{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,17]],"date-time":"2026-06-17T14:33:19Z","timestamp":1781706799492,"version":"3.54.5"},"reference-count":30,"publisher":"MDPI AG","issue":"8","license":[{"start":{"date-parts":[[2024,4,11]],"date-time":"2024-04-11T00:00:00Z","timestamp":1712793600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"National Natural Science Foundation of China","award":["21977120"],"award-info":[{"award-number":["21977120"]}]},{"name":"National Natural Science Foundation of China","award":["32270296"],"award-info":[{"award-number":["32270296"]}]},{"name":"National Natural Science Foundation of China","award":["JCYJ20200109142215045"],"award-info":[{"award-number":["JCYJ20200109142215045"]}]},{"name":"Key Basic Research Program of the Science, Technology, and Innovation Commission of Shenzhen Municipality","award":["21977120"],"award-info":[{"award-number":["21977120"]}]},{"name":"Key Basic Research Program of the Science, Technology, and Innovation Commission of Shenzhen Municipality","award":["32270296"],"award-info":[{"award-number":["32270296"]}]},{"name":"Key Basic Research Program of the Science, Technology, and Innovation Commission of Shenzhen Municipality","award":["JCYJ20200109142215045"],"award-info":[{"award-number":["JCYJ20200109142215045"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The fungus Xylaria sp. Z184, harvested from the leaves of Fallopia convolvulus (L.) \u00c1. L\u00f6ve, has been isolated for the first time. Chemical investigation on the methanol extract of the culture broth of the titles strain led to the discovery of three new pyranone derivatives, called fallopiaxylaresters A\u2013C (1\u20133), and a new bisabolane-type sesquiterpenoid, named fallopiaxylarol A (4), along with the first complete set of spectroscopic data for the previously reported pestalotiopyrone M (5). Known pyranone derivatives (6\u201311), sesquiterpenoids (12\u201314), isocoumarin derivatives (15\u201317), and an aromatic allenic ether (18) were also co-isolated in this study. All new structures were elucidated by the interpretation of HRESIMS, 1D, 2D NMR spectroscopy, and quantum chemical computation approach. The in vitro antimicrobial, anti-inflammatory, and \u03b1-glucosidase-inhibitory activities of the selected compounds and the crude extract were evaluated. The extract was shown to inhibit nitric oxide (NO) production induced by lipopolysaccharide (LPS) in murine RAW264.7 macrophage cells, with an inhibition rate of 77.28 \u00b1 0.82% at a concentration of 50 \u03bcg\/mL. The compounds 5, 7, and 8 displayed weak antibacterial activity against Staphylococcus areus subsp. aureus at a concentration of 100 \u03bcM.<\/jats:p>","DOI":"10.3390\/molecules29081728","type":"journal-article","created":{"date-parts":[[2024,4,11]],"date-time":"2024-04-11T07:09:28Z","timestamp":1712819368000},"page":"1728","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":8,"title":["New Pyranone Derivatives and Sesquiterpenoid Isolated from the Endophytic Fungus Xylaria sp. Z184"],"prefix":"10.3390","volume":"29","author":[{"given":"Yan","family":"Zhang","sequence":"first","affiliation":[{"name":"School of Pharmaceutical Sciences (Shenzhen), Shenzhen Campus of Sun Yat-sen University, Shenzhen 518107, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yang","family":"Jin","sequence":"additional","affiliation":[{"name":"School of Pharmaceutical Sciences (Shenzhen), Shenzhen Campus of Sun Yat-sen University, Shenzhen 518107, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wensi","family":"Yan","sequence":"additional","affiliation":[{"name":"School of Pharmaceutical Sciences (Shenzhen), Shenzhen Campus of Sun Yat-sen University, Shenzhen 518107, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Peishan","family":"Gu","sequence":"additional","affiliation":[{"name":"School of Pharmaceutical Sciences (Shenzhen), Shenzhen Campus of Sun Yat-sen University, Shenzhen 518107, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ziqian","family":"Zeng","sequence":"additional","affiliation":[{"name":"School of Pharmaceutical Sciences (Shenzhen), Shenzhen Campus of Sun Yat-sen University, Shenzhen 518107, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ziying","family":"Li","sequence":"additional","affiliation":[{"name":"School of Pharmacy, Binzhou Medical University, Yantai 264003, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4396-5975","authenticated-orcid":false,"given":"Guangtao","family":"Zhang","sequence":"additional","affiliation":[{"name":"School of Pharmacy, Binzhou Medical University, Yantai 264003, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5761-3970","authenticated-orcid":false,"given":"Mi","family":"Wei","sequence":"additional","affiliation":[{"name":"School of Agriculture, Shenzhen Campus of Sun Yat-sen University, Shenzhen 518107, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9133-6439","authenticated-orcid":false,"given":"Yongbo","family":"Xue","sequence":"additional","affiliation":[{"name":"School of Pharmaceutical Sciences (Shenzhen), Shenzhen Campus of Sun Yat-sen University, Shenzhen 518107, China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2024,4,11]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"770","DOI":"10.1021\/acs.jnatprod.9b01285","article-title":"Natural products as sources of new drugs over the nearly four decades from 01\/1981 to 09\/2019","volume":"83","author":"Newman","year":"2020","journal-title":"J. Nat. Prod."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"1063","DOI":"10.1021\/acs.orglett.8b04107","article-title":"Cytorhizins A-D, four highly structure-combined benzophenones from the endophytic fungus Cytospora rhizophorae","volume":"21","author":"Liu","year":"2019","journal-title":"Org. Lett."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"405","DOI":"10.1021\/acs.orglett.9b04099","article-title":"Herpotrichones A and B, two intermolecular [4+2] adducts with anti-neuroinflammatory activity from a Herpotrichia Species","volume":"22","author":"Han","year":"2020","journal-title":"Org. Lett."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"84","DOI":"10.1016\/j.phytol.2019.09.005","article-title":"Eremophilane sesquiterpenes from the mangrove fungus BCC 60405","volume":"34","author":"Yoiprommarat","year":"2019","journal-title":"Phytochem. Lett."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"1303","DOI":"10.1021\/np100909y","article-title":"Isolation and structural elucidation of proline-containing cyclopentapeptides from an endolichenic Xylaria sp.","volume":"74","author":"Wu","year":"2011","journal-title":"J. Nat. Prod."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"7751","DOI":"10.1021\/acs.orglett.1c02730","article-title":"Xylarins A\u2013D, two pairs of diastereoisomeric isoindoline alkaloids from the endolichenic fungus Xylaria sp.","volume":"23","author":"Xu","year":"2021","journal-title":"Org. Lett."},{"key":"ref_7","doi-asserted-by":"crossref","unstructured":"Chen, W., Yu, M., Chen, S., Gong, T., Xie, L., Liu, J., Bian, C., Huang, G., and Zheng, C. (2024). Structures and biological activities of secondary metabolites from Xylaria spp.. J. Fungi, 10.","DOI":"10.3390\/jof10030190"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"3643","DOI":"10.1021\/acs.jafc.9b00273","article-title":"Cytochalasins and an abietane-type diterpenoid with allelopathic activities from the endophytic fungus Xylaria species","volume":"67","author":"Han","year":"2019","journal-title":"J. Agric. Food. Chem."},{"key":"ref_9","doi-asserted-by":"crossref","unstructured":"Jia, S., Li, J., Li, J., Su, X., Li, X.N., Yao, Y., and Xue, Y. (2022). Anti-neuroinflammatory activity of new naturally occurring benzylated hydroxyacetophenone analogs from the endophytic fungus Alternaria sp. J030. Chem. Biodivers., 19.","DOI":"10.1002\/cbdv.202200751"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"780304","DOI":"10.3389\/fchem.2021.780304","article-title":"Acorenone C: A new spiro-sesquiterpene from a mangrove-associated fungus, Pseudofusicoccum sp. J003","volume":"9","author":"Jia","year":"2021","journal-title":"Front. Chem."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"905708","DOI":"10.3389\/fphar.2022.905708","article-title":"In Vitro and in silico analysis of phytochemicals from Fallopia dentatoalata as dual functional cholinesterase inhibitors for the treatment of Alzheimer\u2019s disease","volume":"13","author":"Wu","year":"2022","journal-title":"Front. Pharmacol."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"2230","DOI":"10.1080\/14786419.2020.1826480","article-title":"Xylariaopyrones E-I, five new \u03b1-pyrone derivatives from the endophytic fungus Xylariales sp. (HM-1)","volume":"36","author":"Yang","year":"2022","journal-title":"Nat. Prod. Res."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"462","DOI":"10.1021\/jm010379f","article-title":"Synthesis and characterization of a series of novel monoacylated ascorbic acid derivatives, 6-O-Acyl-2-O-\u03b1-D-glucopyranosyl-L-ascorbic acids, as skin antioxidants","volume":"45","author":"Yamamoto","year":"2002","journal-title":"J. Med. Chem."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"567","DOI":"10.1080\/10286020.2015.1040776","article-title":"Nodulisporipyrones A-D, new bioactive \u03b1-pyrone derivatives from Nodulisporium sp.","volume":"17","author":"Zhao","year":"2015","journal-title":"J. Asian Nat. Prod. Res."},{"key":"ref_15","first-page":"967","article-title":"Studies on Ketoses, 7\u20135-(\u03b1-D-Glucosyloxymethyl)furfural: Preparation from isomaltulose and exploration of its ensuing chemistry","volume":"9","author":"Lichtenthaler","year":"1993","journal-title":"Eur. J. Org. Chem."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"69","DOI":"10.1016\/0031-9422(95)00221-R","article-title":"Biotransformation of (\u2013)-\u03b1-bisabolol by plant pathogenic fungus, Glomerella cingulata","volume":"40","author":"Miyazawa","year":"1995","journal-title":"Phytochemistry"},{"key":"ref_17","unstructured":"Xu, J. (2021). The Preparation Method and Application of a Pyranoid Compound with Immunosuppressive Activity. CN 108913731."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"1017","DOI":"10.1021\/jm00389a010","article-title":"Inhibition of human sputum elastase by substituted 2-pyrones","volume":"30","author":"Cook","year":"1987","journal-title":"J. Med. Chem."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"98","DOI":"10.1016\/j.phytol.2018.09.014","article-title":"Xylariaopyrones A-D, four new antimicrobial \u03b1-pyrone derivatives from endophytic fungus Xylariales sp.","volume":"28","author":"Guo","year":"2018","journal-title":"Phytochem. Lett."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"7940","DOI":"10.3390\/molecules20057940","article-title":"Effect of culture conditions on metabolite production of Xylaria sp.","volume":"20","author":"Zhang","year":"2015","journal-title":"Molecules"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"866","DOI":"10.1002\/mrc.4282","article-title":"1H and 13C NMR spectral assignments of 2-pyrone derivatives from an endophytic fungus of sarcosomataceae","volume":"53","author":"Tian","year":"2015","journal-title":"Magn. Reson. Chem."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"1471","DOI":"10.1021\/np060307x","article-title":"Eremophilanes from Senecio mairetianus and some reaction products","volume":"69","author":"Arciniegas","year":"2006","journal-title":"J. Nat. Prod."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"1312","DOI":"10.1016\/j.phymed.2016.07.004","article-title":"Isolation and characterization of bioactive metabolites from Xylaria psidii, an endophytic fungus of the medicinal plant Aegle marmelos and their role in mitochondrial dependent apoptosis against pancreatic cancer cells","volume":"23","author":"Arora","year":"2016","journal-title":"Phytomedicine"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"3123","DOI":"10.1016\/0031-9422(88)80012-8","article-title":"De-O-methyldiaporthin, a phytotoxin from Drechslera siccans","volume":"27","author":"Hallock","year":"1988","journal-title":"Phytochemistry"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"1099","DOI":"10.1002\/cbdv.201400005","article-title":"New isocoumarins from a cold-adapted fungal strain Mucor sp. and their developmental toxicity to zebrafish embryos","volume":"11","author":"Feng","year":"2014","journal-title":"Chem. Biodivers."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"449","DOI":"10.1016\/S0040-4039(00)01948-1","article-title":"A novel N-cinnamoylcyclopeptide containing an allenic ether from the fungus Xylaria sp. (strain #2508) from the South China Sea","volume":"42","author":"Lin","year":"2001","journal-title":"Tetrahedron Lett."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"243","DOI":"10.1002\/chir.22138","article-title":"SpecDis: Quantifying the Comparison of Calculated and Experimental Electronic Circular Dichroism Spectra","volume":"25","author":"Bruhn","year":"2013","journal-title":"Chirality"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"1491","DOI":"10.1039\/C9QO00245F","article-title":"The absolute configurations of hyperilongenols A\u2013C: Rare 12,13-seco-spirocyclic polycyclic polyprenylated acylphloroglucinols with enolizable \u03b2, \u03b2\u2032-tricarbonyl systems from Hypericum longistylum Oliv","volume":"6","author":"Zhang","year":"2019","journal-title":"Org. Chem. Front."},{"key":"ref_29","first-page":"193","article-title":"Triterpenoids from whole plants of Phyllanthus urinaria","volume":"9","author":"Wu","year":"2017","journal-title":"Chin. Herb. Med."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"8162","DOI":"10.1021\/acs.jafc.5b03081","article-title":"\u03b1-Glucosidase inhibition and antihyperglycemic activity of phenolics from the flowers of Edgeworthia gardneri","volume":"63","author":"Ma","year":"2015","journal-title":"J. Agric. Food. Chem."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/29\/8\/1728\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T14:26:19Z","timestamp":1760106379000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/29\/8\/1728"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,4,11]]},"references-count":30,"journal-issue":{"issue":"8","published-online":{"date-parts":[[2024,4]]}},"alternative-id":["molecules29081728"],"URL":"https:\/\/doi.org\/10.3390\/molecules29081728","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,4,11]]}}}