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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.


Related in: MedlinePlus

Part of HSQC-TOCSY (a) and HMBC (b) spectra of saccharide 3. ( ) = minor anomer.
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Figure 5: Part of HSQC-TOCSY (a) and HMBC (b) spectra of saccharide 3. ( ) = minor anomer.

Mentions: The NMR spectra of saccharide 3 were analyzed in the same manner as those of saccharide 2. Saccharide 3 was also an anomeric mixture at the Glc'. The β anomer was predominant. The HSQC-TOCSY spectrum revealed the1H and 13C signals of each Glc, Glc' and Fru. The isolated methylene was assigned as H-1" and C-1". The other three methylene carbons were assigned as C-6 in these residues (Fig. 5(a)). The position of the glucosidic linkage and fructosidic linkage was analyzed as follows. The C-3' showed the HMBC correlations between H-1 (Fig. 5(b)). The J (H-1/H-2) value was 7.9 Hz. These results indicated the Glc 1β ->3 Glc' linkage, namely the laminaribiose moiety. The C-2 showed the HMBC correlations to H-6. These results indicated the Glc 6 <-2 β Fru 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-TOCSY (a) and HMBC (b) spectra of saccharide 3. ( ) = minor anomer.
© Copyright Policy
Related In: Results  -  Collection

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

Figure 5: Part of HSQC-TOCSY (a) and HMBC (b) spectra of saccharide 3. ( ) = minor anomer.
Mentions: The NMR spectra of saccharide 3 were analyzed in the same manner as those of saccharide 2. Saccharide 3 was also an anomeric mixture at the Glc'. The β anomer was predominant. The HSQC-TOCSY spectrum revealed the1H and 13C signals of each Glc, Glc' and Fru. The isolated methylene was assigned as H-1" and C-1". The other three methylene carbons were assigned as C-6 in these residues (Fig. 5(a)). The position of the glucosidic linkage and fructosidic linkage was analyzed as follows. The C-3' showed the HMBC correlations between H-1 (Fig. 5(b)). The J (H-1/H-2) value was 7.9 Hz. These results indicated the Glc 1β ->3 Glc' linkage, namely the laminaribiose moiety. The C-2 showed the HMBC correlations to H-6. These results indicated the Glc 6 <-2 β Fru 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