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WO2021187679A1 - Composition comprenant un composé de saponine dérivé du concombre de mer pour prévenir, soulager ou traiter une neuropathie - Google Patents

Composition comprenant un composé de saponine dérivé du concombre de mer pour prévenir, soulager ou traiter une neuropathie Download PDF

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Publication number
WO2021187679A1
WO2021187679A1 PCT/KR2020/009363 KR2020009363W WO2021187679A1 WO 2021187679 A1 WO2021187679 A1 WO 2021187679A1 KR 2020009363 W KR2020009363 W KR 2020009363W WO 2021187679 A1 WO2021187679 A1 WO 2021187679A1
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Prior art keywords
formula
neuropathy
compound
alleviating
preventing
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PCT/KR2020/009363
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English (en)
Korean (ko)
Inventor
이연주
최한솔
이희승
현정미
양정은
송명진
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Korea Institute of Ocean Science and Technology KIOST
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Korea Institute of Ocean Science and Technology KIOST
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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
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
    • 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
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K35/00—Medicinal preparations containing materials or reaction products thereof with undetermined constitution
    • A61K35/56—Materials from animals other than mammals
    • A61K35/616—Echinodermata, e.g. starfish, sea cucumbers or sea urchins
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
    • C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
    • 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
    • A23V2200/322—Foods, ingredients or supplements having a functional effect on health having an effect on the health of the nervous system or on mental function
    • 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
    • A23V2250/204—Animal extracts
    • A23V2250/2042—Marine animal, fish extracts
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2250/00—Food ingredients
    • A23V2250/30—Other Organic compounds

Definitions

  • the present invention relates to a composition for preventing, alleviating or treating neuropathy comprising a sea cucumber-derived saponin compound.
  • TRP channels Transient receptor potential channels are ion channels that exist in animal cell membranes and are involved in the transmission of sensory signals related to temperature, taste, pain, pressure, and visual field by mediating intracellular/extracellular movement of potassium, sodium, and magnesium.
  • the TRP channel is divided into various subgroups according to the amino acid sequence constituting the protein, structure, function, distribution, etc.
  • TRPA1 TRP ankyrin 1
  • TRPA1 TRP ankyrin 1
  • TRP ankyrin 1 has 14 to 18 ankyrin protein sequences in the protein, has been shown to mediate ion transport for the formation of sensations associated with TRPA1 is expressed in various primary sensory neurons constituting the nervous system as well as various cells forming glial cells, and is widely involved in the expression and control of pain-related pathological symptoms.
  • TRPA1 pathological symptoms related to TRPA1 that have been identified so far include cold hypersensitivity, pain caused by irritant compounds or tissue damage, pain caused by bacterial infection or inflammation, migraine or visceral pain, as well as neuropathy. Included.
  • Neuropathy is pain caused by damage or disease of peripheral nerves, and includes allodynia, in which severe pain is felt even with minute symptoms, or hyperalgesia, which is a state in which pain sensitivity to stimuli is increased.
  • Neuropathies caused by various causes include diabetic neuropathy, chemotherapy-induced painful neuropathy, traumatic neuropathy, and inflammatory neuropathy. neuropathy), etc.
  • antidepressants As neuropathy treatments, but antidepressants and anticonvulsants have been reported to have an analgesic effect of 50% in less than 30% of patients. There is a need to develop a treatment for neuropathy with high efficacy and fewer side effects even after long-term use.
  • TRPA1 agonists such as methylglyoxal and 4-hydroxynonenal to increase nerve endings. It has been reported to induce disease.
  • chemotherapy-induced neuropathy the efficacy of TRPA antagonists has been demonstrated in animal experiments.
  • allodynia caused by anticancer drugs paclitaxel, bortezomib, oxaliplatin, etc. is controlled by TRPA1 antagonists. that has been confirmed
  • the function of TRPA1 is also linked to the signaling mechanism of the bradykinin B2 receptor, so it has been reported that it is highly related to cold pain caused by tissue damage or inflammation. Accordingly, the potential for development of TRPA1 antagonists as a treatment for neuropathy is highly evaluated.
  • TRPA1 antagonists include synthetic organic compounds in the form of xanthine, oxime, and sulfonamide. It has been confirmed, and the related efficacy was also confirmed in Shiho ( Bupleuri Radix ) extract and psychosaponin D isolated therefrom. Clinical trials have been conducted on TRPA1 antagonists synthesized in the US and Europe as a treatment for pain, but TRPA1 antagonists that have been approved as pharmaceuticals have not been reported at home or abroad.
  • An object of the present invention is to provide a preventive, alleviating or therapeutic use of a saponin compound derived from sea cucumber having an inhibitory ability of TRPA1 (TRP ankyrin 1) for neuropathy.
  • the present invention provides a pharmaceutical composition for preventing, alleviating or treating neuropathy, comprising a compound of Formula 1 below:
  • R 1 is , , or represents,
  • R 2 and R 3 each independently represents hydrogen or hydroxy, or R 2 and R 3 form a carbon-oxygen double bond between the carbon and oxygen atoms to which they are attached,
  • R 4 represents a sugar
  • the present invention also provides the use of the compound of formula (1) above for the manufacture of a medicament for the prevention, alleviation or treatment of neuropathy.
  • the present invention provides a method for treating neuropathy comprising administering to a subject in need thereof an effective amount of the compound of Formula 1 above.
  • the present invention also provides a food composition for preventing, alleviating or improving neuropathy comprising the compound of Formula 1 above.
  • the present invention also provides the use of the compound of formula 1 for the manufacture of a food for preventing, alleviating or ameliorating neuropathy.
  • the present invention also provides a compound represented by the formula (5):
  • the sea cucumber-derived saponin compound according to the present invention lowers the function of the TRPA1 protein, which mediates the transmission of pain signals through the movement of calcium ions, so that it can be usefully used as an active ingredient in medicine, food, etc. for the prevention, alleviation or treatment of neuropathy.
  • Figure 1a shows the TRPA1 inhibition rate of a fraction obtained from a methanol 90% mobile phase in a fraction of a sea cucumber ( Bohadschia vitiensis ) extract at five concentrations (10 -1.0 , 10 -0.5 , 10 0.0 , 10 0.5 , 10 1.0 , 10 1.5 ⁇ g/mL ) is the result of checking.
  • Figure 1b shows the TRPA1 inhibition rate of the fraction obtained from the methanol 100% mobile phase in the fraction of the sea cucumber ( Bohadschia vitiensis ) extract at five concentrations (10 -1.0 , 10 -0.5 , 10 0.0 , 10 0.5 , 10 1.0 , 10 1.5 ⁇ g/mL ) is the result of checking.
  • Figures 2a to 2f show the TRPA1 inhibition rate of 6 saponin compounds (compounds 1, 2, 3, 4, 5 and 6) isolated from the active fraction of the sea cucumber ( Bohadschia vitiensis ) extract at 5 concentrations (10 -1.0 , 10 ) -0.5 , 10 0.0 , 10 0.5 , 10 1.0 , 10 1.5 ⁇ g/mL).
  • the present invention relates to a pharmaceutical composition for preventing, alleviating or treating neuropathy, comprising a compound of formula (1):
  • R 1 is , , or represents,
  • R 2 and R 3 each independently represents hydrogen or hydroxy, or R 2 and R 3 form a carbon-oxygen double bond between the carbon and oxygen atoms to which they are attached,
  • R 4 represents a sugar
  • the present invention also provides the use of the compound of formula (1) above for the manufacture of a medicament for the prevention, alleviation or treatment of neuropathy.
  • the compound of Formula 1 may specifically include compounds of Formulas 2 to 7:
  • the compound of Formula 1 of the present invention is characterized in that it is derived from a sea cucumber ( Bohadschia vitiensis ) extract.
  • extract refers to a preparation obtained by extracting a crude drug with an appropriate extraction solvent and evaporating the extraction solvent to concentrate, an extract obtained by extraction treatment, a diluted or concentrated liquid of the extract, a dried product obtained by drying the extract, and a crude product thereof Or it may be a purified product.
  • the sea cucumber extract may be prepared using a general extraction method known in the art, for example, hot water extraction, hot water extraction, cold extraction, reflux cooling extraction, or ultrasonic extraction may be used.
  • a crude extract can be obtained by lyophilizing the sea cucumber individual after cutting, extracting it cold with alcohol and filtering it.
  • the compound of Formula 1 is a saponin compound having a saponin matrix structure, and has TRPA1 (Transient receptor potential cation channel, subfamily A, member 1) inhibitory activity that mediates the transmission of a pain signal through the movement of calcium ions. It can be used for prevention, alleviation or treatment.
  • TRPA1 Transient receptor potential cation channel, subfamily A, member 1
  • the compounds of Formulas 2 to 7 have TRPA1 inhibitory ability calculated as IC 50 values, respectively, 0.6 ⁇ M, 1.07 ⁇ M, 1.26 ⁇ M, 2.26 ⁇ M, 1.36 ⁇ M, and 1.33 ⁇ M, respectively, representing TRPA1 as a control. Compared to 0.80 ⁇ M of the antagonist A-967970, it exhibited superior or similar TRPA1 inhibitory ability.
  • neuropathy refers to pain caused by damage or disease of the peripheral nerves, and includes allodynia, in which severe pain is felt even with minute symptoms, or hyperalgesia, which is a state in which pain sensitivity to stimuli is increased.
  • Neuropathies caused by various causes include diabetic neuropathy, chemotherapy-induced painful neuropathy, traumatic neuropathy, and inflammation-induced neuropathy (Inflammatory). neuropathy), etc.
  • treatment refers to any action in which symptoms of neuropathy are improved or cured by administration of the composition according to the present invention.
  • prevention refers to any action that suppresses or delays the symptoms of neuropathy by administration of the composition according to the present invention.
  • the content of the compound of Formula 1 in the pharmaceutical composition according to the present invention can be appropriately adjusted according to the symptoms of the disease, the degree of progression of the symptoms, the condition of the patient, and the like. For example, it may be contained in an amount of 0.0001 to 99.9 wt%, 0.1 to 90 wt%, 1 to 80 wt%, 1 to 70 wt%, 1 to 60 wt%, or 1 to 50 wt% based on the total weight of the composition.
  • the pharmaceutical composition of the present invention may further include suitable carriers, excipients and diluents commonly used in the preparation of pharmaceutical compositions.
  • Carriers, excipients and diluents that may be contained in the composition include, for example, lactose, dextrose, sucrose, sorbitol, mannitol, xylitol, erythritol, maltitol, starch, gum acacia, alginate, gelatin, calcium phosphate, calcium silicate, cellulose, methyl cellulose, microcrystalline cellulose, polyvinyl pyrrolidone, water, methylhydroxybenzoate, propylhydroxybenzoate, talc, magnesium stearate, or mineral oil, but is not limited thereto.
  • the pharmaceutical composition of the present invention may be an oral dosage form.
  • the pharmaceutical composition according to the present invention may be formulated into a suitable dosage form for topical administration using techniques well known to those skilled in the art, and the topical dosage form may include external preparations, effervescent tablets, suppositories, and the like.
  • the pharmaceutical composition of the present invention may be formulated for external use by mixing the compound of Formula 1 with a base well known and commonly used in the art.
  • the external preparations may include emulsions, gels, ointments, creams, patches, linens, powders, aerosols, sprays, lotions, serums, pastes, foams, drops, suspensions, and/or tinctures.
  • the pharmaceutical composition of the present invention may be formulated in the form of oral dosage forms such as pills, powders, granules, tablets, capsules, suspensions, emulsions, syrups and aerosols, external preparations, suppositories, and sterile injection solutions according to conventional methods.
  • oral dosage forms such as pills, powders, granules, tablets, capsules, suspensions, emulsions, syrups and aerosols, external preparations, suppositories, and sterile injection solutions according to conventional methods.
  • a diluent or excipient such as a filler, extender, binder, wetting agent, disintegrant, surfactant, etc. commonly used.
  • Solid preparations for oral administration include tablets, pills, powders, granules, capsules, etc., and these solid preparations include at least one excipient, for example, starch, calcium carbonate, sucrose or lactose, gelatin, etc.
  • Liquid formulations for oral use include suspensions, solutions, emulsions, syrups, etc.
  • various excipients such as wetting agents, sweeteners, fragrances, preservatives, etc. may be included.
  • Formulations for parenteral administration may include sterile aqueous solutions, non-aqueous solutions, suspensions, emulsions, lyophilized formulations, and suppositories.
  • the pharmaceutical composition of the present invention is administered to a subject in a pharmaceutically effective amount.
  • pharmaceutically effective amount means an amount sufficient to treat a disease with a reasonable benefit/risk ratio applicable to medical treatment for medical treatment, and the effective dose level is determined by the type and severity of the subject, age, It can be determined according to factors including sex, drug activity, drug sensitivity, administration time, administration route and excretion rate, duration of treatment, co-administered drugs, and other factors well known in the medical field.
  • the composition of the present invention may be administered as an individual therapeutic agent or in combination with other therapeutic agents, and may be administered sequentially or simultaneously with conventional therapeutic agents. and may be administered single or multiple. Taking all of the above factors into consideration, it is important to administer an amount that can obtain the maximum effect with a minimum amount without side effects, and can be easily determined by those skilled in the art.
  • the pharmaceutical composition of the present invention may vary depending on the age, sex, and weight of the patient, and specifically, 0.1 to 100 mg/kg of the composition of the present invention is administered once a day according to the degree of pain of the patient suffering from neuropathy. It can be administered several times.
  • the dosage may be increased or decreased depending on the route of administration, the degree of pain, sex, weight, age, in particular the pain level of the patient. Accordingly, the above dosage does not limit the scope of the present invention in any way.
  • the present invention also relates to a method of treating neuropathy comprising administering to a subject in need thereof an effective amount of the compound of formula 1 above.
  • the types of neuropathy are as described above.
  • the subject may be a mammal such as a human, a pig, a gorilla, a monkey, a dog, a cat, and a mouse, but is not limited thereto.
  • the present invention also relates to a food composition for preventing, alleviating or improving neuropathy comprising the compound of Formula 1 above.
  • the present invention also provides the use of the compound of formula 1 for the manufacture of a food for preventing, alleviating or ameliorating neuropathy.
  • the compound of Formula 1 and the neuropathy are the same as those mentioned in the pharmaceutical composition, respectively, unless otherwise specified.
  • improvement refers to any action in which the degree of neuropathy is at least reduced, ameliorated or beneficial by administration of the composition according to the present invention.
  • the food may be a health functional food.
  • health functional food refers to food manufactured and processed in the form of tablets, capsules, powders, granules, liquids, pills, etc. using raw materials or ingredients useful for the human body.
  • functionality refers to obtaining useful effects for health purposes, such as regulating nutrients or physiological actions with respect to the structure and function of the human body.
  • the food composition according to the present invention can be prepared by a method commonly used in the art, and during the preparation, it can be prepared by adding raw materials and components commonly added in the art.
  • the food composition of the present invention is used for enhancing or improving the neuropathy treatment effect. It can be taken as a supplement.
  • the amount of the compound of Formula 1 as an active ingredient of the food composition according to the present invention may be appropriately determined depending on the purpose of use (prevention, improvement or therapeutic treatment).
  • the compound of Formula 1 may be included in an amount of 0.001 to 20% by weight, 0.001 to 15% by weight, or 0.001 to 10% by weight of the raw material composition.
  • 0.01 to 2 g, specifically 0.02 to 2 g, more specifically 0.3 to 1 g, based on 100 mL may be added.
  • the above amount may be used below the above range.
  • the content of the compound of Formula 1 added to the food composition in the process of preparing the food composition of the present invention may be appropriately increased or decreased as necessary.
  • the food composition may be in any one formulation selected from the group consisting of pills, tablets, granules, powders, capsules, and liquid solutions.
  • the type of the food is not particularly limited.
  • foods to which the above substances can be added include meat, sausage, bread, chocolate, candy, snacks, confectionery, pizza, ramen, other noodles, gums, dairy products including ice cream, various soups, beverages, tea, drinks, There are alcoholic beverages, vitamin complexes, and the like, and includes all foods in a conventional sense.
  • the food composition of the present invention may contain various flavoring agents or natural carbohydrates as additional ingredients, like conventional food.
  • the above-mentioned natural carbohydrates include monosaccharides such as glucose and fructose, disaccharides such as maltose and sucrose, polysaccharides such as dextrin and cyclodextrin, and sugar alcohols such as xylitol, sorbitol, and erythritol.
  • a natural sweetener such as taumatin or stevia extract, or a synthetic sweetener such as saccharin or aspartame may be used.
  • the food composition of the present invention is a beverage composition
  • the liquid component except for containing the extract in the indicated ratio as an essential component, and it may contain various flavoring agents or natural carbohydrates as an additional component like a conventional beverage.
  • the present invention also provides a compound represented by the formula (5):
  • the HEK-293 cell line expressing TRPA1 was aliquoted on a 384 black clear plate (1.5 ⁇ 10 4 cells/20 ⁇ l/well), 20 ⁇ l FLIRP Calcium 6 assay reagent was added, and incubated for 2 hours. After adding the extract obtained in Example 1 and the control drug (A-967079) to each cell and leaving it for 10 minutes, the change in the intracellular calcium concentration was measured by the change in fluorescence intensity that appeared after 5 ⁇ M AITC was added.
  • the TRPA1 function inhibition rate of the extract was measured at a concentration of 10 ⁇ g/mL by setting the value treated with AITC 5 ⁇ M as 0% inhibition and setting the value not treated with AITC 5 ⁇ M as 100% inhibition. A value of 97% was obtained (Table 1).
  • TRPA1 function inhibition rate was measured in the same manner as in Example 2 at 5 concentrations (10 -1.0 , 10 -0.5 , 10 0.0 , 10 0.5 , 10 1.0 , 10 1.5 ⁇ g/mL) with respect to the fraction obtained in Example 3 to calculate the IC 50 value.
  • the compounds of Formulas 6, 2, 3, 4 and 5 were sequentially separated by performing HPLC from the 90% fraction of methanol obtained in Example 3, and the compound of Formula 7 was purified by performing HPLC from the 100% methanol fraction. did.
  • a semi-preparative ODS column (YMC-Pack Pro C18 (YMC, Kyoto, Japan)) was used for the stationary phase, and a mixed solvent of water and methanol was used for the mobile phase.
  • the TRPA1 function inhibition rate was measured in the same manner as in Example 4 to confirm the TRPA1 inhibitory activity of each compound.
  • the present invention can be usefully used as an active ingredient in medicine, food, etc. for the prevention, alleviation or treatment of neuropathy.

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Abstract

La présente invention concerne une composition comprenant un composé de saponine dérivé du concombre de mer pour prévenir, soulager ou traiter une neuropathie. Plus particulièrement, le composé de saponine dérivé du concombre de mer de la présente invention diminue la fonction de la protéine TRPA1 qui induit la transmission d'un signal de douleur par la migration d'ions calcium et, en tant que tel, peut être avantageusement utilisé en tant que principe actif pour un médicament, un aliment, etc., pour prévenir, soulager ou traiter une neuropathie.
PCT/KR2020/009363 2020-03-19 2020-07-16 Composition comprenant un composé de saponine dérivé du concombre de mer pour prévenir, soulager ou traiter une neuropathie Ceased WO2021187679A1 (fr)

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KR10-2020-0033900 2020-03-19
KR1020200033900A KR20210117552A (ko) 2020-03-19 2020-03-19 해삼 유래 사포닌 화합물을 포함하는 신경병증의 예방, 완화 또는 치료용 조성물

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Citations (2)

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KR101917877B1 (ko) 2017-06-29 2018-11-13 재단법인 경기도경제과학진흥원 항암제 유발 말초신경병증 통증의 치료, 완화 또는 예방용 조성물

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US20090269415A1 (en) * 2005-08-31 2009-10-29 Imex Japan Co., Ltd. Novel therapeutic agent derived from marine organism
KR20130104930A (ko) * 2012-03-16 2013-09-25 합자회사 에스에이치해양수산개발 해삼 유래 사포닌 함유 화장료조성물의 제조방법 및 동 방법에 의한 화장료조성물

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