title: Application of MS and NMR to the structure elucidation of complex sugar moieties of natural products: exemplified by the steroidal saponin from Yucca filamentosa L.
abstract: An approach, using well characterized procedures, is presented that should be of general applicability for the structural elucidation of complex sugar moieties of natural products. The methods used are exemplified by the structure elucidation of a new gitogenin-based steroidal saponin that has a strong leishmanicidal activity similar to preparations used in clinical practice and has been isolated by bioactivity-guided fractionation of the ethanolic extract of Yucca filamentosa L. leaves. The saponin has been characterized as 3-O-((beta-D-glucopyranosyl-(1-->3)- beta-D-glucopyranosy-(1-->2))(alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->3))-beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranosyl)-25R,5alpha-spirostan-2alpha,3beta-diol.
authors.affiliation: Institut für Pharmazie, Humboldt-Universität zu Berlin, Germany.
authors.forename: A
authors.initials: A
authors.lastname: Plock
authors.forename: G
authors.initials: G
authors.lastname: Beyer
authors.forename: K
authors.initials: K
authors.lastname: Hiller
authors.forename: E
authors.initials: E
authors.lastname: Gründemann
authors.forename: E
authors.initials: E
authors.lastname: Krause
authors.forename: M
authors.initials: M
authors.lastname: Nimtz
authors.forename: V
authors.initials: V
authors.lastname: Wray
mesh_terms: D001688:Biological Products / Q000737:chemistry*; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002241:Carbohydrates / Q000032:analysis*; D019668:Liliaceae / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D013058:Mass Spectrometry / Q000379:methods; D008958:Models, Molecular; D008968:Molecular Conformation; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000737:chemistry / Q000302:isolation & purification; D010936:Plant Extracts / Q000737:chemistry; D012503:Saponins / Q000737:chemistry* / Q000302:isolation & purification; D013256:Steroids / Q000737:chemistry* / Q000302:isolation & purification
chemical_list: D001688:Biological Products; D002241:Carbohydrates; D009844:Oligosaccharides; D010936:Plant Extracts; D012503:Saponins; D013256:Steroids