KR20210054950A - A novel compound, (2R,3R)-4’-O-methyltaxifolin 3-O-β-D-glucopyranoside with postprandial anti-hyperglycemia effect - Google Patents

Abstract

The present invention relates to a novel compound having the postprandial anti-hyperglycemic effect and a pharmaceutical composition for preventing or treating diabetes comprising the same, and more particularly, to a pharmaceutical composition for preventing or treating diabetes comprising a compound of chemical formula 3 as an active ingredient. The present invention can provide a pharmaceutical composition for preventing or treating diabetes, which can be easily and simply prepared and has excellent medicinal efficacy. In addition, the present invention can provide a pharmaceutical composition for preventing or treating diabetes, which can minimize side effects such as a weight gain and headache when taken for a long period of time.

Description

Novel (2R,3R)-4'-O-methyltaxifolin 3-O-β-D-glucopyranoside (A novel compound, (2R,3R)-4'-O) isolated and purified from colored rice with postprandial glycemic-inhibiting effect -methyltaxifolin 3-O-β-D-glucopyranoside with postprandial anti-hyperglycemia effect}

The present invention relates to a novel compound having an effect of inhibiting postprandial blood glucose elevation, and a pharmaceutical composition for preventing or treating diabetes containing the same, and more particularly, to a pharmaceutical composition for preventing or treating diabetes containing the compound of Formula 3 as an active ingredient. About.

Various plant-derived chemicals exhibit various physiological activities, including anti-inflammatory and cytoprotective effects, and thus are in the spotlight as useful materials for medicines and health functional foods.

Rice is one of the world's three largest food resources along with corn and wheat. In the East, including Korea, Japan, and China, most countries have rice as a staple food, and about 90% of the world's rice production is produced in Asia.

The nutritional content of rice varies depending on the variety, but it contains 70-80% carbohydrates, 6-7% protein, and 1-2% fat, and white rice with the algal layer removed has more carbohydrates than brown rice and has a lower protein and fat ratio. .

The part of the rice fruit left after peeling is called rice or brown rice, and rice or brown rice consists of starch layer, white rice, wheat flour layer (sokmigang), rice bran (medium rice bran), outer rice bran and germ (rice sprout).

In general, when brown rice is 100, rice bran is 5-6%, rice bran is 2-3%, and the rest of the ingredients are white rice.

The degree of milling is generally divided into 10 or 12 minutes, and when the degree is polished to 10 or 12 minutes, only white rice remains, and as the number of millings decreases, the amount of rice bran or rice snow increases.

Recently, a number of research results on various physiological activities of rice have been reported. In this regard, Korean Patent No. 10-0726834 describes onions extracted using hot water or ethanol in the manufacture of rice including a drying process. Lowering blood sugar using onions, characterized in that it comprises the step of coating the rice with a coating solution further comprising one or more selected from red ginseng extract, goji japonica extract, and Astragalus extract in addition to the above onion extract or under reduced pressure coating on rice. Disclosed is a method for producing rice.

In addition, Korean Patent No. 10-1171258 is a step of mixing 60 to 80% by weight of rice protein, 16 to 38% by weight of rice flour, 1 to 2% by weight of xylose, and 1 to 2% by weight of tagatose; Injecting the mixture into a twin-screw extruder while adding water to extrude the mixture; And drying the molded product obtained in the extrusion molding step.

Meanwhile, Korean Patent Registration No. 10-1300378 in the manufacturing method of functional rice for lowering blood sugar, 10L of rock mineral water is added to 1 kg of mulberry, mulberry leaf or mulberry root, extracted by heating at 90 to 120°C for 30 minutes to 3 hours, and then filtered. 100 parts by weight of mulberry extract, 50 to 150 parts by weight of peach extract, 5 to 20 parts by weight of persimmon vinegar, extracted by adding 10 L of water to 1 kg of shredded Pseudomonas mushrooms, stirred, heated at 90 to 110°C for 3 to 10 hours, and then filtered. , To prepare a coating solution by mixing 1 to 5 parts by weight of sodium alginate, and then discloses a functional rice, characterized in that produced by coating the coating solution on the rice.

However, the technique disclosed in the document is to coat rice with a coating solution or directly use rice protein or rice flour, and the manufacturing method is complex and the medicinal effect is not excellent.

Korean Patent Registration No. 10-0726834 Korean Patent Registration No. 10-1171258 Korean Patent Registration No. 10-1300378

An object of the present invention is to provide a pharmaceutical composition for preventing or treating diabetes, which can be easily and simply prepared and has excellent medicinal efficacy, as to solve the problems of the prior art.

Another object of the present invention is to provide a pharmaceutical composition for preventing or treating diabetes capable of minimizing side effects such as weight gain and headache when taken for a long time.

In order to achieve the above object, the present invention provides a compound represented by the following formula (3).

[Formula 3]

In addition, the present invention (a) separating the rice bran from the super red rice;

(b) heat-extracting the rice bran with a solvent, filtered, concentrated under reduced pressure, and freeze-dried to obtain an extract; And

(c) It provides a method for separating a compound from super red rice, comprising the step of separating the compound of Formula 3 below using HPCCC (High performance counter-current chromatography) from the extract.

[Formula 3]

In one embodiment of the present invention, the heat extraction is characterized in that extraction is performed by adding 500 to 2,000 parts by weight of a solvent to 100 parts by weight of rice bran and heating at 30 to 95° C. for 1 to 3 hours.

In one embodiment of the present invention, the solvent is characterized in that at least one selected from alcohol, ethanol, methanol, hexane, chloroform, methylene chloride, ethyl acetate, and diethylene glycol monoethyl ether.

In addition, the present invention provides a pharmaceutical composition for preventing or treating diabetes, comprising the compound of Formula 3 as an active ingredient.

[Formula 3]

In addition, the present invention provides a food composition for preventing or improving diabetes comprising the compound of Formula 3 as an active ingredient.

[Formula 3]

The present invention can provide a pharmaceutical composition for preventing or treating diabetes that can be prepared easily and simply and has excellent medicinal effects.

In addition, the present invention can provide a pharmaceutical composition for preventing or treating diabetes that can minimize side effects such as weight gain and headache when taken for a long time.

1 shows the HPCCC analysis results of the super red rice extract measured at 280nm and 520nm.
^{2 shows a 1} H-NMR (500MHz) spectrum of the compound of Formula 3.
^{3 shows a 13} C-NMR (125MHz) spectrum of the compound of Formula 3.
4 shows the HSQC spectrum of the compound of Formula 3.
5 shows the HMBC spectrum of the compound of Formula 3.
6 shows the inhibitory activity of the compound of Formula 3 against Rat Intestinal α-glucosidase, α-amylase, Sucrase, Maltase, and Glucoamylase.
7 shows the inhibitory effect of the compound of Formula 3 on the rise of blood glucose after a meal by Sucrose.
8 shows the inhibitory effect of the compound of Formula 3 on the rise of blood glucose after a meal by Starch.

The present invention will be described in detail based on the following examples. The terms, examples, etc. used in the present invention are merely exemplified to describe the present invention in more detail and to aid the understanding of those skilled in the art, and the scope of the present invention should not be construed as being limited thereto.

Technical terms and scientific terms used in the present invention represent the meanings commonly understood by those of ordinary skill in the art, unless otherwise defined.

The present invention relates to a compound represented by the following formula (3).

[Formula 3]

In addition, the present invention (a) separating the rice bran from the super red rice;

(b) heat-extracting the rice bran with a solvent, filtered, concentrated under reduced pressure, and freeze-dried to obtain an extract; And

(c) It relates to a method for separating the compound from the super red rice, comprising the step of separating the compound of the following formula (3) using HPCCC (High performance counter-current chromatography) from the extract.

[Formula 3]

The super red rice is a new variety newly developed by breeding science for the purpose of strengthening functional ingredients, and has a brown or red color in appearance due to its high content of brownish flavonoids.

The recently developed super red rice has a wider breadth and a relatively large volume compared to ordinary rice, while its density is low.

The heat extraction is preferably extracted by adding 500 to 2,000 parts by weight of a solvent based on 100 parts by weight of rice bran and heating at 30 to 95° C. for 1 to 3 hours.

The rice bran may include wheat flour layer (sok rice bran), rice bran (medium rice bran), outer rice bran and germ (rice bran).

The solvent may be at least one selected from alcohol, ethanol, methanol, hexane, chloroform, methylene chloride, ethyl acetate, and diethylene glycol monoethyl ether.

Heat extraction, filtration, concentration under reduced pressure to remove all solvents, and freeze-drying of the concentrate to obtain an extract.

The compound of Formula 3 is isolated from the extract by using high performance counter-current chromatography (HPCCC).

The molecular structure of the isolated compound was ^{determined using nuclear magnetic resonance analysis (NMR) such as 1} H NMR and ¹³ C NMR, melting point, infrared spectroscopy (IR), MS, and the like.

The compound of formula 3 is (2R,3R)-4'-O-methyltaxifolin 3-O-β-D-glucopyranoside ((2R,3R)-4'-O-methyltaxifolin 3-O-β -D-glucopyranoside).

In addition, the present invention relates to a pharmaceutical composition for preventing or treating diabetes, comprising the compound of Formula 3 as an active ingredient.

[Formula 3]

The compound of formula 3 of the present invention can be used for the prevention or treatment of diabetes.

The compound of Formula 3 has excellent antidiabetic activity, antioxidant activity, and postprandial blood sugar control properties, and thus can be effectively used for the prevention or treatment of diabetes.

The pharmaceutical composition of the present invention may further include suitable carriers, excipients, and diluents commonly used in the preparation of pharmaceutical compositions.

The carrier, excipient and diluent include lactose, textrose, sucrose, sorbitol, mannitol, xylitol, erythritol, maltitol, starch, gum acacia, alginate, gelatin, calcium phosphate, calcium silicate, cellulose, methyl cellulose, undecided Vaginal cellulose, polyvinyl phytolidone, water, methylhydroxybenzoate, propyl hydroxybenzoate, talc, magnesium stearate, and mineral oils.

The pharmaceutical composition of the present invention may be formulated and used in the form of oral dosage forms such as powders, granules, tablets, capsules, suspensions, emulsions, syrups and aerosols, external preparations, suppositories, and sterile injectable solutions.

In addition, the present invention relates to a food composition for preventing or improving diabetes comprising the compound of Formula 3 as an active ingredient.

[Formula 3]

Food may be in the form of various foods, candy, beverages, gum, tea, vitamin complexes, health functional foods, and the like, and may be provided in the form of powders, granules, tablets, capsules, beverages, and the like.

The present invention will be described in detail through the following examples. The following examples are only exemplified for the practice of the present invention, and the contents of the present invention are not limited by the following examples.

(Example 1) Preparation of super red rice extract

Rice bran was separated from super red rice according to a general rice bran separation method.

After mixing 6L of methanol (including 0.1% trifluoroacetic acid) to 500 g of rice bran of super red rice, it was extracted for 2 hours at 40°C.

After centrifuging the extract in a centrifuge (8,000 rpm; 4° C.; 30 minutes), the supernatant was filtered through a Watman No. 1 filter.

The filtrate was concentrated under reduced pressure to remove all of the solvent, and then freeze-dried in a freeze dryer to obtain 43 g of an extract.

(Example 2) Separation of active substance from super red rice extract

In order to separate the active material from the super red rice extract, analysis was performed at 280 and 520 nm using HPCCC (High performance counter-current chromatography; preparative scale; MIDI) (Table 1).

Mobile Phase TBME:n-BuOH:MeCN:Water:TFA (1:7:1:5:0.05) Detecter Agilent 1260 DAD Flow 5.0 ml/min Loading amount 10 g

When analyzed at 280 nm, active substances were detected in Fractions 1, 2, 3, and A (FIG. 1).

A compound of Formula 1 was obtained from Fraction 1, a compound of Formula 2 from Fraction 2, and a compound of Formula 3 from Fraction 3.

Fraction A portion was subjected to HPCCC analysis under the conditions of Table 2 to separate the compounds of Formulas 4 and 5.

Mobile Phase n-hexane:ethyl acetate:methanol:water
(2:8:2:8) Detecter Agilent 1260 DAD Flow 5.0 ml/min

(Example 3) Separation of compounds of formulas 1 to 5

The molecular structure of the compounds of Formulas 1 to 5 isolated in Example 2 was ^{determined using 1} H NMR, ¹³ C NMR, MS, and the like.

The compound of formula 1 is cyanidin-3-glucoside (C3G), and the compound of formula 2 is (2R,3R)-dihydroquecetin-3-O-β-D-glucopyranoside ((2R,3R)-dihydroquercetin-3-O-β-D-glucopyranoside), and the compound of Formula 3 is (2R,3R)-4'-O-methyltaxyfoline 3-O-β-D-glu Copyranoside ((2R,3R)-4'-O-methyltaxifolin 3-O-β-D-glucopyranoside), and the compound of Formula 4 is (2R,3R)-dihydroquecetin ((2R,3R)- dihydroquercetin; taxifolin; taxifolin), and the compound of Formula 5 is (2R,3R)-3-methoxy-dihydroquercetin ((2R,3R)-3-methoxy-dihydroquercetin).

The compounds of formula (3) morpholin-ylmethyl-suspended from the MS fragmentation pattern mono- glycoside (molecular formula C ₁₆ H ₁₄ O ₇₎ contains and, [MH] a ^- at 479.1204 m / z, [M- Glc + H] + was 319.0808 At m /z , [M+Na] ⁺ is 503.1152 A peak is shown at m/z.

The anomeric proton and six carbon resonance of the compound of Formula 3 are δ _H 3.72 ppm (1H, d, J =7.7 Hz, H-1″), δ _C 102.56 (C-1) ″), 74.69 (C-2″), 78.38 (C-3″), 71.28 (C-4″), 77.62 (C-5″), 62.65 (C-6″) ppm, which shows a peak at β This is the characteristic peak of the -D-glucopyranoside moiety.

From the HMBC correlation of H-1″ (3.72 ppm) and C-3 (77.23 ppm) and H-3 (5.06 ppm) and C-1″ (102.56 ppm), the glucosyl moiety is 4' -It can be seen that it is linked to C-3 of O-methyltaxifolin.

The CD spectrum of the compound of Formula 3 shows a cotton effect at 329.7 nm ([θ] +7,680) and 293.9 nm ([θ] -27,840), which is the characteristic peak of the 2 R ,3 R -dihydroflavonol group.

The characteristic peaks of the compound of Formula 3 are as follows (Figs. 2 to 5).

-23.4°; CD(MeOH)[θ](nm): +34,560 (221.5), +7,680 (329.7), -27,840 (293.9); ¹H-NMR(500MHz, CD₃OD): δ 7.15 (1H, d, J=1.8 Hz, H-2'), 6.96 (1H, dd, J=8.1, 1.8 Hz, H-6'), 6.86 (1H, d, J=8.1 Hz, H-5'), 5.95 (1H, d, J=2.1 Hz, H-6), 5.94 (1H, d, J=2.1 Hz, H-8), 5.28 (1H, d, J=10.5 Hz, H-2), 5.06 (1H, d, J=10.5 Hz, H-3), 3.91 (3H, s, OCH₃-4'), 3.79 (1H, dd, J=12.0, 2.0 Hz, H-6″a), 3.72 (1H, d, J=7.7 Hz, H-1″), 3.62 (1H, dd, J=12.0, 6.0 Hz, H-6″b), 3.26 (1H, dd, J=9.6, 9.1 Hz, H-4″), 3.25 (1H, dd, J=9.2, 7.7 Hz, H-2″), 3.09 (1H, t, J=9.1 Hz, H-3″), 2.98 (1H, ddd, J=9.6, 6.0, 2.0 Hz, H-5″); ¹³C-NMR(126MHz, CD₃OD): δ 196.23 (C-4), 169.00 (C-7), 165.54 (C-5), 164.27 (C-9), 148.94 (C-4'), 148.43 (C-3'), 129.12 (C-6'), 121.95 (C-2'), 116.12 (C-5'), 112.79 (C-1'), 102.58 (C-10), 102.56 (C-1″), 97.36 (C-8), 96.32 (C-6), 83.84 (C-2), 78.38 (C-3″), 77.62 (C-5″), 77.23 (C-3), 74.69 (C-2″), 71.28 (C-4″), 62.65 (C-6″), 56.48 (4'-OCH₃).

-23.4°; CD(MeOH)[[theta]](nm): +34,560 (221.5), +7,680 (329.7), -27,840 (293.9);^OneH-NMR (500MHz, CD₃OD): δ 7.15 (1H, d,J=1.8 Hz, H-2'), 6.96 (1H, dd,J=8.1, 1.8 Hz, H-6'), 6.86 (1H, d,J=8.1 Hz, H-5'), 5.95 (1H, d,J=2.1 Hz, H-6), 5.94 (1H, d,J=2.1 Hz, H-8), 5.28 (1H, d,J=10.5 Hz, H-2), 5.06 (1H, d,J=10.5 Hz, H-3), 3.91 (3H, s, OCH₃-4'), 3.79 (1H, dd,J=12.0, 2.0 Hz, H-6″a), 3.72 (1H, d,J=7.7 Hz, H-1″), 3.62 (1H, dd,J=12.0, 6.0 Hz, H-6″b), 3.26 (1H, dd,J=9.6, 9.1 Hz, H-4″), 3.25 (1H, dd,J=9.2, 7.7 Hz, H-2″), 3.09 (1H, t,J=9.1 Hz, H-3″), 2.98 (1H, ddd,J=9.6, 6.0, 2.0 Hz, H-5″);¹³C-NMR (126 MHz, CD₃OD): δ 196.23 (C-4), 169.00 (C-7), 165.54 (C-5), 164.27 (C-9), 148.94 (C-4'), 148.43 (C-3'), 129.12 ( C-6'), 121.95 (C-2'), 116.12 (C-5'), 112.79 (C-1'), 102.58 (C-10), 102.56 (C-1″), 97.36 (C-8) ), 96.32 (C-6), 83.84 (C-2), 78.38 (C-3″), 77.62 (C-5″), 77.23 (C-3), 74.69 (C-2″), 71.28 (C -4″), 62.65 (C-6″), 56.48 (4'-OCH₃).

(Example 4) In-vitro antidiabetic activity of the compound of formula 3

(A) Rat intestinal α-glucosidase inhibition assay

● Enzyme: Rat small intestine acetone powder

● Substrate: PNP-glycoside (pNPG, p-Nitrophenyl α-D-gluco-

pyranoside)

After adding 9 ml of 0.1M sodium phosphate buffer (pH 6.9) to 300 mg of rat small intestine acetone powder, ultrasonic irradiation was performed 12 times in an ice water bath for 30 seconds, followed by centrifugation at 13,000 rpm and 4° C. for 30 minutes.

The supernatant was used immediately for assay or was used while being stored at -20°C.

After over 50 µl of the sample solution to 100 µl of rat α-glucosidase solution, the mixture was reacted at 37° C. for 10 minutes.

50 µl of 5 mM pNPG solution was added, reacted at 37° C. for 30 minutes, and absorbance was measured at 405 nm using an ELISA reader to analyze the inhibitory activity against rat α-glucosidase.

The inhibitory activity against Rat Intestinal α-glucosidase represented by the compound of Formula 3 is shown in FIG. 6.

The compound of Formula 3 did not show inhibitory activity depending on the molar concentration.

(B) Porcine pancreatic α-amylase inhibition assay

● enzyme: porcine pancreatic α-amylase

● Substrate: 1% starch solution in 0.02 M sodium phosphate buffer (pH 6.9)

● coloring reagent: 3,5-dinitrosalicylic acid solution (DNS) in 2 M NaOH with 30% sodium potassium tartrate tetrahydrate

200 µl of the sample solution was added to 300 µl of a 1U concentration of porcine pancreatic α-amylase solution dissolved in 0.02M sodium phosphate buffer (pH 6.9; including 0.006M sodium chloride) and incubated at 25°C for 10 minutes.

To this solution, 500 µl of a 1% starch solution pre-incubated at 25°C for 10 minutes was added and reacted at 25°C for 10 minutes.

The reaction was stopped by adding 1 ml of 1% DNS solution dissolved in 30% Rochelle salt, followed by treatment in a boiling water bath for 5 minutes, then cooled to room temperature, and 10 ml of distilled water was added.

Absorbance was measured using an ELISA reader at 540 nm for the reaction solution of the DNS solution with the sugar decomposed from the substrate by α-amylase, and the solvent in which the sample was dissolved was added instead of the sample as a control.

The inhibitory activity against α-amylase represented by the compound of Formula 3 is shown in FIG. 6.

The compound of Formula 3 did not show inhibitory activity depending on the molar concentration.

(C) Rat intestinal glucose oxidase assay (Maltose, Sucrose, Glucoamylase) inhibitory activity analysis

Rat small intestine acetone powder (Sigma S9765) was used as the enzyme, and maltose, sucrose, and starch (Junsei) were used as substrates.

100 mg of rat small intestine acetone powder was added to 3 ml of 0.9% NaCl solution (Junsei), followed by ultrasonic irradiation in an iced water bath 12 times for 30 seconds, followed by centrifugation at 10,000 rpm and 4° C. for 30 minutes.

The separated supernatant was used in the experiment.

As for the measurement method, 50 µl of sample was added to 100 µl of rat α-glucosidase solution on a 96 clear plate, and then allowed to stand in an incubator at 37° C. for 10 minutes.

Depending on each experimental method, 50 µl of 100 mM maltose, 200 mM sucrose, or 1% starch solution was added, reacted at 37°C for 30 minutes, and between reactions for 30 minutes, Glucose oxidase/peroxidase reagent (Sigma G3660) and O-Dianisidine reagent ( Sigma D2679) After putting 1 ml of the mixed solution into a 2 ml Epp Tube, let it stand for 5 minutes in an incubator at 37°C to set the temperature to 37°C, and then add 200µl of a mixture reagent of rat small intestine acetone powder, sample, and substrate solution reacted for 30 minutes. Take and add 1 ml of Glucose oxidase/peroxidase reagent and O-Dianisidine reagent to the solution, and then react for 10 minutes in an incubator at 37°C.

Add 1 ml of each 2 ml Epp tube 12N sulfuric acid to stop the reaction, add 200 μl each to 96 clear plates, measure the absorbance at 540 nm using an ELISA reader, and measure rat intestinal glucose oxidase (maltose, sucrose, glucoamylase). Inhibitory activity was analyzed.

Instead of the sample, a solvent in which the sample was dissolved was added as a control.

The inhibitory activity against Sucrase, Maltase and Glucoamylase represented by the compound of Formula 3 is shown in FIG. 6.

It was shown that the inhibitory activity against Sucrase, Maltase and Glucoamylase significantly increased as the concentration of the compound of Formula 3 increased.

It can be seen that the compound of Formula 3 can help inhibit Sucrase, Maltase, and Glucoamylase.

In particular, the concentration of 50% inhibitory activity of sucrase degrading sucrose is 0.54 mM, the lowest concentration, and the concentration of 50% inhibitory activity of glucoamylase decomposing Starch is 6.73 mM.

(Example 5) Postprandial glycemic control action of the compound of formula 3 by in-vivo test

(A) Experimental animals

Four-week-old male SD rats were purchased from Orient Bio and supplied with general blended feed (Orient Bio Pico 5053) and water in the animal breeding room to adapt to the environment, and adapted to the laboratory environment for a week, and only healthy animals were selected and tested. Was used.

(B) Evaluation of blood sugar increase inhibitory effect on sucrose intake

Control (water), Acarbose (5mg/kg Glucobay, Bayer Korea), Compound of Formula 3 (0.1g/kg, 0.5g/kg) in Sucrose of 2g/kg body weight after fasting the experimental animal for at least 20 hours before the experiment Was administered, and the sample was orally administered at 1 ml/ml using a zone for oral administration.

The administration group was 5 groups, and 6 animals were used for each group. Blood was collected from the tail vein at 30, 60, 120, and 180 minutes after oral administration, and the change in venous blood glucose concentration was measured with a glucometer (Caresens II).

The inhibitory effect of the compound of Formula 3 on postprandial blood glucose elevation by sucrose is shown in FIG. 7.

In the control group, blood glucose was found to rise to 198.40 ± 17.07 mg/dl 0.5 hours after meals.

The blood sugar of the compound of formula 3 (0.5g/kg body weight) is 159.63 ± 4.50 mg/dl at 0.5 hours after meals, and it can be seen that it suppresses the increase in postprandial blood sugar by about 19% compared to the control group. It can be seen that this 156.13 ± 11.85 mg/dl suppresses an increase in postprandial blood glucose by about 15% compared to the control group (185.10 ± 8.05 mg/dl).

Through these results, it can be confirmed that the compound of Formula 3 inhibits a rapid rise in blood sugar after sucrose intake and inhibits absorption of blood sugar.

(C) Evaluation of blood sugar increase inhibitory effect on Starch intake

After fasting the experimental animal for at least 20 hours before the experiment, control (water), Acarbose (5mg/kg_Glucobay, Bayer Korea), and the compound of Formula 3 (0.1g/kg, 0.5g/kg) were added to the starch of 2g/kg body weight. It was administered, and the sample was orally administered at 1 ml/ml using a zone for oral administration.

The administration group was 5 groups, and 6 animals were used for each group. Blood was collected from the tail vein at 30, 60, 120, and 180 minutes after oral administration, and the change in blood glucose concentration in venous blood was measured with a glucometer (Caresens II).

The inhibitory effect of the compound of Formula 3 on postprandial blood glucose elevation by Starch is shown in FIG. 8.

In the control group, blood glucose was increased to 195.25 ± 17.10 mg/dl 0.5 hours after meals.

The blood sugar of the compound of formula 3 (0.5g/kg body weight) is 167.25±10.86 mg/dl at 0.5 hours after meals, and it can be seen that it suppresses the increase in postprandial blood sugar by about 14% compared to the control group. It can be seen that this 159.63 ± 22.18 mg/dl suppresses an increase in postprandial blood glucose by about 12% compared to the control group (182.17 ± 10.05 mg/dl).

Through these results, it can be confirmed that the compound of Formula 3 inhibits a rapid rise in blood sugar after ingestion of starch and inhibits absorption of blood sugar.

Claims (6)

A compound of the following formula (3).

[Formula 3]

(a) separating the rice bran from the super red rice;
(b) heat-extracting the rice bran with a solvent, filtered, concentrated under reduced pressure, and freeze-dried to obtain an extract; And
(c) A method for separating a compound from super red rice comprising the step of separating the compound of Formula 3 below using HPCCC (High performance counter-current chromatography) from the extract.

[Formula 3]

The method of claim 2,
The heat extraction is a method for separating a compound from super red rice, characterized in that extraction is performed by adding 500 to 2,000 parts by weight of a solvent to 100 parts by weight of rice bran and heating at 30 to 95°C for 1 to 3 hours.
The method of claim 3,
The solvent is at least one selected from alcohol, ethanol, methanol, hexane, chloroform, methylene chloride, ethyl acetate and diethylene glycol monoethyl ether.
A pharmaceutical composition for preventing or treating diabetes, comprising the compound of Formula 3 as an active ingredient.

[Formula 3]

A food composition for preventing or improving diabetes comprising a compound of the following formula 3 as an active ingredient.

[Formula 3]

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