{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"institution":[{"name":"bioRxiv"}],"indexed":{"date-parts":[[2026,8,1]],"date-time":"2026-08-01T00:53:37Z","timestamp":1785545617099,"version":"3.56.0"},"posted":{"date-parts":[[2026,7,30]]},"group-title":"Plant Biology","reference-count":87,"publisher":"openRxiv","license":[{"start":{"date-parts":[[2026,7,30]],"date-time":"2026-07-30T00:00:00Z","timestamp":1785369600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc-nd\/4.0\/"}],"funder":[{"name":"DFG","award":["DFG-FOR 3000\/1"],"award-info":[{"award-number":["DFG-FOR 3000\/1"]}]},{"name":"DFG","award":["P4 DA 1201\/10-1"],"award-info":[{"award-number":["P4 DA 1201\/10-1"]}]},{"name":"DFG","award":["415496540"],"award-info":[{"award-number":["415496540"]}]},{"name":"DFG-FZT 118","award":["202548816"],"award-info":[{"award-number":["202548816"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"accepted":{"date-parts":[[2026,7,30]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                <jats:p>\n                  Poisonous plants frequently deploy toxic metabolites in an organ- and ontogenetic-specific manner, yet the developmental dynamics of these plant specialised metabolites remain poorly understood. In the Solanaceae, steroidal glycosides (SGs), including steroidal glycoalkaloids (SGAs) and steroidal saponin glycosides (SSGs), are major defence metabolites with potent ecological and pharmacological activities. Here, we investigated how their metabolic profiles are reorganised during flower and fruit development in\n                  <jats:italic>Solanum dulcamara<\/jats:italic>\n                  using untargeted metabolomics and chemometric molecular networking.\n                <\/jats:p>\n                <jats:p>Non-metric multidimensional scaling (NMDS) using classified metabolite features recovered clear organ-specific and chemotype-specific segregation of samples, which was further strengthened when analyses were restricted to metabolomic features annotated as SGs. In flowers, orthogonal projections to latent structures discriminant analysis (OPLS-DA) separated both floral developmental stage and chemotype, demonstrating that developmental stage and inherited SG polymorphism represent independent axes of chemodiversity in flowers. Chemometric molecular networks showed pronounced diversification of hydroxycinnamate metabolism towards anthesis, including accumulation of caffeoylputrescine in flower buds and progressive acylation of spermidine conjugates across flower development. Upon anthesis, glycosylated hydroxycinnamates and flavonoids, and hydroxycinnamoyl-acylated flavonoid glycosides are accumulated. Fruit ripening followed a contrasting trajectory, in which SGAs were associated with unripe fruit pericarp, whereas ripe pericarp accumulated N- and O-acetylated SGA derivatives, oxidative deamination products, and predicted steroid degradation products, indicating stepwise detoxification of toxic steroidal glycosides during seed maturation.<\/jats:p>\n                <jats:p>\n                  Together, these findings show that the poisonous chemistry in\n                  <jats:italic>S. dulcamara<\/jats:italic>\n                  is highly dynamic and developmentally orchestrated. Flowers accumulate structurally complex metabolites toward anthesis, including conjugates of hydroxycinnamates, whereas fruits metabolise toxic SGAs into less toxic SGs during ripening, linking metabolic remodelling to reproduction and seed dispersal.\n                <\/jats:p>","DOI":"10.64898\/2026.07.29.741467","type":"posted-content","created":{"date-parts":[[2026,7,30]],"date-time":"2026-07-30T10:40:14Z","timestamp":1785408014000},"source":"Crossref","is-referenced-by-count":0,"title":["Bittersweet dynamics from flowers to fruits: chemometric molecular networking reveals metabolic changes towards reduced toxicity over ontogeny in above-ground\n                  <i>Solanum dulcamara<\/i>\n                  chemotypes"],"prefix":"10.64898","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-4896-299X","authenticated-orcid":false,"given":"Redouan Adam","family":"Anaia","sequence":"first","affiliation":[{"name":"Groningen Institute for Evolutionary Life Sciences, University of Groningen, Nijenborgh 7, 9747 AG, Groningen, The Netherlands"},{"name":"German Centre for Integrative Biodiversity Research (iDiv) Halle-Jena-Leipzig"},{"name":"Institute of Biodiversity, Ecology and Evolution (IBEE), Friedrich Schiller University, Jena, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6171-278X","authenticated-orcid":false,"given":"Ilaria","family":"Chiocchio","sequence":"additional","affiliation":[{"name":"Department of Pharmacy and Biotechnology, University of Bologna, Via Gobetti 87, 40129 Bologna, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2622-5446","authenticated-orcid":false,"given":"Nicole M.","family":"van Dam","sequence":"additional","affiliation":[{"name":"Leibniz Institute for Horticultural Sciences (IGZ), Gro\u00dfbeeren, Germany"},{"name":"Institute of Biodiversity, Ecology and Evolution (IBEE), Friedrich Schiller University, Jena, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"54368","reference":[{"key":"2026073115550987000_2026.07.29.741467v1.1","doi-asserted-by":"publisher","DOI":"10.1034\/j.1600-0706.2000.910301.x"},{"key":"2026073115550987000_2026.07.29.741467v1.2","doi-asserted-by":"publisher","DOI":"10.1016\/j.plantsci.2012.07.014"},{"key":"2026073115550987000_2026.07.29.741467v1.3","doi-asserted-by":"publisher","DOI":"10.1093\/pcp\/pcab080"},{"key":"2026073115550987000_2026.07.29.741467v1.4","doi-asserted-by":"publisher","DOI":"10.1111\/plb.13704"},{"key":"2026073115550987000_2026.07.29.741467v1.5","doi-asserted-by":"publisher","DOI":"10.1111\/plb.13704"},{"key":"2026073115550987000_2026.07.29.741467v1.6","doi-asserted-by":"crossref","unstructured":"Anaia, R. A. , & van Dam, N. (n.d.). Beetles, berries, bumble bees and Bittersweet: Do frequency-dependent selection processes contribute to the maintenance of steroidal glycoside diversity in Solanum dulcamara? 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