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WO2003099305A1 - Composition contenant un extrait soluble d'acetate d'ethyle produit a partir de kalopanax pictus nakai, et derives de kalopanaxsaponin a isoles dudit extrait pour prevenir ou traiter une maladie inflammatoire ou rhumatismale - Google Patents

Composition contenant un extrait soluble d'acetate d'ethyle produit a partir de kalopanax pictus nakai, et derives de kalopanaxsaponin a isoles dudit extrait pour prevenir ou traiter une maladie inflammatoire ou rhumatismale Download PDF

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Publication number
WO2003099305A1
WO2003099305A1 PCT/KR2002/002296 KR0202296W WO03099305A1 WO 2003099305 A1 WO2003099305 A1 WO 2003099305A1 KR 0202296 W KR0202296 W KR 0202296W WO 03099305 A1 WO03099305 A1 WO 03099305A1
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Prior art keywords
kalopanaxsaponin
ethyl acetate
extract
kalopanax pictus
inflammatory
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English (en)
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Eun-Bang Lee
Da Wei Li
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    • 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)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/25—Araliaceae (Ginseng family), e.g. ivy, aralia, schefflera or tetrapanax
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • 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]

Definitions

  • the present invention relates to composition
  • composition comprising an extract from Kalopanax pictus Nakai and kalopanaxsaponin A derivatives isolated therein for the prevention and treatment of inflammatory and rheumatic diseases and methods of using such extracts as potent anti-inflammatory and anti-rheumatic agents.
  • RA rheumatoid arthritis
  • RA rheumatoid arthritis
  • OA osteoarthritis
  • the symptoms of arthritis generally relates to arthrosis of spine, e.g., hallux rigidus, arthrosis psoriaticum, rheumatic arthritis.
  • Rheumatoid arthritis (RA) is a common autoimmune disease characterized by joint swelling, deformation and ultimately, destruction, culminating in severe physical disability.
  • Rheumatic diseases include diseases of the muscles, tendons, joints, bones or sinews, which are generally characterized by inflammation and/or degeneration.
  • the conventional drug treatment of RA has been used by the symptomatic anti- inflammatory treatment using drugs such as NSAIDs, glucocortcoid or its joint injection, or the disease modifying treatment using such as the antimalarials, gold salt, sulfasalazine, penicilline and methotrexate.
  • the drug treatment of initial stage of RA usually has been the use of NSAIDs to reduce joint pain and swelling and improve function.
  • the treatment by using the above compounds produces adverse action and did not show significant treating effect so far.
  • Kalopanax pictus Nakai and the same genus plants i.e. Kalopanax pictus Nakai var. chinensis Nakai, Kalopanax pictus Nakai var. magnificus Nakai, Kalopanax pictus Nakai var. maximowiczii Nakai has been used for augmenting stamina and treating neuralgia.
  • its components consists of 13 to 30% tannin, glucose, kalotoxin, kalosaponin, liriodendrin, hederagenin, arabinose, benzoic acid, amino acid, d-mannitol and polyacetylene compound.
  • Kalopanax pictus Nakai The leaves, root and the bark of Kalopanax pictus Nakai has been used for treatment of neuralgia, lumbago, muscular paralysis caused by rheumatism, myalgia, arthritis, psoriasis, ingivostomatitis and the like (Jung, B.S. and Shin, M.K; Hyangyak dictionary, younglimsa, pp437-438, 1998). Recently, the extraction and isolation studies of various saponin, lignin and antioxidants from the plant are progressing vigorously.
  • Natural products including plants and animals, has offered as a vast reservoir of compounds which have pharmacological effects on human. Natural products have been the sources of effective drugs and lately there has been an increased interest in the analysis of these natural products, to find clinically effective compound.
  • the present inventors have endeavored to study the pharmacological effect of Kalopanax pictus Nakai on inflammatory and rheumatic diseases, and finally found that the extract from Kalopanax pictus Nakai and kalopanaxsapanin A isolated from the bark of Kalopanax pictus Nakai are effective in treating rheumatic arthritis and inflammatory diseases.
  • the present invention provides a composition containing an ethyl acetate soluble extract from Kalopanax pictus Nakai for preventing and treating inflammatory and rheumatic diseases.
  • the present invention also provides a pharmaceutical compositions comprising the ethyl acetate soluble extract from Kalopanax pictus Nakai or kalopanaxsaponin A derivatives isolated therein as an active ingredient in an amount effective to preventing and treating inflammatory and rheumatic diseases, together with a pharmaceutically acceptable carrier.
  • the present invention also provides a use of the extract and compounds for the preparation of pharmaceutical composition for treating and preventing inflammatory and rheumatic diseases.
  • the present invention still provides processes for preparing the ethyl acetate soluble extract from Kalopanax pictus Nakai and kalopanaxsaponin A derivatives isolated therein.
  • composition comprising an ethyl acetate soluble extract from Kalopanx pictus Nakai for treating and preventing inflammatory and rheumatic diseases.
  • Ri is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms
  • R 2 is an alkyl group having 1 to 3 carbon atoms.
  • composition for treating inflammatory and rheumatic diseases could contain about 0.01 to 80 w/w%, preferably 0.5 to 50 w/w% of the ethyl acetate soluble extract from Kalopanax pictus Nakai or kalopanaxsaponin A derivatives of present invention based on the total weight of the composition.
  • an inventive extract may be prepared in accordance with the following preferred embodiment.
  • the bark of Kalopanax pictus Nakai is dried at room temperature and cut into small pieces.
  • the each pieces is mixed with 1 to 15-fold, preferably, 4 to 10- fold volume of water, alcohols such as methanol, ethanol, butanol and the like, or the mixtures thereof, preferably, the mixture of water and methanol, more preferably ratio of 1 : 1 to 1 :3; and is heated at the temperature ranging from 20 to 100°C, preferably from 70 to 90°C, for the period ranging from 1 to 48 hours, preferably 2 to 24 hours, with 3 to 10 times, preferably 5 times, by sonication, reflux or conventional extraction to obtain an aqueous crude extract.
  • the crude extract is added with 3 to 10-fold, preferably, 5-fold volume of chloroform and the chloroform soluble extract is removed.
  • the residue is added with 3 to 10-fold, preferably, 5-fold volume of ethyl acetate and filtered to obtain an ethyl acetate extract.
  • the ethyl acetate extract is subjected to silica column chromatography to get kalopanaxsaponin A derivatives according to the conventional isolation procedure disclosed in the literature(Woo, W.S., The Study of Natural chemistry, Seoul national University, pp 17-26, 1996 ).
  • alkylation reagents preferably, diazo alkylation reagents for 1 to 48 hours, preferably, 2 to 12 hours at a temperature ranging from 10 to 60°C , preferably, 30 to 40 ° C
  • alkylation reagents preferably, diazo alkylation reagents for 1 to 48 hours, preferably, 2 to 12 hours at a temperature ranging from 10 to 60°C , preferably, 30 to 40 ° C
  • It is another object of the present invention to provide a pharmaceutical composition comprising the said ethyl acetate soluble extract from Kalopanax pictus Nakai and a pharmaceutically acceptable carrier thereof as an active ingredient for preventing and treating inflammatory and rheumatic diseases.
  • It is another object of the present invention to provide a pharmaceutical composition comprising kalopanaxsaponin A derivatives represented by the formula (I) and a pharmaceutically acceptable carrier thereof as an active ingredient for preventing and treating inflammatory and rheumatic diseases.
  • Inventive pharmaceutical composition can be comprised in pharmaceutically acceptable diluent such as saline, buffered saline, dextrose, water, glycerol, ethanol and the mixture thereof, but it is not limited.
  • pharmaceutically acceptable diluent such as saline, buffered saline, dextrose, water, glycerol, ethanol and the mixture thereof, but it is not limited.
  • Appropriate diluents are listed in the written text of Remington's Pharmaceutical Science(Mack Publishing co, Easton PA).
  • the ethyl acetate soluble extract from Kalopanax pictus Nakai and kalopanaxsaponin A derivatives according to the present invention can be provided as a pharmaceutical composition containing pharmaceutically acceptable carriers, adjuvants or diluents, e.g., lactose, dextrose, sucrose, sorbitol, mannitol, xylitol, erythritol, maltitol, starches, acacia rubber, alginate, gelatin, calcium phosphate, calcium silicate, cellulose, methyl cellulose, polyvinyl pyrrolidone, water, methylhydroxy benzoate, propylhydroxy benzoate, talc, magnesium stearate and mineral oil.
  • pharmaceutically acceptable carriers, adjuvants or diluents e.g., lactose, dextrose, sucrose, sorbitol, mannitol, xylitol, ery
  • the formulations may additionally include fillers, anti-agglutinating agents, lubricating agents, wetting agents, flavoring agents, emulsifiers, preservatives and the like.
  • the compositions of the invention may be formulated so as to provide quick, sustained or delayed release of the active ingredient after their administration to a patient by employing any of the procedures well known in the art.
  • compositions of the present invention can be dissolved in oils, propylene glycol or other solvents which are commonly used to produce an injection.
  • suitable examples of the carriers include physiological saline, polyethylene glycol, ethanol, vegetable oils, isopropyl myristate, etc., but are not limited to them.
  • the compounds of the present invention can be formulated in the form of ointments and creams.
  • Nakai and kalopanaxsaponin A may be prepared in any form, such as oral dosage form (powder, tablet, capsule, soft capsule, aqueous medicine, syrup, elixirs pill, powder, sachet, granule), or topical preparation (cream, ointment, lotion, gel, balm, patch, paste, spray solution, aerosol and the like), or injectable preparation (solution, suspension, emulsion).
  • oral dosage form poowder, tablet, capsule, soft capsule, aqueous medicine, syrup, elixirs pill, powder, sachet, granule
  • topical preparation cream, ointment, lotion, gel, balm, patch, paste, spray solution, aerosol and the like
  • injectable preparation solution, suspension, emulsion
  • the ethyl acetate soluble extract from Kalopanax pictus Nakai or kalopanaxsaponin A derivatives of the present invention in pharmaceutical dosage forms may be used in the form of their pharmaceutically acceptable salts, and also may be used alone or in appropriate association, as well as in combination with other pharmaceutically active compounds.
  • the desirable dose of the inventive extract or compounds varies depending on the condition and the weight of the subject, severity, drug form, route and period of administration, and may be chosen by those skilled in the art. However, in order to obtain desirable effects, it is generally recommended to administer at the amount ranging 0.1 - 500 mg/kg by weight/day of the inventive extract or compounds of the present invention.
  • the dose may be administered in single or divided into several times per day.
  • the ethyl acetate extract from Kalopanax pictus Nakai or kalopanaxsaponin A derivatives should be present between 0.01 to 80% by weight, preferably 0.5 to 50% by weight based on the total weight of the composition.
  • composition of present invention can be administered to a subject animal such as mammals (rat, mouse, domestic animals or human) via various routes. All modes of administration are contemplated, for example, administration can be made orally, rectally or by intravenous, intramuscular, subcutaneous, intrathecal, epidural or intracerebro ventricular injection.
  • the present inventors demonstrated that inhibitory and anti-inflammatory effect of the ethyl acetate extract from Kalopanax pictus Nakai and kalopanaxsaponin A derivatives is potent by accomplishing in vivo experiment, e.g., the inhibition test of capillary transmission, carageenin-induced edema inhibition test, inhibition test of paw edema, Therefore, it is confirmed that above described the ethyl acetate extract from Kalopanax pictus Nakai and kalopanaxsaponin A derivatives are very useful in the prevention or treatment of inflammatory and rheumatic disease
  • a health care food comprising above ethyl acetate soluble extract from Kalopanax pictus Nakai or kalopanaxsaponin A derivatives and a sitologically acceptable additive to prevent inflammatory and rheumatic diseases, e.g., rheumatic arthritis.
  • the ethyl acetate extract from Kalopanax pictus Nakai therein can be added to food or beverage for prevention of inflammatory and rheumatic diseases.
  • the amount of above described extract or compound in food or beverage may generally range from about 0.01 to 50 w/w %, preferably 0.1 to 20 w/w % of total weight of food for the health food composition and 0.02 to 10 g, preferably 0.3 to 1 g on the ratio of 100 ⁇ wl of the health beverage composition.
  • the health beverage composition of present invention contains above described extract or compound as an essential component in the indicated ratio
  • the other component can be various deodorant or natural carbohydrate etc such as conventional beverage.
  • natural carbohydrate are monosaccharide such as glucose, fructose etc; disaccharide such as maltose, sucrose etc; conventional sugar such as dextrin, cyclodextrin; and sugar alcohol such as xylitol, and erythritol etc.
  • natural deodorant such as taumatin, stevia extract such as levaudioside A, glycyrrhizin et al., and synthetic deodorant such as saccharin, aspartam et al.
  • the amount of above described natural carbohydrate is generally ranges from about 1 to 20 g, preferably 5 to 12 g in the ratio of 100 m£ of present beverage composition.
  • the other components than aforementioned composition are various nutrients, a vitamin, a mineral or an electrolyte, synthetic flavoring agent, a coloring agent and improving agent in case of cheese chocolate et al., pectic acid and the salt thereof, alginic acid and the salt thereof, organic acid, protective colloidal adhesive, pH controlling agent, stabilizer, a preservative, glycerin, alcohol, carbonizing agent used in carbonate beverage et al.
  • the other component than aforementioned ones may be fruit juice for preparing natural fruit juice, fruit juice beverage and vegetable beverage, wherein the component can be used independently or in combination.
  • the ratio of the components is not so important but is generally range from about 0 to 20 w/w % per 100 w/w % present composition.
  • Examples of addable food comprising aforementioned extract therein are various food, beverage, gum, vitamin complex, health improving food and the like.
  • Example 1 The ethyl acetate extract of Kalopanax pictus Nakai The bark of dried Kalopanax pictus Nakai (5120g) was crushed, refluxed 3 times in 7. of 70% methanol for 2 hours and concentrated. Finally, 812g of the extract were obtained.
  • the ethyl acetate fraction (61.2g) obtained in the Example 1 was purified by flash column chromatography (7x70cm) on silica gel at the rate 150 m./min with chloroform/methanol (100:1->1:1) as an eluant to give eleven number of fractions.
  • the 8th fraction (llg) which shows relevant activity was purified by flash column chromatography (4x40cm) on silica gel at the rate 80 mi
  • the 4th fraction was purified by flash column chromatography (3x30cm) on silica gel at the rate 50 m_/min with chloroform/methanol (100:1->1:1) as an eluant to give pictoside A whose R f value was 0.45 and pictoside B whose R f value was 0.55 represented by the following formula ( II ), (HI).
  • the isolated compounds were identified as triterpenenoid glycoside whose the C 3 -saccharide moiety as essential groups for recognition, used as samples.
  • the butanol fraction (352.2g) obtained in the Example 1 was added with 5% KOH- methanol 3. at 80 °C.
  • the alkali hydrolysates was neutralized with 3.2% HC1 (3 - ), added with 3-fold ethyl acetate, filtered and the filtrate was concentrated in vacuo to get ethyl acetate fraction (55.6g).
  • the ethyl acetate fraction was purified by flash column chromatography (8x80cm) on silica gel at the rate 300 m_/min with chloroform/methanol (100:1->1:1) as an eluant to give five number of fractions.
  • Kalopanaxsaponin A (12.8g) obtained in the Example 3 was dissolved in small amount of methanol and added with diazomethanol for 20 hours at 20 °C to get kalopanaxsaponin A methyl ester (3-O- ⁇ -L-Arabinopyranoxyl(l->2)- ⁇ -L- Lamnopyranosyl Hedrgenin methyl ester) (13. Og).
  • mice having its mean body weight of 130 to 160g Male ICR mice having its mean body weight of 130 to 160g were used and each group consisting of 8 mice was administrated subcutaneously with 0.1 ml/mouse of complete adjuvant at the sole of its foot and then, 14 days later, administrated orally 1 times/day with 500mg/kg of butanol extract and 300mg/kg of alkali hydrolysates for 4 to 10 days.
  • Loxoprofen (Dong Kwang Pharm. Co., Ltd) was used as control. The edema period of mice was measured by plethysmometer.
  • mice having its mean body weight of 130 to 160g Male ICR mice having its mean body weight of 130 to 160g were used and each group consisting of 10 mice was administrated subcutaneously with 0.1 mC/mouse of complete adjuvant at the sole of its foot and then, 14 days later, administrated orally 1 times/day with 500mg/kg of kalopanaxsaponin A, kalopanaxsaponin A methyl ester (Rheumaster) and 300mg/kg of ethyl acetate for 7 to 10 days. Ibuprofen was used as control. The edema period of mice was measured by plethysmometer.
  • kalopanaxsaponin A methyl ester can be used as a rheumatic arthritis drug to treat rheumatic arthritis without side effects. Therefore, the present invention is very useful in the medical industry in respect to treatment and protection of patients suffering with rheumatic arthritis.
  • mice The acute toxicity tests on ICR mice (mean body weight 25 ⁇ 5g) performed using the ethyl acetate soluble extract from Kalopanax pictus Nakai and kalopanaxsaponin A derivates. Each group consisting of 3 mice or rats was administrated intraperitoneally with 2000mg/kg of test compounds or solvents (0.2 mi., i.p.), respectively and observed for 24 hrs.
  • Powder preparation was prepared by mixing above components and filling sealed package.
  • Tablet preparation was prepared by : mixing above
  • Tablet preparation was prepared by mixing above components and filling gelatin capsule by conventional gelatin preparation method.
  • Injection preparation was prepared by dissolving active component, controlling pH to about 7.5 and then filling all the components in 2 mi ample and sterilizing by conventional injection preparation method.
  • a composition comprising the ethyl acetate soluble extract from Kalopanax pictus Nakai or kalopanaxsaponin A derivatives according to the present invention is useful in the prevention or treatment of inflammatory and rheumatic diseases by determining various relating inflammatory and rheumatic model experiments.

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Abstract

La présente invention concerne un extrait soluble d'acétate d'éthyle produit à partir de Kalopanax pictus Nakai, qui présente une activité inflammatoire et rhumatismale. Elle concerne également une composition pharmaceutique comprenant ledit extrait d'acétate d'éthyle provenant de Kalopanax pictus Nakai, et des dérivés de kalopanaxsaponin A isolés dudit extrait et destinés à prévenir ou traiter une maladie inflammatoire ou rhumatismale.
PCT/KR2002/002296 2002-05-27 2002-12-06 Composition contenant un extrait soluble d'acetate d'ethyle produit a partir de kalopanax pictus nakai, et derives de kalopanaxsaponin a isoles dudit extrait pour prevenir ou traiter une maladie inflammatoire ou rhumatismale Ceased WO2003099305A1 (fr)

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AU2002367988A AU2002367988A1 (en) 2002-05-27 2002-12-06 Composition containing an ethyl acetate soluble extract from kalopanax pictus nakai and kalopanaxsaponin a derivatives isolated therein for protecting and treating inflammatory and rheumatic disease

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KR2002/29419 2002-05-27
KR1020020029419A KR100555660B1 (ko) 2002-05-27 2002-05-27 해동피의 에틸아세테이트 가용 추출물로 부터 분리된 칼로파낙스 사포닌 에이 유도체를 포함하는 관절염 예방 및 치료용 조성물

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CN104761610A (zh) * 2015-02-10 2015-07-08 江西本草天工科技有限责任公司 一类新型的α-常春藤皂苷衍生物及其制备方法和用途
CN107550917A (zh) * 2017-10-19 2018-01-09 广州博济医药生物技术股份有限公司 常春藤皂苷元及其衍生物或其盐在制备治疗骨性关节炎药物中的应用
CN112194701A (zh) * 2020-10-10 2021-01-08 福建师范大学泉港石化研究院 一种改性无患子皂苷相容剂及其制备方法与应用

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KR100896325B1 (ko) * 2002-06-29 2009-05-07 학교법인 상지학원 칼로파낙스사포닌 ｋ 및 이의 대사물 및 이를 함유한 염증및 관절염 치료제
KR101321754B1 (ko) * 2013-03-29 2013-10-28 유한회사한풍제약 류마티스 관절염 및 골관절염의 개선 또는 치료를 위한 조성물

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104761610A (zh) * 2015-02-10 2015-07-08 江西本草天工科技有限责任公司 一类新型的α-常春藤皂苷衍生物及其制备方法和用途
CN107550917A (zh) * 2017-10-19 2018-01-09 广州博济医药生物技术股份有限公司 常春藤皂苷元及其衍生物或其盐在制备治疗骨性关节炎药物中的应用
WO2019075865A1 (fr) * 2017-10-19 2019-04-25 广州博济医药生物技术股份有限公司 Applications d'hederagénine et de dérivé ou de sel d'hederagénine dans la préparation de médicaments pour le traitement de l'arthrose
CN107550917B (zh) * 2017-10-19 2020-04-24 广州博济医药生物技术股份有限公司 常春藤皂苷元及其衍生物或其盐在制备治疗骨性关节炎药物中的应用
CN112194701A (zh) * 2020-10-10 2021-01-08 福建师范大学泉港石化研究院 一种改性无患子皂苷相容剂及其制备方法与应用
CN112194701B (zh) * 2020-10-10 2023-03-03 福建师范大学泉港石化研究院 一种改性无患子皂苷相容剂及其制备方法与应用

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KR100555660B1 (ko) 2006-03-10
AU2002367988A1 (en) 2003-12-12

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