WO1996036346A1 - Extrait hydrosoluble tire de la celosie argentee - Google Patents

Extrait hydrosoluble tire de la celosie argentee Download PDF

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Publication number
WO1996036346A1
WO1996036346A1 PCT/JP1996/001275 JP9601275W WO9636346A1 WO 1996036346 A1 WO1996036346 A1 WO 1996036346A1 JP 9601275 W JP9601275 W JP 9601275W WO 9636346 A1 WO9636346 A1 WO 9636346A1
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WIPO (PCT)
Prior art keywords
water
soluble extract
extract
soluble
liver
Prior art date
Application number
PCT/JP1996/001275
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English (en)
Japanese (ja)
Inventor
Tooru Takahashi
Koji Hase
Tsuneo Namba
Original Assignee
Yamanouchi Pharmaceutical Co., Ltd.
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 Yamanouchi Pharmaceutical Co., Ltd. filed Critical Yamanouchi Pharmaceutical Co., Ltd.
Priority to JP53469796A priority Critical patent/JP3984288B2/ja
Priority to AU57019/96A priority patent/AU5701996A/en
Publication of WO1996036346A1 publication Critical patent/WO1996036346A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/21—Amaranthaceae (Amaranth family), e.g. pigweed, rockwort or globe amaranth
    • 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
    • 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 provides a water-soluble extract containing a polysaccharide as a main component and an active ingredient containing the water-soluble extract obtained by extraction and isolation from a crude drug, Seisho, and is particularly useful for prevention and treatment of liver injury.
  • Pharmaceutical compositions or food additives are particularly useful for prevention and treatment of liver injury.
  • the liver is also called a “silent organ” because the liver has a strong natural healing power and does not show prominent symptoms with a few disorders, and it is important for humans to metabolize, regulate blood sugar, detoxify, regulate bile circulation, store nutrients, etc. It plays an essential function in maintaining life.
  • the number of patients showing liver function abnormalities has increased with the increase in alcohol consumption.
  • the etiology and pathology of hepatic disorder are diverse, the most demanding therapeutic agents are high medical needs and chronic active hepatitis. Research and development of various therapeutic agents ranging from antiviral agents to immunomodulators are being actively conducted.
  • Kampo therapy has been practiced since ancient times, such as Sho-saiko-to (Saiko-Hanaxia ⁇ Ginseng 'Large ⁇ Licorice' ginger ⁇ Huang-gong), Furubai-to Ryo • Herbal medicines such as Kusagosha (Gomiko, Osume, Oso) are used as “cleanse the liver”, “remove the heat of the liver”, and “help the liver”.
  • the active ingredient is not clear. .
  • polysaccharide is a generic name for high molecular compounds in which a large number of monosaccharides are polymerized by glycosidic bonds, and is composed of a single polysaccharide composed of the same monosaccharide molecule and a complex composed of various monosaccharides and their derivatives.
  • polysaccharides There are polysaccharides.
  • dextran formed by linear polymerization of glucose is known as a plasma expander, and lentinan extracted from shiitake and schizophyllan extracted from shirohirotake have antitumor activity. Many have biological activity.
  • Use crude drug-derived polysaccharides for liver disease As a specific example, Japanese Patent Publication No. 6-886481 describes a polysaccharide obtained by fermenting grass fiber in a specific culture solution and having a therapeutic effect on hepatitis B. There is. _Technical issues
  • blue ginger polysaccharides extracted and isolated from seeds of blue ginger (Ce1osiaargentea L.) (hereinafter referred to as blue ginger) are obtained. It has been found that a water-soluble extract containing as a main component and further containing a protein has a remarkable inhibitory effect on liver diseases, thereby completing the present invention.
  • the present invention relates to a water-soluble extract comprising extraction and isolation from green ginger, and more particularly to a water-soluble extract obtained by the following steps (a) to (c).
  • the water-soluble extract of the present invention has a molecular weight of 1 to 300,000 and has the following physicochemical properties (1) and (2).
  • the water-soluble extract of the present invention contains 90 to 99% by weight of polysaccharide and 1 to 10% by weight of protein.
  • the present invention provides a pharmaceutical composition for humans or animals comprising the above-mentioned water-soluble extract as an active ingredient, particularly a composition useful for the prevention and treatment of liver damage in humans or animals, and the above-mentioned water-soluble extract
  • a pharmaceutical composition for humans or animals comprising the above-mentioned water-soluble extract as an active ingredient, particularly a composition useful for the prevention and treatment of liver damage in humans or animals, and the above-mentioned water-soluble extract
  • the present invention relates to a food additive containing:
  • the water-soluble extract obtained by extraction and isolation from the green ginger of the present invention contains 90 to 99% by weight of a polysaccharide and 1 to 10% by weight of a protein. It contains polysaccharide units corresponding to arabinose, rhamnose, mannose, galactose, galacturonic acid, glucose, fucose and glucuronic acid, and further contains trace amounts of sugar alcohols.
  • This water-soluble extract is acidic, has a molecular weight of 1 to 300,000, and contains 0.5 to 1.5% of protein-derived nitrogen atoms.
  • the water-soluble extract of the present invention is obtained by extracting an aqueous extract from a herbal medicine, green ginger, and then treating the aqueous extract with an organic solvent to obtain an organic solvent-insoluble precipitate. It can be obtained by subjecting the medium-insoluble precipitate to purification and isolating the water-soluble extract.
  • the method for extracting and isolating the water-soluble extract of the present invention from blue ginger is as follows.
  • the extraction is carried out by extracting a water-soluble extract with water or an aqueous solvent from a crushed product of the crude drug green ginger, the seeds of its original plant Nogatei or other homologous plants.
  • blue ginger refers to not only the dried crude herb seeds but also the crude drugs sold as green ginger, such as the mature seeds of the above-mentioned cockscomb-contaminated green ginger. Is dried.
  • Notomato which is the original plant
  • examples of such congener plants include corn beetle and japonicus.
  • the pulverized material may be roughly cut or coarsely powdered, but it is advantageous to use the powder, that is, green ginger powder, in order to increase the extraction efficiency.
  • green ginger powder which is an object to be extracted, can be directly applied to the extraction operation without being degreased in advance.
  • an organic solvent generally used for extracting lipids from crude drugs such as black form, methanol, ethanol, acetone and tetrahydrofuran, is suitably used.
  • the water used as the extraction solvent may be ordinary water, but preferably purified water is used.
  • aqueous solvent examples include various buffers commonly used for polysaccharide extraction, such as a phosphate buffer and an acetate buffer, and aqueous solutions of salts such as salt.
  • the amount of water or aqueous solvent used also depends on the method of leaching, and is not particularly limited as long as the extract of the present invention can be extracted. A suitable amount is 5 to 15 times, especially about 0.6 to 10 times.
  • the ginger extract of the present invention is a water-soluble and heat-stable extract, and the extract obtainable by hot extraction achieves the object of providing the preventive / therapeutic agent for liver injury of the present invention. Above all, the extraction is preferably performed by hot extraction.
  • the extraction is performed not only on a laboratory scale Soxhlet extractor and a heated reflux extractor, but also on an industrial scale extractor usually used for extracting physiologically active substances mainly composed of water-soluble polysaccharides from crude drugs. For example, it can be advantageously implemented by various percolators.
  • the extract thus obtained is concentrated according to a conventional method, and separated into solid and liquid by filtration or the like.
  • the extract obtained in the extraction step can be directly subjected to the separation step, but it is preferable to dry the extract in order to increase the separation efficiency by the organic solvent treatment in the separation step.
  • any drying means commonly used for drying crude drug extracts such as ventilation drying, vacuum drying, freeze drying, spray drying and the like can be applied, but freeze drying is advantageous.
  • the dried extract is then treated with an organic solvent to separate a water-soluble and organic solvent-insoluble matter from a water-soluble organic solvent-soluble matter.
  • the organic solvent may be any organic solvent that dissolves a substance that is water-soluble but soluble in the organic solvent in the organic solvent by treatment with the organic solvent.
  • organic solvent In isolating a green ginger extract, black-mouthed form and ethanol are preferred. Cloth form treatment and ethanol treatment can be applied in any order.
  • the water-soluble and organic solvent-insoluble extract of the present invention is separated as a precipitate.
  • the separated precipitate is subjected to solid-liquid separation by a conventional method such as filtration, and then dissolved in water and dialyzed to remove salts and, if necessary, low-molecular substances.
  • Dialysis is a means commonly used for desalination and purification of crude drug components such as electrodialysis, ultrafiltration membranes, and reverse osmosis, and deviations can be applied.
  • dialysis is preferably performed using an ultrafiltration membrane having a molecular sieve.
  • an ultrafiltration membrane that separates with a molecular weight of about 10,000 is suitable.
  • Dialysis with this ultrafiltration membrane usually takes 3 hours to 5 days In particular, in the separation of the green ginger extract of the present invention, about 12 hours to 3 days is preferable.
  • the dissolved and dialyzed green ginger extract is then purified from crude drugs such as chromatography by a purification means generally used for the purification of an extract containing a polysaccharide as a main component, and is isolated as a substance having a single fraction peak. Separated.
  • Chromatography is usually performed using ion exchange chromatography, gel filtration chromatography, affinity chromatography, HPLC, etc. ⁇ Ion exchange chromatography or gel Filter mouth chromatography is advantageous.
  • UV absorption spectrum Figure 1 shows the UV absorption spectrum data measured in distilled water.
  • Figure 2 shows infrared absorption spectrum data measured by the KBr method.
  • compositions for oral administration can be solid or liquid, powders, syrups, capsules, granules,? An L agent, a suspension, a drop, etc. may be used. Carriers or excipients for such compositions are well known.
  • composition may further comprise conventional materials such as binders, stabilizers, emulsifiers, suspending agents, dispersing agents, lubricants, preservatives, bulking agents and the like.
  • water-soluble extract of the present invention can be used as a food additive in health foods, functional foods, and the like.
  • the daily dose of the composition for preventing or treating hepatic injury according to the present invention may be 10 to 100 OmgZ adult in terms of polysaccharide which is a main component of the water-soluble extract. Desirable.
  • the water-soluble extract of the present invention has an inhibitory effect on toxic liver damage caused by alcohol and drugs, and immune liver damage caused by virus and virus, and is useful for prevention and treatment of liver damage.
  • the peroxidation of intracellular organ membrane lipids is caused by free radicals generated in the course of alcohol and drug metabolism, but the water-soluble extract of the present invention has an effect of inhibiting the production of lipid peroxide.
  • tumor necrosis factor (TN) has been reported to be involved in fulminant illness of viral hepatitis and exacerbation of alcoholic hepatitis. It is considered to be one of the major medias every day, but the water-soluble extract of the present invention It also showed a significant inhibitory effect on NF-induced liver injury.
  • Example 3 An aqueous extract obtained by extracting blue ginger with hot water in Example a) described below, an organic solvent-insoluble precipitate obtained by treating the aqueous extract with an organic solvent in Example 2 described below, and In Example 3, the effect of CE 1 obtained by further purifying the organic solvent-insoluble precipitate on CC 14 -induced liver injury was examined.
  • a test drug dissolved in physiological saline or suspended uniformly in a 0.5% CMC aqueous solution was administered to male Sprague-Dawley rats (6 weeks of age) p. After 12, 24 hours, 3 mgZkg of a mixed solution of CC14Z01 oil (1: 4 v / v) was injected subcutaneously into the back or intraperitoneally.
  • the test drug and CC14 were administered by different routes.
  • Condition control group saline, or after administration only 0. 5% C MC solution was injected CC 1 4 similarly.
  • the control group received 100 mg of glycyrrhizin instead of the test drug.
  • Glycyrrhizin is a compound that is used as an active ingredient in licorice such as Sho-Sho-to for liver disease.
  • CC 1 4 will cause a chemical (toxic) liver failure (T. Yokozawa et al., Pharmacognosy magazine 47, 229 (1993), N. I shi da et a to J.Hepatology 13,200 (1991)).
  • trichloromethyl radical ( ⁇ CC 1 3) is produced in the endoplasmic reticulum drug metabolism pathway, which proteins of hepatocytes, covalently bound to a lipid such as It is presumed that the function is changed and also acts on the cell membrane to produce peroxidized lipids (lipidoperoxide, LPO), altering the membrane and eventually causing cell necrosis (Paul B) McCay et al., J. Biological Chem. 259.2135 (1984)).
  • Dg a 1 actos am ine hereinafter abbreviated as D-ga
  • LPS ZL ipopo lys ac cha ri de
  • Example a) The effects of an aqueous extract obtained by extracting blue ginger with hot water in Example a) and CE 1 obtained in Example c) described below on D-ga 1ZL PS-induced liver injury were examined.
  • To the disease state control group only the solvent was administered, and then D-ga1 and LPS were similarly administered.
  • the control group received 10 OmgZ kg of glycyrrhizin instead of the test drug.
  • Blood was collected 8 hours after administration of D-ga1 and LPS, and GOT, GPT, LDH, and pyrilrubin levels were measured.
  • Dg a 1 is metabolized in cells and becomes ur idi ne 5'-di pho spha te (UDP) —galactosamine, uridine phosphide (ur idi ne 5—monophospha te (UMP), UDP, ur idi ne 5'-tri Phosphate (UTP) deficiency occurs.
  • UDP ur idi ne 5'-di pho spha te
  • UDP uridine phosphide
  • UDP ur idi ne 5'-tri Phosphate
  • mice show resistance to this liver injury.
  • Power, power, and galactosamine A remarkable liver injury model can be obtained by administering a small amount of Endotoxin (LPS) to sensitized mice.
  • LPS Endotoxin
  • L TD 4 1 euk 0 triene D 4
  • L TD 4 1 euk 0 triene D 4
  • the blood vessel temporarily becomes ischemic, and superoxide is generated when the blood flow starts flowing again with a decrease in LTD 4 concentration. by. That is, it destroys cells sensitized by Tga-Dga1 secreted from macrophages activated by super-one-year-old oxide (LPS itself is directly activated).
  • Example a) The effects of the aqueous extract obtained by extracting blue ginger with hot water in Example a) and the CE1 obtained in Example c) described below on P. acnesZLPS-induced liver injury were examined.
  • the same test was performed using CE1 and 1 OmgZkg. However, the dose of LPS was 50 mg.
  • the control group received 25 mg Zkg of glycyrrhizin instead of the test drug.
  • Each group consists of 12-14 animals, and the bioassay is K ap 1a It was performed by the n-Me iyer method / generalized Wi 1 coxon test.
  • Example c The inhibitory effect of CE 1 obtained in Example c) described later on lipid peroxide production was examined.
  • Incubated rat Kanmi closo one base Schorr completion to an arm preparative iron complex F e S_ ⁇ 4 or adenosine 5 '-di phospha te (ADP ) / F e C 1 3 and CE 1 were added 37 ° C2 0 minutes, The lipid peroxide produced was determined by the malondialdehyde method.
  • Example c The effect of CE1 obtained in Example c) described later on TNF-induced liver injury was examined.
  • Table 1 shows the levels of various serum enzymes and the magnitude of the blood protective effect when administered at 10 OmgZkg to a CC14-induced liver injury rat.
  • the blood protective action refers to the degree to which the test drug suppresses an increase in serum enzyme levels.
  • Table 2 shows the GPT level, the reduction rate, and the number of dead mice when the aqueous extract was administered to D-ga 1ZL PS-induced liver injury mice at 20 Omg / kg. Table 2 shows that the aqueous extract markedly suppressed the increase in serum GPT level and the mortality of D-gal / LPS-induced liver injury mice.
  • FIG. 3 shows the survival rate of the mice when the aqueous extract was administered to P. acnesZLPS-induced liver injury mice.
  • FIG. 3 shows that the aqueous extract significantly suppressed the mortality of P. ances / LPS-induced liver injury mice.
  • Table 3 Aqueous extract obtained from green pepper was used for black mouth form and methanol.
  • G PT glutamic- pyruvic transaminase
  • Example c The organic solvent-insoluble precipitate obtained in Example) was purified in Example c), cases administered at a dose of 2 SmgZk g of CE 1 obtained by isolated CC 1 4 induced liver failure rats Bok various serum Table 4 shows enzyme levels.
  • CE 1 is a lower dose-than glycyrrhizin, significantly suppressed won the elevated levels of serum parameters CC 1 4-induced liver injury rat, it can be seen that a much more effective liver damage inhibitory effect than glycyrrhizin.
  • Serum enzyme levels when administered at a dose of 5 mg / kg Dosage number of samples Serum GOT level Serum GPT level Serum LDH level Serum pyrilvin level Group
  • GPT glutamic-pyruvic transaminase
  • CE 1 is D—ga 1 no?
  • Table 6 shows the serum GPT levels and their reduction rates when the mice were administered at a dose of 1 OmgZkg and 50 mgZkg to mice with induced liver injury.
  • Table 6 C E1 was added to D-gajZLPS-induced liver injury mice at 10 mg gZkg.
  • G PT glutamic-pyruvic transaminase
  • FIG. 4 shows the mouse survival rate when CE1 was administered to PacnesPSS-induced liver injury mice.
  • CE 1 significantly suppressed the lethality of P. acnes / LPS-induced liver injury mice, indicating that the effect was stronger than that of glycyrrhizin.
  • Table 7 shows the results of measuring the effect of CE 1 on inhibiting lipid peroxide acidity. Table 7 shows that CE 1 suppressed the production of lipid peroxide in a dose-dependent manner.
  • ADP adenosine 5 '-di hosphate
  • Table 8 shows the serum GPT levels and their reduction rates when CE1 was administered to TNF-induced spleen-induced liver injury mice. Table 8 shows that CE 1 suppresses the increase in serum GPT levels induced by TNF-ligand.
  • Serum G ⁇ ⁇ level and its decrease rate Dose Sample No. Serum GPT level GPT decrease rate group
  • FIG. 1 is a graph showing the UV absorption spectrum data of CE1.
  • FIG. 2 is a graph showing infrared absorption spectrum data of CE1.
  • Figure 3 shows (a) a graph showing the effect of the aqueous extract on the survival rate of P. acnes s / LPS-induced liver injury mice and (b) a graph showing the effect of glycyrrhizin on the survival rate of P. acnes sZLPS-induced liver injury mice. It is a graph which shows an effect.
  • FIG. 4 is a graph showing the effect of CE1 on the survival rate of P. acnes ZLPS-induced liver injury mice.
  • FIG. 5 is a diagram showing a purification process of CE1 from blue ginger.

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Abstract

L'invention porte sur un extrait hydrosoluble tiré et isolé de la célosie argentée (Célosia argentea, L.), plante de la famille des amarantacées, et sur une composition médicinale ou un additif alimentaire dont cet extrait constitue le principe actif. Ledit extrait, qui contient de 90 à 99 % en poids de polysaccharides, et de 1 à 10 % en poids de protéines, exerce une action dépressive sur les hépatopathies toxiques liées à la consommation d'alcool et de drogues, et les hépatopathies immunitaires d'origine virale ou autres, et s'avère donc utile pour prévenir ou traiter les hématopathies.
PCT/JP1996/001275 1995-05-17 1996-05-15 Extrait hydrosoluble tire de la celosie argentee WO1996036346A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP53469796A JP3984288B2 (ja) 1995-05-17 1996-05-15 青しょう子由来の予防・治療用組成物
AU57019/96A AU5701996A (en) 1995-05-17 1996-05-15 Water-soluble extract originating in feather cockscomb

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP11758495 1995-05-17
JP7/117584 1995-05-17

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002527457A (ja) * 1998-10-16 2002-08-27 ソシエテ デ プロデユイ ネツスル ソシエテ アノニム 消化の遅いタン白物質およびその使用
JP2005220101A (ja) * 2004-02-06 2005-08-18 Maruzen Pharmaceut Co Ltd 抗老化剤、血小板凝集抑制剤、抗酸化剤、抗アレルギー剤及び飲食品
JP2005320271A (ja) * 2004-05-07 2005-11-17 Maruzen Pharmaceut Co Ltd アルドースリダクターゼ活性阻害剤、糖尿病性合併症予防・治療剤及び糖尿病性合併症予防・治療用飲食品

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4891211A (fr) * 1972-03-11 1973-11-28
JPH02223526A (ja) * 1988-11-04 1990-09-05 Freunt Ind Co Ltd 食品用の含水有機溶剤抽出物含有組成物および医薬用の含水有機溶剤抽出物含有組成物、並びにそれらの製造方法
JPH03223217A (ja) * 1989-03-03 1991-10-02 Asahi Breweries Ltd 抗活性酸素作用剤並びにこれを有効成分とする抗活性酸素剤、食品、化粧料及び医薬品
JPH03255032A (ja) * 1990-03-05 1991-11-13 Sanyo Kokusaku Pulp Co Ltd 抗腫瘍剤
JPH0899889A (ja) * 1994-08-02 1996-04-16 Taisho Pharmaceut Co Ltd アトピー性皮膚炎治療剤

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4891211A (fr) * 1972-03-11 1973-11-28
JPH02223526A (ja) * 1988-11-04 1990-09-05 Freunt Ind Co Ltd 食品用の含水有機溶剤抽出物含有組成物および医薬用の含水有機溶剤抽出物含有組成物、並びにそれらの製造方法
JPH03223217A (ja) * 1989-03-03 1991-10-02 Asahi Breweries Ltd 抗活性酸素作用剤並びにこれを有効成分とする抗活性酸素剤、食品、化粧料及び医薬品
JPH03255032A (ja) * 1990-03-05 1991-11-13 Sanyo Kokusaku Pulp Co Ltd 抗腫瘍剤
JPH0899889A (ja) * 1994-08-02 1996-04-16 Taisho Pharmaceut Co Ltd アトピー性皮膚炎治療剤

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
KANEYOSHI AKAMATSU, (Author), "New Edit. Chinese and Japanese Medicine", 1st Edit., 5th Print, 15 October 1980, ISHIYAKU SHUPPAN K.K., (TOKYO), p. 478. *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002527457A (ja) * 1998-10-16 2002-08-27 ソシエテ デ プロデユイ ネツスル ソシエテ アノニム 消化の遅いタン白物質およびその使用
JP2005220101A (ja) * 2004-02-06 2005-08-18 Maruzen Pharmaceut Co Ltd 抗老化剤、血小板凝集抑制剤、抗酸化剤、抗アレルギー剤及び飲食品
JP2005320271A (ja) * 2004-05-07 2005-11-17 Maruzen Pharmaceut Co Ltd アルドースリダクターゼ活性阻害剤、糖尿病性合併症予防・治療剤及び糖尿病性合併症予防・治療用飲食品
JP4623999B2 (ja) * 2004-05-07 2011-02-02 丸善製薬株式会社 アルドースリダクターゼ活性阻害剤、糖尿病性合併症予防・治療剤及び糖尿病性合併症予防・治療用飲食品

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AU5701996A (en) 1996-11-29

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