Two novel oligosaccharides isolated from a beverage produced by fermentation of a plant extract

An extract from 50 kinds of fruits and vegetables was fermented to produce a new beverage. Natural fermentation of the extract was carried out mainly by lactic acid bacteria (Leuconostoc spp.) and yeast (Zygosaccharomyces spp. and Pichia spp.). Two new saccharides were found in this fermented beverage. The saccharides were isolated using carbon–Celite column chromatography and preparative high performance liquid chromatography. Gas liquid chromatography analysis of methylated derivatives as well as MALDI-TOF MS and NMR measurements were used for structural confirmation. The 1H and 13C NMR signals of each saccharide were assigned using 2D-NMR including COSY, HSQC, HSQC-TOCSY, CH2-HSQC-TOCSY, and CT-HMBC experiments. The saccharides were identified as β-d-fructopyranosyl-(2→6)-β-d-glucopyranosyl-(1→3)-d-glucopyranose and β-d-fructopyranosyl-(2→6)-[β-d-glucopyranosyl-(1→3)]-d-glucopyranose.