KR101761061B1 - Preparation of chitosan­ferulic acid salt compound, and antibacterial composition containing the chitosan-ferulic acid salt compound as an active ingredient - Google Patents

Abstract

The present invention relates to a process for producing a chitosan-ferulic acid salt compound in which chitosan and ferulic acid are reacted with each other to uniformly bind chitosan and ferulic acid in a molecular unit, a chitosan-ferulic acid salt compound and a chitosan- The chitosan-ferulic acid salt compound according to the present invention has a significant antibacterial effect against Pseudomonas aeruginosa known as Pseudomonas aeruginosa and Propionibacterium acnes, known as acne bacteria, Proliferation inhibitory effect, it can be effectively used for preventing or treating diseases caused by Pseudomonas aeruginosa infection and acne infections.

Description

The present invention relates to a preparation method of chitosan ferulic acid salt compound and a chitosan ferulic acid salt compound prepared therefrom as an active ingredient.

The present invention relates to a process for producing a chitosan-ferulic acid salt compound, a chitosan-ferulic acid salt compound prepared therefrom and an antimicrobial composition containing the chitosan-ferulic acid salt compound as an active ingredient, A method for producing chitosan-ferulic acid salt compound in which chitosan and ferulic acid are uniformly bound in a molecular unit by reacting with an acid, a chitosan-ferulic acid salt compound prepared from the chitosan-ferulic acid salt compound and an antibacterial ≪ / RTI >

Antibiotics are generally referred to as antimicrobial agents in general, and in particular, substances which have antimicrobial activity against bacteria, in particular, agents that inhibit systems for synthesizing cell walls and proteins, It means. Antibiotics are predominantly extracted from molds and are used today to treat diseases caused by bacterial infections. The most common antibiotic is penicillin manufactured by the British physician Alexander Fleming in 1928. Penicillin was the first antibiotic manufactured by mankind to respond to bacteria in earnest. A representative antibiotic developed after penicillin is methicillin, which is considered to be more effective than penicillin. Methicillin was made by partially modifying the chemical structure of penicillin.

The methicillin is classified as a beta-lactam class of antibiotics. The beta-lactam antibiotic binds to penicillin-binding proteins (PBPs) And thus the drug efficacy is exerted.

Antibiotic-resistant bacteria refer to bacteria that are resistant to certain antibiotics and that do not respond to antibiotics. For example, penicillin-resistant Staphylococcus aureus, which has no effect on penicillin as described above, is applicable. In addition, there is Methicillin-Resistant Staphylococcus aureus (MRSA), which was first reported to academia in 1961 and has since become a major pathogen in hospitals worldwide. It has been found that MRSA has a unique gene that is resistant to penicillin or methicillin antibiotics. It is reported that the MRSA is mainly infected to a healthy person, mainly to a patient having weak immunity or a patient who has undergone surgery, but in case of infection, it causes sepsis or pneumonia to die.

Pseudomonas aeruginosa ( Pseudomonas aeruginosa) aeruginosa ) is most closely related to human infectious disease among Pseudomonas spp., and it is called Pseudomonas aeruginosa because it forms green. It is widely distributed in nature and is included in the normal gut flora of human intestinal tract, but is isolated only in about 10% of healthy individuals, and may be found in the skin, especially in the body, where it is wetted by the armpit or saliva. Pseudomonas aeruginosa is more resistant to host resistance, such as secondary bacterial infection rather than primary infection, severe burn as an opportunistic infection, wound infection, urinary tract infection, respiratory infection, sepsis, chronic basal disease, steroid or immunosuppressant, Many of the factors that weaken the action, promote the onset and have high resistance to various antibiotics.

As the infections caused by pathogenic microorganisms resistant to the existing chemical-derived antibiotics are increased, recently, antimicrobial agents derived from existing chemical substances are problematic in terms of side effects and resistance, and the demand for development of antimicrobial substances derived from natural materials is increasing , An attempt has been made to develop various medicines or antibiotics using natural products.

The sebaceous glands are present in many areas of the face, back, and chest where acne is common. The sebaceous glands are connected to a tube containing hair called a hair follicle, which produces an oil substance called sebum. The sebum is released to the skin surface through the opening of the hair follicle. The sebaceous follicles stimulate the inner wall of the hair follicle, causing the inner wall cells to fall out more quickly, and the missing cells are clogged to form holes in the hair follicles, forming the basic lesion of acne (comedone, hardened sebaceous glands). Propionibacterium acnes , a germ that resides in the hair follicle, secretes lipolytic enzymes that degrade triglycerides in sebum to form free fatty acids. The formed free fatty acids then stimulate the hair follicles, . Eventually sebum, bacteria and missing cells are released into the skin, causing erythema, edema, pus, or acne.

The propionibacterium acnes produces low molecular weight peptides that chemically induce inflammation by inducing polymorphonuclear leukocyte (PMNK) and by a variety of inflammatory connective factors produced by Propionibacterium acnes It is known that stimulating the immune cells produces cytokines such as interleukin (IL) -8, IL-1 [beta], and TNF-alpha, thereby intensifying inflammation in the skin. To treat acne caused by such a mechanism, oral antibiotics and retinoids are commonly used. In particular, inflammatory acne caused by bacterial infection can alleviate symptoms through antibiotic treatment, but it can cause side effects. Recently, tetracycline, clindamycin, and erythromycin have been used to reduce the proliferation of propionibacterium acnes and to reduce the inflammatory response. However, due to the development of antibiotic resistance, It is known. In addition, the use of corticosteroids (estrogen) or estrogen is a trend to reduce side effects, and the most commonly used vitamin A derivatives (isotretinoin) are sebum inhibitory effects, normalizing hair follicles and occluded pores, It has been shown to have an anti-inflammatory effect, but it also has common side effects such as dry mouth and deadly side effects of malformations.

Therefore, studies to overcome these problems have been actively conducted on the development of preservatives for foods and cosmetics using antibacterial substances that are relatively non-irritating to the skin and harmless to the human body, and development of antimicrobial agents in the medical field.

On the other hand, chitosan is a glucosamine polymer which is contained in crustaceans such as shrimp, crab, bark of insects, and squid bones and obtained by alkali treatment of chitin. The main component is polyglucosamine, which is a colorless amorphous powder with a polymer structure. Chitosan, which is a glucosamine bond, is a very valuable biomaterial because it has a very similar molecular structure to that of human tissue and has very good affinity for human body and does not cause immune reaction. The chitosan can be represented by the following formula, and can be used as a biochemical characteristic cholesterol lowering effect such as cell binding and biotissue culture, antimicrobial activity, hemostatic function, biocompatibility, intestinal metabolism, anticancer activity by immunity enhancement, Lowering action, and detoxifying heavy metals.

[Chemical Formula]

However, since chitosan is not soluble in water, its use is limited. One way to overcome this problem is to introduce a specific functional group in the chemical formula, thereby improving not only the physical properties of chitosan but also the physiological activity .

Ferulic acid is a white to pale yellowish brown crystalline powder which is odorless or has a slight peculiar odor and is contained in plant seeds such as wheat, oats, coffee, apples, oranges, peanuts, pineapples and artichokes. Is a substance that can be used as a raw material for various physiologically active substances because it contains a phenolic hydroxyl group (-OH), a double bond, a carboxyl group (-COOH), etc. as a functional group. As a precursor of lignin that forms plant cell walls, ferulic acid has an antioxidant activity that neutralizes active oxygen such as superoxide ions, nitrogen oxides, and hydroxy radicals, and its effect is to suppress the biooxidation of active oxygen, It is known as superoxide dismutase (SOD). In particular, it has excellent inhibitory effect on lipid oxidation in cells. Ferulic acid has a strong antioxidant power, and it has a very good effect of eliminating melanin pigment and inhibiting the production of spots and freckles, so it has a good cosmetic effect and also has a blood sugar lowering effect and a cholesterol lowering effect. However, there has been no report on a compound in which ferulic acid is bound to chitosan.

Accordingly, the inventors of the present invention have been studying a substance capable of replacing an antimicrobial substance derived from a conventional chemical substance that poses a problem of resistance or safety, and found that a chitosan-ferulic acid salt compound reacted with chitosan and ferulic acid Chitosan or commercial antibiotics, the antimicrobial activity is remarkably improved, and it can be effectively used for the prevention and treatment of diseases caused by Pseudomonas aeruginosa infection and acne bacterial infection, thus completing the present invention.

Korean Patent Publication No. 2006-0048401

It is an object of the present invention to provide a process for preparing a chitosan-ferulic acid salt compound.

Another object of the present invention is to provide a chitosan-ferulic acid salt compound prepared by the above method.

It is still another object of the present invention to provide an antimicrobial composition containing the chitosan-ferulic acid salt compound as an active ingredient.

In order to achieve the above object,

Reacting ascorbic acid with a chitosan solution in which chitosan is dissolved in an acid solution to obtain an intermediate (step 1); And

A process for producing a chitosan-ferulic acid salt compound comprising reacting ferulic acid with the intermediate prepared in step 1 to obtain a chitosan-ferulic acid salt compound (step 2).

Preferably, step 1 is a step of dissolving ascorbic acid in a chitosan solution in which the chitosan having a molecular weight of 1,000 g / mol to 2,000,000 g / mol and a degree of deacetylation of 50% to 99% By weight, and reacting at room temperature for 20 to 40 minutes to obtain an intermediate.

Preferably, the step 2 is a step of mixing 1 - 0.10836 parts by weight of ferric acid with the intermediate prepared in step 1, and reacting the mixture at room temperature for 20 to 30 hours to obtain a chitosan-ferulic acid salt compound.

Preferably, the chitosan-ferulic acid salt compound prepared in step 2 is solidified by a drying method to prepare a solid chitosan-ferulic acid salt compound.

Preferably, the drying method may be selected from freeze drying, vacuum drying, spray drying, heat drying and natural drying.

Further, the present invention provides a chitosan-ferulic acid salt compound having a composition ratio of chitosan to ferulic acid in a weight ratio of 10:90 to 70:30 by the above-described method.

The present invention also provides an antimicrobial composition comprising the chitosan-ferulic acid salt compound as an active ingredient.

The present invention also provides a pharmaceutical composition for preventing or treating diseases caused by infection of a microorganism to be an antibacterial subject comprising the above-mentioned antimicrobial composition.

The present invention also provides a health functional food for preventing or ameliorating diseases caused by infection of a microorganism to be an antibacterial subject, which comprises the above-mentioned antimicrobial composition.

The present invention also provides a health functional food additive for preventing or ameliorating diseases caused by infection of a microorganism to be an antibacterial subject, which comprises the above antimicrobial composition.

The present invention also provides a cosmetic composition comprising the antimicrobial composition.

The present invention also provides a cosmetic additive comprising the antimicrobial composition.

The present invention also provides a detergent comprising the antimicrobial composition.

The chitosan-ferulic acid salt compound according to the present invention exhibits a significant antimicrobial effect and proliferation inhibitory effect on Pseudomonas aeruginosa known as Pseudomonas aeruginosa and Propionibacterium acnes known as acne bacteria, And can be usefully used for the prevention or treatment of diseases and diseases caused by acne fungus infections.

BRIEF DESCRIPTION OF THE DRAWINGS FIG. 1 is a schematic view showing a method of producing a chitosan-ferulic acid salt compound according to an embodiment of the present invention. FIG.
2 is a ¹ H-NMR spectrum of a chitosan-ferulic acid salt compound prepared according to an embodiment of the present invention.

Hereinafter, the present invention will be described in detail.

The process for preparing chitosan-ferulic acid salt compounds according to the present invention comprises

Reacting ascorbic acid with a chitosan solution in which chitosan is dissolved in an acid solution to obtain an intermediate (step 1); And

Reacting the intermediate prepared in Step 1 with ferric acid to obtain a chitosan-ferulic acid salt compound (Step 2).

Hereinafter, a method for producing the chitosan-ferulic acid salt compound will be described in detail with reference to FIG.

First, step 1 is the step of forming a chitosan-ascorbic acid intermediate.

Specifically, in the above step, ascorbic acid is mixed with a chitosan solution in which chitosan is dissolved in an acid solution, and reacted at room temperature for 20 to 40 minutes to form an intermediate.

At this time, the chitosan used may have a molecular weight of 1,000 g / mol to 2,000,000 g / mol and a degree of deacetylation of 50% to 99%, but the present invention is not limited thereto.

At this time, the acid solution used may be a conventional acid, and may be acetic acid, formic acid, lactic acid, and the like, but the present invention is not limited thereto.

At this time, it is preferable to add 1 - 0.1080 parts by weight of ascorbic acid to the chitosan solution, and if it is outside the above range, there is a problem in the solubility of chitosan. This is because chitosan dissolves only in acidic conditions and can not produce a chitosan solution unless acid conditions are met.

Next, Step 2 is a step of reacting the intermediate prepared in Step 1 with ferric acid to produce a chitosan-ferulic acid salt compound.

Specifically, in the above step, ferulic acid is mixed with the intermediate prepared in Step 1 and reacted at room temperature for 20 to 30 hours to obtain a chitosan-ferulic acid salt compound.

In this case, the amount of ferulic acid to be added is preferably in the range of 1 to 0.10836 parts by weight, and if it is outside the above range, the grafting rate is reduced.

The produced chitosan-ferulic acid salt compound can be separated by a method such as dialysis or the like, and if necessary, can be dried to prepare a salt compound having a form such as powder, film, molded product and coating. For example, the chitosan-ferulic acid salt compound of the present invention can be obtained through a process of solidification by various drying methods such as freeze drying, vacuum drying, spray drying, heat drying and natural drying, And lyophilized.

Freeze-drying is a method in which the material is frozen and then sublimated into vapor in a vapor state without passing through a liquid state in a high-vacuum apparatus. Thus, a product of much higher quality than a conventional drying method can be obtained, , The dried product is characterized by having a light film structure and is a drying method capable of obtaining high quality products used for drying food, pharmaceuticals and microorganisms at present. It is preliminarily frozen, sublimated, and dehydrated in three stages do. In the preliminary freezing treatment, careful attention is required to control the freezing temperature because the freezing temperature greatly affects the quality of the dried product. In the present invention, preliminary freezing treatment is performed at a temperature of minus 10 ° C to minus 60 ° C, It is necessary to perform preliminary freezing treatment at a temperature of 40 占 폚.

It is necessary to remove the glass solvent corresponding to 50-90% by weight of the total solvent present in the solution during the sublimation drying treatment, which is carried out by heating in a constant cycle and at a temperature of minus 10 ° C to minus 60 ° C for 10 minutes to 2 hours It is required to perform sublimation drying treatment at a pressure of 100 Torr to 0.1 Torr. The sublimed dry treated solution has 50-90 wt.% Of the bound solvent of the total solvent and can be removed by dehydration drying treatment.

In addition, the present invention provides a chitosan-ferulic acid salt compound prepared by the above-described method.

The chitosan-ferulic acid salt compound produced by the above production method can be represented by the following formula (1), and can be confirmed by an analyzer such as ¹ H NMR.

The chitosan-ferulic acid salt compound produced by the above-described method is preferably uniformly bound to chitosan and ferulic acid in a molecular unit and has a composition ratio of chitosan to ferulic acid ranging from 10:90 to 70:30 by weight, But is not limited to.

The present invention also provides an antimicrobial composition comprising the chitosan-ferulic acid salt compound as an active ingredient.

In the present invention, the antimicrobial composition may have the same meaning as antibiotics, which is generically referred to as an antimicrobial agent, and may have the same meaning as an antimicrobial agent, a bactericide, an antiseptic, a preservative or a bactericidal agent and preferably a gram-positive bacterium, Means a substance capable of inhibiting or inhibiting the growth and function of yeast.

The antimicrobial composition of the present invention may contain the chitosan-ferulic acid salt compound in an amount of 0.001 to 99.99 parts by weight, preferably 0.1 to 99 parts by weight, based on the total weight of the composition, The content of the active ingredient can be appropriately controlled.

The antimicrobial composition may be an antimicrobial composition having an antimicrobial activity against pathogenic microorganisms, specifically gram-positive bacteria or gram-negative bacteria. More particularly, the antimicrobial composition may be selected from Staphylococcus sp., E. coli, Pseudomonas sp. (Pseudomonas sp), Propionibacterium sp., Antimobacillus sp., Streptococcus sp., Candida albicans, and Aspergillus sp. sp.), preferably at least one selected from the group consisting of Staphylococcus aureus, E. coli, Pseudomonas aeruginosa, Propionibacterium acnes, Antimobacillus antinomycetemcomitans, Streptococcus mutans, Candida albicans and Aspergillus, Or more preferably this is at least one selected from the group consisting of (Aspergillus niger), may be an antimicrobial composition having an antimicrobial activity against Pseudomonas aeruginosa or propionyl sludge tumefaciens arc Ness.

The antimicrobial composition of the present invention can be directly applied to animals including humans to exhibit antibacterial activity.

The animal is an organism corresponding to a plant. The animal mainly consumes organic matter as nutrients, and the digestion, excretion and respiratory organs are differentiated. Specifically, the animal is an echinoderm, crustacean, mollusk, fish, amphibian, reptile, Mammals, and preferably mammals such as echinoderms such as sea urchins or sea cucumbers, crabs belonging to arthropods, molluscs such as crustaceans such as shrimp, shrimps, cephalopods, gastropods or bivalves, sea breams, sea breams, A flounder or the like, a bird including poultry such as a pheasant or a chicken, or a mammal such as a human, a pig, or a goat.

The antimicrobial composition of the present invention may contain carbohydrates, proteins, lipids, vitamins and minerals in addition to chitosan-ferulic acid salt compounds.

The saccharide may be appropriately selected depending on the purpose and use of the saccharide, and examples thereof may include honey, dextrin, sucrose, palatinose, glucose, fructose, starch syrup, sugar alcohol, sorbitol, xylitol, maltitol, But is not limited thereto. The protein may be selected depending on the purpose and use of the protein. Examples of the protein include milk-derived proteins such as casein and whey protein, soybean proteins, animal-derived enzymes such as trypsin and pepsin And hydrolysates by neutrase and alkylase, but are not particularly limited thereto. The lipid may be selected depending on the purpose and use of the lipid. For example, the first lipid may be selected from saturated fatty acids, sunflower oil containing polyunsaturated fatty acids, rapeseed oil, olive oil, safflower oil, corn oil , A variety of plant-derived fats such as soybean oil, palm oil and palm oil, middle-chain fatty acid, EPA, DHA, soybean-derived phospholipids and milk-derived phospholipids. The above-mentioned vitamins are not particularly limited, and the minerals may be appropriately selected depending on the purpose and use of the minerals. Examples thereof include potassium phosphate, potassium carbonate, potassium chloride, sodium chloride, calcium lactate, calcium gluconate, calcium pantothenate, , Magnesium chloride, ferrous sulfate, sodium hydrogencarbonate, but is not particularly limited thereto.

The saccharide, protein, lipid, vitamins, and minerals may be contained in the composition as long as the antimicrobial activity of the composition is maintained. The content of each component is not limited as long as the antimicrobial activity is maintained , Preferably 0.1 to 15 parts by weight, preferably 0.5 to 10 parts by weight, based on the total composition.

The antimicrobial composition of the present invention can be used for various purposes and applications requiring antimicrobial activity. Specifically, the antimicrobial composition of the present invention can be used as a pharmaceutical composition for preventing or treating disease caused by pathogenic microorganism infection, a composition for animal feed, Additives, beverages, cosmetic compositions, cosmetic additives or detergents.

The present invention also provides a pharmaceutical composition for preventing or treating diseases caused by infection of the above-mentioned antimicrobial composition-containing microorganism.

For example, the disease refers to various infectious diseases that can be caused by infection with the pathogenic microorganisms. Preferably, the diseases include empyema or otitis media caused by P. aeruginosa infection, folliculitis caused by acne infection, acne, corneal ulcer, and the like.

The pharmaceutical composition for preventing or treating diseases caused by infection of microorganisms of the present invention may further comprise a pharmacologically usable carrier or excipient in addition to chitosan according to the formulation and the method of use, May be administered in combination with other pharmacologically active ingredients to enhance the efficacy of the medicament as a therapeutic agent for the infectious disease.

In this case, the content of the chitosan-ferulic acid salt compound in the pharmaceutical composition for preventing or treating diseases caused by infection with microorganisms may be 0.001 to 99 parts by weight. When the content of the chitosan-ferulic acid salt compound in the composition is less than 0.001 part by weight, a large amount of the composition may be necessary for effective effect. If the content of the chitosan-ferulic acid salt compound is more than 99 parts by weight, the effect may be unstable. In addition, the pharmaceutical composition for preventing or treating disease caused by infection of microorganisms according to the method of use and the intended use can appropriately control the content of chitosan.

The pharmaceutical composition for preventing or treating diseases caused by infection of the microorganism of the present invention may be administered orally or parenterally, and preferably, it may be orally administered. However, since the formulation thereof may vary depending on the method of use, It is not limited to a bar. Examples of formulations include PLASTERS, GRANULES, LOTIONS, POWDERS, SYRUPS, LIQUIDS AND SOLUTIONS, AEROSOLS, OINTMENTS, FLUIDS, There are FLUIDEXTRACTS, EMULSIONS, SUSPENSIONS, INFUSIONS, TABLETS, INJECTIONS, CAPSULES and PILLS.

Further, pharmaceutical compositions for the prevention or treatment of diseases caused by infection of microorganisms of the present invention may be prepared using any suitable method known in the art or by the methods described in Remington's Pharmaceutical Science (recent edition), Mack Publishing Company, Easton PA ). ≪ / RTI >

The pharmaceutical composition for preventing or treating diseases caused by the infection of microorganisms of the present invention can be administered orally or rectally in the form of a pharmacologically acceptable carrier or a diluent, a preservative, a stabilizer, a humectant, an emulsifier, a solubilizer, a sweetener, a colorant, The excipient may be a conventional material according to the formulation, and when formulated, a filler, an extender, a wetting agent, a disintegrant or a surfactant may be used. Representative diluents or excipients include water, dextrin, calcium carbonate, lactose, propylene glycol, polyethylene glycol, vegetable oils such as olive oil, injectable esters such as ethyl oleate, liquid paratine and saline.

Specifically, in the case of oral administration according to the formulation, diluents or excipients such as fillers, extenders, binders, wetting agents, disintegrating agents and surfactants which are usually used can be used. In the case of parenteral administration, sterilized aqueous solutions, Suspensions, emulsions, freeze-dried preparations, suppositories, etc. may be used. The non-aqueous solutions or suspensions may be, for example, vegetable oils such as propylene glycol, polyethylene glycol, olive oil, injectable esters such as ethyl oleate, and the like. Examples of the suppository include wipesol, macrogol, 61, cacao paper, laurin or glycerogelatin.

In addition, the pharmaceutical composition for preventing or treating diseases caused by the infection of microorganisms of the present invention can be used in combination with various carriers that are accepted as medicines such as physiological saline or organic solvent, and can be used in combination with glucose , Antioxidants such as ascorbic acid or glutathione, chelating agents, low molecular weight proteins or other stabilizers such as carbohydrates such as sucrose or dextran, .

The subject of administration of the pharmaceutical composition for preventing or treating diseases caused by infection of the microorganism of the present invention may be an epidermis animal, a crustacean, a mollusk, a fish, an amphibia, a reptile, a bird, a mammal, , Marine animals including molluscs and fishes, and mammals capable of consuming the marine animals. More preferably, the marine animals may be echinoderms such as sea urchins or sea cucumbers, crabs belonging to arthropods, shrimp, And can be cultured fishery products including crustaceans such as crustaceans such as sea cucumbers, cephalopods, gastropods or bivalve, fishes such as red sea bream, sea bream, codfish, flatfish, flounder and the like. It can be livestock such as pigs, cattle, goats, etc. and poultry such as pheasants and chickens.

The dosage or amount of the pharmaceutical composition for preventing or treating diseases caused by the infection of the microorganism of the present invention is determined considering the weight, age, sex, health condition, diet, administration time, administration method, excretion rate and severity of disease of the patient For example, an effective daily dose is usually 10 to 5000 mg / kg, preferably 100 to 3000 mg / kg for an adult (70 kg), can be administered once to several times a day, May be administered one to three times per day.

It will be apparent to those skilled in the art that doses may be additive or subtracted, as the dosage can vary depending on various conditions, and thus the dose is not intended to limit the scope of the invention in any way. The number of administrations can be administered once or several times a day within a desired range, and the administration period is not particularly limited.

In addition, the pharmaceutical composition for preventing or treating disease caused by the infection of the microorganism of the present invention may be added to any food and be routinely ingested.

The present invention also provides a health functional food for preventing or ameliorating a disease caused by infection with the microorganism to be an antibacterial subject, which comprises the above antimicrobial composition.

Preferably, the health functional food is a dry product or a cut product of fruits, vegetables, fruits or vegetables, a fruit juice, a vegetable juice, a mixed juice thereof, or a chip, a noodle, a livestock processed food, a fish processed food, And may be any one or more of one or more of the following foods, cereal foods, cereal foods, fermented food products, confectionery bakery products, condiments, meat products, acid drinks, licorice products and herbal products, more preferably milk products, And 1 to 10 parts by weight based on the weight.

The present invention provides a health functional food additive for preventing or ameliorating a disease caused by infection of a microorganism to be an antibacterial subject, which comprises the above antimicrobial composition. At this time, the antimicrobial composition may be a 20 to 90% high concentration liquid, a powder or a granular form, and the form of the food additive includes any one of powders, granules, tablets, capsules and liquid phases.

In addition, the health functional food or food additive of the present invention may contain known natural substances or compounds known to have antimicrobial activity so as to enhance or reinforce the antimicrobial activity in addition to the antimicrobial composition, , A physiologically active ingredient, a mineral, and the like.

The sweetener may be used in an amount such that the food is in a suitable sweet taste, and may be natural or synthetic. Preferably, natural sweeteners are used. Examples of natural sweeteners include sugar sweeteners such as corn syrup solids, honey, sucrose, fructose, lactose and maltose.

The flavoring agent may be used to improve taste or aroma, and both natural and synthetic flavoring agents may be used.

Preferably, a natural one is used. When using natural ones, the purpose of nutritional fortification can be performed in addition to the flavor. Examples of natural flavoring agents include those obtained from apples, lemons, citrus fruits, grapes, strawberries, peaches, and the like, or those obtained from green tea leaves, Asiatica, Daegu, Cinnamon, Chrysanthemum leaves and Jasmine. Also, those obtained from ginseng (red ginseng), bamboo shoots, aloe vera, banks and the like can be used. The natural flavoring agent may be a liquid concentrate or a solid form of extract. Synthetic flavoring agents may be used depending on the case. Synthetic flavoring agents such as esters, alcohols, aldehydes and terpenes may be used.

As the physiologically active substance, vitamins such as retinol, ascorbic acid, tocopherol, calciferol, thiamine, riboflavin and the like can be used.

Examples of the minerals include calcium, magnesium, chromium, cobalt, copper, fluoride, germanium, iodine, iron, lithium, magnesium, manganese, molybdenum, phosphorous, potassium, selenium, .

In addition, the health functional food or food additive of the present invention may contain preservatives, emulsifiers, acidifiers, thickeners and the like as needed in addition to the above sweeteners. Such preservatives, emulsifiers and the like are preferably added in a very small amount as long as they can attain an application to which they are added. The term " trace amount " means, when expressed numerically, in the range of 0.0005% by weight to about 0.5% by weight based on the total weight of the food composition.

Examples of preservatives that can be used include calcium sodium sorbate, sodium sorbate, potassium sorbate, calcium benzoate, sodium benzoate, potassium benzoate, and EDTA (ethylenediaminetetraacetic acid).

Examples of the emulsifier which can be used include acacia gum, carboxymethyl cellulose, xanthan gum, pectin and the like.

Examples of the acidulant that can be used include citric acid, malic acid (malic acid), fumaric acid, adipic acid, phosphoric acid, gluconic acid, tartaric acid, ascorbic acid, acetic acid, and phosphoric acid. Such an acidulant may be added so that the food composition has a proper acidity for the purpose of inhibiting the growth of microorganisms other than the purpose of enhancing the taste.

In addition, examples of the thickener that can be used include a suspending agent, a sedimentation inhibitor, a gel-forming agent, a swelling agent, and the like.

The present invention also provides a cosmetic composition comprising the antimicrobial composition.

In the present invention, it is preferable that the amount of the antimicrobial composition is 0.01 to 30 parts by weight, preferably 0.01 to 5.0 parts by weight of the total cosmetic composition, and it is preferable that the antimicrobial composition is added to cleansing, cleanser, soap, shampoo, rinse, It is possible to impart antimicrobial properties.

The cosmetic composition according to the present invention can be used variously in cosmetics, cleansers and shampoos. Examples of the products to which the present cosmetic composition can be added include cosmetics such as various creams, lotions and skins, and shampoos, rinses, cleansers, cleansers, soaps, treatments, and essences.

The cosmetic composition of the present invention comprises a composition selected from the group consisting of water-soluble vitamins, oil-soluble vitamins, high molecular weight peptides, polymeric polysaccharides, sphingolipids and seaweed extracts.

The water-soluble vitamin is not particularly limited as long as it can be compounded in cosmetics. Preferably, vitamin B, vitamin B2, vitamin B6, pyridoxine, pyridoxine hydrochloride, vitamin B12, pantothenic acid, nicotinic acid, nicotinic acid amide, folic acid, vitamin C, And their salts (thiamine hydrochloride, sodium ascorbate, etc.) or derivatives (sodium ascorbic acid-2-phosphate, magnesium ascorbate-2-phosphate etc.) can also be added to water-soluble vitamins . The water-soluble vitamin can be obtained by a conventional method such as a microorganism conversion method, a purification method from a culture of a microorganism, an enzymatic method, or a chemical synthesis method.

Usable vitamins include vitamins A, carotene, vitamin D2, vitamin D3, vitamin E (d1-? -Tocopherol, d-? -Tocopherol, d-? -Tocopherol) And their derivatives (such as palmitic acid ascorbin, stearic acid ascorbin, dipalmitic acid ascorbin, dl-α-tocopherol acetate, dl-α-tocopherol vitamin E, DL-pantothenyl alcohol, Alcohol, pantothenyl ethyl ether, etc.) are also included in the usable vitamins used in the present invention.

Usability Vitamins can be obtained by a conventional method such as a microorganism conversion method, a purification method from a culture of a microorganism, an enzyme or a chemical synthesis method.

The polymeric peptide may be any compound as long as it can be compounded in cosmetics, and examples thereof include collagen, hydrolyzed collagen, gelatin, elastin, hydrolyzed elastin, and keratin. The polymeric peptide can be obtained by a conventional method such as purification from a culture broth of a microorganism, an enzymatic method, or a chemical synthesis method, or it can be purified from natural products such as ducks such as pigs and cows and silk fiber of silkworms.

The polymeric polysaccharide may be any compound as long as it can be incorporated in cosmetics, and examples thereof include hydroxyethyl cellulose, xanthan gum, sodium hyaluronate, chondroitin sulfate or a salt thereof (sodium salt, etc.). For example, chondroitin sulfate or a salt thereof can be usually purified from mammals or fish.

Sphingo lipids may be any as long as they can be incorporated in cosmetics, and preferred examples thereof include ceramides, pit-sphingosine and sphingoglycolipids. Sphingoid lipids can be purified from ordinary mammals, fish, shellfish, yeast or plants by conventional methods or can be obtained by chemical synthesis.

The seaweed extract may be any of those which can be compounded in cosmetics. Preferably, the seaweed extract is selected from the group consisting of algae extract, red pepper extract, green algae extract and the like. Also, the algae extract may be colored guanine, arginic acid, Potassium alginate and the like are also included in the seaweed extract used in the present invention. Seaweed extract can be obtained from seaweed by a conventional method.

The cosmetic of the present invention may contain, in addition to the above-mentioned essential ingredients, other ingredients usually added to cosmetics, if necessary.

Examples of the compounding ingredients that may be added include organic solvents such as a preservative component, a moisturizer, an emollient, a surfactant, an organic and inorganic pigment, an organic powder, an ultraviolet absorbent, a preservative, a bactericide, an antioxidant, a plant extract, a pH adjuster, A blood circulation accelerator, a cold agent, an antiperspirant agent, and purified water.

Examples of the oil retaining component include ester-based oil retaining, hydrocarbon-based oil retaining, silicone-based oil retaining, fluoric oil retaining, animal retention and plant retention.

Examples of ester-based fats include glyceryl tri-2-ethylhexanoate, cetyl 2-ethylhexanoate, isopropyl myristate, butyl myristate, isopropyl palmitate, ethyl stearate, octyl palmitate, isostearyl isostearate, Butyl isopropyl myristate, isopropyl myristate, isopropyl myristate, isopropyl myristate, isopropyl myristate, isopropyl myristate, butyl, ethyl linoleate, isopropyl linoleate, ethyl oleate, isosilyl myristate, isostearic acid isostearyl, isostearyl palmitate, octyldodecyl myristate, Trimethylol propane, triisostearic acid trimethylol propane, tetra 2-ethylhexanoic acid pentaerythritol tetra (2-ethylhexanoate) , Decyl caprylate, decyl laurate, hexyl laurate, myristate decyl, myristyl myristate, myristine monoethyl stearate, stearyl stearate, decyl oleate, ricinoleic acid tri , Isostearyl stearate, isostearyl stearate, isodecyl stearate, octyldodecyl oleate, octyldodecyl linoleate, isopropyl isostearate, isopropyl stearate, isopropyl stearate, isopropyl stearate, -Hexyl stearate, stearyl ethylhexanoate, stearyl 2-ethylhexanoate, hexyl isostearate, ethylene glycol dioctanoate, ethylene glycol dioleate, propylene glycol dicaprate, di (capryl, capric acid) propylene glycol, Propyleneglycol propionate, propyleneglycol propionate, dicaproic acid neopentyl glycol, dioctanoic acid neopentyl glycol, tricarboxylic acid glyceryl, triunsaturated glyceryl, triisopalmitic acid glyceryl, triisostearic acid glyceryl, neopentanoic acid octyldodecyl Octanoic acid octanoate, octanoic acid octanoate, octanoic acid octanoate, octanoic acid octanoate, octanoic acid octanoate, octanoic acid octanoate, Octyldecyl lactate, octyldecyl lactate, octyldecyl lactate, polyglycerin oleic acid ester, polyglycerin isostearic acid ester, triisocetyl citrate, triisobutyl citrate, triisooctyl citrate, lauryl lactate, myristyl lactate, But are not limited to, ethyl, acetyltriethyl citrate, acetyltributyl citrate, trioctyl citrate, diisostearyl malate, 2-ethylhexyl hydroxystearate, di-2-ethylhexyl succinate, diisobutyl adipate, diisopropyl sebacate, But are not limited to, dioctyl sebacate, stearic acid cholesteryl, isostearic acid cholesteryl, hydroxystearic acid cholesteryl, oleic acid cholesteryl, oleic acid dihydrocholesteryl, isostearic acid pitostearyl, Stearoyl hydroxystearic acid isostearyl, 12-stearoyl stearyl hydroxystearate, 12-stearo And monohydroxystearic acid and esters such as sostearyl.

Hydrocarbon hydrocarbon-based fats and oils such as squalene, liquid paraffin, alpha-olefin oligomer, isoparaffin, ceresin, paraffin, floating isoparaffin, polybutene, microcrystalline wax,

Examples of silicone based oils include polymethyl silicone, methylphenyl silicone, methylcyclopolysiloxane, octamethylpolysiloxane, decamethylpolysiloxane, dodecamethylcyclosiloxane, dimethylsiloxane methyl cetyloxysiloxane copolymer, dimethylsiloxane methylstearoxysiloxane copolymer, alkyl modified silicone Amino-modified silicone oil, and the like.

Examples of the fluorine-based oil include perfluoropolyether and the like.

Examples of the animal or vegetable oil include avocado oil, almond oil, olive oil, sesame oil, rice bran oil, new flower oil, soybean oil, corn oil, rape oil, apricot kernel oil, palm kernel oil, palm oil, castor oil, It is also possible to use an oil-in-water emulsion which contains at least one component selected from the group consisting of cottonseed oil, palm oil, cucumber oil, wheat germ oil, rice germ oil, shea butter, Canned wax, carnauba wax, liquid lanolin, hardened castor oil, and the like.

Examples of the moisturizing agent include water-soluble low-molecular moisturizing agents, oil-soluble molecular moisturizing agents, water-soluble polymers, and oil-soluble polymers.

Examples of the water-soluble low-molecular moisturizing agent include serine, glutamine, sorbitol, mannitol, sodium pyrrolidone-carboxylate, glycerin, propylene glycol, 1,3-butylene glycol, ethylene glycol, polyethylene glycol (Polymerization degree n = 2 or more), polyglycerin (polymerization degree n = 2 or more), lactic acid, lactic acid salt and the like.

Examples of the lipid-soluble low-molecular moisturizing agent include cholesterol and cholesterol ester.

Examples of the water-soluble polymer include carboxyvinyl polymer, polyaspartic acid, tragacanth, xanthan gum, methylcellulose, hydroxymethylcellulose, hydroxyethylcellulose, hydroxypropylcellulose, carboxymethylcellulose, water-soluble chitin, chitosan, dextrin, etc. .

Examples of the oil-soluble polymer include polyvinylpyrrolidone eicosene copolymer, polyvinylpyrrolidone hexadecene copolymer, nitrocellulose, dextrin fatty acid ester, and polymer silicone.

Examples of the emollients include long chain acyl glutamic acid cholesteryl ester, hydroxystearic acid cholesteryl, 12-hydroxystearic acid, stearic acid, rosin acid and lanolin fatty acid cholesteryl ester.

Examples of the surfactant include nonionic surfactants, anionic surfactants, cationic surfactants, and amphoteric surfactants.

Examples of the nonionic surfactant include self emulsifying monostearate glycerin, propylene glycol fatty acid ester, glycerin fatty acid ester, polyglycerin fatty acid ester, sorbitan fatty acid ester, POE (polyoxyethylene) sorbitan fatty acid ester, POE sorbit fatty acid ester, POE Polyoxyethylene polyoxypropylene) copolymers, POEPOP alkyl ethers, polyether-modified silicones, lauric acid alkanolamides, alkylpolyester esters, polyoxyethylene fatty acid esters, polyoxyethylene fatty acid esters, POE alkyl ethers, POE fatty acid esters, POE hardened castor oil, POE castor oil, POEPOP Amine oxides, hydrogenated soybean phospholipids, and the like.

Examples of the anionic surfactant include fatty acid soap, alpha -acylsulfonate, alkylsulfonate, alkylarylsulfonate, alkylnaphthalenesulfonate, alkylsulfate, POE alkyl ether sulfate, alkylamide sulfate, alkyl phosphate, POE alkyl ginseng salt, Alkylsulfosuccinic acid salts, acylated hydrolyzed collagen peptide salts, and perfluoroalkyl phosphoric acid esters, and the like can be mentioned. have.

Examples of the cationic surfactant include alkyl trimethyl ammonium chloride, stearyl trimethyl ammonium chloride, stearyl trimethyl ammonium bromide, cetostearyl trimethyl ammonium chloride, distearyl dimethyl ammonium chloride, stearyl dimethyl benzyl ammonium chloride, behenyl trimethyl ammonium chloride, Benzalkonium, diethylaminoethylamide stearate, dimethylaminopropylamide stearate, quaternary ammonium salts of lanolin derivatives, and the like.

Examples of the amphoteric surfactant include carboxybetaine type, amide betaine type, sulfobetaine type, hydroxysulfobetaine type, amidosulfobetaine type, phosphobetaine type, aminocarboxylate type, imidazoline derivative type and amide amine type Amphoteric surfactants and the like.

Examples of the organic and inorganic pigments include inorganic pigments such as silicic acid, silicic anhydride, magnesium silicate, talc, sericite, mica, kaolin, Bengala, clay, bentonite, titanium mica, titanium oxide, bismuth chloride, zirconium oxide, magnesium oxide, Inorganic pigments such as calcium carbonate, calcium sulfate, barium sulfate, magnesium sulfate, calcium carbonate, magnesium carbonate, iron oxide, chromium oxide, chromium oxide, chromium hydroxide, carbonamine and carbon black; Polyamide, polyester, polypropylene, polystyrene, polyurethane, vinyl resin, urea resin, phenol resin, fluorine resin, silicon resin, acrylic resin, melamine resin, epoxy resin, polycarbonate resin, divinylbenzene styrene copolymer, silk Organic pigments such as powder, cellulose, CI Pigment Yellow and CI Pigment Orange, and composite pigments of inorganic pigments and organic pigments thereof.

As the organic powder, metallic soap such as calcium stearate; Metal salts of alkyl phosphates such as sodium zinc cetylate, zinc laurylate and calcium lauryl laurate; Acylamino acid polyvalent metal salts such as N-lauroyl- [beta] -alanine calcium, N-lauroyl- [beta] -alanine zinc and N-lauroylglycine calcium; Amidosulfonic acid multivalent metal salts such as N-lauroyl-taurine calcium and N-palmitoyl-taurine calcium; N-acyl basic amino acids such as Nε-lauroyl-L-lysine, Nε-palmitoylidene, Nα-paratyylolinine, Nα-lauroyl arginine and Nα-curing tallow fatty acid acylarginine; N-acylpolypeptides such as N-lauroylglycylglycine; ? -amino fatty acids such as? -aminocaprylic acid,? -aminorauric acid and the like; Polyethylene, polypropylene, nylon, polymethylmethacrylate, polystyrene, divinylbenzene styrene copolymer, ethylene tetrafluoride, and the like.

Examples of the ultraviolet absorber include paraaminobenzoic acid, ethyl paraminobenzoate, amyl paranobenzoate, octyl paranobenzoate, ethylene glycol salicylate, phenyl salicylate, octyl salicylate, benzyl salicylate, butylphenyl salicylate, homomenthyl salicylate, benzyl cinnamate , 2-ethoxyethyl para-methoxy methacrylate, octyl methane methacrylate, dipyrromethoxy cinnamate mono 2-ethylhexane glyceryl, para-methoxy methoxy isopropyl acetate, diisopropyl diisopropyl cinnamate ester mixture, Hydroxymethoxybenzophenone sulfonic acid and salts thereof, dihydroxymethoxybenzophenone, sodium dihydroxymethoxybenzophenone disulfonate, dihydroxybenzophenone, tetrahydrobenzophenone sulfonic acid, 4-tert-butyl-4'-methoxydibenzoylmethane, 2,4,6-trianylino-p- (carbo-2'-ethylhexyl-1'- 5-triazine, 2- (2-hydroxy- 5-methylphenyl) benzotriazole, and the like.

Examples of the disinfectant include hinokitiol, trichloroacid, trichlorohydroxydiphenyl ether, crohexidine gluconate, phenoxyethanol, resorcin, isopropylmethylphenol, azulene, salicylic acid, zinc filitione, benzalkonium chloride, No. 301, mononitro and eicol sodium, and undecylenic acid.

Examples of the antioxidant include butylhydroxyanisole, gallic acid propyl, and eicosorbic acid.

Examples of the pH adjuster include citric acid, sodium citrate, malic acid, sodium malate, fumaric acid, sodium fumarate, succinic acid, sodium succinate, sodium hydroxide, sodium monohydrogenphosphate and the like.

Examples of the alcohol include higher alcohols such as cetyl alcohol.

In addition, any of the above components may be blended within the range not to impair the objects and effects of the present invention, but it is preferably 0.01 to 5 parts by weight, more preferably 0.01 to 5 parts by weight, Preferably 0.01 to 3 parts by weight, based on 100 parts by weight of the composition.

The cosmetic of the present invention may take the form of a solution, an emulsion, a viscous mixture or the like.

Examples of the form of the cosmetic material are not particularly limited and include, for example, emulsions, creams, lotions, packs, foundation, lotions, serum, hair cosmetics and soaps.

Specific examples of the cosmetic of the present invention include eye creams, cleansing creams, cleansing milks, cleansing lotions, massage creams, cold creams, moisturizing creams, milks, lotions, packs, after-shave creams, Hair shampoo, hair shampoo, hair rinse, hair treatment, hair dye, hair dye, hair cream, hair liquid, set lotion, hair spray, hair bridge, color rinse, color spray, permanent wave liquid, press powder, loose powder , Eye shadow, hand cream, lipstick, and the like.

In addition, the present invention provides a cosmetic additive comprising the antimicrobial composition.

The above-mentioned cosmetic additives can be added and used in the production processes of finished cosmetics and skin cleansing products, and have an antibacterial function. It can also be used in creams, lotions, massage packs, body cleansers, soaps, shampoos, and other management preparations.

The present invention also provides a detergent comprising the antimicrobial composition.

The detergent may preferably be a detergent for clothes, a dishwasher, a food cleaner, or a household appliance cleaner. The antimicrobial composition is a natural component and is not harmful to human body. Therefore, it is more preferable to use various antimicrobial properties such as washing of kitchen utensils or various household goods including food washing.

The detergent may further contain an adversely selected additive depending on the purpose and use of the detergent. The detergent may be mixed with other active ingredients, such as detergents, and additives such as pigments, surfactants and preservatives. The detergent may be prepared by pulverizing, granulating, tableting or liquefying according to the purpose and use of the detergent, and a conventional method may be used for packaging for commercialization.

In addition, the amount of the antimicrobial composition used in the cleaning agent may be appropriately used depending on the purpose of use, the application form, the application site, the article to be applied, and the like. For example, the antimicrobial composition may contain 0.01 to 50 parts by weight, The content is not limited thereto. Since the antimicrobial composition of the present invention is not harmful to human body including chitosan, it can be used in various amounts as long as the application purpose can be achieved due to the characteristics of the product.

Hereinafter, the present invention will be described in detail with reference to examples. However, the following examples are illustrative of the present invention, and the present invention is not limited by the following examples.

< Example > The chitosan- Ferulic acid  Preparation of salt compounds

Step 1: Preparation of chitosan-ascorbic acid intermediate

0.25 g of chitosan having a molecular weight of about 30,000 g / mol and a deacetylation degree of 94% was dissolved in 25 ml of 2% acetic acid to prepare a chitosan solution. Then, a 1M hydrogen peroxide solution was added with 0.054 g of ascorbic acid- Ascorbic acid solution were mixed and reacted at room temperature for 30 minutes to prepare chitosan-ascorbic acid intermediate.

Step 2: Preparation of chitosan-ferulic acid salt compound

The chitosan-ascorbic acid intermediate prepared in step 1 was mixed with 0.02709 g of ferric acid at 0.307 M and reacted at room temperature for 24 hours.

The product was dialyzed and then lyophilized to obtain a chitosan-ferulic acid salt compound.

The prepared product was analyzed for its chemical structure by ¹ H NMR and the results are shown in FIG.

As shown in Fig. 2, it can be seen that chitosan and ferulic acid are uniformly bound in a molecular unit.

<Experimental Example> Measurement of antibacterial activity

The antimicrobial activity of the chitosan-ferulic acid salt compound according to the present invention was measured as follows.

The strains used for the determination of the antibacterial activity were Pseudomonas aeruginosa and Propionibacterium acnes .

The culture medium of each strain was Nutrient Agar. Tryptic soy broth (TSB), Muller-Hinton broth (MHB), Luria-Bertani broth (LB) and Brain Heart Infusion Broth + 1% dextrose The culture temperature of each bacterium was 37 ℃.

Minimal inhibitory concentration (MIC) was used to measure the antimicrobial activity. Specifically, for each of the above-mentioned target strains, a bacterial dilution prepared by adjusting the concentration so that the number of cells was 5 x 10 ⁴ CFU / ml, chitosan-ferulic acid salt derivative or chitosan prepared in the above example, erythromycin or lincommycin Were mixed in a liquid medium and incubated with the shaking culture for 6 hours at the temperature conditions and the medium.

100 μl of the cultured medium was plated on a flat solid medium prepared from the medium according to the above strain, and cultured for 60 hours. After culturing in a flat solid medium, the concentration of chitosan in which the growth of the microorganism did not increase was determined as the minimum inhibitory concentration (MIC), and Pseudomonas aeruginosa ) and acne bacteria ( Propionibacterium acnes ) are shown in Tables 1 and 2, respectively.

Pathogen Minimum inhibitory concentration (μg / ml) Pseudomonas
aeruginosa
(KCTC 1637) Chitosan-ferulic acid salt compounds Lincomycin 32 64

Pathogen Minimum inhibitory concentration (μg / ml) Propionibacterium
acnes
(KCTC 3314) Chitosan-ferulic acid salt compounds Chitosan Erythromycin Lincomycin 256 512 1024 1024

As shown in Table 1 and Table 2, the chitosan-ferulic acid salt compound according to the present invention shows antimicrobial activity against Pseudomonas aeruginosa at half the content of lincomycin used as an antibiotic, And the antimicrobial activity against acne bacterium is about four times that of erythromycin and lincomycin which are conventionally used as antibiotics and about two times better than that of chitosan. Therefore, the chitosan-ferulic acid salt compound is effective against P. aeruginosa infection And can be effectively used for the prevention or treatment of diseases caused by acne infection.

The present invention has been described with reference to the preferred embodiments. It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the invention as defined by the appended claims. Therefore, the disclosed embodiments should be considered in an illustrative rather than a restrictive sense. The scope of the present invention is defined by the appended claims rather than by the foregoing description, and all differences within the scope of equivalents thereof should be construed as being included in the present invention.

Claims (9)

Reacting ascorbic acid with a chitosan solution in which chitosan is dissolved in an acid solution to obtain an intermediate (step 1); And
A process for producing a chitosan-ferulic acid salt compound, comprising the step of reacting an intermediate prepared in step 1 with ferulic acid to obtain a chitosan-ferulic acid salt compound (step 2). The method according to claim 1,
Step 1 is a step of mixing 1 - 0.1080 parts by weight of ascorbic acid in a chitosan solution in which chitosan having a molecular weight of 1,000 g / mol to 2,000,000 g / mol and having a degree of deacetylation of 50% to 99% In the presence of a catalyst for 20 to 40 minutes to obtain an intermediate. The method according to claim 1,
The step 2 is a step of mixing 1 - 0.10836 parts by weight of ferric acid with the intermediate prepared in step 1 and reacting at room temperature for 20 to 30 hours to obtain a chitosan-ferulic acid salt compound &Lt; / RTI &gt; The method according to claim 1,
A method for producing a chitosan-ferulic acid salt compound, which comprises solidifying a chitosan-ferulic acid salt compound prepared in Step 2 by a drying method to prepare a solid chitosan-ferulic acid salt compound. 5. The method of claim 4,
Wherein the drying method is selected from freeze drying, vacuum drying, spray drying, heat drying and natural drying. delete An antimicrobial composition comprising a chitosan-ferulic acid compound represented by the following formula (1) as an active ingredient, the composition having a composition ratio by weight of chitosan to ferulic acid of 10:90 to 70:30 by weight,
[Chemical Formula 1]

. A pharmaceutical composition for preventing or treating diseases caused by infection of a microorganism to be an antibacterial subject comprising the antibacterial composition of claim 7. A health functional food for preventing or ameliorating a disease caused by an infection of a microorganism to be an antibacterial subject, which comprises the antibacterial composition of claim 7.

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