{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,14]],"date-time":"2026-10-14T22:38:39Z","timestamp":1792017519284,"version":"4.4.0"},"reference-count":72,"publisher":"Wiley","issue":"8","license":[{"start":{"date-parts":[[2025,5,30]],"date-time":"2025-05-30T00:00:00Z","timestamp":1748563200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100011033","name":"Agencia Estatal de Investigaci\u00f3n","doi-asserted-by":"publisher","award":["PID2020\u2010115747RB\u2010I00"],"award-info":[{"award-number":["PID2020\u2010115747RB\u2010I00"]}],"id":[{"id":"10.13039\/501100011033","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["analyticalsciencejournals.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Phytochemical Analysis"],"published-print":{"date-parts":[[2025,12]]},"abstract":"ABSTRACT<\/jats:title>\n \n Introduction<\/jats:title>\n Weeds are a major threat to crop productivity, competing for essential resources and often developing resistance to herbicides, which underscores the need for novel, sustainable control strategies. The valorization of agricultural and forestry underutilized byproducts, such as plant needles, presents a promising opportunity for developing eco\u2010friendly bioherbicides based on allelopathy.<\/jats:p>\n <\/jats:sec>\n \n Objectives<\/jats:title>\n \n This study investigates the phytotoxicity of\n \n Pinus pinea<\/jats:italic>\n <\/jats:styled-content>\n needle extracts and metabolites to evaluate their potential for controlling dicotyledonous weeds.\n <\/jats:p>\n <\/jats:sec>\n \n Material and Methods<\/jats:title>\n The chemical characterization of extracts and isolated compounds was performed via GC\u2013MS, NMR, and optical methods while phytotoxicity bioassays were carried out using the herbicides Pacifica Plus (Bayer CropScience) and pendimethalin, the active ingredient in Stone Aqua (Tokyo Chemical Industry), as positive controls.<\/jats:p>\n <\/jats:sec>\n \n Results<\/jats:title>\n \n The dichloromethane extract exhibited the highest phytotoxicity, significantly inhibiting\n \n Portulaca oleracea<\/jats:italic>\n <\/jats:styled-content>\n and\n \n Plantago lanceolata<\/jats:italic>\n <\/jats:styled-content>\n weeds. GC\u2013MS analysis revealed an array of aromatic compounds of interest for phytochemical research, and through bio\u2010guided purification, five lignans and the diterpenic acid (+)\u2010isocupressic acid were isolated. (+)\u2010Isocupressic acid showed the strongest phytotoxicity on\n \n P. oleracea<\/jats:italic>\n <\/jats:styled-content>\n , particularly on root growth (\u221283%\u2009\u00b1\u20094% at 1000\u2009\u03bcM), which could be correlated with structural moieties in its structure (fused\u2010ring scaffold with an exocyclic double bond, an exocyclic chain containing a double bond or hydroxyl group, and a carboxylic acid group), a number of H\u2010bond donors \u2264\u20092, and higher lipophilicity (Clog\n p<\/jats:italic>\n \u2009=\u20095.11). Some lignans displayed mild inhibitory or stimulatory effects on\n \n P. lanceolata<\/jats:italic>\n <\/jats:styled-content>\n .\n <\/jats:p>\n <\/jats:sec>\n \n Conclusion<\/jats:title>\n \n \n P. pinea<\/jats:italic>\n <\/jats:styled-content>\n needle extracts and metabolites have demonstrated potential as natural bioherbicides for weed management. Further research is prompted to explore large\u2010scale applicability, environmental safety through ecotoxicological studies, and optimized formulations to enhance their practical use in sustainable agriculture.\n <\/jats:p>\n <\/jats:sec>","DOI":"10.1002\/pca.3546","type":"journal-article","created":{"date-parts":[[2025,5,31]],"date-time":"2025-05-31T01:29:02Z","timestamp":1748654942000},"page":"2374-2384","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":8,"title":["Metabolite Screening From\n \n Pinus pinea<\/i>\n <\/scp>\n Needles Reveals (+)\u2010Isocupressic Acid as a Key Phytotoxin for Weed Management"],"prefix":"10.1002","volume":"36","author":[{"given":"Hajer","family":"Hlaili","sequence":"first","affiliation":[{"name":"Department of Chemical Sciences University of Naples Federico II Naples Italy"},{"name":"Faculty of Science of Bizerte University of Carthage Bizerte Tunisia"},{"name":"Laboratory of Forest Ecology, National Institute of Research in Rural Engineering, Water and Forests (INRGREF) University of Carthage Ariana Tunisia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jes\u00fas\u00a0G.","family":"Zorrilla","sequence":"additional","affiliation":[{"name":"Department of Chemical Sciences University of Naples Federico II Naples Italy"},{"name":"Allelopathy Group, Department of Organic Chemistry, Facultad de Ciencias, Institute of Biomolecules (INBIO) University of Cadiz Puerto Real Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Maria\u00a0Michela","family":"Salvatore","sequence":"additional","affiliation":[{"name":"Department of Veterinary Medicine and Animal Production University of Naples Federico II Naples Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mejda","family":"Abassi","sequence":"additional","affiliation":[{"name":"Laboratory of Forest Ecology, National Institute of Research in Rural Engineering, Water and Forests (INRGREF) University of Carthage Ariana Tunisia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Maria\u00a0Teresa","family":"Russo","sequence":"additional","affiliation":[{"name":"Department of Chemical Sciences University of Naples Federico II Naples Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Miriam\u00a0I.","family":"Mart\u00ednez\u2010Gonz\u00e1lez","sequence":"additional","affiliation":[{"name":"Department of Chemical Sciences University of Naples Federico II Naples Italy"},{"name":"Allelopathy Group, Department of Organic Chemistry, Facultad de Ciencias, Institute of Biomolecules (INBIO) University of Cadiz Puerto Real Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Marina","family":"DellaGreca","sequence":"additional","affiliation":[{"name":"Department of Chemical Sciences University of Naples Federico II Naples Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1551-4237","authenticated-orcid":false,"given":"Alessio","family":"Cimmino","sequence":"additional","affiliation":[{"name":"Department of Chemical Sciences University of Naples Federico II Naples Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Francisco\u00a0A.","family":"Mac\u00edas","sequence":"additional","affiliation":[{"name":"Allelopathy Group, Department of Organic Chemistry, Facultad de Ciencias, Institute of Biomolecules (INBIO) University of Cadiz Puerto Real Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Anna","family":"Andolfi","sequence":"additional","affiliation":[{"name":"Department of Chemical Sciences University of Naples Federico II Naples Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3616-9134","authenticated-orcid":false,"given":"Rosa\u00a0M.","family":"Varela","sequence":"additional","affiliation":[{"name":"Allelopathy Group, Department of Organic Chemistry, Facultad de Ciencias, Institute of Biomolecules (INBIO) University of Cadiz Puerto Real Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0609-8902","authenticated-orcid":false,"given":"Marco","family":"Masi","sequence":"additional","affiliation":[{"name":"Department of Chemical Sciences University of Naples Federico II Naples Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,5,30]]},"reference":[{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1186\/s40066-024-00470-8"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1007\/978-3-319-94232-2_3"},{"key":"e_1_2_7_4_1","unstructured":"SSRana MCRana \u201cPrinciples and Practices of Weed Management \u201d Department of Agronomy College of Agriculture CSK Himachal Pradesh Krishi Vishvavidyalaya Palampur; (2016) 138."},{"key":"e_1_2_7_5_1","first-page":"54","article-title":"Effects of Renewal Time, Taproot Cutting, Ploughing Practice, False Seedbed and Companion Crop on Docks (Rumex spp.) When Renewing Grassland","volume":"10","author":"Ringselle B.","year":"2019","journal-title":"EJA"},{"key":"e_1_2_7_6_1","doi-asserted-by":"publisher","DOI":"10.1146\/annurev-arplant-050213-035645"},{"key":"e_1_2_7_7_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.pbi.2016.06.009"},{"key":"e_1_2_7_8_1","doi-asserted-by":"publisher","DOI":"10.1146\/annurev-arplant-050312-120215"},{"key":"e_1_2_7_9_1","doi-asserted-by":"publisher","DOI":"10.3390\/agronomy10040566"},{"key":"e_1_2_7_10_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1365-3180.1995.tb02028.x"},{"key":"e_1_2_7_11_1","doi-asserted-by":"publisher","DOI":"10.1016\/B978-0-12-823674-1.00002-X"},{"key":"e_1_2_7_12_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules26113453"},{"key":"e_1_2_7_13_1","doi-asserted-by":"publisher","DOI":"10.1614\/0043-1745(2001)049[0290:ITBTMD]2.0.CO;2"},{"key":"e_1_2_7_14_1","doi-asserted-by":"publisher","DOI":"10.1614\/WT-D-14-00101.1"},{"key":"e_1_2_7_15_1","doi-asserted-by":"publisher","DOI":"10.1614\/WS-D-13-00109.1"},{"key":"e_1_2_7_16_1","doi-asserted-by":"publisher","DOI":"10.4236\/as.2018.912110"},{"key":"e_1_2_7_17_1","doi-asserted-by":"publisher","DOI":"10.1021\/jf403860b"},{"key":"e_1_2_7_18_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.scienta.2024.112963"},{"key":"e_1_2_7_19_1","doi-asserted-by":"publisher","DOI":"10.1002\/ps.7444"},{"key":"e_1_2_7_20_1","doi-asserted-by":"publisher","DOI":"10.3390\/agronomy14030486"},{"issue":"25","key":"e_1_2_7_21_1","first-page":"36136","article-title":"Valorization Potential of Pine Needle Waste Biomass: Recent Trends and Future Perspectives","volume":"31","author":"Gupta A.","year":"2024","journal-title":"ESPR"},{"key":"e_1_2_7_22_1","doi-asserted-by":"publisher","DOI":"10.1080\/10549811.2020.1798787"},{"key":"e_1_2_7_23_1","first-page":"9","article-title":"Influence of Stand and Tree Attributes and Silviculture on Cone and Seed Productions in Forests of Pinus pinea L. in Northern Tunisia","volume":"105","author":"Adili B.","year":"2013","journal-title":"Options M\u00e9diterran\u00e9ennes. S\u00e9rie A, S\u00e9minaires M\u00e9diterran\u00e9ens"},{"key":"e_1_2_7_24_1","unstructured":"A.Djaziri \u201c\u00c9tude Stationnelle du Pin Pignon en Italie \u201d I.N.R.F Tunisie: Vari\u00e9t\u00e9 Scientifique (1971):94\u201395p."},{"key":"e_1_2_7_25_1","doi-asserted-by":"publisher","DOI":"10.1007\/s10457-020-00523-4"},{"key":"e_1_2_7_26_1","doi-asserted-by":"publisher","DOI":"10.3390\/f8100367"},{"key":"e_1_2_7_27_1","doi-asserted-by":"publisher","DOI":"10.1007\/s12210-014-0335-8"},{"key":"e_1_2_7_28_1","first-page":"1059","article-title":"Carbon Stocks in a Scots Pine Afforestation Under Different Thinning Intensities Management","volume":"21","author":"Ruiz\u2010Peinado R.","year":"2016","journal-title":"Mitigation and Adaptation Strategies for Global Change"},{"key":"e_1_2_7_29_1","doi-asserted-by":"publisher","DOI":"10.1007\/s10457-016-9975-2"},{"key":"e_1_2_7_30_1","unstructured":"Food and Agriculture Organization of the United Nations (FAO) \u201cSave and Grow\u2014A Policymaker's Guide to the Sustainable Intensification of Smallholder Crop Production \u201d Rome FAO20111\u201315."},{"key":"e_1_2_7_31_1","doi-asserted-by":"publisher","DOI":"10.1017\/wsc.2024.13"},{"key":"e_1_2_7_32_1","doi-asserted-by":"publisher","DOI":"10.1038\/s43016-021-00322-9"},{"key":"e_1_2_7_33_1","doi-asserted-by":"publisher","DOI":"10.1007\/s10340-012-0419-0"},{"key":"e_1_2_7_34_1","doi-asserted-by":"publisher","DOI":"10.1007\/s10725-011-9652-4"},{"key":"e_1_2_7_35_1","first-page":"1","article-title":"Tolerance of Plantain (Plantago lanceolata) to Translocated Herbicides Wiped on Flower Stems","author":"Shrivastav N.","year":"2024","journal-title":"NZJAR"},{"key":"e_1_2_7_36_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1365-3180.2012.00910.x"},{"key":"e_1_2_7_37_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1744-7348.2009.00320.x"},{"key":"e_1_2_7_38_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.nucmedbio.2017.03.003"},{"key":"e_1_2_7_39_1","doi-asserted-by":"publisher","DOI":"10.1002\/cmdc.202000783"},{"key":"e_1_2_7_40_1","doi-asserted-by":"publisher","DOI":"10.1038\/srep42717"},{"key":"e_1_2_7_41_1","doi-asserted-by":"publisher","DOI":"10.1016\/0031-9422(90)85050-P"},{"key":"e_1_2_7_42_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-2006-931565"},{"key":"e_1_2_7_43_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00255a012"},{"key":"e_1_2_7_44_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-2004-815540"},{"key":"e_1_2_7_45_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-2006-961015"},{"key":"e_1_2_7_46_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0031-9422(00)83558-X"},{"key":"e_1_2_7_47_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2007.11.041"},{"key":"e_1_2_7_48_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-2004-827241"},{"key":"e_1_2_7_49_1","doi-asserted-by":"publisher","DOI":"10.1007\/s12272-009-1303-1"},{"key":"e_1_2_7_50_1","doi-asserted-by":"publisher","DOI":"10.1080\/10575639408043917"},{"key":"e_1_2_7_51_1","doi-asserted-by":"publisher","DOI":"10.1021\/jf00039a031"},{"key":"e_1_2_7_52_1","doi-asserted-by":"publisher","DOI":"10.1021\/np034033e"},{"key":"e_1_2_7_53_1","doi-asserted-by":"publisher","DOI":"10.1021\/jf048945d"},{"key":"e_1_2_7_54_1","doi-asserted-by":"publisher","DOI":"10.3390\/agronomy14102353"},{"key":"e_1_2_7_55_1","doi-asserted-by":"publisher","DOI":"10.1080\/14786419.2021.1897810"},{"key":"e_1_2_7_56_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules24091724"},{"key":"e_1_2_7_57_1","doi-asserted-by":"publisher","DOI":"10.3390\/plants9010102"},{"key":"e_1_2_7_58_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.chemosphere.2017.07.002"},{"key":"e_1_2_7_59_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.scienta.2016.12.004"},{"key":"e_1_2_7_60_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11101-013-9311-7"},{"key":"e_1_2_7_61_1","doi-asserted-by":"publisher","DOI":"10.1023\/B:PHYT.0000045487.02836.32"},{"key":"e_1_2_7_62_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.phrs.2019.104284"},{"key":"e_1_2_7_63_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bse.2006.12.009"},{"key":"e_1_2_7_64_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jafc.1c07806"},{"key":"e_1_2_7_65_1","doi-asserted-by":"publisher","DOI":"10.3390\/plants12040697"},{"key":"e_1_2_7_66_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.chemosphere.2012.02.058"},{"key":"e_1_2_7_67_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jafc.3c06901"},{"key":"e_1_2_7_68_1","doi-asserted-by":"publisher","DOI":"10.1002\/minf.201100020"},{"key":"e_1_2_7_69_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.phytochem.2024.113977"},{"key":"e_1_2_7_70_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.toxicon.2024.107769"},{"key":"e_1_2_7_71_1","doi-asserted-by":"publisher","DOI":"10.1155\/2012\/190107"},{"key":"e_1_2_7_72_1","doi-asserted-by":"publisher","DOI":"10.3390\/toxins15060405"},{"key":"e_1_2_7_73_1","doi-asserted-by":"publisher","DOI":"10.1021\/np980064b"}],"container-title":["Phytochemical Analysis"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/analyticalsciencejournals.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/pca.3546","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,12,2]],"date-time":"2025-12-02T10:10:41Z","timestamp":1764670241000},"score":1,"resource":{"primary":{"URL":"https:\/\/analyticalsciencejournals.onlinelibrary.wiley.com\/doi\/10.1002\/pca.3546"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,5,30]]},"references-count":72,"journal-issue":{"issue":"8","published-print":{"date-parts":[[2025,12]]}},"alternative-id":["10.1002\/pca.3546"],"URL":"https:\/\/doi.org\/10.1002\/pca.3546","archive":["Portico"],"relation":{},"ISSN":["0958-0344","1099-1565"],"issn-type":[{"value":"0958-0344","type":"print"},{"value":"1099-1565","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,5,30]]},"assertion":[{"value":"2025-03-19","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-05-22","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-05-30","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}