JP2006249050A - Stabilized composite and method for producing the same - Google Patents

Abstract

The present invention provides a stabilized complex containing a compound having an isoprenoid structure and / or a quinone structure, and a method for producing the same.
SOLUTION: A compound having an isoprenoid structure and / or a quinone structure, particularly one or more compounds selected from the group consisting of farnesol, gefarnate, squalene, manaquinone, tocotrienol, tocopherol and coenzyme Q10 are included in γ-cyclodextrin. By making it, it can be set as the stabilized composite, and is applied to food-drinks, cosmetics, and a pharmaceutical.
[Selection figure] None

Description

  The present invention relates to a stabilized complex characterized by including a compound having an isoprenoid structure and / or a quinone structure in a γ cyclodextrin (hereinafter referred to as γCD) and a method for producing the same. Furthermore, it is related with the food / beverage products, cosmetics, and pharmaceuticals which contained this composite_body | complex.

  Compounds having an isoprenoid structure and / or compounds having a quinone structure include farnesol, gefarnate, squalene, menaquinone, tocotrienol, tocopherol, and coenzyme Q10. : Hereinafter referred to as CoQ10). These are used as active ingredients of pharmaceuticals such as cosmetics, health foods, and anti-ulcer agents, but have a problem that they are unstable to light, heat, and the like (see, for example, Non-Patent Document 1).

  This is presumably because the isoprenoid structure and / or quinone structure of these compounds are easily reacted due to the large number of reactive sites of carbocations and are converted into various compounds. Therefore, development of a stable complex containing a compound having an isoprenoid structure and / or a quinone structure, which can avoid these reactions and maintain the original effect of the compound, and cosmetics, foods and drinks, pharmaceuticals and the like containing the compound. Offer was desired.

Currently, CoQ10 and vitamins are included among the compounds having isoprenoid structure and / or quinone structure, and at least one of them is included in cyclodextrin (hereinafter referred to as CD) to stabilize the composition containing CoQ10. The thing is disclosed (for example, refer patent document 1).
Here, we obtained soft capsules containing vitamin E in a CoQ10-containing solid complex containing CoQ10 in βCD, and soft capsules containing CoQ10 in a vitamin E-containing solid complex containing vitamin E in βCD. The storage stability is shown by the residual ratio (%) of CoQ10 in storage at 40 ° C. for 1 to 3 months.
Here, in order to obtain a CoQ10-containing composition, any CD complex can be used, but in the examples, only βCD is used, and the present inventors conducted experiments in the same manner. As a result, the CoQ10-containing complex using βCD did not exhibit high storage stability such that the residual rate after 3 months was 96.9%.
JP 2005-2005 Biochemistry Dictionary (3rd edition), Tokyo Chemical Co., Ltd., 1998

  An object of the present invention is to provide a stabilized complex characterized in that a compound having an isoprenoid structure and / or a quinone structure is included in γCD, and a method for producing the same. Furthermore, it is an object to provide foods, beverages, cosmetics and pharmaceuticals containing this complex.

  As a result of intensive studies to solve the above problems, the present inventors have found that a stabilized complex can be obtained by inclusion of a compound having an isoprenoid structure and / or a quinone structure in γCD. The headline and the present invention were completed. Furthermore, the present inventors have found that the inclusion of this complex can provide food, drink, cosmetics and pharmaceuticals that can maintain the effect of the compound contained in the complex over a long period of time, thereby completing the present invention.

[式中nは１以上20以下の整数を意味する]を有する化合物である上記（１）に記載の複合体の製造方法。
（３）キノン構造が、（B）以下の構造式：
[化２]

[式中Rは水素、ヒドロキシル又はヒドロキシメチル、ヒドロキシエチル、ヒドロキシプロピル等のヒドロキシアルキルからなる群より選ばれる]を有する化合物である、上記（１）に記載の複合体の製造方法。
（４）化合物が、ファルネゾール、ゲファルナート、スクアレン、メナキノン、トコトリ エノール、トコフェロール、コエンザイムQ10（CoQ10）からなる群より選ばれるいず れか１つ以上である上記（１）〜（３）のいずれかに記載の製造方法。
（５）上記（１）〜（４）のいずれかに記載の製造方法により製造された複合体。
（６）上記（５）に記載の複合体を含有せしめた飲食品。
（７）上記（５）に記載の複合体を含有せしめた化粧品。
（８）上記（５）に記載の複合体を含有せしめた医薬品。 That is, this invention relates to the stabilized composite_body | complex in any one of following (1)-(8), its manufacturing method, food / beverage products, cosmetics, and a pharmaceutical using the composite_body | complex.
(1) A method for producing a stabilized complex, wherein a compound having an isoprenoid structure and / or a quinone structure is included in γ cyclodextrin (γCD).
(2) The isoprenoid structure is (A) the following structural formula:
[Chemical 1]

The method for producing a complex according to the above (1), which is a compound having [wherein n represents an integer of 1 to 20].
(3) The quinone structure is (B) the following structural formula:
[Chemical 2]

The process for producing a complex according to the above (1), wherein R is a compound having [selected from the group consisting of hydrogen, hydroxyl, or hydroxyalkyl such as hydroxymethyl, hydroxyethyl, hydroxypropyl].
(4) Any of (1) to (3) above, wherein the compound is at least one selected from the group consisting of farnesol, gefarnate, squalene, menaquinone, tocotrienol, tocopherol, and coenzyme Q10 (CoQ10). The manufacturing method as described in.
(5) The composite manufactured by the manufacturing method in any one of said (1)-(4).
(6) A food and drink containing the complex according to (5) above.
(7) A cosmetic containing the complex according to (5) above.
(8) A pharmaceutical product containing the complex according to (5) above.

  The complex of the present invention can maintain the effect of the compound having an isoprenoid structure and / or a quinone structure, and sufficient storage stability can be obtained. Therefore, it facilitates the production and storage of foods, drinks, cosmetics and pharmaceuticals containing these as active ingredients.

  The “stabilized complex” of the present invention refers to a substance having improved stability to heat, light, etc. by inclusion of a compound having an isoprenoid structure and / or a quinone structure in γCD. . The composite of the present invention can be used in the form of powder, granule, aqueous solution or the like according to its use.

  The “compound having an isoprenoid structure and / or a quinone structure” of the present invention includes any compound having an isoprenoid structure and / or a quinone structure. In particular, the compound having an isoprenoid structure represented by the structural formula [Chemical Formula 1] Of these, compounds in which n is an integer of 1 to 20 are preferred. Of the quinone structure represented by the structural formula [Chemical Formula 2], R is preferably a compound selected from the group consisting of hydrogen, hydroxyl or hydroxyalkyl such as hydroxymethyl, hydroxyethyl, hydroxypropyl and the like. Furthermore, it is preferable that it is any one or more of farnesol, gefarnate, squalene, menaquinone, tocotrienol, tocopherol, and CoQ10 that can be used as active ingredients of foods, drinks, cosmetics, pharmaceuticals and the like.

In the present invention, “inclusion of a compound having an isoprenoid structure and / or quinone structure with γCD” refers to the production of a γCD inclusion body of a compound having an isoprenoid structure and / or a quinone structure. For the production, a general clathrate production method such as spray drying, freeze-drying method, saturated aqueous solution method, kneading method, mixed pulverization method or the like can be used.
Spray drying and freeze-drying methods include preparing a 10-40% aqueous solution of CD, adding a certain amount of guest compound, and homogenizing (rotation speed: 1,000-3,000 rpm, 30 minutes to 5 hours, room temperature). Then, the clathrate emulsion obtained by the above is spray-dried and freeze-dried to obtain a clathrate. The saturated aqueous solution method creates a saturated aqueous solution of CD, mixes a certain amount of guest compound, and stirs and mixes for 30 minutes to several hours depending on the type of CD and the type of guest compound. And then the clathrate is isolated by evaporating water or lowering the temperature and taking out the precipitate, followed by drying.
The kneading method is a method of isolating a clathrate by adding a small amount of water to CD, adding a certain amount of guest compound, stirring well with a mixer, and then evaporating the water. Yes, the mixing time is longer than the saturated aqueous solution method. The mixed pulverization method is a method obtained by pulverizing CD and a guest compound with a vibration mill.

  Regarding the kneading method or the heating method, for example, in the case where the compound having an isoprenoid structure and / or a quinone structure is, for example, CoQ10, Journal Acta Poloniae, Pharmaceutica (1995), Vol. 52, No5, S.379-386 and ( 1996), Vol. 53, No. 3, S.193-196, describes the conjugation of CoQ10 with various CDs and CD derivatives. Japanese Patent Publication No. 2003-520827 describes a method for obtaining a complex more quickly and easily by using an aqueous mixture of γCD and CoQ10.

  Among the obtained composites, whether or not an inclusion body is formed is determined by using circular dichroism spectrum or NMR spectrum in the solution state, and in the solid state by thermal analysis DSC, powder X-ray or the like CD, It can be confirmed by comparing the guest compound alone, the physical mixture and the clathrate.

  In forming the complex, it is preferable to use the compound having an isoprenoid structure and / or a quinone structure so that the content is 40% or less and γCD is less than 60 to 100%. Furthermore, it is more preferable that the content of the compound having an isoprenoid structure and / or a quinone structure is about 20%, in other words, the γCD content is 4 times or more that of the compound. The lower the content of the compound, the higher the stability of the composite, but if it is 40% or less, sufficient stability can be obtained.

  The complex of the present invention is a capsule, a tablet, a granule, a powder, a liquid, a syrup, a suspension, an ointment, a cream depending on the effect of the compound having an isoprenoid structure and / or a quinone structure and the purpose of use. , Gels, injections and the like. The complex of the present invention may be ingested or applied as it is or after adding an additive, as long as it is within the range corresponding to the possible daily intake, as a food, drink, cosmetic or pharmaceutical product.

Supplements, functional foods, nutritional drinks and the like can be produced as foods and drinks containing the complex of the present invention. When producing a food or drink using the complex of the present invention, a complex containing, for example, squalene, menaquinone, tocotrienol, tocopherol, CoQ10, etc., as a compound having an isoprenoid structure and / or a quinone structure contained in the complex It is preferable to use these components effectively. In addition, the composite of the present invention can be combined with other compounds having an isoprenoid structure and / or a quinone structure and used as a composition having various effects.
In the case of producing a supplement using the complex of the present invention, the complex of the present invention can be tableted as it is, but if necessary, for example, starch, lactose, sucrose, mannitol, carboxy Additives usually used in preparations such as methylcellulose, corn starch and inorganic salts can be added.

Moreover, as a cosmetic containing the composite of the present invention, a lotion, a milky lotion, a beauty cream or the like can be produced. In the case of producing a cosmetic using the complex of the present invention, as a compound having an isoprenoid structure and / or a quinone structure contained in the complex, for example, a complex containing squalene, menaquinone, tocotrienol, tocopherol, CoQ10, etc. It is preferable to use these components effectively. In addition, the composite of the present invention can be combined with other compounds having an isoprenoid structure and / or a quinone structure and used as a composition having various effects.
Furthermore, in addition to the complex of the present invention, cosmetic ingredients such as retinol having effects such as proliferation of skin fibroblasts, and moisturizing ingredients such as jojoba oil and plant extracts can be blended as necessary.

Furthermore, a pharmaceutical product containing the complex of the present invention can be produced. When producing a pharmaceutical product using the complex of the present invention for producing a pharmaceutical product, a compound containing, for example, farnesol, gefarnate, etc. is used as a compound having an isoprenoid structure and / or a quinone structure contained in the complex. It is preferable to use these components effectively. In addition, the composite of the present invention can be combined with other compounds having an isoprenoid structure and / or a quinone structure and used as a composition having various effects.
In the case of producing a pharmaceutical product using the complex of the present invention, necessary components can be blended in addition to the complex of the present invention.

  Hereinafter, the details of the present invention will be described with reference to examples and the like, but the present invention is not limited thereto.

Method for Producing Stabilized Complex Using the compounds shown in Table 1 as compounds having an isoprenoid structure and / or a quinone structure, the compound was mixed with γCD (Wacker Biochem), and a complex was obtained by a kneading method.
1) 1.5 g of farnesol (manufactured by Sigma) and 8.5 g of γCD were mixed, and 10 g of farnesol-γCD clathrate powder was obtained by a kneading method to obtain a composite (A).
2) 1.5 g of menaquinone (manufactured by Sigma) and 8.5 g of γCD were mixed, and 10 g of menaquinone-γCD clathrate powder was obtained by a kneading method to obtain a composite (B).
3) 1 g of tocopherol (manufactured by Bizen Kasei Co., Ltd.) and 9 g of γCD were mixed, and 10 g of tocopherol-γCD clathrate powder was obtained by a kneading method to obtain a composite (C).
4) 2 g of CoQ10 (manufactured by Nisshin Pharma) and 8 g of γCD were mixed, and 10 g of CoQ10-γCD clathrate powder was obtained by a kneading method to obtain a composite (D).
The content rate of Table 1 shows the content rate of the compound contained in each composite_body | complex.

Confirmation of formation of clathrate of complex As compound having isoprenoid structure and / or quinone structure, CoQ10 (manufactured by Nisshin Pharma) was mixed with γCD (manufactured by Cyclochem), and a complex was obtained by kneading method . It was examined by powder X-ray and thermal analysis DSC method that the obtained complex formed an inclusion body, using only CoQ10 or a mixture of CoQ10 and γCD as a control.
As control samples, a) CoQ10 only, b) 1: 1 mixture of CoQ10 and γCD, c) 1: 3 mixture of CoQ10 and γCD, d) 1: 5 mixture of CoQ10 and γCD, e) 1: 1 of CoQ10 and γCD. 10) a) to e) of 10 mixtures, and f) 1: 1 kneaded body of CoQ10 and γCD, g) 1: 3 kneaded body of CoQ10 and γCD, h) 1: 5 kneaded body of CoQ10 and γCD, i ) F) to i) of a 1:10 kneaded body of CoQ10 and γCD was used.
When the obtained results are shown in FIG. 1, a strong peak was observed at one position in the mixture of a) and b) to e), but the peak was weak in the kneaded bodies of f) to i), and the composite Of clathrate formation. Therefore, it was confirmed that a stabilized complex was obtained by the production method of the present invention.

<Examination of the stability of the composite>
(1) Examination of heat and light stability of complex (A) The complex (A) of Example 1 and a farnesol (containing 20%)-γCD mixture were used as a control. The farnesol (containing 20%)-γCD mixture is simply a mixture of farnesol and γCD, and is not particularly included.
Each of these was put in a glass bottle and stored in an open system at 50 ° C. for 0 to 100 days. The farnesol content was determined for each storage period, and the stability of the complex (A) to heat was examined.
Similarly, it was stored in an open system under sunlight exposure at room temperature for 0 to 100 days. The farnesol content was quantified for each storage period, and the stability of the complex (A) to light was examined.
The content of farnesol is 10 mg precisely sampled for each storage period to be measured, add 5 ml of DMF, sonicate for 5 minutes, filter with a syringe filter, and then use HPLC to analyze the following analysis conditions. Was used to measure the amount of farnesol in the complex, and the content of farnesol contained in the sample was calculated. The content rate was calculated | required by the following formula | equation.

<HPLC analysis conditions>
Column: Waters SunFire 5.0μm C ₁₈ 4.6 × 150mm
Column temperature: 40 ° C
Mobile phase: DMF100%
Flow rate: 1.0mL / min
Detection wavelength: UV280nm
Injection volume: 10μL

[Formula 1]
Content rate (%) = (farnesol content / sample weight) × 100

Results The content of farnesol in the heat of the composite (A) is shown in FIG. 2a), and the content of farnesol in the light is shown in FIG. 2b).
As shown in FIGS. 2a) and b), it was confirmed that the farnesol content of the farnesol (containing 20%)-γCD mixture decreased to near 0% with the passage of days due to heat and light. . On the other hand, although the farnesol content of the composite (A) of the present invention slightly decreased with the passage of time, it was shown to have stability against heat and light as compared with the control mixture.

(2) Examination of light stability of complex (B) Using complex (B) of Example 1 and αCD or βCD (both manufactured by Wacker Biochem) instead of γCD as a control, Example 1 Using the same menaquinone (containing 15%)-αCD complex and menaquinone (containing 15%)-βCD complex and menaquinone itself, place them in a glass bottle and irradiate with light at an intensity of 1,000 lux at room temperature. By quantifying the content of menaquinone after 1 week and 2 weeks, the stability of the complex (B) to light was examined. The residual ratio of menaquinone was calculated from the quantified content, with the content at the start of the test as 100%. The residual rate was calculated | required by the following formula | equation.

[Formula 2]
Residual rate (%) = (measured farnesol content / theoretical farnesol content sample amount) × 100
(Theoretical value: Value calculated from prescription)

Results The residual ratio of menaquinone in the light of the complex (B) is shown in FIG. As shown in FIG. 3, menaquinone itself, menaquinone (containing 15%)-αCD complex and menaquinone (containing 15%)-βCD complex, the remaining ratio of menaquinone is reduced to 10% or less in one week by light. In addition, it was confirmed that it decreased to nearly 0% in 2 weeks. On the other hand, although the remaining ratio of menaquinone in the complex (B) of the present invention decreases with the passage of time, it was shown to have stability over a long period of time with respect to light. This indicated that γCD was most effective in providing stable complexes compared to αCD and βCD.

(3) Examination of heat and light stability of complex (C) As complex (C) of Example 1, tocopherol (containing 9%)-γCD complex and tocopherol (containing 13%)-γCD complex As a control, a tocopherol (containing 13%)-starch mixture was used. The tocopherol (containing 13%)-starch mixture is simply a mixture of tocopherol and starch and is not specifically included.
These were each put in a glass bottle, stored under sunlight exposure at 45 ° C. for 0 to 60 hours, the tocopherol content was quantified for each storage period, and the stability of the complex (C) to light was examined. The residual ratio of tocopherol was determined in the same manner as in Examples 1 and (2).

Results The residual ratio of tocopherol in the heat and light of the complex (C) is shown in FIG. As shown in FIG. 4, the tocopherol residual rate of the tocopherol (containing 13%)-starch mixture decreases to near 50% after 30 hours and decreases to 0% after 60 hours due to heat and light. It was confirmed. On the other hand, although the residual ratio of tocopherol of the composite (C) of the present invention slightly decreased with the passage of time, it was shown to be more stable against heat and light than the control mixture.

(4) Examination of heat and light stability of complex (D) The complex (D) of Example 1 and CoQ10 (containing 20%)-starch mixture were used as controls. The CoQ10 (containing 20%)-starch mixture is simply a mixture of CoQ10 and starch and is not specifically clathrated.
Each of these was put in a glass bottle, stored under sunlight exposure at 45 ° C. for 0 to 25 hours, the CoQ10 content was quantified for each storage period, and the stability of the complex (D) to light was examined.
Similarly, the residual rate of CoQ10 was examined by storing in an open system at 60 ° C. for 0 to 6 weeks, and the stability of the complex (D) to heat was examined. The residual ratio of CoQ10 was determined in the same manner as in Examples 1 and (2).

Results The residual rate of CoQ10 in the light of the composite (D) is shown in FIG. 5a), and the residual rate of CoQ10 in heat is shown in FIG. 5b).
As shown in FIGS. 5a) and b), the CoQ10 residual ratio of CoQ10 (containing 20%)-starch mixture can be reduced to less than half to close to 0% with the passage of days due to light and heat. confirmed. On the other hand, the residual ratio of CoQ10 in the complex (D) of the present invention is decreased by light as shown in FIG. 5a), but is not decreased by heat as shown in FIG. 5b). It was shown to be more stable than

<Examination of stability of complex (D) in the presence of vitamins>
CoQ10 (containing 20%)-αCD complex and CoQ10 (containing 20%)-βCD prepared in the same manner as in Example 1 using the composite (D) of Example 1 and αCD or βCD instead of γCD as a control. The composite and CoQ10 itself were used.

(1) Examination of stability of complex (D) in the presence of vitamin E Complex (D), CoQ10 (containing 20%)-αCD complex and CoQ10 (containing 20%)-βCD complex produced above 2.125 g of each body was used and mixed with 0.354 g of vitamin E (manufactured by Bizen Kasei Co., Ltd.) and 2.521 g of glycerin fatty acid (manufactured by Kao Co., Ltd.) to obtain a paste-like CoQ10-containing composition.
For further comparison, CoQ10 (Nisshin Pharma Co., Ltd.) 0.425g was mixed with crystalline cellulose (Bizen Kasei Co., Ltd.) 1.7g, vitamin E (Bizen Kasei Co., Ltd.) 0.354g, glycerin fatty acid (Kao Co., Ltd.) 2.521g, A paste-like Q10-containing composition was obtained.

The CoQ10-containing composition obtained in (1) above is stored under the following storage conditions, and the amount of coenzyme Q10 in the composition is measured under the following analytical conditions using HPLC for each storage period, The residual rate of Coenzyme Q10 was calculated as%.
<Storage conditions>
Storage temperature: 40 ℃
Storage container: Shaded glass bottle airtight container Storage period: 20 days <HPLC analysis conditions>
Column: Waters SunFire 5.0μm C ₁₈ 4.6 × 150mm
Column temperature: 40 ° C
Mobile phase: DMF100%
Flow rate: 1.0mL / min
Detection wavelength: UV280nm
Injection volume: 10μL

Results The residual ratio of CoQ10 in the complex (D) in the presence of vitamin E is shown in FIG. 6a).
As shown in Fig. 6a), CoQ10 itself, CoQ10 (containing 20%)-αCD complex and CoQ10 (containing 20%)-βCD complex in the presence of vitamin E are the remaining percentage of CoQ10 over time. It gradually decreased with time, and was confirmed to decrease to about 75 to 85% 20 days after the start of the test. On the other hand, the residual ratio of CoQ10 in the complex (D) of the present invention was hardly decreased, and it was shown that the complex (D) has high stability even in the presence of vitamin E.

(2) Examination of stability of complex (D) in the presence of vitamin C Complex (D), CoQ10 (containing 20%)-αCD complex and CoQ10 (containing 20%)-βCD complex produced above 2.125 g of each body was used and mixed with 2.875 g of vitamin C (manufactured by Sankyo Lifetech Co., Ltd.) to obtain a powdery CoQ10-containing composition.
For further comparison, 0.425 g of CoQ10 (Nisshin Pharma Co., Ltd.) was mixed with 1.7 g of crystalline cellulose (Bizen Kasei Co., Ltd.) and 2.875 g of vitamin C (Sankyo Lifetech Co., Ltd.) to obtain a powdered CoQ10-containing composition. It was.

  The CoQ10-containing composition obtained in (2) above is stored under the same storage conditions as in (1) above, and the amount of CoQ10 in the composition is measured using HPLC for each storage period. The remaining ratio of CoQ10 was calculated.

Results The residual ratio of CoQ10 in the complex (D) in the presence of vitamin C is shown in FIG. 6b). As shown in Fig. 6b), CoQ10 itself, CoQ10 (containing 20%)-αCD complex and CoQ10 (containing 20%)-βCD complex in the presence of vitamin C are the remaining ratios of days. It gradually decreased with time, and after 20 days from the start of the test, it was confirmed to decrease to about 80 to 85%. On the other hand, although the CoQ10 residual rate of the complex (D) of the present invention slightly decreased with the passage of days, it was shown to have high stability even in the presence of vitamin C.
From the above results, it was shown that even in the presence of vitamin E or vitamin C, a complex using γCD can obtain higher stability than αCD and βCD.

Examination of the stability of the complex in the presence of vitamin E due to the difference in CoQ10 content As a sample, a complex prepared so that γCD and CoQ10 become 4: 1 (γCD / CoQ10 (4: 1) complex), A complex prepared to be 2: 1 (γCD / CoQ10 (2: 1) complex), a complex prepared to be 1: 1 (γCD / CoQ10 (1: 1) complex), control CoQ10 was used as a sample and their stability in the presence of vitamin E was examined.
2.125 g of each of the above samples was used and mixed with 0.354 g of vitamin E (manufactured by Bizen Kasei Co., Ltd.) and 2.521 g of glycerin fatty acid (manufactured by Kao Corporation) to obtain a paste-like CoQ10-containing composition.

  The CoQ10-containing composition obtained above was stored under the same storage conditions as in Example 2 above, and the amount of coenzyme Q10 in the composition was measured under the following analytical conditions using HPLC for each storage period, and at the start of storage. The residual rate of coenzyme Q10 was calculated with 100%.

Results The residual ratio of CoQ10 in each sample in the presence of vitamin E is shown in FIG.
As shown in Fig. 7, it is confirmed that the residual rate of CoQ10 itself in the presence of vitamin E gradually decreases with the passage of days, and decreases to about 75 to 85% after 20 days from the start of the test. It was done. On the other hand, the residual ratio of CoQ10 in the γCD / CoQ10 (4: 1) complex was hardly lowered, indicating that it has high stability even in the presence of vitamin E. In addition, the residual ratio of CoQ10 in the γCD / CoQ10 (2: 1) complex slightly decreased with the passage of days, and further decreased in the γCD / CoQ10 (1: 1) complex, but it was sufficient compared to CoQ10 alone. Stability was shown. From this result, it was shown that the composite having a lower CoQ10 content has higher stability.

  The composite produced by the present invention can stably maintain the effect of the compound contained as a component. In addition, by using this complex as a component, it is possible to easily provide foods, beverages, cosmetics, pharmaceuticals, and the like that can maintain effects over a long period of time.

It is the figure which showed that the composite_body | complex forms the inclusion body. a) It is the figure which showed the content rate of the farnesol in the heat | fever of a composite_body | complex (A). b) It is the figure which showed the residual rate of farnesol in the light of a composite_body | complex (A). Example 1 It is the figure which showed the residual rate of menaquinone in the light of a composite_body | complex (B). Example 1 It is the figure which showed the residual rate of the tocopherol in the heat | fever and light of a composite_body | complex (C). Example 1 a) A diagram showing the residual ratio of CoQ10 in the light of the complex (D). (Example 1) b) The residual ratio of CoQ10 in the heat of the composite (D) is shown in FIG. 4B). Example 1 a) It is the figure which showed the residual rate of CoQ10 of the complex (D) in presence of vitamin E. b) A diagram showing the residual ratio of CoQ10 in the complex (D) in the presence of vitamin C. (Example 2) It is the figure which showed the residual rate of CoQ10 of each composite_body | complex in the presence of vitamin E by the difference in CoQ10 content (Example 3).

Claims (8)

A method for producing a stabilized complex, characterized in that a compound having an isoprenoid structure and / or a quinone structure is included in γ-cyclodextrin (γCD). The isoprenoid structure is (A) the following structural formula:
[Chemical 1]

The method for producing a complex according to claim 1, wherein n is a compound having [wherein n represents an integer of 1 to 20]. The quinone structure is (B) the following structural formula:
[Chemical 2]

2. The method for producing a complex according to claim 1, wherein R is a compound having [selected from the group consisting of hydrogen, hydroxyl, or hydroxyalkyl such as hydroxymethyl, hydroxyethyl, hydroxypropyl]. 4. The production method according to claim 1, wherein the compound is at least one selected from the group consisting of farnesol, gefarnate, squalene, menaquinone, tocotrienol, tocopherol, and coenzyme Q10 (CoQ10). A composite produced by the production method according to claim 1. 6. A food or drink containing the complex according to claim 5. 6. A cosmetic containing the composite according to claim 5. 6. A pharmaceutical product comprising the complex according to claim 5.

Images