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A New Benzopyranyl Cadenane Sesquiterpene and Other Antiplasmodial and Cytotoxic Metabolites from Cleistochlamys kirkii
Univ Dar Es Salaam, Coll Nat & Appl Sci, Chem Dept, POB 35061, Dar Es Salaam, Tanzania;Univ Gothenburg, Dept Chem & Mol Biol, SE-41296 Gothenburg, Sweden.
Univ Dar Es Salaam, Coll Nat & Appl Sci, Chem Dept, POB 35061, Dar Es Salaam, Tanzania;Univ Gothenburg, Dept Chem & Mol Biol, SE-41296 Gothenburg, Sweden.
Univ Dar Es Salaam, Coll Nat & Appl Sci, Chem Dept, POB 35061, Dar Es Salaam, Tanzania.
Univ Gothenburg, Dept Chem & Mol Biol, SE-41296 Gothenburg, Sweden.
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2019 (English)In: Molecules, ISSN 1420-3049, E-ISSN 1420-3049, Vol. 24, no 15, article id 2746Article in journal (Refereed) Published
Abstract [en]

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 (2-13). 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 mu g/mL. The isolated metabolites dichamanetin, (E)-acetylmelodorinol, and cleistenolide showed IC50 = 9.3, 7.6 and 15.2 mu M, 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 mu g/mL (crude extract) and 9.6-30.7 mu M (isolated compounds). Our findings demonstrate the potential applicability of C. kirkii as a source of antimalarial and anticancer agents.

Place, publisher, year, edition, pages
MDPI , 2019. Vol. 24, no 15, article id 2746
Keywords [en]
Cleistochlamys kirkii, Annonaceae, benzopyranyl sesquiterpene, cleistonol, antiplasmodial activity, malaria, cytotoxicity
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-393825DOI: 10.3390/molecules24152746ISI: 000482441100069PubMedID: 31362371OAI: oai:DiVA.org:uu-393825DiVA, id: diva2:1356431
Funder
Swedish Research Council, 2016-05857Australian Research Council, LP120200557Swedish Research CouncilAvailable from: 2019-10-01 Created: 2019-10-01 Last updated: 2019-10-01Bibliographically approved

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