{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,7]],"date-time":"2026-10-07T00:00:31Z","timestamp":1791331231077,"version":"4.3.1"},"reference-count":22,"publisher":"American Chemical Society (ACS)","issue":"31","license":[{"start":{"date-parts":[[2026,7,24]],"date-time":"2026-07-24T00:00:00Z","timestamp":1784851200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by-nc-nd\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100000196","name":"Canada Foundation for Innovation","doi-asserted-by":"publisher","award":["34711"],"award-info":[{"award-number":["34711"]}],"id":[{"id":"10.13039\/501100000196","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100000196","name":"Canada Foundation for Innovation","doi-asserted-by":"publisher","award":["43407"],"award-info":[{"award-number":["43407"]}],"id":[{"id":"10.13039\/501100000196","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100000038","name":"Natural Sciences and Engineering Research Council of Canada","doi-asserted-by":"publisher","award":["227158"],"award-info":[{"award-number":["227158"]}],"id":[{"id":"10.13039\/501100000038","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100007711","name":"British Columbia Knowledge Development Fund","doi-asserted-by":"publisher","award":["103970"],"award-info":[{"award-number":["103970"]}],"id":[{"id":"10.13039\/501100007711","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,8,11]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>The North American fungus Echinodontium tinctorium has not been explored for its small-molecule constituents for 60 years. Herein, we describe chemical investigation of its organic extracts and bioactivity-guided fractionation, which led to the isolation of two new diterpenoids, echinodin A (1) and B (2). Both 1 and 2 contain an unprecedented tetracyclic 5\/3\/7\/5 carbon ring system with the highly constrained cyclopropane motif. Bis(2,4-dihydroxy-6-methylphenyl) methane (4) was isolated for the first time in a natural source together with four other known compounds (3, 5\u20137). The structures of 1\u20137 were determined by a combination of NMR, ESI-MS, and single-crystal X-ray diffraction analyses. Cytotoxic assays revealed that 1, 2, and 4 have weak cytotoxic activity against human cervical adenocarcinoma (HeLa) and human glioblastoma (U251). Echinodol (5) and echinodone (6), investigated for the first time for their bioactivity, exhibited strong cytotoxic activity with IC50 values ranging from 1.2 to 5.5 \u03bcM against a panel of human cancer cell lines. A mechanism of action investigation showed that echinodol (5) induced apoptosis and arrested the cell cycle at the S phase in U251 cells. These findings not only highlight the new chemistry and biology of isolated compounds but also position E. tinctorium as a source for further pharmacognostic exploration.<\/jats:p>","DOI":"10.1021\/acsomega.6c04642","type":"journal-article","created":{"date-parts":[[2026,7,27]],"date-time":"2026-07-27T05:00:16Z","timestamp":1785128416000},"page":"46754-46765","source":"Crossref","is-referenced-by-count":1,"title":["Isolation and Characterization\nof Unusual Terpene\nDerivatives from the Fungus\n                    <i>Echinodontium tinctorium<\/i>"],"prefix":"10.1021","volume":"11","author":[{"given":"Mehreen","family":"Zeb","sequence":"first","affiliation":[{"name":"University of Northern British Columbia , , , ,","place":["Prince George, BC, Canada, V2N 4Z9"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Muhammad Abubakar","family":"Sideeq","sequence":"additional","affiliation":[{"name":"University of Northern British Columbia , , , ,","place":["Prince George, BC, Canada, V2N 4Z9"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8209-4298","authenticated-orcid":true,"given":"Kalindi D.","family":"Morgan","sequence":"additional","affiliation":[{"name":"University of Northern British Columbia , , , ,","place":["Prince George, BC, Canada, V2N 4Z9"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wai-Ming","family":"Li","sequence":"additional","affiliation":[{"name":"University of Northern British Columbia , , , ,","place":["Prince George, BC, Canada, V2N 4Z9"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Victor P.","family":"Liu","sequence":"additional","affiliation":[{"name":"University of Northern British Columbia , , , ,","place":["Prince George, BC, Canada, V2N 4Z9"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2921-8439","authenticated-orcid":true,"given":"Brian O.","family":"Patrick","sequence":"additional","affiliation":[{"name":"University of British Columbia , , , ,","place":["Vancouver, BC, Canada, V6T 1Z1"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhicheng","family":"Xia","sequence":"additional","affiliation":[{"name":"University of British Columbia , , , ,","place":["Vancouver, BC, Canada, V6T 1Z1"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kerry","family":"Reimer","sequence":"additional","affiliation":[{"name":"University of Northern British Columbia , , , ,","place":["Prince George, BC, Canada, V2N 4Z9"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6136-7058","authenticated-orcid":true,"given":"Chow H.","family":"Lee","sequence":"additional","affiliation":[{"name":"University of Northern British Columbia , , , ,","place":["Prince George, BC, Canada, V2N 4Z9"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,7,24]]},"reference":[{"key":"2026081110200323400_cit1","doi-asserted-by":"publisher","first-page":"5793","DOI":"10.1016\/0040-4020(96)00204-9","article-title":"Isolation\nof a fluorone pigment from the Indian paint fungus Echinodontium tinctorium and Pyrofomes albomarginatus","volume":"52","author":"Ye","year":"1996","journal-title":"Tetrahedron"},{"key":"2026081110200323400_cit2","doi-asserted-by":"publisher","first-page":"568","DOI":"10.1080\/00275514.2017.1369830","article-title":"Phylogeny\nand taxonomy of Echinodontium and related genera","volume":"109","author":"Liu","year":"2017","journal-title":"Mycologia"},{"key":"2026081110200323400_cit3","doi-asserted-by":"publisher","DOI":"10.3390\/molecules26020251","article-title":"Medicinal properties and bioactive compounds from wild\nmushrooms native to North America","volume":"26","author":"Zeb","year":"2021","journal-title":"Molecules"},{"issue":"6","key":"2026081110200323400_cit4","doi-asserted-by":"publisher","first-page":"485","DOI":"10.1615\/IntJMedMushrooms.v19.i6.10","article-title":"Growth-inhibitory\nand immunomodulatory activities of wild mushrooms from north-central\nBritish Columbia (Canada)","volume":"19","author":"Smith","year":"2017","journal-title":"Int. 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