WO2023145792A1 - 組成物、経口組成物の微生物増殖抑制方法及びケルセチン又はその配糖体の微生物増殖抑制作用増強剤 - Google Patents
組成物、経口組成物の微生物増殖抑制方法及びケルセチン又はその配糖体の微生物増殖抑制作用増強剤 Download PDFInfo
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- WO2023145792A1 WO2023145792A1 PCT/JP2023/002341 JP2023002341W WO2023145792A1 WO 2023145792 A1 WO2023145792 A1 WO 2023145792A1 JP 2023002341 W JP2023002341 W JP 2023002341W WO 2023145792 A1 WO2023145792 A1 WO 2023145792A1
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- Prior art keywords
- quercetin
- ergothioneine
- composition
- glycoside
- salt
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- DUBCCGAQYVUYEU-ZUGPOPFOSA-N miquelianin Chemical compound O1[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1OC1=C(C=2C=C(O)C(O)=CC=2)OC2=CC(O)=CC(O)=C2C1=O DUBCCGAQYVUYEU-ZUGPOPFOSA-N 0.000 description 1
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- LOJXBHNAFUDMIQ-UHFFFAOYSA-N quercetin-3-alpha-glucuronide Natural products OC1OC(C(O)C(O)C1O)C(=O)Oc1c(oc2cc(O)cc(O)c2c1=O)-c1ccc(O)c(O)c1 LOJXBHNAFUDMIQ-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
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Definitions
- the present invention relates to a composition containing L-ergothioneine or a salt thereof and quercetin or a glycoside thereof.
- the present invention also relates to methods for inhibiting microbial growth of oral compositions.
- the present invention further relates to quercetin or a glycoside thereof that enhances the inhibitory action of microorganisms.
- Quercetin is a kind of flavonoid, and is contained in plants such as onions as it is or as a glycoside.
- Non-Patent Document 1 describes that quercetin inhibited the growth of Escherichia coli and Staphylococcus aureus.
- Ergothioneine is a kind of sulfur-containing amino acid, and naturally exists in the L form.
- L-ergothioneine is known to have useful physiological activities such as antioxidant activity.
- Patent Document 1 when ergothioneine derived from Pleurotus cornucopia is allowed to act on immortalized human keratinocyte cells (HaCaT cells), human ⁇ -defensin-1 (hBD-1) and human ⁇ -defensin-3 (hBD-3) It has been described that the expression level of the mRNA of is increased.
- An object of the present invention is to provide a technique for effectively suppressing the growth of microorganisms in an oral composition or the like.
- L-ergothioneine enhances the microbial growth inhibitory action of quercetin or its glycosides.
- L-ergothioneine or a salt thereof and quercetin or a glycoside thereof in combination it is possible to effectively suppress the growth of microorganisms.
- the present invention relates to the following compositions, methods for inhibiting microbial growth of oral compositions, agents for enhancing microbial growth inhibition of quercetin or its glycosides, and the like.
- [9] Weight ratio of the content of (A) L-ergothioneine or a salt thereof (converted to L-ergothioneine) to the content of (B) quercetin or its glycoside (converted to isoquercitrin) in the oral composition ( (A) in terms of L-ergothioneine/(B) in terms of isoquercitrin) is 0.01 to 1.2, and (A) L-ergothioneine or a salt thereof and (B) quercetin or a glycoside thereof.
- FIG. 1 is a graph showing the sterilization effect of L-ergothioneine (test sample 1), isoquercitrin (test sample 2), and a combination of L-ergothioneine and isoquercitrin (test samples 3-4).
- composition contains (A) L-ergothioneine or a salt thereof and (B) quercetin or a glycoside thereof.
- Quercetin or its glycoside has a microbial growth inhibitory action (antibacterial action).
- a combination of L-ergothioneine or a salt thereof and quercetin or its glycoside can enhance the microbial growth inhibitory action of quercetin or its glycoside. Therefore, by using L-ergothioneine or its salt in combination with quercetin or its glycoside, it is possible to effectively suppress the growth of microorganisms.
- L-ergothioneine is a kind of amino acid.
- the salt of L-ergothioneine is not particularly limited as long as it is a pharmacologically acceptable salt or a salt acceptable for food and drink, and may be either an acid salt or a basic salt.
- Acid salts include, for example, inorganic salts such as hydrochlorides, sulfates, nitrates, phosphates; Examples include organic acid salts such as acid salts and propionate salts.
- Examples of basic salts include alkali metal salts such as sodium salts and potassium salts; alkaline earth metal salts such as calcium salts and magnesium salts; As L-ergothioneine or a salt thereof, preferably L-ergothioneine is used.
- L-ergothioneine or a salt thereof may be a chemically synthesized product, or may be extracted and purified from natural products.
- a large amount of L-ergothioneine is contained in Golden/Yellow Oyster Mushroom (scientific name: Pleurotus cornucopiae var. citrinopileatus), which is a mushroom belonging to the genus Pleurotus of the Oysteraceae family.
- L-ergothioneine is found in white button mushrooms, crimini mushrooms, portabella mushrooms and other mushrooms (scientific name: Agaricus bisporus), gray oyster mushrooms (scientific name: Pleurotus ostreatus), shiitake mushrooms (scientific name: Lentinula edodes), maitake mushrooms (Scientific name: Grifola frondosa), Reishi (Scientific name: Ganoderma lucidum), Hericium erinaceus (Scientific name: Hericium erinaceus), Willow matsutake (Scientific name: Agrocybeaegerita), Chanterelle (Scientific name: Cantharellus cibarius), Porcini Name: Boletus edulis), morels ( It is also contained in mushrooms such as Morchella esculenta (scientific name: Morchella esculenta).
- L-ergothioneine When L-ergothioneine is obtained from a natural product, it is preferably extracted from Pleurotus cornucopia. L-ergothioneine or a salt thereof can also be produced by microbial fermentation. An extract containing L-ergothioneine or a salt thereof produced by microbial fermentation or a product purified therefrom may also be used. Extraction and purification from natural products and the like can be carried out by known methods. L-ergothioneine or a salt thereof may be isolated.
- the content of L-ergothioneine or a salt thereof in the composition is not particularly limited. It may be 50% by weight or less, 10% by weight or less, preferably 0.1% by weight or less, and more preferably 0.01% by weight or less. In one aspect, the content of L-ergothioneine or a salt thereof in the composition may be 0.00001 to 50% by weight, preferably 0.00001 to 10% by weight, in terms of L-ergothioneine. is 0.00001 to 0.1 wt%, more preferably 0.0001 to 0.01 wt%.
- the content of L-ergothioneine or a salt thereof can be measured by a high performance liquid chromatography (HPLC) method.
- the amount in terms of L-ergothioneine or a similar expression means the amount of L-ergothioneine or a salt thereof as L-ergothioneine.
- L-ergothioneine it means the amount
- the salt of L-ergothioneine it means the value obtained by multiplying the number of moles of the salt by the molecular weight of L-ergothioneine.
- quercetin means quercetin, which is a compound belonging to flavonol, which is a kind of polyphenol.
- a quercetin glycoside means a quercetin glycoside, specifically a series of quercetin glycosides in which one or more sugars are glycoside-bonded to the hydroxyl group at the 3-position and/or the hydroxyl group at the 4'-position of quercetin. It is a general term for compounds.
- the quercetin glycoside may be one compound, or two or more compounds.
- Sugars (monosaccharides) bound to quercetin include glucose, rhamnose, galactose, glucuronic acid and the like, preferably glucose and rhamnose.
- the sugar attached to quercetin may be modified (eg malonylated).
- the quercetin glycoside is preferably a compound in which one or more sugars are glycoside-bonded to the hydroxyl group at the 3-position of quercetin.
- a quercetin glycoside in which one or more sugars are glycoside-bonded to the hydroxyl group at the 3-position of quercetin is a compound represented by the following general formula.
- (X)n in the general formula below represents a sugar chain.
- X represents a sugar (monosaccharide) and n is an integer of 1 or more.
- the sugar constituting the sugar chain represented by X glycoside-bonded to quercetin is, for example, glucose, rhamnose, galactose, glucuronic acid, etc., preferably glucose or rhamnose.
- n is not particularly limited as long as it is 1 or more, but is preferably 1-16, more preferably 1-8.
- the X moiety may consist of one type of sugar, or may consist of multiple types of sugars.
- (X)n may be a sugar chain composed of one type of sugar or a sugar chain composed of multiple types of sugars.
- the quercetin glycosides in the present invention include those obtained by treating existing quercetin glycosides with an enzyme or the like to transglycosylate.
- the quercetin glycosides referred to in the present invention include rutin (quercetin 3-rutinoside), enzyme-treated rutin (enzymatically treated rutin), quercitrin (quercetin-3-O-rhamnoside), isoquercitrin ( quercetin 3-glucoside), quercetin 3,4'-diglucoside, quercetin 4'-glucoside, quercetin 3-(6-malonylglucoside), hyperoside (quercetin 3-galactoside), quercetin-3-O-glucuronide, and the like.
- Enzyme-treated rutin is a quercetin glycoside in which a sugar chain is further bound to the glucoside portion of isoquercitrin.
- a preferred example of enzyme-treated rutin is isoquercitrin, which is obtained by treating rutin with enzymes to remove the rhamnose sugar chain portion, and then treating isoquercitrin with a glycosyltransferase. and mixtures thereof as main ingredients.
- quercetin or its glycoside is preferably a quercetin glycoside, more preferably a quercetin glycoside in which one or more sugars are glycoside-bonded to the hydroxyl group at the 3-position of quercetin, isoquercitrin, rutin, enzyme treatment At least one selected from the group consisting of rutin and quercitrin is more preferred, and isoquercitrin and enzyme-treated rutin are even more preferred.
- quercetin glycosides compounds in which 1 to 8 glucoses are glycoside-bonded to the hydroxyl group at the 3-position of quercetin (eg, isoquercitrin, glycosides in which 1 to 7 glucoses are bonded to isoquercitrin) are particularly preferred. Preferred, isoquercitrin being most preferred.
- quercetin or its glycoside there are no particular restrictions on the origin or production method for obtaining quercetin or its glycoside.
- buckwheat, Japanese pagoda, capers, apples, tea, onions, grapes, broccoli, mulukhiya, raspberries, cowberries, cranberries, opuntia, leafy vegetables, and citrus fruits are known as plants containing a large amount of quercetin or its glycosides. Quercetin or its glycoside can be obtained from these plants.
- the quercetin or its glycosides used in the present invention are obtained by extracting extracts derived from natural products such as the above-mentioned plants and performing operations such as concentration and purification to obtain quercetin or its glycosides, as long as the effects of the present invention can be achieved.
- Enriched products such as concentrates or purified extracts containing quercetin or its glycosides can be used.
- a known method can be adopted as a concentration method or a purification method.
- Purified or isolated quercetin or its glycoside may be used in the present invention. Quercetin or its glycoside can also be a chemically synthesized product.
- the content of quercetin or its glycoside in the composition is, for example, preferably 0.0001% by weight or more, more preferably 0.001% by weight or more, and 50% by weight or less in terms of isoquercitrin. and may be 10% by weight or less, preferably 1% by weight or less, more preferably 0.1% by weight or less.
- the content of quercetin or its glycoside in the composition may be 0.0001 to 50% by weight, preferably 0.0001 to 10% by weight, in terms of isoquercitrin. is 0.0001 to 1% by weight, more preferably 0.001 to 0.1% by weight.
- the content of quercetin or its glycoside can be measured by a high performance liquid chromatography (HPLC) method.
- the amount in terms of isoquercitrin or similar expression means the amount of quercetin or its glycoside as isoquercitrin. Specifically, when the compound is isoquercitrin, it means the amount, and when the compound is quercetin or a quercetin glycoside other than isoquercitrin, the number of moles of the compound is multiplied by the molecular weight of isoquercitrin. means the value obtained by
- the weight ratio (in terms of L-ergothioneine) of the content of (A) L-ergothioneine or a salt thereof (in terms of L-ergothioneine) to (B) the content of quercetin or its glycoside (in terms of isoquercitrin) (A)/(B) in terms of isoquercitrin) is preferably 0.01 or more, more preferably 0.02 or more, still more preferably 0.025 or more, and preferably 1.2 or less, It is more preferably 1.1 or less, still more preferably 1 or less.
- (B) the weight ratio of the content of (A) L-ergothioneine or a salt thereof in terms of L-ergothioneine to the content of quercetin or its glycoside in terms of isoquercitrin ((A) in terms of L-ergothioneine / isoc
- (B) in terms of ercitrin is within the above range, the growth inhibitory action of quercetin or its glycoside on microorganisms is effectively enhanced.
- the weight ratio ((A) in terms of L-ergothioneine/(B) in terms of isoquercitrin) is preferably 0.01 to 1.2, more preferably 0.02 to 1.2, More preferably 0.025 to 1.2, even more preferably 0.025 to 1.1, and particularly preferably 0.025 to 1.
- the composition of the present invention preferably contains (A) L-ergothioneine or a salt thereof and (B) quercetin or a glycoside thereof in the above weight ratio.
- composition of the present invention contains (A) L-ergothioneine or a salt thereof and (B) quercetin or a glycoside thereof, the growth of microorganisms is suppressed.
- the composition of the present invention is useful as a composition (preferably an oral composition) in which the growth of microorganisms is suppressed.
- microorganisms include not only bacteria (bacteria) but also fungi (mushrooms, molds, yeasts, etc.), viruses, microalgae, etc.
- microorganisms refer to bacteria (bacteria ).
- Escherichia coli is preferred as the microorganism.
- a combination of L-ergothioneine or a salt thereof and quercetin or a glycoside thereof can exhibit an excellent growth inhibitory effect on E. coli.
- the composition of the present invention can be in the form of, for example, foods and beverages, pharmaceuticals, quasi-drugs, feeds, and the like.
- the composition of the present invention may itself be a food or drink product, a pharmaceutical product, a quasi-drug, a feed, or the like, or may be a material or formulation used by being blended therein.
- the content of L-ergothioneine or a salt thereof in the composition is preferably in terms of L-ergothioneine is 0.0001 to 0.1 wt%, more preferably 0.001 to 0.01 wt%.
- the content of quercetin or its glycoside in the composition is preferably 0.001 to 1% by weight, more preferably 0.01 to 0.1% by weight, in terms of isoquercitrin.
- compositions of the invention are preferably oral compositions.
- Oral compositions include food and drink, oral pharmaceuticals, quasi-drugs, feeds and the like, preferably food and drink or oral pharmaceuticals, more preferably food and drink.
- the composition of the present invention is useful as a microbial growth-inhibited oral composition, preferably an E. coli growth-inhibited oral composition.
- the composition of the present invention is useful, for example, as food and drink, oral pharmaceuticals, oral quasi-drugs, feeds, etc. in which the growth of microorganisms is suppressed.
- the composition of the present invention may contain optional additives and optional components as long as the effects of the present invention are not impaired.
- additives and components can be selected according to the form of the composition, etc., and those generally usable for foods and drinks, pharmaceuticals, quasi-drugs, feeds, etc. can be used.
- the manufacturing method is not particularly limited, and it can be manufactured by a general method.
- the form of the composition of the present invention is not particularly limited, and may be solid (powder, granule, tablet, etc.), liquid, paste, or the like.
- composition of the present invention when used as a food or drink, L-ergothioneine or a salt thereof and quercetin or a glycoside thereof may be added to ingredients usable in food or drink (for example, food materials, food additives used as necessary). products, etc.) can be blended into various foods and drinks.
- the food and drink are not particularly limited, and examples thereof include general food and drink, health food, health drink, food with function claims, food for specified health use, health supplement, and food and drink for the sick.
- Health foods, foods with function claims, foods for specified health uses, health supplements, etc. are various formulations such as fine granules, tablets, granules, powders, capsules, chewable formulations, syrups, liquid formulations, and liquid diets. can be in the form
- composition of the present invention When the composition of the present invention is used as a pharmaceutical or quasi-drug, for example, L-ergothioneine or a salt thereof and quercetin or a glycoside thereof, a pharmacologically acceptable carrier, and additives added as necessary
- a pharmaceutical or quasi-drug for example, L-ergothioneine or a salt thereof and quercetin or a glycoside thereof, a pharmacologically acceptable carrier, and additives added as necessary
- Such carriers, additives, etc. may be those that can be used for pharmaceuticals or quasi-drugs and are pharmacologically acceptable.
- antioxidants, coloring agents and the like can be mentioned.
- the dosage form of pharmaceuticals or quasi-drugs includes oral or parenteral dosage forms, with oral dosage forms being preferred.
- the composition of the present invention is used as a drug or quasi-drug, it is preferably an oral drug or quasi-drug.
- Dosage forms for oral administration include liquids, tablets, powders, fine granules, granules, dragees, capsules, suspensions, emulsions, chewables and the like.
- Dosage forms for parenteral administration include injections and infusions.
- feed When the composition of the present invention is used as a feed, L-ergothioneine or a salt thereof and quercetin or a glycoside thereof may be added to the feed.
- Feed also includes feed additives. Examples of feeds include livestock feeds for cows, pigs, chickens, sheep, horses, etc.; small animal feeds for rabbits, rats, mice, etc.; pet foods for dogs, cats, small birds, etc.;
- composition of the present invention when used as an oral composition, there is no particular limitation on subjects to whom the composition of the present invention is to be ingested or administered (can also be referred to as administration subjects). Humans or non-human mammals are preferred, and humans are more preferred.
- the intake (dosage) of the composition of the present invention is not particularly limited.
- the amount is preferably 2-50 mg, more preferably 5-25 mg, still more preferably 5-20 mg, particularly preferably 10-20 mg.
- a combination of (A) L-ergothioneine or a salt thereof and (B) quercetin or a glycoside thereof can be used as an active ingredient for inhibiting growth of microorganisms.
- the compositions of the present invention can be suitably used, for example, to inhibit microbial growth.
- the composition of the present invention may be a microbial growth inhibitory composition.
- L-ergothioneine or its salts and quercetin or its glycosides are compounds that are contained in natural products and foods and drinks and have been eaten.
- the compositions of the present invention can be suitably used, for example, to inhibit microbial growth in oral compositions.
- the composition of the present invention can be suitably used as an oral composition for inhibiting microbial growth.
- the microbial growth inhibitory composition can also be called a microbial growth inhibitor.
- the composition of the present invention can be suitably used as a composition for suppressing the growth of E. coli.
- compositions of the present invention can be used, for example, in addition to oral compositions.
- the composition of the invention may be added to the oral composition.
- the composition of the present invention can be used as a food additive.
- Oral compositions to which the composition of the present invention is added are not particularly limited, and include food and drink, oral pharmaceuticals, oral quasi-drugs, feeds, etc. Food and drink are preferred.
- composition of the present invention when used as a composition for inhibiting the growth of microorganisms by adding it to a food or drink, (A) L-ergothioneine or a salt thereof and (B) quercetin or
- the total content of glycosides may be, for example, 0.01 to 99% by weight, preferably 0.1 to 90% by weight.
- the amount of addition is such that the content of L-ergothioneine or a salt thereof in the oral composition is converted to L-ergothioneine,
- the amount is preferably 0.00001 to 0.1% by weight, more preferably 0.0001 to 0.01% by weight.
- the amount of quercetin or its glycoside added is such that the content of quercetin or its glycoside in the oral composition is preferably 0.001 to 1% by weight, more preferably 0.001 to 1% by weight, in terms of isoquercitrin. An amount of 01 to 0.1% by weight is preferred. From the viewpoint of obtaining the effect of inhibiting the growth of microorganisms, it is preferable to add the composition in such an amount that the contents of L-ergothioneine or its salt and quercetin or its glycoside are as described above.
- the present invention also includes a method for inhibiting microbial growth of an oral composition, comprising adding (A) L-ergothioneine or a salt thereof and (B) quercetin or a glycoside thereof to the oral composition.
- (A) L-ergothioneine or a salt thereof and (B) quercetin or a glycoside thereof preferred embodiments thereof are the same as those of the composition of the present invention described above.
- quercetin or its glycoside is preferably at least one selected from the group consisting of isoquercitrin, rutin, enzyme-treated rutin and quercitrin.
- the microorganisms and preferred embodiments thereof are the same as described above, preferably Escherichia coli.
- the method of the present invention is preferably an oral composition E. coli growth inhibition method.
- Oral compositions are not particularly limited, and include the above-mentioned food and drink, oral pharmaceuticals, oral quasi-drugs, feeds, and the like.
- the content of (A) L-ergothioneine or a salt thereof (converted to L-ergothioneine) relative to the content of (B) quercetin or its glycoside (converted to isoquercitrin) in the oral composition (A) in terms of L-ergothioneine / (B) in terms of isoquercitrin) is 0.01 or more, and (A) L-ergothioneine or a salt thereof and (B) quercetin or its Glycosides are preferably added to the oral composition.
- the weight ratio ((A) in terms of L-ergothioneine/(B) in terms of isoquercitrin) is more preferably 0.02 or more, still more preferably 0.025 or more, and preferably 1.2 or less. It is more preferably 1.1 or less, still more preferably 1 or less.
- the weight ratio ((A) in terms of L-ergothioneine/(B) in terms of isoquercitrin) is preferably 0.01 to 1.2, more preferably 0.02 to 1.2, More preferably 0.025 to 1.2, even more preferably 0.025 to 1.1, and particularly preferably 0.025 to 1.
- Weight ratio of the content of (A) L-ergothioneine or a salt thereof (converted to L-ergothioneine) to the content of (B) quercetin or its glycoside (converted to isoquercitrin) in the oral composition (L-ergothioneine (A) in conversion/(B) in conversion of isoquercitrin) is within the above range, (A) L-ergothioneine or a salt thereof and (B) quercetin or a glycoside thereof are added to the oral composition. addition is preferred.
- the amount of L-ergothioneine or a salt thereof to be added is such that the content of L-ergothioneine or a salt thereof in the oral composition is preferably 0.00001 to 0.1% by weight, more preferably 0.1% by weight, in terms of L-ergothioneine. 0001 to 0.01% by weight is preferred.
- the amount of quercetin or its glycoside added is such that the content of quercetin or its glycoside in the oral composition is preferably 0.001 to 1% by weight, more preferably 0.01 to 1% by weight, in terms of isoquercitrin. An amount of 0.1% by weight is preferred.
- (A) L-ergothioneine or a salt thereof and (B) quercetin or a glycoside thereof may be added separately to the oral composition. may be added to For example, using the compositions of the invention described above, (A) L-ergothioneine or a salt thereof and (B) quercetin or a glycoside thereof may be added to an oral composition.
- the present invention also includes agents for enhancing the microbial growth inhibitory action of quercetin or its glycosides, including L-ergothioneine or a salt thereof.
- L-ergothioneine or a salt thereof can be used as an active ingredient for enhancing the microbial growth inhibitory action of quercetin or its glycoside.
- L-ergothioneine or a salt thereof can be suitably used, for example, to enhance the E. coli growth inhibitory action of quercetin or its glycoside.
- the present invention also includes the use of (A) L-ergothioneine or a salt thereof and (B) quercetin or a glycoside thereof for producing a composition for inhibiting the growth of microorganisms.
- the present invention also includes the use of L-ergothioneine or its salts to enhance the microbial growth inhibitory action of quercetin or its glycosides.
- a range represented by “1-2” means from 1 to 2 and includes 1 and 2.
- the upper limit and the lower limit may be any combination of ranges.
- L-ergothioneine (hereinafter sometimes simply referred to as ergothioneine) and quercetin glycosides were examined for their sterilizing (inhibiting the growth of microorganisms) effects.
- ergothioneine As a quercetin glycoside, isoquercitrin (quercetin 3-glucoside, Cayman Chemical) was used.
- Escherichia coli NBRC 3972 was used as the test fungus.
- E. coli was inoculated onto a nutrient agar medium and cultured at 30-35° C. for 24 hours. After culturing, the bacterial count was adjusted to 10 8 CFU/mL using physiological saline to prepare a test bacterial solution.
- test sample 1 Phosphate-buffered saline and ergothioneine were mixed to prepare test sample 1 (ergothioneine concentration of 100 ppm (0.01% by weight)).
- Phosphate-buffered saline and isoquercitrin were mixed to prepare test sample 2 (isoquercitrin concentration: 100 ppm (0.01% by weight)).
- test sample 3 Phosphate-buffered saline, ergothioneine and isoquercitrin were mixed to prepare test sample 3 (ergothioneine concentration of 2.5 ppm (0.00025% by weight), isoquercitrin concentration of 100 ppm (0.01% by weight)).
- test sample 4 ergothioneine concentration 100 ppm (0.01% by weight), isoquercitrin concentration 100 ppm (0.01% by weight)
- Phosphate-buffered saline served as control.
- Table 1 shows the concentrations of (A) ergothioneine and (B) isoquercitrin in the test sample, and the weight ratio of (A) ergothioneine to (B) isoquercitrin ((A)/(B)).
- test bacterial solution 0.05 mL of the test bacterial solution was inoculated into 5 mL of the test sample and allowed to stand at room temperature.
- FIG. 1 is a graph showing the sterilization effect of L-ergothioneine (test sample 1), isoquercitrin (test sample 2), and a combination of L-ergothioneine and isoquercitrin (test samples 3-4).
- L-ergothioneine alone was not found to have a bactericidal effect on Escherichia coli.
- Isoquercitrin inhibited the growth of E. coli when used alone, but the E. coli growth inhibitory effect obtained by the combination of L-ergothioneine and isoquercitrin was the effect obtained by using each component alone.
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Abstract
Description
〔1〕(A)L-エルゴチオネイン又はその塩と、(B)ケルセチン又はその配糖体とを含有する組成物。
〔2〕(B)ケルセチン又はその配糖体が、イソクエルシトリン、ルチン、酵素処理ルチン及びクエルシトリンからなる群より選択される少なくとも1種である、上記〔1〕に記載の組成物。
〔3〕(B)ケルセチン又はその配糖体の含有量(イソクエルシトリン換算)に対する、(A)L-エルゴチオネイン又はその塩の含有量(L-エルゴチオネイン換算)の重量比(L-エルゴチオネイン換算の(A)/イソクエルシトリン換算の(B))が0.01~1.2である、上記〔1〕又は〔2〕に記載の組成物。
〔4〕微生物増殖抑制用組成物である、上記〔1〕~〔3〕のいずれかに記載の組成物。
〔5〕経口組成物の微生物増殖抑制用組成物である、上記〔4〕に記載の組成物。
〔6〕微生物が、大腸菌である、上記〔4〕又は〔5〕に記載の組成物。
〔7〕(A)L-エルゴチオネイン又はその塩と、(B)ケルセチン又はその配糖体とを経口組成物に添加する、経口組成物の微生物増殖抑制方法。
〔8〕(B)ケルセチン又はその配糖体が、イソクエルシトリン、ルチン、酵素処理ルチン及びクエルシトリンからなる群より選択される少なくとも1種である、上記〔7〕に記載の方法。
〔9〕経口組成物中の(B)ケルセチン又はその配糖体の含有量(イソクエルシトリン換算)に対する、(A)L-エルゴチオネイン又はその塩の含有量(L-エルゴチオネイン換算)の重量比(L-エルゴチオネイン換算の(A)/イソクエルシトリン換算の(B))が0.01~1.2となるように、(A)L-エルゴチオネイン又はその塩と、(B)ケルセチン又はその配糖体とを経口組成物に添加する、上記〔7〕又は〔8〕に記載の方法。
〔10〕微生物が、大腸菌である、上記〔7〕~〔9〕のいずれかに記載の方法。
〔11〕L-エルゴチオネイン又はその塩を含む、ケルセチン又はその配糖体の微生物増殖抑制作用増強剤。
本発明の組成物は、(A)L-エルゴチオネイン又はその塩と、(B)ケルセチン又はその配糖体とを含有する。
ケルセチン又はその配糖体は、微生物増殖抑制作用(抗菌作用)を有する。L-エルゴチオネイン又はその塩と、ケルセチン又はその配糖体とを組み合わせると、ケルセチン又はその配糖体の微生物増殖抑制作用を増強することができる。このため、L-エルゴチオネイン又はその塩と、ケルセチン又はその配糖体とを組み合わせて使用することで、微生物の増殖を効果的に抑制することが可能となる。
L-エルゴチオネイン又はその塩として、好ましくは、L-エルゴチオネインを使用する。
本明細書中、L-エルゴチオネイン又はその塩について、L-エルゴチオネイン換算の量又はこれに類する表現は、L-エルゴチオネイン又はその塩のL-エルゴチオネインとしての量を意味する。具体的には、L-エルゴチオネインの場合はその量を意味し、L-エルゴチオネインの塩の場合は、当該塩のモル数に、L-エルゴチオネインの分子量を乗じて得られる値を意味する。
本発明に用いられるケルセチン又はその配糖体には、本発明の効果を奏することになる限り、上記の植物等の天然物由来の抽出物を、濃縮、精製等の操作によってケルセチン又はその配糖体の含量を高めたもの、例えば、ケルセチン又はその配糖体を含有する抽出物の、濃縮物又は精製物を用いることができる。濃縮方法又は精製方法は、既知の方法を採用することができる。本発明においては、精製又は単離されたケルセチン又はその配糖体を使用してもよい。ケルセチン又はその配糖体は、化学合成品を使用することもできる。
ケルセチン又はその配糖体の含有量は、高速液体クロマトグラフィー(HPLC)法により測定することができる。
本明細書中、ケルセチン又はその配糖体について、イソクエルシトリン換算の量又はこれに類する表現は、ケルセチン又はその配糖体のイソクエルシトリンとしての量を意味する。具体的には、化合物がイソクエルシトリンの場合はその量を意味し、化合物がケルセチン又はイソクエルシトリン以外のケルセチン配糖体の場合は、当該化合物のモル数に、イソクエルシトリンの分子量を乗じて得られる値を意味する。
本発明において、微生物として、大腸菌が好ましい。L-エルゴチオネイン又はその塩と、ケルセチン又はその配糖体とを組み合わせることで、大腸菌に対して優れた増殖抑制効果を発揮することができる。
一態様において、本発明の組成物は、微生物の増殖が抑制された経口組成物、好ましくは大腸菌の増殖が抑制された経口組成物として有用である。一態様において、本発明の組成物は、例えば、微生物の増殖が抑制された飲食品、経口医薬品、経口医薬部外品、飼料等として有用である。
本発明の組成物の形態は特に限定されず、固体状(粉末状、顆粒状、タブレット状等)、液状、ペースト状等であってよい。
L-エルゴチオネイン又はその塩、及び、ケルセチン又はその配糖体は、天然物や飲食品に含まれ、食経験がある化合物である。本発明の組成物は、例えば、経口組成物における微生物の増殖を抑制するために好適に使用することができる。一態様において、本発明の組成物は、経口組成物の微生物増殖抑制用組成物として好適に使用することができる。微生物増殖抑制用組成物は、微生物増殖抑制剤ということもできる。一態様において、本発明の組成物は、大腸菌増殖抑制用組成物として好適に使用することができる。
本発明は、(A)L-エルゴチオネイン又はその塩と、(B)ケルセチン又はその配糖体とを経口組成物に添加する、経口組成物の微生物増殖抑制方法も包含する。
本発明の方法において、(A)L-エルゴチオネイン又はその塩、及び、(B)ケルセチン又はその配糖体、これらの好ましい態様は、上述した本発明の組成物と同じである。
例えば、ケルセチン又はその配糖体は、イソクエルシトリン、ルチン、酵素処理ルチン及びクエルシトリンからなる群より選択される少なくとも1種であることが好ましい。
本発明は、L-エルゴチオネイン又はその塩を含む、ケルセチン又はその配糖体の微生物増殖抑制作用増強剤も包含する。L-エルゴチオネイン又はその塩は、ケルセチン又はその配糖体の微生物増殖抑制作用を増強するための有効成分として使用することができる。
L-エルゴチオネイン又はその塩は、例えば、ケルセチン又はその配糖体の大腸菌増殖抑制作用を増強するために好適に使用することができる。
本発明は、ケルセチン又はその配糖体の微生物増殖抑制作用を増強するための、L-エルゴチオネイン又はその塩の使用、も包含する。
L-エルゴチオネイン(以下、単にエルゴチオネインと記載する場合がある)及びケルセチン配糖体の除菌(微生物増殖抑制)効果を調べた。
ケルセチン配糖体には、イソクエルシトリン(ケルセチン3-グルコシド、Cayman Chemical社製)を使用した。
試験菌には、大腸菌(Escherichia coli NBRC 3972)を使用した。
大腸菌を普通寒天培地に接種し、30~35℃で24時間培養した。培養後、生理食塩水を用いて菌数が108CFU/mLとなるように調製し、試験菌液とした。
リン酸緩衝生理食塩水及びエルゴチオネインを混合し、試験試料1(エルゴチオネイン濃度100ppm(0.01重量%))を調製した。
リン酸緩衝生理食塩水及びイソクエルシトリンを混合し、試験試料2(イソクエルシトリン濃度100ppm(0.01重量%))を調製した。
リン酸緩衝生理食塩水、エルゴチオネイン及びイソクエルシトリンを混合し、試験試料3(エルゴチオネイン濃度2.5ppm(0.00025重量%)、イソクエルシトリン濃度100ppm(0.01重量%))を調製した。リン酸緩衝生理食塩水、エルゴチオネイン及びイソクエルシトリンを混合し、試験試料4(エルゴチオネイン濃度100ppm(0.01重量%)、イソクエルシトリン濃度100ppm(0.01重量%))を調製した。
リン酸緩衝生理食塩水を対照とした。
表1に、試験試料中の(A)エルゴチオネイン及び(B)イソクエルシトリンの濃度、(B)イソクエルシトリンに対する(A)エルゴチオネインの重量比((A)/(B))を示す。
試験試料5mLに、試験菌液を0.05mL接種し、室温で静置した。
接種1時間後に、試験菌液を接種した試験試料の10倍希釈液をレシチン・ポリソルベート80添加ソイビーン・カゼイン・ダイジェスト液体培地で調製した。得られた大腸菌を含む希釈液を、レシチン・ポリソルベート80添加ソイビーン・カゼイン・ダイジェスト寒天培地に接種し、30~35℃で3~5日間培養した。培養後、形成されたコロニーをカウントし、生菌数を算出した(n=3)。
生菌数(n=3の平均値)から、下記式で除菌効果(%)を求めた。
除菌効果(%)=100-100×(試験試料中の生菌数)/(対照中の生菌数)
結果を図1に示す。
Claims (11)
- (A)L-エルゴチオネイン又はその塩と、(B)ケルセチン又はその配糖体とを含有する組成物。
- (B)ケルセチン又はその配糖体が、イソクエルシトリン、ルチン、酵素処理ルチン及びクエルシトリンからなる群より選択される少なくとも1種である、請求項1に記載の組成物。
- (B)ケルセチン又はその配糖体の含有量(イソクエルシトリン換算)に対する、(A)L-エルゴチオネイン又はその塩の含有量(L-エルゴチオネイン換算)の重量比(L-エルゴチオネイン換算の(A)/イソクエルシトリン換算の(B))が0.01~1.2である、請求項1又は2に記載の組成物。
- 微生物増殖抑制用組成物である、請求項1又は2に記載の組成物。
- 経口組成物の微生物増殖抑制用組成物である、請求項4に記載の組成物。
- 微生物が、大腸菌である、請求項4に記載の組成物。
- (A)L-エルゴチオネイン又はその塩と、(B)ケルセチン又はその配糖体とを経口組成物に添加する、経口組成物の微生物増殖抑制方法。
- (B)ケルセチン又はその配糖体が、イソクエルシトリン、ルチン、酵素処理ルチン及びクエルシトリンからなる群より選択される少なくとも1種である、請求項7に記載の方法。
- 経口組成物中の(B)ケルセチン又はその配糖体の含有量(イソクエルシトリン換算)に対する、(A)L-エルゴチオネイン又はその塩の含有量(L-エルゴチオネイン換算)の重量比(L-エルゴチオネイン換算の(A)/イソクエルシトリン換算の(B))が0.01~1.2となるように、(A)L-エルゴチオネイン又はその塩と、(B)ケルセチン又はその配糖体とを経口組成物に添加する、請求項7又は8に記載の方法。
- 微生物が、大腸菌である、請求項7又は8に記載の方法。
- L-エルゴチオネイン又はその塩を含む、ケルセチン又はその配糖体の微生物増殖抑制作用増強剤。
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Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2008109831A1 (en) * | 2007-03-07 | 2008-09-12 | Oxis Int Inc | Use of ergothioneine as a preservative in foods and beverages |
EP1994923A2 (de) * | 2007-05-23 | 2008-11-26 | Henkel AG & Co. KGaA | Kosmetische und dermatologische Zusammensetzungen gegen trockene Haut |
CN109042651A (zh) * | 2018-06-20 | 2018-12-21 | 北京化工大学 | 苹果渣和苹果叶提取物在植物病原菌防治中的应用 |
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- 2023-01-26 AU AU2023213321A patent/AU2023213321A1/en active Pending
- 2023-01-26 WO PCT/JP2023/002341 patent/WO2023145792A1/ja active Application Filing
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2008109831A1 (en) * | 2007-03-07 | 2008-09-12 | Oxis Int Inc | Use of ergothioneine as a preservative in foods and beverages |
EP1994923A2 (de) * | 2007-05-23 | 2008-11-26 | Henkel AG & Co. KGaA | Kosmetische und dermatologische Zusammensetzungen gegen trockene Haut |
CN109042651A (zh) * | 2018-06-20 | 2018-12-21 | 北京化工大学 | 苹果渣和苹果叶提取物在植物病原菌防治中的应用 |
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