{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,18]],"date-time":"2026-08-18T04:58:39Z","timestamp":1787029119395,"version":"build-2736575974"},"reference-count":51,"publisher":"MDPI AG","issue":"15","license":[{"start":{"date-parts":[[2024,7,27]],"date-time":"2024-07-27T00:00:00Z","timestamp":1722038400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["81960639"],"award-info":[{"award-number":["81960639"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["202205AC160084"],"award-info":[{"award-number":["202205AC160084"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["202401BC070018"],"award-info":[{"award-number":["202401BC070018"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["202402AN360010"],"award-info":[{"award-number":["202402AN360010"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Project of Yunnan Provincial Department of Science and Technology","award":["81960639"],"award-info":[{"award-number":["81960639"]}]},{"name":"Project of Yunnan Provincial Department of Science and Technology","award":["202205AC160084"],"award-info":[{"award-number":["202205AC160084"]}]},{"name":"Project of Yunnan Provincial Department of Science and Technology","award":["202401BC070018"],"award-info":[{"award-number":["202401BC070018"]}]},{"name":"Project of Yunnan Provincial Department of Science and Technology","award":["202402AN360010"],"award-info":[{"award-number":["202402AN360010"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Human DNA topoisomerase I (Topo I) is an essential enzyme in regulating DNA supercoiling during transcription and replication, and it is an important therapeutic target for anti-tumor agents. Bidens pilosa L. is a medicinal herb that is used as a folk medicine for cancers in China. A new flavonoid (1) and a new polyacetylene (20), along with eighteen flavonoids (2\u201319) and nine polyacetylenes (21\u201329), were isolated and identified from the methanol extract of the whole plant of B. pilosa, and some of the compounds (4, 5, 6 and 7) exhibited potent cytotoxicity against a panel of five human cancer cell lines. The DNA relaxation assay revealed that some flavonoids and polyacetylenes exerted inhibitory activities on human DNA Topo I, among them compounds 1, 2, 5, 6, 7, 8, 15, 19, 20, 22, and 24 were the most active ones, with IC50 values of 393.5, 328.98, 145.57, 239.27, 224.38, 189.84, 89.91, 47.5, 301.32, 178.03, and 218.27 \u03bcM, respectively. The structure\u2013activity analysis of flavonoids was performed according to the results from the Topo I inhibition assay. The DNA content analysis revealed that 5, 6, and 7 potently arrested cell cycle at the G1\/S and G2\/M phases in human colon cancer cell DLD-1 depending on the concentration of the inhibitors. The levels of protein expression related to the G1\/S and G2\/M cell cycle checkpoints were in accordance with the results from the DNA content analysis. These findings suggest that flavonoids are one of the key active ingredients accounting for the anti-tumor effect of B. pilosa.<\/jats:p>","DOI":"10.3390\/molecules29153547","type":"journal-article","created":{"date-parts":[[2024,7,29]],"date-time":"2024-07-29T09:50:05Z","timestamp":1722246605000},"page":"3547","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":10,"title":["Inhibition of DNA Topoisomerase \u0399 by Flavonoids and Polyacetylenes Isolated from Bidens pilosa L."],"prefix":"10.3390","volume":"29","author":[{"given":"Guiyuan","family":"Zeng","sequence":"first","affiliation":[{"name":"Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission and Ministry of Education, Yunnan Minzu University, Kunming 650504, China"},{"name":"Yunnan Key Laboratory of Chiral Functional Substance Research and Application, Yunnan Minzu University, Kunming 650504, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yinyue","family":"Wang","sequence":"additional","affiliation":[{"name":"Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission and Ministry of Education, Yunnan Minzu University, Kunming 650504, China"},{"name":"Yunnan Key Laboratory of Chiral Functional Substance Research and Application, Yunnan Minzu University, Kunming 650504, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Meihua","family":"Zhu","sequence":"additional","affiliation":[{"name":"Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission and Ministry of Education, Yunnan Minzu University, Kunming 650504, China"},{"name":"Yunnan Key Laboratory of Chiral Functional Substance Research and Application, Yunnan Minzu University, Kunming 650504, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jumei","family":"Yi","sequence":"additional","affiliation":[{"name":"Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission and Ministry of Education, Yunnan Minzu University, Kunming 650504, China"},{"name":"Yunnan Key Laboratory of Chiral Functional Substance Research and Application, Yunnan Minzu University, Kunming 650504, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Junjie","family":"Ma","sequence":"additional","affiliation":[{"name":"Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission and Ministry of Education, Yunnan Minzu University, Kunming 650504, China"},{"name":"Yunnan Key Laboratory of Chiral Functional Substance Research and Application, Yunnan Minzu University, Kunming 650504, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bijuan","family":"Yang","sequence":"additional","affiliation":[{"name":"Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission and Ministry of Education, Yunnan Minzu University, Kunming 650504, China"},{"name":"Yunnan Key Laboratory of Chiral Functional Substance Research and Application, Yunnan Minzu University, Kunming 650504, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Weiqing","family":"Sun","sequence":"additional","affiliation":[{"name":"Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission and Ministry of Education, Yunnan Minzu University, Kunming 650504, China"},{"name":"Yunnan Key Laboratory of Chiral Functional Substance Research and Application, Yunnan Minzu University, Kunming 650504, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Fang","family":"Dai","sequence":"additional","affiliation":[{"name":"School of Chemistry and Environmental Engineering, Qujing Normal University, Qujing 655011, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Junlin","family":"Yin","sequence":"additional","affiliation":[{"name":"Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission and Ministry of Education, Yunnan Minzu University, Kunming 650504, China"},{"name":"Yunnan Key Laboratory of Chiral Functional Substance Research and Application, Yunnan Minzu University, Kunming 650504, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Guangzhi","family":"Zeng","sequence":"additional","affiliation":[{"name":"Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission and Ministry of Education, Yunnan Minzu University, Kunming 650504, China"},{"name":"Yunnan Key Laboratory of Chiral Functional Substance Research and Application, Yunnan Minzu University, Kunming 650504, China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2024,7,27]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1070","DOI":"10.3390\/molecules16021070","article-title":"Compilation of secondary metabolites from Bidens pilosa L.","volume":"16","author":"Silva","year":"2011","journal-title":"Molecules"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"463","DOI":"10.1016\/j.phymed.2009.08.001","article-title":"Anti-inflammatory activity of a HPLC-fingerprinted aqueous infusion of aerial part of Bidens tripartita L.","volume":"17","author":"Pozharitskaya","year":"2010","journal-title":"Phytomedicine"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"893","DOI":"10.1055\/s-0029-1240814","article-title":"Polyacetylenes and flavonoids from the aerial parts of Bidens pilosa","volume":"76","author":"Wang","year":"2010","journal-title":"Planta Med."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"17","DOI":"10.1007\/s11418-012-0639-x","article-title":"Investigation of the extracts from Bidens pilosa Linn. var. radiata Sch. Bip. for antioxidant activities and cytotoxicity against human tumor cells","volume":"67","author":"Wu","year":"2013","journal-title":"J. Nat. Med."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"624","DOI":"10.1055\/s-0029-1185377","article-title":"Isolation and identification of a potent antimalarial and antibacterial polyacetylene from Bidens pilosa","volume":"75","author":"Tobinaga","year":"2009","journal-title":"Planta Med."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"539","DOI":"10.1016\/j.jep.2008.01.010","article-title":"Protective effects of total flavonoids of Bidens pilosa L. (TFB) on animal liver injury and liver fibrosis","volume":"116","author":"Yuan","year":"2008","journal-title":"J. Ethnopharmacol."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"59","DOI":"10.1055\/s-0028-1088362","article-title":"A promising anticancer and antimalarial component from the leaves of Bidens pilosa","volume":"75","author":"Kumari","year":"2009","journal-title":"Planta Med."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"1246","DOI":"10.1016\/j.phytochem.2009.07.011","article-title":"Anti-diabetic properties of three common Bidens pilosa variants in Taiwan","volume":"70","author":"Chien","year":"2009","journal-title":"Phytochemistry"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"373","DOI":"10.1042\/BCJ20160583","article-title":"Topoisomerases as anticancer targets","volume":"475","author":"Delgado","year":"2018","journal-title":"Biochem. J."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"129","DOI":"10.1016\/j.ejmech.2019.03.034","article-title":"A comprehensive review of topoisomerase inhibitors as anticancer agents in the past decade","volume":"171","author":"Liang","year":"2019","journal-title":"Eur. J. Med. Chem."},{"key":"ref_11","doi-asserted-by":"crossref","unstructured":"Gu, L., Hickey, R.J., and Malkas, L.H. (2023). Therapeutic Targeting of DNA Replication Stress in Cancer. Genes, 14.","DOI":"10.3390\/genes14071346"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"1103","DOI":"10.2174\/1389203721666200918152511","article-title":"Natural Products as Anti-Cancerous Therapeutic Molecules Targeted towards Topoisomerases","volume":"21","author":"Singh","year":"2020","journal-title":"Curr. Protein Pept. Sci."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"75","DOI":"10.2174\/1389202917666160808125213","article-title":"Natural Compounds as Anticancer Agents Targeting DNA Topoisomerases","volume":"18","author":"Jain","year":"2017","journal-title":"Curr. Genom."},{"key":"ref_14","first-page":"627","article-title":"Chemical constituents of the whole plant of Bidens pilosa L.","volume":"31","author":"Zhao","year":"2022","journal-title":"J. Yunnan Minzu Univ. Nat. Sci. Ed."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"218","DOI":"10.1016\/0031-9422(92)80140-A","article-title":"Chalcone glycosides from Bidens campylotheca","volume":"32","author":"Redl","year":"1992","journal-title":"Phytochemistry"},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"3108","DOI":"10.1055\/s-0032-1316784","article-title":"Synthesis and Absolute Configuration of the 7-Phenylhepta-4,6-diyne-1,2-diol Isolated from Bidens pilosa","volume":"44","author":"Cui","year":"2012","journal-title":"Synthesis"},{"key":"ref_17","first-page":"489","article-title":"A new polyacetylene and a new isonicotinic acid glucoside from Bidens parviflora Willd","volume":"55","author":"Li","year":"2020","journal-title":"Acta Pharm. Sin."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"518","DOI":"10.5246\/jcps.2011.05.066","article-title":"Flavonoids from the herb of Bidens pilosa L.","volume":"20","author":"Tian","year":"2011","journal-title":"J. Chin. Pharm. Sci."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"13","DOI":"10.3724\/SP.J.1009.2012.00013","article-title":"A new carbamate with cytotoxic activity from the aerial parts of Siegesbeckia pubecens","volume":"10","author":"Liu","year":"2012","journal-title":"Chin. J. Nat. Med."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"976","DOI":"10.1515\/znc-2002-11-1203","article-title":"Sesquiterpenes and flavonoid aglycones from a Hungarian taxon of the Achillea millefolium group","volume":"57","author":"Glasl","year":"2002","journal-title":"Z. Naturforsch C J. Biosci."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"165","DOI":"10.3184\/030823409X416929","article-title":"A new flavonol glycoside from Tridax procumbens Linn","volume":"2009","author":"Yuan","year":"2009","journal-title":"J. Chem. Res."},{"key":"ref_22","doi-asserted-by":"crossref","unstructured":"Lee, H.J., Sim, M.O., Woo, K.W., Jeong, D.E., Jung, H.K., An, B., and Cho, H.W. (2019). Antioxidant and Antimelanogenic Activities of Compounds Isolated from the Aerial Parts of Achillea alpina L.. Chem. Biodivers., 16.","DOI":"10.1002\/cbdv.201900033"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"257","DOI":"10.3724\/SP.J.1009.2010.00257","article-title":"Flavonoids from the Aerial Parts of Inula japonica","volume":"8","author":"Qin","year":"2010","journal-title":"Chin. J. Nat. Med."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"6357","DOI":"10.3390\/molecules15096357","article-title":"Two new flavones from Tridax procumbens Linn","volume":"15","author":"Xu","year":"2010","journal-title":"Molecules"},{"key":"ref_25","first-page":"283","article-title":"Studies on Chemical Constituents of Bidens bipinnata","volume":"25","author":"Yang","year":"2009","journal-title":"Pharm. J. Chin. People\u2019s Lib. Army"},{"key":"ref_26","first-page":"139","article-title":"Simultaneous quantitative analysis of flavonoids isolated from the leaves of Diospyros kaki","volume":"51","author":"Kim","year":"2020","journal-title":"Korean J. Pharmacogn."},{"key":"ref_27","first-page":"517","article-title":"Isolation, characterization of flavonoids from Seriphidium oliverianum and their antioxidant and anti-urease activities","volume":"36","author":"Shafiq","year":"2014","journal-title":"J. Chem. Soc. Pak."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"1770","DOI":"10.1080\/14786419.2013.778848","article-title":"New methylated flavonol glucosides from Fumana montana Pomel","volume":"27","author":"Laraoui","year":"2013","journal-title":"Nat. Prod. Res."},{"key":"ref_29","first-page":"1838","article-title":"Chemical constituents from Bidens bipinnata","volume":"39","author":"Wang","year":"2014","journal-title":"China J. Chin. Mater. Med."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"1931","DOI":"10.3390\/molecules13081931","article-title":"Flavonoids and a new polyacetylene from Bidens parviflora Willd","volume":"13","author":"Li","year":"2008","journal-title":"Molecules"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"963","DOI":"10.1080\/10286020.2021.1998010","article-title":"A new dihydroflavone and a new polyacetylene glucoside from Bidens parviflora","volume":"24","author":"Cai","year":"2022","journal-title":"J. Asian Nat. Prod. Res."},{"key":"ref_32","first-page":"1040","article-title":"Isolation and Identification of Phenols Compounds in Aurantii Fructus Immaturus","volume":"31","author":"Deng","year":"2020","journal-title":"China Pharm."},{"key":"ref_33","first-page":"2498","article-title":"Studies on flavonoids from Bidens pilosa","volume":"44","author":"Li","year":"2023","journal-title":"Chin. Tradit. Herb. Drugs"},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"557","DOI":"10.3987\/COM-03-S31","article-title":"A New Aurone Glucoside and a New Chalcone Glucoside from Bidens bipinnata Linne","volume":"61","author":"Okuyama","year":"2003","journal-title":"Heterocycles"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"1131","DOI":"10.1002\/jccs.200000152","article-title":"The Low Polar Constituents from Bidens pilosa L. var. Minor (Blume) Sherff","volume":"47","author":"Chang","year":"2013","journal-title":"J. Chin. Chem. Soc."},{"key":"ref_36","first-page":"1121","article-title":"Nematicidal Activities of Acetylene Compounds from Coreopsis lanceolata L.","volume":"63","author":"Kimura","year":"2015","journal-title":"Z. Naturforschung C"},{"key":"ref_37","first-page":"216","article-title":"Studies on Isolation of Polyacetylenes from Bidens pilosa var.radiata and their biological activities","volume":"29","author":"Xie","year":"2021","journal-title":"J. Trop. Subtrop. Bot."},{"key":"ref_38","first-page":"121","article-title":"A New Chalcone Glycoside from Bidens pilosa","volume":"26","author":"Zhao","year":"2004","journal-title":"Acta Bot. Yunnanica"},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"266","DOI":"10.1055\/s-2006-961450","article-title":"Acetylenic glucosides from Microglossa pyrifolia","volume":"58","author":"Kehrbaum","year":"1992","journal-title":"Planta Med."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"532","DOI":"10.1016\/j.jep.2006.10.007","article-title":"Cytopiloyne, a novel polyacetylenic glucoside from Bidens pilosa, functions as a T helper cell modulator","volume":"110","author":"Chiang","year":"2007","journal-title":"J. Ethnopharmacol."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"6515","DOI":"10.1016\/j.bmc.2014.06.051","article-title":"Thiophenes, polyacetylenes and terpenes from the aerial parts of Eclipata prostrate","volume":"22","author":"Xi","year":"2014","journal-title":"Bioorganic Med. Chem."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"113319","DOI":"10.1016\/j.phytochem.2022.113319","article-title":"Polyacetylenes from the roots of Cirsium japonicum var. ussuriense","volume":"202","author":"Lee","year":"2022","journal-title":"Phytochemistry"},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"115731","DOI":"10.1016\/j.ejmech.2023.115731","article-title":"Cantharidin analogue alleviates dextran sulfate sodium-induced colitis in mice by inhibiting the activation of NF-\u03baB signaling","volume":"260","author":"Wu","year":"2023","journal-title":"Eur. J. Med. Chem."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"275","DOI":"10.2174\/1389203718666170111114442","article-title":"Natural Product Inhibitors of Topoisomerases: Review and Docking Study","volume":"19","author":"Scotti","year":"2018","journal-title":"Curr. Protein Pept. Sci."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"313","DOI":"10.1007\/BF02977611","article-title":"Topoisomerase I inhibition and cytotoxicity of licochalcones A and E from Glycyrrhiza inflata","volume":"30","author":"Yoon","year":"2007","journal-title":"Arch. Pharm. Res."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"653","DOI":"10.1042\/bj20020098","article-title":"Luteolin, an emerging anti-cancer flavonoid, poisons eukaryotic DNA topoisomerase I","volume":"366","author":"Chowdhury","year":"2002","journal-title":"Biochem. J."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"217","DOI":"10.1021\/np50116a009","article-title":"Flavonoids as DNA topoisomerase antagonists and poisons: Structure-activity relationships","volume":"58","author":"Constantinou","year":"1995","journal-title":"J. Nat. Prod."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"3787","DOI":"10.1007\/s00204-021-03162-5","article-title":"Topoisomerase poisoning by the flavonoid nevadensin triggers DNA damage and apoptosis in human colon carcinoma HT29 cells","volume":"95","author":"Alfke","year":"2021","journal-title":"Arch. Toxicol."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"1389","DOI":"10.1038\/s41388-019-1079-9","article-title":"Comparison of the different mechanisms of cytotoxicity induced by checkpoint kinase I inhibitors when used as single agents or in combination with DNA damage","volume":"39","author":"Warren","year":"2020","journal-title":"Oncogene"},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"182","DOI":"10.1016\/j.plantsci.2015.09.016","article-title":"Cell cycle stage-specific differential expression of topoisomerase I in tobacco BY-2 cells and its ectopic overexpression and knockdown unravels its crucial role in plant morphogenesis and development","volume":"240","author":"Singh","year":"2015","journal-title":"Plant Sci."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"295","DOI":"10.1146\/annurev.pharmtox.39.1.295","article-title":"Cyclins and cell cycle checkpoints","volume":"39","author":"Johnson","year":"1999","journal-title":"Annu. Rev. Pharmacol. Toxicol."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/29\/15\/3547\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T15:25:09Z","timestamp":1760109909000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/29\/15\/3547"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,7,27]]},"references-count":51,"journal-issue":{"issue":"15","published-online":{"date-parts":[[2024,8]]}},"alternative-id":["molecules29153547"],"URL":"https:\/\/doi.org\/10.3390\/molecules29153547","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,7,27]]}}}