KR100512482B1 - Composition comprising phlorotannins isolated from the extract of Ecklonia stolonifera Okamura having anti-oxidative activity - Google Patents

Abstract

The present invention relates to a composition containing a phlorotannin compound isolated from an extract of Gompi, which exhibits antioxidant activity, wherein the compound of the phlorotannin isolated from the extract of Gompi of the present invention has an effect of effectively eradicating free radicals by DPPH. Since the composition may be usefully used as a pharmaceutical composition for inhibiting aging due to cell membrane lipid peroxidation and an antioxidant composition for food.

Description

Composition comprising phlorotannins isolated from the extract of Ecklonia stolonifera Okamura having anti-oxidative activity}

The present invention relates to a composition having an antioxidant activity containing phlorotannins isolated from an extract of Gompi having antioxidant activity.

Edible fats and oils and fats have an unpleasant odor, taste or toxicity due to various causes during processing and storage. The alteration of oils and fats is mainly caused by automatic oxidation. In addition, one of the causes of aging that is recognized as an oxidation-related phenomenon in vivo is the superoxide anion radical, hydroxyl radical, singlet oxygen and hydrogen peroxide (H) derived from oxygen. The role of free radicals, such as ₂ O ₂ ), has emerged, and interest in them is now very high (L. Fridorich, Science , 201 , p875-881, 1978). Unsaturated fatty acids of phospholipids, which are constituents of biological membranes, initiate peroxidation reactions by free radicals such as reactive oxygen species and proceed in a chain. Therefore, free radical peroxidation not only enhances cell membrane permeability but also results in overall cytotoxicity and induces aging or pathology of various diseases (MT Huang, et al ., Food). phytochemicals for cancer prevention I, pp 50, 57-57, 71-73, 1994; CT Ho, et al ., Food phytochemicals for cancer prevention II, pp 20-31, 155 , 183-186, 1994). Diseases associated with oxidative stress such as peroxidation include cancer, complex arteriosclerosis, arthritis, cardiovascular disease, and Parkinson's disease.

Therefore, many phenolic compounds, flavone derivatives, tocopherols, ascorbic acid, selenium and other antioxidants in fruits and vegetables delay or prevent the oxidation of fats and prevent and delay cancer and cardiovascular diseases. It also plays an important role in anti-aging (G. Papadopoulos, et al ., J. Am. Oil. Chem. Soc. , 68 , p669-673, 1991; PF Yang, et al ., J. food Sci. , 49 , p489-492, 1984).

The rancidity of fats and oils or foods containing oils and fats is mainly caused by the combination with oxygen in the air. To prevent this, many synthetic or natural antioxidants have been developed. However, due to its effectiveness and economic efficiency, the most commonly used synthetic antioxidants are butylated hydroxytoluene (BHT). , BHA (butylated hydroxyanisole), PG (propylgallate), etc. (AL Branen, J. Am. Oil. Chem. Soc. , 55 , p119-123, 1975; JM Deman, Lipids in principles of Food Chemistry, 57 , p507 -512, 1990). Synthetic antioxidants, however, are most commonly used in commercial foods because of their high antioxidant power, but their use is legally regulated due to concerns about safety when used in foods. Natural products, such as tocopherol, are safe but have the disadvantage of being low in cost and expensive in preventing oxidative chain reaction.

Therefore, in recent years, research has been actively conducted to develop natural antioxidants which are safer and have excellent antioxidant effects in various herbal medicines and edible plant extracts.

Gompi ( Ecklonia stolonifera Okamura) is a perennial kelp family distributed in Korea and Japan. It grows at a depth of 2 to 10 m along the coastline and has been used for food with kelp and seaweed for a long time. Seaweed has traditionally been used as a folk remedy for the treatment of anti-anesthetics, anti-inflammatory agents, eczema, gout and gallstones (Hoppe, In Pharmaceutical Science , p9, 1982). The components of gompi include phloroglucinol (Lee JH et al., Arch. Pharm. Res . 19 , pp223-227, 1996), phlorotannins (Taniguchi K. et al., Nippon ). Suisan Gakkaishi , 57 , pp 2065-2071, 1991) and eclonialactones (Kurata K. et al., Chem. Lett. Pp 267-270, 1989; Kurata K. et al., Phytochemistry, 33 , pp155 -159, 1993). Physiological activities include antioxidant activity (Lee JH et al., Arch. Pharm. Res . 19 , pp223-227, 1996), antimutagenic activity (Lee JH et al., J. Food Sci. Nutr ., 1 , pp64- 68, 1996; Lee JH et al., Nat. Prod. Sci . 4 , pp105-114, 1998; Han ES et al., Environ.Mutagen.Carcinogen . 20 , pp104-111, 2000), Eating inhibitory effect (Taniguchi K. et al., Nippon Suisan Gakkaishi , 57 , pp2065-2071, 1991) and tyrosinase inhibitory activity has been reported, but the active ingredient is not yet known (Park DC et al., J. Fish. Sci. Tech . 3 , pp 195-199, 2000). On the other hand, in view of this point, since the components of gompi is a compound separated from gompi, the edible brown algae, it can be said that it can be used to control the pigmentation of food or other organisms. Fukuyama et al. Reported that phlorotannins with a dibenzo-1,4-dioxin ring act as anti-plasmin inhibitors (Fukuyama Y. et al., Chem. Pharm. Bull ., 37 , pp349-353, 1989; Fukuyama Y. et al., Chem. Pharm. Bull ., 37 , pp2438-2440, 1989; Fukuyama Y. et al., Chem. Pharm. Bull ., 38 , pp133-135, 1990; Fukuyama Y. et al., Chem. Lett ., Pp739-742, 1985; Nakayama Y. et al., Agric.Biol . Chem . 53 , pp3025-3030, 1989). In addition, the effect of prolonging the oxidation-inducing group of methyl-α-linolenate (methyl-α-linolenate) was shown, which is reported that the lower the degree of polymerization of phloroglucinol, the greater the effect (Nakamura T. et al., Fish. Sci . 62 , pp923-926,1996). In contrast, the higher the degree of polymerization and polarity of phlorotannins, the higher the inhibitory effect of feeding on marine herbivores (Hay ME, Ann. Rev. Ecol., Syst . 19 , pp111-145, 1988; Taniguchi K. et al., Nippon Suisan Gakkaishi , 57, pp2065-2071, 1991; Altena A. et al, Biochem Syst Ecol, 20, pp493-499, 1992;.... Boettcher AA et al, Ecology, 74, pp891-903 1993;. Targett NM et al , Oecologia 103 , 170-179, 1995). In addition, phlorofucofuroeckol A has been reported to have the largest algicidal effect on microalgae causing red tide (Nagayama K. et al., Aquaculture , 218 , pp 601-611, 2003). However, the free radical scavenging ability of phlorotannins has not been reported so far.

Accordingly, the present inventors have isolated and identified new phlotantanins having free radical scavenging ability in gompi, and then confirmed the scavenging effect to complete the present invention.

An object of the present invention is to provide a new compound having an antioxidant activity, a composition having an antioxidant activity containing a compound of phlorotannins isolated from the gompi extract of the present invention and inhibiting aging by cell membrane lipid peroxidation containing the same It provides a pharmaceutical composition and an antioxidant composition of food.

In order to achieve the above object, the present invention is isolated from the extract Ecklonia stolonifera Okamura (eckstolonol), ecstolonol pentaacetate (eckstolonol pentaacetate), eccol (eckol), phlorofucopuroekol A (phlorofucofuroeckol It provides a pharmaceutical composition for inhibiting aging by cell membrane lipid peroxidation containing a compound selected from the group consisting of A) and dieckol.

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The gompi extract is a crude extract or a non-polar solvent soluble extract, the crude extract includes water, lower alcohols such as ethanol, methanol, butanol or mixed solvents thereof, preferably extracts soluble in methanol, the non-polar solvent soluble extract is non-polar solvent selected from n -hexane, dichloromethane, chloroform or ethyl acetate, preferably those extracted with ethyl acetate.

Hereinafter, the present invention will be described in detail.

The compounds of phlorotannins isolated from the crude extract and nonpolar solvent soluble extract of the present invention can be obtained as follows.

The crude extract of Gompi of the present invention is pulverized after lyophilization and pulverized, and the volume of water, methanol, ethanol and butanol, such as about 3 to 20 times, preferably about 3 to 5 times the dry weight of the gompi Lower alcohol or a mixed solvent having a mixing ratio of about 1: 0.1 to 1:10, preferably about 0.5 hours to 2 days, preferably at an extraction temperature of 20 to 100 ° C., preferably 20 to 70 ° C., with methanol Preferably it is obtained by extracting from 1 to 5 times, preferably 3 times consecutively by extraction method such as hot water extraction, cold needle extraction, reflux cooling extraction or ultrasonic extraction for 1 hour to 1 day, and then filtered under reduced pressure and rotating the filtrate under vacuum Concentrated under reduced pressure at 20 to 100 ℃, preferably 40 to 70 ℃ with a concentrator can be obtained crude extract extracted from water, lower alcohol or a mixed solvent thereof.

The gompi crude extract is suspended in water and extracted with a solvent in the order of n -hexane, dichloromethane, ethyl acetate, n -butanol to obtain a soluble extract of gompi nonpolar solvent, preferably ethylacetate soluble fraction of the present invention. More specifically, n -hexane: water: methanol is mixed in a crude gom extract, that is, gom methanol extract, in a ratio, preferably 10: 9: 1, to obtain n -hexane-soluble fraction and water-soluble fraction. And extracting the water soluble fraction with dichloromethane again to obtain a water soluble fraction and a dichloromethane soluble fraction, and ethyl acetate can be added to the water soluble fraction to obtain an ethyl acetate soluble fraction and a water soluble fraction. Finally, the water-soluble fraction is extracted with butanol to obtain butanol-soluble fraction and water solubility. Sex fractions can be obtained.

Silica gel column chromatography (SiO ₂ column chromatography) may be performed on the nonpolar solvent soluble fraction, and a fixed solvent may be used in a mixed solvent of ethyl acetate: methanol, preferably 50: 1 mixed solvent of ethyl acetate: methanol. Column chromatography can be carried out at a capacity, preferably at a rate of 1000 ml, to give ten fractions from F1 to F10.

The F1 fraction was separated again by silica gel column chromatography using a mixed solvent of hexane: ethyl acetate 1: 1, and then separated using a 20% to 100% methanol solution by concentration gradient elution in column chromatography, and purified by Sephadex. Compounds can be isolated and identified.

The present invention provides a method for isolating and purifying phlorotannin compounds separated from crude extracts of Gompi and non-solvent soluble extracts.

The present invention provides a composition having an antioxidant activity containing a compound of phlorotannins obtained by the above method.

As a result of measuring DPPH free radical scavenging ability in order to investigate the efficacy of the phlorotannin compounds isolated from the Gompi extract as an antioxidant activity composition, the results of the present invention were as follows. It was confirmed that the compound effectively inhibited free groups.

The phlorotannin compounds isolated from the gompi extract of the present invention have little toxicity and side effects, and therefore can be used safely even for long-term use for the purpose of prevention.

The composition showing an antioxidant activity comprising the phlorotannin compound isolated from the extract of the present invention may further include an excipient commonly used in the art to which the present invention belongs.

The present invention also provides a pharmaceutical composition for inhibiting aging by cell membrane lipid peroxidation, which contains a phlorotannin compound isolated from an extract of Gompi as an active ingredient.

The pharmaceutical composition for inhibiting aging by cell membrane lipid peroxidation of the present invention comprises 0.5% to 50% by weight of the compound based on the total weight of the composition.

Pharmaceutical compositions comprising the compounds of the present invention may further comprise suitable carriers, excipients and diluents commonly used in the manufacture of pharmaceutical compositions.

The pharmaceutical compositions comprising the compounds according to the present invention may be prepared in the form of powders, granules, tablets, capsules, suspensions, emulsions, syrups, aerosols and the like, oral preparations, suppositories, and sterile injectable solutions, respectively, according to conventional methods. Carriers, excipients and diluents which may be formulated and used in the composition comprising the extract include 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. When formulated, diluents or excipients such as fillers, extenders, binders, wetting agents, disintegrating agents, and surfactants are usually used. Solid preparations for oral administration include tablets, pills, powders, granules, capsules, and the like, and the solid preparations may include at least one excipient such as starch, calcium carbonate, sucrose in the extract. ) Or lactose, gelatin and the like are mixed. In addition to simple excipients, lubricants such as magnesium styrate talc are also used. Liquid preparations for oral use include suspensions, solvents, emulsions, and syrups, and may include various excipients, such as wetting agents, sweeteners, fragrances, and preservatives, in addition to commonly used simple diluents such as water and liquid paraffin. have. Formulations for parenteral administration include sterile aqueous solutions, non-aqueous solvents, suspensions, emulsions, lyophilized preparations, suppositories. As the non-aqueous solvent and suspending agent, propylene glycol, polyethylene glycol, vegetable oil such as olive oil, injectable ester such as ethyl oleate and the like can be used. As the base of the suppository, witepsol, macrogol, tween 61, cacao butter, laurin butter, glycerogelatin and the like can be used.

The amount of the compound of the present invention may vary depending on the age, sex, and weight of the patient, but in general, the amount of 0.01 to 500 mg / kg, preferably 0.1 to 100 mg / kg, is divided once to several times daily. May be administered. The dosage of the compound can also be increased or decreased depending on the route of administration, the severity of the disease, sex, weight, age, and the like. Therefore, the above dosage does not limit the scope of the present invention in any aspect.

On the other hand, it provides an antioxidant composition for foods containing the phlorotannin compound of the present invention as an active ingredient.

At this time, the composition may be added to the food by immersing, spraying or mixing in the food, the addition rate is generally selected from the range of 0.01% to 10%.

In addition, the food is a fruit, vegetable, dried or cut products of fruit or vegetables, fruit juice, vegetable juice, mixed juice or chips, noodles, livestock processed food, fish processed food, dairy food, fermented milk food, cereal food , Microbial fermented foods, bakery, condiments, meat processing, acidic beverages, licorice, herbs and any one or more.

Hereinafter, the present invention will be described in detail by way of examples.

However, the following Examples and Experimental Examples are merely illustrative of the present invention, and the content of the present invention is not limited by the following Examples and Experimental Examples.

Example 1 Preparation of Gompi Crude Extracts

Gompi used in the present invention was collected from the sea in front of the stool coast of Gijang-gun, Busan. After freeze drying, 3 kg of powder obtained by lyophilization was added with 10 liters of methanol, and the mixture was refluxed and extracted three times at a predetermined time interval (12 h, 6 h, 3 h) at 70 ° C., followed by filtration under reduced pressure with Wattman (USA). Then, the filtrate extract was obtained by removing the methanol at 40 ℃ in a vacuum rotary concentrator to obtain 700 g of gompi crude extract as a residue, 2 g of the extract was used as a sample for the enzyme activity search.

Example 2. Preparation of Gomphy hexane Soluble Extract

4 g of a mixed solvent of hexane: methanol: water = 10: 9: 1 was added to 700 g of the extract of Gompi crude obtained in Example 1, followed by mixing three to four times to obtain 2 L of water-soluble fraction and 2 L of hexane-soluble fraction. After obtaining the hexane soluble fraction was dried to obtain a hexane soluble extract 27.93 g was used as a sample, 2 g of this was used as a sample for enzyme activity screening.

Example 3 Preparation of Gompi Dichloromethane Soluble Extract

       2 L of dichloromethane was added to 2 L of the water-soluble fraction obtained in Example 2, followed by mixing three to four times to obtain 2 L of the water-soluble fraction and 2 L of the dichloromethane-soluble fraction. The dichloromethane-soluble fraction was dried. 25.58 g of a dichloromethane soluble extract was obtained and used as a sample, and 2 g of the sample was used as a sample for enzyme activity search.

Example 4 Preparation of Gompi Ethyl Acetate Soluble Extract

2 L of ethyl acetate was added to 2 L of the water-soluble fraction obtained in Example 3, followed by mixing three to four times to obtain 2 L of the water-soluble fraction and 2 L of the ethyl acetate-soluble fraction, which was then dried. 24.99 g of ethyl acetate soluble extract was obtained and used as a sample, 2 g of which was used as a sample for enzyme activity screening.

Example 5 Preparation of Gompi Butanol Soluble Extract

2 L of butanol was added to 2 L of the water-soluble fraction obtained in Example 4, followed by mixing 3-4 times to obtain 2 L of water-soluble fraction and 2 L of butanol-soluble fraction, and then the water-soluble fraction and butanol-soluble fraction. After drying, 99.59 g of a soluble extract and a butanol soluble extract were obtained and used as a sample, 2 g of which was used as a sample for enzyme activity screening.

Example 6 Isolation of Florotannin Compounds

Silica gel column chromatography was performed on 99.59 g of the Gompi ethyl acetate soluble extract of Example 4. At this time, a 50: 1 mixture of ethyl acetate: methanol was used as a developing solvent, and a fraction of 1000 ml / hour was performed using a Kigel gel 60 (Kiesel gel 60, 230-400 mesh) as a fixed phase. After dividing the fractions, the activity of each fraction was measured, and the most active F1 fraction was used as a solvent, a mixed solvent of hexane: ethyl acetate = 1: 1, and as a stationary phase Kiesel gel 60 (Kiesel gel 60, Silica gel column chromatography (230-400 mesh) was carried out, and then RP-18 CC was used as a fixed phase with Licroprep (Lichroprep, Merck, Germany), and 20% to 100% methanol solution was used as a solvent. Then, the mixture was separated by concentration gradient elution, and then purified by Sephadex LH-20 (St. Louis, MO, Sigma Co., Ltd.) to separate 2-6 compounds of phlorotannins as described below. Analysis of each compound by various analyzers such as NMR and MS is as follows.

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(2) Compound 2: ecstolonol

       Appearance of substance: White powder.

Molecular formula of material: C1 ₈ H ₁₀ O ₉ .

HRFAB-MS: Found, m / z 370.0324 [M] < + >, Calcd for C1 ₈ H ₁₀ O ₉ , m / z 370.0325.

IR (KBr) cm ^-1 : 3243, 1635, 1518, 1494, 1396, 1281, 1243, 1207, 1154, 1118, 1089, 1012, 810.

1 H-NMR (400 MHz, DMSO- d 6): 9.77 (C1-OH), 9.64 (C9-OH), 9.60 (C6-OH), 9.27 (C3-OH), 9.26 (C11-OH), 6.10 ( 1H, s, H-7), 6.04 (1H, d, J = 2.81 Hz, H-2), 6.01 (1H, d, J = 2.66 Hz, H-10), 5.84 (1H, d, J = 2.66 Hz, H-4), and 5.82 (1H, d, J = 2.66 Hz, H-12).

13C-NMR (100 MHz, DMSO- d 6): 153.3 (C-3), 153.0 (C-11), 146.1 (C-1), 146.0 (C-9), 142.1 (C-4a), 141.7 ( C-12a), 140.1 (C-6), 137.2 (C-7a), 131.6 (C-13b), 125.9 (C-5a), 122.7 (C-8a), 122.5 (C-13a), 122.3 (C -14a), 98.8 (C-2, 10), 97.6 (C-7), and 93.9 (C-4, 12).

(3) Compound 2a: ecstolonol pentaacetate

IR (KBr) cm −1: 1769, 1506, 1477, 1371, 1193, 1079, 1021, 885.EI-MS m / z (R. int.): 580 (M +, 21), 538 (45), 496 (47), 454 (72), 412 (52), 370 (100), 341 (30).

1 H-NMR (400 MHz, CDCl 3 + DMSO- d 6): 1.59 (3H, s), 1.61 (3H, s), 1.64 (3H, s), 1.65 (3H, s), 1.73 (3H, s), 5.80 (1H, s), 5.96 (1H, d, J = 2.62 Hz), 5.97 (1H, d, J = 2.62 Hz), 6.00 (1H, d, J = 2.62 Hz), 6.02 (1H, d, J = 2.62 Hz).

(4) compound 3: ecol

Form of material: amorphous powder.

Molecular formula of the substance: C ₁₈ H ₁₂ O _9.

Positive FAB-MS m / z : 372 [M] < + >.

1 H-NMR (400 MHz, CD3 OD): 5.93 (3H, s), 5.94 (2H, s), 6.13 (1H, s).

13C-NMR (100 MHz, CD3OD): 162.4, 160.7, 150.0, 147.7, 147.6, 144.7, 143.8, 139.0, 126.1, 125.3, 125.1, 100.3, 99.9, 98.2, 96.3, 95.9.

(5) Compound 4: phlorofucofuroeckol A

Form of material: amorphous powder.

Molecular formula of material: C ₃ 0H ₁₈ O ₁₄ .

Positive FAB-MS m / z : 602 [M] < + >.

1H-NMR (400 MHz, CD3OD): 6.63 (1H, s), 6.40 (1H, s), 6.26 (1H, s), 5.97 (2H, d, J = 2.08 Hz), 5.94 (1H, t, J = 1.88 Hz), 5.92 (1H, t, J = 1.98 Hz), 5.88 (2H, d, J = 2.08 Hz).

13C-NMR (100 MHz, CD3OD): 162.67, 162.64, 161.00, 160.97, 153.99, 152.50, 151.96, 149.07, 149.03, 146.74, 144.71, 139.19, 136.15, 128.89, 125.86, 125.56, 123.17, 106.15, 106.11. 100.22, 98.60, 98.48, 97.03, 96.24, 96.21.

(6) Compound 5: Dieckol

Form of material: amorphous powder.

Molecular formula of material: C ₃₆ H ₂₁ O ₁₈ . positivity

FAB-MS m / z : 742 [M] < + >.

1 H-NMR (400 MHz, CD3OD): 6.15 (1 H, s), 6.13 (1 H, s), 6.09 (2 H, s), 6.06 (1 H, d, J = 2.85 Hz), 6.05 (1 H, d, J = 2.85 Hz), 5.98 (1H, d, J = 2.76 Hz), 5.95 (1H, d, J = 2.76 Hz), 5.92 (3H, s).

13C-NMR (100 MHz, CD3OD): 162.67, 160.95, 158.61, 156.81, 155.33, 153.19, 148.14, 148.09, 147.92, 147.71, 145.10, 144.95, 144.20, 144.10, 139.44, 139.27, 127.28, 127.28. 125.67, 125.45, 125.38, 100.67, 100.56, 100.30, 100.19, 98.47, 97.02, 96.65, 96.57, 96.17.

Experimental Example 1. Measurement of DPPH radical scavenging assay of phlorotannin compounds isolated from Gompi extract

DPPH radical scavenging activity was measured by the following experiment to determine the antioxidant activity of the phlorotannin compounds isolated from the Gompi extract.

First, 160 μl of the compound of each concentration (1.25 to 320 μg / ml) was dissolved in methanol, and mixed well with 40 μl of a 1.5 × 10 ⁻⁴ M DPPH methanol solution, and the reaction mixture was allowed to stand at room temperature for 30 minutes. The absorbance was then measured at 520 nm with a microplate reader spectrophotometer VERSAmax. Free radical scavenging activity was expressed as a percentage compared to the negative control without the sample, and 50% inhibition concentration (IC ₅₀ ) was calculated. The measured value was taken as the average value of 3 replicate experiments, and the result is shown in following Table 1.

As can be seen in Table 1, the compounds of phlorotannins isolated from the Gompi extract effectively inhibited DPPH radicals, each IC ₅₀ value is 956.9 μM of phloroglucinol, 8.8 μM of axstronole, 11.5 of ecol. μM, phlorofucopurocol was 4.7 μM and dieckol was 6.2 μM. In addition, IC ₅₀ of L-ascorbic acid, a positive control, was 10.3 μM, and extronol, fluorofucopuroexol and dieckol showed much stronger radical scavenging activity than the control.

compound IC ₅₀ μg / ml (μM)   Floroglucinol (1) 120.6 (956.9)   Exxtonolol (2) 3.3 (8.8)   EXCOL (3) 4.3 (11.5)   Florofucopuroeckol (4) 2.8 (4.7)   Dieckol (5) 4.6 (6.2)   L-ascorbic acid 1.8 (10.3)

Examples of the formulation of the pharmaceutical composition will be described below, which is intended to explain in detail only and not intended to limit the present invention.

Formulation Example 1 Preparation of Injection

Florofuocopuro extract of Example 6 ....... 100 mg

Sodium metabisulfite .................. 3.0mg

Methylparaben ...... 0.8 mg

Propylparaben ....................... 0.1mg

Sterile distilled water for injection .............

 The above ingredients were mixed and made into 2 ml by a conventional method, and then filled into 2 ml ampoules and sterilized to prepare an injection.

Formulation Example 2 Preparation of Tablet

Phlorofucopurocol of Example 6. 200 mg

Lactose ......................................... 100 mg

Starch ..................... 100 mg

Magnesium Stearate .....

The tablets were prepared by mixing the above components and tableting according to a conventional method for producing tablets.

Formulation Example 3 Preparation of Capsule

Florofucopurocol of Example 6 100 mg

Lactose ......................................... 50 mg

Starch ......................................... 50 mg

Talc ........................................ 2 mg

Magnesium Stearate ...........

The capsules were prepared by mixing the above components and filling the gelatin capsules according to a conventional method for preparing capsules.

Formulation Example 4 Preparation of Liquid

Phlorofucopurocol of Example 6 ............ 1000 mg

Sugar ........... 20 g

Isomerized sugar ......................... 20 g

Lemon scent ...

Purified water was added to adjust the total volume to 100 ml.

The above-mentioned components were mixed according to a conventional method for preparing a liquid solution, filled into a 100 ml brown bottle, and sterilized to prepare a liquid solution.

The phlorotannins compound isolated from the gompi extract of the present invention effectively eliminates DPPH radicals, and thus can be used as a composition having antioxidant activity, as a pharmaceutical composition for inhibiting aging by cell membrane lipid peroxidation and as an antioxidant composition for food.

Claims (4)

delete Consisting of ecstolonol, ecstolonol pentaacetate, eckol, phlorofucofuroeckol A and dieckol isolated from the extract of Ecklonia stolonifera Okamura A pharmaceutical composition for inhibiting aging by cell membrane lipid peroxidation containing a compound selected from the group of compounds. delete delete