Burdock seed oil-containing composition and method for producing 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

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

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

[0002] Burdock fruit, 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 fruit extract containing a high content of arctigenin from burdock fruit is known (Patent Document 1).

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

[0004] International Publication No. 2012 / 043549

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

[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. Preferred aspects of the present invention include: [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], which contains 1 to 7.5% by mass of arctigenin derived from component (A); [3] the composition according to [1] or [2], in which the content of arctigenin derived from component (A) is 2 to 15% by mass based on the total amount of component (A); [4] the composition according to any one of [1] to [3], in which the content of one or more selected from the group consisting of (B) triethyl citrate, diisopropyl adipate, diethyl sebacate, and phenoxyethanol is 10 to 90% by mass; [5] a method for producing a composition, which includes 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 a step of blending component (A) so that the content of arctigenin derived from component (A) is 1 to 7.5% by mass; [7] A method for producing the composition according to [5] or [6], in which the content of arctigenin derived from component (A) is 2 to 15% by mass based on the total amount of component (A); [8] A method for producing the composition according to any one of [5] to [7], in which the content of one or more selected from the group consisting of (B) triethyl citrate, diisopropyl adipate, diethyl sebacate, and phenoxyethanol is 10 to 90% by mass; [9] A method for producing a composition, comprising 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 method comprising a step of incorporating arctigenin into 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 any one of [2] and [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] The method for producing the composition according to any one of [5] to [9], wherein the composition is substantially free of arctiin derived from burdock seed oil;

[14] The topical or oral preparation according to

[10] or

[11] , which is substantially free of arctiin derived from burdock seed oil; etc.

[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.

[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) an ester or glycol ether, and preferably contains 1 to 7.5% by mass of arctigenin derived from component (A). For example, a composition according to one embodiment is 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, and contains 1 to 7.5% by mass of arctigenin derived from component (A).

[0012] <Component (A)> Burdock seed oil is not particularly limited as long as it is obtained from the seeds of Arctum lappa Linne (Compositae), a member 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, and the like. 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 achieving 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, even 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 types and amounts of other ingredients, the intended use of the composition, the dosage form, and the like.

[0016] <Component (B)> From the viewpoint of achieving the effects of the present invention more significantly, the component (B) is preferably an ester or a 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. Even more preferred are triesters having 12 to 27 carbon atoms such as triethyl citrate (12 carbon atoms) and glyceryl hexanoate (triethylhexanoin) (27 carbon atoms); diesters having 12 to 14 carbon atoms such as isopropyl adipate (12 carbon atoms) and diethyl sebacate (14 carbon atoms); and 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), and ethylene glycol monophenyl ether (phenoxyethanol) (8 carbon atoms). Component (B) has fluidity that allows it to be mixed with component (A) by stirring at 20 to 80°C. A commercially available component (B) can be used. Component (B) may be used singly or in combination of two or more. There are no particular limitations on component (B), as long as it is a publicly known component. While 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 Components) 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 the present 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] The component (A) contained in the composition according to this embodiment can be produced through a process including a step of breaking down burdock seeds, a step of extracting burdock seeds to obtain burdock seed oil, a step of filtering the burdock seed oil, a step of incorporating arctigenin into the burdock seed oil at a high concentration, a concentration step, a solid-liquid separation step, etc. Each step may be appropriately selected from the viewpoint of more significantly achieving the effects of the present invention, and it is not necessary to include all steps.

[0021] <Step of Breaking Burdock Seeds> Burdock seeds can be broken by known means, and a commercially available breaking device can also be used. Commercially available burdock seeds broken to any size (particle size) can also be used. From the viewpoint 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, oil, etc., 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 pressurized extraction. The extraction process can be performed at any temperature, but to more significantly achieve the effects of the present invention, the temperature 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. The temperature 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. The time for which the extraction treatment is carried out is not limited, but is preferably 30 minutes or more, more preferably 35 minutes to 24 hours, even more preferably 45 minutes to 20 hours, and even more preferably 1 hour to 20 hours.

[0023] <Step of filtering burdock seed oil> 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 can be performed using known methods and devices such as gel filtration, gel chromatography, thin layer chromatography, and filters.

[0024] <Step of making burdock seed oil contain arctigenin at a high concentration> 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 at this time 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 step> A known concentration method can be used to remove the solvent contained in the extracted burdock seed oil. It is preferable to concentrate the oil to a concentration that will achieve the effects of the present invention.

[0027] <Solid-Liquid Separation Step> To separate the extraction residue from the extracted burdock seed oil, a known solid-liquid separation method such as filtration, sedimentation, or 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 a known method to confirm the arctigenin content. The composition of the present invention can be obtained by mixing component (A) and component (B), and optionally other components. In 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 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 a known method. Here, the ratio of component (A) to component (B) is not limited, but is preferably about 0.1 to 10 parts by mass, more preferably 0.5 to 5 parts by mass, and even more preferably 0.5 to 1.5 parts by mass of component (B) per 1 part by mass of component (A).

[0029] [3. External or oral preparation] The composition according to the present embodiment may be an external or oral preparation. The composition according to the present embodiment may be prepared as an external or 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), 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 the 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, high-intensity 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 a topical or oral preparation can be provided. The content of each component and other conditions are the same as those described in [1. Composition], [2. Method for producing the composition], and [3. Topical or oral preparations].

[0034] The present invention will be specifically described 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] [Production Example 1] Crushed and broken burdock seeds were added to 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 for extracting burdock seeds to obtain burdock seed oil). Filtration was performed 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 arctigenin was 1.1% by mass and arctiin was 19.3% by mass (a process for filtering burdock seed oil). Sulfuric acid was added to the collected 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. Decolorizing charcoal was added to the burdock seed oil and stirred for 18 hours. Then, the mixture was 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 using high-performance liquid chromatography, and the arctigenin content was 5.4% by mass, and no arctiin was detected.

[0036] [Examples and Comparative Examples] 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. Components (A) and (B) were mixed by stirring at room temperature for 30 minutes to prepare each composition of the Examples. Only burdock seed oil (A) obtained in Production Example 1 was used as a comparative composition. Note that in all cases, component (B) in the table represents 100% of the indicated component.

[0037] Test Example 1 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-type lid. After standing at 4°C for one week, the appearance of the composition was observed for 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]

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

[0040] [Test Example 2] After preparing the composition, the composition was allowed to stand for 5 minutes, and the appearance of the composition was observed for stability. When viewing the composition from the side of the beaker, test solutions in which no areas of color gradation (unevenness) were observed were evaluated as ⊚, test solutions in which the areas in which color gradation occurred were less than 50% were evaluated as ◯, 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 evaluated as △, and test solutions in which separation of components (A) and (B) was observed were evaluated as ×. Test solutions in which no areas in which color gradation occurred were observed but separation of components (A) and (B) was observed were evaluated as ×. The results are shown in Table 2.

[0041]

[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-type lid (the filling rate of the test solution in the container was 90%). The container was left to stand at 60°C for 2 weeks (heat treatment). The arctigenin content of Example 2-1 after the heat treatment was measured by high performance liquid chromatography. The same test was also carried out for Example 2-6. The results are shown in Table 3.

[0043]

[0044] As shown in Table 3, the arctigenin content after heat treatment of the composition containing burdock seed oil and triethyl citrate (Example 2-1) 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 the (B) component also revealed high arctigenin stability.

Claims

1. A composition comprising (A) burdock seed oil and (B) one or more members selected from the group consisting of triethyl citrate, diisopropyl adipate, diethyl sebacate, and phenoxyethanol.

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. 3. The composition according to claim 1, wherein the content of (B) one or more selected from the group consisting of triethyl citrate, diisopropyl adipate, diethyl sebacate, and phenoxyethanol is 10 to 90% by mass.

5. (A) The composition described in claim 1, which is substantially free of arctiin derived from burdock seed oil.

6. A method for producing a composition, comprising a step of 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.

7. 7. A method for producing the composition according to claim 6, comprising a step of blending component (A) so that the content of arctigenin derived from component (A) is 1 to 7.5% by mass.

8. The method for producing a composition according to claim 6 or 7, wherein the content of (B) one or more selected from the group consisting of triethyl citrate, diisopropyl adipate, diethyl sebacate, and phenoxyethanol is 10 to 90 mass%.