WO2013019049A1 - Complexe comprenant des glycosides de stéviol ou de la racine de réglisse et matière faiblement soluble - Google Patents

Complexe comprenant des glycosides de stéviol ou de la racine de réglisse et matière faiblement soluble Download PDF

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WO2013019049A1
WO2013019049A1 PCT/KR2012/006069 KR2012006069W WO2013019049A1 WO 2013019049 A1 WO2013019049 A1 WO 2013019049A1 KR 2012006069 W KR2012006069 W KR 2012006069W WO 2013019049 A1 WO2013019049 A1 WO 2013019049A1
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poorly soluble
licorice
complex
microwave
stevia
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PCT/KR2012/006069
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English (en)
Korean (ko)
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이우송
김영민
노문철
류영배
박수진
정형재
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한국생명공학연구원
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Publication of WO2013019049A1 publication Critical patent/WO2013019049A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • 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
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/30—Artificial sweetening agents
    • A23L27/33—Artificial sweetening agents containing sugars or derivatives
    • A23L27/36—Terpene glycosides
    • 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
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
    • A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
    • A61K31/704—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin
    • 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)
    • A61K36/25—Araliaceae (Ginseng family), e.g. ivy, aralia, schefflera or tetrapanax
    • A61K36/258—Panax (ginseng)
    • 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)
    • A61K36/48—Fabaceae or Leguminosae (Pea or Legume family); Caesalpiniaceae; Mimosaceae; Papilionaceae
    • A61K36/484—Glycyrrhiza (licorice)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates

Definitions

  • the present invention provides a poorly soluble substance-containing complex with increased solubility, a method for preparing the same, a pharmaceutical or food composition comprising the complex, a cosmetic composition or a feed composition comprising the complex, a solubilizer for increasing the solubility of the poorly soluble substance, and A method for solubilizing poorly soluble substances.
  • Solubilization of poorly soluble drugs is an essential technique for administering drugs into the body in oral and injectable form.
  • a method of solubilizing a poorly water-soluble drug firstly, the drug is dissolved in a mixed solvent of a water-miscible organic solvent and water; Second, modifying the structural formula of the drug to form salts of acids or bases that are soluble in water; Third, combining the drug with a third material to form a complex that is soluble in water; Fourth, a method of micellizing a drug in an aqueous solution by adding a surfactant is used (Leon Lachman, "The Theory and Practice of Industrial Pharmacy", Lea & Febiger, Philadelphia, 1986).
  • Alza has developed a technology called nanocrystals, which uses a special mill to break down the particles into nano units and uses new additives to prevent agglomeration between particles. It is applied to soluble drugs and immunosuppressive sirolimus.
  • Glytech is a technology that can promote their absorption by using a taxane-based anticancer agent that is blocked by the P-glycoprotein in combination with a P-glycoprotein inhibitor.
  • Knoll a subsidiary of Abbott, has developed a technology called Meltrex, which significantly improves bioavailability by melting poorly soluble drugs and substrates at high temperatures and then cooling them to amorphize them.
  • SMEDDS self-microemulsifying drug delivery system
  • Paclitaxel which has a market scale of 2 trillion won per year as a single anticancer drug source approved by the US Food and Drug Administration (FDA), is a poorly soluble substance and is not dispersed in distilled water at all. Because of the mixed use has the disadvantage of causing serious side effects to the human body. Therefore, in order to solve this problem, Chitolife Co., Ltd. and Biomedical Polymer Research Team of Sunchon National University prepared advanced chitosan, a non-toxic natural polymer material, and applied it to paclitaxel in 2010, using existing organic solvents. It is much safer than the preparation method, and has a very good redispersibility in distilled water, making the injection formulation much easier to use as an injection.
  • FDA US Food and Drug Administration
  • a method of solubilizing without changing the chemical structure of a drug using a surfactant is widely used as a method for solubilizing various drugs.
  • the surfactant nonionic surfactants such as sorbitan fatty acid ester derivatives (Tween) and polyoxyethylene monoalkyl ether derivatives (BRIJ and MYRJ series) are widely used.
  • Tween sorbitan fatty acid ester derivatives
  • BRIEJ and MYRJ series polyoxyethylene monoalkyl ether derivatives
  • these surfactants are very limited in use due to side effects such as hypersensitivity reactions, there is a disadvantage that the drug is precipitated when left for a relatively long time due to the very low stability of micelles.
  • the present inventors are poorly soluble in a solution to which steviol glycoside or licorice extract is added in order to maximize the solubility of the poorly soluble materials. Not only did solubility increase by dissolving the substance, but also the solubility of the poorly soluble substance was significantly increased as a result of the microwave treatment after dissolving the poorly soluble substance in the solution to which the steviol glycoside or licorice extract was added. By confirming that the present invention was completed, the present invention was completed.
  • Still another object of the present invention is to provide a cosmetic composition comprising the complex.
  • Another object of the present invention is to provide a feed composition comprising the complex.
  • Another object of the present invention relates to a method for producing the composite.
  • Another object of the present invention is to provide the use of the solubilizer.
  • Steviol glycosides included in the complex of the present invention can be used as a solubilizer of a poorly soluble material, the formulation obtained by treating the complex containing the solubilizer with microwave solubility of the poorly soluble material
  • This markedly elevated feature is that it is easy to prepare in oral and injectable formulations, has excellent storage stability, and has excellent drug delivery ability and absorption rate in the body.
  • Figure 1 shows the solubility of curcumin in each condition after dissolving curcumin in a solution containing stevioside at different temperatures.
  • Figure 2 shows the solubility of curcumin in each case by dissolving curcumin in a solution containing steviosides of different concentrations, followed by sonication, a wet sterilizer or a microwave.
  • Figure 3 shows the correlation of four factors by surface response analysis: a, microwave power-stevioside concentration; b, curcumin (KW-100) concentration-microwave power; c, reaction time-microwave power; d, curcumin concentration-stevioside concentration; e, reaction time-stevioside concentration; f, reaction time-curcumin concentration.
  • Figure 4 shows the solubility of curcumin in each case by dissolving curcumin in a solution containing licorice extract of varying concentrations, followed by sonication, wet sterilizer or microwave.
  • the present invention is a steviol glycoside or stevia, or licorice comprising the same; And a poorly soluble material.
  • the present invention provides a pharmaceutical or food composition comprising the complex.
  • the present invention provides a cosmetic composition comprising the complex.
  • the present invention provides a feed composition comprising the complex.
  • the present invention is a steviol glycoside or stevia, or licorice comprising the same, and the first step of mixing a poorly soluble material; And a second step of treating the mixture obtained in the first step with microwaves, thereby providing a method for producing a poorly soluble substance-containing composite having increased solubility.
  • the present invention provides a solubilizer containing licorice as an active ingredient.
  • the present invention provides a method of solubilizing poorly soluble material, comprising mixing licorice with poorly soluble material.
  • the present invention provides the use of licorice in the preparation of a solubilizer.
  • the present invention is a steviol glycoside or stevia, or licorice comprising the same; And a poorly soluble material.
  • the present invention is characterized by using a steviol glycoside as a surfactant that is a solubilizer for poorly soluble substances.
  • the poorly soluble substance when the poorly soluble substance is dissolved in a solution containing steviol glycosides, it was confirmed that the solubility of the poorly soluble substance is significantly increased than when dissolved in water, so that the solubility is increased according to the present invention
  • the complex may comprise stevio glycoside as one component.
  • the term “steviol glycoside” is a compound present in the leaves of Stevia rebaudiana Bertoni, and means a substance that gives a sweet taste.
  • the steviol glycosides are not limited thereto, but the aqueous extract obtained by extracting dried leaves with hot water is concentrated by treatment with an adsorbent resin, and then purified by recrystallization using methyl alcohol or ethyl alcohol, and then dried. And commercially available ones can be used.
  • steviol glycoside is not limited, but stevioside, rebaudioside, rebaudioside A, rebaudioside C, and dulcoside A found in high content in stevia plants
  • rebaudioside B, D, E, F, rubuososide, steviool biosides, steviol monosides and the like can be included, specific chemical structures are as follows.
  • the steviol glycosides of the present invention include enzymatically treated stevia (SWETA), SWETA ML01 containing 50% steviol glycoside, SWETA75 containing 75% steviol glycoside, and the like according to the content and type of steviol glycoside of the chemical structure.
  • SWETA enzymatically treated stevia
  • SWETA ML01 containing 50% steviol glycoside
  • SWETA75 containing 75% steviol glycoside
  • the enzyme treatment stevioside refers to a form in which glucose is added to stevioside (ie, glucosyl stevioside) using a sugar transfer enzyme.
  • the present invention may be prepared using, but not limited to, CGTase (cyclodextringlucanotransferase) or glucose transferase of various microbial origins.
  • steviol glycosides are preferably steviosides.
  • the present invention is to use stevia containing a high content of stevioside, rebaudioside A, rebaudioside C, dulcoside, etc. as a solubilizer for poorly soluble substances. It is characteristic.
  • Stevia is a perennial herbaceous perennial plant with dicotyledonous plants, lanterns, asteraceae, perennial herbaceous perennial herb, inhabiting borderlands and streams and wetlands around South America, Paraguay, Argentina, and Brazil.
  • stevia may be purchased and used commercially, or may be used collected or grown in nature.
  • Stevia is preferably used in the present invention, but is not limited thereto.
  • the stevia is any species of the genus Stevia, such as Stevia rebaudiana, Stevia eupatoria, Stevia ovata, Stevia plummerae, Stevia salicifolia And Stevia serrata.
  • Stevia in the present invention includes the plant itself or a pulverized product, an extract or fraction thereof.
  • stevia may contain about 10 to 95%, preferably about 40 to 85% of steviosides and steviol.
  • the stevia extract can be obtained by extracting with water, a lower alcohol having 1 to 4 carbon atoms (C 1 ⁇ C 4 ) or a mixed solvent thereof. Specifically, about 2 to 10 times the weight of stevia, preferably 2 to 5 times the volume of lower alcohols such as water, ethanol and methanol, preferably ethanol 20 to 50 ° C, preferably 25 to 30 ° C After extraction was obtained by stirring extraction, ultrasonic extraction, continuous extraction 2-3 times by hot water extraction method at 100 °C, filtered through filtrate and the filtrate was removed with a rotary depressurizer, the residue was vacuum lyophilized, hot air drying stevia extract Can be obtained.
  • the stevia extract of the present invention may include any one or more of an extract obtained by the extraction treatment, a dilution or concentrate of the extract, a dried product obtained by drying the extract, and these modifiers or purified products.
  • the present invention is characterized by using licorice as a solubilizer for poorly soluble substances.
  • Licorice is the root of a plant in the genus Glycyrrhiza, which is known to stop coughing, reduce fever, relax the stomach and relieve an emergency.
  • the main component of licorice extract is glycyrrhizinic acid, a white or colorless crystalline powder.
  • Licorice in the present invention includes the plant itself or the pulverized product, extract or fraction thereof. Preferably it may be licorice extract.
  • the licorice extract may be prepared using conventional extraction methods in the art, such as ultrasonic extraction, filtration and reflux extraction.
  • it may be a liquorice dry product obtained by crushing the removed liquorice debris by washing and drying of water, extracted with an alcohol or a mixed solvent of a carbon number of 1 to 4 (C 1 ⁇ C 4) extract, and more preferably It may be an extract extracted with C 1 ⁇ C 4 alcohol, most preferably may be an extract extracted with methanol or ethanol.
  • the extraction solvent is preferably 2 to 20 times the dry weight of licorice.
  • the licorice dry matter is chopped, and then put into an extraction container, a lower alcohol of C 1 to C 4 or a mixed solvent thereof, preferably methanol or ethanol, and allowed to stand at room temperature for a certain period of time, followed by filtration to obtain an alcohol extract. .
  • the extraction is preferably left for 1 week at room temperature, after which it may be further subjected to methods such as concentration or lyophilization.
  • the complex of the present invention may be prepared by purchasing a licorice extract on the market.
  • licorice extract when the poorly soluble substance was dissolved in the solvent containing licorice extract, it was confirmed that the solubility of the poorly soluble substance was significantly increased than when dissolved in water, licorice extract can be used as a solubilizer of poorly soluble substance I found it for the first time.
  • the term “solubilization” refers to a phenomenon in which the solubility of a material that is less soluble in water increases due to the presence of a substance such as a surfactant. Solubilizing oil-soluble vitamins and hormones, such as water-soluble or mixed with fungicides such as phenols to increase the effect, methods for promoting emulsion polymerization are widely applied, etc.
  • a solubilizer steviol glycosides or the like Use stevia, or licorice.
  • the complex of the present invention may be mixed with a steviol glycoside or stevia including the same or licorice with a poorly soluble material to form a complex having a structure in which the poorly soluble material is easily dissolved.
  • steviol glycosides, stevia or licorice containing a range of ratios are not limited, but steviol glycosides or stevia is contained in a concentration of 0.1 to 25% (w / v) (based on solids)
  • licorice is preferably included at a concentration of 0.1 to 30% (w / v) (based on solids).
  • the steviol glycoside or stevia is preferably contained at 1 to 25% (w / v) (based on solids), and licorice is included at a concentration (based on solids) of 0.1 to 25% (w / v). It is desirable to be.
  • the complex of the present invention may be a formulation obtained by treating microwaves.
  • microwave in the present invention is an alternating signal between 300 MHz and 300 GHz in the frequency band or between 1 m and 1 mm in the case of wavelength.
  • a poorly soluble substance when a poorly soluble substance is added to a solution in which stevio glycoside, stevia extract, or licorice extract is mixed, and a homogeneous mixed solution is prepared by sonication, further treatment with ultrasonic treatment is performed.
  • a solubility of the poorly soluble substance by dividing it into the case of microwave treatment and the case of microwave treatment, it was confirmed that the solubilization of the poorly soluble substance was significantly increased when the microwave treatment was performed.
  • the solubility of the poorly soluble material was significantly increased when the microwaves were treated with a wet sterilizer, that is, when it was treated with a high temperature of about 121 ° C. By simply increasing the temperature it can be seen that the solubility is not increased. This is achieved by treating microwaves with a combination of steviol glycosides or licorice that acts as a surfactant and homogenized sparingly soluble material due to sonication, thereby forming a more detailed molecular structure by the instantaneous heat and the wavelength and / or frequency of microwaves alone. Is assumed to be solubilized.
  • the complex is preferably a steviol glycoside or a stevia including the same, or a liquor obtained by mixing the licorice and a poorly soluble substance, followed by sonication. More preferably, steviol glycosides or stevia or licorice comprising the same, and poorly soluble materials are mixed and sonicated, followed by treatment with a wet autoclave, microwave or a mixture thereof, most preferably. Preferably a formulation obtained by treating microwaves.
  • the method of treating the microwave is not limited thereto, but may be reacted to a microwave oven in operation (including general household or synthetic only).
  • the microwave is preferably treated for 1 minute to 20 minutes at 600 W to 800 W in a general household microwave oven, and more preferably, 10 to 20 minutes at 650 W to 750 W, and even more.
  • the treatment is performed at 700 W for 15 minutes.
  • the microwave can be treated for 1 minute to 100 minutes at 50 W to 300 W in a microwave for synthesis only, preferably 1 to 20 minutes to 140 W to 240 W. More preferably, the treatment is performed at 160W to 220W for 6 minutes to 12 minutes, and still more preferably at 180W to 200W for 7 minutes to 10 minutes.
  • the number of microwave treatments is not limited, but is preferably performed two or more times.
  • it can be obtained by adding a step of cooling the complex between each reaction, the formulation can be obtained by the further step of sonicating before reacting in the microwave.
  • the term “poorly soluble substance” refers to a substance having low solubility in water, and specifically, may be a substance having a solubility in water of 50 mg / ml or less.
  • the poorly soluble substance may be, for example, a poorly soluble anticancer agent, an antibacterial agent, a steroid, an anti-inflammatory drug, a sex hormone, an immunosuppressant, an antiviral agent, an anesthetic agent, an antiemetic agent or an antihistamine, and more specifically, paclitaxel, paclitaxel Derivatives, taxotere, adriamycin, teniposide, etoposide, daunomycin, methotrexate, mitomycin C, mitomycin C, carmustine carmustine, busulfan, dactinomycin, lomustine, megestrol acetate, melphalan, mitoxantrone, indomethacin , Etodolac
  • the curcuminoid compound is separated from the turmeric extract, and among them, curcumin having a low solubility (curcumin, solubility of about 11 mg / L) at a concentration of 10 mg / ml, various steviol glycosides It was dissolved in the solution containing.
  • curcumin solubility of about 11 mg / L
  • resveratrol or glucosyl resveratrol was dissolved in a solution containing stevioside, and it was confirmed that 6,200 mg / L resveratrol and 8500 mg / L of glucosyl resveratrol were dissolved. As a result, it was confirmed that the solubility was increased to 9,400 mg / L for resveratrol and 14,300 mg / L for glucosyl resveratrol.
  • the present invention provides a new type of complex which significantly increases the solubility of poorly soluble materials.
  • the present invention relates to a pharmaceutical or food composition comprising the complex described above.
  • the complex is characterized in that it comprises a steviol glycoside or stevia, or licorice containing the same as a solubilizer of poorly soluble substances.
  • the complex is a complex in which the solubility of the poorly soluble substance is significantly increased.
  • the complex When used in a pharmaceutical or food composition, the complex is easy to prepare in oral and injectable form, has excellent storage stability, and delivers drugs. It is characterized by excellent ability and absorption in the body.
  • the therapeutic disease of the pharmaceutical composition of the present invention may vary depending on the type of poorly soluble substance included in the complex, for example, if paclitaxol is included in the complex of the present invention as a poorly soluble substance, the composition may be used for anticancer use. That is, it may be used for the prevention or treatment of cancer, and if curcumin is included in the complex of the present invention as a poorly soluble substance, it may be used for antitumor or anti-inflammatory use, which is a medicinal use of curcumin.
  • composition of the present invention may further comprise a pharmaceutically acceptable carrier.
  • the composition comprising a pharmaceutically acceptable carrier may be in various oral or parenteral formulations.
  • diluents or excipients such as fillers, extenders, binders, wetting agents, disintegrating agents, and surfactants are usually used.
  • Solid form preparations for oral administration include tablets, pills, powders, granules, capsules, and the like, which form at least one excipient such as starch, calcium carbonate, sucrose or lactose (at least one compound). lactose) and gelatin.
  • lubricants such as magnesium stearate, talc and the like are also used.
  • Liquid preparations for oral administration include suspensions, liquid solutions, emulsions, and syrups, and various excipients such as wetting agents, sweeteners, fragrances, and preservatives, in addition to commonly used simple diluents such as water and liquid paraffin, may be included.
  • Formulations for parenteral administration include sterile aqueous solutions, non-aqueous solvents, suspensions, emulsions, lyophilized preparations, suppositories.
  • non-aqueous solvent and the suspension solvent propylene glycol, polyethylene glycol, vegetable oil such as olive oil, injectable ester such as ethyl oleate, and the like can be used.
  • As the base of the suppository witepsol, macrogol, tween 61, cacao butter, laurin butter, glycerogelatin and the like can be used.
  • the pharmaceutical or food composition is selected from the group consisting of tablets, pills, powders, granules, capsules, suspensions, liquid solutions, emulsions, syrups, sterile aqueous solutions, non-aqueous solutions, suspensions, emulsions, lyophilized preparations and suppositories. It can have either formulation.
  • Examples of the food to which the complex can be added include dairy products including meat, sausage, bread, chocolate, candy, snacks, confectionery, pizza, ramen, other noodles, gums, ice cream, various soups, drinks, tea, drinks, Alcoholic beverages and vitamin complexes, and the like and include all of the health foods in the conventional sense.
  • the health beverage composition of the present invention may contain various flavors or natural carbohydrates, etc. as additional components, as in the general beverage.
  • Natural carbohydrates described above are glucose, monosaccharides such as fructose, disaccharides such as maltose and sucrose, and polysaccharides such as dextrin, cyclodextrin, sugar alcohols such as xylitol, sorbitol, and erythritol.
  • sweetening agent natural sweetening agents such as tautin and stevia extract, synthetic sweetening agents such as saccharin and aspartame, and the like can be used.
  • the proportion of the natural carbohydrate is generally about 0.01 to 0.04 g, preferably about 0.02 to 0.03 g per 100 mL of the composition of the present invention.
  • the composition of the present invention includes various nutrients, vitamins, electrolytes, flavors, coloring agents, pectic acid and salts thereof, alginic acid and salts thereof, organic acids, protective colloidal thickeners, pH adjusting agents, stabilizers, preservatives, glycerin, alcohols, And a carbonation agent used for the carbonated beverage.
  • the proportion of such additives is not critical but is usually selected in the range of 0.01 to 0.1 parts by weight per 100 parts by weight of the composition of the present invention.
  • the composition of the present invention may contain a flesh for preparing natural fruit juice, fruit juice beverage and vegetable beverage.
  • the proportion of such pulp is not critical, but is generally selected in the range of 0.01 to 10 parts by weight per 100 parts by weight of the composition of the present invention.
  • the present invention relates to a method for preventing or treating a disease by administering the complex as described above to a subject.
  • the complex is a complex in which the solubility of the poorly soluble substance is significantly increased, and the disease may vary depending on the type of the poorly soluble substance.
  • the term "individual” means all animals including humans that may be infected with the disease, and by administering the complex described in the present invention to the individual, the disease can be effectively prevented and treated.
  • the route of administration of the complex can be administered via any general route as long as it can reach the target tissue.
  • the complex of the present invention may be administered as desired, but is not limited to intraperitoneal administration, intravenous administration, intramuscular administration, subcutaneous administration, intradermal administration, oral administration, intranasal administration, pulmonary administration, rectal administration.
  • the complex may also be administered by any device in which the active agent may migrate to the target cell.
  • the present invention relates to a cosmetic composition comprising the complex described above.
  • the complex is characterized in that it comprises a steviol glycoside or stevia, or licorice containing the same as a solubilizer of poorly soluble substances.
  • the complex is a complex in which the solubility of the poorly soluble substance is significantly increased, and when it is used in a cosmetic composition, it is easy to be formulated into various forms of cosmetics.
  • the cosmetic composition of the present invention may vary depending on the kind of poorly soluble substance included in the complex.
  • the cosmetic composition may be used as a cosmetic composition for whitening.
  • the cosmetic composition of the present invention may be prepared in any formulation commonly prepared in the art, for example, solutions, suspensions, emulsions, pastes, gels, creams, lotions, powders, soaps, surfactant-containing cleansing , Oils, powder foundations, emulsion foundations, wax foundations and sprays, and the like, but are not limited thereto. More specifically, it may be prepared in the form of a flexible lotion, astringent lotion, nutrition lotion, nutrition cream, massage cream, essence, eye cream, cleansing cream, cleansing foam, cleansing water, pack, spray or powder.
  • the formulation of the present invention is a paste, cream or gel, animal oil, vegetable oil, wax, paraffin, starch, trakant, cellulose derivative, polyethylene glycol, silicone, bentonite, silica, talc or zinc oxide, etc. may be used as carrier components.
  • animal oil vegetable oil, wax, paraffin, starch, trakant, cellulose derivative, polyethylene glycol, silicone, bentonite, silica, talc or zinc oxide, etc.
  • trakant cellulose derivative
  • polyethylene glycol silicone
  • bentonite silica
  • talc or zinc oxide etc.
  • the formulation of the present invention is a powder or spray
  • lactose, talc, silica, aluminum hydroxide, calcium silicate or polyamide powder may be used as the carrier component.
  • a solvent, solubilizer or emulsifier is used as the carrier component, such as water, ethanol, isopropanol, ethylcarbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 1 Fatty acid esters of, 3-butylglycol oil, glycerol aliphatic ester, polyethylene glycol or sorbitan.
  • liquid carrier diluents such as water, ethanol or propylene glycol
  • suspending agents such as ethoxylated isostearyl alcohol, polyoxyethylene sorbitol ester and polyoxyethylene sorbitan ester, microcrystals Soluble cellulose, aluminum metahydroxy, bentonite, agar or tracant and the like can be used.
  • the carrier component is an aliphatic alcohol sulfate, an aliphatic alcohol ether sulfate, a sulfosuccinic acid monoester, isethionate, an imidazolinium derivative, a methyltaurate, a sarcosinate, a fatty acid amide ether.
  • Sulfates, alkylamidobetaines, aliphatic alcohols, fatty acid glycerides, fatty acid diethanolamides, vegetable oils, lanolin derivatives or ethoxylated glycerol fatty acid esters and the like can be used.
  • the present invention relates to a feed composition comprising the complex described above.
  • the complex is characterized in that it comprises a steviol glycoside or stevia, or licorice containing the same as a solubilizer of poorly soluble substances.
  • the feed composition also includes the form of a feed additive.
  • the use of the feed composition of the present invention may vary depending on the type of poorly soluble material included in the complex.
  • the poorly soluble substance is curcumin
  • the feed composition may be used as a feed composition to improve influenza virus infection disease and have an anti-influenza effect.
  • the feed may be classified into various types according to nutritional value, main ingredient, distribution, moisture content, blending state and processing type, and the feed may be used as a feed, a rich feed, a supplementary feed, a protein feed, a starch feed, a fat feed or a fiber feed. Possible, but not limited to.
  • the feed composition may additionally contain a carrier that is acceptable to poultry and livestock.
  • the feed can be added as it is or a known carrier, stabilizer and the like, and various nutrients such as vitamins, amino acids and minerals, antioxidants, antibiotics, antibacterial agents and other additives can be added as necessary.
  • the shape may be in a suitable state such as powder, granules, pellets or suspension.
  • poultry, livestock, and the like can be supplied alone or mixed with feed.
  • the present invention relates to a quasi-drug composition comprising the complex described above.
  • the complex is characterized in that it comprises a steviol glycoside or stevia, or licorice containing the same as a solubilizer of poorly soluble substances.
  • the use of the quasi-drug composition of the present invention may vary depending on the kind of poorly soluble substance included in the complex.
  • the type of quasi-drug is not limited thereto, but may be, for example, a disinfectant cleaner, a disinfectant, a shower foam, a gagreen, a wet tissue, a detergent soap, a shampoo, a hand wash, a humidifier filler, a mask, an ointment, or a filter filler.
  • the present invention is a steviol glycoside or stevia, or licorice comprising the same, and the first step of mixing a poorly soluble material; And a second step of subjecting the mixture obtained in the first step to microwaves (microwaves).
  • the steviol glycosides are stevioside, rebaudioside A, rebaudioside C, dulcoside A, which are found in high content in stevia plants, as well as rebaudioside B, D , E, rubisoside, steviol bioside, steviol monoside, SWETA, SWETA ML01, SWETA75 and the like can be included, but is not limited thereto.
  • the poorly soluble substance can be used without limitation as long as it is a substance having low solubility.
  • the present invention is steviol glycosides or stevia, or licorice containing the same, and the poorly soluble substances are mixed in a solvent, or steviol glycosides or stevia, or licorice containing the same, poorly soluble in the solution
  • the material can be added and mixed.
  • the steviol glycoside or stevia in the first step is preferably included in a concentration (solid basis) of 0.1 to 25% (w / v), the licorice is a concentration (solid content of 0.1 to 30% (w / v) It is preferable to include as a reference).
  • the first step is preferably carried out at 60 °C to 80 °C, more preferably at 65 °C to 75 °C, even more preferably at 70 °C.
  • the method of processing the microwave is not limited to this, but may be reacted to a microwave oven in operation (including general household or synthetic only).
  • the microwave is preferably treated for 1 minute to 20 minutes at 600 W to 800 W in a general household microwave oven, and more preferably, 10 to 20 minutes at 650 W to 750 W, even more.
  • the treatment is performed at 700 W for 15 minutes.
  • the microwave can be treated for 1 minute to 100 minutes at 50 W to 300 W in a microwave for synthesis only, preferably 1 to 20 minutes to 140 W to 240 W. More preferably, the treatment is carried out at 160W to 220W for 6 minutes to 12 minutes, and even more preferably at 180W to 200W for 7 minutes to 10 minutes.
  • the number of microwave treatments is not limited, but is preferably performed two or more times.
  • it can be obtained by adding a step of cooling the complex between each reaction, the formulation can be obtained by the further step of sonicating before reacting in the microwave.
  • the solubility of the poorly soluble substance was measured, The solubilization of poorly soluble substances was significantly increased compared to those dissolved in water.
  • the solubility of the poorly soluble substance was measured, and when dissolved in water, after the first step after sonication or wet sterilizer treatment It can be seen that the solubility of the poorly soluble substance was significantly increased.
  • the present invention relates to a solubilizer containing licorice as an active ingredient.
  • licorice comprising the form of the licorice extract of the present invention can be used as a solubilizer, which promotes solubilization of poorly soluble substances.
  • Licorice extract in the solubilizer is not limited thereto, but is preferably included in a concentration of 0.1 to 25% (w / v).
  • the present invention relates to a method of solubilizing poorly soluble materials, comprising mixing licorice with poorly soluble materials.
  • the licorice may be licorice extract.
  • the mixing of the licorice and the poorly soluble substance may be performed as a step of mixing the licorice extract and the poorly soluble substance by adding a poorly soluble substance to the solution containing licorice. Or by mixing licorice extract and poorly soluble material in a solvent.
  • the licorice may increase the solubility of the poorly soluble material and solubilize the poorly soluble material.
  • the method may further comprise treating the microwaves after mixing licorice and the poorly soluble material.
  • the present invention provides the use of licorice in the preparation of solubilizers.
  • the licorice is preferably licorice extract.
  • licorice has a use that can be used to prepare solubilizers of poorly soluble materials.
  • the turmeric used in the present embodiment is generally available in Chinese medicine or on the market, and is dried in the form of dried Root of Curcuma longa Linne and then dried to obtain powder of the present invention to efficiently obtain the extract of the present invention. It was used by grinding. 7.5 L of 100% ethanol (EtOH) was added to 1.6 kg of turmeric, and the mixture was left to stand at room temperature for 5 days, filtered through a filter paper, and concentrated to obtain turmeric ethanol extract (170 g).
  • Example 1-1 170 g of ethanol extract of turmeric obtained in Example 1-1 was added and suspended in 1 L of water. This was placed in a separatory funnel, and fractional extraction using n-hexane and ethyl acetate in order to obtain n-hexane soluble extract (23 g), ethyl acetate soluble extract (85 g) and water soluble extract (34 g).
  • the crude extract was suspended in 1 L of water, mixed with the same amount of ethyl acetate, and fractionated. The procedure was repeated four times to obtain 4 L of ethyl acetate fraction. The ethyl acetate soluble fraction was concentrated under reduced pressure to obtain 80 g of an ethyl acetate soluble extract.
  • the chloroform: methanol 20: 1 fraction in the E. coli ethanol extract, ethyl acetate fraction, and ethyl acetate fraction column chromatography obtained above was analyzed using LC-MS to confirm the resveratrol content.
  • SWETA enzyme treatment stevia
  • curcumin when curcumin was dissolved in a solution containing stevioside, the temperature was set to 30 ° C., 50 ° C., and 70 ° C., and it was confirmed at which temperature the solubilization of curcumin was the highest. As a result, curcumin was dissolved at 110 mg / L at 30 ° C, 170 mg / L at 50 ° C, and 390 mg / L at 70 ° C. That is, it was confirmed that the solubility of curcumin was most increased at 70 °C (Fig. 1).
  • curcumin 10 mg / ml of curcumin is dissolved in stevioside solution and sonicated, followed by sonication, autoclave (121 ° C., 15 psi, 15 minutes), or microwave for 15 minutes in a microwave oven at 700 W. Reaction) were treated for 15 minutes each.
  • the degree of solubilization of curcumin was confirmed under the three conditions, and the results are shown in Table 2 below.
  • solubilized curcumin was optimized using a synthetic-only microwave (CEM's Discover legacy systems model).
  • Basic experiments show four factors: microwave power (50-200 W), stevioside concentration (50-200 mg / L), curcumin concentration (20-200 mg / L), and reaction time 1-10 minutes.
  • microwave power 50-200 W
  • stevioside concentration 50-200 mg / L
  • curcumin concentration 20-200 mg / L
  • reaction time 1-10 minutes. Optimized by surface reaction analysis method at (Table 3).
  • the solubilization of curcumin was excellent at the concentration of licorice extract higher than the low concentration.
  • 10 mg / ml curcumin was dissolved in 0.5, 2, 5, 10% (w / v) licorice extract solution and sonicated, followed by sonication, wet sterilizer (121 ° C., 15 psi, 15 minutes), microwave 15 minutes each.
  • the concentration of licorice extract and the degree of solubilization of curcumin according to the three post-treatments are shown in Table 5 below.
  • Glucosyl resveratrol purchased from Sigma and 20 mg / ml of resveratrol prepared by the method of Example 2 were dissolved for each 0-20% (w / v) stevioside or licorice extract solution, and ultrasonically used at 70 ° C. Treated for 15 minutes. In addition, the microwaves were treated twice each for 15 minutes to quantify the amounts of resveratrol and glucosyl resveratrol solubilized from each solvent using HPLC. The results were compared with the case of only ultrasonic treatment without microwave treatment, and the results are shown in Table 6 below.
  • the amount of resveratrol finally solubilized in the sample to which 20% (w / v) of stevioside was added was 6,200 mg / L, which was 10 mg / L solubilized resveratrol in a solution containing no stevioside It was confirmed that the solubility was significantly increased compared to. In addition, after dissolving resveratrol in a solution containing stevioside, it was confirmed that the amount of solubilized resveratrol was improved to 9,400 mg / L when the microwave treatment.
  • the amount of finally solubilized glucosyl resveratrol in the sample added with 20% (w / v) stevioside was 8,500 mg / L, which was added to 50 mg / L solubilized glucosyl resveratrol in a solution containing no stevioside. Solubility was significantly increased in comparison.
  • microwave treatment of the solution containing steviosides was confirmed that the amount of solubilized resveratrol improved to 14,200 mg / L, which was 71.5% solubilization of the initially added glucosyl resveratrol.
  • the amount of resveratrol finally solubilized in the sample to which 20% (w / v) licorice extract was added was 8,600 mg / L, which was added to 10 mg / L solubilized resveratrol in a solution that did not contain licorice extract. It was confirmed that the solubility was significantly increased. In addition, after dissolving resveratrol in a solution containing licorice extract, when the microwave treatment, the amount of solubilized resveratrol was confirmed to improve to 11,600 mg / L.
  • the amount of finally solubilized glucosyl resveratrol in the sample to which 20% (w / v) licorice extract was added was 10,500 mg / L, which was added to 50 mg / L solubilized glucosyl resveratrol in a solution containing no licorice extract. Solubility was significantly increased in comparison.
  • microwave treatment of the solution containing licorice extract was confirmed that the amount of solubilized resveratrol improved to 17,300 mg / L, which was solubilized 86.5% of the initially added glucosyl resveratrol.
  • the glycyrrhizinic acid purchased from Sigma was dissolved in each 0.1-5% (w / v) stevioside or licorice extract solution at a concentration of 5 mg / ml and treated for 10 minutes using ultrasonic waves at 70 ° C.
  • the amount of glycyrrhizinic acid solubilized from each solvent by treating twice with 15 minutes using microwave was quantified using HPLC.
  • the result of using licorice extract in this manner also showed a gelation reaction when the licorice extract of 0.1-0.5% (w / v) was added, and all of the glycidyl acid initially added with only 1% or more licorice extract was solubilized. It was confirmed to make.
  • Paclitaxol purchased from Sigma was dissolved in each of 0, 5, 10, 20% (w / v) stevioside or licorice extract solution at a concentration of 10 mg / ml, and 10 minutes using ultrasonic waves at 70 ° C.
  • the amount of curcumin solubilized from each solvent was treated and treated twice with 15 minutes using microwaves to quantify using HPLC.
  • solubilization was less than that of stevioside in 10% and 20% (w / v) solutions, but 800 mg / L and microwaves were sonicated when sonicated in 20% (w / v) solutions. It was found that solubilization was improved to 1,900 mg / L when treated.

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Abstract

La présente invention concerne : un complexe présentant une solubilité accrue d'une matière faiblement soluble, comprenant des stéviol glycosides ou des stévia contenant ceux-ci, ou de la racine de réglisse, et une matière faiblement soluble ; un procédé de préparation de celui-ci ; une composition de produit pharmaceutique ou d'aliment contenant le complexe ; une composition cosmétique ou d'aliment contenant le complexe ; un agent de solubilisation pour augmenter la solubilité d'une matière faiblement soluble ; et un procédé pour solubiliser une matière faiblement soluble. Etant donné que le complexe de la présente invention est remarquablement amélioré dans la solubilité d'une matière faiblement soluble, le complexe peut être facilement préparée sous une forme pharmaceutique devant être administrée par voie orale et par injection, présente une excellente stabilité au stockage et a des effets d'aptitude remarquable à l'administration de médicament et de vitesse d'absorption remarquable dans le corps.
PCT/KR2012/006069 2011-07-29 2012-07-30 Complexe comprenant des glycosides de stéviol ou de la racine de réglisse et matière faiblement soluble WO2013019049A1 (fr)

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KR101924159B1 (ko) 2016-04-15 2018-11-30 서울대학교산학협력단 스테비올 배당체를 이용한 수용성이 증가된 커큐미노이드의 추출 방법및 이에 의하여 추출된 수용성이 증가된 커큐미노이드
US10456343B2 (en) 2017-01-26 2019-10-29 L'oreal Microemulsion compositions comprising polydatin and method of use
CN111388676A (zh) * 2020-02-11 2020-07-10 湖南中茂生物科技有限公司 一种提高姜黄素水溶性的组合物及其在制备治疗老年痴呆的复方中的应用

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KR20150086928A (ko) * 2014-01-21 2015-07-29 한국생명공학연구원 커큐미노이드계 화합물, 및 감초 추출물 또는 이의 분획물을 포함하는 인플루엔자 바이러스 감염의 예방 또는 치료용 조성물
KR101719579B1 (ko) * 2015-03-09 2017-03-24 서울대학교산학협력단 용해도가 개선된 난용성 소재와 스테비올 배당체의 복합체 제조 방법 및 이에 의하여 제조된 용해도가 개선된 난용성 소재와 스테비올배당체의 복합체
WO2016143939A1 (fr) * 2015-03-09 2016-09-15 서울대학교산학협력단 Procédé de production d'un complexe de glycoside de stéviol et d'un matériau modérément soluble présentant une solubilité améliorée et complexe de glycoside de stéviol et de matériau modérément soluble, présentant une solubilité améliorée ainsi produit
KR102662257B1 (ko) * 2016-10-26 2024-05-02 주식회사 엘지생활건강 레바우디오사이드 c를 포함하는 화장료 조성물
KR102613550B1 (ko) * 2018-05-17 2023-12-14 한국생명공학연구원 난용성 물질인 커큐민을 포함하는 진세노사이드 복합체
KR20200071028A (ko) * 2018-12-10 2020-06-18 서울대학교산학협력단 유산균 균주를 이용하여 제조된 올리고당을 포함하는 난수용성 물질의 수용액 가용화 조성물
WO2022220521A1 (fr) * 2021-04-12 2022-10-20 표상현 Composé amphipathique, son procédé de préparation et composition tensioactive le comprenant

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JP2004065128A (ja) * 2002-08-07 2004-03-04 Maruzen Pharmaceut Co Ltd 甘草油性抽出物の可溶化組成物、並びに飲料、液状調味料、化粧品及び医薬部外品
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Cited By (3)

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Publication number Priority date Publication date Assignee Title
KR101924159B1 (ko) 2016-04-15 2018-11-30 서울대학교산학협력단 스테비올 배당체를 이용한 수용성이 증가된 커큐미노이드의 추출 방법및 이에 의하여 추출된 수용성이 증가된 커큐미노이드
US10456343B2 (en) 2017-01-26 2019-10-29 L'oreal Microemulsion compositions comprising polydatin and method of use
CN111388676A (zh) * 2020-02-11 2020-07-10 湖南中茂生物科技有限公司 一种提高姜黄素水溶性的组合物及其在制备治疗老年痴呆的复方中的应用

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