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Open AccessArticle

A New Benzopyranyl Cadenane Sesquiterpene and Other Antiplasmodial and Cytotoxic Metabolites from Cleistochlamys kirkii

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Chemistry Department, College of Natural and Applied Sciences, University of Dar es Salaam, Dar es Salaam P.O. Box 35061, Tanzania
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Department of Chemistry and Molecular Biology, University of Gothenburg, SE-412 96 Gothenburg, Sweden
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Sahlgrenska Cancer Centre, University of Gothenburg, SE-405 30 Gothenburg, Sweden
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Department of Chemistry-BMC, Uppsala University, SE-751 23 Uppsala, Sweden
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Discovery Biology, Griffith Institute for Drug Discovery, Griffith University, Nathan Q1d 4111, Australia
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Department of Biochemistry, McGill University, Montréal, QC H3G 1Y6, Canada
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Key Laboratory of Pesticide & 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
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Department of Chemistry, University of Jyvaskyla, P.O. Box 35, FI-40014 Jyvaskyla, Finland
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Authors to whom correspondence should be addressed.
Academic Editor: Alessandra Guerrini
Molecules 2019, 24(15), 2746; https://doi.org/10.3390/molecules24152746
Received: 8 July 2019 / Revised: 24 July 2019 / Accepted: 27 July 2019 / Published: 29 July 2019
(This article belongs to the Special Issue Biological Activities of Plant Secondary Metabolites)
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 (213). 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 μg/mL. The isolated metabolites dichamanetin, (E)-acetylmelodorinol, and cleistenolide showed IC50 = 9.3, 7.6 and 15.2 μM, 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 μg/mL (crude extract) and 9.6–30.7 μM (isolated compounds). Our findings demonstrate the potential applicability of C. kirkii as a source of antimalarial and anticancer agents. View Full-Text
Keywords: Cleistochlamys kirkii; Annonaceae; benzopyranyl sesquiterpene; cleistonol; antiplasmodial activity; malaria; cytotoxicity Cleistochlamys kirkii; Annonaceae; benzopyranyl sesquiterpene; cleistonol; antiplasmodial activity; malaria; cytotoxicity
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MDPI and ACS Style

Nyandoro, S.S.; Maeda, G.; Munissi, J.J.; Gruhonjic, A.; Fitzpatrick, P.A.; Lindblad, S.; Duffy, S.; Pelletier, J.; Pan, F.; Puttreddy, R.; Avery, V.M.; Erdélyi, M. A New Benzopyranyl Cadenane Sesquiterpene and Other Antiplasmodial and Cytotoxic Metabolites from Cleistochlamys kirkii. Molecules 2019, 24, 2746.

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