KR20130077693A - Composition having the activity of antibacterial or antiviral containing rice above ground part extract or flavonolignans compound separated from it - Google Patents

Abstract

PURPOSE: An antibacterial or antivirus composition containing a rice aerial part extract or a flavonolignans compound separated from the extract is provided to prevent influenza virus. CONSTITUTION: Salcolin represented by chemical formula 1, salcolinoside A represented by chemical formula 2, salcolinoside B represented by chemical formula 3, salcolinoside C represented by chemical formula 4, or a pharmaceutically acceptable salt thereof is prepared. An antibacterial or antivirus pharmaceutical composition comprises one or more selected from a group including the salcolin, the salcolinoside A, the salcolinoside B, the salcolinoside C, and the pharmaceutically acceptable salt thereof as an active component. The pharmaceutical composition is useful as a medicine for preventing and treating influenza virus. A food addition of preventing and overcoming a disease infected by bacteria or virus comprises a rice aerial part extract or a fraction thereof. A feed addition of preventing and overcoming a disease infected by bacteria or virus comprises a rice aerial part extract or a fraction thereof.

Description

Composition having the activity of antibacterial or antiviral containing rice above ground part extract or flavonolignans compound separated from it

The present invention relates to a composition having an antibacterial or antiviral activity comprising a rice bran extract or a flavonolignan compound isolated therefrom, and more particularly, salcholine, which is a rice bran extract or a flavonolignan compound isolated therefrom. Since salcolin C, salcolinoside A, salcolinoside B and salcolinoside C have neuraminidase enzymatic inhibitory activity, the above-mentioned rice extract or flan isolated from it The present invention relates to a composition comprising a bonolignan compound as an active ingredient and used for pharmaceuticals, food additives, feed additives, and cleaning composition additives having antibacterial or antiviral activity.

Influenza virus is one of the world's most common viruses affecting both humans and livestock. It is an acute respiratory infection that develops with a rapid incubation period, causing severe systemic symptoms such as systemic boredom, headache, back pain, and muscle pain. Causes respiratory symptoms, including a runny nose.

 Influenza viruses are RNA enveloped viruses having a particle size of about 125 nm in diameter. Influenza viruses basically consist of an internal nucleocapsid or core of ribonucleic acid (RNA) bound to a nucleoprotein surrounded by a viral envelope having a lipid bilayer structure and an outer glycoprotein. The inner layer of the viral envelope consists mainly of matrix proteins, and the outer layer consists mostly of host-derived lipid material. Influenza viruses include two surface antigens, glycoprotein neuraminidase (NA) and hemagglutinin (HA), which appear as spikes of 10-12 nm long at the surface of the particles. It is this surface protein, in particular hemagglutinin, that determines the antigenic specificity of the influenza subtype. Virus strains are of origin, type of subterranean site and year of isolation, serial numbers and influenza viruses are classified as type A, type B, or type C.

 For influenza type A, hemagglutinin and neuraminidase are used as major distinguishing means, and they are called H type antigen and N type antigen, respectively. There are now 16 known H-type antigens (H1-H16), and nine known N-type antigens (N1-N9). The notation is H3N2, H5N1, etc. In the case of B and C viruses, since the mutation does not occur as fast as A, do not use this means of discrimination.

Influenza viruses usually cause pandemics almost every winter with an infection rate of type A or B virus as high as 40% over a period of more than six weeks. Especially in the developed world, elderly people aged 65 or older, accounting for 80-90% of all influenza-related deaths, are vulnerable. Individuals with chronic illnesses are also more likely to experience these complications and infants may have serious illnesses. The initial virus was discovered in Mexico in 2009, but the epidemic was spreading rapidly across the US and Canadian borders, and now new cases are reported in almost all countries around the world.

Neuraminidase refers to an enzyme that separates sialic acid by hydrolyzing neuramic acid. It is found in viruses, bacteria, protozoa, lactic trichomonas (Trichomonas foetus), and animal organs. Influenza virus, Vibrio choleroe, Clostridium perfringens, and the like have high purity crystallized enzymes, and are used as reagents useful in the study of the structure and function of complex sugars. In viruses, they exist on the surface of myxoviruses and paramyxoviruses. It acts when these viruses spill out of red blood cells or normal cells, and is also called a receptor destroying enzyme. It is not known what role this enzyme plays during the course of normal infection. The antigenicity of this enzyme varies depending on the influenza virus type or the virus of the parainfluenza group, and is an indicator of the classification of the virus depending on its presence. Neuraminidase is an influenza virus surface antigen and plays an important role in releasing the newly generated virus out of the cell. Therefore, studies are currently underway in Korea to develop a composition for inhibiting neuraminidase as a treatment for influenza virus.

Conventionally, such neuraminidase inhibitors contain terokapane-based compounds and flavonoid-based compounds isolated from Korean ginseng extract or Korean ginseng fraction as active ingredients in Korean Patent No. 10-1011454 for neuramini for the prevention and treatment of influenza virus infection diseases. A composition for inhibiting day activity has been proposed. In addition, Korean Patent Application Publication No. 2010-0114674 proposes a xanthone-based composition in which a compound isolated from Cucumis japonica extract or a fraction shows an inhibitory effect of neuraminidase. In addition, Korean Patent Publication No. 2011-0004763 proposes a composition for inhibiting neuraminidase activity, which contains a curcuminoid compound of turmeric extract as an active ingredient.

Therefore, much research is needed on improved compositions and methods for treating influenza and there is a need for compositions that have a broad range of immunogenicity against seasonal influenza species and newly emerging influenza species recommended by the WHO. Accordingly, there is an urgent need to develop new materials for neuraminidase inhibitors used as therapeutic agents for influenza virus.

It is an object of the present invention to provide a novel flavonolignan compound isolated from rice plant extracts.

It is an object of the present invention to provide a pharmaceutical composition comprising as an active ingredient a rice bran extract or flavonolignan compound isolated therefrom having antibacterial or antiviral related neuraminidase enzyme inhibitory activity.

It is also an object of the present invention to provide a food additive comprising as an active ingredient a rice bran extract or flavonolignan compound isolated therefrom having antibacterial or antiviral related neuraminidase enzyme inhibitory activity.

It is also an object of the present invention to provide a feed additive comprising as an active ingredient a rice bran extract or flavonolignan compound isolated therefrom having antibacterial or antiviral related neuraminidase enzyme inhibitory activity.

It is also an object of the present invention to provide a cleaning composition additive comprising, as an active ingredient, a rice plant extract having an antibacterial or antiviral related neuraminidase enzyme inhibitory activity or a flavonolignan compound isolated therefrom.

In order to solve the above problems, the present invention provides a composition for the prevention and treatment of influenza virus infection comprising a novel flavonolignan compound extracted from the rice paddy portion as an active ingredient.

In addition, the present invention provides a novel flavonolignan compound, Salcorin C, Salcorinoside A, Salcorinoside B, and Salcorinoside C components, which have antibacterial (antiviral) -related neuraminidase enzyme inhibitory activity isolated from the rice field. It provides a pharmaceutical composition as an active ingredient.

According to the present invention, it is possible to inhibit the activity of neuraminidase through extracts and separation compounds of the rice paddy field and to use in the treatment of diseases related thereto.

In addition, it can prevent influenza virus and has an effect that can be applied as a therapeutic composition.

Figure 1 is a TLC development picture (10% sulfuric acid development) of the purified compound from the rice paddy.
2a, 2b, 2c and 2d are ¹ H-NMR and ¹³ C-NMR spectra for chemical structure identification of the compounds purified from the rice paddy.
Figure 3 is a graph showing the neuraminidase inhibitory activity of the purified compounds separated from the rice paddy portion in the concentration of IC ₅₀ value.

The present invention provides a bacterium or virus by inhibiting neuraidase activity, which comprises a salcholine C compound represented by the following formula (1), which is a novel flavonolignan compound isolated from a rice plant extract, and a salcorin C compound represented by the following formula (1): It provides a composition for the prevention and treatment of infectious diseases.

[Formula 1]

In another aspect, the present invention is a novel flavonolignan compound isolated from the rice plant extracts by inhibiting the neuraminidase activity comprising a salicynoside A compound represented by the formula (2), and a salcorinoside A compound represented by the formula (2) Provided are compositions for the prophylaxis and treatment of bacterial or viral infectious diseases.

[Formula 2]

In another aspect, the present invention is a novel flavonolignan compound isolated from the rice plant extracts by inhibiting the neuraminidase activity comprising a salicynoside B compound represented by the formula (3), and a salcorinoside B compound represented by the formula (3) Provided are compositions for the prophylaxis and treatment of bacterial or viral infectious diseases.

(3)

In another aspect, the present invention is a novel flavonolignan compound isolated from the rice plant extracts by inhibiting the neuraminidase activity comprising a salicynoside C compound represented by the formula (4), and a salcorinoside C compound represented by the following formula (4) Provided are compositions for the prophylaxis and treatment of bacterial or viral infectious diseases.

[Formula 4]

In another aspect, the present invention is a food additive, animal feed additives, or cleaning composition comprising a new flavonolignan compound isolated from the ground of the rice, Salcorin C, Salcorinoside A, Salcorinoside B and Salcorinoside C components as an active ingredient Provide additives.

At this time, the novel flavonolignan compound extracted from the rice paddy field can be used for the treatment of diseases associated with inhibiting the activity of neuraminidase and may be preferably used as a composition for the prevention and treatment of influenza virus infection.

It is preferable to extract and separate the flavonolignan compound derived from the rice paddy field, and to identify their chemical structure using spectroscopy (NMR, IR, LC-Ms / Ms).

Rice ground extract of the present invention may include those extracted from a lower alcohol having 1 to 3 carbon atoms, such as water, methanol, ethanol, or a mixed solvent thereof.

The ground portion of the rice of the present invention is collected and dried or ground, or by using raw raw rice, a volume of water up to about 2 to 15 times, preferably about 5 to 10 times the weight of the sample, and 1 to 3 carbon atoms such as methanol, ethanol, and the like. Filtration and extraction using a polar solvent of lower alcohol or a mixed solvent having a mixing ratio of about 1: 0.1 to 1:10 by using extraction methods such as hot water extraction, cold extraction, reflux cooling extraction or ultrasonic extraction for about 1 day. It can be concentrated to obtain rice ground extract.

The rice varieties include Estimated rice, Nampyeong rice, Ilmi rice, Jado rice, Yeongho Jinmi rice, Goami rice, Shalbo rice, Big eyes rice, Miryang 263, Miryang 234, Hongjin rice, Shinto black rice, Josaeng black rice, Black rice wine It is not limited to such. The pharmaceutical dosage form of the at least one flavonolignan compound selected from Salcholine C, Salcorinoside A, Salcorinoside B, Salcorinoside C compounds represented by the formula (1-4) isolated from the above-ground rice extract of the present invention is It can also be used in the form of their pharmaceutically acceptable salts.

Pharmaceutical composition comprising one or more flavonolignan compounds selected from Salcholine C, Salcorinoside A, Salcorinoside B, Salcorinoside C compound represented by the formula (1-4) isolated from the above-ground rice extract according to the present invention Silver may be used in the form of powders, granules, tablets, capsules, suspensions, emulsions, syrups, aerosols, oral formulations, external preparations, suppositories, and sterile injectable solutions according to conventional methods, but is not limited thereto. It can be properly adjusted according to the method of use and usage. As a carrier, excipient, and diluent that may be included in a composition comprising at least one flavonolignan compound selected from Salmonine C, Salcorinoside A, Salcorinoside B, Salcorinoside C Compounds represented by Formula 1-4 Lactose, dextrose, sucrose, sorbitol, mannitol, xylitol, erythritol, maltitol, starch, acacia rubber, alginate, gelatin, calcium phosphate, calcium silicate, cellulose, methyl cellulose, microcrystalline cellulose, polyvinyl pyrrolidone , Water, methylhydroxybenzoate, propylhydroxybenzoate, talc, magnesium stearate and mineral oil, but are not limited thereto. In the case of formulation, a diluent or excipient such as a filler, an extender, a binder, a wetting agent, a disintegrant, or a surfactant is usually used.

Salmonine C, Salcorinoside A, Salcorinoside B, Salcorinoside C Compounds of Formula 1-4 The preferred dosages of the at least one flavonolignan compound selected are determined by the condition, body weight, and disease of the patient. Depending on the degree, drug form, route of administration, and duration, it may be appropriately selected by those skilled in the art. For the preferred effect, the flavonolignan compound of the present invention is preferably administered at 0.0001 to 100mg / kg, preferably 0.001 to 100mg / kg per day. The administration may be carried out once a day or divided into several times.

The pharmaceutical composition of the present invention can be administered to mammals including humans by various routes. All modes of administration can be administered, for example, by oral, rectal or intravenous, intramuscular, subcutaneous, intrauterine dural or intracerebroventricular injection.

At least one flavonolignan compound selected from Salcholine C, Salcorinoside A, Salcorinoside B, and Salcorinoside C compounds represented by Formula 1-4 having antibacterial or antiviral activity isolated from the sorghum extract Foods that can be added include, but are not limited to, tea, drink, meat, sausage, bread, chocolate, candy, snacks, confectionery, pizza, ramen, gum, ice cream, soups, beverages, alcoholic beverages and vitamin complexes. It doesn't work. At this time, the amount of the flavonolignan compound in the food or beverage may be added to 0.01 to 15% by weight of the total food weight, the health beverage composition is added in a ratio of 0.02 to 5g, preferably 0.3 to 1g based on 100ml It can be adjusted according to the type of food and the method of use.

One or more flavonolignan compounds selected from Salcholine C, Salcorinoside A, Salcorinoside B, Salcorinoside C compounds represented by Formula 1-4 having antibacterial or antiviral activity isolated from the above-ground rice extracts The feed may be added wheat, oats, barley, corn, rice and other grains, rape, soybeans, protein meals such as sunflower, blood meal, meat meal, bone meal, fish meal and animal protein feed. Feeds can be mixed with amino acids, inorganic salts, vitamins, antibiotics, antimicrobials, antioxidants, fungi, enzymes, and live microbial agents.

At least one flavono selected from salcholine C, salcorinoside A, salcorinoside B, salcorinoside C compounds represented by the formula (1-4) having antibacterial or antiviral activity isolated from the ground extracts of rice of the present invention Feed supplemented with lignan compounds can be applied to many animal diets including mammals, poultry and fish. Mammals can be used on pigs, cattle, sheep, goats, laboratory rodents, fur-owned animals, and livestock. Commercial breeding fish such as trout can also be included.

The blending method of the flavonolignan compound is incorporated in an amount of about 0.001 g to 100 g per kg of animal feed. Usually, it is preferable to administer at 0.0001 to 100 mg / kg, preferably at 0.001 to 100 mg / kg.

At least one flavono selected from salcholine C, salcorinoside A, salcorinoside B, salcorinoside C compounds represented by the formula (1-4) having antibacterial or antiviral activity isolated from the ground extracts of rice of the present invention It can be applied to disinfectant cleaners, shower foams, gagrins, wet wipes, detergent soaps, hand washes, humidifier fillers, masks, ointments or filter fillers with added lignan compounds.

In order to have antibacterial or antiviral activity in the composition prepared according to the conventional manufacturing method, it is characterized in that the addition of 0.01 to 15.0% by weight of the flavonolignan compound.

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described concretely with reference to the accompanying drawings, but the present invention is not limited to the embodiments.

Example  1: from the rice paddy field Flavono League  Component Extraction, Isolation and Refining Structure Identification

The ground extract of the rice plant having neuraminidase inhibitory activity was collected from the ground of the rice as shown in FIG. 1, and 26.7 kg of the rice biomass was extracted in 80% aqueous MeOH (18L) at room temperature for 24 hours. The obtained extract was filtered and repeatedly extracted twice by the same method. The obtained extract was collected by filtration, and concentrated under reduced pressure to obtain a MeOH extract. The MeOH extract obtained was partitioned and extracted with n- hexane (3 L x 3) and H ₂ O (3 L), and the H ₂ O layer was extracted with ethyl acetate (EtOAc, 3 L x 3). H ₂ O layer was obtained by partitioning with n -butanol ( n -BuOH, 3L x 3), and each layer was concentrated under reduced pressure, n- hexane (135 g, OSH), EtOAc fraction (47 g, OSE), n- BuOH fraction (90 g, OSB) and H ₂ O fraction were obtained.

Silica gel cc (φ 12 × 20 cm, n-hexane-EtOAc-MeOH = 25: 3: 1 → 23: 3: 1 → CHCl ₃ -MeOH = 20: 1 → 18: 1 → from EtOAc fraction (47 g) 16: 1 → 13: 1 → 7: 1 → 5: 1 → 3: 1 → 1: 1), and 70 ml were separated. Each aliquot was identified by SiO 2 TLC, similar portions were pooled together and concentrated to give 17 fractions (OSE-1 to OSE-17). Among them, OSE-6 fraction (4.2 g) was subjected to SiO2 cc (φ 5.5 cm × 15 cm, CHCl3-MeOH = 15: 1) to obtain nine fractions (OSE6-1 to OSE-6-9). OSE-6-2 fraction (210 mg) was subjected to ODS cc (φ 3.5 × 6 cm, MeOH-H 2 O = 1: 1) to 13 fractions (OSE-6-2-1 to OSE-6-2-13). ), OSE-6-2-10-12 fractions (103 mg) were subjected to SiO2 cc (φ 3 cm × 13 cm, CHCl3-MeOH-H2O = 26: 3: 1) to give 6 fractions. (OSE-6-2-10 ~ 12-1 ~ OSE-6-2-10 ~ 12-6), of which OSE-6-2-10-12-1 ~ 3 fraction (57 mg) was ODS cc (φ 3 × 5 cm, MeOH-H2O = 2: 1) and seven fractions (OSE-6-2-10-12-1 ~ 3-1 ~ OSE-6-2-10-12-12-1 3-7), of which compound 1 [OSE-6-2-10-12-1-3-4 + 5, 24 mg, TLC (RP-18 F254S) Rf 0.5, MeOH-H2O = 4: 1] was separated.

The OSE-12 fraction (1.96 g) was subjected to ODS c.c. (φ 5.5 cm × 7 cm, MeOH-H 2 O = 1: 1.5) to obtain 14 fractions (OSE-12-1 to OSE-12-14). OSE-12-9 fraction (80 mg) was subjected to ODS cc (φ 3.5 × 6 cm, MeOH-H2O = 1: 1) to 12 fractions (OSE-12-9-1 to OSE-12-9-12) Compound 2 [OSE-12-9-10, 20 mg, TLC (RP-18 F254S) Rf 0.5, MeOH-H 2 O = 1: 1] was isolated. The OSE-15 fraction (1.82 g) was subjected to ODS c.c. (φ 4.5 cm × 7 cm, MeOH-H 2 O = 1: 4) to obtain 20 fractions (OSE-15-1 to OSE-15-20). OSE-15-15 fraction (230 mg) was subjected to ODS cc (φ 3.5 × 6 cm, MeOH-H 2 O = 1: 2 → 3: 2) to 12 fractions (OSE-15-15-1 to OSE-15). -15-12), compound 3 [OSE-15-15-12, 19 mg, TLC (RP-18 F254S) Rf 0.5, MeOH-H2O = 1.5: 1] was isolated.

18 fractions (OSE-14-1 to OSE-14-17) were obtained by performing ODSc.c. (φ 4 × 6 cm, MeOH-H20 = 1.5: 1) on the OSE-14 fraction (1.4 g). Of these, OSE-14-11 fraction (152 mg) was subjected to ODS cc (φ 3.5 × 6 cm, MeOH-H 2 O = 1: 1) to eleven fractions (OSE-14-11-1 to OSE-14-). 11-11). Compound 4 [OSE-14-11-6, 34 mg, TLC (RP-18 F254S) Rf 0.5, MeOH-H2O = 1: 1] was isolated.

Example  2: from the rice paddies Flavono League  Component Chemical Structure Identification

Chemical structure identification of the materials obtained in Example 1 was carried out using a nuclear magnetic resonance analyzer (Varian Inova AS 400 MHz) ¹ H-NMR, ¹³ C-NMR, HOMO-COSY, HMQC ( ¹ H-Detected heteronuclear Multiple-Quantum Coherence (HMTC), Heteronuclear Multiple-Bond Coherence (HMBC), and Distortionless Enhancement by Polarization (DEPT) spectra were obtained and the molecular structure was determined. In addition, the molecular weight of each compound was determined by using GC-Mass, and the measurement results are as follows. Salmonine C as Compound 1, Salcorinoside A as Compound 2, Salcorinoside B as Compound 3, and Compound 4 Salcorinoside C was identified. The structure of the isolated polyphenol-based compound is shown in Chemical Formula 1-4.

Formula 1 compound: salcolin C

 1) Physical property: yellow powder

 2) Molecular Weight: 540

 3) Molecular formula: C28H28O11

4) ¹ H-NMR (400 MHz, CD ₃ OD); 7.07 (H-2 ', 6', s), 6.58 (H-3), 6.39 (H-8), 6.13 (H-6), 6.89 (H-2 ", s), 6.73 (H-5" , d, J = 8.0 Hz), 6.81 (H-6 ", dd, J = 8.4 Hz), 4.45 (H-8", d, J = 6 Hz), 3.93 (H-9 "a, dd, J = 12.0, 4.8 Hz), 3.73 (H-9 "b, dd, J = 12.0, 2.6 Hz), 3.29 (H-3 ', H-5', H-7", s), 3.24 (H-3 ", s)

5) ¹³ C-NMR (100 MHz, CD ₃ OD); 183.4 (C-4), 165.9 (C-7), 164.8 (C-2), 162.9 (C-5), 159.1 (C-9), 154.5 (C-3 ', C-5'), 148.6 ( C-3 "), 147.1 (C-4"), 141.4 (C-4 '), 130.9 (C-1 "), 127.3 (C-1'), 105.3 (C-10), 121.9 (C-6 "), 115.5 (C-5"), 111.9 (C-2 "), 105.5 (C-3), 104.7 (C-2 ', 6'), 100.1 (C-6), 95.1 (C-8) , 86.62 (C-8 "), 83.74 (C-7"), 61.7 (C-9 "), 56.7 (C-3 ', C-5'), 56.3 (C-3")

[Formula 2 compound] Salcolinoside A

 1) Physical property: yellow powder

 2) Molecular Weight: 688

 3) Molecular Formula: C33H36O16

4) ¹ H-NMR (400 MHz, CD ₃ OD); 7.13 (H-2 ', 6', s), 6.61 (H-3), 6.39 (H-8), 6.14 (H-6), 7.09 (H-2 ", d, J = 1.2 Hz), 6.76 (H-5 ", d, J = 8.0 Hz), 6.94 (H-6", dd, J = 8.4, 1.6 Hz), 5.18 (H-7 ", d, J = 6.0 Hz), 4.51 (H- 8 ", m), 4.62 (H-1"', d, J = 7.6 Hz), 3.19 (H-3', H-5 ', s), 3.85 (H-3 ", s), 3.69 (H -9 "a, dd, J = 12.0, 4.0 Hz), 3.73 (H-9" b, dd, J = 12.0, 2.4 Hz)

5) ¹³ C-NMR (100 MHz, CD ₃ OD); 183.4 (C-4), 166.1 (C-7), 164.6 (C-2), 162.9 (C-5), 159.1 (C-9), 154.4 (C-3 ', C-5'), 148.3 ( C-3 "), 147.0 (C-4"), 140.2 (C-4 '), 131.5 (C-1 "), 127.7 (C-1'), 105.2 (C-10), 121.2 (C-6 "), 115.5 (C-5"), 112.4 (C-2 "), 105.7 (C-3), 104.8 (C-2 ', 6'), 100.2 (C-6), 95.1 (C-8) , 86.8 (C-8 "), 81.8 (C-7"), 61.6 (C-9 "'), 105.2 (C-1"'), 78.0 (C-3 "'), 77.7 (C-5"'), 75.6 (C-2'"), 71.3 (C-4"'), 62.5 (C-6 "'), 56.9 (C-3 ', C-5'), 56.4 (C-3")

Formula 3 Compound: Salcolinoside B

 1) Physical property: yellow powder

 2) Molecular Weight: 688

 3) Molecular Formula: C33H36O16

4) ¹ H-NMR (400 MHz, CD ₃ OD); 7.19 (H-2 ', 6', brs), 6.62 (H-3), 6.40 (H-8), 6.16 (H-6), 7.10 (H-2 ", brs), 6.76 (H-5" , d, J = 8.0 Hz), 6.91 (H-6 ", dd, J = 8.4, 1.6 Hz), 5.28 (H-7", d, J = 4.0 Hz), 4.43 (H-8 ", m) , 4.18 (H-1 ", d, J = 6.8 Hz), 3.83 (H-3 ', H-5', s), 3.79 (H-3", s), 3.92 (H-9 "a, dd , J = 12.0, 6.4 Hz), 3.68 (H-9 "b, dd, J = 12.0, 6.0 Hz)

5) ¹³ C-NMR (100 MHz, CD ₃ OD); 183.4 (C-4), 166.0 (C-7), 164.9 (C-2), 162.9 (C-5), 159.1 (C-9), 154.4 (C-3 ', 5'), 148.5 (C- 3 "), 147.0 (C-4"), 140.7 (C-4 '), 130.4 (C-1 "), 127.5 (C-1'), 105.2 (C-10), 121.9 (C-6") , 115.4 (C-5 "), 112.8 (C-2"), 105.6 (C-3), 104.6 (C-2 ', 6'), 100.1 (C-6), 95.1 (C-8), 86.8 (C-8 "), 77.8 (C-7"), 61.8 (C-9 "), 100.7 (C-1"'), 77.8 (C-3 "'), 77.7 (C-5"'), 75.0 (C-2 "'), 71.8 (C-4"'), 62.7 (C-6 '"), 56.3 (C-3', C-5 '), 49.6 (C-3")

Formula 4 compound: Salcolinoside C

 1) Physical property: yellow powder

 2) Molecular Weight: 688

 3) Molecular Formula: C33H36O16

4) ¹ H-NMR (400 MHz, CD ₃ OD); 7.04 (H-2 ', 6', s), 6.54 (H-3, s), 6.34 (H-8, s), 6.11 (H-6, s), 7.00 (H-2 ", br s) , 6.73 (H-5 ", d, J = 8.0 Hz), 6.81 (H-6", br d, J = 7.6 Hz), 4.94 (H-7 "), 4.51 (H-8", m), 3.97 (H-9 "), 3.86 (H-3 ', 5', s), 3.81 (H-3", s), 4.33 (H-1 "', d, J = 7.6), 3.99 (H- 9 "a, dd, J = 12.0, 5.2 Hz), 3.68 (H-9" b, dd, J = 12.0, 5.6 Hz)

5) ¹³ C-NMR (100 MHz, CD ₃ OD); 183.3 (C-4), 166.0 (C-7), 164.6 (C-2), 162.8 (C-5), 159.0 (C-9), 154.3 (C-3 ', 5'), 148.4 (C- 3 "), 146.7 (C-4"), 140.4 (C-4 '), 133.2 (C-1 "), 127.2 (C-1'), 105.2 (C-10), 120.8 (C-6") , 115.5 (C-5 "), 111.5 (C-2"), 105.4 (C-3), 104.8 (C-2 ', 6'), 100.2 (C-6), 95.1 (C-8), 86.0 (C-8 "), 74.1 (C-7"), 69.8 (C-9 "), 104.6 (C-1"'), 77.8 (C-3 "'), 77.7 (C-5"'), 75.1 (C-2 "'), 71.5 (C-4"'), 62.6 (C-6 "'), 56.8 (C-3', C-5 '), 56.4 (C-3")

Example  3: rice plant extract and Fraction Neuraminidays  Inhibitory Activity Assay

In order to determine the inhibitory activity against bacterial neuraminidase of the rice plant extract of the present invention or the flavonolignan compound isolated therefrom, the following experiment was performed. Bacterial-derived neuraminidase was purchased from Sigma-Aldrich, and the substrate 2 '-(4-methylumberlyryl) -α-DN-acetylneuraminic acid (2'-(4-methylumbellifery) -α-DN -acetylneuraminic acid) was purchased from Sigma.

First, a flavono lignan compound represented by Formula 1 to 4 separated from rice plant extract or the above was prepared by diluting at a predetermined concentration. The prepared sample and neuraminidase were put in a 3 mL cuvette, 50 mM Tris buffer (pH 7.5, 5 mM, CaCl 2, 200 mM NaCl) was added and mixed well, and then incubated at 37 ° C. for 10 minutes. Subsequently, the excitation wavelength was 365 nm and emission with SpectraMax M2e (Molecular Divices, USA), a fluorometer, by adding 2 '-(4-methylumberlyryl) -alpha-dn-acetylneuraminic acid as a substrate. The wavelength was analyzed at 445 nm. The final concentration of neuraminidase used in the experiment is 2.5 ng, the final concentration of the substrate is 200 μM, the reaction temperature is 37 ℃. The inhibition rate was calculated from the difference in fluorescence intensity from the reaction solution into which ethanol was added instead of the extract, and the results are shown in Table 3 below. On the other hand, Equation 1 applied to the activity evaluation of the enzyme is as follows.

   [Equation 1]

Neuraminidase inhibition rate (%) = (A-B) / A × 100

A: Fluorescence intensity value of no inhibitor added

B: Fluorescence value of the added inhibitor

In addition, the concentration of the extract and the compound (IC50) that inhibits neuraminidase activity by 50% is shown in Tables 1 and 2 below.

Extracts and Fractions Neuraminidays (Clostridium perfringens)
IC50 (ppm) Rice Flour Hydrothermal Extract 37.5 Paddy Ethanol Extract 12.5 Rice ethyl acetate fraction 22.5 Flavono lignan high fraction of rice plant 5.5

In addition, the neuraminidase inhibitory activity (IC ₅₀ ) and the inhibitory pattern (kinetic) of the novel flavonolignans isolated from the above-ground rice field are shown in Table 2.

compound Neuraminidase inhibitory activity (mM, IC ₅₀ ) Inhibition Model and Ki (mM) Value Formula 1 30.04 Non-competitive inhibition, 10.6 (2) 58.61 Non-competitive inhibition, 38.2 (3) 102.83 Non-competitive inhibition, 91.6 Formula 4 58.05 Non-competitive inhibition, 41.2

Claims (10)

Salcolin C represented by the following Chemical Formula 1, salcolinoside A represented by the following Chemical Formula 2, salcolinoside B represented by the following Chemical Formula 3, salcorinoside represented by the following Chemical Formula 4 salcolinoside C, or a pharmaceutically acceptable salt thereof.

[Formula 1]

(2)

(3)

[Chemical Formula 4]

1 or 2 selected from salcolin C, salcolinoside A, salcolinoside B, salcolinoside C and pharmaceutically acceptable salts thereof as defined in claim 1 Pharmaceutical composition useful as an antibacterial agent or an antiviral agent comprising the above as an active ingredient. 3. The method of claim 2,
Pharmaceutical composition useful as a prophylactic and therapeutic agent for influenza virus.  Food additives for the prevention and amelioration of bacterial or viral infectious diseases, including rice extract or fractions. 1 or 2 or more selected from salcolin C, salcolinoside A, salcolinoside B, and salcolinoside C as defined in claim 1 as an active ingredient Food additives for the prevention and improvement of bacterial or viral infections. The method according to claim 4 or 5,
The food is any one selected from the group consisting of meat, sausage, bread, chocolate, candy, snacks, confectionary, pizza, ramen, gum, ice cream, soup, beverage, tea, drink, alcoholic beverage and vitamin complex Food additives.   Animal feed additives for the prevention and improvement of bacterial or viral infectious diseases, including rice extract or fractions. 1 or 2 or more selected from salcolin C, salcolinoside A, salcolinoside B, and salcolinoside C as defined in claim 1 as an active ingredient Animal feed additives for the prevention and improvement of bacterial or viral infections. 1 or 2 or more selected from salcolin C, salcolinoside A, salcolinoside B, and salcolinoside C as defined in claim 1 as an active ingredient A cleaning composition additive for bacteria or virus containing the compound represented by the formula 1,2,3 or 4 of claim 1 or a mixture thereof as an active ingredient. The method of claim 9,
The cleaning agent is a cleaning composition additive, characterized in that it is prepared in the form of a disinfecting detergent, shower foam, gagreen, wet tissue, detergent soap, hand wash, humidifier filler, mask, ointment or filter filler.

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