JPH11269456A - Highly unsaturated fatty acid composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a compsn. which improves the stability of a highly unsatd. fatty acid in vivo and enhances the utilization factor of the acid in vivo by incorporating sesamine and/or an analog thereof and a highly unsatd. fatty acid into the same. SOLUTION: This compsn. contains a highly unsatd. fatty acid and, based on the acid, at least 0.1 wt.% sesamine and/or an analog thereof and improves the stability and utilization factor of the acid in vivo. Sesamine and analogs thereof are dioxabicyclo[3,3,0]octane derivs., including sesamine, sesaminol, episesamine, episesaminol, and sesamolin. Examples of highly unsatd. fatty acids include the (n-3) series such as docosahexaenoic and eicosapentaenoic acids, the (n-6) series such as γ-linolenic, dihomo-γ-linolenic, and arachidonic acids, and the (n-9) series such as mead acid. Easily oxidizable substances include vitamins such as vitamin C and vitamin E.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a composition containing an oxidizable component having improved oxidative stability in a living body, and more particularly to a composition containing sesamin and / or an analog thereof. The present invention relates to a composition having improved in vivo oxidation stability and in vivo utilization. More specifically, the present invention relates to a composition of a polyunsaturated fatty acid containing sesamin and / or episesamin as an antioxidant in a living body.

[0002]

2. Description of the Related Art Fatty acids containing two or more unsaturated bonds are collectively referred to as polyunsaturated fatty acids and are known as in vivo components.
-3) system and (n-6) system. Since these (n-3) and (n-6) polyunsaturated fatty acids cannot be synthesized in the body in animals, it is necessary to ingest these as essential fatty acids from food.

Examples of (n-3) polyunsaturated fatty acids include eicosapentaenoic acid [20: 5 (n-3)] and docosahexaenoic acid [22: 6 (n-3)]. Has attracted attention as a material for functional foods and pharmaceuticals because it has physiological activities such as anti-inflammatory action and antithrombotic action.

[0004] On the other hand, examples of the (n-6) polyunsaturated fatty acids include γ-linolenic acid [18: 3 (n-6)],
There are dihomo-γ-linolenic acid [20: 3 (n-6)], arachidonic acid [20: 4 (n-6)] and the like, which are attracting attention as intermediate metabolites to prostaglandins, leukotrienes and the like. I have.

Many attempts have been made to use these polyunsaturated fatty acids as raw materials for functional foods and pharmaceuticals. However, polyunsaturated fatty acids are liable to be oxidized due to the presence of a plurality of unsaturated bonds, and thus are not used in vivo. And it was difficult to obtain a stable composition. Further, for the purpose of stabilization, an antioxidant such as α-tocopherol has been added, but these effects have not been sufficient (T. Futaki et al .: Antioxidant. June 1994, Gakkai Shuppan. Center).

[0006]

An object of the present invention is to provide a composition which improves the stability of an oxidizable substance in a living body and increases the utilization rate of the oxidizable substance in the living body. Is to give. In particular, the (n-3) system and the (n-
6) It is an object of the present invention to improve the in vivo stability of the essential polyunsaturated fatty acids of the system and to provide a composition in which the utilization of these polyunsaturated fatty acids in vivo is enhanced.

[0007]

Means for Solving the Problems In order to solve the problem, the present inventors have proposed that docosahexaenoic acid (hereinafter, abbreviated as DHA) of (n-3) type highly unsaturated fatty acid as an example of highly unsaturated fatty acid. ) And various antioxidants were prepared, and the combination of antioxidants was intensively studied using DHA concentration in plasma triglyceride of rats bred with the feed as an index. As a result, lignan compounds in sesame seeds Known as an antioxidant and its analogs (Yasuko Fukuda: Study on antioxidant components of sesame seeds. Journal of Shokuiku, 37
Volume, pages 484-492, 1990 and JP-A-6-2
27977)), but D in plasma triglyceride
The inventors have found that the HA concentration is significantly increased, and completed the present invention.

That is, according to the present invention, sesamin and / or its analogs enhance the in vivo oxidative stability and in vivo utilization of polyunsaturated fatty acids which are simultaneously administered as a component of the composition. Compositions containing increased polyunsaturated fatty acids can be obtained. Further, according to the present invention, it is possible to obtain a composition in which the stability of the oxidizable substance in the living body is improved and the utilization rate of the oxidizable substance in the living body is increased.

[0009]

BEST MODE FOR CARRYING OUT THE INVENTION Sesamin and its analogs in the present invention mean, for example, dioxabicyclo [3.3.0] octane derivatives described in JP-A-4-9331. , Sesamin, sesaminol, episesamin, episesaminol, sesamolin and the like.

Further, sesamin and its analogs in the present invention can be obtained, for example, by the method described in JP-A-4-9331, which is used as an extract or as a purified product if necessary. be able to.
Furthermore, metabolites of these compounds can also be used as the sesamin analogs of the present invention as long as they exhibit the effects of the present invention.

On the other hand, examples of the polyunsaturated fatty acids in the present invention include, in addition to docosahexaenoic acid, (n-3) polyunsaturated fatty acids such as eicosapentaenoic acid, γ-linolenic acid, dihomo-γ-linolenic acid, and arachidone. (N-6) -based highly unsaturated fatty acids such as acids, (n-
9) Polyunsaturated fatty acids and the like are exemplified, and any of them can be used without any limitation. Examples of the easily oxidizable substance in the present invention include vitamins such as vitamin C and vitamin E (hereinafter sometimes abbreviated as VE), and unsaturated fatty acids in royal jelly such as 10-.
Hydroxydecenoic acid and the like are exemplified, and can be used without any limitation.

[0012] These sesamin and its analogs can be added to the composition in various ratios. The addition amount of sesamin and its analogs is not particularly limited as long as the effects of the present invention are exhibited, but when added to the polyunsaturated fatty acids, vitamin E to DHA in Evaluation Example 1 described later
Considering that sesamin has the same antioxidant effect as vitamin E,
Preferably, sesamin and its analogs are added in an amount of 0.1% by weight or more based on the polyunsaturated fatty acid.

[0013] The composition of the present invention containing at least sesamin and / or its analogs and a polyunsaturated fatty acid can take various forms, and can be used in general foods, health foods, functional foods, and dietary supplements. Etc. can be provided as food or medicine. Further, it can be used as an additive to foods such as baby milk and pharmaceuticals. Further, it can be used together with conventionally known antioxidants such as vitamin C and vitamin E.

When the composition of the present invention is used as a food or pharmaceutical or as an additive thereof, the amount of the polyunsaturated fatty acid to be used may be appropriately increased or decreased according to the amount required to exhibit its function. However, in the composition of the present invention, since the utilization of polyunsaturated fatty acids in the living body is improved, the amount of use which has been required so far is 50 to 50%.
A similar effect can be expected with a usage amount of about 80%.

[0015]

The mechanism by which sesamin and its analogs stabilize oxidizable substances such as polyunsaturated fatty acids has not been fully elucidated. However, JP-A-6-2279
No. 77 discloses that sesamin and its analogs efficiently reach the liver, where the metabolized compound has a specific scavenging effect on active oxygen and OH radicals. Therefore, it is considered that this ability to scavenge active oxygen in the liver directly prevents the oxidation of easily oxidizable substances such as polyunsaturated fatty acids administered or ingested at the same time.

It has also been shown that sesamin and its analogs prevent the oxidation of vitamin E in vivo (K. Yamashita et. Al., J. Nut).
ratio 122, 2440-2446, 19
1992), since vitamin E is known to prevent the oxidation of edible oils, when sesamin and its analogs are used in combination with an antioxidant such as vitamin E, indirect effects via these antioxidants may occur. A possible antioxidant mechanism for highly unsaturated fatty acids is also considered.

[0017]

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

Embodiment 1 FIG. Of DHA stabilization in rats
Evaluation Wistar male rats (4 weeks old) were divided into 4 groups (1) of a control group, a sesamin group, a DHA group, and a DHA + sesamin group.
(6 animals per group) and were bred for 5 weeks with the feed shown in [Table 1].

[0019]

[Table 1]

After breeding for 5 weeks, the animals were fasted for 24 hours and blood was collected, and the DHA content in plasma triglyceride, vitamin E content in plasma and lipid peroxide content in plasma were measured.

As a result, as shown in FIG.
In the group, an increase in the amount of DHA in plasma triglyceride was observed, but in the DHA + sesamin group combined with sesamin, a further significant increase in the amount of DHA was observed (p <0.01 relative to the DHA group).

Further, as shown in FIG. 2, a decrease in plasma vitamin E concentration was observed in the DHA group as compared with the control group. This is because vitamin E was consumed to prevent oxidation of the ingested DHA.

On the other hand, in the DHA + sesamin group combined with sesamin, the decrease in plasma vitamin E concentration was smaller than that in the DHA group (p <0.01). This indicates that the addition of sesamin also prevents a decrease in plasma vitamin E concentration.

Further, as shown in FIG. 3, DHA +
In the sesamin group, the amount of lipid peroxide in plasma was significantly reduced as compared with the DHA group (p <0.005).

From the results of these experiments, it was found that the added sesamin exhibited an effective antioxidant activity in vivo.

Evaluation Example 1 Oxidation of DHA by vitamin E
Evaluation of Degradation Inhibition Action 1 g of DHA ethyl ester (manufactured by Harima Chemicals, purity: 95% or more) was placed in a test tube, and vitamin E was added in an amount of 0.1% by weight or 1.0% by weight with respect to the DHA ethyl ester. The mixture was aerated and stirred for a certain period of time while keeping the temperature in a heat block at ℃. Samples were collected over time and diluted 250-fold with acetonitrile, and the amount of DHA ethyl ester was quantified by gas chromatography.

The results are shown in FIG. 4, and it was found that the addition of 0.1% by weight of vitamin E suppresses the oxidative decomposition of DHA.

From the above results, it is clear that sesamin exhibits an effective antioxidant activity in vivo and prevents the oxidation of highly unsaturated fatty acids susceptible to oxidative degradation. As the mechanism, an action of directly protecting the polyunsaturated fatty acid by the antioxidant activity and an action of indirectly protecting the polyunsaturated fatty acid while protecting the added antioxidant such as vitamin E or the like can be considered.

[0029]

In the prior art, many antioxidants such as vitamin E have been approved as food additives or pharmaceutical additives. These are primarily intended to protect foods or pharmaceuticals from oxidation before ingestion or administration, and little consideration is given to protecting functional substances or pharmaceuticals in foods from active oxygen generated in the body. Was.

On the other hand, the addition of sesamin and its analogs in the present invention is carried out by oxidizing in vivo after administration or ingestion from active oxygen or free radicals generated in the living body, thereby causing its biological activity or pharmacological activity. The main object of the present invention is to protect polyunsaturated fatty acids that lose their activity, thereby improving their oxidative stability and increasing their utilization.

According to this concept, an antioxidant that immediately eliminates the generated active oxygen and free radicals in the liver, which is considered to generate the most active oxygen and free radicals, is desirable. On the other hand, the present inventors have revealed that sesamin and its analogs are unchanged and rapidly taken up by the liver and metabolized, and that metabolites exhibit remarkably stronger antioxidant activity than the unchanged form. (JP-A-6-227977). The present invention provides a site-specific and efficient in vivo oxidation prevention method utilizing the metabolic reaction in the living body. Therefore, it is also within the technical scope of the present invention to administer or ingest an oxidizable substance simultaneously or in close proximity to sesamin and its analogs to prevent oxidation of the oxidizable substance in vivo. is there.

In the present invention, DHA, which is one of the polyunsaturated fatty acids, was examined as an oxidizable substance, and the action of sesamin and its analogs to protect DHA in vivo was clarified. By this action, by blending sesamin and its analogs with the easily oxidizable functional substance, it is possible to increase the utilization rate of the functional substance.

In addition to polyunsaturated fatty acids, there are many functional materials whose functions are lost by oxidation. From this,
The antioxidant action of sesamin and its analogs in vivo can be applied to any easily oxidizable functional substance, so its application range is not only applicable to health foods but also to pharmaceuticals. is there.

[Brief description of the drawings]

FIG. 1 is a graph showing the amount of DHA in plasma glyceride.

FIG. 2 is a graph showing the amount of vitamin E in plasma.

FIG. 3 is a graph showing the amount of lipid peroxide in plasma.

FIG. 4 is a graph showing the inhibitory effect of vitamin E on the oxidative degradation of DHA.

Claims (7)

[Claims] 1. A composition comprising at least sesamin and / or an analog thereof and a polyunsaturated fatty acid. 2. The composition according to claim 1, wherein the polyunsaturated fatty acid is docosahexaenoic acid. 3. The composition according to claim 1, wherein the in vivo utilization of the polyunsaturated fatty acid in the composition is improved by adding sesamin and / or an analog thereof. 4. The oxidative stability of polyunsaturated fatty acids in a composition in vivo by adding sesamin and / or an analog thereof is improved.
A composition according to claim 1. 5. The composition according to claim 1, wherein the analog of sesamin is episesamin. 6. A composition characterized by improving the in vivo oxidation stability of an easily oxidizable component in a composition by adding sesamin and / or an analog thereof. 7. The composition according to claim 6, wherein the analog of sesamin is episesamin.