WO2006084560A1 - Composition comprising peptide - Google Patents

Composition comprising peptide Download PDF

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Publication number
WO2006084560A1
WO2006084560A1 PCT/EP2006/000501 EP2006000501W WO2006084560A1 WO 2006084560 A1 WO2006084560 A1 WO 2006084560A1 EP 2006000501 W EP2006000501 W EP 2006000501W WO 2006084560 A1 WO2006084560 A1 WO 2006084560A1
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WO
WIPO (PCT)
Prior art keywords
food product
vitamin
food
acid
mmol
Prior art date
Application number
PCT/EP2006/000501
Other languages
French (fr)
Inventor
Angelika De Bree
Cinderella Christina Gerhardt
Original Assignee
Unilever N.V.
Unilever Plc
Hindustan Unilever Limited
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 Unilever N.V., Unilever Plc, Hindustan Unilever Limited filed Critical Unilever N.V.
Priority to EP06706331A priority Critical patent/EP1879465A1/en
Publication of WO2006084560A1 publication Critical patent/WO2006084560A1/en

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Classifications

    • 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
    • A23G9/36—Frozen sweets, e.g. ice confectionery, ice-cream; Mixtures therefor characterised by the composition containing organic or inorganic compounds containing microorganisms or enzymes; containing paramedical or dietetical agents, e.g. vitamins
    • A23G9/366—Frozen sweets, e.g. ice confectionery, ice-cream; Mixtures therefor characterised by the composition containing organic or inorganic compounds containing microorganisms or enzymes; containing paramedical or dietetical agents, e.g. vitamins containing vitamins, antibiotics
    • 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
    • A23C9/12—Fermented milk preparations; Treatment using microorganisms or enzymes
    • A23C9/13—Fermented milk preparations; Treatment using microorganisms or enzymes using additives
    • A23C9/1307—Milk products or derivatives; Fruit or vegetable juices; Sugars, sugar alcohols, sweeteners; Oligosaccharides; Organic acids or salts thereof or acidifying agents; Flavours, dyes or pigments; Inert or aerosol gases; Carbonation methods
    • 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
    • A23C9/12—Fermented milk preparations; Treatment using microorganisms or enzymes
    • A23C9/13—Fermented milk preparations; Treatment using microorganisms or enzymes using additives
    • A23C9/1322—Inorganic compounds; Minerals, including organic salts thereof, oligo-elements; Amino-acids, peptides, protein-hydrolysates or derivatives; Nucleic acids or derivatives; Yeast extract or autolysate; Vitamins; Antibiotics; Bacteriocins
    • 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
    • A23G9/38—Frozen sweets, e.g. ice confectionery, ice-cream; Mixtures therefor characterised by the composition containing organic or inorganic compounds containing peptides or proteins
    • 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
    • A23L33/15—Vitamins
    • 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
    • A23L33/18—Peptides; Protein hydrolysates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • A61K31/525—Isoalloxazines, e.g. riboflavins, vitamin B2
    • 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

  • composition comprising peptide
  • the invention relates to a composition
  • a composition comprising blood pressure lowering peptide, in particular ACE-inhibiting peptide, in particular ACE-inhibiting tripepti.de and/or dipeptide .
  • Hypertension or high blood pressure is considered to be one of the main risk factors for Cardio Vascular Diseases (CVD) .
  • CVD Cardio Vascular Diseases
  • One of the mechanisms which regulates blood pressure is the renin- angiotensin system. This is a cascade of reactions leading to the formation of angiotensin II, which has a strong vasoconstrictive and hence blood pressure increasing effect . Inhibition of one of the key enzymes in this cascade : Angiotensin I Converting Enzyme (ACE) reduces formation of angiotensin II and thus has a blood pressure lowering effect . Long term human intervention studies have shown regular intake of low amounts of ACE inhibitors reduces CVD by 25% (Gerstein et al . (2000) , The Lancet 355, 253-259) .
  • ACE-inhibitors in food products are well known . Such food products have for instance been prepared by fermentation of milk or milk products .
  • the blood pressure lowering effect of sour milk containing the ACE- inhibiting peptides VPP and IPP was shown in hypertensive humans (Hata, Y et al . ( 1996) , American Journal of Clinical Nutrition 64 , 767-771 ) .
  • a commercially available fermented milk product which claims to be “suitable for those with mild hypertension” is Calpis sour milk, fermented with Lactobacillus helveticus and Saccharomyces cervisiae, produced by Calpis Food Industry, Japan.
  • Another commercially available fermented milk product is Evolus produced by Valio, Finland. These fermented milk products are fermented with Lactobacillus helveticus (Lb . helveticus) strains .
  • the products contain tripeptides (VPP and IPP) responsible for in vitro ACE inhibition.
  • the known products have a blood pressure lowering effect, which effect results in a reduction of risk of CVD.
  • Protein hydrolysates or fermentates may contain particular peptides that decrease blood pressure, probably by their inhibitory activity on ACE .
  • the observed blood pressure lowering effects are usually modest .
  • This invention comprises the combination of peptides with additional dietary, bioactive ingredients, in order to obtain a synergistic increase in the blood pressure lowering effect .
  • the invention relates to a food product comprising one or more peptides and one or more B-vitamins , wherein the peptides are chosen from the group consisting of: VPP, IPP, LPP, VY, VF, IW, VAP, AW, LW, HLP, IY, FY, PPL, YP, TPP, MPP; and ( 1) wherein the amount of folic acid in the food product is from 0.02 ⁇ g to 5, 000 ⁇ g, more preferably from 30 ⁇ g to l, 000 ⁇ g, especially from 60 ⁇ g to 400 ⁇ g; and/or
  • the amount of vitamin B2 in the food composition is from 0.2 mg to 40 mg, more preferably from 0.24 mg to 8 mg, especially from 0.5 mg to 3.2 mg; and/or
  • the amount of vitamin B ⁇ in the food composition is from 0.2 mg to 50 mg, more preferably from 0.3 mg to 10 mg, especially from 0.6 mg to 4 mg; and/or (4 ) wherein the amount of vitamin B12 in the food composition is from 0.00001 ⁇ g to 25 ⁇ g, more preferably from 0.15 ⁇ g to 5 ⁇ g, especially from 0.3 ⁇ g to 2 ⁇ g .
  • composition according to the invention comprises one or more peptides .
  • Peptide is herein a peptide having 2-10 amino acids .
  • the peptide is a blood pressure lowering peptide .
  • the peptide (s) are chosen from tripeptides and/or dipeptides .
  • the ACE inhibiting peptide (s) are chosen from the list : VPP, IPP, LPP, VY, VF, IW, VAP, AW, LW, HLP, IY, FY, PPL, YP, TPP, MPP .
  • the peptide is one or more of tripeptides VPP, IPP, LPP.
  • the usual one letter code of aminoacids is used herein for the description of peptides unless otherwise indicated.
  • the peptides mentioned herein have an ACE inhibiting effect as mentioned in table 1.
  • the peptides are stable in the human intestinal tract, and more preferably also absorbed by human enterocytes .
  • WO01/681115 discloses (page 24 , table 4 ) a yeast hydrolysate comprising VPP or IPP tripeptides . Although these hydrolysates may -accidentally- contain minor amounts of vitamin B, this document does not dislcose the specific levels of folic acid or vitamin B2, or vitamin B6 or vitamin B12 as currently claimed.
  • WO01/82836 discloses (pag 12, table 3) a fermented milk product comprising VPP or IPP tripeptides . This document also does not specify the specific levels of folic acid, vitamin B2 , vitamin B6 or vitamin B12 as currently claimed.
  • US04/043942 discloses (example 39, preparation IV) a dietary composition comprising folic acid in combination with the peptide H-GIy-GIy-OH .
  • the specific di- or tripeptides according to the current invention do not seem to be disclosed.
  • Patent application EP1568707 discloses in example 6 a combination of an anti-hypertensive composition an vitamin B. Again this document does not seem to disclose the specific peptides as currently claimed.
  • the peptides may be made by any method known in the art, including synthesis .
  • the peptides are made by (enzymatic) hydrolysis or fermentation of any one or more protein substrates containing the fragments one or more of the fragments VPP, IPP, LPP, VY, VF, IW, HLPLP, VAP, AW, LW, HLP, IY, FY, PPL, YP, TPP, and MPP .
  • the protein substrate contains mor than one, preferably two or more, even more preferably three or more of most preferably four or more of the fragments VPP, IPP, LPP, VY, VF, IW, HLPLP, VAP, AW, LW, HLP, IY, FY, PPL, YP, TPP, and MPP .
  • the production of the biologically active peptides as described before may be maximised.
  • the skilled person trying to maximise the production will know how to adjust the process parameters , such as hydrolysis time, hydrolysis temperature, enzyme type and concentration etc .
  • composition according to the invention further comprises one or more B-vitamins .
  • the B-vitamin is preferably one or more of folic acid, Vitamin B2, Vitamin B6, and Vitamin B12.
  • the composition comprises all of the B-vitamins folic acid, Vitamin B2, Vitamin B6, and Vitamin B12.
  • Folic acid is the synthetic, stable form of naturally occuring folates . Folic acid is known to participate in the metabolism of homocysteine . Herein the term folic acid also includes folates . For a number of years, high homocysteine levels have been correlated to high incidence of cardiovascular disease . It is thought that lowering homocysteine may reduce the risk of cardiovascular disease .
  • Folic acid, vitamines B2, B6 and B12 are important for the degradation of homocysteine .
  • supplementation with folic acid is associated with a blood pressure lowering effect .
  • This blood pressure lowering effect could be due to the lowering effect on homocysteine levels , or to a direct beneficial effect of B- vitamins on blood pressure .
  • compositions according to the invention comprising peptide and one or more of vitamin B6 and vitamin B12 and folic acid have a strong and in combination with peptide (s ) synergistic effect on lowering blood pressure .
  • the B vitamins are preferably selected from folic acid, vitamin B2 , vitamin B6, vitamin B12 and mixtures thereof .
  • the total amount of vitamin B in a food product or food supplement is preferably from 0.01% to 2 , 500%, more preferably from 15% to 500%, still more preferably from 30% to 200% from the Reference Labeling Values from the Scientific Committee on Food of the European Committee as of the date of filing of this application, namely folic acid: 200 ⁇ g, vitamin B2 : 1.6mg, vitamin B6 : 2 mg, vitamin B12 : l ⁇ g.
  • the following preferred ranges of B vitamin inclusion levels are based on the assumption that the particular B vitamin in question is included in the combination .
  • the daily intake of folic acid from the food product is from 0.02 ⁇ g to 5, 000 ⁇ g, more preferably from 30 ⁇ g to l, 000 ⁇ g, especially from 60 ⁇ g to 400 ⁇ g .
  • the intake of vitamin B2 in such a food product is preferably from 0.2 mg to 40 mg, more preferably from 0.24 mg to 8 mg, especially from 0.5 mg to 3.2 mg .
  • the intake of vitamin B ⁇ in the food product is preferably from 0.2 mg to 50 mg, more preferably from 0.3 mg to 10 mg, especially from 0.6 mg to 4 mg.
  • the intake of vitamin B12 from the food product is preferably from 0.00001 ⁇ g to 25 ⁇ g, more preferably from 0.15 ⁇ g to 5 ⁇ g, especially from 0.3 ⁇ g to 2 ⁇ g.
  • Food products according to the invention are defined as products, suitable for human consumption.
  • the food products according to the invention are preferably made according to a process involving the following steps : (a) enzymatic hydrolysis of a protein substrate comprising hydrolysed protein product;
  • step c) using the concentrate prepared in step c) as an ingredient in the preparation of the food product .
  • the enzymatic hydrolysis step (a) may be any enzymatic treatment of a protein substrate leading to hydrolysis of the substrate resulting in liberation of one or more of peptides VPP, IPP, LPP, VY, VF, IW, HLPLP, VAP, AW, LW, HLP, IY, FY, PPL, YP, TPP, and MPP.
  • suitable substrates include whole milk, skimmed milk, acid casein, rennet casein, acid whey products or cheese whey products, collagen based animal proteins such as gelatine as well as bones or fish-bones .
  • vegetable substrates like wheat gluten, milled barley and protein fractions obtained from, for example, soy, rice or corn are suitable substrates . Mixtures of these may also be used as substrate .
  • the substrate is milk or a milk product .
  • the protein substrate is casein .
  • caseins are especially suitable as substrate : casein, casein powder, casein powder concentrates, casein powder isolates, or beta-casein, or alpha-s2-casein .
  • a substrate that has a high content of casein such as casein protein isolate (CPI) .
  • the enzyme may be any enzyme that is able to hydrolyse protein substrate resulting in the liberation of one or more of. VPP, IPP, LPP, VY, VF, IW, HLPLP, VAP, AW, LW, HLP, IY, FY, PPL, YP, TPP, and MPP .
  • a suitable hydrolysate containing ACE inhibiting peptides according to the invention may be obtained by hydrolysis with an endo-protease and a tri-peptidase as described in WO03/102905.
  • the separation step (b) (or concentration step (c) ) may be executed in any way known to the skilled person, e . g. by precipitation, filtration, centrifugation, extraction or chromatography and combinations thereof .
  • the separation step (b) is executed using an ultrafiltration (UF) and/or nanofiltration (NF) techniques .
  • UF ultrafiltration
  • NF nanofiltration
  • the pore size of the membranes used in the filtration step, as well as the charge of the membrane may be used to control the separation of the ACE inhibiting peptides .
  • the fractionation of casein protein hydrolysates using charged UF/NF membranes is described in Y. Poilot et al, Journal of Membrane Science 158 ( 1999) 105-114. Electrodialysis is for instance described in WO00/42066.
  • the separation is executed using acid precipitation .
  • the concentration/drying step (c) involves drying the fraction from step b) to obtain a solid rich in ACE inhibiting peptide .
  • This step may be done in a conventional way, e . g. by spray drying or freeze drying.
  • the product of the separation step is dried until a concentrated solution of hydrolysed protein, having a low Aw is obtained. In such way the formation of off- flavour through Maillard reactions may be avoided.
  • the fraction rich in peptides prepared in step (b) is hereafter designated as ACE-fraction and the solid prepared in step (c) is hereafter designated as ACE-solid.
  • the ACE-fraction and/or the ACE-solid may advantageously be used as an ingredient in a food product .
  • the food product according to the invention or food products derived therefrom may be pasteurised or sterilised.
  • the food products according to the invention may be of any food type . They may comprise common food ingredients in addition to the food product, such as flavour, sugar, fruits, minerals , vitamins, stabilisers , thickeners , etc . in appropriate amounts .
  • the food product comprises 50-200 mmol/kg K + and/or 15-60 mmol/kg Ca 2+ and/or 6-25 mmol/kg Mg 2+ more preferably, 100- 150 mmol/kg K + and/or 30-50 mmol/kg Ca 2+ and/or 10-25 mmol/kg Mg 2+ and most preferably 110-135 rnmol/kg K + and/or 35-45 mmol/kg Ca 2+ and/or 13-20 mmol/kg Mg 2+ .
  • These cations have a beneficial effect of further lowering blood pressure when incorporated in the food products according to the invention.
  • the food product comprises one or more phytosterols , phytostanols and/or analogues or derivatives thereof.
  • the phytosterols, phytostanols and their analogues and derivatives may be selected from one or more of phytosterols, phytostanols, synthetic analogues of phytosterols and phytostanols and esterified derivatives of any of the foregoing, and mixtures of any of these .
  • the total amount of such substances in a food product or food supplement is preferably from 0.01% to 20%, more preferably from 0.1% to 15%, still more preferably from 0.2% to 8% , and most preferably from 0.3% to 8% by weight of the food product composition .
  • the daily intake of such sterol-type component of the combination is from O . lg to 3g, more preferably from 1.5g to 2.5g, especially from 2g to 2.25g per day.
  • Phytosterols also known as plant sterols or vegetable sterols can be classified in three groups, 4-desmethylsterols, 4-monomethylsterols and 4 , 4 ' -dimethylsterols .
  • oils they mainly exists as free sterols and sterol esters of fatty acids although sterol glucosides and acylated sterol glucosides are also present .
  • There are three maj or phytosterols namely beta-sitosterol, stigmasterol and campesterol . Schematic drawings of the components meant are as given in "Influence of Processing on Sterols of Edible Vegetable Oils" , S . P. Kochhar; Prog. Lipid Res . 22 : pp. 161-188.
  • the phytostanols are the respective 5 ⁇ - saturated derivatives of phytosterols such as sitostanol, campestanol and their derivatives .
  • Synthetic analogues of any of the phytosterols or phytostanols may be used.
  • the phytosterol or phytostanol is selected from the group comprising fatty acid ester of ⁇ -sitosterol, ⁇ - sitostanol, campesterol, campestanol, stigmasterol, stigmastanol and mixtures thereof.
  • the optional phytosterol or phytostanol materials recited above may optionally be provided in the form of one or more fatty acid esters thereof. Mixtures of esterified and non-esterified materials may also be used.
  • any of the phytosterols, phytostanols and their synthetic analogues used in the present invention are preferably esterified with a fatty acid.
  • they are esterified with one or more C 2 - 22 fatty acids .
  • the term C 2 -2 2 fatty acid refers to any molecule comprising a C2- 22 main chain and at least one acid group .
  • the C2-22 main chain may contain 1-6 double bonds, be partially substituted or side chains may be present .
  • the C2- 2 2 fatty acids are linear molecules comprising one or two acid group (s ) as end group (s) .
  • Most preferred are linear Ca-22 fatty acids as occur in natural liquid oils .
  • Suitable examples of any such fatty acids are acetic acid, propionic acid, butyric acid, caproic acid, caprylic acid, capric acid.
  • Other suitable acids are for example citric acid, lactic acid, oxalic acid and maleic acid.
  • Most preferred are lauric acid, palmitic acid, stearic acid, arachidic acid, behenic acid, oleic acid, cetoleic acid, erucic acid, elaidic acid, linoleic acid and linolenic acid.
  • a mixture of fatty acids may be used for esterification of the sterols .
  • a naturally occurring fat or oil as a source of the fatty acid and to carry out the esterification via an interesterification reaction.
  • Use of a natural source nearly always results in a mixture of fatty acids .
  • the fatty acid mixture contains a high amount (>50%, preferably >70%, further preferred >80%) of unsaturates, being either monounsaturated fatty acids (MUFA) and/or polyunsaturated fatty acids (PUFA) .
  • MUFA monounsaturated fatty acids
  • PUFA polyunsaturated fatty acids
  • fatty acid mixtures of sunflower, safflower, rapeseed, linseed, olive oil, linola and/or soybean are used.
  • the food products according to the invention are drinks, more preferably fruit juice products or dairy drinks optionally with added fruit juice, dairy type products, frozen confectionary products or spreads/margarines . These preferred types of food products are described in some detail below and in the examples .
  • fruit juice products according to the invention are juices derived from citrus fruit like orange and grapefruit, tropical fruits , banana, peach, peer, strawberry, to which ACE- solid and/or ACE-fraction and optionally one or more heart health ingredients are added.
  • dairy products according to the invention are milk, dairy spreads, cream cheese, milk type drinks and yoghurt, to which ACE-solid and/or ACE-fraction and optionally one or more heart health ingredients are added.
  • the food product may be used as such as a milk type drink. alternatively flavour or other additives may be added.
  • a dairy type product may also be made by adding ACE-solid and/or ACE- fraction to water or to a dairy product .
  • composition for a yoghurt type product is about 50-80 wt . % water, 0.1-15 wt . % ACE-solid and optionally one or more heart health ingredients, 0-15 wt . % whey powder, 0-15 wt . % sugar (e . g. sucrose) , 0.01-1 wt . % yoghurt culture, 0-20 wt . % fruit, 0.05-5 wt . % vitamins and minerals, 0-2 wt . % flavour, 0-5 wt . % stabilizer (thickener or gelling agent) .
  • a typical serving size for a yoghurt type product could be from 50 to 250 g, generally from 80 to 200 g.
  • frozen confectionery product includes milk containing frozen confections such as icecream, frozen yoghurt, sherbet, sorbet, ice milk and frozen custard, water-ices, granitas and frozen fruit purees .
  • the level of solids in the frozen confection is more than 3 wt . %, more preferred from 10 to 70 wt . %, for example 40 to 70 wt . % .
  • Ice cream will typically comprise 0 to 20 wt . % of fat, 0.1 to 20 wt . % ACE-solid and optionally one or more heart health ingredients, sweeteners, 0 to 10 wt . % of non-fat milk components and optional components such as emulsifiers, stabilisers, preservatives, flavouring ingredients, vitamins, minerals, etc, the balance being water.
  • ice cream will be aerated e . g. to an overrun of 20 to 400 %, more specific 40 to 200 % and frozen to a temperature of from -2 to -200 0 C, more specific -10 to -30 0 C . Ice cream normally comprises calcium at a level of about 0.1 wt% .
  • the food product can be prepared by the skilled person based on common general knowledge, protein hydrolysate and optionally one or more heart health ingredients in suitable amounts .
  • Examples of such food products are baked goods, dairy type foods, snacks , etc .
  • the food product is an oil and water containing emulsion, for instance a spread.
  • Oil and water emulsion is herein defined as an emulsion comprising oil and water and includes oil in water (0/W) emulsions and water in oil emulsions (W/0) and more complex emulsions for instance water- in-oil-in-water (W/O/W/O/W) emulsions .
  • Oil is herein defined as including fat .
  • the food product is a spread, frozen confection, or sauce .
  • a spread according to the invention comprises 30-90 wt . % vegetable oil .
  • a spread has a pH of 4.2-6.0.

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Abstract

Composition comprising one or more peptide and one or more B-vitamins. Preferably the ACE inhibiting peptides are chosen from tripeptides and/or dipeptides, more preferably from VPP, IPP, LPP, VY, VF, IW, HLPLP, VAP, AW, LW, HLP, IY, FY, PPL, YP, TPP, and MPP.

Description

Composition comprising peptide
Field of the invention
The invention relates to a composition comprising blood pressure lowering peptide, in particular ACE-inhibiting peptide, in particular ACE-inhibiting tripepti.de and/or dipeptide .
Background to the invention Hypertension or high blood pressure is considered to be one of the main risk factors for Cardio Vascular Diseases (CVD) . One of the mechanisms which regulates blood pressure is the renin- angiotensin system. This is a cascade of reactions leading to the formation of angiotensin II, which has a strong vasoconstrictive and hence blood pressure increasing effect . Inhibition of one of the key enzymes in this cascade : Angiotensin I Converting Enzyme (ACE) reduces formation of angiotensin II and thus has a blood pressure lowering effect . Long term human intervention studies have shown regular intake of low amounts of ACE inhibitors reduces CVD by 25% (Gerstein et al . (2000) , The Lancet 355, 253-259) .
ACE-inhibitors in food products are well known . Such food products have for instance been prepared by fermentation of milk or milk products . In a placebo-controlled study, the blood pressure lowering effect of sour milk containing the ACE- inhibiting peptides VPP and IPP was shown in hypertensive humans (Hata, Y et al . ( 1996) , American Journal of Clinical Nutrition 64 , 767-771 ) .
A commercially available fermented milk product, which claims to be "suitable for those with mild hypertension" is Calpis sour milk, fermented with Lactobacillus helveticus and Saccharomyces cervisiae, produced by Calpis Food Industry, Japan. Another commercially available fermented milk product is Evolus produced by Valio, Finland. These fermented milk products are fermented with Lactobacillus helveticus (Lb . helveticus) strains . The products contain tripeptides (VPP and IPP) responsible for in vitro ACE inhibition.
The known products have a blood pressure lowering effect, which effect results in a reduction of risk of CVD.
Protein hydrolysates or fermentates may contain particular peptides that decrease blood pressure, probably by their inhibitory activity on ACE . The observed blood pressure lowering effects are usually modest . This invention comprises the combination of peptides with additional dietary, bioactive ingredients, in order to obtain a synergistic increase in the blood pressure lowering effect .
Summary of the invention It is an obj ect of the invention to provide a composition providing further reduction of CVD, compared to the known products comprising VPP and/or IPP. Another obj ect is to provide a food product that has a blood pressure lowering effect . It is another object to provide such food products having a good taste . One or more of these objects is attained according to the invention, which provides a composition comprising one or more peptides and one or more B-vitamins .
In particular the invention relates to a food product comprising one or more peptides and one or more B-vitamins , wherein the peptides are chosen from the group consisting of: VPP, IPP, LPP, VY, VF, IW, VAP, AW, LW, HLP, IY, FY, PPL, YP, TPP, MPP; and ( 1) wherein the amount of folic acid in the food product is from 0.02μg to 5, 000μg, more preferably from 30μg to l, 000μg, especially from 60μg to 400μg; and/or
(2 ) wherein the amount of vitamin B2 in the food composition is from 0.2 mg to 40 mg, more preferably from 0.24 mg to 8 mg, especially from 0.5 mg to 3.2 mg; and/or
(3) wherein the amount of vitamin Bβ in the food composition is from 0.2 mg to 50 mg, more preferably from 0.3 mg to 10 mg, especially from 0.6 mg to 4 mg; and/or (4 ) wherein the amount of vitamin B12 in the food composition is from 0.00001 μg to 25 μg, more preferably from 0.15μg to 5μg, especially from 0.3μg to 2μg .
Detailed description of the invention The composition according to the invention comprises one or more peptides . Peptide is herein a peptide having 2-10 amino acids . Preferably the peptide is a blood pressure lowering peptide . More preferably the peptide (s) are chosen from tripeptides and/or dipeptides . Even more preferably the ACE inhibiting peptide (s) are chosen from the list : VPP, IPP, LPP, VY, VF, IW, VAP, AW, LW, HLP, IY, FY, PPL, YP, TPP, MPP . More preferably the peptide is one or more of tripeptides VPP, IPP, LPP.
The usual one letter code of aminoacids is used herein for the description of peptides unless otherwise indicated. The peptides mentioned herein have an ACE inhibiting effect as mentioned in table 1. Preferable the peptides are stable in the human intestinal tract, and more preferably also absorbed by human enterocytes .
WO01/681115 discloses (page 24 , table 4 ) a yeast hydrolysate comprising VPP or IPP tripeptides . Although these hydrolysates may -accidentally- contain minor amounts of vitamin B, this document does not dislcose the specific levels of folic acid or vitamin B2, or vitamin B6 or vitamin B12 as currently claimed.
Similarly WO01/82836 discloses (pag 12, table 3) a fermented milk product comprising VPP or IPP tripeptides . This document also does not specify the specific levels of folic acid, vitamin B2 , vitamin B6 or vitamin B12 as currently claimed.
US04/043942 discloses (example 39, preparation IV) a dietary composition comprising folic acid in combination with the peptide H-GIy-GIy-OH . The specific di- or tripeptides according to the current invention do not seem to be disclosed.
Patent application EP1568707 discloses in example 6 a combination of an anti-hypertensive composition an vitamin B. Again this document does not seem to disclose the specific peptides as currently claimed.
Table 1 : ACE inhibition ( IC50 values ) and preferred amounts of peptides
Figure imgf000006_0001
The peptides may be made by any method known in the art, including synthesis . Preferably the peptides are made by (enzymatic) hydrolysis or fermentation of any one or more protein substrates containing the fragments one or more of the fragments VPP, IPP, LPP, VY, VF, IW, HLPLP, VAP, AW, LW, HLP, IY, FY, PPL, YP, TPP, and MPP . Advantageously the protein substrate contains mor than one, preferably two or more, even more preferably three or more of most preferably four or more of the fragments VPP, IPP, LPP, VY, VF, IW, HLPLP, VAP, AW, LW, HLP, IY, FY, PPL, YP, TPP, and MPP .
Through optimisation of the fermentation or hydrolysis conditions, the production of the biologically active peptides as described before may be maximised. The skilled person trying to maximise the production will know how to adjust the process parameters , such as hydrolysis time, hydrolysis temperature, enzyme type and concentration etc .
When above mentioned peptides are generated by fermentation or enzymatic hydrolysation, highly complex mixtures of hundreds to thousands of peptides arise . Although a large portion of these peptides may show little or no ACE inhibitory activity, their presence may be important to the overall blood pressure lowering effect of the hydrolysate/fermentate e . g. by increasing the bioavailability of the ACE inhibitory peptides .
The composition according to the invention further comprises one or more B-vitamins . The B-vitamin is preferably one or more of folic acid, Vitamin B2, Vitamin B6, and Vitamin B12. Preferably the composition comprises all of the B-vitamins folic acid, Vitamin B2, Vitamin B6, and Vitamin B12.
Folic acid is the synthetic, stable form of naturally occuring folates . Folic acid is known to participate in the metabolism of homocysteine . Herein the term folic acid also includes folates . For a number of years, high homocysteine levels have been correlated to high incidence of cardiovascular disease . It is thought that lowering homocysteine may reduce the risk of cardiovascular disease .
Folic acid, vitamines B2, B6 and B12 are important for the degradation of homocysteine . There are indications that supplementation with folic acid (with or without additional vitamin Bβ) is associated with a blood pressure lowering effect . This blood pressure lowering effect could be due to the lowering effect on homocysteine levels , or to a direct beneficial effect of B- vitamins on blood pressure .
The compositions according to the invention comprising peptide and one or more of vitamin B6 and vitamin B12 and folic acid have a strong and in combination with peptide (s ) synergistic effect on lowering blood pressure .
The B vitamins are preferably selected from folic acid, vitamin B2 , vitamin B6, vitamin B12 and mixtures thereof . The total amount of vitamin B in a food product or food supplement is preferably from 0.01% to 2 , 500%, more preferably from 15% to 500%, still more preferably from 30% to 200% from the Reference Labeling Values from the Scientific Committee on Food of the European Committee as of the date of filing of this application, namely folic acid: 200μg, vitamin B2 : 1.6mg, vitamin B6 : 2 mg, vitamin B12 : lμg. The following preferred ranges of B vitamin inclusion levels are based on the assumption that the particular B vitamin in question is included in the combination . Preferably, the daily intake of folic acid from the food product is from 0.02μg to 5, 000μg, more preferably from 30μg to l, 000μg, especially from 60μg to 400μg . The intake of vitamin B2 in such a food product is preferably from 0.2 mg to 40 mg, more preferably from 0.24 mg to 8 mg, especially from 0.5 mg to 3.2 mg . The intake of vitamin Bβ in the food product is preferably from 0.2 mg to 50 mg, more preferably from 0.3 mg to 10 mg, especially from 0.6 mg to 4 mg. The intake of vitamin B12 from the food product is preferably from 0.00001 μg to 25 μg, more preferably from 0.15μg to 5μg, especially from 0.3μg to 2μg. These amounts apply per food product in its common dosage form, portion or form wherein the product is commercialised (e . g. tub, bottle etc) .
Food products according to the invention are defined as products, suitable for human consumption.
The food products according to the invention are preferably made according to a process involving the following steps : (a) enzymatic hydrolysis of a protein substrate comprising hydrolysed protein product;
(b) separation from the hydrolysed protein product of a fraction rich in ACE inhibiting peptide;
(c) concentration and/or drying of the fraction from step b) to obtain a concentrate rich ACE inhibiting peptide;
(d) using the concentrate prepared in step c) as an ingredient in the preparation of the food product .
The enzymatic hydrolysis step (a) may be any enzymatic treatment of a protein substrate leading to hydrolysis of the substrate resulting in liberation of one or more of peptides VPP, IPP, LPP, VY, VF, IW, HLPLP, VAP, AW, LW, HLP, IY, FY, PPL, YP, TPP, and MPP.
Examples of suitable substrates include whole milk, skimmed milk, acid casein, rennet casein, acid whey products or cheese whey products, collagen based animal proteins such as gelatine as well as bones or fish-bones . Also, vegetable substrates like wheat gluten, milled barley and protein fractions obtained from, for example, soy, rice or corn are suitable substrates . Mixtures of these may also be used as substrate .
Preferably the substrate is milk or a milk product .
Most preferably the protein substrate is casein . The following caseins are especially suitable as substrate : casein, casein powder, casein powder concentrates, casein powder isolates, or beta-casein, or alpha-s2-casein . Preferably a substrate that has a high content of casein, such as casein protein isolate (CPI) .
The enzyme may be any enzyme that is able to hydrolyse protein substrate resulting in the liberation of one or more of. VPP, IPP, LPP, VY, VF, IW, HLPLP, VAP, AW, LW, HLP, IY, FY, PPL, YP, TPP, and MPP .
A suitable hydrolysate containing ACE inhibiting peptides according to the invention may be obtained by hydrolysis with an endo-protease and a tri-peptidase as described in WO03/102905.
The separation step (b) (or concentration step (c) ) may be executed in any way known to the skilled person, e . g. by precipitation, filtration, centrifugation, extraction or chromatography and combinations thereof . Preferably the separation step (b) is executed using an ultrafiltration (UF) and/or nanofiltration (NF) techniques . The pore size of the membranes used in the filtration step, as well as the charge of the membrane may be used to control the separation of the ACE inhibiting peptides . The fractionation of casein protein hydrolysates using charged UF/NF membranes is described in Y. Poilot et al, Journal of Membrane Science 158 ( 1999) 105-114. Electrodialysis is for instance described in WO00/42066.
Most preferably the separation is executed using acid precipitation .
The concentration/drying step (c) involves drying the fraction from step b) to obtain a solid rich in ACE inhibiting peptide .
This step may be done in a conventional way, e . g. by spray drying or freeze drying.
In a preferred embodiment the product of the separation step is dried until a concentrated solution of hydrolysed protein, having a low Aw is obtained. In such way the formation of off- flavour through Maillard reactions may be avoided.
The fraction rich in peptides prepared in step (b) is hereafter designated as ACE-fraction and the solid prepared in step (c) is hereafter designated as ACE-solid. The ACE-fraction and/or the ACE-solid may advantageously be used as an ingredient in a food product .
The food product according to the invention or food products derived therefrom may be pasteurised or sterilised.
The food products according to the invention may be of any food type . They may comprise common food ingredients in addition to the food product, such as flavour, sugar, fruits, minerals , vitamins, stabilisers , thickeners , etc . in appropriate amounts .
Preferably, the food product comprises 50-200 mmol/kg K+ and/or 15-60 mmol/kg Ca2+ and/or 6-25 mmol/kg Mg2+ more preferably, 100- 150 mmol/kg K+ and/or 30-50 mmol/kg Ca2+ and/or 10-25 mmol/kg Mg2+ and most preferably 110-135 rnmol/kg K+ and/or 35-45 mmol/kg Ca2+ and/or 13-20 mmol/kg Mg2+. These cations have a beneficial effect of further lowering blood pressure when incorporated in the food products according to the invention.
Preferably, the food product comprises one or more phytosterols , phytostanols and/or analogues or derivatives thereof.
Typically, the phytosterols, phytostanols and their analogues and derivatives may be selected from one or more of phytosterols, phytostanols, synthetic analogues of phytosterols and phytostanols and esterified derivatives of any of the foregoing, and mixtures of any of these . The total amount of such substances in a food product or food supplement is preferably from 0.01% to 20%, more preferably from 0.1% to 15%, still more preferably from 0.2% to 8% , and most preferably from 0.3% to 8% by weight of the food product composition .
Preferably, the daily intake of such sterol-type component of the combination is from O . lg to 3g, more preferably from 1.5g to 2.5g, especially from 2g to 2.25g per day.
Phytosterols, also known as plant sterols or vegetable sterols can be classified in three groups, 4-desmethylsterols, 4-monomethylsterols and 4 , 4 ' -dimethylsterols . In oils they mainly exists as free sterols and sterol esters of fatty acids although sterol glucosides and acylated sterol glucosides are also present . There are three maj or phytosterols namely beta-sitosterol, stigmasterol and campesterol . Schematic drawings of the components meant are as given in "Influence of Processing on Sterols of Edible Vegetable Oils" , S . P. Kochhar; Prog. Lipid Res . 22 : pp. 161-188.
The phytostanols are the respective 5α- saturated derivatives of phytosterols such as sitostanol, campestanol and their derivatives .
Synthetic analogues of any of the phytosterols or phytostanols (which include chemically modified natural phytosterols or phytostanols) may be used.
Preferably the phytosterol or phytostanol is selected from the group comprising fatty acid ester of β-sitosterol, β- sitostanol, campesterol, campestanol, stigmasterol, stigmastanol and mixtures thereof.
The optional phytosterol or phytostanol materials recited above may optionally be provided in the form of one or more fatty acid esters thereof. Mixtures of esterified and non-esterified materials may also be used.
Thus, any of the phytosterols, phytostanols and their synthetic analogues used in the present invention are preferably esterified with a fatty acid. Preferably, they are esterified with one or more C2-22 fatty acids . For the purpose of the invention the term C2-22 fatty acid refers to any molecule comprising a C2-22 main chain and at least one acid group . Although not preferred within the present context the C2-22 main chain may contain 1-6 double bonds, be partially substituted or side chains may be present . Preferably, however the C2-22 fatty acids are linear molecules comprising one or two acid group (s ) as end group (s) . Most preferred are linear Ca-22 fatty acids as occur in natural liquid oils . Suitable examples of any such fatty acids are acetic acid, propionic acid, butyric acid, caproic acid, caprylic acid, capric acid. Other suitable acids are for example citric acid, lactic acid, oxalic acid and maleic acid. Most preferred are lauric acid, palmitic acid, stearic acid, arachidic acid, behenic acid, oleic acid, cetoleic acid, erucic acid, elaidic acid, linoleic acid and linolenic acid.
When desired a mixture of fatty acids may be used for esterification of the sterols . For example, it is possible to use a naturally occurring fat or oil as a source of the fatty acid and to carry out the esterification via an interesterification reaction. Use of a natural source nearly always results in a mixture of fatty acids .
In a particular embodiment, the fatty acid mixture contains a high amount (>50%, preferably >70%, further preferred >80%) of unsaturates, being either monounsaturated fatty acids (MUFA) and/or polyunsaturated fatty acids (PUFA) . This does not only provide the advantage of e . g. PUFA itself having good blood cholesterol lowering capacity, but also of the sterols esters prepared with such fatty acids .
Preferably fatty acid mixtures of sunflower, safflower, rapeseed, linseed, olive oil, linola and/or soybean are used.
These are typical sources of high PUFA and/or low SAFA.
Suitable esterification conditions are for example described in
WO 92/19640.
The above described food ingredients, contributing to increasing cardiovascular health, K+, Ca2+ and Mg2+, B-vitamins
( folic acid, Vitamin B2, B6, B12 ) and phytosterols, phytostanols and/or analogues or derivatives thereof are herein collectively referred to as heart health ingredients . Preferably the food products according to the invention are drinks, more preferably fruit juice products or dairy drinks optionally with added fruit juice, dairy type products, frozen confectionary products or spreads/margarines . These preferred types of food products are described in some detail below and in the examples .
• Fruit juice products
Examples of fruit juice products according to the invention are juices derived from citrus fruit like orange and grapefruit, tropical fruits , banana, peach, peer, strawberry, to which ACE- solid and/or ACE-fraction and optionally one or more heart health ingredients are added.
• Dairy type products
Examples of dairy products according to the invention are milk, dairy spreads, cream cheese, milk type drinks and yoghurt, to which ACE-solid and/or ACE-fraction and optionally one or more heart health ingredients are added. The food product may be used as such as a milk type drink. alternatively flavour or other additives may be added. A dairy type product may also be made by adding ACE-solid and/or ACE- fraction to water or to a dairy product .
An example of a composition for a yoghurt type product is about 50-80 wt . % water, 0.1-15 wt . % ACE-solid and optionally one or more heart health ingredients, 0-15 wt . % whey powder, 0-15 wt . % sugar (e . g. sucrose) , 0.01-1 wt . % yoghurt culture, 0-20 wt . % fruit, 0.05-5 wt . % vitamins and minerals, 0-2 wt . % flavour, 0-5 wt . % stabilizer (thickener or gelling agent) . To the yoghurt, fruit may be added. A typical serving size for a yoghurt type product could be from 50 to 250 g, generally from 80 to 200 g.
• Frozen Confectionery Products For the purpose of the invention the term frozen confectionery product includes milk containing frozen confections such as icecream, frozen yoghurt, sherbet, sorbet, ice milk and frozen custard, water-ices, granitas and frozen fruit purees .
Preferably the level of solids in the frozen confection (e. g. sugar, fat, flavouring etc) is more than 3 wt . %, more preferred from 10 to 70 wt . %, for example 40 to 70 wt . % .
Ice cream will typically comprise 0 to 20 wt . % of fat, 0.1 to 20 wt . % ACE-solid and optionally one or more heart health ingredients, sweeteners, 0 to 10 wt . % of non-fat milk components and optional components such as emulsifiers, stabilisers, preservatives, flavouring ingredients, vitamins, minerals, etc, the balance being water. Typically ice cream will be aerated e . g. to an overrun of 20 to 400 %, more specific 40 to 200 % and frozen to a temperature of from -2 to -200 0C, more specific -10 to -30 0C . Ice cream normally comprises calcium at a level of about 0.1 wt% .
• Other food products
Other food product according to the invention can be prepared by the skilled person based on common general knowledge, protein hydrolysate and optionally one or more heart health ingredients in suitable amounts . Examples of such food products are baked goods, dairy type foods, snacks , etc . Advantageously the food product is an oil and water containing emulsion, for instance a spread. Oil and water emulsion is herein defined as an emulsion comprising oil and water and includes oil in water (0/W) emulsions and water in oil emulsions (W/0) and more complex emulsions for instance water- in-oil-in-water (W/O/W/O/W) emulsions . Oil is herein defined as including fat . Preferably the food product is a spread, frozen confection, or sauce . Preferably a spread according to the invention comprises 30-90 wt . % vegetable oil . Advantageously a spread has a pH of 4.2-6.0.

Claims

Claims
1. Food product comprising one or more peptides and one or more B-vitamins, wherein the peptides are chosen from the group consisting of: VPP, IPP, LPP, VY, VF, IW, VAP, AW, LW, HLP, IY, FY, PPL, YP, TPP, MPP; and
(1) wherein the amount of folic acid in the food product is from 0.02μg to 5, 000μg, more preferably from 30μg to l, 000μg, especially from 60μg to 400μg; and/or
(2 ) wherein the amount of vitamin B2 in the food composition is from 0.2 mg to 40 mg, more preferably from 0.24 mg to 8 mg, especially from 0.5 mg to 3.2 mg; and/or .
(3) wherein the amount of vitamin B6 in the food composition is from 0.2 mg to 50 mg, more preferably from 0.3 mg to 10 mg, especially from 0.6 mg to 4 mg; and/or
( 4 ) wherein the amount of vitamin B12 in the food composition is from 0.00001 μg to 25 μg, more preferably from 0.15μg to 5μg, especially from 0.3μg to 2μg .
2. Food product according to claim 1, comprising one or more of VPP, IPP, and LPP .
3. Food product according to any of claims 1-2, wherein the food product is a functional food product .
4. Food product according to any of claims 1-3, being a food product capable of angiotensin-converting enzyme inhibition, said product comprising an amount of 0.1 mg/kg or more of VPP, IPP, LPP, VY, VF, IW, HLPLP, VAP, AW, LW, HLP, IY, FY, PPL, YP, TPP, MPP and one or more of the B- vitamins folic acid, Vitamin B2 , Vitamin B6 and Vitamin B12. 5. Food product according to claim 4 , wherein the amount of peptide is 0.
5 mg/kg or more .
6. Food product according to claim 5, wherein the amount of peptide is 1 mg/kg or more .
7. Food product according to any of claims 1-6, further comprising 50-200 mmol/kg K+ and/or 15-60 mmol/kg Ca2+ and/or 6-25 mmol/kg Mg2+.
8. Food product according to claim 7, comprising 110-135 mmol/kg K+ and/or 35-45 mmol/kg Ca2+ and/or 13-20 mmol/kg Mg2+.
9. Food product according to any of claims 1-8 , comprising 3 to 25 wt% sterol, more preferably from 7 to 15 wt% sterol .
10. Food product according to any of claims 1-9 being selected form the group of drinks, preferably fruit juice products or dairy drinks, dairy products, frozen confectionery products and spreads or margarines .
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US10500245B2 (en) 2014-02-18 2019-12-10 Universite De La Rochelle Compositions for preventing and/or treating pathological conditions associated with alpha-glucosidase
AU2015220649B2 (en) * 2014-02-18 2020-08-13 Universite Blaise Pascal-Clermont Ii Compositions for preventing and/or treating pathological conditions associated with alpha-glucosidase
CN111919963A (en) * 2020-07-10 2020-11-13 青岛农业大学 Method for preparing hydrolysate rich in IPP and VPP from wheat gluten protein by enzyme method
CN111919963B (en) * 2020-07-10 2021-06-01 青岛农业大学 Method for preparing hydrolysate rich in IPP and VPP from wheat gluten protein by enzyme method

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