WO2012020892A1 - 활성형 플라보노이드 화합물의 함량이 증가된 옻나무 추출물 및 그의 제조 방법 - Google Patents
활성형 플라보노이드 화합물의 함량이 증가된 옻나무 추출물 및 그의 제조 방법 Download PDFInfo
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- WO2012020892A1 WO2012020892A1 PCT/KR2010/009375 KR2010009375W WO2012020892A1 WO 2012020892 A1 WO2012020892 A1 WO 2012020892A1 KR 2010009375 W KR2010009375 W KR 2010009375W WO 2012020892 A1 WO2012020892 A1 WO 2012020892A1
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- extract
- lacquer
- gas
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- fustin
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
- A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/22—Anacardiaceae (Sumac family), e.g. smoketree, sumac or poison oak
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Definitions
- the present invention is a gas bubbling treatment of the lacquer extract to increase the content of the active flavonoid compound, gas lacquer treatment to the solution containing the lacquer extract prepared by the method, and fustine To convert fustin to picetin.
- Rhus verniciflua Stokes is a deciduous broad-leaved subtree belonging to the Anacardiaceae family. Deciduous or evergreen, mostly arborescent or shrub but partly vine (Barkley Fred Alexander., Ann. Of the Missouri Bot. Garden., 24 (3), pp265-500, 1937).
- lactose The sap of lacquer is called lactose, and in ancient times, dried lacquer removes blood from blood and promotes blood circulation, hookworm, abdominal pain, excessive stomach acid, cough, pulmonary tuberculosis, pain, constipation, diabetes, It is known to have an effect on malaria, anti-inflammatory, arthritis, embalming, dry stomach, and women's jugular dysfunction. Recently, it has been reported about anticancer effect (Namba, T., Colored Illusteations of Wakan Yaku.p215, Hoikusha Publishing Co. Ltd., Osaka, 1980).
- lacquer is effective as compared to wild ginseng, and it is said to be a good medicine for digestive medicine, blood from liver, blood clot from heart, and to remove tuberculosis bacteria from lung, and other neuralgia, arthritis and skin disease. have.
- lacquer contains large amounts of antioxidants.
- the fraction of purified lacquer extract using a silica column has the ability to inhibit human blood cancer cell growth, as well as a strong antioxidant activity in the extract of the lacquer ethanol.
- a substance having an antimicrobial effect was isolated from the ethanol extract of the lacquer tree, and various bioactive effects related to the lacquer extract are known, such as the anti-obesity effect from the lacquer bark methanol extract.
- flavonoids such as phycetin and fustin have a function of protecting blood vessels or capillaries.
- phycetin and fustin are very good physiologically active substances with antioxidant, anti-inflammatory and anticancer activity.
- fustine contained in a large amount of sumac extract has a disadvantage in that it is much lower than phycetin in terms of physiological activity.
- the phycetin has a problem that the common lacquer extract is occupied most of the amount of fustine and a small amount of phycetin compared to the fustine.
- the lacquer extract containing a large amount of phycetin having excellent physiological activity can be prepared, the lacquer extract will have a relatively excellent anti-cancer activity and physiological activity, it can be very useful in the food and pharmaceutical industry It is expected.
- the present inventors conducted a study on a method of preparing the lacquer extract having more excellent physiological activity by controlling the content of the flavonoid compound in the lacquer extract.
- the present inventors have completed the present invention by developing a method for producing a novel lacquer extract containing a large amount of phycetin having various physiological activities including antioxidant activity and anticancer activity.
- an object of the present invention is to provide a lacquer extract with an increased content of an active flavonoid compound by converting fustine, a flavonoid compound contained in a large amount in lacquer extract, into pestin, an active flavonoid.
- the present invention comprises the steps of extracting the lacquer tree using an extraction solvent; And it provides a method for producing a lacquer extract with an increased content of the active flavonoid compound comprising the step of performing a gas bubbling treatment.
- the gas may comprise oxygen
- the gas bubbling treatment may be performed simultaneously with the extraction of the lacquer, or after the extraction of the lacquer is completed.
- the gas bubbling treatment may be a method of bubbling gas into the extraction liquid in the extraction tank, or contacting the extraction liquid with the bubbling gas from the outside of the extraction tank.
- the active flavonoid compound may be picetin.
- the sumac extract is water, alcohol, methanol, methanol, ethanol, propanol, isopropanol, butanol, acetone, acetone, ether ), Benzene, chloroform, ethyl acetate, methylene chloride, n-hexane, hydrochloric acid, acetic acid, formic acid, citric acid and cyclohexane, petroleum ether and It may be extracted with one or more extraction solvents selected from the group consisting of mixtures thereof.
- the gas is air
- the gas bubbling treatment time may be 6 to 24 hours. More preferably, it may be 8 to 12 hours.
- the gas is high purity, preferably at least 95% (v / v) oxygen, more preferably pure oxygen, gas bubbling treatment time may be 5 to 12 hours. . More preferably, it may be 7 to 10 hours.
- the present invention provides a lacquer extract, characterized in that the content of phycetin: fustin prepared by gas bubbling treatment of the lacquer extract is in the range of 1: 0 to 2: 1. This means that the content ratio of phycetin: fustin is 2 or more.
- the present invention also provides a method of converting fustine to picetin, comprising subjecting the solution containing fustine to gas bubbling.
- the gas is air
- the gas bubbling treatment time may be 6 to 24 hours. More preferably, it may be 8 to 12 hours.
- the gas is high purity, preferably at least 95% (v / v) oxygen, more preferably pure oxygen, and the gas bubbling treatment time may be 5 to 12 hours. have. More preferably, it may be 7 to 10 hours.
- the present invention provides a lacquer extract containing pexetin: fustin in a content ratio of 1: 0 to 2: 1.
- the present invention also provides a pharmaceutical composition for preventing or treating cancer containing the sumac extract as an active ingredient.
- the present invention provides a health food for preventing or improving cancer containing the sumac extract as an active ingredient.
- the method for preparing lacquer extract according to the present invention includes a high content of pacetin by converting fustine to pacetin through gas bubbling treatment of the lacquer extract, which previously contained high content of fustine and low content of pacetin.
- Sumac extract can be provided. Therefore, lacquer extract containing a large amount of phycetin according to the present invention can be commercialized as a natural anticancer agent, anti-cancer and cancer prevention foods, health functional foods, etc., due to its excellent physiological activity, and also the development of related industries with high value of sumac Can be induced.
- the method of converting fustine to pacetin according to the present invention can be used as a method of increasing the flavonoid content of high activity by applying to other natural products can be a base technology that can lead to high functionalization of natural products.
- 1 is a graph showing the effect of converting fustin to possetin over time when air bubbling treatment of the sumac extract.
- Figure 2 is a graph showing the effect of converting the fustine to the phycetin over time when the high-purity oxygen bubbling treatment to the sumac extract.
- the present invention comprises the steps of extracting the lacquer tree using an extraction solvent; And it provides a method for producing a lacquer extract with an increased content of the active flavonoid compound comprising the step of performing a gas bubbling treatment.
- Rhus verniciflua is a deciduous broad-leaved tree belonging to the family Lacaceae , distributed in subtropical or tropical regions, and includes 60 to 400 species worldwide.
- Pacetin (2- (3,4-dihydroxyphenyl) -3,7-dihydroxy-4H-chromen-4-one-hydrate, 3,3 ', 4', 7, one of the active flavonoids contained in the lacquer extract '-tetrahydroxyflavone' is anti-cancer (Haddad AQ et.al., Nutr. Cancer, 2010, 62 (5), 668-81), antidementia (Zheng LT et.al., Int. Immunopharmacol.
- flavonoids known as pharmacological ingredients
- fustine a component contained in a large amount of lacquer extract
- useful physiological activity is known to be much lower than that of picetin.
- This is also supported by the comparative experiments of antioxidant activities of fustin and picetin identified by the inventors (see Table 1). That is, according to one embodiment of the present invention, as a result of comparing the antioxidant activity of fustine and pisetin, it was confirmed that the antioxidant activity of picetin is four times better than that of fustin.
- fustine is referred to as "inactive flavonoid" because fustine has a relatively low physiological activity compared to phycetin which is an active flavonoid showing excellent anticancer and antioxidant activity.
- the present invention provides a method for preparing lacquer extract by converting fustine contained in a large amount of lacquer extract into an active flavonoid phycetin having excellent physiological activity, and the lacquer extract prepared by the method of the present invention contains an active flavonoid compound. It is characterized by a large amount.
- the manufacturing method of the lacquer extract according to the present invention includes the step of performing gas bubbling treatment on the lacquer extract.
- the lacquer refers to trees belonging to the lacquer family, the type of lacquer that can be used in the present invention may be any one or more of dog lacquer, oak, olecus, vine lacquer, hawthorn, hawthorn lacquer It is not limited, Preferably, the oak tree can be used.
- water or an organic solvent may be used.
- solvents such as methylene chloride, n-hexane, hydrochloric acid, acetic acid, formic acid, citric acid, cyclohexane, petroleum ether, can be used individually or in mixture. More preferably, water, alcohol, methanol can be used, and most preferably water can be used.
- the lacquer extract of the present invention may be prepared according to a conventional method for preparing an extract, and specifically, may be prepared by a hot water extraction method, a cold leaching extraction method, or a hot leaching extraction method, and using a conventional extraction device, an ultrasonic grinding extractor, or a fractionator. Can be.
- the extract extracted with the solvent may be removed by filtering or performing a concentration or drying process, it can be performed both filtration, concentration and drying. Specifically, the filtration may be used under reduced pressure or pressure filtration using a filter for filtration, the concentration may be concentrated under reduced pressure under vacuum.
- the obtained extract can be completely removed moisture through concentration and drying
- the lacquer extract completely removed the moisture can be used in powder form or the powder is dissolved in distilled water or a common solvent. Therefore, the lacquer extract containing a high proportion of the active flavonoid compound obtained by the extraction and conversion process of the lacquer extract of the present invention can be commercialized as an extract or extract powder through a process of filtration, concentration and drying.
- a gas containing oxygen may be used as long as it does not interfere with the reaction, preferably air or high purity oxygen, more preferably pure oxygen, It is not limited to this.
- Water, spirits, organic solvents or diluting liquids thereof are added to the lacquer tree and extracted by heating.
- gas preferably oxygen-containing gas is bubbled into the extract or concentrate.
- This process is a process of converting fustine, which is already extracted from lacquer tree and contained in a large amount in the extract, into inactive flavonoid compound, pisetin, which is an active flavonoid, and the gas bubbling step is performed simultaneously with extraction or extraction for a predetermined time.
- the extraction can be carried out next or after the concentration of the extracted extract is concentrated to proceed.
- an oxygen-containing gas may be used.
- air or high purity oxygen preferably pure oxygen
- the purity of oxygen contained in the bubbling gas is 20% (v / v) for air. According to the method of supplying high purity oxygen with oxygen purity of more than 95% (v / v), the higher the purity of oxygen, the shorter the conversion time of fustine to pisetin, and the lower the purity of oxygen, the conversion time is It takes longer and takes a long time to make a complete conversion.
- the bubbling treatment time is shorter than 1 hour, there is little or very minimal conversion of fustine to pisetin, so there is a Lag-time without change in the composition of time.
- the bubbling of oxygen causes the fustine to be decomposed again after it has been converted to phystine, so proper selection of time is essential.
- the bubbling treatment gas is air
- the bubbling treatment gas is oxygen of high purity
- the lacquer extract with an increased content of the active flavonoid compound according to the present invention it is preferable to continue the bling treatment for 5 to 12 hours, and 7 to 10 hours. More preferably.
- the amount and time of bubbling oxygen are generally based on the volumetric flow rate of the gas (l / min), and more preferably at the volumetric supply rate (VVM, l / min / Volume).
- the velocity is divided by the volume of solution.
- the feeding time is 1 to 40 hours, which varies depending on the gas supply flow rate. However, since 12 hours later, most of the fustine is converted to picetin. Of course, if the gas supply rate is extremely low, more than 20 hours may be required for complete conversion to picetin. Therefore, the conversion rate of fustin to phystine can be adjusted by changing the flow rate of the gas to be supplied or the gas supply time.
- the present invention can provide a lacquer extract with an increased content of the active flavonoid compound due to the gas bubbling step, 45 to 100% of the existing fustine content in the lacquer extract is converted to pacetin Sumac extract can be provided. That is, the fustine, which was an essential component of the existing lacquer extract through the lacquer extract method according to the present invention, can be substantially converted into picetin, and in the lacquer extract according to the present invention, there is substantially no fustine. Can be.
- the present invention can provide a lacquer extract containing phycetin: fustin in a content ratio of 1: 0 to 2: 1.
- the condition of the gas bubbling in the sumac extract is based on pressure or purity, and in the case of pressure, a method of continuously bubbling at the bottom of the extractor through a blower at atmospheric pressure or by supplying a gas at high pressure to bubbling This is possible and it is not affected by the internal pressure of the extractor. That is, even if the internal pressure of the extractor or concentrator is maintained in the relative pressure range of 0 to 10 atm, there is no change in the effect, and as the pressure increases, the solubility of oxygen increases, thereby shortening the treatment time. The sharp increase in equipment costs to maintain significantly lowers economics and safety.
- Gas bubbling in the production method of the lacquer extract according to the present invention is generally referred to in the case of supplying gas from the lower part of the extraction tank, or by installing a suitable pipe inside the extraction tank and supplying the gas through the same. It may also be provided by a method that provides a separate opportunity for the extract to contact the bubbling gas outside the extraction tank. This may be the case for conventional liquid and gas contacting systems, including providing a larger area in which gas and extract can come into contact with each other in the top of the extraction vessel or in a separate space.
- the gas bubbling treatment step according to the present invention is a method of bubbling gas into the extract in the extraction tank from which the lacquer extract is extracted, a method of contacting the bubbling gas and the extract from the outside of the extraction tank, the gas and the extract is the same Simultaneously flowing in the direction or in the reverse direction, or as a machine for mixing the extract with the gas can be carried out using a device such as an in-line mixer.
- the sumac extract by the manufacturing method of the present invention can be reconstituted into a fraction containing high picetin through an additional fractionation process. That is, when the solution fractionation using acetone, ethyl acetate, n-butanol, chloroform, etc. as an organic solvent, the amount of phycetin is 30-45% from the extract of 5-25% (w / w) of phycetin. fractions improved with w / w) can be prepared. In addition, it is also possible to obtain a purified product having a purity of 90% (w / w) or higher of picetin by recrystallization.
- the method of preparing the lacquer extract is obtained by adding water, spirits or distilled spirits to the lacquer tree, extracting them by heating, and then concentrating / drying them.
- the composition of the flavonoids in the lacquer extract was 10-30% (w / w) of fustin, 1-4% (w / w) of picetin, and 0.1-2% (w / w) of other flavonoids. It is composed.
- the content increases with age of lacquer.
- the ratio of fustine to phycetin in lacquer trees is usually kept within a certain range, and with age the total content increases. In this case, the content ratio of phycetin: fustin is from 1: 2.5 to 1:30 in minimum, and generally has a content ratio of 1: 5 to 1:15.
- the content ratio of phystine to fustine is generally in the range of 1: 2.5 to 30, but the content ratio of phystine to fustine is 1: 0.2 or less in the case of the lacquer extract by the method of preparing the lacquer extract according to the present invention. Can be adjusted low.
- the difference in activity occurs when the content ratio of phystine: fustin is 1: 1, and it is preferable that the ratio is 5: 1 or more. This means that there is 5 times more than cestine in fustine, which indicates that the content of picetin is significantly increased in comparison with conventional lacquer extract.
- the content of polyphenol compounds known to have physiological activities such as antioxidant and immune enhancement is also maintained at a very high value of 40 to 70% (w / w).
- the content ratio of picetin: fustin may be maintained at a level of 1: 0.001. This means that almost all fustins are converted to picetin, and the extract of lacquer tree containing high picetin is a lacquer extract with higher physiological activity.
- the lacquer extract with increased content of the active flavonoid compound according to the present invention has excellent physiological activity, that is, anti-cancer, anti-dementia, memory improvement, arthritis improvement, anti-inflammatory, antioxidant, blood circulation improvement, etc., compared to the conventional lacquer extract.
- the anticancer activity and the antioxidant activity of the lacquer extract prepared by the preparation method according to the present invention is very excellent compared to the ordinary lacquer extract (see Examples 3 and 4).
- the anticancer activity of the lacquer extract according to the present invention in comparison with the anticancer activity of rats in which the lacquer extract according to the present invention and the general lacquer extract in one embodiment of the present invention is compared, According to the rats administered the lacquer extract containing a large amount of phycetin according to the rats, the weight and volume of the tumors were significantly lower than those of the rats treated with the common lacquer extract (see Table 3). This can be said to support the excellent anticancer activity of the lacquer extract according to the present invention containing a large amount of phycetin known to have excellent anticancer activity.
- the present invention can provide an anticancer composition containing the lacquer extract as an active ingredient, containing cestine: fustin in an amount ratio of 1: 0 to 2: 1, wherein the composition of the present invention is used for the prevention of cancer and It can be used as a pharmaceutical composition for treatment.
- the anticancer composition according to the present invention may include 0.1 to 100% by weight of the lacquer extract based on the total weight of the composition.
- Types of cancer that can be prevented or treated by the compositions of the present invention include, but are not limited to, liver cancer, stomach cancer, colon cancer, lung cancer, breast cancer, rectal cancer, blood cancer, and pancreatic cancer.
- the anticancer composition according to the present invention may include a pharmaceutically effective amount of lacquer extract alone, or may include one or more pharmaceutically acceptable carriers, excipients or diluents.
- pharmaceutically effective amount refers to an amount sufficient to prevent, ameliorate and treat cancer symptoms.
- the pharmaceutically effective amount of the lacquer extract according to the present invention is 0.5-100 mg / day / kg body weight, preferably 0.5-5 mg / day / kg body weight.
- the pharmaceutically effective amount may be appropriately changed depending on the extent of cancer symptoms, the age, weight, health condition, sex, route of administration and duration of treatment of the patient.
- the expression “pharmaceutically acceptable” as used herein refers to a physiologically acceptable and normally does not cause adverse reactions such as gastrointestinal disorders, dizziness or similar reactions when administered to humans.
- carriers, excipients and diluents include lactose, dextrose, sucrose, sorbitol, mannitol, xylitol, erythritol, maltitol, starch, acacia rubber, alginate, gelatin, calcium phosphate, calcium silicate, cellulose, methyl cellulose, poly Vinylpyrrolidone, water, methylhydroxybenzoate, propylhydroxybenzoate, talc, magnesium stearate and mineral oil.
- fillers, anti-coagulants, lubricants, wetting agents, fragrances, emulsifiers and preservatives may be further included.
- compositions of the present invention may be formulated using methods known in the art to provide rapid, sustained or delayed release of the active ingredient after administration to a mammal.
- the formulations may be in the form of powders, granules, tablets, emulsions, syrups, aerosols, soft or hard gelatin capsules, sterile injectable solutions, sterile powders.
- the anticancer composition according to the present invention may be administered through various routes including oral, transdermal, subcutaneous, intravenous or muscle, and the dosage of the active ingredient is determined by the route of administration, the age, sex, weight of the patient and the severity of the patient. It may be appropriately selected depending on several factors.
- the anticancer composition of the present invention can be administered in parallel with a known compound having the effect of preventing, improving or treating cancer symptoms. Therefore, the present invention can provide a medicament for the prevention and / or treatment of cancer symptoms containing the sumac extract as an active ingredient.
- the anticancer composition according to the present invention may not only provide an effect of alleviating cancer symptoms through excellent anticancer and antioxidative action, but may be added to a food for the purpose of preventing and improving cancer symptoms. It can also be used as a food composition for the prevention and improvement of cancer symptoms. Therefore, the composition of the present invention can be easily utilized as a food, such as a main raw material, an auxiliary material, a food additive, a functional food or a beverage that is effective in preventing and improving cancer symptoms.
- the "food” means a natural product or processed product containing one or more nutrients, and preferably means that it can be directly eaten through a certain processing step. As a general sense, it means including all foods, food additives, functional foods and beverages.
- foods to which the anticancer composition according to the present invention may be added include various foods, beverages, gums, teas, vitamin complexes, and functional foods.
- foods that can be used in the present invention include special nutritional products (e.g., formulated oils, infants, infant foods, etc.), processed meat products, fish products, tofu, jelly, noodles (e.g. ramen, noodles, etc.), bread, health Supplements, seasoned foods (e.g. soy sauce, miso, red pepper paste, mixed soy sauce), sauces, sweets (e.g. snacks), candy, chocolates, gums, ice creams, dairy products (e.g.
- the food, beverage or food additive may be prepared by a conventional manufacturing method.
- the "functional food” refers to a food group that has added value to the food by using physical, biochemical, biotechnological techniques, etc. to function and express the function of the food for a specific purpose, control of biological defense rhythm, disease of the food composition Means a food processed and designed to fully express the body control function related to prevention and recovery to the living body, specifically, it may be a health functional food.
- the functional food may include food acceptable food additives, and may further include appropriate carriers, excipients and diluents commonly used in the manufacture of functional foods.
- beverage is a generic term for drinking to quench thirst or to enjoy a taste, and includes a functional drink.
- the beverage contains, as an essential ingredient, a composition for preventing and improving the cancer symptoms at an indicated ratio, and there are no particular restrictions on the other ingredients.
- the beverage contains various flavors or natural carbohydrates as additional ingredients, such as ordinary drinks. can do.
- foods containing the composition of the present invention include various nutrients, vitamins, minerals (electrolytes), synthetic flavors and natural flavors such as flavoring agents, colorants and fillers (such as cheese and chocolate), and pectic acid. And salts thereof, alginic acid and salts thereof, organic acids, protective colloidal thickeners, pH adjusting agents, stabilizers, preservatives, glycerin, alcohols, carbonation agents used in carbonated beverages, and the like, which components may be independently or in combination Can be used.
- the amount of the composition according to the present invention may be included in 0.001% to 100% by weight of the total food weight, preferably 0.1% to 40% by weight
- the amount of the composition according to the present invention may be included in a ratio of 0.001g to 5g, preferably 0.01g to 2g based on 100ml, but for long-term intake for health and hygiene purposes or health control purposes It may be less than the above range.
- the active ingredient is not limited to the above range because it may be used in an amount above the above range because there is no problem in terms of safety.
- the present invention can provide a health functional food for the prevention or improvement of cancer diseases containing the lacquer extract according to the present invention as an active ingredient
- the food may be in the form of powder, granules, tablets, capsules or beverages.
- the present invention is not limited thereto.
- the method for producing the lacquer extract with an increased content of the active flavonoid compound according to the present invention converts the inactive flavonoid compound having a relatively low physiological activity into an active flavonoid compound having an excellent physiological activity as described above.
- the inactive flavonoid compound may be fustin
- the active flavonoid compound may be picetin.
- the present invention may provide a method for converting fustin to picetin.
- the method of converting the fustin to pacetin is a method comprising a gas bubbling treatment to a solution containing fustine, the gas bubbling treatment step is to bubble the gas into the extract liquid in the extraction tank Or bubbling gas and the extraction liquid in contact with the outside of the extraction tank.
- the solution containing fustine may be an extract extracted from a natural product, a solution or extract containing both fustine and pisetin at the same time, or a solution or extract containing only fustine.
- the bubbling treatment gas is air
- the bubbling treatment is continued for 6 to 24 hours in order to prepare a solution containing a high content of phystine through the method of converting fustine to phystine according to the present invention. It is preferable to carry out, more preferably, it can last for 8 to 12 hours.
- the bubbling treatment gas is oxygen of high purity
- the bubbling treatment may be carried out in order to prepare a solution containing high content of pacetin through the method of converting fustine to picetin according to the present invention. It is preferred to last for 12 hours, more preferably 7 to 10 hours.
- the present invention can convert an extract or solution containing a large amount of fustin to an extract or solution containing a large amount of phystine, an active flavonoid compound having excellent physiological activity.
- Example ⁇ 1-1> 100 l of water was added to 10 kg of the oak tree as in Example ⁇ 1-1>, and the lacquer extract was extracted at 95 ° C.
- high-purity oxygen purity 95% (v / v) or more
- the bubbling time was 12 hours in total, and the samples were taken for 1 hour to analyze the components.
- the extract of the lacquer tree according to the present invention was prepared using various extraction solvents. To this end, purified water, 50% alcohol, 80% alcohol, 80% methanol, 100% alcohol was used as the extraction solvent. The time at which 90% conversion took place was compared. The lacquer extract was added 10 times the extraction solvent to 10 kg of oak tree as in the case of the above embodiment, extracted at 95 °C, while bubbling high purity oxygen at the bottom of the extractor with 0.3VVM (volume / volume / min) 1 Extracts were sampled on an hourly basis to investigate conversion to picetin. The results are shown in Table 2 below.
- the extract prepared by the method for producing the lacquer extract according to the present invention regardless of the type of solvent used, it can be confirmed that the fustine in the extract is converted to phystine by gas bubbling treatment. there was. However, as the amount of water in the solvent decreases, the treatment time tends to be longer. Therefore, the present inventors have found that the treatment time should be adjusted in order to increase the conversion rate to picetin according to the type of solvent under the extraction conditions.
- the lacquer extract according to the general lacquer extract method prepared in Comparative Example 1 and the lacquer extract of the present invention prepared in Example ⁇ 1-1> and Example 6 The anticancer activity of the "A" samples was compared with each other.
- A549 a non-small cell lung cancer cell line of humans, was injected subcutaneously in 5 ⁇ 10 5 cells of Immunnodeficient mice (male), CanN. Cg-Foxn1nu / CrljBgi. 7 nude mice were assigned to each group, divided into the control group), the group of Comparative Example 1 and the group of Example ⁇ 1-1>. No extracts were administered to the nude mice of the control group, the group of Comparative Example 1 was extracted from the general ordinary lacquer extract of Comparative Example 1, and the group of Example ⁇ 1-1> was extracted from Example ⁇ 1-1>.
- the sumac extract according to the invention was administered.
- the tumors were removed and weighed on day 27.
- V (tumor size, mean tumor volume, mm3) AB 2/2
- the tumor weight and volume of the mice of the Example ⁇ 1-1> group were significantly lower than those of the animal model group to which the conventional extract was administered. From this, it was confirmed that the lacquer extract according to the present invention has an excellent tumor growth inhibitory effect.
- DPPH is an abbreviation of 1,1-diphenyl-2-picrylhydrazyl and has a radical and is widely used as an index for measuring antioxidant activity.
- the experimental procedure is as follows: (1) 2 ml of 0.1 mM DPPH (Sigma, D-9132) dissolved in ethanol is treated with 2 ml of sample dissolved in ethanol. (2) Mix for 10 minutes and leave in a dark place for 30 minutes. (3) Absorbance at 520 nm is measured. (4) Calculate antioxidant level (electron donating ability, EDA).
- EDA antioxidant level
- As a positive control vitamin E (Fluka, 95420) the formula is as follows.
- the lacquer extract enhanced by the present invention showed an antioxidant activity more than four times higher than that of the conventional lacquer extract. This indicates that the antioxidant activity was also greatly improved as fustine, which was contained in a large amount of the existing lacquer extract, was converted to the active flavonoid picetin.
- Example ⁇ 1-1> 10 kg of lacquer was added twice to add 10 times of water, and concentrated to make 20 liters of concentrate. Oxygen gas was then bubbled at 0.4 VVM for 12 hours, and the lacquer extract was concentrated to 1.2% (w / w) fustine and 15.8% (w / w) picetin. 470 g of extract powder was obtained. At this time, the content ratio of phycetin: fustin was 1: 0.076.
- Example ⁇ 1-1> 100 g of each extract obtained in Example ⁇ 1-1> and Comparative Example 1 was dissolved in 5,000 ml of water, 7,500 ml of ethyl acetate was added thereto, followed by vigorous mixing using a mixer for 10 minutes, and left at room temperature. The layers were separated. When the upper ethyl acetate layer was collected, the solvent was removed, and the component analysis was performed. As a result, the sample of Example ⁇ 1-1> (referred to as "A”) had a content of 42.5% (w / w) of cecetin. In the case of the sample of Comparative Example 1 (referred to as "B"), the content of phycetin was 7.5% (w / w).
- Example 6 10 g of the solid content obtained in Example 6 was dissolved in ethanol in 50 ml, and then poured into 500 ml of cold water (cold) at once. At this time, yellow crystals of picetin were minutely produced. This was recovered by centrifugation at 3,000 rpm for 20 minutes. The obtained crystals were dried and analyzed for purity by HPLC. As a result, the water content was 2.8% (w / w) and picetin purity 96.5% (w / w).
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Abstract
Description
물 질 | 항산화 활성(IC50, ㎍/㎖) |
푸스틴 | 33 |
피세틴 | 8 |
용매의 종류 | 물 | 50% 주정 | 80% 주정 | 100% 주정 | 80% 메탄올 |
소요시간(hrs) | 7.9 | 12.9 | 22.2 | 38.5 | 24.9 |
푸스틴:피세틴 함량비값 | 0.18 | 0.21 | 0.23 | 0.35 | 0.25 |
대조군 | <실시예 1-1>군 | <비교예 1>군 | 실시예6 "A" | |
Tumor Weight(g) | 2± 0.4 | 0.75± 0.12 | 1.7± 0.52 | 0.45± 0.12 |
Tumor Volume(mm3) | 610± 180 | 370± 92 | 550± 115 | 180± 101 |
시료명 | 항산화 활성(IC50,㎍/㎖) |
보통 옻나무 추출물(비교예 1) | 58.9 |
본 발명에 따른 옻나무 추출물(실시예 1-1) | 13.3 |
실시예 6 "A" | 10.5 |
순수 푸스틴 | 32 |
순수 피세틴 | 7.8 |
Claims (20)
- 추출용매를 이용하여 옻나무를 추출하는 단계; 및기체 버블링 처리를 수행하는 단계를 포함하는활성형 플라보노이드 화합물의 함량이 증가된 옻나무 추출물의 제조방법.
- 청구항 1에 있어서,상기 추출물 내에서 피세틴:푸스틴의 함량비가 1:0 ∼ 2:1인 것을 특징으로 하는 옻나무 추출물의 제조방법.
- 청구항 1에 있어서,상기 기체 버블링 처리는 옻나무의 추출과 동시에 수행, 옻나무의 추출이 완료된 후 수행 및 옻나무 추출물을 농축한 농축액에서 수행으로 구성된 군으로부터 선택되는 어느 하나 이상에 의해 수행되는 것을 특징으로 하는 옻나무 추출물의 제조방법.
- 청구항 1에 있어서,상기 기체는 산소를 포함하는 기체인 방법.
- 청구항 1에 있어서,상기 기체는 공기이고, 기체 버블링 처리시간은 6∼24시간인 것을 특징으로 하는 옻나무 추출물의 제조방법.
- 청구항 1에 있어서,상기 기체는 95%(v/v) 이상의 고순도의 산소이고, 기체 버블링 처리 시간은 5∼12시간인 것을 특징으로 하는 옻나무 추출물의 제조방법.
- 청구항 1에 있어서,상기 기체 버블링 처리는 추출조 내부에서 기체를 추출액에 직접 버블링하는 방법, 추출조 외부에서 추출액을 기체와 혼합하면서 접촉시키는 방법 및 기체가 가득찬 용기에 추출액을 통과시키면서 접촉시키는 방법으로 구성된 군으로부터 선택되는 어느 한 가지 이상의 방법에 의해 수행되는 것을 특징으로 하는 옻나무 추출물의 제조방법.
- 청구항 1에 있어서,상기 활성형 플라보노이드는 피세틴인 것을 특징으로 하는 옻나무 추출물의 제조방법.
- 청구항 1의 제조방법에 의해 제조되며 활성형 플라보노이드 화합물의 함량이 증가된 옻나무 추출물.
- 청구항 9에 있어서,상기 활성형 플라보노이드 화합물은 피세틴인 옻나무 추출물.
- 청구항 10에 있어서,추출물 내에서 상기 추출물 내에서 피세틴:푸스틴의 함량비가 1:0 ∼ 2:1인 옻나무 추출물.
- 청구항 9 내지 청구항 11 중 어느 한 항의 옻나무 추출물을 유효성분으로 함유하는 항암용 조성물.
- 청구항 9 내지 청구항 11 중 어느 한 항의 옻나무 추출물을 유효성분으로 함유하는 암 예방 또는 개선용 건강기능성 식품.
- 청구항 9 내지 청구항 11 중 어느 한 항의 옻나무 추출물에 유기용매를 가하고, 분획하는 방법에 의하여 얻어지는 것을 특징으로 하는 피세틴의 함량을 증가시킨 옻나무추출물의 분획물.
- 청구항 14에 있어서,상기 유기용매는 아세톤, 에틸아세테이트, n-부탄올, 클로로포름 및 이들의 혼합물로 이루어진 군으로부터 선택되어 얻어지는 분획물.
- 청구항 15에 있어서,분획물 내의 피세틴의 함량이 30∼45%(w/w) 범위인 분획물.
- 푸스틴을 함유하는 용액에 기체 버블링 처리를 하여 상기 푸스틴을 피세틴으로 전환시키는 방법.
- 청구항 17에 있어서,상기 기체는 산소를 포함하는 기체인 방법.
- 청구항 14 내지 청구항 18 중 어느 한 항의 분획물을 유효성분으로 함유하는 항암용 조성물.
- 청구항 14 내지 청구항 18 중 어느 한 항의 분획물을 유효성분으로 함유하는 암 예방 또는 개선용 건강기능성 식품.
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CN201080069545.8A CN103702675B (zh) | 2010-08-11 | 2010-12-27 | 具有增加含量的活性类黄酮化合物的漆树提取物及其制备方法 |
EP10855959.2A EP2604274B1 (en) | 2010-08-11 | 2010-12-27 | Rhus verniciflua stokes extract having increased content of active flavonoid compound and method for preparing same |
US13/519,548 US8551537B2 (en) | 2010-08-11 | 2010-12-27 | Rhus verniciflua stokes extract having increased content of active flavonoid compound and method for preparing same |
US14/024,076 US8859014B2 (en) | 2010-08-11 | 2013-09-11 | Method of converting fustin to fisetin |
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US14/024,076 Division US8859014B2 (en) | 2010-08-11 | 2013-09-11 | Method of converting fustin to fisetin |
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EP3243528A4 (en) * | 2015-01-05 | 2018-08-01 | Luterion Co., Ltd. | Method for inhibiting telomerase in cancer cells by means of luterion |
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KR102046624B1 (ko) * | 2018-02-12 | 2019-11-19 | 경희대학교 산학협력단 | 칠피 추출물의 에틸아세테이트 분획물과 그 소분획물을 포함하는 항암용 조성물, 및 이의 용도 |
CN108836987A (zh) * | 2018-08-02 | 2018-11-20 | 贺州学院 | 一种从漆树皮中制备抑制恶性黑色素瘤提取物的方法 |
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Also Published As
Publication number | Publication date |
---|---|
EP2604274A4 (en) | 2014-05-07 |
EP2604274B1 (en) | 2016-07-13 |
KR101103040B1 (ko) | 2012-01-05 |
US20120283322A1 (en) | 2012-11-08 |
US20140031567A1 (en) | 2014-01-30 |
JP2013535500A (ja) | 2013-09-12 |
KR101314302B1 (ko) | 2013-10-02 |
EP2604274A1 (en) | 2013-06-19 |
CN103702675A (zh) | 2014-04-02 |
CN103702675B (zh) | 2017-06-23 |
US8859014B2 (en) | 2014-10-14 |
KR20120022678A (ko) | 2012-03-12 |
JP5937596B2 (ja) | 2016-06-22 |
US8551537B2 (en) | 2013-10-08 |
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