,"given":"El\u017cbieta","family":"Studzi\u0144ska-Sroka","sequence":"additional","affiliation":[{"name":"Department of Pharmacognosy and Biomaterials, Poznan University of Medical Sciences, Rokietnicka 3 Str., 60-806 Poznan, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6994-8156","authenticated-orcid":false,"given":"Viktor","family":"Papp","sequence":"additional","affiliation":[{"name":"Department of Botany, Hungarian University of Agriculture and Life Sciences, 1118 Budapest, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7852-8364","authenticated-orcid":false,"given":"Imre","family":"Boldizs\u00e1r","sequence":"additional","affiliation":[{"name":"Department of Pharmacognosy, Semmelweis University, 1085 Budapest, Hungary"},{"name":"Department of Plant Anatomy, Institute of Biology, E\u00f6tv\u00f6s Lor\u00e1nd University, 1117 Budapest, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Andr\u00e1s","family":"Dancs\u00f3","sequence":"additional","affiliation":[{"name":"Directorate of Drug Substance Development, Egis Pharmaceuticals Plc., 1475 Budapest, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7056-6825","authenticated-orcid":false,"given":"Szabolcs","family":"B\u00e9ni","sequence":"additional","affiliation":[{"name":"Department of Pharmacognosy, Semmelweis University, 1085 Budapest, Hungary"},{"name":"Department of Analytical Chemistry, Institute of Chemistry, E\u00f6tv\u00f6s Lor\u00e1nd University, 1117 Budapest, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5116-9426","authenticated-orcid":false,"given":"Przemys\u0142aw","family":"Zalewski","sequence":"additional","affiliation":[{"name":"Department of Pharmacognosy and Biomaterials, Poznan University of Medical Sciences, Rokietnicka 3 Str., 60-806 Poznan, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4710-0004","authenticated-orcid":false,"given":"Attila","family":"V\u00e1nyol\u00f3s","sequence":"additional","affiliation":[{"name":"Department of Pharmacognosy, Semmelweis University, 1085 Budapest, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2023,12,30]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"200","DOI":"10.11646\/phytotaxa.452.3.2","article-title":"Xylobolus austrosinensis sp. nov. (Stereaceae, Russulales) and notes on the genus","volume":"452","author":"Cao","year":"2020","journal-title":"Phytotaxa"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"965","DOI":"10.1139\/cjfr-2016-0521","article-title":"Xylobolus subpileatus, a specialized basidiomycete functionally linked to old canopy gaps","volume":"47","author":"Taudiere","year":"2017","journal-title":"Can. J. For. Res."},{"key":"ref_3","first-page":"109","article-title":"The genus Stereum in Israel","volume":"106","author":"Tura","year":"2008","journal-title":"Mycotaxon"},{"key":"ref_4","first-page":"17","article-title":"A note on the genus Xylobolus P. Karst","volume":"30","author":"Ryvarden","year":"2012","journal-title":"Synop. Fungorum"},{"key":"ref_5","first-page":"69","article-title":"Stereoide Pilze in Europa (Stereaceae Pil. Emend. Parm. u. a., Hymenochaete), Mit Besonderer Ber\u00fccksichtigung ihres Vorkommens in der Bundesrepublik Deutschland","volume":"Volume 8","author":"Jahn","year":"1971","journal-title":"Westf\u00e4lische Pilzbriefe"},{"key":"ref_6","unstructured":"Chamuris, G.P. (1988). Mycologia Memoirs, Schweizerbart Science Publishers."},{"key":"ref_7","first-page":"234","article-title":"Decades of fungi. Decades XXIII and XXIV. North and South Carolina Fungi","volume":"1","author":"Berkeley","year":"1849","journal-title":"Hooker\u2019s J. Bot. Kew Gard. Misc."},{"key":"ref_8","unstructured":"Bernicchia, A., and Gorj\u00f3n, S. (2020). Polypores of the Mediterranean Region, Romar."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"287","DOI":"10.1615\/IntJMedMushr.v11.i3.80","article-title":"Species diversity and utilization of medicinal mushrooms and fungi in China (review)","volume":"11","author":"Dai","year":"2009","journal-title":"Int. J. Med. Mushrooms"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"43","DOI":"10.1016\/j.phymed.2018.09.196","article-title":"Ethnopharmacological exploration of medicinal mushroom from Pakistan","volume":"54","author":"Yasin","year":"2019","journal-title":"Phytomedicine"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"188","DOI":"10.1042\/bj0660188","article-title":"Biochemistry of the wood-rotting fungi. IX. Volatile metabolic products of Stereum subpileatum Berk. & Curt","volume":"66","author":"Birkinshaw","year":"1957","journal-title":"Biochem. J."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"1037","DOI":"10.1016\/S0031-9422(00)89935-5","article-title":"New benzofurans from stereum subpileatum, their biosynthesis, and related processes of aromatic aminoacid metabolism in a basidiomycete","volume":"10","author":"Kaye","year":"1971","journal-title":"Phytochemistry"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"932","DOI":"10.1080\/14786419.2016.1255889","article-title":"A new compound from Stereum insigne CGMCC5.57","volume":"31","author":"Tian","year":"2017","journal-title":"Nat. Prod. Res."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"3315","DOI":"10.1021\/acs.orglett.1c00790","article-title":"Ergopyrone, a styrylpyrone-fused steroid with a hexacyclic 6\/5\/6\/6\/6\/5 Skeleton from a mushroom Gymnopilus orientispectabilis","volume":"23","author":"Lee","year":"2021","journal-title":"Org. Lett."},{"key":"ref_15","doi-asserted-by":"crossref","unstructured":"Mah\u00e9, C., Patin, H., Van Hulle, M.T., and Barton, D.H.R. (1981). Structure and chemistry of \u03c0-allyl palladium complexes from steroids. J. Chem. Soc. Perkin Trans. 1, 2504\u20132508.","DOI":"10.1039\/P19810002504"},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"1669","DOI":"10.1016\/S0031-9422(97)00249-5","article-title":"Ergosta-4,6,8,22-tetraen-3-one from the edible fungus, Pleurotus ostreatus (oyster fungus)","volume":"45","author":"Chobot","year":"1997","journal-title":"Phytochemistry"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"171","DOI":"10.1016\/j.phytochem.2014.05.008","article-title":"Rare biscoumarin derivatives and flavonoids from Hypericum riparium","volume":"105","author":"Tanemossu","year":"2014","journal-title":"Phytochemistry"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"1728","DOI":"10.1021\/np0501886","article-title":"Antiviral terpenoid constituents of Ganoderma pfeifferi","volume":"68","author":"Niedermeyer","year":"2005","journal-title":"J. Nat. Prod."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"5713","DOI":"10.1021\/jf900581h","article-title":"Cytotoxic activities of 9,11-dehydroergosteroi peroxide and ergosterol peroxide from the fermentation mycelia of Ganoderma lucidum cultivated in the medium containing leguminous plants on Hep 3B cells","volume":"57","author":"Chen","year":"2009","journal-title":"J. Agric. Food Chem."},{"key":"ref_20","doi-asserted-by":"crossref","unstructured":"Lee, D., Ko, Y., Pang, C., Ko, Y.J., Choi, Y.K., Kim, K.H., and Kang, K.S. (2022). Estrogenic Activity of Mycoestrogen (3\u03b2,5\u03b1,22E)-Ergost-22-en-3-ol via Estrogen Receptor \u03b1-Dependent Signaling Pathways in MCF-7 Cells. Molecules, 27.","DOI":"10.3390\/molecules27010036"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"31","DOI":"10.1016\/j.phytochem.2012.08.008","article-title":"Biosynthesis of fomannoxin in the root rotting pathogen Heterobasidion occidentale","volume":"84","author":"Hansson","year":"2012","journal-title":"Phytochemistry"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"651","DOI":"10.1016\/S0040-4039(01)92717-0","article-title":"Fomannoxin\u2014A toxic metabolite of fomes annosus","volume":"18","author":"Hirotani","year":"1977","journal-title":"Tetrahedron Lett."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"38","DOI":"10.1021\/acs.jnatprod.6b00249","article-title":"Bioactive Constituents from the Termite Nest-Derived Medicinal Fungus Xylaria nigripes","volume":"80","author":"Chang","year":"2017","journal-title":"J. Nat. Prod."},{"key":"ref_24","first-page":"261","article-title":"ChemInform Abstract: Secondary Mould Metabolites. Part 38. Isolation and Structure Elucidation of Dihydrobenzofurans Isolated from Laurilia taxodii","volume":"23","author":"Arnone","year":"2010","journal-title":"Cheminform"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"973","DOI":"10.1038\/s41467-019-08858-y","article-title":"Brain tyrosinase overexpression implicates age-dependent neuromelanin production in Parkinson\u2019s disease pathogenesis","volume":"10","author":"Laguna","year":"2019","journal-title":"Nat. Commun."},{"key":"ref_26","first-page":"461","article-title":"The role of oxidative stress in Parkinson\u2019s disease","volume":"3","author":"Dias","year":"2013","journal-title":"J. Park. Dis."},{"key":"ref_27","first-page":"612","article-title":"Multisociety Consensus Quality Improvement Revised Consensus Statement for Endovascular Therapy of Acute Ischemic Stroke","volume":"13","author":"Sacks","year":"2018","journal-title":"Int. J. Stroke"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"1463","DOI":"10.3233\/JAD-170958","article-title":"A Natural Benzofuran from the Patagonic Aleurodiscus vitellinus Fungus has Potent Neuroprotective Properties on a Cellular Model of Amyloid-\u03b2 Peptide Toxicity","volume":"61","author":"Becerra","year":"2018","journal-title":"J. Alzheimers Dis."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"594","DOI":"10.1016\/j.foodchem.2008.09.093","article-title":"Evaluation of antioxidant, antibacterial and anti-tyrosinase activities of four Macaranga species","volume":"114","author":"Lim","year":"2009","journal-title":"Food Chem."},{"key":"ref_30","doi-asserted-by":"crossref","unstructured":"Studzi\u0144ska-Sroka, E., Majchrzak-Celi\u0144ska, A., Zalewski, P., Szwajgier, D., Baranowska-W\u00f3jcik, E., \u017barowski, M., Plech, T., and Cielecka-Piontek, J. (2021). Permeability of Hypogymnia physodes Extract Component-Physodic Acid through the Blood-Brain Barrier as an Important Argument for Its Anticancer and Neuroprotective Activity within the Central Nervous System. Cancers, 13.","DOI":"10.3390\/cancers13071717"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"88","DOI":"10.1016\/0006-2952(61)90145-9","article-title":"A new and rapid colorimetric determination of acetylcholinesterase activity","volume":"7","author":"Ellman","year":"1961","journal-title":"Biochem. Pharmacol."},{"key":"ref_32","doi-asserted-by":"crossref","unstructured":"Studzi\u0144ska-Sroka, E., Majchrzak-Celi\u0144ska, A., Ba\u0144durska, M., Rosiak, N., Szwajgier, D., Baranowska-W\u00f3jcik, E., Szyma\u0144ski, M., Gruszka, W., and Cielecka-Piontek, J. (2022). Is Caperatic Acid the Only Compound Responsible for Activity of Lichen Platismatia glauca within the Nervous System?. Antioxidants, 11.","DOI":"10.3390\/antiox11102069"}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/29\/1\/213\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T21:44:45Z","timestamp":1760132685000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/29\/1\/213"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,12,30]]},"references-count":32,"journal-issue":{"issue":"1","published-online":{"date-parts":[[2024,1]]}},"alternative-id":["molecules29010213"],"URL":"https:\/\/doi.org\/10.3390\/molecules29010213","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,12,30]]}}}