Burdock seed oil-containing composition and method for producing the same

Abstract

The purpose of the present invention is to produce and provide a burdock seed oil-containing composition that is excellent in stability. The present invention relates to a composition containing (A) burdock seed oil and (B) triethyl citrate and containing 1 to 7.5 mass% of arctigenin derived from the component (A), and a method for producing the same.

Description

[Technical Field]

[0001] The present invention relates to a burdock seed oil-containing composition and a method for producing the same. [Background technology]

[0002] Burdock, the seed of Arctum lappa Linne (Compositae) of the Asteraceae family, is known to contain the lignan glycoside arctiin and its aglycone arctigenin. A method for producing a burdock extract containing a high content of arctigenin from burdock is known (Patent Document 1).

[0003] The stability of burdock seed oil, an extract of burdock seeds, has not been sufficiently investigated. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] International Publication No. 2012 / 043549 Summary of the Invention [Problem to be solved by the invention]

[0005] An object of the present invention is to produce and provide a burdock seed oil-containing composition having excellent stability. [Means for solving the problem]

[0006] The present inventors have found that a composition containing (A) burdock seed oil and (B) an ester or glycol ether is stable, and have completed the present invention.

[0007] The present invention provides a burdock seed oil-containing composition having excellent stability. The present invention also provides a method for producing a burdock seed oil-containing composition having excellent stability.

[0008] That is, the present invention relates to a composition containing (A) burdock seed oil and (B) an ester or glycol ether. A preferred embodiment of the present invention is [1] A composition containing (A) burdock seed oil and (B) one or more selected from the group consisting of triethyl citrate, diisopropyl adipate, diethyl sebacate, and phenoxyethanol; [2] The composition according to [1], containing 1 to 7.5% by mass of arctigenin derived from the component (A); [3] The composition according to [1] or [2], wherein the content of arctigenin derived from component (A) is 2 to 15 mass% based on the total amount of component (A); [4] (B) The composition according to any one of [1] to [3], wherein the content of one or more selected from the group consisting of triethyl citrate, diisopropyl adipate, diethyl sebacate, and phenoxyethanol is 10 to 90 mass%; [5] A method for producing a composition, comprising a step of blending (A) burdock seed oil and (B) one or more selected from the group consisting of triethyl citrate, diisopropyl adipate, diethyl sebacate, and phenoxyethanol; [6] A method for producing the composition according to [5], comprising the step of blending component (A) so that the content of arctigenin derived from component (A) is 1 to 7.5% by mass; [7] The method for producing the composition according to [5] or [6], wherein the content of arctigenin derived from the component (A) is 2 to 15 mass% based on the total amount of the component (A); [8] (B) A method for producing the composition according to any one of [5] to [7], wherein the content of one or more selected from the group consisting of triethyl citrate, diisopropyl adipate, diethyl sebacate, and phenoxyethanol is 10 to 90 mass%; [9] A method for producing a composition, comprising blending (A) burdock seed oil and (B) one or more members selected from the group consisting of triethyl citrate, diisopropyl adipate, diethyl sebacate, and phenoxyethanol, the method comprising a step of incorporating arctigenin into the burdock seed oil at a high concentration;

[10] An external or oral preparation containing the composition according to any one of [1] to [4] and containing burdock seed oil as an active ingredient;

[11] An external or oral preparation containing the composition according to [2] or [3], and containing arctigenin as an active ingredient;

[12] (A) The composition according to any one of [1] to [4], which is substantially free of arctiin derived from burdock seed oil:

[13] A method for producing the composition according to any one of [5] to [9], wherein the composition is substantially free of (A) arctiin derived from burdock seed oil:

[14] (A) The topical or oral preparation according to

[10] or

[11] , which is substantially free of arctiin derived from burdock seed oil, is provided. [Effects of the Invention]

[0009] The burdock seed-containing composition of the present invention has excellent stability because it contains (A) burdock seed oil and (B) esters or glycol ethers. DETAILED DESCRIPTION OF THE INVENTION

[0010] Hereinafter, embodiments of the present invention will be described in detail, but the present invention is not limited to the following embodiments.

[0011] [1. Composition] The composition of the present invention is a composition containing (A) burdock seed oil and (B) esters or glycol ethers, and preferably contains 1 to 7.5% by mass of arctigenin derived from component (A). For example, a composition according to one embodiment contains (A) burdock seed oil and (B) one or more selected from the group consisting of triethyl citrate, diisopropyl adipate, diethyl sebacate, and phenoxyethanol, and the content of arctigenin derived from component (A) is 1 to 7.5% by mass.

[0012] <Component (A)> Burdock seed oil is not particularly limited as long as it is obtained from the seeds of Arctum lappa Linne (Compositae) of the Asteraceae family. Preferably, it can be obtained by extraction from burdock seeds. For example, burdock seed oil can be obtained by production using the method described below, or commercially available burdock seed oil can be used. One type may be used alone, or two or more types may be used in combination.

[0013] The content of component (A) in the composition according to this embodiment is not particularly limited and is set appropriately depending on the types and contents of other blended components, the intended use of the composition, the dosage form, etc. From the viewpoint of more significantly exhibiting the effects of the present invention, the content of component (A) may be, for example, 10 to 90 mass %, or 20 to 80 mass %, preferably 30 to 70 mass %, more preferably 35 to 65 mass %, more preferably 40 to 60 mass %, even more preferably 45 to 60 mass %, and particularly preferably 45 to 55 mass %, based on the total amount of the composition.

[0014] The composition according to the present embodiment contains arctigenin. The content of arctigenin is not particularly limited and is appropriately determined depending on the type and content of other ingredients, the intended use of the composition, the formulation, etc. From the viewpoint of more significantly exhibiting the effects of the present invention, the content of arctigenin may be, for example, 1 to 7.5% by mass, or 1 to 6% by mass, preferably 1 to 5.5% by mass, more preferably 1 to 5% by mass, more preferably 1.5 to 4.5% by mass, even more preferably 2 to 4% by mass, and particularly preferably 2.5 to 3.5% by mass, based on the total amount of the composition.

[0015] The composition according to the present embodiment contains arctigenin derived from component (A). From the viewpoint of more significantly exhibiting the effects of the present invention, the content of arctigenin derived from component (A) may be, for example, 2 to 15% by mass, or 2 to 12% by mass, preferably 2 to 11% by mass, more preferably 2 to 10% by mass, more preferably 3 to 9% by mass, even more preferably 4 to 8% by mass, and particularly preferably 5 to 7% by mass, based on the total amount of component (A). The content of arctigenin derived from component (A) is not particularly limited and is set appropriately depending on the type and amount of other ingredients, the intended use of the composition, the dosage form, etc.

[0016] <(B) component> From the viewpoint of achieving the effects of the present invention more significantly, component (B) is preferably an ester or glycol ether, more preferably an ester having 10 to 30 carbon atoms or a glycol ether having 4 to 15 carbon atoms, and even more preferably an ester having 12 to 27 carbon atoms or a glycol ether having 4 to 8 carbon atoms. Triesters having 12 to 27 carbon atoms, such as triethyl citrate (12 carbon atoms) or glyceryl hexanoate (triethylhexanoin) (27 carbon atoms); diesters having 12 to 14 carbon atoms, such as isopropyl adipate (12 carbon atoms) or diethyl sebacate (14 carbon atoms); or glycol ethers having 4 to 8 carbon atoms, such as butylene glycol (4 carbon atoms), diethylene glycol monoethyl ether (ethoxydiglycol) (6 carbon atoms), methoxymethylbutanol (6 carbon atoms), or ethylene glycol monophenyl ether (phenoxyethanol) (8 carbon atoms) are even more preferred. Component (B) has a fluidity that allows it to be mixed with component (A) by stirring at 20 to 80°C. Commercially available products can be used as component (B). Component (B) may be used singly or in combination of two or more. Component (B) is not particularly limited as long as it is a publicly known and used component. Although not limited thereto, for example, component (B) preferably contains one or more selected from the group consisting of triethyl citrate, diisopropyl adipate, diethyl sebacate, and phenoxyethanol. Alternatively, triethyl citrate may be contained alone. It is also possible to contain at least triethyl citrate and further contain one or more selected from the group consisting of diisopropyl adipate, diethyl sebacate, and phenoxyethanol.

[0017] The content of component (B) in the composition according to this embodiment is not particularly limited and is set appropriately depending on the type of component (B), the types and contents of other blended components, the intended use of the composition, the dosage form, etc. From the viewpoint of more significantly exhibiting the effects of the present invention, the content of component (B) may be, for example, 10 to 90 mass%, or 20 to 80 mass%, preferably 30 to 70 mass%, more preferably 35 to 65 mass%, more preferably 40 to 60 mass%, even more preferably 45 to 60 mass%, and particularly preferably 45 to 55 mass%, based on the total amount of the composition.

[0018] (Other ingredients) In addition to the components (A) and (B), other components may also be added to the composition according to this embodiment.

[0019] The composition according to this embodiment preferably does not contain or substantially does not contain arctiin. Here, "substantially does not contain" means that the amount of arctiin in the composition is 0.01% by mass or less, preferably 0.001% by mass or less, more preferably 0.0001% by mass or less.

[0020] 2. Method for producing the composition Component (A) contained in the composition according to this embodiment can be produced through a process of breaking down burdock seeds, a process of extracting burdock seeds to obtain burdock seed oil, a process of filtering the burdock seed oil, a process of making the burdock seed oil contain arctigenin at a high concentration, a concentration process, a solid-liquid separation process, etc. Each process may be appropriately selected from the viewpoint of more significantly exhibiting the effects of the present invention, and it is not necessary to include all of the processes.

[0021] <Burdock seed breaking process> Burdock seeds can be broken by known means, and commercially available breaking devices can also be used. Commercially available burdock seeds broken to any size (particle size) can also be used. From the perspective of more significantly achieving the effects of the present invention, the arctigenin content of the burdock seeds can be measured and burdock seeds suitable for the present invention can be selected.

[0022] <Step of extracting burdock seeds to obtain burdock seed oil> Burdock seed oil can be obtained by mixing broken burdock seeds with a solvent and performing an extraction process at room temperature or high temperature. In the extraction process, organic solvents such as water, methanol, ethanol, propanol, acetone, and oil, or mixtures thereof, can be used. Preferably, a solvent with good compatibility with arctigenin can be selected to increase the yield of arctigenin. Commercially available solvents can be used. Any known extraction method can be used for the extraction process, such as heated stirring, heated reflux, drip extraction, immersion extraction, or pressure extraction. The extraction process can be performed at any temperature, but to more significantly achieve the effects of the present invention, it can be 35°C or higher, 40°C or higher, 50°C or higher, 55°C or higher, 60°C or higher, or 65°C or higher. It can also be 95°C or lower, 90°C or lower, 85°C or lower, 80°C or lower, or 75°C or lower. Although not limited, for example, 40 to 90° C. is preferable, 55 to 90° C. is more preferable, 60 to 85° C. is even more preferable, and 65 to 80° C. is even more preferable. Although there are no limitations on the time for which the extraction treatment is carried out, 30 minutes or more is preferable, 35 minutes to 24 hours is more preferable, 45 minutes to 20 hours is even more preferable, and 1 hour to 20 hours is even more preferable.

[0023] <Burdock seed oil filtering process> Filtration may be performed as necessary to remove unnecessary components from the extracted burdock seed oil. To determine whether a filtration step is necessary, the components contained in the burdock seed oil may be analyzed and measured in advance. Filtration may be performed using known methods and devices such as gel filtration, gel chromatography, thin layer chromatography, and filters.

[0024] <Process for making burdock seed oil contain high concentrations of arctigenin> In order to make burdock seed oil contain arctigenin at a high concentration, it is preferable to convert the arctiin contained in burdock seed oil into arctigenin.Specifically, methods such as hydrolysis, enzyme treatment, or reflux treatment can be carried out, but are not limited thereto.From the viewpoint of more significantly achieving the effects of the present invention, hydrolysis is preferred.The hydrolysis can be accelerated by adding an acid, but is not limited thereto.The acid used here is preferably a strong acid, and for example, hydrochloric acid, nitric acid, sulfuric acid, etc. can be used.

[0025] The reaction temperature in this step may be 40° C. or higher, 50° C. or higher, 60° C. or higher, or 65° C. or higher, and may be 90° C. or lower, 85° C. or lower, 80° C. or lower, or 75° C. or lower. For example, 40 to 90° C. is preferred, 50 to 85° C. is more preferred, 60 to 80° C. is even more preferred, and 65 to 75° C. is even more preferred. The reaction time is not limited, but is preferably 30 minutes or longer, more preferably 35 minutes to 24 hours, even more preferably 45 minutes to 20 hours, and even more preferably 1 hour to 20 hours.

[0026] <Concentration process> A known concentration method can be used to remove the solvent contained in the extracted burdock seed oil, and it is preferable to concentrate it to a concentration that will produce the effects of the present invention.

[0027] <Solid-liquid separation process> To separate the extraction residue from the extracted burdock seed oil, known solid-liquid separation methods such as filtration, sedimentation, and centrifugation can be used.

[0028] <Step of Mixing Component (A) and Component (B) to Obtain a Composition> The extracted burdock seed oil can be analyzed and measured by known methods to confirm the arctigenin content. The composition of the present invention can be obtained by mixing component (A) and component (B), as well as other components as appropriate. For producing the composition, it is preferable to stir and mix component (A) and component (B) at a temperature of, but not limited to, 20°C to 80°C, preferably 20°C to 60°C, and more preferably 20°C to 40°C. The stirring and mixing time is also not limited, but can be 10 minutes to 10 hours, preferably 20 minutes to 5 hours. The ratio of component (A) to component (B) is also not limited, but is preferably 0.1 to 10 parts by mass, more preferably 0.5 to 5 parts by mass, of component (B) per 1 part by mass of component (A). After mixing component (A) and component (B), the arctigenin content may be confirmed by analyzing and measuring by known methods. Here, the ratio of component (A) to component (B) is not limited, but is preferably about 0.1 to 10 parts by mass of component (B) per 1 part by mass of component (A), more preferably 0.5 to 5 parts by mass, and even more preferably 0.5 to 1.5 parts by mass.

[0029] [3. Topical or oral preparations] The composition according to the present embodiment may be an external preparation or an oral preparation. The composition according to the present embodiment may be prepared as an external preparation or an oral preparation. An external preparation refers to a form that is applied to the outer surface of an organism. An oral preparation refers to a form that is taken into the body through the mouth of an organism and applied.

[0030] In addition to the components (A) and (B), the composition according to this embodiment or a topical preparation containing the composition may further contain one or more of the following components: a whitening component, an anti-inflammatory component, an antibacterial component, a cell activating component, an astringent component, an antioxidant component, an anti-aging component, or a moisturizing component, within a range that does not impair the effects of the present invention. These components are not particularly limited as long as they have been used in the past as components of topical skin preparations in the fields of pharmaceuticals, quasi-drugs, or cosmetics, or will be used in the future, and any component may be appropriately selected and used.

[0031] The composition according to this embodiment or an oral preparation containing the composition may contain, in addition to the components (A) and (B) described above, a pharmacologically active ingredient or a physiologically active ingredient, provided that the effects of the present invention are not impaired. The pharmacologically active ingredient or physiologically active ingredient may be used alone or in combination of two or more. Furthermore, the oral preparation may contain additives such as excipients, binders, disintegrants, lubricants, colorants, flavoring agents, odorants, sugars, sugar alcohols / polyalcohols, intense sweeteners, oils and fats, emulsifiers, thickeners, acidulants, and fruit juices.

[0032] The topical or oral preparation can be used in the form of a medicine, cosmetic, or food. It can be mixed with a known base or carrier to form a topical or oral preparation, as long as the effects of the present invention are not impaired. Known forms include, for example, solutions, suspensions, emulsions, creams, ointments, gels, liniments, lotions, aerosols, foams, powders, patches, sheets of nonwoven fabrics or the like impregnated with a drug solution, sticks such as lipsticks, jellies, syrups, granules, lozenges, chewable tablets, pills, tablets, and capsules.

[0033] [Method for producing topical or oral preparations] In one embodiment of the present invention, a method for producing an external preparation or an oral preparation can be provided. The content of each component and other conditions are the same as those described in [1. Composition], [2. Composition Production Method], and [3. External Preparation or Oral Preparation]. [Example]

[0034] The present invention will be specifically explained below based on test examples, but the present invention is not limited to these. In the following examples, the blending amounts are expressed as mass %.

[0035] [Manufacturing Example 1] Burdock seeds that had been crushed and broken were placed in a sufficient amount of 98% aqueous ethanol solution and stirred at 40°C for 18 hours. The resulting solution was left to stand at room temperature to allow the burdock seed residue to settle. The supernatant was collected to obtain burdock seed oil (a process in which burdock seeds are extracted to obtain burdock seed oil). Filtration was carried out using a pad containing silica gel and celite in a 2:1 ratio. The amounts of arctigenin and arctiin contained in the obtained burdock seed oil were measured using high-performance liquid chromatography, and the results showed that the arctigenin content was 1.1% by mass and the arctiin content was 19.3% by mass (burdock seed oil filtering process). Sulfuric acid was added to the recovered burdock seed oil, and the mixture was stirred at 70°C for 18 hours for hydrolysis. The pH of the burdock seed oil was adjusted to approximately 5.5 using a pH adjuster. Bleaching carbon was added to the burdock seed oil, and the mixture was stirred for 18 hours. The mixture was then filtered using a Celite pad, and the filtered liquid was washed with ethanol (a process for concentrating arctigenin in burdock seed oil at a high concentration). The burdock seed oil was concentrated using a rotary evaporator (30°C) and left to stand in an oven for 12 hours (22°C) to settle the burdock seed oil residue. The separated oil phase was separated from the solid phase and dried overnight in a vacuum oven (concentration process, solid-liquid separation process). The amounts of arctigenin and arctiin contained in the obtained burdock seed oil were measured by high performance liquid chromatography, and the arctigenin content was 5.4 mass %, and no arctiin was detected.

[0036] [Examples and Comparative Examples] The burdock seed oil (A) and (B) components obtained in Production Example 1 were weighed as shown in Table 2 and placed in a cylindrical polyethylene beaker. Component (A) and component (B) were mixed by stirring at room temperature for 30 minutes to prepare each composition of the examples. Only the burdock seed oil (A) obtained in Production Example 1 was used as a comparative composition. Note that all (B) components in the table represent 100% of the indicated component.

[0037] [Test Example 1] The burdock seed oil components (A) and (B) obtained in Production Example 1 were weighed as shown in Table 1 and placed in a glass beaker. Components (A) and (B) were mixed by stirring at room temperature for 30 minutes, then transferred to a cylindrical polyethylene terephthalate container and sealed with a screw-top lid. After standing at 4°C for one week, the appearance of the composition was observed to assess its stability. When viewed from the side of the container near the bottom, test solutions with no precipitate were evaluated as ◎, test solutions with slight precipitate observed were evaluated as ◯, and test solutions with precipitate and color gradation (unevenness) observed were evaluated as ×. The results are shown in Table 1.

[0038] [Table 1]

[0039] As shown in Table 1, the composition (Comparative Example 1-1) containing only burdock seed oil (Production Example 1) was less stable after being left standing at 4° C. for one week. It was revealed that the compositions (Examples 1-1 to 1-4) containing burdock seed oil (Production Example 1) and component (B) were highly stable.

[0040] [Test Example 2] After preparation, the compositions were allowed to stand for 5 minutes, and then their appearance was observed to assess their stability. When viewed from the side of the beaker, test solutions in which no areas of color gradation (unevenness) were observed were rated as ◎, test solutions in which the areas in which color gradation occurred were less than 50% were rated as 〇, test solutions in which the areas in which color gradation occurred were 50% or more but no separation of components (A) and (B) was observed were rated △, and test solutions in which separation of components (A) and (B) was observed were rated ×. Even if no areas with color gradation were observed, test solutions in which separation of components (A) and (B) was observed were evaluated as ×. The results are shown in Table 2.

[0041] [Table 2]

[0042] [Test Example 3] 50 g of Example 2-1 was weighed out and placed in a polypropylene container, which was then sealed with a screw cap (the filling rate of the test liquid in the container was 90%), and left to stand at 60° C. for 2 weeks (heat treatment). The arctigenin content of Example 2-1 after heat treatment was measured by high performance liquid chromatography. The same test was conducted for Example 2-6. The results are shown in Table 3.

[0043] [Table 3]

[0044] As shown in Table 3, the arctigenin content of the composition containing burdock seed oil and triethyl citrate (Example 2-1) after heat treatment was 2.7% by mass. This means that the content of arctigenin derived from component (A) was 5.4% by mass, based on the total amount of (A) burdock seed oil. Since burdock seed oil containing 5.4% by mass of arctigenin was produced in Production Example 1, it was revealed that the arctigenin content of the composition of the present invention did not change upon heat treatment and was highly stable. Similarly to Example 2-1, the test solution (Example 2-6) containing phenoxyethanol as component (B) also revealed high arctigenin stability.

Claims

1. A composition comprising (A) burdock seed oil and (B) one or more selected from the group consisting of triethyl citrate, diisopropyl adipate, diethyl sebacate, and phenoxyethanol, The content of arctiin derived from the burdock seed oil (A) is 0.01% by mass or less of the total amount of the composition, The content of the component (B) is 10 to 90 mass %.

2. The composition according to claim 1, containing 1 to 7.5% by mass of arctigenin derived from component (A).

3. The composition according to claim 1 or 2, wherein the content of arctigenin derived from component (A) is 2 to 15 mass% based on the total amount of component (A).

4. A method for producing a composition, comprising a step of blending (A) burdock seed oil and (B) one or more selected from the group consisting of triethyl citrate, diisopropyl adipate, diethyl sebacate, and phenoxyethanol, The manufacturing method comprises adjusting the content of arctiin derived from (A) burdock seed oil to 0.01 mass% or less of the total amount of the composition, and blending the content of (B) component to 10 to 90 mass%.

5. The method for producing a composition according to claim 4, wherein the component (A) is blended so that the content of arctigenin derived from the component (A) is 1 to 7.5% by mass.

6. A manufacturing method described in claim 4 or 5, wherein the content of arctigenin derived from component (A) is 2 to 15 mass% based on the total amount of component (A).

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