title: Noniosides E - H, new trisaccharide fatty acid esters from the fruit of Morinda citrifolia (Noni).
abstract: Four new trisaccharide fatty acid esters named noniosides E - H ( 4 - 7) were isolated from the fruit of Morinda citrifolia (Noni) by a combination of Sephadex LH-20, high-speed countercurrent chromatography (HSCCC) and semipreparative HPLC. Their structures were elucidated by high resolution mass spectrometry and 1D- and 2D-NMR as 2,6-di- O-(beta-D-glucopyranosyl)-1-O-hexanoyl-beta-D-glucopyranose (4), 2,6-di-O-(beta-D-glucopyranosyl)-1-O-decanoyl-beta-D-glucopyranose (5), 2-O-(6-O-octanoyl-beta-D-glucopyranosyl)-6-O-(beta-D-glucopyranosyl)-1-O-octanoyl-beta-D-glucopyranose (6), and 2-O-(6-O-hexanoyl-beta-D-glucopyranosyl)-6-O-(beta-D-glucopyranosyl)-1-O-octanoyl-beta-D-glucopyranose or 2-O-(6-O-octanoyl-beta-D-glucopyranosyl)-6-O-(beta-D-glucopyranosyl)-1-O-hexanoyl-beta-D-glucopyranose (7), respectively. In addition, an HPLC-MS analysis of a methanolic extract of the fruit powder revealed the presence of further derivatives including new disaccharide and trisaccharide esters with fatty acid residues of various lengths.
authors.affiliation: Institute of Pharmaceutical Biology, University of Basel, Basel, Switzerland.
authors.forename: Petur W
authors.initials: PW
authors.lastname: Dalsgaard
authors.forename: Olivier
authors.initials: O
authors.lastname: Potterat
authors.forename: Fiona
authors.initials: F
authors.lastname: Dieterle
authors.forename: Thomas
authors.initials: T
authors.lastname: Paululat
authors.forename: Till
authors.initials: T
authors.lastname: Kühn
authors.forename: Matthias
authors.initials: M
authors.lastname: Hamburger
mesh_terms: D002851:Chromatography, High Pressure Liquid; D004952:Esters / Q000737:chemistry; D005227:Fatty Acids / Q000737:chemistry; D005638:Fruit; D006017:Glycolipids / Q000737:chemistry*; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D032066:Morinda; D008517:Phytotherapy; D010936:Plant Extracts / Q000737:chemistry*; D014312:Trisaccharides / Q000737:chemistry
chemical_list: D004952:Esters; D005227:Fatty Acids; D006017:Glycolipids; D010936:Plant Extracts; D014312:Trisaccharides