KR102580873B1 - Method of producing extract having enhanced content of quercetin from onion - Google Patents

Abstract

The present invention provides an efficient and economical method for producing processed onions with increased quercetin content through microwave treatment, and the food, pharmaceutical, and cosmetic uses of the processed products, fractions, and single components with increased quercetin content produced thereby. will be.

Description

Method of producing onion extract with enhanced content of quercetin from onion {Method of producing extract having enhanced content of quercetin from onion}

The present invention relates to a method for producing quercetin from onion or its extract using microwaves and its use.

Onion ( Allium cepa L.) is a perennial plant belonging to the Narcissus family that has been cultivated in Europe for about 1,000 years. It has a unique spicy taste and pungent odor, and is one of the seasoning vegetables widely used around the world along with peppers and garlic. Onions have been used since ancient times, both in the East and the West, to nourish and prevent aging, and are also widely used for fever relief, deworming, detoxification, enteritis, and stroke.

Recently, it has been scientifically revealed that onions contain flavonoids, which have antioxidant properties, and sulfur compounds with various physiological activities, as functional ingredients of onions, making them a functional food for preventing adult diseases such as high blood pressure and arteriosclerosis by improving blood circulation. Interest is increasing.

Among the flavonoid components of onions, they contain substances such as quercetin, kaempferol, and rutin. In particular, flavonoids of the quercetin series are powerful antioxidants that play a role in preventing oxidative damage to cells and rancidity of fat. It accounts for more than 80% of all ingredients. Quercetin present in onions is a powerful antioxidant that prevents oxidative damage to cells and rancidity of fat, thereby lowering the concentration of low-density lipoprotein (LDL) cholesterol. The reason for this effect is that it removes free radicals that are highly reactive in vivo and damage various components of cells, and reduces low-density lipoprotein oxidation, which is the cause of arteriosclerosis and heart disease. It is known that this is because it protects and regenerates vitamin E, an antioxidant in the body, and inactivates the harmful effects of metal ions.

Approximately 10% of onions produced domestically are used as processed products, and processed products using onions include snacks containing onions, onion juice, onion vinegar, and onion drinks. In addition, health functional foods using onions include onion extract encapsulation, onion powder tablets, drinks containing onion quercetin, liver function protectors containing quercetin, isoquercetin and natural plant extracts containing them as active ingredients, and anti-aging products containing onion extract. There are beverage compositions, onion tablets using onion powder and red ginseng, onion powder and beta-carotene mixed tablets, liver function protectors and diabetes prevention agents containing quercetin and onion extract containing it as active ingredients.

However, in onion extract, its glycoside compounds, isoquercitrin (Quercetin 3-glucoside) and quercetin 3,4'-diglucoside, are present in greater amounts than quercetin, and are powerful antioxidants. In order to manufacture processed products and health functional foods containing effective quercetin as the main ingredient, specific processing is required.

Accordingly, the present researchers discovered that isoquercetin and quercetin 3,4'-diclucoside, which are glycoside compounds of quercetin, can be efficiently converted to quercetin in a short time through microwave processing, and completed the present invention.

Clean recovery of antioxidant flavonoids from onions: Optimising solvent free microwave extraction method Journal of Chromatography A (Vol. 1216, 2009, pp. 7700-7707). Health Benefits of Quercetin (Defense Life Science Journal. Vol. 2, No. 2, 2017, pp. 142-151)

One aspect provides a method for producing quercetin comprising irradiating onions or extracts thereof with microwaves.

Another aspect provides a pharmaceutical composition comprising quercetin prepared by the above method.

Another aspect provides a health functional food composition containing quercetin prepared by the above method.

Another aspect provides a cosmetic composition comprising quercetin prepared by the above method.

Another aspect provides a method of treating a disease in a subject, comprising administering to the subject a composition containing quercetin prepared by the above method as an active ingredient.

Another aspect provides a method for producing an onion extract with increased quercetin content, comprising irradiating the onion or its extract with microwaves.

Other objects and advantages of the present application will become clearer from the following detailed description together with the appended claims and drawings. Contents not described in this specification can be fully recognized and inferred by a person skilled in the technical field of this application or a similar technical field, so description thereof is omitted.

One aspect provides a method for producing quercetin, comprising irradiating onions or extracts thereof with microwaves.

As used herein, the term “Quercetin” is an antioxidant bioflavonoid found in onions, elderberries, apples, and citrus fruits, and is also called quercetin or quercetin. The quercetin can be expressed by the following formula (1).

[Formula 1]

In the method, the onion or its extract may contain a quercetin glycoside compound. The quercetin glycoside compound refers to a substance in which sugar is bound to quercetin. The quercetin glycoside compound derived from the onion or its extract is isoquercitrin (Quercetin 3-glucoside) and/or quercetin 3,4. It may contain '-diglucoside (Quercetin 3,4'-diglucoside). The isoquercitrin and quercetin 3,4'-diclucoside can be expressed by the following formulas 2 and 3, respectively.

[Formula 2]

[Formula 3]

In the above method, the onion or its extract may be present in the form of a mixture or sample containing quercetin glycoside compounds derived from the onion or its extract. The mixture or sample may include any one containing isoquercitrin and/or quercetin 3,4'-diclucoside. The mixture or sample may contain 1, 3, 5, 10, 15, 20% or more of isoquercitrin and quercetin 3,4'-diclucoside based on the total weight.

The onions may include white onions (oignons blancs), yellow onions (oignons jaunes), red onions (oignons rouges), and their wild seeds, variants, variants, or hybrids. Additionally, onions can be the central core, skin, roots or any part that can contain isoquercitrin and quercetin 3,4'-diclucoside.

In the method, the extract is a crude extract of plant water, C ₁ -C ₄ alcohol, or a mixture thereof; Solvent fractions of n-hexane, methylene chloride, ethyl acetate, butanol, or mixtures thereof of the crude extract; Or it may be a purified product of the solvent fraction.

The crude extract of water, C ₁ -C ₄ alcohol, or a mixture thereof may be, for example, a crude extract of methanol or ethanol. During extraction, extraction may be performed by adding about 5 to 15 times the amount of solvent as the amount of the plant, for example, by adding about 10 times the amount of solvent. After adding the solvent, extraction can be performed by conventional methods such as heat extraction, ultrasonic extraction, and reflux extraction. Preferably, ultrasonic extraction is used. The temperature of the solvent during extraction may be about 50 to 200°C, for example, 120°C. Additionally, the extraction time may be about 2 to 4 hours, for example, about 3 hours. In addition, the number of extractions may be 1 to 5 times, for example, 3 times. The crude extract obtained by this method can be used as the onion extract, but a solvent fraction obtained by additionally extracting the crude extract with an organic solvent can also be used. The organic solvent fraction may be a fraction obtained by extracting the crude extract with methylene chloride, hexane, ethyl acetate, butanol, or a mixture thereof.

In the method, the onion extract may be obtained by a method including the step of incubating a reaction mixture containing onions and an extraction solvent, and the incubation may be performed under ultrasonic irradiation. The ultrasonic irradiation may be performed for 1 hour at 40% power of the ultrasonic extractor.

In the method, the extract may be obtained by a method comprising incubating a reaction mixture containing onion and an extraction solvent, for example, a protic solvent. The incubation may be performed at a reflux temperature of the single solvent or mixed solvent used at 20°C, 30°C, 40°C, or 50°C. The protic solvent may be methanol, ethanol, n-propanol, isopropanol, n-butanol, mixtures thereof, or aqueous solutions thereof.

In the method, the microwave may be a radio wave with a wavelength of 1 m to 1 mm, or a radio wave with a frequency of 300 MHz to 300 GHz. Microwave irradiation may vary depending on the amount or state of the reactant.

In the method, the microwave irradiation is performed under pressure, for example, 1 to 100 atm, 2 to 100 atm, 5 to 100 atm, 7 to 100 atm, 10 to 100 atm, 15 to 100 atm. Atmosphere, 1 atm to 80 atm, 2 atm to 80 atm, 5 atm to 80 atm, 7 atm to 80 atm, 10 atm to 80 atm, 15 atm to 80 atm, 1 atm to 50 atm, 2 atm to 50 atm, 5 to 50 atm, 7 to 50 atm, 10 to 50 atm, 15 to 50 atm, 1 to 30 atm, 2 to 30 atm, 5 to 30 atm, 7 to 30 atm, 10 atm to 30 atm, 15 to 30 atm, 1 to 15 atm, 2 to 15 atm, 5 to 15 atm, 7 to 15 atm, 10 to 15 atm, 1 to 10 atm, 1 to 5 atm, 1 to 3 atm, Alternatively, it may be performed under a pressure of 2 to 10 atmospheres.

In the method, the microwave irradiation is performed at a temperature of 100 to 150° C., for example, 100 to 140° C., 100 to 130° C., 100 to 120° C., 100 to 110° C., 110 to 150° C., 110 to 140° C., 110° C. It may be carried out at 130°C, 110 to 120°C, 120 to 150°C, 120 to 140°C, 120 to 130°C, 130 to 150°C, 130 to 140°C, or 140 to 150°C.

In the above method, the microwave irradiation can be performed for a sufficient time to convert isoquercitrin and quercetin 3,4'-diclucoside contained in onion or its extract into quercetin. The microwave irradiation is performed for 10 minutes to 90 minutes, for example 10 to 80 minutes, 10 to 70 minutes, 10 minutes to 60 minutes, 10 minutes to 50 minutes, 10 minutes to 40 minutes, 10 minutes to 30 minutes, 10 minutes. to 20 minutes, 20 minutes to 90 minutes, 20 minutes to 60 minutes, 20 minutes to 50 minutes, 20 minutes to 40 minutes, 20 minutes to 30 minutes, 30 minutes to 90 minutes, 30 minutes to 60 minutes, 30 minutes to 50 minutes minutes, 30 to 40 minutes, 40 to 90 minutes, 40 to 60 minutes, 40 to 50 minutes, 50 to 90 minutes, 40 to 60 minutes, or 60 to 90 minutes.

In the method, the microwave irradiation may be performed in the presence of amino acids or Lewis acids. The amino acid and Lewis acid may be any acid effective in converting isoquercitrin and quercetin 3,4'-diclucoside contained in onion or its extract to quercetin. Specifically, the amino acid includes leucine, alanine, arginine, and valine. , or glutamine, and the Lewis acid may be an organic acid such as acetic acid, citric acid, or formic acid.

In the above method, the microwave irradiation may be performed in the presence of an acid having the structure of Formula 4 below.

[Formula 4]

In Formula 4, R ₁ , R ₂ and R ₃ are hydrogen (-H), halogen (-F, -Cl, -Br and -I), hydroxy (-OH), amino (-NH ₂ ), car Boxyl (-COOH), nitrile (-CN), nitro (-NO ₂ ), C5-C12 aryl, C2-C20 alkyl, C2-C20 alkenyl, C1-C20 alkynyl, C3-C20 cycloalkyl, C3- C20 cycloketone, C6-C20 arylalkyl or C2-C20 acyl, and the aryl, alkyl, alkenyl, alkynyl, cycloalkyl, cycloketone, arylalkyl or acyl is hydroxy, halogen, amino, carboxyl, nitrile. , nitro, and C1-C10 alkyl. The term "alkyl" refers to a straight-chain or branched saturated hydrocarbon group. Alkyl is for example methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-heptyl, n-octyl, It may contain n-nonyl or n-decyl.

The term "alkenyl" refers to a hydrocarbon group with one or more straight-chain or branched double bonds, and the term "alkynyl" refers to a hydrocarbon group with one or more straight-chain or branched tka double bonds. It means hydrocarbon group.

The term “aryl” refers to an aromatic ring in which each ring-forming atom is a carbon atom. The ring may be monocyclic or polycyclic. The polycyclic ring may include one having a fused ring (e.g., naphthalene) or one having an unfused ring (e.g., biphenyl). The polycyclic ring may have, for example, 2, 3, or 4 rings. The aryl group has, for example, 5 or more, 6 or more, 7 or more, 8 or more, 9 or more, 10 or more, 5 to 12, 5 to 10, or 6 to 10 carbon ring atoms. Such aryl groups include, for example, phenyl, naphthalenyl (eg, naphthalen-1-yl and naphthalen-2-yl), and biphenyl.

The term “cycloalkyl” refers to a non-aromatic carbon ring in which each ring-forming atom is a carbon atom. The cycloalkyl may be monocyclic or polycyclic. The polycyclic ring is one having, for example, 2, 3 or 4 fused rings. The cycloalkyl may include one fused to an aromatic ring. The cycloalkyl contains, for example, 3 or more, 4 or more, 5 or more, 6 or more, 7 or more, 3 to 10, 3 to 7, 5 to 7, or 5 to 6 ring carbon atoms. Cycloalkyls include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclohexadienyl, cycloheptatrienyl, norbornyl, norcanyl, and adamantyl.

The term “cycloketone” refers to the term “cycloalkyl” having a ketone group.

The term “arylalkyl” refers to alkyl substituted with aryl.

The term “halogen” refers to fluoro, chloro, bromo, or iodo.

In the method, the microwave irradiation may be performed in the presence of tri-carboxylic acid. The tricarboxylic acid is an organic acid having three carboxylic acid functional groups, for example, citric acid, isocitric acid, aconitic acid, propane-1,2,3-tricarboxylic acid, agaricic acid, naphthalenetricarboxylic acid, benzenetricarboxylic acid, or trimesic acid. It could be a mountain.

In the method, the concentration of the Lewis acid and amino acid may be any concentration effective for converting the quercetin glycoside compound to quercetin, for example, 1,000 to 10,000 ppm, for example, 1,000 to 9,000 ppm, 1,000 to 8,000 ppm, 1,000 to 1,000 ppm. 7,000 ppm, 1,000 to 6,000 ppm, 1,000 to 5,000 ppm, 1,000 to 4,000 ppm, 1,000 to 3,000 ppm, 1,000 to 2,000 ppm, 2,000 to 10,000 ppm, 2,000 to 9,000 ppm, 2,000 to 8,000 ppm, 2,000 to 7,000 ppm, 2,000 to 6,000 ppm, 2,000 to 5,000 ppm, 2,000 to 4,000 ppm, 2,000 to 3,000 ppm, 3,000 to 10,000 ppm, 3,000 to 9,000 ppm, 3,000 to 8,000 ppm, 3,000 to 7,000 ppm, 3,000 to 6,000 ppm, 3,000 to 5,000 ppm, 3,000 to 4,000 ppm, 4,000 to 10,000 ppm, 4,000 to 9,000 ppm, 4,000 to 8,000 ppm, 4,000 to 7,000 ppm, 4,000 to 6,000 ppm, 4,000 to 5,000 ppm, 5,000 to 10,000 ppm , 5,000 to 9,000 ppm, 5,000 to 8,000 ppm, 5,000 to 7,000 ppm, 5,000 to 6,000 ppm, 6,000 to 10,000 ppm, 6,000 to 9,000 ppm, 6,000 to 8,000 ppm, 6,000 to 7,000 ppm, 7,000 to 10,000 ppm, 7,000 to 9,000 ppm , 7,000 to 8,000 ppm, 8,000 to 10,000 ppm, 8,000 to 8,000 ppm It may be 9,000 ppm or 9,000 to 10,000 ppm.

In the above method, microwave irradiation may be applied to a reaction mixture containing the onion or its extract and a solvent. The solvent is not particularly limited, but may be, for example, a protic polar solvent or an aprotic polar and non-polar solvent. The protic polar solvent may be water, methanol, ethanol, propanol, isopropanol, or butanol. The aprotic polar solvent may be dichloromethane, tetrahydrofuran, ethyl acetate, acetonitrile, dimethylformamide, dimethyl sulfoxide, acetone, 2-butanone, or hexamethylphosphoramide. The non-polar solvent may be pentane, hexane, chloroform, or diethyl ether. The solvent may be a C1-C12 alcohol, a C3-C10 ester, a C3-C10 acetate, a C3-C10 ketone, a C1-C6 unsubstituted or halogenated hydrocarbon, a C2-C10 ring ether, or a mixture thereof. It may be a mixture of one or more of these and water. The solvent may be ethanol, propanol, butanol, acetonitrile, ethyl acetate, acetone, 2-butanone, chloroform, dichloromethane, hexane, mixtures thereof, or a mixture of one or more of the above solvents and water. The hydrocarbon may be an alkane, alkene, or alkyne. The solvent may be an aqueous solution, and the aqueous solution may be a 30 to 99% ethanol aqueous solution. The C1-C12 alcohol may be a C1-C6, C1-C4, or C2-C5 alcohol.

In the method, the solvent may include a 20 to 80% alcohol aqueous solution, for example, 20 to 80%, 30 to 80%, 40 to 80%, 50 to 80%, 60 to 80%, It may contain 20 to 70%, 30 to 70%, 40 to 70%, 50 to 70%, 20 to 60%, 30 to 60%, 40 to 60%, or 30 to 50% ethanol aqueous solution.

The method may further include the step of separating quercetin from the microwave irradiated reaction mixture, and the separating step may include distillation, crystallization, chromatography, or filtration.

In the method, the separating step may include performing chromatography on the reaction mixture irradiated with microwaves. The chromatography may be, for example, reverse-phase C18 column-chromatography, or reverse-phase semi-preparative high-performance liquid chromatography. As a result, the reaction mixture can be separated into a single component of quercetin through preparative liquid chromatography.

The separation method using reversed-phase C18 column chromatography is a separation method commonly used in laboratories. The diameter of the glass tube used and the amount of reversed-phase C18 used may vary depending on the amount of sample to be separated, but usually the inner diameter of the glass tube is A tube of 1 to 10 cm, 10 to 100 cm in length, and a tube filled with 50 to 70% reverse phase C18 at the selected tube height may be used. The composition of the eluent used varies somewhat depending on the amount of sample and the silica gel tube, for example, methanol:water:ethyl acetate = mixed solvent in a volume ratio of 1:1:0 to 1:0:0 to 0:0:1. may be used sequentially according to the mixing ratio.

Separation conditions for reversed-phase preparative HPLC may vary depending on the amount of sample and the size of the column used, but usually reversed-phase preparative HPLC (stationary phase: Phenomenex Luna C18(2) column, particle size 10 μm, length 250x10) mm) was prepared in a liquid chromatography (Shimadzu) instrument, the sample was dissolved in the initial eluent and injected, and the eluent was developed in acetonitrile:water = 50:50 (v/v) and acetonitrile:water for 60 to 90 minutes. =100:0 (v/v) may be separated by increasing.

Other aspects include antioxidant, anti-inflammatory, anti-cancer, neurodegenerative disease prevention, neuronal damage protection, brain nerve protection, prevention of metabolic syndrome, inhibition of weight gain or improvement of dyslipidemia, non-alcoholic fatty liver disease, including quercetin prepared according to the above method. A pharmaceutical composition for improvement is provided. The pharmaceutical composition may be for prevention or treatment. The composition may be in the form of a mixture of substances in which quercetin is not purified into a single compound from the microwave irradiated reaction mixture. The composition may be, for example, a processed extract.

The pharmaceutical composition may contain an onion extract with increased quercetin content prepared according to the above method.

The pharmaceutical composition is used in an amount of 0.01 to 30%, for example, 0.01 to 20%, 0.01 to 15%, 0.01 to 10%, 0.1 to 30%, 0.1 to 20%, 0.1 to 15%, 0.1 to 10%, based on the total weight of the composition. It may include 10%, 0.1 to 5.3%, 0.5 to 5.3%, 1.0 to 5.3%, 0.1 to 5%, 0.1 to 3%, 0.5 to 5%, or 1.0 to 5% quercetin.

The pharmaceutical composition may be formulated in a conventional pharmaceutical formulation known in the art. The pharmaceutical formulation may be formulated and administered in any dosage form. The formulation may include oral administration formulations, injections, suppositories, transdermal administration formulations, and nasal administration formulations. The dosage form may be, for example, a dosage form for oral administration, including liquid preparations such as solutions, emulsions, suspensions, extracts, or syrups, and solid preparations such as powders, granules, tablets, capsules, or pills.

When formulating each of the above formulations, it can be prepared by adding pharmaceutically acceptable excipients or additives necessary for the production of each formulation. Typically, when formulating a solid preparation for oral administration, one or more excipients may be selected from among diluents, lubricants, binders, disintegrants, sweeteners, stabilizers, and preservatives. The excipients may be any pharmaceutically acceptable excipients, and specifically, diluents include lactose, corn starch, soybean oil, microcrystalline cellulose, or mannitol, lubricants include magnesium stearate or talc, and binders include polyvinylpyrrolidone or hydroxide. Roxypropylcellulose is preferred. Additionally, preferred disintegrants include carboxymethylcellulose calcium, sodium starch glycolate, potassium polaacrylin, or crospovidone. When formulating a liquid preparation for oral administration, in addition to water and liquid paraffin, which are commonly used simple diluents, various excipients such as wetting agents, sweeteners, fragrances, and preservatives may be included. The sweeteners include white sugar, fructose, sorbitol, or aspartame, the stabilizers include sodium carboxymethylcellulose, beta-cyclodextrin, white lead, or xanthan gum, and the preservatives include methyl paraoxybenzoate, propyl paraoxybenzoate, or potassium sorbate. desirable. Additionally, one or more types of additives for solid and liquid oral preparations may be selected from flavorings, vitamins, and antioxidants. In addition to the above ingredients, known additives include natural flavorings such as plum flavor, lemon flavor, pineapple flavor, and herb flavor, natural colorings such as natural fruit juice, chlorophyllin, and flavonoids, fructose, honey, sugar alcohol, and sugar to enhance the sense of taste. It can also be used by mixing sweetening ingredients or acidulants such as citric acid and sodium citrate.

The above conventional pharmaceutical formulations can be appropriately prepared by those skilled in the art according to conventional methods known in the art.

The pharmaceutical composition is an active ingredient and is optionally administered several times so that the total daily dose for an adult is about 0.01 mg/kg to 10 g/kg, preferably about 1 mg/kg to 1 g/kg. It can be administered in divided doses. The dosage may be appropriately increased or decreased depending on the route of administration, disease progression, gender, age, weight, etc., or according to the clinical judgment of an expert.

Another aspect provides a method of treating a disease in a subject, comprising administering to the subject a composition containing quercetin as an active ingredient prepared according to the above method. The disease may be prostate cancer, lung cancer, breast cancer, neurodegenerative disease, nerve cell damage, metabolic syndrome, dyslipidemia, and non-alcoholic fatty liver disease. The subject may be a mammal.

Another aspect provides a composition for health functional food containing quercetin prepared according to the above method. The composition may be in the form of a mixture of substances in which quercetin is not purified into a single compound from the microwave irradiated reaction mixture. The composition may be, for example, a processed extract. The food may be a functional food or a health functional food. The composition for health functional food provides antioxidant, anti-inflammatory, anti-cancer, neurodegenerative disease prevention, neuronal damage protection, brain nerve protection, metabolic syndrome prevention, weight gain inhibition, dyslipidemia improvement, and non-alcoholic fatty liver improvement effects. You can.

The composition for health functional food may contain an onion extract with increased quercetin content prepared according to the above method.

The composition for health functional food may be formulated in the formulation of a typical health functional food known in the art.

The health functional food may be manufactured in general dosage forms such as powders, granules, tablets, pills, capsules, suspensions, emulsions, syrups, needles, liquids, extracts, etc., and may be manufactured in meat, sausages, bread, chocolate, candy, etc. It may be manufactured in the form of any health food such as snacks, confectionery, pizza, ramen, other noodles, gum, jelly, dairy products including ice cream, various soups, beverages, tea, drinks, alcoholic beverages, and vitamin complexes. For the formulation of the health food, any food-acceptable carrier or additive can be used, and any carrier or additive known to be usable in the art can be used to prepare the formulation to be manufactured. The above additives include various nutrients, vitamins, electrolytes, flavors, colorants, pectic acid and its salts, alginic acid and its salts, organic acids, protective colloidal thickeners, pH adjusters, stabilizers, preservatives, glycerin, alcohol, and carbonated beverages. It may contain a carbonating agent, etc. In addition, it may contain pulp for the production of natural fruit juice, fruit juice drinks, and vegetable drinks. These additive components can be used independently or in combination, and the ratio of additives is not very important, but may be selected in the range of 0.01 to 0.1 parts by weight per 100 parts by weight of the composition of the present invention.

The content of quercetin in the health functional food composition can be appropriately determined depending on the purpose of use, such as prevention or improvement. Generally, it can be contained in 0.01 to 15% by weight of the total food weight, and when manufactured as a beverage, it can be contained in a ratio of 0.02 to 10 g, preferably 0.3 to 1 g, based on 100 mL.

The beverage may further contain ingredients other than the active ingredients, and may further contain various flavoring agents or natural carbohydrates commonly used in beverages. The natural carbohydrates include common sugars such as monosaccharides (e.g. glucose, fructose, etc.), disaccharides (e.g. maltose, sucrose, etc.), polysaccharides (e.g. dextrin, cyclodextrin, etc.), and xylitol, sorbitol, erythritol, etc. May contain sugar alcohol. Additionally, the flavoring agent may contain natural flavoring agents (e.g., thaumatin, stevia extract, etc.) and synthetic flavoring agents (e.g., saccharin, aspartame, etc.). The natural carbohydrate content is generally about 1 to 20 g, preferably about 5 to 12 g, per 100 mL of beverage.

Health functional foods defined in the present invention have sufficiently established functionality and safety for the human body, which were newly defined through the Health Functional Foods Act, revised in 2008, and have health functions specified in Food and Drug Administration Notice No. 2008-72. It may be a health functional food listed in the regulations on recognition of functional food ingredients.

Another aspect provides a cosmetic composition comprising quercetin prepared according to the above method. The quercetin may be a fraction, a single compound, or a mixture thereof. The cosmetics may be general cosmetics or functional cosmetics. The cosmetic composition containing quercetin, known as a functional ingredient in cosmetics, may be a composition that has antioxidant or anti-inflammatory effects.

The cosmetic composition may contain an onion extract with increased quercetin content prepared according to the above method.

Preparation of the antioxidant or anti-inflammatory cosmetic composition can be performed according to conventional methods.

The cosmetic composition may be prepared in any formulation commonly prepared in the art, but is not limited thereto, for example, a solution; suspension; emulsion; paste; gel; toner; emulsion; essence; Various creams including massage creams, nutritional creams, moisture creams or hand creams; Base makeup products including makeup base, powder, twin cake, foundation or BB cream; Point makeup products for eye makeup or lip makeup; pack; Products for skin cleansing, including soap, cleansing foam, cleansing lotion, cleansing cream, cleansing oil, scrub soap, facial scrub, body scrub, body oil, and body cleanser; spray; and body lotion, preferably a skin cleansing product, more preferably a scrub soap, face scrub, or body scrub. there is.

In addition, the cosmetic composition may include conventional carriers and/or additives suitable for each formulation and well-known in the art, such as, but not limited to, polyols, fat ingredients, moisturizers, softeners, and surfactants. , organic and inorganic pigments, organic powders, sunscreen, preservatives, foam removers, thickeners, disinfectants, antioxidants, plant extracts, pH adjusters, alcohols, pigments, dyes, fragrances, chelating agents, stabilizers, blood circulation promoters, cooling sensation. It may include regulations, restrictions, etc. The type and content can be appropriately selected by a person skilled in the art.

The polyols include glycerin, diglycerin, butylene glycol, propylene glycol, propanediol, pentylene glycol, caprylyl glycol, 1,2-hexanediol, and PEG-6, which are commonly used in cosmetics. and PEG-8, etc., or a mixture thereof may be used, but is not limited thereto, and any one widely known in the art may be used without limitation.

The surfactant includes fatty acid soap commonly used in cosmetics, disodium cocoamphodiacetate, lauryl glucoside, sodium lauryl sulfate, sodium laureth sulfate, disodium laureth sulfosuccinate, ammonium lauryl sulfate, and ammonium. Any one or a mixture thereof selected from the group consisting of laureth sulfate, lauryl glucose carboxylate, potassium glycinate, decyl glucoside, coco glucoside, cocamidopropyl betaine, and cocamidopropyl hydroxysultane may be used. However, it is not limited thereto, and anything that is widely known in the art can be used without limitation.

The pH adjuster may be sodium hydroxide, but any one widely known in the art may be used without limitation.

The chelating agent may be disodium EDTA, but any agent widely known in the art may be used without limitation.

Additionally, the cosmetic composition may contain purified water as the remaining amount excluding the ingredients included in the composition.

Another aspect provides a method for producing an onion extract with increased quercetin content, comprising irradiating the onion or its extract with a microwave.

The method may be to convert quercetin glycoside compounds contained in onions or their extracts to quercetin. Specifically, isoquercitrin and quercetin 3,4'-diclucoside, which are glycoside compounds of quercetin derived from onions, are converted to quercetin. This may increase the content of quercetin.

The onion extract with increased quercetin content may contain 30% or more quercetin based on the total flavonoid weight, for example, 30% to 100%, 40% to 100%, 50% to 100%, 60% to 60%. It may be contained 100%, 70% to 100%, 80% to 100%, or 90% to 100%.

The onion extract with increased quercetin content may contain 30% or more quercetin based on the weight of quercetin, isoquercitrin, and quercetin 3,4'-diclucoside, for example, 30% to 100%, It may be contained 40% to 100%, 50% to 100%, 60% to 100%, 70% to 100%, 80% to 100%, or 90% to 100%.

The onion extract prepared by the above method has a significantly higher quercetin content compared to the simply heat-processed product, resulting in increased medicinal efficacy of quercetin. Quercetin is antioxidant, anti-inflammatory, inhibits proliferation of prostate, lung, and breast cancer, prevents neurodegenerative diseases, protects against nerve cell damage, protects brain nerves, prevents metabolic syndrome, lowers lipoprotein cholesterol (LDL), inhibits weight gain, and dyslipidemia. It is known to be effective in improving liver disease and non-alcoholic fatty liver disease. Therefore, by the continuous microwave irradiation, this effect can be significantly increased compared to a simple heat treatment workpiece.

According to the method for producing quercetin according to one aspect, quercetin can be efficiently produced from onion or its extract.

Compositions according to different aspects can be applied for antioxidant, anti-inflammatory, anti-cancer, neurodegenerative disease prevention, neuronal damage protection, brain nerve protection, metabolic syndrome prevention, weight gain inhibition, dyslipidemia improvement, and non-alcoholic fatty liver disease improvement. .

Figure 1 shows a verification line created by analyzing quercetin by concentration.
Figure 2 shows a verification line created by analyzing isoquacitrin by concentration.
Figure 3 shows a verification line created by analyzing quercetin 3,4'-diclucoside by concentration.
Figure 4 is a UPLC chromatogram analyzing the raw onion extract (Example 1).
Figure 5 is a UPLC chromatogram analyzing the flavonoid components in a product obtained by simply heat-treating a 10,000 ppm solution of onion extract in 50% ethanol for 360 minutes at reflux temperature (Control 1).
Figure 6 is a UPLC chromatogram analyzing the flavonoid components in a product obtained by simply heat-treating a 10,000 ppm solution of onion extract in 50% ethanol for 1,440 minutes at reflux temperature (Control 2).
Figure 7 is a UPLC chromatogram analyzing flavonoid components in a processed product obtained by microwave-processing a 10,000 ppm solution of onion extract in 50% ethanol at 120°C for 30 minutes (Example 2).
Figure 8 is a UPLC chromatogram analyzing flavonoid components in a processed product obtained by microwave-processing a 10,000 ppm solution of onion extract in 50% ethanol at 130°C for 30 minutes (Example 3).
Figure 9 is a UPLC chromatogram analyzing flavonoid components in a processed product obtained by microwave-processing a 10,000 ppm solution of onion extract in 50% ethanol at 140°C for 30 minutes (Example 4).
Figure 10 is a UPLC chromatogram analyzing the flavonoid components in a processed product obtained by microwave-processing a 10,000 ppm solution of onion extract in 50% ethanol at 140°C for 60 minutes (Example 5).
Figure 11 is a UPLC chromatogram analyzing flavonoid components in a processed product obtained by microwave-processing a 10,000 ppm solution of onion extract in 50% ethanol at 150°C for 30 minutes (Example 6).
Figure 12 is a UPLC chromatogram analyzing flavonoid components in a processed product obtained by adding 5 mg of leucine to a 10,000 ppm solution of onion extract in 50% ethanol and microwave processing at 140°C for 30 minutes (Example 7).
Figure 13 is a UPLC chromatogram analyzing flavonoid components in a processed product obtained by adding 5 mg of alanine to a 10,000 ppm solution of onion extract in 50% ethanol and microwave processing at 140°C for 30 minutes (Example 8).
Figure 14 is a UPLC chromatogram analyzing the flavonoid components in a processed product obtained by adding 5 mg of arginine to a 10,000 ppm solution of onion extract in 50% ethanol and microwaved at 140°C for 30 minutes (Example 9).
Figure 15 is a UPLC chromatogram analyzing the flavonoid components in a processed product that was microwaved at 140°C for 30 minutes by adding 5 mg of valine to a 10,000 ppm solution of onion extract in 50% ethanol (Example 10).
Figure 16 is a UPLC chromatogram analyzing the flavonoid components in a processed product obtained by adding 5 mg of glutamine to a 10,000 ppm solution of onion extract in 50% ethanol and microwave processing at 140°C for 30 minutes (Example 11).
Figure 17 is a UPLC chromatogram analyzing the flavonoid components in a processed product obtained by adding 5 mg of citric acid to a 10,000 ppm solution of onion extract in 50% ethanol and microwave processing at 140°C for 30 minutes (Example 12).
Figure 18 is a UPLC chromatogram analyzing the flavonoid component in a processed product obtained by adding 5 mg of acetic acid to a 10,000 ppm solution of onion extract in 50% ethanol and microwaved at 140°C for 30 minutes (Example 13).
Figure 19 is a UPLC chromatogram analyzing flavonoid components in a processed product obtained by adding 5 mg of formic acid to a 1000 ppm solution of onion extract in 50% ethanol and microwaved at 140°C for 30 minutes (Example 14).
Figure 20 is a UPLC chromatogram analyzing the flavonoid components in a processed product obtained by adding 5 mg of citric acid to a 10,000 ppm solution of onion extract in 50% ethanol and microwave processing at 130°C for 30 minutes (Example 15).
Figure 21 is a UPLC chromatogram analyzing the flavonoid components in a processed product obtained by adding 5 mg of citric acid to a 10,000 ppm solution of onion extract in 50% ethanol and microwave processing at 120°C for 30 minutes (Example 16).
Figure 22 is a UPLC chromatogram analyzing the flavonoid components in a processed product obtained by adding 5 mg of citric acid to a 10,000 ppm solution of onion extract in 50% ethanol and microwave processing at 110°C for 30 minutes (Example 17).
Figure 23 is a UPLC chromatogram analyzing the flavonoid components in a processed product obtained by adding 5 mg of acetic acid to a 10,000 ppm solution of onion extract in 50% ethanol and microwave processing at 130°C for 30 minutes (Example 18).
Figure 24 is a UPLC chromatogram analyzing flavonoid components in a processed product obtained by adding 5 mg of acetic acid to a 10,000 ppm solution of onion extract in 50% ethanol and microwaved at 120°C for 30 minutes (Example 19).
Figure 25 is a UPLC chromatogram analyzing the flavonoid components in a processed product obtained by adding 5 mg of citric acid to a 10,000 ppm solution of onion extract in 30% ethanol and microwave processing at 120°C for 30 minutes (Example 20).
Figure 26 is a UPLC chromatogram analyzing flavonoid components in a processed product obtained by adding 5 mg of citric acid to a 10,000 ppm solution of onion extract in 70% ethanol and microwave processing at 120°C for 30 minutes (Example 21).
Figure 27 is a UPLC chromatogram analyzing the flavonoid fraction collected from onion extract by reverse-phase HPLC (Example 22).
Figure 28 is a UPLC chromatogram analyzing the flavonoid component in a processed product obtained by adding 5 mg of citric acid to a solution of 10,000 ppm of the flavonoid fraction in 50% ethanol and microwaved at 120°C for 30 minutes (Example 23).

Below, examples are described in detail to aid understanding of the present invention. However, the embodiments according to the present invention may be modified into various other forms, and the scope of the present invention is not limited to the embodiments described below.

Example 1: Preparation of onion extract

Onions (Muan-gun, Jeollanam-do) were purchased as samples harvested in July 2020, dried and cut into small pieces before use. Put the onion peel, 2.1 kg of onions, and 4 L of ethanol, the extraction solvent, into a 10 L beaker and extract with an ultrasonic extractor (Sonics, VC505) at 40% power for 1 hour, then extract twice at room temperature for 24 hours. I repeated. The extract was concentrated by evaporation under reduced pressure to obtain 116 g of dry extract containing isoquercitrin, quercetin 3,4'-diclucoside, and quercetin. However, accurate quantitative analysis was not possible in the extract due to components other than flavonoids, so 1.5 L of distilled water, 1.2 L of ethyl acetate, and 1.2 L of butanol were sequentially added to the extract to obtain 2.0 g of ethyl acetate layer, 19.0 g of butanol layer, and 1.2 L of butanol as each solvent fraction. and 95.0 g of aqueous layer were obtained. In addition, the following experiment was performed using a butanol layer containing all three flavonoids to measure the conversion rate of isoquercitrin and quercetin 3,4'-diclucoside to quercetin under microwave heat treatment conditions. Analysis of the content of flavonoids contained in the butanol layer was conducted according to the analysis method in Experimental Example 1.

Control groups 1 and 2: simple thermal processing of onion extract

The onion butanol layer extract obtained in Example 1 was processed through heat treatment. Specifically, the onion extract was dissolved at 10,000 ppm in 1 mL of 50% ethanol aqueous solution in a 10 mL container and refluxed in an oil bath for 360 minutes (Control 1) and 1,440 minutes (Control 2), respectively. After simple heat treatment, the processed product was obtained by drying under reduced pressure. Content analysis was conducted according to the analysis method in Experimental Example 1.

Examples 2 to 6: Microwave processing of onion extract

The onion extract obtained in Example 1 was processed by irradiating microwaves. Specifically, onion extract was dissolved at 10,000 ppm in 1 mL of 50% ethanol aqueous solution in a 10 mL container of a microwave irradiator (model number 908005) manufactured by CEM, USA, and after closing the container cap, 120 rpm at 100 W and a frequency of 2450 MHz. 30 minutes at ℃ (Example 2), 30 minutes at 130℃ (Example 3), 30 minutes at 140℃ (Example 4), 60 minutes at 140℃ (Example 5) and 30 minutes at 150℃ (Example Example 6) After each irradiation with a microwave, a microwave irradiation processed product was obtained by drying under reduced pressure. The pressure during microwave irradiation was 1 to 15 atmospheres, and content analysis was performed according to the analysis method in Experimental Example 1.

Examples 7 to 14: Microwave processing of onion extract with amino acids and Lewis acids

The onion extract obtained in Example 1 was processed by irradiating microwaves. Specifically, 5 mg of each amino acid and Lewis acid were dissolved in 1 mL of a 50% ethanol aqueous solution of 10,000 ppm onion extract in a 10 mL container of a microwave irradiator (model number 908005) manufactured by CEM, USA, and the container was closed. It was then performed at 140°C for 30 minutes at 100W and a frequency of 2450 MHz. The amino acids and Lewis acids used were leucine (Example 7), alanine (Example 8), arginine (Example 9), valine (Example 10), glutamine (Example 11), citric acid (Example 12), and acetic acid (Example 12). As Example 13) and formic acid (Example 14), the above amino acid or Lewis acid was added, irradiated with a microwave, and then dried under reduced pressure to obtain a microwave irradiated product. The pressure during microwave irradiation was 1 to 15 atmospheres, and content analysis was performed according to the analysis method in Experimental Example 1.

Examples 15 to 19: Microwave processing temperature optimization of Lewis acid-added onion extract

The onion extract obtained in Example 1 was processed by irradiating microwaves. Specifically, 5 mg of each acid was dissolved in 1 mL of 10,000 ppm onion extract 50% ethanol aqueous solution in a 10 mL container of a microwave irradiator (model number 908005) manufactured by CEM, USA, the container was closed, and then 100W, It was performed at a frequency of 2450 MHz for 30 minutes, and citric acid was added at 130°C (Example 15), 120°C (Example 16), and 110°C (Example 17), and acetic acid was added at 130°C (Example 18). After irradiating with a microwave at 120°C (Example 19), a microwave irradiated product was obtained by drying under reduced pressure. The pressure during microwave irradiation was 1 to 15 atmospheres, and content analysis was performed according to the analysis method in Experimental Example 1.

Examples 20 to 21: Microwave processing of citric acid-added onion extract by solvent

The onion extract obtained in Example 1 was processed by irradiating microwaves. Specifically, 5 mg of citric acid was dissolved in 1 mL of 10,000 ppm onion extract solvent in a 10 mL container of a microwave irradiator (model number 908005) manufactured by CEM, USA, the container was closed, and then irradiated at 100 W and a frequency of 2450 MHz for 120 mL. It was carried out at ℃ for 30 minutes. The solvents used were 30% ethanol aqueous solution (Example 20) and 70% ethanol aqueous solution (Example 21), respectively, and were irradiated with a microwave and then dried under reduced pressure to obtain a microwave irradiated product. The pressure during microwave irradiation was 1 to 15 atmospheres, and content analysis was performed according to the analysis method in Experimental Example 1.

Example 22: Preparation of flavonoid fraction

2 g of the onion extract obtained in Example 1 was mixed with 100% acetonitrile from the initial 10% in water as an eluent on a reverse-phase preparative HPLC (Phenomenex) Luna C18 (2) column, particle size 10 μm, column size 250 x 21.20 mm). The gradient was separated into sections from 17 to 30 minutes at a flow rate of 8 mL/min for 60 minutes to obtain 10 mg of flavonoid fraction.

Example 23: Microwave processing of flavonoid fractions

The flavonoid fraction obtained in Example 22 was processed by irradiating microwaves. Specifically, 5 mg of citric acid was dissolved in 1 mL of 10,000 ppm effective flavonoid fraction solvent in a 10 mL container of a microwave irradiator (model number 908005) manufactured by CEM, USA, the container was capped, and then 100 W, frequency 2450. MHz at 120°C for 30 minutes (Example 23). After irradiation with microwaves, the microwave irradiation processed product was obtained by drying under reduced pressure. The pressure during microwave irradiation was 1 to 15 atmospheres, and content analysis was performed according to the analysis method in Experimental Example 1.

Experimental Example 1: Analysis of flavonoid content in onion extract, simple heat treatment product, and microwave processing product

Based on the verification line values of quercetin, isoquercitrin, and quercetin 3,4'-diclucoside, the flavonoids of the onion extract, simple heat treatment product, and microwave processing were analyzed three times to confirm reproducibility. The single components of quercetin, isoquercitrin, and quercetin 3,4'-diclucoside used in the experiment were 99.3% pure quercetin, 99.4% isoquercitrin, and 99.3% quercetin 3,4' directly isolated from onion raw materials. -Diclucoside was used. According to a general calibration curve measurement method, quercetin, isoquercitrin, and quercetin 3,4'-diclucoside were dissolved in water at 10, 25, 50, 100, and 250 ppm, respectively, to prepare a standard solution, and this was used to prepare a verification line. was written. The elution solvent A used in Ultra Performance Liquid Chromatography (UPLC) is a 0.1% aqueous formic acid solution, and the elution solvent B is acetonitrile, and each was pumped using two pumps. 3 μl of the standard aqueous solution was injected into an analytical reverse-phase column (Phenomenex Luna Omega 1.6 μ Polar C18, 150 Υ 2.1 mm) using a syringe, and an elution solvent with a composition of 90 vol% A and 10 vol% B was added to 1.0%. It flowed at a flow rate of mL/min. Afterwards, the volume % of elution solvent B was gradually changed to 100% (10 min), 100% (15 min), and 10% (17 min). After the above process, each component separated from the column was analyzed through UV spectrum.

Through the above experiment, the flavonoid contents of the above-mentioned control groups 1 and 2 and Examples 1 to 23 were analyzed, and the results of analyzing each component separated from the column by UPLC analysis are shown in Figures 4 to 28 and Tables 1 to 28 below. It is summarized in Table 5.

Experimental Example 2: Comparison of flavonoid contents of simple heat treatment and microwave processing

In order to compare the quercetin content of the simple heat treatment and microwave processing of the onion extract, simple heat treatment samples (control groups 1 and 2) and microwave processing samples of the butanol layer of the onion extract were prepared based on the flavonoid content analysis method in Experimental Example 1. (Examples 2 to 6) Each flavonoid contained in 1g was converted to mg and summarized in Table 1.

division Temperature (℃) - Time (min) quercetin
3,4'-diglucoside iso
Quarcitrin quercetin total amount Processing yield ^*
(Quorcetin content ^** ) Example 1 - 17.7mg 10.8mg 7.9 mg 36.4mg 0%(21.7%) Control group 1 100-360 15.6 mg 9.3mg 8.9mg 33.77mg 6.4%(26.3%) Control group 2 100-1440 15.4mg 9.3mg 8.0mg 33.63mg 0.6%(24.5%) Example 2 120-30 7.0mg 8.8mg 8.4mg 24.2mg 3.2%(34.7%) Example 3 130-30 5.6mg 8.1 mg 9.4mg 23.1mg 9.6%(40.7%) Example 4 140-30 3.5mg 8.1 mg 10.2 mg 21.8mg 14.8%(46.8%) Example 5 140-60 3.4mg 7.9 mg 9.5mg 20.8mg 10.3% (45.7%) Example 6 150-30 n.d. n.d. 7.8mg 7.8mg -0.6% (100%)

( ^* Processing yield = {(final number of quercetin moles - initial quercetin moles)/(initial quercetin 3,4'-diglucoside and isoquercetin moles)}*100

^** Quorcetin content = (Quorcetin mg/Total amount mg)Х100

^*** nd = not detected)

Specifically, the butanol layer of the onion extract was dissolved in 50% ethanol at a concentration of 10,000 ppm, then processed by heat treatment or microwave, and the contents of quercetin 3,4'-diclucoside, isoquercitrin, and quercetin were measured in 1 g of the extract. It is expressed in mg per unit. First, the flavonoids contained in the butanol layer of the onion extract prepared in Example 1, which was not processed by heat treatment or microwave method, were 17.7 mg of quercetin 3,4'-diclucoside, 10.8 mg of isoquercitrin, and quercetin. It was 7.9 mg.

In addition, as a simple thermal processing method, as a result of heating under reflux conditions at 100°C for 360 minutes (control group 1) and 1,440 minutes (control group 2) using an oil bath, the change in flavonoid content was minimal.

Next, when microwave processed at 120°C (Example 2), 130°C (Example 3), 140°C (Example 4), and 150°C (Example 6) for 30 minutes under pressurized conditions, quercetin 3,4 '-The content of diclucoside and isoquercitrin was significantly reduced, and the processing yield converted to quercetin was the highest at 14.8% at 140℃. In particular, at 150℃, quercetin itself tended to be decomposed by heat. showed. Finally, the temperature was fixed at 140°C and microwaved for 60 minutes in the same manner (Example 5), but quercetin showed a tendency to decrease, and the quercetin processing yield was highest under microwave treatment conditions at 140°C for 30 minutes. It was confirmed to be excellent.

Summarizing the above results, it was confirmed that the quercetin processing yield under microwave conditions was overall superior to that under simple heat conditions, and that the microwave processing method under specific conditions was able to obtain a significantly superior quercetin processing yield.

Experimental Example 3: Comparison of flavonoid contents of microwave processed products with added amino acids and Lewis acids

In order to optimize the microwave processing conditions of the onion extract considering the reactivity of quercetin 3,4'-diclucoside and isoquercitrin under microwave conditions and the efficiency of time reduction, based on the flavonoid content analysis method of Experimental Example 1 Each flavonoid contained in 1g of the sample processed by microwave by adding amino acids (Examples 7 to 11) and Lewis acids (Examples 12 to 14) to the butanol layer of the onion extract was converted to mg and summarized in Table 2. .

division Temperature (℃) - Time (min) - Additives quercetin
3,4'-diglucoside iso
Quarcitrin quercetin total amount Processing yield ^*
(Quorcetin content ^** ) Example 1 - 17.7 mg 10.8mg 7.9mg 36.4mg 0%(21.7%) Example 7 140-30-Leucine n.d. 5.9mg 9.1mg 15.0mg 7.7%(60.7%) Example 8 140-30-alanine n.d. 4.9 mg 8.6mg 13.5mg 4.5%(63.7%) Example 9 140-30-Arginine n.d. 2.9mg 7.8mg 10.7mg -0.6% (72.9%) Example 10 140-30-Valine n.d. 4.8mg 9.2 mg 14.0 mg 8.3%(65.7%) Example 11 140-30-Glutamine n.d. 4.8 mg 9.7mg 14.5mg 11.6%(66.9%) Example 12 140-30-citric acid n.d. n.d. 13.3mg 13.3mg 34.7%(100%) Example 13 140-30-acetic acid n.d. 2.3 mg 13.2mg 15.5 mg 34.0%(85.2%) Example 14 140-30-Formic acid n.d. n.d. 9.0mg 9.0mg 7.1%(100%)

( ^* Processing yield = {(final number of quercetin moles - initial quercetin moles)/(initial quercetin 3,4'-diglucoside and isoquercetin moles)}*100

^** Quorcetin content = (Quorcetin mg/Total amount mg)Х100

^*** nd = not detected)

Specifically, the temperature and time were fixed at 140°C and 30 minutes, respectively, and 5 mg each of five amino acids (leucine, alanine, arginine, valine, and glutamine) and three Lewis acids (citric acid, acetic acid, and formic acid) were added. and microwave processed.

As a result, it was confirmed that quercetin 3,4'-diclucoside was completely lost under all conditions under which amino acids were added, but good results were not obtained in terms of yield of processing into quercetin. Next, when reacted in the same manner under Lewis acid conditions, most of quercetin 3,4'-diclucoside and isoquercetin were lost, and 13.3 mg and 13.2 mg of quercetin were obtained under citric acid and acetic acid conditions, respectively. The processing yields were confirmed to be the best at 34.7% and 34.0%, respectively.

Summarizing the above results, it can be seen that when processing onion extract using the microwave method, the overall quercetin processing yield is superior when Lewis acid is added compared to when amino acids are added, especially when citric acid or acetic acid among Lewis acids are added. It can be seen that a significantly excellent quercetin processing yield can be obtained under one condition.

Experimental Example 4: Comparison of flavonoid content by temperature of microwave processed products

In order to compare the processing yield according to temperature under conditions in which citric acid or acetic acid was added during microwave processing, citric acid (Examples 15 to 17) and acetic acid were added to the butanol layer of the onion extract, respectively, based on the flavonoid content analysis method in Experimental Example 1. (Examples 18 and 19) were added and each flavonoid contained in 1g of microwave processed sample was converted to mg and summarized in Table 3.

division Temperature (℃) - Time (min) - Additives quercetin
3,4'-diglucoside iso
Quarcitrin quercetin total amount Processing yield ^*
(Quorcetin content ^** ) Example 1 - 17.7 mg 10.8mg 7.9mg 36.4mg 0%(21.7%) Example 15 130-30-citric acid n.d. n.d. 13.6 mg 13.6 mg 36.6%(100%) Example 16 120-30-citric acid n.d. n.d. 15.2 mg 15.2mg 46.9%(100%) Example 17 110-30-citric acid n.d. 4.2 mg 15.1mg 19.3mg 46.2%(78.2%) Example 18 130-30-acetic acid n.d. 2.1 mg 11.7mg 13.8 mg 24.4%(84.8%) Example 19 120-30-acetic acid 3.9 mg 6.8 mg 11.0 mg 21.7mg 19.9%(50.7%)

( ^* Processing yield = {(final number of quercetin moles - initial quercetin moles)/(initial quercetin 3,4'-diglucoside and isoquercetin moles)}*100

^** Quorcetin content = (Quorcetin mg/Total amount mg)Х100

^*** nd = not detected)

As a result, when experiments were conducted using citric acid at 130℃ and 120℃, the amount and processing yield of quercetin increased as the temperature decreased. 15.2 mg of quercetin was obtained in a 30-minute experiment at 120℃, and the processing yield at this time was the highest. It was confirmed that it was 46.9%. However, when the temperature was further lowered and the experiment was conducted at 110°C, 4.2 mg of isoquercetrin remained, and both quercetin and processing yield were confirmed to be reduced. Next, in the experiment using acetic acid, it was confirmed that both the amount of quercetin and the processing yield decreased when the temperature was lowered and the experiment was conducted at 130°C and 120°C, respectively.

Summarizing the above results, it can be seen that when processing onion extract using the microwave method, the overall quercetin processing yield is superior when citric acid is added compared to when acetic acid is added. In particular, quercetin processing yield is superior at 120°C using citric acid as an additive. It can be seen that both the amount of quercetin and the processing yield were the best when microwave processed for 30 minutes.

Experimental Example 5: Comparison of flavonoid content by solvent in microwave processed products

In order to compare the processing yield according to the solvent under the condition of adding citric acid during microwave processing, citric acid was added to the butanol layer of the above onion extract based on the flavonoid content analysis method of Experimental Example 1, the solvent was changed and microwave processed. Each flavonoid contained in 1g of sample was converted to mg and summarized in Table 4.

division Temperature (℃)-Time (min)-Solvent quercetin
3,4'-diglucoside iso
Quarcitrin quercetin total amount Processing yield ^*
(Quorcetin content ^** ) Example 1 - 17.7mg 10.8mg 7.9mg 36.4mg 0%(21.7%) Example 20 120-30-30% EtOH n.d. n.d. 13.7 mg 13.7mg 37.2%(100%) Example 21 120-30-70% EtOH n.d. 3.7 mg 15.5 mg 19.2mg 48.8%(80.7%)

( ^* Processing yield = {(final number of quercetin moles - initial quercetin moles)/(initial quercetin 3,4'-diglucoside and isoquercetin moles)}*100

^** Quorcetin content = (Quorcetin mg/Total amount mg)Х100

^*** nd = not detected)

Specifically, a microwave processing experiment was performed under the conditions of Example 16 by changing the solvent to 30% ethanol aqueous solution and 70% ethanol aqueous solution. As a result, both quercetin 3,4'-diclucoside and isoquicitrin were lost in the 30% ethanol aqueous solution, but both the amount and processing yield of quercetin were reduced, and in the 70% ethanol aqueous solution, 3.7 mg of isoquercetrin was lost. Although quercetin remained, the result was obtained with a slight increase to 15.5 mg, and the processing yield at this time was confirmed to be 48.8%.

Experimental Example 6: Comparison of flavonoid content of microwave processed products of flavonoid fractions

In order to compare the processing yield during microwave processing of the flavonoid fraction of the onion extract, each flavonoid contained in 1g of the sample processed by microwave using the flavonoid fraction of the onion extract based on the flavonoid content analysis method in Experimental Example 1. Converted to mg and summarized in Table 5.

division Temperature (℃) - Time (min) quercetin
3,4'-diglucoside iso
Quarcitrin quercetin total amount Processing yield ^*
(Quorcetin content ^** ) Example 22 - 115.4mg 216.1mg 49.5mg 381.0mg 0%(13.0%) Example 23 120-30 n.d. 6.1mg 155.2 mg 161.3mg 53.8%(96.2%)

( ^* Processing yield = {(final number of quercetin moles - initial quercetin moles)/(initial quercetin 3,4'-diglucoside and isoquercetin moles)}*100

^** Quorcetin content = (Quorcetin mg/Total amount mg)Х100

^*** nd = not detected)

First, quercetin 3,4'-diclucoside, isoquercitrin, and quercetin contained in 1 g of the flavonoid fraction were 115.4 mg, 216.1 mg, and 49.5 mg, respectively. When the above fraction was dissolved at 10,000 ppm in 50% ethanol solvent, 5 mg of citric acid was added, and microwaved at 120°C for 30 minutes, a trace amount of isoquercitrin was confirmed, but quercetin 3,4'-diclucoside and isoquacitrin were detected. Citrin was converted to quercetin with a yield of 53.8%, and the quercetin content in the processed product was 96.2%.

Summarizing the experimental results of the above experimental examples, when the butanol layer and flavonoid fraction of onion extract were processed using a microwave method, quercetin 3,4'-diclucoside and isoquercitrin, the main flavonoid components of onion, were efficiently converted to quercetin. It can be seen that it can be converted to , and specifically, quercetin 3,4'-diclucoside and isoquercitrin, which are the main flavonoids of onion, have excellent physiological activity at 48.8% in the butanol layer and 53.8% in the flavonoid fraction. It can be seen that eggplant can be obtained as a microwave processed product converted to quercetin.

Therefore, it can be seen that according to the above method, processed products with a high content of quercetin can be mass-produced efficiently in a short period of time under microwave conditions.

The description of the present invention described above is for illustrative purposes, and those skilled in the art will understand that the present invention can be easily modified into other specific forms without changing the technical idea or essential features of the present invention. will be. Therefore, the embodiments described above should be understood in all respects as illustrative and not restrictive.

Claims (14)

A method for producing quercetin, comprising the step of irradiating onions or their extracts with microwaves,
A manufacturing method wherein the microwave irradiation is performed in the presence of citric acid or acetic acid. The method according to claim 1, wherein the onion or its extract contains one or more of isoquercitrin (Quercetin 3-glucoside) and quercetin 3,4'-diglucoside. Manufacturing method. The method according to claim 1, wherein the microwave irradiation is performed under 2 atm to 100 atm. The method of claim 1, wherein the microwave irradiation is performed at 100°C to 150°C. The manufacturing method according to claim 1, wherein the microwave irradiation is performed for 30 to 90 minutes. delete delete delete delete delete delete delete A method for producing onion extract with increased quercetin content, comprising the step of irradiating onions or their extracts with microwaves,
A manufacturing method wherein the microwave irradiation is performed in the presence of citric acid or acetic acid. The method of claim 13, wherein the onion extract with increased quercetin content contains more than 30% of quercetin based on the weight of quercetin, isoquercetin, and quercetin 3,4'-diclucoside.