title: Self-assembly modes of glycyrrhetinic acid esters in view of the crystal packing of related triterpene molecules.
abstract: The crystal structures of three ester derivatives of glycyrrhetinic acid (GE) are reported. X-ray crystallography revealed that despite differences in the size of the ester substituents (ethyl, isopropyl and 2-morpholinoethyl) the scheme of molecular self-assembly is similar in all three cases but differs significantly from that observed in other known GE esters. According to our analysis, the two basic patterns of self-assembly of GE esters observed in their unsolvated crystals correspond to two distinct orientations of the ester groups relative to the triterpene backbone. Moreover, comparison of the self-assembly modes of GE esters in their unsolvated forms with the supramolecular organization of GE and carbenoxolone in their solvated crystals revealed that ester substituents replace solvent molecules hydrogen bonded to the COOH group at the triterpene skeleton, resulting in similar packing arrangements of these compounds.
authors.affiliation: Department of Chemical Technology of Drugs, Poznań Uniwersity of Medical Sciences, Grunwaldzka 6, Poznań 60-780, Poland.
authors.forename: Dominik
authors.initials: D
authors.lastname: Langer
authors.affiliation: Department of Chemical Technology of Drugs, Poznań Uniwersity of Medical Sciences, Grunwaldzka 6, Poznań 60-780, Poland.
authors.forename: Barbara
authors.initials: B
authors.lastname: Wicher
authors.affiliation: Department of Chemical Technology of Drugs, Poznań Uniwersity of Medical Sciences, Grunwaldzka 6, Poznań 60-780, Poland.
authors.forename: Wojciech
authors.initials: W
authors.lastname: Szczołko
authors.affiliation: Faculty of Chemistry, A. Mickiewicz University, Umultowska 89b, Poznań 61-614, Poland.
authors.forename: Maria
authors.initials: M
authors.lastname: Gdaniec
authors.affiliation: Department of Chemical Technology of Drugs, Poznań Uniwersity of Medical Sciences, Grunwaldzka 6, Poznań 60-780, Poland.
authors.forename: Ewa
authors.initials: E
authors.lastname: Tykarska
mesh_terms: D002229:Carbenoxolone / Q000737:chemistry; D018360:Crystallography, X-Ray; D004951:Esterification; D004952:Esters / Q000737:chemistry; D006034:Glycyrrhetinic Acid / Q000031:analogs & derivatives*; D006860:Hydrogen Bonding; D008958:Models, Molecular; D014315:Triterpenes / Q000737:chemistry
chemical_list: D004952:Esters; D014315:Triterpenes; D002229:Carbenoxolone; D006034:Glycyrrhetinic Acid
keywords: glycyrrhetinic acid; intermolecular interactions; supramolecular architecture; triterpenes