AU2022417968A1 - Oral composition and method for suppressing bitterness derived from ergothioneine - Google Patents
Oral composition and method for suppressing bitterness derived from ergothioneine Download PDFInfo
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- AU2022417968A1 AU2022417968A1 AU2022417968A AU2022417968A AU2022417968A1 AU 2022417968 A1 AU2022417968 A1 AU 2022417968A1 AU 2022417968 A AU2022417968 A AU 2022417968A AU 2022417968 A AU2022417968 A AU 2022417968A AU 2022417968 A1 AU2022417968 A1 AU 2022417968A1
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- Australia
- Prior art keywords
- ergothioneine
- theanine
- salt
- composition
- present
- Prior art date
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- SSISHJJTAXXQAX-ZETCQYMHSA-N L-ergothioneine Chemical compound C[N+](C)(C)[C@H](C([O-])=O)CC1=CNC(=S)N1 SSISHJJTAXXQAX-ZETCQYMHSA-N 0.000 title claims abstract description 108
- 229940093497 ergothioneine Drugs 0.000 title claims abstract description 103
- 239000000203 mixture Substances 0.000 title claims abstract description 80
- 235000019658 bitter taste Nutrition 0.000 title claims abstract description 44
- 238000000034 method Methods 0.000 title claims description 33
- DATAGRPVKZEWHA-YFKPBYRVSA-N N(5)-ethyl-L-glutamine Chemical compound CCNC(=O)CC[C@H]([NH3+])C([O-])=O DATAGRPVKZEWHA-YFKPBYRVSA-N 0.000 claims abstract description 136
- 229940026510 theanine Drugs 0.000 claims abstract description 64
- 150000003839 salts Chemical class 0.000 claims abstract description 59
- 235000013305 food Nutrition 0.000 claims description 24
- 235000013361 beverage Nutrition 0.000 claims description 16
- 239000000825 pharmaceutical preparation Substances 0.000 description 20
- 229940127557 pharmaceutical product Drugs 0.000 description 20
- 230000000694 effects Effects 0.000 description 16
- 206010013911 Dysgeusia Diseases 0.000 description 14
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- 238000011156 evaluation Methods 0.000 description 7
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- DATAGRPVKZEWHA-UHFFFAOYSA-N L-gamma-glutamyl-n-ethylamine Natural products CCNC(=O)CCC(N)C(O)=O DATAGRPVKZEWHA-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 230000006870 function Effects 0.000 description 4
- -1 inorganic acid salts Chemical class 0.000 description 4
- 229930014626 natural product Natural products 0.000 description 4
- DATAGRPVKZEWHA-RXMQYKEDSA-N (2r)-2-azaniumyl-5-(ethylamino)-5-oxopentanoate Chemical compound CCNC(=O)CC[C@@H](N)C(O)=O DATAGRPVKZEWHA-RXMQYKEDSA-N 0.000 description 3
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- JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 description 2
- 244000251953 Agaricus brunnescens Species 0.000 description 2
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- 235000015722 Cantharellus cibarius Nutrition 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
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- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 230000003712 anti-aging effect Effects 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
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- 235000020357 syrup Nutrition 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 235000019583 umami taste Nutrition 0.000 description 2
- 230000002087 whitening effect Effects 0.000 description 2
- 230000037373 wrinkle formation Effects 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 244000045069 Agrocybe aegerita Species 0.000 description 1
- 235000008121 Agrocybe aegerita Nutrition 0.000 description 1
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- ULYNPKLPOCHDAZ-JEDNCBNOSA-N CCN.CCNC(=O)CC[C@H](N)C(O)=O Chemical compound CCN.CCNC(=O)CC[C@H](N)C(O)=O ULYNPKLPOCHDAZ-JEDNCBNOSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 102000009127 Glutaminase Human genes 0.000 description 1
- 108010073324 Glutaminase Proteins 0.000 description 1
- 235000007328 Hericium erinaceus Nutrition 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 241001492261 Pleurotaceae Species 0.000 description 1
- 241000222350 Pleurotus Species 0.000 description 1
- 241000392443 Pleurotus citrinopileatus Species 0.000 description 1
- 235000007685 Pleurotus columbinus Nutrition 0.000 description 1
- 206010036618 Premenstrual syndrome Diseases 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 239000003674 animal food additive Substances 0.000 description 1
- 230000003064 anti-oxidating effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000013330 chicken meat Nutrition 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000012136 culture method Methods 0.000 description 1
- 230000016396 cytokine production Effects 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 235000015897 energy drink Nutrition 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 230000028993 immune response Effects 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 235000021056 liquid food Nutrition 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 230000007721 medicinal effect Effects 0.000 description 1
- 230000009245 menopause Effects 0.000 description 1
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 230000002633 protecting effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 238000009495 sugar coating Methods 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/17—Amino acids, peptides or proteins
- A23L33/175—Amino acids
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/142—Amino acids; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4172—Imidazole-alkanecarboxylic acids, e.g. histidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
- A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/18—Antioxidants, e.g. antiradicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Organic Chemistry (AREA)
- Food Science & Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Mycology (AREA)
- Epidemiology (AREA)
- Immunology (AREA)
- Nutrition Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Animal Husbandry (AREA)
- Zoology (AREA)
- Dermatology (AREA)
- Biochemistry (AREA)
- Botany (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
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.
Description
[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 of reducing bitterness derived from ergothioneine.
[0002] Ergothioneine is one of hydrophilic sulfur-containing amino acids and is known to have various physiological activities including an antioxidant ability. Regarding the physiological activities of ergothioneine, for example, Patent Literature 1 reports actions such as one that promotes the immune response activating cytokine production. Ergothioneine, which has various physiological activities, has been drawing attention recently for its use for foods, cosmetics, and pharmaceutical products.
[0003] Regarding a composition containing ergothioneine, for example, Patent Literature 2 discloses a method of reducing changes in smell and/or discoloration of a composition containing ergothioneine and/or a derivative thereof, the method including adjusting the pH of the composition, and/or adding a storage stabilizer to the composition.
CITATION LIST - Patent Literature
[0004]
Patent Literature 1: JP 2017-218431 A Patent Literature 2: JP 2012-241013 A
SUMMARY OF INVENTION - Technical Problem
[00051 As described above, since ergothioneine has useful physiological activities, foods such as supplements containing ergothioneine or a salt thereof are useful for maintaining or promoting health. However, ergothioneine or a salt thereof has a unique aroma and flavor, particularly bitterness (bitter taste) that stings the tongue, so that there is room for improvement in providing an oral composition containing ergothioneine or a salt thereof.
[00061 The present invention aims 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 present invention also aims to provide a method of reducing bitterness of an oral composition containing ergothioneine or a salt thereof, the bitterness being derived from ergothioneine or a salt thereof.
- Solution to Problem
[0007] As a result of extensive studies to solve the above problem, the present inventors found that a combination of ergothioneine or a salt thereof and theanine can effectively reduce the bitterness derived from ergothioneine or a salt thereof.
[00081 The present invention encompasses the following composition and the like. (1) An oral composition containing: a component (A); and a component (B), the component (A) being ergothioneine or a salt thereof, the component (B) being theanine. (2) The composition according to (1) above, wherein the weight ratio (B)/(A) of the component (B) in terms of L-glutamic acid-y-ethylamide to the component (A) in terms of ergothioneine is 2 to 90. (3) The composition according to (1) or (2) above, wherein the composition is a food or beverage. (4) A method of reducing bitterness of an oral composition containing (A) ergothioneine or a salt thereof, the bitterness being derived from (A) ergothioneine or a salt thereof, the method including a step of adding (B) theanine. (5) The method according to (4) above, wherein the component (B) is added such that a weight ratio (B)/(A) of the component (B) in terms of L-glutamic acid-y-ethylamide to the component (A) in terms of ergothioneine in the oral composition is 2 to 90. (6) Use of (B) theanine for reducing bitterness derived from (A) ergothioneine or a salt thereof.
- Advantageous Effects of Invention
[00091 The present invention can provide an oral composition containing ergothioneine or a salt thereof in which the bitterness derived from ergothioneine or a salt thereof is reduced. The present invention can provide a method of reducing bitterness of an oral composition containing ergothioneine or a salt thereof, the bitterness being derived from ergothioneine or a salt thereof.
[0010] The composition of the present invention is an oral composition containing (A) ergothioneine or a salt thereof and (B) theanine.
[0011] Ergothioneine is one of the sulfur-containing amino acids. In the present invention, ergothioneine is preferably L-ergothioneine. The salt of ergothioneine is not limited as long as it is a pharmacologically acceptable salt or a dietary acceptable salt, and it may be either an acid salt or a basic salt. Examples of the acid salt include inorganic acid salts such as hydrochloride, sulfate, nitrate, and phosphate; and organic acid salts such as acetate, citrate, maleate, malate, oxalate, lactate, succinate, fumarate, and propionate. Examples of the basic salt 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 a salt thereof is not limited in any way by its form, production method, or the like. Ergothioneine or a salt thereof that can be used may be a chemically synthesized product or a purified extract from a natural product. L-ergothioneine is abundant in golden/yellow oyster mushrooms (scientific name: Pleurotus cornucopiae var. citrinopileatus) belonging to the genus Pleurotus of the family Pleurotaceae. L-ergothioneine is also present in mushrooms such as common mushrooms (scientific name: Agaricus bisporus) including white button mushrooms, cremini mushrooms, and portabella mushrooms; grey oyster mushrooms (scientific name: Pleurotus ostreatus), shiitake (scientific name: Lentinula edodes), hen-of-the-woods (scientific name: Grifola Frondosa), reishi mushrooms (scientific name: Ganoderma lucidum), lion's mane mushrooms (scientific name: Hericium erinaceus), Yanagi-matsutake (scientific name: Agrocybe aegerita), girolles (scientific name: Cantharellus cibarius), porcini mushrooms (scientific name: Boletus edulis), and morel mushrooms (scientific name: Morchella esculenta). When L-ergothioneine is obtained from a natural product, preferably, it is extracted from a golden/yellow oyster mushroom, for example. Ergothioneine or a salt thereof can also be produced by microbial fermentation. Ergothioneine or a salt thereof may be in an isolated form. For example, the ergothioneine or a salt thereof may be one derived from a golden/yellow oyster mushroom. The composition of the present invention may or may not contain a dried golden/yellow oyster mushroom.
[0013] Theanine is one of the amino acids and is a derivative of glutamic acid. It is also one of umami components of tea. Theanine has a unique aroma and flavor (a lingering unpleasant aftertaste due to excessive umami with slight sweetness). The composition of the present invention reduces the bitterness derived from ergothioneine or a salt thereof, owing to the presence of theanine. This facilitates continuous intake of ergothioneine or a salt thereof. A combination of theanine and ergothioneine or a salt thereof can also reduce the aroma and flavor from theanine.
[0014] Specific examples of theanine include L-glutamic acid-y-ethylamide (L-theanine), L-glutamic acid-y methylamide, D-glutamic acid-y-ethylamide (D-theanine), and D-glutamic acid-y-methylamide. These types of theanine can be used alone or in combination of two or more. An embodiment in which theanine is at least one selected from the group consisting of L-glutamic acid-y ethylamide (L-theanine), L-glutamic acid-y-methylamide, D- glutamic acid-y-ethylamide (D-theanine), and D-glutamic acid-y-methylamide is one of preferred embodiments of the present invention. Theanine is more preferably L-theanine or D-theanine, still more preferably L-theanine.
[0015] Theanine for use in the present invention is not limited in any way by its form, production method, or the like. A chemically synthesized product may be used, or a purified extract from a natural product may be used. Specifically, theanine may be produced by a method such as a separation and purification method from tea leaves, a tissue culture method using tea cells, or a method using an enzyme reaction. One method using an enzyme reaction is a method in which a mixture of glutamine and ethylamine is reacted with glutaminase to obtain theanine. Theanine produced by such a method is also commercially available. Theanine obtained by enzyme reaction is suitably used as theanine (L-form) in the present invention. Such theanine may be, for example, one derived from green tea leaves. 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 ((B) in terms of L-glutamic acid-y ethylamide/(A) in terms of ergothioneine) of the component (B) (in terms of L-glutamic acid-y-ethylamide) to the component (A) (in terms of ergothioneine) is not limited and may be 1 to 100. When the weight ratio of the component (B) (in terms of L-glutamic acid-y-ethylamide) to the component (A) (in terms of ergothioneine) is in the above range, the bitterness derived from the component (A) can be sufficiently reduced. The weight ratio is preferably 2 to 90, so that the aroma and flavor derived from the component (B) can also be sufficiently reduced, making the composition more suitable for ingestion. The weight ratio is more preferably 3 to 80, still more preferably 5 to 70, particularly preferably 8 to 60, most preferably 10 to 50. Herein, regarding the expression for the amount in terms of ergothioneine or an expression similar thereto, in the case of ergothioneine, the expression refers to the amount of ergothioneine; whereas in the case of a salt of ergothioneine, the expression refers to a value obtained by multiplying the molar number of the salt by the molecular weight of ergothioneine.
[0017] The amount of ergothioneine or a salt thereof in the composition of the present invention is not limited and can be set according to the form of the composition or the like. The amount of ergothioneine or a salt thereof in terms of ergothioneine in the composition of the present invention is, for example, preferably 0.1 wt% or more, more preferably 0.5 wt% or more, still more preferably 0.6 wt% or more, yet still more preferably 0.8 wt% or more, particularly preferably 1 wt% or more and is also preferably 50 wt% or less, more preferably 40 wt% or less, still more preferably 30 wt% or less, yet still more preferably 20 wt% or less, particularly preferably 10 wt% or less. In one embodiment, the amount of ergothioneine or a salt thereof in terms of ergothioneine in the composition of the present invention is preferably 0.1 to 50 wt%, more preferably 0.5 to 40 wt%, still more preferably 0.6 to 30 wt%, yet still more preferably 0.8 to 20 wt%, particularly preferably 1 to 10 wt%. The amount of ergothioneine can be measured by high-performance liquid chromatography (HPLC).
[0018] The amount of theanine in the composition of the present invention is not limited and can be set according to the form of the composition or the like. The total amount of theanine in the composition of the present invention is, for example, preferably 1 wt% or more, more preferably 1.5 wt% or more, still more preferably 2 wt% or more, yet still more preferably 2.5 wt% or more, further still more preferably 5 wt% or more, particularly preferably 10 wt% or more, further particularly preferably 20 wt% or more and is also preferably 90 wt% or less, more preferably 85 wt% or less, still more preferably 80 wt% or less, yet still more preferably 75 wt% or less, further still more preferably 70 wt% or less, particularly preferably 60 wt% or less, further particularly preferably 50 wt% or less. In one embodiment, the total amount of theanine in terms of L-glutamic acid-y-ethylamide in the composition of the present invention is preferably 1 to 90 wt%, more preferably 1.5 to 85 wt%, still more preferably 2 to 80 wt%, yet still more preferably 2.5 to 75 wt%, further still more preferably 5 to 70 wt%, particularly preferably 10 to 60 wt%, further particularly preferably 20 to 50 wt%. When the composition contains two or more types of theanine, the total amount is the sum of these. The amount of theanine can be measured by HPLC.
[0019] The amount of ergothioneine or a salt thereof in terms of ergothioneine in the composition of the present invention per adult daily intake is preferably 1 to 100 mg, more preferably 2 to 50 mg, still more preferably 5 to 25 mg, particularly preferably 5 to 20 mg. The amount of theanine in terms of L-glutamic acid-y ethylamide in the composition of the present invention per adult daily intake is preferably 10 to 2000 mg, more preferably 20 to 1000 mg, still more preferably 50 to 500 mg.
[0020]
Ergothioneine or a salt thereof and theanine are compounds that are present in natural products and food and beverages and that have been consumed. Thus, for example, daily ingestion of ergothioneine or a salt thereof and theanine is less likely to cause problems in terms of safety. The present invention can provide a highly safe composition that is easy to ingest because the bitterness derived from ergothioneine or a salt thereof is reduced.
[0021] As described above, ergothioneine or a salt thereof is known to provide various physiological activities and health functions. Known examples include antioxidant action, brain function improving effect, anti-aging action, eye disease alleviating effect, whitening effect, UV absorbing effect, melanin production suppressing effect, active oxygen species scavenging effect, elastase activity inhibitory effect, wrinkle formation suppressing effect, anti-skin sagging effect, and autophagy promoting effect. Thus, the composition of the present invention can be suitably used for antioxidation, brain function improvement, anti-aging, eye disease, whitening, UV absorption, melanin production suppression, active oxygen species scavenging, elastase activity inhibition, wrinkle formation suppression, anti-skin sagging, and autophagy promotion.
[0022] Theanine is known to provide various health functions such as relaxing effect, stress suppressing effect, sleep promoting effect, brain nerve cell protecting effect, effect to improve memory and concentration, effect to prevent high blood pressure, effect to alleviate sensitivity to cold, and effect to alleviate symptoms of premenstrual syndrome and menopause. Since the composition of the present invention contains theanine, the composition can also be used to obtain the above effects provided by theanine.
[0023] The composition of the present invention is applicable for therapeutic use (medical use) and non therapeutic use (non-medical use). The "non-therapeutic" is a concept that does not include medical activities, i.e., a concept that does not include methods of surgery, therapy, or diagnosis of humans. The composition of the present invention can be provided in the form of a food or beverage, a pharmaceutical product, a quasi-pharmaceutical product, feed, or the like. The composition of the present invention may be a material, preparation, or the like to be added to a food or beverage, a pharmaceutical product, a quasi-pharmaceutical product, feed, or the like.
[0024] The composition of the present invention is an oral composition. Specifically, the oral composition may be a food or beverage, an oral pharmaceutical product, an oral quasi-pharmaceutical product, feed, or the like. A food or beverage or an oral pharmaceutical product is preferred, and a food or beverage is more preferred.
[0025] The composition of the present invention can contain optional additives and optional components in addition to ergothioneine or a salt thereof and theanine, as long as the effect of the present invention is not impaired. Such additives and components may be selected depending on the form of the composition, for example, and those generally usable in oral compositions such as food or beverages, pharmaceutical products, quasi-pharmaceutical products, and feed can be used. When the composition of the present invention is provided as a food or beverage, a pharmaceutical product, a quasi-pharmaceutical product, feed, or the like, any general method can be used for production. In one embodiment, the composition of the present invention may consist of ergothioneine or a salt thereof and theanine. The oral composition of the present invention may be in any form such as a solid (e.g., powder, granule, or tablet), liquid, or paste.
[0026] For example, when the composition of the present invention is provided as a food or beverage, components usable in food or beverages (e.g., food materials and optional food additives) can be added to ergothioneine or a salt thereof and theanine to provide various food or beverages. The food or beverage is not limited. Examples thereof include general food or beverages, health foods, health supplements, health drinks, foods with function claims, foods for specified health uses, and foods for the sick. The health foods, health supplements, foods with function claims, foods for specified health uses, and the like can be used in various forms of preparations such as fine granules, tablets, granules, powders, capsules, chewable tablets, dry syrups, syrups, liquid agents, beverages, energy drinks, and liquid foods.
[0027] When the composition of the present invention is provided as a pharmaceutical product or a quasi pharmaceutical product, for example, a pharmacologically acceptable carrier, an optional additive, or the like can be added to ergothioneine or a salt thereof and theanine to provide various dosage forms of pharmaceutical products or quasi-pharmaceutical products. Such a carrier, additive, or the like may be any pharmacologically acceptable one that can be used in pharmaceutical products or quasi pharmaceutical products. Examples thereof include excipients, binders, disintegrants, lubricants, antioxidants, and colorants. One or more of these can be used. Examples of the dosage form for oral administration of pharmaceutical products or quasi-pharmaceutical products include liquids, tablets, powders, fine granules, granules, sugar-coated tablets, capsules, suspensions, emulsions, and chewable tablets.
[0028] When the composition of the present invention is provided as feed, ergothioneine or a salt thereof and theanine are simply added to feed. The feed includes feed additives. Examples of the feed include livestock feed for animals such as cows, pigs, chickens, sheep, and horses; feed for small animals such as rabbits, rats, and mice; and pet food for animals such as dogs, cats, and birds.
[0029] The composition of the present invention may be ingested by or administered to any subject (administration subject). The administration subject is preferably a human or non-human mammal, more preferably a human.
[0030] The present invention also encompasses the following method: A method of reducing bitterness of an oral composition containing (A) ergothioneine or a salt thereof, the bitterness being derived from (A) ergothioneine, the method including a step of adding (B) theanine. In preparing an oral composition, the weight ratio ((B)/(A)) of the component (B) to the component (A) (in terms of ergothioneine) is adjusted to the above range, whereby an oral composition can be obtained in which the bitterness derived from ergothioneine or a salt thereof and the aroma and flavor derived from theanine are reduced. The weight ratio can be adjusted by, for example, adding the component (A) and/or the component (B).
[0031] The present invention also encompasses the following use: Use of (B) theanine for reducing bitterness derived from (A) ergothioneine or a salt thereof.
[0032] The above method and use make it possible to effectively reduce the bitterness derived from ergothioneine. In the above method and use, ergothioneine or a salt thereof and theanine as well as preferred embodiments thereof are as described above for the composition of the present invention. In the above method and use, the mixing ratio and percentage of used amount of the component (B) (in terms of L-glutamic acid-y-ethylamide) to the component (A) (in terms of ergothioneine) are not limited. Preferred ranges are the same as those of the weight ratio of the component (B) (in terms of L-glutamic acid-y-ethylamide) to the component (A) (in terms of ergothioneine) in the composition of the present invention.
[0033] The above method and use can reduce the bitterness derived from ergothioneine or a salt thereof. The above method and use may also be combined with a different bitterness reducing method. Examples of the different bitterness reducing methods include a formulation method including adding a sweetener or flavoring agent to a component having bitterness, a formulation method including sugar-coating a component having bitterness, and a formulation method including encapsulating a component having bitterness.
[0034] The numerical range defined by the lower limit and the upper limit herein, i.e., "the lower limit to the upper limit", includes the lower limit and the upper limit. For example, the range defined by "1 to 2" means 1 or more and
2 or less, with 1 and 2 being inclusive. Herein, the range may be any combination of any upper limit and any lower limit.
[00351 The present invention is described in further detail below with reference to Examples. The present invention is not limited to these Examples.
[00361 The following materials are used in an evaluation test described below. (A) Ergothioneine: raw material containing 100% L ergothioneine (B) Theanine: raw material containing 100% L-theanine
[0037] <Example 1: Aroma and flavor evaluation test on composition containing ergothioneine and theanine> Compositions containing ergothioneine and theanine were prepared and subjected to sensory evaluation by three panelists expertized in sensory evaluation. The components (A) and (B) in the amounts shown in Table 1 were mixed to prepare compositions (compositions containing ergothioneine and theanine) of samples 1 to 5. Table 1 shows the weight ratio (B)/(A) in the compositions of the samples 1 to 5. The three panelists placed the whole amount of the composition prepared (for example, in the case of the sample 1, 10 mg ergothioneine and 10 mg theanine, i.e., 20 mg in total) directly on the tongue. The intensity of the bitterness derived from ergothioneine, and the intensity of the lingering aftertaste derived from theanine were evaluated based on the following criteria.
[00381 (A) Criteria for bitterness derived from ergothioneine Five points were given to the intensity of the bitterness of the (A) ergothioneine alone (10 mg) (control 1). One point was given to the case where no bitterness derived from ergothioneine was felt. The intensity was evaluated with one to five points (five-point scale). Evaluation results by the three panelists were collected. Table 1 shows the average results (points) 5 points: The bitterness derived from ergothioneine is strongly felt. 4 points: The bitterness derived from ergothioneine is felt. 3 points: The bitterness derived from ergothioneine is slightly felt. 2 points: The bitterness derived from ergothioneine is not much felt. 1 point: The bitterness derived from ergothioneine is not felt.
[00391 (B) Criteria for lingering aftertaste derived from theanine Five points were given to the lingering aftertaste of (B) theanine alone (10 mg) (control 2). One point was given to the case where no lingering aftertaste derived from theanine was felt. The lingering aftertaste was evaluated with one to five points (five-point scale). Evaluation results by the three panelists were collected. Table 1 shows the average results (points) 5 points: The lingering aftertaste derived from theanine is strongly felt. 4 points: The lingering aftertaste derived from theanine is felt. 3 points: The lingering aftertaste derived from theanine is slightly felt. 2 points: The lingering aftertaste derived from theanine is not much felt. 1 point: The lingering aftertaste derived from theanine is not felt.
[0040]
[Table 1] Amount added (mg) Ratio Evaluation results (points) Bitterness derived Lingering (A) Ergothioneine (B) Theanine (B)/(A) aftertaste derived from (B) Control 1 10 0 0 5.0 Sample 1 10 10 1 4.0 1.0 Sample 2 10 100 10 2.7 2.3 Sample 3 10 500 50 1.7 3.3 Sample 4 10 1000 100 1.0 4.3 Sample 5 20 200 10 2.3 2.7 Control 2 0 10 - - 5.0
[0041] <Results> The results confirm that a combination of ergothioneine and theanine reduces the bitterness derived from ergothioneine. When theanine is ingested alone, it has a strong lingering aftertaste and is thus not suitable for ingestion. However, the results confirm that a combination of theanine with ergothioneine reduces the degree of lingering aftertaste.
Claims (6)
- Claim 1. An oral composition comprising: a component (A); and a component (B), the component (A) being ergothioneine or a salt thereof, the component (B) being theanine.
- Claim 2. The composition according to claim 1, wherein a weight ratio (B)/(A) of the component (B) in terms of L-glutamic acid-y-ethylamide to the component (A) in terms of ergothioneine is 2 to 90.
- Claim 3. The composition according to claim 1 or 2, wherein the composition is a food or beverage.
- Claim 4. A method of reducing bitterness of an oral composition containing (A) ergothioneine or a salt thereof, the bitterness being derived from (A) ergothioneine or a salt thereof, the method comprising: a step of adding (B) theanine.
- Claim 5. The method according to claim 4, wherein the component (B) is added such that a weight ratio (B)/(A) of the component (B) in terms of L-glutamic acid-y-ethylamide to the component (A) in terms of ergothioneine in the oral composition is 2 to 90.
- Claim 6. Use of (B) theanine for reducing bitterness derived from (A) ergothioneine or a salt thereof.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| JP2021209563 | 2021-12-23 | ||
| JP2021-209563 | 2021-12-23 | ||
| PCT/JP2022/046208 WO2023120367A1 (en) | 2021-12-23 | 2022-12-15 | Oral composition and method for suppressing bitterness derived from ergothioneine |
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| AU2022417968A1 true AU2022417968A1 (en) | 2024-06-20 |
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| JP (1) | JPWO2023120367A1 (en) |
| KR (1) | KR20240127427A (en) |
| CN (1) | CN118414094A (en) |
| AU (1) | AU2022417968A1 (en) |
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| JP2012241013A (en) | 2011-05-20 | 2012-12-10 | Koei Kogyo Kk | Method for controlling flavor change and/or discoloration of composition containing ergothioneine and/or derivative of the same |
| JP6121597B1 (en) | 2016-06-09 | 2017-04-26 | 株式会社スリービー | Immune response activated cytokine production promoter and Th17 cell differentiation promoter |
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