WO2002011552A2 - Oil/fat composition - Google Patents

Oil/fat composition Download PDF

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Publication number
WO2002011552A2
WO2002011552A2 PCT/JP2001/006777 JP0106777W WO0211552A2 WO 2002011552 A2 WO2002011552 A2 WO 2002011552A2 JP 0106777 W JP0106777 W JP 0106777W WO 0211552 A2 WO0211552 A2 WO 0211552A2
Authority
WO
WIPO (PCT)
Prior art keywords
fatty acid
oil
unsaturated fatty
fat
fat composition
Prior art date
Application number
PCT/JP2001/006777
Other languages
French (fr)
Other versions
WO2002011552A3 (en
Inventor
Shin Koike
Takeshi Yasumasu
Tadashi Hase
Takatoshi Murase
Takuji Yasukawa
Yoshihisa Katsuragi
Akira Takei
Original Assignee
Kao Corporation
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 Kao Corporation filed Critical Kao Corporation
Priority to BRPI0113105-2A priority Critical patent/BRPI0113105B1/en
Priority to US10/343,748 priority patent/US7090886B2/en
Priority to DE60143753T priority patent/DE60143753D1/en
Priority to EP01954487A priority patent/EP1315424B1/en
Priority to CA002418350A priority patent/CA2418350C/en
Priority to BR0113105-2A priority patent/BR0113105A/en
Publication of WO2002011552A2 publication Critical patent/WO2002011552A2/en
Publication of WO2002011552A3 publication Critical patent/WO2002011552A3/en

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Classifications

    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23GCOCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G3/00Sweetmeats; Confectionery; Marzipan; Coated or filled products
    • A23G3/34Sweetmeats, confectionery or marzipan; Processes for the preparation thereof
    • A23G3/36Sweetmeats, confectionery or marzipan; Processes for the preparation thereof characterised by the composition containing organic or inorganic compounds
    • A23G3/40Sweetmeats, confectionery or marzipan; Processes for the preparation thereof characterised by the composition containing organic or inorganic compounds characterised by the fats used
    • AHUMAN NECESSITIES
    • A21BAKING; EDIBLE DOUGHS
    • A21DTREATMENT, e.g. PRESERVATION, OF FLOUR OR DOUGH, e.g. BY ADDITION OF MATERIALS; BAKING; BAKERY PRODUCTS; PRESERVATION THEREOF
    • A21D2/00Treatment of flour or dough by adding materials thereto before or during baking
    • A21D2/08Treatment of flour or dough by adding materials thereto before or during baking by adding organic substances
    • A21D2/14Organic oxygen compounds
    • A21D2/16Fatty acid esters
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23DEDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D7/00Edible oil or fat compositions containing an aqueous phase, e.g. margarines
    • A23D7/01Other fatty acid esters, e.g. phosphatides
    • A23D7/011Compositions other than spreads
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23DEDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D7/00Edible oil or fat compositions containing an aqueous phase, e.g. margarines
    • A23D7/01Other fatty acid esters, e.g. phosphatides
    • A23D7/013Spread compositions
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23DEDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D7/00Edible oil or fat compositions containing an aqueous phase, e.g. margarines
    • A23D7/015Reducing calorie content; Reducing fat content, e.g. "halvarines"
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23DEDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D9/00Other edible oils or fats, e.g. shortenings, cooking oils
    • A23D9/007Other edible oils or fats, e.g. shortenings, cooking oils characterised by ingredients other than fatty acid triglycerides
    • A23D9/013Other fatty acid esters, e.g. phosphatides
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23GCOCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G3/00Sweetmeats; Confectionery; Marzipan; Coated or filled products
    • A23G3/34Sweetmeats, confectionery or marzipan; Processes for the preparation thereof
    • A23G3/346Finished or semi-finished products in the form of powders, paste or liquids
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23KFODDER
    • A23K20/00Accessory food factors for animal feeding-stuffs
    • A23K20/10Organic substances
    • A23K20/158Fatty acids; Fats; Products containing oils or fats
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, 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
    • A23L27/00Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/60Salad dressings; Mayonnaise; Ketchup
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, 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
    • A23L33/00Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105Plant extracts, their artificial duplicates or their derivatives
    • A23L33/11Plant sterols or derivatives thereof, e.g. phytosterols
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, 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
    • A23L33/00Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/115Fatty acids or derivatives thereof; Fats or oils
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, 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
    • A23L33/00Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/115Fatty acids or derivatives thereof; Fats or oils
    • A23L33/12Fatty acids or derivatives thereof
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, 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
    • A23L33/00Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/40Complete food formulations for specific consumer groups or specific purposes, e.g. infant formula
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11BPRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B5/00Preserving by using additives, e.g. anti-oxidants
    • C11B5/0092Mixtures
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11CFATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C1/00Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
    • C11C1/02Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils
    • C11C1/04Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils by hydrolysis
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11CFATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/02Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with glycerol
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11CFATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/04Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
    • C11C3/06Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils with glycerol
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23GCOCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G2200/00COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF containing organic compounds, e.g. synthetic flavouring agents
    • A23G2200/08COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF containing organic compounds, e.g. synthetic flavouring agents containing cocoa fat if specifically mentioned or containing products of cocoa fat or containing other fats, e.g. fatty acid, fatty alcohol, their esters, lecithin, paraffins
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23VINDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00Food compositions, function of food ingredients or processes for food or foodstuffs

Definitions

  • the present invention relates to an oil/fat composition having a specific
  • glyceride composition and a specific fatty acid composition, having good stability
  • Lipids (oils or fats), important nutrients in addition to proteins and carbohydrates, are particularly useful as an energy source. It however has a high calorie
  • Nutritionally essential fatty acids are, for
  • linoleic acid examples include arachidonic acid and linolenic acid. These fatty acids are known
  • unsaturated fatty acid polyunsaturated fatty acid or a ratio of ⁇ 6-unsaturated fatty
  • trans unsaturated fatty acids increase the LDL-cholesterol level, thereby exerting a
  • vitamins A, D, E and K can be used only for salty snack foods. This restriction is made for preventing both anal leakage and inhibition of absorption of fat-
  • MCT medium-chain fatty acid triglyceride
  • Patent No. 2035495 an agent for lowering the triglyceride concentration in serum
  • An object ofthe present invention is to provide an extremely useful oil/fat
  • composition which can meet the recent demand and contributes to good health, more
  • the present inventors have found that a diglyceride having a specific unsaturated
  • fatty acid constitution has excellent visceral-fat burning property (visceral-fat reducing
  • the present invention provides an oil/fat composition comprising 60 to 100 wt.%) of a diglyceride wherein the diglyceride has, as its fatty acid constituent, 15 to 90
  • the diglyceride to be used in the present invention is required to have, as 15 to
  • unsaturated fatty acid as used herein means a fatty acid having a first unsaturated bond at the third carbon atom from the -position and having at least two carbon-carbon
  • octadecatrienoic acid and stearidonic acid (all cis-6,9,12,15-octadecatetraenoic acid),
  • the ⁇ 3-unsaturated fatty acid having less than 20 carbon atoms is preferred to
  • a diglyceride in an amount of 20 to 80%, more preferably 30 to 70%,
  • fatty acid is required to be 1 to 6, preferably 1.2 to 5, more preferably 1.4 to 4, especially 1.5 to 3.
  • the trans unsaturated fatty acid is an unsaturated fatty acid having, in the
  • the content ofthe trans unsaturated fatty acid is preferably 5% or less for health
  • the diglyceride preferably contains, as another fatty acid constituent, 2 to 50%,
  • the content of unsaturated fatty acids is preferably 70 to 100%, more preferably 80 to 100%), especially 90 to 100%) ofthe fatty acid constituents ofthe diglyceride.
  • the content of an ⁇ 9-unsaturated fatty acid is preferably 10 to 60% ofthe fatty
  • acids more specifically, oleic acid, eicosamonoenoic acid and docosamonoenoic acid.
  • oleic acid is particularly preferred.
  • olein-olein diglyceride is particularly preferred.
  • the diglyceride containing such fatty acid constituents is incorporated in the oil/fat composition in an amount of 60 to 100%>, but from the viewpoint of physiologically active effects and industrial productivity, their content is preferably 65
  • the remaining components in the oil/fat composition are monoglyceride, triglyceride and free fatty acid.
  • monoglyceride is incorporated in an amount of 0 to 40%>, preferably 0.1 to 10%>, more
  • the oil/fat composition contains a triglyceride as the balance. Its content is preferably 0 to 40%), preferably 0.1
  • composition greater than 15%, preferably not greater than 5%>, especially not greater than 2%> of all the fatty acid constituents, for attaining stability against oxidation.
  • substantially free of such a polyunsaturated fatty acid is most preferred.
  • the oil/fat composition ofthe present invention may be prepared by subjecting an oil or fat having target fatty acid constituents and glycerin to ester exchange reaction or by acting lipase on a mixture ofthe target fatty acid constituents or ester thereof with
  • esterification using lipase is more preferred. Since even in the esterification using lipase, isomerization can happen to occur owing to purifying means after completion of the reaction, it is preferred to purify under mild conditions so as not to cause
  • the oil/fat composition ofthe present invention is preferably provided for use
  • POV peroxide value
  • a preferred oil/fat composition ofthe present invention comprises 65 to 99%> of the diglyceride, 0.1 to 4% ofthe monoglyceride, 0.1 to 34.9% ofthe triglyceride and
  • the triglyceride has, as its fatty acid constituent, 70 to 100% of an unsaturated fatty acid; and the content of a
  • polyunsaturated fatty acid having at least 4 carbon-carbon double bonds is 5% or less based on all the fatty acid constituents ofthe oil/fat composition.
  • a more preferred oil/fat composition ofthe present invention comprises 70 to 80 to
  • constituents 30 to 70% of a -linolenic acid, 10 to 50%) of oleic acid, 5 to 40%) of an
  • the triglyceride has, as its fatty acid constituent, 80 to 100%o of an unsaturated fatty acid; and the content of a
  • polyunsaturated fatty acid having at least 4 carbon-carbon double bonds is 2% or less
  • An especially preferred oil/fat composition ofthe present invention comprises 75
  • the triglyceride has, as its fatty acid constituent, 90 to 100%) of an unsaturated fatty acid; and the content of a
  • polyunsaturated fatty acid having at least 4 carbon-carbon double bonds is 0 in all the fatty acid constituents ofthe oil/fat composition.
  • the oil/fat composition ofthe present invention may contain an antioxidant.
  • Any antioxidant is usable insofar as it is ordinarily employed for foods or
  • catechin tocopherol, vitamin C fatty acid esters, phospholipid and natural antioxidant components.
  • catechin tocopherol, vitamin C fatty acid esters, phospholipid and natural antioxidant components.
  • vitamin C fatty acid esters examples include
  • antioxidant is preferably added to the oil/fat composition ofthe present invention in an
  • the oil/fat composition ofthe present invention preferably contains a phytosterol
  • the phytosterol content in the oil/fat composition depends on its raw
  • oil/fat composition is lower than when obtained by other methods.
  • phytosterol content contents within a range of 0.05%> to 1.2%> are preferred. It may be
  • phytosterol examples include that in free form such as -sitosterol,
  • campestanol and cycloartol that in ester form such as their fatty acid esters, ferulate esters and cinnamate esters.
  • crystallization inhibitor used in the present invention examples include
  • polyol fatty acid esters such as polyglycerin-condensed ricinoleate esters, polyglycerin fatty acid esters, sucrose fatty acid esters, sorbitan fatty acid esters, polyoxyethylene
  • polyol fatty acid esters polyglycerin fatty acid esters, sucrose fatty acid
  • the crystallization inhibitor is preferably added to the oil/fat composition ofthe
  • the oil/fat composition thus obtained exhibits, as well as excellent physiological
  • the composition acts even at a low
  • the oil/fat composition ofthe present invention can be used for an oil/fat- containing food containing the composition as a part ofthe food. Healthy foods which
  • oil/fat-containing foods such as soup, dressing, mayonnaise, coffee creamer, whipped
  • exemplified oil/fat-containing food can be prepared by adding, in addition to the above- described oil/fat composition, food raw materials ordinarily employed depending on the
  • the amount ofthe oil/fat composition ofthe present invention to be any oil/fat composition ofthe present invention.
  • oil/fat derived from the raw material to the oil/fat composition ofthe present invention oil/fat derived from the raw material to the oil/fat composition ofthe present invention
  • oil/fat composition ofthe present invention is mixed with another food raw material and provided as an oil/fat-containing processed food
  • following raw materials can be used.
  • examples include edible oils or fats, for example, natural animal
  • oils or vegetable oils or fats obtained by subjecting these natural animal or vegetable oils or fats to ester exchange reaction, hydrogenation or
  • Preferred examples include soybean oil, rapeseed oil, rice bran oil, corn
  • oils or fats thereof are oils, palm oil, linseed oil, perilla oil and fish oil, and processed oils or fats thereof.
  • an emulsifier examples include various proteins such as egg protein, soybean protein
  • sucrose fatty acid esters sorbitan fatty acid esters, polyoxyethylene
  • sorbitan fatty acid esters glycerin fatty acid monoesters, polyglycerin fatty acid esters,
  • a stabilizer examples include polysaccharide thickeners and starches such as xanthane gum, gellan gum, guar gum, carrageenan, pectin, tragacanth gum and konjac
  • mannan a flavor developing agent such as salt, sugar, vinegar or seasoning,
  • flavoring such as spice and flavor, colorant and antioxidant such as tocopherol or natural
  • antioxidant component can be added.
  • a weight ratio of oil phase to water phase is 1/99 to 90/10, preferably 10/90 to
  • the diglyceride 80/20, especially 30/70 to 75/25 in terms of oil phase/water phase.
  • the content in the oil phase is 60 to 100%, preferably 65 to 99%, especially 75 to 92%.
  • -linolenic acid content in the fatty acid constituents of a diglyceride is 20 to 80%>
  • the phytosterol content is 0 to 10%, preferably 1 to 7%, especially 2 to 5%>, the emulsifier content is 0.01 to 5%, especially
  • the pH is 1.0 to
  • 7.0 preferably 2.0 to 6.0, especially 3.0 to 5.0 and it can be adjusted by an organic acid (or salt thereof) such as vinegar, lemon juice or citric acid, or an inorganic acid (or salt
  • Water-in-oil type oil/fat-containing foods A weight ratio of water phase to oil phase is 90/10 to 1/99, preferably 80/20 to
  • the diglyceride content in the oil phase is 60 to 100%
  • acid constituents of a diglyceride is 20 to 80%>, preferably 30 to 70%>, especially 40 to
  • saturated fatty acid + trans unsaturated fatty acid is 1 to 6, preferably 1.2 to 5
  • the phytosterol content is 0 to 10%>, preferably 1 to 7%>, especially 2
  • the emulsifier content is 0.01 to 5%>, especially 0.05 to 3%.
  • water-in-oil type oil/fat-containing foods such as margarine and spread can be prepared in a conventional manner.
  • the oil/fat content is 1 to 30%>, especially 1 to 20%) and the diglyceride content
  • oil/fat in the oil/fat is 60 to 100%, preferably 65 to 99%, especially 40 to 65%.
  • -linolenic acid content in the fatty acid constituents of a diglyceride is 20 to 80%>
  • the phytosterol content is 0 to 20%
  • Carbohydrate such as sucrose, glucose,
  • fructose, maltose, xylitol, sorbitol, erythritol or starch is preferably added in an amount
  • sodium bicarbonate and an acidic agent such as tartaric acid, fumaric acid or citric acid
  • Oil/fat-containing pocket-size foods such as tablet, candy, caramel and gummy
  • candy can be prepared in a conventional manner by using the above-described materials.
  • the oil/fat content is 1 to 40%>, especially 5 to 35%) and the diglyceride content
  • oil/fat in the oil/fat is preferably 60 to 100%, more preferably 65 to 99%, especially 75 to 92%.
  • the -linolenic acid content in the fatty acid constituents of a diglyceride is 20 to
  • unsaturated fatty acid is 1 to 6, preferably 1.2 to 5, especially 1.5 to 3.
  • the phytosterol content is 0 to 20%>, preferably 1 to 20%>, especially 1 to 15%>.
  • the flour content is 10 to
  • the bakery food is preferred to contain at least one of hen's whole egg, egg yolk and egg white, and separated or decomposed product thereof in an amount of 0 to 30%, especially 5 to 25%.
  • the salt content is
  • the carbohydrate content is 0 to 25%, while the baking powder content is 0 to 1%.
  • bakery foods such as bread, cake, biscuit and cookie can be prepared in a conventional manner.
  • Examples ofthe pharmaceuticals include orally administrable preparations, e.g.,
  • solid preparations such as powder, granule, capsule, pill and tablet, liquid preparations
  • orally administrable agent can be prepared by adding, in addition to the oil/fat
  • composition excipient, disintegrator, binder, lubricant, surfactant, alcohol, water, water-
  • administrable preparation can differ with its purpose or dosage form, but addition in an
  • 0.1 to 50 g preferably 0.5 to 10 g, especially 1 to 7.5 g, in terms ofthe oil/fat
  • composition is preferably administered once or several portions a day.
  • feed examples include livestock feed for cow, pig, fowl and sheep, feed
  • reaction mixture was reacted at 230 °C for 0.5 hour in a nitrogen gas atmosphere.
  • the reaction mixture was
  • oil phase oil/fat composition
  • oil/fat composition oil/fat composition
  • Oil/fat composition 3 was obtained.
  • Oil/fat composition 4 was obtained.
  • Oil/fat Composition 5 is obtained.
  • Oil/fat composition 1 whereby Oil/fat composition 5 was obtained.
  • Oil/fat composition la was prepared by mixing 100 parts by weight of Oil/fat composition 1, 0.04 part by weight of tocopherol (Mix Vitamin E "MDE-6000";
  • Oil/fat composition lb was prepared by mixing 100 parts by weight of Oil/fat
  • composition 1 0.04 part by weight of tocopherol and 0.1 part by weight of catechin.
  • Oil/fat composition 1 c was prepared by mixing 100 parts by weight of Oil/fat
  • composition 1 0.04 part by weight of tocopherol, 0.1 part by weight of catechin, 0.02
  • VCP vitamin C palmitate; product of Roche, Ltd.
  • a diet obtained by replacing a portion corresponding to 4% ofthe starch of a high-fat and high-sucrose diet (control diet) having the below-described composition with an oil/fat composition or oil/fat was administered to C57BL/6J male mice (a model
  • Visceral fat weight and body weight gain of a rat fed with a control diet were each designated as 100.
  • capsule were administered to two groups of 8 normal adult male volunteers, respectively.
  • CT visceral fat area
  • CT subcutaneous fat area
  • triglyceride level blood triglyceride level
  • blood plasminogen activator
  • PAI-1 inhibitor type-1
  • Oil/fat composition or oil/fat (20 g) was charged in a 50 mL sample bottle.
  • ALA-DG synthesized from purified perilla oil (product of Ohta Oil Mill Co., Ltd.) by using immobilized lipase in accordance with the method of Birgitte, et al.
  • the intake amount of ALA-DG was set at 5 capsules/day (2 g/day).
  • the oxygen intake amount was measured after fasting for 12 hours.
  • body mass index was 25.0 ⁇ 0.7.
  • oxygen intake amount was 43.4 ⁇ 2.4 and their BMI was 24.1 ⁇ 0.5.
  • p ⁇ 0.05 meant existence of a significant difference.
  • the blood was collected from the vein at the bent side portion ofthe upper arm and the serum and plasma of it were provided for various biochemical tests.
  • TG serum triglyceride
  • PL phospholipid
  • NEFA free fatty acid
  • T-cho total cholesterol
  • LDL-cho LDL-cho
  • HDL-cho HDL-cho
  • RLP-cho cholesterol
  • RLP-TG remnant lipoprotein triglyceride
  • acetoacetic acid 3-
  • hydroxybutyric acid total keton body and liver function values (GOT, GPT, y -GTP).
  • VLDL-TG (mg/dL) 105.8 ⁇ 14.1 86.8 ⁇ 8.2 *
  • VLDL-PL (mg/dL) 35.0 ⁇ 4.3 .29.2 ⁇ 2.1
  • VLDL-triglyceride showed a significant
  • cho and VLDL-PL showed a decrease.
  • RLP-cho and phospholipid each showed a decrease.
  • Acetoacetic acid showed a significant increase.
  • a resting metabolic rate was calculated from the oxygen intake amount for 3
  • Test was made using, as subjects, sixteen normal male volunteers from 25 to 40
  • Intake amount a day was set at 5 capsules ((400 mg x 5)/day).
  • CT scanning was conducted at the cross-section at the naval part and at a
  • visceral fat area and subcutaneous fat area were determined from the CT image.
  • p ⁇ 0.05 meant the existence of a significant difference.
  • a change in each ofthe weight, BMI, waist circumference and waist hip ratio measured after 12 weeks is shown as a relative value to the initial value of each subject set at 100 (Table 10).
  • Rate of variation means the percentage as the value at 0 week
  • liver/spleen CT ratio indicating a reduction in the liver fat
  • Feeding was carried out using a Roden CAFE (product of Oriental Yeast Co., Ltd./Tokyo) and the feed was changed every 2 days.
  • the feed intake was carried out using a Roden CAFE (product of Oriental Yeast Co., Ltd./Tokyo) and the feed was changed every 2 days. The feed intake
  • ALA-DG was prepared from perilla oil in the presence of immobilized lipase in
  • the DG and TG contents in the acylglycerol of ALA-DG are 85.2% and 14.1%, respectively.
  • diglyceride was about 7:3.
  • safflower oil and rapeseed oil were purchased from The Nisshin Oil Mills Ltd.
  • Vitamin mixture f 1.0 1.0 1.0 1.0 1.0 -potato starch 66.5 28.5 27.5 26.5 24.5
  • Low-fat feed contains therein 5%> of a lipid
  • high-fat feed HF
  • the ALA-DG added feed was prepared by adding 1%,
  • mice were weighed every week. Under fasting for 12 hours after
  • liver weight of each of the ALA-DG- 1 % group and the ALA-DG-4% group showed a significantly low value (p ⁇ 0.05) compared with that ofthe HF group, but no significant difference was recognized from the LF group.
  • Oil/fat composition lb was added. They were mixed, molded and then cut
  • Corn starch (44 parts by weight), 40 parts by weight of crystalline cellulose, 5
  • Example 11 Mayonnaise
  • Oil/fat composition lb ofthe invention 65.0%
  • composition lb ofthe invention in a homomixer, Oil/fat composition lb was added
  • Example 13 Tablets parts by weight
  • the resulting mixture was ground in a mortar.
  • the resulting grind was compressed into tablets, each 2 g in weight, by a tableting machine (24.5 MPa, 4 seconds).
  • Salt 2.5 Refined sugar, salt and Oil/fat composition lb ofthe invention were put into a
  • composition lb was then added, followed by mixing (for 5 minutes at a low speed and 22 minutes at a medium speed). For fermentation, the dough was allowed to rise at
  • dough was divided into pieces, each 37 g in weight, and they were rounded like a ball.
  • the oil/fat composition ofthe present invention has excellent visceral fat

Abstract

Abstract Provided is an oil/fat composition comprising 60 to 100 wt.% of a diglyceride wherein the diglyceride has, as the fatty acid constituent thereof, 15 to 90 wt.% of an φ 3-unsaturated fatty acid having less than 20 carbon atoms and a cis φ 3-unsaturated fatty acid/(cis φ 6-unsaturated fatty acid + saturated fatty acid + trans unsaturated fatty acid) at a weight ratio of 1 to 6. The composition is excellent in visceral fat burning property, body fat burning property and stability against autoxidation.

Description

DESCRIPTION
OIL/FAT COMPOSITION
Technical Field:
The present invention relates to an oil/fat composition having a specific
glyceride composition and a specific fatty acid composition, having good stability
against autoxidation, and being extremely useful for health with excellent visceral-fat
burning and body-fat burning properties.
Background Art:
Lipids (oils or fats), important nutrients in addition to proteins and carbohydrates, are particularly useful as an energy source. It however has a high calorie
content (9 kcal/g) and intake of it promotes obesity and can be causative of problems such as life-style related diseases. A meal rich in lipid is typically delicious and people ofthe present day are accustomed to such a meal. In advanced countries under satiation,
an increase in lipidic intake has come to be a serious nation-wide problem together with a rise in medical expenses. In recent days, people are highly interested particularly in
health promotion and maintenance and preventive treatment of diseases and a number of
investigations have been made on the relationship between lipids and obesity or life¬
style related diseases.
Primary investigations to date have been related to fatty acids constituting a
triglyceride, a principal component of a lipid. Nutritionally essential fatty acids are, for
example, linoleic acid, arachidonic acid and linolenic acid. These fatty acids are known
to be utilized in the body as a constituent of a biomembrane or a raw material of
eicosanoids (prostaglandin, thromboxanes, leukotrienes, etc.). In addition, it is reported that there is a high possibility that saturated fatty acids in a diet have a blood-serum
cholesterol heightening action, leading to atherosclerosis or heart diseases (Lancet, 2,
959(1950)); and a high linoleic acid oil contained much in a diet increases tumor
incidence and size of experimental animals (J. National Cancer Institute, 66,
517(1971)). It is described that an oleic-acid-rich and saturated-fatty-acid-poor diet
lowers LDL-cholesterol level, while maintaining an HDL-cholesterol level, thereby
reducing the risk of heart diseases (J. Lipid Res., 26, 194(1985), New England J.
Medicine, 314, 745(1988)). In addition, physiological activity of various ω 3-
unsaturated fatty acids including antithrombus effects of eicosapentaenoic acid
contained in a fish oil have drawn attention (Ann. Rev. Nutr., 8, 517(1988)). It is however pointed out that eicosapentaenoic acid or docosahexaenoic acid having high physiological activity has more double bonds than the other fatty acids so that it has a serious problem in not only heat stability but also stability against autoxidation. Under
the present state, such fatty acids are practically used only for some products. Based on the study on intake balance of these fatty acids, a number of research reports have been
presented, for example, on a recommendable ratio of saturated fatty acid : mono-
unsaturated fatty acid : polyunsaturated fatty acid or a ratio of ω 6-unsaturated fatty
acid : ω 3-unsaturated fatty acid. Research is still in progress ("Nutrition and Diseases
of Oils and Fats", published by Saiwai Shobo, "The 6th edition of Recommended
Dietary Allowances for Japanese", Ministry of Health and Welfare). It is pointed out
that trans unsaturated fatty acids increase the LDL-cholesterol level, thereby exerting a
bad influence on health, for example, increasing the risk of cardiovascular diseases. In
November, 1999, FDA proposed to include the amount of trans unsaturated fatty acids in nutritional labeling and to limit the amount of trans unsaturated fatty acids in foods
having health claims or products having nutrient content claims (FDA home page).
With a view to preventing obesity, substitutes for fats and oils or non-absorptive
fats and oils have been developed and typical ones include sucrose fatty acid polyester
(U.S. Patent No. 3,600,186). It is excreted without being absorbed in the body so that
the calories derived from fat is 0 kcal/g. There is however a potential problem that it
can cause anal leakage and inhibit absorption of fat-soluble vitamins. In addition, it
does not become a supply source of essential fatty acids. The use of this substance was authorized by FDA in 1996, under the restriction that a semi-solid or solid sucrose fatty
acid polyester having a melting point of 37.8 to 71.1 °C and containing predetermined
amounts of vitamins A, D, E and K can be used only for salty snack foods. This restriction is made for preventing both anal leakage and inhibition of absorption of fat-
soluble vitamins. It is known that a medium-chain fatty acid triglyceride (MCT) is not accumulated on the body, but it has poor heat stability. Similar effects of conjugated
linoleic acid, fish oil or perilla oil are disclosed (Lipids, 32, 853(1997), J. Agric. Food
Chem., 46, 1225(1998)).
Further, disclosed with attention paid to the glyceride structure are an edible oil composition (EP Patent No. 0525,915), a cholesterol-level lowering agent (Japanese
Patent No. 2035495), an agent for lowering the triglyceride concentration in serum
(Japanese Patent Application Laid-Open No. 4-300825), a body weight increase
inhibitor (Japanese Patent Application Laid-Open No. 4-300826), a preventive or
therapeutic agent for fatty liver (Japanese Patent Application Laid-Open No. 4-300828)
and a liquid general-purpose oil/fat composition (US Patent No. 6,004,611). They paid attention only to the effect derived from the diglyceride structure, and did not induce
effects of diglyceride at the maximum.
An object ofthe present invention is to provide an extremely useful oil/fat
composition which can meet the recent demand and contributes to good health, more
specifically, which is free from side effects such as anal leakage or inhibition of
absorption of fat-soluble vitamins, is safe and can overcome the drawback of oils and
fats such as a tendency to obesity, has incomparable body-fat burning • visceral-fat
burning action and has excellent stability against autoxidation.
Disclosure ofthe Invention:
The present inventors have found that a diglyceride having a specific unsaturated
fatty acid constitution has excellent visceral-fat burning property (visceral-fat reducing
property) and body-fat burning property.
The present invention provides an oil/fat composition comprising 60 to 100 wt.%) of a diglyceride wherein the diglyceride has, as its fatty acid constituent, 15 to 90
wt.% of an ω 3-unsaturated fatty acid having less than 20 carbon atoms and has a cis
ω 3-unsaturated fatty acid/(cis ω 6-unsaturated fatty acid + saturated fatty acid + trans
unsaturated fatty acid) at a weight ratio of 1 to 6.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
The diglyceride to be used in the present invention is required to have, as 15 to
90 wt.%) (which will hereafter be described "%" simply) of its fatty acid constituents, an
ω 3-unsaturated fatty acid having less than 20 carbon atoms. The term " ω 3-
unsaturated fatty acid" as used herein means a fatty acid having a first unsaturated bond at the third carbon atom from the -position and having at least two carbon-carbon
unsaturated bonds. Specific examples include -linolenic acid (all cis-9,12,15-
octadecatrienoic acid) and stearidonic acid (all cis-6,9,12,15-octadecatetraenoic acid),
with a -linolenic acid being particularly preferred.
The ω 3-unsaturated fatty acid having less than 20 carbon atoms is preferred to
be incorporated in a diglyceride in an amount of 20 to 80%, more preferably 30 to 70%,
especially 40 to 65% for exhibition of various physiologically active effects.
From the viewpoint of exhibition of physiologically active effects, stability
against autoxidation and balance of fatty acids, a weight ratio of cis ω 3-unsaturated
fatty acid to (cis ω 6-unsaturated fatty acid + saturated fatty acid + trans unsaturated
fatty acid) is required to be 1 to 6, preferably 1.2 to 5, more preferably 1.4 to 4, especially 1.5 to 3.
The trans unsaturated fatty acid is an unsaturated fatty acid having, in the
molecule thereof, at least one trans double bond. It can be measured by infrared absorption spectrum (Standard Methods for the Analysis of Oils, Fats and Derivatives
2.4.4.2 of Japan Oil Chemists' Society) or gas chromatography (JAOCS, 70, 425(1993),
etc.). The content ofthe trans unsaturated fatty acid is preferably 5% or less for health
reasons.
The diglyceride preferably contains, as another fatty acid constituent, 2 to 50%,
preferably 5 to 40%, especially 10 to 30%) of a C18.22 ω 6-unsaturated fatty acid such as
linoleic acid and γ -linolenic acid from the viewpoints of intake balance of fatty acids
and physiologically active effects of an ω 3-unsaturated fatty acid. For physiologically
active effects, the content of unsaturated fatty acids is preferably 70 to 100%, more preferably 80 to 100%), especially 90 to 100%) ofthe fatty acid constituents ofthe diglyceride.
The content of an ω 9-unsaturated fatty acid is preferably 10 to 60% ofthe fatty
acid constituents ofthe diglyceride, and in consideration ofthe intake balance of fatty
acids, physiological activity and stability against oxidation, 10 to 50% is more preferred
and 12 to 30% is especially preferred. Examples ofthe ώ 9-unsaturated fatty acid
include C10-24 ω 9-unsaturated fatty acids, preferably C16.22 ω 9-unsaturated fatty
acids, more specifically, oleic acid, eicosamonoenoic acid and docosamonoenoic acid.
Of these, oleic acid is particularly preferred. For example, olein-olein diglyceride is
preferably contained in an amount less than 45%>, more preferably 40%> or less from the viewpoint of physiological activity.
The diglyceride containing such fatty acid constituents is incorporated in the oil/fat composition in an amount of 60 to 100%>, but from the viewpoint of physiologically active effects and industrial productivity, their content is preferably 65
to 99%o, more preferably 70 to 95%), especially 75 to 92%>. The remaining components in the oil/fat composition are monoglyceride, triglyceride and free fatty acid. The
monoglyceride is incorporated in an amount of 0 to 40%>, preferably 0.1 to 10%>, more
preferably 0.1 to 4%>, especially 0.1 to 2%> in the oil/fat composition in order to bring
about taste masking effects, prevent smoking upon heating and heighten industrial
productivity. An amount of 0.1 to 1.5% is most preferred. Fatty acid constituents ofthe
monoglyceride are preferred to be similar to those ofthe diglyceride. The free fatty acid
(salt) has a strange taste so that in order to prevent a deterioration in taste, its content is
preferably suppressed to 3.5% or less, preferably 2.5% or less, more preferably 1.5% or
less, especially 1% or less, most preferably 0.5 % or less. The oil/fat composition contains a triglyceride as the balance. Its content is preferably 0 to 40%), preferably 0.1
to 34.9%o, more preferably 2 to 29.9%, especially 6 to 24.9%. The triglyceride
preferably contains, as its fatty acid constituents, 55 to 100%, more preferably 70 to
100%, still more preferably 80 to 100%, especially 90 to 100% of C8_24, particularly C16.
22 unsaturated fatty acids from the viewpoint of physiologically active effects.
In the oil/fat composition ofthe present invention, polyunsaturated fatty acids,
such as eicosapentaenoic acid, docosahexaenoic acid and arachidonic acid, having at
least four carbon-carbon double bonds are preferred to be incorporated in an amount not
greater than 15%, preferably not greater than 5%>, especially not greater than 2%> of all the fatty acid constituents, for attaining stability against oxidation. The composition
substantially free of such a polyunsaturated fatty acid is most preferred.
The oil/fat composition ofthe present invention may be prepared by subjecting an oil or fat having target fatty acid constituents and glycerin to ester exchange reaction or by acting lipase on a mixture ofthe target fatty acid constituents or ester thereof with
glycerin, thereby conducting esterification. To prevent isomerization during reaction,
esterification using lipase is more preferred. Since even in the esterification using lipase, isomerization can happen to occur owing to purifying means after completion of the reaction, it is preferred to purify under mild conditions so as not to cause
isomerization of fatty acids. Moreover, use of a raw material oil or fat having a less
trans acid content is preferred.
The oil/fat composition ofthe present invention is preferably provided for use
after purified through degumming, acid-removing, decoloring, washing with water or
deodorizing from the viewpoints of stability against oxidation and taste. It preferably
has a peroxide value (POV, Standard Method for the Analysis of Oils, Fats and Derivatives 2.5.2.1 of Japan Oil Chemists' Society) of 10 or less, preferably 7 or less,
more preferably 5 or less, especially 3 or less, most preferably 1 or less. The color (10R
+ Y) as measured by the Lovibond method (Standard Method for the Analysis of Oils,
Fats and Derivatives 2.2.1.1 of Japan Oil Chemists' Society, 5 1/4 inch glass cell is
used) is preferably 35 or less, more preferably 30 or less, still more preferably 25 or less,
especially 20 or less.
A preferred oil/fat composition ofthe present invention comprises 65 to 99%> of the diglyceride, 0.1 to 4% ofthe monoglyceride, 0.1 to 34.9% ofthe triglyceride and
1.5% or less of a free fatty acid (salt), wherein the diglyceride has, as its fatty acid
constituents, 20 to 80% of -linolenic acid, 10 to 60% of oleic acid, 2 to 50%> of an
ω 6-unsaturated fatty acid, 70 to 100%> of an unsaturated fatty acid and a cis ω 3-
unsaturated fatty acid/(cis ω 6-unsaturated fatty acid + saturated fatty acid + trans
unsaturated fatty acid) at a weight ratio of 1.2 to 5; the triglyceride has, as its fatty acid constituent, 70 to 100% of an unsaturated fatty acid; and the content of a
polyunsaturated fatty acid having at least 4 carbon-carbon double bonds is 5% or less based on all the fatty acid constituents ofthe oil/fat composition.
A more preferred oil/fat composition ofthe present invention comprises 70 to
95%) ofthe diglyceride, 0.1 to 2%> ofthe monoglyceride, 2 to 29.9%> ofthe triglyceride
and 1 % or less of a free fatty acid (salt), wherein the diglyceride has, as its fatty acid
constituents, 30 to 70% of a -linolenic acid, 10 to 50%) of oleic acid, 5 to 40%) of an
ω 6-unsaturated fatty acid, 80 to 100% of an unsaturated fatty acid and a cis ω 3-
unsaturated fatty acid/(cis ω 6-unsaturated fatty acid + saturated fatty acid + trans
unsaturated fatty acid) at a weight ratio of 1.4 to 4; the triglyceride has, as its fatty acid constituent, 80 to 100%o of an unsaturated fatty acid; and the content of a
polyunsaturated fatty acid having at least 4 carbon-carbon double bonds is 2% or less
based on all the fatty acid constituents ofthe oil/fat composition.
An especially preferred oil/fat composition ofthe present invention comprises 75
to 92% ofthe diglyceride, 0.1 to 1.5% ofthe monoglyceride, 6 to 24.9% ofthe
triglyceride and 0.5 %> or less of a free fatty acid (salt), wherein the diglyceride has, as
its fatty acid constituents, 40 to 65% of -linolenic acid, 12 to 30% of oleic acid, 10 to
30%) of an ω 6-unsaturated fatty acid, 90 to 100% of an unsaturated fatty acid and a cis
ω 3-unsaturated fatty acid/(cis ω 6-unsaturated fatty acid + saturated fatty acid + trans
unsaturated fatty acid) at a weight ratio of 1.5 to 3; the triglyceride has, as its fatty acid constituent, 90 to 100%) of an unsaturated fatty acid; and the content of a
polyunsaturated fatty acid having at least 4 carbon-carbon double bonds is 0 in all the fatty acid constituents ofthe oil/fat composition.
The oil/fat composition ofthe present invention may contain an antioxidant.
Any antioxidant is usable insofar as it is ordinarily employed for foods or
pharmaceuticals. Combination of one or more of catechin, tocopherol, vitamin C fatty acid esters, phospholipid and natural antioxidant components is preferred, with catechin
being particularly preferred. Examples ofthe vitamin C fatty acid esters include
palmitate esters and stearate esters, while those ofthe natural antioxidant components
include herbs such as rosemary and extracts from the leaves or roots of a peach. The
antioxidant is preferably added to the oil/fat composition ofthe present invention in an
amount of 0.01 to 5%, especially 0.05 to 1%.
The oil/fat composition ofthe present invention preferably contains a phytosterol
in an amount of 0.05%) or greater, especially 0.3%> or greater because it has a cholesterol lowering effect. The phytosterol content in the oil/fat composition depends on its raw
material oil/fat or preparation process. For example, when a commercially available
fatty acid obtained by distillation is used as a raw material, the phytosterol content in the
oil/fat composition is lower than when obtained by other methods. In the case of
distillative preparation, it is preferred to add the phytosterol to give a content of 0.05%
or greater. Although no particular limitation is imposed on the upper limit ofthe
phytosterol content, contents within a range of 0.05%> to 1.2%> are preferred. It may be
added in an amount of 1.2% to 20%) when a further cholesterol reduction is intended.
Examples ofthe phytosterol include that in free form such as -sitosterol,
j3 -sitosterol, stigmasterol, campesterol, a -sitostanol, j3 -sitostanol, stigmastanol,
campestanol and cycloartenol; and that in ester form such as their fatty acid esters, ferulate esters and cinnamate esters.
It is more preferred to add a crystallization inhibitor to the oil/fat composition of the present invention, if necessary, to provide low temperature stability from a loss of
transparency.
Examples ofthe crystallization inhibitor used in the present invention include
polyol fatty acid esters such as polyglycerin-condensed ricinoleate esters, polyglycerin fatty acid esters, sucrose fatty acid esters, sorbitan fatty acid esters, polyoxyethylene
sorbitan fatty acid esters, and propylene glycol fatty acid esters.
As the polyol fatty acid esters, polyglycerin fatty acid esters, sucrose fatty acid
esters and sorbitan fatty acid esters each having an HLB (calculation formula of Griffin)
of 4 or less, especially 3 or less are preferred.
The crystallization inhibitor is preferably added to the oil/fat composition ofthe
present invention in an amount of 0.02 to 0.5%), especially 0.05 to 0.2%. The oil/fat composition thus obtained exhibits, as well as excellent physiological
activities such as promotion of visceral-fat burning, promotion of body-fat burning,
heightening of resting metabolism and acceleration of lipid metabolism, physiological
activities such as promotion of blood-fat burning, improvement of liver function,
lowering of leptin, lowering of PAI-1, lowering of blood sugar level, improvement of
insulin resistance and lowering of a blood pressure. Moreover, owing to its excellent
stability against autoxidation, it can be stored for a long period and in addition, has an
excellent taste. Since an ω 3-unsaturated acyl group exists not as a free fatty acid but as
an acyl group constituting the diglyceride, the composition acts even at a low
concentration, has an immediate effect, has a good taste and is safe. Such excellent properties make it possible to use the oil/fat composition ofthe present invention for
foods, feeds and pharmaceuticals.
The oil/fat composition ofthe present invention can be used for an oil/fat- containing food containing the composition as a part ofthe food. Healthy foods which
exhibit a special function, thereby promoting health can be given as one example of such oil/fat-containing foods. Specific examples include capsules, tablets, powders,
granules, bakery foods such as bread, cake, cookie, pie and pizza crust, oil-in-water type
oil/fat-containing foods such as soup, dressing, mayonnaise, coffee creamer, whipped
cream and ice cream, water-in-oil type oil/fat-containing foods such as margarine,
spread and butter cream, confections, for example, chocolate, caramel, candy, snacks
such as potato chips, and dessert, beverages, sauces, barbecue sauces, peanut butter,
baking shortening, dough, filling, enrober, meat processed foods such as ham, sausage
and hamburger steak, noodles, frozen foods, retort foods, cheese and roux. The above-
exemplified oil/fat-containing food can be prepared by adding, in addition to the above- described oil/fat composition, food raw materials ordinarily employed depending on the
kind ofthe food. The amount ofthe oil/fat composition ofthe present invention to be
added to the food varies depending on the kind ofthe food, but is usually 0.1 to 100%),
preferably 1 to 80%>, especially 2 to 80%>. It is preferably added in an amount of 0.1 to
50 g, preferably 0.5 to 10 g, especially 1 to 7.5 g, interms ofthe oil/fat composition,
once or several times a day.
When a food contains an oil/fat derived from its raw material, a ratio ofthe
oil/fat derived from the raw material to the oil/fat composition ofthe present invention
is preferably 95:5 to 1:99, more preferably 95:5 to 5:95, still more preferably 85:15 to 5:95, especially 40:60 to 5:95.
When the oil/fat composition ofthe present invention is mixed with another food raw material and provided as an oil/fat-containing processed food, following raw materials can be used. Examples include edible oils or fats, for example, natural animal
or vegetable oils or fats, and processed oils or fats obtained by subjecting these natural animal or vegetable oils or fats to ester exchange reaction, hydrogenation or
fractionation. Preferred examples include soybean oil, rapeseed oil, rice bran oil, corn
oil, palm oil, linseed oil, perilla oil and fish oil, and processed oils or fats thereof.
Examples of an emulsifier include various proteins such as egg protein, soybean protein
and milk protein, proteins separated therefrom or (partially) decomposed products of
these proteins; and sucrose fatty acid esters, sorbitan fatty acid esters, polyoxyethylene
sorbitan fatty acid esters, glycerin fatty acid monoesters, polyglycerin fatty acid esters,
polyglycerin condensed ricinoleate esters, glycerin organic acid fatty acid esters,
propylene glycol fatty acid esters and lecithin, and enzymatically decomposed products
thereof. Examples of a stabilizer include polysaccharide thickeners and starches such as xanthane gum, gellan gum, guar gum, carrageenan, pectin, tragacanth gum and konjac
mannan. In addition, a flavor developing agent such as salt, sugar, vinegar or seasoning,
flavoring such as spice and flavor, colorant and antioxidant such as tocopherol or natural
antioxidant component can be added.
As oil/fat-containing foods ofthe present invention, following ones are
preferred.
(1) Oil-in-water type oil/fat-containing foods
A weight ratio of oil phase to water phase is 1/99 to 90/10, preferably 10/90 to
80/20, especially 30/70 to 75/25 in terms of oil phase/water phase. The diglyceride
content in the oil phase is 60 to 100%, preferably 65 to 99%, especially 75 to 92%. The
-linolenic acid content in the fatty acid constituents of a diglyceride is 20 to 80%>,
preferably 30 to 70%>, especially 40 to 65%). The ratio of cis ω 3-unsaturated fatty
acid/(cis ω 6-unsaturated fatty acid + saturated fatty acid + trans unsaturated fatty acid)
is 1 to 6, preferably 1.2 to 5, especially 1.5 to 3. The phytosterol content is 0 to 10%, preferably 1 to 7%, especially 2 to 5%>, the emulsifier content is 0.01 to 5%, especially
0.05 to 3%, and the stabilizer content is 0.5%>, especially 0.01 o 2%. The pH is 1.0 to
7.0, preferably 2.0 to 6.0, especially 3.0 to 5.0 and it can be adjusted by an organic acid (or salt thereof) such as vinegar, lemon juice or citric acid, or an inorganic acid (or salt
thereof) such as phosphoric acid (salt thereof).
From the above-described materials, oil-in-water type oil/fat containing foods
such as dressing, mayonnaise, coffee creamer, ice cream, sauce, soup and beverage can
be prepared.
(2) Water-in-oil type oil/fat-containing foods A weight ratio of water phase to oil phase is 90/10 to 1/99, preferably 80/20 to
10/90, especially 70/30 to 35/65. The diglyceride content in the oil phase is 60 to 100%),
preferably 65 to 99%, especially 75 to 92%. The -linolenic acid content in the fatty
acid constituents of a diglyceride is 20 to 80%>, preferably 30 to 70%>, especially 40 to
65%). The ratio of cis ω 3-unsaturated fatty acid/(cis ω 6-unsaturated fatty acid +
saturated fatty acid + trans unsaturated fatty acid) is 1 to 6, preferably 1.2 to 5,
especially 1.5 to 3. The phytosterol content is 0 to 10%>, preferably 1 to 7%>, especially 2
to 5%>, and the emulsifier content is 0.01 to 5%>, especially 0.05 to 3%.
From the above-described materials, water-in-oil type oil/fat-containing foods such as margarine and spread can be prepared in a conventional manner.
(3) Pocket-size oil/fat-containing foods
The oil/fat content is 1 to 30%>, especially 1 to 20%) and the diglyceride content
in the oil/fat is 60 to 100%, preferably 65 to 99%, especially 40 to 65%. The
-linolenic acid content in the fatty acid constituents of a diglyceride is 20 to 80%>,
preferably 30 to 70%, especially 40 to 65%. The ratio of cis ω 3-unsaturated fatty
acid/(cis ω 6-unsaturated fatty acid + saturated fatty acid + trans unsaturated fatty acid)
is 1 to 6, preferably 1.2 to 5, especially 1.5 to 3. The phytosterol content is 0 to 20%,
preferably 1 to 20%, especially 2 to 15%). Carbohydrate such as sucrose, glucose,
fructose, maltose, xylitol, sorbitol, erythritol or starch is preferably added in an amount
of 40 to 99%, while a carbonating agent composed of an effervescing agent such as
sodium bicarbonate and an acidic agent such as tartaric acid, fumaric acid or citric acid
is preferably added in an amount of 0 to 20%), especially 1 to 10%. Oil/fat-containing pocket-size foods such as tablet, candy, caramel and gummy
candy can be prepared in a conventional manner by using the above-described materials.
In particular, use of a carbonating agent makes the food melty in the mouth.
(4) Bakery foods
The oil/fat content is 1 to 40%>, especially 5 to 35%) and the diglyceride content
in the oil/fat is preferably 60 to 100%, more preferably 65 to 99%, especially 75 to 92%.
The -linolenic acid content in the fatty acid constituents of a diglyceride is 20 to
80%), more preferably 30 to 70%), especially 40 to 65%. The content ratio of cis ω 3-
unsaturated fatty acid/(cis ω 6-unsaturated fatty acid + saturated fatty acid + trans
unsaturated fatty acid) is 1 to 6, preferably 1.2 to 5, especially 1.5 to 3. The phytosterol content is 0 to 20%>, preferably 1 to 20%>, especially 1 to 15%>. The flour content is 10 to
70%, with 20 to 60% being especially preferred. The bakery food is preferred to contain at least one of hen's whole egg, egg yolk and egg white, and separated or decomposed product thereof in an amount of 0 to 30%, especially 5 to 25%. The salt content is
preferably 0 to 2%, especially 0.1 to 1%. The carbohydrate content is 0 to 25%, while the baking powder content is 0 to 1%.
From these materials, bakery foods such as bread, cake, biscuit and cookie can be prepared in a conventional manner.
Examples ofthe pharmaceuticals include orally administrable preparations, e.g.,
solid preparations such as powder, granule, capsule, pill and tablet, liquid preparations
such as aqueous preparation, suspension and emulsion, and gel preparations. Such an
orally administrable agent can be prepared by adding, in addition to the oil/fat
composition, excipient, disintegrator, binder, lubricant, surfactant, alcohol, water, water-
soluble polymer, sweetening agent, taste corrigent and acidifier, each ordinarily employed according to the dosage form ofthe orally administrable preparation. The
amount ofthe oil/fat composition ofthe present invention to be added to the orally-
administrable preparation can differ with its purpose or dosage form, but addition in an
amount of 0.1 to 100%), preferably 1 to 80%o, especially 5 to 80%> is usually preferred.
As a dose, 0.1 to 50 g, preferably 0.5 to 10 g, especially 1 to 7.5 g, in terms ofthe oil/fat
composition, is preferably administered once or several portions a day.
Examples ofthe feed include livestock feed for cow, pig, fowl and sheep, feed
for small animals such as rabbit, rat and mouse, feed for fishes such as eel, porgy,
yellowtail and shrimp, and pet foods for dog, cat, bird and squirrel. Although the amount ofthe oil/fat composition ofthe present invention to be added to feed differs
depending on the using purpose ofthe feed, 1 to 30%) is usually added, with 1 to 20%>
being especially preferred.
Having generally described this invention, a further understanding can be obtained by reference to certain specific examples which are provided herein for purposes of illustration only and are not intended to be limiting unless otherwise specified.
Examples Example 1
The following oil/fat compositions were prepared.
Oil/fat Composition 1
To a mixture of 650 parts by weight of perilla oil fatty acid and 107 parts by
weight of glycerin, the immobilized lipase preparation, "Lipozyme IM" (product of
Novo Nordisk Bioindustry) was added and the resulting mixture was esterified at 40 °C
for 5 hours at 0.07 hPa, followed by the removal ofthe lipase preparation using
filtration. The resulting reaction mixture was then subjected to molecular distillation (215 °C, 0.07 hPa), followed by decoloring, washing with water and then, deodorizing at
215 °C for 2 hours, whereby Oil/fat composition 1 was obtained.
Oil/Fat Composition 2
A mixture of 400 parts by weight of linseed oil, 200 parts by weight of rapeseed
oil, 120 parts by weight of glycerin and 2 parts by weight of calcium hydroxide was
reacted at 230 °C for 0.5 hour in a nitrogen gas atmosphere. The reaction mixture was
then allowed to stand for 12 hours, followed by removal ofthe glycerin phase. After the
oil phase (oil/fat composition) was washed with a 50% aqueous solution of citric acid in an amount of 2 times the weight ofthe oil phase, an oil/fat mixture was taken out by
centrifugal separation. The mixture was subjected to molecular distillation (at 215 °C,
0.07 hPa), followed by decoloring, washing with water and then, deodorizing at 215 °C
for 2 hours, whereby Oil/fat composition 2 was obtained.
Oil/Fat Composition 3
A mixture of 650 parts by weight of rapeseed fatty acid and 107 parts by weight
of glycerin was esterified in a similar manner to that employed for Oil/fat composition
1. The resulting reaction mixture was subjected to molecular distillation (at 235 °C,
0.07 hPa), followed by washing with water and then, deodorizing at 235 °C for 1 hour,
whereby Oil/fat composition 3 was obtained.
Oil/Fat Composition 4
A mixture of 375 parts by weight of linseed oil, 375 parts by weight of safflower
oil, 250 parts by weight of glycerin and 2 parts by weight of calcium hydroxide was
reacted and purified in a similar manner to that employed for Oil/fat composition 2,
whereby Oil/fat composition 4 was obtained. Oil/fat Composition 5
A mixture of 1286 parts by weight of perilla oil and 514 parts by weight of water
was hydrolyzed by heating at 230 °C for 10 hours in an autoclave. After cooling, the
fatty acid (oil phase) decomposed by centrifugal separation was taken out. A mixture of
650 parts by weight ofthe fatty acid thus obtained by decomposition and 107 parts by
weight of glycerin was reacted and purified in a similar manner to that employed for
Oil/fat composition 1, whereby Oil/fat composition 5 was obtained.
Oil/fat Composition la
Oil/fat composition la was prepared by mixing 100 parts by weight of Oil/fat composition 1, 0.04 part by weight of tocopherol (Mix Vitamin E "MDE-6000";
product of Yashiro Co., Ltd.), 0.2 part by weight of catechin ("Sunkatol No.l"; product of Taiyo Kagaku Co., Ltd.), 0.25 part by weight of rosemary ("Herbalox type HT-0 Extract"; product of Kalsec, Inc.), 0.05 part by weight of phytosterol (product of Tama
Biochemical Co., Ltd.) and 0.1 part by weight of "THL-3" (polyglycerin fatty acid ester, HLB=1; product of Sakamoto Yakuhin Kogyo Co., Ltd.).
Oil/Fat Composition lb
Oil/fat composition lb was prepared by mixing 100 parts by weight of Oil/fat
composition 1, 0.04 part by weight of tocopherol and 0.1 part by weight of catechin. Oil/Fat Composition lc
Oil/fat composition 1 c was prepared by mixing 100 parts by weight of Oil/fat
composition 1, 0.04 part by weight of tocopherol, 0.1 part by weight of catechin, 0.02
part by weight of VCP (vitamin C palmitate; product of Roche, Ltd.) and 2.0 parts by
weight of phytosterol. Table 1
Figure imgf000020_0001
*1: measured by gas chromatography after trimethylsilylation *2: measured by gas chromatography after methylation
Example 2
A diet obtained by replacing a portion corresponding to 4% ofthe starch of a high-fat and high-sucrose diet (control diet) having the below-described composition with an oil/fat composition or oil/fat was administered to C57BL/6J male mice (a model
of dietary type II diabetes) aged seven weeks for continuous 4 weeks in a similar manner
to a usual diet. They were then dissected. The total fat weight (visceral fat weight) of perinephric, epididymal, mesenteric and retroperitoneal fat weights and a weight gain
were measured and their results are shown in Table 2.
Diet composition
Casein 20.0 %
Soybean oil 20.0
Lard 10.0
Mineral mixture 3.5
Vitamin mixture 1.0
Cellulose 4.0
Sucrose 13.0
Starch 28.5
Table 2
Figure imgf000021_0001
: Visceral fat weight and body weight gain of a rat fed with a control diet were each designated as 100.
Test to determine significant difference from control diet group (Student t-test)
*: p < 0.05
**: p < 0.01
The rats fed with a diet containing the oil/fat composition ofthe present
invention were recognized to have a significant difference from the rats fed with a
control diet and a marked reduction in the visceral fat weight and body weight were
recognized. Example 3
After Oil/fat composition 1 and soybean oil, each 2 g/day, encapsulated in a soft
capsule were administered to two groups of 8 normal adult male volunteers, respectively
for continuous 2 months, their body weight, waist circumference, visceral fat area (CT),
subcutaneous fat area (CT), blood triglyceride level, and blood plasminogen activator
inhibitor type-1 (PAI-1) level were measured.
Table 3
Figure imgf000022_0001
#: Each item before administration was designated as 100.
##: Test on significant difference between groups *: P < 0.1 **: P < 0.05
Lowering was recognized in any indexes as a result of administration ofthe soft
capsule containing Oil/fat composition 1 ofthe present invention.
Example 4: Stability against autoxidation
Oil/fat composition or oil/fat (20 g) was charged in a 50 mL sample bottle.
Without a lid, it was allowed to stand at 40 °C for 5 days and then, the peroxide value (POV) was measured (in accordance with Standard Method for the Analysis of Oils,
Fats and Derivatives 2.5.2.1 of Japan Oil Chemists' Society). From the results shown in
Table 4, it has been found that any oil/fat composition ofthe present invention exhibited
good stability against autoxidation.
Table 4
Figure imgf000023_0001
ΔPOV = POV after 5 days - initial POV
Example 5
ALA-DG synthesized from purified perilla oil (product of Ohta Oil Mill Co., Ltd.) by using immobilized lipase in accordance with the method of Birgitte, et al.
(JAOCS, 65, 905(1988)) was encapsulated into capsules, each 400 mg/capsule.
Analyzed results of compositions of glyceride and fatty acid constituents are shown in Table 5.
The intake amount of ALA-DG was set at 5 capsules/day (2 g/day).
Tests were made on thirteen normal male volunteers who were aged from 34 to
51, were a little fat (BMI > 22.0) and had a rather high serum triglyceride level. In order
to study fluctuations in lipid metabolism induced by 6-week intake of ALA-DG, the
fasting blood was collected from them before and after the intake of ALA-DG. An
oxygen intake amount, upon fasting, ofthe seven subjects who consented to this test, among the thirteen blood-collected subjects, was measured. On the day before the test,
they took the same supper having a calorie of 1300 Kcal and containing 30 g of a lipid.
The oxygen intake amount was measured after fasting for 12 hours.
Upon initiation ofthe test, the age of 13 subjects was 40.1 ± 1.7 and their BMI
(body mass index) was 25.0 ± 0.7. The age of 7 subjects who were measured for an
oxygen intake amount was 43.4 ± 2.4 and their BMI was 24.1 ± 0.5.
During these tests, subjects were instructed to have a similar meal and similar
life to that before the initiation ofthe test except for the intake of a test substance. In
conformity with Declaration of Helsinki, the tests were made under the observation of a
doctor after obtaining the approval of Clinical Test Ethics Committee of Kao
Corporation, giving sufficient explanation to the subjects and obtaining a written consent from them.
Table 5: Compositions of ALA-DG
Glycerides (%)
TG 13.4
DG 85.1
Others 1.5
Fatty acids (%)
C16:0 5.6
C18:0 1.5
C18:l 12.8
C18:2 16.4
C18:3 59.3
Method for Physical Examination
For physical examination, height, weight, waist circumference, hip circumference, subcutaneous fat thickness, and ratio of body fat were measured. As the waist circumference and hip circumference, the waist circumference just above the
navel and hip circumference in its widest zone, each in the standing position, measured in accordance by the standards of Japan Obesity Association were adopted. Thickness
of subcutaneous fat was measured at two sites, that is, the midpoint ofthe upper arm
and the below point ofthe shoulder blade in the back by using a fat-o-meter (product of
Takei Scientific Instruments Co., Ltd.) in accordance with the caliper method. The ratio
of body fat was measured at the leg by "BODY FAT ANALYZER TBF-410"
manufactured by Tanita Corporation and at the arm by a body fat analyzer "HBF-302"
manufactured by OMRON Corporation. The data were indicated by mean ± standard error. The paired t-test was
employed for determining a ratio between before and after intake of ALA-DG. In each
case, p<0.05 meant existence of a significant difference.
Measurement of Oxygen Intake Amount and Calculation of Resting Metabolic Amount
Therefrom
The subjects were laid quietly for 10 minutes and then measured for their oxygen
intake amount for 3 minutes upon resting using "METAVINE-N" manufactured by
VINE Corporation. From the value thus obtained, a resting metabolic rate was
calculated. Blood Collection and Analysis of Serum and Plasma Samples
The blood was collected from the vein at the bent side portion ofthe upper arm and the serum and plasma of it were provided for various biochemical tests. Among the
various testing items, analyzed were serum triglyceride (TG), phospholipid (PL), free fatty acid (NEFA), total cholesterol (T-cho), LDL-cho, HDL-cho, remnant lipoprotein
cholesterol (RLP-cho), remnant lipoprotein triglyceride (RLP-TG), acetoacetic acid, 3-
hydroxybutyric acid, total keton body and liver function values (GOT, GPT, y -GTP).
TG, cholesterol (cho) and PL in the VLDL fractions were also measured. • Influence of ALA-DG intake on fasting serum components
Measured results ofthe fasting serum components before and after the intake of ALA-DG are shown in Table 6. Table 6: Changes in Serum Metabolic Indexes by ALA-DG Treatment
Before treatment After treatment
Serum TG (mg/dL) 175.0 ±21.3 145.4 ±11.0
PL(mg/Dl) 236.4 ±9.6 223.8 ±8.3*
NEFA (mEq/L) 0.6 ±0.1 0.6 ±0.1
T-cho (mg/dL) 211.3 ±9.7 203.1 ± 8.0
LDL-cho (mg/dL) 131.7±8.7 124.2 ±6.9
HDL-cho (mg/dL) 51.8±5.7 49.3 ±5.1
RLP-cho (mg/dL) 7.4 ±1.0 5.8 ±0.6*
y -GTP(IU/L) 45.1 ±10.5 41.6 ±9.9
GOT (IU/L) 26.3 ± 4.8 22.2 ±3.1
GPT (IU/L) 37.3 ± 9.9 30.6 ±8.4**
Acetoacetic acid ( μ mol/L) 16.3 ±2.0 22.9 ±3.3*
3-Hydroxybutyric acid ( μ mol/L) 30.3 ±4.8 33.6 ±4.9
Total keton body ( μ mol/L) 44.8 ± 4.0 56.5 ± 7.7
VLDL-TG (mg/dL) 105.8 ±14.1 86.8 ± 8.2*
VLDL-PL (mg/dL) 35.0 ±4.3 .29.2 ±2.1
VLDL-cho (mg/Dl) 27.2 ±3.0 22.3 ±1.4
Values are means ± SE
Significantly different from before treatment, *p<0.05, ** p<0.01 The analytical results ofthe indexes related to lipid metabolism show that
serum-triglyceride was low and particularly, VLDL-triglyceride showed a significant
decrease.
No significant difference was observed in the other VLDL fraction, but VLDL-
cho and VLDL-PL showed a decrease. RLP-cho and phospholipid each showed a
significant decrease. The total keton body showed an increasing tendency but no
significant difference appeared. Acetoacetic acid showed a significant increase. Among
the liver function values, GPT showed a significant decrease.
After 6-week ALA-DG intake, no significant change in each of weight, waist, hip, thickness of subcutaneous fat and body fat ratio was recognized.
• Influence of ALA-DG intake on resting metabolic rate
A resting metabolic rate was calculated from the oxygen intake amount for 3
minutes. As a result, the resting metabolic rate after 6-week ALA-DG intake showed a significant increase by 2.9 ± 0.8 Kcal/kg/day (117.3 ± 4.6%>) (P < 0.05) compared with that before the test.
Example 6
Test was made using, as subjects, sixteen normal male volunteers from 25 to 40
years old belonging to the normal weight to obesity (class 1) judged from BMI based on
the standards ofthe Japan Obesity Association (Obesity Research 6(1), 18-28(2000)).
They were classified into a test group (eight subjects for ALA-DG group) and a control
group (the other eight subjects for LA-TG group) so that these two groups had no
significant difference in BMI before the starting ofthe test.
Upon this test, same ALA-DG with that employed in Example 5 was used. For
LA-TG, soybean oil was employed. Compositions of them are shown below in Table 7. Table 7: Compositions of experimental lipids
LA-TG ALA-DG
Glycerides (%)
TG 97.8 13.4
DG 0.4 85.1
Others 1.8 1.5
Fatty acids (%)
C16:0 10.4 5.6
C18:0 4.4 1.5
C18:l 24.5 12.8
C18:2 51.2 16.4
C18:3 7.4 59.3
Intake amount a day was set at 5 capsules ((400 mg x 5)/day).
Measurement:
Measurement was conducted for each of two groups. Physical examination and abdominal CT scanning were carried out before starting ofthe intake and 12 weeks after the starting of intake.
Method for Physical Examination
Physical examination was carried out by the same method as described in Example 5.
Abdominal CT scanning
CT scanning was conducted at the cross-section at the naval part and at a
position permitting the spleen and liver to be on the same cross-section. In accordance
with the method of Tokunaga, et al., (Int. J. Obes., 7, 437(1983)), the total fat area,
visceral fat area and subcutaneous fat area were determined from the CT image. In
accordance with the method of Katoh, et al. (Acta hepatologica Japonica, 25,
1097(1984)), a liver/spleen CT ratio was determined. For CT scanning, "X Vision
RIAL" of Toshiba Corporation was employed.
Analysis of Meal Based on the meal diary written by each ofthe subjects, intake amounts ofthe
calorie, protein, lipid and sugar and sufficiency of them relative to the recommended
requirements in accordance with the 5th edition of Recommended Dietary Allowances
for Japanese were analyzed.
The data were indicated by mean ± standard error. The paired t-test was
employed for comparison between the initial value and Week 12 after starting of intake,
while t-test was employed for determining the difference in a changing ratio between
groups. In each case, p<0.05 meant the existence of a significant difference.
During these tests, subjects were instructed to have a similar meal and similar life to that before the starting ofthe test except for the intake of a test substance. In conformity with Declaration of Helsinki, the tests were made under the observation of a doctor after obtaining the approval of Clinical Test Ethics Committee of this company, giving sufficient explanation to the subjects and obtaining a written consent ofthe subjects.
The body composition data measured before the test are shown in Table 8.
Table 8: Initial Characteristics of Subjects
LA-TG ALA-DG
Weight (Kg) 80.9 ± 3.8 78.1 ± 4.4
Height (cm) 170.5 ± 1.7 172,3 ± 1.3
BMI (Kg/m2) 27.8 ± 1.1 26.2 ± 1.3
Waist (cm) 94.0 ± 2.8 91.8 ± 3.1
Waist/Hip ratio 0.904 ± 0.018 0.902 ± 0.014
Total fat (cm2) 363.4 ± 41.4 350.9 ± 47.6
Visceral fat (cm2) 145.6 ± 20.4 152.7 ± 20.5
Subcutaneous fat (cm2) 217.8 ± 24.5 198.2 ± 28.8
Liver/Spleen CT ratio 0.85 ± 0.12 0.93 ± 0.11
Values are means ± SE Details ofthe meals for 3 days were studied twice, that is, before starting ofthe
test and during the test and intake amounts and sufficiency, relative to the recommended
dietary allowances, of calorie, protein, lipid and sugar were calculated. An average
intake amount a day during the test is shown in Table 9. It has been confirmed that
there is no significant difference between groups in the intake amount and sufficiency,
which is not shown in the table.
Table 9: Comparison of Nutrients Intake from foods between LA-TG and ALA-DG
groups LA-TG ALA-DG
Calorie (Kcal/day) 2004 ± 111 1937 ± 83
Protein (g/day) 69 ± 4.2 74 ± 4.6
Fat (g/day) 71 ± 7.7 67 ± 5.2
Sugar (g/day) 253 ± 13.5 239 ± 10.7
Values are each mean ± SE
A change in each ofthe weight, BMI, waist circumference and waist hip ratio measured after 12 weeks is shown as a relative value to the initial value of each subject set at 100 (Table 10).
Table 10: Changes in Rate of Variation in Body Indexes
LA-TG ALA-DG
12w 12w
Weight^ 100.66 ± 0.5 100.92 ± 0.6
BMI!) 100.66 ± 0.5 100.92 ± 0.6
Waist1} 100.10 ± 0.7 99.02 ± 0.5
Waist Hip ratio1} 100.54 ± 0.7 99.20 ± 0.6
Total fat1} 98.32 ± 2.5 92.36 ± 2.4#*
Visceral fat 101.40 ± 4.6 88.68 ± 4.3#*
Subcutaneous fat1} 98.18 ± 3.5 94.80 ± 3.4
Liver/Spleen CT ratio13 104.32 ± 5.2 108.09 ± 5.0
Values are means ± SE
1): Rate of variation means the percentage as the value at 0 week
Significantly different from the value at 0 week, #p<0.05, ##p<0.01 Significantly different from LA-TG subjects at 12 weeks, *p<0.05
Compared with the LA-TG group, the ALA-DG group showed an apparent
decrease in the waist and waist/hip ratio 12 weeks after starting of intake.
With regards to a change in each ofthe total fat area, visceral fat area,
subcutaneous fat area and CT ratio 12 weeks after starting of intake, no significant
difference was recognized in the LA-TG group. In the ALA-DG group, on the other
hand, a significant reduction in each ofthe total fat area and visceral fat area compared with the initial value was recognized. Compared with the LA-TG group, the ALA-DG
group showed an increase in liver/spleen CT ratio, indicating a reduction in the liver fat.
Particularly in a change ofthe visceral fat, a significant reduction was recognized in the ALA-DG group compared with the LA-TG group.
Example 7
Reductions in body weight, visceral fat weight and liver weight were measured using rats in accordance with the following method.
Animal and Breeding method
This test was made under the approval and the administration of Animal Care
Committee and Animal Ethics Committee of Kao Corporation. As an experimental
animal, C57BL/6J mice (7 week old, male, purchased from CLEA JAPAN/Tokyo) was
bred at room temperature of 23 ± 2 °C and relative humidity of 55 ± 10%o and under
illumination from 7:00 to 19:00. After they were carried in, seven days were spent for
habituation. They were weighed and classified into test groups so that average weights
of these groups would be substantially equal (n=5/group). They were maintained on
food and water ad libitum. Feeding was carried out using a Roden CAFE (product of Oriental Yeast Co., Ltd./Tokyo) and the feed was changed every 2 days. The feed intake
amount of each test group (n=5/cage/group) per 24 hours was measured once a week
and energy intake amount was determined. Under the above-described conditions, they
were bred for'4 weeks.
Test substance and Raw materials for feed
ALA-DG was prepared from perilla oil in the presence of immobilized lipase in
accordance with the method of Birgitte, et al. (JAOCS, 65, 905(1988)). Compositions of ALA-DG and a mixed oil (SR-oil) of safflower oil and rapeseed oil are shown in
Table 11.
Table 11 : Composition of Test Oils (%)
Fatty Acid SR-oila ALA-DGb
16:0 6\0 5
18:0 2.2 1.8
18:1 29.1 14.0
18:2 57.8 15.9
18:3 2.5 60.8
20:0 0.4 n.d.
20:1 0.6 n.d.
22:0 0.3 n.d.
22:1 0.2 n.d.
Others 0.9 1.8
Glycerides
MG r E 0
DG 1.1 85.2
TG 97.2 14.1
a; safflower oil : rapeseed oil = 70:30 b; -linolenic acid rich diglyceride n.d.; not detected
In SR-oil, oleic acid and linoleic acid account for 29.1%> and 57.8%),
respectively, ofthe fatty acid constituents, while in ALA-DG, -linolenic acid accounts
for 60.8%) ofthe fatty acid constituents. The DG and TG contents in the acylglycerol of ALA-DG are 85.2% and 14.1%, respectively. A ratio of 1,3 -diglyceride to 1,2-
diglyceride was about 7:3. The lard, sucrose, casein, cellulose, mineral mixture, vitamin
mixture and -potato starch were purchased from Oriental Yeast Co., Ltd., while the
safflower oil and rapeseed oil were purchased from The Nisshin Oil Mills Ltd.
Composition and energy amount ofthe feed are shown in Table 12.
Table 12: Composition of Feeds in Experiment (%>)
Ingredients LFa HFb HF+ALA-DG
1% ALA-DG 2% ALA-DG 4% ALA-DG
ALA-DGC - - 1.0 2.0 4.0
SR-oild 5.0 20.0 20.0 20.0 20.0
Lard - 10.0 10.0 10.0 10.0
Sucrose - 13.0 13.0 13.0 13.0
Casein 20.0 20.0 20.0 20.0 20.0
Cellulose 4.0 4.0 4.0 4.0 4.0
Mineral mixture e 3.5 3.5 3.5 3.5 3.5
Vitamin mixture f 1.0 1.0 1.0 1.0 1.0 -potato starch 66.5 28.5 27.5 26.5 24.5
Calorie 399.7 522.2 527.1 532.0 541.8
(Kcal/lOOg)
a; Low-fat diet b; High-fat diet c; -linolenic acid rich diglyceride d; safflower oil : rapeseed oil = 70:30 e; AIN-76 prescription f; AIN-76 prescription + choline bitartrate (20g/100g)
Low-fat feed (LF) contains therein 5%> of a lipid, while high-fat feed (HF)
contains 30% of a lipid and 13% of sucrose. Per 100 g ofthe feed, the calorie of LF is
399.7 Kcal and that of HF is 522.2 Kcal, indicating that the latter has an about 30%
higher calorie than the former. The ALA-DG added feed was prepared by adding 1%,
2% or 4%> of ALA-DG to HF. The amount was balanced with -potato starch. The feed thus prepared was divided into light-shading packages, each containing the feed for 2
days, and after nitrogen purging, these packages were stored at 4 C.
Measurement:
During the test, mice were weighed every week. Under fasting for 12 hours after
completion ofthe test, they were anesthetized with ether. They were sacrificed under
exsanguination and then anatomized. The visceral fat of each part (epididymal,
mesenteric, retroperitoneal and perinephric) and the liver were weighed.
• Body weight (Table 13)
No significant difference in the initial body weight was recognized among test
groups. In each test group, a weight increase was observed in Week 4. In the ALA-DG added group, a weight increase was suppressed compared with the HF group. In Week
4, a significant difference from the HF group was recognized at any concentration group both in weight and weight gain. The final body weight was almost similar to that ofthe LF group (no significant difference from the LF group). In each ofthe body weight and
body weight gain in Week 4, the ALA-DG-4% group showed the lowest value. In the energy intake amount during the test, no significant difference was recognized between
any two groups.
Table 13: Effects of ALA-DG on Body weight at 4 weeks in Experiment
Dietary treatment
HF + ALA-DG*
LFa HF"
ALA-DG1% ALA-DG2% ALA-DG4%
Body weight (g)
Initial 21.6 ± 1.3 21.6 ± 1.3 21.6 ± 0.9 21.6 ± 1.2 21.6 ± 1.2
Final 26.3 ± 1.2* 29.0 ± 1.9 26.4 ± 0.3* 26.6 ± 1.3* 25.9 ± 2.0"
Gain (4 weeks) 4.8 ± 0.4'** 7.4 ± 1.5 4.9 + 0.7"* 5.0 ± 0.7*** 4.3 ± 0.8***
Liver weight (g) 0.92 ± 0.05 0.99 ± 0.07 0.89 ± 0.04* 0.92 ± 0.04 0.89 ± 0.07*
Visceral-fat weight (g)
Total 0.95 ± 0.10** 1.46 ± 0.37 1.11 ± 0.18* 1.00 ± 0.15** 0.94 ± 0.16**
Epididymal 0.49 + 0.06** 0.76 ± 0.21 0.56 ± 0.12* 0.51 ± 0.08** 0.49 ± 0.10**
Mesenteric 0.32 ± 0.04* 0.41 ± 0.08 0.34 + 0.03* 0.33 ± 0.05* 0.30 ± 0.03**
Retroperitoneal 0.10 ± 0.03*** 0.24 + 0.07 0.16 + 0.05* 0.12 ± 0.02"* 0.11 ± 0.03***
Perinephric 0.04 ± 0.00 0.05 ± 0.02 0.04 + 0.01 0.04 ± 0.01 0.04 ± 0.01
Calorie (Kcal/cage/day) 55.8 ± 7.1 62.9 ± 4.2 59.4 + 5.5 57.2 ± 4.7 57.9 + 5.1
Values are means ± SD (n=5) a; Low-fat diet b; High-fat diet c; α-linolenic acid rich diglyceride
Significantly different from HF, *p<0.05, **p<0.01, *p<0.001
Figure imgf000037_0001
• Visceral fat weight and liver weight (Table 13)
In the ALA-DG-added groups, the total visceral-fat weight (l%>-added group
p<0.05, 2%-, 4%-added groups p<0.01), epididymal fat weight (l%>-added group
p<0.05, 2%>- and 4%>-added groups p<0.01), mesenteric fat weight (1%- and 2%- added
groups p<0.05, 4%-added groups p<0.01) and retroperitoneal fat weight (1%-added
group p<0.05, 2%- and 4%ι-added groups p<0.001) each showed a significantly low
value compared with those ofthe HF group. The visceral fat weight was recognized to
show a concentration-dependent decreasing tendency with an increase in the amount of
ALA-DG, and the ALA-DG-4% group showed the lowest value.
The liver weight of each of the ALA-DG- 1 % group and the ALA-DG-4% group showed a significantly low value (p<0.05) compared with that ofthe HF group, but no significant difference was recognized from the LF group.
Example 8: Oil- water separated dressing
To a mixture of wine vinegar, salt, pepper and mustard, Oil/fat composition la
ofthe present invention was added, followed by stirring, whereby an oil- water separated dressing was prepared.
parts by weight
Oil/fat composition la ofthe invention 45.0
Wine vinegar 25.0
(product of Nakano Suten Co., Ltd.)
Salt 1.25
Pepper 0.3 Mustard 0.25
Example 9: Candies
To 200 g of refined sugar, 70 parts by weight of water was added and after
dissolving the former in the latter by heating, boiling was continued to 148 °C. Then
heating was stopped. To 90 parts by weight ofthe resulting thick sugar syrup, 10 parts
by weight of Oil/fat composition lb was added. They were mixed, molded and then cut
into candies.
Example 10: Tablets
Corn starch (44 parts by weight), 40 parts by weight of crystalline cellulose, 5
parts by weight of carboxymethylcellulose calcium, 0.5 part by weight of silicic
anhydride, 0.5 part by weight of magnesium stearate and 10 parts by weight of Oil/fat composition lc were mixed. The resulting mixture was compressed into tablets, each
200 mg in weight, by a tableting machine.
Example 11 : Mayonnaise
Oil/fat composition lb ofthe invention 65.0%
Egg yolk 15.0
Vinegar (acidity: 10%) 7.0
Refined sugar 1.0
Sodium glutamate 0.4
Salt 0.3
Mustard (powder) 0.3
Thickener (xanthane gum) 0.2
Water 10.8 After stirring and mixing the above-described components other than Oil/fat
composition lb ofthe invention in a homomixer, Oil/fat composition lb was added
dropwise to the resulting mixture to preliminary emulsify the mixture. The preliminary
emulsion was homogenized further by a homomixer, whereby a mayonnaise was
prepared (pH 4.0).
Example 12: Margarine-like Spread
(Oil phase) parts by weight
Oil/fat composition lb ofthe invention 33.4
Hardened palm oil (IV=2) 4.0
Hardened soybean oil (IV=43) 2.0
Monoglyceride 0.5
Flavor 0.1
(Water phase) parts by weight
Distilled water 58.4
Skim milk 0.3
Salt 1.3
The above-described oil phase and water phase were prepared, followed by
mixing and emulsification in a homomixer. The resulting emulsion was cooled in a
conventional manner and plasticized into a margarine-like spread.
Example 13: Tablets parts by weight
Xylitol 28.4
Sorbitol 56.9
Oil/fat composition lb ofthe invention 2.5
Phytosterol 2.5
(product of Tama Biochemical Co., Ltd.)
Flavor (ginger oil) 1.2
Citric acid 3.0
Sodium bicarbonate 5.0
Colorant (turmeric powder) 0.5
After mixing the above-described raw materials, the resulting mixture was ground in a mortar. In a conventional manner, the resulting grind was compressed into tablets, each 2 g in weight, by a tableting machine (24.5 MPa, 4 seconds).
Example 14: Short Bread parts by weight
Weak flour 350
Strong flour 150
Refined sugar 150
Whole egg 125
Oil/fat composition lb ofthe invention 200
Salt 2.5 Refined sugar, salt and Oil/fat composition lb ofthe invention were put into a
bowl, followed by stirring by a Hobart mixer. The whole egg was gradually added to
the resulting mixture and they were stirred again by the Hobart mixer. A mixture of
weak flour and strong flour mixed in advance was added in three portions, followed by
stirring by the Hobart mixer. The dough thus prepared was divided into pieces, each 25
g in weight, and filled in a metal mold. After baking in an oven (160 °C, 50 minutes),
they were released from the mold and allowed to cool down, whereby short breads were
prepared.
Example 15: Brioche Parts by weight
Strong flour 100
Whole egg 50
Oil/fat composition lb ofthe invention 30
Refined sugar 15
Water 15
Yeast 5
Yeast food 0.1
Skim milk 4
Salt 2
The above-described raw materials other than Oil/fat composition lb ofthe
invention were mixed in a homomixer at a low speed for 30 seconds. Oil/fat
composition lb was then added, followed by mixing (for 5 minutes at a low speed and 22 minutes at a medium speed). For fermentation, the dough was allowed to rise at
27 °C for 30 minutes and then at low temperature of 5 °C for 15 minutes. The resulting
dough was divided into pieces, each 37 g in weight, and they were rounded like a ball.
After they were allowed to rise at 33 °C for 60 minutes for fermentation, they were
baked in an oven (at 190 °C for 9 minutes), whereby brioches were obtained.
Industrial Applicability
The oil/fat composition ofthe present invention has excellent visceral fat
burning property, body fat burning property and stability against autoxidation.
Obviously, numerous modifications and variations ofthe present invention are possible in light ofthe above teachings. It is therefore to be understood that within the
scope ofthe appended claims, the invention may be practiced otherwise than as specifically described herein
This application is based on Japanese patent application 2000-239573 filed in the Japanese Patent Office on August 8, 2000, the entire contents of which are hereby
incorporated by reference.

Claims

Claims
1. An oil/fat composition comprising 60 to 100 wt.% of a diglyceride, wherein
said diglyceride has, as fatty acid constituents thereof, 15 to 90 wt.% of an ω 3-
unsaturated fatty acid having less than 20 carbon atoms and a cis ω 3-unsaturated fatty
acid/(cis ω 6-unsaturated fatty acid + saturated fatty acid + trans unsaturated fatty acid)
at a weight ratio of 1 to 6.
2. The oil/fat composition according to claim 1, wherein said ω 3-unsaturated
fatty acid is a -linolenic acid.
3. The oil/fat composition according to claim 1 or 2, wherein said diglyceride
has, as the fatty acid constituents thereof, 10 to 60 wt.% of an ω 9-unsaturated fatty
acid.
4. The oil/fat composition according to any one of claims 1 to 3, which
comprises 65 to 99 wt.% of said diglyceride, 0.1 to 4 wt.% of a monoglyceride, 0.1 to 34.9 wt.% of a triglyceride and 1.5 % or less of a free fatty acid (salt), wherein said
diglyceride has, as fatty acid constituents thereof, 20 to 80 wt.% of a -linolenic acid, 10
to 60 wt.% of oleic acid, 2 to 50 wt.% of an ω 6-unsaturated fatty acid, 70 to 100 wt.%
of an unsaturated fatty acid and a cis ω 3-unsaturated fatty acid/(cis ω 6-unsaturated
fatty acid + saturated fatty acid + trans unsaturated fatty acid) at a weight ratio of 1.2 to
5; the triglyceride has, as a fatty acid constituent thereof, 70 to 100% of an unsaturated
fatty acid; and the content of a polyunsaturated fatty acid having at least 4 carbon-
carbon double bonds is 5 wt.% or less based on all the fatty acid constituents of the
oil/fat composition.
5. The oil/fat composition according to any one of claims 1 to 3, which
comprises 70 to 95 wt.% of said diglyceride, 0.1 to 2 wt.% of a monoglyceride, 2 to
29.9 wt.%) of a triglyceride and 1 wt.%> or less of a free fatty acid (salt), wherein said
diglyceride has, as fatty acid constituents thereof, 30 to 70 wt.% of a -linolenic acid, 10
to 50 wt.% of oleic acid, 5 to 40 wt.% of an ω 6-unsaturated fatty acid, 80 to 100 wt.%
of an unsaturated fatty acid and a cis ω 3-unsaturated fatty acid/(cis ω 6-unsaturated
fatty acid + saturated fatty acid + trans unsaturated fatty acid) at a weight ratio of 1.4 to
4; the triglyceride has, as a fatty acid constituent thereof, 80 to 100 wt.%> of an
unsaturated fatty acid; and the content of a polyunsaturated fatty acid having at least 4
carbon-carbon double bonds is 2%> or less based on all the fatty acid constituents ofthe oil/fat composition.
6. The oil/fat composition according to any one of claims 1 to 3, which
comprises 75 to 92 wt.% of said diglyceride, 0.1 to 1.5 wt.% of a monoglyceride, 6 to 24.9 wt.% of a triglyceride and 0.5 wt.% or less of a free fatty acid (salt), wherein said
diglyceride has, as fatty acid constituents thereof, 40 to 65 wt.%> of -linolenic acid, 12
to 30 wt.%) of oleic acid, 10 to 30 wt.%> of an ω 6-unsaturated fatty acid, 90 to 100
wt.%) of an unsaturated fatty acid and a cis ω 3-unsaturated fatty acid/(cis ω 6-
unsaturated fatty acid + saturated fatty acid + trans unsaturated fatty acid) at a weight
ratio of 1.5 to 3; the triglyceride has, as a fatty acid constituent thereof, 90 to 100%) of an
unsaturated fatty acid; and the content of a polyunsaturated fatty acid having at least 4
carbon-carbon double bonds is 0 based on all the fatty acid constituents ofthe oil/fat
composition.
7. The oil/fat composition according to any one of claims 1 to 6, which further
comprises a phytosterol in an amount of 0.05 wt.% or greater.
8. A food comprising the oil/fat composition as claimed in any one of Claims
l to 7.
9. A feed comprising the oil/fat composition as claimed in any one of claims 1
to 7.
10. A pharmaceutical comprising the oil/fat composition of as claimed in any
one of claims 1 to 7..
11. The food according to claim 8, which is an oil-in-water type oil/fat- containing food.
12. The food according to claim 8, which is a water-in-oil type oil/fat-
containing food.
13. The food according to claim 8, which is a pocket-size oil/fat-containing food.
14. The food according to claim 8, which is a bakery food.
15. In a method of preparing a food composition comprising a far or oil, the
improvement comprising preparing said food composition with the oil/fat composition
of claim 1.
PCT/JP2001/006777 2000-08-08 2001-08-07 Oil/fat composition WO2002011552A2 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
BRPI0113105-2A BRPI0113105B1 (en) 2000-08-08 2001-08-07 Oil / fat composition, food, feed and pharmaceutical product comprising said composition and process for preparing a food composition comprising a fat or oil
US10/343,748 US7090886B2 (en) 2000-08-08 2001-08-07 Oil/fat composition
DE60143753T DE60143753D1 (en) 2000-08-08 2001-08-07 OIL / GREASE COMPOSITION
EP01954487A EP1315424B1 (en) 2000-08-08 2001-08-07 Oil/fat composition
CA002418350A CA2418350C (en) 2000-08-08 2001-08-07 Oil/fat composition
BR0113105-2A BR0113105A (en) 2000-08-08 2001-08-07 Oil / fat composition

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2000239573 2000-08-08
JP2000-239573 2000-08-08

Publications (2)

Publication Number Publication Date
WO2002011552A2 true WO2002011552A2 (en) 2002-02-14
WO2002011552A3 WO2002011552A3 (en) 2002-04-18

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US (1) US7090886B2 (en)
EP (1) EP1315424B1 (en)
CN (1) CN1236683C (en)
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CA2418350A1 (en) 2002-02-14
CA2418350C (en) 2010-01-19
WO2002011552A3 (en) 2002-04-18
CN1236683C (en) 2006-01-18
EP1315424A2 (en) 2003-06-04
BR0113105A (en) 2003-07-08
US7090886B2 (en) 2006-08-15
BRPI0113105B1 (en) 2018-03-27
US20040052920A1 (en) 2004-03-18
DE60143753D1 (en) 2011-02-10
CN1468061A (en) 2004-01-14
EP1315424B1 (en) 2010-12-29

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