{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,20]],"date-time":"2026-03-20T11:11:52Z","timestamp":1774005112245,"version":"3.50.1"},"reference-count":37,"publisher":"Elsevier BV","license":[{"start":{"date-parts":[[2026,6,1]],"date-time":"2026-06-01T00:00:00Z","timestamp":1780272000000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/tdm\/userlicense\/1.0\/"},{"start":{"date-parts":[[2026,6,1]],"date-time":"2026-06-01T00:00:00Z","timestamp":1780272000000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/legal\/tdmrep-license"},{"start":{"date-parts":[[2026,6,1]],"date-time":"2026-06-01T00:00:00Z","timestamp":1780272000000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-017"},{"start":{"date-parts":[[2026,6,1]],"date-time":"2026-06-01T00:00:00Z","timestamp":1780272000000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2026,6,1]],"date-time":"2026-06-01T00:00:00Z","timestamp":1780272000000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-012"},{"start":{"date-parts":[[2026,6,1]],"date-time":"2026-06-01T00:00:00Z","timestamp":1780272000000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2026,6,1]],"date-time":"2026-06-01T00:00:00Z","timestamp":1780272000000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-004"}],"funder":[{"DOI":"10.13039\/501100012166","name":"National Key Research and Development Program of China","doi-asserted-by":"publisher","award":["2021YFA0910500"],"award-info":[{"award-number":["2021YFA0910500"]}],"id":[{"id":"10.13039\/501100012166","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["U22A20380"],"award-info":[{"award-number":["U22A20380"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["82373755"],"award-info":[{"award-number":["82373755"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["82173706"],"award-info":[{"award-number":["82173706"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100012226","name":"Fundamental Research Funds for the Central Universities","doi-asserted-by":"publisher","award":["2024BRA018"],"award-info":[{"award-number":["2024BRA018"]}],"id":[{"id":"10.13039\/501100012226","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100013804","name":"Fundamental Research Funds for the Central Universities","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100013804","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003397","name":"Huazhong University of Science and Technology","doi-asserted-by":"publisher","award":["2025JYCXJJ066"],"award-info":[{"award-number":["2025JYCXJJ066"]}],"id":[{"id":"10.13039\/501100003397","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["elsevier.com","sciencedirect.com"],"crossmark-restriction":true},"short-container-title":["Phytochemistry"],"published-print":{"date-parts":[[2026,6]]},"DOI":"10.1016\/j.phytochem.2026.114802","type":"journal-article","created":{"date-parts":[[2026,1,31]],"date-time":"2026-01-31T00:08:32Z","timestamp":1769818112000},"page":"114802","update-policy":"https:\/\/doi.org\/10.1016\/elsevier_cm_policy","source":"Crossref","is-referenced-by-count":0,"special_numbering":"C","title":["1H NMR-guided isolation of ophiobolins from Bipolaris maydis and their bioactivities"],"prefix":"10.1016","volume":"246","author":[{"given":"Yong","family":"Shen","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Xiaotian","family":"Zhang","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Qin","family":"Li","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Mengru","family":"Yu","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yongqi","family":"Li","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Luosheng","family":"Wan","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Xing","family":"Sun","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Chunmei","family":"Chen","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yonghui","family":"Zhang","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hucheng","family":"Zhu","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"78","reference":[{"key":"10.1016\/j.phytochem.2026.114802_bib1","doi-asserted-by":"crossref","first-page":"733","DOI":"10.1016\/S0024-3205(00)00668-8","article-title":"The biology of ophiobolins","volume":"67","author":"Au","year":"2000","journal-title":"Life Sci."},{"key":"10.1016\/j.phytochem.2026.114802_bib2","doi-asserted-by":"crossref","DOI":"10.1016\/j.phytochem.2024.114065","article-title":"Proliferacorins A\u2013M: thirteen undescribed acorane sesquiterpenoids isolated from the fungus Fusarium proliferatum","volume":"221","author":"Bao","year":"2024","journal-title":"Phytochemistry"},{"key":"10.1016\/j.phytochem.2026.114802_bib3","doi-asserted-by":"crossref","first-page":"14629","DOI":"10.3390\/molecules181214629","article-title":"Bio-activity and dereplication-based discovery of ophiobolins and other fungal secondary metabolites targeting leukemia cells","volume":"18","author":"Bladt","year":"2013","journal-title":"Molecules"},{"key":"10.1016\/j.phytochem.2026.114802_bib4","doi-asserted-by":"crossref","first-page":"2268","DOI":"10.1021\/acs.jnatprod.9b00462","article-title":"Ophiobolin-type sesterterpenoids from the mangrove endophytic fungus Aspergillus sp. ZJ-68","volume":"82","author":"Cai","year":"2019","journal-title":"J. Nat. Prod."},{"key":"10.1016\/j.phytochem.2026.114802_bib5","doi-asserted-by":"crossref","first-page":"3652","DOI":"10.1021\/acs.jnatprod.0c00860","article-title":"Ophiobolin sesterterpenoids and farnesylated phthalide derivatives from the deep sea cold-seep-derived fungus Aspergillus insuetus SD-512","volume":"83","author":"Chi","year":"2020","journal-title":"J. Nat. Prod."},{"key":"10.1016\/j.phytochem.2026.114802_bib6","doi-asserted-by":"crossref","first-page":"346","DOI":"10.3390\/md17060346","article-title":"New ophiobolin derivatives from the marine fungus Aspergillus flocculosus and their cytotoxicities against cancer cells","volume":"17","author":"Choi","year":"2019","journal-title":"Mar. Drugs"},{"key":"10.1016\/j.phytochem.2026.114802_bib7","doi-asserted-by":"crossref","first-page":"575","DOI":"10.3390\/md18110575","article-title":"New ophiobolins from the deep-sea derived fungus Aspergillus sp. WHU0154 and their anti-inflammatory effects","volume":"18","author":"Ding","year":"2020","journal-title":"Mar. Drugs"},{"key":"10.1016\/j.phytochem.2026.114802_bib8","doi-asserted-by":"crossref","first-page":"339","DOI":"10.3390\/microorganisms10020339","article-title":"Endophytic fungal terpenoids: natural role and bioactivities","volume":"10","author":"Galindo-Sol\u00eds","year":"2022","journal-title":"Microorganisms"},{"key":"10.1016\/j.phytochem.2026.114802_bib9","doi-asserted-by":"crossref","DOI":"10.1016\/j.bioorg.2022.105817","article-title":"Natural terpenoids with anti-inflammatory activities: potential leads for anti-inflammatory drug discovery","volume":"124","author":"Ge","year":"2022","journal-title":"Bioorg. Chem."},{"key":"10.1016\/j.phytochem.2026.114802_bib10","doi-asserted-by":"crossref","first-page":"12526","DOI":"10.1021\/acs.joc.5b02396","article-title":"Beyond DP4: an improved probability for the stereochemical assignment of isomeric compounds using quantum chemical calculations of NMR shifts","volume":"80","author":"Grimblat","year":"2015","journal-title":"J. Org. Chem."},{"key":"10.1016\/j.phytochem.2026.114802_bib11","doi-asserted-by":"crossref","DOI":"10.1016\/j.biopha.2022.114165","article-title":"Marine life as a source for breast cancer treatment: a comprehensive review","volume":"159","author":"Hussain","year":"2023","journal-title":"Biomed. Pharmacother."},{"key":"10.1016\/j.phytochem.2026.114802_bib12","doi-asserted-by":"crossref","first-page":"74","DOI":"10.1021\/np50115a009","article-title":"Microbial metabolites of ophiobolin A and antimicrobial evaluation of ophiobolins","volume":"58","author":"Li","year":"1995","journal-title":"J. Nat. Prod."},{"key":"10.1016\/j.phytochem.2026.114802_bib13","first-page":"935","article-title":"Bipolarins A\u2013H, eight new ophiobolin-type sesterterpenes with antimicrobial activity from fungus Bipolaris sp. TJ403-B1","volume":"17","author":"Liu","year":"2019","journal-title":"Chin. J. Nat. Med."},{"key":"10.1016\/j.phytochem.2026.114802_bib14","doi-asserted-by":"crossref","first-page":"12091","DOI":"10.1002\/anie.201905966","article-title":"Bipolarolides A\u2013G: ophiobolin-derived sesterterpenes with three new carbon skeletons from Bipolaris sp. TJ403-B1","volume":"58","author":"Liu","year":"2019","journal-title":"Angew. Chem. Int. Ed."},{"key":"10.1016\/j.phytochem.2026.114802_bib15","doi-asserted-by":"crossref","first-page":"588","DOI":"10.1039\/C2RA22701K","article-title":"Terretonin, ophiobolin, and drimaneterpenes with absolute configurations from an algicolous Aspergillus ustus","volume":"3","author":"Liu","year":"2013","journal-title":"RSC Adv."},{"key":"10.1016\/j.phytochem.2026.114802_bib16","doi-asserted-by":"crossref","first-page":"859","DOI":"10.1016\/j.bmcl.2019.02.007","article-title":"Chemistry and biology of ophiobolin A and its congeners","volume":"29","author":"Masi","year":"2019","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"10.1016\/j.phytochem.2026.114802_bib17","doi-asserted-by":"crossref","DOI":"10.1016\/j.phytochem.2023.113722","article-title":"Ten undescribed eremophilane and guaiane sesquiterpenes from Penicillium roqueforti","volume":"212","author":"Mo","year":"2023","journal-title":"Phytochemistry"},{"key":"10.1016\/j.phytochem.2026.114802_bib18","doi-asserted-by":"crossref","first-page":"73","DOI":"10.1002\/wcms.81","article-title":"The ORCA program system","volume":"2","author":"Neese","year":"2012","journal-title":"WIREs Comput. Mol. Sci."},{"key":"10.1016\/j.phytochem.2026.114802_bib19","doi-asserted-by":"crossref","DOI":"10.1002\/wcms.1327","article-title":"Software update: the ORCA program system, version 4.0","volume":"8","author":"Neese","year":"2018","journal-title":"WIREs Comput. Mol. Sci."},{"key":"10.1016\/j.phytochem.2026.114802_bib20","doi-asserted-by":"crossref","first-page":"6072","DOI":"10.1039\/D0OB01470B","article-title":"On the mechanism of ophiobolin F synthase and the absolute configuration of its product by isotopic labelling experiments","volume":"18","author":"Quan","year":"2020","journal-title":"Org. Biomol. Chem."},{"key":"10.1016\/j.phytochem.2026.114802_bib21","doi-asserted-by":"crossref","first-page":"856","DOI":"10.3389\/fmicb.2020.00856","article-title":"Novel antimicrobial compounds as ophiobolin-type sesterterpenes and pimarane-type diterpene from Bipolaris species TJ403-B1","volume":"11","author":"Shen","year":"2020","journal-title":"Front. Microbiol."},{"key":"10.1016\/j.phytochem.2026.114802_bib22","doi-asserted-by":"crossref","first-page":"3549","DOI":"10.1021\/acs.jafc.3c08134","article-title":"Bipoladien A, a sesterterpenoid containing an undescribed 5\/8\/5\/7 carbon skeleton from Bipolaris maydis","volume":"72","author":"Shen","year":"2024","journal-title":"J. Agric. Food Chem."},{"key":"10.1016\/j.phytochem.2026.114802_bib23","doi-asserted-by":"crossref","first-page":"1286","DOI":"10.1021\/acs.jnatprod.5c00024","article-title":"Bipoladisins A\u2013G, uncommon sesterterpenoids with three types of carbon skeletons from Bipolaris maydis and their reversal activity on paclitaxel resistance","volume":"88","author":"Shen","year":"2025","journal-title":"J. Nat. Prod."},{"key":"10.1016\/j.phytochem.2026.114802_bib24","doi-asserted-by":"crossref","first-page":"229","DOI":"10.1002\/chir.20733","article-title":"ECD cotton effect approximated by the Gaussian curve and other methods","volume":"22","author":"Stephens","year":"2010","journal-title":"Chirality"},{"key":"10.1016\/j.phytochem.2026.114802_bib25","doi-asserted-by":"crossref","first-page":"785","DOI":"10.1016\/j.funbio.2017.05.008","article-title":"Characterization of the autophagy-related gene BmATG8 in Bipolaris maydis","volume":"121","author":"Sumita","year":"2017","journal-title":"Fungal Biol."},{"key":"10.1016\/j.phytochem.2026.114802_bib26","doi-asserted-by":"crossref","first-page":"8307","DOI":"10.1021\/acs.orglett.0c02938","article-title":"Pharmacophore-directed retrosynthesis applied to ophiobolin A: simplified bicyclic derivatives displaying anticancer activity","volume":"22","author":"Tao","year":"2020","journal-title":"Org. Lett."},{"key":"10.1016\/j.phytochem.2026.114802_bib27","doi-asserted-by":"crossref","first-page":"229","DOI":"10.3390\/md15070229","article-title":"The biological activities of sesterterpenoid-type ophiobolins","volume":"15","author":"Tian","year":"2017","journal-title":"Mar. Drugs"},{"key":"10.1016\/j.phytochem.2026.114802_bib28","doi-asserted-by":"crossref","first-page":"531","DOI":"10.1016\/0968-0896(96)00036-3","article-title":"Ophiobolin M and analogues, noncompetitive inhibitors of ivermectin binding with nematocidal activity","volume":"4","author":"Tsipouras","year":"1996","journal-title":"Bioorg. Med. Chem."},{"key":"10.1016\/j.phytochem.2026.114802_bib29","doi-asserted-by":"crossref","first-page":"309","DOI":"10.3389\/fphar.2018.00309","article-title":"Endophytic fungi-alternative sources of cytotoxic compounds: a review","volume":"9","author":"Uzma","year":"2018","journal-title":"Front. Pharmacol."},{"key":"10.1016\/j.phytochem.2026.114802_bib30","doi-asserted-by":"crossref","first-page":"220","DOI":"10.1016\/j.fitote.2013.08.002","article-title":"Ophiobolins P\u2013T, five new cytotoxic and antibacterial sesterterpenes from the endolichenic fungus Ulocladium sp","volume":"90","author":"Wang","year":"2013","journal-title":"Fitoterapia"},{"key":"10.1016\/j.phytochem.2026.114802_bib31","doi-asserted-by":"crossref","first-page":"839","DOI":"10.1007\/s13238-016-0325-y","article-title":"3-Anhydro-6-hydroxy-ophiobolin A displays high in vitro and in vivo efficacy against influenza A virus infection","volume":"7","author":"Wang","year":"2016","journal-title":"Protein Cell"},{"key":"10.1016\/j.phytochem.2026.114802_bib32","doi-asserted-by":"crossref","first-page":"11982","DOI":"10.1021\/acs.jafc.3c03352","article-title":"LC\u2013MS\/MS-guided molecular networking for targeted discovery of undescribed and bioactive ophiobolins from Bipolaris eleusines","volume":"71","author":"Wang","year":"2023","journal-title":"J. Agric. Food Chem."},{"key":"10.1016\/j.phytochem.2026.114802_bib33","first-page":"1","article-title":"Advances in pharmacological activities of terpenoids","volume":"15","author":"Yang","year":"2020","journal-title":"Nat. Prod. Commun."},{"key":"10.1016\/j.phytochem.2026.114802_bib34","first-page":"1411","article-title":"Ophiobolin O and 6-epi-ophiobolin O, two new cytotoxic sesterterpenes from the marine derived fungus Aspergillus sp","volume":"7","author":"Zhang","year":"2012","journal-title":"Nat. Prod. Commun."},{"key":"10.1016\/j.phytochem.2026.114802_bib35","doi-asserted-by":"crossref","DOI":"10.1016\/j.bioorg.2024.107280","article-title":"New diarylcyclopentenone enantiomers and biphenyl derivatives from the fungus Talaromyces adpressus","volume":"146","author":"Zheng","year":"2024","journal-title":"Bioorg. Chem."},{"key":"10.1016\/j.phytochem.2026.114802_bib36","doi-asserted-by":"crossref","first-page":"1965","DOI":"10.1021\/acs.jnatprod.4c00385","article-title":"Undobolins A\u2013L, ophiobolin-type sesterterpenoids from Aspergillus undulatus","volume":"87","author":"Zheng","year":"2024","journal-title":"J. Nat. Prod."},{"key":"10.1016\/j.phytochem.2026.114802_bib37","doi-asserted-by":"crossref","first-page":"2","DOI":"10.1021\/acs.jnatprod.7b00335","article-title":"Ophiobolins from the mangrove fungus Aspergillus ustus","volume":"81","author":"Zhu","year":"2018","journal-title":"J. Nat. Prod."}],"container-title":["Phytochemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S003194222600035X?httpAccept=text\/xml","content-type":"text\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S003194222600035X?httpAccept=text\/plain","content-type":"text\/plain","content-version":"vor","intended-application":"text-mining"}],"deposited":{"date-parts":[[2026,3,20]],"date-time":"2026-03-20T09:03:53Z","timestamp":1773997433000},"score":1,"resource":{"primary":{"URL":"https:\/\/linkinghub.elsevier.com\/retrieve\/pii\/S003194222600035X"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,6]]},"references-count":37,"alternative-id":["S003194222600035X"],"URL":"https:\/\/doi.org\/10.1016\/j.phytochem.2026.114802","relation":{},"ISSN":["0031-9422"],"issn-type":[{"value":"0031-9422","type":"print"}],"subject":[],"published":{"date-parts":[[2026,6]]},"assertion":[{"value":"Elsevier","name":"publisher","label":"This article is maintained by"},{"value":"1H NMR-guided isolation of ophiobolins from Bipolaris maydis and their bioactivities","name":"articletitle","label":"Article Title"},{"value":"Phytochemistry","name":"journaltitle","label":"Journal Title"},{"value":"https:\/\/doi.org\/10.1016\/j.phytochem.2026.114802","name":"articlelink","label":"CrossRef DOI link to publisher maintained version"},{"value":"article","name":"content_type","label":"Content Type"},{"value":"\u00a9 2026 Elsevier Ltd. All rights are reserved, including those for text and data mining, AI training, and similar technologies.","name":"copyright","label":"Copyright"}],"article-number":"114802"}}