JP6762027B2 - シアロオリゴ糖の製造方法とその利用 - Google Patents
シアロオリゴ糖の製造方法とその利用 Download PDFInfo
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- JP6762027B2 JP6762027B2 JP2016164565A JP2016164565A JP6762027B2 JP 6762027 B2 JP6762027 B2 JP 6762027B2 JP 2016164565 A JP2016164565 A JP 2016164565A JP 2016164565 A JP2016164565 A JP 2016164565A JP 6762027 B2 JP6762027 B2 JP 6762027B2
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- Prior art keywords
- sialic acid
- test substance
- aqueous solution
- sialooligosaccharide
- production method
- Prior art date
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07G—COMPOUNDS OF UNKNOWN CONSTITUTION
- C07G99/00—Subject matter not provided for in other groups of this subclass
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- A—HUMAN NECESSITIES
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/702—Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages
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- A—HUMAN NECESSITIES
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- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/125—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives containing carbohydrate syrups; containing sugars; containing sugar alcohols; containing starch hydrolysates
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- A—HUMAN NECESSITIES
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Description
シアル酸は細胞間識別機能、感染防御活性、免疫機能制御機能、ミオバチー(Myopathy)改善機能、発毛・育毛機能等を有することが報告されている(非特許文献1〜3)。
[1](1)シアロ糖タンパク質をアルカリ性水溶液中で70〜90℃に加温することにより加水分解する工程;および
(2)加水分解物を精製してシアロオリゴ糖を得る工程;
を含む、含有するシアル酸/ヘキソースの重量比が0.5〜0.9であるシアロオリゴ糖の製造方法。
[3]シアロ糖タンパク質がアナツバメ族の巣に含まれるムチン型糖タンパク質である、[1]または[2]に記載の製造方法。
[5]精製が逆浸透膜濾過または電気透析により行われる、[1]〜[4]のいずれかに記載の製造方法。
(2)加水分解物を精製してシアロオリゴ糖を得る工程;
を含む製造方法によって製造される、含有するシアル酸/ヘキソースの重量比が0.5〜0.9であるシアロオリゴ糖。
[8][6]に記載のシアロオリゴ糖を含む、骨格筋形成促進剤。
本明細書において、「シアル酸」とは、ノイラミン酸のアミノ基やヒドロキシ基が置換された物質を総称するファミリー名である。
本明細書において「ムチン型」とは、ムチンの糖タンパク質にみられる糖鎖とタンパク質の結合様式である。主にセリンまたはトレオニンの水酸基に対し、糖鎖の還元末端のN−アセチルガラクトサミンがα−O−グリコシド結合(ムチン型結合)により高頻度で結合している。
(1)シアロ糖タンパク質をアルカリ性水溶液中で加温することにより加水分解する工程;および
(2)加水分解物を精製してシアロオリゴ糖を得る工程
本発明のシアロオリゴ糖の製造に用いるシアロ糖タンパク質は単離されたものであってもよく、他の成分を含むものであってもよい。好ましくは、ムチン型のシアロ糖タンパク質を含むムチンである。
アルカリ水溶液に用いるアルカリとしては、水酸化カリウム、水酸化ナトリウムなどが挙げられる。
加温は、例えば50〜105℃、好ましくは70〜90℃、より好ましくは75〜85℃で、例えば30分〜3時間、好ましくは30分〜2時間、より好ましくは1〜2時間行う。
加水分解物の精製は、例えば逆浸透膜濾過、透析、電気透析、限外濾過、好ましくは逆浸透膜濾過、透析、または電気透析、より好ましくは逆浸透膜濾過または電気透析により行うことができる。
特に、原料に含まれうる重金属やヒ素の除去の観点から、一態様として、加水分解物を電気透析により精製するのが好ましい。
本発明の製造方法で原料として使用されるシアロ糖タンパク質の例としては、シアロ糖タンパク質を含有する物質、例えば、アナツバメ族の鳥の巣、牛乳などの動物の乳、鶏卵などの動物の卵、家畜などの動物の唾液・消化液、ナマコなどの棘皮動物、クラゲなどの刺胞動物などの天然由来の物質、好ましくはムチンを含有する物質が挙げられる。
アナツバメ族の鳥の巣のムチンに含まれるシアロ糖タンパク質からシアロオリゴ糖を得る場合、酸性条件下ではシアル酸がオリゴ糖から脱離してしまうため、希アルカリ性のマイルドな条件下で加水分解を行う。他のムチン型シアロ糖タンパク質からシアロオリゴ糖を得る場合も、本発明の方法を適用できる。したがって、シアロオリゴ糖の原料をアナツバメ族の鳥の巣に限定するものではない。
希アルカリ処理による方法
市販のアナツバメ(学名:Aerodramus fuciphagus germani)の巣(10g、インドネシアの中国食材店より入手)を1000mlの0.25重量%水酸化カリウム水溶液に加え、ミキサーで粉砕した。80℃に加温し、40分保持した。4℃に冷却した後、遠心分離および濾過により不溶物を除去した。その後、電気透析で塩および不純物を除去し、乾燥させて3.33gを回収し、被験物質1とした。
従来から糖タンパク質から糖を遊離させるのに用いられている酸加水分解の手法を、対比として行った。
被験物質1および2のそれぞれを、1mg/mlの濃度で0.1Mリン酸緩衝液(pH6.8)に溶解させ、ゲル濾過クロマトグラフィー(GFC)を用いて分離分析した。
樹脂:トヨパールHW40S(東ソー社製)(排除限界分子量:〜10,000Da)
カラム:内径20mm×カラム長950mm(山善社製MMカラム(内径20mm×長さ1,000mm)に上記樹脂を950mmの長さで充填して作製)
移動相:0.1Mリン酸緩衝液(pH6.8)
インジェクション:1ml(負荷量:1mg)(ATTO社製インジェクタを使用)
流速:0.3ml/分(Lab−Quatec社製ポンプ、型番:WORK−21,LP6300を使用)
分取:2ml/チューブ(Gilson社製フラクションコレクター、型番:FC203Bを使用)
検出波長:265nmおよび480nm
GFC溶出パターンを図1に示す。
被験物質1が含有するオリゴ糖がシアロオリゴ糖であること、被験物質2にヘキソースが含まれていないことを確認するため、被験物質中のシアル酸量およびヘキソース量の測定を行った。
すなわち、1mlの試料溶液にp‐ジメチルアミノベンズアルデヒド(5g)を塩酸と水の等容量混合液100mlに溶解した試薬を200μl加え、沸騰水浴中で30分間加熱した後、流水で室温まで冷やした。その後、565nmの吸光度を測定した。
すなわち、100μlの試料溶液に5体積%フェノール試薬を100μl加え、よく攪拌した。これに硫酸を1ml加えよく振り混ぜた後、480nmの吸光度を測定した。
実施例1で製造した被験物質およびシアル酸標準品(和光純薬工業社製、N−アセチルノイラミン酸、製品番号011−26173)を飲料水に溶かして濃度を調整してマウス(n=5)に与え、5mg/kg体重/日で被験物質を投与した。3週間飼育した後、末梢血中のIGF−1濃度をELISA法で調べた。結果を表2に示す。
NIH3T3細胞を96穴マイクロプレートに105細胞/ウェルになるように培養し、濃度を調整した被験物質1およびシアル酸標準品(和光純薬工業社製、N−アセチルノイラミン酸、製品番号011−26173)を10μl加え、24時間、CO2インキュベーターで培養を行った(37℃、4.5%CO2)。細胞増殖は、キット(同仁化学社製、Cell Counting Kit−8、製品番号347−07621)を用いたMTTアッセイ法にて測定した。結果を表3に示す。
シアル酸標準品無添加(0mg/ml)を100としてシアル酸標準品の各添加濃度による細胞の増殖率を算出した。
1.スキンケア効果
被験物質1を0.5重量%になるように脱イオン水に溶解したローションを作成し、50歳以上の10名(男性5名、女性5名)の被験者に使用させ、その効果を評価した。肌の水分量を、朝の洗顔前の頬と額の水分量をデジタルモイスチャーチェッカー1175(ワールドジェイビー社製)で測定した。結果を図2に示す。
被験食品として、乳清タンパク質(協同乳業社製、WPC; Whey Protein Concentration)に被験物質1を0.5重量%配合した食品を試作し、60〜80歳代の男性および女性合わせて30名の、つまずきやすくなり若干歩行困難な方、膝・肩・腰等に軽〜中度の障害がある方、原因不明の手腕や下肢の末梢の痺れが治らない方(いずれも自己申告)をサルコペニアの症状を示す被験者として、1ヶ月間、1日当たり本被験食品5g(1包)を摂取してもらった。摂取方法や摂取時間には何ら制限をかけず、本被験食品の作用機序や目的も一切知らせなかった。これはプラセボ効果を最小限にするための処置である。1ヵ月後の変化を4段階で評価した。結果を表5に示す。
良くなったまたは非常に良くなったと回答した27名(男性15名、女性12名)に多かったコメント(複数回答)を表6に示す。
7名の男性被験者(薄毛や抜け毛が増えている)に、被験溶液として被験物質1を0.05重量%、硫酸多糖の一種であるフコイダンを0.01重量%含む水溶液を、夜の洗髪後に適当量塗布させた。1ヵ月後の変化を4段階で評価した。結果を表7に示す。
良くなったまたは非常に良くなったと感じている6名に多かったコメント(複数回答)を表8に示す。
Claims (6)
- (1)シアロ糖タンパク質をアルカリ性水溶液中で70〜90℃に加温することによりアルカリ加水分解する工程、ここでアルカリ性水溶液に含まれるアルカリはシアロオリゴ糖のアルカリ加水分解のためのものである;および
(2)加水分解物を精製してシアロオリゴ糖を得る工程;
を含む、含有するシアル酸/ヘキソースの重量比が0.5〜0.9であるシアロオリゴ糖の製造方法。 - シアロ糖タンパク質がムチン型糖タンパク質である、請求項1に記載の製造方法。
- シアロ糖タンパク質がアナツバメ族の巣に含まれるムチン型糖タンパク質である、請求項1または2に記載の製造方法。
- アルカリ性水溶液が水酸化カリウム水溶液である、請求項1〜3のいずれか一項に記載の製造方法。
- 精製が逆浸透膜濾過または電気透析により行われる、請求項1〜4のいずれか一項に記載の製造方法。
- アルカリ性水溶液の濃度が0.2〜0.5重量%である、請求項1に記載の製造方法。
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CN201710725400.2A CN107778332B (zh) | 2016-08-25 | 2017-08-22 | 唾液酸低聚糖及其制造方法、生发和骨骼肌形成促进剂 |
US15/683,982 US10610537B2 (en) | 2016-08-25 | 2017-08-23 | Methods of producing sialooligosaccharides and uses thereof |
HK18110482.4A HK1250989A1 (zh) | 2016-08-25 | 2018-08-15 | 唾液酸低聚醣及其製造方法、生髮和骨骼肌形成促進劑 |
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JPH0899988A (ja) | 1994-09-29 | 1996-04-16 | Takehiko Yamamoto | シアル酸類含有オリゴ糖の製造法 |
US6323008B1 (en) * | 1997-08-14 | 2001-11-27 | Neose Technologies, Inc. | Methods for producing sialyloligosaccharides in a dairy source |
AUPQ885400A0 (en) * | 2000-07-18 | 2000-08-10 | Proteome Systems Ltd | Release of sugars from biomolecules |
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JP4465164B2 (ja) | 2003-06-20 | 2010-05-19 | 株式会社ヤクルト本社 | シアル酸含有オリゴ糖の製造方法 |
JP5261732B2 (ja) | 2007-07-18 | 2013-08-14 | ニュテックス株式会社 | シアル酸含有オリゴ糖の製造方法 |
NL2001377C2 (nl) | 2008-03-14 | 2009-09-15 | Friesland Brands Bv | Werkwijze voor het isoleren van siaalzuur bevattende oligosachariden, alsmede de hiermee verkrijgbare siaalzuur bevattende oligosachariden bevatttende samenstellingen. |
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