WO2008090999A1 - Inhibiteur de la glucosidase - Google Patents

Inhibiteur de la glucosidase Download PDF

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Publication number
WO2008090999A1
WO2008090999A1 PCT/JP2008/051142 JP2008051142W WO2008090999A1 WO 2008090999 A1 WO2008090999 A1 WO 2008090999A1 JP 2008051142 W JP2008051142 W JP 2008051142W WO 2008090999 A1 WO2008090999 A1 WO 2008090999A1
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Prior art keywords
mash
shochu
residue
fraction
molecular weight
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Application number
PCT/JP2008/051142
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English (en)
Japanese (ja)
Inventor
Hiroyoshi Inoue
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Up Well Co. Ltd.
Priority date (The priority date 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 date listed.)
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Publication date
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Priority to JP2008538065A priority Critical patent/JP4947812B2/ja
Publication of WO2008090999A1 publication Critical patent/WO2008090999A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/06—Fungi, e.g. yeasts
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12F—RECOVERY OF BY-PRODUCTS OF FERMENTED SOLUTIONS; DENATURED ALCOHOL; PREPARATION THEREOF
    • C12F3/00—Recovery of by-products
    • C12F3/10—Recovery of by-products from distillery slops

Definitions

  • the present invention relates to a darcosidase inhibitor.
  • diabetes treatment is to maintain blood glucose levels within the normal range to prevent complications.
  • Complications include nephropathy, retinopathy, neuropathy, and stroke and myocardial infarction due to progression of arteriosclerosis.
  • Atherosclerosis has already been shown to progress, especially from the postprandial hyperglycemic stage. Therefore, a blood glucose control that improves postprandial hyperglycemia is also important to prevent the progression of arteriosclerosis.
  • ⁇ -Dalcosidase inhibitors suppress the breakdown of starch or carbohydrates in the diet and delay the absorption of budu sugar into the body, thereby suppressing a rapid increase in blood glucose level after eating.
  • Known ⁇ -darcosidase inhibitors include carbose, poglibose, and miglitol. '
  • Japanese Patent Application Laid-Open No. 2000-0 1 1 6 4 8 6 describes a food containing a large amount of lactic acid as a food for suppressing an increase in blood glucose level after a meal.
  • lactic acid has an a-darcosidase inhibitory action and an o-amylase inhibitory action, and further suppresses an increase in blood glucose level after meals.
  • the above documents exemplify dairy products made using lactic acid bacteria, such as yogurt, lactic acid bacteria drinks, and sour milk drinks, as foods containing lactic acid. Also, in food production such as sake brewing, soft drinks, confectionery, etc. Lactic acid is used, but these foods He also states that no reports have been found to show the effect of suppressing the increase.
  • Shochu is produced by fermenting starchy raw materials (cereals, potatoes) or saccharide raw materials (brown sugar, natto palm) and then distilling them. In the production process of shochu, the residue mash after distillation is usually discarded. However, environmental issues regarding the disposal of shochu residue and mash are being discussed, and their effective use is required. The power of shochu residue moromi that is known to be used as animal feed is still being researched.
  • Japanese Patent Application Laid-Open No. 2002-371003 describes that a barley fermented extract obtained by concentrating a filtrate of a distilled residue of barley shochu suppressed an increase in blood glucose level after a meal.
  • the blood glucose level elevation inhibitory component described in the above-mentioned document is due to an insulin-like action, and no darcosidase or amylase inhibitory action was observed (paragraph number 0013).
  • Japanese Patent Application Laid-Open No. 2005-224205 describes a health food having a blood glucose lowering effect using buckwheat shochu.
  • the object of the present invention is to find out the usefulness of shochu residue mash that is normally discarded in the production of shochu.
  • the present invention provides an a-darcosidase inhibitor containing, as an active ingredient, a concentrated extract of shochu residue moromi or a filtrate or supernatant extract of the shochu residue moromi.
  • the concentrated extract is a fraction having a molecular weight of 6000 or less obtained from a shochu residue mash filtrate or supernatant.
  • the present invention further provides a concentrated extract of shochu residue moromi or a concentrated extract of the shochu residue moromi filtrate or supernatant and a fibrous substance as an active ingredient.
  • a depressant is also provided.
  • a component having ⁇ -darcosidase inhibitory activity is obtained from the shochu residue mash, and an o-darcosidase inhibitor having this active component is provided.
  • FIG. 1 is a graph showing the inhibition rate of ⁇ -darcosidase activity in wheat, rice, rice bran, and buckwheat shochu residue mash supernatant fractions.
  • FIG. 2 is a graph showing the effect of administration of the wheat flour shochu residue mash supernatant fraction on changes in blood glucose levels of normal rats after sucrose application.
  • FIG. 3 is a graph showing the inhibition rate of ⁇ -darcosidase activity in the wheat bran residue residue mash supernatant fraction divided by molecular weight.
  • FIG. 4 is a graph showing the inhibition rate against ⁇ -darcosidase activity of the rice shochu residue mash supernatant fraction divided by molecular weight.
  • FIG. 5 is a graph showing changes over time in blood glucose levels of normal rats after sucrose administration by administration of a shochu residue mash mash supernatant fraction combined with a fibrous substance.
  • FIG. 6 is a graph showing the sucrose load at various doses and the time course of blood glucose level before and after the test substance administration, 30 minutes after administration of the test substance, and 60 minutes after administration of the test substance.
  • FIG. 7 is a graph showing changes in blood glucose level with time when test substance O g was administered (control) and when 0.5 g was administered.
  • FIG. 8 is a graph showing blood insulin concentrations before and 30 minutes after administration of test substance O g (control) and 0.5 g.
  • “shochu residue moromi” means starchy raw materials (cereals, potatoes, etc.) Or moromi that remains after fermenting saccharide raw materials (brown sugar, natto palm, etc.) and then distilling to remove the alcohol.
  • the production of shochu usually includes a starch saccharification process by koji mold, a sugar fermentation process by yeast, and an alcohol distillation process.
  • wheat or rice is treated in a conventional manner (washing, dipping, draining, steaming, allowing to cool, etc.), and this is inoculated with a seed pod of Aspergillus Kawachii that is usually used in shochu production. , And make the iron for an appropriate period at the appropriate temperature.
  • the yeast used for normal baking production is added and mixed, and saccharified and fermented by a conventional method to obtain primary moromi.
  • the primary moromi baking yeast is propagated.
  • add and mix the shochu main ingredients and water treated by ordinary methods washing, dipping, draining, steaming, allowing to cool, etc.
  • any commonly used ingredient can be used, and examples include, but are not limited to, grains such as barley, wheat, rice, corn, and buckwheat, potatoes, brown sugar, and peanuts. Barley is preferable.
  • the yeast fermentation process preparation is in two stages, but it is not necessary to divide the preparation into two stages. The mash after fermentation is subjected to distillation, and the alcohol is recovered and fired. On the other hand, a residue mash from which the alcohol content has been removed is obtained.
  • the above shochu residue mash is concentrated as it is or separated into solid and liquid by filtration, centrifugation, etc., and then the filtrate or supernatant is heated and concentrated, freeze-dried or spray-dried to obtain a concentrated extract. obtain. Further, the concentrated extract can be used to concentrate the active ingredient using an appropriate column such as a silica gel column, an ODS column, an ion exchange resin, or an ultrafiltration membrane molecular sieve. Of these, the filtrate or supernatant fraction is preferred, and the fraction with a molecular weight of 600 or less is preferred.
  • the concentrated extract As shown in the examples described later, Inhibitory activity of lysase is observed.
  • the inhibition rate of the enzyme reaction of ⁇ -darcosidase under the conditions described in Example 1 is 20 ° /.
  • it is defined as having a-vlucosidase inhibitory activity.
  • the concentrated extract also suppresses an increase in postprandial blood glucose level, as shown in Examples described later. Therefore, the hypoglycemic effect of the concentrated extract is considered to be due to ⁇ -darcosidase inhibition, and the concentrated extract can be used as a ct-glucosidase inhibitor.
  • the concentrated extract in addition to the inhibitory activity of _darcosidase, the inhibitory activity of invertase and ⁇ _amylase is also observed.
  • the concentrated extract or monodalcosidase inhibitor can inhibit a variety of glycolytic enzymes.
  • the fraction of 0 or less contains succinic acid, pyroglutamic acid, and pyruvic acid.
  • These organic acids namely succinic acid, pyroglutamic acid, and pyruvic acid, have _darcosidase inhibitory activity.
  • the concentrated extract or a-darcosidase inhibitor can inhibit the action of ⁇ -darcosidase, which degrades carbohydrates, and delays the absorption of glucose from the small intestine. It can be administered orally for the treatment or prevention of various complications such as disorders, cataracts, kidney disorders, retinopathy, joint sclerosis, atherosclerosis, diabetic lobe.
  • the dose depends on the method of administration and the degree of symptoms, patient age, body weight, etc., but it is usually per adult dose per concentrated dose (especially the molecular weight of the filtrate or supernatant of shochu residue mash) (Fraction of 6 00 or less) may be from 0.05 g to 10 g, preferably from 0.075 g to 5 g, more preferably from 0.1 ⁇ to 1 ⁇ .
  • This dose can be appropriately determined by a known glucose tolerance test by humans.
  • the concentrated extract or ⁇ ; -darcosidase inhibitor can be in the form of a tablet, powder, or liquid. It can also be added to food or beverages.
  • a food for health maintenance having an a-darcosidase inhibitory action or a glycolytic enzyme inhibitory action as described above can also be obtained.
  • Such foods include home-use diabetic foods, liquid foods, foods for the sick (combination foods for adjusting diabetic foods, etc.), foods for specified health use, diet foods, and foods based on carbohydrates.
  • Specific food forms include, but are not limited to, coffee, soft drinks, soups, fruit juices, jams, biscuits, breads, and pasta.
  • the concentrated extract or ⁇ ; -darcosidase inhibitor may itself be contained as a hypoglycemic agent alone or in combination with a fibrous substance. It is particularly useful for suppressing postprandial blood glucose levels. By containing a fibrous substance, the blood glucose lowering effect is further enhanced. Examples of the fibrous material include cellulose and indigestible dextrin, and preferably indigestible dextrin is used. Such a hypoglycemic agent can also be made into a food as described above.
  • shochu residue mash from sweet potato, barley, rice or buckwheat was produced as follows.
  • Barley is shaved with a refining machine, water is added to this and steamed, then about 35-4
  • This supernatant was subjected to an ultrafiltration membrane device (Asahi Kasei; pen-type UF membrane), and a solution having a molecular weight of 600 or less was collected and then freeze-dried. Further, the remaining solution was separated into a fraction having a molecular weight of 500000 or less and a fraction having a molecular weight exceeding 500000, and each solution was freeze-dried.
  • the lyophilizate was used in the following examples.
  • the buckwheat rice was shaved with a refiner, then water was added and steamed.
  • the steamed buckwheat rice was cooled to about 35-40 ° C and mixed with Aspergillus Kawachii (Matsunosuke Hamaguchi Co., Ltd.).
  • Aspergillus Kawachii Matsunosuke Hamaguchi Co., Ltd.
  • To the buckwheat soba noodles the buckwheat oat and rice of the above production examples 1 and 2 are added and mixed so that the ratio of rice: wheat: buckwheat is 1: 1: 1.2, and water is added. It was mixed with an appropriate amount of shochu yeast and fermented at about 25-30 ° C for 10 days to obtain moromi. Subsequently, the residue mash was produced in the same manner as in Production Example 1 above, fractionated according to molecular weight, and freeze-dried.
  • Example 1 Effect of shochu residue moromi on a-darcosidase activity
  • lyophilized products of fractions having a molecular weight of 6 ⁇ 00 or less of wheat, rice, rice bran, and soba shochu residue mash As a control, 10 mg of carboxyl (trade name Darkopai (registered trademark); Bayer) was taken as l Omg and dissolved in 1 mL of 0.02 M phosphate buffer to obtain a test substance solution.
  • carboxyl trade name Darkopai (registered trademark); Bayer
  • reaction solution having the following composition was prepared: 0.4% ⁇ -Nitrophenyl a-D-darcoviranoside (Wako Pure Chemical Industries) 0.2 mL; Substance solution 0.2 mL; and 0.5 U / mL ⁇ -Dalcosidase (Toyobo) 0.1 mL.
  • one unit (U) of ct-dalcosidase is the amount of enzyme that liberates 1 ⁇ of glucose per minute from the non-reducing terminal side of the substrate under the following standard reaction conditions.
  • the above reaction solution was incubated at 37 ° C for 15 minutes to allow the enzyme reaction to proceed.
  • the reaction was stopped by adding 0.5 mL of 2M Tris solution (pH 7.0). 0.02 mL of the solution after stopping the reaction is taken, and the coloring reagent (glucose CII test kit; Wako Pure Chemical Industries, Ltd.) 3. Add (mL) and mix for 5 minutes at 37 ° C. And the absorbance was measured with a spectrophotometer (Beckman) at 500 nm. All measurements were performed twice.
  • Fig. 1 is a graph showing the inhibition rate of these shochu residue moromi to ⁇ -darcosidase activity.
  • carbose which is known to inhibit ct-dalcosidase, are also shown.
  • the vertical axis represents the inhibition rate (%) of ⁇ -darcosidase activity. All shochu residue and moromi showed inhibition of ⁇ -darcosidase activity, and in particular, wheat shochu residue and mash showed inhibition of more than 60%.
  • FIG. 2 is a graph showing the change in blood glucose level over time in each treatment group after sucrose application.
  • the horizontal axis represents the postprandial time (minutes), and the vertical axis represents the blood glucose level (serum darose concentration: mgZmL).
  • the black circle is the control group
  • the white circle is the cellulose administration group
  • the white triangle is the carbose administration group
  • the white square is the shochu residue mash supernatant fraction administration group.
  • the blood glucose level rapidly increased by 30 minutes after the treatment, and gradually decreased thereafter.
  • the cellulose administration group showed the same tendency as the control group.
  • the molecular weight of the wheat shochu residue moromi obtained in Production Example 1 is not more than 600.000; the freezing of the fraction having a molecular weight of more than 60.000 and less than 5.000; and a molecular weight of more than 500.000
  • the effect on the single dalcosidase activity was examined according to the procedure described in Example 1 above.
  • FIG. 3 is a graph showing the inhibition rate for the a-darcosidase activity of the mash supernatant fraction of the wheat shochu residue.
  • the vertical axis represents the inhibition rate (%) of a-darcosidase activity.
  • the fraction with a molecular weight of 6 0 0 0 or less is MW ⁇ 6 0 0 0; the fraction with a molecular weight of more than 6 0 0 0 but less than 5 0 0 0 0 is 6 0 0 0 MW ⁇ 5 0 0 0 0; and a fraction having a molecular weight exceeding 5 0 0 0 0 is represented by 5 0 0 0 minus MW.
  • inhibition of a-darcosidase activity was shown, but the inhibition rate was particularly high in fractions having a molecular weight of 600 or less.
  • the molecular weight of the rice shochu residue moromi obtained in Production Example 2 is not more than 600.000; the freezing of the fraction having a molecular weight of more than 60.000 and less than 5.000; and a molecular weight of more than 500.000
  • the effect on a-darcosidase activity was examined according to the procedure described in Example 1 above.
  • FIG. 4 is a graph showing the inhibition rate for the one dalcosidase activity of the mash residue obtained from the rice baking residue.
  • the vertical axis represents the inhibition rate (%) of a-darcosidase activity.
  • the fraction with a molecular weight of 6 0 0 0 or less is MW ⁇ 6 0 0 0; the fraction with a molecular weight of more than 6 0 0 0 but less than 5 0 0 0 0 is 6 0 0 0 MW + 5 0 0 0 0; and fractions with molecular weights greater than 5 0 0 0 0 at 5 0 0 0 0 ⁇ MW To express. In all fractions, including those with a molecular weight of 6 000 or less, 50 ° /. Inhibition of a-darcosidase activity was observed.
  • the sucrose intake group was orally given 2 g / kg sucrose and nothing else was administered.
  • 2 gZk g of sucrose was orally ingested, and 5 mg Zkg of the wheat shochu residue mash fraction lyophilized fraction of the above production example 1 was intragastrically administered.
  • the cellulose-added group includes 5 mg Zkg of the lyophilized fraction of the malt residue of the wheat shochu residue of Production Example 1 above, with a molecular weight of 600 ⁇ or less.
  • FIG. 5 is a graph showing the change in blood glucose level over time in each treatment group after sucrose application.
  • the vertical axis represents the blood glucose level (serum glucose concentration ⁇ mgZmL).
  • the white circle is the sucrose intake group
  • X is the group administered with the freeze-dried fraction with a molecular weight of 6000 or less of the barley burning residue mash (the barley shochu residue mash supernatant fraction administration group)
  • the white triangle is the above production example A group in which cellulose was added together with a fraction freeze-dried fraction with a molecular weight of 6000 or less of the wheat shochu residue mash (cellulose addition group).
  • the white square is a fraction with a molecular weight of 6000 or less of the mash of the wheat shochu residue in Production Example 1 above.
  • indigestible dextrin added group This is a group to which indigestible dextrin is added together with the lyophilized product (indigestible dextrin added group).
  • Cellulose added group and indigestible dextrin added group are: Compared with the clear fraction administration group, the increase in blood glucose level after meal was further suppressed. In particular, the combination of indigestible dextrin and the wheat flour shochu residue mash supernatant fraction showed an excellent hypoglycemic effect. (Example 6: Composition analysis of shochu residue moromi)
  • HPLC was performed under the following conditions:
  • CDD-6A conductivity detector
  • Detection is by column column loose seed purification method.
  • Buffer 20 mM Bis-Tris solution with 5 mM p-toluenesulfonic acid and 100 ⁇ EDTA
  • the specimen was prepared by dissolving Sample 2. Omg in 2000 ⁇ L of millQ water and filtering it through a 0.45 ⁇ membrane filter. The injection volume was 10 ⁇ L.
  • test substance a fraction having a molecular weight of 6000 or less of the wheat shochu residue mash of Production Example 1 was used. Subjects fasted for 10 hours before the start of the test (free drinking), and at the start of the test, 25 g of sucrose (Wako Pure Chemical Industries, Ltd.) was loaded at the same time as O g (control), 0. lg or 0.5 g test substance was taken and administered. Sucrose loading was measured before administration of the test substance, and 30 and 60 minutes after administration of the test substance. At the time of O g administration (control) and 0.5 g administration, blood was collected for blood tests before and 30 minutes after administration. Each test was performed at intervals of 24 hours or longer, and excessive suppression of food intake was avoided.
  • Figure 6 shows the results of blood glucose levels related to dose effects.
  • the measured values are expressed as relative values with the blood glucose level before sucrose loading as 100%.
  • black circles represent controls, triangles represent test substance 0.1 g administration, and white circles represent test substance 0.5 g administration.
  • the test substance O g administration control
  • 0.1 g of the test substance showed significantly lower values than the control at both 30 minutes and 60 minutes after administration (P 0.05).
  • the amount of the test substance was increased to 0.5 g, but there was no difference from the case of 0.1 lg.
  • the ⁇ -darcosidase inhibitor of the present invention is useful for the treatment or prevention of diabetes and its complications.

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Abstract

L'invention concerne un inhibiteur de la α-glucosidase qui comporte un extrait concentré d'une pâte de moromi de résidu de shochu ou un extrait concentré d'un filtrat ou surnageant de la pâte de moromi de résidu de shochu. L'inhibiteur de l'α-glucosidase peut être utilisé seul ou en combinaison avec une matière fibreuse en tant qu'agent hypoglycémique.
PCT/JP2008/051142 2007-01-22 2008-01-21 Inhibiteur de la glucosidase WO2008090999A1 (fr)

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JP2008538065A JP4947812B2 (ja) 2007-01-22 2008-01-21 グルコシダーゼ阻害剤

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013213021A (ja) * 2012-03-08 2013-10-17 Up Well:Kk 抗糖化剤

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001231499A (ja) * 2000-02-18 2001-08-28 Fancl Corp 食品組成物
JP2002027979A (ja) * 2000-07-14 2002-01-29 Nippon Synthetic Chem Ind Co Ltd:The α−グルコシダーゼ阻害剤の製造法
JP2002027978A (ja) * 2000-07-14 2002-01-29 Nippon Synthetic Chem Ind Co Ltd:The α−グルコシダーゼ阻害剤の製造法
JP2002371003A (ja) * 2001-06-15 2002-12-26 Kikkoman Corp 血糖値上昇抑制剤
JP2005224205A (ja) * 2004-02-16 2005-08-25 Hokko Chem Ind Co Ltd 健康食品

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005287454A (ja) * 2004-04-02 2005-10-20 Matsutani Chem Ind Ltd 保健機能付与飲食品及び飲食品へ保健機能を付与する方法
JP2006347967A (ja) * 2005-06-16 2006-12-28 Yuusu Techno Corporation:Kk 血糖値上昇抑制剤

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001231499A (ja) * 2000-02-18 2001-08-28 Fancl Corp 食品組成物
JP2002027979A (ja) * 2000-07-14 2002-01-29 Nippon Synthetic Chem Ind Co Ltd:The α−グルコシダーゼ阻害剤の製造法
JP2002027978A (ja) * 2000-07-14 2002-01-29 Nippon Synthetic Chem Ind Co Ltd:The α−グルコシダーゼ阻害剤の製造法
JP2002371003A (ja) * 2001-06-15 2002-12-26 Kikkoman Corp 血糖値上昇抑制剤
JP2005224205A (ja) * 2004-02-16 2005-08-25 Hokko Chem Ind Co Ltd 健康食品

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013213021A (ja) * 2012-03-08 2013-10-17 Up Well:Kk 抗糖化剤

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