JPH0975001A - Food or drink containing oils and fats - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a food or drink effective for easily and remarkably accumulating docosahexaenoic acid in the body by the take of a small amount of the food, etc., compared with conventional docosahexaenoic acid supplying source. SOLUTION: This food or drink such as cream, margarine, salad dressing or mayonnaise (excluding a food or drink containing oils and fats for the nutrition of mother and infant and a composition containing oils and fats for medical use) is produced by compounding, as an active component, a mixed triglyceride containing a docosahexaenoic acid residue bonded to the 2-site of glyceride in an amount of <40mol% based on the total amount of the docosahexaenoic acid residue existing in the triglyceride and containing the fatty acid residues of the 1-site and the 3-site distributed regularly or randomly between the sites.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a fat-and-oil-containing food or drink which has a high organ accumulation of docosahexaenoic acid.

[0002]

2. Description of the Related Art N-3 long-chain polyunsaturated fatty acids are widely distributed in the form of phospholipids in nerve-related tissues such as cerebral cortex synaptic membrane of animal brain and photoreceptor membrane of retina. Most of these n-3 long-chain polyunsaturated fatty acids are docosahexaenoic acid (total cis-4, 7, 10, 13, 1).
6,19-docosahexaenoic acid, C _{22: 6} , where the number after C indicates the total number of carbons: the number of double bonds and the same shall apply hereinafter. ), And the content of docosahexaenoic acid in various mammalian cerebrums and retinas is almost constant regardless of the diet, it is speculated that there is a relationship with the brain and nervous system.

The content of docosahexaenoic acid in human brain is
Increased 3-5 times in the last 3 months of gestation, 12 after birth
Further increase 3 to 5 times a week. On the other hand, docosahexaenoic acid accounts for about 35 to 60% of the fatty acids in the phospholipids that make up the rod outer segment of the retina. Regarding the relationship between docosahexaenoic acid and retinal function, experiments using rats and reesus monkeys have been conducted, and a decrease in the visual acuity threshold and a decrease in retina potential due to deficiency of n-3 fatty acids such as docosahexaenoic acid have been observed. Were reported (Bourre et al.,
J. Nutr., Vol. 119, p. 1880, 1989),
It has been suggested that docosahexaenoic acid is deeply associated with retinal function.

In an experiment using rats, docosahexaenoic acid was supplied from the mother rat via the placenta in the fetal period when biosynthesis is low and from milk after birth, and docosahexaenoic acid production capacity in vivo is sufficient. It has been suggested that it becomes supplied from the liver at about 7 weeks of age.
Among them, it has been recognized that a group that continuously ingests docosahexaenoic acid through the placenta during the fetal period, after birth, and from the diet after weaning has significantly superior learning ability. ("Fisheries lipid-its characteristics and physiological activity", Seiseisha Koseikaku (1993)). Also, Lucas et al.
As a result of investigating the IQs of premature infants at the age of 7 to 8, the group fed with breast milk (containing docosahexaenoic acid) has an intelligence index of about 10 compared to the group fed with artificial milk containing no docosahexaenoic acid. Reported to be high (Proc Nat
Acad Sci USA 89 , 7840, (1992)). These studies suggest that docosahexaenoic acid is effective in learning ability and memory retention. Especially human development,
It is considered to be an essential ingredient during growth, and recently, products such as infant formulas fortified with docosahexaenoic acid have been developed.

Soderberg et al. Examined the content of docosahexaenoic acid in the phospholipids of the hippocampus, which is involved in memory in the brain, and found that those who died of Alzheimer's disease (80 on average).
Docosahexaenoic acid in 1 year old) has been reduced to half that of those who died of other diseases (79 years old on average) (Proc Natl Acad Sci USA 89 , 7836,
(1992)). On the other hand, an experiment in which docosahexaenoic acid content in the brain was increased as a result of administration of docosahexaenoic acid to aged rats has been reported (Int News Fats Oils R
elat Mater 1 , 520 (1990)). From these reports, it is considered that docosahexaenoic acid is involved in aging and dementia and is useful for improving brain function in the elderly.

[0006] Therefore, in order to supplement docosahexaenoic acid from the outside of the body, intentionally ingesting foods containing a large amount of fish containing docosahexaenoic acid, or infant formula prepared from fish oil or fish oil concentrates containing docosahexaenoic acid. , Health foods are commercially available. However, in order to obtain the above-mentioned desired effects, it was necessary to ingest or administer these in large amounts over a long period of time.

As a material containing docosahexaenoic acid,
Fish oil is often used. Sardine oil, cod liver oil, herring oil, squid oil, and tuna orbital oil are mainly used as fish oils. When the chemical structures of these oils and fats are examined, all of them have a docosahexaenoic acid residue that forms an ester bond at the 2-position of triglyceride. However, 50 mol% or more of the total amount of docosahexaenoic acid residues present in the triglyceride has a triglyceride structure in which there are more docosahexaenoic acid residues bonded at the 2-position than at the 1- and 3-positions.

On the other hand, polyunsaturated fatty acids such as docosahexaenoic acid, on the other hand, are more likely to be oxidized because they have a larger number of double bonds in the molecule than ordinary fatty acids constituting edible vegetable oils and fats, and are ingested in the body in excess. It is also known to cause harmful effects. When lipid peroxidation proceeds in vivo, it causes damage to biological membranes, ischemic diseases, arteriosclerosis,
It is presumed to cause lesions such as cataract, cancer, Alzheimer's disease, collagen disease, and amyloidosis.

[0009]

DISCLOSURE OF THE INVENTION The present invention has been made in view of such a situation as described above, and it has no side effects on humans and animals, and can be ingested in a smaller amount than the conventional docosahexaenoic acid source. It is an object to provide an oil and fat-containing food and drink (however, excluding an oil and fat-containing food and drink for mother and child nutrition and a medical oil-and-fat containing composition) in which docosahexaenoic acid is likely to be accumulated in an organ.

[0010]

Means for Solving the Problems The inventors of the present invention have conducted extensive studies to achieve the above object, and found that fats and oils having a large amount of docosahexaenoic acid at the 1- and 3-positions of a triglyceride structure were used as a source of docosahexaenoic acid. It was found that docosahexaenoic acid has a higher organ-accumulating effect than the commonly used fish oil having a large amount of docosahexaenoic acid at the 2-position, and the above-mentioned object is achieved. The present invention has been completed based on such findings.

In the present invention, the triglyceride structure of 2
A structure in which the docosahexaenoic acid residues bound to the position are less than 40 mol% of the total amount of the docosahexaenoic acid residues present in the triglyceride, and the fatty acid residues at the 1st and 3rd positions are regularly or randomly distributed between the positions. Oils and fats containing mixed triglycerides with
In addition to the naturally occurring oils and fats such as milk and fats, microbial oils and fats and microalgae oils and fats, oils and fats produced by transesterification using 1,3-position specific lipase are included.

The mixed triglyceride characteristic of the present invention is a triglyceride consisting of a fatty acid containing docosahexaenoic acid and glycerin. When the total amount of docosahexaenoic acid is 100 mol%, the mixed triglyceride is less than 40 mol% and any fatty acid other than docosahexaenoic acid. Is located at the 2-position of the triglyceride, and 60 mol% or more of docosahexaenoic acid and any fatty acid other than docosahexaenoic acid are randomly or non-randomly distributed at the 1- and 3-positions of the triglyceride.

The fatty acids constituting the mixed triglyceride according to the present invention are docosahexaenoic acid and other fatty acids. As the latter fatty acid, any of short-chain, medium-chain and long-chain fatty acids, and saturated and unsaturated fatty acids can be used. Among them, straight-chain, medium-chain having 6 or more carbon atoms Those having a long-chain, saturated or unsaturated fatty acid are preferable. Such fatty acids include caproic acid (C _{6: 0} ), caprylic acid (C _{8: 0} ), capric acid (C _{10: 0} ), lauric acid (C _{12: 0} ), myristic acid (C
_{14: 0} ), palmitic acid (C _{16: 0} ), palmitooleic acid (C _{16: 1} ), stearic acid (C _{18: 0} ), oleic acid (C
_{18: 1} ), elaidic acid (C _{18: 1} ), linoleic acid (C _{18: 2} ), α-linolenic acid (C _{18: 3} , 9, 12, 15)
-Octadecatrienoic acid), α'-linolenic acid (C _{18: 3} , 5,8,11-octadecatrienoic acid), γ
-Linolenic acid ( _C18: 3,6,9,12-octadecatrienoic acid), Eleostearic acid ( _C18: 3,9,11,1)
3-octadecatrienoic acid), octadecatetraenoic acid ( _C18: 4,6,9,12,15-octadecatetraenoic acid), arachidic acid (C20 _{: 0} ), arachidonic acid (C20 _{: 4).} ), Gadoleic acid (C _{20: 1} ), eicosapentaenoic acid (C _{20: 5} , 5,8,11,14,17-eicosapentaenoic acid), behenic acid (C _{22: 0} ), erucic acid (C
_{22: 1} ), brassic acid (C _{22: 1} ), docosapentaenoic acid (C _{22: 5} , 7, 10, 13, 16, 19-docosapentaenoic acid) and the like. These fatty acids may be used alone or may be used as a mixed fatty acid in any proportion. Among these, myristic acid, palmitic acid, stearic acid, oleic acid,
Linoleic acid, α-linolenic acid, arachidonic acid, eicosapentaenoic acid and docosapentaenoic acid are preferred.

In order to produce the mixed triglyceride according to the present invention composed of docosahexaenoic acid and other fatty acids, a technique such as a chemical synthesis method, a transesterification method, or an oil and fat extraction method from the natural product can be used. Good. Examples of the chemical synthesis method include a desired amount and composition of fatty acid,
Fatty acid anhydrides or fatty acid halides (fatty acid chlorides) and glycerin, acidic substances (hydrochloric acid, sulfuric acid, paratoluene sulfonic acid, etc.), alkaline substances (sodium hydroxide, potassium hydroxide, etc.), metals (zinc, tin, titanium) , Nickel, etc.), metal oxides (zinc oxide, alumina, ferrous oxide, etc.), metal halides (aluminum chloride, tin chloride, etc.) in the presence or absence of esterification catalysts, etc. in a nitrogen gas stream. At 100 to 250 ° C., the esterification reaction may be carried out for 1 to 25 hours while removing the produced water.

The esterification product may be subjected to alkali deoxidation treatment, adsorption / fractionation treatment using activated carbon, activated clay, alumina, silica gel, ion exchange resin, etc., hydrophilic organic solvent such as methanol or ethanol and / Or n
-Solvent fractionation treatment using a lipophilic organic solvent such as hexane or xylene to remove impurities such as free fatty acids, monoglycerides, diglycerides, coloring substances, and odorous components. Fractionation or concentration of the triglyceride component such that the content of the docosahexaenoic acid residue bonded to the position is less than 40 mol% of the total content of the docosahexaenoic acid residue bonded to the 1st, 2nd and 3rd positions of the triglyceride. You may. The mixed triglyceride according to the present invention is preferably deodorized by blowing steam under heating and under reduced pressure.

In order to obtain the mixed triglyceride according to the present invention by using the transesterification method, for example, the fatty acid triglyceride (component a-1) containing a large amount of docosahexaenoic acid as a raw material and docosahexaenoic acid are not substantially contained. A small amount of a fatty acid (component a-2), a lower alcohol ester of component a-2 (methyl ester, ethyl ester, etc.) or a triglyceride of component a-2 is mixed in a desired ratio, or docosahexaenoic acid is added. A catalyst is prepared by mixing a required amount of a triglyceride of a fatty acid (component b-1) which is substantially free or contained in a small amount and a fatty acid (component b-2) containing a large amount of docosahexaenoic acid or a lower alcohol ester of a component b-2. As an alkaline substance such as sodium hydroxide and potassium hydroxide, sodium methylate, and nato Umuechirato, metal alcoholates (metal alkoxides) such as lithium butyrate, basic anion exchange resins, ion exchange resins such as acid cation exchange resins, or that causes an ester exchange reaction using a lipase is simple. When transesterification is carried out using a specific lipase as a catalyst, a new fatty acid group can be selectively introduced at the 1-position and 3-position of the triglyceride, as will be described later, and the method for producing the mixed triglyceride according to the present invention. As desirable.

The raw materials for the transesterification are sardine oil, cod liver oil, herring oil, squid oil, fish oils such as tuna orbital oil, and compressed fish obtained from marine mammals such as whales, seals and fur seals as component a-1. Alternatively, extracted oil, milk fat of the animal, chlorella, spirulina, donariella, etc., and also genus Nannochloropsis (eg Nannochloropsis ocul
ata), Trust chytrium (eg Thraustochytri
um aureum), Crypthecodinium (eg Crypth
ecodinium cohnii), isochrysis (eg Isochrys
fats and oils extracted from microalgae belonging to
Fats and oils derived from microorganisms such as the genus Mortierella, and triglyceride of mixed fatty acid with docosahexaenoic acid or the above-mentioned various fatty acids containing the docosahexaenoic acid in any proportion (see paragraph 0013) can be used. Component a-
Various fatty acids (see paragraph 0013) or their derivatives can be used as 2.

As the component b-1, there are triglycerides obtained from plants, animals, microorganisms, microalgae, etc., soybean oil,
Rapeseed oil, cottonseed oil, corn oil, palm oil, palm oil, safflower oil, high oleic safflower oil, sunflower oil, high oleic sunflower oil, olive oil, peanut oil, cacao butter, chinese tallow, sal butter, shea butter, Beef tallow, lard, hydrogenated oils and fats thereof, fractionated oils and fats, and the component a
Examples of the triglyceride of No. 2, medium-chain fatty acid triglyceride and the like can be exemplified, and as the component b-2, there is a fatty acid obtained by the hydrolysis treatment of the component a-1.

In the transesterification reaction, for example, the above raw materials are mixed in a molar ratio of component a-1: component a-2 = 1: 0.1.
5, component b-1: component b-2 = 1: 2 to 10 are mixed, and when an alkali or a metal alcoholate is used as a catalyst, it is in an anhydrous state and is 0.5 to 0.5 at 80 to 120 ° C. Allow transesterification for 3 hours. Similarly, when an ion exchange resin is used, it is also in an anhydrous state, but it is preferable to circulate and contact the raw materials in a column system at room temperature to 40 ° C. When using lipase as a catalyst, the water content in the raw material is set to 1% by weight or less, and commercially available lipase powder or a known carrier such as celite, diatomaceous earth, activated carbon, porous glass, ion exchange resin, chitosan, high Immobilized lipase immobilized on molecular gel, cellulose powder or the like is added, and transesterification reaction is performed at 20 to 80 ° C. for 0.5 to 20 hours.

As the lipase, those originating from the microorganisms described below or those originating from animal organs can be used. Ie Aspergillus niger,
Genus Mucor (eg Mucor miehei), genus Candida (eg Candida cyrindracea), genus Pseudomonas (eg Pseudomonas fragi), genus Alcaligenes (eg Alcaligene described in Japanese Patent Publication No. 58-36953).
s sp.), genus Rhizopus (eg Rhizopus delemar), genus Geotrichum (eg Geotrichum candidum) and the like, and lipases of porcine pancreatic lipase of microbial origin. Of these, lipases originating from microorganisms of the genus Aspergillus, genus Mucor, genus Alcaligenes and genus Rhizopus, and porcine pancreatic lipase specifically act on the 1- and 3-positions of glycerides, and therefore, when producing the triglyceride according to the present invention, It is suitable.

The transesterification reaction product obtained by the above-mentioned various transesterification methods can be the transesterification reaction product itself as the mixed triglyceride according to the present invention depending on the kind of raw material selected. As in the case of the esterification products obtained, if necessary, alkali deoxidation treatment, adsorption / fractionation treatment, solvent fractionation treatment or solventless fractionation (wintering) treatment, etc. are performed in an appropriate combination to remove impurities. The mixed triglyceride according to the present invention can be obtained by fractionating or concentrating the glyceride component. The triglyceride is preferably deodorized.

The mixed triglyceride according to the present invention can also be obtained by a method of extracting fats and oils from a natural product. That is, among those described as the raw materials for transesterification (component a-1), whales and seals (harbor)
seal, harp seal, etc.), body tissues of marine mammals such as fur seals, milk secreted from the animals, cells of microalgae such as chlorella, spirulina, and Donaliella, or cultured cells thereof, Nannochloropsis genus,
Microalgae belonging to the genus Thraustochytrium, genus Crypthecodinium, genus Isochrysis, etc., for example Nannochloropsis oculata
), Trustchytrium aureum (Thraustochytr
ium aureum), Cryptecodynium cornie (Cry
pthecodinium cohnii), Isocrisis galvana (Iso
chrysis galbana) etc. or these cultured cells are used as raw materials. In addition, when it originates from a microorganism, it does not matter if the triglyceride obtained therefrom satisfies the glyceride structure according to the present invention.

These are squeezed or n-hexane,
Chloroform, benzene, methanol, extraction or fractionation using an organic solvent such as diethyl ether to obtain an oil content, which is subjected to degumming, alkaline deoxidation, decolorization, deodorization, etc. to give free fatty acids, phospholipids, The glyceride fraction can be obtained by removing impurities such as glycolipids, unsaponifiable substances, coloring substances and odorous components. This glyceride fraction can be used as the mixed triglyceride according to the present invention. The glyceride fraction is further fractionated by solvent-free low temperature fractionation, solvent fractionation or a silica gel column to give a docosahexaenoic acid residue bonded to the 2-position of triglyceride. It is also possible to produce triglycerides with even fewer groups.

The mixed triglyceride according to the present invention produced by the chemical synthesis method, the transesterification method or the extraction method from a natural product as described above has less than 40 mol% of the total amount of docosahexaenoic acid as its constituent fatty acid. Is an ester bond at the 2-position of the triglyceride, but it is more preferably less than 20 mol%. 40 mol%
In the above case, the desired effect of the present invention becomes small. Further, it has a structure in which 60 mol% or more of the total amount of docosahexaenoic acid and fatty acids other than docosahexaenoic acid are randomly or non-randomly distributed at the 1- and 3-positions of triglyceride to form an ester bond. The mixed triglyceride according to the present invention can be used as an oil or fat as it is, or can be used as an oil or fat by mixing it with an ordinary edible oil or fat as an active ingredient, for example, an animal or vegetable oil or fat as described as the component b-1. At this time, the content of the mixed triglyceride according to the present invention is preferably 5 to 100% by weight, more preferably 10 to 100% by weight, based on the total fat and oil.
Most preferably, it is 20 to 100% by weight. If it is less than 5% by weight, the desired effect of the present invention is small.

In the present invention, the oil and fat prepared by the above-mentioned method, that is, the triglyceride composed of glycerin and the fatty acid containing docosahexaenoic acid,
Less than 40 mol% of the total amount of docosahexaenoic acid and fatty acids other than docosahexaenoic acid are distributed in the second position of the triglyceride, and 60 mol% or more of the total amount of docosahexaenoic acid and any fatty acid other than docosahexaenoic acid are 1% of triglyceride. An oil or fat consisting of mixed triglycerides which are randomly or non-randomly distributed at the 3rd and 3rd positions and ester-bonded to each other, or the mixed triglyceride and any of the edible animal and vegetable oils and fats, wherein the mixed triglyceride content is 5% by weight or more. Foods and drinks are provided which contain as an essential component fats and oils blended as described above.

Since the fats and oils according to the present invention contain polyunsaturated fatty acids, they can be handled in the same manner as ordinary edible fats and oils, except for applications such as frying oil which is subjected to heat treatment for a long time. Can be processed with raw materials. To avoid quality deterioration, tocopherol, ascorbic acid ester (palmitate, stearate, etc.), β-carotene,
It does not matter if other antioxidants are blended in appropriate amounts, or oil-soluble dyes and fragrances are added.

The type of food and drink referred to in the present invention is not particularly limited, but foods and food materials containing fats and oils are preferred, not intended for the case where the oils and fats themselves are eaten and drinked alone. Specifically, natural food materials containing oils and fats such as meat, fish, shellfish, cereals, seeds, milk, chicken eggs, roe and processed foods thereof, butter, margarine, cream, ice cream,
Examples include salad dressing, mayonnaise and mayonnaise-like emulsified food, chocolate, snacks, cakes, donuts, cookies, rice crackers, croquettes and other oil-containing processed foods, soups, soy sauces, sauces and other liquid seasonings. Further, it may be added to juices of fruit juice and vegetable juice, carbonated drinks, coffee drinks, lactic acid bacteria drinks, soft drinks, drinks containing various vitamins and minerals, drinks for supplementing nutrients or calories, foods for the elderly, and the like. It can also be made into capsules, tablets, candies, granules or powders with known excipients. The food and drink of the present invention does not contain a medical oil-and-fat-containing composition (liquid food, infusion solution, fat emulsion, etc.) for medically supplying nutrition or calories for various diseases. Further, the food and drink of the present invention include fat and oil-containing food and drink for nutritional supply to mothers and children, for example, maternal fat and oil-containing special-purpose foods such as milk for lactating women, infant formula, and follow-up milk. Not intended for dairy products, baby foods containing fats and oils (foods for weaning), and foods and drinks for infants.

The content of the fats and oils according to the present invention in these foods and drinks cannot be uniformly defined depending on the difference in the type and form of the foods and drinks, but it should be based on the whole fats and oils contained in or added to the foods and drinks. The mixed triglyceride is generally 5% by weight or more, preferably 10 to 100% by weight,
More preferably, it is 20 to 100% by weight. Further, the content of the mixed triglyceride with respect to the whole food and drink is at least about 0.1% by weight or more, and the upper limit is the amount corresponding to the fat and oil content in the food and drink. The oil / fat according to the present invention (that is, the oil / fat consisting only of the mixed triglyceride and the oil / fat containing 5% by weight or more of the mixed triglyceride) may be appropriately used in such a blending ratio. If it is less than the lower limit value, the organ accumulation effect of docosahexaenoic acid becomes small. The upper limit can be appropriately set within a known range according to the type of food and drink. The method of blending the fats and oils according to the present invention into foods and drinks is not particularly limited, and the same operations as in the case of general edible fats and oils, mixing, dispersion, oil-in-water emulsion, water-in-oil emulsion, and dissolution are performed. Alternatively, it may be solubilized and added to food and drink.

By ingesting the food or drink of the present invention, docosahexaenoic acid can be efficiently accumulated in the organ. Moreover, this effect is remarkably greater than that of the food and drink containing the conventional docosahexaenoic acid source such as fish oil. Furthermore, the food and drink of the present invention can be used for the purpose of maintaining or improving brain and nerve functions based on the above effects.

[0030]

【Example】

Reference Example 1 1 kg of triolein and fish oil (manufactured by Tama Biochemical Co., Ltd., trade name: EPA-18) were hydrolyzed mixed fatty acids at low temperature fractionated fish oil hydrolyzed fatty acid concentrate (C _{20: 5} : 3 in total fatty acids).
7.4 mol%, C22 _{: 5} : 5.4 mol%, C22 _{: 6} : 25.
2 mol%. BHT added 0.01% by weight) and 1: 5
(Molar ratio), and after adjusting the water content to 0.2% by weight, a glass column (10 cmφ) filled with Lipozyme IM20 (trade name; lipase derived from Mucor miehei, manufactured by Novo Nordisk Co., Ltd.) X 60 cm)
Then, a selective transesterification reaction was carried out at 40 ° C.

After removing free fatty acids from the transesterification reaction product by steam distillation and washing with water, stainless steel filled with silica gel (Wako Pure Chemical Industries, Ltd., Wako Gel C100) infiltrated with n-hexane. The mixture was applied to a column and eluted with n-hexane to remove diglyceride to obtain 720 g of mixed triglyceride according to the present invention. The total fatty acid composition constituting the present triglyceride and the fatty acid compositions at the 1st, 3rd and 2nd positions of the glyceride were determined by GLC analysis. Table 1 shows the results. Of the fatty acids constituting this triglyceride, 4 mol% of the total amount of C _{22: 6} (docosahexaenoic acid) was distributed at the 2-position of the triglyceride. This triglyceride was used as a test oil for the following animal experiments.

0.1% by weight of sodium methoxide was added to a part of the present triglyceride, and a random transesterification reaction was carried out at 100 ° C. under reduced pressure, followed by filtration using Celite to give a random transesterification reaction of the present triglyceride. I got a thing. The total fatty acid composition, the respective fatty acid compositions at the 1st, 3rd and 2nd positions were determined in the same manner as described above (see Table 1). At the 2-position of this triglyceride, the total amount of docosahexaenoic acid is 45
The mol% was distributed. This random transesterification product was used as a control oil for animal experiments.

[0033]

[Table 1] * Total carbon number: Displayed as the number of double bonds

Seven 4-week-old SD male rats were used as one test group, and a breeding experiment was carried out using a feed containing 5% by weight of either the test oil or the control oil (see Table 2). During this period, the feed was prepared and fed daily in order to prevent oxidative deterioration of the prepared feed. After free feeding of water and each of the above feeds for 3 weeks, docosahexaenoic acid content in phospholipids (phosphatidylcholine, phosphatidylethanolamine, etc.) in organs and blood of each test group rat The content of docosahexaenoic acid in the fatty acid (the same applies hereinafter) was measured. Table 3 shows the results.
No significant difference was observed in feed intake, body weight gain and liver weight in each test plot. The test for significant difference was based on the T test method (the same applies hereinafter).

From the results of this experiment, the mixed triglyceride according to the present invention (test oil) had no adverse effect on rats, and in the group to which the test oil was added, phosphatidylethanolamine in the brain and phosphatidylcholine in the blood contained docosahexaenoic acid. It was revealed that a large amount of docosahexaenoic acid was present and that docosahexaenoic acid had a high potential for organ accumulation.

[0036]

[Table 2] * 1 Nippon Claire Co., Ltd., AIN-93G-MX * 2 Nippon Claire Co., Ltd., AIN-93-VX * 3 t-Butylhydroquinone

[0037]

[Table 3] 1): Phosphatidylcholine, 2): Phosphatidylethanolamine Note) * indicates that there is a statistically significant difference at the risk rate of 5% or less compared to the control oil added group (the same applies below).

Reference Example 2 Test fats (fats containing the mixed triglyceride of the present invention) and control fats were prepared as follows. The test fat and oil was harp seal fat and oil with dry ice / acetone refrigerant.
It was cooled at 80 ° C. for 1 hour, and the precipitated crystal part was filtered off with filter paper to prepare. The control fats and oils were two types of fish oils with different fatty acid composition (mixed oil of cod liver oil and miscellaneous fish oil, tuna orbital oil), cooled with dry ice / acetone refrigerant in the same manner, and separated and blended to obtain a test fat and total fatty acid. The compositions were matched. Table 4 shows these fatty acid compositions.

[0039]

[Table 4] *: Same as the notes in Table 1.

Seven 4-week-old SD male rats were used as one test group, and oils and fats containing 20% by weight of each of the above-mentioned test oils and control oils and fats (20 parts by weight of test oils or control oils, 50 parts by weight of palm oil, A mixed fat containing 5 parts by weight of oleic safflower oil and 25 parts by weight of high linoleum safflower oil (see Table 5 for the composition of fatty acids), each containing 10% by weight (the composition of the feed is 10% by weight of 5% by weight of fat). And the same experiment as in Reference Example 1 except that 41.7% by weight of corn starch was changed to 36.7% by weight). During this period, the feed was prepared and fed daily in order to prevent oxidative deterioration of the prepared feed. After free feeding of water and each of the above-mentioned feeds and feeding for 3 weeks, the content of docosahexaenoic acid in the phospholipids in the organs and blood of each test group rat was measured. The results are shown in Table 6. No significant difference was observed in feed intake, body weight gain and liver weight in each test plot.

From the results of this experiment, it is clear that the fats and oils according to the present invention have no adverse effects on rats, and that docosahexaenoic acid is present in large amounts in phosphatidylethanolamine in the brain and phosphatidylcholine in blood. It was recognized that the organs of the plant had high accumulation potential.

[0042]

[Table 5] *: Same as the notes in Table 1. * *: Ratio of each fatty acid among saturated fatty acids, monounsaturated fatty acids, n-6 fatty acids (denoted by n-6 in the table) and n-3 fatty acids (denoted by n-3 in the table).

[0043]

[Table 6] 1), 2) and *: Same as the notes in Table 3.

Reference Example 3 Eight 9-week-old female SD rats were used as one test group, and Reference Example 2
Each diet used in 1. was fed for 3 weeks and then mated with male rats to make them pregnant. The same diet was given during pregnancy and after delivery. The content of docosahexaenoic acid in milk fat of the milk of mother rats and the content of docosahexaenoic acid of brain phospholipids (phosphatidylethanolamine) in the rat 2 weeks after birth were measured. The results are shown in Tables 7 and 8. Breeding with the feed containing the oil / fat according to the present invention increased the content of docosahexaenoic acid in the milk of mother rats and also the content of docosahexaenoic acid in the phosphatidylethanolamine of rat rat brain. From these results, it was confirmed that the fats and oils according to the present invention have high organ accumulation of docosahexaenoic acid.

[0045]

[Table 7] *: Same as the notes in Table 3.

[0046]

[Table 8] *: Same as the notes in Table 3.

Reference Example 4 A rat breeding experiment was carried out in the same manner as in Reference Example 2 except that the fats and oils used in Reference Example 2 in which the mixing ratios of the test fats and control fats and oils were changed were added to the feed. That is, 7 4-week-old male SD rats were used as one test group, and the fat or oil containing 10 wt% of the test fat or control fat or oil described in Reference Example 2 (10 wt parts of the test fat or control fat or oil, 50 parts by weight of palm oil) was added. , A mixed fat of 10 parts by weight of high oleic safflower oil and 30 parts by weight of high linoleum safflower oil. Refer to Table 9 for the fatty acid composition. The same as the above). During this time, the feed was prepared daily to prevent oxidative deterioration of the prepared feed. After free feeding of water and each of the above-mentioned feeds and feeding for 3 weeks, the content of docosahexaenoic acid in the phospholipids in the organs and blood of each test group rat was measured. Table 10 shows the results. No significant difference was observed in feed intake, body weight gain and liver weight in each test plot.

From the results of this experiment and the results of Reference Example 2,
The oil and fat according to the present invention has no side effect on rats,
Included a large amount of docosahexaenoic acid in phosphatidylethanolamine in the brain and phosphatidylcholine in blood, including the case of fats and oils mixed with a small amount of test fat compared to the control fat, and it was confirmed that docosahexaenoic acid had a high potential for organ accumulation. Was given.

[0049]

[Table 9] * And **: Same as the notes in Table 5.

[0050]

[Table 10] 1), 2) and *: Same as the notes in Table 3.

Reference Example 5 Microalga Crypthecod
inium cohnii, ATCC 30336) was planted in 30 liters of the medium shown in Table 11, aerobically cultured at 30 ° C. for 100 hours in a jar fermenter, and cultured alga cells were collected by centrifugation and collected. Lyophilized (yield 625 g). The dried algal cells were crushed and extracted in a mixed solvent of chloroform: methanol = 1: 1 (weight ratio) with a hiscotron (trade name; manufactured by Nichine Medical Science Co., Ltd.) to obtain 520 g of an oil component. The oil was supplied to a stainless steel column filled with silica gel (Wako Pure Chemical Industries, Ltd., trade name: Wakogel C100) dispersed in n-hexane, and diethyl ether: n-hexane = 10: 9.
Elution was performed at 0 (volume ratio) to obtain 250 g of the triglyceride according to the present invention. The fatty acid composition of the present triglyceride (this was used as a test fat) was determined in the same manner as in Reference Example 1 (see Table 12).

[0052]

[Table 11] (PH: 6.8)

* 1: Vitamin mix aqueous solution (weight in 1 liter of the aqueous solution) Biotin: 0.003 g Thiamine: 1.000 g * 2: Metal mix aqueous solution (weight in 1 liter of the aqueous solution) Na ₂ EDTA: 1.00 _{g FeCl 3 · 6H 2 O:} 0.05 g H 3 BO 3: 1.00 g MnCl 2 · 4H 2 O: 0.15 g ZnCl 2: 0.01 g CoCl 2 · 6H 2 O: 0.005g

[0054]

[Table 12] *: Same as the notes in Table 1.

The thus-obtained microalgae-derived triglyceride (test oil and fat) and the control oil and fat described in Reference Example 2 in an amount of 10% by weight each (10 parts by weight of the test oil or control oil and fat, 50 parts by weight of palm oil, Hiole) 10 parts by weight of Ick safflower oil and 3 of high linoleum safflower oil
0 parts by weight of mixed fats and oils. See Table 13 for fatty acid composition. 10% by weight of each feed was prepared (the feed composition is the same as in Reference Example 2 except for fat content), and the same breeding test as in Reference Example 4 was performed. The content of docosahexaenoic acid in phospholipids in the organs and blood of rats in each test group was measured. The results are shown in Table 14. No significant difference was observed in feed intake, body weight gain and liver weight in each test plot.

From the results of this experiment and the results of Reference Example 2,
The oil and fat according to the present invention has no side effect on rats,
Included a large amount of docosahexaenoic acid in phosphatidylethanolamine in the brain and phosphatidylcholine in blood, including the case of fats and oils mixed with a small amount of test fat compared to the control fat, and it was confirmed that docosahexaenoic acid had a high potential for organ accumulation. Was given.

[0057]

[Table 13] * And **: Same as the notes in Table 5.

[0058]

[Table 14] 1), 2) and *: Same as the notes in Table 3.

Example 1 20 parts by weight of the oil / fat according to the present invention (test oil) prepared in Reference Example 1, 10 parts by weight of soybean hydrogenated oil, 0.2 parts by weight of lecithin and glycerin fatty acid ester (commercially available from Kao Corporation) Name: Exel 0-95R) 0.2 part by weight was uniformly dissolved to obtain an oil phase part. On the other hand, skim milk powder 3 parts by weight, sorbitol 5 parts by weight, fresh cream 10 parts by weight, polyglycerin fatty acid ester (manufactured by Sakamoto Yakuhin Co., Ltd., trade name: SY Glister MS-310) 0.5 parts by weight and water 51.1.
A part by weight was dissolved to form an aqueous phase part. Then, the oil phase part heated to the same temperature was added to the water phase part heated to 80 ° C.
After pre-emulsification at 5 ° C, pressure is 50 using a homogenizer.
It was treated with kg / cm ² and homogenized, and cooled to room temperature to obtain an oil-in-water cream which is the food and drink of the present invention. Reference Example 1
The oil / fat according to the present invention (test oil / fat 20% by weight) prepared in Reference Example 2 in place of the oil / fat according to the present invention (test oil) prepared in
The oil-in-water cream which is the food or drink of the present invention was obtained in the same manner except that the same amount of the fats and oils contained therein was used. For comparison,
The same amount of soybean salad oil was used in place of the oil and fat according to the present invention, and the same treatment was performed to obtain the same emulsified cream. Professional panel 10
When the flavor and texture of these creams were evaluated by name, there was no effect on the quality of the cream due to the addition of the fat or oil according to the present invention.

Example 2 To 83 parts by weight of oil / fat consisting of hydrogenated soybean oil / fat / oil according to the present invention prepared in Reference Example 1 (test oil) = 2/1 (weight ratio),
0.5 parts by weight of glycerin fatty acid ester (manufactured by Riken Vitamin Co., Ltd., product name: EM-MU), lecithin 0.1
By weight, a trace amount of β-carotene was added, and further 15 parts by weight of water and 1.4 parts by weight of salt were added to emulsify and then kneaded while being rapidly cooled to obtain margarine which is a food and drink of the present invention. Further, the same procedure as in Example 1 was repeated except that the same amount of the oil / fat according to the present invention prepared in Reference Example 2 (oil / fat containing 20% by weight of the test oil / fat) was used instead of the oil / fat according to the present invention (test oil) prepared in Reference Example 1. Margarine, which is the food and drink of the present invention, was obtained. For comparison, the margarine was treated in the same manner by using the same amount of the control fats and oils (the control oil described in Reference Example 1 and the fats and oils containing 20% by weight of the control fats and oils described in Reference Example 2) instead of the fats and oils according to the present invention. Obtained. When the flavor and texture of both margarines were evaluated in the same manner as in Example 1, there was no effect on the quality of margarine due to the addition of the fat or oil according to the present invention.

Further, four kinds of margarines obtained in this Example (containing the oil and fat according to the present invention prepared in Reference Example 1 and those containing the oil and fat according to the present invention prepared in Reference Example 2, Using the control oil described in Reference Example 1 and the control oil described in Reference Example 2),
A rat breeding experiment was carried out by the method described in Reference Example 2,
The content of docosahexaenoic acid in phospholipids in the organs and blood of rats in each test group was measured. At this time, Reference Example 2
In the feed composition described in 1., the total amount of fat (10% by weight) was replaced with any one of the margarines. As a result,
When the fats and oils according to the present invention were added, the content of docosahexaenoic acid as a constituent fatty acid of phosphatidylethanolamine in the brain and phosphatidylcholine in plasma was higher than that in the case where the control fats and oils were added.

Example 3 10 parts by weight of β-cyclodextrin (manufactured by Kanto Chemical Co., Inc., reagent grade) was added to 100 parts by weight of water, and after sufficiently stirring, the oil and fat according to the present invention prepared in Reference Example 4 ( 5 parts by weight of an oil / fat containing 10% by weight of the test oil / fat was added and stirred at room temperature for 2 hours. Then, this was freeze-dried to give a powdery fat and oil-containing material (inclusion material). 30 parts by weight of the powder was added to 70 parts by weight of squeezed carrot to obtain juice as the food or drink of the present invention. When the flavor of this juice was evaluated in the same manner as in Example 1, it was found that there was no discomfort in smell, taste and appearance.

Example 4 Guar gum (0.1 parts by weight), xanthan gum (0.2 parts by weight), water (31.5 parts by weight), vinegar (7 parts by weight) and sugar (11 parts by weight) were thoroughly stirred to hydrate and mix, and then salt. 4 parts by weight and 1.2 parts by weight of pepper powder were added. Then, while stirring this, the oil and fat according to the present invention prepared in Reference Examples 1, 2, 4 and 5 (Reference Example 1: test oil, Reference Example 2: oil and fat containing 20% by weight of test oil and fat, Reference Examples 4 and 5). Any of 45 parts by weight of any of the test fats and oils (10 wt%) was added little by little, and the mixture was passed through a colloid mill to obtain a salad dressing as the food and drink of the present invention. For comparison, a soybean salad oil was used in the same amount instead of the oil and fat according to the present invention, and the same treatment was performed to obtain a salad dressing. The flavor and texture of these salad dressings (inventive products: 4 types, comparative products: 1 type) were evaluated in the same manner as in Example 1, and the quality of the salad dressing was improved by adding the fat according to the present invention. Had no effect.

Example 5 3 parts by weight of gelatin and 30 parts by weight of water were mixed while heating to prepare an aqueous gelatin solution, which was then stirred while mixing 4
Cooled to 0 ° C. In addition to this, Reference Examples 1, 2, 4 and 5
9 parts by weight of any of the fats and oils according to the present invention (same as in Example 4) prepared in 1. and soybean tocopherol (manufactured by Nisshin Oil Co., Ltd., trade name: tocopherol 100S) 0.03
After adding 20 parts by weight and emulsifying to an oil-in-water type using a homogenizer, 30 parts by weight of 10% by weight aqueous solution of gum arabic was added and mixed. While maintaining the temperature at 40 ° C. and continuing stirring, 140 parts by weight of water at the same temperature and 5 parts by weight of 10% by weight acetic acid were added, and the mixture was cooled to 5 ° C. and adjusted to pH 4.0, and further 30% by weight. 1000 parts by weight of an aqueous ethanol solution were mixed with stirring. The slurry was washed with ethanol and dried at 30 ° C. under reduced pressure to obtain microcapsules having a particle size of 10 to 50 μm. When the quality was evaluated in the same manner as in Example 1, there was no discomfort in the odor, taste and appearance.

Example 6 99.5% by weight of any of the fats and oils according to the present invention (same as Example 4) prepared in Reference Examples 1, 2, 4 and 5 was added to soybean tocopherol (same as Example 5). 3 wt% and 0.2 wt% ascorbyl palmitate (reagent grade) were mixed. On the other hand, a 10 wt% gelatin aqueous solution was prepared. These were subjected to a double cylinder type orifice (manufactured by Freund Sangyo Co., Ltd., trade name: Spherex Lab) to obtain a seamless capsule having a diameter of 5 mm using gelatin as a capsule film forming substance. When these evaluations were performed in the same manner as in Example 1, there was no discomfort in the odor, taste and appearance.

[0066]

EFFECTS OF THE INVENTION The food and drink of the present invention have no side effects on humans and animals, and have a greater organ-accumulating effect of docosahexaenoic acid than those of foods and drinks containing a conventional docosahexaenoic acid source, and are highly effective for fish oil and the like. Ingesting a smaller amount than the docosahexaenoic acid source facilitates the accumulation of docosahexaenoic acid in the body.

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[Procedure amendment]

[Submission date] August 12, 1996

[Procedure amendment 1]

[Document name to be amended] Statement

[Correction target item name] 0004

[Correction method] Change

[Correction contents]

In an experiment using rats, docosahexaenoic acid was supplied from the mother rat via the placenta in the fetal period when biosynthesis is low and from milk after birth, and docosahexaenoic acid production capacity in vivo is sufficient. It has been suggested that it becomes supplied from the liver at about 7 weeks of age.
Among them, it has been recognized that a group that continuously ingests docosahexaenoic acid through the placenta during the fetal period, after birth, and from the diet after weaning has significantly superior learning ability. ( Fujimoto Kenshiro eds, "Fisheries lipid-its characteristics and physiological activity", Seiseisha Koseikaku (1993)). Also,
Lucas et al. Examined the intelligence quotients of 300 premature babies at the age of 7 to 8 years, and found that the group fed with breast milk (containing docosahexaenoic acid) was more than the group fed with artificial milk containing no docosahexaenoic acid. The intelligence index is reported to be about 10 higher ( Hairitsu Suzuki, “Food and Development”, Volume 27, N).
o. 8, pages 6-9, 1992, Kenko Sangyo Shimbun
Company ). These studies suggest that docosahexaenoic acid is effective in learning ability and memory retention. In particular, it is considered to be an essential component during human growth and growth, and recently, products such as infant formula and milk powder fortified with docosahexaenoic acid have been developed.

[Procedure amendment 2]

[Document name to be amended] Statement

[Correction target item name] 0005

[Correction method] Change

[Correction contents]

Soderberg et al. Examined the content of docosahexaenoic acid in the phospholipids of the hippocampus, which is involved in memory in the brain, and found that those who died of Alzheimer's disease (80 on average).
Docosahexaenoic acid has been reduced to half the amount of those who died of other diseases (average age 79) ( “Food and Development”, supra ). On the other hand, as a result of administration of docosahexaenoic acid to old rats, experiments docosahexaenoic acid content in the brain was increased have been reported ( "Food
Goods and Development ”, above ). From these reports, it is considered that docosahexaenoic acid is involved in aging and dementia and is useful for improving brain function in the elderly.

[Procedure 3]

[Document name to be amended] Statement

[Correction target item name] 0017

[Correction method] Change

[Correction contents]

The raw materials for the transesterification are sardine oil, cod liver oil, herring oil, squid oil, fish oils such as tuna orbital oil, and compressed fish obtained from marine mammals such as whales, seals and fur seals as component a-1. Alternatively, extracted oil, milk fat of the animal, chlorella, spirulina, donariella, etc., and also genus Nannochloropsis (eg Nannochloropsis ocul
ata, UTEX LB 2164, etc. ), genus Trustchitrium (eg Thraustochytrium aureum, ATCC 28211, 34304)
Etc. ), Crypthecodiniu (eg Crypthecodiniu
m cohnii, ATCC 30021, ibid 30334, ibid 30336, ibid 50052
Etc. ), isochrysis (eg Isochrysis galbana, CC
AP 927/1, UTEX LB 987, etc. ), oils and fats extracted from microalgae belonging to, etc., microorganisms such as Mortierella (Mortierella) genus (M. isabellina, IFO 6336, 6739, 7873, 78)
84, ATCC 44853, etc.) , and triglyceride of mixed fatty acid with docosahexaenoic acid or the above-mentioned various fatty acids (see paragraph 0013) containing docosahexaenoic acid in any proportion. ATCC: American Type Cul
ture Collection (USA), CCAP: Culture Collectiono
f Algae and Protozoa (UK), UTEX: Culture Collec
tion of Algae at the University of Texas (USA),
IFO: An abbreviation for Osaka Fermentation Research Institute. As the component a-2, the above various fatty acids (see paragraph 0013) or derivatives thereof can be used.

[Procedure amendment 4]

[Document name to be amended] Statement

[Correction target item name] 0040

[Correction method] Change

[Correction contents]

Seven 4-week-old SD male rats were used as one test group, and the above-mentioned test fats and control fats and oils containing 20% by weight each (20 parts by weight of test fats or control fats and 50 parts by weight of palm oil) were used. , A mixed oil of 5 parts by weight of high oleic safflower oil and 25 parts by weight of high linoleum safflower oil. See Table 5 for the fatty acid composition. The breeding experiment was carried out in the same manner as in Reference Example 1 except that the amount of cornstarch was 41.7% by weight and the amount of cornstarch was 41.7% by weight.
During this period, the feed was prepared and fed daily in order to prevent oxidative deterioration of the prepared feed. Free intake of water and each of the above feeds 3
After breeding for a week, the content of docosahexaenoic acid in phospholipids in the organs and blood of each test group rat was measured.
The results are shown in Table 6. In addition, feed intake,
No significant difference was observed in weight gain or liver weight.

[Procedure Amendment 5]

[Document name to be amended] Statement

[Correction target item name] 0055

[Correction method] Change

[Correction contents]

The triglyceride derived from microalgae (test fat and oil) thus obtained and the control fat and oil described in Reference Example 2 were used.
Used, the mixed oil and fat. The fatty acid composition of each 10 wt% including fat (test oils or control oil 10 parts by weight, palm oil 50 parts by weight, high-oleic safflower oil 10 parts by weight of high-linoleic safflower oil 30 parts by weight Table 13) was mixed with each 10% by weight (the composition of the feed was the same as in Reference Example 2 except for the fat content), and the same breeding test as in Reference Example 4 was performed. The content of docosahexaenoic acid in phospholipids in the organs and blood of rats in each test group was measured.
The results are shown in Table 14. No significant difference was observed in feed intake, body weight gain and liver weight in each test plot.

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Claims (5)

[Claims] 1. The docosahexaenoic acid residue bonded to the 2-position of the glyceride is less than 40 mol% of the total amount of the docosahexaenoic acid residue present in the triglyceride, and the 1-position and the 3-position.
-Containing foods and fats containing docosahexaenoic acid having a high organ-accumulating property, which contains a mixed triglyceride having a structure in which fatty acid residues at positions are regularly or randomly distributed between the positions (however, foods and fats containing fats and oils for mother and child nutrition) And excluding compositions containing medical fats and oils). 2. The mixed triglyceride comprises an active ingredient composed of naturally occurring fats and oils containing marine mammal fats and oils, milk fats, and microalgae fats and oils, or concentrated and transesterified products thereof. The oil-and-fat-containing food or drink according to 1. 3. The oil / fat-containing food or drink according to claim 2, wherein the marine mammal is a whale or a seal. 4. The oil-and-fat-containing food or drink according to claim 2, wherein the microalgae belongs to the genus Nannochloropsis, the genus Trustchitrium, the genus Isochrysis, or the genus Crypthecodinium. 5. The oil-and-fat-containing food or drink according to claim 1, wherein the mixed triglyceride is composed of an active ingredient composed of triglyceride produced by transesterification reaction using 1,3-specific lipase.