WO2008142267A2 - Process for extracting coumarins - Google Patents

Process for extracting coumarins Download PDF

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Publication number
WO2008142267A2
WO2008142267A2 PCT/FR2008/000462 FR2008000462W WO2008142267A2 WO 2008142267 A2 WO2008142267 A2 WO 2008142267A2 FR 2008000462 W FR2008000462 W FR 2008000462W WO 2008142267 A2 WO2008142267 A2 WO 2008142267A2
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Prior art keywords
extract
plant
agent
polar solvent
solvent
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PCT/FR2008/000462
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French (fr)
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WO2008142267A3 (en
Inventor
Luc Darbonne
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Darome
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Priority to EP08787901A priority Critical patent/EP2271336A2/en
Publication of WO2008142267A2 publication Critical patent/WO2008142267A2/en
Publication of WO2008142267A3 publication Critical patent/WO2008142267A3/en

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/365—Lactones
    • A61K31/366—Lactones having six-membered rings, e.g. delta-lactones
    • A61K31/37—Coumarins, e.g. psoralen
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
    • A01N65/08—Magnoliopsida [dicotyledons]
    • A01N65/10—Apiaceae or Umbelliferae [Carrot family], e.g. parsley, caraway, dill, lovage, fennel or snakebed
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
    • A01N65/08—Magnoliopsida [dicotyledons]
    • A01N65/12—Asteraceae or Compositae [Aster or Sunflower family], e.g. daisy, pyrethrum, artichoke, lettuce, sunflower, wormwood or tarragon
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
    • A01N65/08—Magnoliopsida [dicotyledons]
    • A01N65/22—Lamiaceae or Labiatae [Mint family], e.g. thyme, rosemary, skullcap, selfheal, lavender, perilla, pennyroyal, peppermint or spearmint
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • 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)
    • A61K36/23—Apiaceae or Umbelliferae (Carrot family), e.g. dill, chervil, coriander or cumin
    • 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)
    • A61K36/28—Asteraceae or Compositae (Aster or Sunflower family), e.g. chamomile, feverfew, yarrow or echinacea
    • 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)
    • A61K36/28—Asteraceae or Compositae (Aster or Sunflower family), e.g. chamomile, feverfew, yarrow or echinacea
    • A61K36/282—Artemisia, e.g. wormwood or sagebrush
    • 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)
    • A61K36/53—Lamiaceae or Labiatae (Mint family), e.g. thyme, rosemary or lavender
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs

Definitions

  • the present invention relates to the field of coumarin extraction. It particularly relates to processes for extracting at least one coumarin from a plant part, the extracts obtained by these processes, compositions comprising said extracts and their uses.
  • Coumarins cover more than a thousand identified compounds of type 2H-1-benzopyran-2-ones.
  • Examples of coumarins include coumarin, warfarin, umbelliferone, esculetol, scopoletol and herniarine.
  • compositions enriched with herniarine are generally obtained by chemical synthesis and / or by extraction methods. This may require many steps, involving the use of solvents and / or reagents that may be difficult and dangerous to handle and quite expensive.
  • Said methods of the invention essentially use water as extraction solvent. It should be noted that in addition to solving the problems mentioned above, the use of water in a coumarin extraction process was not obvious insofar as these compounds are known in the art as n ' being not (eg warfarin) or weakly (eg coumarin) soluble in water.
  • the extraction yield could be optimized by playing on the following three parameters: the addition to water of a minimal amount of another polar solvent, preferably an alcohol, the extraction temperature, and / or the extraction time.
  • the subject of the invention is an extraction method comprising at least the following steps:
  • the term "part of a plant” means an element of the structure of a plant, in particular the root, the stem, the bark, the seed, the fruit, the leaf, the head and / or the flower.
  • the term “at least a part of plant” one can also hear a whole plant.
  • the plant part is milled, pulverized and / or minced.
  • the plant may be chosen from the group of asteraceae, lamiaceae, labiae and umbelliferae and in particular Arternisia dracunculus, Satureja hortensis, Anthriscus cerefolium, Anethum graveolens, Thymus vulgaris.
  • the extract may also include garlic, chives (allium schoenoprasum, wild garlic (allium ursinum), garlic (allium sativum).
  • extract means a composition obtained from a plant by a physical and / or chemical operation, in particular by extraction of at least a part of the plant with at least one solvent.
  • said extract is: sterilized, in particular by heating with or without pressure and / or by passage over a membrane; and / or disinfected, in particular by heating with or without pressure and / or by at least one disinfecting agent.
  • said extract comprises herniarine in particular in a content ranging from 0.1% to 30%, preferably from 0.5 to 15%, more preferably from 1 to 5% by weight relative to the weight of the plant. dried.
  • dry plant or “plant in the dry state” is meant a plant whose weight, after passing for 5 hours in an oven at 105 ° C., varies from less than 5% by weight relative to the weight before the last one. passage to the oven.
  • Said extract may further comprise at least one other coumarin, in particular warfarin.
  • coumarin refers to 2H-1-benzopyran-2-one compounds.
  • Examples of coumarins are coumarin (1,2-benzopyrone), warfarin (4-hydroxy-3- (3-oxo-1-phenylbutyl) coumarin), umbelliferone (7-hydroxycoumarin) , esculetol (6,7-dihydroxycoumarin), scopoletol (6-methoxy-7-hydroxycoumarin) and herniarine (7-methoxycoumarin)
  • said extract is dried, in particular by lyophilization and / or by atomization.
  • polar solvent means a solvent having a dipole moment other than zero, and in particular greater than 1.5.
  • the solvent is a protic solvent.
  • the polar solvent may be chosen from:
  • the polar solvent is brought to a pressure greater than atmospheric pressure.
  • the solvent is water, it may be in the subcritical state.
  • water in the subcritical state means water which is at a temperature of between 100 and 374 ° C and at a pressure between 1 and 218 bar sufficient for the water to be in a liquid state. .
  • the polar solvent is brought to a temperature ranging from 4 ° C. to a temperature of 300 ° C. above the boiling point of the solvent, preferably in a range from 4 ° C. to the boiling point of the solvent, most preferably in a range from room temperature (25 ° C) to 30 ° C.
  • boiling point of the solvent means the highest temperature that the solvent can reach before evaporating, in gaseous form, freely. This temperature is calculated at atmospheric pressure of 1 atmosphere (101.3 kPa).
  • the solvent is at least partially reduced or completely eliminated, in particular by evaporation, by sublimation, in particular under reduced pressure.
  • the extraction step of the process according to the invention may comprise at least one step chosen from the group including decoction, maceration, infusion, digestion, percolation or leaching, hot water entrainment, such as distillation or hydrodistillation, microwave assisted solvent extraction, and ion exchange column .
  • the term "maceration” is intended to mean a process consisting in allowing the cold (usually 5 to 15 ° C) or hot (usually 20 to 25 ° C or 40 to 45 ° C) dipping at least a portion of least one plant in at least one polar solvent for a particular time, in order to extract the soluble compounds.
  • the maceration stage has a duration ranging from 1 minute to 15 days, in particular from 1 minute to 8 hours, more particularly from 30 to 60 minutes.
  • it is carried out at a temperature ranging from 10 0 C to 30 0 C, especially at room temperature (25 ° C).
  • infusion means a process consisting of pouring at least one polar solvent, said polar solvent being at a boiling temperature over at least a portion of at least one plant and then leave the mixture for a period of one minute to two hours.
  • digestion is meant a method of heating a mixture comprising at least one part of at least one plant in at least one polar solvent at a temperature below the boiling point, for example in the case of 10 to 89 ° C, and in particular 25 to 70 ° C.
  • percolation or “leaching” is meant a process of passing the solvent through at least a portion of at least one plant.
  • the distillation can be carried out for example by VMHD, or hydrodistillation by microwave under vacuum.
  • the extraction step of the process according to the invention may be continuous or discontinuous.
  • the method according to the invention may comprise a step involving heating, in particular of a duration ranging from 1 second to 15 days, and in particular from 10 seconds to 8 hours.
  • the process according to the invention is carried out under an inert atmosphere, in particular under nitrogen.
  • additive an antioxidant or a preservative, one or more enzymes, in particular intended to degrade the plant walls, for example to facilitate the extraction, an antifoaming agent, an acid or a base, in particular to modify the isoelectric point and promote precipitation.
  • Preservative means a substance for preserving and / or preserving products.
  • a preservative suitable for the polar solvent according to the invention and its content may be identified by the skilled person in view of his general knowledge.
  • the preserving agent according to the invention may be chosen from the group comprising salts derived from sorbic, benzoic and para-hydroxybenzoic acid.
  • the process according to the invention may furthermore comprise a filtration step, in particular carried out on a cellulose filter or on a sintered glass.
  • the plant before being used has been frozen, in particular when the plant is placed in the polar solvent, it is in the frozen state.
  • the plant is in the dry state when it is placed in the polar solvent.
  • the plant is in a fresh state when it is placed in the polar solvent.
  • Frsh plant means a plant that has not been frozen or dried out.
  • the subject of the invention is also an extract, in particular an aqueous or hydroalcoholic extract, of a plant in liquid or solid form comprising a content of coumarin and in particular of higher herniarin or equal to 0.05% by weight relative to the total weight of the extract.
  • the plant in particular aqueous or aqueous-alcoholic, according to the invention, may be chosen from the group of asteraceae, lamiaceae, labiae and umbelliferae and in particular Axternisia dracunculus, Satureja hortensis, Anthriscus cerefolium , Anethum graveolens, Thymus vulgaris.
  • the extract in particular aqueous or aqueous-alcoholic, according to the invention may further comprise at least one preserving agent, a texturing agent and / or flavor, a dye.
  • a preserving agent, a texturing agent and / or flavor and a dye suitable for the extract, in particular aqueous or aqueous-alcoholic, according to the invention may be identified by the skilled person in view of his general knowledge.
  • the subject of the invention is also a composition comprising at least one extract, in particular an aqueous or aqueous-alcoholic extract, according to the invention.
  • compositions may be chosen from the group comprising food compositions, in particular suppletive, cosmetic, therapeutic, nutraceutical, cosmeceutical and food supplement, dietetic products, medical devices, in particular food compositions, nutraceuticals, cosmeceuticals and food supplements and especially nutraceutical compositions, cosmeceuticals and dietary supplements.
  • the term "nutraceutical composition” means a composition comprising a food substance, in a pharmaceutical form, in particular in the form of tablets, powders, capsules, liquids such as beverages or emulsions, said composition may have a beneficial or protective physiological effect.
  • composition within the meaning of the present invention, a composition suitable for cosmetic use, said composition may have a beneficial or protective physiological effect.
  • the term "food supplement” means a composition comprising nutrients or other substances having a physiological nutritional effect alone or in combination, in particular intended to complete a diet.
  • compositions according to the invention are therapeutic or nutraceutical compositions
  • said compositions can be administered by different routes.
  • administration routes that can be used for the therapeutic and nutraceutical compositions according to the invention, mention may be made of the oral, rectal, cutaneous, bronchopulmonary, nasal, sublingual, perlingual or parenteral routes.
  • compositions according to the invention can be administered in one or more times or in continuous release.
  • the therapeutic and nutraceutical compositions according to the invention can be in various forms, in particular, in a form selected from the group consisting of tablets, capsules (soft and hard), dragees, syrups, suspensions, solutions, powders and powder mixtures, gels, transdermal forms, granules, emulsions, microspheres, nanoparticles and injectable solutions, preferably tablets, injectable solutions, sublingual sprays and skin patches.
  • Formulations suitable for parenteral administration the pharmaceutically acceptable vehicles suitable for this route of administration and the corresponding formulation and administration techniques may be carried out according to methods well known to those skilled in the art, in particular those described in Remington's Pharmaceutical Sciences (Mack Publishing Co., Easton, Pa., 20th Edition, 2000).
  • Said therapeutic and nutraceutical compositions according to the invention may further comprise a pharmaceutically acceptable carrier.
  • pharmaceutically acceptable carrier means any "inert” material or technological adjuvant that is suitable for use in a pharmaceutical product.
  • a pharmaceutically acceptable carrier By way of examples of a pharmaceutically acceptable carrier, mention may be made of lactose, optionally modified starch, cellulose and cellulose derivatives, hydroxypropyl cellulose, hydroxypropylmethylcellulose, mannitol, sorbitol and xylitol. , dextrose, fructooligosaccharides, calcium sulphate, calcium phosphate, calcium lactate, dextrates, inositol, calcium carbonate, glycine, bentonite, polyvinylpyrrolidone, and mixtures thereof.
  • the therapeutic and nutraceutical compositions according to the invention may comprise a content of pharmaceutically acceptable carrier ranging from 5% to 99% by weight, in particular from 10% to 90% by weight, and in particular from 20% to
  • compositions according to the invention are food compositions or food supplements
  • said compositions may be in any of the forms conventionally used in the field of food and well known to those skilled in the art.
  • the food compositions according to the invention may be in the form of a powder for dilution, an oral solution or suspension or emulsion, a powder for capsules, tablets, granules, ready meals or ice creams. .
  • the food supplements according to the invention may be in the form of capsules, powder for dilution, lozenges and tablets.
  • compositions according to the invention are cosmetic or "cosmeceutical” compositions
  • said compositions may be in any of the forms conventionally used in the cosmetic and cosmeceutical fields and well known to those skilled in the art.
  • the cosmetic compositions As examples, the cosmetic compositions and
  • Cosmeceuticals may be in the form of an aqueous solution, or alcoholic or aqueous-alcoholic or an oily suspension or a solution or dispersion of the lotion or serum type, a emulsion of liquid or semi-liquid consistency of milk type, obtained by dispersion of a fatty phase in an aqueous phase (oil-in-water emulsion: H / E) or conversely (Water in Oil: W / O), or a suspension or emulsion of soft consistency such as O / W cream or W / O cream or an aqueous or anhydrous gel, an ointment, lotion, or microcapsules or microparticles, or a vesicular dispersion of ionic type and / or nonionic liposomes, especially in the form of liposomes.
  • composition according to the invention may further comprise at least one anti-coagulant agent such as Allium sativum or an extract Allium sativum.
  • anti-coagulant agent means any agent which makes it possible to avoid or slow down the formation of a blood clot.
  • the subject of the invention is also the use of an extract, in particular an aqueous or aqueous-alcoholic extract, according to the invention, such as:
  • anti-coagulant agent in particular as an anti-aggregating agent for fibrins and / or inhibitors of the synthesis of vitamin-dependent coagulation factors, - a stimulating agent for lymphatic drainage, and / or
  • Proteolytic stimulating agent of macrophages in a composition, in particular food including suppletive, cosmetic, therapeutic, nutraceutical, cosmeceutical and a dietary supplement.
  • the subject of the invention is also the use of an extract, in particular aqueous or hydroalcoholic, according to the invention as rodenticide agent.
  • rodenticide agent means an agent having the property of killing including rodents such as mice, rats, moles, voles, field mice.
  • the subject of the invention is also the use of an extract, in particular an aqueous or aqueous-alcoholic extract, according to the invention as an antifungal agent.
  • the subject of the invention is also the use of an extract, in particular an aqueous or aqueous-alcoholic extract, according to the invention for the preparation of a medicament intended to prevent and / or treat varicose veins, thrombophlebitis, venous thromboembolic disease and / or cardiomyopathy.
  • an extract in particular an aqueous or aqueous-alcoholic extract
  • Arterial or venous thrombotic conditions such as venous thrombosis in the presence of heparin therapy, deep phlebitis, pulmonary embolism, atrial fibrillation, heart failure, thrombotic diseases such as congenital or acquired deficiency thrombin III or thrombocytosis, myocardial infarction, coronary artery bypass grafting, stroke.
  • Artemisia dracunculus is dried (Ig) or frozen (10g) and then ground.
  • the ground material is placed in a 250 ml beaker, then water (10 ml) is added, the mixture is heated at 60 ° C. with stirring for 1 h and then this suspension is filtered through a frit. The filtrate is recovered and then reduced to half of its initial volume.
  • the herniarin content is measured by HPLC by comparing the elution profile with a control solution of herniarine in water. The measured content is 1.35% by weight relative to the weight of plant solids.
  • Example 2 Extraction of herniarine from Artemisia dracunculus by infusion according to the standard Kumagawa protocol
  • Artemisia dracunculus is dried (Ig) or frozen (10g) and then ground.
  • the ground material is placed on a filter, then water (10 ml) at boiling temperature is added to the ground material, and the mixture is left for about one hour.
  • the filtrate is recovered and then reduced to half of its initial volume.
  • the herniarin content is measured by HPLC by comparing the elution profile with a control solution of herniarine in water.
  • the measured content is 0.75% by weight relative to the weight of plant solids.
  • Example 3 Extraction of herniarine from Artemisia dracunculus, Satureja hortensis, Anthriscus cerefolium, Anethum graveolens, Thymus vulgaris
  • Herniarin was extracted from different plants according to the method described in Example 1. The herniarin content is expressed as a percentage by weight relative to the weight of dry matter of plant and the results obtained are shown in the table below. .
  • Artemisia dracunculus (Ig) is frozen (10g) and crushed.
  • the ground material is placed in a 250 ml beaker, and then various water / ethanol mixtures (20 ml) having an alcohol content of 30, 50, 70, 80 and 100 are added.
  • the mixture is heated to a temperature ranging from 25 to 80 ° C. with ultrasound stirring for 4 h with sampling every 30 minutes. Then the suspension is filtered on a frit. The filtrate is recovered and then reduced to half of its initial volume.
  • the herniarin content is measured by HPLC.
  • the herniarin plant titre is expressed as a percentage and the results obtained are shown in the tables below according to the alcoholic degree, the temperature and the extraction time used.

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  • Pyrane Compounds (AREA)

Abstract

The present invention relates to the field of extraction of coumarins. It relates most particularly to a process for extracting at least one coumarin from part of a plant, the extracts obtained by these processes, compositions comprising said extracts and uses thereof.

Description

PROCÉDÉ D'EXTRACTION DE COUMARINES PROCESS FOR EXTRACTING COUMARINS
La présente invention se rapporte au domaine de l'extraction de coumarines. Elle concerne tout particulièrement des procédés d'extraction d'au moins une coumarine à partir d'une partie de plante, les extraits obtenus par ces procédés, des compositions comprenant lesdits extraits et leurs utilisations.The present invention relates to the field of coumarin extraction. It particularly relates to processes for extracting at least one coumarin from a plant part, the extracts obtained by these processes, compositions comprising said extracts and their uses.
Les coumarines recouvrent plus d'un millier de composés identifiés de type 2H-l-benzopyran-2-ones. À titre d'exemples de coumarines, on peut citer la coumarine, la warfarine, l'ombelliférone, l'esculétol, le scopolétol et l'herniarine.Coumarins cover more than a thousand identified compounds of type 2H-1-benzopyran-2-ones. Examples of coumarins include coumarin, warfarin, umbelliferone, esculetol, scopoletol and herniarine.
De nombreuses expériences ont montré l'importance physiologique des coumarines, en particulier leur effet anti-coagulant, notamment par l'inhibition de la synthèse de facteurs de la coagulation vitaminoK dépendant (Rohde LE et al., CURRENT OPINION IN CLINICAL NUTRITION AND METABOLIC CARE 10 (1): 1-5 JAN 2007; Dentali F et al., JOURNAL OF THROMBOSIS AND HAEMOSTASIS 4 (9): 1853-1863 SEP 2006; Becquemont L et al., BULLETIN DE L ACADEMIE NATIONALE DE MEDECINE 190 (1): 37-49 JAN 2006).Numerous experiments have shown the physiological importance of coumarins, in particular their anti-coagulant effect, notably by the inhibition of the synthesis of dependent vitamin X-dependent coagulation factors (Rohde LE et al., CURRENT OPINION IN CLINICAL NUTRITION AND METABOLIC CARE 10 (1): 1-5 JAN 2007; Dentali F et al., JOURNAL OF THROMBOSIS AND HAEMOSTASIS 4 (9): 1853-1863 SEP 2006; Becquemont L et al., BULLETIN OF THE NATIONAL ACADEMY OF MEDICINE 190 (1) : 37-49 JAN 2006).
Les coumarines sont également connues pour leurs propriétés stimulantes du drainage lymphatique (Foldi et al., PHLEBOLOGIE 35 (4): 205-210 SEP 2006; BORZEIX MG, et al. ARZNEIMITTEL-FORSCHUNG/DRUG RESEARCH 45-1 (3): 262-266 MAR 1995; KNIGHT KR, et al., INTERNATIONAL JOURNAL OF EXPERIMENTAL PATHOLOGY 72 (5): 533-542 OCT 1991).Coumarins are also known for their stimulating properties of lymphatic drainage (Foldi et al., PHLEBOLOGY 35 (4): 205-210 SEP, 2006; BORZEIX MG, et al., ARZNEIMITTEL-FORSCHUNG / DRUG RESEARCH 45-1 (3): 262 -266 Mar. 1995; KNIGHT KR, et al., INTERNATIONAL JOURNAL OF EXPERIMENTAL PATHOLOGY 72 (5): 533-542 OCT 1991).
Il est donc intéressant d'obtenir des compositions enrichies en herniarine permettant d'utiliser en tout ou partie les propriétés évoquées ci-dessus. Les coumarines sont généralement obtenues par synthèse chimique et/ou par des procédés d'extraction. Ceci peut nécessiter de nombreuses étapes, impliquer l'utilisation de solvants et/ou de réactifs susceptibles d'être difficile et dangereux à manipuler et assez coûteux.It is therefore interesting to obtain compositions enriched with herniarine to use all or part of the properties mentioned above. Coumarins are generally obtained by chemical synthesis and / or by extraction methods. This may require many steps, involving the use of solvents and / or reagents that may be difficult and dangerous to handle and quite expensive.
Il subsiste donc un besoin pour des procédés d'extraction de coumarine présentant des propriétés améliorées, notamment en terme économique, de simplicité et/ou de toxicité.There remains therefore a need for coumarin extraction processes having improved properties, especially in economic terms, simplicity and / or toxicity.
Les inventeurs ont maintenant mis au point des procédés d'extraction permettant de résoudre en tout ou partie les problèmes évoqués ci-dessus.The inventors have now developed extraction processes to solve all or part of the problems mentioned above.
Lesdits procédés de l'invention utilisent essentiellement l'eau comme solvant d'extraction. Il est à noter qu'outre la résolution des problèmes évoqués ci- dessus, l'utilisation d'eau dans un procédé d'extraction de coumarines n'était pas évidente dans la mesure où ces composés sont connus de l'art comme n'étant pas (e.g. warfarine) ou faiblement (e.g. coumarine) solubles dans l'eau. En outre le rendement d'extraction a pu être optimisé en jouant sur les trois paramètres suivants : l'addition à l'eau d'une quantité minime d'un autre solvant polaire, de préférence un alcool, la température d'extraction, et/ou la durée d'extraction.Said methods of the invention essentially use water as extraction solvent. It should be noted that in addition to solving the problems mentioned above, the use of water in a coumarin extraction process was not obvious insofar as these compounds are known in the art as n ' being not (eg warfarin) or weakly (eg coumarin) soluble in water. In addition, the extraction yield could be optimized by playing on the following three parameters: the addition to water of a minimal amount of another polar solvent, preferably an alcohol, the extraction temperature, and / or the extraction time.
Selon un premier aspect, l'invention a pour objet un procédé d'extraction comprenant au moins les étapes suivantes :According to a first aspect, the subject of the invention is an extraction method comprising at least the following steps:
- placer au moins une partie d'au moins une plante dans au moins un solvant polaire constitué d'eau et de 0 à 30% d'au moins un alcool, et éventuellement d'un additif ;placing at least a portion of at least one plant in at least one polar solvent consisting of water and 0 to 30% of at least one alcohol, and optionally an additive;
- procéder à l'extraction de ladite plante ; et - récupérer l'extrait obtenu par l'étape précédente, ledit extrait comprenant au moins une partie du solvant et au moins une coumarine.- proceed to the extraction of said plant; and recovering the extract obtained by the preceding step, said extract comprising at least a part of the solvent and at least one coumarin.
On entend par « partie d'une plante » au sens de la présente invention un élément de la structure d'une plante, notamment la racine, la tige, l'écorce, la graine, le fruit, la feuille, la sommité et/ou la fleur. Bien évidemment, par « au moins une partie de plante », on peut entendre également une plante entière.For the purposes of the present invention, the term "part of a plant" means an element of the structure of a plant, in particular the root, the stem, the bark, the seed, the fruit, the leaf, the head and / or the flower. Of course, by "at least a part of plant", one can also hear a whole plant.
En particulier, la partie de plante est broyée, pulvérisée et/ou hachée.In particular, the plant part is milled, pulverized and / or minced.
Dans le procédé selon l'invention, la plante peut être choisie dans le groupe des astéracées, des lamiacées, des labiées et des ombellifères et en particulier l'Arternisia dracunculus, la Satureja hortensis, l'Anthriscus cerefolium, l'Anethum graveolens, le Thymus vulgaris.In the process according to the invention, the plant may be chosen from the group of asteraceae, lamiaceae, labiae and umbelliferae and in particular Arternisia dracunculus, Satureja hortensis, Anthriscus cerefolium, Anethum graveolens, Thymus vulgaris.
L'extrait peut concerner en outre de l'ail, de la ciboulette (allium schoenoprasum, de l'ail des ours (allium ursinum) , de l'ail (allium sativum) .The extract may also include garlic, chives (allium schoenoprasum, wild garlic (allium ursinum), garlic (allium sativum).
On entend par « extrait », une composition obtenue à partir d'une plante par une opération physique et/ou chimique, en particulier par extraction d'au moins une partie de plante par au moins un solvant.The term "extract" means a composition obtained from a plant by a physical and / or chemical operation, in particular by extraction of at least a part of the plant with at least one solvent.
Selon un mode de réalisation particulier du procédé selon l'invention, ledit extrait est : stérilisé, notamment par chauffage avec ou sans pression et/ou par passage sur une membrane ; et/ou désinfecté, notamment par chauffage avec ou sans pression et/ou par au moins un agent désinfectant. En particulier, ledit extrait comprend de l'herniarine notamment en une teneur allant de 0,1 % à 30 %, de préférence de 0,5 à 15 %, plus préférentiellement de 1 à 5 % en poids par rapport au poids de la plante sèche.According to a particular embodiment of the process according to the invention, said extract is: sterilized, in particular by heating with or without pressure and / or by passage over a membrane; and / or disinfected, in particular by heating with or without pressure and / or by at least one disinfecting agent. In particular, said extract comprises herniarine in particular in a content ranging from 0.1% to 30%, preferably from 0.5 to 15%, more preferably from 1 to 5% by weight relative to the weight of the plant. dried.
Par « plante sèche » ou « plante à l'état sec », on entend une plante dont le poids, après passage pendant 5 heures à l'étuve à 105 0C, varie de moins de 5 % par rapport au poids avant le dernier passage à l'étuve.By "dry plant" or "plant in the dry state" is meant a plant whose weight, after passing for 5 hours in an oven at 105 ° C., varies from less than 5% by weight relative to the weight before the last one. passage to the oven.
Ledit extrait peut comprendre en outre au moins une autre coumarine, en particulier la warfarine.Said extract may further comprise at least one other coumarin, in particular warfarin.
On entend par « coumarine », les composés de type 2H-1- benzopyran-2-ones. À titre d'exemples de coumarines, on peut citer la coumarine ( 1,2-benzopyrone) , la warfarine (4- hydroxy-3-(3-oxo-l-phénylbutyl)coumarine) , l'ombelliférone ( 7-hydroxycoumarine ) , l ' esculétol ( 6 , 7-dihydroxycoumarine ) , le scopolétol (6-methoxy-7-hydroxycoumarine) et l'herniarine (7-méthoxycoumarine)The term "coumarin" refers to 2H-1-benzopyran-2-one compounds. Examples of coumarins are coumarin (1,2-benzopyrone), warfarin (4-hydroxy-3- (3-oxo-1-phenylbutyl) coumarin), umbelliferone (7-hydroxycoumarin) , esculetol (6,7-dihydroxycoumarin), scopoletol (6-methoxy-7-hydroxycoumarin) and herniarine (7-methoxycoumarin)
En particulier ledit extrait est séché, en particulier par lyophilisation et/ou par atomisation.In particular, said extract is dried, in particular by lyophilization and / or by atomization.
On entend par « solvant polaire » un solvant présentant un moment dipolaire différent de zéro, et en particulier supérieur à 1,5.The term "polar solvent" means a solvent having a dipole moment other than zero, and in particular greater than 1.5.
En particulier le solvant est un solvant protique.In particular, the solvent is a protic solvent.
Dans le procédé selon l'invention, le solvant polaire peut être choisi parmi :In the process according to the invention, the polar solvent may be chosen from:
- l'eau, telle l'eau osmosée, distillée, permutée ; et l'eau telle que définie ci-dessus additionnée jusqu'à 30% d'au moins un alcool, de préférence ledit alcool étant choisi parmi le méthanol, l'éthanol, le propanol, le butanol, le pentanol ; et éventuellement additionné d'un additif .Selon un mode de réalisation particulier du procédé selon l'invention, le solvant polaire est porté à une pression supérieure à la pression atmosphérique. En particulier lorsque le solvant est de l'eau, elle peut être à l'état subcritique.- water, such as osmosis water, distilled, permuted; and the water as defined above added up to 30% of at least one alcohol, preferably alcohol being selected from methanol, ethanol, propanol, butanol, pentanol; and optionally added with an additive. According to a particular embodiment of the process according to the invention, the polar solvent is brought to a pressure greater than atmospheric pressure. In particular when the solvent is water, it may be in the subcritical state.
On entend par « eau à l ' état subcritique », de l ' eau qui se trouve à une température comprise entre 100 et 374°C et à une pression entre 1 et 218 bars suffisante pour que l'eau soit à l'état liquide.The term "water in the subcritical state" means water which is at a temperature of between 100 and 374 ° C and at a pressure between 1 and 218 bar sufficient for the water to be in a liquid state. .
En particulier, le solvant polaire est porté à une température comprise dans une gamme allant de 4°C à une température de 3000C au-dessus de la température d'ébullition du solvant, de préférence dans une gamme allant de 4°C à la température d'ébullition du solvant, de manière tout à fait préférée dans une gamme allant de la température ambiante (25°C) à 300C.In particular, the polar solvent is brought to a temperature ranging from 4 ° C. to a temperature of 300 ° C. above the boiling point of the solvent, preferably in a range from 4 ° C. to the boiling point of the solvent, most preferably in a range from room temperature (25 ° C) to 30 ° C.
On entend par « température d'ébullition du solvant », la température la plus élevée que le solvant peut atteindre avant de s'évaporer, sous forme gazeuse, librement. Cette température se calcule à la pression atmosphérique de 1 atmosphère (101,3 kPa).The term "boiling point of the solvent" means the highest temperature that the solvent can reach before evaporating, in gaseous form, freely. This temperature is calculated at atmospheric pressure of 1 atmosphere (101.3 kPa).
Selon un mode de réalisation particulier du procédé selon l'invention, le solvant est au moins en partie réduit, voire totalement éliminé, notamment par évaporation, par sublimation, en particulier sous pression réduite .According to a particular embodiment of the process according to the invention, the solvent is at least partially reduced or completely eliminated, in particular by evaporation, by sublimation, in particular under reduced pressure.
L'étape d'extraction du procédé selon l'invention peut comprendre au moins une étape choisie dans le groupe comprenant la décoction, la macération, l'infusion, la digestion, la percolation ou lixiviation, entraînement à l'eau chaude, comme la distillation ou hydrodistillation, l'extraction par solvant assistée par micro-ondes, et par colonne échangeuse d'ions.The extraction step of the process according to the invention may comprise at least one step chosen from the group including decoction, maceration, infusion, digestion, percolation or leaching, hot water entrainment, such as distillation or hydrodistillation, microwave assisted solvent extraction, and ion exchange column .
On entend par « décoction » , un procédé comprenant les étapes suivantes :The term "decoction" means a process comprising the following steps:
la mise à ébullition d'un mélange comprenant une partie d'au moins une plante dans au moins un solvant polaire ; etboiling a mixture comprising a portion of at least one plant in at least one polar solvent; and
le maintien de cette ébullition pendant une durée particulière, notamment de 1 minute à 2 heures, en particulier environ 20 minutes, puis éventuellement un retour à température ambiante.the maintenance of this boiling for a particular period, in particular from 1 minute to 2 hours, in particular about 20 minutes, then possibly a return to ambient temperature.
On entend par « macération », un procédé consistant à laisser tremper à froid (généralement de 5 à 15°C) ou à chaud (généralement de 20 à 25°C ou de 40 à 45°C) au moins une partie d'au moins une plante dans au moins un solvant polaire pendant une durée particulière, afin d'en extraire les composés solubles.The term "maceration" is intended to mean a process consisting in allowing the cold (usually 5 to 15 ° C) or hot (usually 20 to 25 ° C or 40 to 45 ° C) dipping at least a portion of least one plant in at least one polar solvent for a particular time, in order to extract the soluble compounds.
En particulier, l'étape de macération a une durée allant de 1 minute à 15 jours, en particulier de 1 minute à 8 heures, plus particulièrement de 30 à 60 minutes. De préférence, elle se fait à une température comprise dans une gamme allant de 100C à 300C, tout particulièrement à la température ambiante (25°C).In particular, the maceration stage has a duration ranging from 1 minute to 15 days, in particular from 1 minute to 8 hours, more particularly from 30 to 60 minutes. Preferably, it is carried out at a temperature ranging from 10 0 C to 30 0 C, especially at room temperature (25 ° C).
On entend par « infusion », un procédé consistant à verser au moins un solvant polaire, ledit solvant polaire étant à température d'ébullition sur au moins une partie d'au moins une plante, puis à laisser le mélange pendant une période allant d'une minute à 2 heures.The term "infusion" means a process consisting of pouring at least one polar solvent, said polar solvent being at a boiling temperature over at least a portion of at least one plant and then leave the mixture for a period of one minute to two hours.
On entend par « digestion », un procédé consistant à chauffer un mélange comprenant une partie d'au moins une plante dans au moins un solvant polaire à une température inférieure à la température d'ébullition, par exemple dans le cas de l'eau de 10 à 89°C, et en particulier de 25 à 700C.By "digestion" is meant a method of heating a mixture comprising at least one part of at least one plant in at least one polar solvent at a temperature below the boiling point, for example in the case of 10 to 89 ° C, and in particular 25 to 70 ° C.
On entend par « percolation » ou « lixiviation » , un procédé consistant à faire passer le solvant à travers au moins une partie d'au moins une plante.By "percolation" or "leaching" is meant a process of passing the solvent through at least a portion of at least one plant.
La distillation peut être effectuée par exemple par VMHD, soit hydrodistillation par micro-onde sous vide puisé.The distillation can be carried out for example by VMHD, or hydrodistillation by microwave under vacuum.
L'étape d'extraction du procédé selon l'invention peut être continue ou discontinue.The extraction step of the process according to the invention may be continuous or discontinuous.
Le procédé selon l'invention peut comprendre une étape impliquant le chauffage, en particulier d'une durée allant de 1 seconde à 15 jours, et notamment de 10 secondes à 8 heures.The method according to the invention may comprise a step involving heating, in particular of a duration ranging from 1 second to 15 days, and in particular from 10 seconds to 8 hours.
En particulier, le procédé selon l'invention est effectué sous atmosphère inerte, notamment sous azote.In particular, the process according to the invention is carried out under an inert atmosphere, in particular under nitrogen.
On entend par « additif » , un agent anti-oxydant ou un agent conservateur, une ou des enzymes, notamment destinées à dégrader les parois végétales, par exemple pour faciliter l'extraction, un agent anti-moussant, un acide ou une base, notamment pour modifier le point isoélectrique et favoriser la précipitation. On entend par « agent conservateur » , une substance permettant de conserver et/ou de préserver des produits.The term "additive", an antioxidant or a preservative, one or more enzymes, in particular intended to degrade the plant walls, for example to facilitate the extraction, an antifoaming agent, an acid or a base, in particular to modify the isoelectric point and promote precipitation. "Preservative" means a substance for preserving and / or preserving products.
Un agent conservateur adapté pour le solvant polaire selon l'invention ainsi que sa teneur peuvent être identifiés par l'Homme du Métier au regard de ses connaissances générales.A preservative suitable for the polar solvent according to the invention and its content may be identified by the skilled person in view of his general knowledge.
En particulier, l'agent conservateur selon l'invention peut être choisi dans le groupe comprenant les sels dérivés de l'acide sorbique, benzoique et parahydroxybenzoique .In particular, the preserving agent according to the invention may be chosen from the group comprising salts derived from sorbic, benzoic and para-hydroxybenzoic acid.
Le procédé selon l'invention peut comprendre en outre une étape de filtration, notamment effectuée sur filtre de cellulose ou sur verre fritte.The process according to the invention may furthermore comprise a filtration step, in particular carried out on a cellulose filter or on a sintered glass.
Selon un mode de réalisation particulier du procédé selon l'invention, la plante avant d'être utilisée a été congelée, en particulier lorsque la plante est placée dans le solvant polaire, elle est à l'état congelé.According to a particular embodiment of the process according to the invention, the plant before being used has been frozen, in particular when the plant is placed in the polar solvent, it is in the frozen state.
Selon un mode de réalisation particulier du procédé selon l'invention, la plante est à l'état sec lorsqu'elle est placée dans le solvant polaire.According to a particular embodiment of the process according to the invention, the plant is in the dry state when it is placed in the polar solvent.
Selon un mode de réalisation particulier du procédé selon l'invention, la plante est à l'état frais lorsqu'elle est placée dans le solvant polaire.According to a particular embodiment of the process according to the invention, the plant is in a fresh state when it is placed in the polar solvent.
On entend par « plante à l'état frais », une plante qui n'a ni été congelée ni desséchée."Fresh plant" means a plant that has not been frozen or dried out.
Selon un autre aspect, l'invention a également pour objet un extrait, notamment aqueux ou hydroalcoolique, d'une plante sous forme liquide ou solide comprenant une teneur en coumarine et notamment en herniarine supérieure ou égale à 0,05 % en poids par rapport au poids total de l'extrait.According to another aspect, the subject of the invention is also an extract, in particular an aqueous or hydroalcoholic extract, of a plant in liquid or solid form comprising a content of coumarin and in particular of higher herniarin or equal to 0.05% by weight relative to the total weight of the extract.
On entend par « herniarine », la 7-méthoxycoumarine.The term "herniarine" means 7-methoxycoumarin.
Dans l'extrait, notamment aqueux ou hydroalcoolique, selon l'invention, la plante peut être choisie dans le groupe des astéracées, des lamiacées, des labiées et des ombellifères et en particulier l' Axternisia dracunculus, la Satureja hortensis, l'Anthriscus cerefolium, l'Anethum graveolens, le Thymus vulgaris.In the extract, in particular aqueous or aqueous-alcoholic, according to the invention, the plant may be chosen from the group of asteraceae, lamiaceae, labiae and umbelliferae and in particular Axternisia dracunculus, Satureja hortensis, Anthriscus cerefolium , Anethum graveolens, Thymus vulgaris.
L'extrait, notamment aqueux ou hydroalcoolique, selon l ' invention peut comprendre en outre au moins un agent conservateur, un agent de texture et/ou de saveur, un colorant.The extract, in particular aqueous or aqueous-alcoholic, according to the invention may further comprise at least one preserving agent, a texturing agent and / or flavor, a dye.
Un agent conservateur, un agent de texture et/ou de saveur et un colorant adaptés à l'extrait, notamment aqueux ou hydroalcoolique, selon l'invention peuvent être identifiés par l'Homme du Métier au regard de ses connaissances générales.A preserving agent, a texturing agent and / or flavor and a dye suitable for the extract, in particular aqueous or aqueous-alcoholic, according to the invention may be identified by the skilled person in view of his general knowledge.
Selon un autre aspect, l'invention a également pour objet une composition comprenant au moins un extrait, notamment aqueux ou hydroalcoolique, selon l'invention.According to another aspect, the subject of the invention is also a composition comprising at least one extract, in particular an aqueous or aqueous-alcoholic extract, according to the invention.
La composition selon l'invention peut être choisie dans le groupe comprenant les compositions alimentaires notamment supplétives, cosmétiques, thérapeutiques, nutraceutiques, cosméceutiques et les compléments alimentaires, produits diététiques, dispositifs médicaux en particulier les compositions alimentaires, nutraceutiques, cosméceutiques et les compléments alimentaires et tout particulièrement les compositions nutraceutiques, cosméceutiques et les compléments alimentaires. On entend par « composition nutraceutique » au sens de la présente invention, une composition comprenant une substance alimentaire, sous une forme pharmaceutique, notamment sous la forme de comprimés, de poudres, de gélules, capsules, de liquides comme des boissons ou des émulsions, ladite composition pouvant présenter un effet physiologique bénéfique ou protecteur.The composition according to the invention may be chosen from the group comprising food compositions, in particular suppletive, cosmetic, therapeutic, nutraceutical, cosmeceutical and food supplement, dietetic products, medical devices, in particular food compositions, nutraceuticals, cosmeceuticals and food supplements and especially nutraceutical compositions, cosmeceuticals and dietary supplements. For the purposes of the present invention, the term "nutraceutical composition" means a composition comprising a food substance, in a pharmaceutical form, in particular in the form of tablets, powders, capsules, liquids such as beverages or emulsions, said composition may have a beneficial or protective physiological effect.
On entend par composition « cosméceutique » au sens de la présente invention, une composition appropriée à une utilisation cosmétique, ladite composition pouvant présenter un effet physiologique bénéfique ou protecteur.The term "cosmeceutical" composition within the meaning of the present invention, a composition suitable for cosmetic use, said composition may have a beneficial or protective physiological effect.
On entend par « complément alimentaire » au sens de la présente invention, une composition comprenant des nutriments ou d'autres substances ayant un effet nutritionnel physiologique seuls ou combinés, notamment destinée à compléter un régime alimentaire.For the purposes of the present invention, the term "food supplement" means a composition comprising nutrients or other substances having a physiological nutritional effect alone or in combination, in particular intended to complete a diet.
En particulier, lorsque les compositions selon l'invention sont des compositions thérapeutiques ou nutraceutiques, lesdites compositions sont administrables par différentes voies.In particular, when the compositions according to the invention are therapeutic or nutraceutical compositions, said compositions can be administered by different routes.
À titre d'exemples de voies d'administration utilisables pour les compositions thérapeutiques et nutraceutiques selon l'invention, on peut citer la voie orale, rectale, cutanée, broncho-pulmonaire, nasale, sublinguale, perlinguale ou parentérale.As examples of administration routes that can be used for the therapeutic and nutraceutical compositions according to the invention, mention may be made of the oral, rectal, cutaneous, bronchopulmonary, nasal, sublingual, perlingual or parenteral routes.
Les compositions thérapeutiques et nutraceutiques selon l'invention peuvent être administrées en une ou plusieurs fois ou en libération continue.The therapeutic and nutraceutical compositions according to the invention can be administered in one or more times or in continuous release.
Les compositions thérapeutiques et nutraceutiques selon l'invention peuvent se présenter sous différentes formes, en particulier, sous une forme choisie dans le groupe comprenant les comprimés, les capsules (molles et dures), les dragées, les sirops, les suspensions, les solutions, les poudres et les mélanges de poudres, les gels, les formes transdermiques, les granulés, les émulsions, les microsphères, les nanoparticules et les solutions injectables, de préférence les comprimés, les solutions injectables, les sprays sublinguaux et les patchs cutanés.The therapeutic and nutraceutical compositions according to the invention can be in various forms, in particular, in a form selected from the group consisting of tablets, capsules (soft and hard), dragees, syrups, suspensions, solutions, powders and powder mixtures, gels, transdermal forms, granules, emulsions, microspheres, nanoparticles and injectable solutions, preferably tablets, injectable solutions, sublingual sprays and skin patches.
Ces différentes formes peuvent être obtenues par des techniques bien connues de l'Homme du Métier.These different forms can be obtained by techniques well known to those skilled in the art.
Les formulations appropriées à une administration par voie parentérale, les véhicules pharmaceutiquement acceptables appropriés à cette voie d'administration et les techniques de formulation et d'administration correspondantes peuvent être réalisées selon des méthodes bien connues de l'Homme du Métier, en particulier celles décrites dans le manuel Remington's Pharmaceutical Sciences (Mack Publishing Co., Easton, Pa., 20ème édition, 2000).Formulations suitable for parenteral administration, the pharmaceutically acceptable vehicles suitable for this route of administration and the corresponding formulation and administration techniques may be carried out according to methods well known to those skilled in the art, in particular those described in Remington's Pharmaceutical Sciences (Mack Publishing Co., Easton, Pa., 20th Edition, 2000).
Lesdites compositions thérapeutiques et nutraceutiques selon l'invention peuvent comprendre en outre un support pharmaceutiquement acceptable .Said therapeutic and nutraceutical compositions according to the invention may further comprise a pharmaceutically acceptable carrier.
On entend par « support pharmaceutiquement acceptable », toute matière « inerte » ou adjuvant technologique qui est appropriée à une utilisation dans un produit pharmaceutique.The term "pharmaceutically acceptable carrier" means any "inert" material or technological adjuvant that is suitable for use in a pharmaceutical product.
À titre d'exemples de support pharmaceutiquement acceptable, on peut citer le lactose, l'amidon, éventuellement modifié, la cellulose et les dérivés de la cellulose, l ' hydroxypropyl cellulose, l ' hydroxypropylméthyl cellulose, le mannitol, le sorbitol, le xylitol, le dextrose, les fructooligosaccharides, le sulfate de calcium, le phosphate de calcium, le lactate de calcium, les dextrates, l'inositol, le carbonate de calcium, la glycine, la bentonite, la polyvinylpyrrolidone, et leurs mélanges .By way of examples of a pharmaceutically acceptable carrier, mention may be made of lactose, optionally modified starch, cellulose and cellulose derivatives, hydroxypropyl cellulose, hydroxypropylmethylcellulose, mannitol, sorbitol and xylitol. , dextrose, fructooligosaccharides, calcium sulphate, calcium phosphate, calcium lactate, dextrates, inositol, calcium carbonate, glycine, bentonite, polyvinylpyrrolidone, and mixtures thereof.
Les compositions thérapeutiques et nutraceutiques selon l'invention peuvent comprendre une teneur en support pharmaceutiquement acceptable allant de 5 à 99 % en poids, notamment de 10 à 90 % en poids, et en particulier de 20 àThe therapeutic and nutraceutical compositions according to the invention may comprise a content of pharmaceutically acceptable carrier ranging from 5% to 99% by weight, in particular from 10% to 90% by weight, and in particular from 20% to
75 % en poids par rapport au poids total de la composition.75% by weight relative to the total weight of the composition.
Lorsque les compositions selon l'invention sont des compositions alimentaires ou des compléments alimentaires, lesdites compositions peuvent se présenter sous toutes les formes classiquement utilisées dans le domaine de l'alimentation et bien connues de l'Homme du Métier.When the compositions according to the invention are food compositions or food supplements, said compositions may be in any of the forms conventionally used in the field of food and well known to those skilled in the art.
À titre d'exemples, les compositions alimentaires selon l'invention peuvent se présenter sous la forme de poudre à diluer, de solution ou suspension ou émulsion buvables, de poudre pour capsules, de comprimés, de granules, de plats cuisinés, de crèmes glacées.By way of example, the food compositions according to the invention may be in the form of a powder for dilution, an oral solution or suspension or emulsion, a powder for capsules, tablets, granules, ready meals or ice creams. .
À titre d'exemples, les compléments alimentaires selon l'invention peuvent se présenter sous la forme de gélules, de poudre à diluer, de pastilles et de comprimés.By way of examples, the food supplements according to the invention may be in the form of capsules, powder for dilution, lozenges and tablets.
Lorsque les compositions selon l'invention sont des compositions cosmétiques ou « cosméceutiques » , lesdites compositions peuvent se présenter sous toutes les formes classiquement utilisées dans les domaines cosmétique et cosméceutique et bien connues de l'Homme du Métier.When the compositions according to the invention are cosmetic or "cosmeceutical" compositions, said compositions may be in any of the forms conventionally used in the cosmetic and cosmeceutical fields and well known to those skilled in the art.
À titre d'exemples, les compositions cosmétiques etAs examples, the cosmetic compositions and
« cosméceutiques » selon l'invention peuvent se présenter sous la forme d'une solution ou suspension aqueuse, alcoolique ou hydroalcoolique ou d'une suspension huileuse ou d'une solution ou d'une dispersion de type lotion ou sérum, d'une émulsion de consistance liquide ou semi- liquide de type lait, obtenues par dispersion d'une phase grasse dans une phase aqueuse (émulsion Huile dans Eau : H/E) ou inversement (Eau dans Huile : E/H), ou d'une suspension ou émulsion de consistance molle du type crème H/E ou E/H ou d'un gel aqueux ou anhydre, d'un onguent, d'une lotion, ou encore de microcapsules ou microparticules, ou d'une dispersion vésiculaire de type ionique et/ou non ioniques de liposomes, notamment sous forme de liposomes."Cosmeceuticals" according to the invention may be in the form of an aqueous solution, or alcoholic or aqueous-alcoholic or an oily suspension or a solution or dispersion of the lotion or serum type, a emulsion of liquid or semi-liquid consistency of milk type, obtained by dispersion of a fatty phase in an aqueous phase (oil-in-water emulsion: H / E) or conversely (Water in Oil: W / O), or a suspension or emulsion of soft consistency such as O / W cream or W / O cream or an aqueous or anhydrous gel, an ointment, lotion, or microcapsules or microparticles, or a vesicular dispersion of ionic type and / or nonionic liposomes, especially in the form of liposomes.
La composition selon l'invention peut comprendre en outre au moins un agent anti-coagulant tel que de l'Allium sativum ou un extrait ά'Allium sativum.The composition according to the invention may further comprise at least one anti-coagulant agent such as Allium sativum or an extract Allium sativum.
On entend par « agent anti-coagulant », tout agent qui permet d'éviter ou de ralentir la formation d'un caillot sanguin.The term "anti-coagulant agent" means any agent which makes it possible to avoid or slow down the formation of a blood clot.
Selon un autre aspect, l'invention a également pour objet l'utilisation d'un extrait, notamment aqueux ou hydroalcoolique, selon l'invention comme :According to another aspect, the subject of the invention is also the use of an extract, in particular an aqueous or aqueous-alcoholic extract, according to the invention, such as:
- agent anti-coagulant, en particulier en tant qu'agent anti-aggrégant des fibrines et/ou inhibiteurs de la synthèse des facteurs de la coagulation vitaminoK dépendant, - agent stimulateur du drainage lymphatique, et/ouanti-coagulant agent, in particular as an anti-aggregating agent for fibrins and / or inhibitors of the synthesis of vitamin-dependent coagulation factors, - a stimulating agent for lymphatic drainage, and / or
- agent stimulateur protéolytique des macrophages, dans une composition, en particulier alimentaire notamment supplétive, cosmétique, thérapeutique, nutraceutique , cosméceutique et un complément alimentaire.- Proteolytic stimulating agent of macrophages, in a composition, in particular food including suppletive, cosmetic, therapeutic, nutraceutical, cosmeceutical and a dietary supplement.
Selon un autre aspect, l'invention a également pour objet l'utilisation d'un extrait, notamment aqueux ou hydroalcoolique, selon l'invention en tant qu'agent rodenticide.According to another aspect, the subject of the invention is also the use of an extract, in particular aqueous or hydroalcoholic, according to the invention as rodenticide agent.
On entend par « agent rodenticide » un agent ayant la propriété de tuer notamment les rongeurs tels que les souris, rats, taupes, campagnols, mulots.The term "rodenticide agent" means an agent having the property of killing including rodents such as mice, rats, moles, voles, field mice.
Selon un autre aspect, l'invention a également pour objet l'utilisation d'un extrait, notamment aqueux ou hydroalcoolique, selon l'invention en tant qu'agent antifongique.According to another aspect, the subject of the invention is also the use of an extract, in particular an aqueous or aqueous-alcoholic extract, according to the invention as an antifungal agent.
Selon un autre aspect, l'invention a également pour objet l'utilisation d'un extrait, notamment aqueux ou hydroalcoolique, selon l'invention pour la préparation d'un médicament destiné à prévenir et/ou à traiter des varices, des thrombophlébites, la maladie thrombo-embolique veineuse et/ou la cardiomyopathie. Les états thrombotiques artériels ou veineux, comme les thromboses veineuses en relais d'une héparinothérapie, les phlébites profondes, les embolies pulmonaires, les fibrillations auriculaire, les insuffisances cardiaques, les maladies exposant à des thromboses, comme le déficit congénital ou acquis en anti- thrombine III ou les thrombocytoses, l'infarctus du myocarde, les pontages aorto-coronariens , les accidents vasculaires cérébraux.According to another aspect, the subject of the invention is also the use of an extract, in particular an aqueous or aqueous-alcoholic extract, according to the invention for the preparation of a medicament intended to prevent and / or treat varicose veins, thrombophlebitis, venous thromboembolic disease and / or cardiomyopathy. Arterial or venous thrombotic conditions, such as venous thrombosis in the presence of heparin therapy, deep phlebitis, pulmonary embolism, atrial fibrillation, heart failure, thrombotic diseases such as congenital or acquired deficiency thrombin III or thrombocytosis, myocardial infarction, coronary artery bypass grafting, stroke.
D'autres avantages et caractéristiques de l'invention apparaîtront au regard des exemples qui suivent.Other advantages and features of the invention will become apparent from the following examples.
Les exemples qui suivent sont donnés à titre illustratif et non limitatif. EXEMPLESThe following examples are given for illustrative and not limiting. EXAMPLES
Exemple 1 : Extraction d'herniarine à partir de d'Artemisia dracunculus par digestionExample 1 Extraction of herniarine from Artemisia dracunculus by digestion
L'Artemisia dracunculus est séchée (Ig) ou congelée (10g), puis broyée. Le broyât est placé dans un bêcher de 250 ml, puis on ajoute de l'eau (10 ml), on chauffe à 600C sous agitation pendant Ih, puis on filtre cette suspension sur fritte. Le filtrat est récupéré, puis réduit à la moitié de son volume initial. La teneur en herniarine est mesurée par CLHP en comparant le profil d'élution avec une solution témoin d'herniarine dans l'eau. La teneur mesurée est de 1,35 % en poids par rapport au poids de matière sèche de plante.Artemisia dracunculus is dried (Ig) or frozen (10g) and then ground. The ground material is placed in a 250 ml beaker, then water (10 ml) is added, the mixture is heated at 60 ° C. with stirring for 1 h and then this suspension is filtered through a frit. The filtrate is recovered and then reduced to half of its initial volume. The herniarin content is measured by HPLC by comparing the elution profile with a control solution of herniarine in water. The measured content is 1.35% by weight relative to the weight of plant solids.
Exemple 2 ; Extraction d'herniarine à partir de d' Artemisia dracunculus par infusion selon le protocole standard de KumagawaExample 2; Extraction of herniarine from Artemisia dracunculus by infusion according to the standard Kumagawa protocol
L'Artemisia dracunculus est séchée (Ig) ou congelée (10g), puis broyée. Le broyât est placé sur un filtre, puis on ajoute de l'eau (10 ml) à température d'ébullition sur le broyât, et on laisse le mélange pendant environ une heure. Le filtrat est récupéré, puis réduit à la moitié de son volume initial.Artemisia dracunculus is dried (Ig) or frozen (10g) and then ground. The ground material is placed on a filter, then water (10 ml) at boiling temperature is added to the ground material, and the mixture is left for about one hour. The filtrate is recovered and then reduced to half of its initial volume.
La teneur en herniarine est mesurée par CLHP en comparant le profil d'élution avec une solution témoin d'herniarine dans l'eau. La teneur mesurée est de 0,75 % en poids par rapport au poids de matière sèche de plante.The herniarin content is measured by HPLC by comparing the elution profile with a control solution of herniarine in water. The measured content is 0.75% by weight relative to the weight of plant solids.
Exemple 3 : Extraction d'herniarine à partir de l'Artemisia dracunculus, la Satureja hortensis, l'Anthriscus cerefolium, l'Anethum graveolens, le Thymus vulgaris L'herniarine a été extraite de différentes plantes selon la méthode décrite dans l'exemple 1. La teneur en herniarine est exprimée en pourcentage en poids par rapport au poids de matière sèche de plante et les résultats obtenus sont présentés dans le tableau ci-dessous.Example 3 Extraction of herniarine from Artemisia dracunculus, Satureja hortensis, Anthriscus cerefolium, Anethum graveolens, Thymus vulgaris Herniarin was extracted from different plants according to the method described in Example 1. The herniarin content is expressed as a percentage by weight relative to the weight of dry matter of plant and the results obtained are shown in the table below. .
Figure imgf000017_0001
Figure imgf000017_0001
Exemple 4 : Extraction d' herniarine à partir de l'Artemisia dracunculus par macérationExample 4 Extraction of herniarine from Artemisia dracunculus by maceration
L'Artemisia dracunculus (Ig) est congelée (10g), puis broyée. Le broyât est placé dans un bêcher de 250 ml, puis on ajoute différents mélanges eau/éthanol (20 ml) ayant un degré alcoolique de 30, 50, 70, 80 et 100.Artemisia dracunculus (Ig) is frozen (10g) and crushed. The ground material is placed in a 250 ml beaker, and then various water / ethanol mixtures (20 ml) having an alcohol content of 30, 50, 70, 80 and 100 are added.
Le mélange est chauffé à une température comprise dans une gamme allant de 25 à 8O0C sous agitation par ultrasons pendant 4h avec prélèvement toutes les 30 minutes. Puis la suspension est filtrée sur fritte. Le filtrat est récupéré, puis réduit à la moitié de son volume initial.The mixture is heated to a temperature ranging from 25 to 80 ° C. with ultrasound stirring for 4 h with sampling every 30 minutes. Then the suspension is filtered on a frit. The filtrate is recovered and then reduced to half of its initial volume.
La teneur en herniarine est mesurée par CLHP. Le titre de la plante en herniarine est exprimée en pourcentage et les résultats obtenus sont présentés dans les tableaux ci- dessous en fonction du degré alcoolique, de la température et de la durée d'extraction utilisés.
Figure imgf000018_0001
The herniarin content is measured by HPLC. The herniarin plant titre is expressed as a percentage and the results obtained are shown in the tables below according to the alcoholic degree, the temperature and the extraction time used.
Figure imgf000018_0001
Les résultats montrent qu'à un degré alcoolique de 30, le titre en herniarine est déjà bon (0,14), et n'augmente pas significativement lorsque le degré alcoolique augmente.The results show that at an alcoholic strength of 30, the herniarine titer is already good (0.14), and does not increase significantly when the degree of alcohol increases.
Figure imgf000018_0002
Figure imgf000018_0002
Les résultats montrent qu'à une température de 300C, le titre en herniarine est optimal (0,33).
Figure imgf000019_0001
The results show that at a temperature of 30 ° C., the herniarine titre is optimal (0.33).
Figure imgf000019_0001
Les résultats montrent qu'au bout de 60 minutes d'extraction, le titre en herniarine se stabilise (0,165) et n'augmente pas significativement si la durée d'extraction est prolongée.The results show that after 60 minutes of extraction, the herniarine titre stabilizes (0.165) and does not increase significantly if the extraction time is prolonged.
Compte tenu de l'ensemble des résultats ci-dessus, il apparaît qu'une extraction optimale de coumarines peut être obtenue par macération de l'A. dracunculus à l'aide d'un mélange hydroalcoolique comprenant jusqu'à 30% d'alcool, à une température de 300C, pendant 60 minutes. Taking into account all the above results, it appears that an optimal extraction of coumarins can be obtained by maceration of the A. dracunculus with a hydroalcoholic mixture comprising up to 30% alcohol, at a temperature of 30 0 C, for 60 minutes.

Claims

REVENDICATIONS
1. Procédé d'extraction comprenant au moins les étapes suivantes : - placer au moins une partie d'au moins une plante dans un solvant polaire constitué d'eau et de 0 à 30% d'un alcool, et éventuellement d'un additif ;1. Extraction process comprising at least the following steps: placing at least a part of at least one plant in a polar solvent consisting of water and 0 to 30% of an alcohol, and optionally an additive ;
- procéder à l'extraction de ladite plante ; et- proceed to the extraction of said plant; and
- récupérer l'extrait obtenu par l'étape précédente, ledit extrait comprenant au moins une partie du solvant et au moins une coumarine.recovering the extract obtained by the preceding step, said extract comprising at least a part of the solvent and at least one coumarin.
2. Procédé selon la revendication 1, caractérisé en ce que :2. Method according to claim 1, characterized in that:
- l'alcool est choisi parmi le méthanol, l'éthanol, le propanol, le butanol, le pentanol ; et l'eau est choisie parmi l'eau osmosée, distillée, permutée .the alcohol is chosen from methanol, ethanol, propanol, butanol and pentanol; and the water is selected from osmosis water, distilled, permuted.
3. Procédé selon l'une des revendications 1 ou 2, caractérisé en ce que le solvant polaire est porté à une pression supérieure à la pression atmosphérique.3. Method according to one of claims 1 or 2, characterized in that the polar solvent is brought to a pressure above atmospheric pressure.
4. Procédé selon la revendication 3, caractérisé en ce que le solvant polaire est de l'eau, de préférence à l'état subcritique.4. Method according to claim 3, characterized in that the polar solvent is water, preferably in the subcritical state.
5. Procédé selon l'une quelconque des revendications 1 à 4, caractérisé en ce que le solvant polaire est porté à une température comprise dans une gamme allant de 4°C à une température de 3000C au-dessus de la température d'ébullition du solvant, de préférence dans une gamme allant de 4°C à la température d'ébullition du solvant, de manière tout à fait préférée dans une gamme allant de la température ambiante à 300C.5. Method according to any one of claims 1 to 4, characterized in that the polar solvent is brought to a temperature in a range from 4 ° C to a temperature of 300 0 C above the temperature of boiling of the solvent, preferably in a range from 4 ° C to the boiling point of the solvent, most preferably in a range from room temperature to 30 ° C.
6. Procédé selon l'une quelconque des revendications 1 à 5, caractérisé en ce que l'étape d'extraction comprend au moins une étape choisie dans le groupe comprenant la décoction, la macération, l'infusion et la percolation.6. Method according to any one of claims 1 to 5, characterized in that the extraction step comprises at least one step selected from the group comprising decoction, maceration, infusion and percolation.
7. Procédé selon la revendication 6, caractérisé en ce que l'étape de macération a une durée allant de 1 minute à 8 heures, de préférence une durée allant de 30 à 60 minutes.7. Method according to claim 6, characterized in that the maceration step has a duration ranging from 1 minute to 8 hours, preferably a duration ranging from 30 to 60 minutes.
8. Procédé selon l'une quelconque des revendications 5 à 7, caractérisé en ce qu'il comprend une étape impliquant le chauffage, en particulier d'une durée allant de 1 seconde à 15 jours, et notamment de 10 secondes à 8 heures.8. Process according to any one of claims 5 to 7, characterized in that it comprises a step involving heating, in particular of a duration ranging from 1 second to 15 days, and in particular from 10 seconds to 8 hours.
9. Procédé selon l'une quelconque des revendications 1 à 8, caractérisé en ce que la partie de plante est broyée, pulvérisée et/ou hachée.9. Method according to any one of claims 1 to 8, characterized in that the plant part is crushed, pulverized and / or chopped.
10. Procédé selon l'une quelconque des revendications 1 à 9, caractérisé en ce que l'extrait est :10. Process according to any one of claims 1 to 9, characterized in that the extract is:
- stérilisé, notamment par chauffage avec ou sans pression et/ou par passage sur une membrane ; et/ousterilized, in particular by heating with or without pressure and / or by passage over a membrane; and or
- désinfecté, notamment par chauffage avec ou sans pression et/ou par au moins un agent désinfectant.disinfected, in particular by heating with or without pressure and / or by at least one disinfecting agent.
11. Procédé selon l'une quelconque des revendications 1 à 10, caractérisé en ce que la plante est choisie dans le groupe des astéracées, des lamiacées, des labiées et des ombellifères et en particulier l' Arternisia dracunculus, la Satureja hortensis, l'Anthriscus cerefolium, l'Anethum graveolens, le Thymus vulgaris. 11. Method according to any one of claims 1 to 10, characterized in that the plant is selected from the group of asteraceae, lamiaceae, labiae and umbelliferae and in particular Arternisia dracunculus, Satureja hortensis, the Anthriscus cerefolium, Anethum graveolens, Thymus vulgaris.
12. Procédé selon l'une quelconque des revendications 1 à 11, caractérisé en ce que la partie de la plante est choisie parmi la racine, l'écorce,la tige, la graine, la fleur, la feuille, la sommité, le fruit.12. Method according to any one of claims 1 to 11, characterized in that the part of the plant is selected from the root, the bark, the stem, the seed, the flower, the leaf, the top, the fruit .
13. Procédé selon l'une quelconque des revendications 1 à 12, caractérisé en ce que le solvant est au moins en partie réduit, voire totalement éliminé, notamment par évaporation, par sublimation, en particulier sous pression réduite .13. Method according to any one of claims 1 to 12, characterized in that the solvent is at least partly reduced or completely eliminated, in particular by evaporation, by sublimation, in particular under reduced pressure.
14. Procédé selon l'une quelconque des revendications 1 à 13, caractérisé en ce que l'extrait comprend de l'herniarine notamment en une teneur allant de 0,1 % à 30 %, de préférence de 0,5 à 15 %, plus préférentiellement de 1 à 5 % en poids par rapport au poids de la plante sèche.14. Method according to any one of claims 1 to 13, characterized in that the extract comprises herniarine in particular in a content ranging from 0.1% to 30%, preferably from 0.5 to 15%, more preferably from 1 to 5% by weight relative to the weight of the dry plant.
15. Procédé selon la revendication 14, caractérisé en ce que l ' extrait comprend en outre au moins une autre coumarine .15. The method of claim 14, characterized in that the extract further comprises at least one other coumarin.
16. Procédé selon l'une quelconque des revendications 1 à 15, caractérisé en ce que le procédé est effectué sous atmosphère inerte, notamment sous azote.16. Process according to any one of Claims 1 to 15, characterized in that the process is carried out under an inert atmosphere, in particular under nitrogen.
17. Procédé selon l'une quelconque des revendications 1 à 16, caractérisé en ce que l'étape d'extraction est continue ou discontinue.17. Method according to any one of claims 1 to 16, characterized in that the extraction step is continuous or discontinuous.
18. Procédé selon l'une quelconque des revendications 1 à 17, caractérisé en ce que la plante avant d'être utilisée a été congelée, en particulier lorsque la plante est placée dans le solvant polaire, elle est à l'état congelé. 18. Process according to any one of claims 1 to 17, characterized in that the plant before being used has been frozen, in particular when the plant is placed in the polar solvent, it is in the frozen state.
19. Procédé selon l'une quelconque des revendications 1 à 17, caractérisé en ce la plante est à l'état sec lorsqu'elle est placée dans le solvant polaire.19. Process according to any one of claims 1 to 17, characterized in that the plant is in the dry state when it is placed in the polar solvent.
20. Procédé selon l'une quelconque des revendications 1 à 17, caractérisé en ce que la plante est à l'état frais lorsqu'elle est placée dans le solvant polaire.20. Process according to any one of claims 1 to 17, characterized in that the plant is in the fresh state when it is placed in the polar solvent.
21. Extrait, notairanent aqueux ou hydroalcoolique, d'une plante sous forme liquide ou solide comprenant une teneur en coumarine et notamment en herniarine supérieure ou égale à 0,05% en poids par rapport au poids total de l'extrait, susceptible d'être obtenu par un procédé selon l'une quelconque des revendications 1 à 20.21. Extract, aqueous or hydroalcoholic, of a plant in liquid or solid form comprising a content of coumarin and in particular herniarine greater than or equal to 0.05% by weight relative to the total weight of the extract, susceptible to obtainable by a process according to any one of claims 1 to 20.
22. Extrait selon la revendication 21, caractérisé en ce que la plante est choisie dans le groupe des astéracées, des lamiacées, des labiées et des ombellifères et en particulier l'Artemisia dracunculus, la Satureja hortensis, l'Anthriscus cerefolium, l'Anethum graveolens, le Thymus vulgaris.22. Extract according to claim 21, characterized in that the plant is selected from the group of asteraceae, lamiaceae, labiae and umbelliferae and in particular Artemisia dracunculus, Satureja hortensis, Anthriscus cerefolium, Anethum. graveolens, Thymus vulgaris.
23. Composition comprenant au moins un extrait tel que défini selon l'une des revendications 21 ou 22.23. Composition comprising at least one extract as defined according to one of claims 21 or 22.
24. Composition selon la revendication 23, caractérisée en ce que ladite composition est choisie dans le groupe comprenant les compositions alimentaires notamment supplétives, cosmétiques, thérapeutiques, nutraceutiques, cosméceutiques et les compléments alimentaires, produits diététiques, dispositifs médicaux en particulier les compositions alimentaires, nutraceutiques, cosméceutiques et les compléments alimentaires et tout particulièrement les compositions nutraceutiques, cosméceutiques et les compléments alimentaires. 24. A composition according to claim 23, characterized in that said composition is chosen from the group comprising food compositions including suppletive, cosmetic, therapeutic, nutraceutical, cosmeceutical and food supplements, dietary products, medical devices, in particular food compositions, nutraceuticals. , cosmeceuticals and dietary supplements and especially nutraceutical, cosmeceutical and dietary supplements.
25. Composition selon l'une des revendications 23 ou 24, caractérisée en ce qu'elle comprend en outre au moins un agent anti-coagulant tel que de l 'Allium sativum ou un extrait d'Allium sativum.25. Composition according to one of claims 23 or 24, characterized in that it further comprises at least one anti-coagulant agent such as Allium sativum or an extract of Allium sativum.
26. Utilisation d'un extrait tel que défini selon l'une des revendications 21 ou 22 comme :26. Use of an extract as defined in one of claims 21 or 22 as:
- agent anti-coagulant, en particulier en tant qu'agent anti-aggrégant des fibrines et/ou inhibiteurs de la synthèse des facteurs de la coagulation vitaminoK dépendant,anti-coagulant agent, in particular as an anti-aggregating agent for fibrins and / or inhibitors of the synthesis of vitamin-dependent coagulation factors,
- agent stimulateur du drainage lymphatique, et/ou- stimulating agent of lymphatic drainage, and / or
- agent stimulateur protéolytique des macrophages,macrophage proteolytic stimulating agent,
dans une composition, en particulier alimentaire notamment supplétive, cosmétique, thérapeutique, nutraceutique, cosméceutique et un complément alimentaire, produit diététique, dispositif médical.in a composition, in particular food particularly supportive, cosmetic, therapeutic, nutraceutical, cosmeceutical and a dietary supplement, dietary product, medical device.
27. Utilisation d'un extrait tel que défini selon l'une des revendications 21 ou 22 en tant qu'agent rodenticide.27. Use of an extract as defined in one of claims 21 or 22 as a rodenticide agent.
28. Utilisation d'un extrait tel que défini selon l'une des revendications 21 ou 22 en tant qu'agent anti-fongique.28. Use of an extract as defined in any of claims 21 or 22 as an anti-fungal agent.
29. Utilisation d'un extrait tel que défini selon l'une des revendications 21 ou 22 pour la préparation d'un médicament destiné à prévenir et/ou à traiter des varices, des thrombophlébites, la maladie thrombo-embolique veineuse, la cardiomyopathie. 29. Use of an extract as defined in one of claims 21 or 22 for the preparation of a medicament for preventing and / or treating varicose veins, thrombophlebitis, venous thromboembolic disease, cardiomyopathy.
PCT/FR2008/000462 2007-04-03 2008-04-03 Process for extracting coumarins WO2008142267A2 (en)

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FR0754233 2007-04-03
FR0754233A FR2914552B1 (en) 2007-04-03 2007-04-03 PROCESS FOR EXTRACTING COUMARINS

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WO2008142267A3 WO2008142267A3 (en) 2009-03-12

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NL1038343C2 (en) * 2010-10-29 2012-05-02 Bozo B V PHYTOTHERAPEUTIC PREPARATION WITH STIMULATING EFFECT ON LIBIDO, SPERMATOGENESE AND BODY HYGIENE.

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2471293A (en) * 2009-06-24 2010-12-29 Kenneth Davison The extraction of pharmacological agents from medicinal herbs using subcritical water
GB2471293B (en) * 2009-06-24 2013-10-09 Kenneth Davison The sub-critical water extraction of red clover

Also Published As

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FR2914552A1 (en) 2008-10-10
FR2914552B1 (en) 2012-08-03
WO2008142267A3 (en) 2009-03-12
EP2271336A2 (en) 2011-01-12

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