np7b00579_si_001.pdf (11.48 MB)
Antiplasmodial Chromanes and Chromenes from the Monotypic Plant Species Koeberlinia spinosa
journal contribution
posted on 2017-10-19, 17:33 authored by Christopher
Charles Presley, Ana Lisa Valenciano, Maria L. Fernández-Murga, Yongle Du, Narasimhamurthy Shanaiah, Maria B. Cassera, Michael Goetz, Jason A. Clement, David G. I. KingstonNine new compounds containing either a chromane or chromene ring
moiety were isolated from the monotypic plant Koeberlinia
spinosa. Compounds 1–4 are
chromanes with all possible E and Z isomers of the isoprenoid side
chain, with compound 5 a methylated derivative of 1. Compounds 6 and 7 were assigned
as diastereomeric cyclized derivatives of 2 and were
probably artifacts formed during the extraction or the isolation processes.
Compounds 8 and 9 were characterized as
new chromenes. Structure elucidation of 1–9 was conducted via 1D and 2D NMR spectroscopic data interpretation,
and absolute configurations were determined by ECD spectroscopic analysis.
Compounds 2, 5, 6, and 7 had weak antiplasmodial activity, while none of the compounds
exhibited antiproliferative activity. The isolation, structure elucidation,
and biological evaluation of these compounds are presented.
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compound 5structure elucidationmonotypic plant Koeberlinia spinosaECD spectroscopic analysisCompounds 6Compounds 2diastereomeric cyclized derivativesCompounds 8Antiplasmodial Chromaneschromene ring moietyisoprenoid side chainantiplasmodial activityStructure elucidationMonotypic Plant Species Koeberlinia spinosachromane1 DZ isomersantiproliferative activity2 D NMR spectroscopic data interpretationisolation processes
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