Noniosides E-H, new trisaccharide fatty acid esters from the fruit of Morinda citrifolia (Noni)

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 sernipreparative 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-glucopyranosy)-1-O-decanoyl-beta-D-glucopyranose (5), 2-O-(6-O-octanoyl-beta-Dglucopyranosyl)-6-O-(beta-D-glucopyranosyl)-1 -O-octanoyl-beta-D-copyranose (6), and 2-O-(6-O-hexanoyl-beta-D-glucopyranosyl)-6-O-(beta-D-glucopyranosyl)-1-O-octanoyl-beta-D-glucopyranose or O-(6-O-octanoyl-beta-D-glucopyranosyl)-6-O-(beta-D-glucopyranosyl)-1-O-hexanoyl-beta-D-ghlcopyranose (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.