WO2022173246A2 - Composition pour la prévention ou le traitement d'une infection par le nouveau coronavirus, comprenant un extrait de psidiuma guajava, une fraction de phéophytine de celui-ci, ou un composé à base de méroterpénoïde isolé à partir de celui-ci en tant que principe actif - Google Patents

Composition pour la prévention ou le traitement d'une infection par le nouveau coronavirus, comprenant un extrait de psidiuma guajava, une fraction de phéophytine de celui-ci, ou un composé à base de méroterpénoïde isolé à partir de celui-ci en tant que principe actif Download PDF

Info

Publication number
WO2022173246A2
WO2022173246A2 PCT/KR2022/002045 KR2022002045W WO2022173246A2 WO 2022173246 A2 WO2022173246 A2 WO 2022173246A2 KR 2022002045 W KR2022002045 W KR 2022002045W WO 2022173246 A2 WO2022173246 A2 WO 2022173246A2
Authority
WO
WIPO (PCT)
Prior art keywords
guava
compound
extract
fraction
jeju
Prior art date
Application number
PCT/KR2022/002045
Other languages
English (en)
Korean (ko)
Other versions
WO2022173246A3 (fr
Inventor
오원근
류별
마이반휴
박은진
최영기
김은하
김세미
Original Assignee
서울대학교산학협력단
충북대학교 산학협력단
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 서울대학교산학협력단, 충북대학교 산학협력단 filed Critical 서울대학교산학협력단
Publication of WO2022173246A2 publication Critical patent/WO2022173246A2/fr
Publication of WO2022173246A3 publication Critical patent/WO2022173246A3/fr

Links

Images

Classifications

    • 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)
    • A61K36/61—Myrtaceae (Myrtle family), e.g. teatree or eucalyptus
    • 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]
    • A01N65/28—Myrtaceae [Myrtle family], e.g. teatree or clove
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K10/00—Animal feeding-stuffs
    • A23K10/30—Animal feeding-stuffs from material of plant origin, e.g. roots, seeds or hay; from material of fungal origin, e.g. mushrooms
    • 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
    • A23K20/116—Heterocyclic compounds
    • A23K20/121—Heterocyclic compounds containing oxygen or sulfur as hetero atom
    • 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
    • A61K31/335—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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/02—Local antiseptics
    • 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
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2200/00—Function of food ingredients
    • A23V2200/30—Foods, ingredients or supplements having a functional effect on health
    • A23V2200/324—Foods, ingredients or supplements having a functional effect on health having an effect on the immune system
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2250/00—Food ingredients
    • A23V2250/30—Other Organic compounds

Definitions

  • the present invention is a novel corona virus (SARS-CoV-2) containing as an active ingredient a guava ( Psidium guajava ) extract or a pheophytinated fraction thereof, or a meroterpenoid-based compound isolated therefrom, showing recovery ability against infection. It relates to a composition for the prevention, improvement or treatment of corona, and more specifically, by using a chemical method to increase the content of the active ingredient of the extract and mix it to show a synergistic effect between the constituent compounds to prevent and improve novel coronavirus infection Or it relates to a herbal composition having a synergistic effect in treatment.
  • SARS-CoV-2 novel corona virus
  • Coronavirus is an RNA virus belonging to the coronaviridae, and when viewed under an electron microscope, the shape of spikes on the surface protrude, reminiscent of a crown or the corona of the sun, hence its name (Englund, JA, et al. ., 2019).
  • Coronavirinae and Torovirinae in the coronaviridae, and coronaviruses belong to the former.
  • the coronavirus subfamily is further divided into four genus: Alphacoronavirus , Betacoronavirus , Gammacoronavirus and Deltacoronavirus .
  • SARS Secute Respiratory Syndrome
  • MERS Middle East Respiratory Syndrome
  • Gene vaccine is a method to generate antibodies against the spike protein (S protein) forming gene by injecting mRNA into the human body.
  • S protein spike protein
  • Vaccines manufactured by Pfizer and Moderna reported 90% and 95% effectiveness, respectively.
  • the storage method is -70°C and -20°C, respectively, so it is not easy to secure the stability of the vaccine.
  • the viral vector vaccine is a method to form antibodies to the spike protein (S protein) using a recombinant viral vector by inserting the COVID-19 gene into a virus vector that has lost activity.
  • AstraZeneca reported an effect of more than 62%.
  • the vaccine works effectively, since the coronavirus undergoes mutations and frequent gene recombination in the process of propagation, there is a high possibility that the efficacy of the vaccine will not last long.
  • guava Pumicutica, Psidium guajava
  • guava Psidium guajava
  • the leaves are consumed as tea and the fruit is consumed raw, in juices and jams.
  • Guava has traditionally been used as a medicinal plant.
  • guava was used as a folk remedy for diarrhea, dysentery, and acute gastroenteritis; in Peru, it was used for diarrhea, abdominal pain, vomiting, cough, and menstrual pain.
  • guava was used for sore throat. It was used to rinse the mouth with juice.
  • guava is known as a plant used for metabolic diseases such as obesity or diabetes, and there are studies reporting the antidiabetic effect of guava even in modern times (Huang, CS, et al., 2011; Oh., WK, et al. ., 2005; Shen, SC, et al., 2014).
  • Chemical components reported from guava include flavonoids, benzophenones, tannins, and psidium meroterpenoids (Okuda, T., et al., 1987; Prabu, G.R., et al., 2006; Ukwueze, S.E., et al., 2015).
  • guava contains a phthydium meroterpenoid characterized by a dihydropyran-ring junction between 3,5-diformyl-benzyl phloroglucinol and a terpenoid, and these meroterpenoids has been reported to have antidiabetic, anticancer and PDE4 inhibitor activity (Hou, J.Q., et al., 2019; Qin, X.-J., 2017; Tang, G.-H., et al., 2017) ).
  • Korean Patent No. 102169476 discloses a composition for the prevention or treatment of type 2 severe acute respiratory syndrome coronavirus infection, and includes Zafirlukast, an asthma treatment, and Sulfinpyrazone, a gout treatment. showed inhibitory ability against SARS-CoV-2.
  • Korean Patent Application Laid-Open No. 1020200053057 discloses a preventive and therapeutic agent for coronavirus, and a mixture of 14 substances such as calcium, phosphoric acid, folic acid, and quercetin is presented as a preventive and therapeutic agent for novel coronavirus.
  • Korean Patent Application Laid-Open No. 1020200131784 discloses a composition for the prevention or treatment of type 2 severe acute respiratory syndrome coronavirus infection disease.
  • Candidate drugs including sulfinpyrazone and allopurinol were derived.
  • the anti-inflammatory effect of a composition containing guava in Korean Patent No. 101491493 the anti-inflammatory effect of a composition containing guava in Korean Patent No. 101072905, and guava in Korean Patent No. 101320946
  • the above techniques are the composition of the present invention showing the prevention, improvement or treatment effect of novel coronavirus infection of the guava extract and the pheophytination fraction or the meroterpenoid-based compound isolated therefrom.
  • It is an object of the present invention to provide a composition for preventing, improving or treating novel coronavirus infection comprising, as an active ingredient, a guava ( Psidium guajava ) extract or a pheophytinated fraction thereof or a meroterpenoid-based compound isolated therefrom.
  • a guava Psidium guajava extract or a pheophytinated fraction thereof or a meroterpenoid-based compound isolated therefrom.
  • Another object of the present invention is to provide a health functional food for preventing or improving symptoms of new corona virus infection, comprising as an active ingredient a guava extract or a pheophytinated fraction thereof or a meroterpenoid-based compound isolated therefrom. .
  • Another object of the present invention is to provide a herbal composition having an excellent synergistic effect in preventing, improving or treating novel coronavirus infection, comprising a mixture according to the components of the guava ( Psidium guajava ) extract and a combination thereof.
  • Another object of the present invention is to provide a disinfectant for preventing new corona virus infection comprising, as an active ingredient, a guava extract or a pheophytinated fraction thereof or a meroterpenoid-based compound isolated therefrom.
  • Another object of the present invention is to provide a composition for animal feed for preventing or improving novel coronavirus infection, comprising as an active ingredient a guava extract or a pheophytinated fraction thereof or a meroterpenoid-based compound isolated therefrom.
  • Another object of the present invention is to provide an animal drug for preventing or treating new corona virus infection, comprising a mixture according to the components of the guava ( Psidium guajava ) extract and a combination thereof as an active ingredient.
  • the present invention provides a composition for preventing or treating novel coronavirus infection, comprising as an active ingredient a guava ( Psidium guajava ) extract or a pheophytinated fraction thereof or a meroterpenoid-based compound isolated therefrom.
  • a guava Psidium guajava
  • the guava ( Psidium guajava ) extract is porphyrin chlorophyll a (chlorophyll a), chlorophyll a ' (chlorophyll a '), chlorophyll b (chlorophyll b), chlorophyll b ' (chlorophyll b '), pheophytin It may include one or more selected from the group consisting of a (pheophytin a), pheophytin a' (pheophytin a'), pheophytin b (pheophytin b), and pheophytin b' (pheophytin b'), Preferably, at least one selected from the group consisting of pheophytin a, pheophytin a', pheophytin b, and pheophytin b' may include.
  • the guava ( Psidium guajava ) extract may be obtained by extracting guava leaves or fruits with any one solvent selected from the group consisting of water, C1 to C4 lower alcohols, hexane, acetone, methylene chloride, ethyl acetate, and mixed solvents thereof.
  • the guava leaf or fruit extract is an extract obtained by extracting guava leaves or fruits with 70-100% C1 to C4 aqueous solution of lower alcohol or lower alcohol or acetone, or hexane fractions and extracts obtained by pheophytinizing these hexane fractions and extracts It may be a fraction.
  • the guava leaf or fruit extract was extracted three times by stirring for 2 hours using 95% ethanol on the guava leaf or fruit, and then concentrated under reduced pressure at 40° C. w/v] It can be prepared by concentration under reduced pressure of the hexane fraction obtained by solvent extraction with hexane of the suspension in citric acid solution, or the hexane fraction obtained by suspending the extract in water and storing it at 60° C. for at least one day It can be prepared by concentration under reduced pressure.
  • Chlorophyll a (chlorophyll a), chlorophyll a ', chlorophyll b (chlorophyll b), chlorophyll b' (chlorophyll b '), pheophytin a (pheophytin a) of the porphyrins Pheophytin a', pheophytin b, and pheophytin b' can be prepared under similar conditions in all chlorophyll-producing plants.
  • the polphyrin-based compound contained in the guava leaf or fruit is a hexane fraction of the guava leaf or fruit extracted with 70-100% C1 to C4 aqueous solution of lower alcohol or lower alcohol or acetone, and a hexane fraction obtained by pheophytinizing the extract. It can be obtained by separation, and preferably an extract extracted with 95% ethanol or a hexane fraction obtained by pheophytinizing the extract can be obtained by separating by chromatography.
  • the chromatography is normal phase column chromatography (normal phase column chromatography), reverse phase column chromatography (reverse phase column chromatography), Diaion HP-20 column chromatography (Diaion HP-20 column chromatography), RP-18 column chromatography ( RP-18 column chromatography), LH-20 column chromatography (LH-20 column chromatography), preparative reversed-phase high performance chromatography, medium pressure liquid chromatography, High-performance liquid chromatography (HPLC) or the like may be used.
  • normal phase column chromatography normal phase column chromatography
  • reverse phase column chromatography reverse phase column chromatography
  • Diaion HP-20 column chromatography Diaion HP-20 column chromatography
  • RP-18 column chromatography RP-18 column chromatography
  • LH-20 column chromatography LH-20 column chromatography
  • HPLC High-performance liquid chromatography
  • the guava extract is a guava leaf or fruit extracted with one or more solvents selected from the group consisting of water, C1 to C4 lower alcohols, hexane, acetone, methylene chloride, ethyl acetate, and mixed solvents thereof with distilled water. After suspending, it may be a fraction obtained by fractionation with an organic solvent.
  • the organic solvent may be a C1-4 lower alcohol, ethyl acetate, hexane or acetone.
  • the C1-4 lower alcohol may be methanol, ethanol, propanol, isopropanol, butanol, or the like.
  • they are hexane and ethyl acetate, More preferably, they are hexane.
  • the present invention provides at least one selected from Jeju guar capital A (compound 1 ), Jeju guar capital D (compound 2 ), Jeju guar capital E (compound 3 ) and Jeju guar capital H (compound 4 ) of the following formula 1 compounds may be included.
  • the compound may be derived from guava.
  • the present invention is selected from the group consisting of Jeju guar capital A (compound 1), Jeju guar capital D (compound 2), Jeju guar capital E (compound 3) and Jeju guar capital H (compound 4) of Formula 1 above It may include one or more compounds as an active ingredient, preferably comprising one or more compounds selected from the group consisting of Jeju guar capital A (compound 1) and Jeju guar capital D (compound 2) It relates to a composition for preventing or treating novel coronavirus infection, and animal medicine, a health functional food composition for improvement, and a composition for animal feed.
  • the present invention also provides a guava extract obtained by extracting guava leaves or fruits using at least one selected from the group consisting of water, C1 to C4 lower alcohols, hexane, acetone, methylene chloride, ethyl acetate, and mixed solvents thereof as a solvent.
  • the fractions from the second step were subjected to column chromatography, and Jeju guar capital A (compound 1), Jeju guar capital D (compound 2), Jeju guar capital E (compound 3) and Jeju guar capital H (compound 4) of Formula 1 above
  • the present invention relates to a guava extract and a pheophytinated fraction or Jeju guar capital A (compound 1), Jeju guar capital D (compound 2), Jeju guar capital E (compound 3) and Jeju guar capital H of Formula 1 isolated therefrom (Compound 4) may be a composition for preventing or treating novel coronavirus infection, characterized in that it contains one or more compounds selected from the group consisting of as an active ingredient.
  • the guava extract is porphyrin-type chlorophyll a (chlorophyll a), chlorophyll a' (chlorophyll a'), chlorophyll b (chlorophyll b), chlorophyll b' (chlorophyll b'), pheophytin a (pheophytin a) ), pheophytin a' (pheophytin a'), pheophytin b (pheophytin b), may include one or more selected from the group consisting of pheophytin b' (pheophytin b'), preferably pe It may include at least one selected from the group consisting of ophytin a (pheophytin a), pheophytin a' (pheophytin a'), pheophytin b (pheophytin b), and pheophytin b'
  • the guava extract may be obtained by extracting guava leaves or fruits with any one solvent selected from the group consisting of water, C1 to C4 lower alcohols, hexane, acetone, methylene chloride, ethyl acetate, and mixed solvents thereof.
  • the guava leaf or fruit extract is an extract obtained by extracting guava leaves or fruits with 70-100% C1 to C4 aqueous solution of lower alcohol or lower alcohol or acetone, or hexane fractions and extracts obtained by pheophytinizing these hexane fractions and extracts It may be a fraction.
  • the guava leaf or fruit extract was extracted three times by stirring for 2 hours using 95% ethanol on the guava leaf or fruit, and then suspended in water, 0.5 N hydrochloric acid solution or 1% [w/v] citric acid aqueous solution. It can be prepared by concentrating the hexane fraction obtained by solvent extraction with hexane under reduced pressure, or by suspending the extract in water and storing it at 60° C. for at least one day, and then concentrating the solvent-extracted hexane fraction with hexane under reduced pressure.
  • Chlorophyll a (chlorophyll a), chlorophyll a ', chlorophyll b (chlorophyll b), chlorophyll b' (chlorophyll b '), pheophytin a (pheophytin a) of the porphyrins Pheophytin a', pheophytin b, and pheophytin b' can be prepared under similar conditions in all chlorophyll-producing plants.
  • the polphyrin-based compound contained in the guava leaf or fruit is a hexane fraction of the guava leaf or fruit extracted with 70-100% C1 to C4 aqueous solution of lower alcohol or lower alcohol or acetone, and a hexane fraction obtained by pheophytinizing the extract. It can be obtained by separation, and preferably, an extract extracted with 100% methanol or 95% ethanol or a hexane fraction obtained by pheophytinizing the extract can be obtained by separating by chromatography.
  • the chromatography is normal phase column chromatography (normal phase column chromatography), reverse phase column chromatography (reverse phase column chromatography), Diaion HP-20 column chromatography (Diaion HP-20 column chromatography), RP-18 column chromatography ( RP-18 column chromatography), LH-20 column chromatography (LH-20 column chromatography), preparative reversed-phase high performance chromatography, medium pressure liquid chromatography, High-performance liquid chromatography (HPLC) or the like may be used.
  • normal phase column chromatography normal phase column chromatography
  • reverse phase column chromatography reverse phase column chromatography
  • Diaion HP-20 column chromatography Diaion HP-20 column chromatography
  • RP-18 column chromatography RP-18 column chromatography
  • LH-20 column chromatography LH-20 column chromatography
  • HPLC High-performance liquid chromatography
  • the guava extract is a guava leaf or fruit extracted with one or more solvents selected from the group consisting of water, C1 to C4 lower alcohols, hexane, acetone, methylene chloride, ethyl acetate, and mixed solvents thereof with distilled water. After suspending, it may be a fraction obtained by fractionation with an organic solvent.
  • the organic solvent may be a C1-4 lower alcohol, ethyl acetate, hexane or acetone.
  • the C1-4 lower alcohol may be methanol, ethanol, propanol, isopropanol, butanol, or the like.
  • they are hexane and ethyl acetate, More preferably, they are hexane.
  • Compounds 1 to 4 of Formula 1 may be isolated from guava extract.
  • Compounds 1 to 4 of Formula 1 isolated from the guava extract can be obtained by fractionation of the guava extract by chromatography, and the chromatography is performed by normal phase column chromatography, reverse phase column chromatography ), Diaion HP-20 column chromatography, RP-18 column chromatography, LH-20 column chromatography, Reversed phase preparation - It can be used by selecting from preparative reversed-phase high performance chromatography, medium pressure liquid chromatography, and high-performance liquid chromatography (HPLC).
  • HPLC high-performance liquid chromatography
  • the compound of the present invention may be synthesized according to a conventional method in the art, and may be prepared as a pharmaceutically acceptable salt.
  • the plant is at least one selected from the group consisting of leaves, branches, stems, roots and fruits.
  • the composition may be a composition for preventing or treating novel coronavirus infection.
  • the pharmaceutical composition includes at least one compound selected from the group consisting of guava extract and pheophytination fraction or a meroterpenoid-based compound of Formula 1, which is a meroterpenoid compound isolated therefrom, and a pharmaceutically acceptable carrier. can do.
  • the pharmaceutical composition comprising the guava extract and the pheophytinated hexane fraction or the meroterpenoid-based compound separated therefrom can be prepared as powders, granules, tablets, capsules, suspensions, emulsions, syrups, aerosols, etc. according to a conventional method, respectively. It can be used in the form of oral dosage forms, external preparations, suppositories, and sterile injection solutions.
  • Carriers, excipients and diluents that may be included in the pharmaceutical composition include lactose, dextrose, sucrose, sorbitol, mannitol, xylitol, erythritol, maltitol, starch, acacia gum, alginate, gelatin, calcium phosphate, calcium silicate, cellulose , methyl cellulose, microcrystalline cellulose, polyvinyl pyrrolidone, water, methylhydroxybenzoate, propylhydroxybenzoate, talc, magnesium stearate and mineral oil.
  • Solid preparations for oral administration include tablets, pills, powders, granules, capsules, and the like, and these solid preparations are the guava extract and pheophytinated hexane fraction of the present invention or the meroterpenoid compound isolated therefrom. It is prepared by mixing at least one excipient, for example, starch, calcium carbonate, sucrose or lactose, gelatin, etc. with one or more compounds selected from the group consisting of compounds 1 to 4 of Formula 1.
  • Liquid formulations for oral use include suspensions, solutions, emulsions, syrups, etc.
  • various excipients such as wetting agents, sweeteners, fragrances, preservatives, etc. may be included.
  • Formulations for parenteral administration include sterile aqueous solutions, non-aqueous solutions, suspensions, emulsions, freeze-dried preparations, and suppositories.
  • Non-aqueous solvents and suspending agents include propylene glycol, polyethylene glycol, vegetable oils such as olive oil, and injectable esters such as ethyl oleate.
  • injectable esters such as ethyl oleate.
  • base of the suppository witepsol, macrogol, tween 61, cacao butter, laurin, glycerogelatin, and the like can be used.
  • the dosage of the pharmaceutical composition will vary depending on the age, sex, and weight of the subject to be treated, the specific disease or pathological condition to be treated, the severity of the disease or pathological condition, the route of administration, and the judgment of the prescriber. Dosage determination based on these factors is within the level of one of ordinary skill in the art, and generally the dosage is in the range of 0.1-1000 mg/kg/day. A more preferred dosage is 0.5-500 mg/kg/day. Administration may be administered once a day, or may be administered in several divided doses. The above dosage does not limit the scope of the present invention in any way.
  • the pharmaceutical composition may be administered to mammals such as mice, livestock, companion animals, and humans by various routes. Any mode of administration can be envisaged, for example, by oral, rectal or intravenous, intramuscular, subcutaneous, intrauterine mucosal or intracerebrovascular injection.
  • composition may be a food composition for preventing or treating novel coronavirus infection.
  • the health functional food composition includes at least one compound selected from the group consisting of compounds 1 to 4 of Formula 1, which is a guava extract or a pheophytinated fraction thereof, or a meroterpenoid-based compound isolated therefrom, and a food pharmaceutically acceptable It may contain food supplement additives.
  • At least one compound selected from the group consisting of compounds 1 to 4 of Formula 1, which is the guava extract or a pheophytinated fraction thereof, or a meroterpenoid-based compound isolated therefrom, comprises the total weight of the health functional food composition of the present invention. It may be included as 0.001 to 100% by weight as a basis.
  • the food composition of the present invention includes the form of tablets, capsules, pills or liquids, and the guava extract of the present invention or a pheophytinated fraction thereof or a meroterpenoid-based compound isolated therefrom,
  • Compound 1 of Formula 1 Foods to which one or more compounds selected from the group consisting of 4 can be added include, for example, various foods, beverages, gums, tea, vitamin complexes, health functional foods, and the like.
  • Another aspect of the present invention is one selected from the group consisting of compounds 1 to 4 of Formula 1, which is the guava extract or the pheophytinated fraction thereof of the present invention or a meroterpenoid-based compound isolated therefrom.
  • the composition comprising the above compound provides a composition for animal feed for preventing or improving novel coronavirus infection.
  • the composition for animal feed may include a feed additive.
  • the feed additive of the present invention corresponds to an auxiliary feed under the Feed Management Act.
  • the type of animal feed is not particularly limited, and feeds commonly used in the art may be used.
  • the feed include plant feeds such as grains, root fruits, food processing by-products, algae, fibers, pharmaceutical by-products, oils and fats, starches, gourds or grain by-products; and animal feeds such as proteins, inorganic materials, oils and fats, minerals, oils and fats, single cell proteins, zooplankton, or food. These may be used alone or in combination of two or more.
  • the present invention also relates to a method for isolating compounds 1 to 4 of Formula 1, wherein guava leaves or fruits are mixed with water, C1 to C4 lower alcohols, hexane, acetone, methylene chloride, ethyl acetate, and mixed solvents thereof.
  • the fractions from the second step were subjected to column chromatography, and Jeju guar capital A (compound 1), Jeju guar capital D (compound 2), Jeju guar capital E (compound 3) and Jeju guar capital H (compound 4) of the following formula 1 were added to column chromatography.
  • the organic solvent of the second step may be a C1-4 lower alcohol, ethyl acetate, hexane, acetone, or the like.
  • the C1-4 lower alcohol may be methanol, ethanol, propanol, isopropanol, butanol, or the like.
  • they are hexane and ethyl acetate, More preferably, they are hexane.
  • the fraction of step 2 is most preferably a hexane fraction obtained by suspending the concentrated extract of step 1 in distilled water and then fractionating with hexane.
  • the column chromatography of the above three steps is normal phase column chromatography, reversed phase column chromatography, Diaion HP-20 column chromatography, RP-18 column chromatography, LH-20 column chromatography, preparative reverse phase-high performance liquid chromatography, It can be used by selecting from medium pressure liquid chromatography, high performance liquid chromatography, and the like.
  • the present invention relates to a composition for the prevention, improvement or treatment of novel coronavirus infection comprising, as an active ingredient, a guava extract or a pheophytinated fraction thereof or a meroterpenoid-based compound isolated therefrom, a guava extract and a pheophytinated It was confirmed that the fraction or the meroterpenoid-based compound isolated therefrom exhibited cell lesion recovery ability against novel coronavirus infection.
  • the guava extract of the present invention or its pheophytinated fraction or a meroterpenoid-based compound isolated therefrom can be used for the prevention, improvement or treatment of new corona infection, food, medical supplies, and composition for animal feed. It is expected that it will be possible
  • FIG. 1 is a diagram showing the chemical structure of a compound isolated from guava leaves having an inhibitory effect on novel coronavirus (SARS-CoV-2).
  • FIG. 2 is a chromatogram showing the presence or absence of meroterpenoid compounds in a leaf extract of guava, a hexane fraction thereof, and a pheophytination fraction using an inorganic acid.
  • FIG. 3 is a chromatogram of a pheophytin-based compound using a leaf extract of guava, a hexane fraction of a dried leaf extract, and an inorganic acid.
  • 5 is a chromatogram of a pheophytinated fraction through heat treatment of a guava leaf extract for 1 hour to 48 hours.
  • FIG. 6 is a graph showing the cell lesion recovery ability for novel coronavirus (SARS-CoV-2) infection of each fraction including a leaf extract of guava and a pheophytination reaction.
  • SARS-CoV-2 novel coronavirus
  • FIG. 7 is a graph showing the cell lesion recovery ability against SARS-CoV-2 infection of compounds 1 to 4 isolated from leaf extracts of guava.
  • Jeju Island located in the South Sea of Korea, is gradually approaching a subtropical climate due to global warming, and many farms located on Jeju Island are cultivating guava.
  • the present inventors in the process of studying guava extracts showing recovery ability against novel coronavirus (SARS-CoV-2) infection, guava extracts and fractions or constituent compounds having phosidium meroterpenoid as a basic skeleton, and these constituent compounds It was discovered that the combination of liver is effective in preventing and improving the novel corona, and by using a chemical method, the content of the active ingredient of the extract is increased, and the present invention is completed by mixing it to show a synergistic effect between the constituent compounds.
  • SARS-CoV-2 novel coronavirus
  • the raw leaves and hot air-dried dried leaves of guava of the present invention were purchased from Jungeom Farm located in Jungeom-ri, Aewol-eup, Jeju-si, Korea. After 10 kg of dried guava leaves were crushed, 50 L of 95% [v/v] ethanol was added, and the mixture was extracted three times with an ultrasonic extractor for 99 minutes, and concentrated under reduced pressure to obtain 1.45 kg of a 95% ethanol extract.
  • Fractions were sequentially obtained through chromatography of the extract obtained in Example 1.1, and antiviral activity of each fraction was evaluated to separate four new compounds from the fraction with the highest antiviral activity.
  • Example 1.1 the extract obtained in Example 1.1 was always suspended in 2.0 L of distilled water, followed by sequential solvent fractionation with n -hexane and ethyl acetate to obtain an n -hexane fraction (240.3 g). Then, the n -hexane fraction (240.3 g) was subjected to normal phase column chromatography under gradient elution conditions of n -hexane:ethyl acetate:methanol (1:0:0 ⁇ 0:0:1[v:v:v]) (normal phase column chromatography) phase column chromatography) was performed to obtain 12 fractions (F.1 - 12).
  • F.4 fraction (33.7 g) was subjected to normal phase column chromatography under gradient conditions of n -hexane:ethyl acetate (1:0 ⁇ 9:1 [v:v]) to obtain 7 small fractions (F. .4-1 - 4-7).
  • F.4-7 reverse-phase MPLC was performed under a gradient condition of methanol: distilled water (0.1% formic acid) (9:1 ⁇ 0:1 [v:v]) to obtain 4 small fractions again (F.4- 7-1 - 4-7-4).
  • Pheophytination and preparation of fractions of guava leaf extract are polphyrin-based compounds, which are demetallized, dephytylated, and decarbomethoxylated through a cooking process or digestion process. It is known that derivatives such as pheophytin, pyropheophytin, chlorophyllide, and pheophorbide are produced (Hayes & Ferruzzi, 2020).
  • the present inventors confirmed the antiviral activity against SARS-CoV-2 of the guava extract, particularly the pheophytinated fraction, through a basic experiment, and the four compounds obtained in Example 2 were also abundant in the pheophytinated fraction. It was confirmed that it was included. Accordingly, a method for preparing a pheophytinated fraction capable of significantly increasing the content of pheophytin from guava leaf extract was established.
  • the dried guava extract was suspended using a 0.5 N hydrochloric acid solution, and the solvent was fractionated with n -hexane for about 5 minutes, followed by solvent fractionation 2-3 times with the same volume of water. By lowering the acidity, a pheophytinated n- hexane fraction was finally obtained. Finally, after drying through a lyophilizer, it was dissolved in DMSO to make 10 mg/mL and used in the antiviral activity evaluation experiment.
  • the experiment was performed by varying the concentration using citric acid, which is a safe organic acid present in plants. After drying the fresh guava leaves in the shade, they were extracted three times by stirring with 95% ethanol for 2 hours, and concentrated under reduced pressure to obtain the extract and used in the experiment. After preparing a 10% [w/v] citric acid aqueous solution, serial dilutions were made to prepare 10%, 5%, 1%, 0.5%, 0.25%, 0.1% citric acid aqueous solution.
  • the guava extract prepared in Example 3.2 was suspended in distilled water and then left in a dry oven at 60° C. for 1 hour, 3 hours, 6 hours, 12 hours, 24 hours and 48 hours, followed by solvent fractionation with n -hexane and pheophytinylation An n- hexane fraction was obtained. Finally, fractions for each condition were prepared at 1 mg/mL for HPLC analysis.
  • Example 3.1 95% ethanol extract of dried guava leaves, n -hexane fraction, and pheophytination fraction using 0.5N aqueous hydrochloric acid solution obtained in Example 3.1 were analyzed at a concentration of 10 mg/ml for the extract and 5 for the fraction. It was prepared using methanol or aqueous methanol solution at a concentration of mg/ml. Compounds 1 to 4 isolated in Example 1.2 were prepared at a concentration of 1 mg/ml.
  • HPLC analysis was performed using a Thermo Fisher Scientific UltiMate 3000 system equipped with a DAD-Diode Array Detector 3000, and a YMC-Triart C18 (4.6 ⁇ 250.0 mm, 5 ⁇ m ) column was used.
  • Analytical conditions the mobile phase of liquid chromatography was flowed at a flow rate of 1.0 ml/min using distilled water (mobile phase A) and acetonitrile (mobile phase B) containing 0.1% [v/v] formic acid, and a column temperature of 25 ° C., Analysis was performed at a sample temperature of 10°C, and 20 ⁇ l of each sample was injected.
  • the chromatogram was observed at 290 nm, and the conditions of the mobile phase were as follows. It flowed with a gradient of 70-100% mobile phase B for 0-35.0 minutes, 100% mobile phase B for 35.0-55.0 minutes, and 70% mobile phase B for 55.1-60.0 minutes. Through the retention time and ultraviolet absorption pattern of compounds 1 to 4 isolated in Example 1-2, The presence or absence of the compounds included in each sample was checked, and the results are shown in FIG. 2 .
  • n -hexane fraction and pheophytination fraction of the dried guava leaf extract obtained in Example 3.1 and the n -hexane fraction of the guava leaf extract obtained in Example 3.2 in the shade were mixed with methanol at a concentration of 1 mg/ml for HPLC analysis.
  • methanol at a concentration of 1 mg/ml for HPLC analysis.
  • polphyrin-based compounds were identified in all samples.
  • chlorophyll a, b and pheophytin a, b and their derivatives were all confirmed, whereas the n -hexane fraction of the dried guava leaf was the same as the pheophytinated fraction of the same sample.
  • Only pheophytin a, b and its derivatives were identified. This shows that as the purchased dried guava leaves are hot air-dried samples, pheophytinization by heat has progressed. In Example 5.3 below, pheophytination through heat treatment will be introduced to support these results.
  • Example 3.2 After securing a pheophytination fraction and n -hexane fraction using citric acid for each concentration of the guava leaf extract obtained in Example 3.2, methanol was prepared at a concentration of 1 mg/ml. HPLC analysis was performed using the same system, column and analysis conditions as described in Example 5.1, and through the retention time and UV absorption pattern of the polphyrin-based compounds. The relative content of the substances included in the fractions for each concentration and the degree of pheophytinylation were compared through the intensity of the peak, and the results are shown in FIG. 4 .
  • Example 3.3 After obtaining a pheophytinated fraction and an n -hexane fraction through heat treatment of the guava leaves obtained in Example 3.3, methanol was prepared at a concentration of 1 mg/ml. HPLC analysis was performed using the same system, column and analysis conditions as described in Example 5.1, and through the retention time and UV absorption pattern of the polphyrin-based compounds. The presence or absence of substances contained in each concentration fraction and the degree of pheophytinylation were compared with the relative content through the intensity of the peak, and the results are shown in FIG. 5 .
  • Example 5.1 After concentrating the guava leaf extract, it was suspended in distilled water and left in a dry oven at 60 ° C for 1 hour, 3 hours, 6 hours, 12 hours, 24 hours and 48 hours to perform pheophytinization. It was confirmed that all chlorophyll a, b and derivatives thereof were completely pheophytinized even in samples left only for a period of time.
  • Example 5.1 in the n -hexane fraction of the guava dried leaf extract dried by hot air, chlorophyll a, b and its derivatives were not identified, but only pheophytin a, b and its derivatives were confirmed, which also showed pheophytinylation by heat. to be.
  • the pheophytination reaction is also possible through a method of heating at 60° C. to 100° C. (blanching) or processing the guava leaf itself with heat.
  • SARS-CoV-2 severe acute respiratory syndrome coronavirus 2, NMC-CoV-02 strain
  • SARS-CoV-2 virus was inoculated with mono-layered VERO cells, and after 3 days, the virus culture supernatant was collected, and the virus was inoculated into VERO cells cultured in DMEM medium containing 10% [v/v] FBS. It was used to measure antiviral activity.
  • VERO cells After infecting VERO cells with the SARS-CoV-2 virus prepared in Example 6.1, VERO cells were dispensed at a density of 2 ⁇ 10 4 cells/well in this 96-well plate to 10% [v/v ] FBS (fetal bovine serum), 1% [v/v] PS (penicillin + streptomycin) and L-glutamine (L-glutamine, added 2ml based on 500ml medium) for one day in DMEM culture medium, and then the culture medium Washed with PBS solution.
  • FBS fetal bovine serum
  • PS penicillin + streptomycin
  • L-glutamine L-glutamine
  • infection medium infection media: DMEM
  • SARS-CoV-2 virus at a concentration of 100 TCID 50
  • PBS solution 50 ⁇ l of infection medium (infection media: DMEM) containing SARS-CoV-2 virus at a concentration of 100 TCID 50
  • DMEM infection media
  • the culture medium was washed with PBS solution.
  • the compound of the present invention was treated and cultured for 3 days in DMEM culture medium containing 0.2 ⁇ g/ml trypsin, and the CPE caused by the virus was measured.
  • FIGS. 6 and 7 The results of antiviral activity according to the dilution factor of each compound are shown in FIGS. 6 and 7 below.
  • both the guava leaf extract and the fraction showed antiviral effect at a concentration of 20 ⁇ g /ml or less.
  • the n -hexane fraction and the pheophytinated fraction showed antiviral activity even at 5 ⁇ g /ml and showed the best effect.
  • antiviral activity was confirmed at a concentration of 40 ⁇ M or less for all compounds, which is shown in FIG. 7 .
  • Compounds 1 and 2 showed activity at a concentration of 3.75 ⁇ M and showed the best antiviral effect.
  • the meroterpenoid-based compound and the pheophytin-based compound exhibited antiviral effects, and at the same time, as confirmed through HPLC analysis in Examples 4 and 5.1, meloterpene-based compounds It was confirmed that the n -hexane fraction and the pheophytinated fraction containing the most abundant nooid compound and pheophytin compound exhibited the best antiviral effect.
  • the guava extract, fraction, or pheophytinated fraction thereof of the present invention, or a meroterpenoid-based compound isolated therefrom is effective in preventing, improving or treating novel coronavirus infection.
  • guava extract or pheophytinated fraction of the present invention or Jeju guar capital A (compound 1), Jeju guar capital D (compound 2), Jeju guar capital E (compound 3) and Jeju guar capital H (compound 4) 200 mg of at least one selected from the group consisting of 175.9 g of lactose, 180 g of potato starch and 32 g of colloidal silicic acid were mixed with each. After adding a 10% gelatin solution to this mixture, it was ground and passed through a 14 mesh sieve. This was dried, and 160 g of potato starch, 50 g of talc and 5 g of magnesium stearate were added thereto, and the resulting mixture was made into tablets.
  • guava extract or pheophytinated fraction of the present invention or Jeju guar capital A (compound 1), Jeju guar capital D (compound 2), Jeju guar capital E (compound 3) and Jeju guar capital H (compound 4)
  • At least one selected from the group consisting of flour was added in an amount of 0.1% by weight, and the mixture was used to prepare bread, cake, cookies, crackers and noodles to prepare health-promoting food.
  • guava extract or pheophytinated fraction of the present invention or Jeju guar capital A (compound 1), Jeju guar capital D (compound 2), Jeju guar capital E (compound 3) and Jeju guar capital H (compound 4) At least one selected from the group consisting of tomato juice or carrot juice was added to 1,000 ml of each to prepare vegetable juice for health promotion.

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • Polymers & Plastics (AREA)
  • Botany (AREA)
  • Public Health (AREA)
  • Mycology (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Zoology (AREA)
  • Food Science & Technology (AREA)
  • Biotechnology (AREA)
  • Microbiology (AREA)
  • Virology (AREA)
  • Organic Chemistry (AREA)
  • Epidemiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Animal Husbandry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Molecular Biology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Physiology (AREA)
  • Environmental Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Dentistry (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
  • Medical Informatics (AREA)
  • Nutrition Science (AREA)
  • Alternative & Traditional Medicine (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

La présente invention concerne une composition pour prévenir ou traiter une infection par le nouveau coronavirus, comprenant, en tant que principe actif, un extrait de Psidiuma guajava, une fraction de phéophytine de celui-ci, ou un composé à base de méroterpénoïde isolé à partir de celui-ci. En augmentant, par l'intermédiaire d'un procédé chimique, la teneur en un composé lié à la porphyrine, qui est un composé actif, tout en contenant le composé à base de méroterpénoïde, la composition peut être avantageusement utilisée dans le traitement et la prévention d'une infection par le nouveau coronavirus par des interactions synergiques d'activité antivirale.
PCT/KR2022/002045 2021-02-10 2022-02-10 Composition pour la prévention ou le traitement d'une infection par le nouveau coronavirus, comprenant un extrait de psidiuma guajava, une fraction de phéophytine de celui-ci, ou un composé à base de méroterpénoïde isolé à partir de celui-ci en tant que principe actif WO2022173246A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020210019447A KR20220115432A (ko) 2021-02-10 2021-02-10 구아바(Psidiuma guajava) 추출물 또는 이의 페오피틴화 분획물 또는 이로부터 분리한 메로테르페노이드계 화합물을 유효성분으로 포함하는 신종코로나 바이러스 감염의 예방 또는 치료용 조성물
KR10-2021-0019447 2021-02-10

Publications (2)

Publication Number Publication Date
WO2022173246A2 true WO2022173246A2 (fr) 2022-08-18
WO2022173246A3 WO2022173246A3 (fr) 2022-10-06

Family

ID=82838034

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2022/002045 WO2022173246A2 (fr) 2021-02-10 2022-02-10 Composition pour la prévention ou le traitement d'une infection par le nouveau coronavirus, comprenant un extrait de psidiuma guajava, une fraction de phéophytine de celui-ci, ou un composé à base de méroterpénoïde isolé à partir de celui-ci en tant que principe actif

Country Status (2)

Country Link
KR (1) KR20220115432A (fr)
WO (1) WO2022173246A2 (fr)

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101072905B1 (ko) 2010-02-04 2011-10-17 노상근 구아바와 가시오가피의 추출물을 주성분으로 하는 항당뇨 조성물
KR101320946B1 (ko) 2011-04-01 2013-10-23 경희대학교 산학협력단 구아바 잎 추출물의 헥산 분획물을 유효성분으로 포함하는 전립선암 치료용 조성물
KR101491493B1 (ko) 2013-04-04 2015-02-09 한국식품연구원 감귤 과피 및 구아바 추출물을 포함하는 항염증 약학 조성물
KR20190053490A (ko) * 2017-11-10 2019-05-20 동성제약주식회사 클로로필 함유 천연물로부터 고순도 페오피틴의 제조방법 및 그 페오피틴을 이용한 클로린 e6, 클로린 e6와 PVP(polyvinylpyrrolidone)의 복합체 제조방법
KR102176525B1 (ko) 2018-11-07 2020-11-10 한국과학기술원 희생층을 이용한 계층적 주름 구조체의 제조방법 및 이로부터 제조된 계층적 주름 구조체
KR102169476B1 (ko) 2020-05-20 2020-10-23 (주)신테카바이오 제2형 중증급성호흡기증후군 코로나바이러스 감염 질환의 예방 또는 치료용 조성물
KR20200131784A (ko) 2020-11-04 2020-11-24 (주)신테카바이오 제2형 중증급성호흡기증후군 코로나바이러스 감염 질환의 예방 또는 치료용 조성물

Also Published As

Publication number Publication date
WO2022173246A3 (fr) 2022-10-06
KR20220115432A (ko) 2022-08-17

Similar Documents

Publication Publication Date Title
KR101021830B1 (ko) 크레이스토카릭스 오페르쿠라투스로부터 얻은 조류, 돼지 인플루엔자 및 신종플루에 대한 항바이러스제
WO2012144754A2 (fr) Composition contenant un extrait de galla rhois présentant des effets inhibiteur de virus, ou un composé isolé à partir de celui-ci, comme ingrédient actif et ses utilisations
WO2020246777A1 (fr) Procédé de préparation d'un extrait de fruit noni riche en iridoïde ou d'une fraction de celui-ci, procédé de préparation d'extrait de fruit noni riche en matière active d'amélioration immunitaire ou fraction de celui-ci et utilisation d'un extrait de fruit noni ou d'une fraction de celui-ci
WO2013058484A2 (fr) Composé diterpène de type ingénane et composition pharmaceutique pour le traitement ou la prévention de maladies infectieuses virales le contenant
KR101782532B1 (ko) 백지 추출물 또는 이로부터 분리된 퓨라노쿠마린을 함유하는 조류 인플루엔자, 돼지 인플루엔자 또는 코로나 바이러스의 예방 또는 치료용 조성물
WO2010140734A1 (fr) Composition, pour la prévention ou le traitement d'affections liées à l'obésité et médiées par l'activation d'ampk, et dont les principes actifs dont des lignanes de 2,5-bis-aryl-3,4-diméthyltétrahydrofurane
KR101334143B1 (ko) 폴리갈라 카렌시움 추출물 및 이로부터 분리된 잔톤계 화합물을 함유하는 감기, 조류 인플루엔자, 돼지 인플루엔자 또는 신종플루의 예방 또는 치료용 조성물
KR20180128190A (ko) 망고스틴 추출물 또는 망고스틴 추출물로부터 유래한 잔톤계 화합물을 유효성분으로 포함하는 돼지유행성 설사 예방 또는 치료용 조성물
WO2016032249A1 (fr) Composition pharmaceutique contenant un extrait de vaccinium bracteatum thunb. ou une fraction de celui-ci comme principe actif pour prévenir ou traiter une inflammation des nerfs ou des maladies neurodégénératives
WO2013105693A1 (fr) Composition pharmaceutique comprenant un extrait de cortex d'oryza sativa l. et d'hordeum vulgare var. hexastichon comme principe actif
WO2018208128A1 (fr) Composition pharmaceutique comprenant de la tilianine en tant que principe actif pour le traitement prophylactique ou thérapeutique de la maladie de parkinson
KR20130071032A (ko) 단삼 추출물을 포함하는 코로나 바이러스 감염의 예방 또는 치료용 조성물
WO2018212531A1 (fr) Composition pharmaceutique pour la prévention ou le traitement de la démence et l'amélioration de la fonction cognitive, comprenant un extrait de salicorne
WO2020262799A1 (fr) Composition destinée à inhiber le virus de la grippe comprenant de la nodakénine et/ou de la nodakénétine
WO2011099812A2 (fr) Composition de prévention ou de traitement de l'infection à rotavirus, contenant un extrait de réglisse
WO2013062247A2 (fr) Composé diterpène de type phorbol, et composition pharmaceutique pour le traitement ou la prévention de maladies infectieuses virales le comprenant
WO2022173246A2 (fr) Composition pour la prévention ou le traitement d'une infection par le nouveau coronavirus, comprenant un extrait de psidiuma guajava, une fraction de phéophytine de celui-ci, ou un composé à base de méroterpénoïde isolé à partir de celui-ci en tant que principe actif
WO2017188499A1 (fr) Composition pharmaceutique de prévention ou de traitement des maladies hépatiques, comprenant de l'extrait de réglisse comprenant de la glycyrrhizine et de la liquiritine
KR101384633B1 (ko) 생강 추출물 또는 이의 분획물을 유효성분으로 포함하는 톡소플라즈마증의 예방 및 치료용 조성물
WO2018088777A1 (fr) Composition pour la prévention ou le traitement de la grippe, contenant, en tant que substance active, un extrait d'ecklonia cava ou un composé à base de tannin isolé à partir de celui-ci
WO2015065059A1 (fr) Composition pour prévenir ou traiter une septicémie hémorragique virale chez les poissons comprenant un extrait d'ecklonia cava
KR101427096B1 (ko) 관중 추출물 또는 이로부터 분리된 플로로글루시놀 유도체를 함유하는 코로나 바이러스 관련 질환의 예방 또는 치료용 조성물
WO2011046411A2 (fr) Extraits de marron possédant une activité de protection neurocellulaire et une activité d'inhibition de l'acétylcholinestérase, et leur utilisation
WO2023022523A1 (fr) Composition pour la prévention ou le traitement d'une nouvelle infection au coronavirus comprenant un composé à base de sesquiterpénoïdes obtenu à partir d'un extrait de feuilles de psidiuma guajava ou d'une fraction de celui-ci en tant que principe actif
WO2022173247A2 (fr) Composition contenant un extrait de chlorella sp. et une fraction phéophytinisée de celui-ci ou composé à base de porphyrine ou de caroténone obtenu à partir de celui-ci en tant que principe actif pour la prévention ou le traitement de la maladie du coronavirus-19

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 22753006

Country of ref document: EP

Kind code of ref document: A2

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 22753006

Country of ref document: EP

Kind code of ref document: A2