Structural analysis of three novel trisaccharides isolated from the fermented beverage of plant extracts

Background: A fermented beverage of plant extracts was prepared from about fifty kinds of vegetables and fruits. Natural fermentation was carried out mainly by lactic acid bacteria (Leuconostoc spp.) and yeast (Zygosaccharomyces spp. and Pichia spp.). We have previously examined the preparation of novel four trisaccharides from the beverage: O-beta-D-fructopyranosyl-(2-> 6)-O-beta-D-glucopyranosyl-(1-> 3)-D-glucopyranose, O-beta-D-fructopyranosyl-(2-> 6)-O-[beta-D-glucopyranosyl-(1-> 3)]-D-glucopyranose, O-beta-D-glucopyranosyl-(1-> 1)-O-beta-D-fructofuranosyl( 2 <-> 1)-alpha-D-glucopyranoside and O-beta-D-galactopyranosyl-(1-> 1)-O-beta-D-fructofuranosyl-(2 <-> 1)-alpha-D-glucopyranoside. Results: Three further novel oligosaccharides have been found from this beverage and isolated from the beverage using carbon-Celite column chromatography and preparative high performance liquid chromatography. Structural confirmation of the saccharides was provided by methylation analysis, MALDI-TOF-MS and NMR measurements. Conclusion: The following novel trisaccharides were identified: O-beta-D-fructofuranosyl-(2-> 1)-O-[beta-D-glucopyranosyl-(1-> 3)]-beta-D-glucopyranoside (named 3(G)-beta-D-glucopyranosyl beta, beta-isosucrose), O-beta-D-glucopyranosyl-(1-> 2)-O-[beta-D-glucopyranosyl-(1-> 4)]-D-glucopyranose (4(1)-beta-D-glucopyranosyl sophorose) and O-beta-D-fructofuranosyl-(2-> 6)-O-beta-D-glucopyranosyl-(1-> 3)D-glucopyranose (6(2)-beta-D-fructofuranosyl laminaribiose).