TW201408302A - Soyasapogenol composition - Google Patents

Abstract

A soyasapogenol composition of this invention contains soyasapogenol B (ingredient A) and 3-O-D-glucuronopyranosyl soyasapogenol B (ingredient B). The weight ratio (ingredient B/ingredient A) of the 3-O-D-glucuronopyranosyl soyasapogenol B to the soyasapogenol B is in the range of 0.001 to 10. The composition can be produced by means of partial decomposition of a sugar chain residue of a soy saponin B group glycoside with acid.

Description

Soybean soap alcohol composition

The present invention relates to a soybean soap alcohol composition, a method for producing the same, and a use thereof, and more particularly to a composition for improving the in vivo absorption of soybean soap alcohol B.

Saponin is a large amount of amorphous glycoside present in soybeans, adzuki beans, olives, and the like. Saponin contains a hydrophobic portion and a hydrophilic portion, and a continuous foam occurs when it is mixed with water and vibrates, so the name is given.

Saponin is roughly classified into a steroidal saponin and a triterpenoid saponin depending on the type of glycoside. Soybean (Glycine max), especially the soybean hypocotyl, contains a large amount of soybean saponin, which is one of the triterpenoid saponins. Soy saponin, mainly consisting of soy saponin Aa, Ab, Ac, Ad, Ae, Af, Ag and Ah (hereinafter referred to as soy saponin A group glycoside) having soy saponin A, and The glycoside is composed of soybean saponin I, II, III, IV, and V (hereinafter referred to as soybean saponin B group glycoside) of soybean soap alcohol B (Non-Patent Document 1).

The efficacy of soybean saponin is well known, including: anti-obesity (Non-Patent Document 2), reduction of blood neutral fat, improvement of cholesterol value (Non-Patent Document 3), liver protection (Non-Patent Document 4), antiviral Activity (Non-Patent Document 5) and the like.

The soybean saponin having a high B group content easily suppresses an increase in blood neutral lipids compared to the soybean A saponin having a high A group content (Non-Patent Document 6). The soybean saponin A group has no effect in suppressing an increase in blood sugar level, and the soybean saponin B group can see an effect (Non-Patent Document 7). The reason why the activity of the soybean saponin B group is high is that the in vivo absorption of the group B is higher than that of the group A (Non-Patent Document 6).

The glycoside which removes the sugar chain residue by the soybean saponin is known to have an effect of promoting hyaluronic acid production of skin cells, suppressing melanin production (Patent Document 1), and promoting collagen production (Patent Documents 2 and 3). Moreover, it is a 3-O-D-glucose in which glycosidic acid remains in the glycoside. 3-O-D-Glucurono pyranosyl Soya Soap Alcohol B is known to have an antioxidant function (Patent Document 4).

If the in vivo absorption of the soybean saponin B group can be further improved, a further improvement in physiological activity can be expected. The reason for this is that the glycoside of the soybean saponin B group is converted into a glycoside, that is, soybean soap alcohol B. Examples of the method for producing soybean soap B include a high-temperature and high-pressure hydration method (Patent Document 5), a method for enzymatic decomposition (Patent Document 6), and a chemical synthesis method (Patent Document 7).

However, the glycoside and the glycoside of the soybean isoflavones have a report that the glycoside absorbability is better (Non-Patent Document 8), and there is no difference in absorbability (Non-Patent Document 9). Soy saponin did not investigate the difference in the absorption of glycosides and glycosides in the body.

[Patent Literature]

[Patent Document 1] WO2010-150612

[Patent Document 2] Japanese Patent Laid-Open Publication No. 2009-132739

[Patent Document 3] Japanese Patent Laid-Open Publication No. 2006-213649

[Patent Document 4] Japanese Patent Laid-Open Publication No. 2003-189831

Patent Document 5: WO2008/155890

[Patent Document 6] US2006/0275862

[Patent Document 7] Japanese Patent Laid-Open Publication No. 2005-137201

[Non-patent literature]

[Non-Patent Document 1] Yoshiki et al, Biosci. Biotechnol. Biochem, 62, 2291-2299, 1998

[Non-Patent Document 2] Kawano-Takahashi et al, Int. J. Obes, 10, 293-302, 1986

[Non-Patent Document 3] Basic and Clinical, 16, 135-142, 1982

[Non-Patent Document 4] Medicine and Biology, 127, 409-414, 1993

[Non-Patent Document 5] Nakashima et al, AIDS, 3, 655-658, 1989

[Non-Patent Document 6] Food and Development, 45, 54-56, 2010

[Non-Patent Document 7] Japanese Journal of Clinical Qualifications, 27, 358-366, 2006

[Non-Patent Document 8] Izumi et al, J. Nutr, 130, 1695-1699, 2000

[Non-Patent Document 9] Zubik and Meydani, Am. J. Clin. Nutr, 77, 1459-1465, 2003

As described above, there has not been much review on the improvement of the in vivo absorption of soybean saponin. Therefore, the object of the present invention is to provide a soy saponin composition having high in vivo absorption.

The inventors of the present invention conducted a careful study on improving the in vivo absorption of the soybean saponin B group, and confirmed that the soy saponin B of the soy saponin B group has higher absorbability than the soybean saponin B group. The glycoside, soy soap alcohol B has higher in vivo absorption than soybean saponin A of the glycoside of the soy saponin A group. Further, the inventors of the present invention unexpectedly found that the composition containing soyasapogenol B and 3-OD-glucuronic acid pyranyl soyasapogenol B is administered separately from the glycoside and glycoside of soybean saponin. The invention can be realized by further improving the absorption in the body.

The present invention provides a formula containing (A): Soymilk B, and (B) shown:

3-O-D-glucuronic acid pyranyl soya soap alcohol B is shown. The soybean soap alcohol composition having a weight ratio (B/A) of the component (B) to the component (A) of 0.001 to 10 is used.

In Preparation Example 1 of Patent Document 5, it is described that soybean soap alcohol B is produced by acidic decomposition of soybean saponin glycoside. However, 3-O-D-glucuronic acid pyranyl soyasapogenol B could not be detected from the obtained soybean soap alcohol powder. That is, the conventional technology does not know the soy soap alcohol composition containing both soybean soap alcohol B and 3-O-D-glucuronic acid pyranyl soya soap alcohol B. Even in the soybean material obtained by precipitating the conventional soybean food such as tofu, soy milk, soy flour, miso, soy sauce, and soy protein, and then precipitating with an organic solvent such as ethanol, methanol or butanol, there is no present invention. Composition.

When the composition of the present invention is converted to soybean soap alcohol, the component (A) and the component (B) are preferably contained in an amount of 0.05 to 100% by weight based on the composition.

The present invention provides a method for producing the above-described soybean soap alcohol composition, which comprises the above-described production method for partially decomposing a sugar chain residue of a soybean saponin B group glycoside with an acid. Since the conventional technique does not know the soy soap alcohol composition containing both the (A) component and the (B) component, the above manufacturing method is also an innovative invention.

The foregoing partial decomposition is preferably carried out using a raw material containing 5 wt% or more of the aforementioned soybean saponin B group glycoside.

The present invention further provides the above-mentioned soybean soap alcohol composition, which has the effects of suppressing an increase in blood sugar level, suppressing an increase in blood pressure, improving lipid metabolism, lowering cholesterol, improving metabolic syndrome, eating disorders, preventing obesity, anti-allergic effects, and promoting immunity. Action, adjuvant activity, anti-inflammatory action, anti-tumor activity, anti-ulcer activity, liver protection, inhibition of epithelial cell proliferation, cell hyperpermeability, cell activation, antiviral activity, anti-HIV activity, anti-mutagenic activity, inhibition A medicine for at least one of a group consisting of platelet aggregation, anti-complement activity, promotion of hyaluronic acid production of skin cells, inhibition of melanin production, promotion of collagen production, antioxidation, prevention of kidney stones, and inhibition of dementia.

The present invention also provides a food or health food containing the above-described soybean soap alcohol composition.

The present invention also provides a cosmetic material comprising the above-described soybean soap alcohol composition.

The composition of the present invention contains soyasapogenol B and 3-O-D-glucuronide pyranyl soyasapogen B, which are high in vivo absorbability, that is, a saponin composition having high bioavailability.

The composition of the present invention exhibits physiological activity based on soy soap alcohol B in the living body as long as it is administered in a small amount. Since the composition of the present invention is a component derived from the natural plant of soybean, it can be continuously administered for a long period of time as long as it is lower than the conventional amount. Therefore, the soybean saponin material composition of the present invention is extremely advantageous to the industry.

According to the method for producing a composition of the present invention, the sugar chain residue of the glycoside group of the soybean saponin B is partially decomposed by an acid, and the above composition can be easily produced. Moreover, this method is also very advantageous in terms of easy adjustment of the ratio of soyasapogenol B and 3-O-D-glucuronic acid pyranyl soyasapogenol B.

Hereinafter, embodiments of the present invention will be described in more detail. The composition of the present invention must contain the formula (A): [Chemical 3]

Soymilk B (hereinafter referred to as (A) component) is shown.

The composition of the present invention must further contain the formula (B):

3-O-D-glucuronic acid pyranyl soyasapogenol B (hereinafter referred to as (B) component). (B) Ingredients, the chemical structure of the component (A) is combined with a glycosidic acid-containing glycoside.

The weight ratio (B/A) of the component (B) to the component (A) is preferably 0.001 to 10, preferably 0.01 to 5, preferably 0.01 to 3, more preferably 0.1 to 2.5, and most preferably 0.25 to 2.5. When the value of B/A is 0.001 or less, improvement in the in vivo absorbability of soyasapogenol B cannot be expected. Conversely, even if B/A is higher than 10, the improvement in the in vivo absorption of soyasapogenol B is saturated or reduced.

The content of the component (A) and the component (B) in the composition of the present invention is usually 0.05 to 100% by weight, more preferably 0.5 to 100% by weight, and most preferably 2.5 to 100% by weight in terms of soybean soap alcohol.

The present invention also provides a method for producing the above composition.

The method is characterized in that the sugar chain residue of the soybean saponin B group glycoside, the DDMP glycoside, and the soybean saponin E group glycoside represented by the formula (5) is partially decomposed, and the specific weight ratio can be simultaneously and completely manufactured. The component (A) of the sugar chain residue and the component (B) of the glucuronic acid having the sugar chain residue remaining are removed. The soy saponin B group glycoside is extremely excellent in the stability of raw materials.

The soybean saponin B group glycoside or the soybean saponin glycoside containing the same may be precipitated from the germ, cotyledon, and whole grains of soybean by a known method such as WO2003/075939. The raw material for the acid decomposition method, which is a soy saponin B group glycoside, is usually 5% by weight or more, preferably 15 to 100% by weight, more preferably 30 to 100% by weight. The soybean saponin glycoside can be used as a commercial product, and is not particularly limited. For example, the product name saponin AZ-B (manufactured by J-OIL MILLS, INC.) is a good raw material because the soybean saponin B group glycoside is 50 to 100% by weight higher than the conventional one.

Soy saponin glycoside is dissolved in an organic solvent such as ethanol, methanol or butanol, and then sulfur is added. An acid such as acid, hydrochloric acid or nitric acid. In another method, a soy saponin glycoside is added to a reaction solvent of an acid diluted with water, ethanol, methanol, butanol or ethyl acetate to dissolve it. The soy saponin glycoside is dissolved in an organic solvent from the viewpoint of improving the yield of the composition and the recovery rate, and the composition is recovered in a short time, and then an acid is added.

The concentration of the acid is usually from 1 to 55% by weight, preferably from 3 to 25% by weight, based on the reaction solution. When the concentration of the acid is less than 1% by weight, the component B is hardly obtained, and the composition may be a very low weight. On the other hand, when it is more than 60% by weight, the yield of the A component and the B component is lowered, and the concentration of the glycoside is sometimes very low.

Acid decomposition begins by heating the acid addition solution. The acid decomposition temperature is appropriately selected depending on the type and concentration of the acid, the degree of partial decomposition (that is, B/A). The acid decomposition temperature is usually from room temperature to 150 ° C, preferably from 50 to 80 ° C. The acid decomposition time is usually from 0.5 to 23 hours, preferably from 1 to 6 hours, depending on the acid decomposition temperature.

The partial decomposition is carried out by appropriate inspection means (for example, sampling and chromatography), and sodium hydroxide, potassium hydroxide, sodium carbonate, sodium hydrogencarbonate or potassium hydrogencarbonate is used in the specific weight ratio of B/A. Wait for the base to neutralize the solution.

The solid phase of the neutralized material contains the (A) component and the (B) component, and on the other hand, contains the sugar bound to the glycoside in the aqueous phase. The solid phase containing the component (A) and the component (B) is recovered by centrifugation, filtration, natural precipitation, pressure filtration, and the like of the neutralized product. The recovered solid phase is moderately dried to obtain a dried body.

In addition to the components (A) and (B), the recovered material may also contain impurities such as glycosides, soyasapogen A, proteins, oligosaccharides, monosaccharides, amino acids, free fatty acids, and tri-hepatic acid esters. . In this case, the components (A) and (B) may be purified from the recovered product by an appropriate purification means (for example, column chromatography, solvent separation, distillation, membrane separation, precipitation, etc.). Alternatively, the recyclate is directly used as a composition of the present invention.

The composition of the present invention can also be produced by mixing the individually prepared (A) component and (B) component in a specific weight ratio.

(A) component of soyasapogenol B, which is used to remove sugar chains from soy saponin B group glycosides The method can be obtained. Specifically, the soybean saponin glycoside is subjected to an enzyme reaction (US2006/0275862), high temperature and high pressure treatment (WO2008/155890), fermentation treatment, and the like using glucosidase. Soyasapogenol B can also be obtained by chemical synthesis (JP-A-2005-137201). The above documents are inserted with reference to this specification.

(B) A method for producing a component, for example, after obtaining a composition containing the component (A) and the component (B) by the production method of the present invention, separating the component (B), and making the soybean soap according to the chemical synthesis method described in Patent Document 5 The alcohol B and the glucuronic acid derivative react, and the protective group of the produced reaction product is removed.

The composition of the present invention exhibits the efficacy of soyasapogenol B at a lower than conventional amount because of its excellent absorption in the body. Traditionally known efficacy, for example, inhibiting an increase in blood glucose level, suppressing an increase in blood pressure, improving lipid metabolism, lowering cholesterol, improving the function of metabolic syndrome, eating disorders, preventing obesity, anti-allergic effects, immune-promoting effects, adjuvant activity, and anti-antibiotics Inflammation, anti-tumor activity, anti-ulcer activity, liver protection, inhibition of epithelial cell proliferation, cell hyperpermeability, cell activation, antiviral activity, anti-HIV activity, anti-mutagenic activity, inhibition of platelet aggregation, anti-complement activity It promotes the production of hyaluronic acid in skin cells, inhibits melanin production, promotes collagen production, anti-oxidation, prevents kidney stones, and inhibits dementia. The composition of the present invention can be continuously administered for a long period of time because it is a component derived from natural plants of soybeans and can be used in a long period of time as long as it is lower than the conventional amount.

The composition of the present invention can be suitably used in the form of a product such as a pharmaceutical product, a functional food, a health food, a general processed food, or a cosmetic material. The amount of the composition of the present invention to be added to the above product varies depending on the form of the product and the amount of the product to be taken. However, it is usually 0.001 to 100% by weight, preferably 0.003 to 100% by weight.

The composition added to the composition of the present invention as a third component and having a high degree of utilization is a soybean saponin other than the components (A) and (B), a diluent, a concentration adjuster, and a solvent. Specific examples of the soybean saponin other than the components (A) and (B) include a glycoside of the soybean saponin B group, a glycoside of the soybean saponin A group, a glycoside thereof, and soybean isoflavones. The diluent and the concentration adjuster, if starch, dextrin, cellulose, etc. are used, simply disperse the composition of the present invention. Preferably. When the components (A) and (B) are coated with cyclodextrin, the absorbency of the hydrophobic component of the above components is improved. Further, the in vivo absorbability of the composition of the present invention is improved by dissolving in an emulsifier and a fat or oil.

When the composition of the present invention is used as a medicine, in addition to the components (A) and (B), a general-purpose substance can be added as an adjuvant for medicine. For example, a commonly used excipient, a dissolving agent, a binding agent, a lubricant, a vitamin, a xanthine derivative, an amino acid may be added in a range of quality and quantity which does not impair the effects of the present invention, depending on the dosage form and administration method. , pH adjuster, cooling agent, suspending agent, thickener, dissolution aid, antioxidant, coating agent, plasticizer, surfactant, water, alcohol, water-soluble polymer, sweetener, flavor Materials, sour materials, spices, colorants, etc.

The pharmaceutical form of the composition of the present invention is processed into a solid preparation such as a powder, a granule, a capsule, a pill, a lozenge, a chewable tablet, a drop, or a beverage, a solution, a suspension, An oral preparation such as an emulsion, a syrup or a dry syrup, or a form of a skin absorption agent of a liquid, a solution, an emulsion or an emulsion. Since soy soap alcohol is a powder, the form is preferably a solid preparation.

There is no particular limitation on the method of ingestion when the medicine is used. For example, there are oral, skin absorption, infusion, injection (muscle, abdominal cavity, subcutaneous or intravenous). In view of the fact that the burden on the patient is small, oral ingestion of tablets, capsules and the like is preferred.

The amount of intake used in medicine can be set as appropriate for the symptoms. In general, the daily intake of soyasapogenol B is preferably from 1 to 200 mg, more preferably from 5 to 100 mg.

When the composition of the present invention is used in a health food, a supplement, or a general processed food, in addition to the components (A) and (B), a general-purpose product may be added as an additive for a health food or the like. For example, in the form of a corresponding oral preparation, a general-purpose excipient, a dissolving agent, a binding agent, a lubricant, a vitamin, a xanthine derivative, an amine group may be added within a range that does not impair the quality and quantity of the effect of the invention. Acid, pH adjuster, cooling agent, suspending agent, thickener, dissolution aid, antioxidant, coating agent, plasticizer, surfactant, water, alcohol, water-soluble polymer, sweetener, Flavoring materials, sour materials, spices, colorants, and the like.

In order to use the composition of the present invention as a health food or a functional food, for example, It is processed into a solid preparation such as a powder, a granule, a capsule, a pill, a tablet, a chewing tablet, a drop, or an oral preparation such as a beverage, a solution, a suspension, an emulsion, a syrup, a dry syrup. Since soyasapogenol is a powder, the form is preferably a tablet.

The composition of the present invention can also be directly used as a raw material in the processing of general processed foods such as bread, rice, soup, vegetables, biscuits, and candy.

The amount of intake as a health food and a supplement can be appropriately set for the purpose of use. In general, the intake of soy soap alcohol B in one day is preferably from 1 to 200 mg, more preferably from 5 to 100 mg.

When the composition of the present invention is used as a cosmetic material, in addition to the components (A) and (B), a general purpose may be added as an adjuvant for cosmetics. For example, ethylene glycol, polyethylene glycol, propylene glycol, 1,3-butylene glycol, 1,4-butanediol, dipropylene glycol, glycerin, diglycerin, glycerin polymer, pentanediol, isoprene glycol, a polyvalent alcohol such as glucose, maltose, fructose, xylitol, sorbitol, maltotriose or erythritol; a lower alcohol such as methanol, ethanol, propanol, isopropanol, butanol or isobutanol; Higher fatty acids such as oleic acid, isostearic acid, lauric acid, myristic acid, palmitic acid, stearic acid, diced acid, undecylenic acid; olive oil, corn oil, camellia oil, Hawaiian nuclear oil, cheese Pear oil, rapeseed oil, sesame oil, castor oil, safflower oil, cottonseed oil, jojoba oil, coconut oil, palm oil, etc.; carnauba wax, canary wax, beeswax, lanolin and other waxes ; sugars such as sorbitol, mannitol, glucose, sucrose, lactose, trehalose; red algae, tri-sand, gelatin, pectin, angelica, alginate, dextrin, methylcellulose, ethylcellulose , hydroxypropyl cellulose, hydroxyethyl cellulose, carboxymethyl cellulose, carboxyvinyl polymer, polyvinyl alcohol, polyethylene Thickeners such as pyrrolidone, gum arabic, Sterculia Urens gum, milk vetch gum, damarin gum; phenoxyethanol, methyl paraben, ethyl paraben, pair Propyl hydroxybenzoate, butyl parahydroxybenzoate, paraoxybenzoic acid esters, benzoic acid, salicylic acid and its salts, sorbic acid and its salts, dehydroacetic acid and its salts a preservative such as chlorocresol or hexachlorophenol; a nonionic surfactant such as sodium lauryl sulfate or monooleic acid polyoxyethylene sorbitan, an alkyl sulfate, sodium n-dodecenesulfonate or the like. Anionic surfactant, cationic surfactant such as polyoxyethylene dodecylamine; steroidal and non-steroidal anti-inflammatory agents; vitamins such as vitamin A, vitamin D, vitamin E, vitamin F, vitamin K, etc. or Dicaprylic acid pyridoxine, vitamin B6 bis-lipoate, ascorbic acid, ascorbic acid, ascorbic acid, ascorbic acid, and other antioxidants; flavonoids, carotenoids, etc.; squalane, squalene High-grade aliphatic hydrocarbons such as liquid paraffin; neurolipids such as ceramide, cerebroside, and sphingomyelin; stearyl alcohols such as cholesterol and phytosterol; polymethyl siloxane, polymethyl Phenyl anthracene, Methyl cycloPolySiloxanes, Octamethylcyclooctanetetrasiloxane, Octamethylcyclopentasiloxane, Decamethylcyclopentasiloxane, Methyl Hydrogen Polysiloxane, etc.; for aminoammonic acid, para-aminobenzoic acid monoglyceride, methyl anthranilate, Homomenthyl-N- Ultraviolet absorbers such as methyl aminobenzoate, p-methoxy cinnamic acid octyl, ethyl-4-isocinnamate, etc.; bentonite, smectite, aluminum bentonite, stellite, magnesium bentonite, lithium swell Minerals such as stone, zinc saponite, and saponin; iron oxide, iron oxide yellow, iron oxide black, cobalt oxide, ultramarine blue, indigo, Titanium oxide, zinc oxide, etc. Inorganic pigments; Red No. 202, Yellow No. 4, Blue No. 404 such as the coloring material; perfumes; sesame oil and the like.

In order to use the composition of the present invention as a cosmetic, it is processed into a skin absorption agent such as a liquid preparation, a solution, an emulsion, an emulsion or a powder, such as a powder, a granule, a capsule, a pill, a lozenge, a chewing ingot. The solid preparation of the drop, and the oral form of the liquid such as a beverage, a solution, a suspension, an emulsion, a syrup, a dry syrup, and the like.

As a method of ingestion when the cosmetic is used, it is taken orally or absorbed by the skin. From the viewpoint of the immediate effect as a cosmetic, it is preferred to use a solution, an emulsion, an emulsion, or a milk to absorb the drug.

The amount of intake when using the cosmetic material can be appropriately set as long as the symptoms are appropriately set. In general, the intake of soy soap alcohol B on the 1st should be 0.05 to 50 mg, preferably 0.15 to 10 mg.

[Examples]

Hereinafter, the embodiments of the present invention are described, however, the present invention is not limited thereto.

[saponin analysis method]

Saponin was analyzed by a high-speed liquid liquid chromatography tandem mass spectrometry quadrupole mass spectrometer (manufactured by Nihon Waters K.K.). The chromatograms of soybean soap alcohol A, 3-O-D-glucuronic acid pyranyl soya soap alcohol B, and soybean soap alcohol B are shown in Figures 1A to 1C, respectively. Analysis conditions are as shown below.

1. Analysis conditions

Column: 2.1mm φ x150mm (product name Waters Acquity UPLC RP 18, manufactured by Nihon Waters K.K.)

Column temperature: 40 ° C

Mobile phase: methanol / water = 90/10 (v / v)

Flow rate: 0.200mL/min

Injection volume: 5μL

2. Dissolution time and mass fragment spectroscopy

Soya Soap Alcohol A: 3.6 min m/z = 441 [M+H-H2O]+

3-O-D-glucuronic acid pyranyl soya soap alcohol B: 3.0 min m/z = 635 [M+H]+

Soya soap alcohol B: 4.1 points m / z = 458 [M + H-H2O] +

[Examples 1 to 2]

1. Modulation of soy soap alcohol composition

50 g of soybean saponin glycoside (product name saponin AZ-B, manufactured by J-OIL MILLS, INC.) containing 23.2% by weight of saponin A group glycoside and 53.0% by weight of saponin B group glycoside The glass container was placed in a 5000 ml capacity and dissolved in 1600 ml of 80% ethanol. Concentrated sulfuric acid was added to the solution in such a manner that the sulfuric acid concentration became 2N. The acidic decomposition reaction of the saponin glycoside is started by maintaining the obtained reaction solution at a temperature of 70 °C.

After the start of the reaction, 150 mL of the reaction solution was taken every 1 hour to 8 hours, and neutralized with 1 N NaOH. The pellet obtained by centrifuging each neutralized material was washed with water, and then dried in a Yamato vacuum drying oven DP-301 (Yamato Scientific Co., Ltd.). Dry to obtain a powder. The composition of Example 1 was prepared by mixing 1.07 g of a powder for 2 hours of reaction and 1.43 g of a powder for 3 hours of reaction. Further, the composition of Example 2 was prepared by mixing 1.6 g of a reaction powder for 5 hours and 0.6 g of a powder for 6 hours of reaction. Further, in Comparative Example 1, a pure soybean soap alcohol B product (purity: 98%, manufactured by Tokiwa Institute of Chemical Research, B/A = 0) was prepared. The compositions of the compositions of Examples 1 and 2 and Comparative Example 1 were measured by HPLC-MS. The analytical values are shown in Table 1.

2. Evaluation of in vivo absorption of soy soap alcohol composition

Male Sprague-Dawley rats (SPRAGUE DAWLEY) (CHARLES RIVER LABORATORIES JAPAN, INC.) were divided into 3 groups of 3 to 4 animals. The composition of Examples 1 and 2 and the pure soybean saponin B of Comparative Example 1 were suspended in 0.5% sodium carboxymethylcellulose (CMC) aqueous solution, and the glycoside of (A) + (B) component was used. The method was converted into an equal amount (100 μmol/kg body weight), and a single administration was performed for the rats by feeding. Two hours after the administration, blood was collected and plasma was taken from the blood.

To the obtained plasma, the same amount of 0.2 M sodium acetate buffer (pH 5.5) was added. Next, 3000 units of β -glucuronidase (β-glucuronidase, product name H-2, Sigma-Aldrich Japan) was added, and the enzyme reaction was carried out for 12 hours at a temperature of 37 °C. After the completion of the reaction, 3 ml of a methanol:acetonitrile=1:1 mixture and an internal standard of formononetin (manufactured by Sigma-Aldrich Japan) were added to the enzyme treatment solution, followed by centrifugation, and the supernatant was collected. Further, 3 ml of a mixture of methanol:acetonitrile=1:1 was added to the residue, and the centrifugation operation was repeated twice, and the supernatant was recovered as the case may be. The obtained supernatant was dried under reduced pressure on a rotary evaporator.

The dried product was redissolved in methanol, and the blood saponin concentration (N = 3 or 4) was investigated by HPLC-MS. The concentration of saponin in the blood of each group is shown in Fig. 2. Statistical analysis was performed with a saliency check using Tukey's multiple comparison test. When the hazard ratio is <0.05, and <0.01 is significant, they are indicated by ^* and ^** , respectively.

As shown in Fig. 2, the blood concentrations of Soyasapogenol B of Examples 1 and 2 were significantly higher than Comparative Example 1 in which 3-O-D-glucuronic acid pyranyl soyasapogen B was not used.

The concentration of 3-OD-glucuronic acid pyranyl soyasapogenol B in the composition is higher than that in Example 1 although the blood concentration of soybean soap alcohol B is higher than that of the example 2 1. From this, it can be seen that the blood concentration of soybean soap alcohol B has no correlation with the concentration of 3-O-D-glucuronic acid pyranyl soya soap alcohol B.

[Examples 3 to 4]

1. Modulation of soy soap alcohol composition

The saponin AZ-B (J-OIL MILLS, INC.) was changed from the soybean saponin glycoside of Example 1 to the saponin A group with a glycoside of 31.9% by weight and the saponin B group of glycoside of 60.0% by weight. The acid partial decomposition of the saponin glycoside was carried out in the same manner as in Example 1 except for the preparation.

After the start of the reaction, after 3 hours (Example 3) and 6 hours (Example 4), 300 ml of the reaction solution was taken and neutralized with a 1 N aqueous NaOH solution. The powder obtained by centrifugation of each neutralized product was dried in a Yamato vacuum drying oven DP-301 (Yamato Scientific Co., Ltd.) to obtain a powder. The analytical values of the compositions of Examples 3 and 4 are shown in Table 2.

【Table 2】

2. Evaluation of in vivo absorption of soy soap alcohol composition

8-week-old male SD rats (CHARLES RIVER LABORATORIES JAPAN, INC.) were divided into 4 groups of 1 and the compositions of Examples 3 and 4 and Comparative Example 1 were suspended in 0.5% CMC aqueous solution. It was administered in a single dose (100 μmol/kg body weight) in terms of saponin glycoside, and was administered to rats in a single administration. Blood was collected 1, 3, 8, and 12 hours after the administration, and plasma was obtained from the samples. The pretreatment of the obtained plasma and the HPLC-MS analysis were carried out in the same manner as in Example 1, and the blood concentration of soybean soap B was investigated. In Table 3, the concentration of soyasapogenol B in the blood after 1 to 12 hours of administration and the AUC (area under curve) in the range of 0 to 12 hours are shown.

As shown in Table 3, the AUC of the index of absorbency, Examples 3 and 4 containing soyasapogenol B and 3-OD-glucuronic acid pyranyl soyasapogen B, were higher than soybean soap B alone. example 1.

[Examples 5 to 10]

1. Modulation of soy soap alcohol composition

150 g of the soybean saponin glycoside used in Example 3 was placed in a 3000 ml-capacity glass vessel and dissolved in 1500 ml of 80% ethanol. To the solution, concentrated sulfuric acid was added so that the sulfuric acid concentration of concentrated sulfuric acid became 2N. The solution was kept at a temperature of 80 ° C for 72 hours, and the saponin glycoside was subjected to acid partial decomposition while stirring slowly.

Before the start of the reaction and the reaction time shown in Table 3, 100 mm of the reaction solution was taken, and neutralized with a 1 N aqueous NaOH solution. Drying of each neutralized product was carried out with an evaporator to obtain a powder. The analytical values of the obtained compositions are shown in Table 3.

2. Evaluation of in vivo absorption of soy soap alcohol composition

Five-week-old male SD rats (CHARLES RIVER LABORATORIES JAPAN, INC.) were divided into three groups of three. After the composition shown in Table 3 was suspended in a 0.5% aqueous solution of CMC, it was converted into an equal amount (150 μmol/kg body weight) in terms of the glycoside of the components A and (B), and administered in a single dose to the mouse. . Blood was collected 2 hours after the administration and 4 hours later, and heparin sodium plasma was obtained from the blood.

The analysis of the concentration of saponin in the obtained plasma was carried out in the same manner as in Example 1. The AUC (0-4 hours) was determined from the concentration of saponin in the blood after 2 hours and 4 hours. Further, the AUC at the time of administration of the composition containing the reaction time 0 (glycoside only) was taken as 100, and the relative values of the respective examples and comparative examples shown in Table 4 were obtained and used as the absorbability index. The results are shown in Table 4.

【Table 4】

As shown in Table 4, the composition containing soybean soap alcohol B and 3-OD-glucuronyl pyranyl soya soap alcohol B (Examples 5 to 10) was compared with the comparative example containing only soybean soap alcohol B. 2, has a high blood concentration and high absorption. In addition, from the absorption index of Table 4, the range of B/A should be 0.01 to 5, preferably 0.01 to 3, more preferably 0.1 to 2.5, and most preferably 0.25 to 2.5.

[Examples 11 to 13] Modification of soybean soap alcohol composition

100 mg of soybean saponin glycoside (product name J-saponin, manufactured by J-OIL MILLS, INC.) containing a glycoside of 61.0% by weight of saponin A group and a glycoside of 30.0% by weight of saponin B group The eggplant-shaped flask of 50 ml capacity was placed, and then, 10 ml of 6N sulfuric acid water was added to dissolve the glycoside. The acidic decomposition reaction of the saponin glycoside is started by maintaining the solution at a temperature of 80 °C.

After the start of the reaction, the reaction solution was taken in 2, 4, and 8 hours in total. Neutralization was carried out using a 1 N aqueous NaOH solution. The pellet obtained by centrifuging each neutralized product was dried by a Yamato vacuum drying oven DP-301 (Yamato Scientific Co., Ltd.) to obtain a powder. end. The analytical values of the obtained compositions are shown in Table 5.

[Examples 14 to 17] Preparation of Soybean Soap Alcohol Composition

100 mg of soybean saponin glycoside (product name saponin AZ-B, manufactured by J-OIL MILLS, INC.) containing glycosides of 12.9% by weight of saponin A group and glycosides of 61.6% by weight of saponin B group The eggplant-shaped flask of 50 ml capacity was placed, and then 10 ml of 1N hydrochloric acid water was added to dissolve the glycoside. The acidic decomposition reaction of the saponin glycoside is started by maintaining the solution at a temperature of 80 °C.

After the start of the reaction, the reaction liquids of 1, 8, 16, and 24 hours were taken in full. Neutralization was carried out using a 1 N aqueous NaOH solution. The pellet obtained by centrifugation of each neutralized product was dried in a Yamato vacuum drying oven DP-301 (Yamato Scientific Co., Ltd.) to obtain a powder. The analytical values of the obtained compositions are shown in Table 6.

[Table 6]

The embodiments described above are only intended to illustrate the technical idea and the features of the present invention, and the purpose of the present invention is to enable those skilled in the art to understand the contents of the present invention and to implement the present invention. That is, the equivalent variations or modifications made by the spirit of the present invention should still be included in the scope of the present invention.

Figure 1A is a chromatogram of soy soap alcohol A (labeled A in the figure).

Figure 1B is a chromatogram of 3-O-D-glucuronic acid pyranyl soya soap alcohol B (indicated in GB).

Figure 1C is a chromatogram of soyasapogenol B (indicated in Figure B).

Fig. 2 is a graph showing the concentration of soyasapogenol B in the blood of the SD rats after administration of the composition of the present invention and the pure soybean saponin B of Comparative Example. The blood concentration of Soyasapogenol B of Examples 1 and 2 using the composition containing the component (B) was apparently higher than Comparative Example 1 using only the component (A).

Claims (7)

A soy soap alcohol composition comprising: (A): Soymilk B and (B) shown: The 3-OD-glucuronic acid pyranyl soyasapogen B is shown, wherein the weight ratio (B/A) of the component (B) to the component (A) is 0.001 to 10. The soybean soap alcohol composition according to the first aspect of the invention, which comprises the above-mentioned (A) component and (B) component in an amount of 0.05 to 100% by weight in terms of soybean soap alcohol. A method for producing a soybean soap alcohol composition according to claim 1, which comprises the step of partially decomposing a sugar chain residue of a glycoside of the soybean saponin B group with an acid. The manufacturing method as recited in claim 3, wherein A raw material containing 5% by weight or more of the aforementioned soybean saponin B group glycoside is used. A pharmaceutical composition comprising the soybean soap alcohol composition according to claim 1 which has an effect of suppressing an increase in blood sugar level, suppressing an increase in blood pressure, improving lipid metabolism, lowering cholesterol, improving metabolic syndrome, eating disorders, and preventing obesity , anti-allergic effects, immune enhancement, adjuvant activity, anti-inflammatory, anti-tumor activity, anti-ulcer activity, liver protection, inhibition of epithelial cell proliferation, cell hyperpermeability, cell activation, antiviral activity, anti-HIV activity , anti-mutagenic activity, inhibition of platelet aggregation, anti-complement activity, promotion of hyaluronic acid production of skin cells, inhibition of melanin production, promotion of collagen production, anti-oxidation, prevention of kidney stones, and inhibition of dementia At least one performance. A food or health food comprising: the soybean soap alcohol composition described in claim 1 of the patent application. A cosmetic material comprising: the soybean soap alcohol composition described in claim 1 of the patent application.