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

Okada H, Fukushi E, Yamamori A, Kawazoe N, Onodera S, Kawabata J, Shiomi N - Chem Cent J (2009)

Bottom Line: 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.The following novel trisaccharides were identified: O-beta-D-fructofuranosyl-(2->1)-O-[beta-D-glucopyranosyl-(1->3)]-beta-D-glucopyranoside (named "3G-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).

View Article: PubMed Central - HTML - PubMed

Affiliation: Ohtakakohso, Co, Ltd, Otaru 047-0193, Japan. oelab@ohtakakohso.co.jp

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-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 "3G-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).

No MeSH data available.


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Part of HSQC (a) and HMBC (b) spectra of saccharide 2. ( ) = minor anomer.
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Figure 4: Part of HSQC (a) and HMBC (b) spectra of saccharide 2. ( ) = minor anomer.

Mentions: The NMR spectra of saccharide 2 showed that it was an anomeric mixture at the Glc. The α anomer was predominant. The COSY spectrum was assigned from H-1 to H-6. The C-4 showed the HMBC correlations between H-1" (Fig. 4(a) and 4(b)). The J (H-1"/H-2") value was 7.6–7.8 Hz. These results indicated the Glc" 1β ->4 Glc linkage, namely the cellobiose moiety. The C-2 showed the HMBC correlations to H-1'. The J (H-1'/H-2') value was 7.6 Hz. These results indicated the Glc' 1β ->2 Glc linkage, and all 1H and 13C NMR signals were assigned as shown in Additional file 3.


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

Okada H, Fukushi E, Yamamori A, Kawazoe N, Onodera S, Kawabata J, Shiomi N - Chem Cent J (2009)

Part of HSQC (a) and HMBC (b) spectra of saccharide 2. ( ) = minor anomer.
© Copyright Policy
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC2719632&req=5

Figure 4: Part of HSQC (a) and HMBC (b) spectra of saccharide 2. ( ) = minor anomer.
Mentions: The NMR spectra of saccharide 2 showed that it was an anomeric mixture at the Glc. The α anomer was predominant. The COSY spectrum was assigned from H-1 to H-6. The C-4 showed the HMBC correlations between H-1" (Fig. 4(a) and 4(b)). The J (H-1"/H-2") value was 7.6–7.8 Hz. These results indicated the Glc" 1β ->4 Glc linkage, namely the cellobiose moiety. The C-2 showed the HMBC correlations to H-1'. The J (H-1'/H-2') value was 7.6 Hz. These results indicated the Glc' 1β ->2 Glc linkage, and all 1H and 13C NMR signals were assigned as shown in Additional file 3.

Bottom Line: 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.The following novel trisaccharides were identified: O-beta-D-fructofuranosyl-(2->1)-O-[beta-D-glucopyranosyl-(1->3)]-beta-D-glucopyranoside (named "3G-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).

View Article: PubMed Central - HTML - PubMed

Affiliation: Ohtakakohso, Co, Ltd, Otaru 047-0193, Japan. oelab@ohtakakohso.co.jp

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-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 "3G-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).

No MeSH data available.


Related in: MedlinePlus