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WO2020032365A1 - Composition, comprenant un composé de ginsénoside, pour la prévention ou le traitement d'une maladie inflammatoire médiée par des inflammasomes - Google Patents

Composition, comprenant un composé de ginsénoside, pour la prévention ou le traitement d'une maladie inflammatoire médiée par des inflammasomes Download PDF

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Publication number
WO2020032365A1
WO2020032365A1 PCT/KR2019/006677 KR2019006677W WO2020032365A1 WO 2020032365 A1 WO2020032365 A1 WO 2020032365A1 KR 2019006677 W KR2019006677 W KR 2019006677W WO 2020032365 A1 WO2020032365 A1 WO 2020032365A1
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WO
WIPO (PCT)
Prior art keywords
formula
disease
pharmaceutical composition
diseases
inflammasome
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Ceased
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PCT/KR2019/006677
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English (en)
Korean (ko)
Inventor
도은경
함종천
이웅희
이진하
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Modnbio Inc Co Ltd
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Modnbio Inc Co Ltd
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    • 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
    • A61K31/704—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin
    • 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
    • A23L33/125—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives containing carbohydrate syrups; containing sugars; containing sugar alcohols; containing starch hydrolysates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • 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

Definitions

  • the present invention relates to a composition for preventing, ameliorating or treating an inflammasome-mediated inflammatory disease containing a ginsenoside compound represented by Formula 1 or Formula 2 as an active ingredient.
  • Inflammasomes are caspase-1-activated complex protein complexes that include: 1) the sensory protein, NLRP3 (NOD-like receptor family, pyrin domain-containing 3), and 2) the adapter protein.
  • ASC adaptor protein apoptosis-associated spec-like protein containing a caspase-recruitment domain
  • effector protein procaspase-1 The above inflamasome components are assembled when microbial infection or tissue injury occurs. Inflamasomes activated by assembly in the cytosol activate caspase-1, thereby interleukin (IL) -1 ⁇ .
  • IL interleukin
  • Ginseng contains a variety of ginsenosides, meaning saponins.
  • Ginsenosides are protopanaxadiol-type (PPD type) ginsenosides, Protopanaxatriol-type (PPT type) ginsenosides and oleanolinic acids depending on the structure of aglycone.
  • PPD type protopanaxadiol-type
  • PPT type Protopanaxatriol-type
  • ginsenosides oleanolinic acids depending on the structure of aglycone.
  • Olelic acid type can be classified into three types of ginsenosides. These three groups, in turn, depend on the location of the sugar, the number of sugars, and the type of sugars attached by the glycosidic bonds to the carbon 3, 6 and 20 positions of the aglycone ring in the compound structure. Are classified.
  • Gifenoside LXXV is a ginsenoside compound belonging to the PPD type, and ginsenoside Rf is the PPT type.
  • the ginsenoside compound can be used for the prevention, amelioration or treatment of inflammasome-mediated diseases by inhibiting inflammasome activity.
  • an object of the present invention is to provide a pharmaceutical composition for preventing or treating inflammasome-mediated inflammatory disease, which contains a ginsenoside compound represented by Formula 1 or Formula 2 as an active ingredient.
  • Still another object of the present invention is to provide a food composition for preventing or ameliorating inflammasome mediated inflammatory disease, which contains a ginsenoside compound represented by Formula 1 or Formula 2 as an active ingredient.
  • Another object of the present invention is to administer a therapeutically effective amount of a ginsenoside compound represented by Formula 1 or Formula 2 or a pharmaceutically acceptable salt thereof to a subject in need thereof to prevent or prevent inflammasome mediated inflammatory disease. It is to provide a method of treatment.
  • the inventors of the present invention while searching for various types of ginsenosides, have found the effect of inhibiting the inflammasome activity of Gypenoside LXXV and Ginsenoside Rf to complete the present invention.
  • the present invention provides a pharmaceutical composition for the prevention or treatment of inflammasome-mediated inflammatory disease, comprising a ginsenoside compound represented by Formula 1 or Formula 2 as an active ingredient.
  • Ginsenoside compound represented by General formula (1) of this invention is Gypenoside LXXV which has the following structure.
  • Gypenoside LXXV has a molecular formula of C 42 H 72 O 13 , referred to as ( ⁇ , 12 ⁇ ) -3,12-dihydroxydammar-24-en-20-yl 6-O- ⁇ -D-glucopyranosyl- ⁇ -D-glucopyranoside do.
  • Ginsenoside compound represented by the formula (2) of the present invention is Ginsenoside Rf having the following structure.
  • the molecular formula of Ginsenoside Rf is C 42 H 72 O 14 , (3 ⁇ , 6 ⁇ , 12 ⁇ ) -3,12,20-Trihydroxydammar-24-en-6-yl 2-O- ⁇ -D-glucopyranosyl- ⁇ -D- It is called glucopyranoside.
  • the ginsenoside compound represented by Formula 1 or Formula 2 may be extracted from a plant, and hydrolyzed using an acid, hydrolyzed using heat, hydrolyzed using ultrasonic waves, or enzymes according to methods known in the art. It may be used by hydrolysis or synthesis, or may be commercially available.
  • the compound may be obtained from ginseng extract.
  • the type of ginseng used is not particularly limited, and ginseng, red ginseng, white ginseng, taeguksam, misam and the like can be used.
  • extracts from all parts of ginseng such as stems, roots, leaves, flowers, fruits, etc. can be used and are not limited to extracts of any particular part.
  • a method for extracting the ginsenoside compound represented by Formula 1 or Formula 2 from ginseng extract may use a known method.
  • active ingredient refers to a substance or a group of substances (including herbal medicines for which pharmacologically active ingredients and the like are not known) which are expected to express the efficacy effect of the composition directly or indirectly by inherent pharmacological action. It means to include the main component.
  • the pharmaceutical composition of the present invention may contain the ginsenoside compound represented by Formula 1 or Formula 2 in an amount of 0.001 to 50% by weight based on the total weight of the composition.
  • a pharmaceutical composition containing the compound represented by Formula 1 or Formula 2 of the present invention or a pharmaceutically acceptable salt thereof as an active ingredient effectively inhibits the production of IL-1 ⁇ according to the activation of inflammasomes, thereby causing an inflammasome-mediated inflammatory disease.
  • the prophylactic or therapeutic effect is excellent.
  • the activity of inflamasome induced by Nigericin or ATP and IL-1 ⁇ production in mice and human macrophages was effectively inhibited by the pharmaceutical composition of the present invention. (FIGS. 1-8).
  • the term “inflammasome” is present in the cytoplasm of myeloid cells and is a protein complex consisting of innate immune receptors (NOD-like receptor), ASC protein and caspase-1. It is involved in the conversion of pro-IL-1 ⁇ , a precursor of inflammatory cytokines associated with innate immune defenses, to mature IL-1 ⁇ . Inflamasomes composed of NLRP1, NLRP3, NLRC4, AIM4, etc., of which NLRP3 inflamasomes have been reported to be associated with the development of various autoimmune diseases.
  • IL-1 ⁇ is associated with human or acquired disease in humans, and it has been found that antagonists or receptors of IL-1 ⁇ may help in successful treatment of some diseases. Therefore, the relationship between inadequate inflamasome action and congenital and acquired inflammatory diseases is important in the immune response control mechanism.
  • the composition of the present invention can effectively regulate the amount of inflammatory cytokine IL-1 ⁇ secreted by inhibiting the activity of the inflamasome, has an excellent effect in the prevention and treatment of inflammatory diseases.
  • the pharmaceutical composition containing the compound represented by Formula 1 or Formula 2 of the present invention or a pharmaceutically acceptable salt thereof as an active ingredient may be usefully used for the prevention or treatment of inflammasome mediated inflammatory diseases.
  • inflammasome-mediated inflammatory disease refers to a condition or disease in which a prophylactic, ameliorating, or therapeutic effect can be expected by inhibiting the activity of an inflamasome (eg, NLRP3 inflamasome). Specific kinds of are well known in the art.
  • NLRP3 inflamasome is a metabolic disease, multiple sclerosis, inflammatory bowel disease, cryopyrin-associated periodic syndrome (CAPS), and other autoimmune diseases. And the initiation and progression of autoinflammatory diseases and the like.
  • NLRP3 inflammasome inhibitors such as MCC950 (diacylsulfonylurea-containing compound), ⁇ -hydroxybutyrate (BHB), type I interferon and IFN- ⁇ may be used to treat related diseases through inhibition of IL-1 ⁇ secretion. Suggests that it can be used.
  • an NLRP3 inhibitor specifically inhibits the activity of NLRP3 but not AIM2, NLRC4 or NLRP1 activity, blocks canonical and non-canonical NLRP3 activity, and inhibits IL-1 ⁇ production, thereby autoimmune encephalomyelitis, a disease model of multiple sclerosis ( relieving symptoms of encephalomyelitis (EAE), restoring the postmortal lethality of the CAPS mouse model, and having an activity on ex vivo samples of individuals with Muckel-Wells syndrome, including autoinflammatory and autoimmune diseases Suggests that it is a therapeutic agent for NLRP3-related diseases.
  • EAE encephalomyelitis
  • NLRP3 inflamasomes are associated with Alzheimer's disease, atherosclerosis, metabolic syndrome, and age-related macular degeneration (AMD).
  • AMD age-related macular degeneration
  • gouty arthritis is caused by the deposition of uric acid crystals that induce the activity of NLRP3 inflamasomes and is closely associated with the development of various metabolic diseases, including gouty arthritis. do.
  • the pharmaceutical composition containing the ginsenoside compound represented by Formula 1 or Formula 2 inhibits inflammasome activity.
  • the inflammasome is NLRP3 (NOD-like receptor family, pyrin domain-containing 3).
  • Inflamasome mediated inflammatory diseases in the present invention include at least one disease selected from the group consisting of autoinflammatory diseases, neuroinflammatory diseases and metabolic diseases.
  • auto-inflammatory disease refers to a group of diseases in which systemic inflammation is frequently repeated in the state where autoantibodies or antigen-specific T cells are not found, unlike autoimmune diseases.
  • Welles-Wells syndrome MMS
  • LADA adult delayed autoimmune diabetes
  • FCAS familial cold autoimmune syndrome
  • CAS cryopyrin-related periodic syndromes
  • NOMID neonatal-onset multicenter inflammatory syndrome
  • CINCA Chronic infant nerve skin joint
  • FMF familial Mediterranean fever
  • SJIA systemic onset childhood idiopathic arthritis
  • juvenile rheumatoid arthritis juvenile rheumatoid arthritis, adult rheumatoid arthritis, age-related macular degeneration, atopic dermatitis and psoriasis
  • It may be any one or more selected from, but includes, but is not limited to, other autoinflammatory diseases known in the art.
  • Formulations for parenteral administration may be formulated in the form of sterile aqueous solutions, liquids, non-aqueous solutions, suspensions, emulsions, eye drops, ophthalmic ointments, syrups, suppositories, aerosols, etc., and sterile injectables, respectively, according to conventional methods. It can be used to prepare a pharmaceutical composition of creams, gels, patches, sprays, ointments, warnings, lotions, linings, eye ointments, eye drops, pasta or cataplasma However, the present invention is not limited thereto. Compositions of topical administration may be anhydrous or aqueous, depending on the clinical prescription.
  • non-aqueous solvent and suspending agent propylene glycol, polyethylene glycol, vegetable oils such as olive oil, injectable esters such as ethyl oleate and the like can be used.
  • base of the suppository witepsol, macrogol, tween 61, cacao butter, laurin butter, glycerogelatin and the like can be used.
  • the term “therapeutically effective amount” refers to the amount of the compound represented by Formula 1 or Formula 2 effective for the prevention or treatment of inflammasome mediated inflammatory diseases, which is the disease or disorder being treated. Includes amounts that induce symptomatic relief.
  • the method for preventing or treating inflamasome-mediated inflammatory diseases of the present invention may be performed by administering a therapeutically effective amount of an additional active agent to help treat the disease together with the ginsenoside compound represented by Formula 1 or Formula 2. It may further include, an additional active agent may exhibit a synergistic or auxiliary effect with the ginsenoside compound represented by Formula 1 or Formula 2.
  • the present invention also provides a food composition for preventing or ameliorating an inflamasome-mediated inflammatory disease containing a ginsenoside compound represented by Formula 1 or Formula 2 or a salt thereof.
  • the food composition may be a nutraceutical or dietary supplement.
  • Figure 3 shows the effect of inhibiting the production of Nigericin-induced IL-1 ⁇ according to the concentration of the compound of the present invention.
  • LPS purified from E. coli was obtained from List Biological Laboratory Inc (Hornby, Canada) and dissolved in a non-toxic solution.
  • the ginsenosides used in the experiment used high purity materials of more than 98%.
  • ATP and Nigericin were purchased from Invivogen (San Diego, USA) and IL-1 ⁇ was purchased from R & D Systems (Minneapolis, MN, USA).
  • IL-1 ⁇ For ELISA experiments, the methods described in the known levels of IL-1 ⁇ in cell culture supernatants were determined with an ELISA kit (IL-1 ⁇ : R & D Systems) according to the manufacturer's instructions were used. IL-1 ⁇ levels in cell culture supernatants were determined according to the manufacturer's instructions using an ELISA kit (IL-1 ⁇ : R & D Systems).
  • the compound of Formula 1 or Formula 2 was treated with mouse macrophages at a concentration of 100 ⁇ g / ml, and then treated with 10 ⁇ M of Nigericin, and then measured at a concentration of IL-1 ⁇ 16 hours, induced by Nigericin, an NLRP3 agonist. The effect on the production of mature IL-1 ⁇ was investigated.
  • the compounds of Formula 1 and Formula 2 according to the present invention have an effect of inhibiting the production of IL-1 ⁇ by 50% or more compared to the vehicle induced with IL-1 ⁇ (200 pg / ml) by Nigericin treatment. (FIG. 1).
  • composition of the present invention can be used as a prophylactic, ameliorating or treating agent of NLRP3 inflamasome-related diseases by showing an excellent NLRP3 inflamasome inhibitory activity.
  • the compound of Formula 1 or Formula 2 of the present invention did not significantly affect the cell viability at the treatment concentration of 100 ⁇ g / ml did not have cytotoxicity (Fig. 2).
  • composition of the present invention can be used as a prophylactic, ameliorating, or treating agent of excellent NLRP3 inflamasome-related diseases.

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Abstract

La présente invention concerne une composition comprenant un composé de ginsénoside représenté par la formule chimique 1 ou 2 utilisé comme principe actif pour prévenir, soulager ou traiter une maladie inflammatoire médiée par des inflammasomes.
PCT/KR2019/006677 2018-08-07 2019-06-03 Composition, comprenant un composé de ginsénoside, pour la prévention ou le traitement d'une maladie inflammatoire médiée par des inflammasomes Ceased WO2020032365A1 (fr)

Applications Claiming Priority (2)

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KR10-2018-0092093 2018-08-07
KR1020180092093A KR101928553B1 (ko) 2018-08-07 2018-08-07 진세노사이드 화합물을 함유하는 인플라마좀 매개 염증성 질환의 예방 또는 치료용 조성물

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WO2020032365A1 true WO2020032365A1 (fr) 2020-02-13

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Publication number Priority date Publication date Assignee Title
KR101928553B1 (ko) * 2018-08-07 2018-12-12 주식회사 모든바이오 진세노사이드 화합물을 함유하는 인플라마좀 매개 염증성 질환의 예방 또는 치료용 조성물
KR102045044B1 (ko) * 2019-05-15 2019-11-14 주식회사 모든바이오 지페노사이드 화합물을 포함하는 망막 질환 예방 또는 치료용 조성물
KR102059659B1 (ko) * 2019-06-13 2019-12-26 주식회사 모든바이오 지페노사이드 화합물을 유효성분으로 포함하는 퇴행성 신경질환 치료용 조성물

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