JP2001302509A - Remnant-like lipoprotein depressant - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a serum RLP depressant comprising a diacylglycerol. SOLUTION: The serum RLP can be reduced, when diacylglycerol is ingested as food oil in the daily life whereby arteriosclerosis can be prevented.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

[0001] The present invention relates to a serum remnant-like lipoprotein (RL) which is easy to take in even daily food.
P) For reducing agents.

[0002]

BACKGROUND OF THE INVENTION Remnant-like lipoproteins (also called RLPs, remnant particles or simply remnants) are known as chylomicrons (C
M) and intermediate metabolites in the blood of lipoproteins high in triglycerides such as lipoprotein (VLDL) and very low density lipoprotein. This RLP is easily taken up by the blood vessel wall, cholesterol in the RLP is accumulated in the blood vessel wall, and at the lipoprotein level, as well as low density lipoprotein (LDL), is deeply involved in inducing arteriosclerosis. One study also reports that RLPs, which contain more triglycerides in lipoproteins, are more involved in atherosclerosis than LDL. Therefore, lowering RLP is important for preventing arteriosclerosis. Because it is more important to prevent atherosclerosis by daily diet than to treat it, it can be taken in daily life, and
What can reduce RLP is desired.

[0003]

Means for Solving the Problems The present inventor has focused on diacylglycerol, which is known to suppress an increase in blood triglyceride after meals, and has studied the effect on serum RLP. As a result, they have found that diacylglycerol has an excellent RLP lowering effect and is easy to take in daily life, and thus is useful as a health-conscious food or pharmaceutical.

That is, the present invention provides an RLP lowering agent comprising diacylglycerol.

[0005]

BEST MODE FOR CARRYING OUT THE INVENTION The fatty acids constituting diacylglycerol used in the RLP-lowering agent of the present invention have 8 to 2 carbon atoms.
4, particularly preferably 16 to 22. 70% by weight of unsaturated fatty acids in all constituent fatty acids (hereinafter simply indicated by%)
It is desirable to make the above. Further, a diacylglycerol having an unsaturated fatty acid of 70% or more and a ω3 highly unsaturated fatty acid of 15% or more in all the constituent fatty acids is more preferable. In particular, from the point of further increasing the RLP lowering effect,
The ratio of (cis unsaturated fatty acid content) / (trans unsaturated fatty acid content + saturated fatty acid content) (hereinafter referred to as (cis) / (trans + saturated) weight ratio) is preferably 5.5 or more. More preferably, the (cis) / (trans + saturation) weight ratio is at least 8, more preferably at least 9. Further, among the constituent fatty acids of diacylglycerol, the content of trans unsaturated fatty acid is particularly preferably 5% or less, and the content of saturated fatty acid is also 5%.
The following are particularly preferred. Here, the cis unsaturated fatty acids include oleic acid, α-linoleic acid, α-linolenic acid,
Cis-dihomo γ-linolenic acid, cis-arachidonic acid, cis-eicosadanteenoic acid, cis-docosahexaenoic acid and the like. Examples of the trans-type unsaturated fatty acid include a trans-type of the above-mentioned unsaturated fatty acid. Examples of the saturated fatty acid include palmitic acid, stearic acid, and arachiic acid.

[0006] Diacylglycerol is subjected to an esterification reaction, for example, by subjecting a fat or oil having a desired constituent fatty acid to glycerin or by subjecting a mixture of the desired constituent fatty acid or its ester and glycerin to lipase. It is manufactured by In order to prevent isomerization during the reaction, an esterification reaction using a lipase is more preferable. Also, in order to prevent isomerization in the purification means after the reaction is completed by the esterification reaction using lipase, it is preferable that the purification means is also performed under mild conditions such that fatty acid isomerization does not occur.

[0007] The composition obtained by the above method is a fat or oil composition containing diacylglycerol. In the present invention, the diacylglycerol-containing oil / fat composition is preferably used. It is preferable that the fat composition contains 35% or more of diacylglycerol from the viewpoint of RLP lowering action. Further, the diacylglycerol content in the oil / fat composition is more preferably at least 50%, further preferably at least 60%, particularly preferably at least 80%.

[0008] Normal vegetable oils contain 0.0% of plant sterols.
About 5 to 1.2% is contained. However, the content of plant sterols in a fat or oil composition containing diacylglycerol varies depending on the production method. For example, when a commercially available fatty acid obtained by distillation is used as a raw material, the amount of plant sterol in the composition is reduced. In such a case, it is preferable to add the plant sterol so as to be 0.05% or more. The upper limit of the plant sterol content is not particularly limited. Here, as the plant sterol, for example, α-sitosterol, β-sitosterol, stigmasterol, campesterol, α-
Free forms such as sitostanol, β-sitostanol, stigmasteranol, campestanol, cycloartenol, and fatty acid esters, ferulic acid esters, and cinnamic acid esters thereof are also included.

[0009] Other components contained in the fat and oil composition are triacylglycerol and monoacylglycerol. The monoacylglycerol content is less than 2%, in particular 1.
It is preferably at most 5%. The balance is mostly triacylglycerol.

[0010] As shown in the test examples described below, diacylglycerol and the oil / fat composition containing the same have an excellent serum remnant-like lipoprotein-lowering effect and are easy to take daily. It is useful as a health-oriented food for the purpose and as a pharmaceutical.

The serum RLP lowering agent of the present invention includes components contained in ordinary fats and oils compositions, for example, antioxidants such as tocopherol, ascorbic acid palmitate, ascorbic acid stearate, BHT, BHA, phospholipid, and sucrose fatty acid. Emulsifiers such as esters, polyglycerin fatty acid esters, and organic acid monoglycerides may be blended.

[0012] In general, diacylglycerol raises the melting point as compared with triacylglycerol having the same fatty acid composition. However, the above composition has a merit that it is liquid at normal temperature and can be widely used as an edible oil. Therefore, the RLP-lowering agent of the present invention can be suitably used as cooking oil and various processed fats and oils. Examples of processed foods include drinks, desserts, ice creams,
Oil-in-water type oil-and-fat processed foods such as dressings, toppings, and mayonnaise; water-in-oil type oil-and-fat processed foods such as margarine and spreads; Processed oil-and-fat foods such as peanut butter, flying, baking shortening; potato chips, snacks, cakes, cookies, It can be used for processed foods such as pies, breads and chocolates; bakery mixes; processed meat products; frozen entrées; In addition, it can be used in the form of capsules, tablets and the like.

The daily intake of the RLP lowering agent of the present invention is 0.03 to 25 g as diacylglycerol,
20 g, especially 6 to 15 g, is preferred.

[0014]

Example 1 A fatty acid obtained by hydrolyzing a commercial soybean oil having a trans acid content of 0.8% was reduced in saturated fatty acids by wintering, and then a commercially available immobilized 1,3-position selective lipase was obtained. (Lipoz
The fatty acid and glycerin were reacted at 40 ° C. using yme 3A (manufactured by Novo Industry AS) as a catalyst. After filtering off the lipase preparation, the reaction-completed product was subjected to molecular distillation and purified by a conventional method to obtain a fat / oil composition A.

EXAMPLE 2 A fatty acid obtained by hydrolyzing a commercial rapeseed oil having a trans acid content of 0.6% was converted to a commercially available immobilized 1,3-position selective lipase.
(Lipozyme 3A, manufactured by Novo Industry AS) was used as a catalyst to react the fatty acid with glycerin at 40 ° C. After filtering off the lipase preparation, the reaction-completed product was subjected to molecular distillation and purified by a conventional method to obtain a fat / oil composition B.

Example 3 A fatty acid obtained by hydrolyzing a commercial rapeseed oil having a trans acid content of 2.8% was converted to a commercially available immobilized 1,3-position selective lipase.
(Lipozyme 3A, manufactured by Novo Industry AS) was used as a catalyst to react the fatty acid with glycerin at 40 ° C. After the lipase preparation was separated by filtration, the reaction-completed product was subjected to molecular distillation and purified by a conventional method to obtain an oil / fat composition C.

Example 4 A commercially available DHA-rich oil and glycerin were mixed, and an alkali catalyst (sodium methoxide) was used as a catalyst.
A transesterification reaction was performed at 0 ° C. After filtering off the catalyst,
The reaction-completed product was subjected to molecular distillation and purified by a conventional method to obtain a fat / oil composition D.

The glyceride compositions of Examples 1 to 4 and soybean oil (Comparative Example 1) and the constituent fatty acids of diacylglycerol are shown in Tables 1 and 2.

[Measurement of glyceride distribution] After fats and oils are silylated with a silylating agent (manufactured by Kanto Kagaku, silylating agent TH), a capillary column (manufactured by J & W, DBTM-1) is used.
And analyzed by gas chromatography.

[Distribution of Constituent Fatty Acids of Diacylglycerol] Column chromatogram (manufactured by Wako Pure Chemical Industries, Ltd., "Wakogel C-200 and triacylglycerol fraction were dropped with hexane, and then diacylglycerol fraction was diluted with hexane / ether = 70/30). The diacylglycerol fractions in the fats and oils were collected, methylesterified by a conventional method, and then subjected to a capillary column (manufactured by Chrompack, CP-S).
(IL88) and analyzed by gas chromatography.

[0021]

[Table 1]

[0022]

[Table 2]

Test Example 1 Each of the fats and oils compositions was used for one month, instead of a commonly used edible oil. The daily intake at that time was 10 g as diacylglycerol. Each test was performed on eight adult men and women with higher serum triglycerides. Table 3 shows the effects of Examples and Comparative Examples on RLP. The relative value when the initial value is set to 100 is shown. RLP is
Quantification was performed based on the amount of cholesterol in the fraction obtained by fractionation using an anti-apoB-100 / anti-apoA1 monoclonal antibody affinity mixed gel.

[0024]

[Table 3]

[0025]

EFFECT OF THE INVENTION Serum RL can be obtained by ingesting diacylglycerol or an oil or fat composition containing the same as daily edible oil or fat.
Since P can be reduced, arteriosclerosis can be prevented.

Claims (1)

[Claims] 1. A remnant-like lipoprotein lowering agent comprising diacylglycerol.