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WO2008029846A1 - Inhibiteur de lipase - Google Patents

Inhibiteur de lipase Download PDF

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Publication number
WO2008029846A1
WO2008029846A1 PCT/JP2007/067311 JP2007067311W WO2008029846A1 WO 2008029846 A1 WO2008029846 A1 WO 2008029846A1 JP 2007067311 W JP2007067311 W JP 2007067311W WO 2008029846 A1 WO2008029846 A1 WO 2008029846A1
Authority
WO
WIPO (PCT)
Prior art keywords
fatty acid
oil
fat
active ingredient
acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2007/067311
Other languages
English (en)
Japanese (ja)
Inventor
Toshiharu Arishima
Setsuo Tsujii
Nobuhiko Tachibana
Makiko Kojima
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Fuji Oil Co Ltd (fka Fuji Oil Holdings Inc)
Original Assignee
Fuji Oil 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 Fuji Oil Co Ltd filed Critical Fuji Oil Co Ltd
Publication of WO2008029846A1 publication Critical patent/WO2008029846A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A61K31/23—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms
    • A61K31/231—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms having one or two double bonds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/115—Fatty acids or derivatives thereof; Fats or oils
    • 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
    • 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
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Definitions

  • the present invention relates to a lipase inhibitor and a food containing the same. More specifically, it is safe to digest and absorb lipids in the body, and effectively inhibits the presumptive lipase, which is the key to obesity and hyperlipidemia, and contributes to the prevention and prevention of these diseases.
  • the present invention relates to highly oil-soluble lyase inhibitors. Background art
  • Patent Document 1 Red Scenic Sky, Iwabenkei, Svonou, Bold, Pastia Force, Tormentilla, El Campuri, Tucon Isomatsu, Chuchuashi, Kyak-Luck, Cinnamon, Yam, Sendangsa, Mugigi, Strawberry, Morge, Rose, ⁇ , Se
  • a lipase inhibitor containing at least one species selected from the group of plants consisting of Hypericum perforatum, Tochu and white tea has been proposed.
  • Patent Document 2 at least one material strength selected from the group consisting of yucca, ginseng, jasmine tea, yamako, yellow cocoon tea, rooibos tea, soybean germ, ginger and tochu tea, A lipase inhibitor containing an extract as an active ingredient has been proposed.
  • the extract is almost water-soluble and cannot be mixed with fats and oils, it can only be taken at the time of eating, is complicated, and the effect of the extract is insufficient. Most of them are in the hall!
  • Patent Document 3 proposes to use tetrahydrolipstatin as a gastrointestinal lipase inhibitor. This inhibitor is said to inactivate by covalent bonding directly with the lipase itself, and its effect is quite significant. Although it is more powerful, some have diarrhea symptoms, food safety concerns remain, and oil-soluble lipase inhibitors that are more mildly effective are desired.
  • Patent Literature 4 recently proposed LUU-type triacylglycerol as a lipase inhibitor that exhibits a mild effect! /, And has a melting point of 30 ° C. There is more
  • Patent Document 1 Japanese Patent Application Laid-Open No. 2002-179586
  • Patent Document 2 Japanese Patent Laid-Open No. 2002-275077
  • Patent Document 3 U.S. Pat.No. 4598089
  • Patent Document 4 JP-A-2006-151875
  • An object of the present invention is to contribute to prevention and treatment of obesity caused by excessive intake of fat and diseases caused by obesity, and a low melting point oil-soluble river which can be added to any oil and fat. It is to provide a zeta inhibitor. Means for solving the problem
  • a lipase inhibitor comprising, as an active ingredient, acyl glycerol, an unsaturated fatty acid having an unsaturated bond at an integer ⁇ position less than n / 2 as a constituent fatty acid. (Where n is the number of carbon atoms in the fatty acid, and ⁇ is the position of the carbon atom counted from the end of the carboxyl group.)
  • a lipid absorption inhibitor comprising asyl glycerol as an active ingredient according to (1) or (2).
  • An anti-obesity agent comprising the acyl glycerol described in (1) or (2) as an active ingredient.
  • a liver lipid reducing agent comprising the acyl glycerol as described in (1) or (2) as an active ingredient.
  • a hyperlipidemia ameliorating agent comprising the acyl glycerol described in (1) or (2) as an active ingredient.
  • a medicament comprising the agent according to any one of (1) to (6).
  • acyl glycerol which comprises an unsaturated fatty acid having an unsaturated bond at the ⁇ position of an integer less than n / 2 as a constituent fatty acid, strongly inhibits lipase activity and has a low melting point. It is oil-soluble and can be added to all types of fats and oils. It is effective in preventing and treating obesity caused by excessive intake of fat and diseases caused by obesity.
  • Acylglycerol which is an oil-soluble substance that delays hydrolysis by lipase in the present invention, contains an unsaturated fatty acid residue having an unsaturated bond at the ⁇ position of an integer less than n / 2 in the glyceride. It is acyl glycerol containing more than residues. “N” indicates the number of carbon atoms constituting the fatty acid, “ ⁇ ” indicates the position of the carbon atom counted from the end of the carboxyl group of the fatty acid, and ⁇ is an integer less than n / 2.
  • the first carbon atom is the carbon atom of the carboxyl group, and since it does not participate in the unsaturated bond between carbon atoms, it is excluded from the target power.
  • Examples of unsaturated fatty acids having an unsaturated bond at an integer ⁇ position of less than n / 2 include cis-4-decenoic acid having 10 carbon atoms (obucsylic acid: ⁇ 10 ⁇ 4), cis-4-dodecenoic acid having 12 carbon atoms (lindelic acid: ⁇ 12 ⁇ 4), cis-4-tetradecenoic acid having 14 carbon atoms (zudic acid: ⁇ 14 ⁇ 4), cis-5-tetradecenoic acid (Phyzeteric acid: ⁇ 14 ⁇ 5), cis-6-hexadecenoic acid with 16 carbon atoms ( ⁇ 16 ⁇ 6), cis-6-octadecenoic acid with 18 carbon atoms (petroseric acid: ⁇ 18 ⁇ 6), etc.
  • sorbic acid decadienoic acid, hiragoic acid, ⁇ -linolenic acid, eicosatrienoic acid, docosatrienoic acid, hexadecatetraenoic acid, arachidonic acid, eicosapentaenoic acid, and the like can also be used.
  • petroceric acid is most preferable from the viewpoint of the supply amount that monounsaturated fatty acid is functionally preferred.
  • these fatty acids The melting point of acylglycol containing fatty acids and fatty acids is generally less than 30 ° C, except when other long-chain saturated fatty acids coexist, and is highly versatile and easy to use.
  • the acyl glycerol containing these fatty acids may exist in any of mono-, di-, and tri-forms, but considering the point that crystallization is minimized and the lipase is easily recognized as a substrate.
  • the triacylglycerol form is preferred.
  • the unsaturated fatty acid having an unsaturated bond at an integer ⁇ position less than n / 2 needs to be contained in one or more residues in the glyceride, and preferably in two or more residues.
  • the acyl glycerol containing an unsaturated fatty acid having an unsaturated bond at the ⁇ position of an integer less than n / 2, which is an active ingredient of the lipase inhibitor of the present invention, is various animals, plants, fishes.
  • Oils and fats derived from vegetable oils such as kumoji seed oil, tuna oil, parsley seed oil, sardine seed oil, nakamado oil, red arabic seed oil, purple seed oil, evening primrose oil, borage oil, sardine oil, Animal fats such as shark liver oil and herring oil can be used as raw materials.
  • These acyl glycerols can be fractionated, distilled or concentrated as necessary, and can be transesterified with other animal and plant oils by known methods.
  • the acyl glycerol containing an unsaturated fatty acid having an unsaturated bond at an integer ⁇ position of less than n / 2 may be used as it is as a lipase inhibitor, and optionally, to other base fats and oils. You may blend and use. These oils can be used in place of conventional processing oils. In addition, there is no limitation if the base fat is edible animal or vegetable fat.
  • the lipase inhibitor of the present invention preferably has a mild inhibitory effect on the relaxation and delay of hydrolysis of the ingested oil and fat. Specifically, about 10 to 30% of the ingested oil and fat is preferable. Ideally, it should be in a state where about 20% is hardly decomposed.
  • the lipase inhibitor of the present invention is an acyl oil containing an unsaturated fatty acid having an unsaturated bond at an ⁇ position of an integer less than n / 2, and ingested oil and fat.
  • acyl oil containing an unsaturated fatty acid having an unsaturated bond at an ⁇ position of an integer less than n / 2 By using more than 1% by weight, preferably more than 3% by weight, it is possible to reduce or delay the hydrolysis by lipase. If the amount of acylglyceride containing unsaturated fatty acid having an unsaturated bond at the ⁇ position of an integer less than n / 2 is less than the ingested fat and oil, the lipase inhibitory effect is weakened. Also, an unsaturated bond is formed at the position of an integer ⁇ less than n / 2.
  • the acyl glycerol containing the unsaturated fatty acid having a combination there is almost no effect due to the large amount used. However, since it is difficult to replace fats and oils in all foods, it is usually used at 30% by weight or less, preferably 15% by weight or less of the fats and oils to be ingested.
  • the lipase inhibitor of the present invention can be used as a lipid absorption inhibitor, an anti-obesity agent, a liver lipid reducing agent, and a hyperlipidemia improving agent. These can be used widely in foods that usually contain fats and oils. For example, emulsified foods such as cream, margarine, mayonnaise, dressing, dairy products, processed foods such as confectionery represented by chocolate, bread, ham, sausage, marine processed foods such as power, maboko, chikuwa, etc. It can be added without sacrificing flavor and texture.
  • the lipase inhibitor, lipid absorption inhibitor, anti-obesity agent, hepatic lipid reducing agent, and hyperlipidemia ameliorating agent of the present invention can also be used as pharmaceuticals.
  • the administration method of the medicine containing these may be either oral administration or parenteral administration.
  • the active ingredient can be mixed with a solid or liquid pharmaceutical carrier suitable for administration methods such as oral administration and rectal administration, and administered in the form of a preparation.
  • tripetroserine As shown in Table 1, compared with triolein, tripetroserine has lipase activity.
  • the control soybean oil group (Comparative Zone 1) and the fats and oils extracted from parsley seeds (petrocellinic acid content 75% of acylglycol) were large so that the petroleum oil containing petrothelic acid was 10% in the mixed oil.
  • Rats were purchased from 5-week-old SD male rats, preliminarily raised for 1 week, divided into groups, and the diet composition was 10 for each group of 5 animals in the mixed diet shown in Table 2 with some modifications to the AIN-93G composition. The animals were reared for 6 days and dissected after 6 hours of fasting. Body weight change, feed efficiency, blood fat content, wrinkle Peripheral fat mass, renal circumference
  • Vitamin mix (AIN-93G) ⁇ . ⁇ ⁇ .0 ⁇ .0
  • lipase inhibition is effective for the prevention and treatment of obesity due to excessive intake of fat and obesity due to obesity due to the lipase activity that is slowly inhibited and oil-soluble and can be added to any edible oil. It became possible to obtain an agent and an oil and fat composition containing the agent.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Diabetes (AREA)
  • Emergency Medicine (AREA)
  • Child & Adolescent Psychology (AREA)
  • Epidemiology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Mycology (AREA)
  • Nutrition Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Medicines Containing Plant Substances (AREA)

Abstract

La présente invention concerne un inhibiteur liposoluble de la lipase qui contribue à la prévention et au traitement de l'obésité due à la surconsommation de lipides et des maladies causées par l'obésité et qui peut être ajouté à n'importe graisse ou huile. Il est possible d'obtenir un inhibiteur liposoluble de la lipase largement utilisable en toute sécurité en utilisant en tant que matière active un acylglycérol ayant en tant qu'acide gras constitutif un acide gras insaturé qui comporte une liaison insaturée en position Δ, Δ étant un nombre entier inférieur à n/2, n représentant le nombre d'atomes de carbone de l'acide gras et Δ représentant la position d'un atome de carbone comptée à partir de l'extrémité carboxyle.
PCT/JP2007/067311 2006-09-07 2007-09-05 Inhibiteur de lipase Ceased WO2008029846A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2006-243118 2006-09-07
JP2006243118 2006-09-07

Publications (1)

Publication Number Publication Date
WO2008029846A1 true WO2008029846A1 (fr) 2008-03-13

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ID=39157272

Family Applications (1)

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PCT/JP2007/067311 Ceased WO2008029846A1 (fr) 2006-09-07 2007-09-05 Inhibiteur de lipase

Country Status (1)

Country Link
WO (1) WO2008029846A1 (fr)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5618939A (en) * 1979-07-24 1981-02-23 Junichi Iwamura Effective component in corbicula as a drug and its preparation
JP2002322052A (ja) * 2001-04-26 2002-11-08 Kao Corp 小腸上皮中の脂質代謝改善剤
WO2003056928A1 (fr) * 2001-12-28 2003-07-17 The Nisshin Oillio, Ltd. Compositions de graisse et d'huile permettant de reduire les lipides sanguins

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5618939A (en) * 1979-07-24 1981-02-23 Junichi Iwamura Effective component in corbicula as a drug and its preparation
JP2002322052A (ja) * 2001-04-26 2002-11-08 Kao Corp 小腸上皮中の脂質代謝改善剤
WO2003056928A1 (fr) * 2001-12-28 2003-07-17 The Nisshin Oillio, Ltd. Compositions de graisse et d'huile permettant de reduire les lipides sanguins

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
WEBER N. ET AL.: "Petroselinic acid from dietary triacylglycerols reduces the concentration of arachidonic acid in tissue lipids of rats", J. NUTR., vol. 125, no. 6, 1995, pages 1563 - 1568, XP003021631 *

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