Research article

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

Hideki Okada¹ , Eri Fukushi² , Akira Yamamori¹ , Naoki Kawazoe¹ , Shuichi Onodera³ , Jun Kawabata² and Norio Shiomi³

¹  Ohtakakohso, Co, Ltd Otaru 047-0193, Japan

²  Graduate School of Agriculture, Hokkaido University, Sapporo 060-8589, Japan

³  Department of Food and Nutrition Sciences, Graduate School of Dairy Science Research, Rakuno Gakuen University, Ebetsu 069-8501, Japan

author email corresponding author email

Chemistry Central Journal 2009, 3:8doi:10.1186/1752-153X-3-8

Published:	16 July 2009

Abstract

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-β-D-fructopyranosyl-(2->6)-O-β-D-glucopyranosyl-(1->3)-D-glucopyranose, O-β-D-fructopyranosyl-(2->6)-O-[β-D-glucopyranosyl-(1->3)]-D-glucopyranose, O-β-D-glucopyranosyl-(1->1)-O-β-D-fructofuranosyl-(2<->1)-α-D-glucopyranoside and O-β-D-galactopyranosyl-(1->1)-O-β-D-fructofuranosyl-(2<->1)- α-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-β-D-fructofuranosyl-(2->1)-O-[β-D-glucopyranosyl-(1->3)]-β-D-glucopyranoside (named "3^G-β-D-glucopyranosyl β, β-isosucrose"), O-β-D-glucopyranosyl-(1->2)-O-[β-D-glucopyranosyl-(1->4)]-D-glucopyranose (4¹-β-D-glucopyranosyl sophorose) and O-β-D-fructofuranosyl-(2->6)-O-β-D-glucopyranosyl-(1->3)-D-glucopyranose (6²-β-D-fructofuranosyl laminaribiose).