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WO2016167385A1 - Composition ii pour prévenir ou traiter la maladie d'alzheimer, comprenant un extrait de lycopodiella cernua ou un composé isolé à partir de celui-ci - Google Patents

Composition ii pour prévenir ou traiter la maladie d'alzheimer, comprenant un extrait de lycopodiella cernua ou un composé isolé à partir de celui-ci Download PDF

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Publication number
WO2016167385A1
WO2016167385A1 PCT/KR2015/003790 KR2015003790W WO2016167385A1 WO 2016167385 A1 WO2016167385 A1 WO 2016167385A1 KR 2015003790 W KR2015003790 W KR 2015003790W WO 2016167385 A1 WO2016167385 A1 WO 2016167385A1
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compound
glucopyranoside
extract
apigenin
disease
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PCT/KR2015/003790
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English (en)
Korean (ko)
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민병선
최재수
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Industry Academic Cooperation Foundation of Daegu Catholic University
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Industry Academic Cooperation Foundation of Daegu Catholic University
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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
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • 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
    • A61K36/11—Pteridophyta or Filicophyta (ferns)

Definitions

  • the present invention relates to a composition for the prophylaxis or treatment of Alzheimer's disease comprising an extract of Lycopodiella cernua or a compound isolated therefrom.
  • Alzheimer's disease is the most common type of senile neurological disease, which is the most common degenerative brain disease causing dementia, a brain disease causing memory, thinking and behavioral problems.
  • Dementia is a general term that means severe loss of memory and other intellectual skills that interfere with daily life.
  • Alzheimer's disease is estimated to account for 60-80% of cases of dementia. In the United States, more than five million people have Alzheimer's disease, and the number of Americans with Alzheimer's disease and other dementia is expected to grow each year as the proportion of people age 65 and older in the United States continues to grow.
  • Acetylcholine is one of the neurotransmitters and is found mostly in the area where neurons and skeletal muscle meet.
  • acetylcholine secreted from the nerve terminal is inactivated by decomposing into choline and acetic acid by acetylcholinesterase (AChE) after the transmission of the stimulus, the choline is an enzyme according to the action of cholineacetylase (cholinacetylase) Synthetically synthesized to form acetylcholine.
  • Acetylcholinesterase inhibitors support signaling between neurons by preventing and maintaining high levels of acetylcholine, an important chemical messenger for memory and learning.
  • butyrylcholinesterase breaks down acetylcholine in the brain and plays a role in choline delivery. Therefore, the inhibition of the acetylcholinesterase and butyrylcholinesterase increases the concentration of acetylcholine in the synaptic gap, enhances neurotransmission of acetylcholine, and improves defects.
  • acetylcholinesterase inhibitors which cannot completely prevent the progression of the disease, and alleviate or slow down some pathological symptoms. Only effect.
  • Drugs of this class include donepezil, rivastingmine, galantamine, and tacrine.
  • acetylcholinesterase is the most pharmacological action point in the world, it is possible to develop drugs and functional materials of acetylcholinesterase inhibitor with few side effects and excellent effects using various natural products. There is a need.
  • ⁇ -secretase 1 acts on the amyloid- ⁇ -precursor protein (APP) to generate ⁇ -amyloid fragments.
  • APP amyloid- ⁇ -precursor protein
  • ⁇ -amyloid since the accumulation of ⁇ -amyloid is known as a major cause of Alzheimer's disease, the development of a substance for the inhibitory activity of ⁇ -secretase may be helpful in the treatment of Alzheimer's disease by preventing the cleavage of the ⁇ -amyloid precursor protein. have.
  • ⁇ -secretase inhibitor x-ray crystallography x-ray crystallography
  • x-ray crystallography revealed a clear structure, a variety of inhibitors can be easily developed, but there is no efficacy and still available as a therapeutic agent to be. Therefore, the development of new ⁇ -secretase inhibitors could be of great help in the treatment of Alzheimer's disease.
  • the Lycopodiella cernua is a river of vascular plants that make spores, belonging to the family of cypresses and similar plants. It is widely spread around the world, and consists of four genera and about 1,000 species. Plants in this river are small in size and can grow upright or even grow on other plants. The stem is divided into two branches and pruned. The differentiation of roots, stems, and leaves is distinct, and photosynthesis is possible. The spore sac runs on a special leaf called the spores, which gather together to form a cone-shaped spores. It is an evergreen perennial plant, which inhabits Jeju, Jeonnam, Hambuk, Hamnam, and Gangwon.
  • Korean Laid-Open Patent Publication No. 2011-0118145 suggested that lycopoduim clavatum extract or a compound isolated therefrom is effective in treating cancer, and the anti-memory loss effect of vegetable base isolated from lychee (Chuong, NN et al., 2014), anticholinesterase activity (Konrath, EL et al., 2013) of vegetable bases isolated from South American pine family has been disclosed.
  • the compounds isolated from the pine tree of the present invention have an inhibitory effect of acetylcholinesterase or butyrylcholinesterase or ⁇ -secretase 1.
  • the present invention relates to a composition for the prophylaxis or treatment of Alzheimer's disease comprising an extract of Lycopodiella cernua or a compound isolated therefrom. More specifically, lambnagin (Compound 1), quercetin 3,3'- dimethyl ether (Compound 2), guaiacylglycerol (Compound 3), apigenin (Compound 4), isomorphoside (Compound 1) 5), Bahia genin -4'- O - (2 '', 6 '' - di-p -O- - Kumar in one) - ⁇ -D- gluconic nose Llano side (compound 6), spring Basin -4- O - ⁇ - D - gluconic nose Llano side (compound 7), (7 R, 8 S) -7,8- dihydro-8-hydroxy-7- (3-methoxyphenyl -4- O - ⁇ - D- gluconic nose Llano side) 1'-benzofuran propionic acid (
  • the travertine extract is characterized in that the extract is extracted with at least one solvent selected from the group consisting of water, C1 to C4 lower alcohol, acetone, n-hexane, dichloromethane and ethyl acetate.
  • the present invention is isolated from the Lycopodiella cernua ( Lycopodiella cernua ) of Rhamnajin (Compound 1), Quercetin 3,3'- dimethyl ether (Compound 2), Guaiacylglycerol (Compound 3), Apigenin (Compound 4) ), Isoshaphtoside (compound 5), apigenin-4'- O- (2 '', 6 ''-di-O- p -coumaroyl) - ⁇ -D-glucopyranoside (compound 6) ), Bombacin-4- O- ⁇ - D -glucopyranoside (Compound 7), (7 R , 8 S ) -7,8-dihydro-8-hydroxymethyl-7- (3-methoxy Phenyl-4- O- ⁇ -D-glucopyranoside) -1'-benzofuran propionic acid (Compound 8), apigenin-4'- O- (6 '' -O - p
  • the compound is characterized by inhibiting at least one enzyme activity selected from the group consisting of acetylcholinesterase, butyrylcholinesterase and ⁇ -secretase 1.
  • the present invention is the lambnagin (Compound 1), quercetin 3,3'- dimethyl ether (Compound 2), guaiacylglycerol (Compound 3), apigenin (Compound 4) of the formula 1 isolated from the trachea Isomorphoside (compound 5), apigenin-4'- O- (2 '', 6 ''-di-O- p -coumaroyl) - ⁇ -D-glucopyranoside (compound 6), Basin spring -4- O - ⁇ - D - gluconic nose Llano side (compound 7), (7 R, 8 S) -7,8- dihydro-8-hydroxy-7- (3-methoxyphenyl- 4- O- ⁇ -D-glucopyranoside) -1'-benzofuranpropionic acid (Compound 8), apigenin-4'- O- (6 '' -O - p -coumaroyl) - ⁇ -D 1 type selected from the group
  • the present invention comprises the steps of preparing the extract of the Songseok River with Lycopodiella cernua in water, C1 to C4 lower alcohol or a mixed solvent thereof; Fractionating the travertine extract using n-hexane and ethyl acetate in sequence and re-fractionating the water layer residue with dichloromethane; And chromatographing the water layer except for the re-distilled dichloromethane to lambnazin of the formula (compound 1), quercetin 3,3'-dimethyl ether (compound 2), guaiacylglycerol (compound 3), apigenin ( Compound 4), isomorphoside (compound 5), apigenin-4'- O- (2 '', 6 ''-di-O- p -coumaroyl) - ⁇ -D-glucopyranoside ( compound 6), spring Basin -4- O - ⁇ - D - gluconic nose Llano side (compound 1), quer
  • the present invention also provides (7 R, 8 S) is a novel compound, having the following chemical structure 7,8-dihydro-8-hydroxy-7- (3-methoxyphenyl -4- O - ⁇ -D -Glucopyranoside) -1'-benzofuran propionic acid.
  • the present invention relates to a composition for the prevention or treatment of Alzheimer's disease comprising the compound of formula (I) isolated from the Lycopodiella cernua .
  • the travertine extract may be obtained by extracting the travertine with water, a lower alcohol of C1 to C4 or a mixed solvent thereof, and the lower alcohol of C1 to C4 may use methanol, ethanol, propanol, isopropanol, butanol, and the like. have.
  • the extract may be fractions re-fractionated with an organic solvent, n-hexane, ethyl acetate and dichloromethane may be used as the organic solvent.
  • the compound separated from the travertine can be obtained by fractionating the water layer extract of the travertine, and the chromatography is silica gel column chromatography, HP-20 column chromatography. , RP-18 column chromatography, LH-20 column chromatography, high-performance liquid chromatography, and the like.
  • the compound of the present invention may be synthesized according to a conventional method in the art, and may be prepared as a pharmaceutically acceptable salt.
  • the present invention also provides a pharmaceutical composition for the prevention or treatment of Alzheimer's disease comprising at least one compound selected from the group of compounds of the formula (1) isolated from the extract of the trachea.
  • Pharmaceutical compositions comprising the extracts or compounds are formulated in the form of powders, granules, tablets, capsules, suspensions, emulsions, syrups, aerosols and the like, oral preparations, suppositories, and sterile injectable solutions, respectively, according to conventional methods. Can be used.
  • Carriers, excipients and diluents that may be included in the pharmaceutical composition include lactose, dextrose, sucrose, sorbitol, mannitol, xylitol, erythritol, maltitol, starch, acacia rubber, alginate, gelatin, calcium phosphate, calcium silicate, cellulose , Methyl cellulose, microcrystalline cellulose, polyvinyl pyrrolidone, water, methylhydroxybenzoate, propylhydroxybenzoate, talc, magnesium stearate and mineral oil.
  • Solid preparations for oral administration include tablets, pills, powders, granules, capsules, and the like, and such solid preparations include at least one excipient such as starch, calcium carbonate, sucrose, or the like in the extract or compound of the present invention. Or it is prepared by mixing lactose and gelatin. In addition to simple excipients, lubricants such as magnesium stearate and talc are also used.
  • Oral liquid preparations include suspensions, solvents, emulsions, and syrups, and may include various excipients, such as wetting agents, sweeteners, fragrances, and preservatives, in addition to commonly used simple diluents such as water and liquid paraffin.
  • Formulations for parenteral administration include sterile aqueous solutions, non-aqueous solvents, suspensions, emulsions, lyophilized preparations, suppositories.
  • the non-aqueous solvent and suspending agent 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 dosage of the pharmaceutical composition comprising the extract of the pine needles of the present invention or a compound isolated therefrom is determined by the age, sex, weight of the subject to be treated, the specific disease or pathology to be treated, the severity of the disease or pathology, the route of administration and the It will depend on your judgment. Dosage determination based on these factors is within the level of skill in the art and generally dosages range from 0.01 mg / kg / day to approximately 2000 mg / kg / day. More preferred dosage is 1 mg / kg / day to 500 mg / kg / day. Administration may be administered once a day or may be divided several times. The dosage does not limit the scope of the invention in any aspect.
  • compositions comprising the extract of the pine needles of the present invention or a compound isolated therefrom can be administered to mammals such as rats, livestock, humans and the like by various routes. All modes of administration can be expected, for example, by oral, rectal or intravenous, intramuscular, subcutaneous, intrauterine dural or cerebrovascular injections.
  • the extract of the present invention or a compound isolated therefrom has little toxicity and side effects, and thus is a drug that can be used safely even for prolonged administration for the purpose of prevention.
  • the present invention provides a health functional food for preventing or improving Alzheimer's disease comprising at least one compound selected from the group of the compound of formula 1 isolated from the pineapple extract or the above-mentioned do.
  • the extract or compound may be added as 0.001 to 100% by weight to the health functional food of the present invention.
  • the health functional food of the present invention includes the form of tablets, capsules, pills, or liquids, and the food to which the extract or compound of the present invention may be added, for example, various foods, beverages, gums, teas, Vitamin complexes.
  • the present invention relates to a composition for the prevention or treatment of Alzheimer's disease, including the extract of the Songseok River or a compound isolated therefrom, wherein the extract of the Songseok River or the compound isolated therefrom is an acetylcholinesterase, butyrylcholinesterase and ⁇ -ce Excellent inhibitory effect of Cretease 1 can be usefully used as a composition for the prevention or treatment of Alzheimer's disease.
  • Figure 1 is a novel compound of (7 R, 8 S) -7,8- dihydro-8-hydroxy-7- (3-methoxyphenyl -4- O - ⁇ -D- gluconic nose pyrano of the invention side) is an illustration showing a 1'-benzofuran propionic acid 1 H- 1 H COSY (bold lines ) and the 1 H- 13 C HMBC correlation (arrow) on.
  • Lycopodium cernua used in the present invention was obtained in Lumdongzhou, Vietnam in April 2012, extracting and filtering the reflux of the Songsong River (3 kg) with methanol (2 L ⁇ 3 times), and filtering the filtrate. Distillation under reduced pressure gave 280 g of methanol extract. Then, the methanol extract was suspended in water (2 L) and sequentially partitioned into n-hexane (2 L ⁇ 3 times) and ethyl acetate (2 L ⁇ 3 times), and the n-hexane fraction (48 g) and ethyl acetate fraction (175.5). g) and finally a fraction (55 g) containing the water layer residue.
  • the fraction containing the water layer residue was suspended with 5% [v / v] hydrochloric acid, and then fractionated with dichloromethane to obtain a dichloromethane fraction (1.9 g).
  • the aqueous layers of the fractions with dichloromethane to pH11-12 with 0.1N sodium hydroxide, and then fractionated with dichloromethane.
  • the organic layer was collected, dried over sodium sulfate, and evaporated to obtain a crude alkaloid fraction.
  • the residue containing the water layer was anionic HP- according to the concentration gradient elution condition of aqueous methanol solution (0 ⁇ 100% [v / v]). Fractionation by 20 column chromatography gave 12 fractions (W1-W12).
  • Fraction W6 (1.05 g) was fractionated by silica gel column chromatography (column size: 3.0 ⁇ 50 cm) according to isocratic elution conditions of dichloromethane: methanol: water (3: 1: 0.2 [v: v: v]).
  • W6.1-W6.9 Nine small fractions (W6.1-W6.9) were obtained.
  • W6.2 25 mg in the small fractions afforded Compound 4 (6.2 mg) through filtration.
  • the small fraction W6.9 (167 mg) was fractionated by Sephadex LH-20 column chromatography (column size: 2.0 ⁇ 120 cm) according to isocratic elution conditions of methanol: water (1: 1 [v: v]).
  • Compound 5 (7 mg) and compound 6 (10.3 mg) were obtained.
  • W8 (1.52 g) in the fractions was purified by silica gel column chromatography (column size: 3.0 ⁇ 60 cm) according to isocratic elution conditions of dichloromethane: methanol: water (3: 1: 0.1 [v: v: v]). To obtain eight small fractions (W8.1-W8.8). W8.6 (125 mg) in the small fractions was separated by Sephadex LH-20 column chromatography (column size: 2.0 ⁇ 60 cm) according to isocratic elution conditions of methanol: water (1: 1 [v: v]). Fractionation gave compound 7 (3 mg).
  • Fraction W9 (1.36 g) was purified by silica gel column chromatography (column size: 3.0 ⁇ 60 cm) according to isocratic elution conditions of dichloromethane: methanol: water (3: 1: 0.1 [v: v: v]). Small fractions (W9.1-W9.7) were isolated. W9.4 (45 mg) in the small fractions was separated by Sephadex LH-20 column chromatography (column size: 1.5 ⁇ 120 cm) according to isocratic elution conditions of methanol: water (2: 1 [v: v]). Fractionation gave compound 9 (6.7 mg).
  • quercetin 3,3'-dimethyl ether quercetin 3,3'-dimethyl ether
  • Example 2-8 (7 R ,8 S ) -7,8-dihydro-8-hydroxymethyl-7- (3-methoxyphenyl-4- O - ⁇ -D-glucopyranoside) -1'-benzofuran propionic acid (compound 8)
  • the compound isolated from the extract of the pine tree of the present invention has an inhibitory activity of acetylcholinesterase or butyrylcholinesterase, which can be usefully used as a prophylactic and therapeutic agent for Alzheimer's disease Can be.
  • Example 5-2 Long-term and tissue toxicity experiments in experimental and control groups

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Abstract

La présente invention concerne une composition pour prévenir ou traiter la maladie d'Alzheimer, comprenant un extrait de lycopodiella cernua ou un composé isolé à partir de celui-ci. L'extrait de lycopodiella cernua ou le composé isolé à partir de celui-ci présente un excellent effet d'inhibition de l'acétylcholinestérase, de la butyrylcholinestérase et de la β-sécrétase 1, et peut ainsi être efficacement utilisé en tant que composition pour la prévention ou le traitement de la maladie d'Alzheimer.
PCT/KR2015/003790 2015-04-14 2015-04-15 Composition ii pour prévenir ou traiter la maladie d'alzheimer, comprenant un extrait de lycopodiella cernua ou un composé isolé à partir de celui-ci Ceased WO2016167385A1 (fr)

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KR10-2015-0052664 2015-04-14
KR1020150052664A KR101818084B1 (ko) 2015-04-14 2015-04-14 석송강 추출물 또는 이로부터 분리된 화합물을 포함하는 알츠하이머병의 예방 또는 치료용 조성물-ⅱ

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CN107513084A (zh) * 2017-08-29 2017-12-26 广西中医药大学 白鹤藤碱及其提取方法及其用途
CN108299367A (zh) * 2018-01-26 2018-07-20 南阳师范学院 一种芹菜苷元氨基甲酸酯类化合物、其制备方法及应用
KR101908342B1 (ko) 2017-12-08 2018-10-16 재단법인 전남생물산업진흥원 새싹인삼과 차풀 복합추출물을 유효성분으로 하는 피부상태 개선용 조성물 및 이의 제조방법
CN109364092A (zh) * 2018-12-26 2019-02-22 南京盖斯夫医药科技有限公司 一种白鹤藤碱的新用途
KR20190063880A (ko) 2017-11-30 2019-06-10 주식회사 하연 새싹인삼과 차풀 복합추출물을 유효성분으로 하는 기능성 마스크 팩
CN110963893A (zh) * 2018-09-29 2020-04-07 沈阳药科大学 苯丙素类化合物及其制备方法和用途

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KR20250157739A (ko) 2024-04-29 2025-11-05 인천대학교 산학협력단 이소샤프토사이드를 유효성분으로 포함하는 항노화 조성물

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CN108299367B (zh) * 2018-01-26 2022-04-12 南阳师范学院 一种芹菜苷元氨基甲酸酯类化合物、其制备方法及应用
CN110963893A (zh) * 2018-09-29 2020-04-07 沈阳药科大学 苯丙素类化合物及其制备方法和用途
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