JPH09167A - Concentration of acidic phospholipid - Google Patents

Abstract

PURPOSE: To simply and easily obtain a lipid mixture containing acidic phospholipids in high concentrations, useful as an emulsifier or a bitterness depressant by treating a lecithin with a mixture of a lower alcohol and acetone and removing the mixed solvent fraction. CONSTITUTION: Lecithin (suitably soybean lecithin of >=40% purity) is treated with a mixture of a lower alcohol (suitably ethanol) and acetone, then the mixed solvent fraction is removed. The weight ratio of the lower alcohol to acetone is preferably 10/90 to 95/5. The amount of the mixed solvent is desirably 5-35 pts.wt. per 1 pt.wt. of lecithin. The lecithin is stirred together with the mixed solvent at 25-60 deg.C, filtered to collect the extraction residue and these operations are repeated twice or three times. It is preferred that this lipid mixture contains phosphatidylinositol and phosphatidic acid totally in an amount of 60-85wt.% based on the total of the neutral phospholipids and the acidic phospholipids.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method of concentrating acidic phospholipids useful for foods, oral medicines, emulsifiers for cosmetics, bitterness inhibitors, etc., from lecithin to a high concentration.

[0002]

2. Description of the Related Art Conventionally, pasty lipid mixtures containing lecithin, particularly oil obtained from soybeans, are used in various types of neutral lipids, fatty acids, carbohydrates, proteins, inorganic salts, sterols, pigments, etc. Since it contains various impurities and its unique color and flavor, it has a drawback that the hue and flavor inherent in the food are impaired, especially when added to food. On the other hand, lecithin also contains acidic phospholipids useful as emulsifiers or bitterness suppressors for foods, oral medicines, and cosmetics. Therefore, as a method for removing the impurities, a method of treating with acetone (US Pat. No. 3,268,335 or the like), a method of treating with alcohol, for example, ethanol or the like (US Pat. Nos. 2,945,869, 2724649, and JP-B-59). -5263
Japanese Patent Laid-Open No. 59-51253), a method for extracting lecithin in a two-phase partition system in which a hydrous alcohol or a nonpolar organic solvent is combined (Japanese Patent Laid-Open No. 54-6120).
No. 0) etc., but they are not sufficient for removing impurities, or the purpose is to concentrate phosphatidylcholine. In addition, as a method for extracting the acidic phospholipid from lecithin, there is a method of modifying the phospholipid analog extracted from lecithin and separated, by chemical modification or enzymatic treatment, for example, oil seeds, cabbage, rice bran, etc. Plant-derived phospholipase D, or phospholipase D produced by a microorganism (Japanese Patent Laid-Open No. 2-312551)
Is used to hydrolyze phosphatidylcholine, which is a neutral phospholipid, to obtain phosphatidic acid, and the phospholipase D is used to transesterify the phosphate group to convert phosphatidylcholine to phosphatidylglycerol (JP-A-3
No. 22991) or a method of converting into phosphatidylserine or the like. Further, in order to increase the concentration of acidic phospholipids in the lipid mixture, there is a method in which the lipid mixture is enzymatically decomposed or subjected to solvent fractionation treatment, and then treated with acetone, membrane separation or the like.

However, the concentration of acidic phospholipid obtained from lecithin cannot be said to be sufficient even by these methods, and a method for obtaining an even higher concentration of acidic phospholipid is desired.

[0004]

SUMMARY OF THE INVENTION It is, therefore, an object of the present invention to provide a method for obtaining acidic phospholipids from lecithin at a high concentration.

[0005]

Under such circumstances, as a result of intensive studies, the present inventors have found that treatment of lecithin with a mixed solvent of lower alcohol and acetone can provide acidic phospholipids at a high concentration. The present invention has been completed. That is, the present invention provides a method for concentrating acidic phospholipids by treating lecithin with a mixed solvent of lower alcohol and acetone to remove the mixed solvent fraction.

The raw material lecithin used in the present invention is not particularly limited, but examples thereof include lipid mixtures obtained from animals and plants such as soybean lecithin, egg yolk lecithin, rapeseed lecithin, corn lecithin, and among them, soybean lecithin is particularly preferable. The form of lecithin may be paste or powder. The purity of lecithin is not particularly limited, and may be one obtained by removing impurities by a known purification method in advance, or one having an increased concentration of acidic phospholipid by a known means, but preferably 40% or more in purity. The ones are good.

In lecithin, in addition to acidic phospholipids, neutral phospholipids such as phosphatidylcholine (PC), phosphatidylethanolamine (PE) and their lyso forms; neutral lipids such as triglycerides, diglycerides and monoglycerides; fatty acids. , Sterol lipids, glycolipids and the like may be contained in any proportion, for example, neutral phospholipids 10 to 60% by weight, neutral lipids 0 to 60% by weight, acidic phospholipids 5 to 80% by weight, and others 5 to It is preferably contained at 50% by weight. The method for concentrating acidic phospholipids of the present invention requires treating lecithin with a mixed solvent of lower alcohol and acetone.

Although the lower alcohol is not particularly limited, examples thereof include methanol, isopropanol and ethanol, and among these, ethanol is particularly preferable.

The ratio of lower alcohol to acetone is not particularly limited, but in order to improve the concentration effect, it is 1 by weight.
/ 99 to 99/1 is preferable, and 10/90 to 95/5 is particularly preferable.

The ratio of the mixed solvent of reticine, lower alcohol and acetone is not particularly limited, but 0.1 to 100 parts by weight, preferably 1 to 50 parts by weight of the mixed solvent to 1 part by weight of lecithin, It is particularly preferably 5 to 35 parts by weight. If the amount of the mixed solvent is too small relative to lecithin, the concentration efficiency will be poor, and conversely, if it is too large, the recovery will be reduced, which is not preferable.

The method of treating lecithin with a mixed solvent of lower alcohol and acetone is not particularly limited, but the mixture of lecithin and the mixed solvent is stirred and filtered at a temperature of room temperature or higher, preferably 25 ° C to 60 ° C, and the mixture is mixed. The method of obtaining the extraction residue of a solvent is mentioned. This extraction operation is 2-3
It is preferable to repeat the process once. It is preferable to remove the mixed solvent containing the liquid from the obtained extraction residue to obtain an acidic phospholipid concentrate.

The acidic phospholipids obtained by the method of the present invention include phosphatidylinositol (PI), phosphatidic acid (PA) and phosphatidylserine (P).
S), lysophosphatidic acid (L-PA),
These may be contained in any proportions, but in particular, the total amount of PA and PI in the phospholipid (the total amount of the neutral phospholipid and the acidic phospholipid) is 50 to 90% by weight, preferably , 60 to 85% by weight is preferable.

The lipid mixture containing a high concentration of acidic phospholipids obtained by the method of the present invention (hereinafter, sometimes referred to as "acidic phospholipids concentration method"), when used as a bitterness suppressor of food, The bitterness-reducing effect can be enhanced by removing neutral lipids and neutral phospholipids contained in the lipid mixture by a known method.

The acidic phospholipid concentrate obtained by the method of the present invention can be preferably used for foods including drinks, pharmaceuticals or cosmetics.

Examples of foods to which the acidic phospholipid concentrate obtained by the method of the present invention is applied include citrus fruits such as grapefruit, orange, and lemon, and fruit juices containing them; tomato, pepper, celery, uri, carrot,
Vegetables such as potatoes and asparagus and vegetable juices and vegetable juices containing them; sauces, soy sauce, miso, seasonings such as umami seasoning and peppers; soybean foods such as soymilk and soymilk; creams, dressings, mayonnaise, margarine etc. Emulsified foods; Seafood processed foods such as fish meat, surimi and roe; Nuts such as peanuts; Fermented products such as natto; Meat and processed meat products; Beer, coffee, cocoa, black tea, green tea, fermented tea, semi-fermented tea, Beverages such as soft drinks and functional beverages; Pickles; Noodles; Soups including powdered soups; Dairy products such as cheese and milk; Bread cakes; Confectioneries such as snacks, chewing gum, chocolates; Candies; Health food etc. can be mentioned.

Examples of the oral medicine to which the acidic phospholipid concentrate obtained by the method of the present invention is applied include various kinds of drugs having a bitter taste which have been conventionally used as medicines. In particular, it is effective in reducing the bitterness of acid addition salts of basic drugs (eg, strychnine, quinine, papaverine, berberine, bromethazine, brucine, propranolol, chlorpromazine). Examples of acid addition salts include hydrochloride, nitrate, sulfate, acetate,
Mention may be made of mineral acid salts and organic acid salts such as citrates and carbonates.

Further, as the cosmetics to be applied,
Cosmetics used for the face and cosmetics used for the oral cavity are included. Examples of cosmetics used on the face include lotions, emulsions, creams, packs, lipsticks, foundations, shaving aids, aftershave lotions, cleansing foams and cleansing gels. Also, as cosmetics used for the oral cavity,
Examples include toothpaste, mouthwash, and mouthrinse. Examples of the component exhibiting a bitter taste in cosmetics having such a bitter taste include surfactants such as sodium alkyl sulfate and sodium monoalkyl phosphate, menthol, linalool, phenylethyl alcohol, ethyl propionate, geraniol, linalool acetate. , Fragrances such as benzyl acetate, fungicides such as methylparaben, propylparaben, butylparaben,
Examples include humectants such as lactic acid and sodium lactate, alcohol denaturants such as 8-acetylated sucrose and brucine, and astringents such as aluminum lactate.

[0018]

EFFECT OF THE INVENTION According to the method of the present invention, a lipid mixture containing lecithin in a relatively simple manner and containing a much higher concentration of acidic phospholipids than in the case of using acetone or lower alcohol alone is obtained. be able to. Also,
The lipid mixture is useful as an emulsifier or a bitterness suppressor.

[0019]

EXAMPLES The present invention will now be described more specifically by way of examples, which are merely illustrative and do not limit the present invention.

Example 1 100 g of soybean lecithin (SLP-paste; manufactured by Trurecitin Industry Co., Ltd.) having the composition shown in Table 1 was stirred and filtered with 500 ml of a mixed solvent of 80 parts by weight of ethanol and 20 parts by weight of acetone, and the first extraction was carried out. A residue was obtained. Next, the 1st extraction residue was stirred and filtered with the said mixed solvent of the same ratio, and the 2nd extraction residue was obtained. This operation was repeated and the obtained extraction residue was desolvated.

Example 2 Instead of soybean lecithin, purified soybean lecithin (SLP-
W; manufactured by True Lecithin Industry Co., Ltd.)
An acidic phospholipid concentrate was obtained in the same manner as in.

Comparative Example 1 A lipid mixture was prepared in the same manner as in Example 1 except that purified soybean lecithin was used instead of soybean lecithin and acetone was used instead of a mixed solvent of 80 parts by weight of ethanol and 20 parts by weight of acetone. Got

Comparative Example 2 According to the same method as in Example 1 except that purified soybean lecithin was used in place of soybean lecithin, and 95% ethanol was used in place of a mixed solvent of 80 parts by weight of ethanol and 20 parts by weight of acetone. A lipid mixture was obtained.

Comparative Example 3 10 g of purified soybean lecithin (SLP-W; manufactured by Trurecitin Industry Co., Ltd.) was dissolved in 200 g of hexane, placed in a 300 ml separating funnel, and 5 g of 90% ethanol was added thereto and shaken vigorously. After shaking, the lower layer was removed, the same amount of the above ethanol was added, and the same operation was performed. This operation was repeated 6 times conveniently, the upper layer was collected, and the solvent was topped off to obtain a lipid mixture.

[0025]

[Table 1]

Claims (4)

[Claims] 1. A method for concentrating an acidic phospholipid, which comprises treating lecithin with a mixed solvent of lower alcohol and acetone to remove the mixed solvent fraction. 2. The method for concentrating acidic phospholipids according to claim 1, wherein the lecithin is at least one selected from soybean lecithin, egg yolk lecithin, rapeseed lecithin and corn lecithin. 3. The method for concentrating acidic phospholipids according to claim 1, wherein the lower alcohol is ethanol. 4. The method for concentrating an acidic phospholipid according to claim 1, wherein 0.1-100 parts by weight of a mixed solvent of lower alcohol and acetone is used with respect to 1 part by weight of lecithin.