WO2005013970A1 - Agent attenuant les troubles hepato-biliaires - Google Patents

Agent attenuant les troubles hepato-biliaires Download PDF

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Publication number
WO2005013970A1
WO2005013970A1 PCT/JP2004/011452 JP2004011452W WO2005013970A1 WO 2005013970 A1 WO2005013970 A1 WO 2005013970A1 JP 2004011452 W JP2004011452 W JP 2004011452W WO 2005013970 A1 WO2005013970 A1 WO 2005013970A1
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WO
WIPO (PCT)
Prior art keywords
proanthocyanidin
hepatobiliary
improving
agent
health food
Prior art date
Application number
PCT/JP2004/011452
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English (en)
Japanese (ja)
Inventor
Keiichi Abe
Taeko Iino
Takeshi Kurihara
Original Assignee
Suntory Limited
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 Suntory Limited filed Critical Suntory Limited
Priority to JP2005512988A priority Critical patent/JPWO2005013970A1/ja
Publication of WO2005013970A1 publication Critical patent/WO2005013970A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
    • C07D311/60—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2
    • C07D311/62—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2 with oxygen atoms directly attached in position 3, e.g. anthocyanidins
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics

Definitions

  • the present invention relates to an agent for improving hepato-biliary dysfunction comprising proanthocyanidin as an active ingredient. Further, the present invention relates to a health food for improving hepatobiliary disorders containing proanthocyanidin as an active ingredient.
  • Proanthocyanidins are a kind of polyphenols contained in plants and are known to have various activities such as antioxidant activity (Non-Patent Document 1 and Non-Patent Document 2).
  • Proanthocyanidin is known to have superoxide radical scavenging activity as its action, and a synergistic action with vitamin C having an antioxidant action has been reported (Non-patent Document 1). Further, as a clinical effect, a therapeutic effect on chronic knee inflammation is known (Non-Patent Document 1 and Non-Patent Document 2).
  • hepatobiliary disorders include, for example, acute hepatitis, cirrhosis, drug-induced liver injury, alcoholic liver injury, intrahepatic cholestasis, obstructive jaundice, and the presence of these disorders in the presence of AST (GOT ), ALT (GPT), and alkaline phosphatase (A1_P) levels are known to increase.
  • AST GAT
  • ALT GPT
  • A1_P alkaline phosphatase
  • Non-Patent Document 1 Bagchi D. et al., Toxicology, 2000, Vol. 148, p. 187-189
  • Non-Patent Document 1 Fremont L. et al., Life Sciences, 1999, Vol. 64, p. 2511-2521
  • An object of the present invention is to provide a novel agent for improving hepatobiliary disorders. Another object is to provide a novel health food for improving hepatobiliary disorders.
  • the inventors of the present invention have conducted intensive studies to solve the above-mentioned problems, and as a result, Have been found to have excellent GOT-lowering action, GTP-lowering action, alkaline phosphatase-lowering action, and neutral fat (triglyceride) -lowering action, and are effective in improving hepatobiliary disorders, and thus complete the present invention. Reached.
  • an agent for improving hepatobiliary disorder comprising proanthocyanidin as an active ingredient
  • the hepatobiliary disorder improving agent according to the above (1) which is used in the form of tablets, pills, capsules, granules, powders, powders, and liquid preparations,
  • the composition of the present invention can reduce blood GOT, GPT, and alkaline phosphatase levels, Hepatitis, cirrhosis, drug-induced liver injury, alcoholic liver injury, intrahepatic cholestasis, obstructive jaundice, chronic hepatitis C, chronic hepatitis B, primary biliary cirrhosis (PBC), primary sclerosing cholangitis ( Hepatobiliary disorders such as PSC), autoimmune hepatitis (AIH), fatty liver, and nonalcoholic steatohepatitis (NASH) can be improved.
  • FIG. 1 shows the effect of pine bark extract on AST (GOT) value due to continuous ingestion for one week. * Indicates a significant difference P ⁇ 0.05 compared to before pine bark ingestion.
  • FIG. 2 shows the effect on ALT (GPT) levels of pine bark extract after one week of continuous ingestion. *** indicates a significant difference ⁇ ⁇ 0.001 from that before pine bark ingestion.
  • FIG. 3 shows the effect on alkaline phosphatase (A1-—) levels of pine bark extract for one week in a continuous ingestion. * Indicates a significant difference ⁇ ⁇ 0.05 from before pine bark ingestion.
  • FIG. 4 shows the effect of pine bark extract on neutral fat (triglyceride) levels after one week of continuous ingestion. ** indicates a significant difference ⁇ ⁇ 0.01 from that before pine bark ingestion.
  • the proanthocyanidin used in the present invention refers to a flavan-1-ol and / or flavan-1,3-diol as a constitutional unit having a degree of polymerization of 2 or more, preferably 2-10-mer, Preferably, it refers to a compound group or a derivative composed of a polycondensate of 2- to 4-mer and a stereoisomer thereof.
  • flavan-1-ol and And / or a polycondensate having a degree of polymerization of 2 to 4 containing flavan-1,3-diol as a constitutional unit PC, oligomeric proanthocyaniam.
  • ⁇ PC is a powerful antioxidant (see Japanese Patent Publication No.
  • the proanthocyanidin contained in the composition such as the agent for improving hepatobiliary disorder according to the present invention is not particularly limited with respect to the origin of the raw material or the part used for the raw material, the production method, and the purification method.
  • Food raw materials such as the above bark, crushed fruits or seeds, or extracts thereof can be used.
  • Proanthocyanidins can be prepared by a known method [for example, the method described in Japanese Patent Publication No. Hei 3-7232 or a method for extraction from pine bark; RW Hemingway et al. Phytochemistry, 1983, Vol. 22, p. 275-281] or a method based thereon can easily obtain the above various plant strengths.
  • the pine bark extract is obtained by extracting pine bark with water or an organic solvent. If water is used, hot or hot water is used.
  • an organic solvent acceptable for food or drug production is used, for example, methanol, ethanol, propanol, butanol, butane, acetone, hexane, cyclohexane, propylene glycol , Hydrous ethanol, hydrous propylene glycol, ethyl methyl ketone, glycerin, methyl acetate, ethyl acetate, getyl ether, dichloromethane, edible fats and oils, 1,1,1,2, -tetrafluoroethane, 1,2-trichloroethene And so on.
  • These water and Organic solvents may be used alone or in combination.
  • hot water, hydrous ethanol, and hydrous propylene glycol are preferably used.
  • the method of extracting proanthocyanidins from pine bark is not particularly limited, but, for example, a heating extraction method, a supercritical fluid extraction method, or the like is used.
  • the supercritical fluid extraction method is a method of performing extraction using a supercritical fluid that is a fluid in a state exceeding a critical point (critical temperature, critical pressure) of a gas-liquid of a substance.
  • a supercritical fluid carbon dioxide, ethylene, propane, nitrous oxide (laughing gas) and the like are used.
  • carbon dioxide is preferably used.
  • the supercritical fluid extraction method includes an extraction step of extracting a target component with a supercritical fluid and a separation step of separating the target component from the supercritical fluid.
  • a separation step either extraction separation by pressure change, extraction separation by temperature change, or extraction separation using an adsorbent or absorbent may be performed.
  • a supercritical fluid may be extracted by an entrainer-added kneading method.
  • this method about 2 to 20% of, for example, ethanol, propanol, n-xane, acetone, and toluene are added to a supercritical fluid, and the resulting extraction fluid is used to perform supercritical fluid extraction.
  • This is a method for dramatically increasing the solubility of the extract in the extraction fluid or for enhancing the selectivity of separation, and is a method for efficiently obtaining a pine bark extract.
  • Extraction from pine bark may be carried out by a batch method of liquid carbon dioxide, a reflux method of liquid carbon dioxide, a reflux method of supercritical carbon dioxide, or the like, in addition to the above method.
  • the proanthocyanidin obtained as described above is obtained in a liquid or semi-solid form, and the extraction solvent is removed therefrom by a known method such as distillation under reduced pressure, spray drying, freeze drying and the like. Once removed, it can be used as a proanthocyanidin-containing concentrate or dried product.
  • a known purification means such as column chromatography, countercurrent distribution method and the like can be adopted to achieve the object.
  • Proanthocyanidin in a composition such as the agent for improving hepatobiliary disorders of the present invention is well dissolved in water and has high absorbability to a living body. It is highly stable under any acidic, neutral or alkaline conditions and can be easily incorporated into foods and drinks while maintaining its function. In addition, the effect can be expected shortly after the start of ingestion, and a sufficient effect can be obtained with a small amount of ingestion. Therefore, it is highly useful as a food material for infants and the elderly, who have limited intake and allowance as food and drink.
  • the composition of the present invention may be a composition for improving hepatobiliary disorder, or may be used for such purposes as foods and drinks, health foods, and functional foods. It may be a food, a pharmaceutical composition or the like.
  • the composition can be appropriately prepared in a solid or solution form such as tablets, pills, capsenoles, granules, powders, powders, and liquids by a known method. That is, the solid preparation or liquid preparation useful as the agent for improving the hepatobiliary disorder of the present invention is prepared by mixing proanthocyanidin and various additives as required, and using a well-known well-established preparation method.
  • excipients used as the above composition mixed with a coloring agent, a flavoring agent, a surfactant, a plasticizer or a fragrance.
  • excipients examples include sugar alcohols such as D-sorbitol, D-mannitol and xylitol, sugars such as glucose, sucrose, lactose and fructose, crystalline cellulose, carmellose sodium, calcium hydrogen phosphate, and wheat.
  • sugar alcohols such as D-sorbitol, D-mannitol and xylitol
  • sugars such as glucose, sucrose, lactose and fructose
  • crystalline cellulose such as crystalline cellulose
  • carmellose sodium calcium hydrogen phosphate
  • wheat examples include starch, rice starch, corn starch, potato starch, dextrin, ⁇ -cyclodextrin, light anhydrous anhydrous citric acid, titanium oxide, and magnesium aluminate metasilicate.
  • Examples of the pH adjuster include citric acid, malic acid, sodium hydrogen phosphate and dipotassium phosphate.
  • cooling agent examples include 1-menthol and heart-strength water.
  • suspending agent examples include kaolin, carmellose sodium, xanthan gum, methylcellulose and tragacanth.
  • diluent examples include purified water, ethanol, vegetable oil, and emulsifier.
  • antifoaming agent examples include dimethylpolysiloxane and silicone antifoaming agent.
  • Examples of the thickener include xanthan gum, tragacanth, methylcellulose, dextrin and the like.
  • Examples of the solubilizer include ethanol, sucrose fatty acid ester, and macrogol.
  • disintegrating agent examples include low-substituted hydroxypropylcellulose, carboxymethinoresenolerose kanoresidum, croscarnomelose sodium, hydroxypropinolestarch, partially alpha-starch starch and the like.
  • binder examples include methylcellulose, hydroxypropylcellulose, hydroxypropylmethylcellulose, polyvinylpyrrolidone, gelatin, gum arabic, ethylcellulose, polyvinyl alcohol, pullulan, alpha-monostarch, agar, tragacanth, and alginic acid. And propylene glycol alginate and the like.
  • Examples of the lubricant include stearic acid, magnesium stearate, calcium stearate, polyoxyl stearate, cetanol, talc, hydrogenated oil, sucrose fatty acid ester, dimethyl polysiloxane, beeswax, and beeswax.
  • Can be Examples of the antioxidant include ascorbic acid, dibutylhydroxytoluene (BHT), propyl gallate, butylhydroxydisole (BHA), tocopherol, ascorbic acid and citric acid.
  • Examples of the coating agent include hydroxypropyl methylcellulose, hydroxypropinoresenorelose, methinoresenorelose, etinoresenorelose, hydroxypropinolemethinolecellulose phthalate, hydroxypropyl methylcellulose acetate succinate, carboxymethyl Ethyl cellulose, cellulose acetate phthalate, polybutylacetal getylaminoacetate, aminoalkyl methacrylate copolymer, hydroxypropynolemethylcellulose acetate succinate, methacrylic acid copolymer, polybutylacetate cetylaminoacetate or shellac No.
  • coloring agent examples include cocoon extract, riboflavin, titanium oxide, and carotene solution.
  • Examples of the flavoring agent include cunic acid, adipic acid, ascorbic acid, fructose, D-sorbitol, glucose, sodium saccharin, single syrup, sucrose, honey, amatija, kanzo, citric acid, adipic acid, ascorbic acid, Orange oil, spruce tincture, squid Examples include oil, hearth, and menthol.
  • surfactant examples include polyoxyethylene hydrogenated castor oil, glycerin monostearate, sorbitan monostearate, sorbitan monolaurate, polyoxyethylene polyoxypropylene, polysorbates, sodium lauryl sulfate, macrogol or sucrose fatty acid Esters and the like.
  • plasticizer examples include triethyl tenoate, polyethylene glycol, triacetin, and cetanol.
  • flavor examples include natural flavors such as animal flavors and vegetable flavors, and synthetic flavors such as isolated flavors and purely synthetic flavors.
  • the amount of proanthocyanidin in the preparation is usually about 118% by weight, preferably about 250% by weight, based on the whole preparation.
  • proanthocyanidin In the case of food and drink, it is produced by blending proanthocyanidin or the above-mentioned proanthocyanidin-containing preparation at the time of production of food and drink.
  • solid foods such as bread, chewing gum, tatsuki, chocolate, cereal, etc., jams, ice cream, yogurt, jelly, etc., jams, creams or gels, juices, coffee, cocoa, green tea, oolong tea, black tea It can be in any food form such as beverages. It can also be incorporated into seasonings, food additives and the like.
  • Is not particularly limited amount of the food or beverage, as Puroan Bok Shianijin usually about 0. 0001- 80 weight 0/0, preferably about 0. 005- 50 wt%.
  • the dose is 1 mg / L to 20 g / L, preferably 2 mg / L to 10 g / L.
  • the method for administering the agent for improving hepatobiliary disorders of the present invention may be oral or parenteral.
  • the dosage of the agent for improving the hepatobiliary disorder of the present invention varies depending on its type, dosage form, age, weight, and adaptation symptoms of the patient.
  • One or several doses should be administered in a dose of about 1 to 500 mg, preferably about 3 to 300 mg. Also, when taking it as a health food, there is no problem even if you take it in the same amount as an oral preparation because there is no concern about side effects.
  • Example 1 a pine bark extract rich in OPT as an example, but the present invention is not limited thereto.
  • Example 1 a pine bark extract rich in OPT as an example, but the present invention is not limited thereto.
  • the subjects were 14 smoking adult males (33-48 years old, average 37.5 years old). Subjects were continuously ingested two tablets a day for one week for two weeks without changing daily lifestyle. Blood is collected immediately before the start of ingestion and one week after the start of ingestion. D), alkaline phosphatase and neutral fat (triglyceride) were measured. The results are shown in Table 1-2 below and Figure 1-4.
  • Moderate Increased hepatic / renal contrast ratio and obscure hepatic vessels are observed.
  • Altitude Increased carotenoid contrast ratio, obscure hepatic vessels, and echo attenuation in the deep liver are observed.
  • the ameliorating agent or ameliorating health food for hepatobiliary disorders according to the present invention is useful for the improvement, treatment and / or prevention of hepato-biliary disorders in the medical field or the health food field. Can be.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Food Science & Technology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Nutrition Science (AREA)
  • Mycology (AREA)
  • Botany (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Epidemiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyrane Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Tea And Coffee (AREA)

Abstract

L'invention porte sur un agent atténuant les troubles hépato-biliaires caractérisé en ce qu'il contient de la proanthocyanidine comme principe actif.
PCT/JP2004/011452 2003-08-11 2004-08-10 Agent attenuant les troubles hepato-biliaires WO2005013970A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2005512988A JPWO2005013970A1 (ja) 2003-08-11 2004-08-10 肝胆道系障害改善剤

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2003291779 2003-08-11
JP2003-291779 2003-08-11
JP2004146961 2004-05-17
JP2004-146961 2004-05-17

Publications (1)

Publication Number Publication Date
WO2005013970A1 true WO2005013970A1 (fr) 2005-02-17

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TW (1) TW200505468A (fr)
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006232752A (ja) * 2005-02-25 2006-09-07 Tokyo Univ Of Marine Science & Technology コレステロール及び中性脂肪吸収抑制剤及びこれを含む食品
JP2014508785A (ja) * 2011-03-22 2014-04-10 インダストリアル テクノロジー リサーチ インスティテュート 肝疾患治療用の医薬組成物

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5481274A (en) * 1977-11-25 1979-06-28 Zyma Sa Manufacture of oosubstituted derivative of ****cyanidanee33ol
JPH09291039A (ja) * 1995-12-26 1997-11-11 Suntory Ltd プロシアニジンを有効成分とする抗肥満剤
JPH11246562A (ja) * 1998-03-04 1999-09-14 Agency Of Ind Science & Technol プロアントシアニジンａおよびその誘導体
JP2001500546A (ja) * 1996-09-04 2001-01-16 バイオティクス、リサーチ、コーポレーション レンズマメ由来の抗酸化剤およびその製法と使用
EP1072265A1 (fr) * 1999-07-20 2001-01-31 MEDIS S.r.l. Medical Infusion Systems Utilisation de polyphenols des plantes pour le traitement de la surcharge en fer
JP2003095964A (ja) * 2001-09-21 2003-04-03 Toyo Shinyaku:Kk 抗ストレス剤
JP2004123707A (ja) * 2002-07-29 2004-04-22 Toyo Shinyaku:Kk 血流改善組成物
JP2004269487A (ja) * 2003-01-14 2004-09-30 Efuekuto:Kk 落花生由来のプロアントシアニジンの製造方法

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5481274A (en) * 1977-11-25 1979-06-28 Zyma Sa Manufacture of oosubstituted derivative of ****cyanidanee33ol
JPH09291039A (ja) * 1995-12-26 1997-11-11 Suntory Ltd プロシアニジンを有効成分とする抗肥満剤
JP2001500546A (ja) * 1996-09-04 2001-01-16 バイオティクス、リサーチ、コーポレーション レンズマメ由来の抗酸化剤およびその製法と使用
JPH11246562A (ja) * 1998-03-04 1999-09-14 Agency Of Ind Science & Technol プロアントシアニジンａおよびその誘導体
EP1072265A1 (fr) * 1999-07-20 2001-01-31 MEDIS S.r.l. Medical Infusion Systems Utilisation de polyphenols des plantes pour le traitement de la surcharge en fer
JP2003095964A (ja) * 2001-09-21 2003-04-03 Toyo Shinyaku:Kk 抗ストレス剤
JP2004123707A (ja) * 2002-07-29 2004-04-22 Toyo Shinyaku:Kk 血流改善組成物
JP2004269487A (ja) * 2003-01-14 2004-09-30 Efuekuto:Kk 落花生由来のプロアントシアニジンの製造方法

Non-Patent Citations (3)

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Title
SPRYGIN V.G. ET AL.: "Antioxidant action of oligomeric proanthocyanidis isolated from viburnum in liver lesions by carbon tetra chloride and prevention of the latter's toxicity", GIG. SANIT., vol. 3, May 2003 (2003-05-01) - June 2003 (2003-06-01), pages 57 - 60, XP002995620 *
UBILLAS R. ET AL.: "SP-303, an antiviral oligomeric proanthocyanidin from the latex of Croton lechleri (Sangrede drago)", PHYTOMEDICINE, vol. 1, no. 2, 1994, pages 77 - 106, XP002995621 *
YOSHIKAWA M. ET AL.: "Hepatoprotective and antioxidative properties of Salacia reticulata: preventive effects of phenolic constituents on CC14-induced liver injury in mice", BIOLOGICAL & PHARMACEUTICAL BULLETIN, vol. 25, no. 1, 2002, pages 72 - 76, XP002995622 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006232752A (ja) * 2005-02-25 2006-09-07 Tokyo Univ Of Marine Science & Technology コレステロール及び中性脂肪吸収抑制剤及びこれを含む食品
JP2014508785A (ja) * 2011-03-22 2014-04-10 インダストリアル テクノロジー リサーチ インスティテュート 肝疾患治療用の医薬組成物

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JPWO2005013970A1 (ja) 2007-09-27

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