KR101451298B1 - Soybean leaves of the high-content isoflavone derivatives and preparing method thereof - Google Patents

Abstract

The present invention relates to soybean leaves with high-content of isoflavone derivatives and a preparing method thereof and, more specifically, to soybean leaves with high-content of isoflavone derivatives and the preparing method thereof, which can be used in functional foods and pharmaceutical materials to cure diseases from imbalance of estrogen and antioxidant effect deficiency by identifying the isoflavone derivative content significantly increasing in soybean leaves in which ethylene and ethephon of ethylene donors are processed.

Description

[Technical Field] The present invention relates to an isoflavone derivative having a high content of isoflavone derivatives and a preparation method thereof,

The present invention relates to a method for producing a high content of an isoflavone derivative, a high content of an isoflavone derivative produced by the method, a use of a high content of the isoflavone derivative, and a method for mass production of an isoflavone derivative from a canola.

Isoflavone derivatives are representative flavonoids with excellent pharmacological efficacy, and a great deal of capital is invested in the development of functional plants with high content in the world. Isoflavones are nonsteroidal estrogens, which are known to be phytoestrogenic because they have a chemical structure and physiological characteristics similar to those of estrogen. These are similar to estrogen, a female hormone, and show useful physiological activities expected in estrogen. It has been reported that it reduces the risk of osteoporosis especially after menopause and lowers plasma cholesterol. It is also reported that the antioxidant activity and antioxidant activity of coronary heart disease are lowered.

Isoflavones exist in the form of a glycoside linked to a beta-glycoside or in the form of a non-glycosylated sugar. Examples of non-glycosides include genistein, daidzein and glycitein, and glycosides include genistin, daidzin, and glycitin. . Soybean-derived non-fermented foods contain many glycosides, while fermented foods mainly contain non-glycosides as the sugar is decomposed from the glycosides by bacteria involved in fermentation.

Most of the isoflavones used as food and medicinal materials are extracted from beans and red clover. Many breeding studies have been carried out for the development of soybean containing high levels of isoflavones, but soybeans containing 4000 ㎍ / g total isoflavone have been reported at the highest level ( J. Agric. Food Cehm. 2012, 60, 6045-6055). Korean Patent Laid-Open Publication No. 2003-93025 discloses a method for producing germinated soybean containing high concentration of isoflavone in which washed soybean is soaked in purified water and then germinated to increase the isoflavone content by 40 to 70% The content is low.

On the other hand, canola has been reported to contain very small amounts of isoflavone derivatives. Specifically, there was no significant difference between the concentrations of daidzin (not detected), genistin (90 ㎍ / g), malonyldaidzin (not detected), malonylgenistin (310 ug / g), daidzein (Not detected), and genistein (not detected) (BIOMEDICINE & PHARMACOTHERATY, 2002, 56, 289-295).

The present inventors have made efforts to develop soybean leaves containing high levels of isoflavone derivatives. As a result, when ethylene or ethylene donor ethephon (2-chloroethylphosphonic acid) was treated during soybean cultivation, high concentrations of isoflavone derivatives And thus the present invention has been completed.

It is an object of the present invention to provide a method for producing a high content of an isoflavone derivative-containing soybean leaf comprising treating a soybean leaf with ethylene, an ethylene donor or an ethylene generator.

It is still another object of the present invention to provide a high content of soybean leaf of an isoflavone derivative produced by the above production method.

Still another object of the present invention is to provide food and medicinal materials containing a high content of isoflavone derivatives, such as soybean leaves, soybean leaf extract or fractions thereof.

It is another object of the present invention to provide a method for mass production of isoflavone derivatives from soybean leaves using ethylene, ethylene donor or ethylene generator.

In order to accomplish the object of the present invention, the present invention provides a method for producing a high content of isoflavone derivatives represented by the following formula (1), which comprises treating a soybean leaf with ethylene, an ethylene donor or an ethylene generator to provide;

[Chemical Formula 1]

Wherein R ₁ is independently H or OH, and R ₂ is independently H, glucose or glucose malonate.

Also, the present invention provides an isoflavone derivative high-content soybean leaf prepared by the above-mentioned method.

In addition, the present invention provides a composition comprising a high content of an isoflavone derivative-containing soybean leaf, an extract of the soybean leaf, or a fraction of the extract of the present invention.

The present invention also provides a pharmaceutical composition for the prevention and treatment of diseases caused by estrogen deficiency, which comprises as an active ingredient, an isoflavone derivative high amount of a soybean leaf, an extract of the canola leaf, or a fraction of the extract, according to the present invention.

In addition, the present invention provides a health food for prevention and improvement of diseases caused by estrogen deficiency, which comprises as an active ingredient, an isoflavone derivative high amount of a soybean leaf, an extract of the canola leaf or a fraction of the above extract according to the present invention.

The present invention also provides a pharmaceutical composition for an antioxidant containing an isoflavone derivative high in content of the present invention, an extract of the canola, or a fraction thereof, as an active ingredient.

The present invention also provides an antioxidant health food containing as an active ingredient a high content of an isoflavone derivative of the present invention, an extract of the canola, or a fraction of the extract.

The present invention also provides a cosmetic composition for skin care comprising as an active ingredient, a high content of an isoflavone derivative-containing soybean leaf, an extract of the canola leaf, or a fraction of the extract.

In addition, the present invention provides a cosmetic composition for skin care comprising as an active ingredient a high content of an isoflavone derivative high-content soybean leaf, an extract of the canola leaf, or a fraction of the extract.

The present invention also provides a health food for skin care, comprising as an active ingredient, a high content of an isoflavone derivative, a soybean leaf, an extract of the canola leaf, or a fraction of the extract.

In addition, the present invention provides a tea using a high content of an isoflavone derivative according to the present invention.

In addition, the present invention provides a method for preparing tea using a high content of an isoflavone derivative of the present invention.

The present invention also provides a method for mass production of isoflavone derivatives from soybean leaves using ethylene, ethylene donor or ethylene generator.

In addition,

1) treating the soybean leaf with ethylene, an ethylene donor or an ethylene generator to prepare a soybean leaf; And

2) extracting the soybean leaves of step 1) to isolate the isoflavone derivative, and a method for mass production of the isoflavone derivative.

The present invention confirms that a high content of isoflavone derivatives is accumulated at a high concentration in soybean leaves by treating an ethylene or an ethylene donor, ethephon, in a soybean plant 10 to 90 days after sowing, Contents Not only the production method of soybean leaves but also soybean leaves, soybean leaf extract and extracted fractions containing them can be usefully used as food for diseases and medicinal materials caused by estrogen imbalance and deficiency of antioxidant ability.

FIG. 1 is an UPLC chromatogram showing an increase in the content of isoflavone derivatives according to cultivation period after treatment with ethephon.
FIG. 2 is a graph showing UPLC chromatogram results of extracts of soybean leaves extracted with ethanol before treatment with ethephon.
FIG. 3 is a diagram showing UPLC chromatogram results of an extract obtained by extracting soybean leaves with ethanol after 7 days of treatment with ethephon.
Fig. 4 is a diagram showing a mass spectrometry (Q-TOF MS) result in which the peak 1 of Fig. 3 is identified as daidzin.
FIG. 5 is a graph showing a mass spectrometry (Q-TOF MS) result showing that Peak 2 in FIG. 3 is genistin.
FIG. 6 is a graph showing a mass spectrometry (Q-TOF MS) result showing that the peak 3 of FIG. 3 is malonyldaidzin.
FIG. 7 is a diagram showing a mass spectrometry (Q-TOF MS) result in which Peak 4 of FIG. 3 is identified as malonylgenistin.
FIG. 8 is a graph showing UPLC chromatogram results of an extract obtained by treating beta-glucosidase with an extract of soybean leaves after 7 days of treatment with ethanol.

Hereinafter, the present invention will be described in detail.

The present invention provides a method for producing a high content of an isoflavone derivative-containing soybean leaf comprising treating a soybean leaf with ethylene, an ethylene donor or an ethylene generator.

It is preferable that the above-mentioned canola leaves have been lengthened 10 days or more after sowing, more preferably 40 days have passed after sowing, but the present invention is not limited thereto.

The ethylene donor is preferably ethephon but is not limited thereto. The ethylene is the simplest olefinic hydrocarbon (chemical formula: C ₂ H ₄ ) which is colorless and sweet. As a kind of plant hormone, it has a function of promoting the maturation of plant tissues such as change of physiology after harvest of fruits and vegetables, in particular, maturation of horticultural crops and yellowing of leafy vegetables. Ethephon (2-chloroethylphosphonic acid) is a kind of ethylene generator, which generates ethylene under neutral and alkaline conditions of pH 4.1 or higher. When an aqueous solution of 1000-2000 times in a liquid phase is sprayed on fruits and vegetables Decomposes and generates ethylene to promote maturation, chilling and pigmentation.

The ethylene, ethylene donor or ethylene generator is preferably treated at a concentration of 5 to 500 ppm, more preferably at a concentration of 5 to 100 ppm, but not always limited thereto. The ethylene, ethylene donor or ethylene generator can be treated before harvesting or after harvest.

The isoflavone derivative is preferably a compound represented by the following formula (1), more preferably any one of the compounds represented by the following formulas (2) to (7), but is not limited thereto.

Wherein R ₁ is independently H or OH, and R ₂ is independently H, glucose or glucose malonate.

Also, the present invention provides an isoflavone derivative high-content soybean leaf prepared by the above-mentioned method.

The isoflavone derivative is preferably a compound represented by the formula (1), more preferably any one of the compounds represented by the formulas (2) to (7), but is not limited thereto.

In a specific example of the present invention, the present inventors treated soybean plants (40-100 ppm) diluted in water for 40 days (growth period R4) after soybean sowing, Was significantly increased and reached a maximum at about 5-12 days after treatment (see FIG. 1). In addition, kaempferol-3- O- β-D-glucopyranosyl (1 → 2) -α-L-rhamnopyranosyl (1 → 6) -β-D- galactopyranoside, kaempferol-3- O -β- D-glucopyranosyl (1 → 2) -α-L-rhamnopyranosyl (1 → 6) -β-D-glucopyranoside, kaempferol-3- O - (2,6-di- O -α-L-rhamnopyranosyl) -β- D-glucopyranoside, kaempferol-3- O -β-digalactopyranoside, kaempferol-3- O -β-diglucopyranoside, kaempferol-3- O -α-L-rhamnopyranosyl (1 → 6) -β-D-galactopyranoside as a major compound. However, it was confirmed that four kinds of isoflavone derivatives daidzin, jenestin, malonyldaidzin, and malonyl genistein, which are treated with eshephon, rapidly accumulate in soybean leaves (see Table 1). Further, the extract of the soybean leaves treated with the above-mentioned esophone was extracted with ethanol, and the extract and the extract of the soybean leaf extract treated with beta-glucosidase were separated and purified to obtain six kinds of isoflavone derivatives , Daidzin, genistin, malonylididene, malonyl genistein, daidzein and genistein (see FIGS. 3 to 8).

The present inventors also quantitatively analyzed four isoflavone derivatives, daidzin, genistin, malonylidenejin and malonyl genistin, which were isolated from soybean leaves harvested after treatment with ethephon and soybean leaves treated with post- As a result, the content of isoflavone derivatives in soybean leaves harvested after treatment with espe phage was remarkably increased, and the content of isoflavone derivatives in soybean leaves treated with post-harvest etefone significantly increased By confirming, it was confirmed that the method of harvesting the soybean leaves after treating them with eshephon, and the method of treating the harvested soybean leaves with eshephon were all possible with the method of producing soybean leaves of high content of isoflavone derivatives (see Table 1 and Table 2).

The present invention also provides a method for mass production of isoflavone derivatives from soybean leaves using ethylene, an ethylene donor or an ethylene generator.

Specifically,

1) treating the soybean leaf with ethylene, an ethylene donor or an ethylene generator to prepare a soybean leaf; And

2) isolating the soybean leaves of step 1) and separating the isoflavone derivative.

In the above method, it is preferable that the soybean leaves in step 1) be 10 days or more after sowing, more preferably 40 days after sowing, and most preferably 10 to 90 days after sowing .

In this method, the ethylene, ethylene donor or ethylene generator of step 1) can be treated before harvesting or after harvesting.

In the above method, the ethylene donor of step 1) is preferably ethephon, but not limited thereto, and all the substances which induce or generate ethylene can be used.

In the above method, the ethylene, ethylene donor or ethylene generator of step 1) is preferably treated at a concentration of 5 to 500 ppm, more preferably at a concentration of 5 to 100 ppm.

In the above method, the isoflavone derivative is preferably a compound represented by the above formula (1), and more preferably at least one of the compounds represented by the above formulas (2) to (7).

The present invention can be used as a method for mass production of isoflavone derivatives by preparing soybean leaves containing high levels of isoflavone derivatives by treating ethylene oxide and an ethylene oxide donor esophone to soybean leaves. In addition, it was confirmed that the content of isoflavone derivatives was remarkably increased in both the method of harvesting the leaves after treating the leaves with eshephon and the method of treating leaves with the leaves of esophagus, so that ethylene and ethylene donors To produce a soybean oil having a high content of isoflavone derivatives can be advantageously used as a method for mass production of isoflavone derivatives.

The present invention also provides a composition comprising a high content of an isoflavone derivative produced by treating soybean leaves with ethylene, an ethylene donor or an ethylene generator, an extract of the soybean leaf, or a fraction of the extract.

The soybean curd extract or its fractions are preferably, but not limited to, those produced by a manufacturing method comprising the following steps:

1) extracting soybean leaves with an extraction solvent;

2) filtering the extract of step 1);

3) concentrating the filtered extract of step 2) under reduced pressure and then drying to prepare a soybean leaf extract; And

4) Extracting the extract of the bean curd in step 3) with an organic solvent to prepare a fraction of the bean curd.

In the above method, the soybean leaves of step 1) are collected from soybean plants having a high concentration of isoflavone after treatment with ethephon. The soybean plants treated with the herbicide may be leaves, stems or roots. However, it is not limited thereto. According to a preferred embodiment of the present invention, soybean leaves are preferably used.

In the above method, it is preferable to use water, an alcohol or a mixture thereof in the extraction solvent of the step 1). As the alcohol, a C ₁ to C ₂ lower alcohol is preferably used, and as the lower alcohol, ethanol or methanol is preferably used. As the extraction method, it is preferable to use shaking extraction, Soxhlet extraction or reflux extraction, but it is not limited thereto. The extraction solvent is preferably added by 1 to 10 times, more preferably 4 to 6 times, to the dried soybean leaf. The extraction temperature is preferably 20 占 폚 to 100 占 폚, more preferably 20 占 폚 to 40 占 폚, and most preferably room temperature, but is not limited thereto. The extraction time is preferably 10 to 48 hours, more preferably 15 to 30 hours, most preferably 24 hours, but is not limited thereto. The number of times of extraction is preferably 1 to 5 times, more preferably 3 to 4 times, and most preferably, 3 times, but is not limited thereto.

In the above method, it is preferable to use a vacuum decompression concentrator or a vacuum rotary evaporator for the decompression concentration in step 3), but it is not limited thereto. The drying is preferably performed under reduced pressure, vacuum drying, boiling, spray drying or freeze drying, but not always limited thereto.

In the above method, it is preferable to use a black-brown crude extract, which is an extract of a soybean-bean extract concentrated in a reduced pressure, in step 4), but it is not limited thereto, and the organic solvent is preferably n-hexane, chloroform, ethyl acetate or butanol According to a preferred embodiment of the present invention, it is more preferable that it is chloroform, but it is not limited thereto. The fraction is a n-hexane fraction, a chloroform fraction, an ethyl acetate fraction, a butanol fraction or a water fraction obtained by suspending the soybean leaf extract in water and sequentially fractionating the fraction with n-hexane, chloroform, ethyl acetate, But is not limited thereto. The fraction may be obtained from the soybean leaf extract by repeating the fractionation process one to five times, preferably three times, and is preferably concentrated under reduced pressure, but not limited thereto.

The present invention also relates to a method for the treatment of a disease caused by estrogen deficiency comprising an effective amount of an isoflavone derivative produced by treating ethylene glycol, ethylene donor or ethylene generator in a soybean leaf with a high content of a soybean leaf, an extract of the soybean leaf or a fraction thereof A pharmaceutical composition for prevention and treatment is provided.

The disease caused by the estrogen deficiency is preferably one selected from the group consisting of osteoporosis, heart disease, breast cancer, external sound disease, hyperlipidemia, skin aging and facial flushing, but is not limited thereto.

Since the isoflavone derivatives isolated from the soybean leaves containing the isoflavone of the present invention have established physiological activity, the soybean leaf extract and the fractions thereof containing the compounds are usefully used as a pharmaceutical composition for prevention and treatment of diseases caused by estrogen deficiency .

The composition of the present invention may further comprise suitable carriers, excipients and diluents conventionally used in the preparation of pharmaceutical compositions.

The composition of the present invention can be administered orally or parenterally, and it is preferable to select an external or intraperitoneal injection, intramuscular injection, subcutaneous injection, intravenous injection, intramuscular injection, But is not limited thereto.

The composition of the present invention can be formulated into oral formulations such as powders, granules, tablets, capsules, suspensions, emulsions, syrups and aerosols, external preparations, suppositories and sterilized injection solutions according to conventional methods have. Examples of carriers, excipients and diluents that can be included in the composition include lactose, dextrose, sucrose, sorbitol, mannitol, xylitol, erythritol, maltitol, starch, acacia rubber, alginate, gelatin, calcium phosphate, calcium silicate, Methylcellulose, microcrystalline cellulose, polyvinylpyrrolidone, water, methylhydroxybenzoate, propylhydroxybenzoate, talc, magnesium stearate and mineral oil. In the case of formulation, a diluent or excipient such as a filler, an extender, a binder, a wetting agent, a disintegrant, or a surfactant is usually used. Solid formulations for oral administration include tablets, pills, powders, granules, capsules and the like, which may contain at least one excipient such as starch, calcium carbonate, sucrose ), Lactose, gelatin and the like. In addition to simple excipients, lubricants such as magnesium stearate and talc may also be used. Examples of the liquid preparation for oral use include suspensions, solutions, emulsions, and syrups. In addition to water and liquid paraffin, simple diluents commonly used, various excipients such as wetting agents, sweeteners, fragrances, preservatives and the like may be included . Formulations for parenteral administration include sterilized aqueous solutions, non-aqueous solutions, suspensions, emulsions, freeze-dried preparations, and suppositories. Examples of the suspending agent include propylene glycol, polyethylene glycol, vegetable oil such as olive oil, injectable ester such as ethyl oleate, and the like. Examples of suppository bases include witepsol, macrogol, tween 61, cacao butter, laurin, glycerogelatin, and the like.

The preferred dosage of the composition of the present invention varies depending on the condition and the weight of the patient, the degree of disease, the type of drug, the route of administration and the period of time, but can be appropriately selected by those skilled in the art. However, for the desired effect, the composition is preferably administered at a dose of 0.0001 to 1 g / kg, preferably 0.001 to 200 mg / kg, per day, but is not limited thereto. The above administration may be carried out once a day or divided into several times. The dose is not intended to limit the scope of the invention in any way.

The present invention also relates to a method for the treatment of a disease caused by estrogen deficiency comprising an effective amount of an isoflavone derivative produced by treating ethylene glycol, ethylene donor or ethylene generator in a soybean leaf with a high content of a soybean leaf, an extract of the soybean leaf or a fraction thereof Prevention and improvement of health food.

The disease caused by the estrogen deficiency is preferably one selected from the group consisting of osteoporosis, heart disease, breast cancer, external sound disease, hyperlipidemia, skin aging and facial flushing, but is not limited thereto.

Since the isoflavone derivatives isolated from the soybean leaves of Isoflavones of the present invention have established physiological activity, the soybean leaf extract containing the compounds and the fractions thereof can be effectively used as a health food for prevention and improvement of diseases caused by estrogen deficiency have.

The health food of the present invention can be used appropriately in accordance with a conventional method, such as a high content of the isoflavone derivative, an extract of the canola or the fraction of the extract, or it can be used together with other food or food ingredients.

There is no particular limitation on the kind of the food. Examples of the food include dairy products including functional mixed tea, drink, meat, sausage, bread, biscuit, rice cake, chocolate, candy, snack, confectionery, pizza, ramen, other noodles, gums, ice cream, Alcoholic beverages, and vitamin complexes, all of which include healthy foods in a conventional sense.

The high content of the isoflavone derivative of the present invention, the extract of the canola, or the fraction of the extract may be used as it is, or may be used together with other food or food ingredients, and may be suitably used according to a conventional method. The amount of the active ingredient to be mixed can be suitably determined according to its use purpose (for prevention or improvement). Generally, the amount of the isoflavone derivative high in content of the healthy food, the content of the soybean leaf, the extract of the canola or the fraction of the extract may be 0.01 to 15% by weight of the whole food, 5 g, preferably 0.3 to 1 g. However, in the case of long-term intake intended for health and hygiene purposes or for the purpose of controlling health, the amount may be less than the above range, and since there is no problem in terms of safety, the active ingredient may be used in an amount exceeding the above range.

The health functional beverage composition of the present invention has no particular limitation on the components other than the soybean leaves, the extract of the canola or the fraction of the extract of the present invention as the essential ingredient, Flavoring agents, natural carbohydrates and the like as additional components. Examples of the above-mentioned natural carbohydrates include monosaccharides such as glucose, fructose and the like; Disaccharides such as maltose, sucrose and the like; And polysaccharides, for example, conventional sugars such as dextrin, cyclodextrin and the like, and sugar alcohols such as xylitol, sorbitol and erythritol. Natural flavors (tau martin, stevia extracts (e.g., rebaudioside A, glycyrrhizin, etc.) and synthetic flavors (saccharin, aspartame, etc.) can be advantageously used as flavors other than those described above .

In addition to the above-mentioned foods, the food of the present invention may contain flavors such as various nutrients, vitamins, minerals (electrolytes), synthetic flavors and natural flavors, colorants and heavies (cheese, chocolate etc.), pectic acid and its salts, Salts, organic acids, protective colloid thickeners, pH adjusting agents, stabilizers, preservatives, glycerin, alcohols, carbonating agents used in carbonated beverages and the like. In addition, the high content of the isoflavone derivative of the present invention, the canola leaf extract or the fraction of the above extract may contain natural fruit juice and pulp for the production of fruit juice drinks and vegetable drinks. These components may be used independently or in combination. Although the proportion of such an additive is not so important, it is generally selected from the range of 0 to about 20 parts by weight per 100 parts by weight of the high content of the isoflavone derivative of the present invention, the extract of the canola, or the fraction of the extract.

The present invention also provides an antioxidant pharmaceutical composition containing as an active ingredient, a high content of an isoflavone derivative produced by treating ethylene glycol, an ethylene donor or an ethylene generator on a soybean leaf, an extract of the canola leaf, or a fraction thereof do.

Also, the present invention provides an antioxidant health food containing as an active ingredient, an isoflavone derivative high content soybean leaf, an extract of the canola leaf, or a fraction of the above extract prepared by treating soybean leaves with ethylene, an ethylene donor or an ethylene generator .

Since the isoflavone derivatives isolated from the soybean leaves containing the isoflavone of the present invention have established physiological activity, the soybean leaf extract containing the compounds and fractions thereof can be usefully used as an antioxidant composition.

The present invention also relates to a pharmaceutical composition for skin care comprising an isoflavone derivative high in content of soybean leaves, an extract of the canola leaves, or a fraction of the above extract prepared by treating soybean leaves with ethylene, ethylene donor or ethylene generator to provide.

The present invention also provides a cosmetic composition for skin care comprising an isoflavone derivative high in content of soybean leaves, an extract of the canola, or a fraction of the above extract prepared by treating soybean leaves with ethylene, ethylene donor or ethylene generator do.

Further, the present invention provides a health food for skin care containing an isoflavone derivative high in content of soybean leaves, an extract of the canola leaves, or a fraction of the above extract prepared by treating soybean leaves with ethylene, ethylene donor or ethylene generator do.

Since the isoflavone derivatives isolated from the soybean leaves containing the isoflavone of the present invention have established physiological activity, the soybean leaf extract containing the compounds and the fractions thereof can be usefully used as a composition for skin-beauty treatment.

The cosmetic composition may include, but is not limited to, lotions, ointments, gels, creams, patches or sprays. In producing a cosmetic composition containing a high content of an isoflavone derivative of the present invention, an extract of the canola leaf, or a fraction of the above extract, a composition containing a high content of an isoflavone derivative of the present invention, Or the fraction of the extract may be added in an amount of 3 to 30 parts by weight, preferably 5 or 20 parts by weight.

The cosmetic composition of the present invention may further contain a fatty substance, an organic solvent, a solubilizing agent, a thickening agent and a gelling agent, a softening agent, an antioxidant, a suspending agent Stabilizers, foaming agents, fragrances, surfactants, water, ionic or nonionic emulsifiers, fillers, sequestering and chelating agents, preservatives, vitamins, barrier agents, wetting agents, essential oils, dyes, pigments , Hydrophilic or lipophilic active agents, lipid vesicles or any other ingredient conventionally used in cosmetic compositions.

The components can also be introduced in amounts commonly used in the field of dermatology.

In addition, the present invention provides tea using a high content of an isoflavone derivative of the present invention.

The present invention also provides a mixed tea comprising a high content of an isoflavone derivative of the present invention and a herb plant having a flavor.

The tea using the canola leaves

1) washing and shattering the high content soybean leaves of the isoflavone derivative according to the present invention;

2) roasting the crushed leaves; And

3) drying the roasted leaves.

In this method, the crushing of step 1) is preferably finely crushed to 1 to 5 mm using a crusher, but the size is not limited thereto.

In the above method, the roasting of step 2) is preferably roasted at a temperature of 250 to 300 DEG C for 30 to 60 minutes in a roaster, but the temperature and time are not limited thereto.

In the above method, the drying of step 3) may be carried out by using a natural dryer or a dryer, and drying is preferably performed at a temperature of 30 to 50 ° C for 24 to 36 hours, but the temperature and time are not limited thereto.

The herb plant is preferably at least one selected from the group consisting of chemomail, lemongrass, rosehip, lavender, peppermint, fennel, rosemary, jasmine, hibiscus, rose flower, apple fruit, strawberry fruit, lemon fruit, Hubs are all available.

The tea or mixed tea may be processed into a form selected from the group consisting of a flavored tea, a tea bag, an instant tea, and a can.

Hereinafter, the present invention will be described in detail with reference to Examples and Production Examples. EXAMPLES The following examples and preparative examples are merely illustrative of the present invention, and the present invention is not limited by the following examples and preparative examples.

< Example  1> Isoflavone derivatives High content  Manufacture of canned leaves

RDA is distributing soybean seeds (Glycine max) in a soybean plant from 10 to 90 days after sowing and adding 5 to 100 ppm of ethephon (2-chloroethylphosphonic acid) or 5 500 ppm of ethylene was treated to produce a high content of isoflavone derivative. The manner in which isoflavones accumulate in the lecithin can vary depending on the concentration of the etexone or ethylene to be treated and the growth period of the plant being treated.

Specifically, when soybean plants diluted in water at a concentration of 50 ppm were periodically treated with bean plants for 40 days after sowing, the target isoflavones were rapidly accumulated from day 1 after treatment, On the 12th day, the highest concentration of isoflavone was collected.

In addition, soybean leaves were harvested from soybean plants (10-90 days old) after sowing, and then treated with 5 ~ 100 ppm diluted eshephons periodically. At 3-10 days after treatment, the highest concentration of isoflavone derivatives was collected.

As a result, as shown in Fig. 1, the concentration of the target isoflavone derivative of the soybean leaf was increased after the treatment, and the soybean leaf having the highest concentration of the isoflavone derivative was obtained about 5 to 12 days after the treatment. In addition, it was confirmed that the soybean leaf gradually changed to yellow due to the influence of ethylene, which is a plant aging hormone (Fig. 1). Therefore, from the above results, isoflavone diluted to 5-100 ppm level or 10-500 ppm of ethylene was treated to soybean plants 10 to 90 days after sowing, On the 5th to 12th day, soybean leaves having the maximum content of isoflavone derivatives were obtained.

< Example  2> Production of high content of isoflavone derivatives

The soybean leaves obtained by the method of Example 1 were dried and then extracted with 50-100% alcohol at 20-100 ° C for 3-10 days. The extracted solvent was concentrated under reduced pressure to obtain an extract at a yield of 8-15%.

Specifically, the soybean leaf obtained by the method described in Example 1 was dried, and 1 kg of the dried soybean leaf was extracted with 80% ethanol at room temperature for 7 days, and the extracted solvent was concentrated under reduced pressure to obtain 86 g of an extract. The dried bean leaves were extracted with pure water at 40-100 ° C. The extracted solvent was concentrated under reduced pressure to obtain an extract at a yield of 10-17%.

As a result, as shown in FIG. 2 and FIG. 3, the content of the isoflavone derivative was remarkably high in the extract obtained by extracting the soybean leaves with ethanol after 7 days of treatment with the esophone, compared with the extract obtained by extracting the soybean leaves with ethanol before treatment (Figs. 2 and 3).

< Example  3> Isoflavone derivatives were isolated and purified from soybean leaves

Isoflavone derivatives were separated and purified from the high-content isoflavone ethanol fraction obtained by the method described in Example 2 above using MPLC (Teledyne Isco CombiFlash Companion). C18 silica gel (YMC, 50 μm) was used as the column material. The elution conditions were gradient elution of acetonitrile solvent to 0-90% in water / acetonitrile mixed solution, Respectively.

In order to isolate and purify the isoflavone derivative from the extract of the high content of the isoflavone derivative obtained by the method described in the above Example 2 and treated with beta-glucosidase to the bean leaf ethanol extract, Silica gel chromatography was performed to separate the two isoflavone derivatives of the four isoflavone glycosides converted by beta-glucosidease. Thus, a total of six isoflavone derivatives were isolated.

< Example  4> Structural analysis of isolated isoflavone derivatives

UPLC / Q-TOF MS and NMR spectroscopy were performed to analyze the structures of the six isoflavone compounds separated by the six isoflavone derivative methods separated by the method described in Example 3 above.

As a result, as shown in Fig. 4, it was confirmed that peak 1 of the six isoflavone derivatives was daidzin represented by the following formula (2) (Fig. 4).

(2)

Daidzin (peak 1): ESI-MS (Q -TOF) [M + H] + 417.1186 (. Calc 417.1186, C 21 H 21 O 9, 0.0 ppm); ^{1 H NMR (500MHz, DMSO- d} 6) δ 3.30 (2H, m, H-4 ", 2"), 3.47 (3H, m, H-3 ", H-5", 6˝b), 3.73 ( (2H, d, J = 8.6 Hz, H-3 ', 5'), 6.12 (1H, d, J = 14.2, 7.4 Hz, 7.15 (1H, dd, J = 8.6, 2.1 Hz, H-6), 7.24 (1H, d, J = 2.1 Hz, H-8), 7.41 (2H, d, J = 8.6 Hz, H-2', 6 '), 8.04 (1H, d, J = 8.9 Hz, H-5), 8.39 (1H, s, H-2), and 9.56 (1H, s, 4'-OH); ^{13 C NMR (125 MHz, DMSO-} d 6) δ 61.1 (C-6˝), 70.1 (C-4˝), 73.6 (C-2˝), 76.9 (C-3˝), 77.7 (C-5 1), 115.6 (C-3 ', 5'), 116.0 (C-6), 118.9 (C-4a), 122.8 (C-1), 127.4 (C-5), 130.6 (C-2 &apos;, 6 &apos;), 153.8 C-7), 175.2 (C-4).

Further, as shown in Fig. 5, it was confirmed that Peak 2 was genistin represented by the following Chemical Formula 3 (Fig. 5).

(3)

Genistin (peak 2): ESI-MS (Q -TOF) [M + H] + 433.1139 (. Calc 433.1135, C 21 H 21 O 10, 0.9 ppm); ^{1 H NMR (500 MHz, DMSO-} d 6) δ 3.19 (1H, dd J = 9.9, 4.8 Hz, H-4 "), 3.29 (1H, dd, m, J = 13.4, 7.4 Hz, H-2" ), 3.32 (1H, dd, J = 13.4, 4.8 Hz, H-3 "), 3.45 (1H, m, H-5"), 3.48 (1H, dd, J = 11.4, 5.5 Hz, H-6 " b), 3.73 (1H, dd , J = 11.4, 4.8 Hz, H-6 "a), 5.06 (1H, d, J = 7.4 Hz, H-1"), 6.49 (1H, d, J = 2.1 Hz , H-6), 6.72 ( 1H, d, J = 2.1 Hz, H-8), 6.84 (2H, d, J = 6.6 Hz, H-3', 5'), 7.41 (2H, d, J = 6.6 Hz, H-2 ', 6'), 8.41 (1H, s, H-2), 9.53 (1H, s, 4'-OH), and 12.9 (1H, s, 5-OH). ^{13 C NMR (125 MHz, DMSO-} d 6) δ 61.1 (C-6 "), 70.1 (C-4"), 73.6 (C-2 "), 76.9 (C-3"), 77.6 (C-5 ), 95.0 (C-8), 100.0 (C-6), 100.4 (C-1) C-1 '), 130.5 (C-2', 6 '), 154.9 (C-2), 157.6 C-7), 180.9 (C-4).

Further, as shown in Fig. 6, among the six isoflavone derivatives, Peak 3 was found to be malonyldaidzin represented by the following formula (4) (Fig. 6).

[Chemical Formula 4]

Malonyl daidzin (peak 3): ESI-MS (Q -TOF) [M + H] + 503.1190 (calc 503.1190, C 24 H 23 O 12, 0.0 ppm.); ^{1 H NMR (500 MHz, DMSO-} d 6) δ 3.17 (2H, m, malonyl-CH 2), 3.19 (1H, m, H-4 "), 3.34 (1H, m, H-2"), 3.38 (1H, m, H-6 "), 3.75 (H-5"), 4.14 , J = 7.6 Hz, H- 1 "), 6.52 (2H, d, J = 8.2 Hz, H-3', 5'), 6.74 (1H, d, J = 8.9 Hz, H-6), 7.04 ( 1H, s, H-8), 7.38 (2H, d, J = 8.2 Hz, H-2 ', 6'), 7.95 (1H, d, J = 8.9 Hz, , H-2). ⁴ C NMR (125 MHz, DMSO- d ₆ ) ? 41.9 (malonyl-CH ₂ ), 64.2 (C-6?), 67.3 (C-4a), &lt; / RTI &gt; 75.6 (C-3) , 120.4 (C-3), 121.9 (C-1 '), 130.2 (C-2', 6 '), 157.6 (C-7), 166.8 (malonyl-COOR), 169.5 (malonyl-COOH), 179.9 (C-4).

Further, as shown in Fig. 7, among the six isoflavone derivatives, Peak 4 was found to be malonylgenistin represented by the following formula (5) (Fig. 7).

[Chemical Formula 5]

Malonyl genistein (Peak 4): ESI-MS (Q-TOF) [M + H] ⁺ 519.1138 (calc. 519.1139, C ₂₄ H ₂₃ O ₁₃ , -0.2 ppm); ^{1 H NMR (500 MHz, DMSO-} d 6) δ 3.19 (2H, m, malonyl-CH 2), 3.20 (1H, m, H-4 "), 3.28 (1H, m, H-2"), 3.33 (1H, m, H-3 "), 4.12 (1H, m, H-6" b), 4.35 (1H, m, H-6 "a), 5.12 (1H, d, J = 7.7 Hz, H- (2H, d, J = 8.1 Hz, H-3 ', 5'), 7.39 (2H, d, J = 8.1 Hz, H-2 ', 6'), 8.40 (1H, s, H-2). ^{13 C NMR (125 MHz, DMSO-} d 6) δ 41.6 (malonyl-CH 2), 63.9 (C-6 "), 69.4 (C-4"), 72.7 (C-2 "), 73.6 (C-5 (C-3), 94.3 (C-8), 99.3 (C-1 "), 99.4 (C-6), 106.0 , 120.9 (C-1 '), 122.5 (C-3), 130.2 (C-2', 6 '), 154.6 (C-5), 162.6 (C-7), 167.0 (malonyl-COOR), 167.5 (malonyl-COOH), 180.5 (C-4).

Further, as shown in FIG. 8, it was confirmed that one of the isoflavone derivatives converted from the four isoflavone derivatives was a daidzein represented by the following formula (6) (FIG. 8).

[Chemical Formula 6]

Daidzein: ESI-MS (Q-TOF ) [M + H] + 255.0658 (calc 255.0657, C 15 H 11 O 4, 0.4 ppm.); ^{1 H NMR (500 MHz, DMSO-} d 6) δ 6.84 (2H, d J = 8.6 Hz, H-3', 5') , 6.85 (1H, d, J = 2.0 Hz, H-8), 6.96 (1H, dd, J = 8.8, 2.2 Hz, H-6), 7.38 (2H, d J = 8.6 Hz, H-2 ', 6'), 8.07 (1H, d, J = 8.8 Hz, H-5), 8.15 (1H, s, H-2). ^{13 C NMR (125 MHz, DMSO-} d 6) δ 102.5 (C-8), 115.4 (C-6), 115.6 (C-3', 5'), 117.0 (C-4a), 123.0 (C-1 ), 123.9 (C-3), 127.7 (C-5), 130.5 (C-2 ', 6'), 153.2 163.1 (C-7), 175.1 (C-4).

Further, as shown in Fig. 8, it was confirmed that one of the isoflavone derivatives converted from the four isoflavone derivatives was genistein represented by the following formula (7) (Fig. 8).

(7)

Genistein: ESI-MS (Q-TOF ) [M + H] + 271.0600 (. Calc 271.0606, C 15 H 11 O 5, -2.2 ppm); ^{1 H NMR (500 MHz, DMSO-} d 6) δ 6.21 (1H, d J = 1.6 Hz, H-6), 6.33 (1H, d, J = 1.6 Hz, H-8), 6.86 (1H, dd, J = 6.7, 1.8 Hz, H-3', 5'), 7.38 (1H, dd, J = 6.7, 1.8 Hz, H-2', 6') , 8.06 (1H, s, H-2). ¹³ C (125 MHz, DMSO- d ₆ ) ? 94.0 (C-8), 99.3 (C-6), 104.8 ), 122.7 (C-1 '), 130.5 (C-2', 6 '), 154.3 (C-2), 157.8 164.7 (C-7), 180.6 (C-4).

< Example  5> UPLC Quantitative analysis of isoflavone derivatives using

Quantitative analysis of the four isoflavone compounds isolated from the four kinds of isoflavone compounds separated by the method described in the above Example 3 and the soybean leaves treated with the collected essephenes was carried out using UPLC.

Specifically, the UPLC was an ACQUITY UPLC ^™ system from Waters (USA), and the column was an ODS-based BEH C18 (100 × 2.1 mm). The mobile phase was acetonitrile containing 0.1% acetic acid and 0.1% acetic acid, and gradient elution was applied in which the acetonitrile solvent was increased from 57% at the initial 3% for 15 minutes. The flow rate was adjusted to 0.4 ml / min, the amount of the extracted solution was 2 μl, and the detection wavelength was analyzed at 254 nm. Four isoflavone compounds isolated by the method described in Example 3 were dissolved in methanol to prepare a standard solution in the range of 1-100 μg / ml, subjected to UPLC analysis, and a calibration curve was drawn from the peak area Respectively. The isoflavone standard used in the analysis was four kinds of didegene, genistin, malonyl didezin and malonyl genistein, all of which contained 98% or more of high purity standards (Table 1).

The soybean leaves of the bean plants, which were 10-90 days old after sowing in Example 1, were collected and treated with 50 ppm of the ensemble, and the four isoflavone compounds were separated by the method described in Example 3 , And quantitative analysis was performed as described above (Table 2).

As a result, as shown in Table 1, the isoflavone derivatives were not detected in the ethanol fraction of the soybean leaves not treated with the espe- phon, while the isoflavone derivatives were not detected in the ethanol fraction of the soybean leaves treated with 50 ppm of the espe- phon And the content increased sharply. In particular, it was confirmed that the total isoflavone content was 17073 ㎍ / g at the 7th day after treatment with espe- phon (Table 1).

In addition, as shown in Table 2, it was confirmed that the content of isoflavone derivatives was rapidly increased as in the case of soybean leaves harvested after treating with espe- phon, even in soybean leaves treated with espe- phon after collection (Table 2). Therefore, it was confirmed that the method of preparing the soybean leaves after treating the esophone through the above results, as well as the method of treating the esophone in the harvested soybean leaves, can produce the soybean leaves having a high content of the isoflavone derivatives.

Isoflavone Content (/ / g) No treatment Processing Day 1 Processing Day 3 Processing Day 5 Processing Day 7 Daid Jean ( 1 ) Not detected 1428.3 ± 42.4 1938.2 ± 71.3 2538.0 + - 74.9 2759.5 ± 82.4 Genevieve ( 2 ) Not detected 1463.4 ± 38.2 2254.3 ± 76.1 2648.3 ± 68.2 2863.7 ± 94.1 Malonylide jean ( 3 ) Not detected 2569.6 ± 50.8 3615.2 + - 93.5 4423.7 ± 149.5 5688.6 ± 171.2 Maloney Genestin ( 4 ) Not detected 2608.7 ± 57.1 4275.9 ± 120.7 4899.4 + 141.2 5761.5 ± 136.5 Total isoflavone - 8070.0 ± 189 12083.6 ± 362 14512.4 + - 434 17073.3 ± 484

Isoflavone Content (/ / g) No treatment Processing Day 1 Processing Day 2 Processing Day 3 Daid Jean ( 1 ) Not detected 1280.4 ± 22.9 1551.2 ± 31.4 1991.5 ± 51.8 Genevieve ( 2 ) Not detected 1316.7 ± 27.5 1803.4 ± 48.2 2098.7 ± 56.2 Malonylide jean ( 3 ) Not detected 2312.1 + - 33.4 3337.9 ± 56.2 3528.4 ± 94.1 Maloney Genestin ( 4 ) Not detected 2347.4 ± 37.2 3480.6 + - 72.4 3909.2 ± 91.7 Total isoflavone - 7256.6 ± 121 10173.1 ± 208 11527.8 ± 294

The preparation examples for the composition of the present invention are illustrated below.

< Manufacturing example  1> Preparation of pharmaceutical preparations

<1-1> Sanje  Produce

The isoflavone derivatives of the present invention,

0.1 g of the extract or the fraction of the extract

Lactose 1.5 g

Talc 0.5 g

The above ingredients were mixed and filled in an airtight container to prepare powders.

<1-2> Manufacture of tablets

The isoflavone derivatives of the present invention,

0.1 g of the extract or the fraction of the extract

Lactose 7.9 g

Crystalline cellulose 1.5 g

0.5 g of magnesium stearate

After mixing the above ingredients, tablets were prepared by direct tableting method.

<1-3> Preparation of capsules

The isoflavone derivatives of the present invention,

0.1 g of the extract or the fraction of the extract

Corn starch 5 g

4.9 g of carboxycellulose

After mixing the above components to prepare a powder, the powder was filled in a hard capsule according to a conventional preparation method of a capsule to prepare a capsule.

&Lt; 1-4 > Preparation of injection

The isoflavone derivatives of the present invention,

0.1 g of the extract or the fraction of the extract

Sterile sterilized water for injection

pH adjuster

(2 ml) per ampoule according to the usual injection preparation method.

<1-5> Liquid  Produce

The isoflavone derivatives of the present invention,

0.1 g of the extract or the fraction of the extract

10 g per isomer

5 g mannitol

Purified water quantity

Each component was dissolved in purified water in accordance with a conventional method for producing a liquid agent, and the lemon flavor was added in an appropriate amount, followed by mixing the above components. Then, purified water was added to adjust the total volume to 100 ml, and the solution was filled in a brown bottle and sterilized to prepare a liquid preparation.

< Manufacturing example  2> Manufacture of health food

<2-1> Mixed car  Produce

A mixed tea was prepared by mixing the high content of the isoflavone derivative of the present invention with the soybean leaf, the extract or the fraction of the extract or the herb plant having the flavor.

<2-2> Production of flour food

Bread, cake, cookies, crackers and noodles were prepared by adding 0.5-5.0 parts by weight of a high content of an isoflavone derivative of the present invention to the flour and mixing the mixture with the mixture.

<2-3> soup  And juicy ( gravies )

0.1 to 5.0 parts by weight of a high content of an isoflavone derivative of the present invention, a soybean leaf, an extract thereof or an extract thereof, was added to soups and juices to prepare health promotion meat products, noodle soups and juices.

<2-4> Ground Beef  Produce

A ground beef for health promotion was prepared by adding 10 parts by weight of the high content isoflavone derivative of the present invention to the soybean leaf, its extract or the fraction of the extract.

<2-5> Dairy products ( dairy products )

5 to 10 parts by weight of the high content isoflavone derivative of the present invention is added to milk, and various dairy products such as butter and ice cream are prepared using the milk.

<2-6> Solar  Produce

Brown rice, barley, glutinous rice, and yulmu were alfaltered by known methods, dried, and then powdered to a powder having a particle size of 60 mesh by a pulverizer.

Black soybeans, black sesame seeds, and perilla seeds were steamed and dried by a conventional method, and then they were prepared into powder having a particle size of 60 mesh by a pulverizer.

The high content of the isoflavone derivative of the present invention, the extract or extract fraction thereof was concentrated under reduced pressure in a vacuum concentrator, dried by spraying and dried in a hot air drier, and pulverized to a size of 60 mesh with a pulverizer to obtain a dry powder.

The above-prepared cereals, seeds, and high content of isoflavone derivatives of the present invention were prepared by blending the following ingredients:

(30 parts by weight of brown rice, 15 parts by weight of yulmu, 20 parts by weight of barley)

Seeds (7 parts by weight of perilla, 8 parts by weight of black beans, 7 parts by weight of black sesame seeds)

(3 parts by weight) of the high content isoflavone derivative of the present invention, the extract or extract fraction thereof,

(0.5 part by weight),

(0.5 parts by weight)

< Manufacturing example  3> Manufacture of health drinks

The isoflavone derivatives of the present invention,

100 mg of the extract or the fraction of the extract

Citric acid 100 mg

100 mg of oligosaccharide

2 mg of plum concentrate

100 mg taurine

Purified water was added to 500 ml

The above components were mixed according to a conventional health drink manufacturing method, and the mixture was stirred and heated at 85 DEG C for about 1 hour. The resulting solution was filtered to obtain a sterilized 1 liter container which was sealed and sterilized, &Lt; / RTI &gt;

Although the compositional ratio is relatively mixed with a component suitable for a favorite drink, it is also possible to arbitrarily modify the compounding ratio according to the regional or national preference such as the demand class, the demanding country, and the use purpose.

< Formulation example  4> Cosmetics  Preparation of composition

<4-1> Preparation of cream

The isoflavone derivatives of the present invention,

4.6 parts by weight of the extract or the fraction of the extract

Cetostearyl alcohol 2.8 parts by weight

Beeswax 2.6 parts by weight

Stearic acid 1.4 parts by weight

Glycerin monostearate 2 parts by weight

&Lt; tb &gt; &lt; tb &gt;

Sorbitol sesquioleate 1.4 parts by weight

Jojoba oil 4 parts by weight

Squalane 3.8 parts by weight

Polysorbate 60 1.1 parts by weight

Macadia oil 2 parts by weight

Tocopheryl acetate 0.2 part by weight

Methylpolysiloxane 0.4 part by weight

Ethylparaben 0.1 part by weight

Propylparaben 0.1 part by weight

Euxyl K-400 0.1 part by weight

1,3-butylene glycol 7 parts by weight

Methylparaben 0.05 part by weight

Glycerin 6 parts by weight

d-Pandenol 0.2 part by weight

Triethanolamine 0.2 part by weight

pt 41891 0.2 part by weight

p-H20 46.05 parts by weight

<4-2> Production of Lotion

The isoflavone derivatives of the present invention,

3.5 parts by weight of the extract or the fraction of the extract

Cetostearyl alcohol 1.6 parts by weight

Stearic acid 1.4 parts by weight

Glycerin monostearate of pro-type 1.8 parts by weight

&Lt; tb &gt; &lt; tb &gt;

Sorbitol sesquioleate 0.6 parts by weight

Squalene 4.8 parts by weight

Macadia oil 2 parts by weight

Jojoba oil 2 parts by weight

Tocopheryl acetate 0.4 part by weight

0.2 part by weight of methylpolysiloxane

Ethylparaben 0.1 part by weight

Propylparaben 0.1 part by weight

4 parts by weight of 1,3-butylene glycol

0.1 part by weight of methylparaben

Xanthan gum 0.1 part by weight

Glycerin 4 parts by weight

d-Pandenol 0.15 part by weight

Allantoin 0.1 part by weight

Cargar (2% aq. Sol) 4 parts by weight

Triethanolamine 0.15 part by weight

Ethanol 3 parts by weight

pt 41891 0.1 part by weight

p-H20 48.3 parts by weight

Claims (19)

A method for producing a high content of an isoflavone derivative represented by the following formulas (2) to (5), comprising treating the soybean leaf with ethylene, ethylene donor or ethylene generator at a concentration of 5 to 500 ppm :
(2)

;
(3)

;
[Chemical Formula 4]

;
[Chemical Formula 5]

.
The method according to claim 1, wherein the soybean leaf is a soya bean having been aged 10 to 90 days after sowing, wherein the soybean leaf is represented by the following formulas (2) to (5).
The method according to claim 1, wherein the ethylene donor is ethephon. 2. The method according to claim 1, wherein the ethylene donor is ethephon.
The method according to claim 1, wherein the ethylene, ethylene donor or ethylene generator is treated at a concentration of 5 to 100 ppm, wherein the isoflavone derivative is represented by the following formulas (2) to (5) .
The method according to claim 1, further comprising the step of treating beta-glucosidase. 2. The method according to claim 1, wherein the method comprises the step of treating beta-glucosidase.
6. The method according to claim 5, wherein the soybean leaves further comprise an isoflavone derivative represented by the following formulas (2) to (5), further comprising an isoflavone derivative represented by the following formula (6) : &Lt;
[Chemical Formula 6]

;
(7)

.
A high content of an isoflavone derivative represented by the following formulas (2) to (5) prepared by the production method of (1) or (5).
1) treating the soybean leaf with ethylene, an ethylene donor or an ethylene generator at a concentration of 5 to 500 ppm to prepare a canola; And
2) extracting a large amount of an isoflavone derivative represented by the following formulas (2) to (5), which comprises extracting an isoflavone derivative represented by the following formulas (2) to (5) Production method.
A composition comprising a high content of an isoflavone derivative represented by the following general formulas (2) to (5), a soybean leaf, an extract of the canola or a fraction thereof.
An isoflavone derivative represented by the following formulas (2) to (5): a high content of a soybean leaf, an extract of the canola, or a fraction of the extract;
delete 11. The health food according to claim 10, which is used for prevention and improvement of any one selected from the group consisting of osteoporosis, heart disease, breast cancer, external quality disease, hyperlipidemia, skin aging and facial flushing.
delete delete delete delete A cosmetic composition comprising a high content of an isoflavone derivative represented by the general formulas (2) to (5) of claim 7, an extract of the canola leaf, or a fraction thereof.
delete An isoflavone derivative represented by the following formulas (2) to (5).

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