Determination of the Absolute Configuration of Aegelinol by Crystallization of Its Inclusion Complex with β-Cyclodextrin

Kossay Elasaad, Racha Alkhatib, Thierry Hennebelle, Bernadette Norberg, Johan Wouters

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Abstract

The absolute configuration and structure of aegelinol, a pyranocoumarin isolated from Ferulago asparagifolia Boiss (Apiaceae), has been determined by crystallography. Crystal structure of the inclusion complex of aegelinol in β-cyclodextrin was determined (a = 15.404(1) Å, b = 15.281(1) Å, c = 17.890(1) Å, α = 99.662(1), β = 113.4230(1), γ = 102.481(1)°, P1; R1 = 6.71%) and allowed unambiguous determination of the absolute configuration of the stereogenic center of aegelinol. The pyranocoumarin guest is included within the cylindrical cavity formed by dimeric β-cyclodextrin molecules with a head-to-head arrangement. Crystal structure of aegelinol alone was also determined (a = 6.8921(3) Å, b = 11.4302(9) Å, c = 44.964(3) Å, P212121; R1 = 4.44%) and allowed precise determination of its geometry. Aegelinol crystallizes with three molecules in the asymmetric unit held together by H-bonds and π-stacking interactions.
Original languageEnglish
Pages (from-to)1441-1454
Number of pages14
JournalCrystals
Volume2
Issue number4
DOIs
Publication statusPublished - 26 Oct 2012

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    CCDC 884099: Experimental Crystal Structure Determination

    Alkhatib, R. (Contributor), Kossay, E. (Contributor), Hennebelle, T. (Contributor), NORBERG, B. (Contributor) & WOUTERS, J. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2016

    Dataset

    CCDC 884098: Experimental Crystal Structure Determination

    Alkhatib, R. (Contributor), Kossay, E. (Contributor), Hennebelle, T. (Contributor), NORBERG, B. (Contributor) & WOUTERS, J. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2016

    Dataset

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