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Antiplasmodial Chromanes and Chromenes from the Monotypic Plant Species Koeberlinia spinosa.


ABSTRACT: Nine 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.

SUBMITTER: Presley CC 

PROVIDER: S-EPMC5866173 | biostudies-literature | 2018 Mar

REPOSITORIES: biostudies-literature

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Antiplasmodial Chromanes and Chromenes from the Monotypic Plant Species Koeberlinia spinosa.

Presley Christopher Charles CC   Valenciano Ana Lisa AL   Fernández-Murga Maria L ML   Du Yongle Y   Shanaiah Narasimhamurthy N   Cassera Maria B MB   Goetz Michael M   Clement Jason A JA   Kingston David G I DGI  

Journal of natural products 20171019 3


Nine 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 eluc  ...[more]

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