JP5713571B2 - Maillard reaction inhibitor and AGEs production inhibitor - Google Patents
Maillard reaction inhibitor and AGEs production inhibitor Download PDFInfo
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Description
本発明は、大豆を含む原料の発酵分解物から得られる水溶性高分子物質を有効成分とするメイラード反応阻害剤に関する。さらに、ＡＧＥｓ（Ａｄｖａｎｃｅｄ ｇｌｙｃａｔｉｏｎ ｅｎｄｐｒｏｄｕｃｔｓ、以下ＡＧＥｓとする）生成抑制剤等に関するものである。 The present invention relates to a Maillard reaction inhibitor comprising a water-soluble polymer substance obtained from a fermentative decomposition product of a raw material containing soybean as an active ingredient. Furthermore, it relates to AGEs (Advanced glycation end products, hereinafter referred to as AGEs) production inhibitors and the like.
メイラード反応は、還元糖のカルボニル基とアミノ化合物のアミノ基が縮合するものであり、メイラード反応の他、アミノカルボニル反応、糖化反応、グリケーションなどとよばれている。
食品の調理・加工の過程でメイラード反応によって、色や香りの生成およびテクスチャーの変化がもたらされることから、食品の品質向上・品質劣化の双方に深く関与する反応とされてきた。また、メイラード反応進行に伴う褐変化や風味の変化は食品の加熱履歴や貯蔵時間と相関することから、鮮度低下や品質劣化の指標にもなっている。
The Maillard reaction is a condensation of a carbonyl group of a reducing sugar and an amino group of an amino compound, and is called aminocarbonyl reaction, saccharification reaction, glycation, etc. in addition to Maillard reaction.
The Maillard reaction in the process of food preparation and processing brings about the generation of color and fragrance and changes in texture, and thus has been deeply involved in both quality improvement and quality deterioration of food. Moreover, since the browning change and flavor change accompanying the progress of the Maillard reaction correlate with the heating history and storage time of the food, it is also an index of freshness reduction and quality deterioration.
近年、メイラード反応は生体内においても進行していることが知られ、本反応の後期段階においてＡＧＥｓ（終末糖化産物、後期糖化生成物）とよばれる物質が生成されることが確認されている。食品におけるメイラード反応の産物であるメラノイジン色素もＡＧＥｓの一種と理解されるようになってきている（例えば、非特許文献１、参照）。
このＡＧＥｓの生成過程において、活性酸素が発生する。発生した活性酸素はタンパク質を傷害し、寿命の長いタンパク質では糖化によるタンパク質の構造変化や重合が生じ、機能不全をおこして様々な疾病の原因となる。特に糖尿病状態では、血液中の糖濃度が高い状態で持続するためメイラード反応の進行が速く、ＡＧＥｓが多く蓄積され、糖尿病の合併症を併発すると推測されている。さらに、老化現象、認知症、ガン、高血圧、動脈硬化症などにも関与していることが明らかにされている。
In recent years, it has been known that the Maillard reaction proceeds in vivo, and it has been confirmed that substances called AGEs (terminal glycation products, late glycation products) are produced in the later stage of the reaction. Melanoidin pigment, which is a product of the Maillard reaction in foods, has come to be understood as a kind of AGEs (see Non-Patent Document 1, for example).
In this AGE generation process, active oxygen is generated. The generated active oxygen damages the protein, and in the case of a long-lived protein, the structural change and polymerization of the protein occur due to glycation, resulting in malfunction and causing various diseases. Particularly in the diabetic state, it is presumed that the Maillard reaction progresses rapidly because the sugar concentration in the blood is high, and a large amount of AGEs is accumulated, resulting in complications of diabetes. Furthermore, it has been clarified that it is also involved in aging phenomenon, dementia, cancer, hypertension, arteriosclerosis and the like.
このように、メイラード反応は食品の品質に大きな影響を与えるだけでなく、生体においても様々な疾病に関与するものと考えられる。従って、この反応を阻害または抑制することにより、糖尿病合併症やこれに伴う動脈硬化、心筋異常などの発症・進展を防ぐことが期待されている。
メイラード反応の阻害または抑制能を有する物質として、アミノグアニジンなどいくつかの合成化学品が見つかっており、これらの応用が研究されているが、副作用などの問題から実用化には課題を残している。そこで、本発明者らは、食品原料、特に大豆を原料とした発酵食品から安全なメイラード反応阻害剤を開発することを検討した。
Thus, the Maillard reaction is considered not only to greatly affect the quality of food, but also to be involved in various diseases in the living body. Therefore, by inhibiting or suppressing this reaction, it is expected to prevent the onset and progress of diabetic complications, arteriosclerosis and myocardial abnormality associated therewith.
Several synthetic chemicals such as aminoguanidine have been found as substances having the ability to inhibit or suppress the Maillard reaction, and their application has been studied, but problems remain in practical use due to problems such as side effects. . Therefore, the present inventors examined the development of a safe Maillard reaction inhibitor from food raw materials, particularly fermented foods made from soybeans.
大豆やその発酵物を由来とする糖尿病合併症、動脈硬化、心筋異常などの疾病に有用な物質として、例えば、次のような物質が開示されている。１）大豆発酵産物を主成分とした有効成分がイソフラボンであるとする組成物について、タンパク質の非酵素的糖化の抑制作用を有し、糖尿病合併症を予防することが開示されている（例えば、特許文献１参照）。２）醤油粕の水抽出物や酢酸エチル抽出物がメイラード反応を阻害することが開示されている（例えば、特許文献２参照）。この抽出物には低分子のポリフェノール（ダイゼイン、ゲニステイン、トリプトファン、チロシン等）が含まれており、これらの物質がメイラード反応阻害に大きく関与していると記されている。３）黒大豆の水及びエタノール抽出物のグリケーション阻害活性が示されている（例えば、特許文献３参照）。４）黒大豆種皮の８０％エタノール抽出エキスがアミノ酸やタンパクの糖化阻害活性を持っていることが開示されている（例えば、特許文献４参照）。また、５）黒麹菌Ａｓｐｅｒｇｉｌｌｕｓ ｎｉｇｅｒにより生産される酵素であるオキシドリダクターゼが乳製品のメイラード反応抑制に利用できること（例えば、特許文献５参照）が開示されている。 As substances useful for diseases such as diabetic complications derived from soybeans and fermented products thereof, arteriosclerosis, and myocardial abnormalities, for example, the following substances are disclosed. 1) It is disclosed that an active ingredient mainly composed of a fermented soybean product is isoflavone, has a non-enzymatic glycation-inhibiting action on proteins, and prevents diabetic complications (for example, Patent Document 1). 2) It is disclosed that a water extract or an ethyl acetate extract of soy sauce cake inhibits the Maillard reaction (see, for example, Patent Document 2). This extract contains low-molecular-weight polyphenols (daidzein, genistein, tryptophan, tyrosine, etc.), and it is described that these substances are greatly involved in inhibition of Maillard reaction. 3) Glycation inhibitory activity of black soybean water and ethanol extract is shown (for example, see Patent Document 3). 4) It is disclosed that 80% ethanol extract of black soybean seed coat has glycation-inhibiting activity of amino acids and proteins (for example, see Patent Document 4). 5) It is disclosed that oxidoreductase, an enzyme produced by Aspergillus niger, can be used to suppress the Maillard reaction of dairy products (see, for example, Patent Document 5).
糖尿病等の予防改善剤としては、６）大豆の外皮からアルカリ抽出して得られる多糖類が血糖値上昇抑制効果を示すこと（例えば、特許文献６参照）、７）大豆に糸状菌を培養して発酵させたトウチ（豆鼓）の抽出物や、大豆タンパクの加水分解物がグルコシダーゼ活性阻害により血糖上昇を抑制すること（例えば、特許文献７〜８参照）が開示されている。また、８）大豆イソフラボンアグリコンを含有するインシュリン抵抗性糖尿病の予防・治療剤（例えば、特許文献９参照）や、９）水溶性大豆多糖類などの食物繊維とポリフェノールを併用することによる糖尿病改善剤（例えば、特許文献１０参照）が開示されている。しかし、これらには、メイラード反応の阻害については触れられていない。 As a preventive / ameliorating agent for diabetes and the like, 6) that a polysaccharide obtained by alkali extraction from soybean hulls has an effect of suppressing an increase in blood glucose level (see, for example, Patent Document 6), 7) culturing filamentous fungi on soybean It has been disclosed that an extract of touchi (bean drum) fermented by fermentation and a hydrolyzate of soy protein suppress an increase in blood sugar by inhibiting glucosidase activity (see, for example, Patent Documents 7 to 8). 8) Insulin-resistant diabetes preventive / therapeutic agent containing soy isoflavone aglycone (see, for example, Patent Document 9), 9) Diabetes ameliorating agent by combining dietary fiber such as water-soluble soy polysaccharide and polyphenol (See, for example, Patent Document 10). However, they do not mention inhibition of the Maillard reaction.
また、メイラード反応において、活性酸素が関与する反応が知られている。
抗酸化力とメイラード反応阻害効果は必ずしも一致するものではないが、例えば、１）醤油粕をエタノール等の極性溶媒で抽出して得られた抽出物をクロマト等で処理して得られる組成物が抗酸化力を持つことが開示されている（例えば、特許文献１１参照）。２）醤油製造工程で産する醤油オリ由来の抗酸化剤が提示され、疎水性の合成吸着剤に吸着させた後、水、２０、４０、８０、１００％メタノール、次いで、アセトンで溶出させたとき、特に８０％メタノール溶出画分の活性がもっとも強いことが開示されている（例えば、特許文献１２参照）。３）濃口醤油もしくは膜濃縮した高分子側の濃口醤油に糖類を混和して高温加熱することによって、強い抗酸化力を持った醤油が得られることが示されている（例えば、特許文献１３参照）。また、４）メイラード反応の産物である色素（メラノイジン）は、油脂の自動酸化を抑制する抗酸化力を持つことが知られている。通常メラノイジンはメイラード反応を進行させるものとして知られている。
なお、食品の褐変進行を抑制する物質としてアスコルビン酸や亜硫酸塩などの還元剤が知られているが、物質の安全性や効果の持続性等の問題により成功していない。
In addition, a reaction involving active oxygen is known in the Maillard reaction.
Antioxidant power and Maillard reaction inhibitory effect do not necessarily coincide, but, for example, 1) a composition obtained by treating an extract obtained by extracting soy sauce cake with a polar solvent such as ethanol by chromatography or the like; It has been disclosed that it has an antioxidant power (see, for example, Patent Document 11). 2) An antioxidant derived from soy sauce ori produced in the soy sauce manufacturing process was presented, adsorbed on a hydrophobic synthetic adsorbent, and then eluted with water, 20, 40, 80, 100% methanol, and then acetone. In particular, it is disclosed that the activity of the fraction eluted with 80% methanol is particularly strong (see, for example, Patent Document 12). 3) It has been shown that soy sauce having strong antioxidant power can be obtained by mixing saccharides in concentrated soy sauce or concentrated concentrated soy sauce on the polymer side and heating at high temperature (see, for example, Patent Document 13). ). 4) It is known that a pigment (melanoidin), which is a product of the Maillard reaction, has an antioxidant power that suppresses the autoxidation of fats and oils. Melanoidin is generally known to promote the Maillard reaction.
In addition, although reducing agents, such as ascorbic acid and a sulfite, are known as a substance which suppresses browning progress of a foodstuff, it has not succeeded by problems, such as the safety | security of a substance and the sustainability of an effect.
さらに、５）大豆をリゾープス属の糸状菌で発酵させたテンペの８０％エタノール抽出物が、ｉｎ ｖｉｔｒｏでＬＤＬの酸化を抑制することから、動脈硬化の抑制作用が示唆されており、イソフラボンのアグリコンが活性物質であろうと推測されている。また、テンペの水抽出物にも抗酸化作用があることが示され、活性物質は同様にイソフラボンアグリコンやアミノ酸、ペプチドであろうと推測されている（非特許文献２、３）。
しかしながら、これらの技術においても、メイラード反応の阻害に関しては触れられていない。
5) 80% ethanol extract of tempeh fermented with soybeans of the genus Rhizopus suppresses the oxidation of LDL in vitro, suggesting an inhibitory effect on arteriosclerosis. Is presumed to be the active substance. Moreover, it has been shown that the water extract of tempeh also has an antioxidant action, and it is speculated that the active substance may be isoflavone aglycone, amino acid, and peptide as well (Non-patent Documents 2 and 3).
However, these techniques do not mention inhibition of the Maillard reaction.
このように、メイラード反応阻害剤を開発することは、生体内でのＡＧＥｓ生成抑制や食品などにおける褐変の抑制につながる技術として重要な課題として理解され、メイラード反応の進行を原因のひとつとする各種疾病に対し、その改善や予防を目的として多くの技術が開示されている。しかし、本発明者らが着目した大豆麹や醤油のような大豆を含む原料の発酵分解物から得られる特定の性質を有する水溶性高分子物質において、このような効果を持つことは知られていなかった。 Thus, the development of Maillard reaction inhibitors is understood as an important issue as a technology that leads to suppression of AGEs generation in vivo and browning in foods, etc., and various causes caused by the progress of Maillard reaction Many techniques have been disclosed for the purpose of improving and preventing diseases. However, it is known that water-soluble polymer substances having specific properties obtained from fermented decomposition products of soybean-containing raw materials such as soybean cake and soy sauce, which the present inventors have focused on, have such effects. There wasn't.
醤油麹や醤油のような大豆を含む原料の発酵分解物に含まれる水溶性の高分子物質は、ヒアルロニダーゼ阻害、腸管免疫賦活活性、ヒスタミン遊離抑制活性、マクロファージ活性化作用、抗アレルギー体質強化効果、鉄吸収促進作用、肝機能障害を抑制する効果、血圧上昇抑制効果、または血中の中性脂肪上昇抑制効果等を有する素材であることが開示されている（例えば、特許文献１４〜１８参照）。しかしながら、本発明に関わるメイラード反応阻害活性効果については知られておらず、本発明によって新たなメイラード反応阻害剤の提供が期待された。 Water-soluble polymer substances contained in fermented decomposition products of soybeans such as soy sauce cake and soy sauce are hyaluronidase inhibitory, intestinal immunity activation activity, histamine release inhibitory activity, macrophage activation effect, antiallergic substance strengthening effect, It is disclosed that the material has an effect of promoting iron absorption, an effect of suppressing liver dysfunction, an effect of suppressing an increase in blood pressure, or an effect of suppressing an increase in neutral fat in blood (for example, see Patent Documents 14 to 18). . However, the Maillard reaction inhibitory activity effect related to the present invention is not known, and the present invention has been expected to provide a new Maillard reaction inhibitor.
本発明は、大豆を含む原料の発酵分解物から得られる水溶性高分子物質を有効成分とするメイラード反応阻害剤の提供を課題とする。さらに該水溶性高分子物質を有効成分とするＡＧＥｓ生成抑制阻害剤の提供を課題とする。 This invention makes it a subject to provide the Maillard reaction inhibitor which uses the water-soluble polymeric substance obtained from the fermentative decomposition product of the raw material containing soybean as an active ingredient. It is another object of the present invention to provide an AGEs production inhibitor that contains the water-soluble polymer substance as an active ingredient.
本発明者らは上記課題を解決すべく、鋭意検討を行った結果、醤油等の大豆を含む原料の発酵分解物から得られる、１）水溶性、２）分子量６，０００以上であって、かつ３）エタノールに不溶という性質を有する水溶性高分子物質を得て、この水溶性高分子物質がメイラード反応阻害作用およびＡＧＥｓ生成抑制作用を持つことを見出し、本発明を完成するに至った。 As a result of intensive studies to solve the above problems, the present inventors obtained 1) water solubility, 2) a molecular weight of 6,000 or more obtained from a fermented decomposition product of raw materials containing soybeans such as soy sauce, And 3) obtaining a water-soluble polymer substance having a property of being insoluble in ethanol, and found that the water-soluble polymer substance has a Maillard reaction inhibitory action and an AGEs production inhibitory action, thereby completing the present invention.
すなわち、本発明は以下の（１）〜（１２）に示されるメイラード反応阻害剤等に関する。
（１）次の１）〜３）の性質を有する、大豆を含む原料の発酵分解物から得られる水溶性高分子物質を有効成分として含むメイラード反応阻害剤。
１）水溶性
２）分子量６，０００以上
３）エタノールに不溶
（２）発酵分解物が、大豆を含む原料に糸状菌を作用させる工程を含む製造方法によって得られる発酵分解物である上記（１）に記載のメイラード反応阻害剤。
（３）上記（１）または（２）に記載のメイラード反応阻害剤を有効成分として含む糖尿病予防又は改善剤。
（４）上記（１）または（２）に記載のメイラード反応阻害剤を有効成分として含む動脈硬化の予防又は改善剤。
（５）次の工程を含む、上記（１）または（２）に記載のメイラード反応阻害剤の製造方法。
１）大豆を含む原料の発酵分解物から、水溶性物質を抽出する工程
２）上記１）の水溶性物質より低分子物質を除去する工程
（６）さらに、３）エタノールに溶解しない物質を回収する工程を含む上記（５）に記載のメイラード反応阻害剤の製造方法。
（７）次の１）〜３）の性質を有する、大豆を含む原料の発酵分解物から得られる水溶性高分子物質を有効成分として含むＡＧＥｓ生成抑制剤。
１）水溶性
２）分子量６，０００以上
３）エタノールに不溶
（８）発酵分解物が、大豆を含む原料に糸状菌を作用させる工程を含む製造方法によって得られる発酵分解物である上記（７）に記載のＡＧＥｓ生成抑制剤。
（９）上記（７）または（８）に記載のＡＧＥｓ生成抑制剤を有効成分として含む糖尿病予防又は改善剤。
（１０）上記（７）または（８）に記載のＡＧＥｓ生成抑制剤を有効成分として含む動脈硬化の予防又は改善剤。
（１１）次の工程を含む、上記（７）または（８）に記載のＡＧＥｓ生成抑制剤の製造方法。
１）大豆を含む原料の発酵分解物から、水溶性物質を抽出する工程
２）上記１）の水溶性物質より低分子物質を除去する工程
（１２）さらに、３）高濃度のエタノールに溶解しない物質を回収する工程を含む上記（１１）に記載のＡＧＥｓ生成抑制剤の製造方法。
That is, this invention relates to the Maillard reaction inhibitor etc. which are shown by the following (1)-(12).
(1) A Maillard reaction inhibitor having, as an active ingredient, a water-soluble polymer substance obtained from a fermentative decomposition product of raw materials containing soybean, having the following properties 1) to 3).
1) Water-soluble 2) Molecular weight 6,000 or more 3) Insoluble in ethanol (2) The fermentation degradation product is a fermentation degradation product obtained by a production method including a step of causing filamentous fungi to act on a raw material containing soybean (1) ) Maillard reaction inhibitor.
(3) A diabetes preventive or ameliorating agent comprising the Maillard reaction inhibitor according to (1) or (2) as an active ingredient.
(4) An agent for preventing or improving arteriosclerosis comprising the Maillard reaction inhibitor according to (1) or (2) as an active ingredient.
(5) The manufacturing method of the Maillard reaction inhibitor as described in said (1) or (2) including the following process.
1) Step of extracting water-soluble substances from fermented decomposition products of raw materials containing soybeans 2) Step of removing low molecular weight substances from the water-soluble substances of 1) above (6) 3) Recovery of substances that do not dissolve in ethanol The manufacturing method of the Maillard reaction inhibitor as described in said (5) including the process to do.
(7) An AGEs production inhibitor containing, as an active ingredient, a water-soluble polymer substance obtained from a fermentative decomposition product of a raw material containing soybean, having the following properties 1) to 3).
1) Water-soluble 2) Molecular weight 6,000 or more 3) Insoluble in ethanol (8) Fermentation degradation product is a fermentation degradation product obtained by a production method including a step of causing filamentous fungi to act on a raw material containing soybean (7) AGEs production inhibitor as described in 1).
(9) A diabetes preventive or ameliorating agent comprising the AGEs production inhibitor according to (7) or (8) as an active ingredient.
(10) An agent for preventing or improving arteriosclerosis comprising the AGEs production inhibitor according to (7) or (8) as an active ingredient.
(11) The manufacturing method of the AGEs production | generation inhibitor as described in said (7) or (8) including the following process.
1) Step of extracting water-soluble substances from fermented decomposition products of raw materials containing soybeans 2) Step of removing low-molecular substances from the water-soluble substances of 1) above (12) 3) Not dissolving in high-concentration ethanol The manufacturing method of the AGEs production | generation inhibitor as described in said (11) including the process of collect | recovering a substance.
本発明のメイラード反応阻害剤およびＡＧＥｓ生成抑制剤は、メイラード反応によって生成するＡＧＥｓの生成抑制や、メイラード反応に伴って発生する活性酸素の発生を抑制し、糖尿病や動脈硬化の予防や進行の抑制に役立つ。
本発明のメイラード反応阻害剤およびＡＧＥｓ生成抑制剤は、醤油等の大豆を含む原料の発酵分解物から得られる水溶性高分子物質を有効成分とするものであることから、安全性が高く、継続的な摂取が可能である。また、大量に製造することもでき、食品等への添加が容易であることからも、健康増進や疾病予防などとして貢献できる。
The Maillard reaction inhibitor and the AGEs production inhibitor of the present invention inhibit the production of AGEs produced by the Maillard reaction and the production of active oxygen that accompanies the Maillard reaction, thereby preventing the prevention of diabetes and arteriosclerosis and the progression thereof. To help.
Since the Maillard reaction inhibitor and the AGEs production inhibitor of the present invention contain a water-soluble polymer substance obtained from a fermented decomposition product of raw materials containing soybeans such as soy sauce as an active ingredient, the safety is high and it is continued. Ingestion is possible. It can also be produced in large quantities and can be easily added to foods and the like, which can contribute to health promotion and disease prevention.
本発明の「メイラード反応阻害剤」および「ＡＧＥｓ生成抑制剤」には、大豆を含む原料の発酵分解物から得られる、１）水溶性、２）分子量６，０００以上であって、かつ３）エタノールに不溶という性質を有する水溶性高分子物質を有効成分として含むものであればいずれのものも含まれる。
ここで、大豆を含む原料の醗酵分解物には、例えば大豆を含む原料に麹菌を接種して発酵させた醤油麹や、醤油麹を食塩水中でさらに長時間発酵熟成させた醤油もろみ、これを圧搾して得られる生醤油、さらに、加熱処理やろ過の工程を経て得られる醤油等が例示できる。また、収率は小さいが醤油粕から得ることもできる。この醗酵分解物の製造にあたり、丸大豆、脱脂加工大豆に限らず、おからや大豆皮、なども大豆を含む原料として利用することができる。また、大豆を含んでいればよく、大豆のほかに麹菌の生育が良好となるような小麦などの他の成分を含んでいてもよい。
The “Maillard reaction inhibitor” and “AGEs production inhibitor” of the present invention include 1) water-soluble, 2) molecular weight of 6,000 or more, 3) Any substance containing a water-soluble polymer substance that is insoluble in ethanol as an active ingredient is included.
Here, the fermented decomposition product of the raw material containing soybean includes, for example, a soy sauce cake obtained by inoculating and fermenting the raw material containing soybean with a koji mold, Examples include raw soy sauce obtained by pressing, and soy sauce obtained through heat treatment and filtration. Moreover, although the yield is small, it can also be obtained from soy sauce cake. In the production of this fermentation decomposition product, not only whole soybeans and defatted soybeans but also okara and soybean hulls can be used as raw materials containing soybeans. Moreover, what is necessary is just to contain soybean, and you may contain other components, such as wheat from which a growth of a koji mold becomes favorable other than soybean.
大豆を含む原料の発酵分解物の製造は、大豆を含む原料を蒸煮または焙煎するなどの加熱処理を施し、これに麹菌などの糸状菌を生育させることによって行う。これによって、メイラード反応阻害活性や、ＡＧＥｓ生成抑制活性等を有する本発明の水溶性高分子物質が発現すると考えられる。この発酵分解物の製造に利用できる糸状菌としてはアスペルギルス属やリゾープス属のような食品工業に利用される微生物を例示できるが、醤油や味噌で利用されるアスペルギルス・オリゼー、及びアスペルギルス・ソーヤ等の醤油麹菌が望ましい。糸状菌の培養は通常行われる方法が適用できる。醤油麹であれば通常３０℃程度で２〜５日程度培養され、この培養によって本発明の水溶性高分子物質が産生される。 Manufacture of the fermentative decomposition product of the raw material containing soybean is performed by subjecting the raw material containing soybean to heat treatment such as steaming or roasting, and growing filamentous fungi such as koji molds on this. As a result, it is considered that the water-soluble polymer substance of the present invention having Maillard reaction inhibitory activity, AGEs production inhibitory activity and the like is expressed. Examples of the filamentous fungi that can be used in the production of this fermentation degradation product include microorganisms used in the food industry such as Aspergillus and Rhizopus, but Aspergillus oryzae and Aspergillus soya used in soy sauce and miso Soy sauce koji is desirable. For culturing filamentous fungi, methods usually performed can be applied. If it is a soy sauce cake, it will be normally culture | cultivated at about 30 degreeC for about 2 to 5 days, and the water-soluble polymer substance of this invention will be produced by this culture | cultivation.
このようにして生成した本発明の水溶性高分子物質は、発酵分解物から水、食塩水、またはこれらの混合液等を用いて抽出することによって得ることができる。加える溶媒の量は特に限定されるものではなく５〜１０倍程度で行えばよい。溶媒量の大小は回収量に影響するが、食塩水は２０％程度の濃度でも収率が低下せず、使用することができる。抽出温度は低温、高温のいずれでも可能であり、時間は１時間から１週間程度で行うが、腐敗しないように管理すればさらに長時間を要してもよい。 The water-soluble polymer substance of the present invention thus produced can be obtained by extraction from the fermentation decomposition product using water, saline, or a mixture thereof. The amount of the solvent to be added is not particularly limited, and may be about 5 to 10 times. Although the amount of the solvent affects the recovered amount, the saline solution can be used without reducing the yield even at a concentration of about 20%. The extraction temperature can be either low or high, and the time is about 1 hour to 1 week, but it may take a longer time if it is managed so as not to rot.
また、発酵分解物をさらに長期間発酵させたものも、本発明の水溶性高分子物質を得るために用いることができる。醤油は上記麹菌の培養物（醤油麹）を食塩水中において１０〜３０℃程度の温度で数ヶ月から１年程度発酵熟成させ、圧搾・ろ過等により得られた澄明な液体であるが、この醤油から本発明の水溶性高分子物質を得ることもできる。その効果及び収量は麹から採取する場合とほとんど差がない。
これら発酵分解物中に生成した本発明に関わる水溶性高分子物質はそのまま利用することも可能であるが、より利用しやすくするために以下のように濃縮してから用いることもできる。
Moreover, what fermented the fermentation decomposition product for a long period of time can also be used in order to obtain the water-soluble polymer substance of this invention. Soy sauce is a clear liquid obtained by aging and culturing the above koji mold culture (soy sauce koji) in saline at a temperature of about 10 to 30 ° C. for several months to one year, and pressing and filtering. Thus, the water-soluble polymer substance of the present invention can also be obtained. The effect and yield are almost the same as when harvested from straw.
The water-soluble polymer substance related to the present invention produced in these fermentation decomposition products can be used as it is, but it can also be used after being concentrated as follows for easier use.
本発明の水溶性高分子物質を上記抽出液、または醤油のような液体から回収・濃縮するためには、一般的な水溶性高分子物質の回収技術が利用できる。透析して透析膜を通過しない画分を回収する操作、分画分子量が６，０００程度の膜を利用した限外ろ過により濃縮する操作、または最終濃度が３０％（ｖ／ｖ）以上になるようにエタノールを添加することにより発生する沈殿を回収する操作等が例示できる。これら操作の手順は生理活性物質そのものの機能に影響することはないので、これらを適宜組み合わせることができる。
本発明に関わる水溶性高分子物質を沈殿採取するために加えるエタノールは、最終濃度が３０％（ｖ／ｖ）以上、望ましくは５０％（ｖ／ｖ）以上にできる量がよい。エタノールに代えてメタノールや２−プロパノール等によっても本発明の水溶性高分子物質は回収できるが、安全性の面でエタノールが好ましい。
上記操作によって濃縮された本発明の水溶性高分子物質は、そのまま、または、減圧濃縮や、乾燥などの一般的な方法で加工して利用できる。
In order to recover and concentrate the water-soluble polymer substance of the present invention from the above extract or a liquid such as soy sauce, a general technique for recovering the water-soluble polymer substance can be used. An operation of collecting a fraction that does not pass through a dialysis membrane by dialysis, an operation of concentrating by ultrafiltration using a membrane having a molecular weight cut off of about 6,000, or a final concentration of 30% (v / v) or more. Thus, the operation | movement etc. which collect | recover the precipitation which generate | occur | produces by adding ethanol can be illustrated. Since these operating procedures do not affect the function of the physiologically active substance itself, they can be appropriately combined.
The amount of ethanol added to precipitate and collect the water-soluble polymer substance according to the present invention is such that the final concentration is 30% (v / v) or more, desirably 50% (v / v) or more. Although the water-soluble polymer substance of the present invention can be recovered by using methanol, 2-propanol or the like instead of ethanol, ethanol is preferable in terms of safety.
The water-soluble polymer substance of the present invention concentrated by the above operation can be used as it is or after being processed by a general method such as concentration under reduced pressure or drying.
利用するにあたっては、その目的に応じて加工できるようにすればよく、特に手法を限定する必要はない。液体に溶解するかもしくは分散させる、または、粉末担体と混合するかもしくはこれに吸着させ、飲食品や医薬（医薬部外品も含む）などに適宜配合するなどが例示できる。本発明の「メイラード反応阻害剤」および「ＡＧＥｓ生成抑制剤」は、糖尿病予防又は改善剤、動脈硬化の予防又は改善剤などの有効成分として配合することもできる。
製剤として使用する場合における、本発明の水溶性高分子物質の使用量は製剤の形態によっても異なるが、１日に乾物として０．１ｇ程度以上摂取できる配合量が好ましく、安全性に問題がないので特に上限は規定しない。
飲食物としては、チューインガム、キャンディ、錠菓、グミゼリー、チョコレート、ビスケットまたはスナック等の菓子、アイスクリーム、シャーベットまたは氷菓等の冷菓、飲料、プリン、ジャム、乳製品、調味料等が挙げられ、これらの飲食物を日常的に摂取することが可能である。これらの飲食物に対する本発明の水溶性高分子物質の添加量としては、飲食物の形態によっても異なるが、嗜好性の面から２０重量％程度以下が望ましい。また、カプセルや錠剤型の特定保健用食品や健康食品の場合、その濃度に上限を設ける必要はない。
In use, it is only necessary to allow processing according to the purpose, and there is no need to limit the method. Examples thereof include dissolving or dispersing in a liquid, mixing with a powder carrier, or adsorbing it to a powder carrier, and blending it appropriately in foods and drinks, medicines (including quasi drugs), and the like. The “Maillard reaction inhibitor” and “AGEs production inhibitor” of the present invention can also be blended as active ingredients such as diabetes preventive or ameliorating agent, arteriosclerosis preventing or ameliorating agent.
When used as a preparation, the amount of the water-soluble polymer substance of the present invention to be used varies depending on the form of the preparation, but it is preferable to use a blending amount that can be ingested by about 0.1 g or more as a dry matter per day, and there is no problem with safety. Therefore, no upper limit is specified.
Examples of foods and drinks include chewing gum, candy, tablet confectionery, gummy jelly, chocolate, biscuits or snacks and other confectionery, ice cream, sorbet or iced confectionery, beverages, pudding, jam, dairy products, seasonings, etc. It is possible to ingest daily food and drink. The amount of the water-soluble polymer substance of the present invention to be added to these foods and drinks is preferably about 20% by weight or less from the viewpoint of palatability, although it varies depending on the form of the food and drink. Further, in the case of a capsule or tablet type food for specified health use or health food, there is no need to set an upper limit for the concentration.
以下、実施例をあげて本発明をさらに詳細に説明するが、本発明はこれらに限定されるものではない。 EXAMPLES Hereinafter, although an Example is given and this invention is demonstrated further in detail, this invention is not limited to these.
醤油からの水溶性高分子物質の採取
脱脂加工大豆、丸大豆および小麦を原料とし、麹菌としてアスペルギルス・オリゼーを用いて麹を作り、常法通り発酵熟成させたもろみを圧搾後、加熱及びろ過工程を経て醤油を製造した。この醤油１００ｍｌに、９５％エタノール２００ｍｌを加えて攪拌後１晩放置して発生した沈殿物を遠心分離によって回収した。この沈殿物に水を加えて溶解後、濾紙ろ過して得られた澄明な液を、分画分子量６，０００〜８，０００の透析チューブに充填し、４℃の流水中で一夜透析した。その後、透析内液を凍結乾燥して約１ｇの淡灰色の粉末を得た。これを本発明品１とした。本発明品１は１）水に可溶、２）分子量６，０００以上であって、かつ３）エタノールに不溶という性質を有していた。
Extraction of water-soluble polymer from soy sauce Using defatted soybeans, whole soybeans and wheat as raw materials, making koji using Aspergillus oryzae as koji molds, pressing and mashing moromi that has been fermented and aged as usual Soy sauce was produced. To 100 ml of this soy sauce, 200 ml of 95% ethanol was added, and after stirring, the precipitate was left overnight and collected by centrifugation. Water was added to the precipitate to dissolve it, and the clear liquid obtained by filtration through filter paper was filled in a dialysis tube having a molecular weight cut off of 6,000 to 8,000 and dialyzed overnight at 4 ° C. in running water. Thereafter, the dialysis internal solution was freeze-dried to obtain about 1 g of a light gray powder. This was designated as Product 1 of the present invention. Invention product 1 had the properties of 1) soluble in water, 2) a molecular weight of 6,000 or more, and 3) insoluble in ethanol.
醤油麹からの水溶性高分子物質の採取
３Ｌ容三角フラスコに脱脂加工大豆１００ｇを入れ、熱水１２０ｍｌを加えた後３０分間放置した。続いて、グルコース１０ｇを加えよく撹拌後、１２１℃で４５分間オートクレーブ処理を行った。放冷後、麹菌（アスペルギルス・ソーヤ）を０．１ｇ植菌し、よく撹拌した。その後、３０℃に保持したウォーターバスで７２時間静置培養を行った。その間、３回の攪拌を行った（２０時間後、３０時間後及び４８時間後）。
培養物に純水１Ｌを加えて６０℃で２０時間攪拌抽出した後、７，０００ｒｐｍで３０分間遠心分離を行い、上清を回収した。この液を緩やかに加熱し１０分間沸騰状態を保った後、５５℃で一晩放置後遠心分離を行って澄明な抽出液を得た。この抽出液に２倍量のエタノールを添加して発生した沈殿物を遠心分離によって採取し、７０℃で送風乾燥して、約５ｇのほぼ白色の粉末を得た。これを本発明の本発明品２とした。本発明品２は１）水に可溶、２）分子量６，０００の透析膜で処理すると、ほとんどが透析されずに残存する、かつ、３）エタノールに不溶という性質を有していた。
Extraction of water-soluble polymer substance from soy sauce cake 100 g of defatted soybeans was placed in a 3 L Erlenmeyer flask, and 120 ml of hot water was added and left for 30 minutes. Subsequently, 10 g of glucose was added and stirred well, followed by autoclaving at 121 ° C. for 45 minutes. After standing to cool, 0.1 g of Aspergillus soya was inoculated and stirred well. Then, static culture was performed in a water bath maintained at 30 ° C. for 72 hours. Meanwhile, stirring was performed 3 times (after 20 hours, 30 hours and 48 hours).
After adding 1 L of pure water to the culture and stirring and extracting at 60 ° C. for 20 hours, the culture was centrifuged at 7,000 rpm for 30 minutes, and the supernatant was recovered. This solution was gently heated to maintain a boiling state for 10 minutes, and then left overnight at 55 ° C. and then centrifuged to obtain a clear extract. A precipitate generated by adding twice the amount of ethanol to this extract was collected by centrifugation and blown and dried at 70 ° C. to obtain about 5 g of an almost white powder. This was designated as Product 2 of the present invention. The product 2 of the present invention had the following properties: 1) soluble in water, 2) most treated without dialysis when treated with a dialysis membrane having a molecular weight of 6,000, and 3) insoluble in ethanol.
醤油粕からの水溶性高分子物質の採取
脱脂大豆で製造した醤油の醤油粕１００ｇに１Ｌの水を加えて室温で１時間抽出し、そのろ液を減圧濃縮後乾燥すると約１１ｇの乾燥物が得られた。
この半量（残りの半量は比較品１とした）を約５０ｍｌの水に懸濁すると不溶性物質があったため、遠心分離及び濾紙ろ過によって除去して澄明な溶液を回収した。この液を、分画分子量６，０００の透析膜にいれて流水中で透析して内液を採取し、この液に２倍量の９５％エタノールを加えて発生した沈殿を採取した。さらに、この沈殿物に７０％エタノール１００ｍｌを加えて６０℃で一晩攪拌して洗浄し、その後、遠心分離して沈殿物を回収して乾燥させた。醤油粕からの回収量は約０．３％であった。これを発明品３とした。本発明品３は１）水に可溶、２）分子量６，０００以上であって、かつ３）エタノールに不溶という性質を有していた。また、チロシンやイソフラボン等の低分子物質は検出されなかった。なお、比較品１にはチロシンやイソフラボンの存在が確認できた。
Extraction of water-soluble polymer from soy sauce cake 1L of water is added to 100g of soy sauce sauce made from defatted soybeans and extracted at room temperature for 1 hour. Obtained.
When this half amount (the remaining half amount was Comparative Product 1) was suspended in about 50 ml of water, there was insoluble material, so it was removed by centrifugation and filter paper filtration to recover a clear solution. This solution was placed in a dialysis membrane having a molecular weight cut off of 6,000, dialyzed in running water, and the internal solution was collected. A double amount of 95% ethanol was added to this solution, and the generated precipitate was collected. Further, 100 ml of 70% ethanol was added to the precipitate, and the mixture was washed by stirring overnight at 60 ° C., and then centrifuged to collect the precipitate and dry it. The amount recovered from soy sauce cake was about 0.3%. This was designated as Invention Product 3. The product 3 of the present invention had the properties of 1) soluble in water, 2) a molecular weight of 6,000 or more, and 3) insoluble in ethanol. Moreover, low molecular weight substances such as tyrosine and isoflavone were not detected. In Comparative Product 1, the presence of tyrosine and isoflavone was confirmed.
［試験例１］
ＡＧＥｓ（Ａｄｖａｎｃｅｄ ｇｌｙｃａｔｉｏｎ ｅｎｄｐｒｏｄｕｃｔｓ）生成抑制作用の検証
吉川らの方法（薬学雑誌、１２３、８７１−８８０、２００３）に従い、ＡＧＥｓ生成抑制試験を行った。抑制剤試料として本発明品１〜３、比較品１及び大豆多糖類（ＳＭ７００：三栄源）を比較品２として用いた。反応液最終濃度としてＤ−グルコース１００ｍｇ／ｍｌ、牛血清アルブミン１０ｍｇ／ｍｌ、および０〜５０ｍｇ／ｍｌの本発明品１〜３及び比較品１、２を含む６７ｍＭリン酸緩衝液（ｐＨ ７．２）２．０ｍｌを６０℃で４８時間インキュベーションした。なお、試料中の不溶物による反応への影響を回避するため、本発明品及び比較品は、あらかじめリン酸緩衝液に１００ｍｇ／ｍｌ濃度になるように懸濁し、遠心分離して澄明な液のみを用いて行った。
ＡＧＥｓの生成量は、反応液２００μｌに水２．０ｍｌを加え、蛍光分光光度計を用いて蛍光強度（励起波長３７０ｎｍ、測定波長４４０ｎｍ）を測定することにより求めた。
本発明品１〜３を添加することで濃度依存的に蛍光強度の低下が見られ、ＡＧＥｓ生成抑制に対するＩＣ５０値はそれぞれ９．６ｍｇ／ｍｌ、１２ｍｇ／ｍｌ及び１０ｍｇ／ｍｌであった。また、比較品１、２は５０ｍｇ／ｍｌ以上で、本試験系ではＩＣ５０値は求められなかった。
醤油粕においては高分子画分を採取することにより、ＡＧＥｓ生成阻害の比活性が高くなることが確認できた。また、比較品２は濃度依存性が見られずほとんど活性がないことから、本発明品の水溶性高分子物質は大豆の化学的な処理によって得られた大豆多糖類とは異なり、麹菌による発酵によって何らかの変化を受けたか新たに生成する物質であると思われた。また、麹と醤油では大豆からの収量や比活性が類似しており、麹菌を作用させることが本願発明の活性発現に大きい働きを持っていることが理解される。
[Test Example 1]
Verification of AGEs (Advanced Glycation endproducts) Production Inhibitory Action An AGEs production inhibition test was performed according to the method of Yoshikawa et al. (Pharmaceutical Journal, 123, 871-880, 2003). Inventive products 1 to 3, comparative product 1 and soybean polysaccharide (SM700: Saneigen) were used as comparative products 2 as inhibitor samples. 67 mM phosphate buffer (pH 7.2) containing D-glucose 100 mg / ml, bovine serum albumin 10 mg / ml, and 0 to 50 mg / ml of the present products 1 to 3 and comparative products 1 and 2 as final concentrations of the reaction solution. ) 2.0 ml was incubated at 60 ° C. for 48 hours. In order to avoid the influence of the insoluble matter in the sample on the reaction, the product of the present invention and the comparative product are suspended in a phosphate buffer solution at a concentration of 100 mg / ml in advance and centrifuged to obtain a clear solution only. It was performed using.
The amount of AGEs produced was determined by adding 2.0 ml of water to 200 μl of the reaction solution and measuring the fluorescence intensity (excitation wavelength: 370 nm, measurement wavelength: 440 nm) using a fluorescence spectrophotometer.
By adding the inventive products 1 to 3, the fluorescence intensity decreased in a concentration-dependent manner, and the IC50 values for AGEs production inhibition were 9.6 mg / ml, 12 mg / ml and 10 mg / ml, respectively. Comparative products 1 and 2 were 50 mg / ml or more, and IC50 values were not obtained in this test system.
In soy sauce cake, it was confirmed that the specific activity for inhibiting AGE generation was increased by collecting the polymer fraction. Moreover, since the comparative product 2 does not show concentration dependency and has almost no activity, the water-soluble polymer substance of the product of the present invention is different from soybean polysaccharide obtained by chemical treatment of soybean, and is fermented by koji mold. It seemed to be a substance that had undergone some change or newly generated. In addition, the yield and specific activity from soybean are similar between soy sauce and soy sauce, and it is understood that the action of koji mold has a great effect on the expression of the activity of the present invention.
［試験例２］
本発明品によるメイラード反応阻害効果の検証
食品におけるメイラード反応の進行は、最終的に色や香りの変化となって現れるため、その進行評価は、色の変化を測定することがもっとも端的な手法である。
醤油の着色を評価指標にしてメイラード反応阻害効果を検証した。
ＪＡＳ特級濃口醤油に本発明品１又は２の粉末を０又は１％添加して試験用の醤油を調製した。褐変速度に影響することが知られている全窒素、還元糖は同じであった。この醤油を満量約１５０ｍｌ容の三角フラスコに５０ｍｌを入れて栓をして３０℃で保存した。１ヶ月後に開封して試料１０ｍｌを採取し、再度栓をして２ヶ月後まで保存した。濃化量は使用採取後速やかにＯＤ６１０ｎｍ（光路長３ｍｍ）を測定して評価した。本発明品１及び２を添加した醤油は対照に比べて明らかに濃化が阻害された（表１）。
[Test Example 2]
Verification of Maillard reaction inhibition effect by the product of the present invention The progress of the Maillard reaction in food finally appears as a change in color and scent, so the progress evaluation is most straightforward by measuring the color change. is there.
The Maillard reaction inhibition effect was verified using the coloring of soy sauce as an evaluation index.
A test soy sauce was prepared by adding 0 or 1% of the powder of the product 1 or 2 of the present invention to a JAS special grade thick soy sauce. All nitrogens and reducing sugars known to affect the browning rate were the same. 50 ml of this soy sauce was put into an Erlenmeyer flask having a capacity of about 150 ml, stoppered and stored at 30 ° C. One month later, the container was opened and a 10 ml sample was collected, stoppered again, and stored until two months later. The amount of concentration was evaluated by measuring OD610 nm (light path length 3 mm) immediately after use collection. Concentration of the soy sauce to which the inventive products 1 and 2 were added was clearly inhibited compared to the control (Table 1).
本発明のメイラード反応阻害剤およびＡＧＥｓ生成抑制剤の提供により、メイラード反応を原因のひとつとする糖尿病や動脈硬化の予防や進行の抑制に役立つ。 By providing the Maillard reaction inhibitor and the AGEs production inhibitor of the present invention, it is useful for the prevention of diabetes and arteriosclerosis caused by the Maillard reaction and suppression of progression.
Claims (2)
１）水溶性
２）分子量６，０００以上
３）エタノールに不溶 Diabetes ameliorating agent comprising, as an active ingredient, a Maillard reaction inhibitor comprising, as an active ingredient, a water-soluble polymer substance obtained from a fermentative decomposition product of Aspergillus spp. (However, food and drink aspects are excluded) .
1) Water-soluble
2) More than 6,000 molecular weight
3) Insoluble in ethanol
The diabetes improving agent according to claim 1, wherein the fermentation decomposition product is a fermentation decomposition product obtained by a production method including a step of allowing an Aspergillus microorganism to act on a raw material containing soybean.
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| JP7063506B1 (en) | 2021-05-27 | 2022-05-09 | ケミ・コム・ジャパン株式会社 | Chocolate flavor enhancer, chocolate flavor enhancer composition, and method for producing the same. |
| CN114208864B (en) * | 2021-12-23 | 2024-04-05 | 广州酒家集团利口福食品有限公司 | Application of plumula Nelumbinis polysaccharide in non-fermented baked food |
| CN114916571A (en) * | 2022-05-23 | 2022-08-19 | 湖北工业大学 | Application of EC quinone in improving toughness biscuit quality |
| JP7496914B1 (en) | 2023-05-10 | 2024-06-07 | キユーピー株式会社 | Acidic liquid seasoning, method for preventing oxidation of acidic liquid seasoning, antioxidant, method for reducing sourness, and sourness reducer |
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| JP4809785B2 (en) * | 2006-09-08 | 2011-11-09 | ヒガシマル醤油株式会社 | Applications of high-molecular substances contained in soy sauce |
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