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WO2010056080A2 - Composition comportant l'extrait de rumex aquatique pour la prévention et le traitement de maladie gastrite ou de maladie d'ulcère et son utilisation - Google Patents

Composition comportant l'extrait de rumex aquatique pour la prévention et le traitement de maladie gastrite ou de maladie d'ulcère et son utilisation Download PDF

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Publication number
WO2010056080A2
WO2010056080A2 PCT/KR2009/006727 KR2009006727W WO2010056080A2 WO 2010056080 A2 WO2010056080 A2 WO 2010056080A2 KR 2009006727 W KR2009006727 W KR 2009006727W WO 2010056080 A2 WO2010056080 A2 WO 2010056080A2
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WO
WIPO (PCT)
Prior art keywords
extract
disease
polar solvent
gastritis
rumex
Prior art date
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Ceased
Application number
PCT/KR2009/006727
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English (en)
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WO2010056080A3 (fr
Inventor
Uy Dong Sohn
Wan Kyunn Whang
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Industry Academic Cooperation Foundation of Chung Ang University
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Industry Academic Cooperation Foundation of Chung Ang University
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
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Publication of WO2010056080A2 publication Critical patent/WO2010056080A2/fr
Publication of WO2010056080A3 publication Critical patent/WO2010056080A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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)
    • A61K36/70—Polygonaceae (Buckwheat family), e.g. spineflower or dock
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
    • A61K2236/30—Extraction of the material
    • A61K2236/33—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
    • A61K2236/333—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones using mixed solvents, e.g. 70% EtOH
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
    • A61K9/146—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with organic macromolecular compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2022—Organic macromolecular compounds
    • A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
    • A61K9/2059—Starch, including chemically or physically modified derivatives; Amylose; Amylopectin; Dextrin

Definitions

  • the present invention is related to a composition comprising the extract of Rumex Aquaticus Herba for the prevention and treatment of gastritis disease or ulcer disease and the use thereof.
  • Gastritis disease occurs by hot and salty food and alcoholic beverage, which give rise to vomiting syndrome and gastroesophageal reflux disease.
  • Gastric juice has been regarded as a main offensive factor causing digestive ulcer and gastroesophageal reflux disease therefore the blocking of gastric juice has been a main target to develop treating agents of gastric ulcer, especially, gastric ulcer and gastroesophageal reflux disease (Nakamura K, et al., Jpn. J. Pharmacol ., 32(3), pp445-56, 1982; Okabe S et al., Jpn. J. Pharmacol ., 69(4), pp317-23, 1995).
  • Indomethacin a PGE2 reproduction inhibitor, inhibits the action of both of COX-1 and COX-2 however it has various unfavorable adverse actions, for example, necrotizing enterocelitis, irreversible GFR reduction, gastritis, erosive gastritis, CNS adverse action such as headache or hallucination, hematological change etc (Park, Y. S. et al, Korean Journal of Pediatrics., 50 , p1237, 2007).
  • the inhibition of intrinsic prostaglandin causes to a decrease of mucus volume of epithelial cell and the excretion of hydrogen carbonate, the reductionof epithelial cell proliferation and of resistance against the epithelial cell damage, the decrease of blood flow in mucous membrane, and develops to severe complication such as stomach hemorrhoid, stomach perforation resulting in death.
  • Rumex Aquaticus Herba a perennialherb belonged to polygonaceae genus, is distributed in Korea, Japan, Europe, and North America etc. Among the plants belonged to polygonaceae genus, there have been reported that Rumex japonicas contain 3-acetyl-2-methyl-1,5-dihydroxy-2,3-epoxynaphthoquinol (Zee O.P., et al. Arch. Pharm. Res ., Aug.
  • Rumex chalepensis contains quercetin-3-rhamnoside, kaemperol-3-rhamnopyranosyl(1 ⁇ -6)-ga1actoside, emodin etc (Hasan A, et al., Phytochemistry , Jul. 39(5) , pp1211-3, 1995); and Rumex luminastrum contains chrysophanic acid, emodin, nepodin (2-acetyl-1,8-dihydroxy-3-methyl naphthalene) etc (Abe el-Fattah H., et al., Acta Pharm. Hung , May 64(3) , pp83-5, 1994).
  • the present inventors have investigated the therapeutic activity of the extract of Rumex Aquaticus Herba on gastritis disease or ulcer disease through acute gastritis disease animal model test caused by indomethacin and found that the area of damaged gastric lesion caused by acute gastritis was significantly decreased.
  • the present invention also provides a use of the extract of Rumex Aquaticus Herba for the manufacture of medicament employed for treating or preventing gastritis disease or ulcer disease in human or mammal.
  • the present invention also provides a method for treating gastritis disease or ulcer disease in human or mammal comprising administering to said mammal an effective amount of above-mentioned extract, together with a pharmaceutically acceptable carrier thereof.
  • the present invention provides a pharmaceutical composition comprising the extract of Rumex Aquaticus Herba as an active ingredient for treating or preventing gastritis disease or ulcer disease.
  • the present invention also provides a health functional food comprising the above-described extract for the prevention or improvement of gastritis disease or ulcer disease as an active ingredient in an amount effective to preventing and improving gastritis disease or ulcer disease, together with a sitologically acceptable additive.
  • a pharmaceutical composition comprising the extract of Rumex Aquaticus Herba as an active ingredient for treating or preventing gastritis disease or ulcer disease, together with a pharmaceutically acceptable carrier.
  • the extract of Rumex Aquaticus Herba comprise the (1) crude extract soluble in the solvent selected from distilled water, alcohols such as methanol, ethanol and the like, or the mixtures thereof, preferably, distilled water, ethanol, or the mixtures thereof, more preferably, ethanol or 50-90% ethanol, most preferably, 50-70% ethanol solvent; and (2) the polar solvent-soluble fraction which removed the non-polar solvent-soluble fraction through fractionation step, for example, which can be prepared by the procedure comprising the steps: diluting the crude extract with distilled water and subjecting to fractionation with non-polar solvent such as chloroform, ether or methylene chloride, preferably, chloroform to remove non-polar solvent soluble substance at 1 st step; and collecting the polar solvent soluble fraction to obtain purposed polar solvent-soluble fraction of the present invention.
  • non-polar solvent such as chloroform, ether or methylene chloride, preferably, chloroform to remove non-polar solvent soluble substance at 1 st step
  • a health functional food comprising the above-described extract for the prevention or improvement of gastritis disease or ulcer disease as an active ingredient in an amount effective to preventing and improving gastritis disease or ulcer disease, together with a sitologically acceptable additive.
  • the pharmaceutical composition of the present invention could contain about 0.01 to 95 w/w%, preferably 0.5 to 50 w/w% of inventive extract of present invention based on the total weight of the composition.
  • An inventive extract may be prepared in accordance with the following preferred embodiment.
  • the above-described extract of Rumex Aquaticus Herba can be prepared by following procedure.
  • the Rumex Aquaticus Herba is washed, dried, and mixed with 0.3 to 5-fold, preferably, 1 to 3-fold volume (w/v) of distilled water, alcohols such as methanol, ethanol and the like, or the mixtures thereof, preferably, distilled water, ethanol, or the mixtures thereof, more preferably, ethanol or 50-90% ethanol, most preferably, 50-70% ethanol solvent
  • the solution is enfleuraged at the temperature ranging from 5 to 70°C, preferably, 20 to 60°C, for the period ranging from 1 hour to 3 days, preferably 3 to 24 hours or heated with reflux extraction at the temperature ranging from 80 to 120°C, preferably above 105°C, for the period ranging from 1 to 24 hours, preferably 2 to 5 hours with 2 to 5 times, or extracted by sonication, reflux or conventional extraction, preferably, enfleurage extraction the solution is filtered and dried at below 80°C, to obtain the crude extract of the present invention.
  • the crude extract prepared from the above step is diluted with 1 to 10-fold, preferably, 2 to 6-fold volume (v/w) of distilled water, mixed with non-polar solvent such as chloroform, ether or methylene chloride, preferably, chloroform preferably, with mixed ratio of water: chloroform (1:2; v/v) to remove non-polar solvent soluble substance, and subjected to fractionation to collect the polar solvent soluble of the present invention.
  • non-polar solvent such as chloroform, ether or methylene chloride
  • chloroform preferably, with mixed ratio of water: chloroform (1:2; v/v) to remove non-polar solvent soluble substance
  • It is still another object of the present invention to provide a pharmaceutical composition comprising the extract of Rumex Aquaticus Herba obtained by above described process as an active ingredient for preventing and treating gastritis disease or ulcer disease.
  • the inventive composition of the present invention significantly decrease the area of damaged gastric lesion caused by acute gastritis when the inventive extract of the present invention was orally administrated thereto.
  • the pharmaceutical composition for treating gastritis disease or ulcer disease could contain about 0.01 to 99.9 w/w%, preferably 0.1 to 90 w/w% of the above crude drug composition of present invention based on the total weight of the composition.
  • the inventive composition may additionally comprise conventional carrier, adjuvants or diluents in accordance with a using method. It is preferable that said carrier is used as appropriate substance according to the usage and application method, but it is not limited. Appropriate diluents are listed in the written text of Remington's Pharmaceutical Science (Mack Publishing co, Easton PA).
  • composition according to the present invention can be provided as a pharmaceutical composition containing pharmaceutically acceptable carriers, adjuvants or diluents, e.g., lactose, dextrose, sucrose, sorbitol, mannitol, xylitol, erythritol, maltitol, starches, acacia rubber, alginate, gelatin, calcium phosphate, calcium silicate, cellulose, methyl cellulose, polyvinyl pyrrolidone, water, methylhydroxy benzoate, propylhydroxy benzoate, talc, magnesium stearate and mineral oil.
  • pharmaceutically acceptable carriers e.g., lactose, dextrose, sucrose, sorbitol, mannitol, xylitol, erythritol, maltitol, starches, acacia rubber, alginate, gelatin, calcium phosphate, calcium silicate, cellulose, methyl cellulose, polyvinyl
  • the formulations may additionally include fillers, anti-agglutinating agents, lubricating agents, wetting agents, flavoring agents, emulsifiers, preservatives and the like.
  • the compositions of the invention may be formulated so as to provide quick, sustained or delayed release of the active ingredient after their administration to a patient by employing any of the procedures well known in the art.
  • compositions of the present invention can be dissolved in oils, propylene glycol or other solvents which are commonly used to produce an injection.
  • suitable examples of the carriers include physiological saline, polyethylene glycol, ethanol, vegetable oils, isopropyl myristate, etc., but are not limited to them.
  • the compounds of the present invention can be formulated in the form of ointments and creams.
  • compositions containing inventive composition may be prepared in any form, such as oral dosage form (powder, tablet, capsule, soft capsule, aqueous medicine, syrup, elixirs pill, powder, sachet, granule), or topical preparation (cream, ointment, lotion, gel, balm, patch, paste, spray solution, aerosol and the like), suppository, or sterile injectable preparation (solution, suspension, emulsion).
  • oral dosage form poowder, tablet, capsule, soft capsule, aqueous medicine, syrup, elixirs pill, powder, sachet, granule
  • topical preparation cream, ointment, lotion, gel, balm, patch, paste, spray solution, aerosol and the like
  • suppository sterile injectable preparation
  • inventive composition of the present invention in pharmaceutical dosage forms may be used in the form of their pharmaceutically acceptable salts, and also may be used alone or in appropriate association, as well as in combination with other pharmaceutically active compounds.
  • the desirable dose of the inventive composition varies depending on the condition and the weightof the subject, severity, drug form, route and period of administration, and may be chosen by those skilled in the art. However, in order to obtain desirable effects, it is generally recommended to administer at the amount ranging 0.01-10g/kg, preferably,1 to 5g/kg by weight/day of the inventive composition of the present invention.
  • the dose may be administered in a single or multiple doses per day.
  • the crude drug composition should be present between 0.01 to 80% by weight, preferably 0.5 to 50% by weight based on the total weight of the composition.
  • composition of present invention can be administered to a subject animal such as mammals (rat, mouse, domestic animals or human) via various routes. All modes of administration are contemplated, for example, administration can be made orally, rectally or by intravenous, intramuscular, subcutaneous, intracutaneous, intrathecal, epidural or intracerebroventricular injection.
  • a health functional food comprising the above extract for the prevention or improvement of gastritis disease or ulcer disease as an active ingredient in an amount effective to preventing and improving gastritis disease or ulcer disease, together with a sitologically acceptable additive.
  • the crude drug composition of inventive health functional food is used in the form of pulverized form thereof, extracted form therefrom or dried extract form thereof.
  • the health functional food composition for preventing and improving gastritis disease or ulcer disease could contain about 0.01 to 95 w/w%, preferably 0.5 to 80 w/w% of the above inventive composition of present invention based on the total weight of the composition.
  • composition therein can be added to food, additive or beverage for prevention and improvement of gastritis disease or ulcer disease.
  • amount of above described crude drug composition in food or beverage may generally range from about 0.1 to 15 w/w %, preferably 1 to 10 w/w % of total weight of food for the health food composition and 1 to 30 g, preferably 3 to 10 g on the ratio of 100ml of the health beverage composition.
  • the health beverage composition of present invention contains above described crude drug composition as an essential component in the indicated ratio
  • the other component can be various deodorant or natural carbohydrate etc such as conventional beverage.
  • natural carbohydrate are monosaccharide such as glucose, fructose etc; disaccharide such as maltose, sucrose etc; conventional sugar such as dextrin, cyclodextrin; and sugar alcohol such as xylitol, and erythritol etc.
  • natural deodorant such as taumatin, stevia extract such as levaudioside A, glycyrrhizin et al., and synthetic deodorant such as saccharin, aspartam et al.
  • the amount of above described natural carbohydrate is generally ranges from about 1 to 20 g, preferably 5 to 12 g in the ratio of 100ml of present beverage composition.
  • the other components than aforementioned composition are various nutrients, a vitamin, a mineral or an electrolyte, synthetic flavoring agent, a coloring agent and improving agent in case of cheese chocolate et al., pectic acid and the salt thereof, alginic acid and the salt thereof, organic acid, protective colloidal adhesive, pH controlling agent, stabilizer, a preservative, glycerin, alcohol, carbonizing agent used in carbonate beverage et al.
  • the other component than aforementioned ones may be fruit juice for preparing natural fruit juice, fruit juice beverage and vegetable beverage, wherein the component can be used independently or in combination.
  • the ratio of the components is not so important but is generally range from about 0 to 20 w/w % per 100 w/w % present composition.
  • Examples of addable food comprising aforementioned crude drug composition therein are various food, beverage, gum, vitamin complex, health improving food and the like.
  • the inventive extract significantly decrease the area of damaged gastric lesion caused by acute gastritis when the inventive extract of the present invention was orally administrated to indomethacin-induced acute gastritis animal model.
  • the inventive compositions according to the present invention are useful in the prevention and treatment of gastritis disease or ulcer disease.
  • the extract was filtered with filter paper and the filtrate was concentrated with vacuum concentrator (N-11, ELYA) at below 50°C to obtain 350g of 60% dried crude extract (1) of Rumex Aquaticus Herba (yield: 8.75%, designated as SW0804141, hereinafter).
  • Example 1 350g of the dried extract of Rumex Aquaticus Herba prepared in Example 1 was added with distilled water, mixed with chloroform with the mixed ratio of 1:2 (v/v) and left alone for one day to remove chloroform soluble layer. The remaining water layer was concentrated with vacuum concentrator (N-11, ELYA) to obtain 210g of polar-solvent soluble extract of Rumex Aquaticus Herba (yield: 5.25%, designated as SW0804142, hereinafter).
  • N-11, ELYA vacuum concentrator
  • the extract was filtered with filter paper and the filtrate was concentrated with vacuum concentrator (N-11, ELYA) at below 80°C to obtain 350g of dried crude extract (2) of Rumex Aquaticus Herba (yield: 8.75%, designated as SW0807041, hereinafter).
  • Indomethacin (I7378, Sigma Chemical Co.) was purchased from commercial company to use as a positive control in experimental.
  • mice Male Sprague-Dawley rats (Samtako Co. Korea) weighing 200-220g were used in the experiment and were allowed to access to feed and drinking water. All animals were maintained in a controlled environment with temperatures at 20-25°C and relative humidity at 40-65% with 12 hours of light (150-300 lux) and dark cycles for at least one week prior to use.
  • test groups All the result was analyzed by using pharmacological calculation. The significance between the test groups was evaluated by ANOVA (one-way analysis of variance) and determined by Student's t-test method (*p ⁇ 0.05).
  • Indomethacin (IND) prepared in Reference Example in distilled water (40mg/kg) were orally administrated into the rats and one hour after the treatment, various concentrations of inventive extract prepared in Examples were orally administrated. 6 hours after the treatment, the rates were killed with cervical dislocation to deliver stomach sample and the stomach was fixed with 3% formalin to determine the damaged area of the stomach.
  • the group treated with inventive extracts showed sharply decreased area of damaged region, i.e., SW0804141 (100mg/kg; 9.68 cm 2 ) and SW0804142 (100mg/kg; 24.43mm 2 ) respectively while the group treated with sole indomethacin (40mg/kg) showed more wide ulcer area (36.58 mm 2 ) ( See Table 1).
  • the group treated with inventive extracts showed sharply decreased area of damaged region, i.e., SW0807041 (10mg/kg; 13.68 cm 2 ) and SW0807042 (10mg/kg; 7.18 mm 2 ) respectively, while the group treated with sole indomethacin (40mg/kg) showed more wide ulcer area (36.58 mm 2 ) ( See Table 2).
  • the inventive extract showed potent treating activity of gastritis and gastric ulcer through the result.
  • Powder preparation was prepared by mixing above components and filling sealed package.
  • Tablet preparation was prepared by mixing above components and entabletting.
  • Tablet preparation was prepared by mixing above components and filling gelatin capsule by conventional gelatin preparation method.
  • Injection preparation was prepared by dissolving active component, controlling pH to about 7.5 and then filling all the components in 2ml ample and sterilizing by conventional injection preparation method.
  • Liquid preparation was prepared by dissolving active component, and then filling all the components in 1000ml ample and sterilizing by conventional liquid preparation method.
  • Vitamin A acetate 70 ⁇ g
  • Vitamin E 1.0mg
  • Vitamin B 1 0.13mg
  • Vitamin B 6 0.5mg
  • Vitamin B 12 0.2 ⁇ g
  • Vitamin A 0.2g
  • Vitamin B 1 0.25g
  • Vitamin B 2 0.3g
  • Health beverage preparation was prepared by dissolving active component, mixing, stirred at 85°C for 1 hour, filtered and then filling all the components in 1000ml ample and sterilizing by conventional health beverage preparation method.
  • the inventive extract significantly decrease the area of damaged gastric lesion caused by acute gastritis when the inventive extract of the present invention was orally administrated to indomethacin-induced acute gastritis animal model.
  • the inventive compositions according to the present invention are useful in the prevention and treatment of gastritis disease or ulcer disease.

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  • Health & Medical Sciences (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
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Abstract

La présente invention concerne une composition comportant l’extrait de Rumex aquatique pour la prévention et le traitement de maladie gastrite ou de maladie d’ulcère et son utilisation. L’extrait selon l’invention réduit considérablement la région de lésion gastrique endommagée provoquée par la gastrite aigüe lorsque l’extrait selon la présente invention est administré oralement à un modèle animal de gastrite aigüe induite par l’indométhacine. Les compositions selon la présente invention sont utiles dans la prévention et le traitement de maladie gastrite ou de maladie d’ulcère.
PCT/KR2009/006727 2008-11-17 2009-11-16 Composition comportant l'extrait de rumex aquatique pour la prévention et le traitement de maladie gastrite ou de maladie d'ulcère et son utilisation Ceased WO2010056080A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020080113753A KR101066981B1 (ko) 2008-11-17 2008-11-17 양제엽의 추출물 또는 분획물을 유효성분으로 함유하는위장관 염증 및 궤양의 예방 및 치료를 위한 조성물
KR10-2008-0113753 2008-11-17

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WO2010056080A2 true WO2010056080A2 (fr) 2010-05-20
WO2010056080A3 WO2010056080A3 (fr) 2010-09-16

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KR101395628B1 (ko) * 2012-03-13 2014-05-19 중앙대학교 산학협력단 양제엽 추출물을 유효성분으로 함유하는 급성 대장염 질환의 예방 및 치료를 위한 약학조성물

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JPH0930987A (ja) * 1995-07-20 1997-02-04 Mikio Ito 難治性の潰瘍、胃炎及び皮膚炎の治療乃至予防用製剤
KR100518360B1 (ko) * 2002-05-27 2005-09-30 손의동 토대황에서 분리한 퀘르세틴-3-오-베타-디-글루쿠로니드를 분리하는 방법 및 이 화합물을 함유하는 위염 및 역류성 식도염 질환 예방 및 치료를 위한 조성물

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KR101066981B1 (ko) 2011-09-22
KR20100054923A (ko) 2010-05-26

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