DE4017766A1 - New saponin cpds. - obtd. from Gypsophila paniculata and G. arrostii root, for use as pharmaceuticals - Google Patents

New saponin cpds. - obtd. from Gypsophila paniculata and G. arrostii root, for use as pharmaceuticals

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Publication number
DE4017766A1
DE4017766A1 DE19904017766 DE4017766A DE4017766A1 DE 4017766 A1 DE4017766 A1 DE 4017766A1 DE 19904017766 DE19904017766 DE 19904017766 DE 4017766 A DE4017766 A DE 4017766A DE 4017766 A1 DE4017766 A1 DE 4017766A1
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Prior art keywords
xylopyranosyl
beta
arrostii
gypsophila
saponins
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DE19904017766
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German (de)
Inventor
Denise Frechet
Bruno Christ
Du Sorbier Bertrand Monegier
Hartmut Fischer
Marc Vuilhorgne
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A Natterman und Cie GmbH
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A Natterman und Cie GmbH
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Priority to DE19904017766 priority Critical patent/DE4017766A1/en
Publication of DE4017766A1 publication Critical patent/DE4017766A1/en
Withdrawn legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
    • C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20—Carbocyclic rings
    • C07H15/24—Condensed ring systems having three or more rings
    • C07H15/256—Polyterpene radicals

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Steroid Compounds (AREA)

Abstract

New saponins (I) derived from the roots of Gypsophila paniculata and G. arrostii are claimed. 4 compounds are specifically claimed, including 3-O-beta-galactopyranosyl -(1-2)-(beta-D-xylo pyranosyl-(1-3)-beta-D- glucuronopyranosyl quillaic acid 28-O-beta-D-glucopyranosyl -(1-3)-(beta-D-xylo pyranosyl-(1-4)-alpha-L- rhamnopyranosyl-(1-2)- beta-D-fucopyranoside. The saponins are produced by extracting the roots and separating the cpds. by reverse phase chromatography. USE/ADVANTAGE - The saponins are useful in pharmaceutical preparations (claimed). (N.B. No specific applications are given). They can be made into tablets, pills etc. and can also be made into liq. prepns. for enteral administration.

Description

Die Erfindung betrifft neue Saponine aus den Wurzeln von Gypsophila paniculata und Gypsophila arrostii sowie Verfahren zu ihrer Gewinnung und ihre Verwendung in pharmazeutischen Präparaten.The invention relates to new saponins from the roots of Gypsophila paniculata and Gypsophila arrostii as well Process for their extraction and their use in pharmaceutical preparations.

Saponine sind im allgemeinen pflanzliche Glykoside, die in Wasser seifenartige, kolloidale Lösungen bilden. Sie werden nach der Art ihrer Aglykone (Sapogenine) in Triterpen- und Steroid-Saponine unterschieden. Saponins are generally vegetable glycosides that form soap-like, colloidal solutions in water. they are classified according to the type of their aglycones (sapogenins) A distinction was made between triterpene and steroid saponins.  

Die Triterpen-Saponine sind in der Natur am weitesten verbreitet und können aus den verschiedensten Pflanzen gewonnen werden, zu denen auch die Gypsophila-Arten gehören. Aus Gypsophila paniculata und Gypsophila arrostii konnten jedoch bisher lediglich Gypsosid, ein triterpenoides Saponin, das Gypsogenin und neun Zuckereinheiten enthält, isoliert werden.The triterpene saponins are the farthest in nature spread and can be from a variety of plants can be obtained, including the Gypsophila species belong. From Gypsophila paniculata and Gypsophila arrostii, however, have so far only been able to use gypsoside triterpenoid saponin, the gypsogenin and nine Contains sugar units can be isolated.

Überraschenderweise wurde nun bei der Extraktion der Wurzel von Gypsophila paniculata und Gypsophila arrostii und der anschließenden Bestimmung mittels verschiedener Analysenmethoden vier neue Triterpen- Saponine gefunden, die bisher in der Literatur nicht beschrieben wurden.Surprisingly, the Root of Gypsophila paniculata and Gypsophila arrostii and the subsequent determination by means of four new triterpene Saponins found that have not previously been found in the literature have been described.

Durch Vergleich der mittels Massenspektrometrie , ¹H-NMR und ¹³C-NMR erhaltenen Spektren in Kombination mit den aus der Dünnschichtchromatographie und Hochleistungs­ flüssigkeitschromatographie (HPLC) erhaltenen Ergebnissen konnten für die neuen Verbindungen die in der Abb. 1 angegebenen Strukturen sichergestellt werden.By comparing the spectra obtained by means of mass spectrometry, 1 H-NMR and 13 C-NMR in combination with the results obtained from thin-layer chromatography and high-performance liquid chromatography (HPLC), the structures shown in FIG. 1 could be ensured for the new compounds.

Die erfindungsgemäßen Verbindungen können nach an sich bekannten Verfahren aus den Wurzeln von Gypsophila paniculata und Gypsophila arrostii erhalten werden, etwa durch Extraktion der getrockneten Wurzeln mit einem Alkohol/Wasser-Gemisch und der anschließenden Aufarbeitung des Extraktes durch Säulenchromatographie. Durch entsprechende Fraktionierung und einem geeigneten Laufmittel (Methanol) lassen sich Fraktionen sammeln, in denen die erfindungsgemäßen Verbindungen nachgewiesen werden können.The compounds according to the invention can per se known methods from the roots of Gypsophila paniculata and Gypsophila arrostii are obtained, by extracting the dried roots with an alcohol / water mixture and the following Processing of the extract by column chromatography. By appropriate fractionation and a suitable one Mobile solvents (methanol) can be collected in fractions, in which the compounds of the invention can be demonstrated.

Die neuen Verbindungen können leicht zu pharmazeutischen Präparaten verarbeitet werden, indem eine wirksame Menge der Substanzen zusammen oder im Gemisch mit organischen oder anorganischen, festen oder flüssigen, pharmazeutisch verwendbaren Trägerstoffen, die sich enteral verabreichen lassen, gemischt werden. Die Substanzen können auch als Flüssigpräparat verabreicht werden.The new connections can easily pharmaceutical preparations are processed by an effective amount of the substances together or in  Mixture with organic or inorganic, solid or liquid, pharmaceutically usable carriers, which can be administered enterally, are mixed. The substances can also be used as a liquid preparation be administered.

So verwendet man Tabletten oder Gelatinekapseln, welche den Wirkstoff zusammen mit Verdünnungsmitteln, wie z. B. Lactose, Dextrose, Sucrose, Mannitol, Sorbitol, Cellulose und/oder Glycerin und Schmiermittel, z. B. Kieselerde, Talg, Stearinsäure oder Salze davon, wie Magnesium- und Calciumstearat und/oder Polyethylenglykol aufweisen. Tabletten enthalten ebenfalls Bindemittel, wie z. B. Magnesium, Aluminiumsilikat, Stärke wie Mais, Weizen, Reis, Gelatine, Methylcellulose, Carboxymethylcellulose und/oder Polyvinylpyrolidon, sowie weiterhin Brausemischungen, Absorptionsmittel, Farb- und Geschmacksstoffe sowie Süßmittel.So you use tablets or gelatin capsules, which the active ingredient together with diluents, such as. B. Lactose, dextrose, sucrose, mannitol, sorbitol, Cellulose and / or glycerin and lubricants, e.g. B. Silica, tallow, stearic acid or salts thereof, such as Magnesium and calcium stearate and / or Have polyethylene glycol. Tablets also contain binders, such as. B. Magnesium, aluminum silicate, starch such as corn, wheat, Rice, gelatin, methyl cellulose, carboxymethyl cellulose and / or polyvinyl pyrolidone, as well as further Shower mixes, absorbents, color and Flavors and sweeteners.

Die pharmazeutischen Präparate können in an sich bekannter Weise, etwa mittels konventioneller Misch-, Granulier-, Dragier-, Lösungs- oder Lyophilisierungs­ verfahren, hergestellt werden.The pharmaceutical preparations can in themselves known manner, for example by means of conventional mixing, Granulation, coating, solution or lyophilization process, be manufactured.

Beispiel 1Example 1

Ausgangsmaterial sind kommerziell erhältliche Seifenwurzeln der Arten Gypsophila paniculata und Gypsophila arrostii. Hiervon werden 100 g in getrockneter und gepulverter Form mit 200 ml Ethanol/Wasser (1 : 1) unter Rühren 24 Stunden extrahiert und anschließend das Pflanzenmaterial abfiltriet. Der Extrakt wird im Vakuum auf 20 ml eingeengt und mit 10 ml Wasser versetzt. 3-ml-Protionen des Extrakts werden an einer RP-18-Säule während 8 Stunden (linearer Gradient 30-100% Methanol) chromatographiert. 3,5 Stunden nach Start des Gradienten werden 20-ml-Fraktionen gesammelt und mittels HPLC (NucleosilR 100-C18, linearer Gradient in 25 Min. von 28% auf 35% Acetronil ansteigend) analysiert. Man erhält vier, den erfindungsgemäßen Verbindungen entsprechende Fraktionen. Das Methanol wird im Vakuum entfernt, die Glykoside in Wasser (mit 20% Acetonitril) gelöst und mittels semi-präparativer HPLC gereinigt. Die Reinheit der Proben wurde durch Dünnschichtchromatographie bestätigt. Hierfür wurde als Laufmittelsystem Chloroform/Methanol/Wasser/Essigsäure (64 : 50 : 10 : 2) verwendet.The starting material is commercially available soap roots of the species Gypsophila paniculata and Gypsophila arrostii. 100 g of this are extracted in dried and powdered form with 200 ml of ethanol / water (1: 1) with stirring for 24 hours and then the plant material is filtered off. The extract is concentrated in vacuo to 20 ml and 10 ml of water are added. 3 ml protions of the extract are chromatographed on an RP-18 column for 8 hours (linear gradient 30-100% methanol). 3.5 hours after the start of the gradient, 20 ml fractions are collected and analyzed by means of HPLC (Nucleosil R 100-C18, linear gradient increasing from 28% to 35% acetronil in 25 minutes). Four fractions corresponding to the compounds according to the invention are obtained. The methanol is removed in vacuo, the glycosides are dissolved in water (with 20% acetonitrile) and purified by means of semi-preparative HPLC. The purity of the samples was confirmed by thin layer chromatography. Chloroform / methanol / water / acetic acid (64: 50: 10: 2) was used as the solvent system.

Neben den Massenspektren und ¹H-NMR- und ¹³C-NMR- Aufnahmen wurden die Proben durch folgende Daten charakterisiert:In addition to the mass spectra and 1 H-NMR and 13 C-NMR The samples were recorded by the following data characterized:

Verbindung A:
3-O-β-galactopyranosyl-(1→2)-[β-D- xylopyranosyl-(1→3)]-β-D-glucuronopyranosyl quillajasäure 28-O-β-D-glucopyranosyl-(1→3)- [β-D-xylopyranosyl-(1→4)-α-L-rhamnopyranosyl- (1→2)-β-D-fucopyranosid.
Weißes, amorphes Pulver mit Schmp. 210-213°C.
Rf-Wert: 0,22. Beim Besprühen mit Vanillin- Schwefelsäure-Reagenz zeigt sich ein bräunlicher Fleck.Connection A:
3-O-β-galactopyranosyl- (1 → 2) - [β-D-xylopyranosyl- (1 → 3)] - β-D-glucuronopyranosyl quillaic acid 28-O-β-D-glucopyranosyl- (1 → 3) - [β-D-xylopyranosyl- (1 → 4) -α-L-rhamnopyranosyl- (1 → 2) -β-D-fucopyranoside.
White, amorphous powder with mp. 210-213 ° C.
R f value: 0.22. When sprayed with vanillin-sulfuric acid reagent, a brownish stain appears.

Verbindung B:
3-O-β-galactopyranosyl-(1→2)-[β-D- xylopyranosyl-(1→3)]-β-D-glucuronopyranosyl quillajasäure 28-O-β-D-arabinopyranosyl-(1→4)- β-D-arabinopyranosyl-(1→3)-[β-D-xylopyranosyl- (1→4)]-α-L-rhamnopyranosyl-(1→2)-β-D- fucopyranosid.
Weißes, amorphes Pulver mit Schmp. 213-215°C.
Rf-Wert: 0,18. Beim Besprühen mit Vanillin- Schwefelsäure-Reagenz zeigt sich ein bräunlicher Fleck.Compound B:
3-O-β-galactopyranosyl- (1 → 2) - [β-D-xylopyranosyl- (1 → 3)] - β-D-glucuronopyranosyl quillaic acid 28-O-β-D-arabinopyranosyl- (1 → 4) - β-D-arabinopyranosyl- (1 → 3) - [β-D-xylopyranosyl- (1 → 4)] - α-L-rhamnopyranosyl- (1 → 2) -β-D-fucopyranoside.
White, amorphous powder with mp. 213-215 ° C.
R f value: 0.18. When sprayed with vanillin-sulfuric acid reagent, a brownish stain appears.

Verbindung C:
3-O-β-glucopyranosyl-(1→2)-β-D- glucuronopyranosyl gypsogenin 28-O-β-D- glucopyranosyl-(1→3)-[β-D-xylopyranosyl- (1→4)]-α-L-rhamnopyranosyl-(1→2)-β-D- fucopyranosid.
Weißes, amorphes Pulver mit Schmp. 207-211°C.
Rf-Wert: 0,32. Beim Besprühen mit Vanillin- Schwefelsäure-Reagenz zeigt sich ein grünlicher Fleck.Compound C:
3-O-β-glucopyranosyl- (1 → 2) -β-D-glucuronopyranosyl gypsogenin 28-O-β-D-glucopyranosyl- (1 → 3) - [β-D-xylopyranosyl- (1 → 4)] - α-L-rhamnopyranosyl- (1 → 2) -β-D-fucopyranoside.
White, amorphous powder with mp. 207-211 ° C.
R f value: 0.32. A greenish spot appears when sprayed with vanillin-sulfuric acid reagent.

Verbindung D:
3-O-β-xylopyranosyl-(1→3)-[β-D- galoctopyranosyl-(1→2)]-β-D-glucurono pyranosyl gypsogenin 28-O-β-D-glucopyranosyl-(1→3)-[β-D- xylopyranosyl-(1→4)]-α-L-rhamnopyranosyl- (1→2)-β-D-fucopyranosid.
Weißes, amorphes Pulver mit Schmp. 207-211°C.
Rf-Wert: 0,28. Beim Besprühen mit Vanillin- Schwefelsäure-Reagenz zeigt sich ein grünlicher Fleck.Compound D:
3-O-β-xylopyranosyl- (1 → 3) - [β-D-galoctopyranosyl- (1 → 2)] - β-D-glucurono pyranosyl gypsogenin 28-O-β-D-glucopyranosyl- (1 → 3) - [β-D-xylopyranosyl- (1 → 4)] - α-L-rhamnopyranosyl- (1 → 2) -β-D-fucopyranoside.
White, amorphous powder with mp. 207-211 ° C.
R f value: 0.28. A greenish spot appears when sprayed with vanillin-sulfuric acid reagent.

Claims (7)

1. Neue Saponine aus den Wurzeln von Gypsophila paniculata und Gypsophila arrostii.1. New saponins from the roots of Gypsophila paniculata and Gypsophila arrostii. 2. 3-O-β-galactopyranosyl-(1→2)-[β-D- xylopyranosyl-(1→3)]-β-D-glucuronopyranosyl quillajasäure 28-O-β-D-glucopyranosyl-(1→3)- [β-D-xylopyranosyl-(1→4)]-α-L-rhamnopyranosyl- (1→2)-β-D-fucopyranosid. 2. 3-O-β-galactopyranosyl- (1 → 2) - [β-D- xylopyranosyl- (1 → 3)] - β-D-glucuronopyranosyl quillaja acid 28-O-β-D-glucopyranosyl- (1 → 3) - [β-D-xylopyranosyl- (1 → 4)] - α-L-rhamnopyranosyl- (1 → 2) -β-D-fucopyranoside.   3. 3-O-β-D-galactopyranosyl-(1→2)-[β-D- xylopyranosyl-(1→3)]-β-D-glucuronopyranosyl quillajasäure 28-O-β-D-arabinopyranosyl-(1→4)- β-D-arabinopyranosyl-(1→3)-[β-D-xylopyranosyl- (1→4)]-α-L-rhamnopyranosyl-(1→2)-β-D- fucopyranosid.3. 3-O-β-D-galactopyranosyl- (1 → 2) - [β-D- xylopyranosyl- (1 → 3)] - β-D-glucuronopyranosyl quillaic acid 28-O-β-D-arabinopyranosyl- (1 → 4) - β-D-arabinopyranosyl- (1 → 3) - [β-D-xylopyranosyl- (1 → 4)] - α-L-rhamnopyranosyl- (1 → 2) -β-D- fucopyranoside. 4. 3-O-β-D-glucopyranosyl-(1→2)-β-D- glucuronopyranosyl gypsogenin 28-O-β-D- glucopyranosyl-(1→3)-[β-D-xylopyranosyl- (1→4)]-α-L-rhamnopyranosyl-(1→2)-β-D- fucopyranosid.4. 3-O-β-D-glucopyranosyl- (1 → 2) -β-D- glucuronopyranosyl gypsogenin 28-O-β-D- glucopyranosyl- (1 → 3) - [β-D-xylopyranosyl- (1 → 4)] - α-L-rhamnopyranosyl- (1 → 2) -β-D- fucopyranoside. 5. 3-O-β-D-xylopyranosyl-(1→3)-[β-D- galoctopyranosyl-(1→2)]-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-glucopyranosyl-(1→3)-[β-D- xylopyranosyl-(1→4)]-α-L-rhamnopyranosyl- (1→2)-β-D-fucopyranosid.5. 3-O-β-D-xylopyranosyl- (1 → 3) - [β-D- galoctopyranosyl- (1 → 2)] - β-D-glucuronopyranosyl gypsogenin 28-O-β-D-glucopyranosyl- (1 → 3) - [β-D- xylopyranosyl- (1 → 4)] - α-L-rhamnopyranosyl- (1 → 2) -β-D-fucopyranoside. 6. Verfahren zur Herstellung der Saponine der Ansprüche 1 bis 5, dadurch gekennzeichnet, daß man die erfindungsgemäßen Verbindungen in an sich bekannter Weise aus den Wurzeln von Gypsophila paniculata und Gypsophila arrostii extrahiert und durch Chromatographie an Umkehrphasen einzelne Fraktionen erhält, die die Verbindungen der Ansprüche 2 bis 5 enthalten.6. Process for the preparation of the saponins Claims 1 to 5, characterized in that the compounds of the invention in themselves known way from the roots of Gypsophila paniculata and Gypsophila arrostii extracted and by single phase chromatography Receives fractions which are the compounds of Claims 2 to 5 included. 7. Arzneimittel, die die Verbindungen der Ansprüche 2 bis 5 neben den üblichen Hilfs- und Trägerstoffen enthalten.7. Medicines containing the compounds of claims 2 to 5 in addition to the usual auxiliaries and carriers contain.
DE19904017766 1990-06-01 1990-06-01 New saponin cpds. - obtd. from Gypsophila paniculata and G. arrostii root, for use as pharmaceuticals Withdrawn DE4017766A1 (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995028163A1 (en) * 1994-04-15 1995-10-26 New England Deaconess Hospital Corporation Enteral formulations for the treatment of inflammation and infection containing a saponin, possibly in combination with other compounds
CN102488752A (en) * 2011-12-31 2012-06-13 重庆市畜牧科学院 Chinese herbal medicinal composition for treating animal digestive tract diseases and preparation method of its preparation

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5674853A (en) * 1994-02-25 1997-10-07 Beth Israel Deaconess Medical Center, Inc. Enternal formulations for treatment of inflammation and infection
WO1995028163A1 (en) * 1994-04-15 1995-10-26 New England Deaconess Hospital Corporation Enteral formulations for the treatment of inflammation and infection containing a saponin, possibly in combination with other compounds
CN102488752A (en) * 2011-12-31 2012-06-13 重庆市畜牧科学院 Chinese herbal medicinal composition for treating animal digestive tract diseases and preparation method of its preparation
CN102488752B (en) * 2011-12-31 2013-10-30 重庆市畜牧科学院 Chinese herbal medicinal composition for treating animal digestive tract diseases and preparation method of its preparation

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