Invariom structure refinement, electrostatic potential and toxicity of 4-O-methylalpinumisoflavone, O,O-dimethylalpinumisoflavone and 5-O-methyl-4-O-(3-methylbut-2-en-1-yl)alpinumisoflavone

Robert Kingsford-Adaboh, Birger Dittrich, Christian B. Hübschle, Winfred S.K. Gbewonyo, Hideki Okamoto, Masaro Kimura, Hiroyuki Ishida

Research output: Contribution to journalArticlepeer-review

17 Citations (Scopus)

Abstract

The accurate X-ray single-crystal structures of the isoflavone compounds 4-O-methylalpinumisoflavone, O,O-dimethylalpinumisoflavone and 5-O-methyl-4-O-(3-methylbut-2-en-1yl)alpinumisoflavone {alpinumisoflavone = 5-hydroxy-7-(4-hydroxyphenyl)-2,2-dimethyl-2H,6H-benzo[1,2-b:5,4-b′] -dipyran-6-one} from data sets measured at cryogenic temperature have been obtained from invariom modelling using theoretically predicted Hansen and Coppens multipole-model form factors, which describe the aspherical electron density distribution. Molecular dipole moments and electrostatic potentials obtained from invariom modelling are discussed and compared with results from ab initio theoretical calculations. All three studied compounds are solvent extracts of root bark or seed powder of Millettia thonningii (leguminosae), a plant molluscicide and cercaricide used in Franco West Africa as medication against various diseases. The compounds' toxicities to brine shrimp have been determined and their different potencies tentatively related to conformation differences, intramolecular contacts, dipole moments and electrostatic potential features.

Original languageEnglish
Pages (from-to)843-849
Number of pages7
JournalActa Crystallographica Section B: Structural Science
Volume62
Issue number5
DOIs
Publication statusPublished - Oct 1 2006

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)

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