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-(β-D-glucopyranosyl)-1-O-hexanoyl-β-D-glucopyranose (4), 2,6-di-O-(β-D-glucopyranosyl)-1-O-decanoyl-β-D-glucopyranose (5), 2-O-(6-O-octanoyl-β-D-glucopyranosyl)-6-O-(β-D-glucopyranosyl)-1-O-octanoyl-β-D-glucopyranose (6), and 2-O-(6-O-hexanoyl-β-D-glucopyranosyl)-6-O-(β-D-glucopyranosyl)-1-O-octanoyl-β-D-glucopyranose or 2-O-(6-O-octanoyl-β-D-glucopyranosyl)-6-O-(β-D-glucopyranosyl)-1-O-hexanoyl-β-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.

Key words

Morinda citrifolia - Rubiaceae - trisaccharide fatty acid esters - fatty acid glucosides - fatty alcohol glucosides - noniosides - HSCCC - novel food

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