KR20030039143A - Novel benzofuran compound from Suillus granulatus and antioxidative composition comprising it as an active material - Google Patents

Abstract

PURPOSE: Benzofuran compounds derived from Suillus granulatus (L. ex Fr.) O. Kuntxe and an antioxidative composition containing the same compounds as an active ingredient are provided. The benzofuran compounds have antioxidative activity and no toxicity, so that they can be added to medicines, cosmetics and foods. CONSTITUTION: Benzofuran compounds represented by formula(1) are separated and purified by the steps of: dipping fruit bodies of Suillus granulatus (L. ex Fr.) O. Kuntxe in methanol for 3 days; concentrating the methanol extract under reduced pressure; extracting remnants with ethylacetate and concentrating the ethylacetate extract under reduced pressure; subjecting the methanol extract and the ethylacetate extract to silica gel column chromatography using CHCl3:MeOH to obtain an active fraction; concentrating the active fraction and subjecting it to Sephadex LH-20 column chromatography using CHCl3:MeOH(2:1).

Description

Novel benzofuran compound from Suillus granulatus and antioxidative composition comprising it as an active material

The present invention relates to a novel benzofuran compound derived from lactose net mushroom and an antioxidant composition containing the same as an active ingredient. More specifically, the present invention relates to a novel benzofuran compound having an antioxidant activity obtained by purely extracting and separating lactose net mushrooms and an antioxidant composition containing the same as an active ingredient.

Free radicals are a direct or indirect cause of various diseases, including stroke, myocardial infarction, diabetic vascular disorders, hyperlipidemia, acute inflammation, rheumatic diseases, alcoholic hepatitis, arteriosclerosis, carcinogenesis, and aging due to cerebrovascular disorders. have. Active oxygen scavengers have been reported to reduce or prevent these diseases, and various active oxygen scavengers have been found in microorganisms and plants and are used as pharmaceuticals or cosmetics and food additives.

Highly reactive activity such as superoxide (OH ₂ ), hydroxyl radical (OH) and hydrogen peroxide (H ₂ O ₂ ) due to various oxidation reactions, chemicals, food, human diseases and radiation When oxygen and free radicals are generated in vivo, the phospholipids of the cell membrane containing a large amount of unsaturated fatty acids are oxidized, thereby producing lipid peroxides on the cell membrane. Accumulation of lipid peroxides in the cell membrane reduces the fluidity and functionality of the cell membrane, thereby inhibiting the overall function of the cell and changing the structure of the cell. Therefore, if excessive reactive oxygen and free radicals accumulate in the human body, various human diseases such as stroke, myocardial infarction, diabetic vascular disorders, hyperlipidemia, acute inflammation, rheumatic diseases, alcoholic hepatitis, and the like are caused. Therefore, the active oxygen scavenger that is powerful but not toxic will be very useful as a therapeutic agent for various diseases or as an anti-aging cosmetic additive and food additive. Until now, synthetic antioxidants such as butylated hydroxy toluene (BHT) and butylated hydroxyanisol (BHA) have been used as antioxidant compounds. However, these BHT and BHA have excellent antioxidant activity but are highly likely to cause cancer or malformation. There was a disadvantage. Therefore, it is required to develop an antioxidant that has no toxicity or side effects by creating a new active oxygen scavenger from natural products.

In view of the above, the present inventors collected and investigated various mushrooms and medicinal plants, and obtained pure benzofuran-based compounds by methanol extraction of lactose net mushrooms, and then chromatographic extraction to obtain novel benzofuran compounds. After physicochemical characteristics were investigated, the present invention was completed by evaluating the antioxidant activity by investigating DPH radical scavenging activity and using it in various cosmetic formulations.

Accordingly, an object of the present invention is to provide a novel benzofuran compound having antioxidant activity obtained by purely purified from lactose net mushroom. Another object of the present invention is to provide an antioxidant composition containing a novel benzofuran compound having an antioxidant activity obtained by purely separating and purifying from lactose net mushroom.

The object of the present invention is to extract novel benzofuran compound by methanol extraction of lactose net mushrooms and then purified by chromatography to investigate the chemical structure and physicochemical properties of the python H radical scavenging activity This was achieved by evaluating antioxidant capacity and using it in various cosmetic formulations.

Hereinafter, the configuration of the present invention.

The present invention comprises the steps of pulverizing lactose net mushrooms and extracting with methanol, and purified and purified the novel benzofuran compound purely using chromatography; Examining the chemical structure and physicochemical properties of the compound obtained in the step; Comprising the step of using the compound of the various cosmetic formulations.

The novel benzofuran compound Schulsine according to the present invention has the following formula.

Physical and chemical properties of the novel benzofuran compound according to the present invention are as follows.

Appearance: Yellow Powder

Molecular Weight: 370

Molecular Formula: C ₁₉ H ₁₄ O ₈

Radiance: [α] _D + 4 ( c 1.0, MeOH)

Mass Segmentation Spectrum: HREIMS m / z 370.0705 [M] ⁺

EIMS m / z 370 [M] ⁺

UV absorption spectrum: UV λ max (MeOH) (log ε )

223 (sh) (3.56), 261 (3.21), 311 (sh) (3.30),

348 (3.42) nm

Infrared spectrum: IR (KBr) ν max

3412, 2924, 2852, 1728 (sh), 1703, 1611

1523, 1490, 1439, 1386, 1284, 1218 cm ^-1

Hydrogen Magnetic Resonance Spectrum: ppm (600 MHz)

¹ H NMR (CD ₃ OD): 7.64 (1H, d, J = 2.0 Hz, H-2), 7.42 (1H, dd, J = 8.8, 2.0 Hz, H-6), 6.81 (1H, dd, J = 2.4, 1.0 Hz, H-8), 6.79 (1H, d, J = 8.8 Hz, H-5), 6.68 (1H, d, J = 8.8 Hz, H-5), 6.64 (1H, ddd, J = 8.8, 2.4, 1.0 Hz, H-6), 4.15 (1H, br s, H-8b), 3.72 (3H, s, OC H ₃ ); ¹ H NMR (acetone- d ₆ ) d 9.17 (1H, s, O H ), 8.34 (2H, s, O H ), 8.02 (1H, s, O H ), 7.67 (1H, d, J = 2.2 Hz , H-2), 7.52 (1H, dd, J = 8.4, 2.2 Hz, H-6), 6.90 (1H, d, J = 8.4 Hz, H-5), 6.84 (1H, m, H-8) , 6.69 (1H, m, H-5), 6.69 (1H, m, H-6), 4.27 (1H, br s, H-8b), 3.71 (3H, s, OC H ₃ )

Carbon Magnetic Resonance Spectrum: ppm (150 MHz)

_{^{13 C NMR (CD 3 OD)}} : 197.8 (C-1), 173.5 (C OOCH 3), 153.8 (C-4a), 153.4 (C-7), 151.0 (C-2), 148.3 (C-4) , 146.2 (C-3), 137.2 (C-3), 125.3 (C-1), 123.9 (C-8a), 122.8 (C-6), 117.4 (C-6), 117.1 (C-2), 116.2 (C-5), 112.2 (C-8), 111.7 (C-5), 91.9 (C-3a), 56.9 (C-8b), 53.7 (COO C H ₃ )

From the analysis of the above physicochemical properties and nuclear magnetic resonance spectra, the compound Schullin according to the present invention was identified as a novel benzofuran compound.

The benzofuran compound according to the present invention is extracted from an organic solvent (alcohol, ether, acetone, etc.) from mushroom fruit bodies and mycelium cultures belonging to the genus Mushroom ( Suillus ), distribution of ethyl acetate and water, column chromatography, etc. Known methods used for separation extraction can be easily obtained alone or in combination as appropriate. The crude extract can be further purified according to a commercial method as needed.

Chromatography used in the present invention includes silica gel column chromatography, silica-20 column chromatography, thin layer chromatography (TLC) and high performance liquid chromatography (TLC). high performance liquid chromatography) and the like.

The novel benzofuran compound Schulsine according to the present invention has a function of scavenging DPP radicals and is lower in cytotoxicity than other DPH radical scavenging substances and thus can be utilized as an antioxidant in vivo.

The novel benzofuran compound Schulsine according to the present invention not only shows excellent DPH radical scavenging activity but also has high stability and can be used as an additive for food, beverage and cosmetics as an antioxidant. In addition, it can also be used in various medicines by using the antioxidant activity in vivo.

When applied to pharmaceuticals can be formulated as an oral or parenteral dosage form in the form of a solid, semi-solid or liquid by adding a commercially available inorganic or organic carrier with the compound Schulsin according to the present invention as an active ingredient.

Examples of preparations for oral administration include tablets, pills, granules, soft and hard capsules, powders, fine granules, powders, emulsions, syrups and pellets. have. Preparations for parenteral administration include injections, drops, ointments, lotions, sprays, suspensions, emulsions, suppositories, and the like. In order to formulate the active ingredient of the present invention, it can be easily formulated according to the conventional method, and surfactants, excipients, coloring agents, spices, preservatives, stabilizers, buffers, suspensions, and other commonly used auxiliaries can be suitably used.

Hereinafter, the specific method of the present invention will be described step by step with reference to Examples, but the scope of the present invention is not limited only to these Examples.

Example 1 Isolation and Purification of the Benzofuran Compound Schleusin

Lactose silk mushroom fruiting bodies were immersed in methanol for 3 days and extracted at room temperature. The methanol extract was concentrated under reduced pressure, and the remaining residue was extracted with ethyl acetate, and the extract was concentrated under reduced pressure, and subjected to silica gel column chromatography using CHCl ₃ : MeOH as a developing solvent. After concentrating the active fraction obtained above, Sepadex LH-20 column chromatography was performed using CHCl ₃ : MeOH (2: 1) as a developing solvent. Was separated.

Example 2 Analysis of Physicochemical Properties and Chemical Structure of Benzofuran Compound Schulsin

Compound Schlussin obtained as described above was a yellow powder and the molecular weight was 370 by EI-mass measurement. As a result of high resolution EI-mass measurement, the molecular formula of the compound was determined to be C ₁₉ H ₁₄ O ₈ . UV spectra showed maximum absorption peaks at 223, 261, 311, and 348 nm, and IR spectra showed hydroxyl groups at 3412 cm ^-1 and carbonyl groups at 1728 and 1703 cm ^-1 . ) Bands were observed. The fluorescence was + 4 ° each.

Example 3 Investigation of DPPH Radical Scavenging Activity

100 μg of Schusin was dissolved in 20 μl of methanol and added to 980 μl of 150 μM DPH ethanol solution. The solution was mixed well using a vortex and left at room temperature for 20 minutes, and the absorbance was measured at 517 nm. As a control, the same concentration of 100 ㎍ / ㎖ BHA (butylated hydroxyanisole) and vitamin E was used. As a result, it showed a DPPH radical scavenging activity of 30% of sucrose, 76% of BHA, and 73% of vitamin E. Although Schulsine showed lower activity than the control, the compound is isolated from edible mushrooms and is not toxic and has the advantage of providing a new skeleton antioxidant.

Example 4 Preparation of Cosmetics Containing Lactobacillus Extract

By adding a certain weight% lactose net mushroom extract obtained in Example 1 to prepare a lotion, cosmetic cream and pack according to a conventional conventional process. The blending ingredients of each formulation and the weight percentage of each blending component are shown in Tables 1, 2, and 3 below.

toilet water Ingredient weight% Lactobacillus net mushroom extract 1.0 glycerin 5.0 Polyoxyethylene sorbitan monolaurate 1.5 ethanol 10.0 Preservatives, Antioxidants a very small amount Spices a very small amount Purified water to 100

Nutrition Cream Ingredient weight% Lactobacillus net mushroom extract 0.3 glycerin 5.0 Stearyl alcohol 5.0 Stearic acid 8.0 Skuran 10.0 Self-emulsifying glyceryl monostearate 3.0 Polyoxyethylene cetyl ether 1.0 Propylene glycol 5.0 Potassium hydroxide 0.3 Preservatives, Antioxidants a very small amount Spices a very small amount Purified water to 100

Pack Ingredient weight% Lactobacillus net mushroom extract 1.0 Vinyl acetate resin emulsion 15.0 Polyvinyl alcohol 10.0 olive oil 3.0 glycerin 5.0 Titanium oxide 8.0 Gaolin 7.0 ethanol 5.0 Preservatives, Antioxidants a very small amount Spices a very small amount Purified water to 100

As described above, the compound Schulsine of the present invention, as described through the above examples, has an antioxidant activity and extracts and isolates from edible mushrooms, which are edible mushrooms.

Claims (2)

A novel benzofuran compound represented by the following formula (I). [Formula I] An antioxidant composition containing the compound of claim 1 as an active ingredient.