WO2004064830A1 - Processed fat compositions for preventing and improving lifestyle-related diseases - Google Patents
Processed fat compositions for preventing and improving lifestyle-related diseases Download PDFInfo
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- WO2004064830A1 WO2004064830A1 PCT/JP2004/000599 JP2004000599W WO2004064830A1 WO 2004064830 A1 WO2004064830 A1 WO 2004064830A1 JP 2004000599 W JP2004000599 W JP 2004000599W WO 2004064830 A1 WO2004064830 A1 WO 2004064830A1
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- WIPO (PCT)
- Prior art keywords
- fat
- oil
- group
- dehydrogliasperin
- glycillin
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- 235000005713 safflower oil Nutrition 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 235000012045 salad Nutrition 0.000 description 1
- 235000015067 sauces Nutrition 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229940073490 sodium glutamate Drugs 0.000 description 1
- 235000014214 soft drink Nutrition 0.000 description 1
- 235000014347 soups Nutrition 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 210000004003 subcutaneous fat Anatomy 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 235000019166 vitamin D Nutrition 0.000 description 1
- 239000011710 vitamin D Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 235000008939 whole milk Nutrition 0.000 description 1
Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—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
-
- 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
- A23L33/115—Fatty acids or derivatives thereof; Fats or oils
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/365—Lactones
- A61K31/366—Lactones having six-membered rings, e.g. delta-lactones
- A61K31/37—Coumarins, e.g. psoralen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin
-
- 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
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Definitions
- Oil processing composition for prevention and improvement of lifestyle-related diseases Oil processing composition for prevention and improvement of lifestyle-related diseases
- the present invention is for preventing and / or improving lifestyle-related diseases which can be used in foods and drinks such as health foods and functional health foods (food for specified health use, nutritional foods), pharmaceuticals, quasi-drugs, cosmetics, etc.
- the present invention relates to an oil and fat composition of Background art
- lifestyle-related diseases caused by deterioration of lifestyle such as overnutrition and lack of exercise have become a major social problem.
- the lifestyle-related diseases here include visceral fat obesity, type 2 diabetes, hyperlipidemia, hypertension, and the like, and the multiple-risk 'factor syndrome, which eventually worsens to arteriosclerosis. Therefore, a composition having the effect of preventing and / or improving these lifestyle-related diseases is desired, and the form of the composition is a health food or a health functional food (a food for specified health use, Foods and drinks such as nutritional foods), pharmaceuticals, quasi-drugs, and cosmetics are desired.
- Multiple 'risk' factor syndromes are syndrome X due to Reaven X (Diabetes, 37, 1595-1607, 1988), quartet of death due to Kaplan (Archi Vesof Internal Medicine, 149, 1514-1520) Insulin Resistance Syndrome (Diabetes Care, 14, 173-194, 1991) due to DeFronzo, Visceral Fat Syndrome due to Matsuzawa (Diabetes / Metabo 1 ism Revi ewew) s, 13, 3–13, 1997), and the common causative factor of these syndromes is thought to be insulin resistance.
- thiazolidine derivatives such as troglitazone, pioglitazone, and rosiglitazone, which are ligands for peroxisome proliferator-activated receptor ⁇ (peroxisome prollferator-activatedreceptory PP AR 7), have shown that these drugs are used in patients with type 2 diabetes. It has been shown to improve insulin resistance and show a hypoglycemic effect, and has been clinically applied as an insulin resistance ameliorating drug and a type 2 diabetes drug. Furthermore, it has been clarified that these thiazolidine derivatives increase subcutaneous fat but reduce visceral fat, and have a blood free fatty acid lowering action, a blood pressure lowering action, and a pile inflammatory action.
- a compound having PPARy ligand activity improves insulin resistance and is effective in preventing and / or improving lifestyle-related diseases such as visceral fat obesity, type 2 diabetes, hyperlipidemia, and hypertension.
- Licorice is a plant belonging to the genus Glycyrrhiza in the legume family, and is used for edible and medicinal purposes (herbal medicine).
- the main varieties are Darikiruliza'Glabra (Glycyrrhizaglabra) and G. ensis) and G. infata (G. inf 1 ata).
- All varieties contain glycyrrhizin (daricyrrhizic acid), a hydrophilic component, but the flavonoid, a hydrophobic component, contains specific compounds depending on the cultivar. This cultivar-specific flavonoid may be used to identify licorice varieties.
- hydrophobic extracts containing a large amount of licorice flaponoids and having a very small amount of glycyrrhizin are multiple.Risk 'Factor' may be useful for prevention and / or improvement of symptomatic groups.
- hydrophobic extract of licorice has P PAR ⁇ ligand activity, and its active ingredient is flavonoid, especially prenylflavonoid (WO 03-037316). Above all, the extract derived from G.
- peralensis has high PPARV ligand activity, and the prenyl flavonoids contained in the extract, glycicumarin, glycillin, dehydrodariasperin C and dehydrodariasperin D, have high activity.
- dehydroglasperin D is a compound newly found in WO 03/037316.
- licorice hydrophobic flavonoids are hardly soluble in water, are easily solidified as they are extracted from organic solvents, and color change is rapid. Due to its nature, it is difficult to use. To solve this, licorice hydrophobic flavonoids are dissolved in medium-chain fatty acid triglycerides, and the licorice hydrophobic flaponoid preparations are used as antioxidants, antibacterial agents, enzyme inhibitors, coloring agents, antitumor agents, antiallergic agents, It is used as an antiviral agent, etc. (Patent No. 279443). However, in Patent No. 2794443, there is no limitation on the compound, and no use of the compound as a preventive and / or ameliorating agent for lifestyle-related diseases is known. Summary of the Invention
- the present invention comprises at least one compound selected from the group consisting of glycicoumarin, glycillin, dehydroglasperin C and dehydrodariasperin D, and comprises a health food or a health functional food (specified health food, nutritional food). It is an object of the present invention to provide a composition for preventing and / or improving lifestyle-related diseases, which can be used for foods and drinks, pharmaceuticals, quasi-drugs, cosmetics, and the like.
- the present inventors have conducted intensive studies in view of the above-mentioned circumstances, and as a result, it was possible to specifically dissolve glycicoumarin, glycillin, dehydrogliasperin C and dehydrogliasperin D in certain kinds of oils and fats. It has been found that the stability of these compounds is improved by dissolving them in fats and oils, and that the processability of foods and drinks, pharmaceuticals, quasi-drugs, cosmetics, and the like is also improved, and the present invention has been completed.
- the present invention provides a lifestyle-related disease characterized by containing an oil or fat in which at least one compound selected from the group consisting of glycicoumarin, glycillin, dehydrogliasperin C and dehydrodaria sperin D is dissolved.
- the present invention relates to a fat and oil processing composition for prevention and / or improvement, and a fat and oil processing composition for improving insulin resistance.
- the present invention relates to glycicoumarin, glycillin, dehydrodaria sperin C and ⁇ using a composition containing an oil or fat in which at least one compound selected from the group consisting of dehydrodaria sperin D is dissolved, a method for preventing and / or improving lifestyle-related diseases, a method for improving insulin resistance,
- the present invention relates to a method for preventing and / or improving hyperglycemia, and a method for reducing intraperitoneal fat.
- the oil- and fat-processed la composition for preventing and / or improving lifestyle-related diseases is at least one compound selected from the group consisting of glycitamarin, glycillin, dehydrogliasperin C and dehydrogliasperin D. It is characterized in that it contains oils and fats in which is dissolved.
- the oil / fat processing composition for improving insulin resistance ⁇ t of the present invention has at least one compound selected from the group consisting of glycicoumarin, glycillin, dehydrodariasperin C and dehydrogliasperin D dissolved therein. It is characterized by containing fats and oils.
- the oil and fat processing composition of the present invention preferably contains, among the compounds, dehydrogliasperin D and at least one compound selected from the group consisting of glycicoumarin, glycillin and dehydrogliasperin C. Furthermore, it is more preferable that it contains dehydrologliasperin C and dehydrodariasperin D, and that it contains either glycicoumarin or glycillin. In particular, it is most preferable to include all of glycitamarin, glycillin, dehydrogliasperin C and dehydrogliasperin D.
- the compound has PPARy ligand activity similarly to thiazolidine derivatives such as troglitazone pioglitazone, insulin resistance is improved, and visceral fat obesity, type 2 diabetes, hyperlipidemia, It is effective in preventing and / or improving lifestyle-related diseases such as blood pressure.
- Glycicoumarin (g 1 ycycoumarin) and dalicillin (g 1 ycyrin) used in the present invention are flavonoids classified into 3-arycoumarin (3-arylcoumarin), and are represented by the following general formula (1).
- dehydrodroglyasperin C and the dehydroglyasperin D used in the present invention are classified into isoflav-1-3-ene. It is a flavonoid and a compound represented by the following general formula (2).
- Glicitamarin, glycillin, dehydrogliasperin C and dehydroglia sperin D are components that are specifically contained in Glycyrrhiza peralensis (G1ycyrrhiizarualensils) among licorice, and are hardly contained in other varieties. However, it may be included in hybrids between G. peralensis and other varieties.
- the compound is separated from other flavonoid components by high-performance liquid chromatography (HPLC) using a reversed-phase column such as ODS (a packing material in which octadecylsilyl groups are chemically bonded to a silica gel carrier), and detected and quantified. can do.
- the method for obtaining glycicoumarin, glycillin, dehydrogliasperin C and dehydrogliasperin D is not particularly limited. It can be obtained from cis licorice.
- the method is not particularly limited, and examples thereof include extraction with an organic solvent such as ethanol, ethyl acetate, and acetone.
- the compound is contained in the licorice hydrophobic extract obtained by the above extraction, and the compound may be used as it is, but it may be further purified or purified by column treatment, deodorization treatment, decolorization treatment, etc. Is also good.
- any of compounds derived from other natural sources such as plants, chemically synthesized compounds, and those biosynthesized by cultured cells or the like can be used in the present invention.
- the compound may be used in a purified form, but may be used in a crude form as long as it does not contain unsuitable impurities in foods and drinks, pharmaceuticals, quasi-drugs, cosmetics and the like.
- the fats and oils used in the present invention include glycerin fatty acid esters.
- the glycerin fatty acid ester is preferably a glycerin fatty acid ester containing a medium-chain fatty acid triglyceride and / or a glycerin fatty acid ester containing a partial glyceride.
- the medium-chain fatty acid triglyceride or the partial glyceride preferably accounts for 50% by weight or more of the entire glycerin fatty acid ester, and particularly preferably accounts for 70% by weight or more.
- Glycerin fatty acid esters containing 50% by weight of medium chain fatty acid triglyceride and 50% by weight of partial glyceride can also be used.
- the medium-chain fatty acid triglyceride is a fatty acid having 6 to 12 carbon atoms as a constituent fatty acid.
- the composition ratio of the fatty acid is not particularly limited, but the composition ratio of the fatty acid having 8 to 10 carbon atoms is 50 weight. /. More preferably, 70 weight. /. The above is more preferable.
- medium chain triglycerides having a specific gravity of 0.94 to 0.96 at 20 ° C and a viscosity of 23 to 28 cP at 20 ° C are more preferable.
- any of medium-chain fatty acid triglycerides, such as those of natural origin and those prepared by transesterification, can be used.
- the partial glyceride is diglyceride (1,2-diacylglycerol, 1,3-diacylglycerol) or monoglyceride (1-monoacylglycerol, 2-monoacylglycerol). ). Any of the partial glycerides may be used, or a mixture of both may be used, but diglycerides are preferred from the viewpoint of processability.
- partial glycerides are derived from natural sources and esters. Any of them, such as those prepared by exchange, can be used.
- the partial glyceride those in which the constituent fatty acids have 6 to 24 carbon atoms are preferable.
- a partial glyceride of a medium-chain fatty acid can be used.
- the method for dissolving glycicoumarin, glycillin, dehydrogliasperin C and dehydrogliasperin D in fats and oils is not particularly limited, and can be carried out by ordinary operations such as stirring and mixing.
- an extract containing the compound or a crude product of the compound since impurities other than the compound are contained, the compound is dissolved in fats and oils by stirring, mixing, etc., and then filtered, It is desirable to remove impurities insoluble in fats and oils by operations such as centrifugation.
- a purified product of the compound is used, a homogeneous solution can be easily obtained.
- a method of dissolving in an organic solvent such as ethanol in advance, mixing the solution with fats and oils, and then distilling off the organic solvent should be used. You can also.
- glycicoumarin, quericillin, dehydrodaliasperia C and dehydrogloriasperin D are unstable at a temperature of 40 ° C or more in a powder state, and 25 in a solution in an organic solvent such as ethanol.
- the compound is unstable at a temperature of not less than ° C, but is stable at a temperature of not less than 25 ° C when the compound is dissolved in the fat or oil used in the present invention.
- the oil / fat processing composition for preventing and / or improving lifestyle-related diseases of the present invention is at least selected from the group consisting of visceral fat obesity, type 2 diabetes, hyperlipidemia and hypertension among lifestyle-related diseases. It can be preferably used for one disease, and more preferably for visceral fat type obesity and no or type 2 diabetes. More specifically, it can be preferably used for prevention and / or improvement of hyperglycemia and reduction of intraperitoneal fat.
- the form of the processed fats and oils for preventing and / or improving lifestyle-related diseases and the processed fats and oils for improving insulin resistance of the present invention are not particularly limited in form. It can be used for foods and drinks such as foods and nutritional functional foods), pharmaceuticals, quasi-drugs, and cosmetics.
- the fat or oil in which at least one of the dissolved compounds is dissolved can be used as it is alone for cooking, soft capsule preparation, lotion, and the like. Also, since it can be freely mixed with an oily object, it is possible to adjust the physical properties by mixing with other fats and oils according to the purpose.
- the other fats and oils are preferably edible or medicinal, and the type and amount used are determined in consideration of the individual physical properties required for the product and various conditions such as the temperature range of use, and the type and use By adjusting the amount, characteristics such as consistency and melting point can be controlled.
- oils and fats include, for example, vegetable oils such as corn oil, rapeseed oil, high cinnamon rapeseed oil, soybean oil, olive oil, safflower oil, cottonseed oil, sunflower oil, rice bran oil, palm oil, palm kernel oil; fish oil, tallow And animal oils such as lard, milk fat, and egg yolk oil; oils and fats that have been subjected to separation, hydrogenation, ester exchange, and the like using these as raw materials, and mixed oils thereof, and the like can be used.
- vegetable oils such as corn oil, rapeseed oil, high cinnamon rapeseed oil, soybean oil, olive oil, safflower oil, cottonseed oil, sunflower oil, rice bran oil, palm oil, palm kernel oil
- fish oil, tallow And animal oils such as lard, milk fat, and egg yolk oil
- the oil-and-fat processing composition of the present invention thus obtained can be used as a liquid oil or fat such as salad oil or frying oil, a plastic oil such as margarine or shortening, or into a water-in-oil emulsion or an oil-in-water emulsion. Can be used.
- sweets such as chewing gum, chocolate, candy, jelly, biscuits, and crackers
- cold desserts such as ice cream and ice desserts
- Beverages such as udon, Chinese food, spaghetti, instant food, etc .
- Kneaded products such as kambu, bamboo rings, halves
- seasonings such as dressings, mayonnaise, sauces
- bread, ham Examples include soups, various retort foods, various frozen foods, and the like, and can also be used for pet food and livestock feed.
- various vitamins such as vitamins A, D, and E may be added or used together for the purpose of fortification
- various salts as flavoring agents, various flavors, milk-related substances, for example, whole milk powder milk , Skim milk powder, fermented milk, milk fat and the like may be added and used in combination.
- all antioxidants and coloring agents used in ordinary water-in-oil emulsions, oil-in-water emulsions, and the like can be used.
- the content of glycitamarin, glycillin, dehydrodariasperin C and dehydrodariasperin D in the oil / fat processing composition for preventing and / or improving lifestyle-related diseases of the present invention and the oil / fat processing composition for improving insulin resistance is as follows.
- the life of the compound In order to exert the effect of preventing and / or improving habitual diseases, the total amount of the compound is preferably 0.01 to 10 Omg / kg body weight per adult, more preferably 0.1 to 1 Omg / kg. It is desirable that the fat-and-oil-processing composition contain an amount capable of ingesting body weight.
- the method of the present invention for preventing and Z or improving lifestyle-related diseases include glycicoumarin and glycillin.
- the composition comprises an oil or fat in which at least one compound selected from the group consisting of dehydrogliasperin C and dehydrodaria sperin D is dissolved.
- the obtained MCT solution was diluted 100-fold with methanol for HPLC, and analyzed by HP LC under the following conditions.As a result, glycitamarin, glycillin, dehydrodariasperin C, and dehydrodariasperin D per gram of the MCT solution were 2.Omg each. , 1. 4mg s 6. 8mg, contained 5. 5 mg.
- the analytical column was J, sphere ODS-H80, 4.6 x 250 mm ( ⁇ Was used at a column temperature of 40 ° C.
- the ratio of acetonitrile to 10 mM phosphoric acid aqueous solution was kept constant at 35% from the start of analysis to 15 minutes, and then increased at a fixed ratio to 70% after 15 minutes and 65 minutes after 65 minutes.
- the flow rate was 1 ml / min under gradient conditions that were constant at 70% up to that point.
- the injection volume was 20 ⁇ l and the detection wavelength was 350 nm.
- the retention times were 33.5 minutes for glycicoumarin, 38.0 minutes for dehydrogliasperin C, 49.2 minutes for glycillin, and 56.5 minutes for dehydrogliasperin D.
- the above-mentioned MCT solution was stored at 4 ° C, 25 ° C, and 40 ° C, respectively, for 4 weeks, and the content of glycicoumarin, glycillin, dehydrogliasperin C, and dehydroglasperin D was quantified every week.
- the storage stability was represented by the ratio of the contents at the start of storage after storage, with the contents at the start of storage being 100%.
- Table 1 shows the results of storage at 4 ° C
- Table 2 shows the results of storage at 25 ° C
- Table 3 shows the results of storage at 40 ° C.
- compound 1 represents glycicoumarin
- compound 2 represents glycillin
- compound 3 represents dehydrogliasperin C
- compound 4 represents dehydrogliasperin D.
- Example 1 The licorice hydrophobic extract used in Example 1 was dissolved in ethanol instead of Actor M-2 to obtain a 100 mg / 1 ethanol solution. This ethanol solution was diluted 100-fold with methanol for HPLC, and analyzed by HPLC.As a result, 2.4 mg and 1.6 mg of glycicumarin, glycillin, dehydrogliasperin C and dehydrodaliasperin D per lm of ethanol solution were used, respectively. It contained 7.4 mg and 5.8 mg.
- KK-Ay mice female, 6 weeks old
- a type 2 diabetes model animal were divided into three groups (five animals in each group), divided into groups A, B, and C, and fed the diets shown in Table 4 freely.
- the basal diet casein 20 wt 0/0, corn starch 49.9 48% by weight
- Shiyukurosu 10 weight 0/0 cellulose powder 5 weight 0/0
- AIN one 93 Mineral mixture 3.5 wt 0/0
- group A the blood glucose level of the mice increased over time, and diabetes was observed.
- group B as in group A, the blood glucose level of the mice increased and diabetes occurred, and the effect of MCT was not observed.
- group C the increase in the blood glucose level of the mice was significantly suppressed as compared with the groups A and B, and the diabetes preventive effect of the MCT solution of Example 1 was observed. Was observed.
- C57BL / 6J mice female, 8-week-old were fed a high-fat, high-sugar diet with free intake for 8 weeks, resulting in dietary obesity.
- the high-fat 'high sugar diet casein 2 5 wt 0/0, corn starch 14.869 wt%, Shiyukurosu 20 weight 0 /. , Soybean oil 2% by weight, lard 14% by weight, beef tallow 14% by weight, cellulose powder 5 wt%, AIN- 93 mineral mixture 3.5 weight 0/0, AIN- 93 vitamin mixture 1% by weight, choline bitartrate 0.
- mice were divided into three groups (five mice in each group), which were designated as group A, group B, and group C.
- Group A received CE-2 feed (CLEA Japan)
- Group B received CE-2 feed supplemented with 3% by weight of MCT
- Group C received 3% of the MCT solution of Example 1. /.
- Actor M-2 RIKEN Vitamin Co., Ltd.
- mice that had been deprived of the 1B diet were laparotomized under ether anesthesia, blood was collected from the abdominal aorta and sacrificed, and mesenteric fat, perirenal fat, and perineal fat were extracted and weighed. The sum of the weight of mesenteric fat, the weight of fat around the kidney, and the weight of fat around the uterus was defined as fat weight in the abdominal cavity. Table 6 shows the results. Table 6
- Example 1 The MCT solution of Example 1 was press-fitted into the gelatin membrane using a rotary soft capsule manufacturing apparatus to obtain a soft capsule having an internal volume of 35 O mg.
- Hardened cottonseed oil (trade name: Snow Light, Kanegafuchi Chemical Industry Co., Ltd.) 80 parts by weight, MCT solution of Example 1 20 parts by weight, unsalted butter (Four-leaf Dairy Co., Ltd.) 10 parts by weight Glycerin mono fatty acid ester (trade name: Emulgy MS, RIKEN Vitamin Strain) 0.2 parts by weight of lecithin and 0.2 parts by weight of lecithin were added and dissolved by heating at 60 ° C to prepare an oil phase.
- An aqueous phase was prepared by dissolving 25 parts by weight of skim milk powder, 0.1 part by weight of glycerin fatty acid ester, and 0.1 part by weight of sucrose fatty acid ester in 64.6 parts by weight of water at 60 ° C. After pre-emulsifying the prepared aqueous phase and oil phase, they were sterilized at 145 ° C for 4 seconds with an ultra-high temperature instant (UHT) sterilizer. Then, after vacuum cooling, the mixture was homogenized with a homogenizer at a pressure of 10 MPa and further cooled to 10 ° C on a plate to obtain concentrated milk for processing.
- UHT ultra-high temperature instant
- an oil / fat composition that can be used in foods and drinks such as health foods and functional health foods (foods for specified health use, nutritional foods), pharmaceuticals, quasi-drugs, cosmetics, and the like.
- the oil / fat processing composition of the present invention is effective for improving insulin resistance and for preventing and / or improving lifestyle-related diseases such as visceral fat obesity, type 2 diabetes, hyperlipidemia and hypertension.
Abstract
It is intended to provide a processed fat composition which contains at least one compound selected from the group consisting of glycycoumarin, glycyrin, dehydroglyasperin C and dehydroglyasperin D, is usable in foods and drinks such as health foods and foods with health claims (foods for specified health uses and foods with nutrient function claims), drugs, quasi drugs, cosmetics and so on, and is efficacious in improving insulin resistance and preventing and/or improving lifestyle-related diseases such as obesity with internal fat deposits, type 2 diabetes, hyperlipemia and hypertension. Namely, a processed fat composition wherein at least one compound selected from the group consisting of glycycoumarin, glycyrin, dehydroglyasperin C and dehydroglyasperin D is dissolved in fat (in particular, a medium chain fatty acid triglyceride and/or a partial glyceride) to thereby elevate the stability of the compound and improve processing suitability for foods, drinks, drugs, quasi drugs, cosmetics and so on.
Description
明細書 Specification
生活習慣病予防 ·改善用の油脂加工組成物 技術分野 Oil processing composition for prevention and improvement of lifestyle-related diseases
本発明は、 健康食品や保健機能食品 （特定保健用食品、 栄養機能食品） などの 飲食品、 医薬品、 医薬部外品、 化粧品などに使用することができる生活習慣病予 防及び/又は改善用の油脂加ェ組成物に関する。 背景技術 The present invention is for preventing and / or improving lifestyle-related diseases which can be used in foods and drinks such as health foods and functional health foods (food for specified health use, nutritional foods), pharmaceuticals, quasi-drugs, cosmetics, etc. The present invention relates to an oil and fat composition of Background art
栄養過多や運動不足などの生活習慣の悪化による生活習慣病は大きな社会問題 になっている。 ここでの生活習慣病としては、 内臓脂肪型肥満、 2型糖尿病、 高 脂血症、 高血圧症などが挙げられ、 やがて動脈硬化症へと悪化していくマルチプ ル- リスク 'ファクター症候群である。 そこで、 これらの生活習慣病を予防及び Z又は改善する効果を有する組成物が望まれており、 その組成物の形態は、 3常 的に摂取できる健康食品や保健機能食品 （特定保健用食品、 栄養機能食品） など の飲食品、 医薬品、 医薬部外品、 化粧品などが望まれている。 Lifestyle-related diseases caused by deterioration of lifestyle such as overnutrition and lack of exercise have become a major social problem. The lifestyle-related diseases here include visceral fat obesity, type 2 diabetes, hyperlipidemia, hypertension, and the like, and the multiple-risk 'factor syndrome, which eventually worsens to arteriosclerosis. Therefore, a composition having the effect of preventing and / or improving these lifestyle-related diseases is desired, and the form of the composition is a health food or a health functional food (a food for specified health use, Foods and drinks such as nutritional foods), pharmaceuticals, quasi-drugs, and cosmetics are desired.
マルチプル ' リスク 'ファクター症候群は、 R e a v e nによるシンドローム X (D i a b e t e s, 37, 1595〜 1607， 1 988) , Ka p l a n による死の四重奏 （A r c h i V e s o f I n t e r n a l Me d i c i n e， 149, 1 514〜 1 520， 1 989) 、 D e F r o n z oによるイン スリン抵抗性症候群 （D i a b e t e s C a r e, 14， 1 73〜 1 94, 1 99 1) 、 松澤による内臓脂肪症候群 （D i a b e t e s /M e t a b o 1 i s m Re v i ew s, 1 3， 3〜1 3， 1997) と同じ病態概念であると考え られ、 これら症候群に共通する原因因子はインスリン抵抗性であると考えられて いる。 Multiple 'risk' factor syndromes are syndrome X due to Reaven X (Diabetes, 37, 1595-1607, 1988), quartet of death due to Kaplan (Archi Vesof Internal Medicine, 149, 1514-1520) Insulin Resistance Syndrome (Diabetes Care, 14, 173-194, 1991) due to DeFronzo, Visceral Fat Syndrome due to Matsuzawa (Diabetes / Metabo 1 ism Revi ewew) s, 13, 3–13, 1997), and the common causative factor of these syndromes is thought to be insulin resistance.
近年、 ペルォキシソーム増殖剤応答性受容体 γ (p e r o x i s ome p r o l l f e r a t o r— a c t i v a t e d r e c e p t o r y P P AR 7) のリガンドであるトログリタゾン、 ピオグリタゾン、 ロシグリタゾンなどの チアゾリジン誘導体の研究により、 これらの薬剤は 2型糖尿病患者において、 ィ
ンスリン抵抗性を改善し、 血糖低下作用を示すことが明らかにされており、 イン スリン抵抗性改善薬 · 2型糖尿病治療薬として臨床応用されている。 さらに、 こ れらのチアゾリジン誘導体は、 皮下脂肪を増加させるが內臓脂肪を低減させるこ と、 血中遊離脂肪酸低下作用、 血圧低下作用、 杭炎症作用などを示すことが明ら 力にされている （Ma r t e n s, F. M. , e t a 1 , D r u g s, 62, 1463〜 1480, 2002) 。 すなわち、 PPARyリガンド活性を有する 化合物は、 インスリン抵抗性を改善し、 内臓脂肪型肥満、 2型糖尿病、 高脂血症、 高血圧症などの生活習慣病の予防及び/又は改善に有効である。 In recent years, studies on thiazolidine derivatives such as troglitazone, pioglitazone, and rosiglitazone, which are ligands for peroxisome proliferator-activated receptor γ (peroxisome prollferator-activatedreceptory PP AR 7), have shown that these drugs are used in patients with type 2 diabetes. It has been shown to improve insulin resistance and show a hypoglycemic effect, and has been clinically applied as an insulin resistance ameliorating drug and a type 2 diabetes drug. Furthermore, it has been clarified that these thiazolidine derivatives increase subcutaneous fat but reduce visceral fat, and have a blood free fatty acid lowering action, a blood pressure lowering action, and a pile inflammatory action. (Martens, FM, eta1, Drugs, 62, 1463-1480, 2002). That is, a compound having PPARy ligand activity improves insulin resistance and is effective in preventing and / or improving lifestyle-related diseases such as visceral fat obesity, type 2 diabetes, hyperlipidemia, and hypertension.
甘草はマメ科カンゾゥ属 （G l y c y r r h i z a属） の植物であり、 食用や 医薬用 （生薬） として利用されており、 主な品種としてダリキルリーザ 'グラブ ラ (G l y c y r r h i z a g l a b r a) 、 G. ゥラレンシス （G. u r a 1 e n s i s ) 、 G. インフラータ (G. i n f 1 a t a) などが挙げられる。 いずれの品種にも親水性成分であるグリチルリチン （ダリチルリチン酸） は含ま れているが、 疎水性成分のフラポノィドは品種によって特異的な化合物が含まれ ている。 この品種特異的なフラボノイドは、 甘草の品種同定に利用されることも ある。 Licorice is a plant belonging to the genus Glycyrrhiza in the legume family, and is used for edible and medicinal purposes (herbal medicine). The main varieties are Darikiruliza'Glabra (Glycyrrhizaglabra) and G. ensis) and G. infata (G. inf 1 ata). All varieties contain glycyrrhizin (daricyrrhizic acid), a hydrophilic component, but the flavonoid, a hydrophobic component, contains specific compounds depending on the cultivar. This cultivar-specific flavonoid may be used to identify licorice varieties.
甘草から得られる抽出物のうち、 甘草フラポノイドを多く含み、 グリチルリチ ン含量が極微量である甘草疎水性抽出物は、 マルチプル. リスク 'ファクター症 候群の予防及び/又は改善に有用であることが見出されている （WOO 2/47 699) 。 さらに最新の研究において、 甘草疎水性抽出物に P PAR γリガンド 活性があり、 その活性成分はフラボノイド、 特にプレニルフラボノイドであるこ とが見出されている （WO 03Ζ037316) 。 中でも G. ゥラレンシス由来 の抽出物の P PAR Vリガンド活性が高いこと、 その抽出物に含まれるプレニル フラボノィドであるグリシクマリン、 グリシリン、 デヒ ドロダリアスペリン C及 びデヒドロダリアスペリン Dが高い活性を有する成分であることも見出されてい る （WO 03/037316) 。 なお、 デヒドログリァスペリン Dは WO 03/ 03 73 16において新規に見出された化合物である。 Among the extracts obtained from licorice, hydrophobic extracts containing a large amount of licorice flaponoids and having a very small amount of glycyrrhizin are multiple.Risk 'Factor' may be useful for prevention and / or improvement of symptomatic groups. Found (WOO 2/47 699). Furthermore, in the latest research, it has been found that hydrophobic extract of licorice has P PARγ ligand activity, and its active ingredient is flavonoid, especially prenylflavonoid (WO 03-037316). Above all, the extract derived from G. peralensis has high PPARV ligand activity, and the prenyl flavonoids contained in the extract, glycicumarin, glycillin, dehydrodariasperin C and dehydrodariasperin D, have high activity. (WO 03/037316). Note that dehydroglasperin D is a compound newly found in WO 03/037316.
一方、 甘草疎水性フラボノイドは、 水にほとんど溶解せず、 また、 有機溶媒抽 出物のままでは固結し易く、 着色の進行も早いなど、 経時的変化が著しいという
性質があるため、 利用し難い。 それを解決するために、 甘草疎水性フラボノイド を中鎖脂肪酸トリグリセリ ドに溶解し、 その甘草疎水性フラポノイド製剤を酸化 防止剤、 抗菌剤、 酵素阻害剤、 着色料、 抗腫瘍剤、 抗アレルギー剤、 抗ウィルス 剤等として利用している （特許 2 7 9 4 4 3 3号） 。 しかし、 特許 2 7 9 4 4 3 3号では、 化合物の限定がなく、 また、 生活習慣病の予防及び Z又は改善剤とし ての利用も知られていない。 発明の要約 On the other hand, licorice hydrophobic flavonoids are hardly soluble in water, are easily solidified as they are extracted from organic solvents, and color change is rapid. Due to its nature, it is difficult to use. To solve this, licorice hydrophobic flavonoids are dissolved in medium-chain fatty acid triglycerides, and the licorice hydrophobic flaponoid preparations are used as antioxidants, antibacterial agents, enzyme inhibitors, coloring agents, antitumor agents, antiallergic agents, It is used as an antiviral agent, etc. (Patent No. 279443). However, in Patent No. 2794443, there is no limitation on the compound, and no use of the compound as a preventive and / or ameliorating agent for lifestyle-related diseases is known. Summary of the Invention
上記に鑑み、 グリシクマリン、 グリシリン、 デヒドログリアスペリン C及びデ ヒドログリアスペリン Dは、 P P A R yリガンド活性を有しており、 インスリン 抵抗性を改善し、 内臓脂肪型肥満、 2型糖尿病、 高脂血症、 高血圧症などの生活 習慣病の予防及び/又は改善に有効である。 しカゝし、 該化合物は、 水への溶解性 や安定性が良くないことから、 飲食品や医薬品などへの利用が困難であるという 欠点があった。 よって、 本発明は、 グリシクマリン、 グリシリン、 デヒドログリ ァスペリン C及びデヒドロダリアスペリン Dからなる群より選ばれた少なくとも 1つの化合物を含有し、 健康食品や保健機能食品 （特定保健用食品、 栄養機能食 品） などの飲食品、 医薬品、 医薬部外品、 化粧品などに利用することができる生 活習慣病予防及び/又は改善用の組成物を提供することを課題とする。 In view of the above, glycicoumarin, glycillin, dehydrogliasperin C and dehydrogliasperin D have PPARy ligand activity, improve insulin resistance, visceral fat obesity, type 2 diabetes, high fat It is effective in preventing and / or ameliorating lifestyle-related diseases such as bloodemia and hypertension. However, the compound has a drawback that it is difficult to use it in foods and drinks and pharmaceuticals because of its poor solubility and stability in water. Therefore, the present invention comprises at least one compound selected from the group consisting of glycicoumarin, glycillin, dehydroglasperin C and dehydrodariasperin D, and comprises a health food or a health functional food (specified health food, nutritional food). It is an object of the present invention to provide a composition for preventing and / or improving lifestyle-related diseases, which can be used for foods and drinks, pharmaceuticals, quasi-drugs, cosmetics, and the like.
本発明者らは、 上記実情に鑑み鋭意研究を行った結果、 グリシクマリン、 グリ シリン、 デヒドログリアスペリン C及びデヒドログリアスペリン Dをある種の油 脂に特異的に溶解することができ、 その油脂への溶解によってこれら化合物の安 定性が向上し、 また、 飲食品、 医薬品、 医薬部外品、 化粧品などへの加工性も向 上することを見出し、 本発明を完成するに至った。 The present inventors have conducted intensive studies in view of the above-mentioned circumstances, and as a result, it was possible to specifically dissolve glycicoumarin, glycillin, dehydrogliasperin C and dehydrogliasperin D in certain kinds of oils and fats. It has been found that the stability of these compounds is improved by dissolving them in fats and oils, and that the processability of foods and drinks, pharmaceuticals, quasi-drugs, cosmetics, and the like is also improved, and the present invention has been completed.
すなわち、 本発明は、 グリシクマリン、 グリシリン、 デヒドログリアスペリン C及びデヒドロダリアスペリン Dからなる群より選ばれた少なくとも 1つの化合 物を溶解している油脂を含有することを特徴とする、 生活習慣病予防及び/又は 改善用の油脂加工組成物、 並びに、 インスリン抵抗性改善用の油脂加工組成物に 関する。 That is, the present invention provides a lifestyle-related disease characterized by containing an oil or fat in which at least one compound selected from the group consisting of glycicoumarin, glycillin, dehydrogliasperin C and dehydrodaria sperin D is dissolved. The present invention relates to a fat and oil processing composition for prevention and / or improvement, and a fat and oil processing composition for improving insulin resistance.
また、 本発明は、 グリシクマリン、 グリシリン、 デヒドロダリアスペリン C及
ぴデヒドロダリアスペリン Dからなる群より選ばれた少なくとも 1つの化合物を 溶解している油脂を含有する組成物を用いた、 生活習慣病を予防及び 又は改善 する方法、 インスリン抵抗性を改善する方法、 高血糖を予防及び/又は改善する 方法、 並びに、 腹腔内脂肪を減少させる方法に関する。 発明の詳細な開示 In addition, the present invention relates to glycicoumarin, glycillin, dehydrodaria sperin C and 方法 using a composition containing an oil or fat in which at least one compound selected from the group consisting of dehydrodaria sperin D is dissolved, a method for preventing and / or improving lifestyle-related diseases, a method for improving insulin resistance, The present invention relates to a method for preventing and / or improving hyperglycemia, and a method for reducing intraperitoneal fat. Detailed Disclosure of the Invention
以下に、 本発明の実施の形態を詳しく説明する。 Hereinafter, embodiments of the present invention will be described in detail.
本発明の生活習慣病予防及び 又は改善用の油脂加工 la成物は、 グリシタマリ ン、 グリシリン、 デヒ ドログリアスペリン C及びデヒ ドログリアスペリン Dから なる群より選ばれた少なくとも 1つの化合物を溶解している油脂を含有すること を特^ ¾としている。 The oil- and fat-processed la composition for preventing and / or improving lifestyle-related diseases according to the present invention is at least one compound selected from the group consisting of glycitamarin, glycillin, dehydrogliasperin C and dehydrogliasperin D. It is characterized in that it contains oils and fats in which is dissolved.
また、 本発明のィンスリン抵抗 ¾t改善用の油脂加工組成物は、 グリシクマリン、 グリシリン、 デヒドロダリアスペリン C及ぴデヒ ドログリアスペリン Dからなる 群より選ばれた少なくとも 1つの化合物を溶解している油脂を含有することを特 徴としている。 Further, the oil / fat processing composition for improving insulin resistance Δt of the present invention has at least one compound selected from the group consisting of glycicoumarin, glycillin, dehydrodariasperin C and dehydrogliasperin D dissolved therein. It is characterized by containing fats and oils.
本発明の油脂加工組成物は、 該化合物の中でも、 デヒドログリアスペリン Dを 含み、 かつグリシクマリン、 グリシリン及びデヒドログリアスペリン Cからなる 群より選ばれた少なくとも 1つの化合物を含むことが好ましい。 さらに、 デヒド ログリアスペリン C及びデヒドロダリアスペリン Dを含み、 かつグリシクマリン 又はグリシリンのいずれかを含むことがより好ましい。 とりわけ、 グリシタマリ ン、 グリシリン、 デヒドログリアスペリン C及びデヒドログリアスペリン Dをす ベて含むのが最も好ましい。 該化合物は、 トログリタゾンゃピオグリタゾンなど のチアゾリジン誘導体と同様に、 P P A R yリガンド活性を有していることから、 インスリン抵抗性の改善、 並びに、 内臓脂肪型肥満、 2型糖尿病、 高脂血症、 高 血圧症などの生活習慣病の予防及ぴ 又は改善に有効である。 The oil and fat processing composition of the present invention preferably contains, among the compounds, dehydrogliasperin D and at least one compound selected from the group consisting of glycicoumarin, glycillin and dehydrogliasperin C. Furthermore, it is more preferable that it contains dehydrologliasperin C and dehydrodariasperin D, and that it contains either glycicoumarin or glycillin. In particular, it is most preferable to include all of glycitamarin, glycillin, dehydrogliasperin C and dehydrogliasperin D. Since the compound has PPARy ligand activity similarly to thiazolidine derivatives such as troglitazone pioglitazone, insulin resistance is improved, and visceral fat obesity, type 2 diabetes, hyperlipidemia, It is effective in preventing and / or improving lifestyle-related diseases such as blood pressure.
本発明で使用されるグリシクマリン （g 1 y c y c o u m a r i n ) 及びダリ シリン （ g 1 y c y r i n ) は、 3—ァリ /レクマリン （3— a r y l c o u m a r i n ) に分類されるフラボノイドであり、 下記一般式 （1 ) で表される化合物 である。
〔式中、 R = Hである場合はグリシクマリン、 R==CH3である場合はグリシリ ンである。 〕 Glycicoumarin (g 1 ycycoumarin) and dalicillin (g 1 ycyrin) used in the present invention are flavonoids classified into 3-arycoumarin (3-arylcoumarin), and are represented by the following general formula (1). Compound. Wherein when an R = H is Gurishikumarin, if a R == CH 3 is Gurishiri down. ]
本発明で使用されるデヒドロダリアスペリン C (d e hy d r o g l y a s p e r i n C) 及びデヒ ドロダリアスペリン D (d e hy d r o g l y a s p e r i n D) は、 ィソフラブ一 3—ェン （i s o f 1 a v— 3— e n e) に分類 されるフラボノイ ドであり、 下記一般式 （2) で表される化合物である。 The dehydrodroglyasperin C and the dehydroglyasperin D used in the present invention are classified into isoflav-1-3-ene. It is a flavonoid and a compound represented by the following general formula (2).
〔式中、 R = Hである場合はデヒ ドログリアスペリン C、 R==CH3である場合 はデヒ ドログリアスペリン Dである。 〕 Wherein when the case is R = H is de human de log Rias Perrin C, R == CH 3 is de human de log Asturias Perrin D. ]
グリシタマリン、 グリシリン、 デヒ ドログリァスぺリン C及ぴデヒドログリァ スペリン Dは、 甘草の中でもグリキルリーザ · ゥラレンシス （G 1 y c y r r h i z a u r a l e n s i s) に特異的に含まれている成分であり、 他品種には ほとんど含まれていない。 ただし、 G. ゥラレンシスと他品種との雑種において は含まれる場合もある。 該化合物は、 ODS (シリカゲル担体にォクタデシルシ リル基を化学結合した充填剤） などの逆相カラムを用いた高速液体力ラムクロマ トグラフィー （HPLC) 分析により、 他のフラボノイド成分と分離して検出、 定量することができる。 Glicitamarin, glycillin, dehydrogliasperin C and dehydroglia sperin D are components that are specifically contained in Glycyrrhiza peralensis (G1ycyrrhiizarualensils) among licorice, and are hardly contained in other varieties. However, it may be included in hybrids between G. peralensis and other varieties. The compound is separated from other flavonoid components by high-performance liquid chromatography (HPLC) using a reversed-phase column such as ODS (a packing material in which octadecylsilyl groups are chemically bonded to a silica gel carrier), and detected and quantified. can do.
本発明において、 グリシクマリン、 グリシリン、 デヒドログリアスペリン C及 ぴデヒドログリアスペリン Dを得る方法は、 特に限定されないが、 G. ゥラレン
シス種の甘草より得ることができる。 該化合物を甘草から得る場合、 その方法は 特に限定されないが、 エタノール、 酢酸ェチル、 アセトンなどの有機溶媒による 抽出等が挙げられる。 上記抽出で得られる甘草疎水性抽出物に該化合物は含まれ、 抽出物のまま使用してもよいが、 さらにカラム処理、 脱臭処理、 脱色処理などに より粗精製又は精製したものを使用してもよい。 勿論、 該化合物は、 その他植物 等の天然由来のもの、 化学合成のもの、 あるいは培養細胞などにより生合成した もののいずれも本発明において使用することができる。 また、 該化合物は、 精製 したものを使用することができるが、 飲食品、 医薬品、 医薬部外品、 化粧品など として不適当な不純物を含有しない限り粗精製したものを使用することもできる。 本発明で使用される油脂としては、 グリセリン脂肪酸エステルを挙げることが できる。 グリセリン脂肪酸エステルとしては、 中鎖脂肪酸トリグリセリ ドを含む グリセリン脂肪酸エステル、 及び/又は、 部分グリセリ ドを含むグリセリン脂肪 酸エステルが好ましい。 この場合、 中鎖脂肪酸トリグリセリ ド、 部分グリセリ ド の何れかが、 グリセリン脂肪酸エステル全体の 5 0重量％以上を占めることが好 ましく、 7 0重量％以上を占めることが特に好ましい。 また、 中鎖脂肪酸トリグ リセリ ド 5 0重量％、 部分グリセリ ド 5 0重量％を含むグリセリン脂肪酸エステ ルも用いることができる。 In the present invention, the method for obtaining glycicoumarin, glycillin, dehydrogliasperin C and dehydrogliasperin D is not particularly limited. It can be obtained from cis licorice. When the compound is obtained from licorice, the method is not particularly limited, and examples thereof include extraction with an organic solvent such as ethanol, ethyl acetate, and acetone. The compound is contained in the licorice hydrophobic extract obtained by the above extraction, and the compound may be used as it is, but it may be further purified or purified by column treatment, deodorization treatment, decolorization treatment, etc. Is also good. Of course, as the compound, any of compounds derived from other natural sources such as plants, chemically synthesized compounds, and those biosynthesized by cultured cells or the like can be used in the present invention. Further, the compound may be used in a purified form, but may be used in a crude form as long as it does not contain unsuitable impurities in foods and drinks, pharmaceuticals, quasi-drugs, cosmetics and the like. Examples of the fats and oils used in the present invention include glycerin fatty acid esters. The glycerin fatty acid ester is preferably a glycerin fatty acid ester containing a medium-chain fatty acid triglyceride and / or a glycerin fatty acid ester containing a partial glyceride. In this case, either the medium-chain fatty acid triglyceride or the partial glyceride preferably accounts for 50% by weight or more of the entire glycerin fatty acid ester, and particularly preferably accounts for 70% by weight or more. Glycerin fatty acid esters containing 50% by weight of medium chain fatty acid triglyceride and 50% by weight of partial glyceride can also be used.
ここでの中鎖脂肪酸トリグリセリ ドは、 炭素原子数 6〜1 2の脂肪酸を構成脂 肪酸とするものである。 その脂肪酸の構成比率は特に限定されないが、 炭素原子 数 8〜 1 0の脂肪酸の構成比率は 5 0重量。/。以上が好ましく、 7 0重量。 /。以上が より好ましい。 とりわけ、 2 0 °〇での比重が0 . 9 4〜0 . 9 6、 2 0 °Cでの粘 度が 2 3 ~ 2 8 c Pの中鎖脂肪酸トリグリセリ ドがさらに好ましい。 また、 中鎖 脂肪酸トリグリセリドは、 天然由来のものやエステル交換などにより調製したも のなど、 いずれも使用することができる。 Here, the medium-chain fatty acid triglyceride is a fatty acid having 6 to 12 carbon atoms as a constituent fatty acid. The composition ratio of the fatty acid is not particularly limited, but the composition ratio of the fatty acid having 8 to 10 carbon atoms is 50 weight. /. More preferably, 70 weight. /. The above is more preferable. In particular, medium chain triglycerides having a specific gravity of 0.94 to 0.96 at 20 ° C and a viscosity of 23 to 28 cP at 20 ° C are more preferable. In addition, any of medium-chain fatty acid triglycerides, such as those of natural origin and those prepared by transesterification, can be used.
ここでの部分グリセリ ドとは、 ジグリセリ ド （ 1， 2—ジァシルグリセ口ール、 1， 3—ジァシルグリセロール） 又はモノグリセリ ド （1ーモノアシルグリセ口 ール、 2—モノアシルグリセ口ール) である。 部分グリセリ ドとしては、 いずれ を用いても良いし、 両者が混合されたものを用いても良いが、 加工性の観点から ジグリセリ ドが好ましい。 また、 部分グリセリ ドは、 天然由来のものやエステル
交換などにより調製したものなど、 いずれも使用することができる。 なお、 部分 グリセリ ドとしては、 構成脂肪酸の炭素原子数が 6〜 2 4であるものが好ましい。 さらに、 本発明で使用される部分グリセリ ドは、 中鎖脂肪酸の部分グリセリ ド を用いることもできる。 Here, the partial glyceride is diglyceride (1,2-diacylglycerol, 1,3-diacylglycerol) or monoglyceride (1-monoacylglycerol, 2-monoacylglycerol). ). Any of the partial glycerides may be used, or a mixture of both may be used, but diglycerides are preferred from the viewpoint of processability. In addition, partial glycerides are derived from natural sources and esters. Any of them, such as those prepared by exchange, can be used. As the partial glyceride, those in which the constituent fatty acids have 6 to 24 carbon atoms are preferable. Furthermore, as the partial glyceride used in the present invention, a partial glyceride of a medium-chain fatty acid can be used.
本発明において、 グリシクマリン、 グリシリン、 デヒ ドログリアスペリン C及 びデヒドログリアスペリン Dを油脂に溶解する方法は、 特に限定されず、 通常の 撹拌、 混合などの操作により実施できる。 該化合物を含む抽出物、 あるいは該化 合物の粗精製品を用いる場合、 該化合物以外の不純物が含まれているため、 撹拌、 混合などの操作により該化合物を油脂に溶解した後に、 濾過、 遠心分離などの操 作により油脂に不溶な不純物を除去することが望ましい。 該化合物の精製品を用 いる場合、 容易に均一な溶液を得ることができる。 また、 該化合物を含む抽出物、 あるいは該化合物の粗精製品を用いる場合、 予めエタノールなどの有機溶媒に溶 解し、 その溶液と油脂を混合した後に、 有機溶媒を留去する方法を用いることも できる。 In the present invention, the method for dissolving glycicoumarin, glycillin, dehydrogliasperin C and dehydrogliasperin D in fats and oils is not particularly limited, and can be carried out by ordinary operations such as stirring and mixing. When an extract containing the compound or a crude product of the compound is used, since impurities other than the compound are contained, the compound is dissolved in fats and oils by stirring, mixing, etc., and then filtered, It is desirable to remove impurities insoluble in fats and oils by operations such as centrifugation. When a purified product of the compound is used, a homogeneous solution can be easily obtained. When an extract containing the compound or a crude product of the compound is used, a method of dissolving in an organic solvent such as ethanol in advance, mixing the solution with fats and oils, and then distilling off the organic solvent should be used. You can also.
一般に、 グリシクマリン、 ク"リシリン、 デヒ ドロダリアスペリン C及びデヒド ログリアスペリン Dは、 粉末状態では 4 0 °C以上において不安定であり、 ェタノ ールなどの有機溶媒での溶液状態では 2 5 °C以上において不安定である。 しかし、 該化合物を本発明で使用される油脂に溶解した状態では 2 5 °C以上においても安 定である。 In general, glycicoumarin, quericillin, dehydrodaliasperia C and dehydrogloriasperin D are unstable at a temperature of 40 ° C or more in a powder state, and 25 in a solution in an organic solvent such as ethanol. The compound is unstable at a temperature of not less than ° C, but is stable at a temperature of not less than 25 ° C when the compound is dissolved in the fat or oil used in the present invention.
本発明の生活習慣病予防及び/又は改善用の油脂加工組成物は、 生活習慣病の なかでも内臓脂肪型肥満、 2型糖尿病、 高脂血症及ぴ高血圧症からなる群より選 ばれた少なくとも 1つの疾患に好ましく用いることができ、 内臓脂肪型肥満及び ノ又は 2型糖尿病により好ましく用いることができる。 より具体的には、 高血糖 の予防及び/又は改善、 腹腔内脂肪の減少に好ましく用いることができる。 本発明の生活習慣病予防及び 又は改善用の油脂加工組成物、 並びに、 インス リン抵抗性改善用の油脂加工組成物は、 その形態は特に限定されず、 健康食品や 保健機能食品 （特定保健用食品、 栄養機能食品） などの飲食品、 医薬品、 医薬部 外品、 化粧品などに利用することができる。 例えば、 グリシクマリン、 グリシリ ン、 デヒ ドロダリアスペリン C及ぴデヒドロダリアスペリン Dからなる群より選
ばれた少なくとも 1つの化合物を溶解している油脂をそのまま単独で、 調理用、 ソフトカプセ 製剤用、 ローション用などとして利用することができる。 また、 油性の対象物と自由に混和することができるため、 目的に応じて他の油脂と混合 して物性を調整することが可能である。 この場合、 他の油脂は食用又は医薬用で あることが好ましく、 その種類及び使用量は製品に要求される個々の物性や使用 温度域などの諸条件を考慮して決定され、 その種類及び使用量を調整することに より稠度ゃ融点などの特性をコントロールすることができる。 他の油脂としては、 例えば、 コーン油、 ナタネ油、 ハイエルシンナタネ油、 大豆油、 オリープ油、 紅 花油、 綿実油、 ヒマヮリ油、 米糠油、 パーム油、 パーム核油などの植物油；魚油、 牛脂、 豚脂、 乳脂、 卵黄油などの動物油；これらを原料として分別、 水添、 エス テル交換などを行った油脂、 これらの混合油等を使用することができる。 The oil / fat processing composition for preventing and / or improving lifestyle-related diseases of the present invention is at least selected from the group consisting of visceral fat obesity, type 2 diabetes, hyperlipidemia and hypertension among lifestyle-related diseases. It can be preferably used for one disease, and more preferably for visceral fat type obesity and no or type 2 diabetes. More specifically, it can be preferably used for prevention and / or improvement of hyperglycemia and reduction of intraperitoneal fat. The form of the processed fats and oils for preventing and / or improving lifestyle-related diseases and the processed fats and oils for improving insulin resistance of the present invention are not particularly limited in form. It can be used for foods and drinks such as foods and nutritional functional foods), pharmaceuticals, quasi-drugs, and cosmetics. For example, selected from the group consisting of glycicoumarin, glycilin, dehydrodariasperin C and dehydrodariasperin D The fat or oil in which at least one of the dissolved compounds is dissolved can be used as it is alone for cooking, soft capsule preparation, lotion, and the like. Also, since it can be freely mixed with an oily object, it is possible to adjust the physical properties by mixing with other fats and oils according to the purpose. In this case, the other fats and oils are preferably edible or medicinal, and the type and amount used are determined in consideration of the individual physical properties required for the product and various conditions such as the temperature range of use, and the type and use By adjusting the amount, characteristics such as consistency and melting point can be controlled. Other oils and fats include, for example, vegetable oils such as corn oil, rapeseed oil, high cinnamon rapeseed oil, soybean oil, olive oil, safflower oil, cottonseed oil, sunflower oil, rice bran oil, palm oil, palm kernel oil; fish oil, tallow And animal oils such as lard, milk fat, and egg yolk oil; oils and fats that have been subjected to separation, hydrogenation, ester exchange, and the like using these as raw materials, and mixed oils thereof, and the like can be used.
このようにして得られる本発明の油脂加工組成物は、 サラダ油やフライ油な,ど の液状油脂、 マーガリンゃショートニングなどの可塑性油脂としての利用や、 油 中水型ェマルジヨン、 水中油型ェマルジヨン等へ利用することができる。 また、 これらを原材料にして製造される飲食用の油脂加工組成物として、 チューインガ ム、 チョコレート、 キャンディー、 ゼリー、 ビスケット、 クラッカーなどの菓子 類；アイスクリーム、 氷菓などの冷菓類；乳飲料、 清涼飲料、 栄養ドリンク、 美 容ドリンクなどの飲料； うどん、 中華麵、 スパゲティ一、 即席麵などの麵類；蒲 鋅、 竹輪、 半片などの練り製品； ドレッシング、 マヨネーズ、 ソースなどの調味 料；パン、 ハム、 スープ、 各種レトルト食品、 各種冷凍食品などが例示され、 ぺ ットフードゃ家畜飼料などへも利用することができる。 The oil-and-fat processing composition of the present invention thus obtained can be used as a liquid oil or fat such as salad oil or frying oil, a plastic oil such as margarine or shortening, or into a water-in-oil emulsion or an oil-in-water emulsion. Can be used. In addition, as a processed fat and oil composition for eating and drinking manufactured using these as raw materials, sweets such as chewing gum, chocolate, candy, jelly, biscuits, and crackers; cold desserts such as ice cream and ice desserts; milk drinks and soft drinks Beverages such as udon, Chinese food, spaghetti, instant food, etc .; Kneaded products such as kambu, bamboo rings, halves; seasonings such as dressings, mayonnaise, sauces; bread, ham, Examples include soups, various retort foods, various frozen foods, and the like, and can also be used for pet food and livestock feed.
さらに、 栄養強化を目的として、 ビタミン A、 D、 Eなどの各種ビタミン類を 添加、 併用してもよいし、 呈味剤としての各種塩類、 各種香料、 乳関連物質、 例 えば、 全脂粉乳、 脱脂粉乳、 発酵乳、 乳脂肪などを添加、 併用してもよい。 また、 上記以外の原材料として、 通常の油中水型ェマルジヨン、 水中油型ェマルジヨン 等に使用される酸化防止剤、 着色剤などを全て使用することができる。 Furthermore, various vitamins such as vitamins A, D, and E may be added or used together for the purpose of fortification, and various salts as flavoring agents, various flavors, milk-related substances, for example, whole milk powder milk , Skim milk powder, fermented milk, milk fat and the like may be added and used in combination. As the raw materials other than the above, all antioxidants and coloring agents used in ordinary water-in-oil emulsions, oil-in-water emulsions, and the like can be used.
本発明の生活習慣病予防及び Z又は改善用の油脂加工組成物、 並びに、 インス リン抵抗性改善用の油脂加工組成物におけるグリシタマリン、 グリシリン、 デヒ ドロダリアスペリン C及びデヒドロダリアスペリン Dの含量は、 該化合物の生活
習慣病予防及ぴ 又は改善の効果を発揮するためには、 該化合物の総量として好 ましくは成人一人一 3当たり 0. 01~10 OmgZk g体重、 より好ましくは 0. 1-1 Omg/k g体重を摂取できる量を油脂加工組成物中に含んでいるこ とが望ましい。 The content of glycitamarin, glycillin, dehydrodariasperin C and dehydrodariasperin D in the oil / fat processing composition for preventing and / or improving lifestyle-related diseases of the present invention and the oil / fat processing composition for improving insulin resistance is as follows. The life of the compound In order to exert the effect of preventing and / or improving habitual diseases, the total amount of the compound is preferably 0.01 to 10 Omg / kg body weight per adult, more preferably 0.1 to 1 Omg / kg. It is desirable that the fat-and-oil-processing composition contain an amount capable of ingesting body weight.
また、 本発明の生活習慣病を予防及び Z又は改善する方法、 インスリン抵抗性 を改善する方法、 高血糖を予防及び Z又は改善する方法、 並びに、 腹腔内脂肪を 減少させる方法は、 グリシクマリン、 グリシリン、 デヒドログリアスペリン C及 びデヒドロダリアスペリン Dからなる群より選ばれた少なくとも 1つの化合物を 溶解している油脂を含有する上記組成物を用いることを特徴とする。 発明を実施するための最良の形態 Further, the method of the present invention for preventing and Z or improving lifestyle-related diseases, the method for improving insulin resistance, the method for preventing and Z or improving hyperglycemia, and the method for reducing intraperitoneal fat include glycicoumarin and glycillin. The composition comprises an oil or fat in which at least one compound selected from the group consisting of dehydrogliasperin C and dehydrodaria sperin D is dissolved. BEST MODE FOR CARRYING OUT THE INVENTION
以下に、 実施例を挙げて本突明をさらに具体的に説明するが、 本努明はこれら の実施例に限定されるものではない。 (実施例 1 ) Hereinafter, the present invention will be described more specifically with reference to examples, but the present invention is not limited to these examples. (Example 1)
西北産甘草 （G. ゥラレンシス） 300 k gからエタノール抽出 （1840 L のェタノ一ルに浸し、 35〜 45 °C、 遮光条件下で 2時間抽出する操作を 2度繰 り返し） 、 得られた抽出液を併せて、 次いで濃縮、 晶析、 濾別、 乾燥、 粉砕によ り甘草疎水性抽出物 1 3. 46 k gを得た。 Ethanol extraction from 300 kg of northern northern licorice (G. peralensis) (The procedure of immersing in 1840 L of ethanol and extracting for 2 hours at 35-45 ° C and protected from light is repeated twice). The liquids were combined, and then concentrated, crystallized, filtered, dried, and pulverized to obtain 13.46 kg of a licorice hydrophobic extract.
上記の甘草疎水性抽出物 20 gと中鎖脂肪酸トリグリセリ ド （MC T) である アクター M— 2 (理研ビタミン株式会社：脂肪酸組成は C 8 : C 10 = 99 : 1 ) 180 gを混合し、 約 60°Cに保温しながら約 1時間攪禅した。 その後、 遠心 分離により不溶分を除去し、 オイル層を MC T溶液 （189. 4 g ) として得た。 得られた MCT溶液を HPLC用メタノールにて 100倍希釈し、 下記の条件 にて HP L C分析した結果、 MCT溶液 1 g当たりグリシタマリン、 グリシリン、 デヒドロダリアスペリン C及びデヒドロダリアスペリン Dをそれぞれ 2. Omg、 1. 4mgs 6. 8mg、 5. 5 mg含んでいた。 Mix 20 g of the above licorice hydrophobic extract with 180 g of actor M-2, a medium-chain fatty acid triglyceride (MCT) (RIKEN Vitamin Co., Ltd .: fatty acid composition: C 8: C 10 = 99: 1). The mixture was agitated for about 1 hour while maintaining the temperature at about 60 ° C. Then, the insoluble matter was removed by centrifugation, and the oil layer was obtained as an MCT solution (189.4 g). The obtained MCT solution was diluted 100-fold with methanol for HPLC, and analyzed by HP LC under the following conditions.As a result, glycitamarin, glycillin, dehydrodariasperin C, and dehydrodariasperin D per gram of the MCT solution were 2.Omg each. , 1. 4mg s 6. 8mg, contained 5. 5 mg.
HP LC分析条件 HP LC analysis conditions
分析カラムには J， s p h e r e ODS— H80， 4. 6 X 250mm (ヮ
イエムシィ社製） をカラム温度 40°Cで用いた。 移動相は、 10mMリン酸水溶 液に対してァセトニトリルの比率を分析開始から 15分まで 35%で一定とし、 15分以降 65分後に 70%となるように一定比率で上昇させ、 65分から 70 分まで 70%で一定とするグラジェント条件で、 流速 1m l/分とした。 注入量 は 20 μ 1とし、 検出波長は 350 n mとした。 保持時間は、 グリシクマリンが 33. 5分、 デヒドログリアスペリン Cが 38. 0分、 グリシリンが 49. 2分、 デヒドログリアスペリン Dが 56. 5分であった。 前記の MCT溶液をそれぞれ 4°C、 25°C、 40°Cにて 4週間保存し、 1週間 毎にグリシクマリン、 グリシリン、 デヒドログリアスペリン C及びデヒドログリ ァスペリン Dの含量を定量した。 保存安定性は、 保存開始時のそれぞれの含量を 100%とし、 保存後 Z保存開始時の含量の比で表した。 The analytical column was J, sphere ODS-H80, 4.6 x 250 mm (ヮ Was used at a column temperature of 40 ° C. For the mobile phase, the ratio of acetonitrile to 10 mM phosphoric acid aqueous solution was kept constant at 35% from the start of analysis to 15 minutes, and then increased at a fixed ratio to 70% after 15 minutes and 65 minutes after 65 minutes. The flow rate was 1 ml / min under gradient conditions that were constant at 70% up to that point. The injection volume was 20 μl and the detection wavelength was 350 nm. The retention times were 33.5 minutes for glycicoumarin, 38.0 minutes for dehydrogliasperin C, 49.2 minutes for glycillin, and 56.5 minutes for dehydrogliasperin D. The above-mentioned MCT solution was stored at 4 ° C, 25 ° C, and 40 ° C, respectively, for 4 weeks, and the content of glycicoumarin, glycillin, dehydrogliasperin C, and dehydroglasperin D was quantified every week. The storage stability was represented by the ratio of the contents at the start of storage after storage, with the contents at the start of storage being 100%.
4 °C保存の結果を表 1に、 25 °C保存の結果を表 2に、 40 °C保存の結果を表 3に示す。 なお、 表中の化合物 1はグリシクマリン、 化合物 2はグリシリン、 ィ匕 合物 3はデヒドログリアスペリン C、 化合物 4はデヒドログリアスペリン Dを表 す。 Table 1 shows the results of storage at 4 ° C, Table 2 shows the results of storage at 25 ° C, and Table 3 shows the results of storage at 40 ° C. In the table, compound 1 represents glycicoumarin, compound 2 represents glycillin, compound 3 represents dehydrogliasperin C, and compound 4 represents dehydrogliasperin D.
(比較例 1 ) (Comparative Example 1)
実施例 1で用いた甘草疎水性抽出物をアクター M— 2の代わりにエタノールに 溶解して 100 m g / 1のェタノール溶液を得た。 このエタノール溶液を H P L C用メタノールにて 100倍希釈し、 H P L C分析した結果、 ェタノール溶液 lm 1当たりグリシクマリン、 グリシリン、 デヒドログリアスペリン C及ぴデヒ ドロダリアスペリン Dをそれぞれ 2. 4mg、 1. 6mg、 7. 4mg、 5. 8 mg含んでいた。 The licorice hydrophobic extract used in Example 1 was dissolved in ethanol instead of Actor M-2 to obtain a 100 mg / 1 ethanol solution. This ethanol solution was diluted 100-fold with methanol for HPLC, and analyzed by HPLC.As a result, 2.4 mg and 1.6 mg of glycicumarin, glycillin, dehydrogliasperin C and dehydrodaliasperin D per lm of ethanol solution were used, respectively. It contained 7.4 mg and 5.8 mg.
このエタノール溶液を用い、 実施例 1と同様に保存安定性試験を行つた。 その 結果を表 1〜表 3に示す。
保存安定性 Using this ethanol solution, a storage stability test was performed in the same manner as in Example 1. Tables 1 to 3 show the results. Storage stability
4 保存 4 Save
化合物 1 化合物 2 化合物 3 化合物 4 開始時 100% 100% 100% 100% Compound 1 Compound 2 Compound 3 Compound 4 Starting 100% 100% 100% 100%
M M
C 1週間後 99% 99% 98% 98% T 2週間後 97% 97% 97% 97% 溶 C One week later 99% 99% 98% 98% T Two weeks later 97% 97% 97% 97% Melted
液 3週間後 99% 99% 98% 99% After 3 weeks 99% 99% 98% 99%
4週間後 97% 97% 97% 97% ェ 開始時 100% 100% 100% 100% 夕 4 weeks later 97% 97% 97% 97% D Starting 100% 100% 100% 100% Evening
ノ 1週間後 87% 87% 88% 87% 1 2週間後 86% 86% 85% 86% ル No One week later 87% 87% 88% 87% 1 Two weeks later 86% 86% 85% 86%
溶 3週間後 89% 88% 86% 88% 液 4週間後 93% 92% 91 % 93% Dissolution 3 weeks later 89% 88% 86% 88% Solution 4 weeks later 93% 92% 91% 93%
2 保存安定性 2 Storage stability
25で保存 Save as 25
化合物 1 化合物 2 化合物 3 化合物 4 開始時 100% 100% 100% 100% Compound 1 Compound 2 Compound 3 Compound 4 Starting 100% 100% 100% 100%
M M
C 1週間後 98% 98% 98% 98% T 2週間後 97% 97% 95% 97% 溶 C 1 week later 98% 98% 98% 98% T 2 weeks later 97% 97% 95% 97% soluble
液 .·.......3週間後 96% 97% 96% 96% Liquid 3 weeks later 96% 97% 96% 96%
4週間後 97% 98% 98% 98% ェ 開始時 100% 100% 100% 100% 夕 4 weeks later 97% 98% 98% 98% D Starting 100% 100% 100% 100% Evening
ノ 1週間後 89% 89% 84% 89% ) — 2週間後 90% 89% 76% 88% ル (1 week later 89% 89% 84% 89%) — 2 weeks later 90% 89% 76% 88%
溶 3週間後 88% 87% 68% 86% 彼 4週間後 88% 87% 38% 80%
表 3 After 3 weeks 88% 87% 68% 86% He After 4 weeks 88% 87% 38% 80% Table 3
4 °C保存においては、 化合物 1〜 4はいずれも MC T溶液とエタノール溶液で 安定であった。 25°C保存においては、 化合物 1〜4はいずれも MCT溶液で安 定であるのに対し、 エタノール溶液では特に化合物 3が不安定であった。 40°C 保存においては、 化合物 1〜4はいずれも MCT溶液で安定であるのに対し、 ェ タノール溶液では特に化合物 3及び 4が不安定であつた。 When stored at 4 ° C, compounds 1 to 4 were all stable in the MCT solution and the ethanol solution. When stored at 25 ° C, Compounds 1 to 4 were all stable in the MCT solution, whereas Compound 3 was particularly unstable in the ethanol solution. When stored at 40 ° C, compounds 1 to 4 were all stable in the MCT solution, whereas compounds 3 and 4 were particularly unstable in the ethanol solution.
これらの結果から、 ェタノール溶液では化合物 3及び 4は2 5〜 40 °C保存で 不安定であるが、 MCT溶液では保存温度にかかわらず化合物 1〜4のいずれも 安定であることが示された。 These results indicate that compounds 3 and 4 are unstable when stored at 25 to 40 ° C in ethanol solution, but are stable in MCT solution regardless of storage temperature. .
(実施例 2) 糖尿病予防作用 (Example 2) Diabetes prevention action
2型糖尿病モデル動物である KK一 Ayマウス （雌、 6週齢） を 3群 （各群 5 匹） に分け A群、 B群、 C群とし、 表 4に示す飼料をそれぞれ自由摂取にて 4週 間与えた。 なお、 基本飼料には、 カゼイン 20重量0 /0、 コーンスターチ 49. 9 48重量％、 シユークロース 10重量0 /0、 セルロースパウダー 5重量0 /0、 A I N 一 93ミネラル混合 3. 5重量0 /0、 A I N _ 93ビタミン混合 1重量0 /0、 重酒石 酸コリン 0. 25重量％、 第三プチルヒドロキノン 0. 002重量0 /0及び Lーシ
スチン 0 . 3重量％の組成 （合計 9 0重量。/。） である粉末精製飼料 （A I N— 9 3 G改変、 オリエンタル酵母株式会社） を用い、 また、 M C Tにはアクター M— 2 (理研ビタミン株式会社） を用いた。 KK-Ay mice (female, 6 weeks old), a type 2 diabetes model animal, were divided into three groups (five animals in each group), divided into groups A, B, and C, and fed the diets shown in Table 4 freely. Give for 4 weeks. Note that the basal diet, casein 20 wt 0/0, corn starch 49.9 48% by weight, Shiyukurosu 10 weight 0/0, cellulose powder 5 weight 0/0, AIN one 93 Mineral mixture 3.5 wt 0/0, AIN _ 93 vitamin mixture 1 wt 0/0, heavy tartaric acid choline 0.25 wt%, tertiary heptyl hydroquinone 0.002 wt 0/0 and L over Shi Powdered feed (AIN-93G modified, Oriental Yeast Co., Ltd.) with a composition of 0.3% by weight of stin (total 90%. /.) Was used, and activator M-2 (RIKEN Vitamin Co., Ltd.) was used for MCT. Co., Ltd.) was used.
給餌期間中 1週間毎にマウス尾静脈より少量採血し、 簡易式血糖測定器グルテ ス トエース （株式会社三和化学研究所） を用いて、 血糖値を測定した。 その結果 を表 5に示す。 表 4 A small amount of blood was collected from the tail vein of the mouse every week during the feeding period, and the blood glucose level was measured using a simple blood glucose meter Glute Test Ace (Sanwa Chemical Laboratory Co., Ltd.). Table 5 shows the results. Table 4
平均土標準誤差 (n-5)， * (p<0.05) Average soil standard error (n-5), * (p <0.05)
A群では、 経時的にマウスの血糖値が上昇し、 糖尿病の発症が認められた。 B 群では、 A群と同様にマウスの血糖値が上昇して糖尿病の発症が認められ、 MC Tの影響は認められなかった。 一方、 C群では、 A群及び B群と比較してマウス の血糖値の上昇が有意に抑制され、 実施例 1の M C T溶液による糖尿病予防作用
が認められた。 In group A, the blood glucose level of the mice increased over time, and diabetes was observed. In group B, as in group A, the blood glucose level of the mice increased and diabetes occurred, and the effect of MCT was not observed. On the other hand, in the group C, the increase in the blood glucose level of the mice was significantly suppressed as compared with the groups A and B, and the diabetes preventive effect of the MCT solution of Example 1 was observed. Was observed.
この結果から、 グリシクマリン、 グリシリン、 デヒ ドログリアスペリン C及び デヒドログリアスペリン Dを含む MCT溶液は、 糖尿病の予防に有効であること が示された。 The results showed that the MCT solution containing glycicoumarin, glycillin, dehydrogliasperin C and dehydrogliasperin D was effective in preventing diabetes.
(実施例 3) 内臓脂肪低減作用 (Example 3) Visceral fat reducing action
C 57BL/6 Jマウス （雌、 8週齢） に高脂肪 ·高糖分食を自由摂取にて 8 週間与え、 食餌性の肥満状態にした。 なお、 高脂肪 '高糖分食には、 カゼイン 2 5重量0 /0、 コーンスターチ 14. 869重量％、 シユークロース 20重量0 /。、 大 豆油 2重量％、 ラード 14重量％、 牛脂 14重量％、 セルロースパウダー 5重量 %、 A I N— 93ミネラル混合 3. 5重量0 /0、 A I N— 93ビタミン混合 1重量 %、 重酒石酸コリン 0. 25重量％、 第三プチルヒドロキノン 0. 006重量％ 及び L一シスチン 0. 375重量0 /0の組成である半固形化精製飼料 （オリエンタ ル酵母株式会社） を用いた。 C57BL / 6J mice (female, 8-week-old) were fed a high-fat, high-sugar diet with free intake for 8 weeks, resulting in dietary obesity. Note that the high-fat 'high sugar diet, casein 2 5 wt 0/0, corn starch 14.869 wt%, Shiyukurosu 20 weight 0 /. , Soybean oil 2% by weight, lard 14% by weight, beef tallow 14% by weight, cellulose powder 5 wt%, AIN- 93 mineral mixture 3.5 weight 0/0, AIN- 93 vitamin mixture 1% by weight, choline bitartrate 0. 25 wt%, using a third heptyl hydroquinone 0.006 wt% and L one-cystine 0.375 wt 0/0 semisolid of purified diet with a composition of (orienter yeast Co., Ltd.).
その後マウスを 3群 （各群 5匹） に分け A群、 B群、 C群とした。 A群には C E— 2飼料 (日本クレア株式会社) を、 B群には MCTを 3重量％添加した CE - 2飼料を、 C群には実施例 1の MC T溶液を 3重量。/。添加した C E _ 2飼料を、 それぞれ自由摂取にて 4週間与えた。 なお、 MCTにはアクター M— 2 (理研ビ タミン株式会社） を用いた。 一 B免絶食したマウスをエーテル麻酔下で開腹し、 腹 大動脈から採血して屠殺した後、 腸間膜脂肪、 腎臓周辺脂肪、 子宮周辺脂肪を摘 出し、 重量を測定した。 なお、 腸間膜脂肪重量、 腎臓周辺脂肪重量、 子宮周辺脂 肪重量の和を腹腔内脂肪重量とした。 その結果を表 6に示す。
表 6 Thereafter, the mice were divided into three groups (five mice in each group), which were designated as group A, group B, and group C. Group A received CE-2 feed (CLEA Japan), Group B received CE-2 feed supplemented with 3% by weight of MCT, and Group C received 3% of the MCT solution of Example 1. /. Each of the added CE_2 feeds was fed freely for 4 weeks. Actor M-2 (RIKEN Vitamin Co., Ltd.) was used for MCT. The mice that had been deprived of the 1B diet were laparotomized under ether anesthesia, blood was collected from the abdominal aorta and sacrificed, and mesenteric fat, perirenal fat, and perineal fat were extracted and weighed. The sum of the weight of mesenteric fat, the weight of fat around the kidney, and the weight of fat around the uterus was defined as fat weight in the abdominal cavity. Table 6 shows the results. Table 6
平均土標準誤差 (n=5), * (p<0.05) Mean soil standard error ( n = 5), * (p <0.05)
摂餌量及び体重は、 A群、 B群、 C群において差が認められなかった。 B群で は、 A群に比し、 腸間膜脂肪重量、 腎臓周辺脂肪重量、 子宮周辺脂肪重量及び腹 腔内脂肪重量に差は認められず、 M C Tの影響は認められなかった。 一方、 C群 では、 A群及び B群に比して腸間膜脂肪重量が有意差はないが明らかに減少し、 腎臓周辺脂肪重量、 子宮周辺脂肪重量及び腹腔内脂肪重量が有意に減少した。 す なわち、 高脂肪 .高糖分食の摂取によって蓄積した内臓脂肪が、 実施例 1の MC T溶液を含有する飼料を摂取することにより低減することが認められた。 No difference was observed in food consumption and body weight between groups A, B and C. In group B, there was no difference in mesenteric fat weight, perirenal fat weight, periuterine fat weight, and intraperitoneal fat weight compared to group A, and the effect of MCT was not observed. On the other hand, in group C, there was no significant difference in mesenteric fat weight compared to groups A and B, but it clearly decreased, and perirenal fat weight, periuterine fat weight and intraperitoneal fat weight significantly decreased. . That is, it was recognized that the visceral fat accumulated by ingestion of the high fat / high sugar content diet was reduced by ingesting the feed containing the MCT solution of Example 1.
この結果から、 グリシクマリン、 グリシリン、 デヒ ドログリアスペリン C及び デヒドログリアスペリン Dを含む MC T溶液は、 内臓脂肪の低減に有効であるこ とが示された。 The results showed that the MCT solution containing glycicoumarin, glycillin, dehydrogliasperin C and dehydrogliasperin D was effective in reducing visceral fat.
(実施例 4 ) ソフトカプセル剤の製造 (Example 4) Production of soft capsule
実施例 1の M C T溶液を、 ロータリー式ソフトカプセル製造装置を用いてゼラ チン皮膜に圧入し、 内容量 3 5 O m gのソフトカプセル剤を得た。 The MCT solution of Example 1 was press-fitted into the gelatin membrane using a rotary soft capsule manufacturing apparatus to obtain a soft capsule having an internal volume of 35 O mg.
(実施例 5 ) マーガリンの製造 (Example 5) Production of margarine
硬化綿実油 （商品名：スノーライト、 鐘淵化学工業株式会社） 8 0重量部、 実 施例 1の M C T溶液 2 0重量部、 無塩バター （四つ葉乳業株式会社） 1 0重量部 に、 グリセリンモノ脂肪酸エステル （商品名：エマルジー M S、 理研ビタミン株
式会社） 0. 2重量部、 レシチン 0. 2重量部を添加し、 60°Cに加熱溶解し油 相を調製した。 Hardened cottonseed oil (trade name: Snow Light, Kanegafuchi Chemical Industry Co., Ltd.) 80 parts by weight, MCT solution of Example 1 20 parts by weight, unsalted butter (Four-leaf Dairy Co., Ltd.) 10 parts by weight Glycerin mono fatty acid ester (trade name: Emulgy MS, RIKEN Vitamin Strain) 0.2 parts by weight of lecithin and 0.2 parts by weight of lecithin were added and dissolved by heating at 60 ° C to prepare an oil phase.
調製された油相 84. 9重量部に撹拌しながら水 15.. 1重量部を添加し、 2 0分間乳化を行った後、 コンビネーターで冷却捏和してマーガリンを得た。 15.1 parts by weight of water was added to 84.9 parts by weight of the prepared oil phase while stirring, emulsified for 20 minutes, and then cooled and kneaded with a combinator to obtain margarine.
(実施例 6) 濃縮乳の製造 (Example 6) Production of concentrated milk
実施例 1の M C T溶液 10重量部を 70 °Cに加温溶解後、 レシチン 0. 1重量 部及びポリグリセリン脂肪酸エステル 0. 1重量部を順次溶解して油相を調製し た。 After heating and dissolving 10 parts by weight of the MCT solution of Example 1 at 70 ° C., 0.1 part by weight of lecithin and 0.1 part by weight of polyglycerol fatty acid ester were sequentially dissolved to prepare an oil phase.
脱脂粉乳 25重量部、 グリセリン脂肪酸エステル 0. 1重量部、 ショ糖脂肪酸 エステル 0. 1重量部を 60°Cの水 64. 6重量部に溶解して水相を調製した。 調製した水相と油相を予備乳化した後、 超高温瞬間 （UHT) 殺菌機にて 14 5 °Cで 4秒間殺菌した。 次いで真空冷却した後、 均質化機により 10 MP aの圧 力で均質化し、 更に 10°Cまでプレート冷却して加工用濃縮乳を得た。 An aqueous phase was prepared by dissolving 25 parts by weight of skim milk powder, 0.1 part by weight of glycerin fatty acid ester, and 0.1 part by weight of sucrose fatty acid ester in 64.6 parts by weight of water at 60 ° C. After pre-emulsifying the prepared aqueous phase and oil phase, they were sterilized at 145 ° C for 4 seconds with an ultra-high temperature instant (UHT) sterilizer. Then, after vacuum cooling, the mixture was homogenized with a homogenizer at a pressure of 10 MPa and further cooled to 10 ° C on a plate to obtain concentrated milk for processing.
(実施例 7) マヨネーズの製造 (Example 7) Production of mayonnaise
醸造酢 10重量部、 食塩 1重量部、 砂糖 0. 6重量部、 マスタ一ド粉末 0. 2 重量部、 グルタミン酸ナトリウム 0. 2重量部を混合器の中に加え、 15〜20 °C下で攪拌 ·混合し水相を調製した。 その後、 米白絞油 68重量部、 実施例 1の MCT溶液 10重量部に卵黄 10重量部を加え、 攪拌乳化して得た乳化液 （10 〜15°C) を少しずつ加えながら 15〜20°C下で攪拌し、 予備乳化した。 次い で、 コロイドミルを用いて仕上げ乳化を行いマヨネーズを得た。 産業上の利用可能性 Add 10 parts by weight of brewed vinegar, 1 part by weight of salt, 0.6 parts by weight of sugar, 0.2 parts by weight of mustard powder, 0.2 parts by weight of sodium glutamate in a mixer, and at 15-20 ° C The mixture was stirred and mixed to prepare an aqueous phase. Then, add 10 parts by weight of egg yolk to 68 parts by weight of rice white squeezed oil and 10 parts by weight of the MCT solution of Example 1, and gradually add the emulsion (10 to 15 ° C) obtained by stirring and emulsification for 15 to 20 minutes. The mixture was stirred at ° C and pre-emulsified. Next, finish emulsification was performed using a colloid mill to obtain mayonnaise. Industrial applicability
本発明によれば、 健康食品や保健機能食品 （特定保健用食品、 栄養機能食品） などの飲食品、 医薬品、 医薬部外品、 化粧品などに利用することができる油脂加 ェ組成物を得ることができる。 本発明の油脂加工組成物は、 インスリン抵抗性の 改善、 並びに、 内臓脂肪型肥満、 2型糖尿病、 高脂血症、 高血圧症などの生活習 慣病の予防及び 又は改善に有効である。
According to the present invention, it is possible to obtain an oil / fat composition that can be used in foods and drinks such as health foods and functional health foods (foods for specified health use, nutritional foods), pharmaceuticals, quasi-drugs, cosmetics, and the like. Can be. The oil / fat processing composition of the present invention is effective for improving insulin resistance and for preventing and / or improving lifestyle-related diseases such as visceral fat obesity, type 2 diabetes, hyperlipidemia and hypertension.
Claims
1 . グリシクマリン、 グリシリン、 デヒドログリァスぺリン C及びデヒ ドログ リアスペリン Dからなる群より選ばれた少なくとも 1つの化合物を溶解している 油脂を含有することを特徴とする生活習慣病予防及び/又は改善用の油脂加工組 成物。 1. For prevention and / or improvement of lifestyle-related diseases, characterized by containing an oil or fat in which at least one compound selected from the group consisting of glycicoumarin, glycillin, dehydrogliaspurin C and dehydrogliaspriasperin D is dissolved. Oil and fat processing composition.
2 . グリシクマリン、 グリシリン、 デヒドログリァスペリン C及ぴデヒドログ リアスペリン Dからなる群より選ばれた少なくとも 1つの化合物を溶解している 油脂を含有することを特徴とするインスリン抵抗性改善用の油脂加工組成物。 2. Fat or oil processing for improving insulin resistance, characterized by containing an oil or fat in which at least one compound selected from the group consisting of glycicoumarin, glycillin, dehydrogliasperin C and dehydrogliasperin D is dissolved. Composition.
3 . グリシクマリン、 グリシリン、 デヒドロダリアスペリン C及びデヒド口グ リアスペリン Dからなる群より選ばれた少なくとも 1つの化合物を、 その総量と して成人一人一日当たり 0 . 0 1〜1 0 0 m g / k g体重を摂取できる量を含む ことを特徴とする請求の範囲第 1又は 2項記載の油脂力 Pェ組成物。 3. At least one compound selected from the group consisting of glycicoumarin, glycillin, dehydrodaria sperin C, and dehydrid gliasperin D is used in a total of 0.01 to 100 mg / kg body weight per adult per day. 3. The oil and fat composition according to claim 1 or 2, comprising an amount capable of ingesting.
4 . 油脂が中鎖脂肪酸トリグリセリ ド及ぴ /または部分グリセリ ドを含むグリ セリン脂肪酸エステルである、 請求の範囲第 1〜 3項のいずれか 1項記載の油脂 加工組成物。 4. The fat and oil processing composition according to any one of claims 1 to 3, wherein the fat or oil is a glycerin fatty acid ester containing a medium-chain fatty acid triglyceride and / or a partial glyceride.
5 . 油脂が中鎖脂肪酸トリグリセリ ドを 5 0重量。/。以上含むグリセリン脂肪酸 エステルである、 請求の範囲第 4項記載の油脂加ェ組成物。 5. The fats and oils contain 50 weight of medium-chain fatty acid triglycerides. /. 5. The fat and oil composition according to claim 4, which is a glycerin fatty acid ester containing the above.
6 . 油脂が部分グリセリ ドを 5 0重量％以上含むグリセリン脂肪酸エステルで ある、 請求の範囲第 4項記載の油脂加工組成物。 6. The fat and oil processing composition according to claim 4, wherein the fat or oil is a glycerin fatty acid ester containing 50% by weight or more of a partial glyceride.
7 . 生活習慣病が内臓脂肪型肥満、 2型糖尿病、 高脂血症及び高血圧症からな る群より選ばれた少なくとも 1種である、 請求の範囲第 1項記載の油脂加工組成 物。
7. The oil and fat processing composition according to claim 1, wherein the lifestyle-related disease is at least one selected from the group consisting of visceral fat obesity, type 2 diabetes, hyperlipidemia and hypertension.
8. 生活習慣病が内臓脂肪型肥満及び/又は 2型糖尿病である、 請求の範囲第 1項記載の油脂加工組成物。 8. The fat and oil processing composition according to claim 1, wherein the lifestyle-related disease is visceral fat obesity and / or type 2 diabetes.
9. 飲食用である請求の範囲第 1〜 8項のいずれか 1項記載の油脂加工組成物。 9. The processed oil or fat composition according to any one of claims 1 to 8, which is used for eating and drinking.
10. 医薬用である請求の範囲第 1〜 8項のいずれか 1項記載の油脂加工組成 物。 10. The oil-and-fat processing composition according to any one of claims 1 to 8, which is used for medicine.
11. グリシクマリン、 グリシリン、 デヒドログリアスペリン C及びデヒドロ ダリアスペリン Dからなる群より選ばれた少なくとも 1つの化合物が、 グリキル リ一ザ . ゥラレンシス （G l y c y r r h i z a u r a l e n s i s) 由来で ある請求の範囲第 1〜 10項のいずれか 1項記載の油脂加工組成物。 11. The method according to any one of claims 1 to 10, wherein at least one compound selected from the group consisting of glycycoumarin, glycillin, dehydrogliasperin C and dehydrodariasperin D is derived from Glycyrrhizauralensis. The oil / fat processing composition according to any one of claims 1 to 7.
12. グリシクマリン、 グリシリン、 デヒドログリアスペリン C及びデヒドロ グリアスペリン Dからなる群より選ばれた少なくとも 1つの化合物を溶解してい る油脂を含有する組成物を用いて生活習慣病を予防及ぴ 又は改善する方法。 12. Prevent and / or ameliorate lifestyle-related diseases using a composition containing an oil or fat in which at least one compound selected from the group consisting of glycicoumarin, glycillin, dehydrogliasperin C and dehydrogliasperin D is dissolved Method.
13. グリシクマリン、 グリシリン、 デヒドログリァスぺリン C及ぴデヒドロ ダリアスペリン Dからなる群より選ばれた少なくとも 1つの化合物を溶解してい る油脂を含有する組成物を用いてインスリン抵抗性を改善する方法。 13. A method for improving insulin resistance using a composition containing an oil or fat in which at least one compound selected from the group consisting of glycicoumarin, glycillin, dehydrogliasurin C and dehydrodariasperin D is dissolved.
14. グリシクマリン、 グリシリン、 デヒドログリアスペリン C及ぴデヒドロ グリアスペリン Dからなる群より選ばれた少なくとも 1つの化合物を溶解してい る油脂を含有する組成物を用いて高血糖を予防及び/又は改善する方法。 14. Prevent and / or ameliorate hyperglycemia by using a composition containing an oil or fat in which at least one compound selected from the group consisting of glycicoumarin, glycillin, dehydrogliasperin C and dehydrogliasperin D is dissolved Method.
15. グリシクマリン、 グリシリン、 デヒドログリアスペリン C及ぴデヒドロ ダリアスペリン Dからなる群より選ばれた少なくとも 1つの化合物を溶解してい る油脂を含有する組成物を用いて腹腔内脂肪を減少させる方法。
15. A method for reducing intraperitoneal fat using a composition containing an oil or fat in which at least one compound selected from the group consisting of glycicoumarin, glycillin, dehydrogliasperin C and dehydrodariasperin D is dissolved.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2005508126A JPWO2004064830A1 (en) | 2003-01-24 | 2004-01-23 | Oil processing composition for prevention and improvement of lifestyle-related diseases |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2003-016023 | 2003-01-24 | ||
| JP2003016023 | 2003-01-24 |
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|---|---|
| WO2004064830A1 true WO2004064830A1 (en) | 2004-08-05 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/JP2004/000599 WO2004064830A1 (en) | 2003-01-24 | 2004-01-23 | Processed fat compositions for preventing and improving lifestyle-related diseases |
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| Country | Link |
|---|---|
| JP (1) | JPWO2004064830A1 (en) |
| TW (1) | TW200427410A (en) |
| WO (1) | WO2004064830A1 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007114013A1 (en) * | 2006-03-31 | 2007-10-11 | Suntory Limited | Composition containing lignan compound |
| JP2008096317A (en) * | 2006-10-12 | 2008-04-24 | Toyama Prefecture | Method for identifying variety by composition ratio of flavonoid that plants contain |
| US7943663B2 (en) | 2005-09-30 | 2011-05-17 | Suntory Holdings Limited | Process and an apparatus for producing episesamin-rich compositions |
| CN110354119A (en) * | 2018-03-26 | 2019-10-22 | 中国农业大学 | Application of the glycycoumarin in the drug of preparation prevention and/or medicine physical property hepatic injury |
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| JPH02204417A (en) * | 1989-02-02 | 1990-08-14 | Maruzen Kasei Co Ltd | Hydrophobic licorice flavonoid preparation |
| WO2002047699A1 (en) * | 2000-12-12 | 2002-06-20 | Kaneka Corporation | Compositions for preventing or ameliorating multiple risk factor syndromes |
| WO2003037316A1 (en) * | 2001-10-11 | 2003-05-08 | Kaneka Corporation | Peroxisome proliferator activated receptor ligands and process for producing the same |
| JP2003252784A (en) * | 2002-02-27 | 2003-09-10 | Kanegafuchi Chem Ind Co Ltd | alpha-GLUCOSIDASE INHIBITOR |
| JP2003274856A (en) * | 2002-03-26 | 2003-09-30 | Kanegafuchi Chem Ind Co Ltd | Edible oil and fat composition containing hydrophobic extract of licorice |
-
2004
- 2004-01-20 TW TW093101588A patent/TW200427410A/en unknown
- 2004-01-23 WO PCT/JP2004/000599 patent/WO2004064830A1/en active Application Filing
- 2004-01-23 JP JP2005508126A patent/JPWO2004064830A1/en not_active Withdrawn
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02204417A (en) * | 1989-02-02 | 1990-08-14 | Maruzen Kasei Co Ltd | Hydrophobic licorice flavonoid preparation |
| WO2002047699A1 (en) * | 2000-12-12 | 2002-06-20 | Kaneka Corporation | Compositions for preventing or ameliorating multiple risk factor syndromes |
| WO2003037316A1 (en) * | 2001-10-11 | 2003-05-08 | Kaneka Corporation | Peroxisome proliferator activated receptor ligands and process for producing the same |
| JP2003252784A (en) * | 2002-02-27 | 2003-09-10 | Kanegafuchi Chem Ind Co Ltd | alpha-GLUCOSIDASE INHIBITOR |
| JP2003274856A (en) * | 2002-03-26 | 2003-09-30 | Kanegafuchi Chem Ind Co Ltd | Edible oil and fat composition containing hydrophobic extract of licorice |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7943663B2 (en) | 2005-09-30 | 2011-05-17 | Suntory Holdings Limited | Process and an apparatus for producing episesamin-rich compositions |
| WO2007114013A1 (en) * | 2006-03-31 | 2007-10-11 | Suntory Limited | Composition containing lignan compound |
| US9408803B2 (en) | 2006-03-31 | 2016-08-09 | Suntory Holdings Limited | Compositions containing lignan-class compounds |
| JP2008096317A (en) * | 2006-10-12 | 2008-04-24 | Toyama Prefecture | Method for identifying variety by composition ratio of flavonoid that plants contain |
| CN110354119A (en) * | 2018-03-26 | 2019-10-22 | 中国农业大学 | Application of the glycycoumarin in the drug of preparation prevention and/or medicine physical property hepatic injury |
Also Published As
| Publication number | Publication date |
|---|---|
| TW200427410A (en) | 2004-12-16 |
| JPWO2004064830A1 (en) | 2006-05-18 |
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