Antiplasmodial Chromanes and Chromenes from the Monotypic Plant Species Koeberlinia spinosa

J Nat Prod. 2018 Mar 23;81(3):475-483. doi: 10.1021/acs.jnatprod.7b00579. Epub 2017 Oct 19.

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.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Animals
  • Antimalarials / pharmacology*
  • Benzopyrans / pharmacology*
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Magnetic Resonance Spectroscopy / methods
  • Magnoliopsida / chemistry*
  • Plasmodium falciparum / drug effects*

Substances

  • Antimalarials
  • Benzopyrans