JP4828922B2 - Antiallergic agent - Google Patents

Description

  The present invention relates to an antiallergic agent and food and drink having a degranulation inhibitory effect.

  In recent years, allergic diseases such as hay fever and atopic dermatitis are increasing in a wide range of ages regardless of gender. Allergic diseases are defined as “diseases caused by an immune response to an antigen that would otherwise be harmless”. Although the pathogenesis of allergic diseases is still unclear, the balance of cytokines produced by Th1 cells and Th2 cells among helper T cells is disrupted, resulting in excessive production of immunoglobulin E (IgE) antibodies. It is inferred. That is, the IgE antibody exhibits a strong effector action on mast cells present in the vicinity of blood vessels and connective tissues, and a kind of basophils of leukocytes present in blood. Mast cells and basophils are cells rich in granules containing pharmacologically active amines such as histamine and serotonin. On these cells, there is a receptor that binds IgE antibody and strongly binds IgE antibody. When an antigen binds to an IgE antibody, intracellular granules are released to the outside of the cell. As a result, histamine, serotonin, and leukotriene are released, resulting in contraction of smooth muscle and increase in permeability of capillaries. Removal of the bound material is promoted. If this degranulation reaction is induced excessively, itchy as an allergic reaction, and symptoms such as so-called pruritus appear.

  Treatment methods for allergic diseases start by removing the causative allergen or not ingesting it, and pharmacological treatments such as antihistamines and steroids are performed depending on the symptoms and onset mechanism. However, pharmacotherapy is not effective depending on constitution, and there is a risk of side effects caused by taking for a long time, which is a problem. A safe antiallergic agent that is effective against such allergic diseases and has no side effects is desired.

The α-D-glucopyranosylglycerols according to the present invention are known substances, and have low browning, low Maillard reactivity, heat stability, non-cariogenicity, indigestibility, and high moisture retention. However, it has been reported that it can be used for foods, chemical products, and pharmaceuticals (see Patent Document 1 and Patent Document 2). Further, α-D-glucopyranosylglycerol is a vascular endothelial cell growth promoting factor production promoting action (see Patent Document 3), a blood glucose level increase inhibiting action (see Patent Document 4), an antibacterial action (see Patent Document 5), Cell activation (see Patent Document 6), dermal matrix production promoting action (see Patent Document 7), neutral fat accumulation inhibitory action (see Patent Document 8), melanin production inhibitory action (see Patent Document 9), skin irritation reducing action (Refer patent document 10) The effect | action (patent document 11) which suppresses the feeling of tightness and a squeak after skin washing | cleaning is reported. However, nothing has been known so far regarding the antiallergic action of α-D-glucopyranosylglycerols.
Japanese Patent No. 3569432 JP 2004-229668 A JP 2004-331575 A JP 2004-331576 A JP 2004-331577 A JP 2004-331578 A JP 2004-331579 A JP 2004-331580 A JP 2004-331581 A JP 2004-331582 A JP 2004-331583 A

  The present invention relates to a safe antiallergic agent having no side effects, and a food and drink, for alleviating allergic symptoms of people suffering from allergic diseases that interfere with life and improving quality of life (QOL). The purpose is to provide.

  The inventors of the present invention have been studying the functionality of α-D-glucopyranosylglycerols contained in sake, miso, and miso, traditional Japanese foods that have been eaten for a long time. The inventors have found that nosylglycerols have an excellent antiallergic action, and have further studied and completed the present invention.

  The present invention relates to an antiallergic agent containing α-D-glucopyranosylglycerols as an active ingredient, and a food or drink containing the antiallergic agent and exhibiting an excellent antiallergic effect.

の（２Ｒ）−１−Ｏ−α−Ｄ−グルコピラノシルグリセロール、（２Ｓ）−１−Ｏ−α−Ｄ−グルコピラノシルグリセロール、および２−Ｏ−α−Ｄ−グルコピラノシルグリセロールの少なくとも１つを含むα−Ｄ−グルコピラノシルグリセロール類を有効成分とする抗アレルギー剤、
［２］ 脱顆粒抑制剤である前記［１］に記載の抗アレルギー剤、
［３］ 皮膚外用剤である前記［１］または［２］に記載の抗アレルギー剤、
［４］ 内服剤である前記［１］または［２］に記載の抗アレルギー剤、
［５］ 前記［１］または［２］に記載の抗アレルギー剤が配合されていることを特徴とする飲食品、
［６］ 前記［１］または［２］に記載の抗アレルギー剤を含むことを特徴とする、抗アレルギー作用のために用いられるものである旨の表示を付した飲食品、
［７］ 前記［１］または［２］に記載の抗アレルギー剤を含むことを特徴とする香粧品、および
［８］ 前記［１］または［２］に記載の抗アレルギー剤を含むことを特徴とする、抗アレルギー作用のために用いられるものである旨の表示を付した香粧品、
に関する。 That is, the present invention
[1] Formula 1, Formula 2 and Formula 3

(2R) -1-O-α-D-glucopyranosylglycerol, (2S) -1-O-α-D-glucopyranosylglycerol, and 2-O-α-D-glucopyranosyl An antiallergic agent comprising α-D-glucopyranosylglycerols containing at least one of glycerol as an active ingredient,
[2] The antiallergic agent according to [1], which is a degranulation inhibitor,
[3] The antiallergic agent according to [1] or [2], which is an external preparation for skin,
[4] The antiallergic agent according to [1] or [2], which is an internal medicine,
[5] A food or drink comprising the antiallergic agent according to [1] or [2],
[6] A food or drink with a label indicating that it is used for antiallergic action, comprising the antiallergic agent according to [1] or [2],
[7] A cosmetic comprising the antiallergic agent according to [1] or [2], and [8] comprising the antiallergic agent according to [1] or [2]. Cosmetics with an indication that they are used for antiallergic action,
About.

  The antiallergic agent of the present invention is useful as an excellent antiallergic agent having an antiallergic effect, particularly a degranulation inhibitor having a degranulation inhibitory effect, which is simple and completely safe. By continuously taking or applying the antiallergic agent of the present invention, it is possible to safely alleviate allergic symptoms and improve QOL of people suffering from allergic diseases that interfere with life without causing side effects. .

  The α-D-glucopyranosylglycerols used in the present invention include (2R) -1-O-α-D-glucopyranosylglycerol (formula 1), (2S) -1-O-α- Three components of D-glucopyranosylglycerol (formula 2) and 2-O-α-D-glucopyranosylglycerol (formula 3) are known, and one or a mixture of two or more of these It can be used as -D-glucopyranosylglycerols.

The α-D-glucopyranosylglycerols used in the present invention may be produced according to a conventional method, for example, using known means such as extraction or purification from sake, miso, or miso. Moreover, you may manufacture by the method using the enzyme reaction as described in patent document 1. FIG.
In the present invention, the α-D-glucopyranosylglycerols are (2R) -1-O-α-D-glucopyranosylglycerol (formula 1), (2S) -1-O. A mixture containing three components of -α-D-glucopyranosylglycerol (formula 2) and 2-O-α-D-glucopyranosylglycerol (formula 3) is preferred.
One embodiment of the present invention is an antiallergic agent containing the α-glucopyranosylglycerols as an active ingredient. This medicine can be widely used for the treatment and prevention of allergic diseases.
The allergic disease is not particularly limited, and examples thereof include allergic gastritis, allergic conjunctivitis, allergic contact dermatitis, allergic constitution, allergic rhinitis, bronchial asthma, hay fever and urticaria.

  As the medicament according to the present invention, the α-D-glucopyranosylglycerols may be used as they are, but generally a pharmaceutical preparation comprising the active ingredient and one or more preparation additives. Preferably it has a form. The pharmaceutical preparation is preferably an internal preparation or an external preparation for skin. Examples of the dosage form include tablets, pills, capsules, powders, granules, suppositories, injections, pastes, ointments, creams, gels. Agents, gel creams, lotions, emulsions, suspensions, poultices, plasters, liniments, aerosols, syrups, oral preparations, eye drops, nasal drops and the like.

The pharmaceutical preparation as described above can be produced according to a method well known or commonly used in the field of pharmaceutics.
In the pharmaceutical according to the present invention, for production of solid preparations such as tablets, pills, capsules, powders or granules, for example, excipients, binders, disintegrants, surfactants or lubricants are prepared. It can be used as an additive. Examples of the excipient include sugars such as lactose, sucrose or glucose, starches such as starch, and crystalline cellulose. Examples of the binder include sugars or sugar alcohols such as glucose and maltitol, polysaccharides such as starch, natural polymers such as gelatin, cellulose derivatives such as methylcellulose or carboxymethylcellulose, and synthetic polymer compounds such as polyvinylpyrrolidone. Etc. Examples of the disintegrant include starch, sodium alginate, corn starch, hydroxypropyl starch, polyvinyl pyrrolidone, and croscarmellose sodium. Examples of the lubricant include stearate, talc, boric acid powder, polyethylene glycol and the like. Examples of the surfactant include fatty acid esters.

  When the medicament according to the present invention has a suppository dosage form, the above-mentioned α-D-glucopyranosylglycerols and optionally, for example, topical, lipophilic base, water-soluble base or emulsion base By containing an anesthetic, local astringent, surfactant, preservative, excipient, absorption enhancer and the like, the medicament according to the present invention can be produced.

  When the medicament according to the present invention has a dosage form of an injection, the above α-D-glucopyranosylglycerol and optionally a solubilizing agent, a buffering agent or a solvent are added to a solvent such as a water-soluble solvent or a water-insoluble solvent. The pharmaceutical concerning this invention can be manufactured by containing additives for preparations, such as a soothing agent. The injection of the present invention is preferably sterilized and isotonic with blood, and may contain sodium chloride, glucose, glycerin or the like in order to be isotonic with blood. Furthermore, if desired, the pharmaceutical preparation may contain coloring agents, preservatives, flavoring agents, flavoring agents, sweetening agents and the like.

  When the medicament according to the present invention has an ointment dosage form, for example, an oily base such as petrolatum, liquid paraffin, silicone or vegetable oil; for example, an emulsion base such as hydrophilic petrolatum or purified lanolin; To a substrate such as a water-soluble substrate such as the above α-D-glucopyranosylglycerols and, if desired, emulsifiers such as anionic or nonionic surfactants or paraoxybenzoates The pharmaceutical concerning this invention can be manufactured by containing additives for preparations, such as a preservative.

  When the medicament according to the present invention has a gel dosage form, a gelling agent (eg, carboxyvinyl polymer, hydroxyethylcellulose, hydroxypropylcellulose, methylcellulose, ethylcellulose, carboxymethylcellulose, or propylene glycol alginate) is added to water. In addition to the above-mentioned α-D-glucopyranosyl glycerols and optionally, for example, a pharmaceutical additive such as a lower alcohol, a neutralizing agent, a surfactant or an absorption enhancer in the base material obtained The pharmaceutical concerning this invention can be manufactured.

When the medicament according to the present invention has a cream dosage form, for example, higher fatty acid esters (eg, myristic acid ester, palmitic acid ester, diethyl sebacate, hexyl laurate, cetyl isooctanoate, etc.), lower alcohols (eg: Ethanol, isopropanol, etc.), carbohydrates (eg, liquid paraffin, squalane, etc.), polyhydric alcohols (eg, propylene glycol, 1,3-butylene glycol, etc.) or higher alcohols (eg, 2-hexyldecanol, cetanol, 2-octyldodeca) By adding the above-mentioned α-D-glucopyranosylglycerols and, if desired, pharmaceutical additives such as emulsifiers, preservatives, absorption promoters or anti-rash agents, to a base material including a The pharmaceutical concerning this invention can be manufactured.
Further, in order to obtain a gel cream having intermediate properties between the cream and the gel, a gelling agent and a neutralizing agent may be added to the cream.

When the medicament according to the present invention has a dosage form of a solution for external use, the above-mentioned α-D-glucopyranosylglycerols and optionally, for example, a buffer, a stabilizer, an antiseptic, a pH adjuster, a solvent The pharmaceutical composition according to the present invention can be produced by adding a formulation additive such as a solubilizing agent, a flavoring agent, a gelling agent, a corrigent or a cooling agent. Examples of the solvent include glycerin, propylene glycol, ethanol, isopropanol, butylene glycol, water, sorbitol, mannitol, xylitol, glucose, epsilon aminocaproic acid, glycine, glutamate, sodium hyaluronate, polyethylene glycols, carboxyvinyl polymers, Examples include higher alcohols such as cetanol and stearyl alcohol, fatty acid esters such as medium chain fatty acid esters and isopropyl myristate, higher fatty acids such as stearic acid, squalane, liquid paraffin, white petrolatum, and purified lanolin.
Here, the liquid preparation for external use includes liquid preparations for external use such as washing, injection, poultice, inhalation, spraying, enema, application, medicine bath, wiping, disinfection, eye drop, eye wash, ear drop or nose drop.

An aerosol preparation can be produced by using the external liquid preparation of the present invention together with a normal propellant. Examples of the propellant include dimethyl ether, liquefied petroleum gas, N ₂ gas, nitrous oxide gas, CO ₂ gas, and alternative chlorofluorocarbon gas that are usually used for aerosols. Compressed air can also be used without using a propellant. Moreover, you may use these mixtures.

  The route of administration, dose and frequency of administration of the medicament according to the present invention are not particularly limited, and are appropriately selected according to various conditions such as the type of pathological condition to be treated, the age and weight of the patient, symptoms, and the severity of the disease. Is possible. More specifically, the therapeutic dose as an antiallergic agent is about 50 to 10,000 mg / kg, preferably about 100 to 5000 mg / kg per day for an adult when administered orally. When the medicament according to the present invention is an external preparation intended for antiallergy, the active ingredient is preferably adjusted to about 0.5 to 80% by weight, preferably about 1 to 50% by weight.

  Moreover, the said antiallergic agent can be used for food-drinks. Thus, foods and drinks in which the antiallergic agent is used are also one aspect of the present invention. Examples of such foods and drinks include foods and drinks with an indication that they are used for antiallergic action, including the above-mentioned antiallergic agents. (For example, tablets, granules, powders, capsules, etc.), sols, gels, and liquids may be used.

The food / beverage products of this invention are manufactured as food / beverage products by mixing suitably the said alpha-D-glucopyranosyl glycerols with a foodstuff raw material, a foodstuff raw material, and also a food additive as needed according to a conventional method. . Further, according to a conventional method using the α-D-glucopyranosylglycerols, for example, an oil-and-fat composition mainly containing the α-D-glucopyranosylglycerols, an O / W emulsion, W / An α-D-glucopyranosylglycerol-containing food / beverage additive such as an O-type emulsion or a solubilized liquid is produced, and this α-D-glucopyranosylglycerol-containing food / beverage additive is used as a food / beverage product. You may add and manufacture the food-drinks of this invention.
The said food-drinks can take all food forms, such as a solid food, a cream-like or jam-like semi-fluid food, a gel-like food, and a drink. Examples of the food and drink include soft drinks, drops, candy, chewing gum, chocolate, gummi, yogurt, ice cream, pudding, jelly confectionery, cookies, margarine, shortening, mayonnaise, dressing and the like. The above food and drink are useful as health foods or foods for specified health purposes intended to be used for antiallergic action.

  Examples of the additive, food material, food raw material or food additive used in the preparation of the preparations and foods and beverages include excipients (lactose, dextrin, corn starch, crystalline cellulose, etc.), lubricants (magnesium stearate, Sugar fatty acid esters, glycerin fatty acid esters, etc.), disintegrants (carboxymethylcellulose calcium, anhydrous calcium hydrogen phosphate, calcium carbonate, etc.), binders (starch glue solution, hydroxypropyl cellulose solution, gum arabic solution, etc.), solubilizing agents ( Gum arabic, polysorbate 80, etc.), sweeteners (sugar, fructose / dextrose sugar, honey, aspartame, etc.), coloring agents (β-carotene, food tar pigment, riboflavin, etc.), preservatives (sorbic acid, methyl paraoxybenzoate) , Sodium sulfite, etc.), thickener (Argi) Acid sodium, sodium carboxymethylcellulose, sodium polyacrylate, etc.), antioxidants (BHT, BHA, ascorbic acid, tocopherol, etc.), flavors (mint, strawberry flavor, etc.), acidulants (citric acid, lactic acid, DL-malic acid) Etc.), seasonings (DL-alanine, sodium 5'-inosinate, sodium L-glutamate, etc.), emulsifiers (glycerin fatty acid ester, sucrose fatty acid ester, etc.), pH adjusters (citric acid, trisodium citrate, etc.) Vitamins, minerals, amino acids and the like can be used.

  In the case of the said food / beverage products, content of (alpha) -D-glucopyranosyl glycerol (converted into purity 100 mass%) is about 0.5-90 mass% normally with respect to the total mass of food / beverage products, Preferably it is about 1-80 mass%.

The cosmetics referred to in the present invention include products called cosmetics and fragrance products. When these products are provided, they are lotions, cosmetic creams, emulsions, foundations, lipsticks, hair styling agents, hair tonics, hair restorers, shampoos. Appropriate amounts of α-D-glucopyranosylglycerols for non-oral cosmetics such as rinsing, bathing agents, and oral cosmetics such as toothpastes, mouthwashes, mouthwashes, and oral fragrances Thus, a cosmetic product can be prepared.
These cosmetics include, for example, oils and fats such as vegetable oils, waxes such as lanolin and beeswax, hydrocarbons, fatty acids, higher alcohols, esters, various surfactants, pigments, fragrances, vitamins, plants and Obtained according to conventional methods by appropriately blending additives used as usual cosmetic ingredients such as animal extract ingredients, ultraviolet absorbers, antioxidants, antiseptic / bactericides, and moisturizers (eg urea, hyaluronic acid) be able to.

  In the case of the cosmetic product, the content of α-D-glucopyranosylglycerols (converted to a purity of 100% by mass) is usually about 0.05 to 70% by mass relative to the total mass of the cosmetic product, Preferably it is about 0.1-50 mass%.

  Furthermore, although an Example demonstrates this invention in detail, this invention is not limited to these Examples. First, production examples of the α-D-glucopyranosylglycerols of the present invention are shown.

[Production Example 1]
Releases 1 μmol of p-nitrophenol per minute from 5 mM p-nitrophenyl-α-glucoside to 1000 ml of an aqueous solution of 5% maltose and 35% glycerol at 1U at pH 5.0 and 37 ° C. Α-glucosidase (transglucosidase L-Amano, manufactured by Amano Enzyme), an enzyme derived from Aspergillus niger, is reacted for 24 hours under the conditions of 40 ° C. and reaction pH 5.0, and then maltose every 24 hours. Was continuously added 10 times and allowed to react. The obtained reaction solution was purified by activated carbon chromatography to obtain 140 g of α-D-glucopyranosylglycerols. When the obtained α-D-glucopyranosylglycerols were confirmed by GC-MS analysis, (2R) -1-O-α-D-glucopyranosylglycerol, (2S) -1-O-α- It was a three-component mixture of D-glucopyranosylglycerol and 2-O-α-D-glucopyranosylglycerol.

[Production Example 2]
Shim-pack with 1,000 ml of sake
Fractionation with an SCR-101 (N) (7.9 × 300 mm) column (column temperature; 50 ° C., eluent; water, flow rate; 0.6 ml / min), and 3 g of α-D-glucopyranosylglycerols Got. When the obtained α-D-glucopyranosylglycerols were confirmed by GC-MS analysis, (2R) -1-O-α-D-glucopyranosylglycerol, (2S) -1-O-α- It was a three-component mixture of D-glucopyranosylglycerol and 2-O-α-D-glucopyranosylglycerol.

[Production Example 3]
10 ml of 2% periodic acid was added to 1 ml of 4% maltitol aqueous solution and reacted at room temperature for 4 minutes. After completion of the reaction, barium chloride was added, and the resulting barium periodate precipitate was filtered and removed. Further, after desalting with an ion exchange column, reduction with sodium borohydride was carried out, and fractional purification was performed by activated carbon chromatography and HPLC to obtain 2-O-α-D-glucopyranosylglycerol.

[Pharmacological test]
The results of examining the antiallergic action of α-D-glucopyranosylglycerols obtained in the above production examples will be described. In allergic symptoms, when mast cells and basophils release histamine, serotonin, etc., β-hexosaminidase is released at the same time. Therefore, α-D-glucopyranosylglycerols prepared in Production Example 1 are used. Using as a sample, a β-hexosaminidase release inhibition test from basophils was performed.

Rat basophil leukemia cells RBL-2H3 were seeded on a 24 well culture plate at 2 × 10 ⁵ cells / well, sensitized with an anti-DNP-IgE antibody (0.5 μg / ml), and cultured at 37 ° C. for 18 hours. Next, after washing twice with PBS (−) buffer, Release mixture (116.9 mM NaCl, 5.4 mM KCl, 0.8 mM MgSO ₄ , 5) containing α-D-glucopyranosylglycerols at a predetermined concentration. .6 mM glucose, 25 mM HEPES, 2.0 mM CaCl ₂ , 1 mg / ml BSA), or Release mixture alone was added and incubated at 37 ° C. for 10 minutes. Next, an antigen (DNP-BSA 267 ng / ml) was added thereto and incubated at 37 ° C. for 30 minutes, and then 100 μl from each well and then Triton X-100 was added to lyse the cells, and 100 μl was collected. To this, 40 μl of 50 mM citrate buffer (pH 4.5) containing p-nitro-N-acetyl β-glucosamide, which is a substrate of β-hexosaminidase, was added and reacted at 37 ° C. for 30 minutes. After completion of the reaction, the reaction was stopped with 0.1 M carbonate buffer (pH 10.0), and the absorbance at 405 nm was measured with a microplate reader to measure the intracellular and extracellular β-hexosaminidase activity. The results are shown in FIG.

  As shown in FIG. 1, α-D-glucopyranosylglycerols have an inhibitory effect on β-hexosaminidase release, and the inventor is the first to demonstrate the antiallergic effect of α-D-glucopyranosylglycerols. Came to find.

  The α-D-glucopyranosyl glycerols obtained in the above production examples are appropriately used depending on the use, and the α-D-glucopyranosyl glycerols are blended with anti-allergic agents (external preparations). , Internal use) and examples of food and drink products are described below. In addition, the following prescription is not limited to the following Examples, The manufacturing method followed the conventional method.

[Example 1: External lotion]

(Manufacturing method for external lotion)
In accordance with the formulation shown in Table 1 above, ethanol, hydroxyethyl cellulose, methyl paraoxybenzoate, α-D-glucopyranosylglycerols and purified water were mixed to produce an external lotion.

[Example 2: External emulsion]

  According to the formulation shown in Table 2 above, stearic acid, cetanol, petrolatum, liquid paraffin, polyoxyethylene monooleate, tocopherol acetate, glycerin, methyl paraoxybenzoate, triethanolamine, α-D-glucopyranosylglycerols And purified water were mixed to produce an external emulsion.

[Composition Example 3: Cream for External Use]

According to the formulation shown in Table 3 above, beeswax, cetanol, reduced lanolin, squalene,
Mix glyceryl fatty acid ester, lipophilic glyceryl monostearate, polyoxyethylene (20E.O) sorbitan monolaurate, propylene glycol, methyl paraoxybenzoate, α-D-glucopyranosylglycerols, and purified water. A cream for external use was produced.

[Formulation Example 4: Gel for External Use]

  According to the formulation shown in Table 4 above, dipropylene glycol, carboxyvinyl polymer, potassium hydroxide, methyl paraoxybenzoate, α-D-glucopyranosylglycerols and purified water were mixed to produce a gel for external use.

[Formulation example 5: bath preparation]

  In accordance with the formulation shown in Table 5 above, sodium bicarbonate, sodium sulfate, α-D-glucopyranosylglycerols and perfume were mixed to produce a bath preparation.

[Formulation Example 6: Shampoo]

  Purified water, sodium lauryl sulfate, sodium polyoxyethylene lauryl ether sulfate, coconut oil fatty acid amidopropyl betaine, coconut oil fatty acid diethanolamide, cationized cellulose, ethylene glycol distearate, glycerin, paraoxybenzoic acid according to the formulation shown in Table 6 above Methyl, citric acid, fragrance, and α-D-glucopyranosylglycerols were mixed to obtain a shampoo.

[Formulation Example 7: Beverage]

  In accordance with the formulation shown in Table 7, α-D-glucopyranosylglycerols, fruit juice, citric acid, vitamin C, fragrance and purified water were mixed to obtain a beverage.

[Formulation Example 8: Candy]

  According to the prescription shown in Table 8 above, sucrose, starch syrup, α-D-glucopyranosylglycerols and fragrance were mixed to produce a candy.

  ADVANTAGE OF THE INVENTION By this invention, the antiallergic agent excellent in the antiallergic action which uses (alpha) -D-glucopyranosyl glycerols as an active ingredient can be provided.

It is a figure which shows the inhibitory effect of (beta) -hexosaminidase release | release from a basophil by (alpha) -D-glucopyranosyl glycerols. The control on the horizontal axis is the result of the addition test of α-D-glucopyranosylglycerols.

Claims (6)

Formula 1, Formula 2 and Formula 3

(2R) -1-O-α-D-glucopyranosylglycerol, (2S) -1-O-α-D-glucopyranosylglycerol, and 2-O-α-D-glucopyranosyl An antiallergic medicine comprising α-D-glucopyranosylglycerols containing at least one glycerol as an active ingredient. The medicament of claim 1 antiallergic is degranulation curbing. The medicament of claim 1 or 2 which is for outside the skin. The medicament of claim 1 or 2 which is for oral. Formula 1, Formula 2 and Formula 3

(2R) -1-O-α-D-glucopyranosylglycerol, (2S) -1-O-α-D-glucopyranosylglycerol, and 2-O-α-D-glucopyranosyl An antiallergic cosmetic comprising, as an active ingredient, α-D-glucopyranosylglycerols containing at least one of glycerol. 6. The cosmetic product according to claim 5, wherein the antiallergy is degranulation suppression.

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