WO2006128465A1 - Phosphatidylserine enriched milk fractions for the formulation of functional foods - Google Patents

Phosphatidylserine enriched milk fractions for the formulation of functional foods Download PDF

Info

Publication number
WO2006128465A1
WO2006128465A1 PCT/DK2006/000303 DK2006000303W WO2006128465A1 WO 2006128465 A1 WO2006128465 A1 WO 2006128465A1 DK 2006000303 W DK2006000303 W DK 2006000303W WO 2006128465 A1 WO2006128465 A1 WO 2006128465A1
Authority
WO
WIPO (PCT)
Prior art keywords
source
nutraceutical
milk
drink
phosphatidylserine
Prior art date
Application number
PCT/DK2006/000303
Other languages
French (fr)
Inventor
Hans Burling
Ingemar Andersson
Michael Schneider
Original Assignee
Arla Foods Amba
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=36794932&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=WO2006128465(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Arla Foods Amba filed Critical Arla Foods Amba
Priority to NZ563564A priority Critical patent/NZ563564A/en
Priority to JP2008513930A priority patent/JP5455365B2/en
Priority to BRPI0610945A priority patent/BRPI0610945B1/en
Priority to AU2006254548A priority patent/AU2006254548C1/en
Priority to EP06753297.8A priority patent/EP1901620B1/en
Priority to KR1020077030710A priority patent/KR101352288B1/en
Priority to CA2611121A priority patent/CA2611121C/en
Priority to ES06753297T priority patent/ES2820337T3/en
Priority to DK06753297.8T priority patent/DK1901620T3/en
Publication of WO2006128465A1 publication Critical patent/WO2006128465A1/en

Links

Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
    • A23C9/00—Milk preparations; Milk powder or milk powder preparations
    • 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
    • A23G9/00—Frozen sweets, e.g. ice confectionery, ice-cream; Mixtures therefor
    • A23G9/32—Frozen sweets, e.g. ice confectionery, ice-cream; Mixtures therefor characterised by the composition containing organic or inorganic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
    • A23C13/00—Cream; Cream preparations; Making thereof
    • A23C13/12—Cream preparations
    • 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
    • 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—Cocoa products, e.g. chocolate; Substitutes therefor making liquid products, e.g. for making chocolate milk drinks and the products for their preparation, pastes for spreading, milk crumb
    • 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
    • A23G9/00—Frozen sweets, e.g. ice confectionery, ice-cream; Mixtures therefor
    • A23G9/32—Frozen sweets, e.g. ice confectionery, ice-cream; Mixtures therefor characterised by the composition containing organic or inorganic compounds
    • A23G9/327—Frozen sweets, e.g. ice confectionery, ice-cream; Mixtures therefor characterised by the composition containing organic or inorganic compounds characterised by the fatty product used, e.g. fat, fatty acid, fatty alcohol, their esters, lecithin, glycerides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23J—PROTEIN COMPOSITIONS FOR FOODSTUFFS; WORKING-UP PROTEINS FOR FOODSTUFFS; PHOSPHATIDE COMPOSITIONS FOR FOODSTUFFS
    • A23J7/00—Phosphatide compositions for foodstuffs, e.g. lecithin
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52—Adding ingredients
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/17—Amino acids, peptides or proteins
    • A23L33/175—Amino acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K35/00—Medicinal preparations containing materials or reaction products thereof with undetermined constitution
    • A61K35/12—Materials from mammals; Compositions comprising non-specified tissues or cells; Compositions comprising non-embryonic stem cells; Genetically modified cells
    • A61K35/20—Milk; Whey; Colostrum
    • 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
    • A23G2200/08—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 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
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs

Definitions

  • the present invention is concerned with bovine phosphatidylserine, its preparation and use.
  • Phospholipids are very common substances in the biological world. They make up the membrane in most cells in both plants and animals. These lipids are organized in double layer structures serving as barriers between the various compartments and providing the proper environment for receptors, enzymes and transport proteins. They also serve as transmitters for communication between cells. A great part of the brain is made up by phospholipids. 15 % of the human brain phospholipids pool consists of phosphatidylserine (PS). As brain ages, material is lost and replaced by inactive substances like cholesterol.
  • PS phosphatidylserine
  • PS has lately been shown great interest as an active component in nutraceutical foods for improved cognitive performance, counteraction of memory loss and as a stress release agent.
  • the literature is exemplified by article of Benton et al. Nutritional Neuroscience, Vol. 4 pp 169-178 with title "The influence of Phosphatidylserine Supplementation on Mood and Heart Rate when Faced with an Acute Stressor ".
  • PS Subchronic Phosphatidylserine
  • bovine brain was used as raw material for isolation of PS; but after the outbreak of mad cow disease (BSE) this material is not in use any more for obvious reasons.
  • PS Because of the need to activate the enzyme with calcium in these procedures, PS often ends as a scarcely dispersible Ca salt. Purity of compound can vary from 20-90 %. Another problem associated with the head group exchange procedure is small residues of phospholipase D enzyme activity, which leads to instability of PS in water-based liquid systems. An additional major problem with pure PL fractions derived as a whole is the development of very unpleasant taste in water-based systems. Because of these drawbacks, PS is marketed mostly in capsular form dissolved in oil. For the reasons given above, drink formulations of PS dispersed in water have not been successful so far.
  • Milk contains phospholipids in the milk fat globule membrane (MFGM). This membrane is organized in ordered double layer structures together with special proteins, so-called MFGM proteins.
  • the composition of the phospholipids can be determined, preferably by P 31 NMR (Spectral Service GmbH in Germany).
  • a typical composition of the PL pattern of milk is the following (P31 NMR method):
  • PC Phosphatidylcholine
  • the PL composition in milk is unique in nature due to the high contents of PS and sphingomyelin (SPH).
  • SPH is also a bioactive polar lipid in milk. It reduces the uptake of cholesterol, and is also regarded as having an anti-tumor effect in the colon.
  • the active anticarcinogenic effect is traced to the degradation product of SPH in the intestinal tract, namely ceramide.
  • Whole milk is a poor source of PS. It contains only about 27 mg of PS per litre. Skim milk contains about 10 mg / litre. Buttermilk from churning of cream contains about 130 mg of PS /litre. Buttermilk from butter oil is an even better source of PS, containing about 250 mg of PS / litre.
  • Nutraceutical is defined as any substance that is a food or part of a food and provides medical and/or health benefits, including the prevention and treatment of disease.
  • Buttermilk is defined as the serum phase after production of butter or butter oil
  • PL is an abbreviation for phospholipids
  • PS is an abbreviation for phosphatidylserine
  • SPH is an abbreviation for sphingomyelin
  • MFGM is an abbreviation for milk fat globule membrane
  • PL concentrate as used in this invention is a phospholipid concentrate derived from bovine milk.
  • High performance liquid chromatography (HPLC) with P31 NMR detector is a advanced method for determining phospholipid composition including PS after solvent extraction of dried samples
  • Trier Social Stress Test model as described by Kirschbaum, C, Pirke, KM, Hellhammer, DH, The "Trier Social Stress Test" A tool for investigating psychobiological stress responses in a laboratory setting, Neurophysiobiology, 1993, 28, p.76-81
  • Esprion 300 from DMV International is a whey protein concentrate with about 30 % protein.
  • the present invention concerns a bovine milk derived phosphatidylserine source of natural composition having excellent dispersibility and organoleptic as well as physical stability.
  • Such a source can be derived from buttermilk or the serum phase from butter oil production. It can contain more than 0.2 % PS calculated on the weight of the total solids, such as 0.2 to 10 % PS or 1.5 to 3 % PS calculated on the weight of the total solids.
  • a source of the invention can further supply sphingomyelin in an amount about twice the amount of phosphatidylserine.
  • Such a source is useful in a nutraceutical composition.
  • It can be a nutraceutical ingredient in form of a powder or liquid concentrate in dispersion or in solution.
  • nutraceutical compositions are chocolate, ice cream, drinks, o yoghurt, nutritional bars or any nutraceutical formulation.
  • nutraceutical composition in the form of a drink without problems of precipitation of active ingredient containing an amount of the source of the invention giving a drink containing more than 20 5 mg PS and more than 40 mg SPH per serving, such as 20 mg to 500 mg PS and 40 mg to1500 mg SPH per serving.
  • the daily serving is usually 20 to 1000 ml or 100 to 250 ml.
  • the nutraceutical composition can also be formulated for intake in solid foods giving 20 mg to 500 mg PS and 40 mg to1500 mg SPH per unit or dose.
  • a nutraceutical composition can be based on milk or milk derived drinks like drinking yoghurt or ordinary yoghurt, any other type of drink, including water, o acid fruit juice or similar fruit flavoured drinks having a pH in the range of 2 to
  • the invention also relates to a process for the preparation of a bovine milk derived phosphotidylserine source from serum from production of butteroil comprising concentrating ordinary cream by centrifugation, whereafter the resulting emulsion is broken in a homogenizer, the serum phase is collected, fat-separated and treated by ultrafiltration including diafiltration and finally spray-dried.
  • Such a process can give a milk PL concentrate in which the phospholipid fraction comprises more than 75 % of total lipids in the concentrate.
  • the bovine milk derived phosphotidylserine source is also obtainable from the retentate from microfiltration of whey after defattening.
  • cream for butteroil production is thus concentrated by centrifugation to a cream containing about 80 % of fat.
  • a concentrated butter serum or buttermilk is obtained together with butteroil.
  • the buttermilk so obtained is continuously fat-separated in the process, giving a serum containing about 70 - 80 % of PL of total lipids in the serum.
  • the serum is cooled and ultrafiltered to reduce the lactose and ash contents, and optionally by diafiltration to a retentate with about 17 % PL of total lipids, and in particular about 2.0-2.5 % of PS in total solids.
  • This concentrate is finally spray-dried.
  • Phospholipids 16-19 (in particular about 2 % of PS and 5 % of sphingomyelin) Protein 55-60
  • PS addition was calculated to give a dose of 100 mg of PS for a 200 ml serving of the skim milk based drink.
  • the milk with added PS material was heated to 75 0 C in a jacketed tank and held at the final temperature for 10 min.
  • the dispersion was homogenized in two steps, 40 and 160 bars, respectively, and UHT (ultra high temperature) treated at 142 0 C for 6 s. After cooling, the product was packed in 500 ml sterile flasks and stored at 8 0 C for three months.
  • the milk was tested for taste and PS content (P31 NMR) after one week; 1 month; two and three months.
  • the milk-added PS 20 and PS 60 were physically unstable. Already after one week, 70 % of the PS had precipitated and settled at the bottom of the flasks. The drink made with PS from the source of the invention was found to be chemically stable throughout the test period and showed no precipitation.
  • the PS 20 sample had acquired an unpleasant off- taste typical for soya that made the milk almost undrinkable.
  • the taste of the PS 60 sample was more stable during the test period.
  • only the buttermilk derived PS according to the invention was long term physically stable giving no precipitation of active compound.
  • a test drink containing about 300 mg of phosphatidylserine per dose or serving of 250 ml was formulated using the milk PL concentrate produced in example 2. About 13,5 g milk PL powder was used to obtain the desired phosphatidylserine dose for a serving volume of 250 ml. The drink was used for clinical trial on Endocrine, Autonomic and Psychological parameters according to the Trier Social Stress Test model (TSST). The investigation was made at Institute Daacro / Diagnostic assessment and clinical research organization in Trier, Germany under the leadership of Dr Juliane Hellhammer.
  • TSST Trier Social Stress Test model
  • a placebo drink was made on skim milk powder and butter oil.
  • the drinks were homogenized at 50 bars and heat-treated at 143 deg. C for 4 s.
  • the formulations were flavoured by a vanilla extract and sweetened by addition of sucralose.
  • the lactose was adjusted in the test drink to contain the same content as the placebo.
  • the placebo drink contained almost no phospholipids, which was ascertained after analysis. Both test and placebo contained were thus equivalent in relation to lipids (1 ,3 %), protein (3,2 %) and lactose (4,4 %).
  • test sample and placebo were perfectly stable on storage for at least 4 months and created no off-tastes.
  • the clinical trial comprised in total 46 patients in a double blind arrangement.
  • the test and placebo drinks were consumed in a controlled way for three weeks, where after the patients were exposed to the stress test TSST / Trier Social Stress Test. Both physiological, endocrine and cognitive parameters as memory, mood / stress were measured and compared between the groups.
  • the cholesterol (LDL) was significantly reduced by about 10 % in the blood serum of the test group in comparison with the placebo group.
  • the HDL value was not influenced.
  • Milk chocolate added milk PL concentrate was manufactured according to the following recipe giving a batch of 100 kg finished product.
  • Ice cream was made according to the following recipe giving a batch of 100 kg.
  • Esprion 300 (whey protein concentrate) 0.67
  • a normal daily portion of ice cream is 75 g.
  • At 4.33 % milk PL powder with 2.2 % PS the daily amount of PS is 70 mg (160 mg SPH).
  • the product was comparable to reference both according to taste and stability. The amount of emulsifier could be reduced significantly in the test product.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Mycology (AREA)
  • Inorganic Chemistry (AREA)
  • Biochemistry (AREA)
  • Cell Biology (AREA)
  • Epidemiology (AREA)
  • Biomedical Technology (AREA)
  • Biotechnology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Developmental Biology & Embryology (AREA)
  • Immunology (AREA)
  • Virology (AREA)
  • Zoology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Botany (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Dairy Products (AREA)
  • Non-Alcoholic Beverages (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Confectionery (AREA)

Abstract

Disclosed is a bovine milk derived phosphatidylserine source of natural composition having excellent dispersibility and organoleptic as well as physical stability. The source is usefull in neutraceutical in powder, liquid or dispersion form. The source can be prepared from serum from butter oil production or from the retentate from microfiltration of whey for defatting purposes.

Description

Phosphatϊdylserine enriched milk fractions for the formulation of functional foods
The present invention is concerned with bovine phosphatidylserine, its preparation and use.
Phospholipids (PL) are very common substances in the biological world. They make up the membrane in most cells in both plants and animals. These lipids are organized in double layer structures serving as barriers between the various compartments and providing the proper environment for receptors, enzymes and transport proteins. They also serve as transmitters for communication between cells. A great part of the brain is made up by phospholipids. 15 % of the human brain phospholipids pool consists of phosphatidylserine (PS). As brain ages, material is lost and replaced by inactive substances like cholesterol.
PS has lately been shown great interest as an active component in nutraceutical foods for improved cognitive performance, counteraction of memory loss and as a stress release agent. The literature is exemplified by article of Benton et al. Nutritional Neuroscience, Vol. 4 pp 169-178 with title "The influence of Phosphatidylserine Supplementation on Mood and Heart Rate when Faced with an Acute Stressor ".
Trials have been performed over the years with significant positive results of intake of PS on stress and cognitive performance, see for example Arjan Blokland et al. "Cognition-Enhancing Properties of Subchronic Phosphatidylserine (PS) Treatment in Middle-Aged Rats: Comparison of Bovine Cortex PS With Egg PS and Soybean PS" in Nutrition Vol. 15, No. 10, PS can be used as nutraceutical and introduced in various food formulations, drinks, tablets and different kind of bars containing a concentrate of health beneficial ingredients.
Historically, bovine brain was used as raw material for isolation of PS; but after the outbreak of mad cow disease (BSE) this material is not in use any more for obvious reasons.
During the last few years a semi-synthetic variant derived from soya lecithin has been developed and marketed by companies like Lucas Meyer GmbH /
Degussa, Enzymotec, Chemi and Lipogen. We refer to WO 2005/027822.
The principal procedure used by all mentioned manufacturers of PS is as far as we know making head group exchange of the phospholipids in the substrate, e.g. exchanging the choline group in phosphatidyl choline for serine using phospholipase D as active enzyme for the reaction to occur.
Because of the need to activate the enzyme with calcium in these procedures, PS often ends as a scarcely dispersible Ca salt. Purity of compound can vary from 20-90 %. Another problem associated with the head group exchange procedure is small residues of phospholipase D enzyme activity, which leads to instability of PS in water-based liquid systems. An additional major problem with pure PL fractions derived as a whole is the development of very unpleasant taste in water-based systems. Because of these drawbacks, PS is marketed mostly in capsular form dissolved in oil. For the reasons given above, drink formulations of PS dispersed in water have not been successful so far.
Another problem in relation to marketing is the origin of PS. Head group exchanged PS is not of natural origin. It is in fact a semi-synthetic substance having all the restrictions imposed by the public health authorities for use in human food products. In order to solve the problems described above, a new natural source of PS was searched for.
Milk contains phospholipids in the milk fat globule membrane (MFGM). This membrane is organized in ordered double layer structures together with special proteins, so-called MFGM proteins.
Special MFGM fragments originating from the golgi in the udder and from MFGM material ripped off the fat globules are present in skim milk.
After performing a solvent extraction procedure, the composition of the phospholipids can be determined, preferably by P 31 NMR (Spectral Service GmbH in Germany).
A typical composition of the PL pattern of milk is the following (P31 NMR method):
Molar percentage
Phosphatidylcholine (PC) 27
Phosphatidylinositol (Pl) 7
Phosphatidylserine (PS) 13
Sphingomyelin (SPH) 25
Phosphatidylethanolamine (PE) 27
Others 1 The PL composition in milk is unique in nature due to the high contents of PS and sphingomyelin (SPH).
SPH is also a bioactive polar lipid in milk. It reduces the uptake of cholesterol, and is also regarded as having an anti-tumor effect in the colon. The active anticarcinogenic effect is traced to the degradation product of SPH in the intestinal tract, namely ceramide. We refer to Vesper et al. (1999) Sphingolipids in food and the emerging importance of sphingolipids to nutrition, J. Nutr. 129: p.1239 -1250.
Whole milk is a poor source of PS. It contains only about 27 mg of PS per litre. Skim milk contains about 10 mg / litre. Buttermilk from churning of cream contains about 130 mg of PS /litre. Buttermilk from butter oil is an even better source of PS, containing about 250 mg of PS / litre.
Definitions
The following terms used in the specification has the following meaning:
Nutraceutical is defined as any substance that is a food or part of a food and provides medical and/or health benefits, including the prevention and treatment of disease.
Buttermilk is defined as the serum phase after production of butter or butter oil
PL is an abbreviation for phospholipids
PS is an abbreviation for phosphatidylserine SPH is an abbreviation for sphingomyelin
MFGM is an abbreviation for milk fat globule membrane
PL concentrate as used in this invention is a phospholipid concentrate derived from bovine milk.
High performance liquid chromatography (HPLC) with P31 NMR detector is a advanced method for determining phospholipid composition including PS after solvent extraction of dried samples
Trier Social Stress Test model (TSST) as described by Kirschbaum, C, Pirke, KM, Hellhammer, DH, The "Trier Social Stress Test " A tool for investigating psychobiological stress responses in a laboratory setting, Neurophysiobiology, 1993, 28, p.76-81
Esprion 300 from DMV International is a whey protein concentrate with about 30 % protein.
Description of the invention
The present invention concerns a bovine milk derived phosphatidylserine source of natural composition having excellent dispersibility and organoleptic as well as physical stability.
Such a source can be derived from buttermilk or the serum phase from butter oil production. It can contain more than 0.2 % PS calculated on the weight of the total solids, such as 0.2 to 10 % PS or 1.5 to 3 % PS calculated on the weight of the total solids. A source of the invention can further supply sphingomyelin in an amount about twice the amount of phosphatidylserine.
Such a source is useful in a nutraceutical composition.
5
It can be a nutraceutical ingredient in form of a powder or liquid concentrate in dispersion or in solution.
Examples of nutraceutical compositions are chocolate, ice cream, drinks, o yoghurt, nutritional bars or any nutraceutical formulation.
Especially it is possible to provide a nutraceutical composition in the form of a drink without problems of precipitation of active ingredient containing an amount of the source of the invention giving a drink containing more than 20 5 mg PS and more than 40 mg SPH per serving, such as 20 mg to 500 mg PS and 40 mg to1500 mg SPH per serving.
The daily serving is usually 20 to 1000 ml or 100 to 250 ml.
0 The nutraceutical composition can also be formulated for intake in solid foods giving 20 mg to 500 mg PS and 40 mg to1500 mg SPH per unit or dose.
All values between 20 mg and 500 mg PS and 40 and 1500 SPH can be used. There are no specific limits. However the effect of less than 20 mg PS 5 and 40 mg SPH a day will be difficult to measure. More than 500 mg PS and 1500 mg SPH a day will not be harmful to health.
A nutraceutical composition can be based on milk or milk derived drinks like drinking yoghurt or ordinary yoghurt, any other type of drink, including water, o acid fruit juice or similar fruit flavoured drinks having a pH in the range of 2 to
8. The invention also relates to a process for the preparation of a bovine milk derived phosphotidylserine source from serum from production of butteroil comprising concentrating ordinary cream by centrifugation, whereafter the resulting emulsion is broken in a homogenizer, the serum phase is collected, fat-separated and treated by ultrafiltration including diafiltration and finally spray-dried.
Such a process can give a milk PL concentrate in which the phospholipid fraction comprises more than 75 % of total lipids in the concentrate.
In such a process ordinary fat content of the cream is concentrated from about 40 % to about 80%. The higher the fat concentration is in the cream before phase inversion the higher the PL content including phospahatidylserine in the serum phase.
The bovine milk derived phosphotidylserine source is also obtainable from the retentate from microfiltration of whey after defattening.
In order to obtain a powder containing high contents of primarily PS, cream for butteroil production is thus concentrated by centrifugation to a cream containing about 80 % of fat. After breaking the emulsion by high shearing, a concentrated butter serum or buttermilk is obtained together with butteroil. The buttermilk so obtained is continuously fat-separated in the process, giving a serum containing about 70 - 80 % of PL of total lipids in the serum. After this the serum is cooled and ultrafiltered to reduce the lactose and ash contents, and optionally by diafiltration to a retentate with about 17 % PL of total lipids, and in particular about 2.0-2.5 % of PS in total solids. This concentrate is finally spray-dried. By following this procedure a good source of natural PS has been obtained with the following typical overall composition:
(%) Total lipids 21-25
Phospholipids 16-19 (in particular about 2 % of PS and 5 % of sphingomyelin) Protein 55-60
Lactose 6-9
Ash 6
Surprisingly, we found that when adding the material specified above to a drink base like water or skim milk, giving 100 mg of PS per 200 ml serving, we obtained a very efficient source of PS with no precipitation of PS and no deterioration of taste during long-term storage at refrigerator temperature.
Examples
Example 1
Effect of the source of the invention compared with soy PS products modified by head-group exchange on the market
Three batches of 40 litres of skim milk stored in jacketed tanks were added with three different powders containing PS from different sources, namely:
• Milk PL concentrate according to invention of buttermilk origin containing 2.0 % of PS • "PS 20" from Enzymotec in Israel containing 21 % of PS. PS product from head group exchanged soya lecithin.
• Ditto "PS 60" from Enzymotec, manufactured according to the same principle as "PS 20", containing 62 % of PS.
PS addition was calculated to give a dose of 100 mg of PS for a 200 ml serving of the skim milk based drink.
The milk with added PS material was heated to 75 0C in a jacketed tank and held at the final temperature for 10 min.
The dispersion was homogenized in two steps, 40 and 160 bars, respectively, and UHT (ultra high temperature) treated at 142 0C for 6 s. After cooling, the product was packed in 500 ml sterile flasks and stored at 8 0C for three months.
The milk was tested for taste and PS content (P31 NMR) after one week; 1 month; two and three months.
The conclusion of the test was that the milk-added special fraction of buttermilk was physically and organoleptically stable.
The milk-added PS 20 and PS 60 were physically unstable. Already after one week, 70 % of the PS had precipitated and settled at the bottom of the flasks. The drink made with PS from the source of the invention was found to be chemically stable throughout the test period and showed no precipitation.
As to organoleptic quality, the PS 20 sample had acquired an unpleasant off- taste typical for soya that made the milk almost undrinkable. The taste of the PS 60 sample was more stable during the test period. In conclusion, according to the manufacturing procedure used, only the buttermilk derived PS according to the invention was long term physically stable giving no precipitation of active compound.
Example 2
240 metric tons of cream with 40 % fat content was concentrated at 11 ,5 m3/h at 70°C in a centrifugal separator to give about 80 % fat cream. The concentrated cream was in the next step phase inversed in a homogenizer and the serum phase, enriched in phospholipids, was removed at 1300 liter/h in a two-stage separation procedure and cooled to about 4°C. After ultrafiltration and drying of the serum phase (buttermilk) about 1 ,2 metric tons of milk PL concentrate was obtained with high proportion of PL in relation to total lipids, i.e.19 % PL with a total lipids content of 23,3 %. The composition of milk PL concentrate in more detail is described in the table below:
(%)
Protein (Nx6.38, Kjeldahl) 58.5
Lactose 6.6
Ash 5.3
Moisture 3.5
Total lipids 23.3
Total phospholipids 19,1
- Sphingomyelin 5.1
- Phosphatidylcholine 5.4
- Phosphatidylethanolamine 4.3
- Phosphatidylserine 2.3
- Phosphatidylinositol 1.5
Total ceramides 1.3
Gangliosides 0.59
Cholesterol 0.27
Triglycerides appr. 3
Example 3
Formulation and comparison and clinical trial
A test drink containing about 300 mg of phosphatidylserine per dose or serving of 250 ml was formulated using the milk PL concentrate produced in example 2. About 13,5 g milk PL powder was used to obtain the desired phosphatidylserine dose for a serving volume of 250 ml. The drink was used for clinical trial on Endocrine, Autonomic and Psychological parameters according to the Trier Social Stress Test model (TSST). The investigation was made at Institute Daacro / Diagnostic assessment and clinical research organization in Trier, Germany under the leadership of Dr Juliane Hellhammer.
A placebo drink was made on skim milk powder and butter oil. The drinks were homogenized at 50 bars and heat-treated at 143 deg. C for 4 s. The formulations were flavoured by a vanilla extract and sweetened by addition of sucralose. The lactose was adjusted in the test drink to contain the same content as the placebo. The placebo drink contained almost no phospholipids, which was ascertained after analysis. Both test and placebo contained were thus equivalent in relation to lipids (1 ,3 %), protein (3,2 %) and lactose (4,4 %).
Both test sample and placebo were perfectly stable on storage for at least 4 months and created no off-tastes.
The clinical trial comprised in total 46 patients in a double blind arrangement. The test and placebo drinks were consumed in a controlled way for three weeks, where after the patients were exposed to the stress test TSST / Trier Social Stress Test. Both physiological, endocrine and cognitive parameters as memory, mood / stress were measured and compared between the groups.
Result of clinical test:
The following summary was given from the evaluation of trial:
Taken together the results of the present study suggest that intake of 13,5 g milk PL powder as specified above (i.e. an additive of the invention) in a drink formulation give strong indications of enhancing working memory performance while dampening the physiological and endocrine stress responses. The contents of serum and saliva Cortisol levels were e.g. significantly lowered in the test group.
In addition it was noted that the cholesterol (LDL) was significantly reduced by about 10 % in the blood serum of the test group in comparison with the placebo group. The HDL value was not influenced.
Example 4
Milk chocolate formulation
Milk chocolate added milk PL concentrate was manufactured according to the following recipe giving a batch of 100 kg finished product.
Quantity (kg)
Sugar 39.00
Cocoa mass 16.50 Cocoa butter 18.50
Lactose 4.00
Milk powder 17.50
Milk PL powder 4.50
Vanillin 0.03
The product was physically and organoleptically fully comparable with reference without milk PL. A daily portion of 100 g of chocolate would provide 100 mg of PS ( plus 160 mg SPH ) Example 5
Ice cream formulation
Ice cream was made according to the following recipe giving a batch of 100 kg.
Quantity (kg)
Cream (40 % fat) 25.00
SMP (Skim milk powder) 3.62
Esprion 300 (whey protein concentrate) 0.67
Sugar 9.00
Fructose syrup 9.00
Emulsifier (LBG) 0.12
Guar gum 0.08
Milk PL powder 4.33
Water to 100
A normal daily portion of ice cream is 75 g. At 4.33 % milk PL powder with 2.2 % PS the daily amount of PS is 70 mg (160 mg SPH). The product was comparable to reference both according to taste and stability. The amount of emulsifier could be reduced significantly in the test product.

Claims

Claims:
1. A bovine milk derived phosphatidylserine source of natural composition having excellent dispersibility and organoleptic as well as physical stability.
2. A source of claim 1 derived from buttermilk or the serum phase from butter oil production.
3. A source of claim 1 containing more than 0.2 % PS calculated on the weight of the total solids.
4. A source of claim 1 containing 0.2 to 10 % PS calculated on the weight of the total solids.
5. A source of claim 1 containing 1.5 to 3 % PS calculated on the weight of the total solids.
6. A source of claim 1 supplying sphingomyelin in an amount about twice the amount of phosphatidylserine.
7. A nutraceutical composition containing a nutraceutical ingredient in the form of a source of claim 1.
8. A nutraceutical composition claim 7 in the form of chocolate, ice cream, a drink, a yoghurt, nutritional bars or any nutraceutical formulation.
9. A nutraceutical compostion of claim 8 in the form of a drink containing an amount of the source of claim 1 giving a drink containing more than 20 mg PS and more than 40 mg SPH per serving.
10. A nutraceutical composition of claim 9 in the form of a drink containing an amount of the source of claim 1 giving a drink containing 20 mg to 500 mg PS and 40 mg to1500 mg SPH per serving.
11. A nutraceutical compostion of claim 10, where the daily serving is 20 to 1000 ml.
12. A nutraceutical composition of claim 11 , where the daily serving is 100 to 250 ml.
13. A nutraceutical composition of claim 8 for intake as solid giving 20 mg to 500 mg PS and 40 mg to1500 mg SPH per unit or dose.
14. A nutraceutical composition of claim 6 based on milk.
15. A nutraceutical compostion of claim 6 based on another type of drink, including water, acid fruit juice or similar fruit flavoured drinks having a pH in the range of 2 to 8.
16. A process for the preparation of a source of claim 1 from serum from production of butter oil comprising concentrating ordinary cream by centrifugation, whereafter the resulting emulsion is broken in a homogenizer, the serum phase is collected, fat separated and treated by ultrafiltration including diafiltration and finally spray-dried.
17. A process according to 16 giving a milk PL concentrate in which the phospholipid fraction comprises more than 75 % of total lipids in the concentrate.
18. A process of claim 16 where the ordinary fat content of the cream is concentrated from about 40 % to about 80%.
19. A source of claim 1 obtainable by the process of claim 16.
20. A source of claim 1 obtainable from the retentate from microfiltration of whey for defatting purposes.
PCT/DK2006/000303 2005-05-31 2006-05-31 Phosphatidylserine enriched milk fractions for the formulation of functional foods WO2006128465A1 (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
NZ563564A NZ563564A (en) 2005-05-31 2006-05-31 Phosphatidylserine enriched milk fractons for the formulation of functional foods
JP2008513930A JP5455365B2 (en) 2005-05-31 2006-05-31 Phosphatidylserine-enriched milk fraction for the production of functional foods
BRPI0610945A BRPI0610945B1 (en) 2005-05-31 2006-05-31 Process for the preparation of a source of phosphatidylserine derived from bovine milk, source and nutraceutical composition comprising the same”
AU2006254548A AU2006254548C1 (en) 2005-05-31 2006-05-31 Phosphatidylserine enriched milk fractions for the formulation of functional foods
EP06753297.8A EP1901620B1 (en) 2005-05-31 2006-05-31 Phosphatidylserine enriched milk fractions for the formulation of functional foods
KR1020077030710A KR101352288B1 (en) 2005-05-31 2006-05-31 Phosphatidylserine enriched milk fractions for the formulation of functional foods
CA2611121A CA2611121C (en) 2005-05-31 2006-05-31 Phosphatidylserine enriched milk fractions for the formulation of functional foods
ES06753297T ES2820337T3 (en) 2005-05-31 2006-05-31 Phosphatidylserine fortified milk fractions for the formulation of functional foods
DK06753297.8T DK1901620T3 (en) 2005-05-31 2006-05-31 Phosphatidylserine-enriched milk fractions for the formulation of functional foods

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US68552705P 2005-05-31 2005-05-31
US60/685,527 2005-05-31

Publications (1)

Publication Number Publication Date
WO2006128465A1 true WO2006128465A1 (en) 2006-12-07

Family

ID=36794932

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/DK2006/000303 WO2006128465A1 (en) 2005-05-31 2006-05-31 Phosphatidylserine enriched milk fractions for the formulation of functional foods

Country Status (14)

Country Link
US (2) US20060280779A1 (en)
EP (2) EP2308324A1 (en)
JP (2) JP5455365B2 (en)
KR (1) KR101352288B1 (en)
AR (1) AR057042A1 (en)
AU (1) AU2006254548C1 (en)
BR (1) BRPI0610945B1 (en)
CA (1) CA2611121C (en)
DK (1) DK1901620T3 (en)
ES (1) ES2820337T3 (en)
NZ (1) NZ563564A (en)
PT (1) PT1901620T (en)
RU (1) RU2420083C2 (en)
WO (1) WO2006128465A1 (en)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007089535A (en) * 2005-09-30 2007-04-12 Snow Brand Milk Prod Co Ltd Powder highly containing compound lipid derived from milk
WO2009110205A1 (en) * 2008-03-04 2009-09-11 ナガセケムテックス株式会社 Agent for increasing the quantity of hyaluronic acid
JP2009256331A (en) * 2008-03-25 2009-11-05 Nagase Chemtex Corp Agent for preventing, alleviating or treating hyperuricemia or gout
EP2127540A1 (en) * 2007-01-30 2009-12-02 Snow Brand Milk Products, Co., Ltd. Skin-beautifying agent
WO2010112255A1 (en) * 2009-04-02 2010-10-07 Sojasun Technologies Method for manufacturing a dairy product having a reduced carbohydrate content and enriched with phospholipids, in particular choline, proteins, and calcium
WO2011121151A1 (en) 2010-03-31 2011-10-06 Vegenat, S.A. Functional food supplement intended, in particular, for nutrition and for prevention and improvement in cases of neurological alterations, neurodegenerative alterations or cognitive disorders
WO2011121150A1 (en) 2010-03-31 2011-10-06 Vegenat, S.A. Enteral or oral food product intended, in particular, for nutrition and for the prevention and improvement of neurological alterations, neurodegenerative alterations or cognitive disorders
AU2007236638B2 (en) * 2006-04-07 2013-09-26 Megmilk Snow Brand Co., Ltd. Fat accumulation inhibitor
EP2939550A4 (en) * 2012-12-28 2016-11-02 Kao Corp Sphingomyelin-containing supplement
DE102019120026A1 (en) * 2019-07-24 2021-01-28 Molkerei Alois Müller GmbH & Co. KG Processes for producing dairy products and dairy products produced using such processes
US11331353B2 (en) * 2014-03-25 2022-05-17 Kabushiki Kaisha Yakult Honsha Sleep quality improver

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IN2012DN02664A (en) * 2004-10-12 2015-09-11 Fonterra Co Operative Group
EP1880612A1 (en) 2006-07-17 2008-01-23 Corman S.A. Dairy ingredient enriched in polar lipids and use thereof
JP5818300B2 (en) * 2010-12-27 2015-11-18 雪印メグミルク株式会社 Milk ceramide-containing food and method for producing the same
US10834935B2 (en) * 2012-02-01 2020-11-17 Koninklijke Douwe Egberts B.V. Dairy mineral-fortified liquid dairy products and methods of making
US10849334B2 (en) 2012-02-01 2020-12-01 Koninklijke Douwe Egberts B.V. Dairy mineral-fortified liquid dairy products and methods for making the dairy mineral-fortified liquid dairy products
CN102885136A (en) * 2012-10-16 2013-01-23 九三粮油工业集团有限公司 Phospholipid yoghourt with health-care function, and preparation method thereof
US20150282502A1 (en) * 2012-10-31 2015-10-08 Nestec S.A. Frozen confection product
ES2671633T5 (en) * 2012-10-31 2021-06-29 Nestle Sa Frozen confectionery product
IL223373A (en) 2012-12-02 2013-09-30 Ilan Perry Processes for the preparation of phospholipid-enriched dairy products as neutraceuticals for the formulation of functional foods and nutraceutical and/or pharmaceutical compositions comprising them
US10561674B2 (en) 2012-12-02 2020-02-18 Lipogen Ltd. Processes for the preparation of phospholipid-enriched dairy products as neutraceuticals for the formulation of functional foods
JP6970498B2 (en) * 2016-11-29 2021-11-24 花王株式会社 milk beverage
US11425915B2 (en) 2018-05-02 2022-08-30 Land O'lakes, Inc. Methods of concentrating phospholipids
JP2021010374A (en) * 2020-10-13 2021-02-04 雪印メグミルク株式会社 Bdnf production promoting agent

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5591479A (en) * 1993-12-31 1997-01-07 Institut De Recherche Biologique Brain phospholipid composition and method of making for an infant formula
US5677472A (en) * 1993-02-11 1997-10-14 Svenska Mejeriernas Riksfoerening Ekonomi Ab Method for extracting sphingomyelin
RU2210925C1 (en) * 2002-01-08 2003-08-27 Тимофеенко Татьяна Ильинична Fat-and-oil functional food product
US20030190392A1 (en) * 2002-03-29 2003-10-09 Seiichi Hiratsuka Method for extracting lipid mixture containing phospholipids comprising polyunsaturated fatty acids from viscera of fish, method for preserving viscera prior to extraction, and lipid mixture extracted thereby
JP2003304814A (en) * 2002-04-17 2003-10-28 Fancl Corp Composition with high phosphatidyl serine content
US20040022922A1 (en) * 2002-06-16 2004-02-05 David Rutenberg Infant formula supplemented with phospholipids
US20040234587A1 (en) * 2001-07-27 2004-11-25 Fotini Sampalis Natural marine source phospholipids comprising flavonoids, polyunsaturated fatty acids and their applications
WO2005023271A1 (en) * 2003-09-04 2005-03-17 Bioghurt Biogarde Gmbh & Co. Kg Physiologically active composition based on phosphatidylserine
WO2005099876A1 (en) * 2004-04-16 2005-10-27 UNIVERSITé LAVAL Method for extracting lipids from biological solutions

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0108838B1 (en) * 1982-11-15 1987-04-08 Melkunie Holland B.V. Pulverized products, containing little lactose
US4447463A (en) * 1982-11-19 1984-05-08 Land O'lakes, Inc. Process for producing a butter/margarine blend product
ES2044041T3 (en) 1989-12-19 1994-01-01 Nestle Sa PROCEDURE FOR PREPARING AN EVAPORATED DAIRY PRODUCT.
TWI244484B (en) * 1998-06-09 2005-12-01 Takara Bio Inc Pharmaceutical composition containing oxy-containing hexacyclic compound
WO2002034062A1 (en) * 2000-10-27 2002-05-02 Nv Marc Boone Method for obtaining products enriched in phospho- and sphingolipids
TWI317636B (en) * 2002-11-22 2009-12-01 Meiji Dairies Corp Nutritional compositions for liver disease patients or for patients underhigh levels of invasive stress
JP4390598B2 (en) * 2003-05-13 2009-12-24 株式会社Ａｄｅｋａ Plastic oil-in-water emulsion composition and method for producing the same
IL158139A0 (en) 2003-09-25 2004-09-27 Enzymotec Ltd Stabilized formulations of phosphatidyl serine
IN2012DN02664A (en) 2004-10-12 2015-09-11 Fonterra Co Operative Group

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5677472A (en) * 1993-02-11 1997-10-14 Svenska Mejeriernas Riksfoerening Ekonomi Ab Method for extracting sphingomyelin
US5591479A (en) * 1993-12-31 1997-01-07 Institut De Recherche Biologique Brain phospholipid composition and method of making for an infant formula
US20040234587A1 (en) * 2001-07-27 2004-11-25 Fotini Sampalis Natural marine source phospholipids comprising flavonoids, polyunsaturated fatty acids and their applications
RU2210925C1 (en) * 2002-01-08 2003-08-27 Тимофеенко Татьяна Ильинична Fat-and-oil functional food product
US20030190392A1 (en) * 2002-03-29 2003-10-09 Seiichi Hiratsuka Method for extracting lipid mixture containing phospholipids comprising polyunsaturated fatty acids from viscera of fish, method for preserving viscera prior to extraction, and lipid mixture extracted thereby
JP2003304814A (en) * 2002-04-17 2003-10-28 Fancl Corp Composition with high phosphatidyl serine content
US20040022922A1 (en) * 2002-06-16 2004-02-05 David Rutenberg Infant formula supplemented with phospholipids
WO2005023271A1 (en) * 2003-09-04 2005-03-17 Bioghurt Biogarde Gmbh & Co. Kg Physiologically active composition based on phosphatidylserine
WO2005099876A1 (en) * 2004-04-16 2005-10-27 UNIVERSITé LAVAL Method for extracting lipids from biological solutions

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Section Ch Week 200367, Derwent World Patents Index; Class D13, AN 2003-706261, XP002395571 *
PATENT ABSTRACTS OF JAPAN vol. 2003, no. 12 5 December 2003 (2003-12-05) *
See also references of EP1901620A1 *

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2452567A1 (en) * 2005-09-30 2012-05-16 Snow Brand Milk Products Co., Ltd. Powder being rich in milk-origin complex lipids
EP1938695A1 (en) * 2005-09-30 2008-07-02 Snow Brand Milk Products, Co., Ltd. Powder being rich in milk-origin complex lipids
EP1938695A4 (en) * 2005-09-30 2009-08-19 Snow Brand Milk Products Co Ltd Powder being rich in milk-origin complex lipids
JP2007089535A (en) * 2005-09-30 2007-04-12 Snow Brand Milk Prod Co Ltd Powder highly containing compound lipid derived from milk
AU2007236638B2 (en) * 2006-04-07 2013-09-26 Megmilk Snow Brand Co., Ltd. Fat accumulation inhibitor
AU2008210936B2 (en) * 2007-01-30 2013-07-04 Megmilk Snow Brand Co., Ltd. Skin-beautifying agent
EP2127540A4 (en) * 2007-01-30 2010-12-01 Snow Brand Milk Products Co Ltd Skin-beautifying agent
EP2127540A1 (en) * 2007-01-30 2009-12-02 Snow Brand Milk Products, Co., Ltd. Skin-beautifying agent
WO2009110205A1 (en) * 2008-03-04 2009-09-11 ナガセケムテックス株式会社 Agent for increasing the quantity of hyaluronic acid
JP5561614B2 (en) * 2008-03-04 2014-07-30 ナガセケムテックス株式会社 Hyaluronic acid extender
JP2009256331A (en) * 2008-03-25 2009-11-05 Nagase Chemtex Corp Agent for preventing, alleviating or treating hyperuricemia or gout
FR2943893A1 (en) * 2009-04-02 2010-10-08 Sojasun Technologies PROCESS FOR THE PRODUCTION OF A MILK PRODUCT WITH REDUCED CARBOHYDRATE CONTENT AND ENRICHED WITH PHOSPOLIPIDS, IN PARTICULAR CHOLINE, PROTEINS AND CALCIUM
WO2010112255A1 (en) * 2009-04-02 2010-10-07 Sojasun Technologies Method for manufacturing a dairy product having a reduced carbohydrate content and enriched with phospholipids, in particular choline, proteins, and calcium
WO2011121151A1 (en) 2010-03-31 2011-10-06 Vegenat, S.A. Functional food supplement intended, in particular, for nutrition and for prevention and improvement in cases of neurological alterations, neurodegenerative alterations or cognitive disorders
WO2011121150A1 (en) 2010-03-31 2011-10-06 Vegenat, S.A. Enteral or oral food product intended, in particular, for nutrition and for the prevention and improvement of neurological alterations, neurodegenerative alterations or cognitive disorders
EP2939550A4 (en) * 2012-12-28 2016-11-02 Kao Corp Sphingomyelin-containing supplement
US9649322B2 (en) 2012-12-28 2017-05-16 Kao Corporation Sphingomyelin-containing supplement
US11331353B2 (en) * 2014-03-25 2022-05-17 Kabushiki Kaisha Yakult Honsha Sleep quality improver
DE102019120026A1 (en) * 2019-07-24 2021-01-28 Molkerei Alois Müller GmbH & Co. KG Processes for producing dairy products and dairy products produced using such processes

Also Published As

Publication number Publication date
ES2820337T3 (en) 2021-04-20
NZ563564A (en) 2011-02-25
EP2308324A1 (en) 2011-04-13
CA2611121A1 (en) 2006-12-07
AU2006254548B9 (en) 2012-05-10
JP5727392B2 (en) 2015-06-03
JP2008541740A (en) 2008-11-27
AU2006254548C1 (en) 2012-09-20
BRPI0610945A2 (en) 2010-08-03
KR101352288B1 (en) 2014-01-16
JP5455365B2 (en) 2014-03-26
CA2611121C (en) 2014-01-28
RU2007148557A (en) 2009-07-20
KR20080018917A (en) 2008-02-28
RU2420083C2 (en) 2011-06-10
AR057042A1 (en) 2007-11-14
EP1901620A1 (en) 2008-03-26
AU2006254548A1 (en) 2006-12-07
US20090123630A1 (en) 2009-05-14
BRPI0610945B1 (en) 2016-09-20
US8231922B2 (en) 2012-07-31
EP1901620B1 (en) 2020-07-01
JP2012061012A (en) 2012-03-29
DK1901620T3 (en) 2020-09-28
PT1901620T (en) 2020-09-28
US20060280779A1 (en) 2006-12-14
AU2006254548B2 (en) 2012-03-22

Similar Documents

Publication Publication Date Title
CA2611121C (en) Phosphatidylserine enriched milk fractions for the formulation of functional foods
US20230292781A1 (en) Methods of maintaining or increasing growth or cognitive development
Dewettinck et al. Nutritional and technological aspects of milk fat globule membrane material
AU2010257271B8 (en) Beta-serum dairy products, neutral lipid-depleted and/or polar lipid-enriched dairy products, and processes for their production
MX2011013194A (en) Omega-3 fatty acid enriched beverages.
JP2001128642A (en) Food composition
Burling et al. Milk–A new source for bioactive phospholipids for use in food formulations
JP6970498B2 (en) milk beverage
JP5469454B2 (en) Foods based on dairy products containing central nervous system lipids
JP2020198896A (en) Yogurt
US20150265639A1 (en) Processes for the preparation of phospholipid-enriched dairy products as neutraceuticals for the formulation of functional foods
NZ556699A (en) Dairy product and process

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application
DPE1 Request for preliminary examination filed after expiration of 19th month from priority date (pct application filed from 20040101)
WWE Wipo information: entry into national phase

Ref document number: 563564

Country of ref document: NZ

WWE Wipo information: entry into national phase

Ref document number: 2611121

Country of ref document: CA

Ref document number: 2008513930

Country of ref document: JP

NENP Non-entry into the national phase

Ref country code: DE

WWW Wipo information: withdrawn in national office

Ref document number: DE

WWE Wipo information: entry into national phase

Ref document number: 2006753297

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 2006254548

Country of ref document: AU

WWE Wipo information: entry into national phase

Ref document number: 1020077030710

Country of ref document: KR

NENP Non-entry into the national phase

Ref country code: RU

WWW Wipo information: withdrawn in national office

Ref document number: RU

WWE Wipo information: entry into national phase

Ref document number: 2007148557

Country of ref document: RU

ENP Entry into the national phase

Ref document number: 2006254548

Country of ref document: AU

Date of ref document: 20060531

Kind code of ref document: A

WWP Wipo information: published in national office

Ref document number: 2006254548

Country of ref document: AU

WWP Wipo information: published in national office

Ref document number: 2006753297

Country of ref document: EP

ENP Entry into the national phase

Ref document number: PI0610945

Country of ref document: BR

Kind code of ref document: A2