JP2010018559A - Cosmetic composition containing biosurfactant - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a cosmetic composition compounded with a vegetable extract containing a flavonoid-based or non-flavonoid-based secondary metabolic product, suitable as an external preparation for skin and having excellent stability, to provide a cosmetic composition, a quasi-drug composition, a medical supply composition, a sanitary good composition and a medicine composition which contain the cosmetic composition, and to provide a cosmetic, a quasi-drug, a medical supply, a sanitary good, and a medicine which contain the composition. <P>SOLUTION: The cosmetic composition is compounded with a biosurfactant and a vegetable extract containing a flavonoid-based or non-flavonoid-based secondary metabolic product. <P>COPYRIGHT: (C)2010,JPO&INPIT

Description

  The present invention relates to a cosmetic composition containing a plant extract containing a flavonoid or non-flavonoid secondary metabolite using a biosurfactant as a solubilizing agent, and a flavonoid or non-flavonoid secondary metabolite The plant extract containing is related to cosmetics, quasi-drugs, medical supplies, hygiene products, and pharmaceuticals, which are extracts from plants selected from Momijigasa, Wasabi, Horseradish, Cosmos, Nanko, and Garlic. More specifically, the biosurfactant includes mannosyl erythritol lipid (MEL) or mannosyl alditol lipid (MAL) containing alditol other than erythritol (MAL includes mannosyl mannitol lipid (MML), mannosyl sorbitol lipid (MSL), mannosyl arabitol lipid ( MAraL) and mannosyl ribitol lipid (MRL)).

Recently, attention has been paid to the biological function-adjusting action of secondary metabolites present in plants, and various useful components have been identified from plants and their relation to physiological functions has been investigated. Plant secondary metabolites are classified into three types, terpenoids having isoprene structures as basic units, phenolic compounds, and alkaloids of nitrogenous organic bases having various structures. Typical components include terpenoids, essential oils, saponins, cardiac glycosides, phenolic compounds, polyphenols, and alkaloids, which have a wide variety of chemical structures and have significant pharmacological effects. There are many things that have been done.
Among the secondary metabolites, polyphenol and the like have been recently attracting attention. Polyphenols are said to be 4000 or 5000 types, and are composed of those having a flavonoid skeleton or a non-flavonoid skeleton, and are classified into low molecular weight polyphenols and high molecular weight polyphenols (tannins) in terms of molecular weight. High-molecular polyphenols include proanthocyanidins, which are condensed tannins obtained by polymerization of catechins, and hydrolyzable tannins in which polyphenolcarboxylic acids and glucose are ester-bonded. High molecular weight polyphenols have a high molecular weight and a complex structure, and have been used in some complex systems as traditional medicines. Among them, proanthocyanidins, which are condensed tannins, are on the market. Regarding the physiological action of polyphenols in these plants, various actions such as a whitening action and an anti-inflammatory action are known centering on an antioxidant action (Non-patent Document 1).

  On the other hand, individual aging and the various diseases that accompany this are closely related to the aging of all cells that divide (decrease in division rate and cell function). For example, the skin is composed of epidermal cells, fibroblasts, and extracellular matrices such as elastin and collagen that support these extracellular skin structures. In young skin, moisture retention, flexibility, and elasticity are ensured by maintaining the constancy of the interaction between these skin tissues, and the skin has a firm and glossy appearance and is kept fresh. However, aging, ultraviolet rays, drying, stress, etc. cause deterioration of the function of the extracellular matrix and fibroblasts in particular. As a result, the skin's flexibility and moisturizing function are reduced, and the skin loses its tension and gloss and becomes rough. Aging symptoms such as wrinkles and dullness occur.

  For the purpose of developing anti-aging agents, search for antioxidants and the like has been conducted at the cellular level. For example, extracts such as Momijigasa (patent document 1), cosmos, soybean germ (patent document 2), and wheat germ (patent document 2) are known as plants.

  Ultraviolet light induces damage to cellular DNA. One of the causes of ultraviolet pigmentation is DNA damage and repair. That is, a substance such as thymidine dimer generated by DNA damage stimulates melanocytes and enhances tyrosinase activity. It is also clear from the fact that pigmentation is reported to occur when thymidine dimer-like substances are applied to guinea pig skin.

  Also, whitening agents from plants have been searched, for example, horseradish etc. are considered, but it is reported that extracts of horseradish containing antimutagenic substances show whitening action and antimutagenic action. Has been.

Sawa Wasabi and broccoli extracts contain methylsulfinyl-type isothiocyanate, which has a chemical carcinogenic inhibitory effect (Non-patent Documents 2, 3, and 4), and radish contains mail-thioalkyl isothiocyanate and is UV-induced. It has been reported that the action of repairing mutations (Non-Patent Document 5) and the Kyo vegetable extract have such an action (Non-Patent Documents 6, 7, and 8). On the other hand, horseradish phenethyl isothiocyanate has been reported to suppress chemical carcinogenesis (Non-patent Document 9) and to protect against ultraviolet damage (Patent Document 3).

Further, as a non-flavonoid plant secondary metabolite, “kacarol” is one of the representative Momijigasa extract components, and 5,6,7,8-tetrahydro-3,4,5-trimethylnaphtho [ 2,3-b] furan-9-ol structure.

  Momijigasa is also known as Sidke, Sidki, Sidkina, Shindoki, Kinoshita, Toukichi, Tokichina, Sudoke, Sitgi, Sudoke, and is widely distributed in the country and is eaten as a wild vegetable. A whitening effect is known for the extract of Japanese maple (Patent Document 4). Kakalol exists as one of the main components of the maple extract, and it is known that kakarol has an excellent antioxidant ability to suppress lipid peroxidation (Non-patent Document 10). As the physiological action of kakalol, antibacterial action (Non-patent Document 11) and blood glucose lowering action (Non-Patent Document 12) have been reported. As described above, the maple extract containing kakarol is expected to have various uses such as a whitening agent and an anti-aging agent.

  In this way, plant extracts contain flavonoid or non-flavonoid secondary metabolites, and although they exhibit useful physiological functions, flavonoids or non-flavonoid secondary metabolites have low water solubility. In many cases, it is insolubilized in cosmetics, which causes a decrease in the stability of the product, i.e., causes oliage.

On the other hand, a biosurfactant is an amphipathic lipid that is produced outside by a microorganism. In recent years, there has been a lot of interest in these new microorganism-derived materials against the backdrop of increasing production of plant resources due to the development of biotechnology and lowering costs of downstream processes due to advances in separation technology. Mannosyl erythritol lipid (MEL), a kind of biosurfactant, is a natural surfactant produced by yeast, and various physiological effects have been reported (Non-patent Document 13). Recently, mannosyl mannitol lipid (MML) in which erythritol is replaced with mannitol has been found (Patent Document 5). Use as an external preparation or cosmetic is useful as an anti-inflammatory agent and antiallergic agent (Patent Document 6), a hair nourishing / hair restoring agent (Patent Document 7), an antibacterial action (Patent Document 8), and a decrease in surface tension. The action (Patent Document 9) is known. Moreover, the effect (patent document 10) which MEL acts as a substitute of ceramide and improves rough skin is reported.

MEL includes 4-O-β-D-mannopyranosyl-meso-erythritol structure and 1-O-β-D-mannopyranosyl-meso represented by the following formula (1) as optical isomers of erythritol having a sugar skeleton. -An erythritol structure (the following formula (2)) exists.

However, by making these MEL and plant extracts containing flavonoid or non-flavonoid secondary metabolites coexist, a stable and highly flexible flavonoid or non-flavonoid secondary metabolite-containing skin external preparation can be obtained. The technology was not known.
FFI Journal, 212, 91, 2007 FFI Journal, 192, 27, 2001 Proc. Natl. Acad. Sci. US. , 91, 3147, 1994 Proc. Natl. Acad. Sci. US. , 99, 7610, 2002 J. et al. Agric. Food Chem. , 49, 5755, 2001 Environ. Mutagen Res. , 26, 259, 2004 Biosci. Biotechnol. Biochem. , 64, 2575, 2000 Biosci. Biotechnol. Biochem. , 62, 1161, 1998 Carcinogenesis, 21, 2287, 2000 Biosci. Biotechnol. Biochem. , 68, 1393, 2004 J. et al. Natural Prod. , 64, 432, 2001 J. et al. Natural Prod. , 62, 1088, 1999 J. et al. Biosci. Bioeng. , 94, 187, 2002 JP2007-217305A JP2007-291027 JP2007-31316A Japanese Unexamined Patent Publication No. 05-345705 JP 2005-104837 A JP 2005-68015 A JP 2003-261424 A JP-A-57-145896 JP-A-61-205450 WO2007 / 060956

Plant extracts contain flavonoid or non-flavonoid secondary metabolites, and despite their useful physiological effects, many flavonoid or non-flavonoid secondary metabolites have low water solubility, It is insolubilized in cosmetics, which causes a decrease in product stability, i.e., oliage. It is an object of the present invention to develop a solubilizing agent for preventing this orientation and preventing a decrease in the stability of the appearance of the product, and is a stable flavonoid or non-flavonoid secondary metabolite suitable as an external preparation for skin. It is providing the cosmetic composition etc. which mix | blended the plant extract containing this.
Furthermore, a cosmetic composition containing the cosmetic composition, a quasi-drug composition, a medical product composition, a hygiene product composition, a pharmaceutical composition, and a cosmetic, a quasi-drug, medical product, and hygiene containing the composition. It is to provide supplies and medicines.

As a result of diligent efforts to achieve the above object, the present inventors have sought a cosmetic composition containing a plant extract containing a stable flavonoid or non-flavonoid secondary metabolite, and biosurfactant, particularly MEL. MAL containing alditols other than erythritol (MAL includes mannosyl mannitol lipid (MML), mannosyl sorbitol lipid (MSL), mannosyl arabitol lipid (MAraL), mannosyl ribitol lipid (MRL)), triacyl MEL and triacyl It has been found that it is effective to contain MAL, and the present invention has been completed. That is, the present invention includes the following inventions.
(1) A cosmetic composition comprising a plant extract containing a biosurfactant and a flavonoid or non-flavonoid secondary metabolite.
(2) The cosmetic composition according to (1), wherein the biosurfactant has a mannose skeleton.
(3) The cosmetic composition according to (1) or (2), wherein the biosurfactant has a sugar alcohol linked to a glycoside bond to the hydroxyl group at the 1-position of the mannose skeleton.
(4) The biosurfactant having a mannose skeleton is selected from the group consisting of mannosyl erythritol lipid (MEL), mannosyl mannitol lipid (MML), mannosyl sorbitol lipid (MSL), mannosyl arabitol lipid (MAraL), and mannosyl ribitol lipid (MRL). The cosmetic composition according to (3), which is one or more selected compounds.
(5) MEL is mannosyl erythritol lipid A (MEL-A), mannosyl erythritol lipid B (MEL-B), mannosyl erythritol lipid C (MEL-C), mannosyl erythritol lipid D (MEL-D), or MEL-A. The cosmetic composition according to (4), which is one or more compounds selected from the group consisting of a triacyl body, a triacyl body of MEL-B, a triacyl body of MEL-C, and a triacyl body of MEL-D object.
(6) The cosmetic composition according to any one of (1) to (5), wherein the biosurfactant contains a saturated fatty acid and / or an unsaturated fatty acid.
(7) The cosmetic composition according to any one of (1) to (6), wherein the biosurfactant forms a lamellar structure and / or a liposome.
(8) The cosmetic composition according to (7), wherein the active ingredient which coexists is embedded in the lamellar structure formed by the biosurfactant and / or the liposome.
(9) The plant extract containing a flavonoid or non-flavonoid secondary metabolite is an extract from one or more kinds of plants selected from Momijigasa, Wasabi, Cosmos, wheat germ and soybean germ. The cosmetic composition according to any one of (1) to (8).
(10) The cosmetic composition according to any one of (1) to (9), which is used as a cosmetic, a quasi-drug, a medical product, a hygiene product, or a pharmaceutical product.

A cosmetic composition containing a plant extract containing a stable flavonoid or non-flavonoid secondary metabolite can be provided by the cosmetic composition containing the biosurfactant of the present invention. Can provide hygiene products, medicines. In addition, since biosurfactant is a biologically derived natural surfactant, it is excellent in safety, and the cosmetic composition according to the present invention has an effect that it can sufficiently withstand long-term use. Furthermore, since biosurfactants can be produced by culturing microorganisms, raw material costs are low, and mass production is possible. Therefore, the cosmetic composition according to the present invention has an effect that it can be provided at a low price. The biosurfactant may be used as a premix product.

  A cosmetic composition containing biosurfactant has both cleansing properties, moisturizing effect, collagen production promoting effect, cell activation effect, anti-aging effect, hair growth and skin roughening effect, vesicle formation and liquid crystal form performance, etc. It is also useful as a cosmetic ingredient.

(Biosurfactant)
“Biosurfactant” is a general term for substances having surface-active ability and emulsifying ability produced by living organisms, and not only exhibits excellent surface activity and high biodegradability, but also has various physiological functions. Therefore, there is a possibility of developing different behaviors and functions from synthetic surfactants. Biosurfactants can be produced in large quantities by culturing microorganisms and may be used as premixed products.

  A “premix product” is a product obtained by adding a dispersing agent or the like in addition to a functional material, or diluting with a solvent so that it can be easily used during cosmetic production.

  Examples of biosurfactants include mannosyl erythritol lipid (MEL), mannosyl alditol lipid (MAL) (for MAL, mannosyl mannitol lipid (MML), mannosyl sorbitol lipid (MSL), mannosyl arabitol lipid (MAraL), mannosyl ribitol lipid (MAL). MRL)), trehalose lipids, rhamnolipids, sophorolipids, surfactins, spiculsporic acid, emalzan and the like, and any of them can be used as the activator according to the present invention. Among these, it is preferable to use a biosurfactant that forms a lamellar structure, and MEL and MAL are particularly preferable. These biosurfactants may be either a mixture of fermented products, a purified product or a lamellar structure.

(MEL)
MEL is classified into four types, MEL-A, MEL-B, MEL-C, and MEL-D, based on the presence or absence of acetyl groups at the 4-position and 6-position of mannose. Formula (3) shows the structure of MEL-A. In formula (3), R1 and R2 represent a hydrocarbon group. That is, MEL-A is a compound having an alkanoyl group having 6 to 20 carbon atoms at the 2nd and 3rd positions of mannose and the acetyl group at the 4th and 6th positions of mannose in formula (3). In MEL-B, mannose 4-position acetyl group (CH ₃ CO) in formula (3) is H, and MEL-C is mannose 6-position acetyl group (CH ₃ CO) in formula (3). H and MEL-D is H in the acetyl group (CH ₃ CO) at the 4-position and 6-position of mannose in the formula (3).

[R ¹ and R ² are the same or different and each represents a hydrogen atom or an alkyl group having 1 to 18 carbon atoms, preferably 2 to 16 carbon atoms, more preferably 4 to 12 carbon atoms having a straight chain or a branched chain, or An alkenyl group, alkadienyl group or alkatrienyl group having a straight chain or branched chain having 2 to 18 carbon atoms, preferably 2 to 16 carbon atoms, more preferably 2 to 14 carbon atoms. ]

According to the formula (3), MEL is a saturated or unsaturated straight chain having 1 to 19, preferably 1 to 17, more preferably 1 to 15 carbon atoms at the 2nd and 3rd positions of mannose. Alternatively, it is a compound having a branched alkanoyl group and the mannose 4th and 6th positions are acetyl groups (one of the mannose 4th and 6th acetyl groups, or both are hydroxyl groups). It is good.) The total number of carbon atoms of the 2nd and 3rd alkanoyl groups is preferably 10 to 38, more preferably 14 to 30.

Preferable groups for R ¹ and R ² include C _{7 to} C ₁₁ alkyl groups such as CH ₃ (CH ₂ ) ₆ , CH ₃ (CH ₂ ) ₈ , and CH ₃ (CH ₂ ) ₁₀ . MEL-A of R ^1, R ² is an alkyl group of C ₇ -C ₁₁ Formula (3), myristic acid, palmitic acid, stearic acid, oleic acid or an ester (mono alkyl ester, mono -, di - , Tri-glyceride, or fats and oils containing these saturated or monounsaturated fatty acids) and the like can be obtained by adding them to the medium. Similarly, MEL-A of the formula (3) in which R ¹ and R ² are an alkenyl group, an alkadienyl group or an alkatrienyl group is a linoleic acid, linolenic acid, arachidonic acid having two or more double bonds as a raw material. It can be obtained by adding raw materials such as esters (monoalkyl esters, mono-, di-, tri-glycerides, oils and fats containing these highly unsaturated fatty acids, etc.) to the medium. Preferred alkanoyl groups represented by R ¹ and R ² include C _{7 to} C ₁₁ alkenyl groups such as C ₇ H ₁₄ , C ₉ H ₁₈ , and C ₁₁ H ₂₂ . Preferable alkadienyl groups represented by R ¹ and R ² include C _{7 to} C ₁₁ alkadienyl groups such as C ₇ H ₁₂ , C ₉ H ₁₆ , and C ₁₁ H ₂₀ . Preferable alkatrienyl groups represented by R ¹ and R ² include C _{7 to} C ₁₁ alkatrienyl groups such as C ₇ H ₁₀ , C ₉ H ₁₄ , and C ₁₁ H ₁₈ .

  The structure of MAL other than MEL is shown in Formula (4) (wherein either one or both of the acetyl groups at the 4th and 6th positions of mannose may be hydroxyl groups). Mannitol, arabitol, ribitol, and sorbitol are added as sugar alcohols (alditol) other than erythritol (n = 4: mannitol, sorbitol, n = 2: arabitol, ribitol). According to the formula (4), MAL is a saturated or unsaturated straight chain having 2 to 20 carbon atoms, preferably 4 to 18 carbon atoms, more preferably 6 to 14 carbon atoms at the 2nd and 3rd positions of mannose. Alternatively, it is a compound having a branched alkanoyl group and the mannose 4th and 6th positions are acetyl groups (wherein either one of the mannose 4th and 6th acetyl groups, or both are hydroxyl groups) It may be.)

[R ¹ and R ² are the same or different and each represents a hydrogen atom or an alkyl group having 1 to 18 carbon atoms, preferably 2 to 16 carbon atoms, more preferably 4 to 12 carbon atoms having a straight chain or a branched chain, or An alkenyl group, alkadienyl group or alkatrienyl group having a straight chain or branched chain having 2 to 18 carbon atoms, preferably 2 to 16 carbon atoms, more preferably 2 to 14 carbon atoms. ]

(Triacyl derivative)
The biosurfactant used in the present invention may be MEL triacyl and MAL triacyl other than MEL. The triacyl biosurfactant is a biosurfactant having higher hydrophobicity than MEL or MAL other than MEL. For example, it also exists in the culture solution of MEL-producing bacteria, and when it is obtained in a large amount, it can be produced by reacting MEL with various vegetable oils using enzymes.

  The triacyl form of MEL, that is, triacyl mannosyl erythritol lipid (sometimes referred to as triacyl MEL) has a structure represented by the formula (5).

  In the formula (5), R1, R2 and R3 each independently represent a hydrocarbon group or an oxygen atom-containing hydrocarbon group, and one or both of the hydroxyl groups at the 4-position and 6-position of mannose are acetylated. It may be substituted with a group. The hydrocarbon group may have only a saturated bond or may have an unsaturated bond. When it has an unsaturated bond, it may have a plurality of double bonds. The carbon chain may be linear or branched. In the case of an oxygen atom-containing hydrocarbon group, the number and position of oxygen atoms contained are not limited.

  In the formula (5), R1 and R2 preferably have 1 to 18 carbon atoms, and have an ester bond with the hydroxyl groups at the 2- and 3-positions of mannose as the aliphatic acyl group (RCO-), An acetyl group may be ester-bonded to the hydroxyl group. R3 is preferably an aliphatic acyl group having 2 to 20 carbon atoms, and has an ester bond with the primary hydroxyl group of erythritol as an aliphatic acyl group (RCO-).

  Triacyl MEL has a structure in which a fatty acid ester is added and has high hydrophobicity, and therefore is superior as an emollient in that it can be easily combined with various oil components as compared with conventional MEL.

These biosurfactants may be used alone, or two or more biosurfactants can be used in combination.

(Biosurfactant production method)
The method for producing the biosurfactant is not particularly limited, and a fermentation method using microorganisms may be arbitrarily selected. For example, culture production of MEL (MEL-A, MEL-B, MEL-C) can be produced by Pseudozyma antarctica NBRC 10736 according to a conventional method, and Pseudozyma antarctica, Pseudozyma sp., Etc. can be used as microorganisms. . It is a well-known fact that an MEL mixture can be easily obtained with any microorganism. The MEL mixture can be purified using silica gel column chromatography to isolate MEL-A, MEL-B and MEL-C. Moreover, Pseudozyma antarctica and Pseudozyma tsukubaensis, Kurzmanomycessp are known as bacteria producing MEL-B, and these bacteria may be used. Pseudozyma hubeiensis and Pseudozyma graminicola are known as bacteria that produce MEL-C, and these bacteria may be used. The microorganism having the ability to produce MEL is not particularly limited, and can be appropriately used depending on the purpose.

  Fermentation media for producing biosurfactants are generally composed of N sources such as yeast extract and peptone, C sources such as glucose and fructose, and inorganic salts such as sodium nitrate, dipotassium hydrogen phosphate and magnesium sulfate heptahydrate. A medium with a typical composition can be used, including oils and fats such as olive oil, soybean oil, sunflower oil, corn oil, canola oil and coconut oil, and water-insoluble substrates such as hydrocarbons such as liquid paraffin and tetradecane. These can be used alone or in combination of two or more.

  Fermentation conditions such as pH and temperature, culture time, and the like can be arbitrarily set, and the culture solution after fermentation can be used as it is as the biosurfactant of the present invention. In addition, it is possible to appropriately add any operation such as filtration, centrifugation, extraction, purification, sterilization and the like to the culture solution after fermentation, and the obtained extract can be diluted, concentrated and dried. .

  As oils and fats used as raw materials, vegetable oils and fats are preferable. Vegetable fats and oils are not particularly limited, and can be appropriately selected according to the purpose. For example, soybean oil, rapeseed oil, corn oil, peanut oil, cottonseed oil, safflower oil, sesame oil, olive oil, palm oil, etc. Among them, soybean oil and olive oil are biosurfactants (especially MEL) production efficiency (production amount) , Production rate, and yield) are particularly preferable. These may be used alone or in combination of two or more.

  There is no restriction | limiting in particular as an inorganic nitrogen source, Although it can select suitably according to the objective, For example, ammonium nitrate, urea, sodium nitrate, ammonium chloride, ammonium sulfate, etc. are mentioned.

  There are no particular limitations on the method for recovering and purifying the biosurfactant, and it can be appropriately selected according to the purpose. For example, it can be recovered by centrifuging the culture solution to recover the oil, and extracting and concentrating with an organic solvent such as ethyl acetate.

Examples of the extraction solvent include water, alcohols (for example, lower alcohols such as methanol, absolute ethanol, and ethanol, or polyhydric alcohols such as propylene glycol and 1,3-butylene glycol), ketones such as acetone, diethyl ether, and dioxane. , Esters such as acetonitrile and ethyl acetate, and organic solvents such as xylene, benzene, and chloroform can be used alone or in any combination of two or more kinds, and each solvent extract is combined. Can also be used.

  There are no particular limitations on the extraction method, but usually it may be in the range of the boiling point of the solvent from room temperature to normal pressure. After extraction, it is filtered or adsorbed, decolored and purified using an ion exchange resin to form a solution. , Paste, gel, and powder. In many cases, it can be used as it is, but if necessary, further purification treatment such as deodorization and decolorization may be added as long as the effect is not affected. As a purification treatment means such as deodorization and decolorization, an activated carbon column or the like may be used, and a normal means generally applied depending on the extracted substance may be arbitrarily selected. If necessary, a high-purity biosurfactant can be obtained by purification using a silica gel column.

(Triacyl production method)
A method for obtaining a biosurfactant triacyl form will be described by taking a method for producing a MEL triacyl form as an example, but the biosurfactant triacyl form used in the present invention is not limited to a triacyl MEL.

  For example, in order to obtain a triacyl MEL, a triacyl MEL fraction can be purified from a culture solution produced by fermenting a microorganism as described above. In order to obtain a large amount, MEL is dissolved in an organic solvent, a fatty acid derivative such as vegetable oil is added, and esterification or transesterification is performed in the presence of a hydrolase.

  The fatty acid introduced into the erythritol part of MEL may be a long-chain hydrocarbon monovalent carboxylic acid. Further, it may be a saturated fatty acid or an unsaturated fatty acid. In the case of an unsaturated fatty acid, it may have a plurality of double bonds. The carbon chain may be linear or branched. Furthermore, a fatty acid derivative that is a derivative of a fatty acid may be used in the present invention, or a mixture of a fatty acid and a fatty acid derivative may be used in the present invention. The fatty acid or fatty acid derivative introduced into the erythritol part of MEL is preferably derived from oils, higher fatty acids, and synthetic esters.

  The “oils” may be vegetable oils, animal oils, mineral oils, and hardened oils thereof. Specifically, avocado oil, olive oil, sesame oil, camellia oil, evening primrose oil, turtle oil, macadamian nut oil, corn oil, mink oil, rapeseed oil, egg yolk oil, persic oil, wheat germ oil, sasanqua oil, castor oil , Linseed oil, safflower oil, cottonseed oil, eno oil, soybean oil, peanut oil, tea seed oil, kaya oil, rice bran oil, kiri oil, jojoba oil, cacao butter, palm oil, horse oil, palm oil, palm kernel oil Animal and vegetable oils such as beef tallow, sheep fat, pork tallow, lanolin, whale wax, beeswax, carnauba wax, molasses, candelilla wax, squalane and their hardened oils. Examples thereof include mineral oil such as liquid paraffin and petrolatum, and synthetic triglycerin such as glycerin tripalmitate. Preferably avocado oil, olive oil, sesame oil, camellia oil, evening primrose oil, turtle oil, macadamia nut oil, corn oil, mink oil, rapeseed oil, egg yolk oil, persic oil, wheat germ oil, southern oil, castor oil, flaxseed oil , Safflower oil, cottonseed oil, eno oil, soybean oil, peanut oil, tea seed oil, kaya oil, rice bran oil, and more preferably olive oil and soybean oil.

  Examples of the “higher fatty acid” include caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, oleic acid, linoleic acid, linolenic acid, stearic acid, behenic acid, 12-hydroxystearic acid, isostearic acid, Examples include undecic acid, tolic acid, eicosapentaenoic acid, docosahexaenoic acid, and the like. Preferred are lauric acid, myristic acid, palmitic acid, oleic acid, linoleic acid, linolenic acid, stearic acid and undecylenic acid, and more preferred are oleic acid, linoleic acid and undecylenic acid.

  Examples of the “synthetic ester” include methyl caproate, methyl caprylate, methyl caprate, methyl laurate, methyl myristate, methyl palmitate, methyl oleate, methyl linoleate, methyl linolenate, methyl stearate, undecine. Methyl acid, ethyl caproate, ethyl caprylate, ethyl caprate, ethyl laurate, ethyl myristate, ethyl palmitate, ethyl oleate, ethyl linoleate, ethyl linolenate, ethyl stearate, ethyl undecinate, vinyl caproate , Vinyl caprylate, vinyl caprate, vinyl laurate, vinyl myristate, vinyl palmitate, vinyl oleate, vinyl linoleate, vinyl linolenate, vinyl stearate, vinyl undecinate, cetyl octanoate , Octyldodecyl myristate, isopropyl myristate, myristyl myristate, isopropyl palmitate, butyl stearate, hexyl laurate, Oren'i acid decyl dimethyl octanoate, cetyl lactate, myristyl lactate, and the like. Preferred are methyl laurate, methyl myristate, methyl palmitate, methyl oleate, methyl linoleate, methyl linolenate, methyl stearate, methyl undecylate, more preferably methyl oleate, methyl linoleate, and methyl undecylate. .

  Triacyl MEL can be produced by dissolving MEL in an organic solvent and reacting as described above. The organic solvent is not limited as long as it can solubilize MEL. What is necessary is just to be able to solubilize a part even if not all can be solubilized. The organic solvent may be a mixture of a plurality of organic solvents. Specifically, for example, methanol, ethanol, propanol, butanol, acetone, propanone, butanone, pentan-2-one, 1,2-ethanediol, 2,3-butanediol, dioxane, acetonitrile, 2-methyl-butane -2-ol, tertiary butanol, 2-methylpropanol, 4-hydroxy-2-methylpentanone, tetrahydrofuran, hexane, DMF, DMSO, pyridine, methyl ethyl ketone and the like. Acetone, tetrahydrofuran, tertiary butanol, acetonitrile and dioxane are preferable, and acetone is more preferable.

  Examples of hydrolases include lipases, proteases, and esterases. It is preferable to use at least one selected from these, and a plurality of hydrolases may be used. Lipase and esterase are preferable, and lipase is more preferable.

  Specifically, for example, MEL purified from a culture solution of MEL-producing microorganisms is dissolved in an organic solvent (for example, acetone), and commercially available lipase (for example, Novozyme 435 (manufactured by Novozymes) etc.) and vegetable oils and fats are dissolved therein. Added.

  In the case of this production method, the reaction temperature is 10 to 100 ° C., preferably 20 to 50 ° C., more preferably 25 to 40 ° C., and stirring may be performed for 1 to 7 days. Further, molecular sieves may be added to the reaction solution. By this manufacturing method, MEL added as a material becomes a triacyl body almost quantitatively.

  The purification of triacyl MEL can be performed according to the above-described purification of MEL.

(Method for producing MEL having saturated fatty acid side chain)
MEL having a saturated side chain can be produced in accordance with the above-described method for producing biosurfactant. At that time, as the fats and oils used as a raw material, it is carried out by adding one or more water-insoluble substrates such as olive oil, saturated fatty acids or esters thereof, hydrocarbons such as liquid paraffin and tetradecane.
The MEL having a saturated side chain can be purified according to the above-described MEL purification.

(Manufacturing method of MAL such as MML)
The production of MAL having alditol other than erythritol, such as MML, can be carried out according to the above-described method for producing biosurfactant. In that case, as a raw material, it carries out by adding alditol, such as mannitol, arabitol, ribitol, sorbitol, alone or in combination.
Purification of MAL having an alditol other than erythritol such as MML can be performed according to the above-described purification of MEL.

(Method for obtaining liposome)
Biosurfactants may be dissolved in oil-soluble bases or oil-soluble ingredients and blended into cosmetics, and are preferably blended in the form of liposomes in cosmetics, particularly water-based cosmetics such as lotions and moisturizing liquids. . Biosurfactants blended in liposomes are preferable because they are fused with skin cells to improve absorbability. As a method for preparing the liposome, any known preparation method may be adopted, and it is not particularly limited. Examples thereof include an ethanol injection method and a bangham method.

For example, the preparation of the MEL-B liposome solution by the ethanol injection method may be performed as follows. That is, 10 mg of MEL-B is dissolved in 0.5 ml of ethanol, 1 ml of distilled water previously warmed to around 70 ° C. is added and lightly shaken, and then the remaining ethanol is distilled off with a rotary evaporator. This may be sonicated for about 5 minutes using a water bath type ultrasonic device (W-220R, Honda Electronics Co., Ltd.) and then diluted with distilled water.

For example, the preparation of the MEL-B liposome solution by the Bangham method may be performed as follows. That is, 10 mg of MEL-B may be dissolved in 1 ml of chloroform, and the solvent may be distilled off with a rotary evaporator to form a thin film. What is necessary is just to add 1 ml of distilled water there and sonicate for about 5 minutes using a water bath type ultrasonic device (W-220R, Honda Electronics Co., Ltd.).

(Method for producing cosmetic composition containing biosurfactant)
The addition amount of the biosurfactant in the cosmetic composition may be added in a range that does not impair the action of stabilizing the flavonoid or non-flavonoid secondary metabolite in which the biosurfactant is stable, and usually 0.001 to 50% by mass Is preferable, 0.01-25 mass% is more preferable, 0.05-15 mass% is further more preferable, and 0.01-10 mass% is especially preferable. Here, the use form of the biosurfactant added to the cosmetic composition is arbitrary. For example, the biosurfactant may be used as it is as an extract from the culture solution, or after being purified, purified or suspended in water, or dissolved in an organic solvent such as ethanol.

Plant extracts containing biosurfactants and flavonoid or non-flavonoid secondary metabolites include soybean germ extract, wheat germ extract, cosmos extract, maple extract, horseradish (leaf and rhizome) extract, Acerola extract, Ages extract, Fire bud extract, Chamomile extract, Chamomile flower extract / (Urea), Kiwi extract, Rumor extract, Arnica extract, Ogon extract, Sowakuhi extract, Psycho extract, Bow fu extract, Manntake mycelium culture or its extraction , Linden extract, peach leaf extract, ages extract, cucumber extract, jujube extract, toki extract, yokuinin extract, oyster leaf extract, daiou extract, button pi extract, hamamelis extract, malonie extract, hypericum extract, oil-soluble licorice , Fennel extract, Dutch mustard extract, saffron extract, ginseng extract, carrot extract, carrot extract, chimpi extract, cypress root extract, dodami extract, button extract, litchi extract, merilot extract, gypsum extract, genochocolate extract, Arnica extract, Arnica flower extract, Auren extract, Odrianthus extract, Catfish ear extract, Chamomile extract, Calamine, Kawaramugi extract, Licorice extract, Gardenia extract, Kumazasa extract, Gentiana extract, Black tea extract, Comfrey extract, Comfrey leaf extract, Shikon extract , Purple root extract, perilla extract, perilla leaf extract, shimotake extract, peony extract, honeysuckle extract, sage extract, kizuta extract, chickpea Extract, Achillea millefolium extract, Assembly extract, Sakuhakhi extract, Toki-senka extract, Biwa leaf extract, Fuyubodaiju extract, Peach fruit extract, Cornflower extract, Yukinoshita extract, Artemisia extract, Lettuce extract, Roman chamomile extract, Walnut extract , Jiou extract, Tychou extract, Gypsophila extract, Kidachi aloe extract, Burdock extract, Arnica extract, Arnica extract, Asparagus extract, Ashitaba extract, Amachiya extract, Altea extract, Aloe vera extract, Oyster extract, Barley extract, Brown algae extract, Karin extract, Raspberry extract, cucumber extract, cucumber fruit extract, guava confection extract, quince seed extract, grapefruit extract, grapefruit Fruit extract, clematis extract, hawthorn extract, shiitake extract, horsetail extract, mallow extract, tomato extract, wild rose extract, fukuno extract, loofah extract, lily extract, apple extract, forsythia extract. Herbal medicine extracts and extracts include Asen Yaku (Asen Yaku), Altea, Arnica, Avocado, Achacha (Amacha), Nettle, Ginkgo (Ginkgo Leaves, Ginkgo), Usba Saishin (Spicy), Ume (Plum), Vulgaris, Snorkele, Neubara (fruit), Hikikoshi (life-prolonging grass), Ogi (yellow tuna), Yamazakura (cherry bark), yellowfin (yellow tuna), Ouren (yellow ream), Panax ginseng (carrot), Hypericum perennial (brother cut grass), Odrichosium, Dutch garashi , Orange, Itohimehagi (distant), eel-brush (summer hay), tsurugokudami (what neck 烏), Enju (槐花), gadget (莪 朮), kudu (kuzukone), valerian (valerian), chamomile, kikarasuuri (Gurone) , Fukidan popo (section winter flower, winter winter leaf), raspberry, yellow bellflower (kikyo), chrysanthemum (flower chrysanthemum), cattle bean (fruit) Genus plant fruit (fruit), tachibana (tachibana bark), Udo or Shishido (clam, lively), apricot (apricot kernel), wolfberry (earthbone bark, coconut, coconut leaf), Clara (bitter ginseng), camphor, kumazasa , Nikkei, Keigai, Ebisugusa (Keriko), Maruba asagao or Asagao (ken beef), safflower (safflower), gobaishi (penta), comfrey, copaiba, gardenia, gentian, honoki (thick) Pak), Hinata Taikozuchi (cow knee), Goshuyu (Kurei), Korean ginger (Gomiko), Rice, Rice bran, Mishima Saiko (Saiko), Saffron, Sabonso, Salamander (Samurai), Salvia, Sancychin carrot (37) Carrots), shiitake (shiitake), shikunshi (messoon prince), purple (purple), oysters (salmon), peonies (glaze), psyllium (car front child, Antecedents), Ginger (Ginger), Shobu (Sardine), Scotch Mochi (Sadako), Shimosukeso, Birch, Honeysuckle (Gin Silver Flower, Shinobi), Ivy, Achillea millefolium, Elderberry, Azuki (Red Azuki), Elderberry Tree), mallow, senkyu (river cucumber), sea bream (this medicine), mulberry (mulberry white skin, mulberry leaf), jujube (large cocoon), soybean, taranki, chikutsutsujinjin (bamboo ginseng), hanasuge (knowing mother) , Walnut mushroom (butterfly), dokudami (ten medicines), fuyusuminatsusakutake (clover insects), red pepper, physalis (Torone), prickly pear, ryokcha (green tea), kocha (tea), clove (chome), unshimikan Chen), camellia, camellia, pearl millet, daidai (orange peel), bitumen (corn), corn ( Washi), Tochu (Tochu, Tochu), Nanten (Minami Tenmi), Garlic (Daisan), Hakusen (White Birch), Janohige (Wat Gate Winter), Parsley, Batata, Pepper (Thick), Hamamelis, Rose , Loquat leaves, pine pods, grapes or their leaves, bodaiju, hops, maikai (my buds), pine needles, marronnier, mannenrou, mukuroji, melissa, melirote, bokeh (tree cocoons), coconut palm, halibut (Dried), areca (bamboo shoot), pheasant (beneficial herb), cornflower, saxifrage (tiger ear grass), bayberry (bamboo ume), yachabushi (yarrow), mugwort, sagebrush, lavender, apple fruit, ganoderma , Lemon fruit, forsythia, forsythia, genus shochu (old lady's grass), ashridokoro (roth root), etc. Can be mentioned.

  The addition amount of the plant extract is usually preferably 0.0001 to 10% by mass, more preferably 0.001 to 5% by mass, further preferably 0.01 to 1% by mass, and 0.05 to 0.5% by mass. Is particularly preferred. Here, the usage form of the plant extract added to the cosmetic composition is arbitrary. For example, it may be used in the form of a solution or powder.

(Method of using cosmetic composition containing biosurfactant)
The form of the cosmetic composition characterized by blending a plant extract containing a biosurfactant and a flavonoid or non-flavonoid secondary metabolite is not particularly limited. Therefore, it may take any state such as solid, liquid, paste, jelly, and powder. In order to form such a state, it can be solidified using, for example, a gelling agent, or can be dispersed using a liquid. Moreover, a solvent can be added to make a solution, or it can be spray-dried to form a powder.

The cosmetic composition characterized by blending the biosurfactant of the present invention with a plant extract containing a flavonoid or non-flavonoid secondary metabolite has an excellent moisturizing effect and rough skin preventing effect, etc. It has been confirmed that the skin surface is moderately moisturized to maintain smoothness, and that vesicle formation and liquid crystal type performance are achieved. That is, the cosmetic composition comprising the biosurfactant of the present invention and a plant extract containing a flavonoid or non-flavonoid secondary metabolite has a stability that prevents the insolubility of poorly soluble substances such as polyphenols. The object is to provide a high external preparation for skin. Therefore, a cosmetic composition comprising the biosurfactant of the present invention and a plant extract containing a flavonoid or non-flavonoid secondary metabolite is required to improve rough skin, improve keratin or protect the skin. Can be used extremely effectively.

For example, a cosmetic composition comprising the biosurfactant of the present invention and a plant extract containing a flavonoid or non-flavonoid secondary metabolite can be used as a cosmetic. For example, cosmetic soap, shampoo, facial cleanser, rinse, eye cream, eye shadow, cream / milky lotion, lotion, perfume, funny, cosmetic oil, hair cosmetic, hair dye, perfume, powder, pack, cleansing cream, shaving Cream, beard shave lotion, suntan oil, sunscreen oil, sunscreen lotion, sunscreen lotion, suntan cream, sunscreen cream, foundation, powdered perfume, blusher, mascara, eyebrow, nail cream, beautiful nail enamel, beautiful nail enamel It can be used as a remover, hair wash, bath cosmetic, lipstick, lip balm, eyeliner, toothpaste, deodorant, eau de cologne, hair nourishing agent, and hair restorer. Moreover, the cosmetic composition characterized by blending the biosurfactant of the present invention with a plant extract containing a flavonoid or non-flavonoid secondary metabolite can also be used as an ointment or poultice.

The cosmetic composition containing a flavonoid or non-flavonoid secondary metabolite using the biosurfactant of the present invention as a solubilizer contains a whitening agent, an anti-aging agent, a moisturizing agent depending on the purpose of use. Various components such as an agent, an ultraviolet absorber and an antibacterial agent can be further added.

(Whitening agent)
The whitening agent may be a melanin production inhibitor and / or a tyrosinase activity inhibitor.

Examples of whitening agents include L-ascorbic acid and its derivatives, hydroquinone and its derivatives, lucinol, edetic acid and its derivatives, placenta extract, t-AMCHA, and the like.

These whitening agents can be used alone or in combination of two or more.

(Anti-aging agent)
The anti-aging agent may be an anti-inflammatory agent and / or an antioxidant.

For example, anti-inflammatory agents and antioxidants are used as anti-aging agents. Anti-inflammatory agents include glycyrrhizic acid and its salts, glycyrrhetinic acid and its salts, isopropylaminocaproic acid and its salts, allantoin, lysozyme chloride, guaiazulene, salicylic acid. Examples of methyl, γ-oryzanol, and antioxidants include carotenoids such as α-carotene, β-carotene, γ-carotene, lycopene, cryptoxanthine, lutein, zeaxanthin, isozeaxanthin, rhodoxanthine, capsanthin, and crocetin; 1,4-diazacyclo Octane, 2,5-dimethylfuran, 2-methylfuran, 2,5-diphenylfuran, 1,3-diphenylisobenzofuran, α-tocopherol, β-tocopherol, γ-tocopherol, d-tocopherol, histidine, tryptophan, Thionine, alanine or alkyl esters thereof; dibutylhydroxytoluene, butylhydroxyanisole, ascorbic acid, tannic acid, epicatechin, epicacatechin, epicatechin gallate, tannins such as rucaine, flavonoids such as rutin, and other gallic acids Propyl, astaxanthin, carotene, tocopherol, ascorbic acid, tetrasodium edetate, erythorbic acid, tocopherol acetate, retinol acetate, dibitylhydroxytoluene, ascorbyl stearate, ascorbyl palmitate, methylsilanol dioletocopherol / silicic acid mixture, nicotine Benzyl acid, photosensitizer 401, aspartic acid, adenosine triphosphate 2Na, aminobutyric acid, caffeine, chlorella extract, folic acid, Tinol, retinol palmitate, inositol, turmeric extract, oryzanol, carotene, ergocalciferol, pyridoxine dicaprylate, batyl alcohol, glycyrrhetinyl stearate, glycyrrhizic acid, glycyrrhetinic acid, diphenhydramine hydrochloride, lysozyme chloride, aminocaproic acid, glycyrrhetinic acid 2K Examples include acid stearyl, methyl salicylate, zinc oxide, and the like.

These anti-aging agents can be used individually by 1 type or in combination of 2 or more types.

(Humectant)
The moisturizing agent may be a hydrophilic moisturizing agent and / or a lipophilic moisturizing agent. As the hydrophilic moisturizing agent, amino acids, peptides, proteins, higher alcohols and derivatives thereof, and as the lipophilic moisturizing agent, phospholipid, sugar. Lipids and steroids may be used.

  As moisturizer, sodium pyridonecarboxylate, glycol, glycerin, glucose, maltose, maltitol, sucrose, fructose, xylitol, sorbitol, maltotriose, threitol, erythritol, amylolytic sugar-reducing alcohol, sorbitol, polyhydric alcohols Is ethylene glycol, 1,4-butylene glycol, diglycerin, triglycerin, tetraglycerin, 1,3-butylene glycol, propylene glycol, dipropylene glycol, polyethylene glycol, 1,3-propanediol, other serine, glycine, Threonine, alanine, collagen, hydrolyzed collagen, hydronectin, fibronectin, keratin, elastin, royal jelly, chondroitin sulfate hepa Glycerophospholipid, glyceroglycolipid, sphingophospholipid, sphingoglycolipid, linoleic acid or its esters, eicosapentaenoic acid or its esters, pectin, bifidobacteria fermentation product, lactic acid fermentation product, yeast extract, litchi mycelium Culture or extract thereof, soybean phospholipid, γ-oryzanol, pyrrolidone carboxylic acid, camellia oil, soybean phospholipid, hyaluronic acid, threonine, ammonium glycolate, methyl silanol alginate, yoquinin, DNA-Na, PCA-Na, RNA- Na, aspartic acid, alanine, arginine, sodium alginate, hydrolyzed keratin, hydrolyzed collagen, hydrolyzed conchiolin, hydrolyzed egg shell membrane, hydrolyzed egg white, hydrolyzed silk, hydrolyzed soy protein, xylitol, chitosan, glycine, glycerin, Gluco , Chondroitin sulfate Na, fish collagenase, glycerin, cystine, cysteine, serine, sorbitol, soy protein, tomato extract, lactate Na, lactobacilli, urea sulphate / novara extract almond meal, corn oil, honey, sodium hyaluronate , Betaine, loofah extract, maltitol, maltose, mannitol, lactoferrin, lysine, royal jelly, lanolin fatty acid polyethylene glycol 1000, lanolin fatty acid isopropyl, isopropyl myristate, isobutyl myristate, hexyldecanol, myristyl lactate, lanolin fatty acid, tricaprylglyceryl, oleyl Alcohol, octyldodecyl oleate, decyl oleate, reduced lanolin, octyldodecanol, almond oil, avocado oil, olive oil, oleic acid, Orange rough oil, cacao butter, carrot extract, sesame oil, sasanqua oil, safflower oil, dihydrocholesterol, squalane, cholesteryl stearate, ceramide 2, evening primrose oil, sunflower oil, sunflower oil, cefnide 3, sunflower seed oil hybrid sunflower oil Phytosphingosine, grape seed oil, jojoba oil, jojoba seed oil, mineral oil, mink oil, macadamia nut oil, meadow foam oil, yuri oil, eucalyptus leaf oil, lanolin, linoleic acid, rosehip oil, petrolatum and polyglutamic acid Illustrated.

These humectants can be used alone or in combination of two or more.

(UV absorber)
As UV absorbers, use benzoic acid UV absorbers, anthranilic acid UV absorbers, salicylic acid UV absorbers, cinnamic acid UV absorbers, triazine UV absorbers, benzophenone UV absorbers, etc. Also good.

For example, as an ultraviolet absorber, amyl benzoate, octyl paraaminobenzoate, ethylene glycol salicylate, phenyl salicylate, octyl salicylate, benzyl salicylate, butylphenyl salicylate, homomentyl salicylate, benzyl cinnamate, paramethoxycinnamate 2 -Ethoxyethyl, octyl paramethoxycinnamate, glyceryl mono-2-ethyl hexanoate diparamethoxycinnamate, isopropyl paramethoxycinnamate, diisopropyl diisopropyl cinnamate ester, urocanic acid, ethyl urocanate, hydroxymethoxy Benzophenone, hydroxymethoxybenzophenonesulfonic acid and its salts, dihydroxymethoxybenzophenone, dihydroxymethoxybenzophenone disulfonic acid Sodium, dihydroxybenzophenone, tetrahydroxybenzophenone, 4-tert-butyl-4′-methoxy-dibenzoylmethane, 2,4,6-trianilino-p- (carbo-2′-ethylhexyl-1′-oxy) -1, 3,5-triazine, 2- (2-hydroxy-5-methylphenyl) benzotriazole, 2-ethylhexyl paradimethylaminobenzoate, ethyl paraaminobenzoate, topylmethoxydipenzoylmethane, oxybenzone-1, ethyl guaiazulenesulfonate Examples of zinc oxide, sinoxate, and anthranilic acid-based ultraviolet absorbers include homomenthyl-N-acetylanthranylate.

These ultraviolet absorbers can be used alone or in combination of two or more.

(Antimicrobial agent)
The antibacterial agent may be an organic antibacterial agent and / or an inorganic antibacterial agent.

For example, as an antibacterial agent, buckwheat extract, halocarban, chlorophenesin, lysozyme chloride, alkyldiaminoethylglycine hydrochloride, isopropylmethylphenol, thymol, hexachlorophene, berberine, thioxolone, salicylic acid and their derivatives, benzoic acid, sodium benzoate , Paraoxybenzoic acid ester, parachlormetacresol, benzalkonium chloride, phenoxyethanol, isopropylmethylphenol, carboxylic acid, sorbic acid, potassium sorbate, hexachlorophene, chlorhexidine chloride, trichlorocarbanilide, photosensitizer, bis (2-pyridylthio) -1-oxide) zinc, thianthol, hinokitiol, triclosan, trichlorohydroxydiphenyl ether, chlorhexidine gluconate Phenoxyethanol, resorcin, azulene, salicylic acid, zinc pyrithione, sodium mononitroguayacol, fennel extract, pepper extract, cetylpyridinium chloride, etc. benzethonium chloride and undecylenic acid derivatives.

These antibacterial agents can be used alone or in combination of two or more.

A cosmetic composition containing a plant extract containing a flavonoid or non-flavonoid secondary metabolite using the biosurfactant of the present invention as a solubilizing agent has a biosurfactant, a whitening agent, an anti-aging agent depending on the purpose of use. Various components other than the agent, humectant, ultraviolet absorber, and antibacterial agent can be further added.

For example, in a cosmetic composition comprising a biosurfactant and a plant extract containing a flavonoid or non-flavonoid secondary metabolite, a surfactant, a lower alcohol, a polyhydric alcohol, olive oil, squalane, It may be used by dissolving with natural fats and oils such as fatty acids.

  For example, as the surfactant, anionic surfactant (carboxylate, sulfonate, sulfate ester salt, phosphate ester salt), cationic surfactant (amine salt, quaternary ammonium salt), amphoteric surfactant ( Carboxylic acid type amphoteric surfactant, sulfate ester type amphoteric surfactant, sulfonic acid type amphoteric surfactant, phosphate ester type amphoteric surfactant), nonionic surfactant (ether type nonionic surfactant, ether ester) Type nonionic surfactant, ester type nonionic surfactant, block polymer type nonionic surfactant, nitrogen-containing type nonionic surfactant), other surfactants (natural surfactants, protein hydrolysates) Derivatives, polymer surfactants, surfactants containing titanium and silicon, fluorocarbon surfactants, and the like.

  Nonionic surfactants include, for example, sorbitan fatty acid esters (for example, sorbitan monooleate, sorbitan monoisostearate, sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan sesquioleate, sorbitan trioleate). Glycerol, penta-2-ethylhexyl diglycerol sorbitan, tetra-2-ethylhexyl diglycerol sorbitan, etc.); glycerin polyglycerin fatty acids (eg mono cottonseed oil fatty acid glycerin, monoerucic acid glycerin, sesquioleate glycerin, glyceryl monostearate) , Α, α′-oleic acid pyroglutamate glycerin, monostearate glycerin malate, etc.); propylene glycol fatty acid esters (for example, monos Propylene glycol tea acrylate, etc.); hardened castor oil derivative; glycerin alkyl ether and the like.

  Examples of the POE-based hydrophilic nonionic surfactant include POE-sorbitan fatty acid esters (for example, POE-sorbitan monooleate, POE-sorbitan monostearate, POE-sorbitan monooleate, POE-sorbitan tetraoleate). POE sorbite fatty acid esters (eg, POE-sorbite monolaurate, POE-sorbite monooleate, POE-sorbite pentaoleate, POE-sorbite monostearate, etc.); POE-glycerin fatty acid esters (eg, POE-glycerol monostearate, POE-glycerin monoisostearate, POE-monooleate such as POE-glycerol triisostearate, etc.); POE-fatty acid esters (for example, POE-distearate) POE-alkyl ethers (for example, POE-lauryl ether, POE-oleyl ether, POE-stearyl ether, POE-behenyl ether, POE-2-octyldodecyl ether), POE-monodiolate, ethylene glycol distearate, etc. POE-cholestanol ether, etc.); Pluronic type (for example, Pluronic, etc.); POE • POP-alkyl ethers (for example, POE • POP-cetyl ether, POE • POP-2-decyltetradecyl ether, POE • POP−) Monobutyl ether, POE / POP-hydrogenated lanolin, POE / POP-glycerin ether, etc.); tetra-POE / tetra-POP-ethylenediamine condensates (for example, Tetronic, etc.); POE-castor oil-cured castor Oil derivatives (eg POE-castor oil, POE-hardened castor oil, POE-hardened castor oil monoisostearate, POE-hardened castor oil triisostearate, POE-hardened castor oil monopyroglutamic acid monoisostearic acid diester, POE -Hardened castor oil maleic acid, etc.); POE-beeswax lanolin derivatives (eg POE-sorbite beeswax etc.); alkanolamides (eg coconut oil fatty acid diethanolamide, lauric acid monoethanolamide, fatty acid isopropanolamide etc.); POE- Examples thereof include propylene glycol fatty acid ester; POE-alkylamine; POE-fatty acid amide; sucrose fatty acid ester; alkylethoxydimethylamine oxide; trioleyl phosphate.

  Examples of the lower alcohol include ethanol, propanol, isopropanol, isobutyl alcohol, t-butyl alcohol and the like.

  Examples of the polyhydric alcohol include divalent alcohols (for example, ethylene glycol, propylene glycol, trimethylene glycol, 1,2-butylene glycol, 1,3-butylene glycol, tetramethylene glycol, 2,3-butylene glycol, Pentamethylene glycol, 2-butene-1,4-diol, hexylene glycol, octylene glycol, etc.); trivalent alcohol (eg, glycerin, trimethylolpropane, etc.); tetravalent alcohol (eg, 1, 2, 6) Pentaerythritol such as hexanetriol, etc .; pentavalent alcohol (eg, xylitol, etc.); hexavalent alcohol (eg, sorbitol, mannitol, etc.); polyhydric alcohol polymer (eg, diethylene glycol, dipropylene glycol, Tylene glycol, polypropylene glycol, tetraethylene glycol, diglycerin, polyethylene glycol, triglycerin, tetraglycerin, polyglycerin, etc.); divalent alcohol alkyl ethers (for example, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol) Monobutyl ether, ethylene glycol monophenyl ether, ethylene glycol monohexyl ether, ethylene glycol mono 2-methylhexyl ether, ethylene glycol isoamyl ether, ethylene glycol benzyl ether, ethylene glycol isopropyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol Dibutyl Dihydric alcohol alkyl ethers (for example, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol butyl ether, diethylene glycol methyl ethyl ether, triethylene glycol monomethyl ether, triethylene glycol) Monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, propylene glycol isopropyl ether, dipropylene glycol methyl ether, dipropylene glycol ethyl ether, dipropylene glycol Dibutyl alcohol ether ester (for example, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene glycol monobutyl ether acetate, ethylene glycol monophenyl ether acetate, ethylene glycol diazebate, ethylene glycol disuccine) , Diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, propylene glycol monophenyl ether acetate, etc.); glycerin monoalkyl ether (example) Sugar alcohol (eg, sorbitol, maltitol, maltotriose, mannitol, sucrose, erythritol, glucose, fructose, starch-degrading sugar, maltose, xylitol, starch degradation) Sugar-reduced alcohol, etc.); Glysolid; Tetrahydrofurfuryl alcohol; POE-Tetrahydrofurfuryl alcohol; POP-Butyl ether; POP / POE-Butyl ether; Tripolyoxypropylene glycerin ether; POP-glycerin ether; POP-glycerin ether phosphate POP · POE-pentane erythritol ether, polyglycerin and the like.

  Oils include avocado oil, olive oil, sesame oil, camellia oil, evening primrose oil, turtle oil, macadamian nut oil, corn oil, mink oil, rapeseed oil, egg yolk oil, persic oil, wheat germ oil, sasanca oil, castor oil , Linseed oil, safflower oil, cottonseed oil, eno oil, soybean oil, peanut oil, tea seed oil, kaya oil, rice bran oil, kiri oil, jojoba oil, cacao butter, palm oil, horse oil, palm oil, palm kernel oil Animal and vegetable oils such as beef tallow, sheep fat, pork tallow, lanolin, whale wax, beeswax, carnauba wax, molasses, candelilla wax, squalane and their hardened oils. There are mineral oils such as liquid paraffin and petrolatum, and synthetic triglycerins such as glycerin tripalmitate.

  Examples of higher fatty acids include lauric acid, myristic acid, palmitic acid, oleic acid, linoleic acid, linolenic acid, stearic acid, behenic acid, 12-hydroxystearic acid, isostearic acid, undecylic acid, tallic acid, eicosapentaenoic acid, docosahexaene. There are acids. Examples of higher alcohols include lauryl alcohol, cetyl alcohol, stearyl alcohol, behenyl alcohol, myristyl alcohol, oleyl alcohol, cetostearyl alcohol, jojoba alcohol, lanolin alcohol, batyl alcohol, 2-decyltetrathececinol, cholesterol, phytosterol, and isostearyl. There is alcohol. Synthetic esters include, for example, cetyl octanoate, octyldodecyl myristate, isopropyl myristate, myristyl myristate, isopropyl palmitate, butyl stearate, hexyl laurate, decyl orenate, dimethyl octanoate, cetyl lactate, myristyl lactate, etc. There is. Examples of silicone include linear polysiloxanes such as dimethylpolysiloxane and methylphenylpolysiloxane, cyclic polysiloxanes such as decamethylcyclopolysiloxane, and three-dimensional network structures such as silicone resins.

  As described above, a cosmetic composition comprising a biosurfactant and a plant extract containing a flavonoid or non-flavonoid secondary metabolite according to the present invention is a quasi-drug, medical product, or hygiene product. It is preferable to blend it with pharmaceuticals.

  A cosmetic composition comprising a biosurfactant according to the present invention and a plant extract containing a flavonoid or non-flavonoid secondary metabolite, a quasi-drug, medical product, hygiene product, pharmaceutical form The dosage form is not limited, and ampules, capsules, powders, granules, pills, tablets, solids, solutions, gels, bubbles, emulsions, creams, ointments, sheets, mousses, bath preparations, etc. It can be.

  Specifically, quasi-drugs, medical supplies, sanitary products, and pharmaceuticals include basic cosmetics such as internal and external pharmaceutical preparations, lotions, emulsions, creams, ointments, lotions, oils, packs, and facial cleansing agents. And skin cleansers, shampoos, rinses, hair treatments, hair creams, pomades, hair sprays, hair styling agents, permanents, hair nickings, hair dyes, hair growth and hair restorations, foundations, white powder, white hair, lipstick, Makeup cosmetics such as blusher, eyeshadow, eyeliner, mascara, eyebrows, eyelashes, cosmetics for finishing such as nail care, perfumes, bath preparations, toothpastes, mouth fresheners, gargles, liquid odors -Examples include deodorants, sanitary products, sanitary cotton, and wet tissue. More specifically, cosmetic soap, shampoo, facial cleanser, rinse, eye cream, eye shadow, cream / milky lotion, lotion, perfume, funny, cosmetic oil, hair cosmetics, hair dye, paste perfume, powder, pack, Cleansing cream, shaving cream, shave lotion, suntan oil, sunscreen oil, sunscreen lotion, sunscreen lotion, sunscreen cream, sunscreen cream, foundation, powdered perfume, blusher, mascara, eyebrow, nail cream, beauty nail enamel , Nail enamel remover, hair wash, cosmetics for bath, lipstick, lip balm, eyeliner, toothpaste, deodorant agent, cologne, hair nourishing agent and hair restorer. The cosmetic composition containing the biosurfactant of the present invention can also be used as an ointment or a poultice.

  A cosmetic composition comprising a biosurfactant and a plant extract containing a flavonoid or non-flavonoid secondary metabolite according to the present invention is preferably applied to humans, As long as the effects of the above can be expected, it can also be applied to animals other than humans.

  A cosmetic composition comprising a biosurfactant according to the present invention and a plant extract containing a flavonoid or non-flavonoid secondary metabolite is included as long as the effect of the present invention is not impaired as required. Ingredients and additives used in quasi-drugs, medical supplies, hygiene products, and pharmaceuticals can be used in combination.

  Examples of waxes include beeswax, carnauba wax, whale wax, lanolin, liquid lanolin, reduced lanolin, hard lanolin, candelilla wax, montan wax, shellac wax, and the like.

  Examples of mineral oils include liquid paraffin, petrolatum, paraffin, ozokelide, ceresin, microcristan wax, polyethylene powder, squalene, squalane, and pristane.

For example, fatty acids include lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, oleic acid, 12-hydroxystearic acid, undecylenic acid, tall oil,
Examples include natural fatty acids such as lanolin fatty acid, and synthetic fatty acids such as isononanoic acid, caproic acid, 2-ethylbutanoic acid, isopentanoic acid, 2-methylpentanoic acid, 2-ethylhexanoic acid, and isopentanoic acid.

  For example, as alcohols, natural alcohols such as ethanol, isopropylanol, lauryl alcohol, cetanol, stearyl alcohol, oleyl alcohol, lanolin alcohol, cholesterol, phytosterol, synthetic alcohols such as 2-hexyldecanol, isostearyl alcohol, 2-octyldodecanol, etc. , Ethylene oxide, ethylene glycol, diethylene glycol, triethylene glycol, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, polyethylene glycol, propylene oxide, propylene glycol, polypropylene glycol, 1,3-butylene Glycol, glycerin Batyl alcohol, pentaerythritol, sorbitol, mannitol, glucose, polyhydric alcohols such as sucrose and the like.

  For example, esters include isopropyl myristate, isopropyl palmitate, butyl stearate, hexyl laurate, myristyl myristate, oleyl oleate, decyl oleate, octyldodecyl myristate, hexyl decyl dimethyloctanoate, cetyl lactate, lactic acid Examples include myristyl, diethyl phthalate, dibutyl phthalate, lanolin acetate, ethylene glycol monostearate, propylene glycol monostearate, propylene glycol dioleate, and the like.

  For example, examples of the metal soap include aluminum stearate, magnesium stearate, zinc stearate, calcium stearate, zinc palmitate, magnesium myristate, zinc laurate, and zinc undecylate.

  For example, gum and water-soluble polymer compounds include gum arabic, benzoin gum, danmar gum, guaiac oil, Irish moss, Karaya gum, tragacanth gum, carob gum, quinseed, agar, casein, dextrin, gelatin, pectin, starch, carrageenan, Carboxyalkylchitin, chitosan, hydroxyalkylchitin, low molecular chitosan, chitosan salt, sulfated chitin, phosphorylated chitin, alginic acid and its salt, hyaluronic acid and its salt, chondroitin sulfate, heparin, ethylcellulose, methylcellulose, carboxymethylcellulose, carboxyethylcellulose , Sodium carboxyethyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, nitrocellulose, crystalline cellulose Scan, polyvinyl alcohol, polyvinyl methyl ether, polyvinyl pyrrolidone, polyvinyl methacrylate, polyacrylic acid salts, polyalkylene oxide or crosslinked polymer thereof such as polyethylene oxide or polypropylene oxide, carboxyvinyl polymers, such as polyethyleneimine.

  For example, vitamins such as retinol, retinal (vitamin A1), dehydroretinal (vitamin A2), carotene, lycopene (provitamin A), vitamin B group, thiamine hydrochloride, thiamine sulfate (vitamin B1) ), Riboflavin (vitamin B2), pyridoxine (vitamin B6), cyanocobalamin (vitamin B12), folic acid, nicotinic acids, pantothenic acids, biotins, choline, inositols, vitamin C, ascorbic acid and its derivatives, vitamin D In the group, ergocalciferol (vitamin D2), cholecalciferol (vitamin D3), dihydrotaxosterol, in vitamin E group, tocopherol and its derivatives, ubiquinones, in vitamin K group, phytonadione (vitamin K1), Naquinone (vitamin K2), menadione (vitamin K3), menadiol (vitamin K4) and the like.

  For example, amino acids include valine, leucine, isoleucine, threonine, methionine, phenylalanine, tryptophan, lysine, glycine, alanine, asparagine, glutamine, serine, cysteine, cystine, tyrosine, proline, hydroxyproline, aspartic acid, glutamic acid, hydroxylysine , Arginine, ornithine, histidine, and the like, and sulfates, phosphates, nitrates, citrates, and amino acid derivatives such as pyrrolidone carboxylic acid.

    Examples of microbial culture metabolites include yeast extract, zinc-containing yeast extract, germanium-containing yeast extract, selenium-containing yeast extract, magnesium-containing yeast extract, rice fermentation extract, Euglena extract, and lactic acid fermented milk powder. .

  For example, examples of the α-hydroxy acid include glycolic acid, citric acid, malic acid, tartaric acid, and lactic acid.

  For example, inorganic pigments include anhydrous silicic acid, magnesium silicate, talc, kaolin, bentonite, mica, titanium mica, bismuth oxychloride, zirconium oxide, magnesium oxide, zinc oxide, titanium oxide, calcium carbonate, magnesium carbonate, yellow oxide Examples include iron, bengara, black iron oxide, gunjo, chromium oxide, chromium hydroxide, carbon black, and calamine.

  For example, astringents include lactic acid, tartaric acid, succinic acid, citric acid, allantoin, zinc chloride, zinc sulfate, zinc oxide, calamine, zinc p-phenolsulfonate, potassium aluminum sulfate, resorcin, ferric chloride, tannic acid Etc.

  Examples of the bactericidal / disinfectant include acrinol, sulfur, benzalkonium chloride, benzethonium chloride, methyl rosaniline chloride, cresol, calcium gluconate, chlorhexidine gluconate, sulfamine, mercurochrome, lactoferrin or a hydrolyzate thereof.

  For example, selenium disulfide, alkylisoquinolinium bromide, zinc pyrithione, biphenamine, thianthol, castari tincture, ginger tincture, pepper tincture, quinine hydrochloride, strong ammonia water, potassium bromate, sodium bromate And thioglycolic acid.

  For example, as perfumes, natural animal perfumes such as musk, civet, castorium, ambergris, anise essential oil, angelica essential oil, Iran essential oil, Iris essential oil, fennel essential oil, orange essential oil, cananga essential oil, caraway essential oil, cardamom essential oil, guayakwood essential oil , Cumin essential oil, black letter essential oil, cinnamon essential oil, cinnamon essential oil, geranium essential oil, copaiba balsam essential oil, coriandel essential oil, perilla essential oil, cedarwood essential oil, citronella essential oil, jasmine essential oil, gingergrass essential oil, cedar essential oil, spearmint essential oil, western peppermint essential oil , Otsuka perfume essential oil, tuberose essential oil, clove essential oil, orange flower essential oil, winter green essential oil, trout balsam essential oil, buttery essential oil, rose essential oil, palmarosa essential oil, persimmon essential oil, hiba essential oil, sandalwood essential oil, petitgren essential oil, bay essential oil, vetiva essential oil, bell Vegetable fragrances such as Mott essential oil, Peruvian balsam essential oil, Boad Rose essential oil, melamine essential oil, mandarin essential oil, eucalyptus essential oil, lime essential oil, lavender essential oil, linaloe essential oil, lemongrass essential oil, lemon essential oil, rosemary essential oil, Japanese seed mint essential oil, Other synthetic fragrances can be mentioned.

  For example, as a dye / colorant, a red cabbage dye, a red rice dye, an akane dye, an anato dye, an squid dye, a turmeric dye, an enju dye, a krill dye, an amber dye, a caramel, a gold, a silver, a gardenia dye, a corn dye, Examples include onion pigment, tamarind pigment, spirulina pigment, buckwheat whole plant pigment, cherry pigment, laver pigment, hibiscus pigment, grape juice pigment, marigold pigment, purple potato pigment, purple yam pigment, lac pigment and rutin.

  Examples of sweeteners include sugar, sweet tea, fructose, arabinose, galactose, xylose, mannose, maltose, honey, glucose, miraculin, monelin and the like.

  For example, examples of the nutrient fortifier include shell calcined calcium, cyanocolabamine, yeast, wheat germ, soybean germ, egg yolk powder, hemicellulose, heme iron and the like.

  Others, hormones, sequestering agents, pH adjusters, chelating agents, antiseptic / antibacterial agents, refreshing agents, stabilizers, emulsifiers, animal / plant proteins and their degradation products, animal / plant polysaccharides and their Degradation product, animal / plant glycoprotein and its degradation product, blood flow promoter, anti-inflammatory agent / antiallergic agent, cell activator, keratolytic agent, wound treatment agent, foam enhancer, thickener, oral preparation, Deodorizing / deodorizing agents, bittering agents, seasonings, enzymes and the like.

A cosmetic composition containing a plant extract containing a flavonoid or non-flavonoid secondary metabolite using the biosurfactant of the present invention as a solubilizer has a moisturizing effect, a collagen production promoting effect, a cell activation effect, an anti-aging effect. It can be widely used when an effect, a hair-growth effect, and a rough skin improvement effect are required. The amount to be used is determined within a range in which the desired moisturizing effect, collagen production promoting effect, cell activation effect, anti-aging effect, hair-growth effect, and rough skin improving effect are sufficiently exhibited.

  The following examples further illustrate the present invention in detail but are not to be construed to limit the scope thereof.

Example 1 Production of MEL-A and Triacyl MEL-A Inoculum culture was performed by inoculating P. antarctica NBRC 10736 into a seed medium (20 ml / 500 ml Sakaguchi flask × 4). Cultured overnight at 30 ° C. The obtained culture broth was used as an inoculum. The composition of the seed medium was 4% Glucose, 0.3% NaNO ₃ , 0.02% MgSO ₄ .7H ₂ O, 0.02% KH ₂ PO ₄ , and 0.1% yeast extract. For the culture, 75 ml of the above inoculum was inoculated into 1.5 L (5 L-jar) of the production medium and cultured using 5 L-jar under the conditions of 30 ° C., 300 rpm (stirring rotation), 0.5 L / min (Air). The composition of the production medium was 3% soybean oil, 0.02% MgSO4 · 7H ₂ O, 0.02% KH ₂ PO ₄ and 0.1% yeast extract. 250 ml of the culture solution was centrifuged (6500 rpm, 30 min), the supernatant was removed, and the precipitate (bacteria) was collected. 50 ml of ethyl acetate was added to the precipitate, and after sufficient stirring, the mixture was centrifuged (8500 rpm, 30 min), separated into a precipitate and a supernatant, and the supernatant was concentrated with an evaporator. Elution with hexane: acetone = 5: 1 and hexane: acetone = 1: 2 was performed using silica gel to obtain MEL-A and triacyl MEL-A fractions.

Example 2 Preparation of MEL-B and triacyl MEL-B
0.2 ml of P. tsukubaensis NBRC1940 was inoculated into a 20 ml seed medium / 500 ml Sakaguchi flask and cultured overnight at 26 ° C. and 180 rpm to obtain a seed fungus. The composition of the seed medium was 4% Glucose, 0.3% NaNO ₃ , 0.02% MgSO 4 · 7H ₂ O, 0.02% KH ₂ PO ₄ , and 0.1% yeast extract. 20 ml of the inoculum was inoculated into 2 L of production medium / 5 L Jar and cultured at 26 ° C., 300 rpm (1/4 VVM, 0.5 L air / min) for 8 days. The culture solution was centrifuged at 7,900 rpm for 60 minutes at 4 ° C. to separate the cells (including MEL-B) and the supernatant. 80 ml of ethyl acetate was added to each bacterial cell fraction, and the mixture was stirred up and down so that the bacterial cells were sufficiently suspended, and then centrifuged at 4,900 rpm for 30 minutes at 4 ° C. An equal amount of saturated saline was added to the obtained supernatant and stirred to obtain an ethyl acetate layer. An appropriate amount of anhydrous sodium sulfate was added to the ethyl acetate layer and the mixture was allowed to settle for 30 minutes and then evaporated to obtain a crude MEL-B product. The obtained MEL-B crude product was eluted with hexane: acetone using a silica gel column to obtain MEL-B and triacyl MEL-B fraction purified products.

Example 3 Preparation of MEL-C and triacyl MEL-C
0.2 ml of P. hubeiensis frozen stock was inoculated into a 20 ml seed medium / 500 ml Sakaguchi flask and cultured overnight at 26 ° C. and 180 rpm to form a seed fungus. The composition of the seed medium was 4% Glucose, 0.3% NaNO ₃ , 0.02% MgSO 4 · 7H ₂ O, 0.02% KH ₂ PO ₄ , and 0.1% yeast extract. 20 ml of the inoculum was inoculated into 2 L of production medium / 5 L Jar and cultured at 26 ° C., 300 rpm (1/4 VVM, 0.5 L air / min) for 8 days. The culture solution was centrifuged at 7,900 rpm for 60 minutes at 4 ° C. to separate the cells (including MEL-C) and the supernatant. 80 ml of ethyl acetate was added to each bacterial cell fraction, and the mixture was stirred up and down so that the bacterial cells were sufficiently suspended, and then centrifuged at 4,900 rpm for 30 minutes at 4 ° C. An equal amount of saturated saline was added to the obtained supernatant and stirred to obtain an ethyl acetate layer. An appropriate amount of anhydrous sodium sulfate was added to the ethyl acetate layer and the mixture was allowed to settle for 30 minutes and then evaporated to obtain a crude MEL-B product. The obtained MEL-C crude purified product was eluted with hexane: acetone using a silica gel column to obtain MEL-C and triacyl MEL-C fraction purified products.

Example 4
In the production of MEL in Example 1, soybean oil was used as a raw material for production, but instead, olive oil was used and cultured in the same manner as in Example 1 to isolate MEL-A, MEL-B, and MEL-C. Purify. The MEL fraction obtained at this time is referred to as MEL-A (OL), MEL-B (OL), and MEL-C (OL) in order to distinguish from the MEL of Example 1.

Example 5 Mannosyl Mannitol Lipid (MML) Production Pseudozymaparantarctica JCM 11752 strain was cultured. That is, Pseudozyma parantarctica JCM 11752 strain preserved in a preservation medium (malt extract 3 g / L, yeast extract 3 g / L, peptone 5 g / L glucose 10 g / L, agar 30 g / L) In a test tube containing 2 mL of liquid medium having a composition of glucose 20 g / L, yeast extract 1 g / L, sodium nitrate 3 g / L, potassium dihydrogen phosphate 0.3 g / L, and magnesium sulfate 0.3 g / L. One platinum loop was inoculated and cultured with shaking at 30 ° C. for 1 day. Subsequently, the obtained bacterial cell culture solution was mixed with olive oil 50 g / L as a vegetable oil, mannitol 100 g / L as a sugar alcohol, yeast extract 1 g / L, sodium nitrate 3 g / L, potassium dihydrogen phosphate 0.3 g / L. And a Sakaguchi flask containing 30 mL of a liquid medium having a composition of magnesium sulfate 0.3 g / L, and cultured at 34 ° C. for 7 days. The above culture broth was collected, the mannosyl alditol lipids in the broth were extracted with ethyl acetate, purified by silica gel chromatography, and the structure of the product was analyzed by ¹³ C NMR and ¹ H NMR.

Example 6 Production of mannosyl arabitol lipid (MAraL) MAraL was produced by culturing in the same manner as in Example 5 except that culture in Example 5 was carried out in a medium containing 100 g / L of arabitol as a sugar alcohol.

Example 7 Production of Mannosyl Sorbitol Lipid (MSL) MSL was produced by culturing in the same manner as in Example 5 except that the culture of Example 5 was carried out in a medium containing 100 g / L of sorbitol as a sugar alcohol.

Example 8 Production of mannosyl ribitol lipid (MRL) MRL was produced by culturing in the same manner as in Example 5 except that cultivation of Example 5 was carried out in a medium containing 100 g / L of ribitol as a sugar alcohol.

Example 9 Preparation of Soybean Germ Extract A diluted internal standard solution (1,7-diaminoheptane, internal standard amount = 1200 nmol) and 500 ml of 5% aqueous perchloric acid solution were added to 100 g of soybean germ (manufactured by Foryou) at room temperature. And left for 1 hour. Thereafter, 16 g of polyclar VT (manufactured by ISP), which is a polyphenol adsorbent, was added, and the soybean germ was sufficiently crushed with a blender mixer and then extracted under acidic conditions by leaving it at room temperature for 30 minutes. The crushed material is centrifuged at 2 ° C. and 22,000 × g for 20 minutes to collect a liquid fraction, neutralized with a 30% sodium hydroxide solution, and this solution is used as a plant extract (soybean germ extract). did. The plant extract contained 23.5 mg of putrescine as polyamine, 24.0 mg of spermidine, and 9.6 mg of spermine, and the total amount was 57.1 mg. Further, the recovered plant extract was passed through a column packed with a cation exchange resin (AG 50W-X4, 200-400 mesh, H + type, manufactured by Bio-Rad), and the polyamine was adsorbed on the resin. The column was washed by flowing 0.7N NaCl / 0.1M sodium phosphate solution (pH 8.0), water and 1N hydrochloric acid sequentially. After removing the impurities, the polyamine was eluted with 6N hydrochloric acid and neutralized with 30% sodium hydroxide to obtain a purified plant extract (purified soybean germ extract). The purified plant extract contained 20.4 mg of putrescine, 22.3 mg of spermidine and 7.7 mg of spermine as polyamines, for a total of 50.4 mg. Plant extract (soybean germ extract) and purified plant extract (purified soybean germ extract) were desalted with an electrodialyzer (Acylizer, manufactured by Astom), concentrated by freeze-drying, and used for various evaluations. .

  To 1 kg of soybean germ (manufactured by Foyu), a diluted internal standard solution (1,7-diaminoheptane, internal standard amount = 10 μmol) and 5 L of 1N hydrochloric acid solution were added and left at room temperature for 1 hour. Thereafter, 80 g of polyphenol VT (ISP), which is a polyphenol adsorbent, was added, and the soybean germ was sufficiently crushed with a homogenizer and then left for 1 hour at room temperature to extract under acidic conditions. The crushed material is centrifuged at 2 ° C. and 22,000 × g for 30 minutes to collect a liquid fraction, neutralized with a 30% sodium hydroxide solution, and this solution is used as a plant extract (soybean germ extract). did. The plant extract contained 235.1 mg of putrescine as polyamine, 241.8 mg of spermidine, and 80.1 mg of spermine, for a total of 557.0 mg. Sharp single peaks of putrescine (detection time: 10.925 minutes), spermidine (detection time: 15.898 minutes), and spermine (detection time: 20.025 minutes) were detected. The single peak at 13.002 minutes is the diluted internal standard solution (1,7-diaminoheptane). A sharp single peak of each polyamine was detected in the plant extract, confirming that the polyamine was the main component. The reason why the plant extract is highly pure is that only the germ (embryo) part is used to reduce the contamination of seed proteins and the like, and the addition of a polyphenol adsorbent and extraction under acidic conditions results in the addition of seed proteins, etc. The fact that impurities are denatured and adsorbed and removed has a great influence. The plant extract (soybean germ extract) was desalted with an electrodialyzer (Acylizer, manufactured by Astom), concentrated by freeze-drying, and used for various evaluations.

Example 10 Preparation of Wheat Germ Extract 100 g of wheat germ (cultured and roasted type, manufactured by Nisshin Pharma) diluted internal standard solution (1,7-diaminoheptane, internal standard amount = 1200 nmol), 500 ml of 5% excess An aqueous chloric acid solution was added and the mixture was allowed to stand at room temperature for 1 hour. Thereafter, 16 g of polyclar VT (manufactured by ISP), which is a polyphenol adsorbent, was added, and the soybean germ was sufficiently crushed with a blender mixer and then extracted under acidic conditions by leaving it at room temperature for 30 minutes. The crushed material is centrifuged at 2 ° C. and 22,000 × g for 20 minutes to collect a liquid fraction, neutralized with a 30% sodium hydroxide solution, and this solution is used as a plant extract (wheat germ extract). did. The plant extract contained 6.4 mg of putrescine, 23.9 mg of spermidine and 14.3 mg of spermine as polyamines, for a total of 44.6 mg. Further, the recovered plant extract was passed through a column packed with a cation exchange resin (AG 50W-X4, 200-400 mesh, H + type, manufactured by Bio-Rad), and the polyamine was adsorbed on the resin. The column was washed by flowing 0.7N NaCl / 0.1M sodium phosphate solution (pH 8.0), water and 1N hydrochloric acid sequentially. After removing the impurities, the polyamine was eluted with 6N hydrochloric acid and neutralized with 30% sodium hydroxide to obtain a purified plant extract (purified wheat germ extract). The purified plant extract contained 5.7 mg of putrescine as polyamine, 21.5 mg of spermidine, and 12.9 mg of spermine, for a total of 40.1 mg. Plant extracts (wheat germ extract) and purified plant extracts (purified wheat germ extract) were desalted with an electrodialyzer (Acylizer, manufactured by Astom), concentrated by freeze-drying, and used for various evaluations. .

  Diluted internal standard solution (1,7-diaminoheptane, internal standard amount = 10 μmol) is added to 1 kg of wheat germ (cultured and roasted type, manufactured by Nisshin Pharma) and left at room temperature for 1 hour. did. Thereafter, 80 g of polyphenol VT (ISP), which is a polyphenol adsorbent, was added, and the wheat germ was sufficiently crushed with a homogenizer, and then allowed to stand at room temperature for 1 hour and extracted under acidic conditions. The crushed material is centrifuged at 2 ° C. and 22,000 × g for 30 minutes to collect a liquid fraction, neutralized with a 30% sodium hydroxide solution, and this solution is used as a plant extract (wheat germ extract). did. The plant extract contained 75.1 mg of putrescine, 294.0 mg of spermidine and 119.4 mg of spermine as polyamines, for a total of 488.5 mg. Sharp single peaks of putrescine (detection time: 10.110 minutes), spermidine (detection time: 15.892 minutes), and spermine (detection time: 20.19 minutes) were detected. The single peak at 12.994 minutes is a diluted internal standard solution (1,7-diaminoheptane). A sharp single peak of each polyamine was detected in the plant extract, confirming that the polyamine was the main component. The reason why the plant extract is highly pure is that the germ (embryo) part is used to reduce contamination of seed proteins and the like, and polyphenol adsorbent is added and extracted under acid conditions to remove impurities such as proteins. Degeneration or adsorption removal has a great influence. The plant extract (wheat germ extract) was desalted with an electrodialyzer (Acylizer, manufactured by Astom), concentrated by freeze-drying, and used for various evaluations.

Example 11 Preparation of Cosmos Extract 78.2 g of Kibana Cosmos flower was cut into pieces and freeze-dried for 2 days and nights. This was pulverized with a mixer to form a powder, 1 L of a dichloromethane-methanol (1: 1) solution was added, and the mixture was extracted by stirring at room temperature for 1 hour. Then, the solvent was distilled off by suction filtration, and hexane precipitation was performed to remove the coexisting fats and sterols. The solvent was concentrated under reduced pressure to obtain 1.63 g of extract.

Example 12 Preparation of Momijigasa Extract 2 kg of Momijigasa leaf was lyophilized and stirred with a mixer to obtain 212 g of powder. 4 L of ethanol was added to this powder, stirred for 12 hours, filtered to remove insoluble matters, and concentrated to obtain 16 g of a green primary extract. To this primary extract, 500 ml of 60% ethanol was added, and after sonication for 15 minutes, the mixture was allowed to stand overnight in a refrigerator. Centrifugation was performed at 7000 rpm for 15 minutes, and the supernatant after separating the precipitate was concentrated to obtain 8 g of a dried product. When the Kakalol content and chlorophyll content in the supernatant and the precipitate were measured, it was 1132 mg Kakalol and 3 mg chlorophyll in the supernatant, and 294 mg Kakalol and 718 mg in the precipitate. By collecting the dried supernatant, It has been found that a kakarol extract with a reduced chlorophyll content can be obtained. Subsequently, 500 ml of 20% ethanol was added to the dried product of the obtained 60% ethanol extraction supernatant, and after sonication, it was allowed to stand overnight in a refrigerator. Centrifugation was performed at 7000 rpm for 15 minutes to obtain 1.5 g of a precipitate. The Kakarol content and chlorophyll content in the supernatant and the precipitate were measured. As a result, Kakalol extract in the supernatant was 67 mg Kakarol and 0.1 mg in chlorophyll, Kakalol 728 mg in the precipitate and 3 mg in chlorophyll, and the Kakarol extract from which polar substances were removed Could get.
The concentration of kakarol in the extract was determined by HPLC analysis under the following conditions. Column: XterraMSC18, flow rate: 1 ml / min, solvent: gradient from 5% acetonitrile 20 mM phosphoric acid (A) to 95% acetonitrile 20 mM phosphoric acid (B), detection: diode array detector 200-700 nm, column temperature: room temperature, injection Amount: 20 μl. The concentration of chlorophyll was obtained by dissolving the extract in acetone and measuring the absorbance at 660 nm and 642.5 nm to determine the amount of chlorophyll according to the total amount of chlorophyll (mg / l) = 7.12D ₆₆₀ + D _642.5 .

Example 13 Preparation of Horseradish (Leaf and Rhizome) Extract 100 g each of horseradish leaves and rhizomes was cut into small pieces, 1000 ml of ethanol was added and the mixture was extracted for 24 hours at room temperature, and the extract was filtered. The residue was further re-extracted in the same manner by adding 200 ml of ethanol. The extract was collected and concentrated under reduced pressure. After distilling off the solvent, 20 ml of water and 80 ml of ethyl acetate were added, and this was transferred to a separatory funnel, shaken vigorously, and allowed to stand to separate into two layers. The ethyl acetate layer was collected. This was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 1.367 g of horseradish leaf extract and 0.2 g of rhizome extract.

Example 14 Blending Test and Performance Test Flavonoids obtained in Examples 9 to 13 or non-obtained using the biosurfactants obtained in Examples 1 to 8 with the raw materials and blending ratios shown in Tables 1, 2, 3, and 4, respectively. A cosmetic composition excellent in stability was prepared as a trial product, which was formulated with a plant extract containing a flavonoid secondary metabolite.

Table 5 shows a comparative example in which a cosmetic composition to which no biosurfactant is added is produced as a comparative example. The formulations in Tables 1, 2, 3, 4, and 5 are expressed in mass%, and “-” means no formulation.

Specifically, in both the Examples and Comparative Examples, first, each of the A phase raw materials and the B phase raw materials are separately mixed, and the A phase is heated to 70 ° C. and dissolved and mixed. The above solution was added and heated to 50 ° C. to emulsify with a homomixer to prepare a cosmetic composition.

<Feeling of familiarity with skin>
The panel (evaluator) was allowed to use 5 people, the feeling of use was scored as follows, and the total was obtained as an evaluation score. Based on this, the following criteria were used.
《Points》
2 points: Refreshed at the time of application, and feels familiar after application.
1 point: There is stickiness at the time of application, and there is a feeling of familiarity after application.
0 point: There is a sticky feeling both during coating and after coating.
<Criteria>
◎: Sum 10 to 9 points ... Very good ○: Sum 8 to 7 points… Good △: Sum 6 to 5 points… Good ×: Sum 4 or less… Bad <Stability over time>
Stability over time The stability over time was determined visually for those stored at 50 ° C. for 1 month, and was determined according to the following criteria.
◎: No change in appearance ○: Some change in appearance, but no oil separation, water separation, precipitation, etc. Δ: Some change in appearance, oil separation, water separation, precipitation Things that happened
×: Appearance changed significantly and oil separation, water separation, precipitation, etc. occurred

(Time stability test results)
In the state returned to 20 ° C. after completion of the storage test, Formulation Examples 1 to 25 to which MEL was added were uniformly dispersed after shaking, and it was confirmed that there was no deterioration in quality when stored at 50 ° C. Further, in Comparative Examples 1 to 6, partial precipitation was also observed. From this, it became clear that the skin external preparation of this invention can mix | blend a plant extract stably.

(Usability test results)
As a result of comparing the usability of Formulation Examples 1 to 25 to which MEL was added and Comparative Examples 1 to 6, it became clear that the familiarity to the skin was improved by the addition of MEL.

A cosmetic composition comprising the biosurfactant of the present invention and a plant extract containing a flavonoid or non-flavonoid secondary metabolite at any blending ratio shown in Tables 1, 2, 3 and 4. In addition to the familiarity with the intended skin, it was confirmed that the effect of preventing oli and enhancing the stability of the skin lotion containing the plant extract was confirmed.

A cosmetic composition excellent in stability can be provided in which a plant extract containing a flavonoid or non-flavonoid secondary metabolite is blended using the biosurfactant of the present invention. Further, a cosmetic composition containing the cosmetic composition, a quasi-drug composition, a medical product composition, a hygiene product composition, a pharmaceutical composition, and a cosmetic, quasi-drug, medical product, hygiene containing the composition. It is to provide supplies and medicines.

Claims (10)

  A cosmetic composition comprising a plant extract containing a biosurfactant and a flavonoid or non-flavonoid secondary metabolite.   The cosmetic composition according to claim 1, wherein the biosurfactant has a mannose skeleton.   The cosmetic composition according to claim 1 or 2, wherein the biosurfactant has a sugar alcohol linked to a glycoside bond to the hydroxyl group at the 1-position of the mannose skeleton. The biosurfactant having a mannose skeleton was selected from the group consisting of mannosyl erythritol lipid (MEL), mannosyl mannitol lipid (MML), mannosyl sorbitol lipid (MSL), mannosyl arabitol lipid (MAraL) and mannosyl ribitol lipid (MRL). 4. Cosmetic composition according to claim 3, characterized in that it is one or more compounds. MEL is mannosyl erythritol lipid A (MEL-A), mannosyl erythritol lipid B (MEL-B), mannosyl erythritol lipid C (MEL-C), mannosyl erythritol lipid D (MEL-D), a triacyl derivative of MEL-A, The cosmetic composition according to claim 4, wherein the cosmetic composition is one or more compounds selected from the group consisting of a triacyl form of MEL-B, a triacyl form of MEL-C, and a triacyl form of MEL-D. The cosmetic composition according to any one of claims 1 to 5, wherein the biosurfactant contains a saturated fatty acid and / or an unsaturated fatty acid. The cosmetic composition according to any one of claims 1 to 6, wherein the biosurfactant forms a lamellar structure and / or a liposome. The cosmetic composition according to claim 7, wherein a coexisting active ingredient is embedded in a lamellar structure and / or liposome formed by a biosurfactant. The plant extract containing a flavonoid or non-flavonoid secondary metabolite is an extract from one or more kinds of plants selected from Momijigasa, Wasabi, Cosmos, wheat germ and soybean germ. Item 9. A cosmetic composition according to any one of Items 1 to 8. The cosmetic composition according to any one of claims 1 to 9, which is used as a cosmetic, a quasi-drug, a medical product, a hygiene product, or a pharmaceutical product.