EP1951376A2 - Durch ein extraktionsverfahren mit lösungsmitteln pflanzlichen ursprungs erhaltener pflanzenextrakt - Google Patents

Durch ein extraktionsverfahren mit lösungsmitteln pflanzlichen ursprungs erhaltener pflanzenextrakt

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Publication number
EP1951376A2
EP1951376A2 EP06831106A EP06831106A EP1951376A2 EP 1951376 A2 EP1951376 A2 EP 1951376A2 EP 06831106 A EP06831106 A EP 06831106A EP 06831106 A EP06831106 A EP 06831106A EP 1951376 A2 EP1951376 A2 EP 1951376A2
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EP
European Patent Office
Prior art keywords
solvent
mixture
plant
limonene
solvents
Prior art date
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Application number
EP06831106A
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English (en)
French (fr)
Inventor
Hervé André Gérard DURAND
Fabien Durand
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Laboratoire Limotech
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Laboratoire Limotech
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Publication of EP1951376A2 publication Critical patent/EP1951376A2/de
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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)
    • A61K36/88—Liliopsida (monocotyledons)
    • A61K36/906—Zingiberaceae (Ginger family)
    • A61K36/9066—Curcuma, e.g. common turmeric, East Indian arrowroot or mango ginger
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9755—Gymnosperms [Coniferophyta]
    • A61K8/9767—Pinaceae [Pine family], e.g. pine or cedar
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783—Angiosperms [Magnoliophyta]
    • A61K8/9789—Magnoliopsida [dicotyledons]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783—Angiosperms [Magnoliophyta]
    • A61K8/9794—Liliopsida [monocotyledons]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin

Definitions

  • Vegetable extract obtained by a process of extraction using solvents of vegetable origin
  • the invention relates to the field of processes for extracting active compounds from raw materials of natural origin used in the formulation of pharmaceutical, cosmetic or food compositions and / or organic chemistry and in particular the chemistry of the parent compounds natural.
  • Plants and natural products are the source of molecules that can be used as extracts in many areas: pharmaceutical, cosmetic or food. It can be therapeutic extracts (active ingredients of vegetable origin: digitalis, morphine ... etc.), presenting a particular cosmetic activity
  • Drying has certainly been the first means used to conserve plant activity, but this technique does not allow to concentrate or preserve the active compounds of oxidation.
  • Hydrodistillation or steam distillation is a conventional technique limited to the extraction of essential oils. This process uses a large amount of energy to produce the vapor that causes the volatile compounds and the water required to condense the vapors is discharged as hot effluent also causing energy losses.
  • the essential oils thus obtained are subjected to temperatures close to 100 ° C. and the components sensitive to heat or hydrolysis are often altered.
  • Extraction using synthetic organic solvents or from petrochemical refining processes is the method that is of the greatest importance from an industrial point of view because of the standardization of methods, the requirement of reproducibility and of characterization of the extracts obtained.
  • organic solvents conventionally used, mention may also be made of glycol ethers, hexane, ether, acetone, methylene chloride, alcohols, aliphatic or aromatic hydrocarbons, chlorinated and fluorinated solvents or synthetic molecules such as N-methylpyrrolidone or dimethoxymethane, for example.
  • Synthetic solvents such as perchlorethylene, methylene chloride, chlorinated solvents and certain fractions derived from petroleum such as hexane have been widely used for the extraction of flavors, fragrances, dyes and active principles of plants.
  • these organic solvents are particularly targeted by international regulations which impose very low residual solvent contents (of the order of 1 to 5 ppm).
  • These regulations that limit or prohibit their use for food or therapeutic applications involve costly reprocessing to remove residual solvents, such as additional heating, and the active ingredients can be degraded.
  • the chemical nature of these solvents can render the active products unstable.
  • Alcoholic or hydro-alcoholic extraction allows the production of hydrophilic compounds, but does not allow the efficient extraction of apolar lipophilic compounds and can lead to the extraction of undesirable compounds such as tannins which are highly water-soluble.
  • a process for extracting organic compounds with therapeutic activity contained in the plants and products thus obtained is known from Le GaII (Patent FR 77 36976), characterized in that a plant previously ground with natural essences taken from the ground is treated. group that includes the essence of citral, the essence of bergamot, the essence of mint and the essence of rosemary.
  • the essence used for plant extraction is previously distilled by steam distillation under reduced pressure, so as to use only the low-boiling fraction, ie the fraction distilling at most at 95 ° C under 20 mm of mercury but this fraction is nevertheless composed of a mixture of uncharacterized chemical entities resulting in the impossibility of characterizing the extract and obtaining a purified extract by removal of the residual solvent. This elimination is, moreover, neither described nor suggested.
  • the high-boiling liquid is mixed with a light solvent of known type to carry out the extraction, said light solvent being either a solvent of synthesis, either from petrochemicals.
  • Pisacane PCT patent application WO 01/07135 A2
  • a process for extracting flowers and plants from the chrysanthemum family and the family Helianthus to produce insecticidal substances Said insecticidal substances are pyrethrins, hydrophope compounds and insoluble in water.
  • the method described uses solvents extracted from plants such as terpenes in a maceration phase at room temperature (20 ° C), for about ten minutes, with mechanical stirring. After this maceration phase, the solid residue is filtered and optionally the solvent can be removed or reduced by evaporation or distillation, but can be retained for use as a carrier or carrier of the activity after formulation.
  • ROSENBERG M. et al (Carotenoid base food dye extracted from orange peel by d-limonene-extraction-process and use) discloses a method for extracting carotenoids at two stages (2 minutes each) at a temperature of 20 ° C. C, in which butylated hydroxytoluene (BHT), a synthetic substance, was added to d-limonene as an extraction solvent.
  • BHT butylated hydroxytoluene
  • the present invention makes it possible to satisfy these needs and consists of an alternative method for extracting and purifying lipophilic and / or partially polar molecules using a solvent and / or a mixture of solvents of plant origin whose constituents are characterized and chemically defined.
  • solvent will be used and it will include both plant-derived solvents (these will be isolated and pure molecules) and both solvent mixtures of plant origin whose constituents are characterized, that is, all identified, and chemically defined, that is, pure.
  • the extraction is made from plant material that can be very varied. They may be leaves, stems, roots, rootlets, rhizomes, flowers, flower heads, seeds, seeds, stones, seeds, bark, fragments of trunks. of various plant species, which may have previously been dried and / or crushed and / or mixed ... These can be used alone or as a mixture.
  • the process makes it possible to obtain extracts rich in lipophilic molecules but surprisingly and unexpectedly, it also allows the concomitant extraction of polar-type molecules that participate in the activity of the cells. whole plants.
  • the present invention relates to a plant extract obtained by a single-phase extraction process, characterized in that it comprises the following steps:
  • a mixture of solvents, said solvent and / or at least one of the constituents of said solvent mixture being selected from the group consisting of terpene solvents, having a purity of at least 98%, and being poor in peroxides.
  • the present invention relates to a plant extract obtained by a single-phase extraction process as described above, characterized in that it is free of polyphenol, anthocyanin and / or tannin and that it comprises a fraction of lipophilic compounds and / or a fraction of polar compounds.
  • the extract comprises at most 0, 1% tannins.
  • the tannins are water-soluble phenolic compounds having a molecular weight of between 500 and 3000 which, besides conventional phenol reactions, have the property of precipitating alkaloids, gelatin and other proteins.
  • These polyphenols (or phenol polymers) are mainly polyesters of gallic and ellagic acids.
  • hydrophilic compounds are often troublesome during the extraction phases, such as anthocyanins, which are proanthocyanidol polymers.
  • the invention also relates to an extract as defined above, characterized in that the compounds having a lipophilic character are chosen in particular from unsaponifiable compounds.
  • Unsaponifiables are the non-glyceride constituents of oils. They represent 0.3 to 2% of the oils: they are hydrocarbons, carotenoids, sterols (sitosterol, stigmasterol, campesterol), tocopherols (vitamin E), aliphatic alcohols of high molecular weight, terpene alcohols.
  • lipophilic compounds By way of example, mention may be made of the following lipophilic compounds:
  • beta sitosterol, campesterol, stigmasterol, cholesterol and their derivatives for example green coffee extracts,
  • curcumin and curcuminoids for example extracted from turmeric, carotenoids for example carrot extracts, lycopene, for example tomato extract,
  • sesquiterpene lactones and helenanine for example extracts from Arnica
  • parthenolides and flavonoids aglycones for example extracts of feverfew. It also relates to an extract as defined above, characterized in that the polar-type compounds are chosen from alkaloids, neoxanthines, glycosylated xanthones, flavonoids or glycosylated flavonoids.
  • Alkaloids include caffeine, theophylline and / or theobromine.
  • glycosylated xanthones mention may be made of Gentian gentioside.
  • glycosylated flavonoids mention may be made of the apigenin glycoside of feverfew.
  • the invention relates to a plant extract, directly obtained by means of a process as described above, characterized in that it comprises at most 0.1% of tannins.
  • turmeric extract characterized in that it comprises at least 8% of curcuminoids and at most 0.1% of tannins. It also relates to an extract of Arnica montana flowers characterized in that it comprises at least 5% of sesquiterpene lactones expressed in helenanine and at most 0.1% of tannins.
  • celandine extract characterized in that it comprises at least 0.75% of total alkaloids expressed as chelidonine or crystals of chelidonine hydrochloride and at most 0.1% of tannins.
  • Gentian extract characterized in that it comprises at least 3% of free xanthones with at least 0.5% of gentioside and at most 0.1% of tannins.
  • the present invention also relates to a feverfew extract characterized in that it comprises at least 0.83% of parthenolides, flavonoids aglycones, apigenin glucosides and at most 0.1% of tannins.
  • the present invention also relates to a single-phase extraction process characterized in that it comprises the following steps:
  • said solvent and / or at least one of the constituents of said solvent mixture being chosen from the group consisting of terpene solvents, having a purity of at least equal to 98%, and being poor in peroxides.
  • the step of contacting the plant material with the solvent and / or solvent mixture is a maceration of the plant material with the solvent and / or mixture of solvents. It can also be a soaking, spraying ...
  • the step of removing the plant material is a filtration of the plant material.
  • the constituent (s) of the solvent according to the present invention are characterized: the solvent is of plant origin and it is composed of terpenes which are all identified.
  • Terpenic solvents are a class of isoprenoidal hydrocarbons that are the main constituents of many species of plants or essential oils.
  • the precursor of all terpenes is mevalonic acid.
  • All terpenes can be formally decomposed into isoprenic units.
  • the main terpenes are pinene, camphene and limonene, and their isomers, but also terpenes of orange, pine and their oxygenates, linalool or terpineol, for example, or paramenthane.
  • the invention therefore relates to a single-phase extraction process with a solvent and / or a mixture of solvents of vegetable origin, characterized in that the solvent and / or Solvent mixture is an isomer or mixture of limonene isomer and / or pinene alone or in admixture.
  • the solvent used is a mixture of d-limonene and alpha-pinene. In one embodiment, the solvent used is a mixture of d-limonene and alpha-pinene, with at least 50% of d-limonene.
  • the mixture comprises 70% d-limonene and 30% alpha-pinene.
  • ethanol may be used in admixture with at least one terpene solvent.
  • the solvents used will be binary or ternary mixtures, for example:
  • alpha-pinene / 95% ethanol 70% / 30%
  • d-limonene / alpha-pinene / 95% ethanol 50% / 20%
  • D-Limonene is a natural compound of the family of monoterpenes which is present in quantity in citrus zest. It is a by-product of the fruit juice industry. In this sense, it is abundant and cheap. This monoterpene is also a hydrocarbon with very high solvent power.
  • Alpha-pinene is also produced in large quantities from pine (turpentine) species by the wood and paper industry.
  • the d-limonene and alpha-pinene used refer to isolated and characterized molecules. These are not the trade names of commonly used d-limonene and alpha-pinene. Indeed, from the fruit juice industry, the wood industry or the deterpenation of essential oils, the by-products, which are often mixtures of different terpenes actually containing a significant part of d-limonene or alpha-pinene, are often marketed under the improper name "d-limonene” and "alpha-pinene” because they are actually mixtures of various terpenes which also contain many impurities (impurities from transport, derivatives oxides, waxes, greases and other non-volatile residues, peroxides). These solvents are used in the prior art to prepare extracts or products having low degrees of purity.
  • d-limonene and the term “alpha-pinene” denote chemically defined solvents with reference to the chemical nature of said molecules, which are isolated and characterized to a degree of purity close to 100%, less than 98%.
  • the industrial-grade d-limonene and alpha-pinene can easily be purchased for example from the following companies: Capua Sri, Campo Calabro, Italy or Resin and Terpenic Derivatives, Dax, France, these same organic-grade solvents can be purchased from companies such as Montecitrus, Monte Azul Paulista, Brazil or Sirius, Paris, France with a purity of at least 98%.
  • the solvents from these industrial sources contain in particular a small part of impurities consisting of oxidation products of d-limonene or alpha-pinene which represents between 0.3 and 0.6% by weight of the products.
  • this non-volatile fraction at 40 ° C. at atmospheric pressure may or may not be eliminated, for example by azeotropic distillation of d-limonene or alpha-pinene with water vapor, which allows obtain solvents that are at least 98% pure or at least 99% pure, or even 99.95% pure.
  • the constituent or constituents of the solvent according to the present invention are chemically defined: the terpene solvent used according to the present invention has a very high degree of purity and a very low content of peroxides.
  • the solvent and / or the constituent (s) of the solvent mixture has undergone a preliminary purification step.
  • This purification step may for example be chosen from azeotropic entrainment with water vapor or by evaporation under vacuum.
  • the terpene solvent and / or at least one of the constituents of the solvent mixture has a degree of purity of at least 98%.
  • the purity level is greater than or equal to 99%. In a particular example, the purity level is 99.95%.
  • the terpene solvent and / or at least one of the constituents of the solvent mixture is also very low in peroxides. This characteristic is fundamental because the formation of peroxides - which occurs during any mixing or heating operation during the extraction steps - is initiated by the peroxides already present in the solvent. These same peroxides can alter the compounds of interest.
  • the higher the terpene solvent is initially rich in peroxides the more it will tend to degrade (radical runaway effect).
  • the more initially the solvent will be poor in peroxides the less it peroxidated during extraction and more easily it can be recycled at the end of the process.
  • the peroxide content is less than 15 mEQ / kg. In another embodiment, the peroxide content is less than 1 1, 1 mEQ / kg.
  • the nonvolatile residue level is also very low. In one embodiment, this rate is less than 0.1%. In another embodiment, this rate is less than 0.01%.
  • Solvents of plant origin whose constituent (s) are characterized and chemically defined are biodegradable, non-flammable, non-toxic and environmentally friendly. In addition, they are easy to use: dilutable and rinsable with water with conventional surfactants.
  • terpenic solvents can be eliminated by various techniques: by azeotropic steam entrainment at 35 ° C. under vacuum (15 mmHg) 2000 Pa.
  • the injection of vapor into the filtrate makes it possible to elimination of 97.26 to 99.99% of d-limonene and 98.2 to 99.99% of alpha-pinene;
  • the invention therefore also relates to the process according to the invention characterized in that the step of removing the solvent is a azeotropic steam distillation step.
  • the invention also relates to the process according to the invention characterized in that the step of removing the solvent is a molecular distillation under vacuum.
  • the process according to the invention is carried out with proportions by weight plant material / solvent (plant material / monoterpene hydrocarbon) of 1/4 to 1/10.
  • the extraction temperature is between 40 and 45 ° C.
  • the duration of maceration can be about
  • a microwave irradiation step is performed during maceration. This step can be performed at 100 W for 2 minutes 30 seconds. This allows a reduction of the extraction time.
  • EXAMPLE 1 Simultaneous Extraction of Unsaponifiable Compounds and Caffeine from Green Coffee and Removal of the Solvent at Low Temperature by Azeotropic Conduction with Vacuum Water Vapor Green Coffee usually contains 14% fat, 0.1% unsaponifiable compounds and at least 1% caffeine. 1.5 kg of green coffee beans of biological quality and milled in 15 liters of d-limonene are macerated for 3 h 30 with stirring at 40 ° C. (vegetable material / solvent ratio: 1/10).
  • the particles are removed by filtration to obtain a charged solution of compounds of interest which is then removed d-limonene by azeotropic entrainment with water vapor.
  • the entire device is placed under vacuum (10-40 mmHg or 1300-5300 Pa), which allows to considerably lower the temperatures used and facilitates the evaporation of the solvent: a boiler makes it possible to produce steam of water at 30 ° C. which is injected at the surface or into the extract to be desolventized, itself heated to 45 ° C.
  • the d-limonene is vaporized and then recycled using a condenser maintained at 0 ° C. for subsequent extraction operations while the unsaponifiable compounds are recovered in the extractor.
  • Solvent 4 d-Limonene Biological Grade 14.07%
  • Solvent 5 Alpha-Pinene 13.65%
  • Solvent 6 Alpha-Pinene Biological Grade 14.72%
  • Solvent 7 Limonene / alpha-pinene mixture 70/30 (v / v): 14.52%
  • the extraction yields obtained with monoterpene hydrocarbons are better than that obtained with hexane.
  • the best extraction yields are obtained with the biological alpha-pinene, the mixture of limonene / alpha-pinene 70/30 (v / v), the biological d-limonene, the mixture of limonene / alcohol 95 ° in 70/30 mixture (v / v).
  • a synergistic effect of the solvent mixture d-limonene / alpha-pinene 70/30 (v / v) is observed.
  • the extracts thus obtained contain less than 0.05% of residual solvent, this limit not being acceptable for the extract obtained with hexane.
  • Solvent 1 0.815% undetectable Solvent 2 0.895% 2.53% Solvent 3 0.825% 3.68% Solvent 4 0.912% 2.47% Solvent 5 0.789% 2.64% Solvent 6 0.805% 2.74% Solvent 7 0.952% 3.98%
  • the above method therefore makes it possible to selectively extract unsaponifiable compounds and caffeine and to concentrate them.
  • This exemplary embodiment demonstrates one of the characteristics of the invention, that is to say that monoterpene hydrocarbons allow the concomitant extraction of compounds of a lipophilic nature (for example, unsaponifiables) and polar-type compounds (for example: caffeine) and their concentration, while excluding other components (polyphenols, tannins) yet present in large quantities in the raw material.
  • the process according to the invention effectively allows the selective extraction of lipophilic compounds and intermediate polarity.
  • the resulting extract rich in unsaponifiable compounds and caffeine can be directly integrated into dermopharmaceutical formulations, thereby reducing the solubilization steps often required when introducing active ingredients into topical formulations.
  • EXAMPLE 2 Simultaneous extraction of unsaponifiable compounds and caffeine from green coffee and removal of the solvent at low temperature under vacuum in the absence of water.
  • EXAMPLE NO. 3 Extraction of curcuminoids from turmeric, according to the process of the invention in comparison with an extraction method using hexane.
  • Turmeric rhizomes (Curcuma longa L.) contain 8% curcuminoids. 1 kg of finely ground biological quality turmeric powder is macerated in 10 liters of d-limonene for 3 h 30 with stirring at 40 0 C (plant material / solvent ratio: 1/10).
  • the particles are removed by filtration to obtain a highly colored solution of orange, which is then removed d-limonene by azeotropic driving with water vapor as described in Example 1.
  • Solvent 4 d-Limonene Biological Grade 8.36%
  • Solvent 5 Alpha-Pinene 8
  • Solvent 6 Alpha-Pinene Biological Grade 8.55%
  • Solvent 7 Imonene / alpha-pinene mixture 70/30 (v / v): 8.85%
  • the extraction yields obtained with monoterpene hydrocarbons are better than that obtained with hexane.
  • the best extraction yields are obtained with the biological alpha-pinene, the mixture of limonene / alpha-pinene 70/30 (v / v), the biological d-limonene, the mixture of limonene / alcohol 95 ° in 70/30 mixture (v / v).
  • a synergistic effect of the mixtures of limonene / alpha-pinene 70/30 (v / v) is observed.
  • the extracts thus obtained contain less than 0.05% of residual solvent, this limit not being acceptable for the extract obtained with hexane.
  • the above method therefore makes it possible to selectively extract the curcuminoids and to concentrate them.
  • Turmeric only one extraction stage is necessary. It is also possible to extract curcuminoids from turmeric using a continuous countercurrent extraction device.
  • the antioxidant activity of the Turmeric extract obtained with the solvent n ° 2 (d-limonene) was studied using the xanthine / xanthine oxidase test according to the method adapted from RICE EVANS et al (Techniques in free radical research, 1991, Elsevier, Paris) and (MASAKI et al., Antioxygen scavenging activity of plant extracts, Biol Pharm Bull, 1995, 18 (1),
  • Arnica montana flower heads contain 0.4% lactonic sesquiterpenes (0.2-0.5% helenanine in the plant) that are responsible for the anti-inflammatory and healing activity of Arnica .
  • 200 g Arnica montana flower heads (Arnica montana.) Are macerated whole and of biological quality in 5 liters of d-limonene for 3:30 with stirring at 40 ° C. (ratio plant material / solvent:
  • Solvent 3 Blend of limonene / alcohol 95 ° mixed 70/30 (v / v) 9.48%
  • Solvent 4 d-Limonene Biological Grade 10.38%
  • Solvent 6 Alpha-Pinene Biological Grade 9.1 1%
  • Solvent 7 Limonene / alpha-pinene mixture 70/30 (v / v): 10.47%
  • the extracts thus obtained contain less than 0.05% of residual solvent, this limit not being acceptable for the extract obtained with hexane.
  • the tannin content determined by the method described in the European Pharmacopoeia 5,02 package "Determination of tannins in vegetable drugs (2.8.14.)" Is less than 0.1%.
  • the above method therefore makes it possible to selectively extract the sesquiterpene lactones and to concentrate them.
  • a cylindrical glass cell around which microwave generators (2000-3000 Mhz) are placed is filled with 10 g of coarsely ground green coffee and 50 g of d-limonene.
  • the cell receives microwave power of 100 W for 2 minutes 30 seconds.
  • the solution which is maintained at a temperature below 40 0 C is colored quickly in green-brown and is filtered.
  • the d-limonene is removed as described in Example 2.
  • the extract thus obtained contains 0.917% of unsaponifiable compounds and 2.51% of caffeine.
  • EXAMPLE 7 Extraction of sesquiterpene lactones from Arnica in a reduced time by the process according to the invention and irradiation by means of microwaves.
  • EXAMPLE 8 Extraction of alkaloids of celandine (Chelidonium majus) by the method according to the invention.
  • the particles are removed by filtration to obtain a charged solution of compounds of interest which is then removed d-limonene in the absence of water by ultra-high vacuum rectification (133.2 Pa) as described in Example 2.
  • EXAMPLE NO. 1 Extraction of Free Xanthones from Gentian by a Process According to the Invention
  • Gentiana lutea 100 g of Gentian rhizomes (Gentiana lutea) are macerated
  • the tannin content determined by the method described in
  • This exemplary embodiment again demonstrates a characterization of the invention, that is to say that monoterpene hydrocarbons allow the concomitant extraction of lipophilic compounds (example: xanthones) and polar compounds (example: glycosides ), their concentration, while excluding the other components (for example, iridoid responsible for the bitterness of gentian extracts) yet present in large quantities in the raw material.
  • monoterpene hydrocarbons allow the concomitant extraction of lipophilic compounds (example: xanthones) and polar compounds (example: glycosides ), their concentration, while excluding the other components (for example, iridoid responsible for the bitterness of gentian extracts) yet present in large quantities in the raw material.
  • This method effectively allows the selective extraction of lipophilic compounds and compounds having an intermediate polarity.
  • the xanthonic compounds and the glycosylated forms thus extracted from gentian can easily be incorporated into oral administration forms in humans and without bitterness.
  • the flower heads of Tanacetum parthenium contain 1.5% sesquiterpene lactones (mainly parthenolide) which are responsible for the anti-migraine activity of Feverfew. 100 g of flowering buds of Grande are macerated
  • the particles are removed by filtration to obtain a solution very strongly colored yellow, which is then removed d-limonene by azeotropic driving with water vapor as described in Example 1.
  • the examples above can be applied to many other plants, for example Liquorice, Ginger and Serenoa repens, without this list being limiting.
  • the extracts according to the invention can be easily integrated in pharmaceutical or cosmetic compositions, liquid or semi-liquid in order to be in the pharmaceutical forms commonly used in human medicine and prepared according to the usual methods.
  • the extract (s) according to the invention may be incorporated into excipients usually employed in pharmaceutical compositions, such as aqueous or non-aqueous vehicles, various wetting agents, preservatives, thickeners.
  • the subject of the present invention is also pharmaceutical and / or cosmetic compositions comprising, as active ingredient, an extract according to the invention and / or the process for the preparation of said compositions, characterized in that the mixture is mixed according to known methods. in themselves, the extract (s) according to the invention with acceptable excipients or solvents, in particular pharmaceutically or cosmetically acceptable solvents.
  • extraction using solvents of plant origin whose constituent (s) are characterized and chemically defined, such as, for example, monoterpene hydrocarbons of biological quality, said extraction is a new alternative technical solution for non-vapor-drivable molecules as well as than supercritical CO2 extraction, and it is effective for a fairly wide range of molecules used in cosmetics and pharmacy.
  • the extracts obtained according to this process comprise compounds which have a lipophilic character or an intermediate polarity.

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  • Natural Medicines & Medicinal Plants (AREA)
  • Epidemiology (AREA)
  • Botany (AREA)
  • Birds (AREA)
  • Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • Microbiology (AREA)
  • Mycology (AREA)
  • Chemical & Material Sciences (AREA)
  • Medical Informatics (AREA)
  • Alternative & Traditional Medicine (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Dermatology (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Extraction Or Liquid Replacement (AREA)
  • Compounds Of Unknown Constitution (AREA)
  • Cosmetics (AREA)
EP06831106A 2005-11-10 2006-11-10 Durch ein extraktionsverfahren mit lösungsmitteln pflanzlichen ursprungs erhaltener pflanzenextrakt Ceased EP1951376A2 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0511451A FR2892933B1 (fr) 2005-11-10 2005-11-10 Extrait vegetal obtenu par un procede d'extraction a l'aide de solvants d'origine vegetale
PCT/FR2006/002506 WO2007057549A2 (fr) 2005-11-10 2006-11-10 Extrait vegetal obtenu par un procede d'extraction a l'aide de solvants d'origine vegetale

Publications (1)

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EP1951376A2 true EP1951376A2 (de) 2008-08-06

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EP06831106A Ceased EP1951376A2 (de) 2005-11-10 2006-11-10 Durch ein extraktionsverfahren mit lösungsmitteln pflanzlichen ursprungs erhaltener pflanzenextrakt

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US (1) US20090306386A1 (de)
EP (1) EP1951376A2 (de)
FR (1) FR2892933B1 (de)
WO (1) WO2007057549A2 (de)

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FR2926190B1 (fr) * 2008-01-14 2013-07-05 Thiomed Procede de preparation d'extraits vegetaux permettant l'obtention d'une nouvelle forme galenique
FR2939689B1 (fr) * 2008-12-15 2015-09-04 Valagro Carbone Renouvelable Procede d'extraction d'un compose mineur d'un corps gras, notamment d'une huile vegetale ou animale ou de leurs co-produits au moyen de terpene.
EP2260856A1 (de) 2009-05-12 2010-12-15 URSAPHARM Arzneimittel GmbH Immunstimulatorische Zusammensetzung mit einem Extrakt aus Arona S. in Kombination mit Selen und/oder Zink
FR2986534B1 (fr) 2012-02-07 2014-06-27 Univ D'avignon Et Des Pays De Vaucluse Procede d'enrichissement d'un corps gras en carotenoides
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CN103908478B (zh) * 2014-04-15 2016-08-31 中国农业科学院兰州畜牧与兽药研究所 黄花补血草总鞣质的提取方法
CN104398542B (zh) * 2014-10-30 2017-11-07 厦门大学 一种从含有黄酮的植物中提取与纯化黄酮的方法
US20170095467A1 (en) * 2015-10-01 2017-04-06 Rhizofeed, LLC Encapsulation of isoquinoline alkaloids
FR3042498A1 (fr) * 2015-10-14 2017-04-21 Naturex Nouveau solvant d'extraction et/ou de solubilisation organique, procede d'extraction mettant en oeuvre ledit solvant, et extraits issus dudit procede
CN105541856B (zh) * 2015-12-24 2018-01-09 利穗科技(苏州)有限公司 利用层析技术提取血根碱和白屈菜红碱的方法
CN106008432A (zh) * 2016-06-12 2016-10-12 王伟明 从桄榔果实中制备白屈菜酸盐的方法
IT201800005451A1 (it) * 2018-05-16 2019-11-16 Procedimento per la preparazione di una composizione farmaceutica da substrati organici e composizione cosi' ottenuta
CN109439433A (zh) * 2018-11-11 2019-03-08 陕西海升果业发展股份有限公司乾县分公司 一种提高天然果蔬香精醛类、酯类的生产方法
FR3110422B1 (fr) * 2020-05-19 2023-03-17 Int Flavors & Fragrances Inc Absolue de Lavandula pour son utilisation cosmétique
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MA61739B1 (fr) * 2023-08-08 2025-07-31 Les Conserves De Meknes Solvant éthano-terpénique, son procédé d’obtention et ses utilisations

Also Published As

Publication number Publication date
US20090306386A1 (en) 2009-12-10
FR2892933B1 (fr) 2010-11-05
WO2007057549A2 (fr) 2007-05-24
WO2007057549A3 (fr) 2007-10-18
FR2892933A1 (fr) 2007-05-11

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