Oligosaccharide ingredient

FIELD: chemistry.

SUBSTANCE: oligosaccharide ingredient, which is intended to increase content of sialic acid in baby formula, contains glycosylated amino acids and peptides of general formula RnSacm, where R is an amino acid residue, Sac is a monosaccharide selected from a group comprising N-acetyl-neuraminic acid, N-acetyl galactosamine and galactose n has a value from 1 to 10, under the condition that if n=1, then R is a threonine residue or a serine residue and if n has a value between (2) and (10) the peptide contains at least one threonine or serine residue, m has a value from 2 to 4 and at least 20 mol % of the ingredient is N-acetyl-neuraminic acid, where the oligosaccharide component contains 10-25 mol % N-acetyl galactosamine, 10-25 mol % galactose, 20-50 mol % N-acetyl-neuraminic acid and 15-50 mol % threonine or serine or mixture thereof.

EFFECT: obtaining an oligosaccharide ingredient intended for increasing content of sialic acid in baby formula.

6 cl, 2 ex

 

The technical field to which the invention relates.

The present invention relates to an oligosaccharide ingredient with a high content of sialic acid, foods that contain the specified oligosaccharide ingredient, and methods of production of the specified oligosaccharide ingredient.

The level of technology

It is known that breast milk contains a large number of not digested oligosaccharides. Actually nevereverever oligosaccharides are the third largest solid component (after lactose and lipids) breast milk contains colostrum at a concentration of 12-15 g/l, and in Mature milk at a concentration of 5-8 g/L. breast milk Oligosaccharides are resistant to enzymatic hydrolysis, which suggests that these oligosaccharides can have vital functions, not directly related to their energy value.

Over the past two decades, the chemical structure of breast milk oligosaccharides studied by NMR spectroscopy and mass spectrometry. Each individual oligosaccharide is based on a combination of glucose, galactose, sialic acid (N-acetylneuraminic acid), fucose and/or N-acetylglucosamine, which are connected in many different ways, which leads to a huge number of different oligosacharide is found in breast milk - to date, identified more than 130 of these structures. Almost all of them have a fragment of lactose to pampering the end, while sialic acid (in case of its presence) occupies a terminal position on the non-end.

Of particular interest is the large number sililirovany oligosaccharides in breast milk. Sialic acid is debatepedia sugar, which represents an essential structural and functional component of gangliosides in the brain. It is believed that it plays an important role in the momentum transfer nerve cells, the formation of memory and the contacts between the cells. Studies in young rats showed that the addition of sialic acid at an early age increases the content of sialic acids in gangliosides of the brain and improves learning ability in well-nourished and malnourished animals, and that these changes persist into adulthood.

Breast milk is recommended for all infants. However, in some cases, breastfeeding is not enough or it unsuccessfully for medical reasons, or mother chooses not to breastfeed. For such cases were developed mixture for baby food. However, cow's milk, which is typically used as the basis for commercially available mixtures for detskogo the power has much less content sililirovany oligosaccharides compared with mother's milk. As the composition of breast milk and functions of the individual components are becoming better understood, it becomes apparent that it may be desirable to increase the content of sialic acid in children mixtures based on cow's milk.

There are several known sources of sialic acids, including N-acetylneuraminic acid, sialyllactose and other sililirovanie oligosaccharides containing sialic acid gangliosides and protein casinolocated. Casinolocated or CGMP is a large carbohydrate-rich, hydrophilic protein, the C-terminal fragment of the K-casein, from which it can be split enzymatically or by treatment with acid. In the application US 2005/0096295 proposed to improve the content of sialic acid in children mixtures by incorporating new CGMP ingredient with increased concentration of sialic acid. This ingredient has the content of sialic acid above 60 mg/g of protein, compared to 40-60 mg/g of protein in natural CGMP. It can be obtained either by fractionation using anion chromatography, or a partial hydrolysis with subsequent fractionation using anion chromatography.

However, it remains potrebnosti get other ingredients, rich in sialic acid, which can be used for enrichment of infant formula and other nutritional compositions specified an important component.

The invention

In the present invention are described oligosaccharide ingredient containing glycosylated amino acids and proteins the General formula RnSacmwhere R represents the balance of amino acids, Sac is a monosaccharide selected from the group consisting of N-acetylneuraminic acid, N-atsetilgalaktozamin and galactose, n has a value from 1 to 10, provided that when n=1, then R is a threonine residue or a serine residue and if n has a value from 2 to 10, the peptide contains at least one residue is threonine or serine, m has a value from 2 to 4, and at least 20 mol.% this ingredient is an N-acetylneuraminic acid.

Described ingredient is a new ingredient in the food category of quality, rich in sialic acid, which is suitable to add in the nutritional composition, such as a mixture of baby food, to increase the content of sialic acid in the composition.

The present invention also encompasses a method for the production of oligosaccharide ingredient containing glycosylated amino acids and proteins the General formula RnSacmwhere R represents the STATCOM amino acids, Sac is a monosaccharide selected from the group consisting of N-acetylneuraminic acid, N-atsetilgalaktozamin and galactose, n has a value from 1 to 10, provided that when n=1, then R is a threonine residue or a serine residue and if n has a value from 2 to 10, the peptide contains at least one residue is threonine or serine, m has a value from 2 to 4, and at least 20 mol.% this ingredient is an N-acetylneuraminic acid that includes a hydrolysis step of casinolocated using ectoprocta and endoprotease with the mixture of free amino acids and proteins with chain length from 2 to 10, and nanofiltration received the hydrolyzed mixture with retention fraction having a molecular weight of 1000-2000 Yes.

The present invention also includes a food product containing the above oligosaccharide ingredient. In particular, this food product is a baby food or infant formula, but this product may be any food or drink consumed by children, infants or adults. Consumption of food containing such oligosaccharide ingredient can improve the incorporation of sialic acids in gangliosides of the brain, and thereby improve the corresponding functions of the neurons, such as neurotransmission is.

Disclosure of inventions

In the present description listed next to the words have definitions that need to be taken into account when reading and interpretation of the description, examples and claims.

"CGMP": casinolocated, i.e. glycomacropeptide, which is cleaved from bovine K-casein by the action of the enzyme rennin.

"Infant formula": food for a balanced diet of infants during the first 1-6 months of their life, and for partial power after this period. This term includes mixtures for the initial period of feeding and for subsequent feeding period.

"Sialic acid"N-acetylneuraminic acid.

In the present invention are described oligosaccharide ingredient containing glycosylated amino acids and proteins the General formula RnSaCmwhere R represents the balance of amino acids. Sac is a monosaccharide selected from the group consisting of N-acetylneuraminic acid, N-atsetilgalaktozamin and galactose, n has a value from 1 to 10, provided that when n=1, then R is a threonine residue or a serine residue and if n has a value from 2 to 10, the peptide contains at least one residue is threonine or serine, m has a value from 2 to 4, and at least 20 mol.% this ingredient is an N-acetil erminology acid, and food for children or adults, containing such oligosaccharide ingredient.

Preferably, n has a value of 1-3, and m has a value of 3 or 4.

Described ingredient contains at least 20 mol.% sialic acid as part sacharides chain associated with a hydroxyl group of threonine or serine. Sialic acid can form part of the chain, or may itself be a Deputy monosaccharide fragment in the chain. So, oligosaccharide ingredient may contain the following monosaccharides:

ConnectionMol.%
N-atsetilgalaktozamin (GalNAc)10-25
Galactose (Gal) g10-25
N-acetylneuraminic acid (NeuAc)50-20

Oligosaccharide ingredient may contain from 15 to 50 mol.% a mixture of serine and/or threonine.

Oligosaccharide ingredient may contain the following glycosylated amino acids or peptides:

NeuAc-α-2,3-Gal-β-l,3-(NeuAc-α-2,6-)-GalNAc-Rn

NeuAc-α-2,3-Gal-β-1,3-GalNAc-Rn

Gal-β-l,3-(NeuAc-α-2,6-)-GalNAc-Rn

Gal-β-l,3-GalNAc-Rn

Oligosaccharide ingredient of the present invention can be obtained hydro is Isom CGMP using ectoprocta and endoprotease with the mixture of free amino acids and proteins with chain length from 2 to 10, and nanofiltration received the hydrolyzed mixture with retention fraction having a molecular weight of 1000 to 2000 daltons.

CGMP itself is a byproduct of cheese making, in which whole milk is treated with the enzyme rendina to precipitate the casein. In this process, CGMP cleaved from K-casein and remains in solution with whey protein. This product is known as sweet whey. CGMP can be separated from whey protein by any method known in the art. A suitable method is described in patent EP 986312.

The hydrolysis can be accomplished using any appropriate combination of enzymes. One example of a commercially available enzymatic system with Exo - and endoprotease activity is the product sold under the trademark Flavourzyme® office Novozymes company Novo Nordisk.

The product of hydrolysis is a mixture of free amino acids, glycosylated threonine and serine, glycosylated peptides containing at least one residue is threonine or serine, and deglycosylated peptides, and the peptides are in the chain from 2 to 10 amino acid residues. The resulting mixture is subjected to nanofiltration for the separation and retention fraction, having a molecular weight in the range from 1000 to 2000 daltons. This fraction is oligosaccharide ingredient for infusion is his invention.

In a preferred aspect of the present invention described above oligosaccharide ingredient is injected into the food product. In the context of the present invention, the term "food product" includes any usable products. Thus, it can be a product designed for human consumption, in particular the mixture for infants, the mixture for later feeding, baby food, such as porridge for infant feeding, etc. In particular, oligosaccharide ingredient of the present invention can be included in the composition of mixtures for infants, infant formula for children 1-3 years of age and milk powder or grain mixtures.

The food product can be prepared by any method known in the art, in accordance with the type of product, and oligosaccharide ingredient of the present invention can be added to the product at appropriate stages of the production process. For example, a mixture for infants can be prepared by mixing in suitable proportions source of protein, any of carbohydrates other than lactose, and fat source. Optionally, you can add emulsifiers. At this point you can add vitamins and minerals, but usually they are added later in order to avoid thermal destruction. Any lipophilic vitamins, emulsifiers, etc. can be settled before mixing to dissolve the source of fat. You can then add water, preferably passed through reverse osmosis to form a liquid mixture.

The liquid mixture can then be thermally processed to reduce levels of bacteria. For example, the liquid mixture can be quickly heated to a temperature in the range from about 80°to about 110°C for a period of time from about 5 seconds to about 5 minutes. This can be done by injection of steam or by using a heat exchanger, for example a plate heat exchanger.

Then, the liquid mixture can be cooled to a temperature of from about 60°to about 85°C., for example, by instant cooling. Then, the liquid mixture can be homogenized, for example, in two stages: at a pressure of from about 7 MPa to about 40 MPa in the first stage, and from about 2 MPa to about 14 MPa in the second stage. Gomogenizirovannogo mixture can then be cooled to add heat-sensitive components, such as vitamins and minerals. Usually at this point in time, pH and dry matter content of a homogenized mixture of traditionally lead to default values.

Gomogenizirovannogo the mixture is transferred into a suitable dryer such as a spray drier or freeze drier, and turned into powder. The resulting powder should have a moisture content less than about 5 wt.%.

Oligosaccharide ingredient present is Adamu invention can be added directly to a mixture of baby food by dry mixing, or, if the mixture has a liquid consistency, in the above-described stage of mixing. In both cases, a qualified specialist will be clear that the addition of this ingredient entails the simultaneous addition of a certain amount of amino nitrogen, and therefore may be necessary to adjust the protein content in the mixture for baby food or other products, to which is added the ingredient in question. The resolved protein content and amino acid profile of the mixtures specified in legislative acts, such as the European Commission Directive 91/3 21/EEC of 14 may 1991, and a qualified expert in this field will easily be able to adjust the protein content and amino acid profile of a mixture of baby food with regard to additional amino nitrogen introduced with the ingredient of the present invention, as well as additional content of threonine and serine.

The final concentration of oligosaccharide ingredient in the food product for feeding children or infants may be from 0.2 to 4.0 wt.%, preferably from 0.5 to 2.0 wt.% to the weight of dry matter. However, the above values should not be considered as limiting, and should be adapted to specific target audiences, for example, based on the weight and the age or health of the child or infant. Preference is sustained fashion, blend or food product containing oligosaccharide ingredient of the present invention, give the baby at each feeding.

Although preferably the introduction of the described additives in food products designed specifically for babies or infants, a positive effect can be adding the described additives in foods that do not have a specific target audience, or in food products intended for adults. For example, oligosaccharide ingredient of the present invention can be introduced into the composition of food for the sick and food for the elderly. Such foods may include, among others, milk, yogurt, curd, cheese, fermented milk products, fermented milk products, ice cream, fermented foods based on cereals or products on milk basis. In addition to the oligosaccharide ingredient of the present invention a food product, such as infant formula may contain one or more oligosaccharides, which is added separately.

The present invention will be further illustrated using the following examples.

Example 1

The following is an example of the composition of the mixture for baby food containing oligosaccharide ingredient of the present invention.

Nutrient100 kcal1 liter
Energy value (kcal)100670
Protein (g)1,8312,3
Fat (g)5,335,7
Linoleic acid (g)0,795,3
α-linolenic acid (mg)101675
Lactose (g)11,274,7
Oligosaccharide ingredient(g)0,151,0
Minerals (g)0,372,5
Na (mg)23150
K (mg)89590
CL (mg)64430
CA (mg)62410
P (mg)31210
Mg (mg)750
Mn (µg)850
Se (µg)213

Vitamin a (µg RE)105700
Vitamin D (µg)1,510
Vitamin E (mg TE)0,8of 5.4
Vitamin K1 (μg)854
Vitamin C (mg)1067
Vitamin B1 (mg)0,070,47
Vitamin B2 (mg)0,151,0
Niacin (mg) 16,7
Vitamin B6 (mg)0,0750,50
Folic acid (µg)960
Pantothenic acid (mg)0,453
Vitamin b 12 (g)0,32
Biotin (µg)2,215
Choline (mg)1067
Fe (mg)1,28
I(g)15100
Cu (mg)0,060,4
Zn (mg)0,755

Example 2

50 g of casinolocated (Biopure GMP, Davisco, USA) was dissolved at a concentration of 10% (wt./about.) in 500 ml of deionized water. The resulting solution was heated for 30 minutes at 40°C with careful stirring and recirculation through l the responsibility system of tangential flow filtration (Millipore, USA) with one filter cartridge Pellicon 1000 daltons (0.1 m3) when the inlet pressure of 1.2 bar and the lack of pressure retentate.

Then added aminopeptidase from Aspergillus oryzae (Flavourzyme 1000L containing 1000 units of amino peptidases per gram (LAPU/r), Novozymes, Denmark) in the amount of 3500 LAPU 50 grams of protein. After about an hour started diafiltration, increasing the pressure retentate to 3 bar inlet pressure of 3 bar. After 5 hours was stopped by filtration and collected retentate. Retentate and 7 fractions of the filtrate collected during the process, liofilizovane. Then determined the dry matter content (DM) of sialic acid in each fraction. The content of sialic acid was determined after mild acid hydrolysis, and the introduction of labels, using the method DMB (1.2-diamino-4,5-methylenedioxybenzene the dihydrochloride) and analysis by HPLC with reversed-phase column Shodex 18 and fluorescence detection, using authentic NeuAc as an external standard. Table 1 shows the mass balance and the content of sialic acid in the source material, the fractions of the filtrate and retentate.

Table 1
Weight (g)NeuAc (% dry matter)Output (%) enrichment
Source material507,51001,00
The filtrate 14,320,28,640,03
The filtrate 23,10,26,20,02
The filtrate 36,10,312,20,04
The filtrate 44,291,48,580,18
The filtrate 5of 3.560,87,120,10
The filtrate 62,80,45,60,05
The filtrate 72,940,35,880,04
Retentate22,614.445,21,92

The content of galactose and N-atsetilgalaktozamin in retentate was determined after acid hydrolysis using high-performance anion-exchange chromatography (NRAES) using analytical column Dionex CarboPac PA1 and a pulsed amperometric detector. Briefly, retentate was dissolved in water and added triperoxonane acid to a final concentration of 2M. The solution was heated for 3 hours at 100°C, dried in a stream of nitrogen and was again dissolved in water. The sample was analyzed after filtration through a fine filter with a pore size of 22 μm. Quantification was performed using authentic galactose and galactosamine (N-atsetilgalaktozamin becomes galactosamine during processing acid) as external standards. Threonine is quantitatively determined by HPLC after acid hydrolysis in 6 BC model HC1.

The final dried product retentate contained 29,6 wt.% (NeuAc)2-3-Gal-GalNAc-Thr with type structure NeuAc-α-2,3-Gal-β-l,3-(NeuAc-α-2,6-)-GalNAc-threonine/peptide with 30 mol.% sialic acid, 15 mol.% galactose, 13 mol.% N-atsetilgalaktozamin and 42 mol.% threonine.

1. Oligosaccharide ingredient that is intended to increase the content of sialic acid in mixtures for detsk the th power, containing glycosylated amino acids and peptides of the General formula RnSacmwhere R is an amino acid residue, Sac is a monosaccharide selected from the group consisting of N-acetylneuraminic acid, N-atsetilgalaktozamin and galactose, n has a value from 1 to 10, provided that when n=1, then R is the residue of threonine or serine, and if n has a value from 2 to 10, the peptide contains at least one residue is threonine or serine, m has a value from 2 to 4, and N-acetylneuraminic acid comprises at least 20 mol.% ingredient, where the oligosaccharide component contains from 10 to 25 mol.% N-atsetilgalaktozamin, from 10 to 25 mol.% galactose, from 20 to 50 mol.% N-acetylneuraminic acid and from 15 to 50 mol.% threonine or serine, or a mixture thereof.

2. Oligosaccharide ingredient according to claim 1, in which n has a value from 1 to 3.

3. Oligosaccharide ingredient according to claim 1, in which m has the value 2 or 3.

4. The infant formula containing oligosaccharide ingredient according to any one of claims 1 to 3.

5. The infant formula according to claim 4, which contains from 0.2 to 4.0 wt.% oligosaccharide ingredient.

6. Method for the production of oligosaccharide ingredient according to any one of claims 1 to 3, which includes a step of hydrolysis of casinolocated using ectoprocta and endoprotease to obtain a mixture of free amino acids and peptides with the Lina chain from 2 to 10 and the stage nanofiltration obtained hydrolyzed mixture for sampling fractions, having a molecular weight of 1000-2000 Yes.



 

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2 cl, 2 ex

FIELD: cosmetics, pharmacy.

SUBSTANCE: invention relates to associates containing trehalose and calcium chloride as a crystalline monohydrate comprising above said components and water in the molar ratio = 1:1:1, or as anhydrous crystal containing above said components in the molar ratio = 1:2. Indicated crystals of two species of associates of trehalose and calcium chloride can be used in different branches in production of foodstuffs, cosmetic agents and others.

EFFECT: valuable properties of compounds.

3 cl, 20 tbl, 15 dwg, 30 ex

FIELD: biotechnology, biochemistry, enzymes.

SUBSTANCE: invention relates to a method for preparing 4-O-β-D-galactopyranosyl-D-xylose used for in vivo assay of lactase activity in human intestine. Method involves interaction of D-xylose with β-D-galactopyranoside for 2-48 h in a solution at pH 5-9, at temperature that changes from the mixture freezing point to 45°C, and the following addition of 10-1000 U of β-D-galactosidase per 1 g of β-D-galactopyranoside. Reaction is terminated by inactivation of enzyme followed by isolation and crystallization of fraction containing 4-O-β-D-galactopyranosyl-D-xylose in the crystallization mixture chosen from acetone/methanol = (5-1):(20-1) and acetone/water = (5-1):(20-1). Invention provides increasing content of 4-O-β-D-galactopyranosyl-D-xylose in the final mixture.

EFFECT: improved preparing method.

42 cl, 2 tbl, 9 ex

The invention relates to food industry, namely breast

The invention relates to new derivatives of 3-deoxyanthocyanins formula I, in which X denotes a radical of the formula V or a radical of the formula C; Y denotes a radical of the formula D; R1, R3, R5, R7, R8, R10, R13- the same or different, represent each a linear or branched CNS radical with 1-6 C-atoms or the radical-OSO-3; R2, R4, R6, R9, R11- the same or different, represent each a hydrogen atom, a linear or branched CNS radical with 1-6 C-atoms or the radical-OSO-3, R12means a hydroxyl radical or a radical-OSO-3however , provided that at least one of the substituents R2or R4or R6or R9or R11denotes a hydrogen atom; in the form of pharmaceutically acceptable salts and the corresponding acids

FIELD: medicine.

SUBSTANCE: group of inventions refers to medicine, namely to paediatrics and may be used for preparing a composition for oral administration into an infant born by Cesarean section. This purpose is achieved by using at least one microorganism, and at least one nondigestible oligosaccharide. The composition contains at least one species Bifidobacteria specified in a group consisting of Bifidobacterium breve, Bifidobacterium infantis, Bifidobacterium bifidum, Bifidobacterium catenulatum, Bifidobacterium adolescentis and Bifidobacterium longum and galactooligosaccharides as an oligosaccharide. What is also presented is a method for preparing the infant food suitable for the infant born by Cesarean section.

EFFECT: group of inventions provides the general population Bifidobacteria growth in 2,5 times and increase of the various strains Bifidobacteria, thereby providing a greater variety of Bifidobacterium.

9 cl, 2 tbl, 6 ex

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