{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,31]],"date-time":"2026-01-31T01:53:45Z","timestamp":1769824425080,"version":"3.49.0"},"reference-count":47,"publisher":"MDPI AG","issue":"10","license":[{"start":{"date-parts":[[2021,10,3]],"date-time":"2021-10-03T00:00:00Z","timestamp":1633219200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100006769","name":"Russian Science Foundation","doi-asserted-by":"publisher","award":["20-74-00073"],"award-info":[{"award-number":["20-74-00073"]}],"id":[{"id":"10.13039\/501100006769","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["JoF"],"abstract":"<jats:p>Ten-membered lactones (nonenolides) demonstrate phytotoxic, antimicrobial, and fungicidal activity promising for the development of natural product-derived pesticides. The fungus Stagonospora cirsii is able to produce phytotoxic stagonolides A (1), J (2), K (3) and herbarumin I (4) with high yield. The aim of this study was to create a set of structurally related nonenolides and to reveal the structural features that affect their biological activity. Stagonolide A (1) and C-7 oxidized stagonolide K (11) showed the highest phytotoxicity in leaf puncture assay and agar seedlings assay. The oxidation of C-7 hydroxyl group (as in 1, acetylstagonolide A (10) and (11) led to the manifestation of toxicity to microalgae, Bacillus subtilis and Sf9 cells regardless of the configuration of C-9 propyl chains (R in 1 and 10, S in 11). C-7 non-oxidized nonenolides displayed none or little non-target activity. Notably, 7S compounds were more phytotoxic than their 7R analogues. Due to the high inhibitory activity against seedling growth and the lack of side toxicity, mono- and bis(acetyl)- derivatives of herbarumin I were shown to be potent for the development of pre-emergent herbicides. The identified structural features can be used for the rational design of new herbicides.<\/jats:p>","DOI":"10.3390\/jof7100829","type":"journal-article","created":{"date-parts":[[2021,10,7]],"date-time":"2021-10-07T16:23:58Z","timestamp":1633623838000},"page":"829","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":16,"title":["Structure\u2013Activity Relationship of Phytotoxic Natural 10-Membered Lactones and Their Semisynthetic Derivatives"],"prefix":"10.3390","volume":"7","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-2391-0982","authenticated-orcid":false,"given":"Anna","family":"Dalinova","sequence":"first","affiliation":[{"name":"All-Russian Institute of Plant Protection, Saint Petersburg 196608, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5160-171X","authenticated-orcid":false,"given":"Anatoly","family":"Fedorov","sequence":"additional","affiliation":[{"name":"All-Russian Institute of Plant Protection, Saint Petersburg 196608, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7816-625X","authenticated-orcid":false,"given":"Vsevolod","family":"Dubovik","sequence":"additional","affiliation":[{"name":"All-Russian Institute of Plant Protection, Saint Petersburg 196608, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0966-1270","authenticated-orcid":false,"given":"Olga","family":"Voitsekhovskaja","sequence":"additional","affiliation":[{"name":"Komarov Botanical Institute, Russian Academy of Sciences, Saint Petersburg 197376, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Elena","family":"Tyutereva","sequence":"additional","affiliation":[{"name":"Komarov Botanical Institute, Russian Academy of Sciences, Saint Petersburg 197376, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Sergey","family":"Smirnov","sequence":"additional","affiliation":[{"name":"The Research Resources Center for Magnetic Resonance, St. Petersburg State University, Saint Petersburg 198504, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Dmitry","family":"Kochura","sequence":"additional","affiliation":[{"name":"Research Institute of Hygiene, Occupational Pathology and Human Ecology, Federal Medical Biological Agency, Saint Petersburg 188663, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Leonid","family":"Chisty","sequence":"additional","affiliation":[{"name":"Research Institute of Hygiene, Occupational Pathology and Human Ecology, Federal Medical Biological Agency, Saint Petersburg 188663, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Igor","family":"Senderskiy","sequence":"additional","affiliation":[{"name":"All-Russian Institute of Plant Protection, Saint Petersburg 196608, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0612-6996","authenticated-orcid":false,"given":"Alexander","family":"Berestetskiy","sequence":"additional","affiliation":[{"name":"All-Russian Institute of Plant Protection, Saint Petersburg 196608, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2021,10,3]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1231","DOI":"10.1021\/np300024u","article-title":"Natural Products as Sources for New Pesticides","volume":"75","author":"Cantrell","year":"2012","journal-title":"J. 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