WO2001030359A1 - Cholesterol lowering and blood lipids lowering composition - Google Patents

Cholesterol lowering and blood lipids lowering composition Download PDF

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Publication number
WO2001030359A1
WO2001030359A1 PCT/SE2000/002100 SE0002100W WO0130359A1 WO 2001030359 A1 WO2001030359 A1 WO 2001030359A1 SE 0002100 W SE0002100 W SE 0002100W WO 0130359 A1 WO0130359 A1 WO 0130359A1
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WO
WIPO (PCT)
Prior art keywords
composition
fatty acids
lowering
blood lipids
esters
Prior art date
Application number
PCT/SE2000/002100
Other languages
French (fr)
Inventor
kjell SJÖBERG
Original Assignee
Triple Crown Ab
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 Triple Crown Ab filed Critical Triple Crown Ab
Priority to EP00975114A priority Critical patent/EP1227816A1/en
Priority to AU13211/01A priority patent/AU1321101A/en
Priority to US10/111,614 priority patent/US7785620B1/en
Publication of WO2001030359A1 publication Critical patent/WO2001030359A1/en

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/70Carbohydrates; Sugars; Derivatives thereof
    • A61K31/715Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
    • A61K31/716Glucans
    • A61K31/718Starch or degraded starch, e.g. amylose, amylopectin
    • 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
    • A23L33/20Reducing nutritive value; Dietetic products with reduced nutritive value
    • A23L33/21Addition of substantially indigestible substances, e.g. dietary fibres
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/21Esters, e.g. nitroglycerine, selenocyanates
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/56Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/575Compounds 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/06Antihyperlipidemics
    • 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

  • Phytosterols such as ⁇ -sitosterol and ⁇ -sitostanol and their derivatives are used in medicine
  • Sterols and/or stanols are initially mixed with :.'. oil such as fish oil and esters of shorter fatty acids and glycerol.
  • the mixture is transestcrificd in a known manner to mainly monoglycerides of fatty acids from fish oil or shorter fatty acids.
  • the concentrate can be used such, be tabletted, encapsulated or mixed with food.
  • the concentrate can also be mixed with hydroly ⁇ :! r :brcs in gel- or powder form.
  • the mixture contains all desired components for blood lipids lowering and cholesterol lowering effects.
  • the obtained mixture can be mixed into food such as bread, cakes, flakes and other or be encapsulated or tabletted.
  • the advantages besides the pure biological are that the oxygene sensitive polyunsaturated fatty acids are ⁇ tabilsed by the hydrolysed meal.
  • the manufacturing process is simple and cheap. For different applications one or more of the
  • the mixture can be kept under inert athmosph ⁇ re.
  • the obtained composition can be used as is or be mixed into various food.
  • EXAMPLE 2 50g of oil containing polyunsaturated fatty aA'.s, 25 g of oils from short chain fatty acids, 18 g of glycerol and 40 g of sterols are mixed in v. vessel under inert athmosphere and are transesterified at elevated temperatures in k'-.c.vn way. After cooling to 50-80 °C the mixture
  • the obtained composition is added to 2500 g of a gel based on hydrolysed oats fibre under good stirring.
  • the obtained composition can be used as is or be mixed into into various food.
  • the obtained composition can be used as is or mixed into various food.
  • EXAMPLE 4 500 g of fish oil, 100 g of oil of short chain fatty acids, 150 g of glycerol and 300 g of sterols
  • composition 65 g of oils of short chain fatty acids, 18 g of glycerol and 40 g of sterols are mixed in a vessel under inert athmosphere and transesterified at elevated temperature in known way. After cooling to 50-80 °C the mixture is added under good stirring to 400 g of gel based on hydrolysed oats fibre.
  • the obtained composition can be used as is, be encapsulated, tabletted
  • EXAMPLE 6 40 g of sterols are dissolved in 50 g offish oil and 40 g of a inonoglyceride in a vessel under inert athmosphere at 100 °C.
  • the composition obtained can be used as is, be encapsulated, tabletted or mixed into different food.
  • sterols 50 g are mixed with 65 g of oils of short chain fatty acids and 15 g of glycerol and
  • the obtained composition can be used as is, be

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Mycology (AREA)
  • Botany (AREA)
  • Polymers & Plastics (AREA)
  • Food Science & Technology (AREA)
  • Nutrition Science (AREA)
  • Molecular Biology (AREA)
  • Emergency Medicine (AREA)
  • Diabetes (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Organic Chemistry (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Fats And Perfumes (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)
  • Edible Oils And Fats (AREA)

Abstract

The present invention is a composition containing cholesterol lowering and blood lipids lowering components such as phytosterols in a biologically easily available form in combination with unsaturated fatty acids or esters, short chain fatty acids or esters and/or hydrolyzed flour containing β-glucan and amylodextrin; food containing such a composition and a method for manufacturing of such a composition.

Description

Patent application no 9903915-8 Cholesterol lowering and blood lipids lowering
composition. Priority date Octobe.29,1999.
CHOLESTEROL LOWERING AND BLOODL1P1DS LOWERING COMPOSITION
BACKGROUND
Phytosterols such as β-sitosterol and β-sitostanol and their derivatives are used in medicine
owing to their ability to lower total and LDL- cholesterol levels in blood. Recent research has shown that n-3 polyunsatiiratcd fatty acids present in fish oils such as eicosapentaenic acids (EPA) and docosahexaenic acids (DHA) positively effect our blood lipids (1 ). They are also building blocks in prostaglandins Further a positive effect on blood lipids has been noted by intake of shorter fatty acids (2) Finally, the importance of a daily
intake of β-glucan and amylodextrins is recommended by USDA. (3,4). These compounds
can be recovered by hydrolysis of oat meal and can be made in gelform as hydrocolloids
DESCRIPTION OF THE INVENTION In the present invention is shown how sterols and/or stanols in a biologially easily available
form has sucessfully been combined with other blood lipids lowering and cholesterol lowering
compounds such as unsaturated fatty acids or their derivatives and/ or shorter fatty acids or
derivatives of these and/or hydrolyscd fibres containing β-glucan or amylodextrines. A clear distinction between blood lipids lowering and cholesterol lowering action of these compound is not present, furthermore interactive effects may occur.
Sterols and/or stanols are initially mixed with :.'. oil such as fish oil and esters of shorter fatty acids and glycerol. The mixture is transestcrificd in a known manner to mainly monoglycerides of fatty acids from fish oil or shorter fatty acids. In this way we obtain in only one process step an entirely new combination of cholesterol lowering sterols and or stanols and good fatty acids in a concentrate, in some cases in the same molecule. The concentrate can be used such, be tabletted, encapsulated or mixed with food. The concentrate can also be mixed with hydrolyε :! r:brcs in gel- or powder form. The obtained
mixture contains all desired components for blood lipids lowering and cholesterol lowering effects. The obtained mixture can be mixed into food such as bread, cakes, flakes and other or be encapsulated or tabletted.. The advantages besides the pure biological are that the oxygene sensitive polyunsaturated fatty acids are εtabilsed by the hydrolysed meal. The manufacturing process is simple and cheap. For different applications one or more of the
components can be excluded. The present invention will be described below by non limiting
examples.
EXAMPLE 1
55 g of fishoil, 25 g of short chain fatty acids, 18 g of glycerol and 40 g of sterols are mixed
in a vessel under inert athmosphere and are tπv.'ε slerified at elevated temperatures in known way. After cooling to 50-80 °C the mixture is r .lAd to 400 g of a gel based on hydrolysed
SUBSTlTUTl SHEET (RULE 26) meal under good stirring. If desired stabilisers for unsaturated fatty acids can be added and/or
the mixture can be kept under inert athmosphεre.
The obtained composition can be used as is or be mixed into various food.
EXAMPLE 2 50g of oil containing polyunsaturated fatty aA'.s, 25 g of oils from short chain fatty acids, 18 g of glycerol and 40 g of sterols are mixed in v. vessel under inert athmosphere and are transesterified at elevated temperatures in k'-.c.vn way. After cooling to 50-80 °C the mixture
is added to 2500 g of a gel based on hydrolysed oats fibre under good stirring. The obtained composition can be used as is or be mixed into into various food.
EXAMPLE 3
55 g of an oil containing polyunsaturated fatty acids, 10 g of glycerol and 40 g of sterols are
transesterified in known way as in example 1. After cooling to 50-80 °C the mixture is added to 400 g of a gel based on hydrolysed oats fibre under good stirring.
The obtained composition can be used as is or mixed into various food.
EXAMPLE 4 500 g of fish oil, 100 g of oil of short chain fatty acids, 150 g of glycerol and 300 g of sterols
transesterified as in ex 1 The composition obtained can be used as such or mixed into different food, be encapsulated or tabletted. EXAMPLE 5
65 g of oils of short chain fatty acids, 18 g of glycerol and 40 g of sterols are mixed in a vessel under inert athmosphere and transesterified at elevated temperature in known way. After cooling to 50-80 °C the mixture is added under good stirring to 400 g of gel based on hydrolysed oats fibre. The obtained composition can be used as is, be encapsulated, tabletted
or mixed into different food.
EXAMPLE 6 40 g of sterols are dissolved in 50 g offish oil and 40 g of a inonoglyceride in a vessel under inert athmosphere at 100 °C. The composition obtained can be used as is, be encapsulated, tabletted or mixed into different food.
EXAMPLE 7
50 g of sterols are mixed with 65 g of oils of short chain fatty acids and 15 g of glycerol and
the mixture is transesterified as in ex 1. The obtained composition can be used as is, be
encapsulated, tabletted or mixed into different food.
EXAMPLE 8
20g of sterols are dissolved in 40g of monoglycerides at 85°C and added to 200g of gelbased hydrolysed oats fibre under good stirring. The composition obtained can beused as is, been
capsulated, tabletted or mixed into various food.

Claims

1. A composition containing cholesterol lowering and blood lipids lowering components in which phytosterols, mixed with esters of unsaturated fatty acids and/or esters of short chain fatty acids, are distributed in monomolecular, low associated or cluster form in hydrolysed
fibres containing β-glucan and amylodext ines.
2. A composition as in claim 1 in which the cholesterol lowering component contains
β-sitosterol and/or β-sitostanol.
3. A composition as in claim 1 in which the cholesterol lowering composition contains
β-sitosteryl esters and/or β-sitostanyl esters of polyunsaturated fatty acids.
4. A composition as in claim 1 in which the cholsterol lowering component contains
β-sitosteryl esters and/or β-sitostanyl esters of short chain fatty acids.
5. A composition as in claim 1 in which the blood lipids lowering component contains fish
oil and /or mono and diglycerides of polyunsaturated fatty acids.
6. A composition as in claim 1 in which the blood lipids lowering component contains tri-
and/or mono- and diglycerides of short chain fatty acids.
7. A composition as in claim 1 in which the blood lipids lowering component contains a
mixture offish oil and triglycerides of short chain fatty acids.
8. A composition as in claim 1 in which the blood lipids lowering and stabilising component
contains hydrolysed meal containing a soluble fibre such as β-glucan or amylodextrins.
9. Method to prepare a composition as in the claims 1 -8 in which fish oil and/or triglycerides
of short chain fatty acids are mixed with glycerol and phytosterols, transesterified at elevated temperatures at 130 - 230 °C and that the mixture obtained is spread and stabilised in a gel based on hydrolysed fibres.
10. Food containing a composition as in the claims 1 -8 in a suitable amount for a cholesterol and blood lipids lowering effect.
11. Capsule or tablet containing a composition as in claims 1-8.
REFERENCES
1. Bartram, H.P.; Gostner, A. et al. Effect of dietaiy fish oil on fecal bile acid and neutral sterol excredon in healthy volunteers. Z. Ernaehrungsv.,iss. (1998), 37(Supl. 1), 139-
141
2. Inglett,G.E.; Newrnan.R.K. Plant Foods Hum. Nutr. 1994, 45,53-61
3. Anderson, James W.; Smith, Belinda M.; Gustafson, Nansy J. Am. J. Clin. Nutr. 1994, 59(5, Suppi.), 1242-1247
4. Inglett, George E. Nutraceuticals: The key to healthier eating ChemTech. 1999, October, 38-42.
PCT/SE2000/002100 1999-10-29 2000-10-27 Cholesterol lowering and blood lipids lowering composition WO2001030359A1 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP00975114A EP1227816A1 (en) 1999-10-29 2000-10-27 Cholesterol lowering and blood lipids lowering composition
AU13211/01A AU1321101A (en) 1999-10-29 2000-10-27 Cholesterol lowering and blood lipids lowering composition
US10/111,614 US7785620B1 (en) 1999-10-29 2000-10-27 Cholesterol lowering and blood lipids lowering composition

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
SE9903915-8 1999-10-29
SE9903915A SE517769C2 (en) 1999-10-29 1999-10-29 Cholesterol and blood fat lowering composition, containing phytosterols, mixed with monoglycerides

Publications (1)

Publication Number Publication Date
WO2001030359A1 true WO2001030359A1 (en) 2001-05-03

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PCT/SE2000/002100 WO2001030359A1 (en) 1999-10-29 2000-10-27 Cholesterol lowering and blood lipids lowering composition

Country Status (5)

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US (1) US7785620B1 (en)
EP (1) EP1227816A1 (en)
AU (1) AU1321101A (en)
SE (1) SE517769C2 (en)
WO (1) WO2001030359A1 (en)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002082929A1 (en) * 2001-04-12 2002-10-24 Raisio Benecol Oy Improved edible compositions for lowering cholesterol
EP1361264A1 (en) * 2001-02-15 2003-11-12 Asahi Denka Kogyo Kabushiki Kaisha PRODUCTS CONTAINING $G(b)-GLUCAN
WO2004009093A1 (en) * 2002-07-23 2004-01-29 Nutrinova Nutrition Specialties & Food Ingredients Gmbh Cholesterol-reducing agent made of dietary fibre and cholesterol-reducing substances
EP1600062A1 (en) * 2004-05-25 2005-11-30 Cognis IP Management GmbH Oral and/or topical compositions comprising prebiotics and sterols
EP1600060A1 (en) * 2004-05-25 2005-11-30 Cognis IP Management GmbH Oral and/or topical compositions comprising prebiotics and fatty acid
EP1614357A1 (en) * 2004-07-10 2006-01-11 Cognis IP Management GmbH Dietary supplements comprising prebiotics and fatty acid
EP1983989A1 (en) * 2006-02-09 2008-10-29 National Research Council of Canada Combinations of botanical extracts for promoting cardiovascular health
US7732000B2 (en) * 2002-06-20 2010-06-08 General Mills, Inc. Food intermediate having sequestered phytosteryl esters in a polysaccharide matrix
IT201800002663A1 (en) * 2018-02-13 2019-08-13 Ciro Langella MULTIFUNCTIONAL COMPLEX FOR THE PRODUCTION OF FOOD NUTRACEUTICS, DRUGS OR COSMETICS

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6115647A (en) * 1984-06-30 1986-01-23 Asahi Denka Kogyo Kk Oil and fat food
WO1992019640A1 (en) * 1991-05-03 1992-11-12 Raision Margariini Oy A substance for lowering high cholesterol level in serum and a method for preparing the same
WO1999015546A1 (en) * 1997-09-09 1999-04-01 Raisio Benecol Ltd. Use of organic acid esters in dietary fat
WO1999025362A1 (en) * 1997-11-14 1999-05-27 Cognis Deutschland Gmbh Use of mixtures of active agents containing phytostenol for producing hypocholesteraemic preparations

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ZA72698B (en) 1972-02-03 1973-09-26 Liebenberg R W Method of preparing medicinal compositions
US4218334A (en) 1975-06-06 1980-08-19 Henkel Corporation Phytosterol blends
US4996063A (en) * 1989-06-30 1991-02-26 The United States Of America, As Represented By The Secretary Of Agriculture Method for making a soluble dietary fiber composition from oats
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
EP0756828B2 (en) * 1995-08-04 2010-09-22 N.V. Nutricia Nutritional composition containing fibres
US5883273A (en) * 1996-01-26 1999-03-16 Abbott Laboratories Polyunsaturated fatty acids and fatty acid esters free of sterols and phosphorus compounds
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.
US6149961A (en) * 1997-11-21 2000-11-21 W. K. Kellogg Institute Fat substitute formulation and methods for utilizing same
CN1267030C (en) 1998-03-24 2006-08-02 花王株式会社 Beverage products

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6115647A (en) * 1984-06-30 1986-01-23 Asahi Denka Kogyo Kk Oil and fat food
WO1992019640A1 (en) * 1991-05-03 1992-11-12 Raision Margariini Oy A substance for lowering high cholesterol level in serum and a method for preparing the same
WO1999015546A1 (en) * 1997-09-09 1999-04-01 Raisio Benecol Ltd. Use of organic acid esters in dietary fat
WO1999025362A1 (en) * 1997-11-14 1999-05-27 Cognis Deutschland Gmbh Use of mixtures of active agents containing phytostenol for producing hypocholesteraemic preparations

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
DATABASE CA [online] (COLUMBUS, OHIO, USA); ASAHI DENKA KOGYO K.K.: "Health food containing unsaturated fatty acid glycerides and plant sterols", XP002909866, accession no. STN International Database accession no. 104:167216 *
GEORGE E. INGLETT: "Nutraceuticals; The key to healthier eating. Grandma was right about eating your porridge. Three new fat substitutes provide safe and functional alternatives to fat additives in foods", CHEMTECH, October 1999 (1999-10-01), pages 38 - 42, XP002937207 *
HELENA GYLLING ET AL.: "Plant sterols in nutrition", SCANDINAVIAN JOURNAL OF NUTRITION, vol. 44, 2000, pages 155 - 157, XP002937208 *

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2002233639B2 (en) * 2001-02-15 2007-03-01 Adeka Corporation Products containing $G(b)-glucan
EP1361264A1 (en) * 2001-02-15 2003-11-12 Asahi Denka Kogyo Kabushiki Kaisha PRODUCTS CONTAINING $G(b)-GLUCAN
EP1361264A4 (en) * 2001-02-15 2005-03-16 Asahi Denka Kogyo Kk PRODUCTS CONTAINING $G(b)-GLUCAN
US8414913B2 (en) 2001-04-12 2013-04-09 Raisio Benecol Oy Edible compositions for lowering cholesterol
WO2002082929A1 (en) * 2001-04-12 2002-10-24 Raisio Benecol Oy Improved edible compositions for lowering cholesterol
US7794745B2 (en) 2001-04-12 2010-09-14 Raisio Nutrition Ltd. Edible compositions for lowering cholesterol
US8168248B2 (en) 2002-06-20 2012-05-01 General Mills, Inc. Food intermediate having sequestered phytosteryl esters in a polysaccharide matrix
US7732000B2 (en) * 2002-06-20 2010-06-08 General Mills, Inc. Food intermediate having sequestered phytosteryl esters in a polysaccharide matrix
WO2004009093A1 (en) * 2002-07-23 2004-01-29 Nutrinova Nutrition Specialties & Food Ingredients Gmbh Cholesterol-reducing agent made of dietary fibre and cholesterol-reducing substances
EP1600060A1 (en) * 2004-05-25 2005-11-30 Cognis IP Management GmbH Oral and/or topical compositions comprising prebiotics and fatty acid
WO2005115172A1 (en) * 2004-05-25 2005-12-08 Cognis Ip Management Gmbh Oral and/or topical compositions comprising prebiotics and fatty acid
WO2005115171A1 (en) * 2004-05-25 2005-12-08 Cognis Ip Management Gmbh Oral and/or topical compositions comprising prebiotics and sterols
US8329672B2 (en) 2004-05-25 2012-12-11 Cognis Ip Management Gmbh Oral and/or topical compositions comprising prebiotics and fatty acid
EP1600062A1 (en) * 2004-05-25 2005-11-30 Cognis IP Management GmbH Oral and/or topical compositions comprising prebiotics and sterols
WO2006005464A3 (en) * 2004-07-10 2006-05-04 Cognis Ip Man Gmbh Dietary supplements comprising prebiotics and fatty acid
WO2006005464A2 (en) * 2004-07-10 2006-01-19 Cognis Ip Management Gmbh Dietary supplements comprising prebiotics and fatty acid
EP1614357A1 (en) * 2004-07-10 2006-01-11 Cognis IP Management GmbH Dietary supplements comprising prebiotics and fatty acid
EP1983989A1 (en) * 2006-02-09 2008-10-29 National Research Council of Canada Combinations of botanical extracts for promoting cardiovascular health
EP1983989A4 (en) * 2006-02-09 2009-07-08 Ca Nat Research Council Combinations of botanical extracts for promoting cardiovascular health
JP2009525990A (en) * 2006-02-09 2009-07-16 ナショナル・リサーチ・カウンシル・オブ・カナダ Pharmaceutical composition
US8895079B2 (en) 2006-02-09 2014-11-25 National Research Council Of Canada Combinations of botanical extracts for promoting cardiovascular health
IT201800002663A1 (en) * 2018-02-13 2019-08-13 Ciro Langella MULTIFUNCTIONAL COMPLEX FOR THE PRODUCTION OF FOOD NUTRACEUTICS, DRUGS OR COSMETICS

Also Published As

Publication number Publication date
SE9903915D0 (en) 1999-10-29
SE517769C2 (en) 2002-07-16
US7785620B1 (en) 2010-08-31
EP1227816A1 (en) 2002-08-07
AU1321101A (en) 2001-05-08
SE9903915L (en) 2001-04-30

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