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Three fructooligosaccharide derivatives without a terminal glucose residue, designated saccharides 1, 2 and 3, were generated in the stored burdock roots. They were purified from the sugar extract using carbon-Celite column chromatography. Saccharides 1, 2 and 3 have R-sucrose values (retention time of sucrose = 1) of 1.55, 2.15 and 2.73 by HPAEC, reducing terminal, molar ratios (reducing sugar to D-fructose) of 0.50, 0.33 and 0.25 and degrees of polymerization of 2, 3 and 4 by TOF-MS, respectively. Analyses by GLC and NMR confirmed the three different following structures: first was inulobiose [β-D-fructofuranosyl-(2→1)-β-D-fructopyranose], and the two others were inulotriose [β-D-fructofuranosyl-(2→1)-β-D-fructofuranosyl-(2→1)-β-D-fructopyranose] and inulotetraose [β-D-fructofuranosyl-(2→1)-β-D-fructofuranosyl-(2→1)-β-D-fructopyranose]. The NMR spectra showed that 70 to 80 % of the terminal fructose residue of the three saccharides is pyranosyl form, while 20 to 30 % is furanosyl form. The ^\u003c13\u003eC_- and ^1H-signals were also assigned by 2D-NMR including COSY, HSQC, HSQC-TOCSY and HMBC. These saccharides could be synthesized by purified burdock fructan:fructan 1-frustosyltransferase from 1-kestose to free D-fructopyranose giving inulobiose and sucrose, while elongation of fructoranosyl units occurred at this trasferred fructofuranosyl residue to produce inuloolisaccharides having one, two and more additional units of fructofuranose. 新鮮ごぼう根を地下1mの土中で11月から翌年の5月まで6カ月間貯蔵した。この貯蔵ごぼうに末端グルコース残基を有しないフルクトオリゴ糖が新しく生成された。このごぼうから抽出した糖液について電気化学検出器付陰イオン交換高速液体クロマトグラフィー(HPAEC)分析を行ったところ,糖1は1- kestose (3a)のあとに溶出され,糖2,3はnystose (4a), fructosylnystose (5a)のあとにそれぞれ溶出された。この糖抽出液について活性炭-セライトカラムクロマトグラフィーを行うことにより糖1,2,3を単離した。糖 1,2,3はHPAECによる相対保持時間(sucrose = 1),1.55,2.15,2.73を有し,還元末端をそれぞれもっていた。また,糖1,2,3のフルクトースに対する還元糖の比は 0.50,0.33,0.25であることとTOF-MS分析の結果から糖1,2,3の重合度は2,3,4であることがわかった。これらの結果と各糖の NMR分析,糖メチル誘導体のGLC分析結果から,糖1,2,3はそれぞれβ-D-fructofuranosyl-(2→1)-β-D-fructopyranose (inulobiose),β-D-fructofuranosyl-(2→1)-β-D-fructofuranosyl-(2→1)-β-D-fructopyranose (inulotriose),β-D-fructofuranosyl-(2→1)-β-D-fructofuranosyl-(2→1)-β-D-fructofuranosyl-(2→1)-β-D-fructo-pyranose (inulotetraose)と同定された。13C-NMR分析により各糖の還元末端フルクトース残基の70-80%がピラノース構造をとることがわかった。それぞれの糖の13C-,1H- シグナルの完全帰属も初めて行った。さらに上述のごぼう貯蔵中に生成されたinulobiose,inulotriose,inulotetraoseと同様の糖が,ごぼうから精製したfructan fructan 1-fructosyltransferase (1-FFT)のフルクトシル転移作用により1-kestoseとD-フルクトピラノースから合成されることを初めて見出した。", "subitem_description_type": "Abstract"}]}, "item_2_full_name_3": {"attribute_name": "著者別名", "attribute_value_mlt": [{"nameIdentifiers": [{"nameIdentifier": "2855", "nameIdentifierScheme": "WEKO"}], "names": [{"name": "石黒, 陽二郎"}]}, {"affiliations": [{"affiliationNames": [{"affiliationName": "", "lang": "ja"}], "nameIdentifiers": [{"nameIdentifier": "", "nameIdentifierScheme": "ISNI", "nameIdentifierURI": "http://www.isni.org/isni/"}]}], "familyNames": [{"familyName": "上野", "familyNameLang": ""}], "givenNames": [{"givenName": "敬司", "givenNameLang": ""}], "nameIdentifiers": [{"nameIdentifier": "2856", 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"permalink_uri": "http://hdl.handle.net/10659/1764", "pubdate": {"attribute_name": "公開日", "attribute_value": "2011-03-31"}, "publish_date": "2011-03-31", "publish_status": "0", "recid": "1261", "relation": {}, "relation_version_is_last": true, "title": ["Isolation and structural determination of reducing fructooligosaccharides newly produced in stored edible burdock"], "weko_shared_id": -1}
Isolation and structural determination of reducing fructooligosaccharides newly produced in stored edible burdock
http://hdl.handle.net/10659/1764
http://hdl.handle.net/10659/176445d2004a-d179-46ea-aa8c-4de2f2775e6e
名前 / ファイル | ライセンス | アクション |
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S-809_Ueno.pdf (750.5 kB)
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Item type | 学術雑誌論文 / Journal Article(1) | |||||
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公開日 | 2011-03-31 | |||||
タイトル | ||||||
タイトル | Isolation and structural determination of reducing fructooligosaccharides newly produced in stored edible burdock | |||||
言語 | ||||||
言語 | eng | |||||
資源タイプ | ||||||
資源タイプ識別子 | http://purl.org/coar/resource_type/c_6501 | |||||
資源タイプ | journal article | |||||
著者 |
Ishiguro, Yojiro
× Ishiguro, Yojiro× Ueno, Keiji× Abe, Masami× Onodera, Shuichi× Fukushi, Eri× Benkeblia, Noureddine× Shiomi, Norio |
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著者別名 | ||||||
姓名 | 石黒, 陽二郎 | |||||
著者別名 | ||||||
姓名 | 上野, 敬司 | |||||
著者別名 | ||||||
姓名 | 阿部, 雅美 | |||||
著者別名 | ||||||
姓名 | 小野寺, 秀一 | |||||
著者別名 | ||||||
姓名 | 福士, 江里 | |||||
著者別名 | ||||||
姓名 | 塩見, 徳夫 | |||||
抄録 | ||||||
内容記述タイプ | Abstract | |||||
内容記述 | Fresh edible burdock roots were stored in soil of 1 m depth underground from November to May. Three fructooligosaccharide derivatives without a terminal glucose residue, designated saccharides 1, 2 and 3, were generated in the stored burdock roots. They were purified from the sugar extract using carbon-Celite column chromatography. Saccharides 1, 2 and 3 have R-sucrose values (retention time of sucrose = 1) of 1.55, 2.15 and 2.73 by HPAEC, reducing terminal, molar ratios (reducing sugar to D-fructose) of 0.50, 0.33 and 0.25 and degrees of polymerization of 2, 3 and 4 by TOF-MS, respectively. Analyses by GLC and NMR confirmed the three different following structures: first was inulobiose [β-D-fructofuranosyl-(2→1)-β-D-fructopyranose], and the two others were inulotriose [β-D-fructofuranosyl-(2→1)-β-D-fructofuranosyl-(2→1)-β-D-fructopyranose] and inulotetraose [β-D-fructofuranosyl-(2→1)-β-D-fructofuranosyl-(2→1)-β-D-fructopyranose]. The NMR spectra showed that 70 to 80 % of the terminal fructose residue of the three saccharides is pyranosyl form, while 20 to 30 % is furanosyl form. The ^<13>C_- and ^1H-signals were also assigned by 2D-NMR including COSY, HSQC, HSQC-TOCSY and HMBC. These saccharides could be synthesized by purified burdock fructan:fructan 1-frustosyltransferase from 1-kestose to free D-fructopyranose giving inulobiose and sucrose, while elongation of fructoranosyl units occurred at this trasferred fructofuranosyl residue to produce inuloolisaccharides having one, two and more additional units of fructofuranose. 新鮮ごぼう根を地下1mの土中で11月から翌年の5月まで6カ月間貯蔵した。この貯蔵ごぼうに末端グルコース残基を有しないフルクトオリゴ糖が新しく生成された。このごぼうから抽出した糖液について電気化学検出器付陰イオン交換高速液体クロマトグラフィー(HPAEC)分析を行ったところ,糖1は1- kestose (3a)のあとに溶出され,糖2,3はnystose (4a), fructosylnystose (5a)のあとにそれぞれ溶出された。この糖抽出液について活性炭-セライトカラムクロマトグラフィーを行うことにより糖1,2,3を単離した。糖 1,2,3はHPAECによる相対保持時間(sucrose = 1),1.55,2.15,2.73を有し,還元末端をそれぞれもっていた。また,糖1,2,3のフルクトースに対する還元糖の比は 0.50,0.33,0.25であることとTOF-MS分析の結果から糖1,2,3の重合度は2,3,4であることがわかった。これらの結果と各糖の NMR分析,糖メチル誘導体のGLC分析結果から,糖1,2,3はそれぞれβ-D-fructofuranosyl-(2→1)-β-D-fructopyranose (inulobiose),β-D-fructofuranosyl-(2→1)-β-D-fructofuranosyl-(2→1)-β-D-fructopyranose (inulotriose),β-D-fructofuranosyl-(2→1)-β-D-fructofuranosyl-(2→1)-β-D-fructofuranosyl-(2→1)-β-D-fructo-pyranose (inulotetraose)と同定された。13C-NMR分析により各糖の還元末端フルクトース残基の70-80%がピラノース構造をとることがわかった。それぞれの糖の13C-,1H- シグナルの完全帰属も初めて行った。さらに上述のごぼう貯蔵中に生成されたinulobiose,inulotriose,inulotetraoseと同様の糖が,ごぼうから精製したfructan fructan 1-fructosyltransferase (1-FFT)のフルクトシル転移作用により1-kestoseとD-フルクトピラノースから合成されることを初めて見出した。 | |||||
書誌情報 |
Journal of applied glycoscience 巻 56, 号 3, p. 159-164, 発行日 2009-09 |
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ISSN | ||||||
収録物識別子タイプ | ISSN | |||||
収録物識別子 | 1344-7882 | |||||
著者版フラグ | ||||||
出版タイプ | VoR | |||||
出版タイプResource | http://purl.org/coar/version/c_970fb48d4fbd8a85 | |||||
出版者 | ||||||
出版者 | 日本応用糖質科学会 | |||||
資源タイプ | ||||||
内容記述タイプ | Other | |||||
内容記述 | Article |