JP2019205398A - Anti-glycation agent - Google Patents
Anti-glycation agent Download PDFInfo
- Publication number
- JP2019205398A JP2019205398A JP2018103252A JP2018103252A JP2019205398A JP 2019205398 A JP2019205398 A JP 2019205398A JP 2018103252 A JP2018103252 A JP 2018103252A JP 2018103252 A JP2018103252 A JP 2018103252A JP 2019205398 A JP2019205398 A JP 2019205398A
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- Prior art keywords
- bagasse
- decomposition
- extract
- treatment
- glycation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Abstract
Description
本発明は、抗糖化剤に関する。 The present invention relates to an anti-glycation agent.
糖化とはメイラード反応とも呼ばれ、１９１２年にフランスの科学者L.C. Maillardによって発見されたアミノ酸・タンパク質と還元糖の非酵素的な化学反応である。糖化は食品の加熱中におこる着色、香り・風味の変化等食品化学の分野で注目されてきた。 Saccharification is also called Maillard reaction, and is a non-enzymatic chemical reaction between amino acids / proteins and reducing sugar discovered in 1912 by French scientist L.C. Maillard. Saccharification has attracted attention in the field of food chemistry, such as coloring, aroma and flavor changes that occur during heating of food.
生体における糖化は、グルコースなどの還元糖のカルボニル基とタンパク質とが非酵素的に反応し、シッフ塩基（schiff base）の形成を経てアマドリ転移により不可逆的な物質である糖化タンパク質となり、3-デオキシグルコソン（３ＤＧ）、グリオキサール、メチルグリオキサール、グリセルアルデヒド、グルタールアルデヒドなどのカルボニル化合物を中心とする反応中間体生成を経て、糖化最終生成物（advanced glycation endproducts:ＡＧＥｓ）の生成に至る反応である。 In glycation in the living body, a carbonyl group of a reducing sugar such as glucose reacts with a protein non-enzymatically, forms a schiff base, and becomes a glycated protein that is an irreversible substance by Amadori transfer. In the reaction leading to the production of advanced glycation endproducts (AGEs) through the production of reaction intermediates centering on carbonyl compounds such as glucosone (3DG), glyoxal, methylglyoxal, glyceraldehyde, and glutaraldehyde. is there.
近年、ＡＧＥｓと、人の皮膚の老化、動脈硬化、糖尿病疾病、糖尿病の三大合併症（神経障害、網膜症、腎症）、成人病疾患等との関係性について種々の研究がなされており、これらの疾患の治療・改善及び老化防止・予防には、抗糖化剤が用いられる。そして、これまでにも、種々の抗糖化剤が提案されている。例えば、特許文献１には、焼酎残渣もろみの濃縮エキスを有効成分として含有する、抗糖化剤が開示されている。
In recent years, various studies have been conducted on the relationship between AGEs and human skin aging, arteriosclerosis, diabetic illness, three major complications of diabetes (neuropathy, retinopathy, nephropathy), adult disease, etc. Anti-glycation agents are used for treatment / improvement of these diseases and prevention / prevention of aging. And until now, various anti-glycation agents have been proposed. For example,
本発明は、新規な抗糖化剤を提供することを目的とする。 An object of the present invention is to provide a novel anti-glycation agent.
本発明は、バガスの分解抽出物を有効成分として含む抗糖化剤に関する。本発明の抗糖化剤は、バガスの分解抽出物を有効成分として含むため、抗糖化活性に優れている。 The present invention relates to an anti-glycation agent containing a decomposition extract of bagasse as an active ingredient. Since the anti-glycation agent of the present invention contains a bagasse degradation extract as an active ingredient, it has excellent anti-glycation activity.
バガスの分解抽出物は、水熱処理、酸処理、アルカリ処理、亜臨界水処理、微粉砕処理及び爆砕処理からなる群より選ばれる少なくとも１種の分解処理により得られる分解処理液であってよい。 The decomposition extract of bagasse may be a decomposition treatment liquid obtained by at least one decomposition treatment selected from the group consisting of hydrothermal treatment, acid treatment, alkali treatment, subcritical water treatment, pulverization treatment and explosion treatment.
バガスの分解抽出物は、分解処理液を、固定担体を充填したカラムに通液することより得られる画分であってもよい。固定担体は、好ましくは、合成吸着剤又はイオン交換樹脂である。 The bagasse decomposition extract may be a fraction obtained by passing the decomposition treatment liquid through a column packed with a fixed carrier. The fixed carrier is preferably a synthetic adsorbent or an ion exchange resin.
固定担体が合成吸着剤である場合、バガスの分解抽出物は、該合成吸着剤に吸着された成分を、水、メタノール、エタノール及びこれらの混合物からなる群より選ばれる少なくとも１種の溶媒で溶出させることにより得られる画分であってもよい。 When the fixed carrier is a synthetic adsorbent, the bagasse decomposition extract elutes the components adsorbed on the synthetic adsorbent with at least one solvent selected from the group consisting of water, methanol, ethanol and mixtures thereof. It is also possible to obtain a fraction obtained by making it occur.
合成吸着剤は、好ましくは、芳香族系樹脂、アクリル酸系メタクリル樹脂、又はアクリロニトリル脂肪族系樹脂である。 The synthetic adsorbent is preferably an aromatic resin, an acrylic acid-based methacrylic resin, or an acrylonitrile aliphatic resin.
バガスの分解抽出物は、分解処理液を、固定担体としての合成吸着剤を充填したカラムに通液し、該合成吸着剤に吸着された成分を、エタノール及び水の混合溶媒で溶出させて得られる画分であってよく、この場合、合成吸着剤は、無置換基型の芳香族系樹脂であり、カラムの温度は２０〜６０℃であり、混合溶媒のエタノール及び水の体積比（エタノール／水）は５０／５０〜６０／４０であってもよい。 The decomposition extract of bagasse is obtained by passing the decomposition treatment liquid through a column packed with a synthetic adsorbent as a fixed carrier and eluting the components adsorbed on the synthetic adsorbent with a mixed solvent of ethanol and water. In this case, the synthetic adsorbent is an unsubstituted aromatic resin, the column temperature is 20 to 60 ° C., and the volume ratio of ethanol and water (ethanol / Water) may be 50/50 to 60/40.
上記抗糖化剤は、抗糖化活性に優れているため、抗糖化用飲食品として好適に用いることができる。 Since the anti-glycation agent is excellent in anti-glycation activity, it can be suitably used as a food or drink for anti-glycation.
本発明によれば、新規な抗糖化剤を提供することが可能となる。 According to the present invention, it is possible to provide a novel anti-glycation agent.
以下、本発明を実施するための形態について詳細に説明する。なお、本発明は、以下の実施形態に限定されるものではない。 Hereinafter, embodiments for carrying out the present invention will be described in detail. In addition, this invention is not limited to the following embodiment.
本明細書における抗糖化剤は、抗糖化活性を有するものであり、具体的には、糖化最終生成物（ＡＧＥｓ）の、生成抑制作用（糖化反応阻害作用）、蓄積抑制作用又は分解作用を有するものであってよい。言い換えれば、本実施形態の抗糖化剤は、例えば、糖化最終生成物の生成抑制剤（糖化反応阻害剤）、蓄積抑制剤又は分解剤（分解促進剤）であってよい。 The anti-glycation agent in the present specification has anti-glycation activity, and specifically has a production-inhibiting action (glycation reaction-inhibiting action), accumulation-inhibiting action, or decomposition action of the final glycation products (AGEs). It may be a thing. In other words, the anti-glycation agent of the present embodiment may be, for example, a glycation end product production inhibitor (a saccharification reaction inhibitor), an accumulation inhibitor, or a degradation agent (degradation accelerator).
糖化最終生成物（終末糖化産物）は、糖化反応（メイラード反応）による生成物の総称である。糖化最終生成物としては、例えば、ＣＭＬ（Ｎε−（ｃａｒｂｏｘｙｍｅｔｈｙｌ）ｌｙｓｉｎｅ）、ペントシジン（ｐｅｎｔｏｓｉｄｉｎｅ）、ピラリン（ｐｙｒｒａｌｉｎｅ）、クロスリン（ｃｒｏｓｓｌｉｎｅ）が挙げられる。また、本実施形態の抗糖化剤は、糖化反応における反応中間体の、生成抑制作用、蓄積抑制作用又は分解促進作用を有することにより、結果として、上述の抗糖化活性を有するものであってよい。糖化反応における反応中間体としては、具体的には、グリオキサール（ＧＯ）、３−デオキシグルコソン（３ＤＧ）、メチルグリオキサール（ＭＧＯ）等であってよい。 The saccharification end product (terminal saccharification product) is a general term for products resulting from a saccharification reaction (Maillard reaction). Examples of the saccharification end product include CML (N ε- (carboxymethyl) lysine), pentosidine, pyraline, and crossline. Moreover, the anti-glycation agent of this embodiment may have the above-mentioned anti-glycation activity as a result of having a production-inhibiting action, an accumulation-inhibiting action or a decomposition-promoting action of a reaction intermediate in a saccharification reaction. . Specifically, the reaction intermediate in the saccharification reaction may be glyoxal (GO), 3-deoxyglucosone (3DG), methylglyoxal (MGO), or the like.
本実施形態の抗糖化剤は、バガスの分解抽出物を有効成分として含む。 The anti-glycation agent of this embodiment contains the decomposition extract of bagasse as an active ingredient.
抗糖化剤におけるバガスの分解抽出物の含有量は、抗糖化剤全量基準で、０．０１〜１００質量％であってもよく、０．１〜１００質量％であってもよい。 The content of the decomposition extract of bagasse in the anti-glycation agent may be 0.01 to 100% by mass or 0.1 to 100% by mass based on the total amount of the anti-glycation agent.
一実施形態に係る抗糖化剤は、バガスの分解抽出物を有効成分として含有する。バガスの分解抽出物には、ｐ−クマル酸、フェルラ酸、カフェ酸及びバニリン等のフェニルプロパノイド、並びにリグニン及びその分解物からなる群より選ばれる少なくとも１種が含まれていることが好ましい。 The anti-glycation agent according to one embodiment contains a decomposition extract of bagasse as an active ingredient. The decomposition extract of bagasse preferably contains at least one selected from the group consisting of phenylpropanoids such as p-coumaric acid, ferulic acid, caffeic acid and vanillin, and lignin and decomposition products thereof.
「バガス」とは、典型的には原料糖製造工程における製糖過程で排出されるバガスをいう。原料糖工場における製糖過程で排出されるバガスには、最終圧搾機を出た最終バガスだけではなく、第１圧搾機を含む以降の圧搾機に食い込まれた細裂甘蔗をも含む。好適なバガスは、原料糖工場において圧搾工程により糖汁を圧搾した後に排出されるバガスである。当該バガスは、甘蔗の種類、収穫時期等により、その含まれる水分、糖分及びそれらの組成比が異なるが、本発明においては、これらのバガスを任意に用いることができる。さらに、本実施形態では、原料のバガスとして、原料糖工場と同様に、例えば黒糖製造工場において排出される甘蔗圧搾後に残るバガス、又は実験室レベルの小規模な実施により甘蔗から糖液を圧搾した後のバガスも用いることができる。 “Bagasse” typically refers to bagasse discharged in the sugar production process in the raw sugar production process. The bagasse discharged in the sugar production process at the raw sugar factory includes not only the final bagasse that has left the final press, but also shredded sweet potato that has been bitten by the subsequent press including the first press. A suitable bagasse is bagasse discharged after squeezing the sugar juice in the raw sugar factory. The bagasse has different moisture content, sugar content and composition ratio depending on the type of sweet potato, harvest time, etc., but these bagasse can be used arbitrarily in the present invention. Furthermore, in the present embodiment, as the raw material bagasse, as in the raw sugar factory, for example, the bagasse remaining after the sweet potato pressing discharged in the brown sugar manufacturing factory, or the sugar solution was pressed from the sweet potato by small-scale implementation at the laboratory level Later bagasse can also be used.
バガスの分解抽出物は、一実施形態において、バガス（及び／又はその加工物）の分解処理液であってよい。分解処理液は、アルカリ処理、水熱処理、酸処理、亜臨界水処理、微粉砕処理及び爆砕処理からなる群から選ばれる少なくとも１種以上の分解処理により得ることができる。分解処理は、バガスの分解抽出物を得やすい観点から、好ましくはアルカリ処理又は水熱処理である。 In one embodiment, the bagasse decomposition extract may be a decomposition solution of bagasse (and / or a processed product thereof). The decomposition treatment liquid can be obtained by at least one decomposition treatment selected from the group consisting of alkali treatment, hydrothermal treatment, acid treatment, subcritical water treatment, pulverization treatment, and explosion treatment. The decomposition treatment is preferably alkali treatment or hydrothermal treatment from the viewpoint of easily obtaining a bagasse decomposition extract.
アルカリ処理は、バガスにアルカリ性溶液を接触させる処理であってよい。アルカリ性溶液を接触させる方法としては、例えば、アルカリ性溶液をバガスに振りかける方法、バガスをアルカリ性溶液に浸漬させる方法等が挙げられる。バガスをアルカリ性溶液に浸漬させる方法においては、バガス及びアルカリ性溶液の混合物を撹拌しながら浸漬させてもよい。 The alkali treatment may be a treatment in which an alkaline solution is brought into contact with bagasse. Examples of the method of bringing the alkaline solution into contact include a method of sprinkling an alkaline solution over bagasse, a method of immersing bagasse in an alkaline solution, and the like. In the method of immersing bagasse in the alkaline solution, the mixture of bagasse and alkaline solution may be immersed while stirring.
アルカリ性溶液としては、水酸化ナトリウム水溶液、水酸化カリウム水溶液、アンモニア水溶液等が挙げられる。アルカリ性溶液は、これらの溶液を１種単独で又は２種以上を混合して用いられてよい。アルカリ性溶液は、安価であり、食品製造工程で容易に用いられる観点から、好ましくは水酸化ナトリウム水溶液である。 Examples of the alkaline solution include an aqueous sodium hydroxide solution, an aqueous potassium hydroxide solution, and an aqueous ammonia solution. These alkaline solutions may be used alone or as a mixture of two or more of these solutions. The alkaline solution is preferably an aqueous sodium hydroxide solution from the viewpoint of being inexpensive and easily used in the food production process.
アルカリ性溶液の温度（液温）は、分解処理の処理時間を短縮する観点から、好ましくは４０℃以上であり、より好ましくは１００℃以上であり、更に好ましくは１３０℃以上である。アルカリ性溶液の温度は、分解処理液に多糖類を残存させないようにする観点から、好ましくは２５０℃以下であり、より好ましくは２００℃以下であり、更に好ましくは１５０℃以下である。 The temperature (liquid temperature) of the alkaline solution is preferably 40 ° C. or higher, more preferably 100 ° C. or higher, and further preferably 130 ° C. or higher, from the viewpoint of shortening the processing time of the decomposition treatment. The temperature of the alkaline solution is preferably 250 ° C. or less, more preferably 200 ° C. or less, and further preferably 150 ° C. or less, from the viewpoint of preventing polysaccharides from remaining in the decomposition treatment solution.
アルカリ処理は、常圧下で行われてよく、加圧して行われてもよい。加圧する場合、圧力は、０．１ＭＰａ以上、０．２ＭＰａ以上であってよく、４．０ＭＰａ以下、１．６ＭＰａ以下、又は０．５ＭＰａ以下であってよい。 The alkali treatment may be performed under normal pressure or may be performed under pressure. When pressurizing, the pressure may be 0.1 MPa or more, 0.2 MPa or more, 4.0 MPa or less, 1.6 MPa or less, or 0.5 MPa or less.
水熱処理は、バガスに高温の水又は水蒸気を高圧下で接触させる処理であってよい。水熱処理は、より具体的には、例えば、バガスの固形物濃度が０．１〜５０％となるように水を加え、高温・高圧条件下で分解処理を行う方法であってもよい。水又は水蒸気の温度は１３０〜２５０℃であることが好ましく、加える圧力は、各温度の水の飽和水蒸気圧に、更に０．１〜０．５ＭＰa高い圧力であることが好ましい。 The hydrothermal treatment may be a treatment in which bagasse is brought into contact with hot water or steam under high pressure. More specifically, the hydrothermal treatment may be, for example, a method in which water is added so that the solids concentration of bagasse is 0.1 to 50% and the decomposition treatment is performed under high temperature and high pressure conditions. The temperature of water or water vapor is preferably 130 to 250 ° C., and the pressure applied is preferably 0.1 to 0.5 MPa higher than the saturated water vapor pressure of water at each temperature.
酸処理は、バガスに酸性溶液を接触させる処理であってよい。酸性溶液としては、希硫酸等が挙げられる。バガスに酸性溶液を接触させる方法、酸処理における酸溶液の温度、酸処理における圧力条件は、上述したアルカリ処理における方法又は条件と同様であってよい。 The acid treatment may be a treatment in which an acidic solution is brought into contact with bagasse. Examples of the acidic solution include dilute sulfuric acid. The method of bringing the acid solution into contact with the bagasse, the temperature of the acid solution in the acid treatment, and the pressure condition in the acid treatment may be the same as the method or conditions in the alkali treatment described above.
亜臨界水処理は、バガスに亜臨界水を接触させる処理であってよい。バガスに亜臨界水を接触させる方法は、上述したアルカリ処理における方法と同様であってよい。亜臨界水処理の条件は特に制限されないが、亜臨界水の温度を１６０〜２４０℃とし、処理時間を１〜９０分間とすることが好ましい。 The subcritical water treatment may be a treatment in which subcritical water is brought into contact with bagasse. The method of bringing the subcritical water into contact with the bagasse may be the same as the method in the alkali treatment described above. The conditions for the subcritical water treatment are not particularly limited, but the temperature of the subcritical water is preferably 160 to 240 ° C., and the treatment time is preferably 1 to 90 minutes.
微粉砕処理は、圧縮、衝撃、せん断、摩擦などによりバガスを数μｍ〜数百μｍに粉砕する処理であってよい。爆砕処理は、水熱処理によりバガスに含まれる不溶性キシランをある程度分解させた後、耐圧反応容器に設けられたバルブを一気に開放すること等によって、瞬間的に大気圧に放出することによりバガスを粉砕する処理であってよい。 The fine pulverization process may be a process of pulverizing bagasse to several μm to several hundred μm by compression, impact, shear, friction, or the like. Explosive treatment is performed by decomposing insoluble xylan contained in bagasse to some extent by hydrothermal treatment, and then pulverizing bagasse by instantaneously releasing it to atmospheric pressure by opening a valve provided in the pressure-resistant reaction vessel at once. It may be a process.
分解処理液においては、上述した分解処理の後、固形分及び液分を分離する処理がなされてもよい。この場合、分離後に得られた液分を分解処理液とすることができる。固形分及び液分を分離する方法は、ストレーナー、ろ過、遠心分離、デカンテーション等による分離であってよい。 In the decomposition treatment liquid, a process of separating the solid content and the liquid content may be performed after the above-described decomposition treatment. In this case, the liquid obtained after the separation can be used as the decomposition treatment liquid. The method for separating the solid content and the liquid content may be separation by strainer, filtration, centrifugation, decantation, or the like.
分解処理液においては、膜分離により多糖類等の高分子成分が除去されてもよい。この場合、膜分離後の液分を分解処理液とすることができる。分離膜は、限外濾過膜（ＵＦ膜）であれば特に限定されない。限外濾過膜の分画分子量は、好ましくは２，５００〜５０，０００であり、より好ましくは２，５００〜５，０００である。 In the decomposition treatment liquid, polymer components such as polysaccharides may be removed by membrane separation. In this case, the liquid after membrane separation can be used as the decomposition treatment liquid. The separation membrane is not particularly limited as long as it is an ultrafiltration membrane (UF membrane). The molecular weight cutoff of the ultrafiltration membrane is preferably 2,500 to 50,000, more preferably 2,500 to 5,000.
限外濾過膜の素材としては、ポリイミド、ポリエーテルスルホン（ＰＥＳ）、ポリスルホン（ＰＳ）、ポリアクリロニトリル（ＰＡＮ）、ポリフッ化ビニルデン（ＰＶＤＦ）、再生セルロース、セルロース、セルロースエステル、スルホン化ポリスルホン、スルホン化ポリエーテルスルホン、ポリオレフィン、ポリビニルアルコール、ポリメチルメタクリレート、ポリ四フッ化エチレン等を使用することができる。 Ultrafiltration membrane materials include polyimide, polyethersulfone (PES), polysulfone (PS), polyacrylonitrile (PAN), polyvinylidene fluoride (PVDF), regenerated cellulose, cellulose, cellulose ester, sulfonated polysulfone, and sulfonated. Polyethersulfone, polyolefin, polyvinyl alcohol, polymethyl methacrylate, polytetrafluoroethylene and the like can be used.
限外濾過膜の濾過方式は、デッドエンド濾過、クロスフロー濾過であってよいが、膜ファウリング抑制の観点から、クロスフロー濾過であることが好ましい。 The filtration method of the ultrafiltration membrane may be dead-end filtration or crossflow filtration, but from the viewpoint of suppressing membrane fouling, crossflow filtration is preferable.
限外濾過膜の膜形態としては、平膜型、スパイラル型、チューブラー型、中空糸型等、適宜の形態のものが使用できる。より具体的には、ＧＥ Ｐｏｗｅｒ＆ＷａｔｅｒのＧＥシリーズ、ＧＨシリーズ、ＧＫシリーズ、ＤＥＳＡＬ社のＧ−５タイプ、Ｇ−１０タイプ、Ｇ−２０タイプ、Ｇ−５０タイプ、ＰＷタイプ、ＨＷＳＵＦタイプ、ＫＯＣＨ社のＨＦＭ−１８０、ＨＦＭ−１８３、ＨＦＭ−２５１、ＨＦＭ−３００、ＨＦＫ−１３１、ＨＦＫ−３２８、ＭＰＴ−Ｕ２０、ＭＰＳ−Ｕ２０Ｐ、ＭＰＳ−Ｕ２０Ｓ、Ｓｙｎｄｅｒ社のＳＰＥ１、ＳＰＥ３、ＳＰＥ５、ＳＰＥ１０、ＳＰＥ３０、ＳＰＶ５、ＳＰＶ５０、ＳＯＷ３０、旭化成株式会社製のマイクローザ（登録商標）ＵＦシリーズの分画分子量３，０００から１０，０００に相当するもの、日東電工株式会社製のＮＴＲ７４１０、ＮＴＲ７４５０等が挙げられる。 As the membrane form of the ultrafiltration membrane, those having an appropriate form such as a flat membrane type, a spiral type, a tubular type, and a hollow fiber type can be used. More specifically, GE Power & Water's GE series, GH series, GK series, DESAL G-5 type, G-10 type, G-20 type, G-50 type, PW type, HWSUF type, KOCH HFM-180, HFM-183, HFM-251, HFM-300, HFK-131, HFK-328, MPT-U20, MPS-U20P, MPS-U20S, SPE1 from Sinder, SPE3, SPE5, SPE10, SPE30, SPV5 SPV50, SOW30, those corresponding to a fractional molecular weight of 3,000 to 10,000 in the Microza (registered trademark) UF series manufactured by Asahi Kasei Corporation, NTR7410, NTR7450 manufactured by Nitto Denko Corporation, and the like.
バガスの分解抽出物は、他の実施形態において、上述した分解処理液を、固定担体を充填したカラムに通液することより得られる画分であってもよい。分解処理液をカラムに通液することにより、分解処理液中の抗糖化活性を有する成分（有効成分）が固定担体に吸着され、糖類及び無機塩類の大部分がそのまま流出する。 In another embodiment, the bagasse decomposition extract may be a fraction obtained by passing the decomposition treatment liquid described above through a column packed with a fixed carrier. By passing the decomposition treatment liquid through the column, the component (active ingredient) having anti-glycation activity in the decomposition treatment liquid is adsorbed to the fixed carrier, and most of saccharides and inorganic salts flow out as they are.
上述した分解処理液は、直接又は水で任意の濃度に調整して、カラムに通液することができる。分解処理液においては、カラムの通液前にｐＨを調整してもよい。吸着率を向上させる観点から、分解処理液は、ｐＨ６以下に調整されていることが好ましい。分解処理液のｐＨは、４．５を超え６以下であってもよい。 The decomposition treatment liquid described above can be adjusted directly to an arbitrary concentration with water or passed through the column. In the decomposition treatment liquid, the pH may be adjusted before passing through the column. From the viewpoint of improving the adsorption rate, the decomposition treatment liquid is preferably adjusted to pH 6 or less. The pH of the decomposition treatment liquid may be more than 4.5 and 6 or less.
固定担体は、好ましくは、合成吸着剤又はイオン交換樹脂のいずれかである。 The immobilization carrier is preferably either a synthetic adsorbent or an ion exchange resin.
合成吸着剤は、好ましくは合成多孔質吸着剤である。合成吸着剤（合成多孔質吸着剤）としては、好ましくは有機系樹脂が用いられる。有機系樹脂は、好ましくは、芳香族系樹脂、アクリル酸系メタクリル樹脂、又はアクリロニトリル脂肪族系樹脂である。 The synthetic adsorbent is preferably a synthetic porous adsorbent. As the synthetic adsorbent (synthetic porous adsorbent), an organic resin is preferably used. The organic resin is preferably an aromatic resin, an acrylic acid-based methacrylic resin, or an acrylonitrile aliphatic resin.
芳香族系樹脂としては、例えば、スチレン−ジビニルベンゼン系樹脂が挙げられる。芳香族系樹脂としては、疎水性置換基を有する芳香族系樹脂、無置換基型の芳香族系樹脂、無置換基型に特殊処理をした芳香族系樹脂等の多孔質性樹脂も挙げられ、このうち、無置換基型の芳香族系樹脂又は無置換基型に特殊処理をした芳香族系樹脂が好ましい。 Examples of the aromatic resin include styrene-divinylbenzene resin. Examples of aromatic resins include porous resins such as aromatic resins having a hydrophobic substituent, unsubstituted aromatic resins, and aromatic resins specially processed into unsubstituted groups. Of these, an unsubstituted aromatic resin or an aromatic resin specially treated to an unsubstituted group is preferred.
合成吸着剤で市販のものとしては、ダイヤイオン（商標）ＨＰ−１０、ＨＰ−２０、ＨＰ−２１、ＨＰ−３０、ＨＰ−４０、ＨＰ−５０（以上、無置換基型の芳香族系樹脂、いずれも商品名、三菱ケミカル株式会社製）；ＳＰ−８２５、ＳＰ−８００、ＳＰ−８５０、ＳＰ−８７５、ＳＰ−７０、ＳＰ−７００（以上、無置換基型に特殊処理を施した芳香族系樹脂、いずれも商品名、三菱ケミカル株式会社製）；ＳＰ−９００（芳香族系樹脂、商品名、三菱ケミカル株式会社製）；アンバーライト（商標）ＸＡＤ−２、ＸＡＤ−４、ＸＡＤ−１６、ＸＡＤ−２０００（以上、芳香族系樹脂、いずれも商品名、株式会社オルガノ製）；ダイヤイオン（商標）ＳＰ−２０５、ＳＰ−２０６、ＳＰ−２０７（以上、疎水性置換基を有する芳香族系樹脂、いずれも商品名、三菱ケミカル株式会社製）；ＨＰ−２ＭＧ、ＥＸ−００２１（以上、疎水性置換基を有する芳香族系樹脂、いずれも商品名、三菱ケミカル株式会社製）；アンバーライト（商標）ＸＡＤ−７、ＸＡＤ−８（以上、アクリル酸エステル樹脂、いずれも商品名、株式会社オルガノ製）；ダイヤイオン（商標）ＨＰ１ＭＧ、ＨＰ２ＭＧ（以上、アクリル酸メタクリル樹脂、いずれも商品名、三菱ケミカル株式会社製）；セファデックス（商標）ＬＨ２０、ＬＨ６０（以上、架橋デキストランの誘導体、いずれも商品名、ファルマシア バイオテク株式会社製）等が挙げられる。中でも、無置換基型の芳香族系樹脂（例えば、ＨＰ−２０）又は無置換基型に特殊処理を施した芳香族系樹脂（例えば、ＳＰ−８５０）が好ましい。 Synthetic adsorbents that are commercially available are Diaion (trademark) HP-10, HP-20, HP-21, HP-30, HP-40, HP-50 (above, unsubstituted aromatic resin , All trade names, manufactured by Mitsubishi Chemical Corporation); SP-825, SP-800, SP-850, SP-875, SP-70, SP-700 SP-900 (aromatic resin, trade name, manufactured by Mitsubishi Chemical Corporation); Amberlite (trademark) XAD-2, XAD-4, XAD- 16, XAD-2000 (above, aromatic resins, all trade names, manufactured by Organo Corporation); Diaion (trademark) SP-205, SP-206, SP-207 (above, aroma having hydrophobic substituents) Family tree , Both trade names, manufactured by Mitsubishi Chemical Corporation); HP-2MG, EX-0021 (above, aromatic resins having hydrophobic substituents, both trade names, manufactured by Mitsubishi Chemical Corporation); Amberlite (trademark) ) XAD-7, XAD-8 (above, acrylate resin, both trade names, manufactured by Organo Corporation); Diaion (trademark) HP1MG, HP2MG (above, methacrylic acrylate resin, both trade names, Mitsubishi Chemical) Sephadex (trademark) LH20, LH60 (above, derivatives of crosslinked dextran, both trade names, manufactured by Pharmacia Biotech Co., Ltd.) and the like. Among them, an unsubstituted aromatic resin (for example, HP-20) or an aromatic resin (for example, SP-850) obtained by subjecting an unsubstituted group to a special treatment is preferable.
カラムに充填する合成吸着剤の量は、カラムの大きさ、合成吸着剤の種類等によって適宜決定することができる。 The amount of the synthetic adsorbent packed in the column can be appropriately determined depending on the size of the column, the type of the synthetic adsorbent, and the like.
固定担体として合成吸着剤を用いる場合、分解処理液を通液するときの通液速度は、カラムの大きさ、溶出溶媒の種類、合成吸着剤の種類等によって適宜変更が可能であるが、好ましくは、ＳＶ＝１〜３０時間−１である。なお、ＳＶ（Ｓｐａｃｅ Ｖｅｌｏｃｉｔｙ、空間速度）は、１時間当たり樹脂容量の何倍量の液体を通液するかという単位である。 When a synthetic adsorbent is used as the fixed carrier, the flow rate when the decomposition treatment liquid is passed can be appropriately changed depending on the size of the column, the type of elution solvent, the type of synthetic adsorbent, etc. Is SV = 1 to 30 hours −1 . In addition, SV (Space Velocity, space velocity) is a unit of how many times the amount of the liquid is passed per hour.
合成吸着剤に吸着された吸着成分（有効成分）は、溶媒（溶出溶媒）により溶出させることができる。吸着成分をより効率よく回収する観点から、吸着成分を溶出させる前に、カラムに残留する糖類及び無機塩類を水洗により洗い流すことが好ましい。この場合、溶出させた成分をバガスの分解抽出物とすることができる。 The adsorbed component (active component) adsorbed on the synthetic adsorbent can be eluted with a solvent (elution solvent). From the viewpoint of recovering the adsorbed component more efficiently, it is preferable to wash away saccharides and inorganic salts remaining in the column with water before eluting the adsorbed component. In this case, the eluted component can be used as a decomposition extract of bagasse.
固定担体として合成吸着剤を用いる場合、溶出溶媒は、水、メタノール、エタノール及びこれらの混合物からなる群より選ばれる少なくとも１種であってよい。溶出溶媒は、アルコール及び水の混合溶媒が好ましく、エタノール及び水の混合溶媒がより好ましく、吸着成分が室温においてより効率よく溶出可能となる観点から、体積比が５０／５０〜６０／４０（エタノール／水）であるエタノール及び水の混合溶媒が更に好ましい。 When a synthetic adsorbent is used as the fixed carrier, the elution solvent may be at least one selected from the group consisting of water, methanol, ethanol, and mixtures thereof. The elution solvent is preferably a mixed solvent of alcohol and water, more preferably a mixed solvent of ethanol and water, and a volume ratio of 50/50 to 60/40 (ethanol from the viewpoint that the adsorbed component can be eluted more efficiently at room temperature. More preferred is a mixed solvent of ethanol and water.
固定担体として合成吸着剤を用いる場合、溶出する際のカラムの温度（カラム温度）は室温であってよいが、室温よりもカラム温度を高温にすることにより、エタノール及び水の混合溶媒においてエタノールの混合割合を減らすことができ、吸着成分をより効率的に溶出させることができる。温度は、好ましくは２０〜６０℃であり、より好ましくは４０〜６０℃である。カラム内は常圧条件下であっても、加圧条件下であってもよい。 When a synthetic adsorbent is used as a fixed carrier, the column temperature at the time of elution (column temperature) may be room temperature, but by increasing the column temperature to a temperature higher than room temperature, ethanol in a mixed solvent of ethanol and water The mixing ratio can be reduced, and the adsorbed component can be eluted more efficiently. The temperature is preferably 20 to 60 ° C, more preferably 40 to 60 ° C. The inside of the column may be under normal pressure or under pressure.
固定担体として合成吸着剤を用いる場合、溶出速度は、カラムの大きさ、溶出溶媒の種類、合成吸着剤の種類等によって適宜設定することが可能であるが、好ましくは、ＳＶ＝０．１〜１０時間−１である。 When a synthetic adsorbent is used as the fixed carrier, the elution rate can be appropriately set depending on the column size, the type of elution solvent, the type of synthetic adsorbent, etc., preferably, SV = 0.1 10 hours -1 .
イオン交換樹脂は、樹脂の形態に基づいて、ゲル型樹脂と、ポーラス型、マイクロポーラス型又はハイポーラス型等の多孔性樹脂とに分類されるが、特に制限はない。イオン交換樹脂は、好ましくは陰イオン交換樹脂である。陰イオン交換樹脂としては、強塩基性陰イオン交換樹脂又は弱塩基性陰イオン交換樹脂が用いられてよい。アルカリ処理液を原料として使用する場合、好ましくは、強塩基性陰イオン交換樹脂が用いられるが、その他の処理による分解処理液を原料とする場合は特に制限はない。 The ion exchange resin is classified into a gel type resin and a porous resin such as a porous type, a microporous type, or a high porous type based on the form of the resin, but there is no particular limitation. The ion exchange resin is preferably an anion exchange resin. As the anion exchange resin, a strong basic anion exchange resin or a weak basic anion exchange resin may be used. When an alkaline treatment liquid is used as a raw material, a strongly basic anion exchange resin is preferably used, but there is no particular limitation when a decomposition treatment liquid by other treatment is used as a raw material.
市販の強塩基性陰イオン交換樹脂としては、ダイヤイオン（商標）ＰＡ３０６、ＰＡ３０８、ＰＡ３１２、ＰＡ３１６、ＰＡ３１８Ｌ、ＨＰＡ２５、ＳＡ１０Ａ、ＳＡ１２Ａ、ＳＡ１１Ａ、ＳＡ２０Ａ、ＵＢＡ１２０（以上、三菱ケミカル株式会社製）、アンバーライト（商標）ＩＲＡ４００Ｊ、ＩＲＡ４０２Ｂｌ、ＩＲＡ４０４Ｊ、ＩＲＡ９００Ｊ、ＩＲＡ９０４、ＩＲＡ４５８ＲＦ、ＩＲＡ９５８、ＩＲＡ４１０Ｊ、ＩＲＡ４１１、ＩＲＡ９１０ＣＴ（以上、オルガノ株式会社製）、ダウエックス（商標）マラソンＡ、マラソンＭＳＡ、ＭＯＮＯＳＰＨＥＲＥ５５０Ａ、マラソンＡ２（以上、ダウケミカル日本株式会社製）等が挙げられる。 Examples of commercially available strong base anion exchange resins include Diaion (trademark) PA306, PA308, PA312, PA316, PA318L, HPA25, SA10A, SA12A, SA11A, SA20A, UBA120 (above, manufactured by Mitsubishi Chemical Corporation), Amberlite (Trademark) IRA400J, IRA402B1, IRA404J, IRA900J, IRA904, IRA458RF, IRA958, IRA410J, IRA411, IRA910CT (above, manufactured by Organo Corporation), Dowex (trademark) Marathon A, Marathon MSA, MONOSSPHERE550A, Marathon A2 (above, Dow Chemical Japan Co., Ltd.).
市販の弱塩基性陰イオン交換樹脂としては、ダイヤイオン（商標）ＷＡ１０、ＷＡ２０、ＷＡ２１Ｊ、ＷＡ３０（以上、三菱ケミカル株式会社製）、アンバーライト（商標）ＩＲＡ４７８ＲＦ、ＩＲＡ６７、ＩＲＡ９６ＳＢ、ＩＲＡ９８、ＸＥ５８３（以上、オルガノ株式会社製）、ダウエックス（商標）マラソンＷＢＡ、６６、ＭＯＮＯＳＰＨＥＲＥ６６、ＭＯＮＯＳＰＨＥＲＥ７７（以上、ダウケミカル日本株式会社製）等が挙げられる。 Examples of commercially available weakly basic anion exchange resins include Diaion (trademark) WA10, WA20, WA21J, WA30 (above, manufactured by Mitsubishi Chemical Corporation), Amberlite (trademark) IRA478RF, IRA67, IRA96SB, IRA98, XE583 (above , Organo Co., Ltd.), Dowex (trademark) Marathon WBA, 66, MONOSSPHERE 66, MONOSSPHERE 77 (above, manufactured by Dow Chemical Japan Co., Ltd.) and the like.
カラムに充填するイオン交換樹脂の量は、カラムの大きさ、イオン交換樹脂の種類などによって適宜決定できるが、分解処理液の固形分に対して２〜１０，０００倍湿潤体積量が好ましく、５〜５００倍湿潤体積量がより好ましい。 The amount of the ion exchange resin to be packed in the column can be appropriately determined depending on the size of the column, the type of the ion exchange resin, and the like, but preferably 2 to 10,000 times wet volume with respect to the solid content of the decomposition treatment liquid. A wet volume of ˜500 times is more preferred.
通液条件は、前処理液の種類、イオン交換樹脂の種類等により適宜設定することが可能である。好ましくは、流速はＳＶ＝０．３〜３０時間−１であり、通液する液量はイオン交換樹脂の１００〜３００％であり、カラム温度は４０〜９０℃である。カラム内は常圧又は加圧された状態であってもよい。 The liquid passing conditions can be appropriately set depending on the kind of pretreatment liquid, the kind of ion exchange resin, and the like. Preferably, the flow rate is SV = 0.3 to 30 hours− 1 , the amount of liquid to be passed is 100 to 300% of the ion exchange resin, and the column temperature is 40 to 90 ° C. The column may be at normal pressure or under pressure.
固定担体としてイオン交換樹脂を用いる場合、バガスの分解抽出物は、イオン交換樹脂を充填したカラムに通液し、塩や酸、アルコール又はこれらの混合水溶液等の溶離液で溶出させることで得られる画分であってもよい。溶離液は脱気処理されていてもよい。 When an ion exchange resin is used as a fixed carrier, the bagasse decomposition extract is obtained by passing through a column packed with ion exchange resin and eluting with an eluent such as a salt, acid, alcohol, or a mixed aqueous solution thereof. It may be a fraction. The eluent may be degassed.
バガスの分解抽出物は、一実施形態においては、上述した分解処理液又は画分を濃縮した濃縮物であってもよい。濃縮方法は公知の方法であってよく、例えば、減圧下での溶媒留去、凍結乾燥等の方法であってよい。濃縮を行う場合、分解処理液又は画分を１５〜３０倍に濃縮して、濃縮後の成分をバガスの分解抽出物とすることができる。 In one embodiment, the decomposition extract of bagasse may be a concentrate obtained by concentrating the above-described decomposition treatment liquid or fraction. The concentration method may be a known method, for example, a method such as solvent distillation under reduced pressure, freeze drying, or the like. When concentration is performed, the decomposition treatment liquid or fraction can be concentrated 15 to 30 times, and the concentrated component can be used as a bagasse decomposition extract.
バガスの分解抽出物は、例えば、次のようにして得ることができる。バガスに、固形物濃度が０．１〜５０％となるように１質量％の水酸化ナトリウム水溶液を添加して１００℃で煮沸を行い、分解処理液（アルカリ処理液）を得る。分解処理液を分画分子量２５００〜５０００のＵＦ膜にて限外濾過を行い、得られた濾過液を酸性に調整してから、無置換基型の芳香族系樹脂を充填したカラムに、カラム温度２０〜６０℃にて通液する。その後、カラムに吸着された成分を、カラム温度２０〜６０℃にて、体積比が５０／５０〜６０／４０（エタノール／水）のエタノール及び水の混合溶媒（溶出溶媒）で溶出させ、エタノール及び水の混合溶媒での溶出開始時点から集めた溶出液の量が該芳香族系樹脂の４５倍湿潤体積量以内に溶出する画分を回収する。回収された画分（抗糖化活性を有する成分を含む画分）を集め、慣用の手段（減圧下での溶媒留去、凍結乾燥等）により濃縮して、バガスの分解抽出物を得ることができる。このようにして得られたバガスの分解抽出物は、固形分が３０質量％以上になるように濃縮した液状又は粉末状の抽出物として保存することができる。抽出物の保存は、当該抽出物が液状の場合、冷蔵で行うことが好ましい。 The bagasse decomposition extract can be obtained, for example, as follows. A 1 mass% sodium hydroxide aqueous solution is added to bagasse so that a solid substance concentration may be 0.1 to 50%, and it boils at 100 degreeC, and obtains a decomposition processing liquid (alkali processing liquid). The decomposition treatment liquid is subjected to ultrafiltration with a UF membrane having a molecular weight cut off of 2500 to 5000, the resulting filtrate is adjusted to acidity, and then the column is packed into a column filled with an unsubstituted aromatic resin. The liquid is passed at a temperature of 20 to 60 ° C. Thereafter, the components adsorbed on the column are eluted with a mixed solvent (elution solvent) of ethanol and water having a volume ratio of 50/50 to 60/40 (ethanol / water) at a column temperature of 20 to 60 ° C. And the fraction which the amount of the eluate collected from the elution start time with the mixed solvent of water elutes within 45 times wet volume of the aromatic resin is collected. The collected fractions (fractions containing components having anti-glycation activity) are collected and concentrated by conventional means (e.g., solvent distillation under reduced pressure, lyophilization, etc.) to obtain a bagasse decomposition extract. it can. The bagasse decomposition extract thus obtained can be stored as a liquid or powdery extract concentrated so that the solid content is 30% by mass or more. When the extract is liquid, it is preferable to store the extract by refrigeration.
バガスの分解抽出物は、他の例として、例えば、次のようにして得ることもできる。すなわち、バガスに固形物濃度が０．１〜５０％となるように加水して１３０〜２５０℃の水により、０．２〜４．０Ｍｐａの圧力下で水熱処理を行い、濾過による固液分離で分解処理液（水熱処理液）を得る。得られた水熱処理液について、無置換基型に特殊処理を施した芳香族系樹脂を充填したカラムに、温度２０〜６０℃にて通液した後、カラムに吸着された成分を、カラム温度２０〜６０℃にて、体積比が５０／５０〜６０／４０（エタノール／水）のエタノール及び水の混合溶媒（溶出溶媒）で溶出させ、エタノール及び水の混合溶媒での溶出開始時点から集めた溶出液の量が該芳香族系樹脂の５倍湿潤体積量以内に溶出する画分を回収する。回収された画分（抗糖化活性を有する成分を含む画分）を集め、慣用の手段（減圧下での溶媒留去、凍結乾燥等）により濃縮して、バガスの分解抽出物を得ることができる。このようにして得られたバガスの分解抽出物は、固形分が３０質量％以上になるように濃縮した液状又は粉末状の抽出物として保存することができる。抽出物の保存は、当該抽出物が液状の場合、冷蔵で行うことが好ましい。 The decomposition extract of bagasse can also be obtained as follows, for example. That is, water is added to bagasse so that the solid concentration is 0.1 to 50%, hydrothermal treatment is performed with water at 130 to 250 ° C. under a pressure of 0.2 to 4.0 Mpa, and solid-liquid separation by filtration is performed. To obtain a decomposition treatment liquid (hydrothermal treatment liquid). The obtained hydrothermal treatment liquid was passed through a column filled with an aromatic resin that had been subjected to a special treatment on an unsubstituted group at a temperature of 20 to 60 ° C., and then the components adsorbed on the column were treated with the column temperature. Elution is performed with a mixed solvent (elution solvent) of ethanol and water having a volume ratio of 50/50 to 60/40 (ethanol / water) at 20 to 60 ° C. and collected from the start of elution with the mixed solvent of ethanol and water. The fraction that elutes within 5% wet volume of the aromatic resin is recovered. The collected fractions (fractions containing components having anti-glycation activity) are collected and concentrated by conventional means (e.g., solvent distillation under reduced pressure, lyophilization, etc.) to obtain a bagasse decomposition extract. it can. The bagasse decomposition extract thus obtained can be stored as a liquid or powdery extract concentrated so that the solid content is 30% by mass or more. When the extract is liquid, it is preferable to store the extract by refrigeration.
上述した各実施形態におけるバガスの分解抽出物は、液状又は粉末状であってよい。粉末状のバガスの分解抽出物は、例えば、液状のバガス分解抽出物を用いて、スプレードライ法、凍結乾燥法、流動層造粒法、又は賦形剤を用いた粉末化法等により製造することができる。 The bagasse decomposition extract in each embodiment described above may be liquid or powder. The powdered bagasse decomposition extract is produced by using, for example, a liquid bagasse decomposition extract by a spray drying method, a freeze drying method, a fluidized bed granulation method, or a powdering method using an excipient. be able to.
本実施形態の抗糖化剤は、バガスの分解抽出物以外に賦形剤などを含んでもよい。賦形剤として、抗糖化剤が動物用である場合、コーンスターチ、及び小麦デンプン等の各種デンプン、デキストリン、各種グルテン、小麦粉、ふすま、各種米糠、大豆かす、及び黄粉などの大豆類、グルコース又は乳糖などの糖類、植物・動物油等の油脂類、魚粉類、酵母類、ケイ素化合物類、各種リン酸塩、ケイソウ土又はベントナイトなどの鉱物類、飼料及び飼料添加物の製剤を製造する上で使用できる賦形剤が挙げられる。また、抗糖化剤がヒト用である場合、乳糖、デンプン及びマルトース等の糖類、その他ヒト用の製剤を製造する上で使用できる賦形剤が挙げられる。これらのうち、コーンスターチ、デキストリン及び脱脂米糠は、製剤用担体として用いることができ、これらと甘蔗由来の抽出物を混合することで、抗糖化剤を、例えば、粉末状、顆粒状、又は錠剤状の固形製剤とすることができる。 The anti-glycation agent of this embodiment may contain an excipient | filler other than the decomposition extract of bagasse. As an excipient, when the anti-glycation agent is for animals, various starches such as corn starch and wheat starch, dextrin, various gluten, wheat flour, bran, various rice bran, soybean meal, soybean flour, and other soybeans, glucose or lactose Can be used in the manufacture of pharmaceuticals such as sugars, oils and fats such as vegetable and animal oils, fish meal, yeasts, silicon compounds, various phosphates, diatomaceous earth or bentonite, feed and feed additives Excipients are mentioned. Moreover, when an anti-glycation agent is for humans, saccharide | sugar, such as lactose, starch, and maltose, and the excipient | filler which can be used when manufacturing a formulation for humans are mentioned. Among these, corn starch, dextrin and defatted rice bran can be used as a carrier for pharmaceutical preparations, and by mixing these with an extract derived from sweet potato, an anti-glycation agent can be used, for example, in the form of powder, granules, or tablets It can be set as a solid preparation.
本実施形態の抗糖化剤は、ヒト又は動物に投与（経口投与又は非経口投与）することにより、抗糖化効果を奏するものであってよい。 The anti-glycation agent of this embodiment may exhibit an anti-glycation effect by administration (oral administration or parenteral administration) to humans or animals.
抗糖化剤が非経口投与される場合、投与量としては、例えば、バガスの分解抽出物が体重１ｋｇ当たり１回に１００μｇ以上となるように投与されるのが好ましく、１５０μｇ以上となるように投与されるのがより好ましく、２００μｇ以上となるように投与されるのが更に好ましい。また、バガスの分解抽出物が体重１ｋｇ当たり１日に２００μｇ以上となるように投与されるのが好ましく、３００μｇ以上となるように投与されるのがより好ましく、４００μｇ以上となるように投与されるのが更に好ましい。また、バガスの分解抽出物が、体重１ｋｇ当たり１回に２０００ｍｇ以下となるように投与されるのが好ましく、１５００ｍｇ以下となるように投与されるのがより好ましく、１０００ｍｇ以下となるように投与されるのが更に好ましい。また、バガスの分解抽出物が体重１ｋｇ当たり１日に４０００ｍｇ以下となるように投与されるのが好ましく、３０００ｍｇ以下となるように投与されるのがより好ましく、２０００ｍｇ以下となるように投与されるのが更に好ましい。この範囲であれば、十分な血中濃度を達成することができ、抗糖化活性をよりよく発現することができる。 When the anti-glycation agent is administered parenterally, the dosage is, for example, preferably administered such that the bagasse degradation extract is 100 μg or more per kg body weight, and is administered so that it is 150 μg or more. It is more preferable that the dose is 200 μg or more. The bagasse degradation extract is preferably administered so as to be 200 μg or more per day per kg of body weight, more preferably 300 μg or more, and more preferably 400 μg or more. Is more preferable. The bagasse decomposition extract is preferably administered to 2000 mg or less per kg body weight, more preferably 1500 mg or less, more preferably 1000 mg or less. More preferably. In addition, the bagasse degradation extract is preferably administered at a dose of 4000 mg or less per kg body weight per day, more preferably at a dose of 3000 mg or less, and a dose of 2000 mg or less. Is more preferable. If it is this range, sufficient blood concentration can be achieved and anti-glycation activity can be expressed better.
抗糖化剤が経口投与される場合、抗糖化剤の投与量は、バガスの分解抽出物の精製度、形態、対象とする動物の種類、健康状態、成長の度合い等により適宜決定し得る。特に投与の形態、例えば集中投与又は長期投与のいずれかであるかは、投与量を決定する上で重要な要因である。集中投与である場合、抗糖化剤の投与量は、バガスの分解抽出物の全量基準（固形分）で、体重１ｋｇ当たり１日に５０〜３，０００ｍｇ、又は１００〜２，０００ｍｇであってよい。また、集中投与の場合の投与期間は、１〜２０日間であってよい。日常的に長期投与する場合、抗糖化剤の投与量は、バガスの分解抽出物の全量基準（固形分）で、体重１ｋｇ当たり１日に１〜５００ｍｇ又は、１〜１００ｍｇであってよい。長期投与の場合の投与期間は、例えば、数週間から数ヶ月間（例えば、２０〜１８０日間）であってよい。この範囲であれば、十分な血中濃度を達成することができ、抗糖化活性をよりよく発現することができる。 When the anti-glycation agent is orally administered, the dose of the anti-glycation agent can be appropriately determined depending on the degree of purification of the bagasse degradation extract, the form, the type of animal to be treated, the health condition, the degree of growth, and the like. In particular, the mode of administration, such as intensive or long-term administration, is an important factor in determining the dosage. In the case of intensive administration, the dose of the anti-glycation agent may be 50 to 3,000 mg per kg body weight per day or 100 to 2,000 mg per kg body weight based on the total amount (solid content) of the bagasse degradation extract. . Moreover, the administration period in the case of intensive administration may be 1 to 20 days. In the case of daily long-term administration, the dose of the anti-glycation agent may be 1 to 500 mg or 1 to 100 mg per day per kg of body weight based on the total amount (solid content) of the bagasse degradation extract. The administration period in the case of long-term administration may be, for example, several weeks to several months (for example, 20 to 180 days). If it is this range, sufficient blood concentration can be achieved and anti-glycation activity can be expressed better.
本実施形態の抗糖化剤は、医薬品、医薬部外品、飲食品（食品組成物）、飼料、飼料添加物等の製品の成分として使用することができる。飲食品(飲料及び食品)としては、例えば、健康食品、機能性表示食品、特別用途食品、栄養補助食品、サプリメント又は特定保健用食品等が挙げられる。また、上記抗糖化剤は、調味料（醤油、味噌等）、菓子類等の食品、又は水、清涼飲料水、果汁飲料、アルコール飲料等の飲料における成分として使用することもできる。 The anti-glycation agent of the present embodiment can be used as a component of products such as pharmaceuticals, quasi drugs, food and drink (food composition), feed, feed additives and the like. Examples of the foods and drinks (beverages and foods) include health foods, functional display foods, special-purpose foods, nutritional supplements, supplements, and foods for specified health use. Moreover, the said anti-glycation agent can also be used as a component in foodstuffs, such as seasonings (soy sauce, miso, etc.), confectionery, or drinks, such as water, soft drinks, fruit juice drinks, and alcoholic drinks.
飼料としては、ドッグフード、キャットフード等のコンパニオン・アニマル用飼料、家畜用飼料、家禽用飼料、養殖魚介類用飼料等が挙げられる。「飼料」には、動物が栄養目的で経口的に摂取するもの全てが含まれる。具体的には、養分含量の面から分類すると、粗飼料、濃厚飼料、無機物飼料、特殊飼料の全てを包含し、また公的規格の面から分類すると、配合飼料、混合飼料、単体飼料の全てを包含する。また、給餌方法の面から分類すると、直接給餌する飼料、他の飼料と混合して給餌する飼料、または飲料水に添加し栄養分を補給するための飼料の全てを包含する。 Examples of feed include feed for companions and animals such as dog food and cat food, feed for livestock, feed for poultry, and feed for cultured seafood. “Feed” includes anything that animals orally take for nutritional purposes. Specifically, when classified from the aspect of nutrient content, it includes all of roughage, concentrated feed, inorganic feed, and special feed, and from the aspect of official standards, it includes all of mixed feed, mixed feed, and simple feed. Includes. Further, when classified from the aspect of the feeding method, it includes all feeds that are fed directly, feeds that are mixed with other feeds, or feeds that are added to drinking water to supplement nutrients.
本実施形態の抗糖化剤からなる、又は抗糖化剤を含む上記製品（例えば、飲食品）は、抗糖化用であってよい。すなわち、本実施形態の抗糖化剤を含有する飲食品は、抗糖化用飲食品として好適に用いることができる。上記抗糖化剤を含有する、上記製品の形状は、固形又は液体のいずれの形状であってもよい。 The product (for example, food or drink) comprising or containing the anti-glycation agent of the present embodiment may be for anti-glycation. That is, the food / beverage products containing the anti-glycation agent of this embodiment can be used suitably as food / beverage products for anti-glycation. The shape of the product containing the anti-glycation agent may be either solid or liquid.
上記製品に含まれる抗糖化剤の含有量は、上記製品の種類及び摂取方法に応じて、適宜決定してよい。抗糖化効果をより一層有効に発揮する観点から、上記製品は、固形分として０．００１質量％以上となるような量のバガスの分解抽出物を含むことが好ましい。抗糖化剤を含有する、上記製品を集中的に摂取する場合、上記製品の摂取量（１日当たりの摂取量）は、バガスの分解抽出物の全量基準（固形分）で、好ましくは５０〜３，０００ｍｇ／ｋｇ（体重）であり、より好ましくは１００〜２，０００ｍｇ／ｋｇ（体重）である。日常的に長期摂取する場合、上記製品の摂取量（１日当たりの摂取量）は、バガスの分解抽出物の全量基準（固形分）で、好ましくは１〜５００ｍｇ／ｋｇ（体重）である。 The content of the anti-glycation agent contained in the product may be appropriately determined according to the type of the product and the intake method. From the viewpoint of more effectively exhibiting the anti-glycation effect, the product preferably contains a decomposition extract of bagasse in an amount such that the solid content is 0.001% by mass or more. When the above product containing an anti-glycation agent is intensively consumed, the intake amount of the product (intake amount per day) is preferably 50 to 3 on the basis of the total amount (solid content) of the decomposition extract of bagasse. 1,000 mg / kg (body weight), more preferably 100 to 2,000 mg / kg (body weight). In the case of daily long-term ingestion, the above-mentioned product intake (daily intake) is preferably 1 to 500 mg / kg (body weight), based on the total amount (solid content) of the bagasse degradation extract.
以下、実施例に基づいて本発明をより具体的に説明する。ただし、本発明は、以下の実施例により限定されるものではない。バガスの分解抽出物は、以下、単に「抽出物」と表現することがある。 Hereinafter, based on an Example, this invention is demonstrated more concretely. However, the present invention is not limited to the following examples. Hereinafter, the decomposition extract of bagasse may be simply referred to as “extract”.
＜バガスの分解抽出物の製造＞
［製造例１］
サトウキビの搾りかすであるバガス１５ｋｇ（含水率５０質量％）及び０．５％（ｗ／ｗ）水酸化ナトリウム水溶液１００Ｌを混合し、１５０℃の条件でアルカリ処理を行った。アルカリ処理後の混合液を固形分と液分に分離して、液分を約１００Ｌ得た。分画分子量２５００のＵＦ膜（ＧＥウォーター＆プロセス・テクノロジー社、ＧＨ８０４０Ｆ３０）を用いて限外濾過を行い、濾過液８０Ｌを得た。合成吸着剤（三菱ケミカル株式会社製、ＨＰ−２０）１リットルを樹脂塔（内径８０ｍｍ、高さ４００ｍｍ）に充填し、これに上記の濾過液を、ｐＨを６に調整してから流速１０リットル／時間（ＳＶ＝１０．０（時間−１））で通液した。
<Manufacture of decomposition extract of bagasse>
[Production Example 1]
15 kg of bagasse (water content 50% by mass) and 100 L of 0.5% (w / w) sodium hydroxide aqueous solution, which are sugarcane pomace, were mixed and subjected to alkali treatment at 150 ° C. The mixed liquid after the alkali treatment was separated into a solid content and a liquid content, and about 100 L of the liquid content was obtained. Ultrafiltration was performed using a UF membrane (GE Water & Process Technology Co., Ltd., GH8040F30) with a molecular weight cut off of 2500 to obtain 80 L of filtrate. 1 liter of a synthetic adsorbent (manufactured by Mitsubishi Chemical Co., Ltd., HP-20) is packed in a resin tower (inner diameter: 80 mm, height: 400 mm), and the above filtrate is adjusted to pH 6 and the flow rate is 10 liters. Per hour (SV = 10.0 (hour- 1 )).
続いて、５リットルの精製水を、流速１０リットル／時間（ＳＶ＝１０．０（時間−１））で樹脂塔に通液して洗浄した。次に、溶出溶媒として６０％エタノール水溶液（エタノール／水＝６０／４０（体積／体積））２リットルを、流速２リットル／時間（ＳＶ＝２．０（時間−１））で樹脂塔に通液した。続けて、２リットルの精製水を流速２リットル／時間（ＳＶ＝２．０（時間−１））で樹脂塔に通液し、合成吸着剤に吸着した成分を溶出させた。樹脂塔から溶出した画分を、ロータリーエバポレーターにて約１０倍の濃度に減圧濃縮したのち、一晩凍結乾燥して、バガスの分解抽出物として、茶褐色の粉末２０ｇを得た。これを抽出物Ａとした。 Subsequently, 5 liters of purified water was passed through the resin tower and washed at a flow rate of 10 liters / hour (SV = 10.0 (hour- 1 )). Next, 2 liters of a 60% ethanol aqueous solution (ethanol / water = 60/40 (volume / volume)) as an elution solvent was passed through the resin tower at a flow rate of 2 liters / hour (SV = 2.0 (time- 1 )). Liquid. Subsequently, 2 liters of purified water was passed through the resin tower at a flow rate of 2 liters / hour (SV = 2.0 (hour- 1 )) to elute the components adsorbed on the synthetic adsorbent. The fraction eluted from the resin tower was concentrated under reduced pressure to a concentration of about 10 times using a rotary evaporator, and then freeze-dried overnight to obtain 20 g of a brown powder as a decomposition extract of bagasse. This was designated as Extract A.
［製造例２］
サトウキビの搾りかすであるバガス３０ｋｇ（含水率５０質量％）を、２００℃の熱水１００Ｌで水熱処理を行った。前処理後の混合液を固形分と液分に分離して、液分を約８８Ｌ得た。分画分子量２５００のＵＦ膜（ＧＥウォーター＆プロセス・テクノロジー社、ＧＨ８０４０Ｆ３０）を用いて限外濾過を行い、濾過液７０Ｌを得た。合成吸着剤（三菱ケミカル株式会社製、ＳＰ−８５０）１リットルを樹脂塔（内径８０ｍｍ、高さ４００ｍｍ）に充填し、これに上記の濾過液のうち２５Ｌを、流速２０リットル／時間（ＳＶ＝２０．０（時間−１））で通液した。
[Production Example 2]
30 kg of bagasse (moisture content of 50% by mass), which is a pomace of sugarcane, was hydrothermally treated with 100 L of hot water at 200 ° C. The pretreated liquid mixture was separated into a solid content and a liquid content to obtain about 88 L of the liquid content. Ultrafiltration was performed using a UF membrane (GE Water & Process Technology Co., Ltd., GH8040F30) having a molecular weight cut off of 2500 to obtain a filtrate 70L. 1 liter of a synthetic adsorbent (manufactured by Mitsubishi Chemical Corporation, SP-850) is packed into a resin tower (
続いて、３．３リットルの精製水を、流速２０リットル／時間（ＳＶ＝２０．０（時間−１））で樹脂塔に通液して洗浄した。次に、溶出溶媒として６０％エタノール水溶液（エタノール／水＝６０／４０（体積／体積））２リットルを、流速２リットル／時間（ＳＶ＝２．０（時間−１））で樹脂塔に通液した。続けて、２リットルの精製水を流速２リットル／時間（ＳＶ＝２．０（時間−１））で樹脂塔に通液し、合成吸着剤に吸着した成分を溶出させた。樹脂塔から溶出した画分を、ロータリーエバポレーターにて約１０倍の濃度に減圧濃縮したのち、一晩凍結乾燥して、バガスの分解抽出物として、茶褐色の粉末４０ｇを得た。これを抽出物Ｗとした。 Subsequently, 3.3 liters of purified water was passed through the resin tower and washed at a flow rate of 20 liters / hour (SV = 20.0 (hour- 1 )). Next, 2 liters of a 60% ethanol aqueous solution (ethanol / water = 60/40 (volume / volume)) as an elution solvent was passed through the resin tower at a flow rate of 2 liters / hour (SV = 2.0 (time- 1 )). Liquid. Subsequently, 2 liters of purified water was passed through the resin tower at a flow rate of 2 liters / hour (SV = 2.0 (hour- 1 )) to elute the components adsorbed on the synthetic adsorbent. The fraction eluted from the resin tower was concentrated under reduced pressure to a concentration of about 10 times using a rotary evaporator, and then freeze-dried overnight to obtain 40 g of brown powder as a decomposition extract of bagasse. This was designated as Extract W.
＜抽出物Ａの抗糖化活性評価（試験例１〜２）＞
試験例１：ヒト血清アルブミンモデルにおける抗糖化活性の評価
グルコース−ヒト血清アルブミン（ＨＳＡ）の反応により生成されるＡＧＥｓに対するバガスの分解抽出物（抽出物Ａ）の抗糖化活性（ＡＧＥｓ生成抑制作用）を調べた。
<Evaluation of anti-glycation activity of Extract A (Test Examples 1-2)>
Test Example 1: Evaluation of anti-glycation activity in human serum albumin model Anti-glycation activity (AGEs production inhibitory action) of bagasse degradation extract (Extract A) on AGEs produced by glucose-human serum albumin (HSA) reaction I investigated.
（サンプル調製）
バガスの分解抽出物である抽出物Ａを１００ｍｇ／ｍＬとなるように蒸留水で溶解し試験液原液を調製した。この試験原液を蒸留水で希釈して、０．０１〜１００ｍｇ／ｍＬの溶液を調製した。これを試験用のサンプルとした。陽性対照として、糖化反応阻害剤であるアミノグアニジンの水溶液（濃度３．０ｍｇ／ｍＬ）を調製した。
(Sample preparation)
Extract A, which is a decomposition extract of bagasse, was dissolved in distilled water to a concentration of 100 mg / mL to prepare a test solution stock solution. This test stock solution was diluted with distilled water to prepare a 0.01-100 mg / mL solution. This was used as a test sample. As a positive control, an aqueous solution (concentration: 3.0 mg / mL) of aminoguanidine which is a saccharification reaction inhibitor was prepared.
（糖化反応条件）
０．１ｍｏｌ／Ｌリン酸緩衝液（ｐＨ７．４）、８ｍｇ／ｍＬヒト血清アルブミン（ＨＳＡ、Ｓｉｇｍａ−Ａｌｄｒｉｃｈ社製）、及び０．２ｍｏｌ／Ｌグルコース水溶液からなる反応液中に、調製した各濃度のサンプルを１／１０濃度（反応終濃度）になるように添加し、６０℃で４０時間インキュベーションした。陰性対照としてサンプルの代わりに蒸留水を添加したものを用いた。陽性対照として上述のアミノグアニジン水溶液を用いた。なお、陽性対照に対するブランクとしてグルコースの代わりに蒸留水を添加したものを用いた。
(Saccharification reaction conditions)
Each concentration prepared in a reaction solution consisting of 0.1 mol / L phosphate buffer (pH 7.4), 8 mg / mL human serum albumin (HSA, Sigma-Aldrich), and 0.2 mol / L glucose aqueous solution. Were added to a concentration of 1/10 (final reaction concentration) and incubated at 60 ° C. for 40 hours. What added distilled water instead of the sample was used as a negative control. The above aminoguanidine aqueous solution was used as a positive control. In addition, what added distilled water instead of glucose was used as a blank with respect to a positive control.
（抗糖化活性の測定）
糖化反応終了後、反応液に生成した蛍光性ＡＧＥｓをマイクロプレートリーダー（ＳｐｅｃｔｒａＭａｘ ｉ３、モレキュラーデバイス社）で測定した（励起波長３７０ｎｍ、蛍光波長４４０ｎｍ）。ＡＧＥｓの生成阻害率（以下、単に「阻害率」ともいう）は、糖化反応においてサンプルを添加した反応液の蛍光強度をＦ１とし、グルコース水溶液の代わりに蒸留水を添加してインキュベーションした反応液の蛍光強度をＦ２とし、バガスの分解抽出物又はアミノグアニジンを添加せずにインキュベーションした反応液の蛍光強度をＦ３とし、ブランクとして、バガスの分解抽出物又はアミノグアニジンを添加せずに、グルコース水溶液の代わりに蒸留水を添加してインキュベーションした反応液の蛍光強度をＦ４として、下記の式に従って算出した。
蛍光性ＡＧＥｓ阻害率（％）＝（１−（Ｆ１−Ｆ２）／（Ｆ３−Ｆ４））×１００
(Measurement of anti-glycation activity)
After the saccharification reaction, fluorescent AGEs generated in the reaction solution were measured with a microplate reader (SpectraMax i3, Molecular Devices) (excitation wavelength 370 nm, fluorescence wavelength 440 nm). The AGE generation inhibition rate (hereinafter also simply referred to as “inhibition rate”) is a reaction solution in which the fluorescence intensity of the reaction solution to which the sample is added in the saccharification reaction is F 1 and distilled water is added instead of the glucose aqueous solution and incubated. the fluorescence intensity and F 2, the fluorescence intensity of the reaction solution was incubated without addition of decomposition extract or aminoguanidine bagasse and F 3, as a blank, without the addition of a decomposition extract or aminoguanidine bagasse, The fluorescence intensity of the reaction solution incubated with distilled water added instead of the glucose aqueous solution was defined as F 4 and calculated according to the following formula.
Fluorescence AGEs inhibition rate (%) = (1− (F 1 −F 2 ) / (F 3 −F 4 )) × 100
バガスの分解抽出物（抽出物Ａ）の各反応終濃度（０．１ｍｇ／ｍＬ、０．３ｍｇ／ｍＬ又は１ｍｇ／ｍＬ）における蛍光性ＡＧＥｓ（ＨＳＡ）の阻害率を図１に示す。図１のとおり、抽出物Ａは、濃度依存的に阻害率が増加し、抗糖化活性（蛍光性ＡＧＥｓ（ＨＳＡ）生成抑制作用）を示した。陽性対照であるアミノグアニジンの０．３ｍｇ／ｍＬにおける蛍光性ＡＧＥｓ（ＨＳＡ）の阻害率は８１．２±１．４％であった。アミノグアニジンは、抗糖化活性（蛍光性ＡＧＥｓ（ＨＳＡ）生成抑制作用）を有することが確認された。抽出物Ａの各濃度におけるサンプルの阻害率から算出したＩＣ５０（５０％生成阻害濃度）は、０．１９ｍｇ／ｍＬで、ヒト血清アルブミンモデルにおいて、抽出物Ａは抗糖化活性を有していることが示された。 FIG. 1 shows the inhibition rate of fluorescent AGEs (HSA) at each reaction final concentration (0.1 mg / mL, 0.3 mg / mL or 1 mg / mL) of the decomposition extract of bagasse (Extract A). As shown in FIG. 1, the extract A increased in inhibition rate in a concentration-dependent manner and exhibited anti-glycation activity (fluorescence AGEs (HSA) production inhibitory action). The inhibition rate of fluorescent AGEs (HSA) at 0.3 mg / mL of aminoguanidine as a positive control was 81.2 ± 1.4%. It was confirmed that aminoguanidine has anti-glycation activity (fluorescence AGEs (HSA) production inhibitory action). IC 50 (50% production inhibitory concentration) calculated from the inhibition rate of the sample at each concentration of Extract A was 0.19 mg / mL, and in the human serum albumin model, Extract A has anti-glycation activity. It was shown that.
試験例２：ＡＧＥｓ架橋切断試験（ＡＧＥｓ分解活性の評価）
次に、ＡＧＥｓ架橋切断試験により、バガスの分解抽出物（抽出物Ａ）のＡＧＥｓ分解活性を評価した。ＡＧＥｓ分解活性（ＡＧＥｓ架橋切断作用）は、公知の方法（例えば、Ｇｌｙｃａｔｉｖｅ Ｓｔｒｅｓｓ Ｒｅｓｅａｒｃｈ ２０１５年，２巻（２号），ｐｐ．５８−６６）である、αジケトン構造を有する１−フェニルー１，２−プロパンジオン（ｌ−ｐｈｅｎｙｌ−１，２−ｐｒｏｐａｎｅｄｉｏｎｅ：ＰＰＤ）をモデル基質とした反応系を使用した方法で評価した。
Test Example 2: AGEs cross-linking cleavage test (evaluation of AGEs degradation activity)
Next, the AGEs decomposition activity of the bagasse decomposition extract (Extract A) was evaluated by an AGEs cross-linking test. The AGEs degradation activity (AGEs cross-linking cleavage activity) is a known method (for example, Glycatable Stress Research 2015, Vol. 2 (No. 2), pp. 58-66), 1-phenyl-1,2 having an α-diketone structure. -Evaluation was performed by a method using a reaction system using propanedione (1-PD-1,2-propanedion: PPD) as a model substrate.
（サンプル調製）
バガスの分解抽出物である抽出物Ａを２０ｍｇ／ｍＬとなるように蒸留水で溶解し、試験用のサンプルを調製した。
(Sample preparation)
Extract A, a decomposition extract of bagasse, was dissolved in distilled water to 20 mg / mL to prepare a sample for testing.
（架橋切断反応条件）
０．１６ｍｏｌ／Ｌのリン酸緩衝液（ｐＨ７．４）、２ｍｍｏｌ／ｍＬのＰＰＤの組成の反応液中に、上記で調製したサンプルを１／２濃度（１０ｍｇ／ｍＬ）になるように添加し、３７℃で８時間インキュベーションした。陰性対照としてはサンプルの代わりに蒸留水を添加したものを用いた。陽性対照としてＰＴＢ（Ｎ−ｐｈｅｎａｃｙｌｔｈｉａｚｏｌｉｕｍｂｒｏｍｉｄｅ）を用いた。反応液を２０℃、３０００×ｇで１０分間遠心分離し、上清を得た。上清中の安息香酸量を逆相ＨＰＬＣで分析した。反応液中の安息香酸量は、別途測定したサンプル中の安息香酸量を差し引いて求めた。１ｍｏｌのＰＰＤは１ｍｏｌの安息香酸を生成することから、以下の式で架橋切断率を算出した。
架橋切断率（％）＝｛（Ａ−Ｂ）／Ｃ｝×１００
Ａ：反応液中の安息香酸量
Ｂ：サンプル中の安息香酸量
Ｃ：反応に供したＰＰＤ量（基質量）
(Crosslinking reaction conditions)
The sample prepared above was added to a reaction solution having a composition of 0.16 mol / L phosphate buffer (pH 7.4) and 2 mmol / mL PPD so that the concentration was ½ (10 mg / mL). And incubated at 37 ° C. for 8 hours. As a negative control, a sample to which distilled water was added instead of the sample was used. PTB (N-phenacylthiazolium bromide) was used as a positive control. The reaction solution was centrifuged at 3000 × g for 10 minutes at 20 ° C. to obtain a supernatant. The amount of benzoic acid in the supernatant was analyzed by reverse phase HPLC. The amount of benzoic acid in the reaction solution was determined by subtracting the amount of benzoic acid in the sample measured separately. Since 1 mol of PPD produces 1 mol of benzoic acid, the crosslinking cleavage rate was calculated by the following formula.
Crosslink cutting rate (%) = {(A−B) / C} × 100
A: Amount of benzoic acid in reaction solution B: Amount of benzoic acid in sample C: Amount of PPD subjected to reaction (base mass)
（架橋切断試験結果）
サンプル及びＰＴＢ溶液（５ｍｍｏｌ／Ｌ）における架橋切断率と、ＰＴＢ（５ｍｍｏｌ／Ｌ）を１００％としたときのサンプルにおける架橋切断率の値（切断率相対値）を求めたところ、サンプルの架橋切断率は８．５０、ＰＴＢの架橋切断率は２０．１であり、サンプルの切断率相対値は４２．２９％であった。よって、抽出物ＡがＡＧＥｓの分解活性を有していることが示された。
(Results of cross-linking cutting test)
When the crosslink breakage rate in the sample and PTB solution (5 mmol / L) and the value of the crosslink breakage rate (cutting rate relative value) in the sample when PTB (5 mmol / L) is taken as 100%, the crosslink breakage of the sample was obtained. The rate was 8.50, the cross-linking cutting rate of PTB was 20.1, and the relative value of the cutting rate of the sample was 42.29%. Therefore, it was shown that the extract A has the activity of degrading AGEs.
＜抽出物Ｗの抗糖化活性評価（試験例３〜４）＞
試験例３：ヒト血清アルブミンモデルにおける抗糖化活性の評価
バガスの分解抽出物として上述の抽出物Ｗを用いたこと、サンプルの調製において蒸留水ではなくジメチルスルホキシド（ＤＭＳＯ）を用いたこと以外は、試験例１と同様にして、抗糖化活性を評価した。陽性対照としては、アミノグアニジンの水溶液（最終濃度０．３ｍｇ／ｍＬ）を用いた。陽性対照であるアミノグアニジンの０．３ｍｇ／ｍＬにおける蛍光性ＡＧＥｓ（ＨＳＡ）の阻害率は７４．６±０．８％であった。測定結果を図２に示す。また、抽出物Ｗの各濃度におけるサンプルの阻害率から算出したＩＣ５０（５０％生成阻害濃度）は、０．１４ｍｇ／ｍＬで、抽出物Ｗは、抗糖化活性を有していることが示された。
<Evaluation of anti-glycation activity of extract W (Test Examples 3 to 4)>
Test Example 3: Evaluation of anti-glycation activity in a human serum albumin model Except that the above extract W was used as a decomposition extract of bagasse, and that dimethyl sulfoxide (DMSO) was used instead of distilled water in sample preparation. The anti-glycation activity was evaluated in the same manner as in Test Example 1. As a positive control, an aminoguanidine aqueous solution (final concentration 0.3 mg / mL) was used. The inhibition rate of fluorescent AGEs (HSA) at 0.3 mg / mL of aminoguanidine as a positive control was 74.6 ± 0.8%. The measurement results are shown in FIG. The IC 50 (50% production inhibitory concentration) calculated from the inhibition rate of the sample at each concentration of the extract W is 0.14 mg / mL, and the extract W has anti-glycation activity. It was done.
試験例４：ＡＧＥｓ架橋切断試験（ＡＧＥｓ分解活性の評価）
（サンプル調製）
バガスの分解抽出物である抽出物Ｗを５０％ＤＭＳＯで溶解し、２０ｍｇ／ｍＬ溶液を調製した。この溶液を５０％ＤＭＳＯで段階希釈して、試験用のサンプルとした。陽性対照としては、１０ｍｍｏｌ／ＬのＰＴＢ（Ｎ−ｐｈｅｎａｃｙｌｔｈｉａｚｏｌｉｕｍｂｒｏｍｉｄｅ）溶液を用いた。
Test Example 4: AGEs cross-linking cleavage test (evaluation of AGEs degradation activity)
(Sample preparation)
Extract W, which is a decomposition extract of bagasse, was dissolved in 50% DMSO to prepare a 20 mg / mL solution. This solution was serially diluted with 50% DMSO to prepare a test sample. As a positive control, a 10 mmol / L PTB (N-phenacylthiolium bromide) solution was used.
（架橋切断反応条件）
試験溶液又はＰＴＢ溶液（１０ｍｍｏｌ／Ｌ）と、１０ｍｍｏｌ／ＬのＰＰＤ溶液と、０．２ｍｏｌ／Ｌリン酸緩衝液（ｐＨ７．４）と、を５：１：４の割合で混合し、３７℃で８時間反応させた（ｎ＝３）。反応終了後、塩酸を加えて反応停止させた。その後、反応液を２０℃で３，０００×ｇで１０分間遠心分離し、上清中の安息香酸量を逆相ＨＰＬＣで分析した。反応液中の安息香酸量は、別途測定したサンプル中の安息香酸量を差し引いて求めた。１ｍｏｌのＰＰＤは１ｍｏｌの安息香酸を生成することから、以下の式で架橋切断率を算出した。架橋切断の相対値（切断率相対値）はＰＴＢの架橋切断率を１００としたときの、各濃度の架橋切断率の値（％）である。なお、測定装置としては、島津超高速液体クロマトグラフＮｅｘｅｒａシステム（株式会社島津製作所製）を用いた。
架橋切断率（％）＝｛（Ａ−Ｂ）／Ｃ｝×１００
Ａ：反応液中の安息香酸量
Ｂ：サンプル中の安息香酸量
Ｃ：反応に供したＰＰＤ量（基質量）
(Crosslinking reaction conditions)
The test solution or PTB solution (10 mmol / L), 10 mmol / L PPD solution, and 0.2 mol / L phosphate buffer (pH 7.4) were mixed at a ratio of 5: 1: 4, and the temperature was changed to 37 ° C. For 8 hours (n = 3). After completion of the reaction, hydrochloric acid was added to stop the reaction. Thereafter, the reaction solution was centrifuged at 3,000 × g for 10 minutes at 20 ° C., and the amount of benzoic acid in the supernatant was analyzed by reverse phase HPLC. The amount of benzoic acid in the reaction solution was determined by subtracting the amount of benzoic acid in the sample measured separately. Since 1 mol of PPD produces 1 mol of benzoic acid, the crosslinking cleavage rate was calculated by the following formula. The relative value of the crosslink cutting (cutting rate relative value) is the value (%) of the crosslink cutting rate at each concentration when the crosslink cutting rate of PTB is 100. In addition, as a measuring apparatus, Shimadzu ultra-high performance liquid chromatograph Nexera system (made by Shimadzu Corporation) was used.
Crosslink cutting rate (%) = {(A−B) / C} × 100
A: Amount of benzoic acid in reaction solution B: Amount of benzoic acid in sample C: Amount of PPD subjected to reaction (base mass)
（架橋切断試験結果）
サンプル及びＰＴＢ溶液（５ｍｍｏｌ／Ｌ）における架橋切断率と、ＰＴＢ（５ｍｍｏｌ／Ｌ）を１００％としたときのサンプルにおける架橋切断率の値（切断率相対値）を求めたところ、サンプルの架橋切断率は１０．０７、ＰＴＢの架橋切断率は２２．４であり、サンプルの切断率相対値は４４．８７％であった。よって、抽出物ＷがＡＧＥｓの分解活性を有していることが示された。
(Results of cross-linking cutting test)
When the crosslink breakage rate in the sample and PTB solution (5 mmol / L) and the value of the crosslink breakage rate (cutting rate relative value) in the sample when PTB (5 mmol / L) is taken as 100%, the crosslink breakage of the sample was obtained. The rate was 10.07, the cross-linking cleavage rate of PTB was 22.4, and the relative value of the cutting rate of the sample was 44.87%. Therefore, it was shown that the extract W has the activity of degrading AGEs.
Claims (8)
前記合成吸着剤は、無置換基型の芳香族系樹脂であり、
前記カラムの温度は２０〜６０℃であり、
前記混合溶媒のエタノール及び水の体積比（エタノール／水）は５０／５０〜６０／４０である、請求項２に記載の抗糖化剤。 In the bagasse decomposition extract, the decomposition treatment liquid is passed through a column packed with a synthetic adsorbent as a fixed carrier, and the components adsorbed on the synthetic adsorbent are eluted with a mixed solvent of ethanol and water. Fraction obtained by
The synthetic adsorbent is an unsubstituted aromatic resin,
The temperature of the column is 20-60 ° C.
The anti-glycation agent according to claim 2, wherein a volume ratio (ethanol / water) of ethanol and water of the mixed solvent is 50/50 to 60/40.
The food-drinks for anti-glycation containing the anti-glycation agent as described in any one of Claims 1-7.
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2018103252A JP2019205398A (en) | 2018-05-30 | 2018-05-30 | Anti-glycation agent |
| US17/058,756 US20210369597A1 (en) | 2018-05-30 | 2019-05-30 | Anti-Obesity Agent, Anti-Dementia Agent, Deodorant, Anti-Aging Agent, Anti-Glycation Agent, Anti-Type I Allergy Agent, Hypotensive Agent, Flavor Improving Agent, Muscle Enhancing Agent, and Bone Metabolism Improving Agent |
| PCT/JP2019/021592 WO2019230907A1 (en) | 2018-05-30 | 2019-05-30 | Anti-obesity agent, anti-dementia agent, deodorant, anti-aging agent, anti-glycation agent, anti-type i allergy agent, hypotensive agent, flavor improving agent, muscle enhancing agent, and bone metabolism improving agent |
| AU2019277620A AU2019277620A1 (en) | 2018-05-30 | 2019-05-30 | Anti-obesity agent, anti-dementia agent, deodorant, anti-aging agent, anti-glycation agent, anti-type i allergy agent, hypotensive agent, flavor improving agent, muscle enhancing agent, and bone metabolism improving agent |
| CN201980035152.6A CN112203672A (en) | 2018-05-30 | 2019-05-30 | Obesity inhibitor, antidementia agent, deodorant, antiaging agent, anti-glycation agent, anti-type I allergy agent, antihypertensive agent, flavor improving agent, muscle strengthening agent and bone metabolism improving agent |
| US17/222,343 US20210251884A1 (en) | 2018-05-30 | 2021-04-05 | Anti-Obesity Agent, Anti-Dementia Agent, Deodorant, Anti-Aging Agent, Anti-Glycation Agent, Anti-Type I Allergy Agent, Hypotensive Agent, Flavor Improving Agent, Muscle Enhancing Agent, and Bone Metabolism Improving Agent |
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| JP2018103252A JP2019205398A (en) | 2018-05-30 | 2018-05-30 | Anti-glycation agent |
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Citations (2)
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|---|---|---|---|---|
| JP2010070541A (en) * | 2008-08-22 | 2010-04-02 | Kao Corp | Tg synthesis inhibitor |
| WO2013100105A1 (en) * | 2011-12-27 | 2013-07-04 | 森下仁丹株式会社 | Maillard reaction inhibitor |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010070541A (en) * | 2008-08-22 | 2010-04-02 | Kao Corp | Tg synthesis inhibitor |
| WO2013100105A1 (en) * | 2011-12-27 | 2013-07-04 | 森下仁丹株式会社 | Maillard reaction inhibitor |
Non-Patent Citations (3)
| Title |
|---|
| SADOWSKA-BARTOSZ IZABELA, ET AL.: "Prevention of Protein Glycation by Natural Compounds", MOLECULES, vol. 20, JPN6019025444, 2015, pages 3309 - 3334, XP055662150, ISSN: 0004936346, DOI: 10.3390/molecules20023309 * |
| 三菱ケミカル: "合成吸着剤", [ONLINE], JPN6019025437, 4 April 2017 (2017-04-04), ISSN: 0004936347 * |
| 古田到真 他: "国内製糖工場廃棄物からの有価物製造におけるＧＨＧ削減技術実証", 精糖技術研究会誌, vol. 63, JPN6019025436, 2017, pages 7 - 10, ISSN: 0004936345 * |
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