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WO2019245243A1 - Composition pharmaceutique pour prévenir et traiter des lésions hépatiques comprenant un extrait de curcuma - Google Patents

Composition pharmaceutique pour prévenir et traiter des lésions hépatiques comprenant un extrait de curcuma Download PDF

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Publication number
WO2019245243A1
WO2019245243A1 PCT/KR2019/007272 KR2019007272W WO2019245243A1 WO 2019245243 A1 WO2019245243 A1 WO 2019245243A1 KR 2019007272 W KR2019007272 W KR 2019007272W WO 2019245243 A1 WO2019245243 A1 WO 2019245243A1
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Prior art keywords
formula
liver damage
compound represented
preventing
liver
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Ceased
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PCT/KR2019/007272
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English (en)
Korean (ko)
Inventor
이대영
이영섭
김금숙
최두진
이재원
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Korea Rural Development Administration
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Korea Rural Development Administration
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Ceased legal-status Critical Current

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    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
    • A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
    • 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)
    • A61K36/88—Liliopsida (monocotyledons)
    • A61K36/906—Zingiberaceae (Ginger family)
    • A61K36/9066—Curcuma, e.g. common turmeric, East Indian arrowroot or mango ginger
    • 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
    • A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • 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

Definitions

  • the present invention relates to a composition for preventing and treating liver damage, and more particularly, to improve the liver cell protection effect according to liver toxicity, turmeric extract, fractions thereof and / or components separated therefrom which can prevent and treat liver damage. It relates to a pharmaceutical composition for preventing and treating liver damage.
  • the liver is the most active organ of the human body in vivo metabolism is also the largest organ of the human body.
  • the liver is located between the digestive system and the systemic circulatory system and serves to defend the whole body from in vitro substances from outside.
  • the liver is also a very important organ responsible for various metabolism, detoxification, degradation, synthesis and secretion.
  • the liver has a function of managing the energy metabolism, all the nutrients absorbed from the food is metabolized into a substance capable of producing energy in the liver is supplied or stored throughout the body, about 2,000 kinds of enzymes, albumin, coagulation Serum proteins, bile acids, phospholipids, and fats such as cholesterol are synthesized, stored and distributed in the liver.
  • the liver also plays an important role in maintaining our lives because it has the ability to excrete various metabolites into the duodenum through the bile ducts and immune function.
  • the liver detoxifies drugs, alcohol, toxic substances and the like as a detoxifying and degrading function, hepatocytes are susceptible to damage and therefore drug, toxic, alcoholic liver diseases, and the like can frequently occur.
  • the ex vivo substance enters the liver the liver has a higher risk of being exposed to many toxic substances in addition to the nutrients, which is more likely to be damaged.
  • acetaminophen is an analgesic and anti-inflammatory drug known as Tylenol and is the most commonly used in the world, but it is reported to cause acute liver damage (liver necrosis, neurotoxins, liver cirrhosis, etc.) when overdose. have.
  • turmeric is a kind of Zingiberaceae and its scientific name is Curcuma longa . It is used as a spice in tropical regions of Southeast Asia, and has been widely used as a traditional medicine due to its strong antioxidant and anti-inflammatory properties. Curcuma longa has antifungal activity (Apisariyakul Amphawan et al., 1995, Antifungal activity of turmeric oil extracted from Curcuma longa, Journal of Ethnopharmacology, Vol. 49, No. 3, pp.163 ⁇ 169), anti-inflammatory, anti-HIV Biological activities (CAC Araujo et al., 2001, Biological activities of Curcuma longa L., MEMORIAS DO INSTITUTO OSWALDO CRUZ, pp. 723-728) have been reported. There have been no studies showing that turmeric extracts are effective in preventing and treating liver damage caused by liver toxicity.
  • the present invention has been made in view of the above, it is possible to prevent and treat liver damage by improving the liver cell protection effect according to liver toxicity, liver composition prevention and treatment pharmaceutical composition for liver damage comprising turmeric extract and functional ingredients or It is an object to provide a food composition for preventing and improving liver damage.
  • the present invention provides a pharmaceutical composition for the prevention and treatment of liver damage, comprising turmeric ( Curcuma longa ) extract or a fraction thereof containing the compound represented by the following formula (1) as an active ingredient.
  • the extract may be extracted through water, C1 ⁇ C4 alcohol or a mixed solvent thereof.
  • the fraction may be obtained by fractionating the turmeric extract through a solvent roll containing n-butanol.
  • liver damage may be due to acetaminophen (Acetaminophen) drug.
  • the present invention provides a pharmaceutical composition for preventing and treating liver damage, comprising a compound represented by the following formula (1) or a salt thereof as an active ingredient.
  • the compound represented by Chemical Formula 1 may be derived from Curcuma longa .
  • the present invention provides a food composition for preventing and improving liver damage, which comprises Curcuma longa extract or a fraction thereof including the compound represented by the following Formula 1 as an active ingredient.
  • the present invention provides a food composition for preventing and improving liver damage comprising a compound represented by the following formula (1) or a salt thereof as an active ingredient.
  • the compound represented by Chemical Formula 1 may be derived from Curcuma longa .
  • prevention in the present invention means any action that inhibits liver delay or delays the onset by administration of the composition.
  • treatment means any action that improves or advantageously changes the symptoms caused by liver damage by administration of the composition.
  • composition according to the present invention it is possible to significantly prevent, treat or improve liver damage by protecting the liver cells from liver damage caused by liver toxicity, in particular, liver toxicity caused by the drug, and thus preventing, treating and improving liver damage. It can be widely applied as a functional food.
  • Figure 1 is a graph of liver cell survival rate according to one embodiment and a comparative example of the present invention treated to human liver cell line induced liver damage by acetaminophen.
  • Figure 2 is a graph of the AST activity of liver cells according to one embodiment of the present invention and a comparative example treated with human liver cell line induced liver damage by acetaminophen.
  • Figure 3 is a graph of the LDH concentration of liver cells according to one embodiment of the present invention and a comparative example treated with human liver cell line induced liver damage by acetaminophen.
  • the present invention relates to a pharmaceutical composition for the prevention and treatment of liver damage, comprising a curcuma longa extract or a fraction thereof comprising the compound represented by the following formula (1) as an active ingredient, or to a method for preventing and treating liver damage .
  • the pharmaceutical composition for preventing and treating liver damage includes Curcuma longa extract or a fraction thereof including the compound represented by the following Chemical Formula 1 as an active ingredient.
  • turmeric extract will be described.
  • the turmeric (Cu rcuma longa) to be extracted may be purchased and used commercially, or may be one that is collected or grown in nature.
  • the turmeric may use any one or more portions of the root, stem, and leaves, preferably root.
  • the turmeric is not limited to whether the object is dried or pulverized during extraction, but preferably dried and pulverized may be used.
  • the turmeric extract may be extracted using a conventional extraction method in the art, and may be, for example, ultrasonic extraction, filtration and reflux extraction.
  • the turmeric pulverized pulverized turmeric from which the foreign matter is removed by washing and drying may be extracted through water, C1 ⁇ C4 alcohol or an extraction solvent that is a mixed solvent thereof. More preferably, the extraction solvent may be extracted using ethanol or ethanol aqueous solution. At this time, the extract may be extracted for 15 to 36 hours at a temperature condition of 20 ⁇ 30 °C.
  • the extract is filtered and the remaining extract is extracted again 2 to 4 times under the same conditions to obtain an extract.
  • the obtained extract may be included in the composition as it is, or concentrated under reduced pressure.
  • the decompression concentration can be carried out under conditions conventionally used in the art, and thus the detailed description thereof will be omitted.
  • the fraction may be a fraction of the turmeric extract obtained by the above-mentioned method using water, ethyl acetate and any one or more fractions of n-butanol using a conventional fractionation method in the art, preferably preventing liver damage , N-butanol fraction for turmeric ethanol extract in terms of the content of the therapeutically active ingredient.
  • the turmeric ethanol extract is partitioned and extracted through water and ethyl acetate, and then the aqueous layer is partitioned and extracted with n-butanol, and each layer is concentrated under reduced pressure to obtain an ethyl acetate fraction, n-butanol. Fractions and water fractions can be obtained.
  • the extract and the fraction comprises a compound represented by the following formula (1), through which can express a significant effect on the prevention and treatment of liver damage.
  • the compound represented by Formula 1 has an effect of inhibiting liver toxicity induced by acetaminophen treatment, thereby improving cell survival rate of human liver cancer cell line (HepG2), and in particular, hepatocytes even when treated at a lower concentration than the positive control silymarin It can be seen that the protective effect is more excellent.
  • the compound represented by Chemical Formula 1 may be referred to as an active ingredient included in turmeric extract or a fraction thereof to prevent and treat liver damage, and the compound may be, for example, silica gel column chromatography or reverse phase of turmeric extract or a fraction thereof. Separation and purification through silica gel column chromatography and Sephadex LH-20 column chromatography, can be carried out from one to several times until a single compound is purified, concentrated as needed, Recrystallization can be carried out.
  • the obtained n-butanol fraction may be fractionated using silica gel column chromatography (inner diameter 10 ⁇ 20 cm, elution solvents CHCl 3, MeOH and H 2 O by volume ratio 10-20: 2-5: 1). After confirming each aliquot by thin layer chromatography (TLC), silica gel column chromatography (inner diameter 3 ⁇ 20 cm, elution solvent CHCl 3, MeOH and H 2 O) was again performed on each of the five fractions obtained. Volume fraction of 5 to 15: 2 to 5: 1) to obtain a re-fraction for each fraction.
  • the yield of the compound represented by Formula 1 may be about 10 mg of the compound represented by Formula 1 based on 50 g of n-butanol fraction.
  • the compound represented by Chemical Formula 1 separated and purified by the above-described method may be included in the form of a pharmaceutically acceptable salt.
  • acid addition salts formed by pharmaceutically acceptable free acid are useful.
  • Acid addition salts include inorganic acids such as hydrochloric acid, nitric acid, phosphoric acid, sulfuric acid, hydrobromic acid, hydroiodic acid, nitrous acid or phosphorous acid and aliphatic mono and dicarboxylates, phenyl-substituted alkanoates, hydroxy alkanoates and alkanes. Obtained from non-toxic organic acids such as dioates, aromatic acids, aliphatic and aromatic sulfonic acids.
  • Such pharmaceutically toxic salts include sulfate, pyrosulfate, bisulfate, sulfite, bisulfite, nitrate, phosphate, monohydrogen phosphate, dihydrogen phosphate, metaphosphate, pyrophosphate chloride, bromide and iodide.
  • the acid addition salt is a conventional method, for example, by dissolving the compound represented by the formula (1) in an excess of an aqueous solution of acid, and dichloride is a water miscible organic solvent, such as methanol, ethanol, acetone or acetonitrile Can be prepared by precipitation.
  • dichloride is a water miscible organic solvent, such as methanol, ethanol, acetone or acetonitrile Can be prepared by precipitation.
  • the compound represented by Formula 1 of the present invention can be used in the form of a pharmaceutically acceptable metal salt using a base.
  • Alkali metal or alkaline earth metal salts can be obtained, for example, by dissolving the compound in an excess of alkali metal hydroxide or alkaline earth metal hydroxide solution, filtering the insoluble compound salt, and evaporating and drying the filtrate. At this time, it is pharmaceutically suitable to prepare sodium, potassium or calcium salt as the metal salt.
  • Corresponding silver salts can also be obtained by reacting alkali or alkaline earth metal salts with a suitable silver salt (eg, silver nitrate).
  • compositions according to one embodiment of the present invention may include a pharmaceutically acceptable carrier.
  • the composition comprising a pharmaceutically acceptable carrier may be in various oral or parenteral formulations.
  • Solid form preparations for oral administration include tablets, pills, powders, granules, capsules, and the like, which form at least one excipient such as starch, calcium carbonate, sucrose or lactose (at least one compound). lactose) and gelatin.
  • excipients such as starch, calcium carbonate, sucrose or lactose (at least one compound). lactose) and gelatin.
  • lubricants such as magnesium stearate, talc and the like are also used.
  • Liquid preparations for oral administration include suspensions, liquid solutions, emulsions, and syrups, and various excipients such as wetting agents, sweeteners, fragrances, and preservatives, in addition to commonly used simple diluents such as water and liquid paraffin, may be included.
  • Formulations for parenteral administration may include sterile aqueous solutions, non-aqueous solvents, suspensions, emulsions, lyophilized preparations, suppositories.
  • non-aqueous solvent and the suspension solvent propylene glycol, polyethylene glycol, vegetable oil such as olive oil, injectable ester such as ethyl oleate, and the like can be used.
  • As the base of the suppository witepsol, macrogol, tween 61, cacao butter, laurin butter, glycerogelatin and the like can be used.
  • the pharmaceutical composition is selected from the group consisting of tablets, pills, powders, granules, capsules, suspensions, liquid solutions, emulsions, syrups, sterile aqueous solutions, non-aqueous solutions, suspensions, emulsions, lyophilized preparations and suppositories. It can have either formulation.
  • compositions of the present invention may be administered in a pharmaceutically effective amount.
  • pharmaceutically effective amount means an amount sufficient to treat a disease at a reasonable benefit / risk ratio applicable to medical treatment, and the effective dose level is the degree of liver damage, the cause of liver damage, age, sex , The activity of the drug, the sensitivity to the drug, the time of administration, the route of administration and the rate of release, the duration of treatment, factors including the drug used concurrently and other factors well known in the medical field.
  • the pharmaceutical composition according to one embodiment of the present invention is preferably administered at 0.0001 to 100 mg / kg, preferably at 0.001 to 100 mg / kg, and the compound represented by the formula (1)
  • the compound represented by 2, or a mixture thereof is preferably administered at 0.0001 to 100 mg / kg, preferably at 0.001 to 10 mg / kg .
  • the compositions of the present invention may be administered as individual therapeutic agents or in combination with other therapeutic agents and may be administered sequentially or simultaneously with conventional therapeutic agents. And single or multiple administrations. Taking all of the above factors into consideration, it is important to administer an amount that can obtain the maximum effect in a minimum amount without side effects, and can be easily determined by those skilled in the art.
  • composition according to one embodiment of the present invention may be administered by various methods known in the art, for example, intraperitoneal administration, intravenous administration, intramuscular administration, subcutaneous administration, intradermal administration, oral administration, intranasal administration Administration, intrapulmonary administration, rectal administration, but is not limited thereto.
  • the pharmaceutical composition for preventing and treating liver damage includes the compound represented by the following formula (1) or a salt thereof as an active ingredient.
  • the compound represented by Chemical Formula 1 may be derived from turmeric (Cu rcuma longa) .
  • the pharmaceutical composition for preventing and treating liver damage according to the present invention as described above is effective in preventing and treating liver damage caused by various causes, and in particular, may express excellent efficacy on liver damage caused by acetaminophen drugs.
  • the present invention includes a food composition for preventing and improving liver damage, which includes turmeric (Cu rcuma longa) extract or a fraction thereof including the compound represented by Chemical Formula 1 as an active ingredient.
  • turmeric Cu rcuma longa extract or a fraction thereof including the compound represented by Chemical Formula 1 as an active ingredient.
  • turmeric extract or fractions thereof may be added to the food composition for the purpose of preventing and improving liver damage.
  • the extract and fractions thereof include the compound represented by the above formula (1).
  • the extract, fractions may be added as it is or used with other foods or food ingredients, and may be appropriately used according to conventional methods.
  • the mixed amount of the active ingredient may be suitably determined depending on the purpose of use (prevention, health or therapeutic treatment).
  • turmeric extract of the present invention or fractions thereof in the manufacture of food or beverage may be added in an amount of 0.01 to 10% by weight, preferably 0.1 to 3% by weight of the raw material composition, but is not limited thereto. It may be added in consideration of the period and the like.
  • various flavors or natural carbohydrates, etc. may be contained as additional ingredients, as in the usual beverage.
  • the natural carbohydrates described above may be glucose, monosaccharides such as fructose, disaccharides such as maltose, sucrose, and polysaccharides such as dextrin, cyclodextrin, sugar alcohols such as xylitol, sorbitol, erythritol.
  • sweetening agent natural sweetening agents such as tautin and stevia extract, synthetic sweetening agents such as saccharin and aspartame, and the like can be used.
  • the ratio of the natural carbohydrate may generally be about 0.01 to 0.04 g, preferably about 0.02 to 0.03 g, per 100 ml of the composition of the present invention, but is not limited thereto.
  • the proportion of such additives is not critical but is usually selected in the range of 0.01 to 0.1% by weight, based on the total composition weight.
  • Others may contain pulp for the production of natural fruit juices, fruit juice drinks and vegetable drinks. The proportion of such pulp is not critical but is usually selected in the range of 0.01 to 10% by weight, based on the total composition weight.
  • the liver composition for preventing and improving liver damage includes a compound represented by the following formula (1) or a salt thereof as an active ingredient.
  • the compound represented by Chemical Formula 1 may be derived from turmeric (Cu rcuma longa) .
  • composition for preventing and improving liver damage according to the present invention is effective in preventing and improving liver damage caused by various causes, but may exhibit particularly excellent effect on liver damage caused by acetaminophen drugs.
  • n-butanol fraction (CUB) obtained 50 g was subjected to silica gel column chromatography (inner diameter 10 ⁇ 20 cm, elution solvents CHCl 3, MeOH and H 2 O in a volume ratio of 15: 3: 1), and each aliquot (200). ml) was confirmed by thin layer chromatography (TLC) to obtain five fractions (CUB-1 to CUB-10).
  • Example 1 Turmeric, ethyl acetate and water fractions obtained in Example 1 were carried out in the same manner as in Example 1 to separate and purify each fraction. As a result, the compound represented by Formula 1 was not detected.
  • HepG2 cell 10% (v / v) fetal bovine serum (HepG2 cell) was used. FBS), penicillin (100 U / mL) and streptomycin (100 ⁇ g / mL) were added and cultured in a cell incubator maintained with 5% CO 2 at a temperature of 37 ° C.
  • the compound represented by Formula 1 according to Example 1 was treated with hepatocytes at a concentration of 10 ⁇ M for 2 hours, followed by 10 mM acetaminophen. Cell viability was measured after induction of hepatotoxicity for 24 hours.
  • hepatic cancer cell line treated with acetaminophen was not treated as a normal control group, and hepatic cancer cell line treated with only acetaminophen as a negative control group was used.
  • MTT assay was used for the measurement of cell viability, and the cells after the reaction were reacted with Thiazolyl blue tetrazolium bromide (MTT) reagent at a final concentration of 1 mg / ml for 1 hour.
  • MTT Thiazolyl blue tetrazolium bromide
  • the compound represented by the formula (1) has the effect of improving the cell survival rate of human liver cancer cell line (HepG2) by inhibiting liver toxicity induced by acetaminophen treatment, in particular lower than the positive control silymarin It can be seen that even if treated with a concentration, hepatocellular protective effect is more excellent.
  • AST activity level was evaluated, not the cell viability. Specifically, the AST activity was measured at 450 nm using an Aspartate Aminotransferase (AST) activity assay kit (Sigma). After quantified by the following AST activity calculation method, the results are shown in Figure 2 below.
  • AST Aspartate Aminotransferase
  • the compound represented by the formula (1) can be confirmed that the AST activity value increased by acetaminophen treatment is significantly reduced through the treatment of the compound represented by the formula (1) or the compound represented by the formula (2).
  • more effective in reducing the AST activity level than silymarin treated at a higher concentration can be seen.
  • the experiment was performed in the same manner as in Experimental Example 1, but the change in LDH concentration was measured instead of cell viability. That is, when hepatocytes are killed by injury, LDH (Lactate dehydrogenase) enzymes present in hepatocytes are released from the cells and the concentration is increased. Therefore, if the LDH concentration can be reduced, it can be regarded as an inhibitory effect on hepatocyte death.
  • LDH Lacate dehydrogenase
  • the LDH activity was measured for absorbance at 490 nm using LDH Cytotoxicity Detection Kit (TAKARA), expressed as a percentage of the absorbance ratio of the sample treated group compared to the normal control group without treatment. 3 is shown.
  • TAKARA LDH Cytotoxicity Detection Kit
  • Purified water was added to 1000 mg of the compound represented by Chemical Formula 1 of Example 1, 1000 mg of citric acid, 100 g of oligosaccharide, 2 g of plum concentrate, and 1 g of taurine, and the above ingredients were mixed according to a total 900 ml conventional health beverage preparation method. Next, after stirring and heating at 85 ° C for about 1 hour, the resulting solution was filtered and obtained in a sterilized 2L container, sealed sterilized and then refrigerated and prepared as a healthy beverage.

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Abstract

La présente invention concerne une composition visant à prévenir et à traiter des lésions hépatiques. Plus spécifiquement, la présente invention concerne une composition pharmaceutique pour prévenir et traiter des lésions hépatiques, comprenant un extrait de curcuma, qui est capable de prévenir et de traiter des lésions hépatiques par l'amélioration de l'effet protecteur de cellules hépatiques contre une hépatotoxicité.
PCT/KR2019/007272 2018-06-18 2019-06-17 Composition pharmaceutique pour prévenir et traiter des lésions hépatiques comprenant un extrait de curcuma Ceased WO2019245243A1 (fr)

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KR1020180069903A KR102069125B1 (ko) 2018-06-18 2018-06-18 강황 추출물을 포함하는 간손상 예방 및 치료용 약학 조성물
KR10-2018-0069903 2018-06-18

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Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20170120509A (ko) * 2016-04-21 2017-10-31 경희대학교 산학협력단 인진, 지유 및 울금 추출물 및 항바이러스제를 유효성분으로 포함하는 간질환 예방 또는 치료용 조성물

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20170120509A (ko) * 2016-04-21 2017-10-31 경희대학교 산학협력단 인진, 지유 및 울금 추출물 및 항바이러스제를 유효성분으로 포함하는 간질환 예방 또는 치료용 조성물

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
KALANTARI, H.: "The protective dffect of the Curcuma longa extract on acetaminophen-induced hepatotoxicity in mice", JUNDISHAPUR JOURNAL OF NATURAL PHARMACEUTICAL PRODUCTS, 2007 *
KHORSANDI, L.: "Protective effect of Curcuma longa extract on acetaminophen induced nephrotoxicity in mice", DARU, vol. 16, no. 3, 2008, pages 155 - 159, XP055665885 *
PARK, J.-H.: "New bisabolane sesquiterpenes from the rhizomes of Curcuma xanthorrhiza Roxb. and their inhibitory effects on UVB-induced MMP-1 expression in human keratinocytes", HELVETICA CHIMICA ACTA, 2014, XP055665880 *
SIRAT, H. M.: "Chemistry of xanthorrhizol: synthesis of several bisabolane sesquiterpenoids from xanthorrhizol", TETRAHEDRON LETTERS, 2007, XP005730758 *

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