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WO1997031933A1 - Nouveaux composes de saponine de ginseng, processus de preparation de ces composes et agent antitumoral comprenant ces composes en qualite de composant actif - Google Patents

Nouveaux composes de saponine de ginseng, processus de preparation de ces composes et agent antitumoral comprenant ces composes en qualite de composant actif Download PDF

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Publication number
WO1997031933A1
WO1997031933A1 PCT/KR1996/000123 KR9600123W WO9731933A1 WO 1997031933 A1 WO1997031933 A1 WO 1997031933A1 KR 9600123 W KR9600123 W KR 9600123W WO 9731933 A1 WO9731933 A1 WO 9731933A1
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WO
WIPO (PCT)
Prior art keywords
compound
compounds
ginseng
water
formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/KR1996/000123
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English (en)
Inventor
Man Ki Park
Seung Ki Lee
Jeong Hill Park
Jong Moon Kim
Kwang Youl Lee
Sang Beom Han
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
CJ Corp
Original Assignee
CJ Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by CJ Corp filed Critical CJ Corp
Priority to AU65334/96A priority Critical patent/AU6533496A/en
Publication of WO1997031933A1 publication Critical patent/WO1997031933A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C07J17/005—Glycosides

Definitions

  • the present invention relates to novel ginseng saponin compounds having an anti-tumor activity. More specifical ⁇ ly, the present invention relates to novel ginseng saponin compounds having a potent anti-tumor activity, which are represented by the following formulas (I) and (II) .
  • the present invention also relates to a process for preparation thereof, and an anti-tumor composition com ⁇ prising the same as an active component.
  • the present inventors have concentratedly stud ⁇ ied to find a method for enhancing the pharmacological effect of ginseng by treating ginseng under specific conditions to increase the contents of specific components and further for separating the respective components so that the study of their pharmacological effect can be made.
  • a ginseng is heat-treated for 0.5 to 20 hours at a high temperature of 110 to 180°C, the contents of effec ⁇ tive components which are present in a minor amount in ginseng increase, and consequently a processed ginseng having an enhanced pharmacological effect compared with fresh ginseng, white ginseng or red ginseng is prepared.
  • the present invention relates to saponin compounds identified as novel active components contained in ginseng.
  • the first object of the present invention is to pro ⁇ vide the novel saponin compounds represented by the fol ⁇ lowing formulas (I) and (II) .
  • the compounds of formulas (I) and (II) according to the present invention can be prepared by an extraction from the processed product of plant of Panax genus or by a synthetic method using known ginsenoside components as a starting material.
  • roots or leaves of the plant of Panax genus for example, Panax ginseng, Panax notoginseng, Panax quinque fol i um, Panax japoni cus , etc., or tissue cultures thereof, or extracts therefrom with water or lower alcohol are heated for 0.5 to 20 hours at a temperature of 110 to 180°C.
  • the proc ⁇ essed ginseng thus obtained is extracted with water, or a suitable organic solvent, for example, lower alcohols such as methanol, ethanol, etc., or a solvent mixture thereof, and then the extract is concentrated under reduced pres- sure, suspended in water and then extracted with a nonpo- lar organic solvent such as hexane, ether, dichlorometh- ane, chloroform, ethylacetate or a solvent mixture there ⁇ of.
  • a nonpo- lar organic solvent such as hexane, ether, dichlorometh- ane, chloroform, ethylacetate or a solvent mixture there ⁇ of.
  • the remaining aqueous layer is extracted with a polar organic solvent such as butanol and then the extract is subjected to chromatography to obtain a fraction con ⁇ taining compounds (I) and (II) .
  • This fraction is crys ⁇ tallized from a suitable solvent system, for example a solvent mixture of water and lower alcohol, preferably a solvent mixture of water and methanol in a ratio of 1:1 by volume, to prepare the desired pure saponin compounds (I) and (II) .
  • a suitable solvent system for example a solvent mixture of water and lower alcohol, preferably a solvent mixture of water and methanol in a ratio of 1:1 by volume, to prepare the desired pure saponin compounds (I) and (II) .
  • a sugar moiety attached, to the 20th carbon of panaxadiol saponins present in ginseng such as ginsenosides Ra, Rb-,, Rb 2 , Re, Rd, etc. is removed and an acetyl group is introduced into the 6th position of the terminal glucose of the sugar moiety attached to 3rd carbon to produce the novel saponin compound (I) .
  • the saponin compound (I) can also be produced by removing the sugar moiety attached to the 20th carbon from ginsenosides Rs j and Rs 2 .
  • the saponin compound (II) is produced by removing the OH group attached to the 20th carbon and hydrogen at the 22th-position from the compound (I) through dehydration reaction. In this reaction, the stereochemical structure of the double bond at 20th-posi- tion can have cis or trans configuration.
  • the contents of the desired compounds (I) and (II) can be more increased by repeatedly carrying out chromatography.
  • the order of the heat-treatment step and extraction step with organic solvent in this process can be inverted to obtain the same result.
  • (II) can be obtained by acetylating the known ginsenoside compounds.
  • the compound of formula (I) can be produced by acetylating the known ginsenoside Rg 3 of formula (III)
  • the compound of formula (II) can be prepared by acetylating the known 20 ⁇ 22 ⁇ -ginsenoside Rg 3 of formula (IV) which is formed by the dehydration reac ⁇ tion at 20th-position of ginsenoside Rg 3 .
  • Such acetylation reaction can be conducted using acetic anhydride (Ac 2 0) or acetyl chloride as an acetylat ⁇ ing agent.
  • the acetylating agent can be used in a molar ratio of 1:1-4, preferably 1:1.2-2 with respect to the compound (III) or (IV) . It is appropriate to carry out this reaction at a temperature of -40°C to 20°C, preferably -40°C to 0°C, for 1 to 48 hours.
  • novel saponin compound of formula (I) or (II) thus obtained can be further purified by a conventional work- ing-up method, for example, selective crystallization, column chromatograpy, etc.
  • composition containing the compounds (I) and/or (II) of the present invention When the composition containing the compounds (I) and/or (II) of the present invention is applied for clini- cal purposes as an anti-tumor agent, it can be combined with pharmaceutically acceptable carriers to prepare various formulations conventionally used in the pharmaceu- tical field, for example, oral preparations such as tab ⁇ lets, capsules, troches, solutions, suspensions, etc.; injectable preparations such as injectable solutions or suspensions, or ready-to-use dried powder which can be applied after re-constituted with injectable distilled water before injection, etc.; or locally applicable prepa ⁇ rations such as ointments, creams, solutions, etc.
  • oral preparations such as tab ⁇ lets, capsules, troches, solutions, suspensions, etc.
  • injectable preparations such as injectable solutions or suspensions, or ready-to-use dried powder which can be applied after re-constituted with injectable distilled water before injection, etc.
  • the carriers which can be used in the composition of the present invention are conventional ones in the pharma ⁇ ceutical field, for example, binders, lubricants, disinte ⁇ grating agents, excipients, solubilizers , dispersing agents, stabilizers, suspending agents, coloring agents, flavors and the like in the case of oral preparations; preservatives, agents for painlessness , solubilizers, stabilizers and the like in the case of injectable prepa ⁇ rations; bases, excipients, lubricants, preservatives and the like in the case of locally applicable preparations.
  • the pharmaceutical preparations thus produced can be administered orally, or parenterally such as for example intravenously, peritoneally, subcutaneously , or can be topically applied.
  • the oral preparations may be administered together with an antacid or in the form of an enteric-coated preparation which is formulated by covering the orally administrable solid preparation such as tablet with the enteric coatings, in order to prevent decomposition of the preparation by gastric acid when it is administered per orally.
  • the administration dosage to a human being of the novel saponin compounds (I) and (II) according to the present invention can be selected depending on the absorp ⁇ tion, inactivating rate and excretion rate of the active component in the body, age, sex and condition of the subject patient, severity of the disorders to be treated and the like, it is generally administered to an adult in an amount of 5 to 500mg, preferably 10 to 200mg daily. Therefore, when the composition of the present invention is formulated into the dosage unit form, each of the dosage unit form can contain the compounds (I) and/or (II) in an amount of 5 to 500mg, preferably 10 to 200mg on the basis of the effective amount range as mentioned above.
  • the dosage unit form thus formulated can be administered using a specialized method according to the judgement of the specialist who arranges or observes the administration and the requirement of the individuals.
  • the total daily dosage can also be divided into several portions and administered over several times, preferably 1 to 6 times.
  • lOOg of fresh ginseng was introduced into a sealed container and then heated for 2 hours at 130°C.
  • the obtained processed ginseng was extracted with 200ml of methanol to obtain the methanol extract and then methanol was removed from the extract by evaporation.
  • the remain ⁇ ing residue was suspended in 100ml of water, extracted 3 times with 100ml of ether, and then the remaining aqueous layer was extracted 3 times with 100ml of butanol saturat- ed with water to obtain the butanol extract containing saponins.
  • Example 2 lg of the fraction containing the compound (I) pre- pared in Example 2 above was subjected to silica gel column chromatograpy according to the same manner as Example 1 using the mixed solvent of ethyl acetate/metha ⁇ nol/water (20 : 1 : 1) as an eluent to obtain 400mg of a fraction containing 92% of the desired compound (I) .
  • the fraction thus obtained was crystallized from the solvent mixture of methanol/water (1:1, v/v) to obtain 200mg of the desired compound (I) .
  • the compound (I) thus obtained exhibits the following physico-chemical characteristics :
  • Example 2 lg of the fraction containing the compound (II) pre ⁇ pared in Example 2 above was subjected to silica gel column chromatography according to the same manner as Example 1 using the solvent mixture of ethyl acetate/ methanol/water (20 : 1:1) as an eluent to obtain 300mg of a fraction containing 95% of the desired compound (II) .
  • the fraction thus obtained was crystallized from the solvent mixture of methanol/water (1:1, v/v) to obtain 150mg of the desired compound (II) .
  • ginsenoside Rg 3 50mg of ginsenoside Rg 3 was dried under reduced pres ⁇ sure and 1ml of 2,4, 6-collidine was added thereto and then stirred for 10 minutes at -40°C. lO ⁇ l of acetyl chloride was introduced thereinto and then the mixture was allowed to react for 3 hours. The reaction mixture was warmed slowly to room temperature and allowed to stand for 1 hour at room temperature . 1ml of methanol was added and the reaction solution was subjected to silica gel column chromatography according to the same manner as Example 1 to obtain 20mg of the desired compound (I) .
  • Test Example 1 Anti-tumor activity of the compounds (I) and (II)
  • the anti-tumor activity of the novel saponin compounds of formulas (I) and (II) according to the present inven ⁇ tion was determined by the method for measuring the incor- poration amount of 3 H thymidine as described in the fol ⁇ lowing.
  • DMEM Dulbecco's Modified Eagle's Medium, manufactured by Gibco Co.
  • DMEM Dulbecco's Modified Eagle's Medium, manufactured by Gibco Co.
  • IL deion-ized water
  • pH 7.4 sodium carbon ⁇ ate and hydrochloric acid solution
  • 10% calf serum, 1x10 M of insulin and 50mg/L of gentamycin were added thereto.
  • the mixture was then sterilized by means of a millipore filter to prepare the culture solution.
  • both the compounds (I) and (II) remarkably decrease the amount of incorporated radioactive thymidine at a concentration of 0. l ⁇ M or more, particularly 5 ⁇ M or more. Therefore, it can be seen that the compounds (I) and (II) significantly inhibit the growth of hepatoma sk-Hep-1 cells.
  • Test Example 2 Cell growth-inhibitory activity of the compounds (I) and (II) against human hepatoma cells
  • DMEM Dulbecco's Modified Eagle's Medium, manufactured by Gibco Co.
  • DMEM Dulbecco's Modified Eagle's Medium, manufactured by Gibco Co.
  • 10% calf serum, 1x10 " 'M of insulin and 50mg/L of genta ycin were added thereto.
  • the mixture was then sterilized by means of a millipore filter to prepare the culture solution.
  • Test Example 3 Acute toxicity test of the compounds (I) and (II)
  • mice weighing 20 to 40g were used as test animal and divided into 2 groups including 20 mice, respectively.
  • Each of the compounds (I) and (II) according to the present invention was suspended in 1ml of physiological saline and orally administered to each group. After 14 days from administration, the number of survived test animal was counted. To the control group, 1ml of physio ⁇ logical saline was orally administered. The results are described in the following Table 4. 17
  • Test group Dosage Number of Number of (mg/kg,Oral) Test animals Survived animals

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Steroid Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

La présente invention concerne de nouveaux composés de saponine de ginseng qui possèdent une puissante activité antitumorale et correspondent aux formules (I) et (II). Les nouveaux composés correspondant aux formules (I) et (II) peuvent être obtenus en chauffant des végétaux du genre ginseng pendant une durée de 0,5 à 20 heures et à une température élevée variant entre 110 et 180° C. Ces composés peuvent également être synthétisés par l'acétylation de ginsénoside Rg3 et de Δ20(22)-ginsénoside Rg¿3? qui sont des composés connus de saponine de ginseng, respectivement. La présente invention concerne également une composition antitumorale comprenant les composés (I) et/ou (II) en qualité d'ingrédients actifs.
PCT/KR1996/000123 1996-02-27 1996-07-29 Nouveaux composes de saponine de ginseng, processus de preparation de ces composes et agent antitumoral comprenant ces composes en qualite de composant actif Ceased WO1997031933A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU65334/96A AU6533496A (en) 1996-02-27 1996-07-29 Novel ginseng saponin compounds, process for preparation thereof and anti-tumor agent comprising the same as an active component

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1996/4879 1996-02-27
KR1019960004879A KR0169536B1 (ko) 1996-02-27 1996-02-27 신규한 인삼 사포닌, 그의 제조방법 및 이를 유효성분으로 하는 항종양제

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WO1997031933A1 true WO1997031933A1 (fr) 1997-09-04

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AU (1) AU6533496A (fr)
WO (1) WO1997031933A1 (fr)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999016786A1 (fr) * 1997-09-26 1999-04-08 Institute Of Radiation Medicine, Academy Of Military Medical Sciences Of The Pla Utilisation de composes de saponine et de steroides pour prevenir la senilite et nouveaux composes de saponine steroide
WO2003010182A1 (fr) * 2001-07-24 2003-02-06 Panagin Pharmaceuticals Inc. Nouvelles sapogenines dammaranes, leur utilisation comme agents anticancereux et leur procede de production
WO2003086439A1 (fr) * 2002-04-08 2003-10-23 Ginseng Science Inc. Nouvelle utilisation de l'extrait traite provenant du genre panax et compose de saponine isole a partir de ladite plante
WO2003086438A1 (fr) * 2002-04-08 2003-10-23 Ginseng Science Inc. Extrait de plante du genre panax transforme, procede de preparation de cet extrait et compositions contenant cet extrait
US6949523B2 (en) 2001-07-24 2005-09-27 Panagin Pharmaceuticals, Inc. Aglycon dammarane sapogenins, their use as anti-cancer agents, and a process for producing same
US7138427B2 (en) 1999-03-26 2006-11-21 Phytopharm Plc. 5-β-sapogenin and pseudosapogenin derivatives and their use in the treatment of dementia
US7875650B2 (en) * 2004-02-03 2011-01-25 Yale University Compounds and methods to increase anti-P-glycoprotein activity of baicalein by alkylation on the A ring
CN103316119A (zh) * 2013-05-17 2013-09-25 胡庆华 一种治疗白血病的中药药物
WO2016095248A1 (fr) * 2014-12-17 2016-06-23 富力 Dérivé de 20(r)-ginsénoside rg3, son procédé de préparation et application
RU2673885C1 (ru) * 2014-12-17 2018-12-03 Ли ФУ Полиацилированные производные 20(r)-гинзенозида rg3, их получение и применение

Families Citing this family (2)

* Cited by examiner, † Cited by third party
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KR100485936B1 (ko) * 2002-10-23 2005-04-27 주식회사 바이오사포젠 진세노사이드 Rh2 및 Rg3 항암 조성물
KR100746799B1 (ko) * 2003-06-19 2007-08-23 최용석 사포닌 조성액의 제조방법

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DE4001895A1 (de) * 1990-01-23 1991-07-25 Harrier Gmbh Herstellung von insbesondere steroidglykosiden

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DE4001895A1 (de) * 1990-01-23 1991-07-25 Harrier Gmbh Herstellung von insbesondere steroidglykosiden

Non-Patent Citations (3)

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CHEMICAL ABSTRACTS, Vol. 107, No. 3, 20 July 1987 (Columbus, Ohio, USA), page 642, Abstract No. 23596r, L.N. ATOPKINA et al., "Glycosylation of Dammarane Type Triterpenoids. IV. beta-D-Glucopyranosides of Betulafolienetriol and its Derivatives"; & KHIM. PRIR. SOEDIN., 1968, (3), 301-12. *
CHEMICAL ABSTRACTS, Vol. 112, No. 19, 07 May 1990 (Columbus, Ohio, USA), page 432, Abstract No. 175597h, I. KITAGAWA et al., "Chemical Studies on Crude Drug Processing. VI. Chemical Structures of Malonyl-ginsenosides Rb1, Rb2, Rc and Rd Isolated from the Root of Panax Ginseng C.A. Meyer"; & CHEM. PHARM. BULL., 1989, *
CHEMICAL ABSTRACTS, Vol. 123, No. 9, 28 August 1995 (Columbus, Ohio, USA), page 748, Abstract No. 122844g, D.S. KIM et al., "Preparation and Structur Determination of a New Glycoside, (20E)-Ginsenoside Rh3 and Its isomer from Diol-Type Ginseng Saponins"; & YAKHAK HOECHI, 1995, 39(1), 85-93. *

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6593301B1 (en) 1997-09-26 2003-07-15 Institute Of Radiation Medicine Use of steroidal saponins for the prophylaxis or treatment of dementia, and novel steroidal saponin compounds
WO1999016786A1 (fr) * 1997-09-26 1999-04-08 Institute Of Radiation Medicine, Academy Of Military Medical Sciences Of The Pla Utilisation de composes de saponine et de steroides pour prevenir la senilite et nouveaux composes de saponine steroide
CN1131237C (zh) * 1997-09-26 2003-12-17 中国人民解放军军事医学科学院放射医学研究所 甾体皂甙防治老年性痴呆的用途及新的甾体皂甙
US7507720B2 (en) 1998-03-26 2009-03-24 Phytopharm Plc 5-Beta-sapogenin and pseudosapogenin derivatives and their use in the treatment of dementia
US7138427B2 (en) 1999-03-26 2006-11-21 Phytopharm Plc. 5-β-sapogenin and pseudosapogenin derivatives and their use in the treatment of dementia
WO2003010182A1 (fr) * 2001-07-24 2003-02-06 Panagin Pharmaceuticals Inc. Nouvelles sapogenines dammaranes, leur utilisation comme agents anticancereux et leur procede de production
CN100473661C (zh) * 2001-07-24 2009-04-01 博新药业股份有限公司 达玛烷皂苷配基,它们作为抗癌剂的应用和生产它们的方法
US6888014B2 (en) 2001-07-24 2005-05-03 Panagin Pharmaceuticals Inc. Dammarane sapogenins, their use as anti-cancer agents, and a process for producing same
US6949523B2 (en) 2001-07-24 2005-09-27 Panagin Pharmaceuticals, Inc. Aglycon dammarane sapogenins, their use as anti-cancer agents, and a process for producing same
WO2003086438A1 (fr) * 2002-04-08 2003-10-23 Ginseng Science Inc. Extrait de plante du genre panax transforme, procede de preparation de cet extrait et compositions contenant cet extrait
WO2003086439A1 (fr) * 2002-04-08 2003-10-23 Ginseng Science Inc. Nouvelle utilisation de l'extrait traite provenant du genre panax et compose de saponine isole a partir de ladite plante
US7875650B2 (en) * 2004-02-03 2011-01-25 Yale University Compounds and methods to increase anti-P-glycoprotein activity of baicalein by alkylation on the A ring
CN103316119A (zh) * 2013-05-17 2013-09-25 胡庆华 一种治疗白血病的中药药物
WO2016095248A1 (fr) * 2014-12-17 2016-06-23 富力 Dérivé de 20(r)-ginsénoside rg3, son procédé de préparation et application
CN105777838A (zh) * 2014-12-17 2016-07-20 富力 20(R)-人参皂苷Rg3衍生物、制备方法及其应用
RU2673885C1 (ru) * 2014-12-17 2018-12-03 Ли ФУ Полиацилированные производные 20(r)-гинзенозида rg3, их получение и применение
RU2695380C1 (ru) * 2014-12-17 2019-07-23 Ли ФУ Полиацилированные производные 20(r)-гинзенозида rg3, их получение и применение

Also Published As

Publication number Publication date
KR0169536B1 (ko) 1999-01-15
KR970061910A (ko) 1997-09-12
AU6533496A (en) 1997-09-16

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