Polyoxygenated Cyclohexenes and Other Constituents of Cleistochlamys kirkii Leaves

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dc.contributor.authorNyandoro, Stephen S.
dc.contributor.authorMunissi, Joan J.E
dc.contributor.authorGruhonjic, Amra
dc.contributor.authorDuffy, Sandra
dc.contributor.authorPan, FangFang
dc.contributor.authorPuttreddy, Rakesh
dc.contributor.authorHolleran, John P.
dc.contributor.authorFitzpatrick, Paul A.
dc.contributor.authorPelletier, Jerry
dc.contributor.authorAvery, Vicky M.
dc.contributor.authorRissanen, Kari
dc.contributor.authorErdelyi, Mate
dc.date.accessioned2018-11-08T10:12:17Z
dc.date.available2018-11-08T10:12:17Z
dc.date.issued2016-12-21
dc.description.abstractThirteen 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.en_US
dc.description.sponsorshipSwedish Research Council (SRC)en_US
dc.identifier.citationPolyoxygenated Cyclohexenes and Other Constituents of Cleistochlamys kirkii Leaves 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, and Máté Erdélyi Journal of Natural Products 2017 80 (1), 114-125 DOI: 10.1021/acs.jnatprod.6b00759en_US
dc.identifier.doi10.1021/acs.jnatprod.6b00759
dc.identifier.urihttp://hdl.handle.net/20.500.11810/4971
dc.language.isoenen_US
dc.publisherAmerican Chemical Societyen_US
dc.subjectCleistochlamys kirkii, polyoxygenate cyclohexenesen_US
dc.titlePolyoxygenated Cyclohexenes and Other Constituents of Cleistochlamys kirkii Leavesen_US
dc.typeJournal Article, Peer Revieweden_US
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