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• Elasaad, K
• Alkhatib, R
• Hennebelle, T
• Norberg, B
• Wouters, J
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Crystals 2012, 2(4), 1441-1454; doi:10.3390/cryst2041441

Article

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

Kossay Elasaad ^1,2,* , Racha Alkhatib ³ , Thierry Hennebelle ³ , Bernadette Norberg ¹  and Johan Wouters ^1,*

¹ Department of Chemistry, University of Namur (FUNDP), 61 rue de Bruxelles, B-5000 Namur, Belgium ² Ministry of Higher Education in Syrian Arab Republic, Mezzeh Gamarik Square, Damascus 9251, Syria ³ EA4481, Faculty of Pharmaceutical and Biological Sciences, Université Lille Nord de France Lille2, 3 rue du Professeur Laguesse, F-59006 Lille, France

* Authors to whom correspondence should be addressed.

Received: 28 June 2012; in revised form: 28 August 2012 / Accepted: 26 September 2012 / Published: 17 October 2012

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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.

Keywords: absolute configuration; crystallography; aegelinol; inclusion complex; β-cyclodextrin

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