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

Abstract

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; R 1 = 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, P2 1 2 1 2 1 ; R 1 = 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. OPEN ACCESSCrystals 2012, 2 1442

Inclusion complexes of β-cyclodextrin and polymorphs of mebendazole: Physicochemical characterization

“…These common features were independent of the nature of the guest molecule included. The observed diffractions for FD A and FD C at 2θ 5.79°, 9.36°and 10.30°are in agreement with the dimeric head-to-head β-CD complex with an intermediate crystal packing structure (Elasaad et al, 2012).…”

Targeted Isolation of Indolopyridoquinazoline Alkaloids from Conchocarpus fontanesianus Based on Molecular Networks

“…The 16 known compounds were identified by comparison of their physical and spectroscopic data with published values as dimorphamide C ( 1 ), N-cis- feruloyltyramine ( 2 ), paprazine ( 3 ), confusameline ( 4 ), moupinamide ( 6 ), (−)-syringaresinol ( 7 ), aegelinol ( 8 ), haplopine ( 9 ), 1-methyl-2-phenyl-4-quinolone ( 10 ), skimmianine ( 11 ), γ-fagarine ( 12 ), grossamide ( 13 ), 10-hydroxyrutaecarpine ( 14 ), cannabisin F ( 15 ), flindersine ( 17 ), and 8-methoxyflindersine ( 18 ) . The structure elucidation of the six new indolopyridoquinazoline alkaloids ( 5 , 16 , 19 – 22 ) (Figure ) is described below.…”