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

Journal article
Authors Stephen S. Nyandoro
Gasper Maeda
J. J. E. Munissi
Amra Gruhonjic
Paul A. Fitzpatrick
S. Lindblad
S. Duffy
J. Pelletier
F. F. Pan
R. Puttreddy
V. M. Avery
Mate Erdelyi
Published in Molecules
Volume 24
Issue 15
Publication year 2019
Published at Sahlgrenska Cancer Center
Department of Chemistry and Molecular Biology
Language en
Links dx.doi.org/10.3390/molecules2415274...
Keywords Cleistochlamys kirkii, Annonaceae, benzopyranyl sesquiterpene, cleistonol, antiplasmodial activity, malaria, cytotoxicity, cadinane-type sesquiterpenes, absolute-configuration, circular-dichroism, uvaria, constituents, flavonoids, roots, Biochemistry & Molecular Biology, Chemistry
Subject categories Biochemistry and Molecular Biology

Abstract

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.

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Utskriftsdatum: 2019-12-08