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We isolated a novel aryltetralin lactone lignan from Taiwania flousiana, identified as 4-O-\u03b1-thevetopyranosyldiphyllin. The compound showed potent pre- and postemergence herbicidal activity against 13 monocot and dicot weeds, with IC50 values ranging from 0.18 to 4.72 \u03bcg\/mL. Under greenhouse conditions, foliar application at 80 \u03bcg\/mL for 7 days achieved over 85% inhibition in two test weeds, comparable to glyphosate. It exhibited systemic translocation and selectivity in crops such as rice. Soil degradation half-lives were 25.1 days in paddy soil and 63.0 days in vegetable soil. The compound disrupted microtubule organization by inhibiting tubulin polymerization, specifically binding to \u03b2-tubulin (TUB7) with a high affinity of \u22128.30 kcal\/mol, as confirmed by molecular docking and dynamics simulations. These results indicated that 4-O-\u03b1-thevetopyranosyldiphyllin was a promising lead compound for the development of a new class of systemic herbicides targeting \u03b2-tubulin.<\/jats:p>","DOI":"10.1021\/acs.jafc.5c11985","type":"journal-article","created":{"date-parts":[[2026,5,28]],"date-time":"2026-05-28T20:17:21Z","timestamp":1779999441000},"page":"17764-17782","source":"Crossref","is-referenced-by-count":0,"title":["4-\n                    <i>O<\/i>\n                    -\u03b1-Thevetopyranosyldiphyllin\nfrom\n                    <i>Taiwania flousiana<\/i>\n                    : A Novel \u03b2-Tubulin\nInhibitor with Broad-Spectrum Herbicidal Activity for Sustainable\nWeed Management"],"prefix":"10.1021","volume":"74","author":[{"given":"Yuan","family":"Xie","sequence":"first","affiliation":[{"name":"South China Agricultural University , , ,","place":["Guangzhou, China, 510642"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yifeng","family":"Zhou","sequence":"additional","affiliation":[{"name":"Hubei Minzu University , , ,","place":["Enshi, China, 445000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hongmei","family":"Liu","sequence":"additional","affiliation":[{"name":"South China Agricultural University , , ,","place":["Guangzhou, China, 510642"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jialin","family":"Li","sequence":"additional","affiliation":[{"name":"South China Agricultural University , , ,","place":["Guangzhou, China, 510642"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Qiaoyu","family":"Tang","sequence":"additional","affiliation":[{"name":"Hubei Minzu University , , ,","place":["Enshi, China, 445000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lilong","family":"Gao","sequence":"additional","affiliation":[{"name":"Hubei Minzu University , , ,","place":["Enshi, China, 445000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yao","family":"Li","sequence":"additional","affiliation":[{"name":"Hubei Minzu University , , ,","place":["Enshi, China, 445000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4490-2738","authenticated-orcid":true,"given":"Jiguang","family":"Huang","sequence":"additional","affiliation":[{"name":"South China Agricultural University , , ,","place":["Guangzhou, China, 510642"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7720-4138","authenticated-orcid":true,"given":"Lijuan","family":"Zhou","sequence":"additional","affiliation":[{"name":"South China Agricultural University , , ,","place":["Guangzhou, China, 510642"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,5,28]]},"reference":[{"key":"2026073021184289900_cit1","doi-asserted-by":"publisher","first-page":"79","DOI":"10.1021\/bk-2015-1204.ch007","article-title":"Discovery of\nNew Herbicide Modes of Action with Natural Phytotoxins","volume-title":"Discovery and Synthesis of Crop Protection Products","author":"Duke","year":"2015"},{"issue":"9","key":"2026073021184289900_cit2","doi-asserted-by":"publisher","first-page":"341","DOI":"10.3390\/plants8090341","article-title":"Current\nstatus and future prospects in herbicide discovery","volume":"8","author":"Dayan","year":"2019","journal-title":"Plants"},{"issue":"3","key":"2026073021184289900_cit3","doi-asserted-by":"publisher","first-page":"1090","DOI":"10.1104\/pp.114.239061","article-title":"Natural compounds\nas next-generation herbicides","volume":"166","author":"Dayan","year":"2014","journal-title":"Plant Physiol."},{"issue":"1","key":"2026073021184289900_cit4","first-page":"115","article-title":"Allelopathic\npotential of berberine, isolated and identified from Coptis chinensis Franch on five invasive weeds","volume":"39","author":"Zhou","year":"2016","journal-title":"Allelopathy J."},{"issue":"30","key":"2026073021184289900_cit5","doi-asserted-by":"publisher","first-page":"6100","DOI":"10.1021\/acs.jafc.7b01259","article-title":"Herbicidal\nspectrum, absorption and transportation, and physiological effect\non Bidens pilosa of the natural alkaloid berberine","volume":"65","author":"Wu","year":"2017","journal-title":"J. Agric. Food Chem."},{"issue":"4","key":"2026073021184289900_cit6","doi-asserted-by":"publisher","first-page":"437","DOI":"10.1002\/cbdv.201500130","article-title":"Herbicidal and cytotoxic constituents\nfrom Aralia armata (Wall.) Seem","volume":"13","author":"Miao","year":"2016","journal-title":"Chem. Biodiversity"},{"key":"2026073021184289900_cit7","doi-asserted-by":"publisher","first-page":"9994","DOI":"10.1021\/jf102087c","article-title":"Phytotoxicity\nof sarmentine isolated from long pepper (Piper longum) fruit","volume":"58","author":"Huang","year":"2010","journal-title":"J. Agric. Food Chem."},{"issue":"8","key":"2026073021184289900_cit8","first-page":"1002","article-title":"Terpenoids and phenols from Taiwania flousiana","volume":"46","author":"Xiang","year":"2004","journal-title":"Acta Bot. 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Thesis, Northwest A&F University, Yangling, China, 2004;"},{"issue":"3","key":"2026073021184289900_cit20","doi-asserted-by":"publisher","first-page":"1934578X1801300302","DOI":"10.1177\/1934578x1801300302","article-title":"Phytotoxic lignans from Artemisia arborescens","volume":"13","author":"Labruzzo","year":"2018","journal-title":"Nat. Prod. Commun."},{"key":"2026073021184289900_cit21","doi-asserted-by":"publisher","first-page":"634018","DOI":"10.3389\/fpls.2021.634018","article-title":"Dinitroaniline herbicide\nresistance and mechanisms in weeds","volume":"12","author":"Chen","year":"2021","journal-title":"Front. 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Soc."}],"container-title":["Journal of Agricultural\nand Food Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.jafc.5c11985","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/jafcau\/article-pdf\/74\/23\/17764\/66263131\/acs.jafc.5c11985.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/jafcau\/article-pdf\/74\/23\/17764\/66263131\/acs.jafc.5c11985.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,7,31]],"date-time":"2026-07-31T01:18:51Z","timestamp":1785460731000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/jafcau\/article\/74\/23\/17764\/5232943\/4-O-Thevetopyranosyldiphyllin-from-Taiwania"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,5,28]]},"references-count":39,"journal-issue":{"issue":"23","published-online":{"date-parts":[[2026,5,28]]},"published-print":{"date-parts":[[2026,6,17]]}},"URL":"https:\/\/doi.org\/10.1021\/acs.jafc.5c11985","relation":{},"ISSN":["0021-8561","1520-5118"],"issn-type":[{"value":"0021-8561","type":"print"},{"value":"1520-5118","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,5,28]]}}}