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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.


High performance liquid chromatogram of fermentation products. A: The beverage of plant extract was fermented for 0 days. B: The beverage of plant extract was fermented for 180 days. The beverage (100 mL) fermented for 0 or 180 days was mixed with charcoal (10 g), stirred for 3 h. and filtered. The charcoal was extracted with 30% ethanol (500 mL) three times. The ethanol extracts were combined, concentrated to dryness and solubilized with one mL of distilled water. The sugar solution was analyzed by HPAEC.
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Figure 6: High performance liquid chromatogram of fermentation products. A: The beverage of plant extract was fermented for 0 days. B: The beverage of plant extract was fermented for 180 days. The beverage (100 mL) fermented for 0 or 180 days was mixed with charcoal (10 g), stirred for 3 h. and filtered. The charcoal was extracted with 30% ethanol (500 mL) three times. The ethanol extracts were combined, concentrated to dryness and solubilized with one mL of distilled water. The sugar solution was analyzed by HPAEC.

Mentions: Synthesis of the saccharides by fermentation of plant extracts was investigated using HPAEC. Almost all of the monosaccharides were removed from the fermented and unfermented beverages of plant extracts by the batch method with Charcoal. The saccharides 1, 2, and 3 were observed in the fermented beverage, but were not present in the unfermented one. Therefore, saccharides 1, 2, and 3 were confirmed to have been produced during fermentation of the beverage of plant extracts (Fig. 6).


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)

High performance liquid chromatogram of fermentation products. A: The beverage of plant extract was fermented for 0 days. B: The beverage of plant extract was fermented for 180 days. The beverage (100 mL) fermented for 0 or 180 days was mixed with charcoal (10 g), stirred for 3 h. and filtered. The charcoal was extracted with 30% ethanol (500 mL) three times. The ethanol extracts were combined, concentrated to dryness and solubilized with one mL of distilled water. The sugar solution was analyzed by HPAEC.
© Copyright Policy
Related In: Results  -  Collection

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

Figure 6: High performance liquid chromatogram of fermentation products. A: The beverage of plant extract was fermented for 0 days. B: The beverage of plant extract was fermented for 180 days. The beverage (100 mL) fermented for 0 or 180 days was mixed with charcoal (10 g), stirred for 3 h. and filtered. The charcoal was extracted with 30% ethanol (500 mL) three times. The ethanol extracts were combined, concentrated to dryness and solubilized with one mL of distilled water. The sugar solution was analyzed by HPAEC.
Mentions: Synthesis of the saccharides by fermentation of plant extracts was investigated using HPAEC. Almost all of the monosaccharides were removed from the fermented and unfermented beverages of plant extracts by the batch method with Charcoal. The saccharides 1, 2, and 3 were observed in the fermented beverage, but were not present in the unfermented one. Therefore, saccharides 1, 2, and 3 were confirmed to have been produced during fermentation of the beverage of plant extracts (Fig. 6).

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.