WO2008146942A1

WO2008146942A1 - Method for production of phospholipid-containing functional material, and method for production of plasmalogen-type glycerophospholipid

Info

Publication number: WO2008146942A1
Application number: PCT/JP2008/060120
Authority: WO
Inventors: Yoshitaka Nadachi; Takehiko Fujino; Siro Mawatari; Osamu Kukino; Keiji Umeda
Original assignee: Umeda Jimusho Ltd.; Institute Of Rheological Function Of Food Co., Ltd.
Priority date: 2007-05-28
Filing date: 2008-05-27
Publication date: 2008-12-04
Also published as: JPWO2008146942A1; JP5774816B2

Abstract

Disclosed is a method for producing a phospholipid-containing functional material or a high-purity plasmalogen-type glycerophospholipid from a poultry breast meat by a simple manipulation and in high yield. Specifically disclosed are: a method for producing a phospholipid-containing functional material by transforming the shape of a poultry breast meat by at least one process selected from the following processes (a) to (c): (a) a process of mincing the poultry breast meat in a low-temperature and low-oxygen atmosphere; (b) a process of pasting the poultry breast meat together with an emulsifying/dispersing agent at a low temperature; and (c) a process of powderizing the poultry breast meat by drying at a low temperature; and a method for producing a plasmalogen-type glycerophospholipid, which comprises the following steps (A) to (C): (A) extracting the entire fat material from a powder of a poultry breast meat and drying the extracted fat material; (B) extracting the dried entire fat material with a solvent to separate into an insoluble fraction and a soluble fraction; and (C) extracting the soluble fraction with a solvent to separate and collect the insoluble fraction.

Description

Specification

Method for producing phospholipid-containing functional material and plasmalogen type glyce mouth Method for producing phospholipid Technical Field

The present invention provides a simple operation of a phospholipid-containing functional material useful as a functional food material, a pharmaceutical material, a cosmetic material, etc. The present invention relates to a method for producing with good yield, and also relates to a plasmalogen type glyceport phospholipid. Background art

Lipid refers to a substance that has a long-chain fatty acid or a similar hydrocarbon chain in a molecule and exists in a living body or is derived from a living organism. This lipid can be classified into simple lipids and complex lipids. Simple lipids are composed of C, H, and O, and are generally soluble in acetone. The simple lipid triacylglycerol exists in an animal body as a reservoir of energy in adipose tissue. On the other hand, complex lipids are a group of lipids including phosphoric acid P and base N. Therefore, complex lipids consist of a hydrophobic part (fatty acid part) and a hydrophilic part (phosphoric acid or base part), exhibiting amphipathic properties. Generally, the simple lipid is soluble in acetone. In contrast, complex lipids are insoluble in acetone. Such complex lipids are constituents of biological membranes.

Examples of the complex lipid include (1) glyceline phospholipids [phosphatidylcholine (also known as lecithin), phosphatidylethanolamine, and the like. ], (2) Sphingolin lipids (sphingomyelin, ceramide dosylatin, etc.), (3) Glycosphingolipids (celebral mouthsides, sulfatides) TJP2008 / 060120 and Gandarioside belong. ), And (4) Groseroglycolipids (including those in which various cocoons are bound to diacylglycerol present in microorganisms and higher plants). The (2) sphingolipid lipid and the (3) sphingoglycolipid are collectively referred to as sphingolipids.

The glyceport phospholipid is a general term for phospholipids having daricerophosphate as a skeleton, and includes phosphatidylcholine (lecithin), phosphatidylethanolanolin, diphosphitidylglycerol, and the like. Of these glyceport phospholipids, the nonpolar part is often an ester of a fatty acid, but there is also a plasmalogen type having a butyl ether bond.

This glyceport phospholipid is important as a component of biological membranes. Among them, plasmalogen-type glycerophospholipid has been recently attracting attention as an antioxidant phospholipid because it is highly sensitive to vinyl ether bonds. It has been. Recently, plasmalogen-type glyceport phospholipids have contributed to the oxidative stability of phospholipid membranes containing cholesterol by a mechanism different from that of α-tocopherol (vitamin E), an antioxidant component of cell membranes. (See, for example, “J. Lipid Res.”, Pp. 44, pp. 164-171 (2000 3 ′).) Also, the plasmalogen-type Darissello phospholipid is It has been pointed out that cell membranes are not only involved in the antioxidant properties of lipoproteins, but also have an important role in the cell signaling system (for example, “J. Mo 1. N eurosci.”, No. 16卷, pp. 2 63 3 to 2 7; see discussion 2 7 9 to 2 84 (2 0 0 1)).

Such plasmalogen-type glyceport phospholipids are expected to prevent brain neuronal cell death in dementia, but in reality there are no sources that are safe and available in large quantities. By the way, in order to produce a relatively large amount of sphingomyelin from total lipids of foods, animal tissues, etc., it can be produced by elution stepwise in a column chromatography using a key acid or the like, or a solvent Manufactured by fractionation using a fractionation method. Both require complex procedures. In the solvent fractionation method, acetone is added to total lipids to precipitate complex lipids (phospholipids) (insoluble part), and the insoluble part is washed with ether to remove the glyceport phospholipids. A method of fractionation is common. This fraction contains not only sphingomyelin but also glycosphingolipids such as cerebroside.

It is known that chicken skin phospholipids are rich in human sphingomyelin and plasmalogen-type dariceroline qualities.

Chicken skin is more useful as a raw material for human sphingomyelin compared to conventional raw material sources, but it contains a large amount of subcutaneous fat, sometimes exceeding 70% by mass, and this removal is extremely complicated. There's a problem. Chicken skin contains plasmalogen-type glycerophospholipid at the same level as human sphingomyelin, and the ratio of phosphatidylcholine (lecithin) and phosphatidinorethanolamine is significantly higher in the latter. is there.

The present inventors have eagerly developed a raw material that surpasses chicken skin, and the neutral lipid content in chicken meat, especially rice meat, is 30 to 70 times smaller than chicken skin, and it is a human sphingo. The total content of myelin and plasmalogen-type glyceport phospholipids is several times greater. However, the ratio of plasmalogen-type glyceguchi phospholipids to human sphingomyelin is more than 85% by mass, In addition, the composition ratio of plasma mouth type darisserophospholipid is 50-75% by mass in adult chickens, phosphatidylcholine in young chickens, and phosphatidylethanolamine in young chickens. Plasmalogen-type phosphatidylcholine content is more than 30 times that of chicken skin, plasmalogen-type phosphatidylethanol in young chickens As a raw material for extraction of plasmalogen-type glyce mouth phospholipid (mixed in two kinds), plasmalogen-type phosphatidylcholine alone, and plasmalogen-type phosphatidylethanolamine alone, which is about twice as low as chicken skin, conventional examples We succeeded in finding a poultry fillet that was not cost-effective.

Adult fillet has 1 mass of total fat. /. 80% of them are phospholipids (neutral lipids are as small as 0.2% by mass), of which 45% by mass is plasmalogen-type glycerophospholipid (70% of which is plasmalogen-type) in phospha Chijirukori down) content in the raw breast 0s. 3 6 wt% (human type Sufi Ngomierin is slightly 0.0 3 mass ^_0/0), which is high, Rudake be processed as a main material Can be used to prepare functional foods with high added value. By the way, poultry fillet, along with thighs, has a high rate of meat collection, but because it is hard and crunchy and lacks juicy taste, it has been treated as low-use meat for a long time despite being healthy. Is receiving. The annual meat culled from 100 million hens and 200,000 tons of minced meat is 15,000 tons, and it is strongly required to use them as domestic livestock. Disclosure of the invention

Problems to be solved by the invention

Under such circumstances, the present invention is a method for producing a functional material containing a large amount of plasmalogen-type glyce mouth phospholipid from poultry, particularly chicken fillet, and poultry fillet powder, An object of the present invention is to provide a method for producing a high-purity plasmalogen-type glyceport phospholipid from the above functional material with a simple operation and in a high yield. Means for solving the problem

As a result of intensive research to achieve the above object, the present inventors have obtained a functional material containing a large amount of plasmalogen-type glycerophospholipid by applying a specific process to poultry, particularly chicken fillet. It has been found that high-purity plasma-single-type glycepore phospholipids can be obtained efficiently by applying a specific process to poultry fillet powder, and based on this finding, the present invention is It came to be completed.

That is, the present invention

(1) Poultry fillet (a) Mince process at low temperature and low oxygen atmosphere, (b) Paste process at low temperature using emulsifying dispersant (c) Low temperature drying A method for producing a functional material containing a phospholipid by transforming its shape by at least one process selected from the powdering processes of the above, comprising the sum of plasmalogen-type glycerophospholipid and sphingomyelin A phospholipid-containing functional material in which the content of the former in the amount is 85% by mass or more and the content of all phospholipids in the total lipid is 40% by mass or more is obtained. , Manufacturing method of functional material containing phospholipid,

(2) The method according to (1) above, wherein the poultry fillet is a peeled fillet,

(3) The poultry are adult chickens (hereinafter sometimes referred to as abandoned chickens), and the former is 40% by mass or more in the composition ratio of phosphatidylcholine and phosphatidylethanolamine in the plasmalogen-type glycerophospholipid. The method described in (1) or (2) above,

(4) The poultry are adult broiler chickens and males, and the composition ratio of phosphatidinorecholine and phosphatidylethanolamine in plasmalogen-type glycerophospholipid is 50% by mass or more, (1) or the method described in (2), (5) The poultry is a pleuler, and the latter is 50% by mass or more in the composition ratio of phosphatidylcholine and phosphatidylethanolamine in the plasmalogen-type glycepore phospholipid, as described in (1) or (2) above the method of,

(6) (A) Extracting the total lipid from the poultry fillet powder and drying it. (B) Drying the total lipid obtained in the step (A), using an aliphatic hydrocarbon solvent and a water-soluble ketone system. Extraction with a solvent mixture with a solvent, and separation into an insoluble part and a soluble part mainly composed of plasmalogen-type glyceport phospholipids (C) A portion of the plasmalogen-type glyceport phospholipid, characterized by comprising: a step of subjecting the product to drying treatment, followed by extraction with a water-soluble ketone solvent, and separating and recovering insoluble portions mainly composed of plasmalogen-type glyceport phospholipid. Production method,

(7) The mixed solvent in step (B) contains n-hexane and acetone in a volume ratio of 4: 6 to 6: 4, and the amount used is 1 per 1 g of dry total lipid. The method according to item (6), which is 0 to 30 mL,

(8) The water-soluble ketone solvent in step (C) is acetone, and the amount used is 10 to 30 mL per 1 g of the dried processed product of the soluble part obtained in step (B). The method described in (6) or (7) above,

(9) A plasmalogen-type glyceport phospholipid characterized by being obtained using the method according to any one of (6) to (8) above,

Is to provide. The invention's effect

According to the present invention, a plasmalogen-type glyce mouth which is useful as a functional food material, a pharmaceutical material, a cosmetic material, etc. from poultry, particularly chicken breast meat. A method for producing a phospholipid-containing functional material in which the former is 80% or more of the total phospholipid and sphingomyelin, and the proportion of total phospholipids in the total lipid is 40% or more. A method for producing a plasmalogen-type glycerophospholipid, a plasmalogen-type phosphatidinorecollin simple substance, and a plasmalogen-type phosphatidylethanolamine simple substance from a lipid-containing functional material with a simple operation and a high yield. Plasmalogen-type glycerophospholipid, plasmalogen-type phosphatidylcholine simple substance, and plasmalogen-type phosphatidinoleethanolamine simple substance can be provided.

The poultry fillet shape-changing technology of the present invention and the pasting technology using emulsified and dispersed natural preparations are secondary functions that do not harden by heat treatment and maintain a succulent feeling with no by-product dripping even during freezing and thawing treatment. Therefore, the rice paste is extremely useful as a high-value-added food material for rice meat, and the present invention is the beginning of high-value-added rice meat, resulting in an increase in consumption. It is expected to contribute to health promotion. Brief Description of Drawings

Fig. 1 ELS D detection chromatogram of substances obtained from waste chicken fillet by each operation.

Fig. 2 ELSD detection chromatograms of substances obtained by each operation from waste chicken fillet of organic farming breeding hens (local chickens).

Fig. 3 ELSD detection chromatograms of substances obtained from each operation of commercially available young chicken breast meat.

Fig. 4 Half-fried meatball hi-L0HS 1 15 ° C 5.5 minutes heating 5 minutes preheating heating time · temperature chart. PT / JP2008 / 060120

BEST MODE FOR CARRYING OUT THE INVENTION

The method for producing a phospholipid-containing functional material of the present invention comprises at least one step selected from the following steps ( _a ), (b) and (c): The production method of type glyceguchi phospholipid is composed of (A) step, (B) step and (C) step.

First, the manufacturing method of the phospholipid containing functional material of this invention is demonstrated.

[(a) Process]

This step (a) is a mincing step in a low temperature / low oxygen atmosphere. In the process (a), poultry fillet, especially chicken fillet, if it has a skin, it is first skinned with a skinner treatment and then minced as usual. Lower the temperature, preferably 5. It is desirable to set the minced size and minced rate with priority given to avoiding local heat generation at the shredded portion after cooling to C or lower. In addition, the minced meat and air exposure after mincing is minimized, and furthermore, with air purifiers to suppress air oxidation and bacterial infection, the room temperature is low, preferably in a semi-enclosed space of 15 ° C or less It is preferable to implement the treatment and its sealed packaging. The obtained mince should be vacuum-packed with a high barrier film and stored refrigerated.

[(b) Process]

This step (b) is a pasting step at a low temperature using an emulsifying dispersant.

In the step (b), skinned fillet meat, preferably the meat that has been minced in the step (a) and vacuum-packed refrigerated and stored, preferably a non-enzymatic emulsion-dispersed natural preparation for protein foodstuffs. Add an aqueous solution dissolved in an appropriate amount of water, mix evenly with an appropriate cutter mixer or processor, and paste into a straight (straight type). It is recommended that the pasted type be prepared, and this paste be cooled with a high-parity film and then cooled and stored at a low temperature, preferably refrigerated. Refrigeration is possible for long-term storage.

[(c) Process]

This step (c) is a powdering step by low temperature drying.

In the step (c), skinned meat, preferably minced meat that has been refrigerated and stored in vacuum in the step (a), or in some cases, any of the straight type pastes in the step (b) According to the method, it is better to dry it in a minimally invasive manner with a commercially available freeze-drying device, and if necessary, pulverize it by low-temperature pulverization, and store this powder refrigerated under light shielding after vacuum packaging of a hybrid film.

In the phospholipid-containing functional material obtained in this way, the content ratio of the former in the total amount of plasmalogen glyce mouth phospholipid and sphingomyelin is 85% by mass or more, and The total content of phospholipids is 40% by mass or more.

In addition, when the poultry are adult chickens, the composition ratio of phosphatidylcholine and phosphatidylethanolamine in the plasmalogen-type glyce mouth phospholipid is 50% by mass or more of the former, and adult broiler chickens , The composition ratio of phosphatidylcholine and phosphatidylethanolamine in the plasmalogen-type glycerin lipid is 50 masses in the former. / Is ₀ or more, if a broiler, phosphine Achijiruko Li down and the component ratio of phosphatidyl ethanolamine plasmalogen type glycerin port Li down lipids, the latter 5 0 mass. / ₀ or more.

Next, a method for producing the plasmalogen glyceport phospholipid of the present invention will be described. [(A) Process]

This step (A) is a step of extracting the total fat from the poultry fillet powder, preferably the chicken fillet powder, and drying it. In the step (A), first, poultry fillet powder is prepared. In that case, the rice trimet meat may be dried and pulverized as it is, and minced and pasted as necessary. Then, it may be dried and powdered. Preferably, a powder that is refrigerated and stored in a shaded state after vacuum packaging of the high barrier film obtained in [Step (c)] is used. Next, the total lipid is extracted from the poultry fillet powder thus obtained using a solvent and dried to obtain a dry total lipid. Solvents used for extraction of total lipids are those that are safe for food hygiene and have good extraction efficiency. As such a solvent, ethanol is particularly suitable. This extraction process can be performed according to a conventional method. However, ethanol-soluble non-lipid components are also extracted in this extraction process.

According to a conventional method, the extract can be obtained by removing the solvent using a rotary evaporator or by introducing nitrogen gas.

[(B) Process]

In the step (B), the dry total lipid obtained in the step (A) is extracted with a mixed solvent of an aliphatic hydrocarbon solvent and a water-soluble ketone solvent, and an insoluble portion and a soluble portion are extracted. It is the process of separating into.

In the step (B), examples of the aliphatic hydrocarbon solvent that is one component of the mixed solvent used for the extraction treatment of the dried total lipid include n-pentane, isopentane, n-hexane, isohexane, n Examples include monoheptane, isoheptane, cyclopentane, cyclohexane, etc., and these may be used alone or in combination of two or more. N Monohexane is preferred.

Further, as the water-soluble ketone solvent which is the other component of the mixed solvent, for example, acetone and / or methyl ethyl ketone can be used, and among these, acetone is preferable.

When a mixture of n-hexane and acetone is used as the mixed solvent, the ratio is preferably 4: 6 to 6: 4 in terms of volume ratio, and 4.5: 5.5 to 5.5: 4.5. Is more preferable.

The amount of the mixed solvent is usually about 10 to 30 mL per gram of dry total lipid.

[(C) Process]

In the step (C), the soluble part obtained in the step (B) is dried and then extracted with a water-soluble ketone solvent, and the insoluble part (hereinafter referred to as plasmalogen-type glyceport phospholipid) This is sometimes referred to as crude plasmalogen-type glycepore phospholipid.

In the step (C), first, the soluble part obtained in the step (B) is dried according to a conventional method. For example, a method of distilling off the mixed solvent in the soluble part using a rotary evaporator can be used. Next, the dried product obtained in this way is extracted with a water-soluble ketone solvent according to a conventional method. Examples of the water-soluble ketone solvent used in this case include acetone and / or methyl ethyl ketone, but aceton is preferable.

When acetone is used as the extraction solvent, it is usually about 10 to 30 mL per lg of dried product. If the amount of solvent used is less than 10 mL, the extraction process cannot be performed sufficiently, and the purity and recovery rate of the plasmalogen-type glycepore phospholipid in the insoluble part may be reduced. Meanwhile, over 30 mL Therefore, the effect of improving the purity and recovery rate of plasmalogen-type glycerophospholipid is hardly exhibited for the amount. The preferable amount of the solvent used is 15 to 25 mL per 1 g of the dried processed product.

The extraction solution can be separated into a soluble part and an insoluble part (crude plasmalogen-type darice cellophospholipid) mainly composed of plasmalogen-type glycepore phospholipid by subjecting it to a centrifugal separation treatment. The amount of plasmalogen-type glyceport phospholipid in the insoluble part is usually 40% by mass or more.

According to such a method of the present invention, plasmalogen-type glyceport phospholipid can be produced with high purity and high yield from the total fat of poultry fillet, preferably chicken fillet, by simple means. .

According to the method of the present invention, 0.1 to 3 mass of crude plasma mouth-type glyce mouth phospholipid is usually obtained from the dry powder of chicken breast meat. / ₀ can be obtained at a rate of about ₀ .

The crude plasmalogen glycerophospholipid obtained by the method of the present invention mainly contains phosphatidylcholine (P C) and partly phosphatidylethanolamine (P E). About 30% by mass of the PC is a plasmalogen type, and PE contains about 65% by mass of a plasma single-gen type.

The following formulas (II) and (II I) show the structures of diacyl glycated phospholipid and plasmalogen glycated phospholipid, respectively.

R ¹ , R ² = long chain aliphatic group

X = —CH ₂ CH ₂ NH ₂ , 1 CH ₂ CH ₂ N (CH ₃ ) ₃ Normal glyce mouth phospholipid (lecithin) is a glycerol sn-1 (position 1) as shown in formula (II). ) Has an ester bond with a fatty acid acyl group, and the plasmalogen type has a butyl ether bond with an alkenyl group on sn-1 of glycerol as shown in formula (III).

When X is an aminomino group, it is phosphatidylethanolamine, and when X is a trimethylaminoethyl group, it is phosphatidylcholine.

The plasmalogen glycerophospholipid is attracting attention as an antioxidant phospholipid because of its high radical sensitivity of vinyl ether bond, and is known to contribute to the oxidative stability of phospholipid membranes containing cholesterol. . In addition, it has been pointed out that plasmalogen-type glyceport phospholipids are not only involved in the antioxidant properties of cell membranes and lipoproteins, but also have an important role in the cell signaling system. Such plasmalogen-type glyceport phospholipids are expected to have the effect of preventing brain neuronal cell death in dementia and the onset prevention effect of atherosclerosis.

The present invention is also characterized by being obtained using the method of the present invention described above. A plasmalogen-type glyceport phospholipid is also provided. Example

Next, the present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples.

Example 1

1. Functional mince containing higher-order functional phospholipids

1) Organic farming breeding egg collection chicken waste meat

Freshly degassed and chilled chilled meat harvested from organic chicken laying hens (manufactured by Agricultural Union Enchikin (Chiran-cho, Minamikyushu-shi, Kagoshima)) (hereinafter sometimes referred to as "organic meat") ) Using a commercial minced device installed in an air-cooled chamber while minimizing air exposure during the process, 1 mm of minced with a size of several millimeters while maintaining the internal temperature at 1 oC or less, 95 mass Take the mince obtained in% yield in a high-paria film wrapping material, immediately deaerate and store in a refrigerator.

The refrigerated mince was subjected to the following component analysis.

10 mg of the total amount of phospholipid (content: 0.9 9 mass%) was prepared by precipitating 20 6.2 mg of total lipid extracted by Bligh &Dyer's method with 10 ml of aceton by 10 mg ) This was analyzed by HP LC, and the constituent ratio of the constituent phospholipids was calculated from the peak area ratio by evaporative light scattering (ELSD). Based on this, the content and content of phospholipid molecules were determined and the results are shown in Table 1. 60120 Table 1

(The composition ratio and the content are mass%.)

The characteristics of the fillet phospholipids in the waste chickens of organic farming breeding eggs are as follows.

2. 50% of the total lipid is only 1% by mass, and more than half of it is overwhelmingly PC. Reflecting this, PL-PC is the next higher function type, followed by P L_P E is large, but SM is extremely small. Higher-order function type refers to a function that is directly involved in life homeostasis; for example, a function that inhibits apoptosis of cranial neurons or a function related to myocardial homeostasis. . Furthermore, the total PC is actually less than 70%. Next to this, total PE is less than 20%, of which 60% is P L-PE, in contrast to P L-PC in total PC, which is just over 20%. It is also noteworthy that the SM content is extremely low at 2% by mass, even compared to the skin described later.

2) Egg waste chicken

1. Lipid analysis was performed as in 1). The results are summarized in Table 2. TJP2008 / 060120 Table 2

(The composition ratio and the content are mass%.)

The characteristic feature of the henrye phospholipids is that, first of all, it accounts for more than 80% of the total lipids with a content of only 1% by mass. Furthermore, almost 70% of the total PC is overwhelmingly large. Reflecting this, the higher-order function type has a high P L_PC of 30% by mass or more, but the SM is extremely low. Next to this, total PE is slightly over 17% by mass, of which, over 75% by mass is PL-PE, and in contrast to that PL-PC in total PC is over 45% by mass. It is. It is also noted that the SM content is extremely low at 3.2% by mass even compared to the epidermis described later.

3) Adult broiler chickens

(1) Adult broiler chicken

Degassed and chilled fresh peeled minced meat (from Agricultural Union) made from 5 chunky varieties (average mass 5.9 kg) Take 20 g samples from each In the same manner as in 1), an average total lipid of 0.2 g (average yield of 1%) was extracted. An average of 0.15 g of a phospholipid fraction of 75% by mass was separated from each total lipid. The composition of the phospholipid by HP LC / ELSD analysis is p 1 PC (2 8. 7%), p 1 PE (1 1.2%), PC (4 3.7%), PE (3 .2%), SM (5.1%), p 1 The composition ratio of the total mold was 39.9% (content ratio in fillet 0.28%).

(2) Broiler breeder female adults

Degassed and chilled fresh peeled minced meat (from Agricultural Association) made from 5 chunky varieties (average mass 3.8 kg) Take 20 g samples from each 1) Similar to total lipid average 0.47 g (average yield)

2. 35%) was extracted. An average of 0.3 g of phospholipid fraction of 65% by mass was separated from each total lipid. The composition of the phospholipid by HP LC / ELSD analysis was as follows: p1PC (21.4%), p1PE (13.4%), PC (50.3%), PE (4.8 %), SM (1.3%), the composition ratio of p1 type total is

3 5% (content ratio in fillet 0.5 4%).

4) Young chicken fillet

A commercial broiler was procured and lipid analysis was performed in the same manner as in 1.1). The results are summarized in Table 3. The characteristics of young chicken (broiler) fillet phospholipids are only 1 mass, similar to the previous two adult chickens. /. The ratio of strong total lipids is as high as 2/3, the total PC is a little less than 70%, and the total PE is more than 20%. The higher-functional, SM is as low as 2 wt%, nearly ^70% of the total PE is PL-PE at a point similar to adult chickens, but the field of adult chickens in the composition of the total PC previous two cases Unlike the case, the proportion of PL-PC is markedly reduced to the 13% by mass range, and its content is also reduced to 1/3. Table 3

(The composition ratio and content rate are mass%.)

5) Comparison control: Egg collection waste chicken epidermis

The deoiled minced skin prepared in Example 3 to be described later is 1.

Carried out. The results are summarized in Table 4.

Table 4

(The composition ratio and the content are mass%.)

The crucial difference from the above 3 cases of meat is that the total lipid is more than 10 times, even though it has been deoiled more than half, and the content is the same, but the total phospholipid The proportion of SM is drastically reduced to 10% or less. In the high-order functional type, the SM content increases dramatically by about 6 times. In the total PL type, the PL-PE is at the same level. PC 3 mass ⁰ /. It is noteworthy that the result is a marked difference between the meat and the tissue specificity.

In the raw epidermis, the total lipid content jumps to at least about three times this, so the content of phospholipids decreases evenly by a fraction.

2. Preparation of functional paste containing higher functional phospholipid

Freshly evacuated packaged chilled meat (produced by the Agricultural Union Act, artificial nuchikin) taken from waste eggs from egg-laying hens, preferably 1.2) described in mince 3 550 g, protein-treated natural preparation KO— X (Prepared by Osamu Kukino (Ichiki Kushikino Nashina 1126-1)) Dissolve 50 g in 2 50 ml of cold water, mix with refrigerated mince, and quickly with a food processor of a commercial home appliance. Then, 34.3 g of seasonings and spices were added and mixed well to obtain 6500 g of seasoned fillet minced meat (yield 95% by mass). This was deaerated and sealed and left in the refrigerator for several hours.

3. Freeze drying of fillet

1.2) Prepared by packaging (1) 100 g of minced minced chicken stock preserved in an ordinary manner and lyophilized in a commercial lyophilizer to obtain 31.5 g of dried powdered meat Rate 98% by mass). Example 2 Concentration and separation of plasmalogen-type glyceport phospholipids

1. Waste chicken fillet

Example 1 of waste chicken fillet 3. Extraction of 400 g of freeze-dried powder using the method described above using 100 mL of ethanol as an extraction solvent, followed by extraction The effluent was dried by a rotary evaporator to obtain 12 g of total lipids. Then, the dried total lipids, per the lg, 2 0111] ^ ₁ 1 over hexane / Aseton (volume ratio 1Z 1) mixed solvent was added and 1 hour extraction process under ice cooling. Thereafter, the extraction solution was centrifuged at 100 G for 10 minutes to separate the soluble portion and the precipitate (insoluble portion) of the supernatant. Next, 20 mL of acetone per lg was added to the dried product obtained by drying the soluble part with a rotary evaporator, and extraction was performed. Thereafter, the extraction solution was centrifuged at 100 G for 10 minutes to separate the soluble portion and the precipitate (insoluble portion) of the supernatant. As an insoluble part, 8.6 g of a phospholipid fraction from which sphingomyelin was removed was obtained, most of which was a mixture of plasmalogen-type glyce mouth phospholipid (45 mass%) and PC · PE (4 5% by mass). The HP LC chart is shown in Fig. 1.

2. Fillet of organic breeding egg collection waste chicken

In the same manner as in 1. above, 400 g of freeze-dried powder was used to obtain 10.8 g of phospholipid fraction from 25 g of the separated total lipid. The HPLC measurement results (Fig. 2) showed that the main components were P L—P C + P L—P E (28 mass%) and P C ′ (53 mass%).

3. Proila kind of adult chickens

1) Adult broiler chicken

Example 1 1. 3) Concentrated and separated in the same manner as in Example 2 1. using 2 g of the total lipid obtained in (1) to obtain a concentrated phospholipid fraction of 1.4 g (yield 7 0%) was prepared. As a result of this HP L C_ ELSD analysis, [pi PC (70%) + 1 PE (30%)] 0.5 9 g (yield 4 2%) and [PC (9 4%) + PE ( 6%)] 0.69 g (yield 49.5%). 2) Female laying hens

Example 1 1. 3) Concentrated and separated in the same manner as in Example 2 1. using 2 g of the total lipid obtained in (2). Rate 63.7%) was prepared. As a result of this HPLC / ELSD analysis, [pl PC (60%) + p1PE (4 0%)] 0.45 g (yield 35.3%) and [PC (9 0%) + It was found to be PE (1 0%)] 0.71 g (yield 55.7%).

4. Broiler fillet

In the same manner as in 1. above, 400 g of lyophilized powder was used to obtain a phospholipid fraction of 13.5 g to 8.7 g of separated total lipid. As HPLC measurement results (Fig. 3) or al major component was shown to be a PC (6 0 mass ^_0/0) and PL- PC + PL- PE (2 3 mass%). Example 3 Preparation of functional chicken meatballs containing higher order functional phospholipids

1) Preparation of minced and deoiled eggs

Fresh epidermis collected from waste chickens of egg-collecting hens was minced 8 mm under low temperature using the above-mentioned apparatus to obtain 4700 g (yield 94% by mass) of chicken skin mince. This was vacuum-packed with a high barrier film wrapping material and stored refrigerated. 300 g of this chicken skin minced is heated and deoiled minimally invasively at 105 ° C for 15 minutes with a low-oxygen hybrid steam heating device (made by Taiyoichi Seisakusho Co., Ltd. (Hito-Shimizugawa); hi-L0HS device). Thus, deoiled chicken skin 8 mm mince 14 45 g (yield 48 mass%) was obtained, vacuum-packed with a high barrier film packaging material, and stored refrigerated.

2) Preparation of chicken meatballs

Refrigerated seasoned minced meat minced 45 5 g with chilled deoiled chicken skin minced 50 g After mixing, fryer with meatball molding device (1700 ° CZ for 3 minutes) To give about 30 g of meatballs 4550 g (yield 90 mass%) in a half-fried state. This half-fried meatball is heated at the above-mentioned hi-L0HS 1 1 5 ° C for 5.5 minutes, then left for 5 minutes and left to heat (Fig. 4). 3% by mass) was obtained. This was allowed to cool at room temperature, and then stored in a deaerated package frozen.

The frozen cooked chicken meat poles 10 pieces 2 95 5 g were thawed and heated in a microwave oven, and 2 9 2 g (yield 99% by mass) of hot chicken meat tops were obtained without dripping. .

3) Sensory test of frozen 'thawed chicken meatballs'

The hot chicken meat pole obtained above was subjected to a two-choice sensory test with 12 adult men and women. As shown in Table 2, a high score was obtained. There were many impressions that the fried food was not oily and refreshed, and the texture was soft and juicy, and the taste and aroma of chicken were delicious.

Table 5

4) Component analysis of frozen chicken meatballs

Lipid component analysis of frozen chicken meatballs was performed.

As shown in Table 6, human sphingomyelin derived from the raw materials used, and the plasmalogen-type glycerophospholipid, lassmarogen-type phosphitidylcholine and lassmalogen-type phosphatidylethanolamine, were not worn out and were frozen chicken meatballs. It was revealed that it remained inside. Table 6

(The composition ratio and the content are mass%.)

Industrial applicability

According to the method for producing a phospholipid-containing functional material and a plasmalogen-type glycepore phospholipid of the present invention, a phospholipid-containing functional material useful as a functional food material, a pharmaceutical material, a cosmetic material, etc. Oral phospholipids can be produced with high yield by simple operations.

Claims

The scope of the claims

1. Poultry fillet (a) Mince process in low temperature and low oxygen atmosphere, (b) Paste process in low temperature using emulsifying dispersant, and (c) Powder process in low temperature drying A method of producing a phospholipid-containing functional material by converting its shape through at least one process selected from the above, wherein the content of the former in the total amount of plasmalogen glycerophospholipid and sphingomyelin There are 85 masses. /. A method for producing a phospholipid-containing functional material, characterized in that a phospholipid-containing functional material having a total phospholipid content in the total lipid of 40% by mass or more is obtained.

2. The method according to claim 1, wherein the poultry fillet is a peeled fillet.

3. The poultry are adult chickens (hereinafter sometimes referred to as abandoned chickens), and the former is 40% by mass in the composition ratio of phosphatidinorecholine and phosphatidylethanolamine in plasmalogen glyce mouth phospholipids. The method according to claim 1 or 2 as described above.

4. The poultry are adult broiler chickens and males, and the former is 50% by mass or more in the composition ratio of phosphatidylcholine and phosphatidylethanolamine in plasmalogen-type darisserophospholipid. The method described in 1.

5. The method according to claim 1 or 2, wherein the poultry is a broiler and the latter is 50% by mass or more in the composition ratio of phosphatidylcholine and phosphatidylethanolamine in the plasmalogen-type glyce mouth phospholipid. .

6. (A) Extracting total lipid from poultry fillet powder and drying (B) Dry total lipid obtained in step (A) is mixed with aliphatic hydrocarbon solvent and water-soluble ketone solvent. Extract with a mixed solvent with insoluble parts, and plasmalogen A step of separating the soluble part mainly composed of type glyceport phospholipid, (C) The soluble part obtained in the step (B) is dried and then extracted with a water-soluble ketone solvent, and plasmalogen And a step of separating and recovering an insoluble part mainly composed of type glyceport phospholipid, and a method for producing plasmalogen type glyceport phospholipid.

7. The mixed solvent in step (B) contains n-xane and acetone in a volume ratio of 4: 6 6: 4, and the amount used is 10 3 0 per 1 g of dry total lipid. The method according to claim 6, which is mL.

8. The water-soluble ketone solvent used in step (C) is acetone, and the amount used is 100 mL per 1 g of the dried product of the soluble part obtained in step (B). The method according to 6 or 7.

9. A plasmalogen-type glyceport phospholipid obtained by using the method according to any one of claims 6 to 8.