{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,21]],"date-time":"2026-01-21T05:19:04Z","timestamp":1768972744382,"version":"3.49.0"},"reference-count":27,"publisher":"MDPI AG","issue":"15","license":[{"start":{"date-parts":[[2019,7,29]],"date-time":"2019-07-29T00:00:00Z","timestamp":1564358400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100004359","name":"Vetenskapsr\u00e5det","doi-asserted-by":"publisher","award":["2016-05857"],"award-info":[{"award-number":["2016-05857"]}],"id":[{"id":"10.13039\/501100004359","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100013443","name":"Swedish Insitute","doi-asserted-by":"publisher","award":["00045\/2014"],"award-info":[{"award-number":["00045\/2014"]}],"id":[{"id":"10.13039\/100013443","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100000923","name":"Australian Research Council","doi-asserted-by":"publisher","award":["LP120200557"],"award-info":[{"award-number":["LP120200557"]}],"id":[{"id":"10.13039\/501100000923","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Phytochemical investigations of ethanol root bark and stem bark extracts of Cleistochlamys kirkii (Benth.) Oliv. (Annonaceae) yielded a new benzopyranyl cadinane-type sesquiterpene (cleistonol, 1) alongside 12 known compounds (2\u201313). The structures of the isolated compounds were established from NMR spectroscopic and mass spectrometric analyses. Structures of compounds 5 and 10 were further confirmed by single crystal X-ray crystallographic analyses, which also established their absolute stereochemical configuration. The ethanolic crude extract of C. kirkii root bark gave 72% inhibition against the chloroquine-sensitive 3D7-strain malaria parasite Plasmodium falciparum at 0.01 \u03bcg\/mL. The isolated metabolites dichamanetin, (E)-acetylmelodorinol, and cleistenolide showed IC50 = 9.3, 7.6 and 15.2 \u03bcM, respectively, against P. falciparum 3D7. Both the crude extract and the isolated compounds exhibited cytotoxicity against the triple-negative, aggressive breast cancer cell line, MDA-MB-231, with IC50 = 42.0 \u03bcg\/mL (crude extract) and 9.6\u201330.7 \u03bcM (isolated compounds). Our findings demonstrate the potential applicability of C. kirkii as a source of antimalarial and anticancer agents.<\/jats:p>","DOI":"10.3390\/molecules24152746","type":"journal-article","created":{"date-parts":[[2019,7,29]],"date-time":"2019-07-29T11:20:18Z","timestamp":1564399218000},"page":"2746","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":21,"title":["A New Benzopyranyl Cadenane Sesquiterpene and Other Antiplasmodial and Cytotoxic Metabolites from Cleistochlamys kirkii"],"prefix":"10.3390","volume":"24","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-4659-0187","authenticated-orcid":false,"given":"Stephen S.","family":"Nyandoro","sequence":"first","affiliation":[{"name":"Chemistry Department, College of Natural and Applied Sciences, University of Dar es Salaam, Dar es Salaam P.O. Box 35061, Tanzania"},{"name":"Department of Chemistry and Molecular Biology, University of Gothenburg, SE-412 96 Gothenburg, Sweden"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Gasper","family":"Maeda","sequence":"additional","affiliation":[{"name":"Chemistry Department, College of Natural and Applied Sciences, University of Dar es Salaam, Dar es Salaam P.O. Box 35061, Tanzania"},{"name":"Department of Chemistry and Molecular Biology, University of Gothenburg, SE-412 96 Gothenburg, Sweden"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Joan J.E.","family":"Munissi","sequence":"additional","affiliation":[{"name":"Chemistry Department, College of Natural and Applied Sciences, University of Dar es Salaam, Dar es Salaam P.O. Box 35061, Tanzania"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Amra","family":"Gruhonjic","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Molecular Biology, University of Gothenburg, SE-412 96 Gothenburg, Sweden"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Paul A.","family":"Fitzpatrick","sequence":"additional","affiliation":[{"name":"Sahlgrenska Cancer Centre, University of Gothenburg, SE-405 30 Gothenburg, Sweden"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Sofia","family":"Lindblad","sequence":"additional","affiliation":[{"name":"Department of Chemistry-BMC, Uppsala University, SE-751 23 Uppsala, Sweden"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Sandra","family":"Duffy","sequence":"additional","affiliation":[{"name":"Discovery Biology, Griffith Institute for Drug Discovery, Griffith University, Nathan Q1d 4111, Australia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jerry","family":"Pelletier","sequence":"additional","affiliation":[{"name":"Department of Biochemistry, McGill University, Montr\u00e9al, QC H3G 1Y6, Canada"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Fangfang","family":"Pan","sequence":"additional","affiliation":[{"name":"Key Laboratory of Pesticide &amp; Chemical Biology of Ministry of Education, Hubei International Scientific and Technological Cooperation Base of Pesticide and Green Synthesis, College of Chemistry, Central China Normal University, Luoyu Road 152, Wuhan 430079, China"},{"name":"Department of Chemistry, University of Jyvaskyla, P.O. Box 35, FI-40014 Jyvaskyla, Finland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2221-526X","authenticated-orcid":false,"given":"Rakesh","family":"Puttreddy","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University of Jyvaskyla, P.O. Box 35, FI-40014 Jyvaskyla, Finland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4914-2299","authenticated-orcid":false,"given":"Vicky M.","family":"Avery","sequence":"additional","affiliation":[{"name":"Discovery Biology, Griffith Institute for Drug Discovery, Griffith University, Nathan Q1d 4111, Australia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0359-5970","authenticated-orcid":false,"given":"M\u00e1t\u00e9","family":"Erd\u00e9lyi","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Molecular Biology, University of Gothenburg, SE-412 96 Gothenburg, Sweden"},{"name":"Department of Chemistry-BMC, Uppsala University, SE-751 23 Uppsala, Sweden"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2019,7,29]]},"reference":[{"key":"ref_1","unstructured":"Verdcourt, B. (1971). 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