WO2021256473A1 - 抗コロナウイルス剤 - Google Patents

抗コロナウイルス剤 Download PDF

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Publication number
WO2021256473A1
WO2021256473A1 PCT/JP2021/022744 JP2021022744W WO2021256473A1 WO 2021256473 A1 WO2021256473 A1 WO 2021256473A1 JP 2021022744 W JP2021022744 W JP 2021022744W WO 2021256473 A1 WO2021256473 A1 WO 2021256473A1
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WIPO (PCT)
Prior art keywords
tea
tea leaves
coronavirus
cells
agent according
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Ceased
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PCT/JP2021/022744
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English (en)
French (fr)
Japanese (ja)
Inventor
修 松田
えり子 扇谷
政春 新屋
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Kyoto Prefectural PUC
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Kyoto Prefectural PUC
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Priority to JP2022531844A priority Critical patent/JPWO2021256473A1/ja
Publication of WO2021256473A1 publication Critical patent/WO2021256473A1/ja
Anticipated expiration legal-status Critical
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
    • A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
    • A01N65/08—Magnoliopsida [dicotyledons]
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P1/00—Disinfectants; Antimicrobial compounds or mixtures thereof
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23F—COFFEE; TEA; THEIR SUBSTITUTES; MANUFACTURE, PREPARATION, OR INFUSION THEREOF
    • A23F3/00—Tea; Tea substitutes; Preparations thereof
    • A23F3/16—Tea extraction; Tea extracts; Treating tea extract; Making instant tea
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • 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
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • 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
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/82—Theaceae (Tea family), e.g. camellia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783—Angiosperms [Magnoliophyta]
    • A61K8/9789—Magnoliopsida [dicotyledons]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations

Definitions

  • the present invention relates to an anti-coronavirus agent and the like.
  • Coronavirus is a species of virus belonging to the subfamily Coronaviridae of the Coronaviridae family, and is a plus-strand RNA virus that infects humans and animals and causes respiratory, digestive, vascular, or neurological disorders. Coronavirus can be transmitted from any infected host animal and cause a large-scale infectious disease in humans. Examples of coronaviruses include SARS coronavirus 1 (SARS-CoV-1), which was prevalent in 2002 and 2003, and Middle East respiratory syndrome coronavirus (MERS-CoV). Recently, a worldwide epidemic of SARS coronavirus 2 (SARS-CoV-2) has occurred, and since the treatment technology has not been established, great damage continues in various fields such as medical treatment and economy.
  • SARS-CoV-1 SARS coronavirus 1
  • MERS-CoV Middle East respiratory syndrome coronavirus
  • An object of the present invention is to provide an anti-coronavirus agent, particularly an anti-coronavirus agent against SARS-CoV-2.
  • the present inventor has described above if it is an anti-corona virus agent containing at least one selected from the group consisting of tea extract, catechin compound, and theaflavin compound. I found that I could solve the problem.
  • the present inventor has completed the present invention as a result of further research based on this finding. That is, the present invention includes the following aspects.
  • Item 1 An anti-coronavirus agent containing at least one selected from the group consisting of tea extract, catechin compound, and theaflavin compound.
  • Item 2. The coronavirus agent according to Item 1, wherein the coronavirus is SARS-CoV-2.
  • Item 3 The anti-coronavirus agent according to Item 1 or 2, wherein the tea extract is tea or a concentrate thereof.
  • the tea extract is at least one extract selected from the group consisting of matcha tea leaves, roasted tea leaves, roasted tea leaves, new tea leaves, black tea leaves, pouer tea leaves, and oolong tea leaves.
  • the anti-corona virus agent according to any one of Items 1 to 3.
  • Item 5 The anti-coronavirus agent according to any one of Items 1 to 4, wherein the tea extract is at least one extract selected from the group consisting of matcha tea leaves, roasted tea leaves, and black tea leaves.
  • Item 6 The anti-coronavirus agent according to any one of Items 1 to 5, which contains epigallocatechin gallate as the catechin compound.
  • Item 7. The anti-coronavirus agent according to any one of Items 1 to 6, which is used for application to a living body.
  • Item 8 The anti-coronavirus agent according to Item 7, which is a pharmaceutical, cosmetics, food composition, food additive, disinfectant or detergent.
  • Item 9 The anti-coronavirus agent according to Item 7 or 8, which is a preventive or therapeutic agent for COVID-19.
  • Item 10. The anti-coronavirus agent according to any one of Items 1 to 6, which is used for applying to articles.
  • Item 11 The anti-coronavirus agent according to Item 10, which is a disinfectant or a cleaning agent.
  • an anti-coronavirus agent particularly an anti-coronavirus agent against SARS-CoV-2.
  • the results of Test Example 4 are shown.
  • the vertical axis is the CPE suppression rate.
  • the abbreviations on the horizontal axis are as follows. EC: (-)-Epigallocatechin, ECg: (-)-Epigallocatechin gallate, EGC: (-)-Epigallocatechin, EGCg: (-)-Epigallocatechin gallate.
  • the results of Test Example 5 are shown.
  • the vertical axis is the CPE suppression rate.
  • the results of Test Example 6 are shown.
  • the vertical axis is the cell death suppression rate.
  • the abbreviations on the horizontal axis are as follows.
  • the present invention in one aspect thereof, is an anti-coronavirus agent containing at least one selected from the group consisting of a tea extract, a catechin compound, and a theaflavin compound (referred to as "the agent of the present invention” in the present invention. It may be shown.). This will be described below.
  • Active ingredient is at least one selected from the group consisting of tea extract, catechin compound, and theaflavin compound.
  • the tea extract is not particularly limited as long as it is obtained by extracting from a tea plant.
  • tea plant preferably include Camellia plants, and particularly preferably Camellia sinensis.
  • the part of the tea plant used for extraction is not particularly limited, and examples thereof include leaves and branches. Among these, leaves are preferably mentioned.
  • the tea plant used for extraction may be, for example, an unfermented one in which the enzyme is inactivated by heat treatment (for example, steaming, frying, roasting on fire, sun-drying, etc.) after harvesting, or the enzyme. It may be fermented (semi-fermented) to some extent by an enzyme by weakening the inactivation intensity of the enzyme or delaying the timing thereof, or it may not weaken the inactivation intensity of the enzyme or inactivate the enzyme. It may be completely fermented by an enzyme or the like, or it may be fermented by adding a microorganism such as lactic acid bacteria.
  • heat treatment for example, steaming, frying, roasting on fire, sun-drying, etc.
  • the tea plant used for extraction is preferably tea leaves.
  • the tea leaves include matcha tea leaves, roasted tea leaves, roasted tea leaves, new tea leaves, black tea leaves, pouer tea leaves, oolong tea leaves and the like.
  • examples of tea leaves include green tea leaves (for example, Tamaro, Bancha, brown rice tea, etc.), white tea leaves, yellow tea leaves, black tea leaves, flower tea leaves, and the like.
  • examples of the tea leaves include matcha tea leaves, roasted tea leaves, roasted tea leaves, new tea leaves, tea leaves, pouer tea leaves, oolong tea leaves, and the like, and more preferably matcha tea leaves, roasted tea leaves, and roasted tea leaves.
  • examples thereof include tea leaves of tea, tea leaves of tea, tea leaves of oolong tea, and particularly preferably tea leaves of matcha, tea leaves of roasted tea, and tea leaves of tea.
  • pretreatments such as steaming, rough kneading, kneading, medium kneading, fine kneading, drying, and squeezing can be performed.
  • the tea plant may be one kind alone or a combination of two or more kinds.
  • the extraction solvent is not particularly limited.
  • Extraction solvents include water; lower monohydric alcohols such as methanol, ethanol, propanol and butanol; liquid polyhydric alcohols such as glycerin, propylene glycol and 1,3-butylene glycol; ketones such as acetone; ethers such as ethyl ether.
  • Esters such as methyl acetate, ethyl acetate, propyl acetate, butyl acetate; supercritical carbon dioxide and the like.
  • the extraction solvent may be one kind alone or a combination of two or more kinds. Examples of the extraction solvent include a solvent containing water (for example, 50% by mass or more, 70% by mass or more, 80% by mass or more, 90% by mass or more, or 95% by mass or more), and water is particularly preferable. Be done.
  • the temperature of the solvent at the time of extraction is not particularly limited, but is, for example, 4 to 100 ° C, preferably 50 to 100 ° C, and more preferably 60 to 100 ° C.
  • the temperature can be appropriately set according to the type of tea plant and the like.
  • the amount of the extraction solvent used is not particularly limited, but is, for example, 1 to 2000 parts by mass, 5 to 1000 parts by mass, or 10 to 500 parts by mass with respect to 1 part by mass of the tea plant.
  • the amount used can be appropriately set according to the type of tea plant and the like.
  • the extraction time varies depending on the extraction method, solvent, temperature, etc., and is not particularly limited.
  • the extraction time is, for example, 10 seconds to 1 hour, or 30 seconds to 10 minutes.
  • the extraction time can be appropriately set according to the type of tea plant and the like.
  • the extraction residue can be removed as needed.
  • the method for removing is not particularly limited, and for example, a method such as free fall, centrifugation, or filtration can be adopted by one type or a combination of two or more types.
  • the properties of the tea extract are not particularly limited and may be, for example, liquid, slurry, paste, solid, powder or the like.
  • the tea extract may be the extract itself, a concentrate of the extract (including a dried product), or a mixture thereof.
  • the tea extract is preferably tea or a concentrate thereof.
  • Tea is a beverage obtained by extracting a tea plant with a solvent suitable for drinking (usually water), and is not particularly limited as long as this is the case.
  • the tea extract may be one kind alone or a combination of two or more kinds.
  • the catechin compound is not particularly limited as long as it is a derivative in which flavan-3-ol is substituted with a plurality of hydroxy groups or an aromatic carboxylic acid (for example, gallic acid) ester thereof.
  • Examples of the catechin compound include catechin (C), epicatechin (EC), gallocatechin (GC) or epigallocatechin (EGC), which is a free catechin, or catechin gallate (CG), which is an ester type (gallate type) catechin.
  • Catchin gallate (ECG), gallocatechin gallate (GCG), epigallocatechin gallate (EGCG) and the like can be mentioned.
  • epigallocatechin gallate is particularly preferable from the viewpoint of antiviral action (particularly, antiviral action against SARS-CoV-2).
  • the catechin compound may be used alone or in combination of two or more.
  • the catechin compound may be obtained from a tea extract and used, or may be obtained from a plant or food other than tea and used. In that case, it may be obtained by adding some processes such as concentration and / or fractionation and / or purification. Moreover, you may synthesize and use a catechin compound.
  • the theaflavin compound is not particularly limited as long as it is theaflavin and its derivatives.
  • theaflavin compounds include theaflavin, theaflavin-3-gallate (eg, theaflavin-3-O-galat, theaflavin-3'-O-galat), and theaflavin digalat (teaflavin-3-3'-di-O-gallate). ), 3-Isotheaflavin-3-gallate and the like.
  • the theaflavin compound is preferably theaflavin-3-3'-di-O-galat, theaflavin-3'-O-galat, theaflavin from the viewpoint of antiviral action (particularly, antiviral action against SARS-CoV-2). -3-O-gallate and the like, more preferably theaflavin-3-3'-di-O-gallate, theaflavin-3'-O-gallate and the like, and particularly preferably theaflavin-3-3'- Theaflavin is mentioned.
  • the theaflavin compound may be used alone or in combination of two or more.
  • the theaflavin compound may be obtained from a tea extract and used, or may be obtained from a plant or food other than tea and used. In that case, it may be obtained by adding some processes such as concentration and / or fractionation and / or purification. Moreover, the theaflavin compound may be synthesized and used.
  • tea extract is particularly preferable.
  • the active ingredient may be one kind alone or a combination of two or more kinds.
  • the target coronavirus of the agent of the present invention is not particularly limited as long as it is a virus belonging to the subfamily Orthocoronavirus.
  • the coronavirus include alpha coronavirus genus, beta coronavirus genus, gamma coronavirus genus, delta coronavirus genus, and the like, and among these, beta coronavirus genus is preferable.
  • the beta coronavirus genus include SARS-related coronavirus (SARSr-CoV), coronavirus HKU1, and MERS coronavirus, and among these, SARSr-CoV is preferable.
  • SARSr-CoV include SARS-CoV-2 and SARS-CoV-1, and among these, SARS-CoV-2 is preferable.
  • the agent of the present invention can be particularly preferably used for SARS-CoV-2.
  • the agent of the present invention can exert an antiviral effect against coronavirus.
  • the antiviral action include a virus infection suppressing action, a virus-induced cell death suppressing action, a virus inactivating action, a virus growth suppressing action, a virus sprouting suppressing action, and a virus resistance-inducing action.
  • it can also be used as a prophylactic or therapeutic agent for coronavirus infections (particularly COVID-19).
  • the agent of the present invention can be widely used in various fields requiring antiviral properties.
  • the agent of the present invention can be used in various fields such as industry, cleaning, medical care, food, and daily necessities.
  • the use of the agent of the present invention is mainly divided into a use applied to a living body and a use applied to an article described later.
  • Applications for living organisms include, for example, pharmaceuticals, cosmetics, food compositions (including health foods, health enhancers, dietary supplements (supplements, etc.)), food additives, disinfectants, and cleaning agents. And so on.
  • the application target in this case is not particularly limited, and examples thereof include various mammals such as humans, monkeys, mice, rats, dogs, cats, rabbits, pigs, horses, cows, sheep, goats, and deer.
  • the agent of the present invention By applying the agent of the present invention to a living body, it is possible to exert an antiviral effect at a site where the active ingredient comes into contact.
  • the form of the agent of the present invention is not particularly limited, and the form usually used in each application can be taken depending on the use of the agent of the present invention.
  • the use is pharmaceutical, for example, an injection, a drip, a mouthwash, an inhalant, a patch (a plaster, a tape such as a plaster (reservoir type, matrix type, etc.), a pap, a patch).
  • a plaster a tape such as a plaster (reservoir type, matrix type, etc.)
  • a pap a patch
  • Suitable for oral ingestion of including), rounds, granules, fine granules, powders, hard capsules, soft capsules, dry syrups, liquids (including drinks, suspensions and syrups), jelly, etc.
  • examples thereof include a formulation form (oral formulation form), a tube nutritional supplement, an enteral nutritional supplement, a nasal catheter preparation, an esophageal fistula catheter preparation, and a gastric fistula catheter preparation.
  • Examples of the form include liquids, gels, creams, ointments, sprays, sticks, etc. when the use is cosmetics.
  • liquid, gel or solid foods such as juices, soft drinks, tea, soups, soy milk and other beverages, salad oils, dressings, yogurts, jellies, puddings, sprinkles, etc.
  • dairy products eg, powder, liquid, gel, solid, etc.
  • bread e.g., cookies, etc.
  • a health enhancer, a dietary supplement supplied, etc.
  • it includes, for example, tablets (intraoral disintegrating tablets, chewable tablets, effervescent tablets, troches, jelly-like drops, etc.). ), Rounds, granules, fine granules, powders, hard capsules, soft capsules, dry syrups, liquids (including suspensions and syrups), jelly and the like.
  • a disinfectant or cleaning agent for example, a liquid (solution, emulsion, suspension, spray, etc.), a semi-solid (gel, cream, paste, etc.), a solid (tablet, particulate agent, etc.) It can take any form such as a capsule, a film, a kneaded product, a molten solid, a waxy solid, an elastic solid, etc.).
  • dentifrice dentifrice, liquid dentifrice, liquid dentifrice, powdered dentifrice, etc.
  • mouthwash coating agent
  • patch mouth refreshing agent
  • food for example, chewing gum, candy, candy, gummies, films, troches, etc.
  • a spray-type nasal drop or the like can be mentioned.
  • soaps, body soaps, shampoos, conditioners, sprays and the like can be mentioned.
  • the agent of the present invention may further contain other components, if necessary.
  • the other components are not particularly limited as long as they are components that can be blended in, for example, pharmaceuticals, cosmetics, disinfectants, detergents, etc., but for example, bases, carriers, solvents, dispersants, emulsifiers, buffers, etc. Examples include stabilizers, excipients, binders, disintegrants, lubricants, thickeners, moisturizers, colorants, fragrances, chelating agents and the like.
  • the buffering agent is not particularly limited, and an appropriate buffering agent that is acceptable can be adopted depending on the intended use.
  • Preferred examples include a phosphate buffer solution and an acetic acid buffer solution.
  • the content of the active ingredient of the agent of the present invention depends on the type, use, mode of use, application target, state of application target, etc. of the active ingredient, and is not limited, but is, for example, 0.000001 to 100% by weight. It can be preferably 0.01 to 50% by weight.
  • the amount of the agent of the present invention applied is not particularly limited as long as it is an effective amount that exerts a desired effect, and is usually 0.1 to 0.1 per day as the weight of the active ingredient. 1000 mg / kg body weight.
  • the above dose is preferably administered once a day or divided into 2 to 3 times, and may be appropriately increased or decreased depending on the age, pathological condition, and symptom.
  • Applications applied to articles examples include disinfectants, detergents, and the like.
  • the application target in this case is not particularly limited, and examples thereof include industrial products and raw materials thereof used in various fields.
  • articles include masks, face masks, gloves and the like.
  • OA equipment home appliances, air conditioning equipment, vacuum cleaners, desks, chairs, sofas, benches, windows, leather, handles, seats, automatic ticket gates, automatic ticket vending machines, vending machines, doors, fences, handrails, tableware, Cooking utensils, packaging films, packaging bags, bottles, bottles, packaging packs, sinks, toilet bowls, stationery, books, shelves, toothbrushes, mirrors, air conditioning filters, masks, coats, jackets, trousers, skirts, shirts, knit shirts, blouses, Sweaters, cardigans, nightwear, underwear, underwear, diapers, supporters, socks, tights, stockings, hats, scarves, mufflers, scarves, stalls, gloves, clothes linings, clothes cores, clothes batting, work clothes, Examples include clothing such as uniforms and school children's uniforms, curtains, ami doors, duvets, duvet cotton, duvet covers, pillowcases, sheets, mats, carpets, towels, handker
  • the agent of the present invention By applying the agent of the present invention to an article, it is possible to exert an antiviral effect at a site where the active ingredient comes into contact.
  • the site where the active ingredient comes into contact is not limited to the site on the article, but also includes the site in the living body when the article is applied to a living body or the like.
  • the dosage form of the agent of the present invention is not particularly limited and can be appropriately selected according to its intended use.
  • the dosage form include liquids such as liquids, emulsions, suspensions, dispersants, sprays and aerosols; solid or semi-solids such as wettable powders, powders, granules, fine granules and flowables. Be done. It can be applied or coated on various articles.
  • the agent of the present invention may further contain other components, if necessary.
  • the other components are not particularly limited as long as they are components that can be blended in, for example, detergents and disinfectants for articles, but for example, bases, carriers, solvents, dispersants, emulsifiers, buffers, stabilizers, etc. , Excipients, binders, disintegrants, lubricants, thickeners, moisturizers, colorants, fragrances, chelating agents and the like.
  • the buffering agent is not particularly limited, and an appropriate buffering agent that is acceptable can be adopted depending on the intended use.
  • Preferred examples include a phosphate buffer solution and an acetic acid buffer solution.
  • the content of the active ingredient of the agent of the present invention depends on the type, use, mode of use, application target, state of application target, etc. of the active ingredient, and is not limited, but is, for example, 0.000001 to 100% by weight. It can be preferably 0.001 to 50% by weight.
  • the tea in the following reference example was prepared according to the method described on the product packaging.
  • Reference example 1 Preparation of Matcha Matcha tea leaf powder (Matcha in front, manufactured by Ochanomaru Kosha) was mixed with 1.5 g of hot water at 70 ° C and stirred several times. The tea leaves were removed by filtration through 100 mesh and allowed to stand until the temperature reached room temperature. The supernatant was filtered through a filter having a pore size of 0.22 ⁇ m to obtain matcha. It was stored at 4 ° C. until it was used in Test Examples 1 and 2 described later.
  • Reference example 3 Preparation of roasted green tea 5 g of roasted green tea leaves (organic roasted green tea, manufactured by Ocha no Maruyuki Co., Ltd.) and 100 mL of boiling water were mixed and allowed to stand for 60 seconds. The tea leaves were removed by filtration through 100 mesh and allowed to stand until the temperature reached room temperature. The supernatant was filtered through a filter having a pore size of 0.22 ⁇ m to obtain roasted green tea. It was stored at 4 ° C until it was used in Test Example 2 described later.
  • Reference example 4 Preparation of new tea 5 g of tea leaves (made by a tea farmer, picked in April 2nd year of Reiwa, manufactured by Tsubo City Tea Chapo Co., Ltd.) and 100 mL of hot water at 70 ° C were mixed and allowed to stand for 60 seconds. The tea leaves were removed by filtration through 100 mesh and allowed to stand until the temperature reached room temperature. The supernatant was filtered through a filter having a pore size of 0.22 ⁇ m to obtain new tea. It was stored at 4 ° C. until it was used in Test Examples 1 and 2 described later.
  • Reference example 7 Preparation of oolong tea 4 g of oolong tea leaves (oolong tea tea bar, manufactured by Tsubo City Chachapo Co., Ltd.) and 1 L of boiling water were mixed and allowed to stand for 15 minutes. The tea leaves were removed by filtration through 100 mesh and allowed to stand until the temperature reached room temperature. The supernatant was filtered through a filter having a pore size of 0.22 ⁇ m to obtain oolong tea. It was stored at 4 ° C. until it was used in Test Examples 1 and 2 described later.
  • Reference example 8 Preparation of pot water After boiling purified water for drinking, it was cooled to room temperature. It was stored at 4 ° C. until it was used in Test Examples 1 and 2 described later.
  • Test example 1 Evaluation test of antiviral effect 1 The antiviral activity of each sample of Reference Examples 1 to 2 and 4 to 8 (storage period at 4 ° C.: 11 days) was evaluated as follows.
  • Day -1 Vero E6 / TMPRSS2 cells were seeded on a 96-well plate at 5.0 x 10 4 cells / 100 ⁇ L.
  • the medium is DMEM medium supplemented with 5% fetal bovine serum. Incubated for 24 hours at 37 ° C., 5% CO 2 / 95% air.
  • Test example 2 Evaluation test of antiviral effect 2
  • Sample O Reference Examples 1 to 2 and 4 to 8, storage period at 4 ° C: 20 days
  • Sample N Reference Examples 2 to 8, storage period at 4 ° C: 2 hours
  • Test example 3 Antiviral evaluation test Day -1 Vero E6 / TMPRSS2 cells were seeded on a 96-well plate at 5.0 x 10 4 cells / 100 ⁇ L.
  • the medium is DMEM medium supplemented with 5% fetal bovine serum. Incubated for 24 hours at 37 ° C., 5% CO 2 / 95% air.
  • Test example 4 Antiviral evaluation test Day -1 Vero E6 / TMPRSS2 cells were seeded on a 96-well plate at 5.0 x 10 4 cells / 100 ⁇ L. The medium is DMEM medium supplemented with 5% fetal bovine serum. Incubated for 24 hours at 37 ° C., 5% CO 2 / 95% air.
  • a virus infection score was given for each of the three Triplewell wells as shown in Table 5. After that, the average value of the three wells was calculated.
  • the CPE suppression rate was calculated as follows.
  • Test Example 5 Day -1 Vero E6 / TMPRSS2 cells were seeded on a 96-well plate at 5.0 x 10 4 cells / 100 ⁇ L. Incubated for 24 hours at 37 ° C., 5% CO 2 / 95% air.
  • Theaflavin-3-O-gallate, Theaflavin-3'-O-gallate, Theaflavin-3-3'-di-O-gallate (purchased from Nagara Science) are diluted with 10% FBS-containing medium (Theaflavin-3-O).
  • -gallate is 10mM, 5mM;
  • Theaflavin-3'-O-gallate is 10mM, 5mM, 2.5mM;
  • Theaflavin-3-3'-di-O-gallate is 10mM, 5mM, 2.5mM, 1.25mM), 2 ⁇ L SARS-CoV-2 (30TCID 50 / 100 ⁇ L) was added to 200 [mu] L, were incubated for 5 min.
  • the final concentration of each drug is 100 ⁇ M, 50 ⁇ M for Theaflavin-3-O-gallate; 100 ⁇ M, 50 ⁇ M, 25 ⁇ M for Theaflavin-3'-O-gallate; 100 ⁇ M, 50 ⁇ M for Theaflavin-3-3'-di-O-gallate. , 25 ⁇ M, 12.5 ⁇ M.
  • the culture supernatant was discarded from the 96-well plate in which the cells were seeded and cultured on the previous day (Day -1), 100 ⁇ L of each virus solution was added (Quadruplicate), and the temperature was 37 ° C., 5% CO 2 / 95% under air. Incubated for 72 hours.
  • a virus infection score was given for each of the four Quadruplicate wells as shown in Table 6. After that, the average value of the four wells was calculated.
  • the CPE suppression rate was calculated as follows.
  • the results are shown in Fig. 2.
  • Theaflavin-3-O-gallate, Theaflavin-3'-O-gallate, and Theaflavin-3-3'-di-O-gallate were all found to suppress SARS-CoV-2 infection.
  • Test Example 6 Method Day -1 Vero E6 / TMPRSS2 cells were seeded on a 96-well plate at 5.0 x 10 4 cells / 100 ⁇ L. Incubated for 24 hours at 37 ° C., 5% CO 2 / 95% air.
  • Day 0 Day (Day -1) to Discard the culture supernatant from the 96 well plates was started by seeding cells cultured and SARS-CoV-2 a (30 TCID 50 / 100 ⁇ L) was 100 [mu] L added. Incubated at 37 ° C., 5% CO 2 / 95% air for 1 hour. After 1 hour, discard the virus solution and add 100 ⁇ L of EC, ECG, EGC, EGCG (final concentrations 200 ⁇ M, 100 ⁇ M, 50 ⁇ M, 25 ⁇ M) diluted in 0.5% FBS-containing medium (Quadruplicate), 37 ° C, 5%. Incubated for 72 hours under CO 2 / 95% air.
  • Test Example 7 Add an equal amount of serum-free (SF) 2X DMEM to the sample (EGCG or TFDG (theaflavin-3,3'-di-O-gallate)) solution to adjust the osmotic pressure, and then use SF DMEM (MS) in two steps. Diluted and used immediately. 10 ⁇ l of SARS-CoV-2 (1.5 X 10 ⁇ 6/50 ⁇ l) was added to 100 ⁇ l of Sample solution of each concentration or SF DMEM (MS) (control), and the mixture was allowed to stand at room temperature for 1 minute.
  • SF serum-free
  • MS SF DMEM
  • the supernatant was removed from a 96-well plate in which Vero E6 / TMPRSS2 cells were sown at 5 X 10 ⁇ 4/100 ⁇ l / well and cultured for 15 hours the day before, and 50 ⁇ l of the above virus / sample solution was added (MOI 3). After 1h adsorption, the virus solution was removed and MS was added at 100 ⁇ l / well. Incubated for 30 hours. The viability of the cells was quantified by the following method. Medium was removed from the Plate and washed with PBS. 20% of Cell Count Reagent SF (Nacalai) was mixed with phenol red-free medium, 50 ⁇ l / well was added to the cells, and the cells were cultured for 50 minutes.
  • a well in which only the reagent mixture was added to the well in which the cells were not cultured was also prepared. After completion of the reaction, 20 ⁇ l / well of 10% SDS was added to inactivate the virus remaining in the well. The absorbance at a wavelength of 450 nm was measured with a plate reader. The measurement was performed with tetraplicate.
  • Test Example 8 Saliva from 5 healthy subjects was purchased from Lee Biosolutions (Maryland Heights, MO, USA) and sterilized by UV irradiation for 30 minutes. Was added SARS-CoV-2 only 3.0 ⁇ 10 5 TCID 50/5 ⁇ L to 45 [mu] L of saliva or distilled water. Green tea or black tea was added to this in a volume of 1: 1 and incubated for 10 seconds. Immediately afterwards, serum-free DMEM medium was used for 1000-fold dilution, followed by MS for 10-fold serial dilution.
  • Test Example 9 Saliva from 5 healthy subjects was purchased from Lee Biosolutions (Maryland Heights, MO, USA) and sterilized by UV irradiation for 30 minutes. Saliva 45 [mu] L of SARS-CoV-2, was added by 3.0 ⁇ 10 5 TCID 50/5 ⁇ L. Green tea or black tea was added to this in a volume of 1: 1 and incubated for 10 seconds. Immediately afterwards, serum-free DMEM medium was used for 1000-fold dilution, followed by MS for 10-fold serial dilution.
  • TCID 50 was calculated by the Reed-Muench method.
  • FIG. 6A A schematic diagram of the method in FIG. 6A, the results (mean ⁇ standard deviation of the TCID 50/50 [mu] L of each group) is shown in Figure 6B.
  • N 3. * p ⁇ 0.05 (between groups) (Student's t test).
  • Test Example 10 Saliva from 5 healthy subjects was purchased from Lee Biosolutions (Maryland Heights, MO, USA) and sterilized by UV irradiation for 30 minutes. Saliva 45 [mu] L of SARS-CoV-2, was added by 3.0 ⁇ 10 5 TCID 50/5 ⁇ L. Black tea was added to this in a volume of 1: 1 and incubated for 10 seconds. Immediately afterwards, serum-free DMEM medium was used for 1000-fold dilution, followed by MS for 10-fold serial dilution.
  • FIG. 7A A schematic diagram of the method is shown in FIG. 7A, and the results (mean ⁇ standard deviation of the culture supernatant of each group and the intracellular relative N gene RNA level) are shown in FIG. 7B.
  • Test Example 11 A sample of the stated concentration (EGCG or TFDG) and SARS-CoV-2 at a concentration of 1.25 x 10 7 TCID50 / mL were added to 500 ⁇ L and allowed to stand at room temperature for 1 minute. The supernatant was removed from a 24-well plate in which Vero E6 / TMPRSS2 cells were sown at 2.5 ⁇ 10 5 / well and cultured for 15 hours the day before, and 100 ⁇ l of the above virus / saliva / sample solution was added. (MOI 5). After adsorption for 1 hour, the virus solution was removed, washed with PBS, and MS was added at 100 ⁇ l / well.
  • Step-One Plus Real-Time PCR system (Applied Biosystems, Foster City, CA, USA) and virus N gene-specific primers / probes (Forward primer, 5'-AAATTTTGGGGACCAGGAAC-3' (SEQ ID NO:) 1); reverse primer, 5'-TGG-CAGCTGTGTAGGTCAAC-3'(SEQ ID NO: 2); and probe, 5'-(FAM) ATGTCGCGCATTGGCATGGA (BHQ) -3'(SEQ ID NO: 3)).
  • the Ct value of each sample was analyzed by StepOne Software (ABI, Warrington, UK).
  • Cellular N gene RNA levels were standardized at the 18S rRNA level of each sample. Relative RNA levels (mean ⁇ SD) were untreated. It is a relative value with the control infected with the virus as 1.0.
  • FIG. 8a A schematic diagram of the method is shown in FIG. 8a, and the results are shown in FIG. 8b.
  • Both EGCG and TFDG act on the virus in a concentration-dependent manner to suppress intracellular amplification after infection of the cell (on b), and to produce a secondary virus from the cell (b center). And below) can be seen to have been suppressed.
  • EGCG 500 to 1000 ⁇ M or more and TFDG of 60 ⁇ M or more completely suppressed cell death due to virus infection.
  • N 4. * P ⁇ 0.05, ** p ⁇ 0.01, *** p ⁇ 0.001 vs. Control (Tukey ’s multiple comparison test).
  • Test Example 12 Whether EGCG and TFDG suppressed the interaction between SARS-CoV-2 spike protein RBD and ACE2 was measured with the SARS-CoV-2 Surrogate Virus Neutralization Test Kit from GenScript (Piscataway, NJ, USA). That is, a sample of the stated concentration (EGCG or TFDG or a control containing neither (0 ⁇ M)), or a positive control or negative control included in the kit, with a horseradish peroxidase (HRP) -conjugated recombinant RBD fragment 1: 1 (volume). The ratio) was added and the mixture was incubated at 37 ° C. for 30 minutes. 100 ⁇ L of the mixture was added to wells coated with human ACE2 protein.
  • GenScript GenScript
  • HRP horseradish peroxidase
  • TMB 3,3', 5,5'-tetramethyl-benzidene

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WO2023026867A1 (ja) * 2021-08-24 2023-03-02 株式会社Hpg 保存安定性に優れたカテキン類含有水溶液組成物及びその用途
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WO2025086933A1 (en) * 2023-10-26 2025-05-01 Gt Comfort Health Corp. Tea fraction for treating idiopathic pulmonary fibrosis

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