{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,26]],"date-time":"2026-10-26T12:30:35Z","timestamp":1793017835236,"version":"4.5.0"},"reference-count":52,"publisher":"MDPI AG","issue":"14","license":[{"start":{"date-parts":[[2025,7,14]],"date-time":"2025-07-14T00:00:00Z","timestamp":1752451200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"German Academic Exchange Service (DAAD)","award":["57561808"],"award-info":[{"award-number":["57561808"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Malaria continues to pose a significant global health burden, driving the search for novel antimalarial agents to address emerging drug resistance. This study evaluated the antiplasmodial potential of Ziziphus mauritiana Lam. (Rhamnaceae) roots through an integrated phytochemical and pharmacological approach. The ethanol extract, along with its derived fractions, demonstrated potent in vitro activity against the chloroquine-sensitive Plasmodium falciparum strain 3D7 (Pf3D7), with the ethyl acetate-soluble (IC50 = 11.35 \u00b5g\/mL) and alkaloid-rich (IC50 = 4.75 \u00b5g\/mL) fractions showing particularly strong inhibition. UHPLC-DAD-ESI-QTOF-MS\/MS-based molecular networking enabled the identification of thirty-two secondary metabolites (1\u201332), comprising twenty-five cyclopeptide alkaloids (CPAs), five of which had not yet been described (11, 20, 22, 23, 25), and seven known triterpenoids. Bioactivity-guided isolation yielded thirteen purified compounds (5, 6, 14, 26\u201330, 32\u201336), with betulinic acid (30; IC50 = 19.0 \u00b5M) and zizyberenalic acid (32; IC50 = 20.45 \u00b5M) exhibiting the most potent antiplasmodial effects. Computational ADMET analysis identified mauritine F (4), hemisine A (10), and nummularine R (21) as particularly promising lead compounds, demonstrating favourable pharmacokinetic properties, low toxicity profiles, and predicted activity against both family A G protein-coupled receptors and evolutionarily distinct Plasmodium protein kinases. Quantitative analysis revealed exceptionally high concentrations of key bioactive constituents, notably zizyberenalic acid (24.3 mg\/g) in the root extracts. These findings provide robust scientific validation for the traditional use of Z. mauritiana in malaria treatment while identifying specific cyclopeptide alkaloids and triterpenoids as valuable scaffolds for antimalarial drug development. The study highlights the effectiveness of combining advanced metabolomics, bioassay-guided fractionation, and computational pharmacology in natural product-based drug discovery against resistant malaria strains.<\/jats:p>","DOI":"10.3390\/molecules30142958","type":"journal-article","created":{"date-parts":[[2025,7,14]],"date-time":"2025-07-14T10:55:41Z","timestamp":1752490541000},"page":"2958","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":6,"title":["Bioactive Cyclopeptide Alkaloids and Ceanothane Triterpenoids from Ziziphus mauritiana Roots: Antiplasmodial Activity, UHPLC-MS\/MS Molecular Networking, ADMET Profiling, and Target Prediction"],"prefix":"10.3390","volume":"30","author":[{"ORCID":"https:\/\/orcid.org\/0009-0004-3665-8370","authenticated-orcid":false,"given":"Sylvestre Saidou","family":"Tsila","sequence":"first","affiliation":[{"name":"Department of Organic Chemistry, Faculty of Science, University of Yaound\u00e9 I, Yaound\u00e9 P.O. Box 812, Cameroon"},{"name":"Department of Chemistry, Higher Teacher Training College, University of Yaound\u00e9 I, Yaound\u00e9 P.O. Box 47, Cameroon"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9910-2319","authenticated-orcid":false,"given":"Mc Jesus","family":"Kinyok","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Higher Teacher Training College, University of Yaound\u00e9 I, Yaound\u00e9 P.O. Box 47, Cameroon"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Joseph Eric Mbasso","family":"Tameko","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Higher Teacher Training College, University of Yaound\u00e9 I, Yaound\u00e9 P.O. Box 47, Cameroon"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7220-3358","authenticated-orcid":false,"given":"Bel Youssouf G.","family":"Mountessou","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Higher Teacher Training College, University of Yaound\u00e9 I, Yaound\u00e9 P.O. Box 47, Cameroon"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kevine Johanne Jumeta","family":"Dongmo","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry, Faculty of Science, University of Yaound\u00e9 I, Yaound\u00e9 P.O. Box 812, Cameroon"},{"name":"Department of Chemistry, Higher Teacher Training College, University of Yaound\u00e9 I, Yaound\u00e9 P.O. Box 47, Cameroon"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0004-6494-7583","authenticated-orcid":false,"given":"Jean Koffi","family":"Garba","sequence":"additional","affiliation":[{"name":"Department of Basic Science Education, National Advanced School of Maritime and Ocean Science and Technology, University of Ebolowa, Kribi P.O. Box 292, Cameroon"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6160-724X","authenticated-orcid":false,"given":"Noella Molisa","family":"Efange","sequence":"additional","affiliation":[{"name":"Department of Biochemistry and Molecular Biology, Faculty of Science, The University of Buea, Buea P.O. Box 63, Cameroon"},{"name":"Malaria Research Service, Centre Pasteur du Cameroun, Yaound\u00e9 P.O. Box 1274, Cameroon"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7717-4832","authenticated-orcid":false,"given":"Lawrence","family":"Ayong","sequence":"additional","affiliation":[{"name":"Malaria Research Service, Centre Pasteur du Cameroun, Yaound\u00e9 P.O. Box 1274, Cameroon"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9311-9945","authenticated-orcid":false,"given":"Yannick St\u00e9phane Fotsing","family":"Fongang","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Higher Teachers\u2019 Training College, The University of Maroua, Maroua P.O. Box 55, Cameroon"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8483-6080","authenticated-orcid":false,"given":"Jean Jules Kezetas","family":"Bankeu","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Higher Teacher Training College, University of Yaound\u00e9 I, Yaound\u00e9 P.O. Box 47, Cameroon"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0309-2655","authenticated-orcid":false,"given":"Norbert","family":"Sewald","sequence":"additional","affiliation":[{"name":"Organic and Bioorganic Chemistry, Faculty of Chemistry, Bielefeld University, D-33501 Bielefeld, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9095-6660","authenticated-orcid":false,"given":"Bruno Ndjakou","family":"Lenta","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Higher Teacher Training College, University of Yaound\u00e9 I, Yaound\u00e9 P.O. Box 47, Cameroon"},{"name":"Organic and Bioorganic Chemistry, Faculty of Chemistry, Bielefeld University, D-33501 Bielefeld, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2025,7,14]]},"reference":[{"key":"ref_1","unstructured":"(2025, February 14). World Malaria Report 2024. Available online: https:\/\/www.who.int\/teams\/global-malaria-programme\/reports\/world-malaria-report-2024."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"985","DOI":"10.1093\/infdis\/jiaa687","article-title":"Changing Prevalence of Potential Mediators of Aminoquinoline, Antifolate, and Artemisinin Resistance Across Uganda","volume":"223","author":"Asua","year":"2021","journal-title":"J. Infect. Dis."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"1923","DOI":"10.1021\/acsinfecdis.0c00900","article-title":"A proteasome mutation sensitizes P. falciparum Cam3.II K13C580Y Parasites to DHA and OZ439","volume":"7","author":"Rosenthal","year":"2021","journal-title":"ACS Infect. Dis."},{"key":"ref_4","first-page":"274","article-title":"Ziziphus mauritiana: An in-depth Review of its Medicinal Attributes and Pharmacological Activities","volume":"2","author":"Jha","year":"2024","journal-title":"Intell. Pharm."},{"key":"ref_5","first-page":"111","article-title":"Antiplasmodial effects of the aqueous ethanolic seed extract of Ziziphus mauritiana against Plasmodium berghei in Swiss albino mice","volume":"4","author":"Mishra","year":"2014","journal-title":"Int. J. Pharmacol. Res."},{"key":"ref_6","first-page":"107","article-title":"Review on ethnomedicinal uses, Pharmacological activity and phytochemical constituents of Ziziphus mauritiana & jujuba Lam., non Mill)","volume":"2","author":"Goyal","year":"2012","journal-title":"J. Complement. Med. Drug Discov."},{"key":"ref_7","unstructured":"Orwa, C., Mutua, A., Kindt, R., Jamnadass, R., and Anthony, S. (2025, May 21). Agroforestree Database: A Tree Reference and Selection Guide Version 4.0. Available online: https:\/\/apps.worldagroforestry.org\/treedb\/AFTPDFS\/Ziziphus_mauritiana.pdf."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"63","DOI":"10.1002\/ptr.6769","article-title":"A panoramic view on phytochemical, nutritional, and therapeutic attributes of Ziziphus mauritiana Lam.: A comprehensive review","volume":"35","author":"Prakash","year":"2021","journal-title":"Phytother. Res."},{"key":"ref_9","first-page":"106","article-title":"Triterpenes from the root of the Ziziphus mauritiana","volume":"2","author":"Panseeta","year":"2010","journal-title":"JST"},{"key":"ref_10","doi-asserted-by":"crossref","unstructured":"Nilofar, N., Sinan, K.I., Dall\u2019Acqua, S., Sut, S., Uba, A.I., Etienne, O.K., Ferrante, C., Ahmad, J., and Zengin, G. (2024). Ziziphus mauritiana Lam. Bark and Leaves: Extraction, Phytochemical Composition, In Vitro Bioassays and In Silico Studies. Plants, 13.","DOI":"10.3390\/plants13162195"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"105144","DOI":"10.1016\/j.yrtph.2022.105144","article-title":"Standardization, in-silico and in-vivo safety assessment of methanol extract of Ziziphus mauritiana Lam leaves","volume":"131","author":"Ramar","year":"2022","journal-title":"Regul. Toxicol. Pharmacol."},{"key":"ref_12","doi-asserted-by":"crossref","unstructured":"Khanam, A., Ijaz Hussain, A., Mohammed, E.H., Nahar, L., and Rathore, H.A. (2025). Phenolic Profile of Seedless Ziziphus mauritiana Fruits and Leaves Extracts with In Vivo Antioxidant and Anti-Inflammatory Activities: Influence on Pro-Inflammatory Mediators. Chem. Biodivers., 22.","DOI":"10.1002\/cbdv.202401728"},{"key":"ref_13","doi-asserted-by":"crossref","unstructured":"Guo, S., Duan, J.-A., Li, Y., Wang, R., Yan, H., Qian, D., Tang, Y., and Su, S. (2017). Comparison of the Bioactive Components in Two Seeds of Ziziphus Species by Different Analytical Approaches Combined with Chemometrics. Front. Pharmacol., 8.","DOI":"10.3389\/fphar.2017.00609"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"11","DOI":"10.32996\/ijbpcs.2022.4.2.2","article-title":"Identification of Chemical Compounds in Ziziphus mauritiana Fruit Juice by GC-MS and LC-MS\/MS Analysis","volume":"4","author":"Soraya","year":"2022","journal-title":"Int. J. Biol. Phys. Chem. Stud."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"909","DOI":"10.1016\/j.phytochem.2011.03.003","article-title":"Antiplasmodial and antimycobacterial cyclopeptide alkaloids from the root of Ziziphus mauritiana","volume":"72","author":"Panseeta","year":"2011","journal-title":"Phytochemistry"},{"key":"ref_16","first-page":"1715","article-title":"Anticancer activity of Ziziphus mauritiana roots against human breast cancer cell line","volume":"32","author":"Batool","year":"2019","journal-title":"Pak. J. Pharm. Sci."},{"key":"ref_17","doi-asserted-by":"crossref","unstructured":"Shady, N.H., Soltane, R., Maher, S.A., Saber, E.A., Elrehany, M.A., Mostafa, Y.A., Sayed, A.M., and Abdelmohsen, U.R. (2022). Wound Healing and Antioxidant Capabilities of Zizyphus mauritiana Fruits: In-Vitro, In-Vivo, and Molecular Modeling Study. Plants, 11.","DOI":"10.3390\/plants11111392"},{"key":"ref_18","first-page":"1934578X2110549","article-title":"UHPLC-ESI-Orbitrap-HR-MS Analysis of Cyclopeptide Alkaloids from Ziziphus joazeiro","volume":"16","author":"Laub","year":"2021","journal-title":"Nat. Prod. Commun."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"45","DOI":"10.5478\/MSL.2016.7.2.45","article-title":"UHPLC-ESI-qTOF-MS analysis of cyclopeptide alkaloids in the seeds of Ziziphus jujuba var. spinosa","volume":"7","author":"Kang","year":"2016","journal-title":"Mass Spectrom. Lett."},{"key":"ref_20","doi-asserted-by":"crossref","unstructured":"Collett, L.A., Davies-Coleman, M.T., Gournelis, D.C., Laskaris, G.G., Rivett, D.E.A., and Verpoorte, R. (1998). Fortschritte der Chemie Organischer Naturstoffe\/Progress in the Chemistry of Organic Natural Products, Springer Chemistry.","DOI":"10.1007\/978-3-7091-6507-2"},{"key":"ref_21","first-page":"165","article-title":"The cyclopeptide alkaloids","volume":"Volume 15","author":"Manske","year":"1975","journal-title":"The Alkaloids: Chemistry and Physiology"},{"key":"ref_22","doi-asserted-by":"crossref","unstructured":"Bla\u017eenovi\u0107, I., Kind, T., Ji, J., and Fiehn, O. (2018). Software tools and approaches for compound identification of LC-MS\/MS data in metabolomics. Metabolites, 8.","DOI":"10.3390\/metabo8020031"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"840","DOI":"10.1021\/cr040699h","article-title":"Plant cyclopeptides","volume":"106","author":"Tan","year":"2006","journal-title":"Chem. Rev."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"6377","DOI":"10.1016\/j.bmcl.2012.08.074","article-title":"Zizimauritic acids A\u2013C, three novel nortriterpenes from Ziziphus mauritiana","volume":"22","author":"Ji","year":"2012","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_25","doi-asserted-by":"crossref","unstructured":"Mu\u00f1oz-Nu\u00f1ez, E., Quiroz-Carre\u00f1o, S., Pastene-Navarrete, E., Seigler, D.S., C\u00e9spedes-Acu\u00f1a, C., Mart\u00ednez Valenzuela, I., Oppliger Mu\u00f1oz, M., Salas-Burgos, A., and Alarc\u00f3n-Enos, J. (2022). Assessments of Ceanothanes Triterpenes as Cholinesterase Inhibitors: An Investigation of Potential Agents with Novel Inspiration for Drug Treatment of Neurodegenerative Diseases. Metabolites, 12.","DOI":"10.3390\/metabo12070668"},{"key":"ref_26","first-page":"88","article-title":"Isolation and characterisation of stigmasterol and \u03b2-sitosterol from Odontonema Strictum (Acanthaceae)","volume":"2","author":"Pierre","year":"2015","journal-title":"J. Innov. Pharm. Biol. Sci."},{"key":"ref_27","first-page":"1","article-title":"Isolation and characterization of \u03b2-sitosterol-3-O-\u03b2-D-glucoside from the extract of the flowers of Viola odorata. Br","volume":"16","author":"Peshin","year":"2017","journal-title":"J. Pharm. Res."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"2473","DOI":"10.1080\/14786419.2022.2050227","article-title":"Two new 5 (14)-membered type cyclopeptide alkaloids from root bark of Ziziphus spina-christi (L.) Desf","volume":"37","author":"Adam","year":"2022","journal-title":"Nat. Prod. Res."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"2571","DOI":"10.1021\/np200755t","article-title":"Cyclopeptide alkaloids from Ziziphus apetala","volume":"74","author":"Han","year":"2011","journal-title":"J. Nat. Prod."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"163","DOI":"10.3329\/bjb.v48i1.47435","article-title":"Isolation of zizyberenalic acid and biological studies of Ziziphus mauritiana Lam. growing in Bangladesh","volume":"48","author":"Karim","year":"2019","journal-title":"Bangladesh J. Bot."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"535","DOI":"10.1248\/cpb.54.535","article-title":"Ceanothane- and lupane-type triterpenes with antiplasmodial and antimycobacterial activities from Ziziphus cambodiana","volume":"54","author":"Suksamrarn","year":"2006","journal-title":"Chem. Pharm. Bull."},{"key":"ref_32","doi-asserted-by":"crossref","unstructured":"Tuenter, E., Segers, K., Kang, K., Viaene, J., Sung, S., Cos, P., Maes, L., Heyden, Y., and Pieters, L. (2017). Antiplasmodial activity, cytotoxicity and Structure-Activity Relationship Study of Cyclopeptide Alkaloids. Molecules, 22.","DOI":"10.3390\/molecules22020224"},{"key":"ref_33","doi-asserted-by":"crossref","unstructured":"Banerjee, P., Kemmler, E., Dunkel, M., and Preissner, R. (2024, June 25). ProTox 3.0: A Webserver for the Prediction of Toxicity of Chemicals. Nucleic Acids Res (Web Server Issue 2024). Available online: https:\/\/tox.charite.de\/protox3.","DOI":"10.1093\/nar\/gkae303"},{"key":"ref_34","doi-asserted-by":"crossref","unstructured":"Daina, A., Michielin, O., and Zoete, V. (2017). SwissADME: A free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules. Sci. Rep., 7.","DOI":"10.1038\/srep42717"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"1353","DOI":"10.1016\/j.cell.2009.11.034","article-title":"Sensory Neuron-Specific GPCR Mrgprs Are Itch Receptors Mediating Chloroquine-Induced Pruritus","volume":"39","author":"Liu","year":"2009","journal-title":"Cell"},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"2803","DOI":"10.1021\/jm201725v","article-title":"Multiple Determinants for Selective Inhibition of Apicomplexan Calcium-Dependent Protein Kinase CDPK1","volume":"55","author":"Larson","year":"2012","journal-title":"J. Med. Chem."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"149","DOI":"10.1042\/BJ20091119","article-title":"Comparison of the cellular and biochemical properties of Plasmodium falciparum choline and ethanolamine kinases","volume":"425","author":"Alberge","year":"2009","journal-title":"Biochem. J."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"456","DOI":"10.2174\/156802612799362922","article-title":"Targeting Protein Kinases in the Malaria Parasite: Update of an Antimalarial Drug Target","volume":"12","author":"Zhang","year":"2012","journal-title":"Curr. Top. Med. Chem."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"604","DOI":"10.1016\/j.bbapap.2009.10.009","article-title":"Malaria: Targeting parasite and host cell kinomes","volume":"1804","author":"Doerig","year":"2010","journal-title":"Biochim. Biophys. Acta"},{"key":"ref_40","doi-asserted-by":"crossref","unstructured":"Cassiano, G.C., Tavella, T.A., Nascimento, M.N., Rodrigues, D.A., Cravo, P.V.L., Andrade, C.H., and Costa, F.T.M. (2021). Targeting malaria protein kinases. Advances in Protein Chemistry and Structural Biology, Elsevier.","DOI":"10.1016\/bs.apcsb.2020.10.004"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"279","DOI":"10.1517\/14728222.11.3.279","article-title":"Antimalarial drug discovery: Targeting protein kinases","volume":"11","author":"Doerig","year":"2007","journal-title":"Expert Opin. Ther. Targets"},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"528","DOI":"10.1021\/acscentsci.6b00162","article-title":"Modeling Reactivity to Biological Macromolecules with a Deep Multitask Network","volume":"2","author":"Hughes","year":"2016","journal-title":"ACS Cent. Sci."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"797","DOI":"10.1021\/acs.chemrestox.5b00017","article-title":"Site of reactivity models predict molecular reactivity of diverse chemicals with glutathione","volume":"28","author":"Hughes","year":"2015","journal-title":"Chem. Res. Toxicol."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"3183","DOI":"10.1093\/bioinformatics\/btw350","article-title":"A Simple Model Predicts UGT-Mediated Metabolism","volume":"32","author":"Hughes","year":"2016","journal-title":"Bioinformatics"},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"447","DOI":"10.1038\/s41587-023-01690-2","article-title":"Integrative analysis of multimodal mass spectrometry data in MZmine 3","volume":"41","author":"Schmid","year":"2023","journal-title":"Nat Biotechnol."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"308","DOI":"10.1038\/s41467-022-35734-z","article-title":"Annotations of Natural Product Compound Families Using Molecular Networking Topology and Structural Similarity Fingerprinting","volume":"14","author":"Morehouse","year":"2023","journal-title":"Nat. Commun."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"905","DOI":"10.1038\/s41592-020-0933-6","article-title":"Feature-based molecular networking in the GNPS analysis environment","volume":"17","author":"Nothias","year":"2020","journal-title":"Nat. Methods"},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"828","DOI":"10.1038\/nbt.3597","article-title":"Sharing and community curation of mass spectrometry data with Global Natural Products Social Molecular Networking","volume":"34","author":"Wang","year":"2016","journal-title":"Nat. Biotechnol."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"4035","DOI":"10.1038\/s41467-018-06082-8","article-title":"Dereplication of microbial metabolites through database search of mass spectra","volume":"9","author":"Mohimani","year":"2018","journal-title":"Nat. Commun."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"3718","DOI":"10.1038\/s41467-021-23986-0","article-title":"MolDiscovery: Learning mass spectrometry fragmentation of small molecules","volume":"12","author":"Cao","year":"2021","journal-title":"Nat. Commun."},{"key":"ref_51","doi-asserted-by":"crossref","unstructured":"Borelli, T.C., Arini, G.S., Feitosa, L.G.P., Dorrestein, P.C., Lopes, N.P., and Da Silva, R.R. (2023). Improving annotation propagation on molecular networks through random walks: Introducing ChemWalker. Bioinformatics, 39.","DOI":"10.1093\/bioinformatics\/btad078"},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"484","DOI":"10.1645\/0022-3395(2005)091[0484:HMPICC]2.0.CO;2","article-title":"Human Malaria Parasites in Continuous Culture","volume":"91","author":"Trager","year":"2005","journal-title":"J. Parasitol."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/30\/14\/2958\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,9]],"date-time":"2025-10-09T18:09:33Z","timestamp":1760033373000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/30\/14\/2958"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,7,14]]},"references-count":52,"journal-issue":{"issue":"14","published-online":{"date-parts":[[2025,7]]}},"alternative-id":["molecules30142958"],"URL":"https:\/\/doi.org\/10.3390\/molecules30142958","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,7,14]]}}}