WO2004107875A1

WO2004107875A1 - Phospholipid-containing emulsifiable composition

Info

Publication number: WO2004107875A1
Application number: PCT/JP2004/008180
Authority: WO
Inventors: Misa Shiihara; Xiaoli Liu; Naruyuki Taniwaki
Original assignee: Nagase Chemtex Corporation
Priority date: 2003-06-06
Filing date: 2004-06-04
Publication date: 2004-12-16

Abstract

A phospholipid-containing emulsifiable composition which comprises phosphatidylserine, phosphatidylinosytol, and a neutral phospholipid and has excellent emulsifiability. In the composition, the phosphatidylserine and the phosphatidylinosytol are contained in amounts of 5 to 85 wt.% and 2.5 to 30 wt.%, respectively, based on all phospholipids. The amount of all acidic phospholipids contained, including the phosphatidylserine and phosphatidylinosytol, is 1.0 to 7.4 parts by weight per part by weight of the neutral phospholipid.

Description

Phospholipid-containing emulsifying composition

Technical field

The present invention relates to a phospholipid-containing emulsifiable composition containing phosphatidylserine and having excellent emulsifiability.

Akita

Background art

Phosphatidylserine (hereinafter sometimes abbreviated as PS) is a type of acidic phospholipid and is a substance that is commonly found in plants and animals. In recent years, it has been reported that brain function is improved by taking PS at a rate of 100 to 300 mg Z days (Amaducci L. and the SMID group, Phychophar macol. Bull., 24, pl30 -134, 1988 and Cenacchi T. et. Al., Aging Clin. Exp. Res., 5, pl23-133, 1993). PS has been known to have an antidepressant action, an anti-stress action, and an action of suppressing cortisol, a hormone that causes muscle tissue depletion. These effects have attracted attention and are widely used in nutritional supplements for sports, health foods for menopause, mood-in proofers, etc. (US Pat. No. 6,410,522 and US Pat. (See 19767)). As described above, PS has been attracting attention as a multifunctional food component more than a mere nutritional component.

Ps in phospholipids, a natural component, does not exceed a few percent in plants and more than 20% in the brains of animals, which are considered the most common. For this reason, it is difficult to ingest from the diet enough PS to exert physiological functions, and it is a practical method to supplementally ingest materials containing high concentrations of PS. Material containing high concentration of PS As a method for obtaining the raw material, there are a method of fractionating phospholipids extracted from natural products, and a method of producing phosphatidyl group by a phosphatidyl group transfer reaction from other compounds to serine. There are various methods for ingesting PS, such as intravenous administration and oral administration.In the case of oral administration, for example, mixing with other excipients such as phospholipids, sugars, and proteins will improve the ease of handling and storage. Formulations added to improved capsules and granules are used. Furthermore, since there is no problem in terms of safety, PS may be added to foods and drinks taken daily.

However, PS or a phospholipid-containing material containing a high concentration of PS has low solubility in fats and oils (such as soybean oil), and even if it is dissolved by applying heat, it hardens when the temperature drops, and foods This is not preferable in producing In addition, its low solubility in water makes it difficult to handle. For this reason, PS is mainly used as a capsule or granular preparation (see Shinsei Kagaku Kenkyusho 4, 1 Lipid II Phospholipid, edited by The Biochemical Society of Japan, p. 549, Tokyo Kagaku Dojin (1991)).

As described above, PS is useful as a material for health foods and the like, but its application range is limited due to its low solubility in oils and fats and low water solubility. On the other hand, it is conceivable that PS is emulsified with an emulsifier or a surfactant to be contained in food. As food additives that can be used in foods, pharmaceuticals, etc., lecithin, sucrose fatty acid esters, glycerin fatty acid esters, sorbitanic acid esters, propylene glycol fatty acid esters, and the like are widely used. Among them, like the above PS, a lecithin is preferred from the viewpoint of being a lipid and a natural emulsifier, but relatively mild foods such as fatty acid monoglyceride, sucrose fatty acid ester, and polyglycerin fatty acid ester are preferable. There is a disadvantage that the emulsion stability is inferior to that of the additive surfactant. As a result of studying the modification of lecithin, it contains phosphatidylglycerol (hereinafter sometimes abbreviated as PG), which has improved emulsifying ability and emulsifying stabilizing ability compared to lecithin. An emulsifying material for foods containing lysolecithin (hereinafter sometimes abbreviated as LPL) has been reported (Japanese Patent Application Laid-Open No. 61-19949749, See Japanese Patent Application Laid-Open Nos. 7-28993 and 6-090663). However, it is necessary to perform emulsification by adding these emulsifiers, and the operation is complicated.

Disclosure of the invention

An object of the present invention is to solve the above problems, and an object of the present invention is to provide an emulsifying composition capable of effectively emulsifying PS. Another object of the present invention is to provide an emulsifiable yarn composition capable of blending Ps in a food or drink without using a commonly used emulsifier, surfactant or the like, and the composition. It is to provide a food containing.

The present inventors have conducted intensive studies to solve the above problems, and as a result, have found that a predetermined composition containing PS and phosphatidylinositol (hereinafter sometimes abbreviated as PI) has excellent emulsifying function and high stability. And found that this invention was completed.

The first phospholipid-containing emulsifiable composition of the present invention contains phosphatidylserine, phosphatidylinositol, and neutral phospholipid, and the composition contains, based on the weight of the entire phospholipid, phosphatidylserine 5-8 5 by weight ^_0/0, and phosphatidylinositol are containing organic at a rate of 2.5 to 3 0 wt ^_0/0, and with respect to the neutral phospholipid 1 part by weight, the phosphatidylserine And acidic phospholipids including phosphatidylinositol in a total amount of 1.0 to 7.4 parts by weight.

The second phospholipid-containing emulsifiable composition of the present invention contains phosphatidylserine, phosphatidylinositol, and phosphatidic acid, and the composition contains the phosphatidylserine based on the weight of the entire phospholipid. Is 5 ~ 8 5 weight ^_0/0 and phosphatidylinositol 2,. 5-3 0 is in a weight percent proportion, and when the weight of total phospholipid, total weight of phosphatidyl phosphate Contact Yopi phosphatidylinositol Ranges from more than 2.5% to 36% by weight.

The present invention includes a food containing the first or second phospholipid-containing emulsifiable composition.

BEST MODE FOR CARRYING OUT THE INVENTION

The first emulsifiable phospholipid-containing composition of the present invention contains acidic phospholipids of PS and PI, and a neutral phospholipid, and optionally contains acidic phospholipids other than PS and PI. The second phospholipid-containing emulsifiable composition of the present invention contains PS, PI, and phosphatidic acid (hereinafter, may be abbreviated as PA), and optionally contains other than PS, PI, and PA. Contains acidic phospholipids, neutral phospholipids, etc. Furthermore, these first and second emulsifiable compositions may contain general-purpose emulsifiers, additives and the like.

The origin of the PS contained in the first and second compositions of the present invention is not particularly limited. For example, PS derived from plants such as soybean, wheat, barley, corn, castor, rape, peanut, cottonseed, and rice; PS derived from yolk; PS derived from animal brain such as cow, pig, sheep, chicken, fish, etc. PS; PS derived from microorganisms such as yeast; and PS derived from animal meat or offal such as chicken, chicken offal, fish body, fish meat and the like can be used. From these raw materials, for example, the Folch method (see J. Folch, I. Ascoli, M. Lees, JA Meath, FN LeBaron, J. Biol. Chem., 191, 833 (1951)), the Bligh-Dyer method (EG Blig, WJ Dyer, Can. J. Biochem. Physiol., 37, 911 (1959)) and the like. Alternatively, PS is a compound having a phosphatidyl group, for example, a phosphatidyl group transfer reaction between phosphatidylcholine and L-serine, or It can be produced by other organic synthesis methods.

PS is contained in a proportion of 5 to 85% by weight, preferably 7 to 30% by weight, based on the total weight of the phospholipid contained in the composition of the present invention. If the amount is less than 5% by weight or exceeds 85% by weight, problems may occur in terms of a decrease in emulsifying power and a decrease in emulsion stability. The purity of PS used is not particularly limited, and it is preferable to include the PS so that the final phospholipid composition in the composition falls within a desired range. Therefore, it is possible to use any of the purified PS, the above extract, the fractionated concentrate of the extract, and the product obtained by synthesis.

PI contained in the composition of the present invention, like PS, is a kind of acidic phospholipid and usually widely exists mainly as a component of cell membranes of animals, plants, microorganisms and the like. In particular, the content is high in plant seeds such as soybean, rapeseed and linseed, and yeast. PI is a substance that is involved in the signaling of cells in vivo and is attracting attention in physiology along with its lysate (J.EA.Bleasdale, et al (eds), Inositol and Phosphoinositides, Humana Press, 1985) See). Furthermore, it has been reported that as a component of oils and fats for heating cooking, it shows excellent action in flavor and release properties (Japanese Patent Application Laid-Open Nos. 4-330253 and 5-116680). No. 4).

The origin of the PI used in the present invention is not particularly limited. For example, PI derived from plants such as soybean, wheat, barley, corn, castor, rape, peanut, cottonseed, and rice; PI derived from egg yolk; PI derived from animal brain such as cow, pig, sheep, chicken, fish, etc. Any of PI derived from microorganisms such as yeast; and PI derived from animal meat or offal such as chicken, chicken offal, fish body, fish meat and the like. It can be obtained by concentrating extracts obtained from these raw materials by, for example, the Folch method or the Bligh-Dyer method. Specifically, the cell thread is homogenized by a conventional method, and a lipid component is obtained by a method such as fractionation or extraction. When treated with an adsorbent such as silica gel or a liquefied gas under supercritical conditions, the mixed phospholipids can be concentrated and purified to the purity used in the present invention through the state of the mixed phospholipid. Alternatively, PI can be produced by an organic synthesis method.

PI is contained in a proportion of 2.5 to 30% by weight based on the total weight of the phospholipid contained in the composition of the present invention. If the amount is less than 2.5% by weight or exceeds 30% by weight, problems may occur in terms of a decrease in emulsifying power and a decrease in emulsion stability. The purity of the PI used is not particularly limited, and it is preferable to include the PI so that the final phospholipid composition in the composition falls within a desired range.

Neutral phospholipids that can be contained in the composition of the present invention include phosphatidylcholine (hereinafter sometimes abbreviated as PC), phosphatidylethanolamine (hereinafter sometimes abbreviated as PE), lysolecithin (hereinafter, abbreviated as PE). (Sometimes abbreviated as LPL; lysolecithin may be an acidic phospholipid). The first phospholipid-containing emulsifying composition of the present invention preferably contains 1.0 to 7.4 parts by weight of an acidic phospholipid with respect to 1 part by weight of the neutral phospholipid. If the amount of the acidic phospholipid is less than 1.0 part by weight or exceeds 7.4 parts by weight, inconvenience may occur in terms of a reduction in emulsifying power and a reduction in emulsification stability. is there.

When the above-mentioned lysolecithin (LPL) is contained in the phospholipid-containing emulsifiable composition of the present invention, its content is 5% by weight or less from the viewpoint of preventing a decrease in emulsifying power and emulsion stability. Preferably, there is.

PA which can be contained in the composition of the present invention is an acidic phospholipid like PS and PI described above. The origin of this PA is not particularly limited. For example, PA from plants such as soybean, wheat, barley, corn, castor, rape, peanut, cottonseed, and rice; PA from egg yolk, PA from animal brain such as cow, pig, sheep, chicken, fish, and yeast; yeast. Microorganisms such as PA; and animals such as chicken, chicken offal, fish, and fish meat Either meat or offal-derived PA can be used, and it can be obtained by concentrating an extract obtained from these raw materials by, for example, the above-mentioned Folch method or Bligh-Dyer method. Alternatively, PA may be produced by a hydrolysis reaction using phospholipase D (PLD), or may be obtained by fractionating and concentrating them, or may be produced by an organic synthesis method.

When PA is contained in the composition, the PA is preferably contained in a proportion of 1.0 to 15.0% by weight based on the total weight of the phospholipid. By containing PA, the emulsifying power can be further increased. Further, in this composition, the total weight of PA and PI preferably ranges from more than 2.5% to 36% by weight, more preferably 19% by weight, based on the total weight of the phospholipid. ~ 36% by weight. If the total weight is less than 2.5% by weight, or if it exceeds 36% by weight, inconvenience may occur in terms of a decrease in emulsifying power and emulsion stability. The purity of the PA used is not particularly limited, and it is preferable that the final phospholipid thread in the composition is contained in a desired range.

Examples of the general-purpose emulsifier contained in the phospholipid-containing emulsifying composition of the present invention include sucrose fatty acid esters.

The phospholipid-containing emulsifiable composition of the present invention is suitably used for emulsification of fats and oils, particularly for producing emulsified foods containing a large amount of fats and oils. The type of the fat is not particularly limited, and may be any fat or oil that is liquid at normal temperature. For example, vegetable oils such as soybean oil, corn oil, safflower oil, olive oil, and peanut oil; animal oils such as fish oil; oils such as medium-chain fatty acid triglycerides produced by ester synthesis using enzymes. .

The method for emulsifying fats and oils using the phospholipid-containing emulsifiable composition of the present invention is not particularly limited, and it is not necessary to employ a special emulsification method. For example, by using almost the same as a conventional emulsifier consisting of soybean lecithin, which is a phospholipid mixture, Fats and oils can be emulsified. Specifically, for example, each component of the composition of the present invention is added to and dissolved in fats and oils to be emulsified, and mixed with water or an aqueous solution of another material to emulsify. At this time, if a water-soluble emulsifier (preferably an emulsifier having an HLB power of S5 or more; for example, a sucrose fatty acid ester) is added to the aqueous layer, emulsification becomes easy. A homogenizer, ultrasonic waves, or the like can be used for mixing, and the mixture can be heated to a temperature of about 50 ° C. or higher during the treatment. In the case of producing a food containing the composition of the present invention, an emulsion is prepared in advance by mixing each component of the composition with a fat (liquid fat) to be contained in the food. May be mixed with other components of the food, or emulsification may be directly performed using each component of the composition and a component to be contained in the food.

Foods containing the phospholipid-containing emulsifiable composition of the present invention are not particularly limited, but are preferably dairy products such as ice cream, cheese, powdered milk, pudding, and taroim; breads, cakes, and biscuits. And flour-containing foods such as coconut and ；; margarine, mayonnaise, chocolate, fried (for example, pork), and tempura-containing foods; and beverages such as canned coffee, soy milk, milk, and cocoa. The shape of the food product is not particularly limited. For example, the food product can be used as retort food (food obtained by pressurizing plastic bag-packed food or canned food). Furthermore, this food can be used as a health food (a food containing ingredients for promoting health, such as peptides, oligosaccharides, DHA, and aloe).

The content of the composition of the present invention in the food varies depending on the type of food, processing conditions, and the like, but is, for example, 0.001 to 5% by weight, and preferably 0.01 to 2% by weight. The content of fats and oils in foods is not particularly limited, but is usually 4 to 90% by weight, preferably 4 to 75% by weight, and the water content is usually 9 to 95% by weight, preferably 25 to 25% by weight. ~ 95% by weight. Since the first and second phospholipid-containing emulsifying compositions of the present invention both have a specific composition containing PS and PI, they have excellent emulsifying ability and emulsifying stability. ? 3 hours? 1 has low solubility in fats and oils (for example, soybean oil) and water, and is difficult to contain in a stable state in foods, for example. However, a stable emulsified state can be obtained by using the composition of the present invention having a specific composition having these in combination. Therefore, a stable emulsified food can be obtained by using this, and daily ingestion of PS becomes very easy.

(Example)

Hereinafter, the present invention will be described based on examples, but the present invention is not limited to these examples.

Example 1

Phosphorus is converted from commercially available soy lecithin (product name: BHN PS-20P, manufactured by B.A.C.H.) by the Bligh-Dyer method (see EG Bligh, WJ Dyer, Can. J. Biochem. Physiol., 37, 911 (1959)). The lipid was extracted. Commercially available soybean lecithin (Product name: SLP-PC70, manufactured by Tsuru-Lecithin Industry Co., Ltd., Product name: SLP-PI powder-1, manufactured by Tsuru-Lecithin Industry Co., Ltd .; Product name: SLP White, Tsuru-Lecithin Industry Co., Ltd. Was used without extraction. Separately, another commercially available soybean lecithin (product name: SLP-PC70, made by Tsuruichi Lecithin Industry Co., Ltd.) was hydrolyzed with phospholipidase D (PLD) to obtain hydrolyzed lecithin.

The extracted phospholipid, soybean lecithin (SLP-PC70), and hydrolyzed lecithin were appropriately mixed to obtain a phospholipid-containing emulsifiable material having the composition shown in Table 1. The ratio of each phospholipid in Table 1 is the content (% by weight) based on the total weight of the phospholipid in the obtained emulsifiable material.

1 g of this phospholipid-containing emulsifying material is added to 74 m1 of soybean oil and 25 m1 of water, and the milk is added using a homogenizer (Nippon Seiki Co., Ltd.) at room temperature for 5 minutes. And an emulsion was obtained. A stability test was performed on the obtained emulsion. This test was performed by allowing the emulsion to stand at room temperature and visually observing the properties of the emulsion after 24 hours. Stability was determined by the following criteria:

◎: stable after 24 hours

〇: Slight signs of separation are observed after 24 hours

Δ: Slightly separated after 24 hours

▲: Separation starts in a few hours, but there is an emulsified part after 24 hours

X: completely separated after 24 hours.

The results are shown in Table 1. Examples 2 to 4

A phospholipid, a commercially available soybean lecithin, and a hydrolyzed lecithin obtained by extraction in the same manner as in Example 1 were prepared, and these were appropriately mixed to obtain a phospholipid-containing emulsifying material having the composition shown in Table 1. . The stability of the emulsion containing these was evaluated in the same manner as in Example 1. The results are shown in Table 1. table 1

PS: phosphatidylserine PC: phosphatidylcholine

ΡΙ: phosphatidylinositol PE: phosphatidylethanolamine

ΡΑ: phosphatidic acid As shown in Table 1, when the phospholipid-containing emulsifiable material of the present invention having a predetermined composition containing PS and PI is used, an emulsion having excellent stability can be obtained. Example 5

1 g of the phospholipid-containing emulsifiable material obtained in Example 3 was mixed with soybean oil and water in the amounts shown in Table 2, and water was added as necessary to obtain a mixture having a final volume of 100 mL. Was. This was emulsified at room temperature for 5 minutes using a homogenizer (manufactured by Nippon Seiki Co., Ltd.) to obtain an emulsion. This emulsion was subjected to the same stability test as in Example 1. The results are shown in Table 2. The criteria for determining stability are the same as those in the first embodiment.

'' Table 2

As shown in Table 2, the phospholipid-containing emulsifiable material was 1% by weight / volume, and the fat and oil was 4 to 89 volumes. It can be seen that the emulsion containing / ₀ and water in a proportion of 95 to 10% by volume exhibits excellent emulsification stability. Comparative Examples 1-2

A phospholipid, a commercially available soybean lecithin, and a hydrolyzed lecithin obtained by extraction in the same manner as in Example 1 were prepared, and these were appropriately mixed to obtain a phospholipid-containing curable material having the composition shown in Table 3. Was. The proportion of each phospholipid in Table 3 is the content (% by weight) based on the total weight of the phospholipid in the obtained emulsifiable material. 1 g of this phospholipid-containing emulsifying material is added to 74 m1 of soybean oil and 25 m1 of water and emulsified at room temperature for 5 minutes using a homogenizer (manufactured by Nippon Seiki Co., Ltd.). A liquid was obtained. The obtained emulsion was subjected to a stability test in the same manner as in Example 1. The results are shown in Table 3. The criteria for determining stability are the same as in the first embodiment. Table 3

PS: phosphatidylserine PC: phosphatidylcholine

PI: phosphatidylinositol PE: phosphatidylethanolamine

PA: phosphatidic acid

As shown in Table 3, the emulsifying materials of Comparative Examples 1 and 2 containing PS but not containing PI showed low emulsification stability. Comparative Example 3 A phospholipid-containing emulsifying material (soy lecithin) consisting only of PS was prepared, and 1 g of this emulsifying material was mixed with the amount of soybean oil and water shown in Table 4 and homogenized at room temperature for 5 minutes (Japan). The mixture was emulsified by using Seiki Co., Ltd.) to obtain an emulsion. This emulsion was subjected to a stability test in the same manner as in Example 5. The results are shown in Table 4. The criteria for determining stability are the same as in the first embodiment. Table 4

As shown in Table 4, it is clear that the phospholipid composition composed only of PS has low emulsification stability. Comparative Example: ~ 7

Commercially available soy lecithin (product name: SLP—white, vinegar lecithin industrial Co., Ltd.) as a material for Comparative Example 4, commercially available soybean lecithin (product name: SLP—PI powder, vinegar As a material for Comparative Example 6, soybean lysolecithin (product name: SLP—white lyso, Tsuru-Lecithin Industry Co., Ltd.) was prepared. Separately, using commercially available soybean lecithin (product name: SLP-PC70, manufactured by Tsuruichi Lecithin Industry Co., Ltd.) A phosphatidyl glycerol preparation was obtained by performing a phosphatidyl group transfer reaction in the presence of lyserol pLD, and this was used as a material for Comparative Example ⁷ . Table 5 shows the composition of these materials. The proportion of each phospholipid in Table 5 is the content (% by weight) based on the weight of the total phospholipids in each material. Using these materials as phospholipid-containing emulsifiable materials, emulsions were prepared in the same manner as in Example 1, and the same stability test was performed. Table 5 shows the results. The criteria for determining stability are the same as in the first embodiment.

Table 5

PS: phosphatidylserine PE: phosphatidylethanolamine

PI: phosphatidylinositol LPL: lysolecithin

PA: phosphatidic acid PG: phosphatidylglycerol

PC: phosphatidylcholine

As shown in Table 5, the stability of the emulsified liquid of the phospholipid-containing emulsifying composition which did not contain PS and PI at a predetermined ratio was extremely poor.

Industrial applicability

According to the present invention, as described above, a phospholipid-containing emulsifying composition containing phosphatidylserine, phosphatidylinositol, and a neutral phospholipid or phosphatidic acid at a predetermined ratio and having excellent emulsifying function and high stability. Things are obtained. The composition is used in various forms of food, including mayonnaise, cream, bread, biscuits, beverages, and seasonings.

Claims

The scope of the claims

1. A phospholipid-containing emulsifying composition comprising phosphatidylserine, phosphatidylinositol, and neutral phospholipid,

The phosphatidylserine is contained in a proportion of 5 to 85% by weight, and the phosphatidylinositol is contained in a proportion of 2.5 to 30% by weight, based on the total weight of the phospholipid, and

An acidic phospholipid including phosphatidylserine and phosphatidylinositol is contained in a proportion of 1.0 to 7.4 parts by weight in total with respect to 1 part by weight of the neutral phospholipid.

A phospholipid-containing emulsifiable composition.

2. A phospholipid-containing emulsifiable composition comprising phosphatidinoreserin, phosphatidizoleinoscitonore, and phosphatidic acid,

Based on the weight of the entire phospholipids, wherein phosphatidylserine 5-8 5 weight ^_0/0, and phosphatidylinositol are contained in an amount of 2.5 to 3 0 wt%, and

The total weight of phosphatidic acid and phosphatidylinositol based on the weight of the entire phospholipid is 2.5 weight. / ₀ to 36% by weight,

A phospholipid-containing emulsifiable composition.

3. A food containing the phospholipid-containing emulsifiable composition according to claim 1 or 2.