JP3678451B2 - Caries inhibitor, its production method and use - Google Patents

Description

【００３８】
表１の結果から明らかなように、本発明の有効成分であるα−イソマルトシルα−グルコシドは、メイラード反応による着色度は極めて低く、同じ重合度の還元性糖質であるイソマルトトリオースの着色度の３％程度であり、トレハロースと同様、メイラード反応を実質的に示さない糖質であることが判明した。同時に試験したα−イソマルトシル α−トソマルトシド及びα−イソマルトトリオシル α−グルコシドもα−イソマルトシル α−グルコシドと同様、メイラード反応を示さない糖質であることが判明した。
【００３９】
【実験４ 消化試験】
実験１の方法で調製したα−イソマルトシル α−グルコシドを用いて、岡田等が『日本栄養・食糧学会誌』、第４３巻、第１号、第２３乃至２９頁（１９９０年）で報告している方法に準じて、生体外（インビトロ）での消化試験を行ない、そのα−イソマルトシル α−グルコシドの消化の程度を分解率（全糖に対するグルコースの割合）により調べた。また、実験１の方法で調製したα−イソマルトシル α−イソマルトシド及びα−イソマルトトリオシル α−グルコシドも同様に試験した。比較例として、マルトース、トレハロース及びイソマルトースを用いて同様に試験した。結果を表２に示す。
【００４０】
【表２】

【００４１】
表２の結果から明らかなように、比較例のマルトース及びイソマルトースが主として小腸粘膜酵素でよく分解を受けるのに対し、本発明のα−イソマルトシルα−グルコシドは、主として小腸粘膜酵素によりわずかしか分解を受けないことから、経口摂取した場合、その大部分が大腸に到達するものと判断される。α−イソマルトシル α−イソマルトシド及びα−イソマルトトリオシル α−グルコシドも、小腸粘膜酵素による分解率に多少の差が見られるものの、実質的にはα−イソマルトシル α−グルコシドと同様、消化性の低い糖質、換言すれば、低カロリー糖質と判断される。
【００４２】
【実験５ 腸内細菌による資化性試験】
実験１の方法で調製したα−イソマルトシル α−グルコシドを用いて、光岡知足著、『腸内菌の世界（嫌気性菌の分離と同定）』、第３２５頁、叢文社（１９８４年）に記載されているＰＹＦ培地及びＰＹＦ培地に糖を０．５ｗ／ｖ％を添加した加糖ＰＹＦ培地で３７℃で９６時間嫌気培養を行ない、この培養液を５倍希釈し、その濁度（１ｃｍセルでの７５０ｎｍにおける吸光度）から腸内細菌の生育度を求め、その資化性の良否を判定した。また、実験１で調製したα−イソマルトシル α−イソマルトシド及びα−イソマルトトリオシル α−グルコシドも同様に試験した。また、比較例として、グルコース、トレハロース及びイソマルトースを用いて同様に試験した。判定基準は表３に、結果は表４及び表５に示した。
【００４３】
【表３】

【００４４】
【表４】

【表５】

【００４５】
表４及び表５の結果から明らかなように、比較例のグルコース及びトレハロースとは違って、本発明のα−イソマルトシル α−グルコシドは、ビフィドバクテリウムによる選択的資化性が高く、同様にα−イソマルトシル α−イソマルトシド及びα−イソマルトトリオシル α−グルコシドもビフィドバクテリウムによる選択的資化性の高い糖質であることが判明した。実験４の結果と合わせ考えると、α−イソマルトシル α−グルコシドは、α−イソマルトシル α−イソマルトシド及びα−イソマルトトリオシル α−グルコシドとともに、経口摂取により、その大部分は大腸に到達し、ビフィズス菌増殖促進剤として機能しうるものと判断される。
【００４６】
【実験６ 生体内でのビフィズス菌増殖促進作用に及ぼす影響】
被験者５名（男性、平均年齢４０．６才、平均体重６２．２ｋｇ）が、α−イソマルトシル α−グルコシド又はα−イソマルトシル α−イソマルトシドを毎日１回、昼食時に１０ｇを熱いスープに溶解して摂取し、これを１４日間続けた。実験順序は、α−イソマルトシル α−イソマルトシド摂取実験の後、１４日間のコントロール期間を設け、次いで、α−イソマルトシル α−グルコシドの摂取実験をした。摂取前と１４日間摂取後の１日当たりの糞便重量、糞便重量相対変化、糞便ｐＨ、糞便グラム当たりの総菌数、総菌数に占めるビフィズス菌の割合、並びに総ビフィズス菌数の相対変化を求め、被験者５名の平均値を算出した。この内、総菌数は、光岡知足著、『腸内菌の世界（嫌気性菌の分離と同定）』、第５３乃至６５頁、叢文社（１９８４年）に記載される方法に従って測定した。すなわちＭ１０培地を除く１３種の培地を使用して、出現したコロニーがいずれの菌群（属）に属するかの判定並びに菌数の測定を行った。各菌群の菌数は、最も高い菌数を与えた培地での菌数を真の菌数とした。このようにして得られた各菌群の菌数の総計を糞便の総菌数とした。総菌数に占めるビフィズス菌（ビフィドバクテリウム属）の割合（％）は、ビフィズス菌の菌数を総菌数で除した値に１００を乗じて求めた。総ビフィズス菌数の相対変化は、糞便グラム当たりのビフィズス菌の菌数に糞便重量を乗じた値を求め、摂取前の総ビフィズス菌の菌数を１００とし、１４日間摂取後の総ビフィズス菌の菌数を相対値で示した。糞便重量、糞便ｐＨと糞便中総ビフィズス菌数の変化を表６にまとめた。
【００４７】
【表６】

【００４８】
表６の結果から明らかなように、α−イソマルトシル α−グルコシド又はα−イソマルトシル α−イソマルトシドを摂取することによって、摂取前より１日当たりの糞便重量が増加し、糞便グラム当たりのビフィズス菌数が増加し、総菌数に占めるビフィズス菌数の割合が約２倍に高まり、総ビフィズス菌数においては、約２．３乃至２．５倍もの増加が見られ、糞便ｐＨにおいては約０．６乃至０．８の低下が見られることが判明した。α−イソマルトトリオシル α−グルコシドを、α−イソマルトシル α−イソマルトシド及びα−イソマルトシルα−グルコシドと同様に経口摂取試験したところ、消化管で消化されにくく、その大部分は大腸に到達し、同様にビフィズス菌増殖促進効果を発揮することが判明した。
【００４９】
【実験７ う蝕誘発菌による酸生成】
実験１の方法で調製したα−イソマルトシル α−グルコシドを用いて、竹内が『歯科基礎医学会雑誌』、第２６巻、第６９８乃至７１３頁（１９８４年）で報告している方法に準じて、う蝕誘発菌であるストレプトコッカス・ソブリヌス（Ｓｔｒｅｐｔｏｃｏｃｃｕｓ ｓｏｂｒｉｎｕｓ）ＡＴＣＣ２７３５１によって酸発酵を受けるかどうかを調べた。
【００５０】
ステファン緩衝液（ｐＨ７．０）に懸濁した生菌５０ｗ／ｖ％懸濁液と、同緩衝液に溶解した０．０２Ｍ濃度の試験糖質溶液とを混合し、３７℃で振とうし、そのｐＨを経時的に測定した。また、実験１の方法で調製したα−イソマルトシル α−イソマルトシド及びα−イソマルトトリオシル α−グルコシドも同様に試験した。比較例として、蔗糖、トレハロース及びイソマルトースを用いて同様に試験した。結果を表７に示した。
【００５１】
【表７】

【００５２】
表７の結果から明らかなように、蔗糖では、ｐＨが急激に低下し、トレハロースでは遅れて低下し、イソマルトースではわずかに低下したのに対し、α−イソマルトシル α−グルコシドは、ほとんどｐＨ低下を示さず、実質的に酸発酵を受けないことが判明した。α−イソマルトシル α−イソマルトシド、α−イソマルトトリオシル α−グルコシドも同様に実質的に酸発酵を受けないことが判った。
【００５３】
【実験８ う蝕誘発菌のグルコシルトランスフェラーゼによる不溶性グルカン合成の阻害】
実験１の方法で調製したα−イソマルトシル α−グルコシドを用いて、竹内が『歯科基礎医学会雑誌』、第２６巻、第６９８乃至７１３頁（１９８４年）で報告している方法に準じて、ストレプトコッカス・ソブリヌス ＡＴＣＣ２７３５１のグルコシルトランスフェラーゼによる蔗糖からの不溶性グルカン合成に対する影響を調べた。
【００５４】
濃度１％ｗ／ｖの蔗糖溶液１ｍｌ、濃度１％ｗ／ｖの試験糖質溶液１ｍｌ及び０．１Ｍリン酸緩衝液（ｐＨ６．８）１．５ｍｌからなる混液に、０．５ｍｌの粗グルコシルトランスフェラーゼ標品（総蛋白質量として１０ｍｇを含む）を加え、３０度の仰角で固定した小試験管内で、３７℃、１６時間反応させた。その反応液を他の試験管に静かに移した後、残存する管壁付着物を４ｍｌの水で温和に洗浄し、その洗液を反応液と合わせ、これを更に遠心分離して得られる沈澱物を非付着グルカンとした。また、反応試験管に残存する管壁付着物を付着グルカンとした。付着及び非付着グルカン生成量は、それぞれアンスロン硫酸法で定量し、両グルカン生成量の合計を不溶性グルカン生成量とした。試験糖質溶液の代わりに水を使用した反応系、換言すれば蔗糖のみの反応系を対照とし、不溶性グルカン生成阻害率は、対照の不溶性グルカン生成量に対する試験糖質反応系の不溶性グルカン生成量の百分率を１００から減じて求めた。実験１の方法で調製したα−イソマルトシル α−イソマルトシド及びα−イソマルトトリオシル α−グルコシドも同様に試験した。比較例として、トレハロース及びイソマルトースを用いて同様に試験した。結果を表８に示した。
【００５５】
【表８】

【００５６】
表８の結果から明らかなように、α−イソマルトシル α−グルコシドは、蔗糖のみ（対照）と比較すると、非付着グルカン、付着グルカンともにその生成量が顕著に少なく、また比較例のトレハロース、イソマルトースよりも不溶性グルカン生成を強く阻害することが判明した。また、同時に試験したα−イソマルトシル α−イソマルトシド及びα−イソマルトトリオシル α−グルコシドも、α−イソマルトシル α−グルコシドと同様に不溶性グルカン生成を強く阻害することが判明した。
【００５７】
以上の結果を実験７の結果とあわせて考えると、α−イソマルトシル α−グルコシドは、α−イソマルトシル α−イソマルトシド及びα−イソマルトトリオシル α−グルコシドとともに、う蝕誘発菌により酸発酵を受けず、またう蝕誘発菌による蔗糖からの不溶性グルカン生成を阻害し、加えて平滑面への付着を強く防止するので、蔗糖と併用される場合、蔗糖の持つう蝕作用を積極的に阻害する効果を有する糖質であって、う蝕抑制剤として好適であると判断される。
【００５８】
【実験９ 急性毒性試験】
マウスを使用して、実験１において調製したα−イソマルトシル α−グルコシド標品を経口投与して急性毒性試験を行った。その結果、投与可能な最大投与量においても死亡例は認められなかった。従って、そのＬＤ₅₀値は、５０ｇ／ｋｇ以上であって、α−イソマルトシル α−グルコシドは極めて低毒性の物質である。また、実験１で調製したα−イソマルトシル α−イソマルトシド及びα−イソマルトトリオシル α−グルコシドを同様に試験したところ、それらのＬＤ₅₀値は、５０ｇ／ｋｇ以上であって、いずれも極めて低毒性の物質である。
【００５９】
以下、本発明のα−イソマルトシル α−グルコシド、又はα−イソマルトシル α−イソマルトシド及び／又はα−イソマルトシル α−グルコシドを有効成分とするう蝕抑制剤の製造方法を実施例Ａで、有効成分としてα−イソマルトシル α−グルコシド、又はα−イソマルトシル α−イソマルトシド及び／又はα−イソマルトシル α−グルコシドを含有せしめたう蝕抑制作用を有する組成物を実施例Ｂで示す。
【００６０】
【実施例Ａ−１】
トレハロース１重量部及びデキストリン（ＤＥ１８、松谷化学工業株式会社製、商品名パインデックス＃４）１重量部を水２．５重量部に加熱溶解し、この溶液を温度６０℃、ｐＨ５．５にして、アスペルギルス・ニガー由来のα−グルコシダーゼを固形物グラム当たり５単位加えて２０時間反応させ、次いで、９５℃で３０分間保持して酵素を失活させた。本溶液を常法に従って、活性炭にて脱色、濾過し、Ｈ型及びＯＨ型イオン交換樹脂により脱塩して精製し、濃縮して、濃度７５％のα−イソマルトシル α−グルコシド含有シラップを固形物当たり、約９２％の収率で得た。
【００６１】
本品は、固形物当たり、α−イソマルトシル α−グルコシドを約２１％、α−イソマルトシル α−イソマルトシドを約５％及びα−イソマルトトリオシルα−グルコシドを約７％含有しており、う蝕抑制剤として好適であり、また、ビフィズス菌増殖促進剤、ミネラル吸収促進剤などとしても利用できる。更に、本品は、温和な甘味、適度の粘度、保湿性を有しており、甘味料、呈味改良剤、安定剤、賦形剤などとして、各種飲食物、化粧品、医薬品など各種組成物に有利に利用できる。
【００６２】
【実施例Ａ−２】
実施例Ａ−１の方法で得た反応液を精製し、濃度５０％に濃縮して原糖液とし、α−イソマルトシル α−グルコシドの含量を高めるため、実験１の方法に準じてナトリウム型強酸性カチオン交換樹脂『ＸＴ−１０１６』を用いたイオン交換カラムクロマトグラフィーを行った。樹脂を内径５．４ｃｍのジャケット付ステンレス製カラム４本に充填し、直列につなぎ、樹脂層全長２０ｍとした。
【００６３】
カラム内温度６０℃に維持しつつ、糖液を樹脂に対して、５ｖ／ｖ％加え、これに６０℃の温水をＳＶ０．１５で流して分画し、マルトース、グルコースなどの夾雑糖類を除去し、α−イソマルトシル α−グルコシド高含有画分を採取した。更に、精製、濃縮し、真空乾燥し、粉砕して、α−イソマルトシル α−グルコシド高含有粉末を固形物当たり、約２５％の収率で得た。
【００６４】
本品は、α−イソマルトシル α−グルコシドを約７０％、α−イソマルトシル α−イソマルトシドを約４％及びα−イソマルトトリオシル α−グルコシドを約５％含有しており、う蝕抑制剤として好適であり、また、ビフィズス菌増殖促進剤、ミネラル吸収促進剤などとしても利用できる。更に、本品は、低い還元性、まろやかで上品な甘味を有しており、甘味料、呈味改良剤、安定剤、賦形剤などとして、各種飲食物、化粧品、医薬品など各種組成物に有利に利用できる。
【００６５】
【実施例Ａ−３】
１０％馬鈴薯澱粉乳に最終濃度０．１％となるように炭酸カルシウムを加えた後、ｐＨ６．０に調整し、これにα−アミラーゼ（ナガセ生化学工業株式会社製、商品名『スピターゼＨＳ』）を澱粉グラム当たり０．１％加えて、攪拌下加熱し、糊化、液化させ、ただちにオートクレーブ（１２０℃）を２０分間行った後、温度４０℃、ｐＨ６．５に調整した。これにイソアミラーゼ（株式会社林原生物化学研究所製）を澱粉グラム当たり５００単位、本出願人が特願平６−７９２９１号明細書で開示したアルスロバクター・スピーシーズ（Ａｒｔｈｒｏｂａｃｔｅｒ ｓｐ．）Ｑ３６（寄託番号 ＦＥＲＭ ＢＰ−４３１６）由来の非還元性糖質生成酵素を３単位及び同菌株由来のトレハロース遊離酵素を１５単位加えて、１２時間反応させ、トレハロース約５５％を含む糖液を得た。次いで、９５℃に３０分間保持して酵素を失活させた後、固形物濃度４５％になるまで濃縮し、更に、温度６０℃、ｐＨ５．０にして、キャンディダ・トロピカリス（Ｃａｎｄｉｄａ ｔｒｏｐｉｃａｌｉｓ）ＩＦＯ０５８９由来のα−グルコシダーゼ（株式会社林原生物化学研究所製）を固形物当たり３単位加えて、２４時間反応させた。本反応液を９５℃で３０分間保持して酵素を失活させた後、常法に従って活性炭で脱色、濾過し、Ｈ型及びＯＨ型イオン交換樹脂により脱塩して精製し、更に濃縮して濃度約７５％のα−イソマルトシル α−グルコシド含有シラップを固形物当たり、約９５％の収率で得た。
【００６６】
本品は、固形物当たり、α−イソマルトシル α−グルコシドを約２０％、α−イソマルトシル α−イソマルトシドを約３％及びα−イソマルトトリオシルα−グルコシドを約５％含有しており、う蝕抑制剤として好適であり、また、ビフィズス菌増殖促進剤、ミネラル吸収促進剤などとしても利用できる。更に、本品は、温和な甘味、適度の粘度、保湿性を有しており、甘味料、呈味改良剤、安定剤、賦形剤などとして、各種飲食物、化粧品、医薬品など各種組成物に有利に利用できる。
【００６７】
【実施例Ａ−４】
３０％とうもろこし澱粉乳に最終濃度０．１％となるように炭酸カルシウムを加えた後、ｐＨ６．５に調整し、これにα−アミラーゼ（ノボ社製、商品名『ターマミール６０Ｌ』）を澱粉グラム当たり０．２％加え、攪拌下加熱し、糊化、液化させ、ただちにオートクレーブ（１２０℃）を２０分間行った後、５５℃に冷却し、これにイソアミラーゼ（株式会社林原生物化学研究所製）を澱粉グラム当たり５００単位及びβ−アミラーゼ（ナガセ生化学工業株式会社製）を澱粉グラム当たり３０単位の割合になるように加え、４８時間反応させ、マルトース含量約８４％の糖液を得た。この反応液を９５℃で３０分間加熱した後、温度６０℃、ｐＨ７．０に調整し、これに本出願人が特願平６−１４４０９２号明細書（特開平７−１７０９７７号公報）で開示したサーマス・アクアティカス（Ｔｈｅｒｍｕｓ ａｑｕａｔｉｃｕｓ）ＡＴＣＣ３３９２３由来のマルトース・トレハロース変換酵素を澱粉グラム当たり１単位の割合になるよう加え、２４時間反応させ、トレハロースを約５０％含む糖液を得た。その反応液をｐＨ５．５に調整し、アスペルギルス・ニガー由来のα−グルコシダーゼを固形物グラム当たり３単位加えて６０℃、２４時間反応させた。次いで、９５℃で３０分間保持して酵素を失活させた後、常法に従って活性炭で脱色、濾過し、Ｈ型及びＯＨ型イオン交換樹脂により脱塩して精製し、更に濃縮、真空乾燥、粉砕して、α−イソマルトシル α−グルコシド含有粉末を固形物当たり、約９０％の収率で得た。
【００６８】
本品は、固形物当たり、α−イソマルトシル α−グルコシドを約２０％、α−イソマルトシル α−イソマルトシドを約４％及びα−イソマルトトリオシルα−グルコシドを約６％含有しており、う蝕抑制剤として好適であり、また、ビフィズス菌増殖促進剤、ミネラル吸収促進剤などとしても利用できる。更に、本品は、温和な甘味、適度の粘度、保湿性を有しており、甘味料、呈味改良剤、安定剤、賦形剤などとして、各種飲食物、化粧品、医薬品など各種組成物に有利に利用できる。
【００６９】
【実施例Ａ−５】
３０％馬鈴薯澱粉乳に最終濃度０．１％となるように炭酸カルシウムを加え、ｐＨ６．５に調整し、これにα−アミラーゼ（ナガセ生化学工業株式会社製、商品名『スピターゼＨＳ』）を澱粉グラム当たり０．０１％加え、攪拌下加熱し、糊化、液化させ、ただちにオートクレーブ（１２０℃）を５分間行った後、５５℃に冷却し、ＤＥ１未満の液化澱粉液を得、ｐＨ７．０に調整し、プルラナーゼ（株式会社林原生物化学研究所製）及びマルトテトラオース生成アミラーゼ（株式会社林原生物化学研究所製）をそれぞれ澱粉グラム当たり１５０単位及び８単位の割合で加え、５０℃で３６時間反応させた。本反応液を９５℃で３０分間加熱し、次いで４５℃に冷却し、これに本出願人がヨーロッパ特許出願公開０６０６７５３Ａ２号公報で開示したリゾビウム・スピーシーズ（Ｒｈｉｚｏｂｉｕｍｓｐ．）Ｍ−１１（寄託番号 ＦＥＲＭ ＢＰ−４１３０）由来の非還元性糖質生成酵素を澱粉グラム当たり２単位加え６４時間反応させた後、温度６０℃、ｐＨ５．０に調整して、キャンディダ・トロピカリス ＩＦ００５８９由来のα−グルコシダーゼを澱粉グラム当たり３単位の割合になるように加え、２４時間反応させた。その反応液を、９５℃で３０分間保持して酵素を失活させた後、常法に従って活性炭で脱色、濾過し、Ｈ型及びＯＨ型イオン交換樹脂により脱塩して精製し、更に濃縮、真空乾燥、粉砕して、α−イソマルトシル α−グルコシド含有粉末を固形物当たり約９０％の収率で得た。
【００７０】
本品は、固形物当たり、α−イソマルトシル α−グルコシドを約１８％、α−イソマルトシル α−イソマルトシドを約４％及びα−イソマルトトリオシルα−グルコシドを約５％含有しており、う蝕抑制剤として好適であり、また、ビフィズス菌増殖促進剤、ミネラル吸収促進剤などとしても利用できる。更に、本品は、温和な甘味、適度の粘度、保湿性を有しており、甘味料、呈味改良剤、安定剤、賦形剤などとして、各種飲食物、化粧品、医薬品など各種組成物に有利に利用できる。
【００７１】
【実施例Ａ−６】
３０％とうもろこし澱粉乳に最終濃度０．１％となるように炭酸カルシウムを加えた後、ｐＨ６．５に調整し、これにα−アミラーゼ（ノボ社製、商品名『ターマミール６０Ｌ』）を澱粉グラム当たり０．３％加え、攪拌下加熱し、糊化、液化させ、ただちにオートクレーブ（１２０℃）を３０分間行った後、５５℃に冷却し、ＤＥ約４の液化澱粉液を得、これにアルスロバクター・スピーシーズＱ３６由来の非還元性糖質生成酵素を澱粉グラム当たり４単位、イソアミラーゼを澱粉グラム当たり３００単位及びシクロマルトデキストリン・グルカノトランスフェラーゼ（株式会社林原生物化学研究所製）を澱粉グラム当たり５単位の割合になるように加え、ｐＨ６．３、温度４５℃で４８時間反応させた。本反応液を、９５℃で３０分間加熱した後、温度５５℃、ｐＨ５．５に調整し、これにβ−アミラーゼを澱粉グラム当たり１０単位加えて、１６時間反応させ、９５℃で３０分間保持して酵素を失活させた後、６０℃に冷却し、アスペルギルス・ニガー由来のα−グルコシダーゼを固形物グラム当たり３単位加えて、２４時間反応させた。その反応液を、９５℃で３０分間保持して酵素を失活させた後、常法に従って活性炭で脱色、濾過し、Ｈ型及びＯＨ型イオン交換樹脂により脱塩して精製し、更に濃縮して、α−イソマルトシル α−グルコシド含有シラップを固形物当たり約９５％の収率で得た。
【００７２】
本品は、固形物当たり、α−イソマルトシル α−グルコシドを約１８％、α−イソマルトシル α−イソマルトシドを約２％及びα−イソマルトトリオシルα−グルコシドを約３％含有しており、う蝕抑制剤として好適であり、また、ビフィズス菌増殖促進剤、ミネラル吸収促進剤などとしても利用できる。更に、本品は、温和な甘味、適度の粘度、保湿性を有しており、甘味料、呈味改良剤、安定剤、賦形剤などとして、各種飲食物、化粧品、医薬品など各種組成物に有利に利用できる。
【００７３】
【実施例Ａ−７】
実施例Ａ−１の方法で得た反応液を、常法に従って、精製し、濃縮した濃度約５０％のシラップをオートクレーブに入れ、ラネーニッケル１０％を添加し、撹拌しながら濃度を９０乃至１２０℃に上げ、水素圧を２０乃至１２０ｋｇ／ｃｍ²に上げて水素添加を完了させ、次いで、ラネーニッケルを除去し、脱色、脱塩して精製し、濃縮して、濃度７０％のシラップを固形物当たり８０％の収率で得た。本品は、固形物当たりα−イソマルトシル α−グルコシドを約２１％、α−イソマルトシル α−イソマルトシドを約５％及びα−イソマルトトリオシルα−グルコシドを約７％とともに糖アルコールを含有しており、う蝕抑制剤として好適であり、また、本品は、ビフィズス菌増殖促進剤、ミネラル吸収促進剤などとしても有利に利用できる。更に、本品は、還元性を示さず、温和な甘味、適度の粘度、保湿性を有し、甘味料、呈味改良剤、安定剤、賦形剤などとして各種飲食物、化粧品、医薬品など各種組成物に有利に利用できる。
【００７４】
【実施例Ａ−８】
実施例Ａ−２の方法で得たα−イソマルトシル α−イソマルトシド高含有画分を、常法に従って、精製し、濃縮した濃度約５０％のシラップを実施例Ａ−７の方法に準じて、水素添加し、精製、濃縮、真空乾燥、粉砕して、α−イソマルトシル α−イソマルトシド高含有粉末を、固形物当たり約７０％の収率で得た。本品は、固形物当たりα−イソマルトシル α−グルコシドを約３２％、α−イソマルトシル α−イソマルトシドを約２０％及びα−イソマルトトリオシルα−グルコシドを約２８％とともに糖アルコールを含有しており、う蝕抑制剤として好適であり、また、本品は、ビフィズス菌増殖促進剤、ミネラル吸収促進剤などとしても有利に利用できる。更に、本品は、還元性を示さず、まろやかで上品な甘味を有し、甘味料、呈味改良剤、品質改良剤、安定剤、賦形剤などとして、各種飲食物、化粧品、医薬品など各種組成物に有利に利用できる。
【００７５】
【実施例Ａ−９】
実施例Ａ−５の方法で得たα−イソマルトシル α−イソマルトシド生成反応液を、常法に従って、精製し、濃縮した濃度約５０％のシラップを実施例Ａ−７の方法に準じて、水素添加し、精製、濃縮して、濃度約７０％のシラップを固形物当たり約８０％の収率で得た。本品は、固形物当たりα−イソマルトシル α−グルコシドを約１８％、α−イソマルトシル α−イソマルトシドを約４％及びα−イソマルトトリオシル α−グルコシドを約５％とともに糖アルコールを含有しており、う蝕抑制剤として好適であり、また、本品は、ビフィズス菌増殖促進剤、ミネラル吸収促進剤などとしても有利に利用できる。更に、本品は、還元性を示さず、温和な甘味、適度の粘度、保湿性を有し、甘味料、呈味改良剤、安定剤、賦形剤などとして、各種飲食物、化粧品、医薬品など各種組成物に有利に利用できる。
【００７６】
【実施例Ｂ−１ 甘味料】
実施例Ａ−２の方法で得たα−イソマルトシル α−グルコシド高含有粉末１重量部に、α−グリコシルステビオシド（東洋精糖株式会社製、商品名『αＧスイート』）０．０１重量部及びＬ−アスパルチル−Ｌ−フェニルアラニンメチルエステル（商品名『アスパルテーム』）０．０１重量部を均一に混合し、顆粒成形機にかけて、顆粒状甘味料を得た。本品は、う蝕誘発菌による酸の生成が少なく、不溶性グルカンの生成も少ないことより虫歯を抑制する飲食物などに対する甘味付けに好適である。また、本品は、甘味の質が優れ、蔗糖の約２．５倍の甘味度を有し、甘味度当たりのカロリーは、蔗糖の約１／２．５に低下している。更に、本品は、それに配合した高甘味度甘味物の分解もなく、安定性に優れており、低カロリー甘味料として、カロリー摂取を制限している肥満者、糖尿病者などのための低カロリー飲食物などに対する甘味付けに好適である。また、本品は、ビフィズス菌増殖促進作用、ミネラル吸収促進作用を有し、美容食品、健康食品としても好適である。
【００７７】
【実施例Ｂ−２ ハードキャンディー】
濃度５５％蔗糖溶液１００重量部に実施例Ａ−１の方法で得たα−イソマルトシル α−グルコシド含有シラップ３０重量部を加熱混合し、次いで減圧下で水分２％未満になるまで加熱濃縮し、これにクエン酸１重量部及び適量のレモン香料と着色料とを混和し、常法に従って成型し、製品を得た。本品は、低う蝕性のビフィズス菌増殖促進作用を有するハードキャンディーである。また、本品は、歯切れ、呈味良好で、蔗糖の晶出も起こらない高品質のハードキャンディーである。
【００７８】
【実施例Ｂ−３ チューインガム】
ガムベース３重量部を柔らかくなる程度に加熱溶融し、これに結晶マルチトール粉末３重量部及び実施例Ａ−８の方法で得たα−イソマルトシル α−グルコシド高含有粉末４重量部とを加え、更に適量の香料と着色料とを混合し、常法に従って、ロールにより練り合わせ、成形、包装して製品を得た。本品は、難う蝕性のビフィズス菌増殖促進作用を有するチューインガムである。また、本品はテクスチャー、風味とも良好なチューインガムである。
【００７９】
【実施例Ｂ−４ 野菜ジュース】
トマトジュースを主体とした野菜ジュース１，０００重量部に、実施例Ａ−９の方法で得たα−イソマルトシル α−グルコシド含有シラップ１０重量部及びプルラン（分子量約１０，０００）５重量部を溶解し、常法に従って加熱殺菌し、缶詰して製品を得た。本品は、う蝕抑制作用に加えて、ビフィズス菌増殖促進作用、ミネラル吸収促進作用を有する美容飲料、健康飲料として好適である。
【００８０】
【実施例Ｂ−５ カスタードクリーム】
コーンスターチ１００重量部、実施例Ａ−３の方法で得たα−イソマルトシルα−グルコシド含有シラップ１００重量部、マルトース８０重量部、蔗糖２０重量部及び食塩１重量部を充分に混合し、鶏卵２８０重量部を加えて攪拌し、これに沸騰した牛乳１，０００重量部を徐々に加え、更に、これを火にかけて攪拌を続け、コーンスターチが完全に糊化して全体が半透明になった時に火を止め、これを冷却して適量のバニラ香料を加え、計量、充填、包装して製品を得た。本品は、う蝕抑制作用に加えて、ビフィズス菌増殖促進作用、ミネラル吸収促進作用を有する美容食品、健康食品として好適である。また、本品は、なめらかな光沢を有し、温和な甘味で美味である。
【００８１】
【実施例Ｂ−６ ういろうの素】
米粉９０重量部に、コーンスターチ２０重量部、蔗糖４０重量部、実施例Ａ−４の方法で得たα−イソマルトシル α−グルコシド含有粉末８０重量部及びプルラン４重量部を均一に混合してういろうの素を製造した。ういろうの素と適量の抹茶と水とを混練し、これを容器に入れて６０分間蒸し上げて抹茶ういろうを製造した。本品は、う蝕抑制作用に加えて、ビフィズス菌増殖促進作用を有する美容食品、健康食品として好適である。また、本品は、照り、口当たりも良好で、風味も良い。また、澱粉の老化も抑制され、日持ちも良い。
【００８２】
【実施例Ｂ−７ 加糖練乳】
原乳１００重量部に実施例Ａ−７の方法で得たα−イソマルトシル α−グルコシド含有シラップ３重量部及び蔗糖１重量部を溶解し、プレートヒーターで加熱殺菌し、次いで濃度７０％に濃縮し、無菌状態で缶詰して製品を得た。本品は、温和な甘味で、風味もよく、乳幼児食品、フルーツ、コーヒー、ココア、紅茶などの調味用に有利に利用できる。また、本品は、う蝕抑制作用に加えて、ビフィズス菌増殖促進作用、ミネラル吸収促進作用を有する美容食品、健康食品として好適である。
【００８３】
【実施例Ｂ−８ 錠剤】
実施例Ａ−２の方法で得たα−イソマルトシル α−グルコシド高含有粉末２０重量部、含水結晶トレハロース３０重量部、乳酸カルシウム１重量部、シュガーエステル１重量部及び適量の粉末香料を均一に混合した後、常法に従って、１錠約３５０ｍｇになるように打錠機にて打錠し錠剤を得た。本品は、う蝕抑制作用に加えて、ビフィズス菌増殖促進作用、カルシウム吸収促進作用を有する美容食品、健康食品として好適である。また、本品は、ひび割れもなく安定性良好な飲みやすい錠剤で、成人１日当たり、通常、約１乃至４０錠、望ましくは、約２乃至２０錠摂取する。
【００８４】
【実施例Ｂ−９ 錠剤】
実施例Ａ−４の方法で得たα−イソマルトシル α−グルコシド含有粉末２０重量部、ラクトスクロース含有粉末（登録商標『乳果オリゴ』、株式会社林原商事販売）１０重量部、ラクトース２０重量部、第三リン酸カルシウム１重量部、乳酸カルシウム１重量部、シュガーエステル１重量部、粉末食用色素適量及び粉末香料適量を均一に混合した後、常法に従って、１錠約６８０ｍｇになるように打錠機にて打錠し製品を得た。本品は、う蝕抑制作用に加えて、ビフィズス菌の増殖促進作用、カルシウム吸収促進作用を有する美容食品、健康食品として好適である。本品を、成人１日当たり、通常、約１乃至４０錠、望ましくは、約２乃至２０錠摂取する。
【００８５】
【実施例Ｂ−１０ 栄養剤】
無水結晶マルトース４８０重量部、乾燥卵黄１９０重量部、脱脂粉乳２０９重量部、実施例Ａ−２の方法で得たα−イソマルトシル α−グルコシド高含有粉末１１５重量部、塩化ナトリウム４．４重量部、塩化カリウム１．８５重量部、硫酸マグネシウム４重量部、チアミン０．０１重量部、アスコルビン酸ナトリウム０．１重量部、ビタミンＥアセテート０．６重量部及びニコチン酸アミド０．０４重量部からなる配合物を調製し、この２５ｇずつを、ラミネートアルミ製小袋に充填し、ヒートシールして、用時溶解タイプの栄養剤を得た。本品は、低温貯蔵の必要もなく、室温下で長期間安定であり、その上、溶解性、分散性に優れている。本品は、１袋分を約１５０乃至３００ｍｌの温水に溶解して、経口又は経管方法により、鼻腔、食堂、胃などから摂取することにより、栄養補給とともにう蝕抑制作用、ビフィズス菌増殖促進作用、ミネラル吸収促進作用を発揮し、患者の回復を促進する。特に大腸内でビフィズス菌の増殖を促進し、ｐＨを低下し、腐敗物質などによる有害物質の産生を抑制する。また、糞便量を増大し、患者に起こりがちな便秘を予防することができる。なお、本品は、ヒトのみならず、家畜のための経口摂取又は経管摂取用ビフィズス菌増殖促進作用を有する組成物としても有利に利用できる。
【００８６】
【実施例Ｂ−１１ 栄養剤】
無水結晶トレハロース１４．５重量部、蔗糖４．０５重量部、粉末うんしゅう果汁３．２重量部、実施例Ａ−５の方法で得たα−イソマルトシル α−グルコシド含有粉末３．０重量部、クエン酸０．１１重量部、アスコルビン酸０．０２重量部及び粉末オレンジ香料０．１重量部からなる配合物を調製し、この４００ｇずつをねじ蓋式缶に充填密封して、用時溶解タイプの栄養剤を製造した。本品は、実施例Ｂ−１０と同様に安定性、溶解性が良好である。本品は、ビフィズス菌増殖促進作用を有する組成物であって、約２５ｇを約１００乃至１５０ｍｌの温水に溶解して、実施例Ｂ−１０と同様に経口又は経管方法により摂取することにより、栄養補給とともにビフィズス菌増殖促進作用、ミネラル吸収促進を発揮し、患者の回復を促進する。また、蔗糖の持つう蝕性を低減させた栄養剤としても有利に利用できる。
【００８７】
【実施例Ｂ−１２ 練歯磨】
第二リン酸カルシウム４５重量部、プルラン２．９５重量部、ラウリル硫酸ナトリウム１．５重量部、グリセリン２０重量部、ポリオキシエチレンソルビタンラウレート０．５重量部、防腐剤０．０５重量部、実施例Ａ−６の方法で得たα−イソマルトシル α−グルコシド含有シラップ１５重量部、スクロース５重量部及び水１０重量部を常法に従って混合し、練歯磨を得た。本品は、適度の甘味を有しており、特に子供用練歯磨として好適である。
【００８８】
【発明の効果】
上記から明らかなように、本発明の有効成分である非還元性オリゴ糖α−イソマルトシル α−グルコシド、又はα−イソマルトシル α−グルコシドとともにα−イソマルトシル α−イソマルトシド及び／又はα−イソマルトトリオシル α−グルコシドは、それ自身極めて安定であり、また、良質で温和な甘味を有している。本非還元性オリゴ糖は、う蝕誘発菌などによって発酵されにくく、う蝕誘発菌による蔗糖からの不溶性グルカンの合成を阻害し、歯垢形成を抑え、虫歯を抑制する。
【００８９】
また、非還元性オリゴ糖は、化学的に安定であり、褐変反応を起こし易いアミノ酸、オリゴペプチド、更には、有効成分、活性の失われやすい生理活性物質などを安定化し得る性質を有している。加えて、浸透圧調節性、賦活性、照り付与性、保湿性、粘性、他糖の晶出防止、難発酵性、澱粉の老化防止性などの性質を有している。これら諸性質は、飲食物、嗜好物、飼料、餌料、医薬品など各種う蝕抑制作用を有する組成物に有利に利用できる。本組成物は、う蝕抑制作用のみならず、ビフィズス菌増殖促進作用、ミネラル吸収促進作用を有しており、各種美容、健康飲食品として好適である。
【００９０】
従って、本発明のα−イソマルトシル α−グルコシド、またはα−イソマルトシル α−グルコシドとともにα−イソマルトシル α−イソマルトシド及び／又はα−イソマルトトリオシル α−グルコシドを有効成分とするう蝕抑制剤とその製造方法並びに用途の確立は、食品、化粧品、医薬品分野における工業的意義が極めて大きい。
【図面の簡単な説明】
【図１】α−イソマルトシル α−イソマルトシドの構造を示す図である。
【図２】α−イソマルトシル α−グルコシドの構造を示す図である。
【図３】α−イソマルトトリオシル α−グルコシドの構造を示す図である。[0001]
[Industrial application fields]
TECHNICAL FIELD The present invention relates to a caries inhibitor, a method for producing the same, and use thereof. Specifically, α-isomaltosyl α-glucoside, or α-isomaltosyl α-glucoside together with α-isomaltosyl α-isomaltoside and / or α-isomalt. The present invention relates to a caries inhibitor containing triosyl α-glucoside as an active ingredient, a method for producing the same, and use.
[0002]
[Prior art]
Trehalose (α, α-trehalose) is a non-reducing disaccharide having glucose as a constituent sugar, and is present in a wide range of nature such as mold, yeast, bacteria, mushrooms, higher plants, insects and the like in small amounts. Because trehalose is non-reducing, it does not cause Maillard reaction (aminocarbonyl reaction) with substances having amino groups such as amino acids and proteins, and does not damage amino acid-containing substances, and is itself a stable carbohydrate. It can be used and processed without worrying about browning and deterioration, and a wide range of uses has been expected. As an example of its use, JP-A-63-240758 discloses that trehalose is a bifidobacteria proliferating saccharide and a low carious saccharide. In subsequent studies, although their actions are superior to sucrose, they are relatively small and the development of better carbohydrates is desired.
[0003]
On the other hand, isomaltoligosaccharides such as isomaltotriose (also known as dextrantriose) and isomalttetraose (also known as dextrantetraose) are “Chemical & Pharmaceutical Bulletin”, Vol. 26. 3306 to 3311 (1978), which is known as a bifidobacteria proliferating saccharide and disclosed in Japanese Patent Publication No. 5-39584, Japanese Patent Publication No. 5-53465, and the like. As is known, it is also known as difficult caries carbohydrate or anti-cariogenic carbohydrate.
[0004]
However, isomaltoligosaccharides are reducing saccharides, and are susceptible to browning reaction with amino acids, and have the disadvantage of easily causing deterioration and deterioration in food processing, and further development of superior saccharides is desired. .
[0005]
The present inventors focused on these characteristics of trehalose and isomaltoligosaccharides. Among oligosaccharides having both a trehalose structure and an isomaltose structure, the present inventors are non-reducing and excellent in anti-cariogenic properties. The study was started with the strong expectation that a selectively proliferative carbohydrate exists. For oligosaccharides having both a trehalose structure and an isomaltose structure, see, for example, Sakasomyces Spices, in “Carbohydrate Research”, Volume 199, pp. 227-234 (1990). O-α-D-glucopyranosyl- (1 → 6) -α-D- by a condensation reaction from trehalose and glucose with (Saccharomyces sp.) Α-glucosidase or Rhizopus niveus glucoamylase. Glucopyranosyl α-D-glucopyranoside, α-isomaltosyl α-glucoside, has been reported, and Gold et al., “Starch Science”, 40, 349 (1993), Arthrobacter O-α-D-glucopyranosyl- (1 → 6) -O-α-D-glucopyranosyl- (1 → 6) from dextran and trehalose by transglycosylation of isomaltoxextrinase of Arthrobacter globiformis T6 -Α-D-glucopyranosyl α-isomaltriosyl α-glucoside represented by α-D-glucopyranoside is reported. However, it has been found that these reports do not disclose any carbohydrate characteristics expected by the present inventors.
[0006]
[Problems to be solved by the invention]
The present invention establishes a caries inhibitor containing a non-reducing carbohydrate having both a trehalose structure and an isomaltose structure in the molecule as an active ingredient and a method for producing the same, and intends to provide its use.
[0007]
[Means for Solving the Problems]
In order to solve the above problems, the present inventors have continued intensive studies on a caries inhibitor containing the non-reducing carbohydrate as an active ingredient and a method for producing the same.
[0008]
As a result, α-isomaltosyl α-glucoside, or α-isomaltosyl α-glucoside and α-isomaltosyl α-isomaltosid and / or α-isomaltotriosyl α-glucoside are non-reducing oligosaccharides, excellent in stability and remarkable. The present invention was completed by finding a caries inhibitory action, establishing a caries inhibitor containing the non-reducing oligosaccharide as an active ingredient, a method for producing the same, and an application.
[0009]
Α-Isomaltosyl α-glucoside, α-isomaltosyl α-isomaltoside, and α-isomaltotriosyl α-glucoside, which are the active ingredients of the present invention, can be chemically synthesized, but industrially, It is advantageous to produce the chemical reaction, in particular by the action of α-glucosidase (EC 3.2.1.20) on an aqueous solution containing trehalose and starch.
[0010]
In addition, as an aqueous solution containing trehalose and starch, α-glucosidase acts and α-isomaltosyl α-glucoside, or α-isomaltosyl α-glucoside together with α-isomaltosyl α-isomaltosid and / or α-isomalt trio. As long as it produces sil-α-glucoside, not only an aqueous solution containing trehalose and starch as respective compounds, but also a trehalose structure and a starch structure of α-1,4 glucoside binding mode in the molecule An aqueous solution containing a compound having both can also be advantageously used.
[0011]
When trehalose and starch are used as the respective compounds, commercially available trehalose may be used, and if necessary, a known method such as a bacterium having the ability to produce trehalose or extract from yeast. It may be prepared and used by separating it from the culture broth or by subjecting it to an enzymatic action on the starch described later. As the starch, for example, starch such as gelatinized starch, liquefied starch, soluble starch, malto-oligosaccharide or a partially decomposed product of starch can be used as appropriate. In the case of using a partially decomposed starch, it can be advantageously decomposed by acting a liquefying enzyme such as α-amylase or a starch debranching enzyme such as pullulanase or isoamylase on the starch.
[0012]
Further, as a method for simultaneously producing trehalose and starch, for example, the applicant of the present application has disclosed Japanese Patent Application No. 5-156338 and Japanese Patent Application No. 6-79291. (JP-A-7-213283) As disclosed in Japanese Patent Application No. 5-199971 and Japanese Patent Application No. 6-144092, a non-reducing saccharide-forming enzyme and trehalose-releasing enzyme are allowed to act on an aqueous solution containing starch. Specification (Japanese Patent Laid-Open No. 7-170977) As disclosed in the above, a method of allowing maltose / trehalose converting enzyme to act on an aqueous solution containing maltose can be advantageously used.
[0013]
Next, when using a compound having both a trehalose structure and an α-1,4 glucoside-linked starch structure in the molecule, for example, the present applicant disclosed in European Patent Application Publication No. 06067553A2. A compound having a trehalose structure at the end of a molecule having a starch structure of α-1,4 glucoside bond by allowing a non-reducing saccharide-forming enzyme to act on an aqueous solution containing starch, Japanese Patent Application No. 5-178623, Japanese Patent Application No. 6-167486 (JP-A-8-127487) As disclosed in the above, a non-reducing saccharide-forming enzyme and cyclomaltodextrin / glucanotransferase are allowed to act on an aqueous solution containing starch, so that a trehalose structure and an α-1,4 glucoside binding mode are formed inside the molecule. What is necessary is just to manufacture and utilize the compound which has a starchy structure.
[0014]
The α-glucosidase used in the present invention may be an enzyme capable of converting starch α-1,4 glucoside bond to α-1,6 glucoside bond. For example, Aspergillus niger, Aspergillus niger Aspergillus awamori, Aspergillus saitoi, Mucor javanicus, Penicillium crisogenum and Penicillium crisogenum, etc. it can.
[0015]
The conditions for the enzyme reaction may be α-isomaltosyl α-glucoside, or α-isomaltosyl α-glucoside together with α-isomaltosyl α-isomaltoside and / or α-isomaltotriosyl α-glucoside. In an aqueous solution containing trehalose and starch, 0.1 unit or more, preferably 1 to 100 units of α-glucosidase per gram of starchy substance, under conditions selected from a temperature of 20 to 80 ° C. and a pH of 3 to 9; The action may be performed for 1 to 100 hours, preferably about 1 to 70 hours. One unit of activity of α-glucosidase used in the present invention is defined as the amount of enzyme that produces 2 μmol of glucose per minute under the conditions of 40 ° C. and pH 5.5 using 0.2 w / v% maltose as a substrate. . As a result of this enzymatic reaction, α-isomaltosyl α-glucoside and α-isomaltosyl α-isomaltoside, α-isomaltotriosyl α-glucoside, and one to several α-glucosyl groups with α-1,6 linkages. Bound oligosaccharides such as α-isomaltotriosyl α-isomaltoside, α-isomaltotetraosyl α-isomaltoside, α-isomaltotriosyl α-isomaltotrioside and the like are produced. This reaction solution usually contains reducing sugars such as glucose, maltose, maltotriose, unreacted trehalose, starch and the like. When glucoamylase is allowed to act on this, α-isomaltosyl α-glucoside and α-isomaltosyl α-isomaltoside are accumulated and produced as non-reducing carbohydrates, which may be collected and used.
[0016]
The α-isomaltosyl α-glucoside-containing solution produced by the enzyme reaction as described above is usually 5 to 40 w / w% (hereinafter referred to as non-reducing oligosaccharides having both a trehalose structure and an isomaltose structure per solid). In the present specification, unless otherwise specified, w / w% is abbreviated as%.) And α-isomaltosyl α-glucoside is contained in an amount of about 5 to 30%, which is filtered and purified. It is optional to use in a liquid state, to concentrate and use in a syrup form, or to dry and use in a solid state.
[0017]
If necessary, in order to take advantage of the characteristics of α-isomaltosyl α-glucoside, the α-isomaltosyl α-glucoside production solution is further separated and purified to be used as a high α-isomaltosyl α-glucoside content. As the method, for example, a method of separating and removing contaminating saccharides by a yeast fermentation method, a membrane filtration method, a fractional precipitation method, an alkali treatment method, column chromatography or the like can be appropriately employed. In particular, by column chromatography using a salt type strongly acidic cation exchange resin disclosed in JP-B-62-50477, JP-B-4-50319, etc., α-isomaltosyl α-glucoside The method of collecting the contained fraction can be advantageously carried out. At this time, it is optional to adopt any of a fixed floor method, a moving floor method, and a simulated moving floor method.
[0018]
In addition, if necessary, α-isomaltosyl α-glucoside-containing saccharide is hydrogenated according to a conventional method, and reducing saccharides such as glucose and maltose contained therein are converted into sugar alcohols, and the reducing power is substantially eliminated. It can be advantageously carried out to produce an α-isomaltosyl α-glucoside-containing saccharide that does not exhibit reducing properties.
[0019]
Α-Isomaltosyl α-glucoside, which is an active ingredient of the present invention, or α-isomaltosyl α-isomaltoside and / or α-isomaltotriosyl α-glucoside together with α-isomaltosyl α-glucoside is itself non-reducing, It is extremely stable, has low sweetness but has good quality and mild sweetness, is not easily fermented by caries-inducing bacteria, etc., inhibits insoluble glucan synthesis from sucrose by caries-inducing bacteria, and prevents plaque formation. By suppressing it, it can be advantageously used as a sweetener that does not cause caries and as a caries inhibitor. In addition, it can stabilize amino acids and oligopeptides that are chemically stable and easily undergo a browning reaction with saccharides, as well as active ingredients and bioactive substances that tend to lose activity. It has properties such as irradiability, moisture retention, viscosity, anti-crystallization of other sugars, difficult fermentation, and anti-starch resistance. Furthermore, it is difficult to digest in the digestive tract by oral ingestion, most of it reaches the large intestine, and can be advantageously used as a bifidobacteria growth promoter. The selective growth of bifidobacteria produces organic acids such as acetic acid and lactic acid to lower the pH in the large intestine and suppress the growth of harmful bacteria such as bacteria and spoilage bacteria that cause spontaneous infections. It also suppresses the generation of harmful substances such as ammonia, indole and cresol produced by spoilage bacteria. In addition, it moderately stimulates the intestines, moderately promotes peristaltic movement, and exhibits an intestinal action. Bifidobacteria growth-promoting carbohydrates generate organic acids in the large intestine to lower the pH, increase the solubility of minerals that are easily deficient, such as calcium, magnesium, iron, copper, zinc, and phosphorus, and promote their absorption Therefore, it can be advantageously used as a mineral absorption promoter.
[0020]
These properties of α-isomaltosyl α-glucoside, which is an active ingredient of the present invention, and α-isomaltosyl α-isomaltoside and / or α-isomaltotriosyl α-glucoside together with α-isomaltosyl α-glucoside It can be advantageously used in compositions having various caries-inhibiting effects such as taste products, feeds, feeds, and pharmaceuticals. In particular, it can be advantageously carried out to produce a composition having a caries inhibitory action by containing the active ingredient of the present invention together with one or more ingredients selected from sucrose, sugar alcohol and mineral.
[0021]
The α-isomaltosyl α-glucoside-containing saccharide as an active ingredient of the present invention and the high α-isomaltosyl α-glucoside-containing product that can be separated therefrom can be used as a seasoning for sweetening as it is. If necessary, for example, flour, glucose, maltose, trehalose, sucrose, lactosucrose, isomerized sugar, honey, maple sugar, sorbitol, maltitol, lactitol, dihydrochalcone, stevioside, α-glycosyl stevioside, rebaudioside, glycyrrhizin, L-aspartyl-L-phenylalanine methyl ester, saccharin, glycine, alanine etc. may be used in admixture with one or more suitable amounts of other sweeteners, and if necessary, dextrin, starch It can also be used by mixing with a bulking agent such as lactose.
[0022]
Further, the α-isomaltosyl α-glucoside-containing saccharide as an active ingredient of the present invention and the powdered product of the α-isomaltosyl α-glucoside-rich product obtained therefrom can be used as they are, or as necessary. It is also optional to mix with excipients, binders, etc., and use them in various shapes such as granules, spheres, short bars, plates, cubes and tablets.
[0023]
Further, the sweetness of the α-isomaltosyl α-glucoside-containing saccharide of the present invention and the high α-isomaltosyl α-glucoside content obtained from the saccharide is different from other tastes such as sourness, salt to taste, astringency, umami, and bitterness. It is well harmonized with various substances having taste, and has high acid resistance and heat resistance. Therefore, it can be advantageously used for sweetening and taste improvement of general foods and drinks, and quality improvement.
[0024]
For example, soy sauce, powdered soy sauce, miso, powdered miso, moromi, hashio, sprinkle, mayonnaise, dressing, vinegar, three cups of vinegar, powdered sushi vinegar, Chinese element, tentsuyu, noodle soup, sauce, ketchup, takuanzuke, Chinese cabbage It can be advantageously used as various seasonings such as nori, yakiniku sauce, curry roux, stew, soup, dashi, compound seasoning, mirin, new mirin, table sugar, coffee sugar.
[0025]
In addition, for example, Japanese rice cakes such as rice crackers, hail, rice cakes, rice cakes, manju, oirou, chanterelles, sheep mushrooms, water sheep rice cakes, brocade balls, jelly, castella, rice cakes, bread, biscuits, crackers, cookies, pie , Pudding, butter cream, custard cream, cream puff, waffle, sponge cake, donut, chocolate, chewing gum, caramel, candy and other Western confectionery, ice cream, sherbet and other ice confectionery, fruit syrup pickled, syrup such as ice honey, flower Pastes such as paste, peanut paste, fruit paste, spread, fruit such as jam, marmalade, syrup pickles, sugar cane, processed foods of vegetables, pickles such as Fukujin pickles, bedara pickles, thousand pieces pickles, pickled pickles, hams, sausages, etc. Livestock meat products, fish Manufactured with fish products such as ham, fish sausage, kamaboko, chikuwa, tempura, various delicacies such as sea urchin, salted squid, vinegared konbu, suki-shime, fugumi-rin, dried fish, shellfish, small fish, shellfish, etc. Stewed food such as rutsuda boiled food, boiled beans, potato salad, konbu roll, dairy products, fish meat, livestock meat, fruit, bottled vegetables, canned foods, sake, synthetic liquor, liqueur, Western liquor, tea, coffee, cocoa , Juices, carbonated beverages, lactic acid beverages, soft drinks such as lactic acid bacteria beverages, pudding mixes, hot cake mixes, instant foods such as instant soups, instant soups, and various foods such as baby foods, therapeutic foods, and drinks It can be advantageously used for improving taste and improving quality.
[0026]
Moreover, it can also be used for the purpose of improving the palatability of feed, feed, etc. for domestic animals, poultry, and other domestic animals such as bees, cormorants and fish. In addition, tobacco, toothpaste, lipstick, lip balm, oral solution, tablets, troches, liver oil drops, mouth fresheners, mouth fragrances, gargles, etc. It can be advantageously used as a sweetener for various compositions, as a taste improver, a taste corrector, and as a quality improver.
[0027]
As the quality improver and stabilizer, it can be advantageously applied to various physiologically active substances that easily lose active ingredients, activities, etc., health foods and pharmaceuticals containing the same. For example, vitamin-containing liquids such as thiamine, riboflavin, L-ascorbic acid, liver oil, carotenoid, ergosterol, tocopherol, lipase, elastase, urokinase, protease, β-amylase, isoamylase, glucanase, lactase and other enzyme-containing liquids, medicinal products Ginseng extract, Suppon extract, Chlorella extract, Aloe extract, propolis extract and other extracts, viable bacteria such as viruses, lactic acid bacteria and yeast, and various physiologically active substances such as royal jelly are stable without losing their active ingredients and activities. Can easily produce high quality health foods and medicines.
[0028]
The method for incorporating the α-isomaltosyl α-glucoside-containing saccharide as an active ingredient of the present invention into the various compositions as described above or a high α-isomaltosyl α-glucoside-containing material that can be separated therefrom is completed. For example, a known method such as mixing, dissolution, melting, dipping, infiltration, spraying, coating, coating, spraying, pouring, and solidification is appropriately selected. The amount is usually 0.1% or more, preferably 0.5% or more. Α-Isomaltosyl α-glucoside which is an active ingredient of the present invention, or α-isomaltosyl α-glucoside together with α-isomaltosyl α-isomaltoside and / or α-isomaltotriosyl α-glucoside itself is a low caries sweetener. It can be advantageously used to produce a composition in which cariesiness of sucrose is positively suppressed by using this together with sucrose. When used in combination with sucrose, the active ingredient of the present invention is preferably used in an amount of 5% or more, preferably 10% or more based on sucrose. Next, the present invention will be described more specifically by experiments.
[0029]
[Experiment 1 Preparation of α-Isomaltosyl α-Glucoside, α-Isomaltosyl α-Isomaltoside and α-Isomaltriosyl α-Glucoside]
60 parts by weight of trehalose (manufactured by Hayashibara Biochemical Laboratories Co., Ltd.) and 40 parts by weight of maltotetraose (manufactured by Hayashibara Biochemical Laboratories Co., Ltd.) are heated and dissolved in 150 parts by weight of water. 5, α-glucosidase derived from Aspergillus niger (manufactured by Amano Pharmaceutical Co., Ltd., trade name “Transglucosidase Amano”) was added for 5 units per maltotetraosegram, reacted for 24 hours, and then heated to 100 ° C. for 20 minutes. The enzyme was deactivated. This solution contains about 22% α-isomaltosyl α-glucoside, about 4% α-isomaltosyl α-isomaltoside, about 6% α-isomaltotriosyl α-glucoside, in addition to glucose, maltose, It contained reducing sugars such as maltotriose, unreacted trehalose and maltotetraose. This solution was decolorized with activated carbon, purified by desalting with an ion exchange resin (H type and OH type), concentrated to a concentration of about 50%, and then column chromatography packed with a salt type strongly acidic cation exchange resin. Then, α-isomaltosyl α-glucoside-rich fraction was collected.
[0030]
The resin for fractionation is an alkali metal strong acid cation exchange resin (manufactured by Tokyo Organic Chemical Industry Co., Ltd., trade name “XT-1016”, Na ⁺ And a stainless steel column with a jacket having an inner diameter of 5.4 cm was packed in water suspension. At this time, four columns with a resin layer length of 5 m were connected in series so that the resin layer length was about 20 m. While maintaining the temperature in the column at 60 ° C., 5 v / v% of the raw sugar solution was added, and 60 ° C. warm water was flowed at SV 0.15 for fractionation, and α-isomaltosyl α-glucoside-rich fraction, α-Isomaltosyl α-isomaltoside and α-isomaltotriosyl α-glucoside-rich fractions were collected, respectively.
[0031]
α-Isomaltosyl α-Isomaltoside and α-Isomaltotriosyl The α-glucoside-rich fraction was adjusted to a concentration of about 2% and pH 5.0, and 5 units of glucoamylase was added per gram of solid matter, acting at 40 ° C for 20 hours. Thus, a contaminating carbohydrate having an α-1,4 glucoside bond mainly at the non-reducing end was decomposed. Next, after heating to 100 ° C. for 20 minutes to inactivate the enzyme, this was cooled, desalted and purified according to a conventional method, concentrated to a concentration of about 40%, and packed with octadecyl silica gel (stock) Chromatography with the company YMC, trade name “YMC-Pack R-355-15”), α-isomaltosyl α-isomaltoside-rich fraction and α-isomaltotriosyl α-glucoside-rich fraction Each was collected. The α-isomaltosyl α-isomaltoside-rich solution collected by repeating this method was desalted, purified, concentrated, and vacuum-dried to obtain about 2 parts by weight of α-isomaltosyl α-isomaltoside-containing powder. This powder preparation contained about 97% α-isomaltosyl α-isomaltoside per solid.
[0032]
In addition, in the same manner, about 12 parts by weight of α-isomaltosyl α-glucoside-rich powder (containing about 98% α-isomaltosyl α-glucoside per solid) and α-isomaltotriosyl α-glucoside high About 3 parts by weight of powder (containing about 97% α-isomaltriosyl α-glucoside per solid) was obtained.
[0033]
[Experiment 2 α-Isomaltosyl Physicochemical Properties of α-Isomaltside]
The physicochemical properties were examined using α-isomaltosyl α-isomaltoside-rich powder preparation prepared by the method of Experiment 1.
(1) Elemental analysis
Measured value C = 42.1% H = 6.3% O = 51.6%
Theoretical value C = 41.98% H = 6.17% O = 51.85%
(Molecular formula: C _{twenty four} H ₄₂ O _{twenty one} )
(2) Molecular weight
666.6 Dalton
(3) UV absorption
No characteristic absorption is shown when measured in aqueous solution.
(4) Taste
The sweetness is about 1/5 that of sucrose, the taste is good, and there is no odor.
(5) Solubility in drugs
Easily soluble in water, 0.1N-NaOH, 0.1N-HCl.
Insoluble in methanol and ethanol.
Insoluble in chloroform and ethyl acetate.
(6) Color reaction
Shows green color by anthrone-sulfuric acid reaction.
Ferring's liquid reduction reaction is negative.
Iodine reaction is negative.
(7) Structure
(A) When hydrolyzed with 1N-sulfuric acid, only D-glucose is produced.
(B) This substance is methylated and then hydrolyzed with an acid, followed by reduction and acetylation to give glycitol acetate. The obtained methyl hexitol acetate is analyzed by gas chromatography. -O-acetyl-2,3,4,6-tetra-O-methylglucitol and 1,5,6-tri-O-acetyl-2,3,4-tri-O-methylglucitol are 1 Obtained in a molar ratio of 1 to 1.
(C) It is partially decomposed by the action of glucoamylase to produce glucose, trehalose and α-isomaltosyl α-glucoside. Isomalt dextranase is not subject to degradation.
(D) Carbon nuclear magnetic resonance analysis ( ¹³ C-NMR), 12 ¹³ A C signal was obtained. Reference material, α-, reported by JH Bradbury et al. In “Carbohydrate Research”, Vol. 126, pages 125-156 (1984) From the chemical shift of D-glucopyranose, each carbon is assigned, and this substance is judged to be a carbohydrate composed of O-α-D-glucopyranosyl- (1 → 6) -α-D-glucopyranoside. Furthermore, from the results of molecular weight and constituent sugar analysis, it is a tetrasaccharide consisting of glucose, which is half of 24 carbons. ¹³ Since it showed a C signal, the substance had a point contrast structure, namely O-α-D-glucopyranosyl- (1 → 6) -α-D-glucopyranosyl O-α-D-glucopyranosyl- (1 → 6)- It is judged to have the structure of α-D-glucopyranoside. From the above results, the chemical structure of this substance can also be shown as in FIG.
[0034]
From this structure, this substance is named α-isomaltosyl α-isomaltoside.
[0035]
α-Isomaltosyl α-Isomaltosyl α-glucoside and α-isomaltotriosyl α-glucoside obtained in the same manner as α-isomaltoside are respectively O-α-D-glucopyranosyl- ( 1 → 6) -α-D-glucopyranosyl α-D-glucopyranoside and O-α-D-glucopyranosyl- (1 → 6) -O-α-D-glucopyranosyl- (1 → 6) -α-D-glucopyranosyl It is judged to be α-D-glucopyranoside. The chemical structures of these substances can be shown as in FIGS.
[0036]
[Experiment 3 Maillard reaction]
A solution containing 10% α-isomaltosyl α-glucoside, 1% glycine and 50 mM phosphate buffer (pH 7.0) prepared by the method of Experiment 1 was kept at 100 ° C. for 90 minutes, and after cooling, Absorbance at 480 nm and 1 cm cell was measured. Further, α-isomaltosyl α-isomaltoside and α-isomaltotriosyl α-glucoside prepared by the method of Experiment 1 were similarly tested. As comparative examples, trehalose, isomaltose, isomalt triose, and isomalt tetraose were similarly tested. The results are shown in Table 1.
[0037]
[Table 1]

[0038]
As is apparent from the results in Table 1, α-isomaltosyl α-glucoside, which is the active ingredient of the present invention, has a very low coloration degree due to the Maillard reaction, and isomaltotriose, which is a reducing sugar having the same polymerization degree. It was found to be about 3% of the degree, and, like trehalose, it is a carbohydrate that does not substantially show a Maillard reaction. Α-Isomaltosyl α-tosomatoside and α-isomaltotriosyl α-glucoside, which were tested at the same time, were found to be carbohydrates that did not show Maillard reaction, as did α-isomaltosyl α-glucoside.
[0039]
[Experiment 4 Digestion Test]
Using the α-isomaltosyl α-glucoside prepared by the method of Experiment 1, Okada et al. Reported in the Journal of Japanese Society of Nutrition and Food, Vol. 43, No. 1, pages 23 to 29 (1990). The digestion test was performed in vitro (in vitro) and the degree of digestion of α-isomaltosyl α-glucoside was examined by the degradation rate (ratio of glucose to total sugars). Further, α-isomaltosyl α-isomaltoside and α-isomaltotriosyl α-glucoside prepared by the method of Experiment 1 were similarly tested. As comparative examples, maltose, trehalose and isomaltose were similarly tested. The results are shown in Table 2.
[0040]
[Table 2]

[0041]
As is apparent from the results in Table 2, maltose and isomaltose of the comparative example are mainly degraded by small intestinal mucosal enzymes, whereas α-isomaltosyl α-glucoside of the present invention is slightly degraded mainly by small intestinal mucosal enzymes. Therefore, it is determined that most of them reach the large intestine when taken orally. α-Isomaltosyl α-Isomaltosid and α-Isomaltriosyl α-Glucoside is also less digestible in the same way as α-Isomaltosyl α-glucoside, although there are some differences in the degradation rate by small intestinal mucosal enzymes Carbohydrates, in other words, low-calorie carbohydrates.
[0042]
[Experiment 5: Utilization test by intestinal bacteria]
Using the α-isomaltosyl α-glucoside prepared by the method of Experiment 1, it is described in Mitsuoka Tomoshi, “The World of Enterobacteria (Separation and Identification of Anaerobic Bacteria)”, p. 325, Sobunsha (1984). An anaerobic culture was performed at 37 ° C. for 96 hours in a PYF medium and a sugar-added PYF medium supplemented with 0.5% w / v sugar in the PYF medium, and this culture solution was diluted 5 times and its turbidity (in a 1 cm cell) The degree of intestinal bacterial growth was determined from the absorbance at 750 nm, and the quality of the assimilation was determined. In addition, α-isomaltosyl α-isomaltoside and α-isomaltotriosyl α-glucoside prepared in Experiment 1 were similarly tested. Moreover, it tested similarly using glucose, a trehalose, and isomaltose as a comparative example. The judgment criteria are shown in Table 3, and the results are shown in Tables 4 and 5.
[0043]
[Table 3]

[0044]
[Table 4]

[Table 5]

[0045]
As is apparent from the results of Tables 4 and 5, unlike glucose and trehalose of the comparative examples, the α-isomaltosyl α-glucoside of the present invention has high selective utilization by Bifidobacterium, and similarly α-Isomaltosyl α-Isomaltoside and α-isomaltotriosyl α-glucoside were also found to be carbohydrates with high selective utilization by Bifidobacterium. Considering together with the results of Experiment 4, α-isomaltosyl α-glucoside, together with α-isomaltosyl α-isomaltoside and α-isomaltotriosyl α-glucoside, reaches the large intestine by oral ingestion, and bifidobacteria It is judged that it can function as a growth promoter.
[0046]
[Experiment 6: Effect on Bifidobacteria Growth Promotion in vivo]
Five subjects (male, average age 40.6 years, average body weight 62.2 kg) ingested α-isomaltosyl α-glucoside or α-isomaltosyl α-isomaltoside once daily and 10 g dissolved in hot soup at lunch time. This was continued for 14 days. The experimental sequence was an α-isomaltosyl α-isomaltoside intake experiment followed by a 14-day control period, followed by an α-isomaltosyl α-glucoside intake experiment. Obtain the relative change in stool weight, stool weight relative change, stool pH, total number of bacteria per gram of stool, ratio of bifidobacteria in total number of bacteria, and total number of bifidobacteria before and after intake for 14 days The average value of 5 subjects was calculated. Among these, the total number of bacteria was measured according to the method described in Mitsuoka Chitoshi, “The World of Enterobacteria (Separation and Identification of Anaerobic Bacteria)”, pp. 53 to 65, Shubunsha (1984). That is, using 13 types of medium excluding the M10 medium, it was determined which bacterial group (genus) the appearing colony belongs to and the number of bacteria was measured. The number of bacteria in each group was defined as the true number of bacteria in the medium that gave the highest number of bacteria. The total number of bacteria in each bacterial group thus obtained was defined as the total number of fecal bacteria. The ratio (%) of bifidobacteria (Bifidobacterium) in the total number of bacteria was determined by multiplying the value obtained by dividing the number of bifidobacteria by the total number of bacteria by 100. The relative change in the total number of bifidobacteria is obtained by multiplying the number of bifidobacteria per gram of stool by the weight of stool, and the total number of bifidobacteria before ingestion is taken as 100. The number of bacteria was shown as a relative value. Changes in fecal weight, fecal pH, and total number of bifidobacteria in feces are summarized in Table 6.
[0047]
[Table 6]

[0048]
As is apparent from the results in Table 6, by ingesting α-isomaltosyl α-glucoside or α-isomaltosyl α-isomaltoside, the stool weight per day increased from before the intake, and the number of bifidobacteria per gram of stool increased. However, the ratio of the number of bifidobacteria to the total number of bacteria has increased about twice, the total number of bifidobacteria has increased by about 2.3 to 2.5 times, and the fecal pH has about 0.6 to about It was found that a reduction of 0.8 was seen. α-Isomaltotriosyl α-Glucoside was tested for oral ingestion in the same manner as α-Isomaltosyl α-Isomaltosid and α-Isomaltosyl α-Glucoside. It has been found that it exhibits a bifidobacteria growth promoting effect.
[0049]
[Experiment 7: Acid production by caries-inducing bacteria]
Using α-isomaltosyl α-glucoside prepared by the method of Experiment 1, according to the method reported by Takeuchi in “Journal of Dental Basic Medicine”, Vol. 26, pages 698 to 713 (1984), It was examined whether or not it was subjected to acid fermentation by Streptococcus sobrinus ATCC 27351, a caries-inducing bacterium.
[0050]
A 50% w / v suspension of viable bacteria suspended in Stefan buffer (pH 7.0) and a test carbohydrate solution having a concentration of 0.02M dissolved in the same buffer are mixed and shaken at 37 ° C. The pH was measured over time. Further, α-isomaltosyl α-isomaltoside and α-isomaltotriosyl α-glucoside prepared by the method of Experiment 1 were similarly tested. As comparative examples, sucrose, trehalose and isomaltose were similarly tested. The results are shown in Table 7.
[0051]
[Table 7]

[0052]
As is clear from the results in Table 7, sucrose decreased pH rapidly, trehalose decreased later, and isomaltose decreased slightly, whereas α-isomaltosyl α-glucoside almost decreased pH. Not shown and found to be substantially free of acid fermentation. α-Isomaltosyl α-Isomaltosid and α-isomaltotriosyl α-glucoside were also found to be substantially free from acid fermentation.
[0053]
[Experiment 8 Inhibition of insoluble glucan synthesis by glucosyltransferase of caries-inducing bacteria]
Using α-isomaltosyl α-glucoside prepared by the method of Experiment 1, according to the method reported by Takeuchi in “Journal of Dental Basic Medicine”, Vol. 26, pages 698 to 713 (1984), The effect of Streptococcus sobrinus ATCC27351 on the synthesis of insoluble glucan from sucrose by glucosyltransferase was examined.
[0054]
0.5 ml of crude glucosyl in a mixture of 1 ml of 1% w / v sucrose solution, 1 ml of 1% w / v test carbohydrate solution and 1.5 ml of 0.1M phosphate buffer (pH 6.8) A transferase sample (containing 10 mg of total protein) was added, and the mixture was reacted at 37 ° C. for 16 hours in a small test tube fixed at an elevation angle of 30 degrees. After the reaction solution is gently transferred to another test tube, the remaining tube wall deposits are gently washed with 4 ml of water, the wash solution is combined with the reaction solution, and the resulting precipitate is further centrifuged. The material was non-adherent glucan. Moreover, the tube wall deposits remaining in the reaction test tube were used as an attached glucan. The amount of attached and non-attached glucan was quantified by the anthrone sulfate method, and the total amount of both glucans produced was defined as the amount of insoluble glucan produced. The reaction system using water instead of the test carbohydrate solution, in other words, the reaction system using only sucrose, was used as a control, and the insoluble glucan production inhibition rate was the amount of insoluble glucan produced in the test carbohydrate reaction system relative to the amount of insoluble glucan produced in the control. The percentage was calculated by subtracting from 100. Α-Isomaltosyl α-isomaltoside and α-isomaltotriosyl α-glucoside prepared by the method of Experiment 1 were similarly tested. As a comparative example, the same test was performed using trehalose and isomaltose. The results are shown in Table 8.
[0055]
[Table 8]

[0056]
As is apparent from the results of Table 8, α-isomaltosyl α-glucoside produced significantly less non-adhered glucan and adhering glucan compared to sucrose alone (control), and trehalose and isomaltose in the comparative examples. It was found to inhibit the production of insoluble glucan more strongly. It was also found that α-isomaltosyl α-isomaltoside and α-isomaltotriosyl α-glucoside, which were tested at the same time, strongly inhibited insoluble glucan production in the same manner as α-isomaltosyl α-glucoside.
[0057]
Considering the above results together with the results of Experiment 7, α-isomaltosyl α-glucoside, together with α-isomaltosyl α-isomaltosid and α-isomaltotriosyl α-glucoside, is not subjected to acid fermentation by caries-inducing bacteria. In addition, it inhibits the production of insoluble glucan from sucrose by caries-inducing bacteria and, in addition, strongly prevents adhesion to smooth surfaces, so when used together with sucrose, it effectively inhibits the caries action of sucrose It is judged that it is suitable as a caries inhibitor.
[0058]
[Experiment 9: Acute toxicity test]
Using mice, the acute toxicity test was conducted by orally administering the α-isomaltosyl α-glucoside preparation prepared in Experiment 1. As a result, no death was observed even at the maximum dose that could be administered. Therefore, its LD ₅₀ The value is 50 g / kg or more, and α-isomaltosyl α-glucoside is an extremely low toxicity substance. Further, α-isomaltosyl α-isomaltoside and α-isomaltotriosyl α-glucoside prepared in Experiment 1 were tested in the same manner. ₅₀ The value is 50 g / kg or more, both of which are extremely low toxicity substances.
[0059]
Hereinafter, the production method of a caries inhibitor containing α-isomaltosyl α-glucoside of the present invention, or α-isomaltosyl α-isomaltoside and / or α-isomaltosyl α-glucoside as an active ingredient in Example A, and α as an active ingredient Example I shows a composition having caries inhibitory action containing isomaltosyl α-glucoside, or α-isomaltosyl α-isomaltosid and / or α-isomaltosyl α-glucoside.
[0060]
Example A-1
1 part by weight of trehalose and 1 part by weight of dextrin (DE18, manufactured by Matsutani Chemical Industry Co., Ltd., trade name: Paindex # 4) are heated and dissolved in 2.5 parts by weight of water, and the solution is adjusted to a temperature of 60 ° C. and a pH of 5.5. The α-glucosidase derived from Aspergillus niger was added for 5 units per gram of the solid substance and reacted for 20 hours, and then kept at 95 ° C. for 30 minutes to inactivate the enzyme. This solution was decolorized and filtered with activated carbon according to a conventional method, purified by desalting with H-type and OH-type ion exchange resins, and concentrated to obtain a syrup containing α-isomaltosyl α-glucoside having a concentration of 75% as a solid substance. Per yield of about 92%.
[0061]
This product contains about 21% α-isomaltosyl α-glucoside, about 5% α-isomaltosyl α-isomaltoside and about 7% α-isomaltotriosyl α-glucoside per solid. It is suitable as an inhibitor, and can also be used as a bifidobacteria growth promoter, a mineral absorption promoter, and the like. Furthermore, this product has mild sweetness, moderate viscosity, and moisturizing properties, and as a sweetener, a taste improver, a stabilizer, an excipient, etc., various compositions such as various foods, cosmetics, and pharmaceuticals. Can be advantageously used.
[0062]
Example A-2
In order to purify the reaction solution obtained by the method of Example A-1 and concentrate it to a concentration of 50% to obtain a raw sugar solution to increase the content of α-isomaltosyl α-glucoside, the sodium-type strong acid was used according to the method of Experiment 1. Ion exchange column chromatography using a cationic cation exchange resin “XT-1016”. The resin was packed into four jacketed stainless steel columns with an inner diameter of 5.4 cm and connected in series to a total resin layer length of 20 m.
[0063]
While maintaining the internal temperature of the column at 60 ° C, the sugar solution is added to the resin at 5 v / v%, and hot water at 60 ° C is added to the solution at SV0.15 for fractionation to remove maltose such as maltose and glucose. Then, a fraction containing high α-isomaltosyl α-glucoside was collected. Furthermore, purification, concentration, vacuum drying, and pulverization gave α-isomaltosyl α-glucoside-rich powder in a yield of about 25% per solid.
[0064]
This product contains about 70% α-isomaltosyl α-glucoside, about 4% α-isomaltosyl α-isomaltoside and about 5% α-isomaltotriosyl α-glucoside, which is suitable as a caries inhibitor. It can also be used as a bifidobacteria growth promoter, mineral absorption promoter, and the like. Furthermore, this product has low reducibility, mellow and elegant sweetness, and can be used as a sweetener, taste improver, stabilizer, excipient, etc. in various foods, cosmetics, pharmaceuticals and other compositions. It can be used advantageously.
[0065]
Example A-3
After adding calcium carbonate to 10% potato starch milk to a final concentration of 0.1%, the pH is adjusted to 6.0, and α-amylase (trade name “Spitase HS”, manufactured by Nagase Seikagaku Corporation) is added. ) Was added at 0.1% per gram of starch, heated with stirring, gelatinized and liquefied. Immediately after autoclaving (120 ° C.) for 20 minutes, the temperature was adjusted to 40 ° C. and pH 6.5. To this, 500 units of amylase (manufactured by Hayashibara Biochemical Laboratories Co., Ltd.) per gram starch, Arthrobacter sp. Q36 (deposited) disclosed in Japanese Patent Application No. 6-79291 by the applicant of the present application. No. FERM BP-4316) -derived non-reducing saccharide-forming enzyme and 3 units of trehalose-free enzyme derived from the same strain were added and reacted for 12 hours to obtain a sugar solution containing about 55% trehalose. Next, the enzyme was inactivated by maintaining at 95 ° C. for 30 minutes, and then concentrated to a solid concentration of 45%. Further, the temperature was adjusted to 60 ° C. and pH 5.0, and Candida tropicalis. 3 units of α-glucosidase derived from IFO0589 (manufactured by Hayashibara Biochemical Laboratories Co., Ltd.) was added per solid and reacted for 24 hours. This reaction solution is kept at 95 ° C. for 30 minutes to inactivate the enzyme, then decolorized and filtered with activated carbon according to a conventional method, purified by desalting with H-type and OH-type ion exchange resins, and further concentrated. A syrup containing α-isomaltosyl α-glucoside at a concentration of about 75% was obtained in a yield of about 95% per solid.
[0066]
This product contains about 20% α-isomaltosyl α-glucoside, about 3% α-isomaltosyl α-isomaltoside and about 5% α-isomaltotriosyl α-glucoside per solid. It is suitable as an inhibitor, and can also be used as a bifidobacteria growth promoter, mineral absorption promoter, and the like. Furthermore, this product has mild sweetness, moderate viscosity, and moisturizing properties, and as a sweetener, a taste improver, a stabilizer, an excipient, etc., various compositions such as various foods, cosmetics, and pharmaceuticals. Can be advantageously used.
[0067]
Example A-4
Calcium carbonate is added to 30% corn starch milk to a final concentration of 0.1%, and then adjusted to pH 6.5, and α-amylase (trade name “Termameal 60L” manufactured by Novo) is added to the starch gram. 0.2% per unit, heated with stirring, gelatinized and liquefied, immediately autoclaved (120 ° C) for 20 minutes, then cooled to 55 ° C, and isoamylase (produced by Hayashibara Biochemical Laboratories, Inc.) ) Per 500 grams of starch and β-amylase (manufactured by Nagase Seikagaku Co., Ltd.) at a rate of 30 units per gram of starch and reacted for 48 hours to obtain a sugar solution having a maltose content of about 84%. . The reaction solution was heated at 95 ° C. for 30 minutes and then adjusted to a temperature of 60 ° C. and a pH of 7.0, and the applicant of the present application described in Japanese Patent Application No. 6-144092. (Japanese Patent Laid-Open No. 7-170977) The maltose trehalose converting enzyme derived from Thermus aquaticus ATCC 33923 disclosed in 1) was added at a rate of 1 unit per gram of starch and reacted for 24 hours to obtain a sugar solution containing about 50% trehalose. The reaction solution was adjusted to pH 5.5, and 3 units of α-glucosidase derived from Aspergillus niger was added per gram of solid matter and reacted at 60 ° C. for 24 hours. Next, after maintaining the temperature at 95 ° C. for 30 minutes to inactivate the enzyme, it was decolorized and filtered with activated carbon according to a conventional method, purified by desalting with H-type and OH-type ion exchange resins, further concentrated, vacuum dried, By grinding, an α-isomaltosyl α-glucoside-containing powder was obtained in a yield of about 90% per solid.
[0068]
This product contains about 20% α-isomaltosyl α-glucoside, about 4% α-isomaltosyl α-isomaltoside and about 6% α-isomaltotriosyl α-glucoside per solid. It is suitable as an inhibitor, and can also be used as a bifidobacteria growth promoter, a mineral absorption promoter, and the like. Furthermore, this product has mild sweetness, moderate viscosity, and moisturizing properties, and as a sweetener, a taste improver, a stabilizer, an excipient, etc., various compositions such as various foods, cosmetics, and pharmaceuticals. Can be advantageously used.
[0069]
Example A-5
Calcium carbonate is added to 30% potato starch milk to a final concentration of 0.1%, adjusted to pH 6.5, and α-amylase (trade name “Spitase HS”, manufactured by Nagase Seikagaku Corporation) is added thereto. Add 0.01% per gram starch, heat with stirring, gelatinize and liquefy, immediately autoclave (120 ° C) for 5 minutes, then cool to 55 ° C to obtain a liquefied starch solution of less than DE1, pH 7. Adjust to 0, and add pullulanase (produced by Hayashibara Biochemical Laboratories Co., Ltd.) and maltotetraose-producing amylase (produced by Hayashibara Biochemical Laboratories Co., Ltd.) at a rate of 150 units and 8 units per gram of starch, respectively. The reaction was performed for 36 hours. The reaction solution was heated at 95 ° C. for 30 minutes and then cooled to 45 ° C., to which Rhizobium sp. M-11 (deposit number FERM BP) disclosed by the present applicant in European Patent Application Publication No. 06067553A2 was disclosed. -4130) -derived non-reducing saccharide-forming enzyme was added for 2 hours per gram starch and reacted for 64 hours, and then adjusted to a temperature of 60 ° C. and pH 5.0 to obtain α-glucosidase derived from Candida tropicalis IF00589. The mixture was added at a rate of 3 units per gram of starch and allowed to react for 24 hours. The reaction solution was kept at 95 ° C. for 30 minutes to inactivate the enzyme, then decolorized and filtered with activated carbon according to a conventional method, purified by desalting with H-type and OH-type ion exchange resins, further concentrated, Vacuum-dried and pulverized to obtain an α-isomaltosyl α-glucoside-containing powder with a yield of about 90% per solid.
[0070]
This product contains about 18% α-isomaltosyl α-glucoside, about 4% α-isomaltosyl α-isomaltoside and about 5% α-isomaltotriosyl α-glucoside per solid matter. It is suitable as an inhibitor, and can also be used as a bifidobacteria growth promoter, a mineral absorption promoter, and the like. Furthermore, this product has mild sweetness, moderate viscosity, and moisturizing properties, and as a sweetener, a taste improver, a stabilizer, an excipient, etc., various compositions such as various foods, cosmetics, and pharmaceuticals. Can be advantageously used.
[0071]
Example A-6
Calcium carbonate is added to 30% corn starch milk to a final concentration of 0.1%, and then adjusted to pH 6.5, and α-amylase (trade name “Termameal 60L” manufactured by Novo) is added to the starch gram. 0.3% per unit, heated with stirring, gelatinized and liquefied, immediately autoclaved (120 ° C) for 30 minutes, then cooled to 55 ° C to obtain a liquefied starch solution of DE about 4 Non-reducing saccharide-forming enzyme derived from Slobacter sp. Q36 is 4 units per gram starch, isoamylase is 300 units per gram starch, and cyclomaltodextrin glucanotransferase (produced by Hayashibara Biochemical Laboratories) is starch gram. The mixture was added at a rate of 5 units per hour and reacted at pH 6.3 and a temperature of 45 ° C. for 48 hours. This reaction solution is heated at 95 ° C. for 30 minutes, adjusted to a temperature of 55 ° C. and a pH of 5.5, added with 10 units of β-amylase per gram of starch, reacted for 16 hours, and held at 95 ° C. for 30 minutes. After inactivating the enzyme, the mixture was cooled to 60 ° C., 3 units of α-glucosidase derived from Aspergillus niger was added per gram of solid matter, and reacted for 24 hours. The reaction solution is kept at 95 ° C. for 30 minutes to inactivate the enzyme, then decolorized and filtered with activated carbon according to a conventional method, purified by desalting with H-type and OH-type ion exchange resins, and further concentrated. Thus, α-isomaltosyl α-glucoside-containing syrup was obtained in a yield of about 95% per solid.
[0072]
This product contains about 18% α-isomaltosyl α-glucoside, about 2% α-isomaltosyl α-isomaltoside and about 3% α-isomaltotriosyl α-glucoside per solid. It is suitable as an inhibitor, and can also be used as a bifidobacteria growth promoter, a mineral absorption promoter, and the like. Furthermore, this product has mild sweetness, moderate viscosity, and moisturizing properties, and as a sweetener, a taste improver, a stabilizer, an excipient, etc., various compositions such as various foods, cosmetics, and pharmaceuticals. Can be advantageously used.
[0073]
Example A-7
The reaction solution obtained by the method of Example A-1 was purified according to a conventional method, and concentrated syrup having a concentration of about 50% was put into an autoclave, 10% of Raney nickel was added, and the concentration was adjusted to 90 to 120 ° C. with stirring. The hydrogen pressure is increased to 20 to 120 kg / cm ² To complete the hydrogenation, then Raney nickel was removed, decolorized, desalted and purified, and concentrated to give 70% concentration of syrup in 80% yield per solid. This product contains sugar alcohol together with about 21% α-isomaltosyl α-glucoside, about 5% α-isomaltosyl α-isomaltoside and about 7% α-isomaltriosyl α-glucoside per solid. It is suitable as a caries inhibitor, and the product can be advantageously used as a bifidobacteria growth promoter, a mineral absorption promoter and the like. Furthermore, this product does not show reducibility, has mild sweetness, moderate viscosity, and moisturizing properties, and as a sweetener, taste improver, stabilizer, excipient, etc., various foods, cosmetics, pharmaceuticals, etc. It can be advantageously used in various compositions.
[0074]
[Example A-8]
The α-isomaltosyl high α-isomaltoside-rich fraction obtained by the method of Example A-2 was purified according to a conventional method, and a concentrated syrup having a concentration of about 50% was prepared according to the method of Example A-7. Addition, purification, concentration, vacuum drying and grinding gave α-isomaltosyl-rich α-isomaltoside-rich powder in a yield of about 70% per solid. This product contains sugar alcohol together with about 32% α-isomaltosyl α-glucoside, about 20% α-isomaltosyl α-isomaltoside and about 28% α-isomaltriosyl α-glucoside per solid. It is suitable as a caries inhibitor, and the product can be advantageously used as a bifidobacteria growth promoter, a mineral absorption promoter and the like. Furthermore, this product does not show reducibility, has a mild and elegant sweetness, and as a sweetener, taste improver, quality improver, stabilizer, excipient, etc., various foods, cosmetics, pharmaceuticals, etc. It can be advantageously used in various compositions.
[0075]
Example A-9
Α-Isomaltosyl α-isomaltoside production reaction solution obtained by the method of Example A-5 was purified according to a conventional method, and concentrated syrup having a concentration of about 50% was hydrogenated according to the method of Example A-7. And purified and concentrated to give a syrup concentration of about 70% in a yield of about 80% per solid. This product contains sugar alcohol together with about 18% α-isomaltosyl α-glucoside, about 4% α-isomaltosyl α-isomaltoside and about 5% α-isomaltriosyl α-glucoside per solid. It is suitable as a caries inhibitor, and the product can be advantageously used as a bifidobacteria growth promoter, a mineral absorption promoter and the like. Furthermore, this product does not exhibit reducibility, has mild sweetness, moderate viscosity, and moisturizing properties, and as a sweetener, taste improver, stabilizer, excipient, etc., various foods, cosmetics, pharmaceuticals It can be advantageously used for various compositions.
[0076]
Example B-1 Sweetener
To 1 part by weight of α-isomaltosyl α-glucoside-rich powder obtained by the method of Example A-2, 0.01 part by weight of α-glycosyl stevioside (trade name “αG Sweet” manufactured by Toyo Seika Co., Ltd.) and L- 0.01 parts by weight of aspartyl-L-phenylalanine methyl ester (trade name “Aspartame”) were uniformly mixed and subjected to a granulating machine to obtain a granular sweetener. This product is suitable for sweetening foods and the like that suppress dental caries because it produces less acid by caries-inducing bacteria and produces less insoluble glucan. Moreover, this product has excellent sweetness quality and has a sweetness level about 2.5 times that of sucrose, and the calorie per sweetness level is reduced to about 1 / 2.5 of sucrose. In addition, this product has no stability of the high-sweetness sweetener blended in it, has excellent stability, and as a low-calorie sweetener, it is a low-calorie for obese and diabetics who have restricted caloric intake. Suitable for sweetening foods and drinks. Moreover, this product has a bifidobacteria growth promoting action and a mineral absorption promoting action, and is also suitable as a beauty food and a health food.
[0077]
[Example B-2 Hard Candy]
30 parts by weight of α-isomaltosyl α-glucoside-containing syrup obtained by the method of Example A-1 was heated and mixed with 100 parts by weight of a 55% sucrose solution, and then heated and concentrated under reduced pressure until the water content was less than 2%. This was mixed with 1 part by weight of citric acid and an appropriate amount of lemon flavor and coloring, and molded according to a conventional method to obtain a product. This product is a hard candy having a low cariogenic bifidobacteria growth promoting action. In addition, this product is a high quality hard candy that is crisp, tastes good and does not cause sucrose crystallization.
[0078]
Example B-3 Chewing gum
3 parts by weight of gum base was heated and melted to a degree of softening, and 3 parts by weight of crystalline maltitol powder and 4 parts by weight of α-isomaltosyl α-glucoside-rich powder obtained by the method of Example A-8 were further added. Appropriate amounts of perfume and coloring were mixed, kneaded by rolls, molded and packaged in accordance with conventional methods to obtain a product. This product is a chewing gum that has a hard cariogenic bifidobacteria growth promoting action. This product is a chewing gum with good texture and flavor.
[0079]
[Example B-4 vegetable juice]
Dissolve 10 parts by weight of α-isomaltosyl α-glucoside-containing syrup obtained by the method of Example A-9 and 5 parts by weight of pullulan (molecular weight of about 10,000) in 1,000 parts by weight of vegetable juice mainly composed of tomato juice. The product was sterilized by heat according to a conventional method and canned to obtain a product. This product is suitable as a beauty drink and a health drink having a bifidobacteria growth promoting action and a mineral absorption promoting action in addition to the caries inhibitory action.
[0080]
[Example B-5 Custard cream]
100 parts by weight of corn starch, 100 parts by weight of α-isomaltosyl α-glucoside-containing syrup obtained by the method of Example A-3, 80 parts by weight of maltose, 20 parts by weight of sucrose and 1 part by weight of sodium chloride were thoroughly mixed, and 280 weights of chicken egg Add 1,000 parts by weight of the boiled milk, and continue to stir it over fire. When the corn starch is completely gelatinized and the whole becomes translucent, stop the fire. Then, this was cooled, an appropriate amount of vanilla flavor was added, and weighed, filled and packaged to obtain a product. This product is suitable as a beauty food and a health food having a bifidobacteria growth promoting action and a mineral absorption promoting action in addition to the caries inhibitory action. In addition, this product has a smooth gloss, mild sweetness and deliciousness.
[0081]
Example B-6 Uiro Element
90 parts by weight of rice flour is mixed with 20 parts by weight of corn starch, 40 parts by weight of sucrose, 80 parts by weight of α-isomaltosyl α-glucoside-containing powder obtained by the method of Example A-4 and 4 parts by weight of pullulan. The element was manufactured. Uiro-no-Momo, an appropriate amount of Matcha and water were kneaded, and this was placed in a container and steamed for 60 minutes to produce Matcha Uiro. This product is suitable as a beauty food or health food having bifidobacteria growth promoting action in addition to caries inhibitory action. In addition, this product has good shine, mouthfeel, and good flavor. Moreover, the aging of starch is suppressed and the shelf life is good.
[0082]
[Example B-7 Sweetened condensed milk]
In 100 parts by weight of raw milk, 3 parts by weight of α-isomaltosyl α-glucoside-containing syrup and 1 part by weight of sucrose obtained by the method of Example A-7 are dissolved, sterilized by heating with a plate heater, and then concentrated to a concentration of 70%. The product was obtained by canning under aseptic conditions. This product has a mild sweet taste and good flavor, and can be advantageously used for seasoning infant foods, fruits, coffee, cocoa, tea and the like. Moreover, this product is suitable as a beauty food or health food having bifidobacteria growth promoting action and mineral absorption promoting action in addition to caries inhibiting action.
[0083]
[Example B-8 Tablet]
Uniform mixing of 20 parts by weight of α-isomaltosyl α-glucoside-rich powder obtained by the method of Example A-2, 30 parts by weight of hydrous crystal trehalose, 1 part by weight of calcium lactate, 1 part by weight of sugar ester and an appropriate amount of powdered flavor. After that, according to a conventional method, tablets were tableted with a tableting machine so that one tablet was about 350 mg to obtain tablets. This product is suitable as a beauty food or health food having a bifidobacteria growth promoting action and a calcium absorption promoting action in addition to a caries inhibitory action. In addition, this product is an easy-to-drink tablet that does not crack and has good stability, and is usually about 1 to 40 tablets, preferably about 2 to 20 tablets per day for an adult.
[0084]
[Example B-9 Tablet]
20 parts by weight of α-isomaltosyl α-glucoside-containing powder obtained by the method of Example A-4, 10 parts by weight of lactosucrose-containing powder (registered trademark “milk oligo”, sold by Hayashibara Corporation), 20 parts by weight of lactose, After uniformly mixing 1 part by weight of tribasic calcium phosphate, 1 part by weight of calcium lactate, 1 part by weight of sugar ester, an appropriate amount of powdered food coloring and an appropriate amount of powdered fragrance, the tableting machine is adjusted to about 680 mg per tablet according to a conventional method. And tableted to obtain the product. This product is suitable as a beauty food or health food having bifidobacteria growth promoting action and calcium absorption promoting action in addition to caries inhibitory action. This product is usually taken about 1 to 40 tablets, preferably about 2 to 20 tablets per day for an adult.
[0085]
[Example B-10 Nutrient]
480 parts by weight of anhydrous crystalline maltose, 190 parts by weight of dried egg yolk, 209 parts by weight of skim milk powder, 115 parts by weight of α-isomaltosyl high α-glucoside powder obtained by the method of Example A-2, 4.4 parts by weight of sodium chloride, Formulation consisting of 1.85 parts by weight of potassium chloride, 4 parts by weight of magnesium sulfate, 0.01 part by weight of thiamine, 0.1 part by weight of sodium ascorbate, 0.6 part by weight of vitamin E acetate and 0.04 part by weight of nicotinamide A 25g portion of each was filled into a laminated aluminum sachet and heat-sealed to obtain a dissolving type nutrient. This product does not require low-temperature storage, is stable for a long time at room temperature, and has excellent solubility and dispersibility. This product is dissolved in about 150 to 300 ml of warm water for 1 bag and taken from the nasal cavity, cafeteria, stomach, etc. by oral or tube method, providing nutritional support and caries-suppressing action, promoting bifidobacteria growth It exerts action and mineral absorption promotion action, and promotes patient recovery. In particular, it promotes the growth of bifidobacteria in the large intestine, lowers the pH, and suppresses the production of harmful substances such as spoilage substances. Moreover, the amount of feces can be increased and constipation that tends to occur in patients can be prevented. In addition, this product can be advantageously used not only for humans but also as a composition having a bifidobacteria growth promoting action for oral intake or tube feeding for domestic animals.
[0086]
[Example B-11 Nutrient]
14.5 parts by weight of anhydrous crystalline trehalose, 4.05 parts by weight of sucrose, 3.2 parts by weight of powdered persimmon juice, 3.0 parts by weight of α-isomaltosyl α-glucoside-containing powder obtained by the method of Example A-5, A compound consisting of 0.11 part by weight of citric acid, 0.02 part by weight of ascorbic acid and 0.1 part by weight of powdered orange fragrance is prepared, and 400 g of each is filled and sealed in a screw-cap can, Manufactured nourishment. This product has good stability and solubility as in Example B-10. This product is a composition having a bifidobacteria growth-promoting action, which is obtained by dissolving about 25 g in about 100 to 150 ml of warm water and ingesting it by the oral or tube method as in Example B-10. Along with nutritional supplementation, it promotes the growth of bifidobacteria and promotes the absorption of minerals and promotes patient recovery. Moreover, it can be advantageously used as a nutrient that reduces the caries of sucrose.
[0087]
[Example B-12 Toothpaste]
Dicalcium phosphate 45 parts by weight, pullulan 2.95 parts by weight, sodium lauryl sulfate 1.5 parts by weight, glycerin 20 parts by weight, polyoxyethylene sorbitan laurate 0.5 parts by weight, preservative 0.05 parts by weight, Examples 15 parts by weight of α-isomaltosyl α-glucoside-containing syrup obtained by the method of A-6, 5 parts by weight of sucrose and 10 parts by weight of water were mixed according to a conventional method to obtain a toothpaste. This product has moderate sweetness and is particularly suitable as a toothpaste for children.
[0088]
【The invention's effect】
As is apparent from the above, the non-reducing oligosaccharide α-isomaltosyl α-glucoside, which is an active ingredient of the present invention, or α-isomaltosyl α-isomaltoside and / or α-isomaltotriosyl α together with α-isomaltosyl α-glucoside -Glucoside itself is very stable and has good quality and mild sweetness. This non-reducing oligosaccharide is hardly fermented by caries-inducing bacteria and the like, inhibits synthesis of insoluble glucan from sucrose by caries-inducing bacteria, suppresses plaque formation, and suppresses caries.
[0089]
Non-reducing oligosaccharides are chemically stable and have the property of stabilizing amino acids and oligopeptides that are prone to browning reactions, as well as active ingredients and physiologically active substances that easily lose their activity. Yes. In addition, it has properties such as osmotic pressure controllability, activation, irradiability, moisture retention, viscosity, prevention of crystallization of other sugars, difficulty of fermentation, and starch aging prevention. These various properties can be advantageously used for compositions having various caries-inhibiting effects such as foods and drinks, foods, feeds, feeds, and pharmaceuticals. This composition has not only a caries inhibitory action, but also a bifidobacteria growth promoting action and a mineral absorption promoting action, and is suitable as various beauty and health foods and drinks.
[0090]
Accordingly, a caries inhibitor containing α-isomaltosyl α-glucoside or α-isomaltosyl α-glucoside of the present invention together with α-isomaltosyl α-isomaltoside and / or α-isomaltotriosyl α-glucoside and its production The establishment of methods and uses has great industrial significance in the food, cosmetic and pharmaceutical fields.
[Brief description of the drawings]
FIG. 1 is a diagram showing the structure of α-isomaltosyl α-isomaltoside.
FIG. 2 is a diagram showing the structure of α-isomaltosyl α-glucoside.
FIG. 3 is a diagram showing the structure of α-isomaltotriosyl α-glucoside.

Claims (4)

  The caries inhibitor which uses (alpha) -isomaltosyl (alpha) -glucoside or (alpha) -isomaltosyl (alpha) -glucoside and (alpha) -isomaltosyl (alpha) -isomaltoside and / or (alpha) -isomaltotriosyl (alpha) -glucoside as an active ingredient.   Α-glucosidase or α-glucosidase and glucoamylase are allowed to act on an aqueous solution containing trehalose and starch, and α-isomaltosyl α-isomaltoside and / or α-isomaltotriosyl α- together with α-isomaltosyl α-glucoside Α-Isomaltosyl α-glucoside or α-isomaltosyl α-glucoside together with α-isomaltosyl α-isomaltoside and / or α-isomaltotriosyl α -Manufacturing method of the caries inhibitor which uses glucoside as an active ingredient.   When an aqueous solution containing trehalose and starch is reacted with a non-reducing saccharide-forming enzyme and trehalose-releasing enzyme in an aqueous solution containing starch or maltose / trehalose converting enzyme is allowed to act on an aqueous solution containing maltose. It is an aqueous solution containing the resulting trehalose and starch as compounds, or a non-reducing saccharide-forming enzyme is allowed to act on an aqueous solution containing starch or non-reducing to an aqueous solution containing starch 3. An aqueous solution containing a compound having both a trehalose structure and an α-1,4 glucoside-linked starch structure in a molecule obtained by the action of a saccharide-forming enzyme and cyclomaltodextrin / glucanotransferase. The manufacturing method of the caries inhibitor of description.   The caries inhibitor according to claim 2 or 3, wherein the method of collecting comprises a step of collecting a high content of α-isomaltosyl α-glucoside using column chromatography packed with a salt type strongly acidic cation exchange resin. Manufacturing method.

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