{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,30]],"date-time":"2026-09-30T13:57:45Z","timestamp":1790776665831,"version":"4.1.0"},"reference-count":56,"publisher":"American Chemical Society (ACS)","issue":"38","license":[{"start":{"date-parts":[[2026,9,16]],"date-time":"2026-09-16T00:00:00Z","timestamp":1789516800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2026,9,16]],"date-time":"2026-09-16T00:00:00Z","timestamp":1789516800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2026,9,16]],"date-time":"2026-09-16T00:00:00Z","timestamp":1789516800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"funder":[{"DOI":"10.13039\/501100002858","name":"China Postdoctoral Science Foundation","doi-asserted-by":"publisher","award":["GZC20231130"],"award-info":[{"award-number":["GZC20231130"]}],"id":[{"id":"10.13039\/501100002858","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100010855","name":"Jiangsu Provincial Department of Human Resources and Social Security","doi-asserted-by":"publisher","award":["2023ZB075"],"award-info":[{"award-number":["2023ZB075"]}],"id":[{"id":"10.13039\/501100010855","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100012166","name":"National Key Research and Development Program of China","doi-asserted-by":"publisher","award":["2021YFD1700100"],"award-info":[{"award-number":["2021YFD1700100"]}],"id":[{"id":"10.13039\/501100012166","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,9,30]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Natural products are an important source of lead compounds for novel pesticide discovery. In this study, we investigated the phytotoxicity and mode of action of the phenolic natural product apocynin. Chlorophyll fluorescence analysis indicated that apocynin induces leaf lesions by blocking photosystem II (PSII) electron transport beyond the primary quinone acceptor QA. Molecular docking and isothermal titration calorimetry (ITC) identified the D1 protein as the molecular target of apocynin, pinpointing His215 and His272 as critical binding residues. Guided by this interaction model, we designed thirty-six apocynin derivatives, among which two compounds (A4 and A6) with higher binding affinity and lower toxicity than apocynin were synthesized. Structure-activity relationship analysis further confirmed that both derivatives exhibit significantly stronger PSII inhibitory activity and superior herbicidal efficacy compared with the parent compound. This work establishes apocynin as a natural PSII inhibitor and highlights its phenolic scaffold as a promising platform for herbicide development.<\/jats:p>","DOI":"10.1021\/acs.jafc.6c01434","type":"journal-article","created":{"date-parts":[[2026,9,16]],"date-time":"2026-09-16T09:02:07Z","timestamp":1789549327000},"page":"29869-29886","source":"Crossref","is-referenced-by-count":0,"title":["Apocynin as a Novel\nNatural Photosystem II Inhibitor:\nTarget Identification and Structure-Based Design of Potent Herbicidal\nDerivatives"],"prefix":"10.1021","volume":"74","author":[{"given":"He","family":"Wang","sequence":"first","affiliation":[{"name":"Nanjing Agricultural University , , ,","place":["Nanjing, P. R. China, 210095"]},{"name":"Anhui Academy of Agricultural Sciences , , ,","place":["Hefei, P. R. China, 230001"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yanjing","family":"Guo","sequence":"additional","affiliation":[{"name":"Nanjing Agricultural University , , ,","place":["Nanjing, P. R. China, 210095"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mingli","family":"Wu","sequence":"additional","affiliation":[{"name":"Nanjing Agricultural University , , ,","place":["Nanjing, P. R. China, 210095"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Qizhen","family":"Chen","sequence":"additional","affiliation":[{"name":"Nanjing Agricultural University , , ,","place":["Nanjing, P. R. China, 210095"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Qianlong","family":"Zhang","sequence":"additional","affiliation":[{"name":"Nanjing Agricultural University , , ,","place":["Nanjing, P. R. China, 210095"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Qing","family":"Liu","sequence":"additional","affiliation":[{"name":"Nanjing Agricultural University , , ,","place":["Nanjing, P. R. China, 210095"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8762-1373","authenticated-orcid":true,"given":"Shiguo","family":"Chen","sequence":"additional","affiliation":[{"name":"Nanjing Agricultural University , , ,","place":["Nanjing, P. R. China, 210095"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,9,16]]},"reference":[{"key":"2026093009073930600_cit1","doi-asserted-by":"publisher","first-page":"17200","DOI":"10.1021\/acs.jafc.4c01834","article-title":"Design, synthesis, and herbicidal\nactivity of natural naphthoquinone derivatives containing diaryl ether\nstructures","volume":"72","author":"Wang","year":"2024","journal-title":"J. Agric. 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Food Chem."},{"key":"2026093009073930600_cit28","unstructured":"Heap, I.\n          \n          The international herbicide-resistant\nweed database.http:\/\/weedscience.org\/Pages\/MOA.aspx?MOAID=6. (Accessed on 28 September 2025)."},{"key":"2026093009073930600_cit29","doi-asserted-by":"publisher","first-page":"106558","DOI":"10.1016\/j.fitote.2025.106558","article-title":"A comprehensive update on phytochemistry and medicinal\ndevelopments of apocynin","volume":"183","author":"Bhatia","year":"2025","journal-title":"Fitoterapia"},{"issue":"1","key":"2026093009073930600_cit30","doi-asserted-by":"publisher","first-page":"15","DOI":"10.1186\/s12933-017-0657-9","article-title":"Influence\nof apocynin on cardiac remodeling in rats with streptozotocin-induced\ndiabetes mellitus","volume":"17","author":"Gimenes","year":"2018","journal-title":"Cardiovasc. Diabetol."},{"key":"2026093009073930600_cit31","doi-asserted-by":"publisher","first-page":"2482","DOI":"10.1002\/ps.5402","article-title":"An evaluation of tenuazonic\nacid, a potential biobased herbicide in cotton","volume":"75","author":"Zhou","year":"2019","journal-title":"Pest Manage. Sci."},{"key":"2026093009073930600_cit32","doi-asserted-by":"crossref","first-page":"321","DOI":"10.1007\/978-1-4020-3218-9_12","article-title":"Analysis\nof the Chlorophyll a Fluorescence Transient","volume-title":"Chlorophyll Fluorescence: A Signature of Photosynthesis","author":"Strasser","year":"2004"},{"key":"2026093009073930600_cit33","unstructured":"Protein Data Bank.\n          \n          Cryo-EM structure\nof the PSII\nsupercomplex from Arabidopsis thaliana. https:\/\/www.rcsb.org\/structure\/5MDX. (Accessed on 28 September 2025)."},{"key":"2026093009073930600_cit34","doi-asserted-by":"publisher","first-page":"214","DOI":"10.1002\/prot.340210304","article-title":"Modeling the quinone-B binding-site of the photosystem-II\nreaction center using notions of complementarity and contact-surface\nbetween atoms","volume":"21","author":"Sobolev","year":"1995","journal-title":"Proteins"},{"key":"2026093009073930600_cit35","unstructured":"National Center for Biotechnology Information.\n          \n          Photosystem\nII protein D1 of Arabidopsis thaliana. https:\/\/www.ncbi.nlm.nih.gov\/protein\/NP_051039.1. 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Biol."},{"key":"2026093009073930600_cit48","doi-asserted-by":"publisher","first-page":"560","DOI":"10.32615\/ps.2020.003","article-title":"Probing the photosynthetic apparatus\nnoninvasively in the laboratory of Reto Strasser in the countryside\nof Geneva between 2001 and 2009","volume":"58","author":"To\u0301th","year":"2010","journal-title":"Photosynthetica"},{"key":"2026093009073930600_cit49","doi-asserted-by":"publisher","first-page":"2054","DOI":"10.1002\/pro.5560051012","article-title":"Modeling of\nthe D1\/D2 proteins and cofactors of the\nphotosystem II reaction center: Implications for herbicide and bicarbonate\nbinding","volume":"5","author":"Xiong","year":"1996","journal-title":"Protein Sci."},{"key":"2026093009073930600_cit50","doi-asserted-by":"crossref","first-page":"101","DOI":"10.1016\/B978-044451167-6.50011-8","article-title":"The Mode of Action\nof Triazine Herbicides in Plants","volume-title":"The Triazine\nHerbicides","author":"Trebst","year":"2008"},{"issue":"1","key":"2026093009073930600_cit51","doi-asserted-by":"publisher","first-page":"17","DOI":"10.1038\/s43586-023-00199-x","article-title":"Isothermal titration calorimetry","volume":"3","author":"Bastos","year":"2023","journal-title":"Nat. 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Chem."}],"container-title":["Journal of Agricultural\nand Food Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.jafc.6c01434","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/jafcau\/article-pdf\/74\/38\/29869\/68527909\/acs.jafc.6c01434.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/jafcau\/article-pdf\/74\/38\/29869\/68527909\/acs.jafc.6c01434.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,30]],"date-time":"2026-09-30T13:14:04Z","timestamp":1790774044000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/jafcau\/article\/74\/38\/29869\/5431039\/Apocynin-as-a-Novel-Natural-Photosystem-II"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,9,16]]},"references-count":56,"journal-issue":{"issue":"38","published-online":{"date-parts":[[2026,9,16]]},"published-print":{"date-parts":[[2026,9,30]]}},"URL":"https:\/\/doi.org\/10.1021\/acs.jafc.6c01434","relation":{},"ISSN":["0021-8561","1520-5118"],"issn-type":[{"value":"0021-8561","type":"print"},{"value":"1520-5118","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,9,16]]}}}