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Polyoxygenated Cyclohexenes and Other Constituents of Cleistochlamys kirkii Leaves

Journal article
Authors Stephen S. Nyandoro
Joan J. E. Munissi
Amra Gruhonjic
Sandra Duffy
Fangfang Pan
Rakesh Puttreddy
John P. Holleran
Paul A. Fitzpatrick
Jerry Pelletier
Vicky M. Avery
Kari Rissanen
Mate Erdelyi
Published in Journal of natural products
Volume 80
Issue 1
Pages 114-125
ISSN 0163-3864
Publication year 2017
Published at Swedish NMR Centre at Göteborg University
Sahlgrenska Cancer Center
Department of Chemistry and Molecular Biology
Pages 114-125
Language en
Links dx.doi.org/10.1021/acs.jnatprod.6b0...
Keywords Cleistochlamys kirkii, natural product, malaria, NMR
Subject categories Chemical Sciences, Organic Chemistry, Bioorganic chemistry, Medicinal Chemistry, Chemistry, Pharmacognosy

Abstract

Thirteen new metabolites, including the polyoxygenated cyclohexene derivatives cleistodiendiol (1), cleistodienol B (3), cleistenechlorohydrins A (4) and B (5), cleistenediols A–F (6–11), cleistenonal (12), and the butenolide cleistanolate (13), 2,5-dihydroxybenzyl benzoate (cleistophenolide, 14), and eight known compounds (2, 15–21) were isolated from a MeOH extract of the leaves of Cleistochlamys kirkii. The purified metabolites were identified by NMR spectroscopic and mass spectrometric analyses, whereas the absolute configurations of compounds 1, 17, and 19 were established by single-crystal X-ray diffraction. The configuration of the exocyclic double bond of compound 2 was revised based on comparison of its NMR spectroscopic features and optical rotation to those of 1, for which the configuration was determined by X-ray diffraction. Observation of the co-occurrence of cyclohexenoids and heptenolides in C. kirkii is of biogenetic and chemotaxonomic significance. Some of the isolated compounds showed activity against Plasmodium falciparum (3D7, Dd2), with IC50 values of 0.2–40 μM, and against HEK293 mammalian cells (IC50 2.7–3.6 μM). While the crude extract was inactive at 100 μg/mL against the MDA-MB-231 triple-negative breast cancer cell line, some of its isolated constituents demonstrated cytotoxic activity with IC50 values ranging from 0.03–8.2 μM. Compound 1 showed the most potent antiplasmodial (IC50 0.2 μM) and cytotoxic (IC50 0.03 μM, MDA-MB-231 cell line) activities. None of the compounds investigated exhibited translational inhibitory activity in vitro at 20 μM.

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