EP1318825A2 - Extrait de plante - Google Patents

Extrait de plante

Info

Publication number
EP1318825A2
EP1318825A2 EP01956248A EP01956248A EP1318825A2 EP 1318825 A2 EP1318825 A2 EP 1318825A2 EP 01956248 A EP01956248 A EP 01956248A EP 01956248 A EP01956248 A EP 01956248A EP 1318825 A2 EP1318825 A2 EP 1318825A2
Authority
EP
European Patent Office
Prior art keywords
extract
forster
extracts
piper methysticum
leaf
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.)
Withdrawn
Application number
EP01956248A
Other languages
German (de)
English (en)
Inventor
Bernd BÜTER
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.)
Vitaplant AG
Original Assignee
Vitaplant AG
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 Vitaplant AG filed Critical Vitaplant AG
Publication of EP1318825A2 publication Critical patent/EP1318825A2/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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)
    • A61K36/67—Piperaceae (Pepper family), e.g. Jamaican pepper or kava
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
    • A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P23/00—Anaesthetics
    • 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
    • A61P25/08—Antiepileptics; Anticonvulsants
    • 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
    • A61P25/22—Anxiolytics
    • 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 an extract from Piper methysticum G.
  • Forster which differs from the known extracts from this plant and offers various advantages in terms of action and recovery.
  • Extracts from Piper methysticum G are known, e.g. from WO 92/04036 and from EP-A-0 987 026 and have anxiolytic, anticonvulsive, muscle relaxant, anesthetic-potentiating, analgesic, sleep-inducing and neuroprotective effects.
  • the effects are attributed to the occurrence of Kavapyrone or Kavalactone, and in particular to Kavain, 7,8-Dihydrokavain, Methysticin, 7,8-Dihydromethysticin, Yangonin and 5,6-Desmethoxyyangonin.
  • Kavapyrone in their entirety are responsible for the pharmacological effects.
  • the pharmacological examinations were carried out on the one hand with synthetically produced kavapyrones or mixtures thereof or on the other hand with plant extracts, as in particular by R. Hansel in "Kava-Kava in Modern Pharmaceutical Research", Zeitschrift für Phytotherapie (Hippokrates Verlag Stuttgart) 17 (1996 ), 180-195, where the chemical structures of the active ingredients are also described
  • the plant material used to produce these known plant extracts are the roots or the dried rhizome of Piper methysticum G.
  • Forster also known as kava-kava rhizoma or kavarhizom
  • the roots attached to the rhizome or the secondary roots or a mixture of Rhizome parts, secondary roots and the so-called "kava peelings", ie the strip-like peeled, partly rolled-up, partly gray-brown, yellowish-yellow parts of the rootstock on the inside.
  • kava peelings ie the strip-like peeled, partly rolled-up, partly gray-brown, yellowish-yellow parts of the rootstock on the inside.
  • Suitable extraction methods are described in the literature cited above.
  • the chemical structures of the main components of extracts from the rootstock the plant mentioned are described in Chimia 52 (1998) 443.
  • a first embodiment of the extract according to the invention is defined in claim 1.
  • Preferred embodiments of the extract according to the invention have the features specified in claims 2-5.
  • Another general embodiment of the extract according to the invention has the features specified in claim 6, preferred embodiments having the features specified in claim 7.
  • the invention further a method with the specified in claim 8
  • Extract is understood to mean a substance which is obtained by extraction or maceration or percolation of the plant material with a suitable solvent and, if appropriate, subsequent either partial or complete removal of the solvent.
  • Extracts according to the present invention are either so-called evaporated to dryness Suitable extracts, maceration or percolation or the like are known to the person skilled in the art, such as acetone, chloroform, ethyl acetate, lower alcohols with 1 to 4 carbon atoms, preferably methanol and ethanol, or mixtures thereof Water is particularly suitable, and carbon dioxide in liquid or supercritical form as well as other pressurized liquid gases with solvent properties.
  • above-ground plant material from Piper methysticum G.
  • Forster is understood to mean fresh or dried material from the leaves and / or stems, which can be harvested from the plants without significantly impairing the ability to grow, even if to a considerable extent , for example up to 90% and typically about 50%, which has the advantage over extracts from root material that crops of this perennial plant can be harvested repeatedly without replanting, but this is not the only advantage of the extracts according to the invention from above-ground growing
  • the extract according to the invention can be processed together with the usual pharmaceutical auxiliaries to form capsules, (film) tablets, coated tablets or the like. So it is understood that pharmaceutical auxiliaries in particular fillers, binders, lubricants and / or coating agents, e.g. for film-coated tablets and coated tablets.
  • pharmaceutical preparations produced with the extract according to the invention can contain further active pharmaceutical ingredients.
  • the extract according to the invention or the medicaments produced therewith have anxiolytic, anticonvulsive, muscle relaxant, anesthetic-potentiating, analgesic, sleep-inducing, anti-inflammatory and / or neuroprotective effects.
  • the extract according to the invention can be used as such or post-processed e.g. for removing coloring flavocavine. This can be achieved, for example, by cold precipitation or by extraction in the presence of suitable adsorbents, such as particulate ⁇ -aluminum oxide, or by other known measures.
  • FIG. 1 shows the HPLC diagram of an extract of Piper methysticum G. Forster from leaf material according to the invention
  • FIG. 2 shows the corresponding HPLC diagram of a known extract of Piper methysticum G. Forster from root material.
  • FIG. 3 shows the HPLC diagram of a further extract according to the invention of Piper methysticum G. Forster (morphotype Nene) from leaf material; and
  • FIG. 4 shows the FIPLC diagram of a further extract according to the invention of Piper methysticum G. Forster (morphotype PNG) from leaf material.
  • the HPLC analysis for recording the diagrams in FIGS. 1 and 2 was carried out as follows: 500 mg of dried powdered leaves (for FIG. 1) or dried powdered rhizome of Piper methysticum G. Forster were sonicated twice with 30 ml of methanol each time Extracted for 10 minutes. The combined extracts of the respective samples were filtered and, after evaporation of the solvent, redissolved in 10 ml of methanol. For HPLC analysis, an aliquot was regenerated through a membrane
  • the samples were eluted with a mixture of 22 vol.% Acetonitrile, 18 vol.% Methanol and 60 vol.% Phosphoric acid (H 3 PO) at a flow rate of 0.8 ml / minute at 60 ° C.
  • the Kavalactone was identified by comparing the retention times and the UV spectra with authentic samples. The chromatograms of both extracts showed different peaks, which as
  • Kavalactones could be identified.
  • the leaf extract (Fig. 1) differs significantly from the root extract (Fig. 2). So there is no methysticin in the methanolic leaf extract and the proportions of the Kavalactone are clearly different in both extracts.
  • Dihydrometysticin and dihydrokavain predominate in the leaf extract compared to the root extract.
  • the leaf extract shows a characteristic additional peak, which is presumably significant and is completely absent from the root extract. -
  • the mobile phase consisted of two solvent systems with a flow rate of 0.6 ml min, namely a mixture (A) of 19 vol.% Acetonitrile, 80 vol.% Water and 1 vol.% H 3 PO on the one hand, and a mixture (B ) from 59 vol.% acetonitrile, 40 mvol.% methanol and 1 vol.% H 3 PO 4 on the other hand with a linear gradient (0 - 8 minutes 100 vol.% A, 8 - 30 minutes 50 vol.% A, 30 - 75 minutes 0 vol.% A). 10 ⁇ l were injected with an autosampler. The detection was carried out at UV / VIS 200-600 nm.
  • the identification of the compounds was carried out at 253 nm either by external standard methods or by the UV spectra. Rutoside, hyperoside, isoquertcitrin, quercitrin, quervetin (all from Roth, Germany), Kaempferol (Sigma and Fluka, Switzerland), amentoflavone (Extrasynthese, France) were used as external standards. Accuracy and selectivity were determined by analyzing the individual compounds and their mixture. The chromatograms of both extracts of Figures 3 and 4 are the same in different essential peaks, and comparably showed different peaks in the more lipophilic range.
  • extract from Piper methysticum G. Forster is characterized by an HPLC diagram, which essentially has the features of Figure 1.
  • plant material of Piper methysticum G preferably leaf material, growing above ground is used.
  • morphotypes preferably of this plant are used which have a sufficiently high active ingredient content through breeding.
  • the present invention is explained in more detail below with the aid of receptor-ligand interaction or binding studies.
  • the receptor-ligand interaction studies in particular illustrate the increased pharmacological effectiveness of extracts from leaf material from Piper methysticum G. Forster compared to extracts from root material of Piper methysticum G. Forster.
  • the leaves and the root material were harvested and dried with the aid of a ventilation dryer at 35 ° C. for a period of 48 hours.
  • the dried samples were pulverized and extracted twice with methanol in an ultrasonic bath for 15 minutes each. After the solvent had been spun in to dryness, the residues were again taken up in methanol and a concentration of 50 mg / ml was established.
  • the extracts obtained in this way were kept at -20 ° C. until used in the receptor studies and for HPLC analyzes. A methanol concentration of 2% was not exceeded in the receptor studies.
  • Table 1 lists the percentage of selected Kavapyrone based on the dry weight of the leaf and root material examined in the four cultivars of Piper methysticum G. Forster mentioned, which was determined by HPLC analysis. For this purpose, a Jasco-HPLC system was used, which was coupled to a diode array detector (Jasco-MD-910), the measurements being carried out on an analytical Spherisorb-5 ODS column (5 mm, 250 x 4.6 mm). The samples were eluted with a mixture of 22% acetonitrile, 18% methanol and 60% H 3 PO 4 (50 M) at a flow rate of 0.8 ml / minute at 60 ° C within 50 minutes.
  • Methysticin occurs in the root extracts on a similar scale to Kavain, ie between 1% and 2%, whereas it could not be detected in the leaf extracts.
  • the percentage of DHM and DHK is usually higher in the leaf extracts than in the root extracts. Exceptions are the Mahakea plant and the NG plant in the case of DHK.
  • the sum of the relative content of the six Kavapyrones based on the dry weight of the leaf extract is 2.4% for Purple Moi, 4.4% for PNG and 5.0% for Nene.
  • the sum of the relative content of the six Kavapyrones based on the dry weight of the root extract is in a range between 5.1% (for Purple Moi) and 9.1 (for M ⁇ h ⁇ ke ⁇ ).
  • GABA A and dopamine D 2 receptors the receptors used for the study were formed using the Semliki Forest Virus Expression System (hereinafter abbreviated as SFV).
  • SFV Semliki Forest Virus Expression System
  • Benzodiazepine receptors were made from rat cortex (rat cortex), GABA A receptors from rat cerebellum (rat cerebellum), and dopamine D 2 receptors from calf striatum (calf striatum).
  • Electroporation method introduced. After 24 hours, the recombinant virus particles were collected.
  • CHO-infected cells (CHO stands for Chinese hamster ovary) were washed within 16-48 hours after infection with 5 mM Hepes buffer pH 7.4, 2 mM EDTA and lysed in the same buffer for 20 minutes at 4 ° C. The lysed cells were transferred to 10 ml centrifuge tubes, centrifuged at 40,000 g for 15 minutes and in 50 mM Tris / HCl buffer pH 7.8, 1 mM EDTA and 5 mM MgCl 2 using a Polytron homogenizer . suspended again. After renewed Centrifugation at 40,000 g for 15 minutes, the sediment or pellet was collected and stored at -80 ° C.
  • the GABAA receptor was produced from rat brains by Wistar Ratten from Biological Research Laboratories Ltd., Bushingdorf, Switzerland. After isolation of the cerebellum, this was in a 50-fold volume of a Tris-HCl buffer (50 mM Tris-HCl, pH 7.4, 0.32 M sucrose, 1 mM EDTA 0.02% NaN 3 , and 0.1 mM PMSF) with a Polytron homogenizer over the Homogenized for 30 seconds, and then centrifuged at 4 ° C at 500 g for 10 minutes.
  • Tris-HCl buffer 50 mM Tris-HCl, pH 7.4, 0.32 M sucrose, 1 mM EDTA 0.02% NaN 3 , and 0.1 mM PMSF
  • the supernatant or the supernatant liquid was then diluted with twice the volume of the buffer and centrifuged again at 4 ° C., 18,000 g for 45 minutes. The supernatant thus obtained was discarded and the pellet washed twice with the buffer, the suspension being centrifuged under the same conditions for 30 minutes and the supernatant liquid being discarded to obtain the membrane pellet.
  • the benzodiazepine receptor was produced from cortex material from rat brains. This was then homogenized in 40-fold volume of a Tris-HCl buffer (15 mM Tris-HCl, pH 7.4, 118 mM NaCl, 4.8 mM KCl, 1.2 mM CaCl 2 , 1.2 mM MgCl 2 ) over a period of 30 seconds. The suspension was then further diluted with 120 times the volume of the buffer and centrifuged at 4 ° C, 18000 g for 10 minutes. After decanting the supernatant or the supernatant liquid, the membrane pellets were obtained.
  • Tris-HCl buffer 15 mM Tris-HCl, pH 7.4, 118 mM NaCl, 4.8 mM KCl, 1.2 mM CaCl 2 , 1.2 mM MgCl 2
  • the suspension was then further diluted with 120 times the volume of the buffer and centrifuged at 4 ° C, 18000 g for 10 minutes
  • the preparation of the dopamine D 2 receptor was carried out from the striatum of the calf brain, which was in 40 times the volume of a Tris-HCl buffer (50 mM Tris-HCl, pH 7.4, 0.1% ascorbic acid, 120 mM NaCl, 5 mM KCl, 2 mM CaCl 2 , 1 mM MgCl 2 ) was homogenized over a period of 60 seconds. The homogenate was then centrifuged at 4 ° C, 18000 g for 10 minutes. After decanting the supernatant or the supernatant liquid, the membrane pellets were obtained.
  • Tris-HCl buffer 50 mM Tris-HCl, pH 7.4, 0.1% ascorbic acid, 120 mM NaCl, 5 mM KCl, 2 mM CaCl 2 , 1 mM MgCl 2
  • the protein concentration was determined in all cases by the BCA method according to the report by P.K. Smith et al. in Analytical Biochemistry 150 (1985), 76-85.
  • the receptor-ligand interaction studies were repeated in triplicate (experiment 1-3) in a total volume of 500 ⁇ l among the in Table 2 conditions carried out.
  • the binding experiments were terminated by rapid filtration with a GF / C filter under reduced pressure and subsequent washing three times with ice-cooled 5 ml Tris HCl pH 7.4 buffer.
  • the radioactivity in the filter was determined by liquid scintillation analysis (Tri-Carb 2100 TR, Packard Bioscience Company).
  • the IC JO values were determined from curves which were based on the individual measurements and approximated to these (P ⁇ 0.01). They are to be understood as mean + standard deviation.
  • Mahakea leaf extract 510 ⁇ 35 68 ⁇ 4 4 ⁇ 1 19 ⁇ 5 240 ⁇ 30 36 ⁇ 7 4 ⁇ 1> 1000 127 ⁇ 32
  • IC50 inhibitory concentration, 50% of the specific binding are displaced.
  • the root extracts investigated were less strongly inhibited, where IC50 values in the range from 5 ⁇ g / ml (Nene) to 87 ⁇ g / ml (Mahakea) were determined.Histamine H 2 receptors for leaf extracts from Mahakea with an IC 50 value of approximately 4 were also able to inhibit very strongly ⁇ g / ml are observed, while the Mahakea root extracts only have an IC 50 value of approximately 806 ⁇ g / ml.
  • Leaf extracts also more strongly inhibit binding to dopamine D 2 , opioid, serotonin (5-HT 7 ) and histamine receptors (Hi and H 2 ) than
  • Root extracts So moderate to strong affinities of the leaf extracts could be determined (1 ⁇ IC50 values ⁇ 100 ⁇ g / ml), whereas the root extracts showed only weak activities with ICso values from 100 ⁇ g / ml to more than 1000 ⁇ g / ml. There are major differences in the inhibition of binding between the individual cultivars. The strongest inhibition at the histamine receptors (Hi and H 2 ) for the leaf extracts of the Mahakea and the lowest inhibition for the root extracts of the Purple Moi and Nene were detected.
  • Hi and H 2 histamine receptors
  • benzodiazepine and serotonin receptors (5-HT ⁇ and 5-HT 7 ) was only slightly inhibited by the extracts of Piper methysticum G. Forster.
  • the IC 50 values were 500 ⁇ g / ml and higher
  • Serotonin 5-HT ⁇ receptors even at> 1000 ⁇ g / ml.
  • the IC50 values for leaf extracts were between 127 ⁇ g / ml (Mahakea) and 395 ⁇ g / ml (Purple Moi).

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Neurology (AREA)
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  • Neurosurgery (AREA)
  • Microbiology (AREA)
  • Alternative & Traditional Medicine (AREA)
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  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Anesthesiology (AREA)
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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines Containing Plant Substances (AREA)

Abstract

L'invention concerne de l'extrait de <i>piper methysticum</i> G. Forster, obtenu à partir de parties aériennes de cette plante, notamment de feuilles. Cet extrait présente des avantages en termes d'action et d'extraction et se différencie nettement des extraits connus obtenus à partir de racines, selon l'analyse par chromatographie liquide à haute performance. Un tel extrait s'obtient par extraction de matière végétale aérienne de <i>piper methysticum</i> G. Forster, de préférence de feuilles et s'utilise pour des médicaments à effet anxiolytique, anticonvulsif, myorelaxant, potentialiseur de narcose, analgésique, somnifère, anti-inflammatoire et/ou neuroprotecteur.
EP01956248A 2000-07-26 2001-07-26 Extrait de plante Withdrawn EP1318825A2 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH147600 2000-07-26
CH14762000 2000-07-26
PCT/CH2001/000462 WO2002007743A2 (fr) 2000-07-26 2001-07-26 Extrait de plante

Publications (1)

Publication Number Publication Date
EP1318825A2 true EP1318825A2 (fr) 2003-06-18

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP01956248A Withdrawn EP1318825A2 (fr) 2000-07-26 2001-07-26 Extrait de plante

Country Status (4)

Country Link
US (1) US20030180395A1 (fr)
EP (1) EP1318825A2 (fr)
AU (1) AU2001278341A1 (fr)
WO (1) WO2002007743A2 (fr)

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US20220110852A1 (en) * 2020-10-14 2022-04-14 Chanda Zaveri Pigment Stabilizers
CN115006314B (zh) * 2022-07-11 2023-07-11 科乐美(广州)生物科技有限公司 一种卡瓦胡椒提取物及其制备方法和应用

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