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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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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