title: New analogues of the potent cytotoxic saponin OSW-1.
abstract: Saponin OSW-1 (5e-G2; 3 beta,16 beta,17 alpha-trihydroxycholest-5-en-22-one 16-O-{O-[2-O-(4-methoxybenzoyl)-beta-D-xylopyranosyl]-(1-->3)-2-O-acetyl-alpha-arabinopyranoside}) analogues: with modified side chain (5a/d-G2), 22-deoxo-23,24,25,26,27-pentanor- (14), 22-deoxo-23-oxa- (17), glycosylated with various monosaccharides (5e-G4/G6/G8), and OSW-1 structural isomer (10) were obtained. The analogues were synthesized using a previously published method for the synthesis of OSW-1. The structures of analogues were fully confirmed by spectroscopic methods, and the S-chirality at C-22 of the structural isomer was established by conformational analysis combined with the NMR spectrometry. The cytotoxicity of the analogues toward several types of malignant tumor cells was examined and compared with that of OSW-1. The results suggest that modification of the steroidal aglycone may lead to compounds with high cytotoxicity.
authors.affiliation: Institute of Chemistry, University of Białystok, al. Pilsudskiego 11/4, 15-443 Bialystok, Poland. jeremy@uwb.edu.pl
authors.forename: Agnieszka
authors.initials: A
authors.lastname: Wojtkielewicz
authors.forename: Maciej
authors.initials: M
authors.lastname: Długosz
authors.forename: Jadwiga
authors.initials: J
authors.lastname: Maj
authors.forename: Jacek W
authors.initials: JW
authors.lastname: Morzycki
authors.forename: Michał
authors.initials: M
authors.lastname: Nowakowski
authors.forename: Joanna
authors.initials: J
authors.lastname: Renkiewicz
authors.forename: Miroslav
authors.initials: M
authors.lastname: Strnad
authors.forename: Jana
authors.initials: J
authors.lastname: Swaczynová
authors.forename: Agnieszka Z
authors.initials: AZ
authors.lastname: Wilczewska
authors.forename: Jacek
authors.initials: J
authors.lastname: Wójcik
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor; D002783:Cholestenones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D012503:Saponins / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D002783:Cholestenones; D012503:Saponins; C106408:OSW 1