title: In vitro anticancer studies of alpha- and beta-D-glucopyranose betulin anomers.
abstract: Four derivatives of betulin containing a D-glucopyranosyl moiety at C3 position were synthesized and characterized by (1)H and (13)C NMR spectroscopy as well as mass spectrometry. The crystal structure of 28-O-acetylbetulin-3-yl-beta-D-(2',3',4',6'-tetra-O-acetyl)glucopyranoside was determined. The compounds were tested against fifteen tumor cell lines of different histogenic origins. The alpha- and beta-anomers of 28-O-acetylbetulin-3-yl-D-glucopyranoside, exerted a dose dependent antiproliferative action towards the tumor cell lines. Treatment of HCT-116 cells for 24h induced apoptosis, which was confirmed by the appearance of a typical ladder pattern in the DNA fragmentation assay and cell cycle analysis. The alpha- and beta-anomers of 28-O-acetylbetulin-3-yl-D-glucopyranoside seem to induce apoptosis by activation of different upstream caspases on colon cancer HCT-116 cell line.
authors.affiliation: Martin-Luther-Universität Halle-Wittenberg, Halle, Germany.
authors.forename: Harish
authors.initials: H
authors.lastname: Kommera
authors.forename: Goran N
authors.initials: GN
authors.lastname: Kaluderović
authors.forename: Martin
authors.initials: M
authors.lastname: Bette
authors.forename: Jutta
authors.initials: J
authors.lastname: Kalbitz
authors.forename: Petra
authors.initials: P
authors.lastname: Fuchs
authors.forename: Simone
authors.initials: S
authors.lastname: Fulda
authors.forename: Walter
authors.initials: W
authors.lastname: Mier
authors.forename: Reinhard
authors.initials: R
authors.lastname: Paschke
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D017209:Apoptosis / Q000187:drug effects* / Q000502:physiology; D053148:Caspase 3 / Q000378:metabolism; D002453:Cell Cycle / Q000187:drug effects / Q000502:physiology; D045744:Cell Line, Tumor; D053938:DNA Fragmentation / Q000187:drug effects; D004354:Drug Screening Assays, Antitumor; D005947:Glucose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D045325:HCT116 Cells; D006801:Humans; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D053978:Pentacyclic Triterpenes; D013997:Time Factors; D014315:Triterpenes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D014961:X-Ray Diffraction; D000094062:Betulinic Acid
chemical_list: D000970:Antineoplastic Agents; D053978:Pentacyclic Triterpenes; D014315:Triterpenes; C002503:betulin; D053148:Caspase 3; D005947:Glucose; D000094062:Betulinic Acid