title: Influence of intramolecular hydrogen bonds on regioselectivity of glycosylation. Synthesis of lupane-type saponins bearing the OSW-1 saponin disaccharide unit and its isomers.
abstract: A series of lupane-type saponins bearing OSW-1 disaccharide unit as well as its regio- and stereoisomers were prepared and used for the structure-activity relationships (SAR) study. Unexpected preference for 1→4-linked regioisomers and an unusual inversion of the conformation of the sugar rings were noted. Cytotoxic activity of new lupane compounds was evaluated in vitro and revealed that some saponins exhibited an interesting bioactivity profile against human cancer cell lines. Influence of the protecting groups on the cytotoxicity was investigated. These results open the way to the synthesis of various lupane-type triterpene and saponin derivatives as potential anticancer compounds.
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland.
authors.forename: Kinga
authors.initials: K
authors.lastname: Kuczynska
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland.
authors.forename: Piotr
authors.initials: P
authors.lastname: Cmoch
authors.affiliation: Department of Chemical Biology and Genetics, Centre of the Region Haná for Biotechnological and Agricultural Research, Palacký University, Šlechtitelů 27, 783 71 Olomouc, Czech Republic.
authors.forename: Lucie
authors.initials: L
authors.lastname: Rárová
authors.affiliation: Laboratory of Growth Regulators, Centre of the Region Haná for Biotechnological and Agricultural Research, Institute of Experimental Botany ASCR & Palacký University, Šlechtitelů 27, 783 71 Olomouc, Czech Republic.
authors.forename: Jana
authors.initials: J
authors.lastname: Oklešťková
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland.
authors.forename: Anna
authors.initials: A
authors.lastname: Korda
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland. Electronic address: zbigniew.pakulski@icho.edu.pl.
authors.forename: Zbigniew
authors.initials: Z
authors.lastname: Pakulski
authors.affiliation: Laboratory of Growth Regulators, Centre of the Region Haná for Biotechnological and Agricultural Research, Institute of Experimental Botany ASCR & Palacký University, Šlechtitelů 27, 783 71 Olomouc, Czech Republic. Electronic address: miroslav.strnad@upol.cz.
authors.forename: Miroslav
authors.initials: M
authors.lastname: Strnad
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D001089:Arabinose / Q000737:chemistry; D045744:Cell Line, Tumor; D060326:Chemistry Techniques, Synthetic; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D006031:Glycosylation; D006801:Humans; D006860:Hydrogen Bonding; D012503:Saponins / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014315:Triterpenes / Q000737:chemistry*; D053978:Pentacyclic Triterpenes
chemical_list: D000970:Antineoplastic Agents; D001089:Arabinose; D004187:Disaccharides; D012503:Saponins; D014315:Triterpenes; C480546:lupane; D053978:Pentacyclic Triterpenes
keywords: Glycosylation; Hydrogen bond network; Lupane saponins; OSW-1 disaccharide; SAR