JPWO2019188490A1 - Composition for improving UV resistance - Google Patents

Abstract

An object of the present invention is to provide a composition for improving ultraviolet resistance. A means for solving the problem is to use one or more compounds selected from the group consisting of a lophenol compound and a cyclolanostane compound as an active ingredient of a composition for improving ultraviolet resistance.

Description

The present invention relates to a composition for improving ultraviolet resistance.

Solar ultraviolet rays are classified into UVA (320-400 nm), UVB (280-320 nm), and UVC (λ <280 nm). Here, although UVC (λ <280 nm) does not reach the ground surface, UVA (320-400 nm) and UVB (280-320 nm) reach the ground surface and cause skin disorders. Exposure of the skin to ultraviolet rays causes erythema and edema of the skin, promotion of the formation of wrinkles and sagging, decreased elasticity of the skin, increased spots and freckles, pigmentation, and decreased skin immune function. Is known (Non-Patent Document 1). In addition, exposure of the skin to ultraviolet rays also induces an increase in yellowing of the skin, a decrease in the skin barrier function, dryness of the skin, and the like (Non-Patent Documents 1 and 2).

To reduce the effect of ultraviolet rays on the skin, it is effective to prevent the skin from being exposed to ultraviolet rays by applying cosmetics such as sunscreen to the surface of the skin.
Further, there is known a means for reducing UV damage to the skin by protecting the skin with cosmetics and increasing the resistance of the skin to UV rays (Patent Document 1).

So far, as a composition for reducing damage caused by ultraviolet rays, an erythema preventive agent containing an apple extract as an active ingredient (Patent Document 1) and an oral ultraviolet resistance improving agent containing methyl hesperidine as an active ingredient (Patent Document 2). , An oral ultraviolet resistance improver containing acetyltryptophan or a salt thereof as an active ingredient (Patent Document 3) is disclosed.

By the way, among plant sterols, compounds having a cyclolanostane skeleton and compounds having a lophenol skeleton have an effect of reducing the amount of lipid peroxide in blood in arteriosclerosis model animals, and the number of plaques formed in the thoracic aorta. It has been found that it has an action of suppressing the above, and its use as an antioxidant has been proposed (Patent Document 4). However, the effect of these compounds on the resistance to UV light was not known at all.

Japanese Unexamined Patent Publication No. 2013-95704 JP-A-2015-42292 Japanese Unexamined Patent Publication No. 2016-41765 International Publication No. 2010/088795 Pamphlet

J Cosmet Chem Jpn 47: 197-201, 2013 Journal of Pharmacy 126 (9): 677-693, 2006

As disclosed in Patent Documents 1-3, while materials for improving ultraviolet resistance have been proposed, the development of highly effective and safe materials has been required.
An object of the present invention is to provide a functional material that can be safely ingested or applied on a daily basis and improves resistance to ultraviolet rays, and a pharmaceutical composition, a food or drink composition, and a cosmetic composition using the same. .. In addition, the present invention provides skin erythema, edema, sagging, wrinkles, actinic keratitis, photosensitivity, photokeratosis, precancerous tumors, and finally skin cancer, etc., with as little pain as possible. It is an object of the present invention to provide a novel composition for improving ultraviolet resistance, which can prevent or ameliorate the symptoms of.

In order to solve the above problems, the present inventors have diligently searched for a component having an inhibitory effect on skin disorders induced by ultraviolet rays, and one or more selected from the group consisting of lophenol compounds and cyclolanostane compounds. The present invention was completed by finding that the compound of the above compound has an effect of improving ultraviolet resistance.

That is, the first invention for solving the above-mentioned problems is a composition for improving ultraviolet resistance, which comprises one or more compounds selected from the group consisting of a lophenol compound and a cyclolanostane compound as an active ingredient.

The first invention includes the following forms.

In a preferred embodiment of the invention, the cyclolanostane compound is selected from the group consisting of 9,19-cyclolanostane-3-ol and 24-methylene-9,19-cyclolanostane-3-ol.

In a preferred embodiment of the invention, the lophenol compounds are 4-methylcholest-7-en-3-ol, 4-methylergost-7-en-3-ol, and 4-methylstigmast-7-en-. Selected from the group consisting of 3-all.

In a preferred embodiment of the present invention, the composition for improving ultraviolet resistance contains 0.00001% by mass or more of the compound in total.

The composition for improving UV resistance of the present invention is preferably used for preventing or ameliorating a skin condition or disease caused by exposing the skin to UV rays.

Preferred forms of the condition or disease are erythema, edema, actinic dermatitis, photosensitivity, photokeratosis, precancerous tumors, or skin cancer.

In addition, the composition for improving ultraviolet resistance of the present invention is preferably used for suppressing tumor formation.

In a preferred embodiment of the present invention, the composition for improving ultraviolet resistance is a food or drink composition or a cosmetic composition.
Further, in a preferred embodiment of the present invention, the composition for improving ultraviolet resistance is a pharmaceutical composition.

A second invention that solves the above problems is the use of a compound selected from the group consisting of a lophenol compound and a cyclolanostane compound in the production of a composition for improving ultraviolet resistance, which is a preferable form of the compound. Is as described above.

In addition, the second invention includes the following forms.

A preferred embodiment of the present invention is the use of a composition containing 0.00001% by mass or more of the compound in total in the production of a composition for improving ultraviolet resistance.

In a preferred embodiment of the invention, the composition is used for the prevention or amelioration of skin conditions or diseases caused by exposing the skin to UV light.

In a preferred embodiment of the invention, the composition is used for the prevention or amelioration of erythema, edema, actinic dermatitis, photosensitivity, photokeratosis, precancerous tumors, or skin cancer.

In a preferred embodiment of the invention, the composition is used to suppress tumorigenesis.

Further, the third invention for solving the above-mentioned problems is a compound selected from the group consisting of a lophenol compound and a cyclolanostane compound used for improving ultraviolet resistance, and a preferable form of the compound is as described above. Is.

In addition, the third invention includes the following forms.

In a preferred embodiment of the invention, the compound is used for the prevention or amelioration of skin conditions or diseases caused by exposing the skin to UV light.

In a preferred embodiment of the invention, the compound is used for the prevention or amelioration of erythema, edema, actinic dermatitis, photosensitivity, photokeratosis, precancerous tumors, or skin cancer.

In a preferred embodiment of the invention, the compound is used to suppress tumorigenesis.

A fourth invention that solves the above problems is a method for improving ultraviolet resistance, which comprises administering to a subject a compound selected from the group consisting of a lophenol compound and a cyclolanostane compound. The preferred form is as described above.

In addition, the fourth invention includes the following forms.

In a preferred embodiment of the present invention, a composition containing a total amount of 0.00001% by mass or more of a compound selected from the group consisting of the lophenol compound and the cyclolanostane compound is administered to the subject.

In a preferred embodiment of the present invention, the method for improving UV resistance is a method for preventing or improving a skin condition or disease caused by exposing the skin to ultraviolet rays.

In a preferred embodiment of the present invention, the method for improving UV resistance is a method for preventing or improving erythema, edema, actinic dermatitis, photosensitivity, photokeratosis, precancerous tumor, or skin cancer.

In a preferred embodiment of the present invention, the method for improving UV resistance is a method for suppressing tumor formation.

3 is a photomicrograph of a three-dimensional skin model exposed to Compound 1 or Compound 2 irradiated with ultraviolet rays and then antibody-stained with a Thymine Dimer antibody.

Next, a preferred embodiment of the present invention will be described in detail. However, the present invention is not limited to the following preferred embodiments, and can be freely modified within the scope of the present invention. In this specification, the percentage is expressed by mass unless otherwise specified.

The composition for improving ultraviolet resistance of the present invention contains one or more compounds selected from the group consisting of a lophenol compound (Compound 1) and a cyclolanostane compound (Compound 2) as an active ingredient. The lophenol compound (Compound 1) is represented by the following general formula (1).

In the general formula (1), R1 is a linear or branched alkyl group having 5 to 16 carbon atoms, or an alkenyl group containing one or two double bonds. Further, the alkyl group or alkenyl group may be a substituted alkyl group or a substituted alkenyl group in which 1 or 2 hydrogen atoms are substituted with a hydroxyl group and / or a carbonyl group.
Further, R2 and R3 are independently hydrogen atoms or alkyl groups having 1 to 3 carbon atoms. Here, as the alkyl group having 1 to 3 carbon atoms, a methyl group, an ethyl group and the like are preferable, and a methyl group is particularly preferable. Further, the alkyl group may be a substituted alkyl group in which at least one hydrogen atom is substituted with a hydroxyl group and / or a carbonyl group.

Further, R4 forms C = O together with the carbon atoms constituting the ring, or is either _{−OH or −OCOCH 3.}

In the general formula (1), R1 is preferably any of the groups represented by the following formula.

Further, in the general formula (1), one of R2 and R3 is preferably a hydrogen atom, the other is preferably a methyl group, and R4 is preferably a hydrogen group.

Compound 1 preferably includes 4-methylcholest-7-en-3-ol, 4-methylergost-7-en-3-ol and 4-methylstigmast-7-en-3-ol. .. Each compound has a structure represented by the following formula.

Compound 1 can be chemically produced according to a known production method.
For example, Vitali Mathish et al. , PLOS BIOLOGY, Volume 2, Issue 10, e280, 2004, and can be synthesized according to the supplement data described.

Further, it is known that compound 1 is contained in plants, and compound 1 can be produced according to a known method for producing lophenol (Biochemical Experimental Method 24, Lipid Lipid Metabolism Experimental Method, etc.). Akihiro Yamada, Academic Publishing Center, p. 174, 1989).
For example, the fact that compound 1 is contained can be extracted from a plant by a method such as a hot water extraction method, an organic solvent extraction method, a supercritical extraction method or a subcritical extraction method (for example, a patent). (See Japanese Patent Application Laid-Open No. 3905913). Compound 1 can be extracted from, for example, plants of the Liliaceae, Leguminosae, Gramineae, Solanaceae and Bananas families.
The molecular weight, structure, and the like of the compound 1 produced as described above can be determined or confirmed by, for example, a mass spectrum (MS) method, a nuclear magnetic resonance spectrum (NMR) method, or the like.

In addition, compound 1 may be a salt that is acceptable for the pharmaceutical composition. Acceptable salts in pharmaceutical compositions include both metal salts (inorganic salts) and organic salts, the list of which is "Remington's Pharmaceutical Sciences, 17th Edition". , 1985, No. 1418 Tribute ”is illustrated.
Specifically, inorganic acid salts such as hydrochloride, sulfate, phosphate, diphosphate, and hydrobromide, malate, maleate, fumarate, tartrate, and succinate. , Citrate, acetate, lactate, methanesulfonate, p-toluenesulfonate, pamoate, salicylate, and organic acid salts such as stearate are included, but not limited to.
It can also be a salt of a metal such as sodium, potassium, calcium, magnesium or aluminum, or a salt with an amino acid such as lysine. Further, a solvate such as a hydrate of a salt permitted for the compound or a pharmaceutical composition thereof can also be used.

The cyclolanostane compound (Compound 2) is represented by the following general formula (2).

In the general formula (2), R5 is a linear or branched alkyl group having 6 to 8 carbon atoms and an alkenyl group containing one or two double bonds. Further, the alkyl group or alkenyl group may be a substituted alkyl group or a substituted alkenyl group in which 1 or 2 hydrogen atoms are substituted with a hydroxyl group and / or a carbonyl group. Further, R6 and R7 are independently hydrogen atoms or methyl groups, respectively. Further, R8 forms C = O together with the carbon atoms constituting the ring, or is either of the following formulas.

In the general formula (2), R5 is preferably any of the groups represented by the following formula.

Further, in the general formula (2), one of R6 and R7 is preferably a hydrogen atom, the other is preferably a methyl group, and R8 is preferably a hydroxyl group.

Compound 2 preferably includes 9,19-cyclolanostane-3-ol and 24-methylene-9,19-cyclolanostane-3-ol. Each compound has a structure represented by the following formula.

Compound 2 can be chemically produced according to a known production method. For example, 24-methylene-9,19-cyclolanostan-3-ol (common name: 24-methylenecycloaltanol) is available from JP-A-57-018617 and WO2012 / 023599 (γ-oryzanol). It is possible to produce by the method disclosed in (Method for synthesizing from). In addition, Compound 2 can be produced using a hydrolyzate of cycloartenol ferlate as a starting material by the method disclosed in JP-A-2003-277269.

Compound 2 is also known to be contained in plants such as Liliaceae, Leguminosae, Gramineae, Solanaceae and Bananas ([Phytochemicals, USA, 1977, Vol. 16]. , Pages 140-141], [Handbook of Phytochemical Constituts of GRAS Herbs and Other Economic Plants (Handbook of phytochemical compounds of GRAS herbs and nights) , USA, CRC Press], or [Hager's Handbuch der Pharmazeutischen Praxis, Vol. 2-6, 1969-1979, Springer Fairerk Berlin, Germany ]reference). Therefore, compound 2 can be extracted from these plants by using a known method such as an organic solvent extraction method or a hot water extraction method (see, for example, Japanese Patent No. 3924310). Compound 2 is preferably extracted from a plant belonging to the genus Aloe of the Liliaceae family.
The molecular weight, structure, and the like of the compound produced as described above can be determined or confirmed by, for example, a mass spectrum (MS) method, a nuclear magnetic resonance spectrum (NMR) method, or the like.

In addition, compound 2 may be a salt that is acceptable for the pharmaceutical composition. Such salts are as exemplified for Compound 1.

The composition for improving ultraviolet resistance of the present invention contains one or more compounds selected from Compound 1 and Compound 2 as an active ingredient. In addition, one or more of each of compound 1 and compound 2 can be used as an active ingredient. The active ingredient may be either Compound 1 or Compound 2 alone or a mixture of Compound 1 and Compound 2, but a mixture of Compound 1 and Compound 2 is more preferable. That is, in a preferred embodiment, one or more selected from compound 1 and one or more mixtures selected from compound 2 are contained as active ingredients.
When compound 1 or compound 2 is used alone, compound 1 (mainly 4-methylcholest-7-en-3-ol, 4-methylergost-7-en-3-ol, or 4-methyls) is used. Either thygmast-7-en-3-ol) or compound 2 (mainly 9,19-cyclolanostane-3-ol or 24-methylene-9,19-cyclolanostane-3-ol). Is preferable.
Among them, 4-methylcholest-7-en-3-ol is particularly preferable as the compound 1 in terms of physical properties such as solubility which are considered when used as an active ingredient of the composition for improving ultraviolet resistance, and as the compound 2, the compound 2 is used. Of particular preference is 9,19-cyclolanostan-3-ol.
When compound 1 and compound 2 are compared, compound 1 (mainly 4-methylcholest-7-en-3-ol, 4-methylergost-7-en-3-ol or 4-methylstig) Mast-7-en-3-ol) is more preferable.
Further, in each of the compound 1 or the compound 2, one kind of compound may be used, or a plurality of compounds may be mixed and used.
The composition for improving UV resistance of the present invention preferably contains 4-methylcholest-7-en-3-ol, 4-methylergost-7-en-3-ol, and 4-methylstigmast-7-. Contains one or more compounds selected from the group consisting of en-3-ol, 9,19-cyclolanostan-3-ol, 24-methylene-9,19-cyclolanostane-3-ol as an active ingredient. To do.

When both compound 1 and compound 2 are combined (a mixture of compound 1 and compound 2), the range of the mass ratio of compound 1 and compound 2 is, for example, as follows.
Compound 1: Compound 2 is preferably 5: 1 to 1: 5, more preferably 3: 1 to 1: 3, and particularly preferably 2: 1 to 1: 2.

The content of the compound in the composition for improving ultraviolet resistance of the present invention can be appropriately selected depending on the symptoms and the like, but the total amount is preferably at least 0.00001% by mass, more preferably at least 0. It is 0001% by mass or more, more preferably at least 0.0005% by mass or more, and particularly preferably at least 0.001% by mass or more. The upper limit of the amount of the composition for improving ultraviolet resistance of the present invention is not particularly limited, but the total amount is exemplified by 90% by mass or less, preferably 70% by mass or less, and more preferably 50% by mass or less.

Further, the composition for improving ultraviolet resistance of the present invention has a form in which a composition containing 0.00001% by mass or more of one or a plurality of compounds selected from the group consisting of compound 1 and compound 2 is contained as an active ingredient. You can also do it.
Such compositions are obtained, for example, from an extract obtained from a plant containing the above-mentioned compound 1, an extract obtained from a plant containing compound 2, and a plant containing both compound 1 and compound 2. Extracts, as well as mixtures thereof.

Here, examples of the plant containing the compound 1 and the compound 2 include plants of the family Liliaceae, the family Leguminosae, the family Gramineae, the family Solanaceae, and the family Bananas.

As an example contained in natural plants, in aloe vera, compound 1 (mainly 4-methylcholest-7-en-3-ol, 4-methylergost-7-en-3-ol and 4-methyl ergost-7-en-3-ol) Methyl stigmast-7-en-3-ol) and compound 2 (mainly 9,19-cyclolanostane-3-ol and 24-methylene-9,19-cyclolanostane-3-ol) It is known to be included.

Therefore, using aloe vera as a raw material, 4-methylcholest-7-en-3-ol, 4-methylergost-7-en-3-ol, or 4-methylstigmast-7-en-3-ol Purify any of (Compound 1), 9,19-cyclolanostane-3-ol, or 24-methylene-9,19-cyclolanostane-3-ol (Compound 2), respectively. It is possible to obtain a mixture containing Compound 1: Compound 2 in an amount of 5: 1 to 1: 5, preferably 3: 1 to 1: 3, and particularly preferably 2: 1 to 1: 2. The composition thus obtained is suitable as an active ingredient of the composition for improving ultraviolet resistance of the present invention.

By administering one or more compounds selected from the group consisting of lophenol compounds and cyclolanostane compounds, it has an effect of improving the resistance to ultraviolet rays of the administration target as compared with the case where it is not ingested.
The composition for improving UV resistance of the present invention can be used for preventing or ameliorating a skin condition or disease caused by exposing the skin to ultraviolet rays.
Examples of the skin condition or disease include erythema, edema, photokeratosis, precancerous tumor, skin cancer, sun dermatitis, photosensitivity, and photoaging.

Further, as shown in a test described later, it was found that Compound 1 or Compound 2, which is an active ingredient of the composition for improving ultraviolet resistance of the present invention, has a DNA damage suppressing effect.
Here, exposure to ultraviolet light causes DNA damage, and DNA damage causes canceration (Pharmaceutical Journal 126 (9): 677-693, 2006).
As shown in Examples described later, the composition for improving ultraviolet resistance of the present invention has an effect of suppressing the occurrence of erythema and at the same time suppressing DNA damage caused by ultraviolet rays, and thus has an effect of suppressing photokeratosis and precancerous tumors. It has the effect of suppressing the progression, and eventually the progression to skin cancer.

The composition for improving ultraviolet resistance of the present invention can be a pharmaceutical composition.
The pharmaceutical composition of the present invention is orally or parenterally administered to mammals including humans.

In addition, the pharmaceutical composition of the present invention contains one or more compounds selected from the group consisting of a lophenol compound and a cyclolanostane compound in a total amount, more preferably at least 0.0001% by mass or more, still more preferably at least 0. It is preferable that the composition contains a composition containing 0005% by mass or more, particularly preferably at least 0.001% by mass or more, as an active ingredient.

The form of the pharmaceutical composition of the present invention is not particularly limited, and can be appropriately selected depending on the usage. Specific examples include tablets, pills, powders, liquids, suspensions, emulsions, granules, capsules, syrups, suppositories, injections, ointments, patches, eye drops, nasal drops, etc. it can.

The administration time of the pharmaceutical composition of the present invention is not particularly limited, and can be appropriately selected depending on the target disease. In addition, the dose is preferably determined according to the formulation form, usage, age, sex, other conditions, degree of symptom, etc. of the patient.
The dose of the pharmaceutical composition of the present invention is appropriately selected depending on the usage, age, sex, degree of disease, other conditions and the like of the patient. Usually, in terms of the amount of the active ingredient, the guideline is preferably 0.0001 to 100 mg / day, more preferably 0.001 to 50 mg / day, and particularly preferably 0.01 to 10 mg / day.

The pharmaceutical composition of the present invention may contain additives that are commonly used in pharmaceutical compositions. Examples of the additive include excipients, binders, disintegrants, lubricants, stabilizers, flavoring agents, diluents, surfactants, solvents for injections and the like.

The pharmaceutical composition of the present invention can be produced by blending the compound as an active ingredient in a carrier for a pharmaceutical composition. The pharmaceutical composition of the present invention can be produced, for example, by formulating the compound together with the above-mentioned additives.
In addition, the pharmaceutical composition of the present invention is an extract obtained by extracting with hot water or various solvents, supercritical extraction, and subcritical extraction using a known plant or the like containing the compound as a raw material. It can also be produced by formulating with an additive.
In particular, the pharmaceutical composition of the present invention containing Compound 1 and Compound 2 in the specific mass ratio range can be produced by mixing each compound in the mass ratio range. Further, such a pharmaceutical composition is prepared by a method such as extraction using hot water or various solvents, supercritical extraction, subcritical extraction, etc., using known plants or the like containing Compound 1 and Compound 2 as raw materials. It can also be manufactured.

The pharmaceutical composition of the present invention can be obtained from plants such as Liliaceae, Leguminosae, Gramineae, Solanaceae and Bananas, for example.

In the pharmaceutical composition of the present invention, the compound functions as an active ingredient and has a preventive or ameliorating effect on symptoms caused by exposure of the skin to ultraviolet rays.

Further, the composition for improving ultraviolet resistance of the present invention can be a food and drink composition. In the present invention, the "food and drink composition" includes foods and drinks ingested by humans as well as feeds ingested by animals other than humans.

The food and drink composition of the present invention contains a compound selected from the group consisting of Compound 1 and Compound 2 as an active ingredient. The compound may be one kind, that is, either Compound 1 or Compound 2, alone, or a mixture of Compound 1 and Compound 2.
When compound 1 or compound 2 is used alone, compound 1 (mainly 4-methylcholest-7-en-3-ol, 4-methylergost-7-en-3-ol, or 4-methyls) is used. Either thygmast-7-en-3-ol) or compound 2 (mainly 9,19-cyclolanostane-3-ol or 24-methylene-9,19-cyclolanostane-3-ol). Is preferable.
Among them, 4-methylcholest-7-en-3-ol is particularly preferable as compound 1, and 9, as compound 2, from the viewpoint of physical properties such as solubility which are considered when used as an active ingredient of a food or drink composition. 19-Cyclolanostan-3-ol is particularly preferred.
When compound 1 and compound 2 are compared, compound 1 (mainly 4-methylcholest-7-en-3-ol, 4-methylergost-7-en-3-ol or 4-methylstig) Mast-7-en-3-ol) is more preferable.
Further, in each of the compound 1 or the compound 2, one kind of compound may be used, or a plurality of compounds may be mixed and used.
The food and drink composition of the present invention preferably contains 4-methylcholest-7-en-3-ol, 4-methylergost-7-en-3-ol, and 4-methylstigmast-7-en-3. The active ingredient contains one or more compounds selected from the group consisting of −ol, 9,19-cyclolanostane-3-ol, 24-methylene-9,19-cyclolanostane-3-ol.

When both compound 1 and compound 2 are combined (a mixture of compound 1 and compound 2), the range of the mass ratio of compound 1 and compound 2 is, for example, as follows.
Compound 1: Compound 2 is preferably 5: 1 to 1: 5, more preferably 3: 1 to 1: 3, and particularly preferably 2: 1 to 1: 2.

The content of the compound in the food and drink composition of the present invention can be appropriately selected depending on the symptoms and the like, but the total amount is preferably at least 0.00001% by mass, more preferably at least 0.0001% by mass. As mentioned above, it is more preferably at least 0.0005% by mass or more, and particularly preferably at least 0.001% by mass or more. The upper limit of the amount in the food and drink composition of the present invention is not particularly limited, but the total amount is exemplified by 90% by mass or less, preferably 70% by mass or less, and more preferably 50% by mass or less.

In addition, the food and drink composition of the present invention contains, as an active ingredient, a composition containing 0.00001% by mass or more of one or more compounds selected from the group consisting of compound 1 and compound 2. The compound may be one kind or a plurality of kinds.
Such compositions are obtained, for example, from an extract obtained from a plant containing the above-mentioned compound 1, an extract obtained from a plant containing compound 2, and a plant containing both compound 1 and compound 2. Extracts, as well as mixtures thereof.

For example, in aloe vera, as an example contained in natural plants, compound 1 (mainly 4-methylcholest-7-en-3-ol, 4-methylergost-7-en-3-ol and 4-Methylstigmast-7-en-3-ol), and Compound 2 (mainly 9,19-cyclolanostane-3-ol and 24-methylene-9,19-cyclolanostane-3-ol). ) Is known to be included.

Therefore, using aloe vera as a raw material, 4-methylcholest-7-en-3-ol, 4-methylergost-7-en-3-ol, or 4-methylstigmast-7-en-3-ol Purify any of (Compound 1), 9,19-cyclolanostane-3-ol, or 24-methylene-9,19-cyclolanostane-3-ol (Compound 2), respectively. It is possible to obtain a mixture containing Compound 1: Compound 2 in an amount of 5: 1 to 1: 5, preferably 3: 1 to 1: 3, and particularly preferably 2: 1 to 1: 2. The composition thus obtained is suitable as an active ingredient of the food and drink composition of the present invention.

In addition, the food and drink composition of the present invention contains one or a plurality of compounds selected from the group consisting of a lophenol compound and a cyclolanostane compound in a total amount, more preferably at least 0.0001% by mass or more, still more preferably at least. It is preferable that the composition contains 0.0005% by mass or more, particularly preferably at least 0.001% by mass or more, as an active ingredient.

The food and drink composition of the present invention is effective in preventing or ameliorating skin symptoms caused by exposure of the skin to ultraviolet rays.
The symptoms include erythema, edema, actinic keratosis, actinic dermatitis, photosensitivity, and photoaging.

The total amount of the compound in the food or drink composition is preferably 0.0001 to 100 mg / day, more preferably 0.001 to 50 mg / day, and particularly preferably 0.001 to 50 mg / day, depending on the form thereof. The amount may be suitable for ingestion in the range of 0.01 to 10 mg / day. Therefore, the food and drink composition of the present invention ingests the compound in a total amount of preferably 0.0001 to 100 mg / day, more preferably 0.001 to 50 mg / day, and particularly preferably 0.01 to 10 mg / day. It is preferable that it is used as such.

The food or drink is preferably a food with health claims. "Health functional foods" are foods that have a direct or indirect indication of the preventive effect of the disease or the effect of reducing the risk of developing the disease, and the business operator is responsible for functioning in the product package based on scientific evidence. It means food that has been notified to the Consumer Affairs Agency as an indication of sex. For example, foods currently sold in Japan in the form of foods for specified health use, foods with functional claims, dietary supplements, and the like can be mentioned.

The form of the food or drink is not particularly limited, but beverages such as soft drinks, carbonated drinks, nutritional drinks, fruit juice drinks, and lactic acid bacteria drinks (including concentrated stock solutions and preparation powders of these drinks) can efficiently use the compound. Especially preferable from the viewpoint of ingestion.

In addition, it is preferable that the functional food or drink is in the form of granules, tablets, or liquid supplements because it is easy for the ingestor to grasp the intake amount of the active ingredient.

In addition, such functional foods and drinks include "to improve resistance to ultraviolet rays", "to prevent or improve the condition of the skin caused by exposing the skin to ultraviolet rays", "erythema, edema, etc." It is also preferable that the form is marked with the purpose of "for prevention or improvement of photokeratosis". That is, the food or drink of the present invention is one or more compounds selected from the group consisting of Compound 1 and Compound 2, for example, for the purpose of "preventing or ameliorating erythema, edema, photokeratosis". Is preferably sold as a food or drink for improving resistance to ultraviolet rays, which contains the above as an active ingredient.

The "indication" includes all indications having a function of informing the consumer of the use. That is, any display that can be recalled or inferred from the above-mentioned use falls under the above-mentioned "display" regardless of the purpose of the display, the content of the display, the object / medium to be displayed, and the like. Further, the "labeled" means that there is a labeling act of associating the labeling with a food or drink (product) to be recognized. It is preferable that the display act is such that the consumer can directly recognize the use. Specifically, the act of describing the above-mentioned use on the product or product packaging of the food or drink of the present invention, the above-mentioned use on the advertisement, price list or transaction document (including those provided by an electromagnetic method) related to the product. The description act of is illustrated.

On the other hand, the displayed content (display content) is a display approved by the government, etc. (for example, a display obtained based on various systems established by the government and performed in a manner based on such approval). Is preferable.
For example, labeling of health foods, functional foods and drinks, enteric nutritional foods, special purpose foods, health functional foods, foods for specified health use, nutritional functional foods, foods with functional claims, external products for pharmaceutical compositions, etc. is illustrated. be able to. In particular, a label approved by the Consumer Affairs Agency, for example, a label approved by a food system for specified health use or a system similar thereto can be exemplified. Examples of the latter include labeling as a food for specified health use, labeling as a food for specified health use as a condition, labeling indicating that it affects the structure and function of the body, labeling for reducing the risk of illness, and the like. Speaking of which, labeling as a food for specified health use (especially labeling for health uses) stipulated in the Health Promotion Law Enforcement Regulations (April 30, 2003, Ministry of Health, Labor and Welfare Ordinance No. 86), and similar The display can be enumerated as a typical example.

The wording expressing the above-mentioned use shall be included in the scope of the present invention as long as it is a wording expressing an action or effect of improving resistance to ultraviolet rays or preventing or ameliorating a condition caused by exposure to ultraviolet rays. Needless to say.
Further, it is preferable that the food or drink of the present invention includes, in addition to the indication of the above-mentioned use, the indication of the active ingredient, and further, the indication indicating the relationship between the use and the active ingredient.

The food or drink can be produced by blending one or more compounds selected from the group consisting of compound 1 and compound 2 as an active ingredient. The food and drink of the present invention can be produced, for example, by mixing the compound with a food and drink raw material and processing it.
Further, in the food and drink, an extract obtained by extraction using hot water or various solvents, supercritical extraction, and subcritical extraction using a known plant or the like containing the compound as a raw material is processed together with the food and drink raw material. It can also be manufactured by doing so.

In addition, when the form of the food or drink is a granular, tablet-like or liquid supplement, the compound which is an active ingredient is, for example, sugars such as lactulose, maltitol, and lactitol, and other sugars. , For example, dextrin, starch, etc .; proteins such as gelatin, soy protein, corn protein; amino acids such as alanine, glutamine, isoleucine; polysaccharides such as cellulose, arabic rubber; , It is also preferable to formulate.

Further, the composition for improving ultraviolet resistance of the present invention can be a cosmetic composition.

The preferred form of the type and ratio of the active ingredient contained in the cosmetic composition of the present invention is the same as that of the food and drink composition of the present invention.

The content of the compound in the cosmetic composition of the present invention can be appropriately selected depending on the symptoms and the like, but the total amount is preferably at least 0.00001% by mass or more, more preferably at least 0.0001% by mass or more. , More preferably at least 0.0005% by mass or more, and particularly preferably at least 0.001% by mass or more. The upper limit of the amount in the cosmetic composition of the present invention is not particularly limited, but the total amount is exemplified by 90% by mass or less, preferably 70% by mass or less, and more preferably 50% by mass or less.

The cosmetic composition of the present invention is effective in preventing or ameliorating a skin condition or disease caused by exposing the skin to ultraviolet rays.
The symptoms include erythema, edema, actinic keratosis, actinic dermatitis, photosensitivity, and photoaging.

The "cosmetic composition" includes cosmetics and quasi-drugs under the Pharmaceutical Affairs Law, and examples thereof include cosmetics used on the skin, bathing agents, and fragrances.

In the cosmetic composition, commonly used ingredients can be appropriately blended. Further, the form of the cosmetic composition is not particularly limited.
The cosmetic composition of the present invention includes, for example, soap, synthetic cosmetic soap, liquid body cleaning agent (body soap), cleaning agent such as washing pigment, cleansing cream, cleaning lotion, lotion, milky lotion, beauty liquid, lotion. , Liquid packs, paste packs, etc., white powder, water white powder, white powder, etc., cosmetics such as dusting, foundation, lipstick, cheek red, eyeliner, eye shadow, etc., sunscreen Examples thereof include cosmetics such as cosmetics, suntan cosmetics and hair removal cosmetics, and cosmetics for shaving such as shaving lotion and after-shaving lotion, but the present invention is not limited thereto.

The cosmetic composition of the present invention contains an effective amount of the above compound, and can exhibit an effect of improving ultraviolet resistance by use.

In addition to the above compounds, ingredients usually used in cosmetics can be appropriately selected and added to the cosmetic composition within a range that does not impair the purpose, action, and effect of the present invention. Such components include, for example, surfactants, oils, moisturizers, softeners, feel improvers, oily agents, emulsifiers, antioxidants, preservatives, fungicides, emollients, pH adjusters, chelating agents, stables. Agents, UV absorbers, alcohols, silicon compounds, thickeners, viscosity regulators, solubilizers, pearlizing agents, fragrances, refreshing agents, bactericides, antibacterial agents, natural extracts, colorants, anti-fading agents , Purified water and other solvents, propellants, etc., but are not limited thereto.

[Test 1]
In this test, the effect of suppressing erythema by UVB irradiation of a composition containing Compound 1 or Compound 2 was examined using hairless mice.

(1) Preparation of feed Compound 1 and Compound 2 were added to the AIN-93G feed to prepare a test feed containing 0.00002% (0.2 ppm) of Compound 1 and Compound 2 in total. In addition, ordinary AIN-93G was used as a control feed. The mass ratio of compound 1 and compound 2 in the test feed depends on the mass ratio of each compound contained in the aloe powder, and is therefore in the range of 5: 1 to 1: 5.

(2) Test method Hos: HR-1 mice (7 weeks old, female) were purchased from Hoshino Test Animal Breeding Center (Nippon SLC). After 1 week of preliminary breeding, 56 mice were grouped into the following 7 setting groups of 8 mice each.

After grouping, the UVB non-irradiated group and the control group were fed with AIN-93G feed as they were, and the test feed group was fed with a test feed containing compound 1 and compound 2 and bred for 14 days. On the 14th day, the control group and the test feed group were irradiated with ^{UVB 180 mJ / cm 2 once.} The UVB non-irradiated group was not irradiated with UVB.
After 14 days of breeding for the UVB non-irradiated group, and before UVB irradiation and 3, 24, 48 hours after the irradiation for the control group and the test feed group, a spectrophotometer (Konica Minolta CM-700d) was used. Erythema formation was evaluated by measuring the skin color (a ^{* value) on the back.}

(3) Test results The results are shown in Table 2. In the table, the significance probability by the Student's t-test is indicated by the symbol * or the symbol #. The symbol * indicates the significance probability of the same group after irradiation and before irradiation, and the symbol # indicates the significance probability of the test feed group with respect to the control group.

As is clear from the results in Table 2, the a ^* value of the back skin of the test feed group suppressed the increase in redness due to ultraviolet irradiation as compared with ^{the a *} value of the back skin of the control group. all right. That is, it was found that the mice in the test feed group had improved resistance to ultraviolet rays.

[Test 3] Evaluation of DNA damage inhibitory effect In this test, the repair effect on DNA damage of compound 1, compound 2, or a composition containing these was examined using hairless mice.

(1) Preparation of feed Compound 1 and Compound 2 were added to the AIN-93G feed to prepare a test feed containing 0.00002% (0.2 ppm) of Compound 1 and Compound 2 in total. In addition, ordinary AIN-93G was used as a control feed. The mass ratio of compound 1 and compound 2 in the test feed depends on the mass ratio of each compound contained in the aloe powder, and is therefore in the range of 5: 1 to 1: 5. The effects on the generation of DNA damage and the expression of DNA damage repair enzymes were examined by the following methods.

(2) Test method Hos: HR-1 mice (7 weeks old, female) were purchased from Hoshino Test Animal Breeding Center (Nippon SLC). After 1 week of pre-rearing, 15 mice were grouped into the following 3 setting groups with 5 mice each.

After grouping, the UVB non-irradiated group and the control group were fed with AIN-93G feed as they were, and the test feed group was fed with a test feed containing compound 1 and compound 2 and bred for 14 days. On the 14th day, the control group and the test feed group were irradiated with ^{UVB 180 mJ / cm 2 once.} The UVB non-irradiated group was not irradiated with UVB.
For the UVB non-irradiated group, after 14 days of breeding, for the control group and the test feed group, before UVB irradiation and 24 hours after irradiation, the back skin tissue was collected, the amount of DNA photoproduct was measured, and the photorepair enzyme was measured. The change in the expression level of was measured.
Regarding the amount of DNA photoproducts, the amounts of cyclobutane-type dimer (CPD) and 6-4 photoproducts (6-4PP), which are indicators of DNA damage, are used in OxiSelect Cellar UV-Induced DNA Damage ELISA Kit (CPD) and Measurements were made using the OxiSelect Cellar UV-Induced DNA Damage ELISA Kit (6-4PP) (see PLOS ONE October 2013, Vol. 8 Issue10 e77308).
Regarding the expression level of the photorepair enzyme, the expression of XPA and XPC, which are repair enzymes involved in nucleotide repair, was measured by the real-time RT-PCR method. As the oligonucleotide of RT-PCR, XPA MA128484 and XPC MA096119 manufactured by Takara Bio Inc. were used.

(3) Test results The results are shown in Tables 4 and 5. The expression levels of XPA and XPC shown in Table 5 are shown as relative values with respect to the UVB non-control group.

As is clear from the results in Table 4, it was confirmed that the production of CPD and 6-4PP was significantly increased by irradiation with ultraviolet rays (control group). It was confirmed that the production of CPD and 6-4PP was significantly suppressed in the test feed group as compared with this control group.

As is clear from the results in Table 5, it was confirmed that the expression levels of XPA and XPC, which are repair enzymes involved in nucleotide excision, showed significantly lower values by irradiation with ultraviolet rays (control group). On the other hand, in the test feed group, it was revealed that the expression of these repair enzymes was significantly restored.

[Test 4]
In this test, a three-dimensional skin model EFT-400 (manufactured by MatTek) is used to add and culture a cyclolanostane compound or a lophenol compound to suppress the formation of DNA damage induced by ultraviolet irradiation. Was examined.

(1) Test method (1-1) Preparation of test medium By dissolving compound 1 or compound 2 in DMSO and adding it to EFT-400-ASY medium (manufactured by MatTek: obtained from Kurabou Co., Ltd.). , 1 μM of compound 1 or compound 2 and 0.2% of DMSO were prepared as a test medium.
In addition, as a negative control, a test medium containing 0.2% DMSO was prepared.

(1-2) Culturing of skin model The three-dimensional skin model was cultured in a medium for exclusive use of EFT-400 (manufactured by MatTek) at 37 ° C. under 5% CO2 conditions. The three-dimensional skin model was cultured for 4 days using the test medium or control medium described above. After collecting the medium on the 5th day, the 3D skin model was washed with PBS (−), and then the 3D skin model was immersed in 2.5 mL of PBS (−) and irradiated with ^{UVB 120 mJ / cm 2.} The 3D skin model was transferred again to test medium or control medium and cultured for 6 hours. In addition, the cells were cultured in a test medium containing 0.2% DMSO for 6 hours without irradiation with UVB.
The three-dimensional skin model was fixed in formalin, embedded in paraffin, and sliced to a thickness of 5 μm. Sections were heat-treated in the presence of EDTA buffer, and Monoclonal antibody-Thymine Dimer CPD antibody H3 (abcam) 5 μg / mL was diluted 100-fold as the secondary antibody, and Rabbit antibody-mouse Immunoglobulin-FITC (DACO) was used. The antibody was stained with Thymine Dimer.

(2) Test Results FIG. 1 shows a micrograph of a tissue section of a three-dimensional skin model irradiated with ultraviolet rays, which was antibody-stained with a Thymine Dimer antibody.
In the UVB non-irradiated group, the formation of Thymine Dimer (CPD), which is an index of DNA damage, was not confirmed.
In the control group irradiated with ultraviolet rays, the formation of Thymine Dimer (CPD), which is an index of DNA damage, was confirmed, indicating that the irradiation of ultraviolet rays induces DNA damage in cells. On the other hand, culturing in the presence of Compound 1 or Compound 2 reduced the formation of Thymine Dimer even under UV irradiation conditions, indicating that the test substance suppresses DNA damage due to UV irradiation.
It was found that the feed containing 1 μM of Compound 1 or Compound 2 had an effect of suppressing DNA damage.

From the results of Tests 1 to 3, it was found that Compound 1 or Compound 2 has an effect of suppressing the occurrence of erythema caused by ultraviolet rays. It was also found that these compounds have a DNA damage suppressing effect. From this, it was clarified that Compound 1 or Compound 2 improved the UV resistance of the skin, and as a result, erythema was suppressed.

[Test 5]
In this test, hairless mice (Hos: HR-1 mice (7 weeks old, female)) were used to examine the inhibitory effect of UVB irradiation on the composition containing Compound 1 or Compound 2.

(1) Preparation of feed By adding compound 1 and compound 2 to the AIN-93G feed, a test feed containing 0.00002% (0.2 ppm) of compound 1 and compound 2 in a mass ratio of 1: 1 in total. Was produced.
In addition, a positive control feed containing 0.13% of Neutrox sun (a component containing citrus fruit extract and rosemary extract) was prepared for administration to the positive control group.
In addition, AIN-93G was used as the normal feed to be administered to the UVB non-irradiated group and the negative control group.

(2) Test method Hairless mice (Hos: HR-1 mice (7 weeks old, female)) were purchased from Hoshino Test Animal Breeding Center (Nippon SLC). After 1 week of preliminary breeding, 32 hairless mice were grouped into 4 setting groups shown in Table 5 by 8 mice each.

After grouping, the feeds shown in Table 6 were fed and bred.
On the 14th day from the start of breeding with the above feed, the negative control group, the test feed group, and the positive control group were irradiated with ^{UVB 180 mJ / cm 2 once.}
The UVB non-irradiated group was not irradiated with UVB.

For the control group and the test feed group, erythema formation was performed by measuring ^{the skin color (a *} value) of the back using a back spectrophotometer (Konica Minolta CM-700d) before UVB irradiation and 24 hours after irradiation. evaluated.
In the UVB non-irradiated group, after 14 days of breeding, erythema formation was evaluated by measuring ^{the skin color (a * value) of the back using a back spectrophotometer (Konica Minolta CM-700d).}

(3) Test results The results are shown in Table 6. In Table 6, the significance probability by the Student's t-test is indicated by the symbol * or the symbol #. The symbol * is the significance probability of the same group after irradiation (a ^* value) and before irradiation (a ^* value), and the symbol # is after irradiation of the sample administration group (a ^* value) and after irradiation of the negative control group (a * value). ^{Indicates the} significance probability for a * value).

^{From the results in Table 6, it was found that the a *} value of the back skin of the test feed group was significantly suppressed from the increase of redness due to ultraviolet irradiation as compared with ^{the a *} value of the back skin of the negative control group. .. That is, it was found that the mice in the test feed group had improved resistance to ultraviolet rays.

Moreover, when the results of the positive control group and the negative control group in Table 6 were compared, there was no significant difference between the positive control group and the negative control group.
Here, it is known that Neutrox sun (Monteroeder) contained in the positive control feed contains a citrus fruit extract and a rosemary extract as participating components and has an effect of suppressing an increase in redness due to ultraviolet irradiation.
That is, it was found that Compound 1 or Compound 2 has an effect of suppressing an increase in redness due to ultraviolet irradiation as compared with Neutrox Sun (a substance having an effect of suppressing an increase in redness due to Ultraviolet irradiation).

(4) Discussion From the results of Test 5, it was found that Compound 1 or Compound 2 has an effect of suppressing the occurrence of erythema caused by ultraviolet rays.

[Manufacturing Example 1]
A pharmaceutical composition having the following composition and having an ultraviolet resistance improving action was produced by the following method.
Carboxymethyl cellulose (CMC: manufactured by Daiichi Kogyo Seiyaku Co., Ltd.) was added to a mixture containing a lophenol compound and a cyclolanostane compound in a mass ratio of lophenol compound: cyclolanostane compound = 1: 1. 2% by mass of the composition containing 0.001% by mass of the mixture prepared by dispersion, 2% by mass of medium chain fatty acid (MCT: manufactured by RIKEN Vitamin Co., Ltd.), and 4 mass% of glycerin fatty acid ester (manufactured by RIKEN Vitamin Co., Ltd.). Mass%, Saponin (manufactured by Maruzen Pharmaceutical Co., Ltd.) 0.5 mass%, Ethanol (manufactured by Nippon Alcohol Industry Co., Ltd.) 0.2 mass%, Martinol (manufactured by Hayashihara Co., Ltd.) 1.3 mass%, Glycerin A mixture of a lophenol compound (Compound 1) and a cyclolanostane compound (Compound 2) by mixing 78% by mass of (manufactured by Nichiyu Co., Ltd.) and further adding water so that the total amount is 100% by mass. Produced a syrup-like preparation containing 0.00002% by mass at the final concentration.
The pharmaceutical composition of Production Example 1 has an effect of improving resistance to ultraviolet rays.

[Manufacturing Example 2]
A food and drink composition having the following composition and having an ultraviolet resistance improving effect was produced by the following method.
A mixture containing a lophenol compound and a cyclolanostane compound in a mass ratio of lophenol compound: cyclolanostane compound = 6.1: 3.9 was contained in an amount of 4% by mass, and a medium-chain fatty acid (MCT) was also contained. : 2% by mass of Riken Vitamin Co., Ltd., 4% by mass of glycerin fatty acid ester (manufactured by Riken Vitamin Co., Ltd.), 0.5% by mass of saponin (manufactured by Maruzen Pharmaceutical Co., Ltd.), ethanol (manufactured by Nippon Alcohol Industry Co., Ltd.) 0. 2 mass%, Martinol (manufactured by Hayashihara Co., Ltd.) 1.3 mass%, glycerin (manufactured by Nichiyu Co., Ltd.) 78 mass%, and water 10 mass% are mixed to prepare a mixture of cyclolanostane compound and lophenol compound. The containing food additive was produced.

A food or drink composition containing 0.00002% by mass of a mixture of a lophenol compound (Compound 1) and a cyclolanostane compound (Compound 2) in a final concentration by adding the produced food additive to a beverage and uniformly mixing the mixture. Manufactured.
The food and drink composition of Production Example 2 has an effect of improving resistance to ultraviolet rays.

[Manufacturing Example 3]
<Cream>
A cream exhibiting the effect of improving resistance to ultraviolet rays was produced by the formulation shown below.
(Prescription)
(1) Stearic acid 5.0% by mass
(2) Stearyl alcohol 4.0% by mass
(3) Isopropyl millistate 18.0% by mass
(4) Glycerin monostearic acid ester 3.0% by mass
(5) Propylene glycol 10.0% by mass
(6) Cyclolanostane compound and lophenol compound mixture 0.0002% by mass
(7) Potassium hydroxide 0.2% by mass
(8) Sodium bisulfite 0.01% by mass
(9) Preservatives Appropriate amount (10) Fragrances Appropriate amount (11) Ion-exchanged water Residual

(Manufacturing method)
(5) to (7) were added to ion-exchanged water to dissolve them, and the mixture was heated and kept at 70 ° C. to prepare an aqueous phase portion. Further, apart from the aqueous phase portion, all the remaining components were mixed, heated and melted, and kept at 70 ° C. to prepare an oil phase portion. Next, the oil phase part was gradually added to the aqueous phase part, and after all the addition was completed, the temperature was kept at that temperature for a while, then uniformly emulsified with a homomixer, and cooled to 30 ° C. while mixing well to prepare a cream. ..

[Manufacturing Example 4]
<Emulsion>
With the formulation shown below, a milky lotion exhibiting the effect of improving resistance to ultraviolet rays was produced.
(Prescription)
(1) Stearic acid 2.5% by mass
(2) Cetyl alcohol 1.5% by mass
(3) Vaseline 5.0% by mass
(4) Liquid paraffin 10.0% by mass
(5) Polyoxyethylene (10 mol) monooleic acid ester 2.0% by mass
(6) Polyethylene glycol 1500 3.0% by mass
(7) Triethanolamine 1.0% by mass
(8) Carboxyvinyl polymer 0.05% by mass
(9) Cyclolanostane compound and lophenol compound mixture 0.00002 mass%
(10) Sodium bisulfite 0.01% by mass
(11) Ethylparaben 0.3% by mass
(12) Appropriate amount of fragrance (13) Residual ion-exchanged water

(Manufacturing method)
(8) was dissolved in a part of ion-exchanged water to prepare one liquid. Further, apart from the above 1 liquid, (6) and (7) were added to the remaining ion-exchanged water and dissolved by heating to prepare a 2 liquid at 70 ° C. In addition to the above 1st and 2nd liquids, all the remaining components were mixed and dissolved at 70 ° C. to obtain 3rd liquid. Then, after adding 3 liquids to 2 liquids, 1 liquid was further added thereto and uniformly emulsified with a homomixer, and after emulsification, the mixture was cooled to 30 ° C. while stirring well to prepare a milky lotion.

[Manufacturing Example 5]
With the formulation shown below, a sunscreen agent that exerts the effect of improving resistance to ultraviolet rays was produced.
<Sunscreen agent>
(Prescription)
(1) Cyclic silicon 21.9 mass%
(2) Zinc oxide 10.0% by mass
(3) Titanium oxide 10.0% by mass
(4) Dimethicone 5.5% by mass
(5) Octyl methoxycinnamate 5.5% by mass
(6) Glycerin 3.0% by mass
(7) Quotanium-18 bentonite 1.0% by mass
(8) Diglycerin 1.0% by mass
(9) Phenoxyethanol 0.1% by mass
(10) Cyclolanostane compound and lophenol compound mixture 0.00002% by mass
(11) Appropriate amount of fragrance (12) Methylparaben 0.1% by mass
(13) Ethanol 1.0% by mass
(14) 1,3-butylene glycol 3.0% by mass
(15) Residual ion-exchanged water

(Manufacturing method)
(1) to (11) were dispersed while stirring at room temperature to obtain a phase A. Water and 1,3-butylene glycol were stirred and dissolved at room temperature to prepare a B phase. Methylparaben and ethanol were stirred and dissolved at room temperature to prepare a C phase. While stirring the A phase with a disper, the B phase and the C phase were added and emulsified (1000 rpm, 3 minutes). Then, it was cooled to 35 ° C. while stirring with a paddle.

The cosmetic compositions of Production Examples 3 to 5 have an effect of improving resistance to ultraviolet rays.

The present invention can be used as a food or drink composition or a cosmetic composition for improving resistance to ultraviolet rays.

Claims (11)

A composition for improving ultraviolet resistance, which contains one or more compounds selected from the group consisting of a lophenol compound and a cyclolanostane compound as an active ingredient. The UV resistance according to claim 1, wherein the cyclolanostane compound is selected from the group consisting of 9,19-cyclolanostane-3-ol and 24-methylene-9,19-cyclolanostane-3-ol. Composition for improving sex. The lophenol compound consists of the group consisting of 4-methylcholest-7-en-3-ol, 4-methylergost-7-en-3-ol, and 4-methylstigmast-7-en-3-ol. The composition for improving UV resistance according to claim 1 or 2, which is selected. The composition for improving ultraviolet resistance according to any one of claims 1 to 3, which contains 0.00001% by mass or more of the compound in total. The composition for improving ultraviolet resistance according to any one of claims 1 to 4, which is used for preventing or ameliorating a skin condition or disease caused by exposing the skin to ultraviolet rays. The composition for improving ultraviolet resistance according to any one of claims 1 to 5, which is a food or drink composition or a cosmetic composition. The composition for improving ultraviolet resistance according to any one of claims 1 to 5, which is a pharmaceutical composition. The ultraviolet ray according to any one of claims 5 to 7, wherein the skin condition or disease is selected from erythema, edema, photokeratosis, precancerous tumor, sun dermatitis, photosensitivity and skin cancer. Composition for improving resistance. Use of a compound selected from the group consisting of lophenol compounds and cyclolanostane compounds in the production of compositions for improving UV resistance. A compound selected from the group consisting of lophenol compounds and cyclolanostane compounds used for improving UV resistance. A method for improving ultraviolet resistance, which comprises administering a compound selected from the group consisting of a lophenol compound and a cyclolanostane compound to a subject.

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