WO1999056729A1 - Cholesterol lowering composition - Google Patents

Cholesterol lowering composition Download PDF

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Publication number
WO1999056729A1
WO1999056729A1 PCT/SE1999/000721 SE9900721W WO9956729A1 WO 1999056729 A1 WO1999056729 A1 WO 1999056729A1 SE 9900721 W SE9900721 W SE 9900721W WO 9956729 A1 WO9956729 A1 WO 9956729A1
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Prior art keywords
composition
cholesterol lowering
solution
matrix
preceeding
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PCT/SE1999/000721
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French (fr)
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WO1999056729B1 (en
Inventor
kjell SJÖBERG
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Triple Crown AB
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Triple Crown AB
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First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=20411164&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=WO1999056729(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Triple Crown AB filed Critical Triple Crown AB
Priority to US09/509,281 priority Critical patent/US6491952B1/en
Priority to DK99948541T priority patent/DK1009385T4/en
Priority to AT99948541T priority patent/ATE244557T1/en
Priority to DE69909413T priority patent/DE69909413T3/en
Priority to AU43035/99A priority patent/AU4303599A/en
Priority to EP99948541A priority patent/EP1009385B2/en
Publication of WO1999056729A1 publication Critical patent/WO1999056729A1/en
Publication of WO1999056729B1 publication Critical patent/WO1999056729B1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G1/00—Cocoa; Cocoa products, e.g. chocolate; Substitutes therefor
    • A23G1/30—Cocoa products, e.g. chocolate; Substitutes therefor
    • A—HUMAN NECESSITIES
    • A21—BAKING; EDIBLE DOUGHS
    • A21D—TREATMENT OF FLOUR OR DOUGH FOR BAKING, e.g. BY ADDITION OF MATERIALS; BAKING; BAKERY PRODUCTS
    • A21D2/00—Treatment of flour or dough by adding materials thereto before or during baking
    • A21D2/08—Treatment of flour or dough by adding materials thereto before or during baking by adding organic substances
    • A21D2/14—Organic oxygen compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
    • A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
    • A23D7/005—Edible oil or fat compositions containing an aqueous phase, e.g. margarines characterised by ingredients other than fatty acid triglycerides
    • A23D7/0056—Spread compositions
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G1/00—Cocoa; Cocoa products, e.g. chocolate; Substitutes therefor
    • A23G1/30—Cocoa products, e.g. chocolate; Substitutes therefor
    • A23G1/32—Cocoa products, e.g. chocolate; Substitutes therefor characterised by the composition containing organic or inorganic compounds
    • A23G1/42—Cocoa products, e.g. chocolate; Substitutes therefor characterised by the composition containing organic or inorganic compounds containing microorganisms or enzymes; containing paramedical or dietetical agents, e.g. vitamins
    • A23G1/426—Cocoa products, e.g. chocolate; Substitutes therefor characterised by the composition containing organic or inorganic compounds containing microorganisms or enzymes; containing paramedical or dietetical agents, e.g. vitamins containing vitamins or antibiotics
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G1/00—Cocoa; Cocoa products, e.g. chocolate; Substitutes therefor
    • A23G1/30—Cocoa products, e.g. chocolate; Substitutes therefor
    • A23G1/56—Liquid products; Solid products in the form of powders, flakes or granules for making liquid products, e.g. for making chocolate milk, drinks and the products for their preparation, pastes for spreading or milk crumb
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives
    • A23L33/11—Plant sterols or derivatives thereof, e.g. phytosterols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/575—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of three or more carbon atoms, e.g. cholane, cholestane, ergosterol, sitosterol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
    • A61K9/145—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with organic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2095—Tabletting processes
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G2200/00—COCOA; 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
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G2200/00—COCOA; 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
    • A23G2200/04—COCOA; 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 vitamins, antibiotics, other medicaments
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
    • A61K9/0056—Mouth soluble or dispersible forms; Suckable, eatable, chewable coherent forms; Forms rapidly disintegrating in the mouth; Lozenges; Lollipops; Bite capsules; Baked products; Baits or other oral forms for animals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2022—Organic macromolecular compounds
    • A61K9/2063—Proteins, e.g. gelatin

Definitions

  • the present application describes a composition containing a cholesterol lowering component, as ⁇ -sitosterol and /or ⁇ -sitostanol, food containing such a composition, and a method to prepare the composition.
  • /3-sitosterol is also understood mixtures containing ⁇ -sitosterol, ⁇ -sitostanol and campesterol isolated from for instance soy or tall oil.
  • ⁇ -sitostanol is also understood fully or partly hydrogenated ⁇ -sitosterol as above.
  • sterols and stanols by simple methods can be stabilised in monomolecular, low associated or "cluster" form by distributing and immobilising a solution of high concentration or a melt of sterols and/or stanols in a matrix.
  • Sterols and/or stanols are initially dissolved in an organic phase, for instance in mono- , di- or triglycerides, fatty acids, lecithin and others preferentially at an elevated temperature.
  • the solution is then mixed with a stabilising phase, matrix, containing a high molecular material e.g. gelatin, casein, starch syrup, pectin, ethylhydroxyethylcellulose or other at an elevated temperature.
  • the mixture is then allowed to set to a solid, rubberlike or highly viscous mass.
  • the stabilising phase can also be based on solvents being solid at room temperature.
  • An alternative way to make the composition is to foam a solution of the sterols and /or stanols containing a solvent solid at room temperature possibly in the presence of a foam building component under rapid cooling.
  • the surface of sterols and/or stanols accessible to the stomach thus becomes extremely large.
  • Foaming can be done in different known ways. Some percent of ethanol can be added to the sterols and/or stanols, the mixture is melted at elevated temperatures, the alcohol evaporated in vacuo under formation of foam.
  • solutions described above can also be mixed into different food e.g. chocolate, dough/bread, jelly, mashed potatoes, butter/margarine, youghurt and others or be encapsulated or mixed into tablets.
  • 30% solution can be used directly or stored as a prefabricate after cooling as a homogenous mass.
  • the liquid highly viscous composition was immediately cast in small forms, where it solidified as a gel containing ⁇ -sitostanol in a stabilised monomolecular or low associated form.
  • composition can be used as such or be mixed into food and/or be foamed, encapsulated or made into tablets.
  • the homogenised stabilised composition was then treated as in example 1.
  • composition 30 g of ⁇ -sitostanol were dissolved in 30 g stearic acid at 130 °C on an oil bath. A few drops of ethanol were added under intensive stirring and the composition was placed under vacuum. The mass bubbled up and was allowed to solidify as a foamed material that could be mixed for instance flour, dough, mashed potatoes or other food material, encapsulated or tabletted. Alternatively the composition can be directly cooled and used as such, mixed into food, encapsulated or tabletted.
  • Ikeda I., Sugano, M., Comparison of absorption and metabolism of beta-sitosterol in rats, Atherosclerosis, 30, 227, (!978) Sugano, M., Marioka, H. and Ikeda, I., A comparison of hypocholesterolemic activity of ⁇ -sitosterol och ⁇ -sitostanol in rats, J., Nutr., 107, 2011-2019,(1977).

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Epidemiology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Botany (AREA)
  • Nutrition Science (AREA)
  • Inorganic Chemistry (AREA)
  • Microbiology (AREA)
  • Mycology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Bakery Products And Manufacturing Methods Therefor (AREA)
  • Confectionery (AREA)
  • Edible Oils And Fats (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Steroid Compounds (AREA)

Abstract

The present invention concerns a composition containing a cholesterol lowering component such as β-sitosterol and/or β-sitostanol in a monomolecular, low associated or 'cluster' form, where a melt and/or solution of the said components are distributed, immobilised and stabilised in a matrix; food containing such a composition and a method of preparing this composition.

Description

Cholesterol lowering composition.
Technical field.
The present application describes a composition containing a cholesterol lowering component, as β-sitosterol and /or β-sitostanol, food containing such a composition, and a method to prepare the composition.
Background of the invention.
A daily intake of some compounds similar to cholesterol has been shown to have a cholesterol lowering effect. Specifically this is true for β-sitosterol and the hydrogenated form/3-sitostanol (1-5).
Under /3-sitosterol is also understood mixtures containing β-sitosterol, β-sitostanol and campesterol isolated from for instance soy or tall oil. Under β-sitostanol is also understood fully or partly hydrogenated β-sitosterol as above.
It is known that sterols and stanols are compounds with a very low solubility. They also crystallise easily. Several researchers have pointed at the importance that β- sitosterol and β-sitostanol must be adminstered in a formulation giving the optimal cholesterol lowering effect in the body. In a crystalline form even after efficient micronisation and/or in suspension the effect is lower than for solutions or emulsions (6-15). Hitherto described solutions and emulsions, however, have the disadvantage being too dilute to allow a simple intake in doses nescessary of about 1.5 g/dav (16- 18).
The solubility in fat of sterols and stanols, both being alcohols, can be increased considerably by esterification with fatty acids. These esters are hydrolysed in the stomach and sterols and stanols are liberated as the initial alcohols in a concentration low enough not to allow recrystallisation. The cholesterol lowering effect in the gut is thus improved (16-20).
We have now shown that it is not necessary to esterify sterols and stanols to be able to distribute them in a sufficiently high concentration in a monomolecular, low associated or "cluster form" to reach necessary daily doses.
Description of the invention
In the present invention we show how sterols and stanols by simple methods can be stabilised in monomolecular, low associated or "cluster" form by distributing and immobilising a solution of high concentration or a melt of sterols and/or stanols in a matrix. Sterols and/or stanols are initially dissolved in an organic phase, for instance in mono- , di- or triglycerides, fatty acids, lecithin and others preferentially at an elevated temperature. The solution is then mixed with a stabilising phase, matrix, containing a high molecular material e.g. gelatin, casein, starch syrup, pectin, ethylhydroxyethylcellulose or other at an elevated temperature. The mixture is then allowed to set to a solid, rubberlike or highly viscous mass. The stabilising phase can also be based on solvents being solid at room temperature.
An alternative way to make the composition is to foam a solution of the sterols and /or stanols containing a solvent solid at room temperature possibly in the presence of a foam building component under rapid cooling. The surface of sterols and/or stanols accessible to the stomach thus becomes extremely large. Foaming can be done in different known ways. Some percent of ethanol can be added to the sterols and/or stanols, the mixture is melted at elevated temperatures, the alcohol evaporated in vacuo under formation of foam.
The solutions described above can also be mixed into different food e.g. chocolate, dough/bread, jelly, mashed potatoes, butter/margarine, youghurt and others or be encapsulated or mixed into tablets.
The special characteristics of the present innovation are also shown by the enclosed claims.
The present innovation is described below by not limiting examples, If not otherwise stated the given values are in weight or weight %.
Example 1.
30 g of β-sitostanol were dissolved in 70 g of a monoglyceride such as Dimodan RT at 90 C on a hot water bath and stirred till the stanol was completely dissolved. The
30% solution can be used directly or stored as a prefabricate after cooling as a homogenous mass.
20 g of the solution obtained were slowly added under intensive stirring to 80 g of a
35% solution of gelatin and agar 10:1 , starch syrop, sugar and aroma in water placed on a hot water bath at 65 °C.
The liquid highly viscous composition was immediately cast in small forms, where it solidified as a gel containing β-sitostanol in a stabilised monomolecular or low associated form.
The composition can be used as such or be mixed into food and/or be foamed, encapsulated or made into tablets.
Example 2.
10 g of β-sitostanol were dissolved in 10 g of Dimodan RT at 120 C on an oil bath. The solution was carefully under intensives stirring added to 80 g of a 30% solution of gelatin in water, also containing sugar and aroma, placed on a water bath of 85 C. The homogenous stabilised composition was then treated as in example 1. Example 3.
10 g of β-sitosterol were dissolved in 10 g of rapeseed oil at 120 °C on an oil bath. The solution was carefully under intensive continous stirring added to 30 g of a 30% solution of gelatin in water, containing sugar and aroma, placed on a hot water bath of 95 °C. The homogenous stabilised composition was then treated as in example 1.
Example 4.
10 g of β-sitostanol were dissolved in 10 g of rapeseed oil at at 130 C on an oil bath. The solution was carefully added under intensive continous stirring to 50 g of a 30% solution of gelatin in water, containing sugar and aroma, placed on a hot oil bath of 1 10 °C.
The homogenised stabilised composition was then treated as in example 1.
Example 5.
10 g of β-sitostanol were dissolved in 10 g of Dimodan RT at 120 C on an oil bath. In another flask 80 g of chocolatemass were melted on the same bath. The 50% solution of β-sitostanol was slowly added under continous stirring to the chocolate. The composition was directly cast in forms, where it solidified and could be used as such or mixed into food or tableted, encapsulated or foamed.
Example 6.
10 g of β-sitostanol were dissolved in 10 g of rapeseed oil at 130 °C on an oil bath. In another flask 40 g of chocolatemass were melted at 110 °C on an oil bath. The 50% solution of β-sitostanol was added under continous stirring to the chocolate. The composition was directly cast in forms where it solidified and can be used as such or mixed inte food or be tabletted, encapsulated or foamed.
Example 7.
30 g of β-sitostanol were dissolved in 30 g stearic acid at 130 °C on an oil bath. A few drops of ethanol were added under intensive stirring and the composition was placed under vacuum. The mass bubbled up and was allowed to solidify as a foamed material that could be mixed for instance flour, dough, mashed potatoes or other food material, encapsulated or tabletted. Alternatively the composition can be directly cooled and used as such, mixed into food, encapsulated or tabletted.
Example 8.
2.5 g of β-sitosterol were dissolved in 2.5 g of Dimodan ML at 80 °C. The solution was added to 1 litre of a 3% solution of sodium caseinate at 60-80 °C under strong stirring with a Turrax. After 5 minutes the emulsion was cooled to 20 C and can be used as a beverage. The emulsion can be kept in a fridge during at least 3 days. The same result is obtained using milk.
Example 9.
12.5 g of β-sitosterol were dissolved in 25 g of Dimodan ML at 60 o C. . The solution was added to 80 g of melted margarine and mixed with 125 g of flour, 175 g of oatflakes, 2.5 g of baking powder and 80 g of sugar to a dough. The mixture was baked into 25 cakes of 18-20 g each containing 0.5 g of β-sitosterol.
REFERENSES
Pollak, O.J., Reduction of blood cholesterol in man. Cirkulation, 7, 702-706, (1953) Grundy, S.M., Ahrens, E. H. Jr., and Davignon, J., The interaction of cholesterol absorption and cholesterol synthesis in man. J. Lipid Res., 10, 304,(1969). Farguhar, J. W. .and Sokolow, M., Responce of serum lipids and lipoproteins of man to beta-sitosterol and sanflower oil - Along term study, Cirkulation, 17, 890,(1956). Oster, P., Schlierf, G., Heuck, C.C., Greten, H.,Gundert-Remy, U., Haase, W. Klose, G., Nothelfer, A.,Raetzer, H., Schellenberg, B. und Schmidt-Gauk, H., Sitosterin bei familiaren HyperlipoproteinMmmie Tyo II. Eine randomisierte gekreuzte Doppelblindstudie, Dtsch. Med. Wschr., 101, 1308-1311, (1976). Grundy, S.M., Mok, H.Y.I., Effekts of low dose phytosterols on cholesterol absorption in man, "Lipoprotein metabolism". ,pll4-118 ,Ed greten, H., Berlin, Heidelberg, New York,Springer-Verlag, (1976). Miettinen, T.A., Siurala, M., Bile salts, sterols, sterol esters glycerides and fatty acids in micellar and oil phases of inerstinal contents during fat digestion in man, Z. Klin. Chem. Biochem., 9, 47-52, (1979) Kudchodkar,BJ, Horlick, L., Sodhi, H,S. Effekts of plant sterols on cholesterol metabolism in man, Atherosclerosis, 23, 239 ,(1976). Hassan, A.s., Rampone, A. J., Intestinal absorption and lymhatic transport of cholesterol and β-sitostanol in the rat, J. Lipid Res., 20, 646-653, (1979). Heinemann, T., Kullak-Ublick, G.-K., Pietruck, B., von Bergman, K., Mechanisms of action of plants sterols on inhibition of cholesterol absorption, Eur. J. Clin. Pharmacol., 40 Suppl., 50-63,(1991). Ikeda, I., Tanaka, K., Sugano, M., Vahouny, G.V., Gallo, I L,. Inhibition of cholesterol absorption in rats by plant sterols, J. Lipid Res., 29, 1573-1582, (1988) Ikeda, I., Tanaka, K., Sugano, M., Vahouny, G.V., Gallo, I L,. Discrimination between cholesterol and sitosterol for absorption in rats, J. Lipid Res., 29, 1583-1592, (1988) Ikeda, I., Tanabe, Y and Sugano, M., Effects of sitosterol och sitotanol on micellar solubility of cholesterol, J. Nutr. Sci. Vitaminol., 35, 361-369, (1989). Ikeda, I., Sugano, M., Comparison of absorption and metabolism of beta-sitosterol in rats, Atherosclerosis, 30, 227, (!978) Sugano, M., Marioka, H. and Ikeda, I., A comparison of hypocholesterolemic activity of β-sitosterol och β-sitostanol in rats, J., Nutr., 107, 2011-2019,(1977). Heinemann, T., Pietruck,B., Kullak-Ublick, G.-K., Pietruck, B., von Bergman, K.,Comparison of sitosterol and sitostanol on inhibition of intestinal cholesterol absorption, , Agents Action (Suppl), 26, 117-122, (1988). Heinemann, T., Leiss, O., B., von Bergman, K., Effects of low-dose sitotanol onserum cholesterol in patients with hypercholesterolemia, Atherosclerosis, 61, 219-223, (1986). Miettinen, T.A., Vanhanen,H., Dietary sitostanol related to absorbtion,syntesis and serum level of cholestol in different apolipoprotein e- phenotypes, Atherosclerosis, 105, 217-226, (1994). Mattson, F.,H., Volpenstein, R.,A., Erickson, B.,A., Effects of plant sterol esters on the absorption of dietary cholesterol, J. Nutr., 107, 1139-1146 (1977) Mattson, F.,H., Grundy, S.M., Crouse, J.R., Optimizing the effekt of plant sterols on cholesterol absorptionin man, Am. J. Clin. Nutr., 35, .697-700, /1982). A substance for lowering high cholesterol level in serum and method for preparing the same. Patent C07J 9/00, A61K 31/575

Claims

Claims
1. Composition containing a cholesterol lowering component such as ^-sitosterol and/or β-sitostanol in a monomolecular, low associated or "cluster" form, in which a melt and/or solution of said compounds is distributed, immobilised and stabilised in a matrix.
2. Composition as in claim 1 , in which the matrix is based on a solid or highly viscous material such as gelatin, caseine, pectin, agar, starch, starch syrop, ethylhydroxyethyl cellulose, stearic acid, chocolate mass and similar or a mixture of two or more of these.
3. Composition as in claim 1 , in which the melt and/or solution is in an organic phase.
4. Composition as in one or more of preceeding claims, in which the melt and/or solution is in an organic phase such as a monoglyceride, diglyceride, triglyceride,fatty acid, alcohol, lecithin and similar or a mixture of two or more of these.
5. Composition as in one or more of preceeding claims, in which the cholesterol lowering component includes β-sitosterol.
6. Composition as in one or more of preceeding claims,in which the cholesterol lowering component includes β-sitostanol.
7. Composition as in one or more of preceeding claims, in which the organic phase contains a monoglyceride such as Dimodan RT.
8. Composition as in one or more of preceeding claims, in which the matrix is based on a 10-50% solution of gelatin in water and if chosen taste and aroma compounds.
9. Composition as in claim 1 , in which the matrix at room temperature is a solid solvent such as stearic acid and/or a foam building agent.
10. Composition as in claim 1, in which the cholesterol lowering agent is 1-99% of the organic phase for instance Dimodan RT.
11. Food containing a composition as in one or more of claims 1-10, in an amount to ensure a cholesterol lowering effect.
12. Food as in claim 11 being butter, butter substitute, margarine, chocolate, jelly, bread, mashed potaoes, yoghurt, soup and similar.
13. Food as in claims 11-12, in which mentioned composition is included in the food in up to 60 %.
14. Procedure to manufacture a composition as in any of the claims 1-10, in which a cholesterol lowering component is melted or dissolved in an organic phase under elevated temperature, and the obtained melt or solution, before crystallising or associating in other ways, is distributed in a matrix so that mentioned component is stabilised mainly in monomolecular or low associated or "cluster" form.
15. Procedure as in claim 14 to produce a composition as in claim 9 in which the cholesterol lowering component is dissolved at an elevated temperature in a solvent solid at room temperature and is cooled or foamed under fast cooling.
16. Procedure as in claim 14 in which the elevated temperature preferably is up to 160 °C.
17. Procedure as in claim 14 in which the elevated temperature preferaby is in the interval about 60 °C to 150 °C.
18. Capsule, tablet or foam containing a composition as in claims 1-13.
PCT/SE1999/000721 1998-04-30 1999-04-30 Cholesterol lowering composition Ceased WO1999056729A1 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
US09/509,281 US6491952B1 (en) 1998-04-30 1999-04-30 Cholesterol lowering composition
DK99948541T DK1009385T4 (en) 1998-04-30 1999-04-30 Composition for lowering cholesterol levels
AT99948541T ATE244557T1 (en) 1998-04-30 1999-04-30 COMPOSITION FOR LOWERING CHOLESTEROL LEVELS
DE69909413T DE69909413T3 (en) 1998-04-30 1999-04-30 COMPOSITION FOR REDUCING THE CHOLESTEROL MIRROR
AU43035/99A AU4303599A (en) 1998-04-30 1999-04-30 Cholesterol lowering composition
EP99948541A EP1009385B2 (en) 1998-04-30 1999-04-30 Cholesterol level lowering composition

Applications Claiming Priority (2)

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SE9801536A SE512958C2 (en) 1998-04-30 1998-04-30 Cholesterol-lowering composition containing beta-sitosterol and / or beta-sitostanol and process for its preparation
SE9801536-5 1998-04-30

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WO1999056729A1 true WO1999056729A1 (en) 1999-11-11
WO1999056729B1 WO1999056729B1 (en) 1999-12-09

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AT (1) ATE244557T1 (en)
AU (1) AU4303599A (en)
DE (1) DE69909413T3 (en)
DK (1) DK1009385T4 (en)
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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1005859A1 (en) * 1998-11-30 2000-06-07 McNEIL-PPC, INC. Method for producing dispersible sterol and stanol compounds
US6123978A (en) * 1998-08-31 2000-09-26 Mcneil-Ppc, Inc. Stable salad dressings
WO2001032029A3 (en) * 1999-11-03 2001-09-20 Forbes Medi Tech Inc Compositions comprising edible oils or fats and phytosterols and/or phytostanols substantially dissolved therein
US6376481B2 (en) 1998-09-02 2002-04-23 Mcneil-Ppc, Inc. Sterol esters in tableted solid dosage forms
US6610320B2 (en) 2000-04-14 2003-08-26 Mars, Incorporated Compositions and methods for improving vascular health
US6623780B1 (en) 2002-03-26 2003-09-23 Cargill, Inc. Aqueous dispersible sterol product
US6677327B1 (en) 1999-11-24 2004-01-13 Archer-Daniels-Midland Company Phytosterol and phytostanol compositions
WO2004014141A1 (en) * 2002-07-26 2004-02-19 Unilever N.V. Phytosterols or phytostanols and their use in food products
EP1632137A1 (en) 2004-08-10 2006-03-08 Kraft Foods Holdings, Inc. Compositions and processes for water-dispersible phytosterols and phytostanols
US7306819B2 (en) 2002-06-12 2007-12-11 The Coca-Cola Company Beverages containing plant sterols
US7335389B2 (en) 2002-06-12 2008-02-26 The Coca-Cola Company Beverages containing plant sterols
WO2009099392A1 (en) * 2008-02-06 2009-08-13 Edio Healthcare Ab Compositions of phytosterols with enhanced bioavailability
US9125425B2 (en) 2010-09-22 2015-09-08 Conopco, Inc. Edible fat continuous spreads
US9610276B2 (en) 2013-06-17 2017-04-04 Kgk Synergize, Inc. Compositions and methods for glycemic control of subjects with impaired fasting glucose

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7144595B2 (en) * 2001-11-16 2006-12-05 Brandeis University Prepared foods containing triglyceride-recrystallized non-esterified phytosterols
US7329429B2 (en) * 2003-09-25 2008-02-12 Chimel Mark J Bars and confectioneries containing cocoa solids having a high cocoa polyphenol content and sterol/stanol esters and processes for their preparation
US20050181049A1 (en) * 2003-11-19 2005-08-18 Dong Liang C. Composition and method for enhancing bioavailability
ATE413817T1 (en) * 2004-01-30 2008-11-15 Unilever Nv PARTICLE PRODUCT CONTAINING PHYTOSTEROLS AND FOOD COMPOSITIONS CONTAINING THIS WHITENING AGENT
US20070026126A1 (en) * 2005-08-01 2007-02-01 Bryan Hitchcock Sterol fortified beverages
US7575768B2 (en) * 2005-09-07 2009-08-18 Brandeis University Dietary supplements and prepared foods containing triglyceride-recrystallized non-esterified phytosterols
US7601380B2 (en) * 2005-11-17 2009-10-13 Pepsico, Inc. Beverage clouding system and method
US8039025B1 (en) 2010-10-15 2011-10-18 Life Plus, LLC Methods and dosage forms for the treatment of human cancers
FI125947B (en) 2013-07-05 2016-04-29 Ravintoraisio Oy Serum cholesterol-lowering composition
US10532060B2 (en) * 2014-03-03 2020-01-14 Raisio Nutrition Ltd. Serum cholesterol lowering edible product
US11369895B2 (en) * 2017-01-20 2022-06-28 Nutech Ventures Nanoporous starch aerogels impregnated with phytosterols and methods of preparing the nanoporous starch aerogels

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1365661A (en) * 1972-02-03 1974-09-04 Liebenberg R W Prparation of medicinal and food compositions
JPS62126966A (en) * 1985-11-27 1987-06-09 Nisshin Oil Mills Ltd:The Improved instant powder composition
EP0357967A1 (en) * 1988-09-01 1990-03-14 Roecar Holdings (Netherlands Antilles) N.V. Phyto- and zoosterols and their derivatives soluble in water
DE4038385A1 (en) * 1990-12-01 1992-06-04 Roecar Holdings Nv Sitosterol and its glycoside(s) with improved bio-availability - are in the form of microemulsions using lecithin as the carrier, isopropyl-myristate as the emulsifier and isopropanol as co-emulsifier

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3881005A (en) 1973-08-13 1975-04-29 Lilly Co Eli Pharmaceutical dispersible powder of sitosterols and a method for the preparation thereof
US4218334A (en) † 1975-06-06 1980-08-19 Henkel Corporation Phytosterol blends
US5244887A (en) 1992-02-14 1993-09-14 Straub Carl D Stanols to reduce cholesterol absorption from foods and methods of preparation and use thereof
CA2091152C (en) † 1993-03-05 2005-05-03 Kirsten Westesen Solid lipid particles, particles of bioactive agents and methods for the manfuacture and use thereof
JPH06329588A (en) † 1993-05-19 1994-11-29 Riken Vitamin Co Ltd Water-dispersible monoglyceride
US6423363B1 (en) † 1997-08-22 2002-07-23 Lipton, Division Of Conopco, Inc. Aqueous dispersion
ES2222553T3 (en) † 1997-08-22 2005-02-01 Unilever N.V. FAT-BASED FOOD PRODUCT THAT INCLUDES STEROLS.
IN185730B (en) * 1998-02-19 2001-04-14 Mcneil Ppc Inc
FI109327B (en) * 1998-02-27 2002-07-15 Spice Sciences Oy Process for the preparation of a fat-like mixture of beta-sitosterol which lowers total serum and LDL cholesterol levels
BR9904796B1 (en) * 1998-03-24 2012-02-22 phytosterol-containing oil or fat composition, oil or fat composition, food product, beverage product, and cooking table oil.

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1365661A (en) * 1972-02-03 1974-09-04 Liebenberg R W Prparation of medicinal and food compositions
JPS62126966A (en) * 1985-11-27 1987-06-09 Nisshin Oil Mills Ltd:The Improved instant powder composition
EP0357967A1 (en) * 1988-09-01 1990-03-14 Roecar Holdings (Netherlands Antilles) N.V. Phyto- and zoosterols and their derivatives soluble in water
DE4038385A1 (en) * 1990-12-01 1992-06-04 Roecar Holdings Nv Sitosterol and its glycoside(s) with improved bio-availability - are in the form of microemulsions using lecithin as the carrier, isopropyl-myristate as the emulsifier and isopropanol as co-emulsifier

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Week 8728, Derwent World Patents Index; AN 87-196297, NISSHIN OIL MILLS LTD: "Instant powder compsns with improved dispersibility - contg. lecithin and sterol (deriv.)" *

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6123978A (en) * 1998-08-31 2000-09-26 Mcneil-Ppc, Inc. Stable salad dressings
US6399137B1 (en) 1998-08-31 2002-06-04 Mcneil-Ppc, Inc. Stable salad dressings
US6376481B2 (en) 1998-09-02 2002-04-23 Mcneil-Ppc, Inc. Sterol esters in tableted solid dosage forms
US6242001B1 (en) 1998-11-30 2001-06-05 Mcneil-Ppc, Inc. Method for producing dispersible sterol and stanol compounds
US6387411B2 (en) 1998-11-30 2002-05-14 Mcneil-Ppc, Inc. Method for producing dispersible sterol and stanol compounds
EP1005859A1 (en) * 1998-11-30 2000-06-07 McNEIL-PPC, INC. Method for producing dispersible sterol and stanol compounds
WO2001032029A3 (en) * 1999-11-03 2001-09-20 Forbes Medi Tech Inc Compositions comprising edible oils or fats and phytosterols and/or phytostanols substantially dissolved therein
US6677327B1 (en) 1999-11-24 2004-01-13 Archer-Daniels-Midland Company Phytosterol and phytostanol compositions
US6610320B2 (en) 2000-04-14 2003-08-26 Mars, Incorporated Compositions and methods for improving vascular health
US6623780B1 (en) 2002-03-26 2003-09-23 Cargill, Inc. Aqueous dispersible sterol product
US7306819B2 (en) 2002-06-12 2007-12-11 The Coca-Cola Company Beverages containing plant sterols
US7335389B2 (en) 2002-06-12 2008-02-26 The Coca-Cola Company Beverages containing plant sterols
WO2004014141A1 (en) * 2002-07-26 2004-02-19 Unilever N.V. Phytosterols or phytostanols and their use in food products
EP1632137A1 (en) 2004-08-10 2006-03-08 Kraft Foods Holdings, Inc. Compositions and processes for water-dispersible phytosterols and phytostanols
WO2009099392A1 (en) * 2008-02-06 2009-08-13 Edio Healthcare Ab Compositions of phytosterols with enhanced bioavailability
RU2485808C2 (en) * 2008-02-06 2013-06-27 Эдио Хэлткеар Аб Composition with phytosterols of high bioavailability
US9078464B2 (en) 2008-02-06 2015-07-14 Edio Healthcare Ab Compositions of phytosterols with enhanced bioavailability
US9125425B2 (en) 2010-09-22 2015-09-08 Conopco, Inc. Edible fat continuous spreads
US9610276B2 (en) 2013-06-17 2017-04-04 Kgk Synergize, Inc. Compositions and methods for glycemic control of subjects with impaired fasting glucose

Also Published As

Publication number Publication date
SE512958C2 (en) 2000-06-12
SE9801536D0 (en) 1998-04-30
US6491952B1 (en) 2002-12-10
DK1009385T3 (en) 2003-11-03
EP1009385B2 (en) 2007-01-03
SE9801536L (en) 1999-10-31
EP1009385A2 (en) 2000-06-21
DE69909413T2 (en) 2004-06-09
DE69909413D1 (en) 2003-08-14
WO1999056729B1 (en) 1999-12-09
EP1009385B1 (en) 2003-07-09
DK1009385T4 (en) 2007-04-23
DE69909413T3 (en) 2007-08-16
ATE244557T1 (en) 2003-07-15
AU4303599A (en) 1999-11-23

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