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WO2007119837A1 - Inhibiteur de lipase - Google Patents

Inhibiteur de lipase Download PDF

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Publication number
WO2007119837A1
WO2007119837A1 PCT/JP2007/058209 JP2007058209W WO2007119837A1 WO 2007119837 A1 WO2007119837 A1 WO 2007119837A1 JP 2007058209 W JP2007058209 W JP 2007058209W WO 2007119837 A1 WO2007119837 A1 WO 2007119837A1
Authority
WO
WIPO (PCT)
Prior art keywords
extract
myricitrin
syzygium
lipase inhibitor
food
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2007/058209
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English (en)
Japanese (ja)
Inventor
Tetsuya Seki
Katsuya Suzuki
Koichi Ishii
Katsunori Kobayashi
Keishi Kameyama
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Ajinomoto Co Inc
Original Assignee
Ajinomoto Co Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ajinomoto Co Inc filed Critical Ajinomoto Co Inc
Publication of WO2007119837A1 publication Critical patent/WO2007119837A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/99—Enzyme inactivation by chemical treatment
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • 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)
    • A61K36/61—Myrtaceae (Myrtle family), e.g. teatree or eucalyptus
    • 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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • 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
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/06—Antihyperlipidemics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/74—Biological properties of particular ingredients
    • A61K2800/78—Enzyme modulators, e.g. Enzyme agonists
    • A61K2800/782—Enzyme inhibitors; Enzyme antagonists
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments

Definitions

  • the present invention relates to a novel lipase inhibitor containing myristitrin as an active ingredient, a method for inhibiting lipase comprising administering myristitrin, and myristitrin in the manufacture of a medicine for inhibiting lipase.
  • a novel lipase inhibitor containing myristitrin as an active ingredient a method for inhibiting lipase comprising administering myristitrin, and myristitrin in the manufacture of a medicine for inhibiting lipase.
  • the present invention relates to the use of millicitrin in the prevention or treatment of so-called lifestyle-related diseases such as obesity, diabetes, hypertension, hyperlipidemia, arteriosclerosis, and metabolic syndrome.
  • lifestyle-related diseases such as obesity, diabetes, hypertension, hyperlipidemia, arteriosclerosis, and metabolic syndrome.
  • Insulin resistance is a term indicating a state in which the sensitivity of target organs such as skeletal muscle, liver, and adipose tissue to insulin secreted by spleen 8 cells is reduced. Insulin resistance is due to a genetic predisposition, but most is due to obesity.
  • the body is compensated for the insulin resistance caused by obesity by vigorous insulin secretion from spleen ⁇ 8 cells, and hyperinsulinemia keeps blood glucose close to normal. However, if this persists, the splenic ⁇ -cells become exhausted, the insulin secretory ability gradually decreases, and progresses to a diabetic state. Therefore, the improvement of obesity is extremely effective for the reduction of blood insulin concentration and the improvement of insulin resistance, and thus the prevention of diabetes.
  • Lipase is a digestive enzyme of fat, and spleen power is also secreted in humans. This river By the hydrolysis, the ester bond of tridalycelide, which is the main component of fat, is hydrolyzed to produce monodalyceride and free fatty acid. These are absorbed from the small intestine and consumed as energy in the body. Excessive fat intake is not used for energy consumption in the body and causes fat to accumulate in tissues, leading to obesity. Thus, lipase is closely related to obesity and hyperlipidemia, and sarcophagus is closely related to insulin resistance, hyperinsulinemia, metabolic syndrome, diabetes, arteriosclerosis, and inhibits lipase activity. It is considered that these substances are effective in preventing and treating these diseases.
  • lipase produced by microorganisms resident in human skin degrades lipids on the skin into glycerin and free fatty acids. Some of these free fatty acids have adverse effects on the skin, and it is known that they can cause skin diseases such as comedones, and free fatty acids can be further decomposed to cause body odor. . Inhibition of lipase activity is also effective in solving such problems.
  • epigalocatechin gallate which is a component of green tea (Patent Document 1), water extracts such as bell pepper, pumpkin, shimeji, hijiki, green tea, oolong tea (Patent Document 2), Examples include tamarind seed coat extract containing procyanidins (Patent Document 3), hot water extract of defatted rice bran (Patent Document 4), and polyphenolic substances contained in hops (Patent Document 5). it can.
  • lipase inhibitors containing various flavonoids other than epigallocatechin gallate have been reported (Patent Documents 6 to 8).
  • Patent Document 1 Japanese Patent Laid-Open No. 3-228664
  • Patent Document 2 JP-A-3-219872
  • Patent Document 3 Japanese Patent Laid-Open No. 9-291039
  • Patent Document 4 Japanese Patent Laid-Open No. 2001-97880
  • Patent Document 5 Japanese Patent Laid-Open No. 2001-321166
  • Patent Document 6 Japanese Patent Laid-Open No. 7-61972
  • Patent Document 7 Japanese Patent Laid-Open No. 9-143070
  • Patent Document 8 Japanese Unexamined Patent Publication No. 2003-321351
  • Patent Document 9 JP 2001-231500 A
  • Non-Patent Document 1 J. Ethnopharmacol. 1999 Dec 15; 68 (1-3): 307— 14. Disclosure of Invention
  • An object of the present invention is a lifestyle-related disease comprising, as an active ingredient, an extract isolated from food raw materials or a compound contained in a plant that can be safely ingested by being contained in a pharmaceutical or food. It is to provide a lipase inhibitor useful for the prevention and treatment of metabolic syndrome.
  • the present invention is as follows.
  • a lipase inhibitor characterized by containing mycitrin as an active ingredient.
  • the lipase inhibitor according to (1) which is obtained from a plant selected from the group consisting of flora (Eugenia uniflora) or an extract thereof.
  • the lipase inhibitor according to (1) or (2) comprising a plant containing 0.05% by weight or more of myricitrin or an extract thereof.
  • a lipase inhibitor characterized by comprising:
  • a method for producing a myristitrine-containing extract comprising a step of extracting a plant containing mycitrin with water, an organic solvent, or a mixed solvent thereof.
  • a method for inhibiting lipase in a subject comprising administering to the subject an effective amount of myricitrin.
  • Esukiyurenta (Colocasia esculenta), The method according to (14), which is obtained from a plant selected from the group consisting of Psi dium littorale Raddi and Eugenia uniflora or an extract thereof. .
  • the medicine is at least one selected from fat absorption inhibitor, blood fat concentration inhibitor, anti-obesity agent, insulin resistance improving agent, blood insulin concentration reducing agent or metabolic syndrome improving or preventing agent power, (18) The use according to any one of (23).
  • lipase inhibition is at least one selected from suppression of fat absorption, suppression of blood fat concentration, anti-obesity, improvement of insulin resistance, reduction of blood insulin concentration or improvement or prevention of metabolic syndrome. Food listed.
  • Myricitrin which is an active ingredient in the present invention, has the following chemical formula:
  • [0016] is a glycoside of myricetin, which is one of flavonols, and has excellent lipase inhibitory activity and suppresses absorption in the body after intake of fat.
  • the myricitrin used in the present invention may be natural or synthesized.
  • the synthesis of myricitrin can be carried out by conventional methods, for example, by alkylating the 3-hydroxyl group of myricetin with aglycone such as rutin and protecting it, and then replacing the sugar with rhamnose. can do.
  • a raw material for obtaining myricitrin or myricitrin-containing extract mature or immature fruit, pericarp, seed, leaf, stem, petiole, branch, root, flower, whole, etc. of the above plant are used. Of these, leaves or stems are preferably used.
  • the plants that can be used in the present invention include all dried products obtained by drying the plants themselves, pulverized products, juices obtained by squeezing and extracting the plants themselves, crude extracts, purified products of the extracts, etc. It is.
  • the lipase inhibitor of the present invention preferably contains a plant containing 0.05% by weight or more of myristitrin or an extract thereof.
  • the method for producing the extract in the present invention is not particularly limited.
  • a plant containing mycitrin as a component (hereinafter also referred to as myristitrin-containing plant) is mixed with water or an organic solvent (alcohol (methanol, ethanol). Etc.) can be obtained by extraction with a mixed solvent thereof. Thereafter, when the obtained extract is further purified by partition using an organic solvent or purified by adsorption resin, a good quality extract can be obtained.
  • the obtained myricitrin-containing extract is used after being appropriately concentrated, purified, sterilized, dried and the like.
  • organic solvent used here examples include ethyl acetate, glycerin, 1,3-butylene glycol, chloroform, dichloromethane, alcohol (methanol, ethanol, etc.), and the like.
  • ethyl acetate or the like in which a water-insoluble organic solvent is preferred, is more preferred.
  • Alcohols (methanol, ethanol, etc.) are preferred for purification by adsorbent resin.
  • the extraction may be performed at room temperature to under heating, and is usually performed at 1 to 100 ° C, preferably 20 to 90 ° C.
  • Concentration and drying of the extract may be carried out by adding excipients (for example, lactose, sucrose, starch, cyclodextrin, etc.) as appropriate, where the extract may be concentrated and dried as it is. Also good.
  • excipients for example, lactose, sucrose, starch, cyclodextrin, etc.
  • a myrcitrin-containing extract containing 0.05 to 90% by weight, particularly 1 to 45% by weight of myritol in the above-described production method in a ratio to the dry extract. Since the extract obtained by the above production method has high water solubility, it also has an advantage that it can be easily formulated. In addition, when taken orally, the mycitrin-containing extract obtained in this way is difficult to precipitate, so that it reaches the small intestine and is easily absorbed, so a high effect can be expected.
  • the present invention also provides a fat absorption inhibitor, a blood fat concentration inhibitor, an anti-obesity agent, an insulin resistance improving agent, a blood insulin concentration reducing agent based on the lipase inhibitory action of myricitrin, Provide metabolic syndrome improvement or prevention agent.
  • the present invention provides foods and cosmetics containing myricitrin.
  • the lipase inhibitor of the present invention is especially useful for daily continuous intake in the form of food with high safety.
  • Food in the present invention means various forms of food such as solid, semi-solid, and liquid. In addition to general food including so-called health food, it is specified in the health function food system of the Ministry of Health, Labor and Welfare. It is a concept that encompasses functional health foods such as health foods and functional nutritional foods, and so-called functional foods, dietary supplements (nutritional supplements), feeds, food additives, and the like are also included in the foods of the present invention. Is done.
  • lipase inhibitor of the present invention as a food.
  • the lipase inhibitor of the present invention is used as a health food, food additive, dietary supplement, etc., for example, using conventional means, tablets, capsules, powders, granules, suspensions, chewables, etc. Can be prepared in the form of an agent, syrup and the like. Furthermore, it is also possible to provide such foods as functional health foods, which include lipase inhibition, fat absorption inhibition, blood fat concentration inhibition, anti-obesity, insulin resistance improvement, blood insulin Also included are foods that are labeled for use in reducing concentrations, improving metabolic syndrome and preventing Z or metabolic syndrome, especially foods for specified health use.
  • the present invention can also be applied to feed applications, and can be ingested or administered to poultry and livestock even when added to normal feed.
  • Metabolic syndrome refers to a condition in which a series of pathological conditions such as type 2 diabetes, hyperlipidemia, hypertension, visceral fat obesity, and fatty liver based on insulin resistance are combined. Also known as insulin resistance syndrome, visceral fat syndrome, multiple risk factor syndrome.
  • improvement of metabolic syndrome means alleviation or cure of the symptoms in at least one selected disease state group force that is generally known as a disease state of metabolic syndrome such as the above-mentioned disease states.
  • prevention of metabolic syndrome means preventing or delaying the occurrence of symptoms in at least one pathological condition that is generally selected as a pathological condition of metabolic syndrome such as the above-mentioned pathological conditions. To do.
  • the amount of myricitrin in the food and food composition varies depending on the addition form and the intake form, and can be selected from a wide range. Usually 0.05% to 100% by weight, preferably 0.5% % To 90% by weight may be blended.
  • the blended amount of processed food products, processed fishery products, solid foods such as bread, dairy products, confectionery and jelly, and semi-solid foods is 0.05 to 25% by weight, preferably 0.5%. Weight percent to 10 weight percent is preferred.
  • the amount of liquid food such as soft drinks, water, and milk is 0.05% to 20% by weight, preferably 0.5% to 10% by weight.
  • the amount of myricitrin in these dosage forms Is preferably 0.05 to 100% by weight, preferably 0.5 to 90% by weight, more preferably 1 to 80% by weight.
  • the amount of myricitrin is 0.05 to 90% by weight, preferably 0.5 to 90% by weight, more preferably 5% by weight. % To 50% by weight is preferred.
  • the blending amount of the myricitrin-containing plant or the extract thereof varies depending on the addition form and the intake form, but can be selected from a wide range, for example, In the case of food, it is desirable to add 1 to: L00% by weight, particularly 10% to 90% by weight or more in terms of solvent-extracted dried product.
  • a mycitolin-containing plant or an extract thereof is added to a solid food such as processed meat products, processed fishery products, bread, dairy products, confectionery, jelly, or semi-solid food
  • solvent extraction 1% to 40% by weight preferably 1% to 20% by weight, in terms of dry matter.
  • the amount of liquid foods such as soft drinks, water, and milk is 1% by weight to 20% by weight, preferably 2% by weight to 10% by weight, in terms of solvent-extracted dried product.
  • mycitrin-containing plants or extracts thereof are used in health foods, food additives, dietary supplements, etc., for example, in the case of solid forms such as tablets, powders, granules, powders, etc.
  • the compounding amount in the form is 1% to 100% by weight, preferably 5% to 90% by weight, more preferably 10% to 80% by weight in terms of the solvent-extracted dried product.
  • the amount of liquid foods such as suspensions and syrups is 1% to 100% by weight, preferably 5% to 80% by weight, more preferably 10% to 50% by weight is preferred.
  • the dosage should be 0.1 mg to 5 g, preferably 5 mg to 2 g per adult per day when ingesting purified or synthesized mycitrin. It is preferable to take or take 10 mg to 0.5 g once a day in several divided doses. In this case, the daily intake or the intake per time can be made into one unit package.
  • the form is not particularly limited, and myritol is used as it is or, for example, tablets, granules, fine granules, powders, capsules, It can be formulated into injections, solutions, suspensions, emulsions, creams, suppositories, etc. and administered orally or parenterally (for example, topical, rectal, intravenous administration, etc.). These can be formulated as various preparations by a method known per se using pharmacologically acceptable carriers and additives.
  • Examples of the pharmaceutical carrier used include lactose, glucose, D-manntol, starch, crystalline cellulose, calcium carbonate, kaolin, starch, gelatin, and hydroxypropyl.
  • myricitrine is usually 0.05 to 100% by weight in the preparation. / 0 , preferably 5 to 90% by weight.
  • myritolin-containing plant or an extract thereof is included in the preparation, the myristitrin-containing plant or the extract thereof is 1 to: LOO wt%, preferably 10 Up to 90% by weight can be blended.
  • the administration target of the lipase inhibitor of the present invention includes mammals such as mice, rats, hamsters, rabbits, cats, nu, ushi, hidge, monkeys and humans.
  • the dose of myricitrin varies depending on the patient's pathology, age, administration method, etc., but is usually 0.01 to 20 gZ days per day for human adults.
  • the dose is preferably about 0.05 to 10 gZ days, more preferably about 0.1 to 3 gZ days, and this is divided into 1 to 5 doses as needed.
  • oils, waxes, fatty acids, and the like that are usually used in cosmetics depending on the purpose within a range that does not impair the effects of the agent.
  • Combine ingredients such as surfactants, alcohols, esters, hydrocarbons, vitamins, amino acids, enzymes, nucleic acids, etc. that are listed in the Cosmetic Raw Material Standards, Japanese Pharmacopoeia, Food Additives, etc. Also good.
  • cosmetics it can be used in the form of basic cosmetics such as creams, lotions, emulsions, knocks, makeup cosmetics such as foundations, bathing agents, stone jars and the like.
  • millicitrin is 0.05 to 100 weight. / 0 , preferably 5 to 90% by weight or more.
  • the myristitrin-containing plant or an extract thereof is added in an amount of 1 to LOO% by weight, preferably 10 to 90% by weight in terms of a solvent-extracted dried product. sell.
  • foods, pharmaceuticals and cosmetics containing the lipase inhibitor of the present invention are known to be used in foods, pharmaceuticals and cosmetics as long as they do not adversely affect the lipase inhibitory activity of myricitrin as a whole.
  • Components such as xanthine derivatives,
  • the xanthine derivative that can be used in the present invention is not particularly limited.
  • these xanthine derivatives those synthesized or those substantially isolated from plants such as tea can be used.
  • the ⁇ -adrenergic agonist that can be used in the present invention is not particularly limited. Chlorprenalin, Hexoprenalin, Trimethoquinol, Proterol hydrochloride, Prenalterol, Forskolin, Disodium (R, R) — 5— [[[[2— (3—Black mouthfeel) 1 2 Hydrochetyl ] Amino] propyl] fur] phenoxyacetic acid, [2 hydroxy 5— [2— [[2 —hydroxy 1 3— [4— (1-methyl 4 trifluoromethyl) 1H-imidazol 1-2-yl] ] Phenoxy] propyl] amino] ethoxy] benzamide monomethanesulfonate, ELIS mouthpiece DL—1— (7-methinoreida One 4-Iruokishi) and 3-isopropylamino-pig Hmm 2- ol and pharmaceutically acceptable salts of these pharmacologically like.
  • Examples of pharmacologically acceptable salts include pharmaceutically acceptable acid addition salts, metal salts, ammonium salts, and organic amine addition salts.
  • isoproterenol, dobutamine, salbutamol and their pharmacologically acceptable salt strength are selected as one type or It is preferable to use two or more types of salts. In this case, hydrochloride and sulfate are preferred.
  • the a 2 adrenergic inhibitor that can be used in the present invention is not particularly limited. Toxins, laurosine, piperoxane and pharmacologically acceptable salts thereof may be mentioned. These can be used alone or in combination of two or more. As the pharmacologically acceptable salt, mesylate, tartrate and hydrochloride are preferred.
  • the biviridine derivatives used in the present invention are not particularly limited, but include amrinone, milrinone, 5ciano [3,4, monobiviridine] -6 (1H) -one, 5-streptylamylone [3,4, 1 biviridine] -6 (1H) -one and pharmacologically acceptable salts thereof.
  • the present invention provides a method of inhibiting lipase in a subject, comprising administering to the subject an effective amount of myricitrin, and the use of millicitrin in the manufacture of a medicament for inhibiting lipase.
  • a lipase inhibitor and the lipase inhibitor should be used or capable of being used for fat absorption suppression, blood fat concentration suppression, anti-obesity, insulin resistance improvement, blood insulin concentration reduction and metabolic syndrome improvement or prevention And provide a commercial package that includes documentation that states
  • Test example 1 Lipase activity case. Harm test, test
  • TES aminoethanesulfonic acid
  • a substrate solution was prepared. Enzyme solution 25 / zl and test sample 12.51 in Table 1 dissolved in pure water were mixed and allowed to stand at room temperature for 5 minutes, then substrate solution 12.51 was added and reacted at room temperature for 60 minutes. . After the reaction, the reaction solution of 41 was taken, and the amount of fatty acid decomposed and released by lipase was measured with NEFA C test kit (Wako Pure Chemical Industries, Ltd.).
  • Samples lg were obtained from Mizlenbu, Teriha bunjirou, Banjiro, Tachibana adek, Gurumiyama, Jabochikapa, Rembu's leaves. Take a sample in a container equipped with a stirrer, add 40 ml of water, stir at a temperature of 30 ° C for 2 hours, then filter the contents at room temperature under reduced pressure using a Buchner funnel and filter paper (5A) to extract the solid content. The liquid was separated into 40 ml. 40 ml of ethyl acetate was added to the obtained extract and the extraction was repeated 3 times to obtain 120 ml of ethyl acetate extract.
  • the extract was analyzed by the following method to analyze the myristitrin content.
  • each extract was dispersed in 50 ml of methanol. This dispersion was used as an analysis sample. This analysis sample was subjected to high performance liquid chromatography under the following conditions to analyze myristitrin. As a standard sample, commercially available myricitrin purchased from ChromaDex was used.
  • the elution peak of myricitrin was detected around 50 minutes. Quantification was performed using the area ratio of the detected peaks.
  • the adsorbed resin was sequentially washed with 4 ml of water and 20% ethanol, and then eluted with 4 ml of 40% ethanol. 4 ml of this 40% ethanol-eluted fraction was transferred to a vacuum dryer, and then the extraction solvent was distilled off at 40 ° C for 1 hour under a reduced pressure of 50 mmHg to obtain 0.05 g of a myristitrin-containing extract.
  • the extract was analyzed by the same method as in (1) to analyze the myristitrin content. As shown in Table 3, all mycitrin contents of the extracts were high.
  • Test Example 2 Mizurenb, Terihabanjiro Blood Fat Concentration Test, Test (Soybean Oil Test, Test)
  • the prepared extract contained 1.0% by weight in the case of the mycitrin extract mizurembu extract and 1.5% by weight in the case of the terihabanjirou extract.
  • Plasma tridalycide levels were measured with a Fuji Dry Chemslide (Fuji Film). The difference between the triglyceride value before administration of each individual and the tridalylide value at each time after administration was determined to determine the plasma triglyceride change / area under the time curve. The results are shown in Figure 1. As can be seen from the figure, the increase in plasma tridalylide level was suppressed in the group administered with the extract.
  • Extraction was carried out at room temperature with 10 ml of 70% ethanol solution per lg of Gurumiyama leaves, and the dried up ones were used for the test.
  • Male ICR mice (6 weeks old) were orally administered 20% soybean oil at 10 mlZkg, and 0.5% sodium carboxymethylcellulose (Control) or the prepared extract was suspended in Control at a dose of 500 mgZkg. Orally administered.
  • the prepared extract contained 1.2% by weight of myristitrin. Blood samples were collected from the fundus vein before administration and 2, 3, and 4 hours after administration, and plasma tridalylide values were measured with Fuji Dry Chem Slide (manufactured by Fuji Film).
  • Test Example 4 Japotikaba or Rembu Serum Fat Concentration Test, Experiment (soybean oil loaded mi
  • Jaboticapa or Lembu leaves were extracted with 10 ml of 70% ethanol solution per lg at room temperature and dried up and used for the test.
  • Male ICR mice (8 weeks old) were orally administered 20% soybean oil in lOmlZkg and immediately suspended in 0.5% carboxymethylcellulose sodium (Control) or the prepared extract in Control solvent at a dose of 500mgZkg. Orally.
  • mycitrin is extracted from jaboticapa in the prepared extract.
  • 0.9% by weight and in the case of Rembu extract, 1.2% by weight were contained.
  • blood was collected from the fundus vein, and plasma tridalylide value was measured with Fuji Dry Chemslide (Fuji Film).
  • the area under the plasma triglyceride change time curve was determined by taking the difference between the tridalyceride value before administration and the tridalylide value at each time after administration. The results are shown in Figure 3. As is apparent from the figure, the increase in plasma triglyceride level was suppressed in the group administered with the extract.
  • Test ⁇ Row 5 Japachikaba ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ jj3 ⁇ 43 ⁇ 4 l! II ⁇ ⁇ ( ⁇ ⁇ : 3 ⁇ 4 load test)
  • Extraction was carried out at room temperature with 10 ml of 70% ethanol solution per lg of jaboticapa, and the dried up product was used for the test.
  • Male ICR mice (7 weeks old) were orally administered 20% soybean oil at 10 mlZkg, and immediately, 0.5% sodium carboxymethylcellulose (Control) or a suspension of the prepared extract in Control solvent was administered at a dose of 500 mgZkg. Was administered orally.
  • the prepared extract contained 0.3% by weight of myristitrin. Blood samples were collected from the fundus vein before administration, 2, 3, and 4 hours after administration, and plasma tridalycelide levels were measured with Fuji Dry Chemslide (Fuji Film).
  • Test example 7 Blood fat level of myricitrin Control test, test (olive oil loading test)
  • Myricitrin purchased from Wako was used for the test.
  • Blood samples were collected from the fundus vein before administration, 2, 4, and 6 hours after administration, and plasma triglyceride values were measured with Fuji Dry Chem Slide (manufactured by Fuji Film). The result is shown in FIG. As is clear from the figure, the increase in plasma triglyceride levels was suppressed in the group administered myricitrin.
  • Example 2 Example of tablet manufacturing
  • Tachibana adek leaf extract (prepared as in Example 1) 1.
  • the tablet After mixing each of the above components, the tablet can be tableted with a single tableting machine to obtain a tablet with a diameter of 10 mm and a weight of 400 mg.
  • Tachibana adek leaf extract (prepared as in Example 1) 1.5 kg
  • a pressure bias is obtained with a roller compactor.
  • This pressure-biased product is pulverized with an oscillator, and after sizing, it is passed through a sieve to obtain granules having a particle size of 20 to L00 mesh.
  • Example 4 Granules notification example
  • extrusion granulation is performed by a conventional method, and then passed through a sieve to obtain a particle size of 20
  • Capsules can be prepared by filling 250 mg of powder of Tachibana adek leaf extract prepared in the same manner as in Example 1 into hard capsules.
  • Tachibana adek leaf extract (prepared as in Example 1) 300. Og
  • Vitamin E 30 0g
  • the lipase inhibitor of the present invention has effects such as suppression of fat absorption, suppression of blood fat concentration, anti-obesity, improvement of insulin resistance, reduction of blood insulin concentration, improvement or prevention of metabolic syndrome, It is useful as an absorption inhibitor, blood fat concentration inhibitor, anti-obesity agent, insulin resistance improving agent, blood insulin concentration lowering agent, or metabolic syndrome improving or preventing agent.
  • the lipase inhibitor of the present invention suppresses absorption in the body after fat intake, Suppresses subsequent increase in triglycerides, can help improve the health status of people who tend to eat fat, and makes it difficult for people who are concerned about body fat and triglycerides Such effects can also be provided. Therefore, it is effective for prevention or treatment of diseases such as obesity, diabetes, hypertension, hyperlipidemia, arteriosclerosis, and other lifestyle-related diseases and metabolic syndrome.

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Abstract

L'invention concerne un inhibiteur de lipase qui peut être ingéré sans risque en le mélangeant à un produit pharmaceutique ou à un aliment, qui contient, comme principe actif, un extrait isolé d'une matière première alimentaire ou d'un composé contenu dans une plante, et qui est utile pour la prévention/le traitement d'une maladie apparentée à un mode de vie ou à un syndrome métabolique. L'inhibiteur de lipase comprend de la myricitrine comme principe actif.
PCT/JP2007/058209 2006-04-14 2007-04-13 Inhibiteur de lipase Ceased WO2007119837A1 (fr)

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Cited By (19)

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Publication number Priority date Publication date Assignee Title
WO2009021740A2 (fr) 2007-08-15 2009-02-19 Sanofis-Aventis Nouvelles tétrahydronaphtalines substituées, leurs procédés de préparation et leur utilisation comme médicaments
WO2010005004A1 (fr) * 2008-07-07 2010-01-14 花王株式会社 Inhibiteur de la xanthine oxydase et inhibiteur de la production d’acide urique
JP2010043008A (ja) * 2008-08-08 2010-02-25 Kansai Koso Co Ltd リパーゼ活性抑制剤及びこれを含有する化粧料
JP2010132564A (ja) * 2008-12-02 2010-06-17 Lotte Co Ltd 消臭剤及びそれを含む口腔用組成物並びに飲食品
JP2011037720A (ja) * 2009-08-06 2011-02-24 Kao Corp Ｄｇａｔ阻害剤
WO2011107494A1 (fr) 2010-03-03 2011-09-09 Sanofi Nouveaux dérivés aromatiques de glycoside, médicaments contenants ces composés, et leur utilisation
WO2011157827A1 (fr) 2010-06-18 2011-12-22 Sanofi Dérivés d'azolopyridin-3-one en tant qu'inhibiteurs de lipases et de phospholipases
WO2011161030A1 (fr) 2010-06-21 2011-12-29 Sanofi Dérivés de méthoxyphényle à substitution hétérocyclique par un groupe oxo, leur procédé de production et leur utilisation comme modulateurs du récepteur gpr40
CN102304158A (zh) * 2011-05-20 2012-01-04 中国人民解放军第二军医大学 酰化黄酮苷化合物及其在制备补体抑制剂药物中的应用
WO2012004269A1 (fr) 2010-07-05 2012-01-12 Sanofi Dérivés d'acide ( 2 -aryloxy -acétylamino) - phényl - propionique, procédé de production et utilisation comme médicament
WO2012004270A1 (fr) 2010-07-05 2012-01-12 Sanofi Dérivés 1,3-propanedioxyde à substitution spirocyclique, procédé de préparation et utilisation comme médicament
WO2012010413A1 (fr) 2010-07-05 2012-01-26 Sanofi Acides hydroxy-phényl-hexiniques substitués par aryloxy-alkylène, procédé de production et utilisation comme médicament
WO2012120054A1 (fr) 2011-03-08 2012-09-13 Sanofi Dérivés oxathiazine di- et tri-substitués, procédé pour leur préparation, utilisation en tant que médicament, agent pharmaceutique contenant ces dérivés et utilisation
WO2012120053A1 (fr) 2011-03-08 2012-09-13 Sanofi Dérivés oxathiazine ramifiés, procédé pour leur préparation, utilisation en tant que médicament, agents pharmaceutiques contenant ces dérivés et leur utilisation
WO2012120056A1 (fr) 2011-03-08 2012-09-13 Sanofi Dérivés oxathiazine tétra-substitués, procédé pour leur préparation, utilisation en tant que médicament, agent pharmaceutique contenant ces dérivés et utilisation
WO2012120055A1 (fr) 2011-03-08 2012-09-13 Sanofi Dérivés oxathiazine di- et tri-substitués, procédé pour leur préparation, utilisation en tant que médicament, agent pharmaceutique contenant ces dérivés et utilisation
WO2012120052A1 (fr) 2011-03-08 2012-09-13 Sanofi Dérivés d'oxathiazine substitués par des carbocycles ou des hétérocycles, leur procédé de préparation, médicaments contenant ces composés et leur utilisation
WO2013037390A1 (fr) 2011-09-12 2013-03-21 Sanofi Dérivés amides d'acide 6-(4-hydroxyphényl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylique en tant qu'inhibiteurs de kinase
WO2013045413A1 (fr) 2011-09-27 2013-04-04 Sanofi Dérivés d'amide d'acide 6-(4-hydroxyphényl)-3-alkyl-1h-pyrazolo[3,4-b] pyridine-4-carboxylique utilisés comme inhibiteurs de kinase

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Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009021740A2 (fr) 2007-08-15 2009-02-19 Sanofis-Aventis Nouvelles tétrahydronaphtalines substituées, leurs procédés de préparation et leur utilisation comme médicaments
WO2010005004A1 (fr) * 2008-07-07 2010-01-14 花王株式会社 Inhibiteur de la xanthine oxydase et inhibiteur de la production d’acide urique
US9827279B2 (en) 2008-07-07 2017-11-28 Kao Corporation Xanthine oxidase inhibitor and uric acid production inhibitor
JP2010043008A (ja) * 2008-08-08 2010-02-25 Kansai Koso Co Ltd リパーゼ活性抑制剤及びこれを含有する化粧料
JP2010132564A (ja) * 2008-12-02 2010-06-17 Lotte Co Ltd 消臭剤及びそれを含む口腔用組成物並びに飲食品
JP2011037720A (ja) * 2009-08-06 2011-02-24 Kao Corp Ｄｇａｔ阻害剤
WO2011107494A1 (fr) 2010-03-03 2011-09-09 Sanofi Nouveaux dérivés aromatiques de glycoside, médicaments contenants ces composés, et leur utilisation
WO2011157827A1 (fr) 2010-06-18 2011-12-22 Sanofi Dérivés d'azolopyridin-3-one en tant qu'inhibiteurs de lipases et de phospholipases
WO2011161030A1 (fr) 2010-06-21 2011-12-29 Sanofi Dérivés de méthoxyphényle à substitution hétérocyclique par un groupe oxo, leur procédé de production et leur utilisation comme modulateurs du récepteur gpr40
WO2012004270A1 (fr) 2010-07-05 2012-01-12 Sanofi Dérivés 1,3-propanedioxyde à substitution spirocyclique, procédé de préparation et utilisation comme médicament
WO2012004269A1 (fr) 2010-07-05 2012-01-12 Sanofi Dérivés d'acide ( 2 -aryloxy -acétylamino) - phényl - propionique, procédé de production et utilisation comme médicament
WO2012010413A1 (fr) 2010-07-05 2012-01-26 Sanofi Acides hydroxy-phényl-hexiniques substitués par aryloxy-alkylène, procédé de production et utilisation comme médicament
WO2012120054A1 (fr) 2011-03-08 2012-09-13 Sanofi Dérivés oxathiazine di- et tri-substitués, procédé pour leur préparation, utilisation en tant que médicament, agent pharmaceutique contenant ces dérivés et utilisation
WO2012120053A1 (fr) 2011-03-08 2012-09-13 Sanofi Dérivés oxathiazine ramifiés, procédé pour leur préparation, utilisation en tant que médicament, agents pharmaceutiques contenant ces dérivés et leur utilisation
WO2012120056A1 (fr) 2011-03-08 2012-09-13 Sanofi Dérivés oxathiazine tétra-substitués, procédé pour leur préparation, utilisation en tant que médicament, agent pharmaceutique contenant ces dérivés et utilisation
WO2012120055A1 (fr) 2011-03-08 2012-09-13 Sanofi Dérivés oxathiazine di- et tri-substitués, procédé pour leur préparation, utilisation en tant que médicament, agent pharmaceutique contenant ces dérivés et utilisation
WO2012120052A1 (fr) 2011-03-08 2012-09-13 Sanofi Dérivés d'oxathiazine substitués par des carbocycles ou des hétérocycles, leur procédé de préparation, médicaments contenant ces composés et leur utilisation
CN102304158B (zh) * 2011-05-20 2014-07-30 中国人民解放军第二军医大学 酰化黄酮苷化合物及其在制备补体抑制剂药物中的应用
CN102304158A (zh) * 2011-05-20 2012-01-04 中国人民解放军第二军医大学 酰化黄酮苷化合物及其在制备补体抑制剂药物中的应用
WO2013037390A1 (fr) 2011-09-12 2013-03-21 Sanofi Dérivés amides d'acide 6-(4-hydroxyphényl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylique en tant qu'inhibiteurs de kinase
WO2013045413A1 (fr) 2011-09-27 2013-04-04 Sanofi Dérivés d'amide d'acide 6-(4-hydroxyphényl)-3-alkyl-1h-pyrazolo[3,4-b] pyridine-4-carboxylique utilisés comme inhibiteurs de kinase

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