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Determination of the Absolute Configuration of Aegelinol by Crystallization of Its Inclusion Complex with β-Cyclodextrin
Department of Chemistry, University of Namur (FUNDP), 61 rue de Bruxelles, B-5000 Namur, Belgium
Ministry of Higher Education in Syrian Arab Republic, Mezzeh Gamarik Square, Damascus 9251, Syria
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
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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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.
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(4):1441-1454.
Elasaad, Kossay; Alkhatib, Racha; Hennebelle, Thierry; Norberg, Bernadette; Wouters, Johan. 2012. "Determination of the Absolute Configuration of Aegelinol by Crystallization of Its Inclusion Complex with β-Cyclodextrin." Crystals 2, no. 4: 1441-1454.