{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,11]],"date-time":"2026-09-11T05:03:32Z","timestamp":1789103012261,"version":"build-2803163510"},"reference-count":35,"publisher":"MDPI AG","issue":"23","license":[{"start":{"date-parts":[[2019,12,3]],"date-time":"2019-12-03T00:00:00Z","timestamp":1575331200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100000780","name":"European Commission","doi-asserted-by":"publisher","award":["FP7-PEOPLE-2013-IIF, Grant Agreement No. 629482"],"award-info":[{"award-number":["FP7-PEOPLE-2013-IIF, Grant Agreement No. 629482"]}],"id":[{"id":"10.13039\/501100000780","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100005156","name":"Alexander von Humboldt-Stiftung","doi-asserted-by":"publisher","award":["Research Group Linkage funding 2015\/2018 to the Sewald\/Wansi"],"award-info":[{"award-number":["Research Group Linkage funding 2015\/2018 to the Sewald\/Wansi"]}],"id":[{"id":"10.13039\/100005156","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100000803","name":"Directorate-General for Development and Cooperation - EuropeAid","doi-asserted-by":"publisher","award":["Project ENOCH (No. CZ.02.1.01\/0.0\/0.0\/16_019\/0000868)"],"award-info":[{"award-number":["Project ENOCH (No. CZ.02.1.01\/0.0\/0.0\/16_019\/0000868)"]}],"id":[{"id":"10.13039\/501100000803","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>A phytochemical study of the root and bark of Brucea antidysenterica J. F. Mill. (Simaroubaceae) afforded three new compounds, including a stilbene glycoside bruceanoside A (1), and two canthinone alkaloids bruceacanthinones A (3) and B (4), along with ten known secondary metabolites, rhaponticin (2), 1,11-dimethoxycanthin-6-one (5), canthin-6-one (6), 1-methoxycanthin-6-one (7), 2-methoxycanthin-6-one (8), 2-hydroxy-1,11-dimethoxycanthin-6-one (9), \u03b2-carboline-1-propionic acid (10), cleomiscosin C (11), cleomiscosin A (12), and hydnocarpin (13). The structures of all the compounds were determined using spectrometric and spectroscopic methods including 1D and 2D NMR, and HRSEIMS. The identities of the known compounds were further confirmed by comparison of their data with those reported in the literature. The root and bark methanolic extracts, the dichloromethane and ethyl acetate soluble fractions, and the isolated compounds (3\u201313), were assessed for their cytotoxicity against the cancer cell lines A-549, MCF-7, and PC-3. The results suggested that compounds in the extracts might possess a synergic action in their cytotoxicity.<\/jats:p>","DOI":"10.3390\/molecules24234412","type":"journal-article","created":{"date-parts":[[2019,12,3]],"date-time":"2019-12-03T04:58:39Z","timestamp":1575349119000},"page":"4412","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":23,"title":["Cytotoxic Stilbenes and Canthinone Alkaloids from Brucea antidysenterica (Simaroubaceae)"],"prefix":"10.3390","volume":"24","author":[{"given":"Yves Salomon","family":"Makong","sequence":"first","affiliation":[{"name":"Department of Chemistry, Faculty of Science, University of Douala, P.O. Box 24157 Douala, Cameroon"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9659-6125","authenticated-orcid":false,"given":"Gervais","family":"Mouth\u00e9 Happi","sequence":"additional","affiliation":[{"name":"Organic and Bioorganic Chemistry, Department of Chemistry, Bielefeld University, 33501 Bielefeld, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Judith Liliane","family":"Djouaka Bavoua","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Faculty of Science, University of Douala, P.O. Box 24157 Douala, Cameroon"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5111-4361","authenticated-orcid":false,"given":"Jean Duplex","family":"Wansi","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Faculty of Science, University of Douala, P.O. Box 24157 Douala, Cameroon"},{"name":"Organic and Bioorganic Chemistry, Department of Chemistry, Bielefeld University, 33501 Bielefeld, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lutfun","family":"Nahar","sequence":"additional","affiliation":[{"name":"Laboratory of Growth Regulators, Institute of Experimental Botany ASCR &amp; Palack\u00fd University, \u0160lechtitel\u016f 27, 78371 Olomouc, Czech Republic"},{"name":"Centre for Natural Products Discovery (CNPD), School of Pharmacy and Biomolecular Sciences, Liverpool John Moores University, James Parsons Building, Byrom Street, Liverpool L3 3AF, UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alain Fran\u00e7ois","family":"Kamdem Waffo","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Faculty of Science, University of Douala, P.O. Box 24157 Douala, Cameroon"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Claire","family":"Martin","sequence":"additional","affiliation":[{"name":"Department of Biological Sciences, School of Science and the Environment, University of Worcester, Henwick Grove, Worcester WR2 6AJ, UK"}],"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, Department of Chemistry, Bielefeld University, 33501 Bielefeld, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4038-0514","authenticated-orcid":false,"given":"Satyajit Dey","family":"Sarker","sequence":"additional","affiliation":[{"name":"Centre for Natural Products Discovery (CNPD), School of Pharmacy and Biomolecular Sciences, Liverpool John Moores University, James Parsons Building, Byrom Street, Liverpool L3 3AF, UK"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2019,12,3]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"57","DOI":"10.1002\/cbdv.200700409","article-title":"Chemical constituents of plants from the genus Brucea","volume":"6","author":"Liu","year":"2009","journal-title":"Chem. Biodiver."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"1725","DOI":"10.1128\/AAC.32.11.1725","article-title":"Use of microdilution to assess in vitro antiamoebic activities of Brucea javanica fruits, Simarouba amara stem, and a number of quassinoids","volume":"32","author":"Wright","year":"1988","journal-title":"Antimicrob. Agents Chemother."},{"key":"ref_3","first-page":"1157","article-title":"Antiproliferative and apoptosis-inducing activity of Brucea javanica extract on human carcinoma cells","volume":"16","author":"Lau","year":"2005","journal-title":"Int. J. Mol. Med."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"972","DOI":"10.1021\/np50042a017","article-title":"Antitumor agents, 74. Bruceanol-A and -B, Two new antileukemic quassinoids from Brucea antidysenterica","volume":"48","author":"Okano","year":"1985","journal-title":"J. Nat. Prod."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"468","DOI":"10.1021\/np50082a011","article-title":"Antitumor agents, 127. Bruceoside C, a new cytotoxic quassinoid glucoside, and related compounds from Brucea javanica","volume":"55","author":"Fukamiya","year":"1992","journal-title":"J. Nat. Prod."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"1416","DOI":"10.1248\/cpb.42.1416","article-title":"Indonesian medicinal plants. VIII. Chemical structures of three new triterpenoids, bruceajavanin A, dihydrobruceajavanin A, and bruceajavanin B, and a new alkaloidal glycoside, bruceacanthinoside, from the stems of Brucea javanica (Simaroubaceae)","volume":"42","author":"Kitagawa","year":"1994","journal-title":"Chem. Pharm. Bull."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"41","DOI":"10.1021\/np50049a007","article-title":"Plants as sources of antimalarial drugs, Part 4: Activity of Brucea javanica fruits against chloroquine-resistant Plasmodium falciparum in vitro and against Plasmodium berghei in vivo","volume":"50","author":"Bray","year":"1987","journal-title":"J. Nat. Prod."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"1527","DOI":"10.1248\/cpb.45.1527","article-title":"Anti-tuberculosis activity of quassinoids","volume":"45","author":"Rahman","year":"1997","journal-title":"Chem. Pharm. Bull."},{"key":"ref_9","unstructured":"Watt, J.M., and Breyer-Brandwijk, M.G. (1962). The Medicinal and Poisonous Plants of Southern and Eastern Africa, E. and S. Livingstone. [2nd ed.]."},{"key":"ref_10","unstructured":"Mill, J.F. (2008). Brucea Antidysenterica, Medicinal Plants\/Plantes Medicinales, PROTA."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"269","DOI":"10.1021\/np030304+","article-title":"Antitumor activity of bruceantin. An old drug with new promise","volume":"67","author":"Cuendet","year":"2004","journal-title":"J. Nat. Prod."},{"key":"ref_12","first-page":"131","article-title":"Phytochemical screening and antioxidant activity investigations on the crude extracts of Brucea antidysenterica leaves","volume":"1","author":"Dilnesa","year":"2016","journal-title":"Int. J. Res. Dev."},{"key":"ref_13","first-page":"14","article-title":"Wound healing effect of aqueous extracts of Brucea antidysenterica and Croton marcostachys from Northwest Ethiopia in albino mice","volume":"8","author":"Mekonnen","year":"2019","journal-title":"J. Afr. Pharmacol. Ther."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"118","DOI":"10.1186\/s12906-016-1098-9","article-title":"Antimalarial properties of crude extracts of seeds of Brucea antidysenterica and leaves of Ocimum lamiifolium","volume":"16","author":"Kefe","year":"2016","journal-title":"BMC Compl. Altern. Med."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"178","DOI":"10.1021\/jo00941a049","article-title":"Bruceantin, a new potent antileukemic simaroubolide from Brucea antidysenterica","volume":"38","author":"Kupchan","year":"1973","journal-title":"J. Org. Chem."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"173","DOI":"10.2174\/0929867053363351","article-title":"Biologically active quassinoids and their chemistry: potential leads for drug design","volume":"12","author":"Guo","year":"2005","journal-title":"Curr. Med. Chem."},{"key":"ref_17","doi-asserted-by":"crossref","unstructured":"Makong, Y.S., Fotso, G.W., Mouthe, G.H., Lenta, B., Rennert, R., Sewald, N., Arnold, N., Wansi, J.D., and Ngadjui, B.T. (2019). Bruceadysentoside A, a new pregnane glycoside and others secondary metabolites with cytotoxic activity from Brucea antidysenterica JF Mill. (Simaroubaceae). Nat. Prod. Res., 1\u20137.","DOI":"10.1080\/14786419.2019.1655024"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"407","DOI":"10.1016\/S0031-9422(00)00341-1","article-title":"Anti-platelet stilbenes from aerial parts of Rheum palaestinum","volume":"55","author":"Aburjai","year":"2000","journal-title":"Phytochemistry"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"428","DOI":"10.1021\/np50045a007","article-title":"Antitumor agents, 79. Cytotoxic antileukemic alkaloids from Brucea antidysenterica","volume":"49","author":"Narihiko","year":"1986","journal-title":"J. Nat. Prod."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"1532","DOI":"10.1248\/cpb.24.1532","article-title":"Studies on the constituents of Ailanthus altissima Swingle. The alkaloidal constituents","volume":"24","author":"Ohmoto","year":"1976","journal-title":"Chem. Pharm. Bull."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"259","DOI":"10.1055\/s-2006-959664","article-title":"2-Methoxycanthin-6-one: A new alkaloid from the stem wood of Quassia amara","volume":"59","author":"Njar","year":"1993","journal-title":"Planta Med."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"151","DOI":"10.1055\/s-2007-969432","article-title":"Canthin-6-one alkaloids from Brucea antidysenterica root bark","volume":"51","author":"Harris","year":"1985","journal-title":"Planta Med."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"911","DOI":"10.1016\/0031-9422(95)00039-A","article-title":"Alkaloids and quassinoids of Brucea mollis var. tonkinensis","volume":"39","author":"Yishan","year":"1995","journal-title":"Phytochemistry"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"209","DOI":"10.1016\/S0040-4020(01)83488-8","article-title":"Structures of cleomiscisins, coumarinolignoids of Cleome Viscosa seeds","volume":"41","author":"Ray","year":"1985","journal-title":"Tetrahedron"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"550","DOI":"10.1021\/np50033a030","article-title":"Antitumor agents, 65. Brusatol and cleomiscosin-A, antileukemic principles from Brucea javanica","volume":"47","author":"Lee","year":"1984","journal-title":"J. Nat. Prod."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"2219","DOI":"10.1016\/j.bmc.2008.10.076","article-title":"Bioactivity-guided isolation of cytotoxic constituents of Brucea javanica collected in Vietnam","volume":"17","author":"Pan","year":"2009","journal-title":"Bioorg. Med. Chem."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"649","DOI":"10.1016\/S0367-326X(01)00295-7","article-title":"A new stilbene glycoside from Elephantorrhiza goetzei","volume":"72","author":"Wanjala","year":"2001","journal-title":"Fitoterapia"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"803","DOI":"10.1016\/S0031-9422(02)00108-5","article-title":"Chalconoid and stilbenoid glycosides from Guibourtia tessmanii","volume":"60","author":"Fuendjiep","year":"2002","journal-title":"Phytochemistry"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"1517","DOI":"10.1016\/S0031-9422(00)89569-2","article-title":"13C NMR spectra of pentacyclic triterpenoids-a compilation and some salient features","volume":"37","author":"Mahato","year":"1994","journal-title":"Phytochemistry"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"653","DOI":"10.1002\/ptr.2136","article-title":"Antibacterial activity of two canthin-6-one alkaloids from Allium neapolitanum","volume":"21","author":"Gibbons","year":"2007","journal-title":"Phytother. Res."},{"key":"ref_31","doi-asserted-by":"crossref","unstructured":"L\u00f3pez, C., Pastrana, M., R\u00edos, A., Cogollo, A., and Pab\u00f3n, A. (2018). Huberine, a new canthin-6-one alkaloid from the bark of Picrolemma huberi. Molecules, 23.","DOI":"10.3390\/molecules23040934"},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"55","DOI":"10.1016\/0022-1759(83)90303-4","article-title":"Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays","volume":"65","author":"Mosmann","year":"1983","journal-title":"J. Immunol. Meth."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"944","DOI":"10.1002\/ptr.5329","article-title":"Comparative cytotoxicity of Glycyrrhiza glabra roots from different geographical origins against immortal human keratinocyte (HaCaT), lung adenocarcinoma (A549) and liver carcinoma (HepG2) cells","volume":"29","author":"Basar","year":"2015","journal-title":"Phytother. Res."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"1215","DOI":"10.1002\/ptr.5842","article-title":"Cytotoxic properties of the stem bark of Citrus reticulata Blanco (Rutaceae)","volume":"31","author":"Tahsin","year":"2017","journal-title":"Phytother. Res."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"108","DOI":"10.1016\/j.jcis.2015.07.005","article-title":"On the photocatalytic reduction of MTT tetrazolium salt on the surface of TiO2 nanoparticles: Formazan production kinetics and mechanism","volume":"457","author":"Popescu","year":"2015","journal-title":"J. Colloid Interface Sci."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/24\/23\/4412\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T13:39:38Z","timestamp":1760189978000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/24\/23\/4412"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2019,12,3]]},"references-count":35,"journal-issue":{"issue":"23","published-online":{"date-parts":[[2019,12]]}},"alternative-id":["molecules24234412"],"URL":"https:\/\/doi.org\/10.3390\/molecules24234412","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2019,12,3]]}}}