KR101753244B1 - Composition comprising trigonelline as an active ingredient for care of hangover or protection of liver - Google Patents
Composition comprising trigonelline as an active ingredient for care of hangover or protection of liver Download PDFInfo
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- KR101753244B1 KR101753244B1 KR1020160014904A KR20160014904A KR101753244B1 KR 101753244 B1 KR101753244 B1 KR 101753244B1 KR 1020160014904 A KR1020160014904 A KR 1020160014904A KR 20160014904 A KR20160014904 A KR 20160014904A KR 101753244 B1 KR101753244 B1 KR 101753244B1
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- South Korea
- Prior art keywords
- composition
- trigonelline
- hangover
- present
- liver
- Prior art date
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
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- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4425—Pyridinium derivatives, e.g. pralidoxime, pyridostigmine
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
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- 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)
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- A23V2200/00—Function of food ingredients
- A23V2200/30—Foods, ingredients or supplements having a functional effect on health
- A23V2200/334—Foods, ingredients or supplements having a functional effect on health treating the effects of consuming alcohol, narcotics or other addictive behavior, e.g. treating hangover or reducing blood alcohol levels
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Abstract
The present invention relates to a composition containing trigonelline as an active ingredient and exhibiting an effect of reducing hangover, improving liver function and reducing non-steroidal analgesic hepatotoxicity by increasing acetaldehyde decomposing enzyme (ALDH2), functional food and animal feed ≪ / RTI >
Description
The present invention takes advantage of the fact that Trigonelline, one of the ingredients contained in coffee beans, induces a hangover, which is a harmful physical symptom that can be caused by alcohol consumption, to induce elevation of metabolic enzymes in the liver, The present invention relates to a composition for dissolving. The present invention also relates to a composition for protecting liver function, which can be applied to the reduction of liver toxicity, which is a side effect of acetaminophen, which is a typical non-steroidal analgesic agent, and a pharmaceutical composition for reducing hepatotoxicity.
Trigonelline (IUPAC name: 1-Methylpyridinium-3-carboxylate), which is represented by the following
≪ Formula 1 >
Looking at the prior art relating to trigonelline, it has been found that a novel composition as a dopaminergic agent in the treatment of dopamine related diseases, including Parkinson's disease, in patent application No. 1020090126253, Inhibiting compounds to reduce the side effects caused by prolactin elevation, alleviate side effects caused by prolactin elevation, alleviate the side effects caused by prolactin elevation, and relieving mental alertness .
In addition, Japanese Patent Application Laid-Open No. 1020050096242 discloses a method of inhibiting or ameliorating itching or scalp itching caused by a sensitive skin disease by inhibiting the binding of substance P (Substance P) -NK1 receptor, which is the main mediator of itching, and alleviating allergic itching Skin cleansing agents, cleansers, soaps and creams from scalp cleansing compositions, hypoallergenic cosmetics, and UVs containing an extract containing nellin or trigonellin as an active ingredient in an amount of 0.0001 to 10 wt% , A disposable diaper, an atopic infant product, and the like. Also disclosed in U.S. Patent No. 1020120036963 is the use of trigonelline to increase muscle mass during exercise and to reduce the amount of muscle loss during periods of low muscle activity.
However, until now, there have been no patents and research papers related to reduction of trigonelline, hangover, and hepatotoxicity, and besides the use of the known trigonelline, promotion of the production and regeneration of neuronal cells, prevention of cavities, Research findings are published in international journals.
Therefore, the technique related to the relief of hangover or protection of liver function using trigonelline has not yet been known. In the present invention, the present invention treats alcohol, which is a substance that triggers liver toxicity and hangover, through the synergistic effect of hepatic metabolism enzyme Respectively. These results can be expected to be effective in the protection of the liver and protection of the human and animal, and in the resolution of hangover. In addition, it is possible to produce a combination preparation which can expect a synergistic effect with the existing liver protecting material, and it is possible to produce a drug having a scientifically proven efficacy through rapid decomposition of acetaldehyde, which is a causative substance of hangover caused by alcohol metabolism in the body A hangover remedy can be produced.
In other words, by inventing effective ingredients that can be used in various fields related to alcohol toxicity, which is not a simple hangover remedy, it is possible to improve medicines useful for patients suffering from liver diseases caused by drinking and environmental stress, And the like, so that the present invention has been practiced.
The present invention confirms that trigonellin, which is a phytoestrogen contained in foods such as coffee, fenugreek and the like, has a hangover resolution, liver function improvement and protection effect, and based on this, a hangover And a composition for protecting or preventing liver disease, a functional food, and an animal feed additive.
It is also an object of the present invention to provide a pharmaceutical composition for reducing hepatic toxicity of non-steroidal analgesic by confirming that trigonellin has an effect of increasing acetaldehyde decomposing enzyme (ALDH2).
The present invention provides a composition for improving liver function comprising a compound represented by the following formula (1) or a pharmaceutically acceptable salt thereof as an active ingredient.
≪ Formula 1 >
The present invention also provides a composition for relieving hangover comprising the compound represented by the formula (1) or a pharmaceutically acceptable salt thereof as an active ingredient.
As another example, the present invention provides a pharmaceutical composition for reducing the hepatotoxic side effect of a non-steroidal analgesic agent comprising the compound represented by Formula 1 or a pharmaceutically acceptable salt thereof as an active ingredient.
As another example, the present invention provides a health functional food for hangover relief and hepatic function protection comprising trigonellin as an active ingredient.
As another example, the present invention provides a composition for animal feed additive for protecting liver function comprising trigonelline as an active ingredient.
The compound is characterized in that 1-Methylpyridinium-3-carboxylate (generic name: trigonelline) is extracted from coffee or fenugreek, and trigonelline has an effect of controlling ALDH2.
The composition of the present invention is in any one of the group consisting of a pill, a powder, a granule, a tablet, a capsule, a solution, a suppository, and an injection.
The health functional foods are selected from nutritional products including drinks, alcoholic beverages and vitamin complexes including dairy products including soups, meats, sausages, breads, candies, snacks, noodles, ice cream, soups and ionic drinks.
The present invention is based on the finding that trigonellin, which is most abundantly contained in coffee, has an effect of regulating the expression level of acetaldehyde decomposing enzyme (ALDH2), thus exhibiting an effect of removing hangover and improving liver function. It can be advantageously used as a composition for addition.
FIG. 1 shows the morphological changes of human hepatocyte HepG2 cells after treatment with ethanol and trigonellin and ALDA-1, an ALDH2 inducer.
FIG. 2 shows the result of comparing the protein expression of ALDH2 metabolizing enzyme with that of human hepatocyte strain HepG2 cell after treatment with ethanol and trigonellin and ALDH2 inducer, ALDA-1 preparation.
Hereinafter, preferred embodiments of the present invention will be described in detail. It is to be understood that both the foregoing general description and the following detailed description are exemplary and explanatory and are intended to provide further explanation of the invention as claimed. It will be obvious to those who have knowledge of. In the following description of the present invention, a detailed description of known functions and configurations incorporated herein will be omitted when it may make the subject matter of the present invention rather unclear.
The present invention was accomplished by confirming the effect of improving the hangover resolution and liver function on metabolic enzymes at the cell stage by using trigone neurin, a plant hormone and niacin synthesis precursor.
Trigonelin is a metabolite of nicotinic acid related substances that has been discovered so far and has the effect of stopping cell division of muscle cells in the G2 phase. This trigonelline has been found to be the most abundant in unheated coffee beans. It contains 0.25 ~ 1.0% of coffee beans and 0.94 ~ 1.69% of water soluble instant coffee. Bitter taste is one fourth of caffeine, less toxic than caffeine, and lethal dose in rat is 3 g / kg. 50 to 80% of coffee beans are decomposed in roasting, resulting in non-volatile components such as nicotinic acid and N-methylnicotinamide. On the other hand, pyrolysis products react with other components to form fragrance, and pyridine (46% 3%), bicyclic compounds (29%) and other (22%). It is known to have antioxidant properties and has been shown to act as a plant hormone and react with estrogen receptors. Based on the various effects Trigonelin has, functional coffee has been produced in Japan, but it has not been shown to be associated with hangover relief and liver protection. Therefore, we examined the alcohol tolerance model of alcohol - ethanol by inducing hangover and hepatotoxicity in liver cell lines, and then we tested the ability of trigonelin to reduce hangover and liver toxicity by metabolic enzyme level.
The trigonelline used in the present invention refers to 1-methylpyridinium-3-carboxylate as a compound represented by the following general formula (1), and is extracted from coffee bean sprouts. When extract is used, it is not limited to an extraction source. The method can be used without limitation.
≪ Formula 1 >
Until now, edible trigonelline has not been sold as a nutritional supplements and health functional food. It is known as an unstable raw material which can be obtained from plants according to the conditions of the extraction method, and high purity is sold at a high price.
In the present invention, ethanol refers to ethyl alcohol and refers to alcohol as a main component of alcohol. Ethanol is an aliphatic hydrocarbon derivative in which a hydrogen atom is replaced with a hydroxyl group (-OH) in ethane (C 2 H 6 ) having two carbon atoms in an aliphatic hydrocarbon compound. It is colorless and has a unique aroma-melting point of -114 ° C, boiling point of 78 ° C and anesthetic. The boiling point of ethanol is much higher than that of ethane having the boiling point of -89 ℃ in the same carbon number because alcohol has a characteristic of forming a hydrogen bond between molecules. Alcohol having hydroxyl group as a functional group is a very stable compound. Also, since the hydroxy group, which is the functional group of the alcohol, does not ionize, the alcohol is a neutral substance. The alcohol that we usually eat and drink is called ethanol because the alcohol is oxidized in the body and acetaldehyde is produced the next day when we drink alcohol.
On the other hand, acetaminophen is classified as a general medicine and can be purchased without a doctor's prescription. It is a substance having side effects of hepatotoxicity as a side effect. Acetaminophen or paracetamol is a major component of tylenol, penicillin, gaborin, camphorin, and cancer growth. Both acetaminophen and paracetamol are abbreviations for their chemical name, para-acetylaminophenol. Acetaminophen is converted into N-acetyl-p-benzoquinone imine (NAPQI) in the body by an enzyme called cytochrome P450 (Cytochrome P450). This metabolite is a strong oxidizing substance in the body, which reduces the glutathione, which protects the liver, and lowers liver function. Recently, in the EMBO Report of the International Journal, the results and mechanism that ALDH2 inhibited hepatotoxicity of acetaminophen metabolism NAPQI were identified. In addition, when acetaminophen is consumed as a headache after drinking alcohol, ALDH2 and glutathione are consumed to metabolize alcohol, so that NAPQI, a strong oxidizing substance, is left in the liver, leading to strong hepatotoxicity. Therefore, it is believed that ALDH2 raised by trigonellin, which is the main result of this patent, will make a great contribution to metabolism of NAPQI, a toxic product metabolized by acetaminophen. In other words, it can be used as an adjuvant to reduce side effects of non-steroidal analgesic drugs.
In the present invention, it has been found that trigonellin has an effect of increasing acetaldehyde dehydrogenase 2 (ALDH2) in hepatocytes in which ethanol is depleted, and it has been found that hangover is eliminated, liver function is improved and liver toxicity is reduced Respectively. Accordingly, the present invention has been applied to a composition for improving hangover, a composition for improving liver function, a pharmaceutical composition for preventing and treating hepatotoxic diseases, a health functional food, and a composition for adding animal feed.
In the present invention, the pharmaceutical composition may have a strong antioxidant efficacy, an elevated expression of ALDH2, and a homeostatic function, though not limited thereto. It can also have hepatocyte death suppression function.
The composition containing the trigonelline of the present invention contains 0.01 to 60% by weight based on the total weight of the composition. The compositions comprising the trigonelline of the present invention may further comprise suitable carriers, excipients or diluents according to conventional methods. Examples of carriers, excipients and diluents that can be included in the composition of the present invention include lactose, dextrose, sucrose, sorbitol, mannitol, xylitol, erythritol, maltitol, starch, acacia rubber, alginate, gelatin, calcium phosphate, calcium silicate, Cellulose, methylcellulose, microcrystalline cellulose, polyvinylpyrrolidone, water, methylhydroxybenzoate, propylhydroxybenzoate, talc, magnesium stearate and mineral oil. The composition comprising trigonelline according to the present invention may be administered orally in the form of powders, granules, tablets, capsules, oral preparations such as suspensions, emulsions, syrups and aerosols, external preparations, suppositories or sterilized injection solutions And can be used as formulations. More specifically, when formulating the composition, it can be prepared using a diluent or an excipient such as a filler, an extender, a binder, a wetting agent, a disintegrant, a surfactant, and the like. Solid formulations for oral administration include tablets, pills, powders, granules, capsules and the like, which may contain at least one excipient such as starch, calcium carbonate, sucrose, lactose, gelatin, Can be prepared. In addition to simple excipients, lubricants such as magnesium stearate and talc may also be used. Examples of liquid formulations for oral use include suspensions, solutions, emulsions and syrups. In addition to water and liquid paraffin which are commonly used simple diluents, various excipients such as wetting agents, sweeteners, fragrances, preservatives and the like have. Formulations for parenteral administration include sterile aqueous solutions, non-aqueous solutions, suspensions, emulsions, freeze-dried preparations and suppositories.
Examples of the suspending agent include propylene glycol, polyethylene glycol, vegetable oil such as olive oil, injectable ester such as ethyl oleate, and the like. Examples of the suppository base include witepsol, macrogol, tween 61, cacao butter, laurin, glycerogelatin and the like.
The trigonelline of the present invention may vary depending on the age, sex and body weight of the patient, but is generally administered in an amount of 0.001 to 500 mg / kg, preferably 0.1 to 100 mg / kg, can do. The dosage may also be increased or decreased depending on the route of administration, degree of disease, sex, weight, age, and the like. Thus, the dosage amounts are not intended to limit the scope of the invention in any manner.
The pharmaceutical composition of the present invention can be administered to mammals such as rats, mice, livestock, humans, and the like in various routes. All modes of administration may be expected, for example, by oral, rectal or intravenous, intramuscular, subcutaneous, intra-uterine dural or intracerebral injection.
In addition, the trigonelline of the present invention provides a health functional food for hangover relief and liver function improvement comprising a food-acceptable food supplementary additive. Examples of the foods to which the compound of the present invention can be added include various foods such as beverages, gums, tea, vitamin complexes and health supplements. Examples of such foods include pills, powders, granules, infusions, tablets, Can be used. In this case, the amount of the compound (trigonelline) in the food or beverage may generally be 0.01 to 15% by weight of the total food weight of the health food composition of the present invention, 0.02 To 10 g, preferably from 0.3 to 1 g. The health beverage composition of the present invention is not particularly limited to liquid ingredients other than the above-mentioned compounds as essential ingredients in the indicated ratios, and may contain various flavors or natural carbohydrates as additional ingredients such as ordinary beverages.
The present invention provides a composition for animal feed additives comprising trigonelline.
The composition for animal feed additive may be 20 to 90% high concentrate or may be in the form of powder or granules.
The composition for animal feed additive of the present invention is a composition containing an organic acid such as citric acid, fumaric acid, adipic acid, lactic acid and malic acid, a phosphate such as sodium phosphate, potassium phosphate, acid pyrophosphate, polyphosphate (polymerized phosphate), polyphenol, catechin ), Natural antioxidants such as alpha-tocopherol, rosemary extract, vitamin C, green tea extract, licorice extract, chitosan, tannic acid and phytic acid.
Animal feed additive containing the composition of the present invention and feeds containing the composition of the present invention may be supplemented with various adjuvants such as amino acids, inorganic salts, vitamins, antibiotics, antimicrobials, antioxidants, antifungal enzymes, living microbial agents, For example, crushed or shredded wheat, oats, barley, corn and rice; Vegetable protein feedstuffs, for example, based on rapeseed, soybeans and sunflower; Animal protein feeds such as blood, meat, bone meal and fish meal; It is preferable to mix all of the dry ingredients comprising the sugar and the milk product such as the various powdered milk and the whey powder and the dry additive and then mix the liquid ingredient with the ingredient to be liquid after heating, In addition to the main components such as fat and vegetable fat, can be used together with materials such as nutritional supplements, digestion and absorption enhancers, growth promoters, disease prevention agents and the like.
The composition for the animal feed additive can be administered alone to the animal in combination with other feed additives in the edible carrier.
In addition, the composition for animal feed additives can be easily administered as top dressing or they can be mixed directly with animal feed, or separately from feed, in separate oral formulations, by injection or percutaneously, or in combination with other ingredients. Typically, a single daily dose or a divided daily dose can be used as is well known in the art.
The animal feed additive may be added to the animal feed by immersion, spraying or mixing.
The present invention is applicable to a number of animal diets including mammals, poultry, and fish. More specifically, the diets include, but are not limited to, commercially important mammals such as pigs, cows, sheep, goats, laboratory animals (rats, mice, hamsters and gerbils), fur- Zoo animals (eg, monkeys and tailless monkeys), as well as livestock (eg, cats and dogs). Common commercially important poultry include chicken, turkey, duck, goose, pheasant and quail. Commercial breeding fish such as trout can also be included.
The animal feed compounding method comprising the composition according to the present invention is such that the composition is incorporated into animal feed in an amount of about 1 g to 100 g per kg of feed on a dry weight basis.
Also, after the feed mixture is thoroughly mixed, lightly viscous granulation or granulation material is obtained depending on the degree of crushing of the components. It is supplied as a mesh or is formed into a desired discrete shape for further processing and packaging. At this time, in order to prevent separation during storage, it is preferable to add water to the animal feed, followed by a conventional pelleting, expansion, or extrusion process. Excess water can be dried off.
Hereinafter, the present invention will be described in more detail by way of examples. However, the following examples serve to illustrate the present invention, and the scope of the present invention is not limited to the following examples.
.
Example 1: Reagents and preparations
Experiments were designed to confirm hangover relief and hepatoprotective efficacy of trigonellin at the cellular level. Trigonelin, ethanol and ALDA-1 were purchased from Sigma. Human hepatocyte HepG2 cells were purchased from the American Type Culture Collection. Culture media and reagents for cell growth were purchased from Thermo fischer. The molecular structure of the purchased trigonelline is shown in the above formula (1). Cell culture medium was used for dilution to the concentration.
Example 2 : Trigonelline Evaluation of protective efficacy in hepatocytes treated with ethanol
Experimental Method
In vitro model was in human hepatocytes the master HepG2 cell 5% carbon dioxide in DMEM medium containing 10% fetal bovine serum, using stabilized 37 ℃ after growth culture under the following conditions.
In order to confirm the expression of Aldehyde dehydrogenase 2 (ALDH2), the most intimately related enzyme with hangover resolution, ALDA-1, which elevates ALDH2 in the control and test groups, was treated with 20 μM as a positive control. Trigonelin was treated with 1 , 10, and 100 μM. And then cultured for 12 hours.
Ethanol, the causative agent of hangover, was treated with 200 mM, and pretreated with trigonelin for 1 hour and then cultured for 12 hours.
After incubation for the specified time, the cells were morphologically analyzed at a magnification of 100x under an optical microscope. Cell protein was separated and the amount of ALDH2 protein expression was measured using a Western blotting technique.
Cytologic morphological change
When ALDA-1 cells were treated with ALDH2, the density of cell growth was lowered. In the case of trigonelline, it was stable up to 10 μM. In the case of 100 [mu] M, the density was low and the unstable shape of the cells was confirmed. In the ethanol-only group, the density of cell growth was lower than that of the control group, and it was confirmed that the pre-treatment of ALDA-1 was even worse. Surprisingly, pretreatment of 1 μM of trigone neurin showed that the cell density was improved to the control level than that of ethanol alone, and 100 μM was worse. (See FIG. 1)
ALDH2 Change in expression level
Ethanol is metabolized and released in vivo. Absorbed ethanol is first metabolized to acetaldehyde by an enzyme called alcohol dehydrogenase. This acetaldehyde is metabolized by ALDH2 to Acetic acid and H2O2. A person's sense of discomfort with hangover usually occurs in Acetaldehyde, which causes elevated body temperature, headache, nausea, and sweating. Therefore hangover relief is to metabolize this Acetaldehyde as soon as possible and discharge it out of the body. ALDH2 is the most important indicator protein and Western blotting technique was used to confirm that the enzyme was elevated in trigone. As a result, ALDH2 expression was significantly increased not only in the positive control group ALDA-1 but also in the treatment of ethanol after pretreatment. In the ethanol alone treatment group, the expression of ALDH2 was almost not expressed. However, in the group treated with trigonelline, the expression of ALDH2 was increased to the same level as that of the ethanol-untreated negative control group. . (See FIG. 2)
As a result, it was confirmed from the in vitro cell test results that trigonellin increased the ALDH2 metabolic enzyme capable of rapidly degrading and discharging ethanol-induced acetaldehyde, and had a biological activity to prevent hepatocyte apoptosis.
Formulation Example 1: Preparation of powder
Trigonelin 20 mg
10 mg of talc
The above components were mixed and filled in airtight bags to prepare powders.
Formulation Example 2: Preparation of tablets
10 mg trigonelline
2 mg of magnesium stearate
After mixing the above components, tablets were prepared by tableting according to a conventional tablet preparation method.
Formulation Example 3: Preparation of capsules
10 mg trigonelline
3 mg of crystalline cellulose
Lactose 14.8 mg
2 mg of magnesium stearate
The above components were mixed according to a conventional capsule preparation method and filled in gelatin capsules to prepare capsules.
Formulation example 4: Manufacture of health drinks
10 mg trigonelline
Vitamin C 15 g
Vitamin E (powder) 100 g
19.75 g of ferrous lactate
3.5 g of zinc oxide
Nicotinic acid amide 3.5 g
Vitamin A 0.2 g
Vitamin B1 0.25 g
Vitamin B2 0.3 g
Water appropriate amount
The above components were mixed according to a conventional health drink manufacturing method, and the resulting solution was stirred and heated at 85 DEG C for about 1 hour, filtered, sterilized in a sterilized 2 L container, To prepare a health beverage composition. Although the composition ratio is relatively mixed with a component suitable for a favorite beverage as a preferred embodiment, the blending ratio may be arbitrarily varied depending on the regional or national preference such as the demand class, the demanded country, and the intended use.
Animal feeds were prepared by mixing 5,000 mg of trigonelline with 1 kg of commercial soft feed for cats according to a conventional method of preparing the feed.
While the present invention has been described in connection with what is presently considered to be practical exemplary embodiments, it is to be understood that the invention is not limited to the disclosed embodiments, but, on the contrary, Of course it is possible. Accordingly, the scope of the present invention should not be construed as being limited to the above-described embodiments, but should be determined by equivalents to the appended claims, as well as the following claims.
Claims (11)
≪ Formula 1 >
The health functional food is selected from a drink, meat, sausage, bread, candy, snack, noodle, dairy product, soup, beverage, alcoholic beverage,
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110118316A1 (en) * | 2007-02-28 | 2011-05-19 | Trigendo Sp. Z O.O. | Use of Quaternary Pyridinium Compounds for Vasoprotection and/or Hepatoprotection |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110118316A1 (en) * | 2007-02-28 | 2011-05-19 | Trigendo Sp. Z O.O. | Use of Quaternary Pyridinium Compounds for Vasoprotection and/or Hepatoprotection |
Non-Patent Citations (1)
| Title |
|---|
| 논문1(ASIAN PACIFIC JOURNAL OF TROPICAL MEDICINE, 2015)* |
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