Oral composition and method for suppressing bitterness derived from ergothioneine

JP7899224B2Active Publication Date: 2026-08-03SUNTORY HLDG LTD
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Authority / Receiving Office
JP · JP
Patent Type
Patents
Current Assignee / Owner
SUNTORY HLDG LTD
Filing Date
2022-12-15
Publication Date
2026-08-03

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Abstract

The purpose of the present invention is to provide an oral composition which contains ergothioneine or a salt thereof and in which the bitterness derived from ergothioneine or a salt thereof is reduced. The present invention pertains to an oral composition containing components (A) and (B): (A) ergothioneine or a salt thereof; and (B) theanine.
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Description

Technical Field

[0001] The present invention relates to an oral composition containing ergothioneine or a salt thereof and theanine. The present invention also relates to a method for suppressing the bitterness derived from ergothioneine.

Background Art

[0002] Ergothioneine is one of the hydrophilic sulfur-containing amino acids and is known to have various physiological activities including antioxidant ability. Regarding the physiological activity of ergothioneine, for example, Patent Document 1 reports an action of promoting the production of immunoresponse-activating cytokines. Since ergothioneine has various physiological activities, it has recently attracted attention for use in foods, cosmetics, and pharmaceuticals.

[0003] Regarding a composition containing ergothioneine, for example, Patent Document 2 discloses a method for suppressing off-odor and / or discoloration, which is characterized by adjusting the pH of a composition containing ergothioneine and / or its derivative and / or blending a storage stabilizer in the composition.

Prior Art Documents

Patent Documents

[0004]

Patent Document 1

Patent Document 2

Summary of the Invention

Problems to be Solved by the Invention

[0005] As mentioned above, ergothioneine possesses beneficial physiological activity, and therefore, supplements and other foods containing ergothioneine or its salts are useful for maintaining or improving health. However, ergothioneine or its salts have a distinctive flavor, particularly a pungent bitterness, which could be improved when formulated as an oral composition.

[0006] The object of the present invention is to provide an oral composition containing ergothioneine or a salt thereof in which the bitterness derived from ergothioneine or a salt thereof is reduced. The object of the present invention is also to provide a method for suppressing the bitterness derived from ergothioneine or a salt thereof in an oral composition containing ergothioneine or a salt thereof. [Means for solving the problem]

[0007] As a result of diligent research to solve the above problems, the inventors have found that combining ergothioneine or a salt thereof with theanine can effectively suppress the bitterness derived from ergothioneine or a salt thereof.

[0008] The present invention includes the following compositions, etc. [1] The following components (A) and (B): An oral composition comprising (A) ergothioneine or a salt thereof, and (B) theanine. [2] The composition according to [1] above, wherein the weight ratio ((B) / (A)) of component (B) (equivalent to L-glutamic acid-γ-ethylamide) to component (A) (equivalent to ergothioneine) is 2 to 90. [3] The composition described in [1] or [2] above, which is a food or beverage. [4] (A) A method for suppressing bitterness derived from ergothioneine or a salt thereof in an oral composition containing ergothioneine or a salt thereof, comprising the step of (B) incorporating theanine. [5] The method according to [4] above, wherein component (B) is blended in the oral composition such that the weight ratio ((B) / (A)) of component (B) (in terms of L-glutamic acid-γ-ethylamide) to component (A) (in terms of ergothioneine) is 2 to 90. [6] (B) Theanine is used to suppress the bitterness derived from (A) ergothioneine or a salt thereof. [Effects of the Invention]

[0009] According to the present invention, it is possible to provide an oral composition containing ergothioneine or a salt thereof in which the bitterness derived from ergothioneine or a salt thereof is reduced. According to the present invention, it is possible to provide a method for suppressing the bitterness derived from ergothioneine or a salt thereof in an oral composition containing ergothioneine or a salt thereof. [Modes for carrying out the invention]

[0010] The composition of the present invention is an oral composition containing (A) ergothioneine or a salt thereof, and (B) theanine.

[0011] Ergothioneine is a type of sulfur-containing amino acid. In the present invention, ergothioneine is preferably L-ergothioneine. The salt of ergothioneine is not particularly limited as long as it is a pharmacologically acceptable salt or a salt acceptable in food and beverages, and may be either an acidic salt or a basic salt. Examples of acidic salts include inorganic salts such as hydrochloride, sulfate, nitrate, and phosphate; and organic salts such as acetate, citrate, maleate, malate, oxalate, lactate, succinate, fumarate, and propionate. Examples of basic salts include alkali metal salts such as sodium salt and potassium salt; and alkaline earth metal salts such as calcium salt and magnesium salt.

[0012] Ergothioneine or its salts are not limited in any way by their form or manufacturing method. Ergothioneine or its salts may be chemically synthesized or extracted and purified from natural sources. L-ergothioneine is abundant in the Golden / Yellow Oyster Mushroom (Pleurotus cornucopiae var. citrinopileatus), a mushroom belonging to the genus Pleurotus in the family Pleurotaceae. L-ergothioneine is also found in mushrooms such as white button mushrooms, crimson mushrooms, portabella mushrooms, oyster mushrooms (Pleurotus ostreatus), shiitake mushrooms (Lentinula edodes), maitake mushrooms (Grifola frondosa), lychee mushrooms (Ganoderma lucidum), lion's mane mushrooms (Hericium erinaceus), willow mushrooms (Agrocybe aegerita), chanterelle mushrooms (Cantharellus cibarius), porcini mushrooms (Boletus edulis), and morel mushrooms (Morchella esculenta). When obtaining L-ergothioneine from natural sources, extraction from Pleurotus ostreatus is preferable. Ergothioneine or its salts can also be produced by microbial fermentation. Ergothioneine or its salts may be isolated. As the ergothioneine or salt thereof mentioned above, for example, one derived from Pleurotus ostreatus can be used, but the composition of the present invention may or may not contain dried Pleurotus ostreatus.

[0013] Theanine is a type of amino acid, a derivative of glutamic acid, and one of the umami components of tea. Theanine has a distinctive flavor (a persistent, unpleasant aftertaste resulting from the coexistence of excessive umami with a slight sweetness). The composition of the present invention reduces the bitterness derived from ergothioneine or its salt by including theanine. Therefore, it facilitates the continuous intake of ergothioneine or its salt. By combining theanine with ergothioneine or its salts, the flavor derived from theanine can also be suppressed.

[0014] Specific examples of theanine include L-glutamic acid-γ-ethylamide (L-theanine), L-glutamic acid-γ-methylamide, D-glutamic acid-γ-ethylamide (D-theanine), and D-glutamic acid-γ-methylamide. One or more of these can be used as theanine. A form in which theanine is at least one selected from the group consisting of L-glutamic acid-γ-ethylamide (L-theanine), L-glutamic acid-γ-methylamide, D-glutamic acid-γ-ethylamide (D-theanine), and D-glutamic acid-γ-methylamide is one of the preferred embodiments of the present invention. Theanine is more preferably L-theanine or D-theanine, and even more preferably L-theanine.

[0015] The theanine used in this invention is not limited in any way by its form or manufacturing method, and may be a chemically synthesized product or one extracted and purified from a natural product. Specific examples of theanine production methods include separation and purification from tea leaves, tissue culture using tea cells, and methods utilizing enzymatic reactions. One method utilizing enzymatic reactions involves reacting a mixture of glutamine and ethylamine with glutaminase to obtain theanine; theanine produced in this way is also available commercially. Theanine obtained by the enzymatic reaction is preferably used as theanine (L-isomer) in the present invention. As the theanine, for example, those derived from green tea leaves can be used, but the composition of the present invention may or may not contain green tea leaves.

[0016] In the composition of the present invention, the weight ratio of component (B) (in terms of L-glutamic acid-γ-ethylamide) to component (A) (in terms of ergothioneine) (weight of (B) in terms of L-glutamic acid-γ-ethylamide / weight of (A) in terms of ergothioneine) is not particularly limited, but may be 1 to 100. When the weight ratio of component (B) (in terms of L-glutamic acid-γ-ethylamide) to component (A) (in terms of ergothioneine) is within the above range, the bitterness derived from component (A) can be sufficiently suppressed. The above weight ratio is preferably 2 to 90. Thereby, the flavor derived from component (B) can also be sufficiently suppressed, and the composition becomes easier to ingest. The above weight ratio is more preferably 3 to 80, still more preferably 5 to 70, particularly preferably 8 to 60, and most preferably 10 to 50. In this specification, the amount in terms of ergothioneine or an expression similar thereto means the amount in the case of ergothioneine, and in the case of a salt of ergothioneine, it means the value obtained by multiplying the number of moles of the salt by the molecular weight of ergothioneine.

[0017] The content of ergothioneine or its salt contained in the composition of the present invention is not particularly limited and can be set according to its form and the like. The content of ergothioneine or its salt in the composition of the present invention is preferably 0.1% by weight or more, more preferably 0.5% by weight or more, still more preferably 0.6% by weight or more, even more preferably 0.8% by weight or more, particularly preferably 1% by weight or more, and preferably 50% by weight or less, more preferably 40% by weight or less, still more preferably 30% by weight or less, even more preferably 20% by weight or less, particularly preferably 10% by weight or less, in terms of ergothioneine. In one aspect, the content of ergothioneine or its salt is preferably 0.1 to 50% by weight, more preferably 0.5 to 40% by weight, still more preferably 0.6 to 30% by weight, even more preferably 0.8 to 20% by weight, particularly preferably 1 to 10% by weight, in the composition of the present invention in terms of ergothioneine. The content of ergothioneine can be measured by high performance liquid chromatography (HPLC).

[0018] The content of theanine contained in the composition of the present invention is not particularly limited and can be set according to its form and the like. The total content of theanine in the composition of the present invention is preferably 1% by weight or more, more preferably 1.5% by weight or more, still more preferably 2% by weight or more, even more preferably 2.5% by weight or more, still more preferably 5% by weight or more, particularly preferably 10% by weight or more, particularly even more preferably 20% by weight or more, and preferably 90% by weight or less, more preferably 85% by weight or less, still more preferably 80% by weight or less, even more preferably 75% by weight or less, still more preferably 70% by weight or less, particularly preferably 60% by weight or less, particularly even more preferably 50% by weight or less, in the composition. In one aspect, the total content of theanine is preferably 1 to 90% by weight, more preferably 1.5 to 85% by weight, still more preferably 2 to 80% by weight, even more preferably 2.5 to 75% by weight, still more preferably 5 to 70% by weight, particularly preferably 10 to 60% by weight, particularly even more preferably 20 to 50% by weight, in the composition of the present invention in terms of L-glutamic acid-γ-ethylamide. When the above total content contains two or more kinds of theanine, it is the total content of these. The content of theanine can be measured by the HPLC method.

[0019] The composition of the present invention preferably contains ergothioneine or a salt thereof in terms of ergothioneine equivalent of 1 to 100 mg per adult daily intake, more preferably 2 to 50 mg, even more preferably 5 to 25 mg, and particularly preferably 5 to 20 mg. The composition of the present invention preferably contains theanine in the form of 10 to 2000 mg, more preferably 20 to 1000 mg, and even more preferably 50 to 500 mg, in terms of L-glutamic acid-γ-ethylamide, per the daily intake for adults.

[0020] Ergothioneine or its salts and theanine are compounds found in natural products and foods and beverages, and have a history of being consumed. Therefore, from a safety standpoint, it is considered that ergothioneine or its salts and theanine pose little problem even when consumed daily. According to the present invention, it is possible to provide a composition that is highly safe and easy to consume, with reduced bitterness derived from ergothioneine or its salts.

[0021] As mentioned above, ergothioneine or its salts are known to exhibit a variety of physiological activities and health benefits. For example, they are known to have antioxidant effects, improve brain function, have anti-aging effects, improve eye diseases, have skin whitening effects, absorb ultraviolet rays, inhibit melanin production, scavenge reactive oxygen species, inhibit elastase activity, inhibit wrinkle formation, inhibit skin sagging, and promote autophagy. Therefore, the compositions of the present invention can be suitably used for antioxidant purposes, brain function improvement, anti-aging, eye disease treatment, skin whitening, UV absorption, melanin production suppression, reactive oxygen species scavenging, elastase activity inhibition, wrinkle formation suppression, skin sagging suppression, autophagy promotion, and the like.

[0022] Theanine is known to exhibit various health benefits, including relaxation, stress reduction, sleep promotion, brain nerve cell protection, improved memory and concentration, prevention of high blood pressure, improvement of cold sensitivity, and alleviation of premenstrual syndrome and menopausal symptoms. Since the composition of the present invention contains theanine, it can also be used to obtain the above-mentioned effects exhibited by theanine.

[0023] The compositions of the present invention can be applied to either therapeutic (medical) or non-therapeutic (non-medical) uses. Non-therapeutic means that the use does not involve medical procedures, i.e., human surgery, treatment, or diagnosis. The composition of the present invention can be in the form of food and beverages, pharmaceuticals, quasi-drugs, animal feed, etc. The composition of the present invention may also be a material or formulation used in food and beverages, pharmaceuticals, quasi-drugs, animal feed, etc.

[0024] The composition of the present invention is an oral composition, and specific examples of oral compositions include food and beverages, oral pharmaceuticals, quasi-drugs, animal feed, etc. Preferably, it is a food and beverage or an oral pharmaceutical, and more preferably a food and beverage.

[0025] The composition of the present invention may contain any additives and components in addition to ergothioneine or its salt and theanine, as long as the effects of the present invention are not impaired. These additives and components can be selected according to the form of the composition, and generally, those that can be used in oral compositions such as food and beverages, pharmaceuticals, quasi-drugs, and animal feed can be used. When the composition of the present invention is used in food and beverages, pharmaceuticals, quasi-drugs, or animal feed, the method of manufacture is not particularly limited and can be manufactured by general methods. In one embodiment, the composition of the present invention may consist of ergothioneine or its salt and theanine. The form of the oral composition of the present invention is not particularly limited and may be solid (powder, granules, tablets, etc.), liquid, paste, etc.

[0026] For example, when the composition of the present invention is used as a food or beverage, various food and beverages can be made by blending ergothioneine or its salt and theanine with ingredients usable in food and beverages (e.g., food materials, food additives used as needed). Food and beverages are not particularly limited and include, for example, general food and beverages, health foods, health supplements, health drinks, foods with functional claims, foods for specified health uses, and food and beverages for sick people. The above-mentioned health foods, health supplements, foods with functional claims, foods for specified health uses, etc., can be used in various formulation forms such as fine granules, tablets, granules, powders, capsules, chewable tablets, dry syrups, syrups, liquids, beverages, drinks, and liquid foods.

[0027] When the composition of the present invention is used as a pharmaceutical or quasi-drug, for example, ergothioneine or its salt and theanine can be combined with a pharmacologically acceptable carrier, additives as needed, etc., to produce pharmaceuticals or quasi-drugs in various dosage forms. Such carriers, additives, etc., only need to be pharmacologically acceptable and usable in pharmaceuticals or quasi-drugs, and examples include one or more excipients, binders, disintegrants, lubricants, antioxidants, colorants, etc. Dosage forms for oral administration of pharmaceuticals or quasi-drugs include liquids, tablets, powders, granules, sugar-coated tablets, capsules, suspensions, emulsions, chewables, etc.

[0028] When the composition of the present invention is used as feed, ergothioneine or its salt and theanine may be added to the feed. Feed additives may also be included in the feed. Examples of feed include livestock feed for cattle, pigs, chickens, sheep, horses, etc.; small animal feed for rabbits, rats, mice, etc.; and pet food for dogs, cats, small birds, etc.

[0029] The subjects (or recipients) to whom the composition of the present invention is administered are not particularly limited. Preferably, they are humans or non-human mammals, and more preferably, humans.

[0030] The present invention also includes the following methods. (A) A method for suppressing bitterness derived from ergothioneine in an oral composition containing ergothioneine or a salt thereof, comprising the step of (B) incorporating theanine. In preparing an oral composition, by adjusting the weight ratio of component (B) to component (A) (in terms of ergothioneine) ((B) / (A)) to the above range, an oral composition can be obtained in which the bitterness derived from ergothioneine or its salt and the flavor derived from theanine are suppressed. The above weight ratio can be adjusted, for example, by adding component (A) and / or component (B).

[0031] The present invention also includes the following uses: (B) The use of theanine to suppress the bitterness derived from (A) ergothioneine or its salts.

[0032] The above method and usage make it possible to effectively suppress the bitterness derived from ergothioneine. In the above methods and uses, ergothioneine or its salts and theanine, and preferred embodiments thereof, are the same as those in the compositions of the present invention described above. Furthermore, in the above method and use, the mixing ratio and amount of component (B) (L-glutamic acid-γ-ethylamide equivalent) to component (A) (ergothioneine equivalent) are not particularly limited, but a preferred range is the same as the weight ratio of component (B) (L-glutamic acid-γ-ethylamide equivalent) to component (A) (ergothioneine equivalent) in the composition of the present invention.

[0033] The above method and use can suppress bitterness derived from ergothioneine or its salts, but it may also be combined with other methods for suppressing bitterness. Other methods for suppressing bitterness include, for example, adding a sweetener or flavoring agent to the bitter component during formulation, coating the bitter component with sugar during formulation, or encapsulating it during formulation.

[0034] In this specification, a numerical range expressed by a lower limit and an upper limit, i.e., "lower limit to upper limit," includes those lower and upper limits. For example, a range expressed as "1 to 2" means 1 or more and 2 or less, including 1 and 2. In this specification, the upper and lower limits may be any combination of ranges. [Examples]

[0035] The present invention will be described more specifically below based on examples. However, the present invention is not limited to these examples.

[0036] The materials used in the evaluation tests described below are as follows: (A) Ergothioneine: Raw material containing 100% L-ergothioneine (B) Theanine: Raw material containing 100% L-theanine

[0037] <Example 1: Flavor evaluation test of a composition containing ergothioneine and theanine> A composition containing ergothioneine and theanine was prepared, and three panelists skilled in sensory evaluation performed a sensory evaluation. The compositions of Samples 1 to 5 (compositions containing ergothioneine and theanine) were prepared by mixing the amounts of (A) and (B) shown in Table 1. The weight ratio of (B) / (A) in the compositions of Samples 1 to 5 is shown in Table 1. Three panelists each placed the entire amount of the prepared composition (for example, 20 mg in total for Sample 1, consisting of 10 mg of ergothioneine and 10 mg of theanine) directly on their tongues and evaluated the intensity of the bitterness derived from ergothioneine and the intensity of the lingering aftertaste derived from theanine according to the following criteria.

[0038] (A) Evaluation criteria for bitterness derived from ergothioneine The bitterness of (A) ergothioneine alone (10 mg) was assigned a score of 5 (control 1), and the bitterness of not feeling any bitterness from ergothioneine was assigned a score of 1, with a total score of 1 to 5 (5-point scale). The evaluations of the three panelists were compiled, and the average score is shown in Table 1. 5 points: I strongly taste the bitterness derived from ergothioneine. 4 points: I can taste the bitterness derived from ergothioneine. 3 points: I can taste a slight bitterness derived from ergothioneine. 2 points: I don't really taste the bitterness derived from ergothioneine. 1 point: I don't taste the bitterness derived from ergothioneine.

[0039] (B) Evaluation criteria for persistent aftertaste derived from theanine The intensity of the persistent aftertaste from (B) theanine alone (10 mg) was rated as 5 points (control 2), and the absence of a persistent aftertaste derived from theanine was rated as 1 point, with a scale of 1 to 5 points (5-point scale). The evaluations of the three panelists were compiled, and the average score is shown in Table 1. 5 points: I strongly felt the lingering aftertaste derived from theanine. 4 points: I feel a lingering aftertaste from theanine. 3 points: I can slightly feel a lingering aftertaste from theanine. Points 2: I don't really notice the lingering aftertaste that comes from theanine. 1 point: No lingering aftertaste from theanine.

[0040] [Table 1]

[0041] <Result> We confirmed that combining ergothioneine and theanine suppresses the bitterness derived from ergothioneine. Regarding theanine, we confirmed that while theanine alone leaves a strong, lingering aftertaste that makes it difficult to consume, combining it with ergothioneine mitigates the severity of this aftertaste.

Claims

1. The following components (A) and (B): (A) Ergothioneine or a salt thereof, and (B) An oral composition containing theanine, The content of ergothioneine or its salt is 0.1 to 50% by weight, in terms of ergothioneine equivalent. An oral composition having a total theanine content of 5 to 90% by weight, calculated as L-glutamic acid-γ-ethylamide.

2. The composition according to claim 1, wherein the weight ratio ((B) / (A)) of component (B) (equivalent to L-glutamic acid-γ-ethylamide) to component (A) (equivalent to ergothioneine) is 2 to 90.

3. The composition according to claim 1 or 2, which is a food or beverage.

4. (A) A method for suppressing bitterness derived from ergothioneine or a salt thereof in an oral composition containing 0.1 to 50% by weight of ergothioneine in terms of ergothioneine equivalent, The process includes a step of formulating theanine such that the total content of (B) theanine in the oral composition is 5 to 90% by weight in terms of L-glutamic acid-γ-ethylamide. A method for suppressing the bitterness derived from ergothioneine or its salts.

5. The method according to claim 4, wherein component (B) is formulated in an oral composition such that the weight ratio ((B) / (A)) of component (B) (in terms of L-glutamic acid-γ-ethylamide) to component (A) (in terms of ergothioneine) is 2 to 90.

6. (A) an oral composition containing 0.1 to 50% by weight of ergothioneine or a salt thereof in terms of ergothioneine equivalent, wherein (B) theanine is used to suppress the bitterness derived from ergothioneine or a salt thereof, (B) The amount of theanine used is such that the total content of (B) theanine in the oral composition is 5 to 90% by weight in terms of L-glutamic acid-γ-ethylamide.