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

Chemistry Central Journal, Dec 2009

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 "3G-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).

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

Hideki Okada 2 Eri Fukushi 1 Akira Yamamori 2 Naoki Kawazoe 2 Shuichi Onodera 0 Jun Kawabata 1 Norio Shiomi 0 0 Department of Food and Nutrition Sciences, Graduate School of Dairy Science Research, Rakuno Gakuen University , Ebetsu 069-8501, Japan 1 Graduate School of Agriculture, Hokkaido University , Sapporo 060-8589, Japan 2 Ohtakakohso, Co , Ltd Otaru 047-0193, Japan 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--D-fructopyranosyl-(2->6)-O-D-glucopyranosyl-(1->3)-D-glucopyranose, O--D-fructopyranosyl-(2->6)-O-[-Dglucopyranosyl-(1->3)]-D-glucopyranose, O--D-glucopyranosyl-(1->1)-O--D-fructofuranosyl(2<->1)--D-glucopyranoside and O--D-galactopyranosyl-(1->1)-O--D-fructofuranosyl-(2<->1)-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. - Background A beverage was produced by fermentation of an extract from 50 kinds of fruits and vegetables (see Additional file 1) [1,2]. The extract was obtained using sucrose-osmotic pressure in a cedar barrel for seven days and was fermented by lactic acid bacteria (Leuconostoc spp.) and yeast (Zygosaccharomyces spp. and Pichia spp.) for 180 days. The fermented beverage showed scavenging activity against 1,1'-diphenyl-2-picrylhydrazyl (DPPH) radicals, and significantly reduced the ethanol-induced damage of gastric mucosa in rats [1]. Analysis by high performance anion exchange chromatography (HPAEC) showed that this beverage contained high levels of saccharides, estimated between 550 and 590 g/L; mainly glucose and fructose, and a small amount of undetermined oligosaccharides. Recently, it was reported that different positions of glycosidic linkage of oligosaccharide isomers affected physiological properties as well as physical properties [3-5]. Development of HPLC analysis with high sensitivity and separation ability enables the detection and isolation of oligosaccharides in the fermented beverage. We have previously examined the preparation of saccharides of the fructopyranoside series from the fermented beverage of plant extracts, such as O--D-fructopyranosyl(2->6)-D-glucopyranose [2], O--D-fructopyranosyl-(2>6)-O--D-glucopyranosyl-(1->3)-D-glucopyranose and O--D-fructopyranosyl-(2->6)-O-[-D-glucopyranosyl(1->3)]-D-glucopyranose [6]. The characteristics of O-D-fructopyranosyl-(2->6)-D-glucopyranose were non-cariogenicity and low digestibility, and the unfavorable bacteria that produce mutagenic substances did not use the saccharide [7,8]. Recently, we have studied isolation and identification of novel non-reducing trisaccharides, such as O--D-glucopyranosyl-(1->1)-O--D-fructofuranosyl(2<->1)--D-glucopyranoside and O--D-galactopyranosyl-(1->1)-O--D-fructofuranosyl-(2<->1)- -D-glucopyranoside from the beverage [9], and those saccharides were confirmed to be produced by fermentation. In this paper, we have confirmed structures of the novel trisaccharides (Fig. 1): O--D-fructofuranosyl-(2->1)-O[-D-glucopyranosyl-(1->3)]--D-glucopyranoside (named "3G--D-glucopyranosyl , -isosucrose"), O-D-glucopyranosyl-(1->2)-O-[-D-glucopyranosyl-(1>4)]-D-glucopyranose (41--D-glucopyranosyl sophorose) and O--D-fructofuranosyl-(2->6)-O--D-glucopyranosyl-(1->3)-D-glucopyranose (62--Dfructofuranosyl laminaribiose), isolated from the fermented beverage using methylation analysis, MALDITOF-MS and NMR measurements. Results and discussion Saccharides 1, 2 and 3 were isolated from the fermented beverage of plant extracts using carbon-Celite column chromatography, and were shown to be homogeneous using anion exchange HPLC [tR, sucrose (relative retention time; retention time of sucrose = 1.0): 1.89, 2.23 and 2.40 respectively]. The retention time of saccharides 1, 2 and 3 did not correspond to that of any authentic saccharides [glucose (0.62), fructose (0.68), sucrose (1.00), maltose (1.43), trehalose (0.58), laminaribiose (1.33), raffinose (1.23), 1-kestose (1.47), 6-kestose (1.75), neokestose (1.90), maltotriose (2.59), panose (1.87), nystose (2.06), fructosylnystose (3.81), O--D-fructopyranosyl-(2->6)-Dglucopyranose (0.83) [2], O--D-fructopyranosyl-(2->6)O--D-glucopyranosyl-(1->3)-D-glucopyranose (1.74) [6], O--D-fructopyranosyl-(2->6)-O-[-D-glucopyranosyl-(1->3)]-D-glucopyranose (1.72) [6], O--D-glucopyranosyl-(1->1)-O--D-fructofuranosyl-(2<->1)- -Dglucopyranoside (1.24) [9], O--D-galactopyranosyl-(1 HO HO 5 O 2 3 Glc OH 1 3 Glc O 1 OH OH gySFlrtiuragcunuocortpseuyrrl1e-a(sn1o->sfey23Ol)-(-](2-1 (...truncated)


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Hideki Okada, Eri Fukushi, Akira Yamamori, Naoki Kawazoe, Shuichi Onodera, Jun Kawabata, Norio Shiomi. Structural analysis of three novel trisaccharides isolated from the fermented beverage of plant extracts, Chemistry Central Journal, 2009, pp. 8, Volume 3, Issue 1, DOI: 10.1186/1752-153X-3-8