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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

1,2,* , 3
,
3
,
1
 and
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 / Revised: 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 absolute configuration; crystallography; aegelinol; inclusion complex; β-cyclodextrin
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Elasaad, K.; Alkhatib, R.; Hennebelle, T.; Norberg, B.; Wouters, J. Determination of the Absolute Configuration of Aegelinol by Crystallization of Its Inclusion Complex with β-Cyclodextrin. Crystals 2012, 2, 1441-1454.

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