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WO2019245245A1 - Composition pharmaceutique pour la prévention et le traitement d'une lésion hépatique comprenant un extrait de curcuma - Google Patents

Composition pharmaceutique pour la prévention et le traitement d'une lésion hépatique comprenant un extrait de curcuma Download PDF

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Publication number
WO2019245245A1
WO2019245245A1 PCT/KR2019/007278 KR2019007278W WO2019245245A1 WO 2019245245 A1 WO2019245245 A1 WO 2019245245A1 KR 2019007278 W KR2019007278 W KR 2019007278W WO 2019245245 A1 WO2019245245 A1 WO 2019245245A1
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WO
WIPO (PCT)
Prior art keywords
formula
compound represented
liver damage
preventing
extract
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/KR2019/007278
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English (en)
Korean (ko)
Inventor
이영섭
이대영
김금숙
최두진
이재원
진잉유
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.)
Man Bang Bio Co Ltd
Korea Rural Development Administration
Original Assignee
Man Bang Bio Co Ltd
Korea Rural Development Administration
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 Man Bang Bio Co Ltd, Korea Rural Development Administration filed Critical Man Bang Bio Co Ltd
Publication of WO2019245245A1 publication Critical patent/WO2019245245A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT 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
    • A61K31/12—Ketones
    • 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
    • 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
    • A23V2250/00—Food ingredients
    • A23V2250/20—Natural extracts
    • A23V2250/21—Plant extracts
    • A23V2250/2112—Curcumin, turmeric

Definitions

  • 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 preventing and treating liver damage comprising turmeric ( Curcuma longa ) extract or a fraction thereof as an active ingredient.
  • the extract may be extracted through water, C1 ⁇ C4 alcohol or a mixed solvent thereof.
  • the fraction may be a fraction of the turmeric extract through a solvent roll containing ethyl acetate.
  • liver damage may be due to acetaminophen (Acetaminophen) drug.
  • the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 may be derived from Curcuma longa .
  • the extract or a fraction thereof may include a compound represented by the following formula (1), a compound represented by the formula (2), or a mixture thereof.
  • 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, a compound represented by the formula (2) or a salt thereof, or a mixture thereof as an active ingredient.
  • 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.
  • the present invention relates to a pharmaceutical composition for preventing and treating liver damage or a method for preventing and treating liver damage, which comprises Curcuma longa extract or a fraction thereof including the compound represented by Formula 1 or Formula 2 as an active ingredient.
  • the pharmaceutical composition for preventing and treating liver damage includes Curcuma longa extract or a fraction thereof as an active ingredient.
  • 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 , Ethylacetate fraction for turmeric ethanol extract in terms of the content of the active ingredient for treatment.
  • 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 compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 have an effect of inhibiting liver toxicity induced by acetaminophen treatment to improve cell survival rate of human liver cancer cell line (HepG2), and particularly, silymarin, a positive control group. Even if treated at a lower concentration it can be seen that hepatocellular protective effect is more excellent.
  • the compound represented by Chemical Formula 1 or the compound represented by Chemical Formula 2 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, a turmeric extract or a fraction thereof.
  • the obtained ethyl acetate fractions may be separated by silica gel column chromatography (inner diameter 10 ⁇ 20 cm, eluent CHCl 3 and volume ratio 40-60: 1), and each aliquot is thin layer chromatography ( After thin layer chromatography (TLC), each of the five fractions obtained was subjected to silica gel column chromatography (inner diameter 5 ⁇ 20 cm, eluting solvent CHCl 3 and a volume ratio of MeOH 10-30: 1). Refractions can be obtained for each fraction.
  • the yield of the compound represented by Formula 1 and the compound represented by Formula 2 may be about 30 mg of the compound represented by Formula 1 based on 100 g of ethyl acetate fraction, and the compound represented by Formula 2 is about 15 mg.
  • ODS cc octadecyl silica gel column chromatography
  • the compound represented by the formula (1) or the compound represented by the formula (2) 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 dissolved in a conventional method, for example, the compound represented by the formula (1) or the compound represented by the formula (2) in an excess of an aqueous acid solution, and the salt is a water miscible organic solvent, such as methanol, It can be prepared by precipitation with ethanol, acetone or acetonitrile.
  • a water miscible organic solvent such as methanol
  • the compound represented by the formula (1) or the compound represented by the formula (2) 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 compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 may be derived from Curcuma 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 comprising turmeric (Cu rcuma longa) extract or a fraction thereof as an active ingredient.
  • turmeric Cu rcuma longa
  • 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 may include a compound represented by Chemical Formula 1, a compound represented by Chemical Formula 2, or a mixture thereof.
  • 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 food composition for preventing and improving liver damage includes a compound represented by the following formula (1) or a salt thereof, a compound represented by the formula (2) or a salt thereof, or a mixture thereof as an active ingredient. .
  • Example 1 Turmeric, n-butanol 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 compounds represented by Formulas 1 and 2 were not detected.
  • the compounds represented by Formula 1 according to Example 1 and the compounds represented by Formula 2 according to Example 2 were each 10 ⁇ M in hepatocytes. After 2 hours of treatment with concentration, acetaminophen 10 mM treatment was used to measure cell viability after inducing 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) and the compound represented by the formula (2) has the effect of improving the cell survival rate of the human liver cancer cell line (HepG2) by inhibiting liver toxicity induced by acetaminophen treatment, In particular, even when treated at a lower concentration than the positive control silymarin can be confirmed that the 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) and the compound represented by the formula (2) is markedly through the treatment of the compound represented by the formula (1) or the compound represented by the formula (2) AST activity value elevated by acetaminophen treatment It can be confirmed that the degradation. In addition, it can be seen that more effective in reducing the AST activity level than silymarin treated at a higher concentration.
  • 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
  • Example 1 Turmeric Ethyl Acetate Fraction of Example 1 1000 mg, Vitamin A Acetate 70 ⁇ g, Vitamin E 1.0 mg, Vitamin B1 0.13 mg, Vitamin B2 0.15 mg, Vitamin B6 0.5 mg, Vitamin B12 0.2 ⁇ g, Vitamin C 10 mg, Biotin 10 ⁇ g , Nicotinic acid amide 1.7 mg, folic acid 50 ug, calcium pantothenate 0.5 mg, ferrous sulfate 1.75 mg, zinc oxide 0.82 mg, magnesium carbonate 25.3 mg, potassium monophosphate 15 mg, dicalcium phosphate 55 mg, potassium citrate 90 mg , 100 mg of calcium carbonate and 24.8 mg of magnesium chloride may be mixed, and the compounding ratio may be arbitrarily modified.

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Abstract

La présente invention concerne une composition pour la prévention et le traitement d'une lésion hépatique et, plus particulièrement, une composition pharmaceutique pour la prévention et le traitement d'une lésion hépatique qui comprend un extrait de curcuma et peut prévenir et traiter une lésion hépatique par l'amélioration des effets de protection des cellules hépatiques contre une hépatotoxicité.
PCT/KR2019/007278 2018-06-18 2019-06-17 Composition pharmaceutique pour la prévention et le traitement d'une lésion hépatique comprenant un extrait de curcuma Ceased WO2019245245A1 (fr)

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KR1020180069900A KR102092729B1 (ko) 2018-06-18 2018-06-18 강황 추출물을 포함하는 간손상 예방 및 치료용 약학 조성물
KR10-2018-0069900 2018-06-18

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KR20240055323A (ko) 2022-10-20 2024-04-29 주식회사 팜스킨 강황 초음파 추출물 또는 이의 분획물을 유효성분으로 포함하는 항산화 및 블루라이트 차단용 화장료 조성물

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KHORSANDI, L. ET AL.: "Protective effect of Curcuma longa extract on acetaminophen induced nephrotoxicity in mice", DARU, vol. 16, no. 3, 1 January 2008 (2008-01-01), pages 155 - 159, XP055665677 *
XIAO, Y. C. ET AL.: "Bisabocurcumin, a new skeleton curcuminoid from the rhizomes of Curcuma longa L", CHINESE CHEMICAL LETTERS, vol. 22, no. 12, 6 September 2011 (2011-09-06), pages 1457 - 1460, ISSN: 1001-8417, DOI: :10.1016/j.cclet.2011.09.002 *
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KR20190142672A (ko) 2019-12-27

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