KR101162511B1 - New Anthocyanin Isolated from Purple-Fleshed Potatoes and Preparing Method For the Same - Google Patents

Abstract

The present invention relates to a novel compound exhibiting antioxidant and anticancer activity isolated from colored potatoes and a method for preparing the same, and more particularly, to be isolated and identified from Solanum tuberosum L. cv Jayoung and named by the applicant. The present invention relates to a novel compound, Petunanin JY, and a preparation method thereof.

The novel compounds of the present invention are isolated from colored potato, which is an edible plant, and have almost no side effects on normal cells, and thus exhibit high antioxidant and anticancer activity, and thus are used together with anti-cancer and cancer prevention effects and treatments for various diseases. The treatment and prevention effect can be increased, and the effect can be expected to be applied to functional foods exhibiting cancer prevention and antioxidant effects, and functional cosmetics expressing antioxidant effects.

Colored Potato, Potato, Anthocyanin, Antioxidant, Anticancer

Description

New Anthocyanin Compound Isolated from Colored Potatoes and Preparation Method of It {New Anthocyanin Isolated from Purple-Fleshed Potatoes and Preparing Method For the Same}

The present invention relates to a novel anthocyanin compound isolated from colored potatoes and a method for producing the same.

Potatoes ( Solanum tuberosum L.) are a perennial plant belonging to the family Solanaceae, originating from the central highlands of the Andes of South America, from the north-central part of Chile to Bolivia, Peru, and Ecuador. It is reported that the same cultivar was cultivated more than 1,000 years ago and was introduced to the West by the Spanish in the 16th century. In Korea, seed potatoes were introduced and cultivated from China by the Dutch around 1830.

Potatoes are grown in more than 130 countries because of their short growing period, high yield per unit area, and high environmental adaptability, and are considered to be the world's major food crops alongside rice, wheat, soybeans, and corn. Potato tubers currently grown all over the world are predominantly white or light yellow, but in nature, due to the diversity of genes involved in tuber color formation, various colors containing anthocyanin pigments such as red and purple are found. Colored potatoes also exist.

Currently, potato is mostly used as food in Korea, and it is grown all over Korea, and most of potato used for food is common species with tuber color in white-yellowish color. As this heightens, some colored potatoes are being cultivated in Korea.

Colored potatoes containing red or purple anthocyanin pigments in tubers not only have their own color and unique taste, but also retain their color after cooking when used for salads or fries. Increasing consumer demand for color, color potato is reported to contain a large amount of anthocyanin pigments and phenolic acid, in the United States the amount of color potato consumed as vegetables is 135 pounds per person Is reaching.

Recently, anti-oxidation, anti-mutation and growth inhibition effects of certain cancer cells of colored potato extract have been reported, but there is no information on the source of each activity.

An object of the present invention is to identify the source material of the activity having a colored potato and to identify and provide it.

As an example for achieving the above object, the present invention provides a novel compound or a salt thereof represented by the following formula (1).

[Formula 1]

As another example for achieving the above object, the present invention provides a colored potato extract, characterized in that it comprises a compound represented by the formula (1) or a salt thereof.

As another example for achieving the above object, the present invention is to extract the colored potato with an alcohol containing acid and concentrated under reduced pressure to obtain an alcohol extract, concentrating the alcohol extract and mixing the acid-containing water and alcohol After dissolving in a solvent to perform chromatography (chromatography) and to concentrate the fractions for each solvent to obtain a concentrate, the active fraction concentrate the active fraction of the concentrate in the acid-containing alcohol and then chromatograph the activity Collecting the fractions, and separating the active fractions by chromatography, removing the solvent, and lyophilizing to obtain a target compound.

In the above production method, the acid in the acid-containing alcohol and the acid-containing water is more preferably contained 0.1 to 5% (w / w).

As another example for achieving the above object, the present invention, the compound represented by the formula (1) or a pharmaceutically acceptable salt thereof, or a pharmaceutical showing an anticancer and antioxidant effect, characterized in that it contains a colored potato extract comprising the same To provide a composition.

As another example for achieving the above object, the present invention, having a compound represented by the formula (1) or a pharmaceutically acceptable salt thereof, or a colored potato extract comprising the same as an active ingredient having an antioxidant activity Provide cosmetics.

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As another example for achieving the above object, the present invention, the compound represented by the formula (1) or food-acceptable salts thereof, or a colored potato extract comprising the same as an active ingredient, prevention of cancer It provides a food additive having a function.

As another example for achieving the above object, the present invention provides a health functional food having a preventive function of cancer, characterized by containing the food additive.

Hereinafter, the present invention will be described in detail.

The inventors of the present invention purely separated one anthocyanin compound from the methanol extract of the colored potato tuber, unlike the general yellow potato, and as a result of structural identification using instrumental analysis such as NMR, it is a new compound which is unknown until now. It was identified and named petunanin JY.

The novel compound is a red powder, molecular weight is 1110, and the molecular formula is C ₅₃ H ₅₇ O ₂₆ ⁺ .

The novel compounds of the present invention represented by Chemical Formula 1 may be used as pharmaceutically acceptable salts or foods, and as salts, acid addition salts formed by free or pharmaceutically acceptable food acids may be used. useful.

The novel compounds of the present invention represented by Chemical Formula 1 may form pharmaceutically or food acceptable acid addition salts according to a conventional method in the art. Organic acids and inorganic acids may be used as the acid, hydrochloric acid, bromic acid, sulfuric acid, phosphoric acid may be used as the inorganic acid, and citric acid, acetic acid, lactic acid, tartaric acid, maleic acid, and fumaric acid may be used as the organic acid. (fumaric acid), formic acid, propionic acid, oxalic acid, trifluoroacetic acid, benzoic acid, gluconic acid, methanesulfonic acid, glycolic acid, succinic acid, 4-toluenesulfonic acid, galluxuronic acid, embonic acid, glutamic acid or aspartic acid Etc. can be used.

The present invention includes a colored potato extract including a novel compound represented by the formula (1) or a salt thereof, and the colored potato extract may be used as a component of food or cosmetics.

 The colored potato extract may be used in the conventional extraction methods, such as ultrasonic extraction, filtration, reflux extraction, it can be used for extraction, acetic acid, formic acid, citric acid and the like. If the extract preparation method is different, the quantitative data of the new compound may vary, but the qualitative data does not differ.

In another aspect, the present invention provides a method for extracting, separating and purifying the novel compound of the present invention represented by the formula (1).

The manufacturing method of the present invention includes, first, extracting a colored potato with an acid-containing alcohol and concentrating under reduced pressure to obtain an alcohol extract. The alcohol may be an alcohol having 1 to 3 carbon atoms, an acid may be an organic acid and an inorganic acid, hydrochloric acid, bromic acid, sulfuric acid, phosphoric acid, etc. may be used as the inorganic acid, citric acid, acetic acid as an organic acid , Lactic acid, tartaric acid, maleic acid, fumaric acid, formic acid, propionic acid, oxalic acid, trifluoroacetic acid, benzoic acid, gluconic acid, methanesulfonic acid, glycolic acid, succinic acid, 4-toluenesulfonic acid It may be used to select galgluturonic acid, embon acid, glutamic acid or aspartic acid.

Colored potato is a red, purple known to have a purple, in the present invention, but the use of Solanum tuberosum L. cv Jayoung varieties registered with the Rural Development Administration, but is not limited thereto, commercially available colored potato or cultivated You can use a variety of colored potatoes.

The skin of the colored potato is removed and the fine living body is extracted at room temperature for 24 to 48 hours using an alcohol containing a small amount of acid. It may be desirable to include colored potato biomass in the range of 5-10% (w / w) in the acid-containing alcohol. Inclusion of the acid in the alcohol is to increase the stability of the pigment contained in the colored potato, the acid content is to be about 0.1 to 5% (w / w) of the acid-containing alcohol used, when using hydrochloric acid In the case of using an organic acid of 0.1 to 1% (w / w), it may be used in the range of 0.1 to 5% (w / w).

The alcohol extract is concentrated, dissolved in an acid-containing water and alcohol mixed solvent, and chromatographed to obtain a fraction for each solvent.

In detail, the obtained alcohol extract was concentrated and then chromatographed while changing the ratio of acid-containing water and alcohol-containing alcohol in a column filled with silica gel such as silica, which was dissolved in acid-containing water (distilled water) and octadecylsilylated silica. To obtain a fraction for each solvent.

After dissolving the active fraction concentrate of the active fraction in each of the solvent fractions obtained in an acid-containing alcohol and performing a chromatography to collect the active fractions.

To explain this in detail, after performing chromatography by varying the ratio of water and alcohol, the fractions containing the major anthocyanins in each fraction obtained are concentrated to dry, and it is preferable to use a reduced pressure concentrated dryer at 40 ° C. Thus concentrated to dryness to obtain an active fraction concentrate.

The active fraction may be separated by chromatography, the solvent is removed, and lyophilized to obtain the target compound, thereby obtaining the compound of Chemical Formula 1.

That is, the active fraction is dissolved in an acid-containing alcohol (20%) and subjected to high purity separation using Preparative-HPLC to obtain the target compound. The target compound was identified by FAB-MS, NMR, or the like to obtain a new compound represented by Chemical Formula 1, which was named as petunanin JY.

The new compound obtained has little side effects on normal cells, and exhibits high antioxidant and anticancer activity, so that the new compound can be used in combination with therapeutic agents for the treatment and prevention of cancer and for the treatment of various diseases. .

The present invention also provides an anticancer agent and an antioxidant containing a novel compound represented by Formula 1 or a pharmaceutically acceptable salt thereof.

Since the anticancer agent contains a compound represented by Formula 1 or an pharmaceutically acceptable salt thereof as an active ingredient showing antioxidant activity and anticancer activity, it can be usefully used to inhibit or prevent various cancers by inhibiting growth of cancer cells. have. In addition, since antioxidants inhibit lipid peroxidation and have an excellent ability to remove free radicals, they may be usefully used for the inhibition and prevention of diseases when used in combination with therapeutic agents for various diseases.

The novel compounds can be administered orally or parenterally, for example, intravenously, subcutaneously, intraperitoneally or topically, during clinical administration and can be used in the form of general pharmaceutical formulations.

Pharmaceutical compositions comprising the novel compounds of the invention may be formulated for oral administration such as tablets, troches, lozenges, aqueous or oily suspensions, prepared powders or granules, emulsions, hard or soft capsules. , Syrup or elixirs. Binders such as lactose, saccharose, sorbitol, mannitol, starch, amylopectin, cellulose or gelatin for preparation in formulations such as tablets and capsules; Excipients such as dicalcium phosphate; Disintegrants such as corn starch or sweet potato starch; Lubricants such as magnesium stearate, calcium stearate, sodium stearyl fumarate or polyethylene glycol wax. In the case of a capsule formulation, in addition to the above-mentioned substances, a liquid carrier such as fatty oil is contained.

In addition, pharmaceutical compositions comprising the novel compounds of the present invention may be administered parenterally, and parenteral administration may be by subcutaneous injection, intravenous injection, intramuscular injection or intrathoracic injection. To formulate into parenteral dosage forms, the novel compounds are mixed in water with stabilizers or buffers to prepare solutions or suspensions, which are formulated in unit dosage forms of ampoules or vials.

The effective dose of the novel compound of the present invention represented by Chemical Formula 1 is generally 1 to 50 mg / day, preferably 5 to 20 mg / day, per kg of adult patient, and is fixed according to the judgment of a doctor or pharmacist. It may be administered several times a day at intervals of time, preferably two to three times a day.

The novel compounds of the present invention represented by the above formula (1) are considered to exhibit activity on specific cancer cell lines, and exhibit high anticancer activity against specific cancer cell lines, and thus do not significantly affect normal cells, and thus are used as anticancer agents. It is expected to be used as a combination treatment stabilizer and a synergist to increase the treatment efficiency to secure the stability of existing anticancer drugs.

In addition, since the novel compounds of the present invention are safe for normal cells and have high antioxidant activity, wrinkles of the skin are increased or elasticity is reduced due to the increase of free radicals or active harmful oxygen in the human body, such as blemishes, freckles, and brown mushrooms. It is expected that the aging of the skin typified by pigmentation and the like can be suppressed. Therefore, the antioxidant may be used in cosmetics. Such a novel compound may be used in the form of a separated compound in the cosmetics, but it may be preferable to include in the cosmetics in the form of colored potato extract in terms of economics. When the new compound of the present invention or a salt thereof is included in cosmetics in the form of colored potato extract, it can be used in the range of 0.001 to 20% (w / w), preferably 0.01 to 10% (w / w) of the total weight of the cosmetic. If the content is less than the above range, the anti-aging effect of the skin due to the expression of antioxidant activity will be insignificant. If the content is more than the above range, there is little synergy effect due to the excess input, which tends to be economical.

When introducing a new compound of the present invention or a salt thereof, or a colored potato extract containing the same to the cosmetics, ingredients such as stabilizers, solubilizers, vitamins, pigments and fragrances commonly used as cosmetic ingredients It may include. In addition, the cosmetic formulation is not particularly limited and may be prepared in any formulation commonly prepared in the art, for example, softening water, astringent makeup, nutrient cosmetics, essences, lotions, eye cream, nutrition cream, massage It may be prepared in the form of creams, cleansing creams, cleansing foams, cleansing water, powders, packs, gels, ointments, patches, sprays and the like.

In addition, since it has been identified and separated from the edible colored potatoes, it is stable to the human body and is suitable for use in addition to food, and thus can be developed as a food additive and health functional food having a function of preventing cancer.

When developing as a food additive, food additives may be used as food additives, and may be prepared as a main or secondary ingredient of the food or added to other foods.

0.01 to 50% (w / w) of the total weight, preferably 1 to 30% (w / w) when the new compound of the present invention or a salt thereof is included in a food additive or a health functional food in the form of a colored potato extract It can be used in a range, if the content is less than the above range, the effect obtained due to the expression of the antioxidant effect activity will be insignificant, and if the content exceeds the above range, there is a tendency that is not economical because there is little synergistic effect due to the excess input.

That is, various foods can be prepared by a conventionally known method by adding them in conventional palates such as noodles, tofu, cereals, breads, chewing gum, candy, confectionary, such as ramen noodles, raw noodles, tablets, granules, It may be formulated into general formulations such as pills, hard capsules, soft capsules, liquid formulations, and the like, and may be prepared in juice, pouches, beverages, and teas. Other ingredients in addition to the above components may be appropriately selected by those skilled in the art according to the dosage form. It can mix.

The new compound is isolated from edible colored potatoes and is stable without toxicity to the human body, and has antioxidant activity and anticancer activity.

In other words, it can be confirmed that the novel compound pethunanin JY of the present invention exhibits stable lipid peroxidation inhibitory activity in the early stage of lipid peroxidation, and thus can be expected to be effective as a novel antioxidant.

In addition, the novel compound pethunanin JY of the present invention exhibits high growth inhibitory activity against cancer cell lines, and thus can be expected to be effective as a novel anticancer agent.

In particular, the novel compound pethunanin JY of the present invention not only exhibits high anticancer activity against certain cancer cell lines, but also does not significantly affect normal cells, so that it can be used as an anticancer agent and the stability of combination treatment to stabilize the existing anticancer agent. It can be expected to be used as a synergist to raise the cost.

Although the present invention will be described in detail with reference to the following Examples, the present invention is not limited by the following Examples.

Example 1. Materials and Methods

1) Instruments and Reagents.

Distilled water used for extraction of anthocyanin containing colored potatoes was made from ultrapure distilled water with a specific resistance of 18 MΩ or more in an ultrapure water maker (Milli-Q system, USA), and methanol (methanol) used a domestic GR grade. The hydrochloric acid solution was purchased from Japan Hwagwang Pure Chemical Co., Ltd., and the acetonitrile and formic acid used as mobile phase solvents of Preparative-HPLC and Analytical-HPLC were Merck Inc. HPLC grade (USA) was purchased and used.

Octadecylsilica gel (ODS) for column chromatography for anthocyanin separation was used Lichroprep RP-18 (40-63 μm, Merck, Germany), and the solvent for NMR used in the instrument analysis was methanol -d4, Dcl (Merck, Germany) was used.

Preparative-HPLC and Analytical-HPLC were used for high-purity separation and qualitative analysis of anthocyanins containing colored potatoes.Agillent 1200 series (Agillent, Wilmington, DE, USA) was used, and HRFAB-MS was JMS 700 (JEOL, Kyoto, Japan). Measured using. UV spectrophotometer was used for Shimadzu UV-1601 (Shimadzu, Kyoto, Japan), and the non-luminescence was measured using Polarimeter P-1020 (JASCO, Kyoto, Japan). NMR was measured with a 400 MHz, Inova AS 400, FT-NMR spectrometer (Varian, CA, USA).

2) Experimental materials.

The colored potato used in the present invention was a solanum tuberosum L. cv Jayoung, a variety registered by the Rural Development Administration (KNU-HMRAL-20080612). ) Was used to perform the experiment.

Example 2. Isolation of New Compounds.

The skin of the colored potato Jayoung was removed and 1 kg of the living body incised about 2-3 mm was extracted with 1% hydrochloric acid-methanol (20 L) at room temperature for 24 hours. The obtained extract was filtered and the remaining one was extracted twice more in the same manner. The obtained filtrates were combined and concentrated under reduced pressure at 40 ° C to obtain a concentrated solution.

100 mL of the obtained 1% hydrochloric acid-methanol concentrate was collected, concentrated under reduced pressure again, and 100 mL of 1% hydrochloric acid-distilled water was added to the remaining concentrate, followed by ODS column chromatography (φ 5 × 50 cm, containing 1% hydrochloric acid H). ₂ O: MeOH = 9: 1 → 8: 2 → 7: 3 → 6: 4 → 5: 5 → 4: 6 was carried out to obtain five fractions (StJ-1 ~ StJ-5), Among them, the StJ-3 fraction, which is the major anthocyanin, was concentrated and dried again under reduced pressure concentrator at 40 ℃, dissolved in 20% methanol (50 mL) containing 1% hydrochloric acid, and then separated by high purity by Preparative-HPLC. Compound 1 (19 mg) was purely separated as a result of prep by performing [Fig. 1].

At this time, the prep column used as a separation condition of Preparative-HPLC was used HiQ sil C18-10 (21.0 × 250 mm, KYA TECH, Japan), the analysis wavelength 530 nm, flow rate 10 mL per minute, A solvent as the analysis solvent Distilled water containing 5% formic acid, B solvent was acetonitrile containing 5% formic acid (0 minutes: 85% A, 15 minutes: 85% A, 20 minutes: 70% A, 21 minutes: 85% A, 30 minutes: 85% A), and the sample injection volume was adjusted to 2 mL to perform high purity separation.

Compound 1: red amorphous powder; [a] ²⁵ _D = -24.0 ° (c = 0.10, MeOH); UV (MeOH) λ _max 527 nm; pos. FAB-MS m / z: 1110 [M + H] ⁺ , 933 [M-feruloly + H] ⁺ , 787 [M-coumaroyl + H] ⁺ , 641 [M-rhamnose + H] ⁺ , 479 [M-glucose + H] +; 1 H-NMR (400 MHz): 8.89 (1 H, s, H-4), 7.86 (1 H, d, 2.0 Hz, H-2 '), 7.70 (1 H, d, 2.0 Hz, H-6'), 7.50 (1H, d, 16.0 Hz, H-7f), 7.48 (1H, d, 16.0 Hz, H-7p), 7.37 (2H, d, 7.8 Hz, H-2p, 6p), 7.01 (1H, d, 1.6 Hz, H-2f), 6.99 (1H, br s, H-8), 6.96 (1H, br s, H-6), 6.91 (1H, dd, 7.4, 1.6 Hz, H-6f), 6.78 (1H , 7.8 Hz, H-3p, 5p), 6.75 (1H, d, 7.4 Hz, H-5f), 6.19 (1H, d, 16.0 Hz, H-8f), 6.17 (1H, d, 16.0 Hz, H- 8p), 5.62 (1H, d, 8.0 Hz, H-1``), 5.27 (1H, dd, 8.0, 8.0 Hz, H-4 '''), 5.24 (1H, d, 8.8 Hz, H-1 '''), 4.88 (1H, dd, 9.5, 9.5 Hz, H-4``''), 4.72 (1H, br s, H-1''''), 4.05 (1H, br d, 11.0 Hz , H-6''a), 3.93 (3H, s, petunidin-OCH3), 3.78 (1H, br d, 11.0 Hz, H-6''b), 3.90-3.50 (sugar moiety), 3.39 (3H, s, feruloyl-OCH 3), 0.97 (3H, d, 6.4 Hz, H-6`` ''); 13C-NMR (100 MHz): 169.5 (C-9p), 168.9 (C-9f), 168.2 (C-7), 163.6 (C-4p), 161.2 (C-2), 156.7 (C-5), 156.4 (C-9), 149.6 (C-3 '), 147.4 (C-4'), 147.1 (C-5 '), 146.9 (C-f4). 146.7 (C-7f, 7p), 146.0 (C-3), 133.9 (C-4), 131.2 (C-2p, 6p), 127.5 (C-3f), 127.0 (C-1p), 122.9 (C- 6f), 119.5 (C-1 '), 116.8 (C-3p, 5p), 116.5 (C-5f), 115.1 (C-2f), 115.0 (C-8p, 8f), 114.9 (C-1f), 113.8 (C-6 '), 112.9 (C-10), 109.4 (C-2'), 105.4 (C-6), 102.5 (C-1 ''), 102.2, (C-1 '''), 102.1 (C-1`` ''), 97.4 (C-8), 78.5 (C-5 '''), 78.1 (C-5''), 77.7 (C-3'''), 77.5 (C -3 ''), 75.2 (C-4 ''''), 74.7 (C-2 '', 2 '''), 72.0 (C-4'''), 71.9 (C-3 '''' ), 70.8 (C-4``), 70.2 (C-2 ''''), 67.7 (C-5 ''''), 67.2 (C-6``), 62.0 (C-6 ''' ), 57.1 (petunidin-OCH ₃ ), 49.8 (feruloyl-OCH ₃ ), 17.8 (C-6`` '')

One novel anthocyanin compound was isolated by ODS column chromatography and preparative-HPLC separation of 1% hydrochloric acid-methanol extract of colored potato Ja-young.

Compound 1, which is a red powder, was developed by TLC and observed as a result of UV absorption. 10% aq. When sprayed, dried, and heated with H ₂ SO ₄ , it developed a dark red color. A peak of m / z: 1110 [M + H] ⁺ was observed from the FAB-MS spectrum, and a UV spectrum was observed. Λmax 527 nm was measured, and it could be estimated that it was an anthocyanin compound. Δ H 8.89 (1H, s, H-4), 7.86 (1H, d, 2.0 Hz, H-2 ′), 7.70 (1H, d, 2.0 Hz,) in IH-NMR (400 MHz, CDCl ₃ ) spectrum Olefinic methine proton signal was identified from the values of H-6 ′), 6.99 (1H, br s, H-8) and 6.96 (1H, br s, H-6). It is the structure of cyanidin substituted 1,2,3,5-4 of A-ring and 1,3,4,5-4 substituted of B-ring from the coupling pattern of (signal) Could be expected. δ H of 5.62 (1H, d, 8.0 Hz, H-1``), 5.24 (1H, d, 8.8 Hz, H-1 '''), 4.72 (1H, br s, H-1'''') Anomer protons of sugar molecules were observed in the signal, and three sugar molecules were expected. In the oxygen-substituted region, a number of oxygenated methine and methylene proton signals (δ H 3.90 to 3.50, sugar moiety) were observed, and a methoxy signal (δ H 3.93, petunidin-OCH) was observed. <sub>3</sub> and δ H 3.39, feruloyl-OCH <sub>3</sub> ) were observed. In addition, the olefin methine signal (δH 7.50 (1H, d, 16.0 Hz, H-7f), 7.48 (1H, d, 16.0 Hz, H-7p), 7.37 (2H, d, 7.8 Hz, H-2p, 6p), 7.01 (1H, d, 1.6 Hz, H-2f), 6.91 (1H, dd, 7.4, 1.6 Hz, H-6f), 6.78 (1H, 7.8 Hz, H -3p, 5p), 6.75 (1H, d, 7.4 Hz, H-5f), 6.19 (1H, d, 16.0 Hz, H-8f), 6.17 (1H, d, 16.0 Hz, H-8p)] As expected, two phenolic acids were expected. A methyl proton signal (δH 0.97 (d, 6.4 Hz, H-6`` '')) was observed in the high magnetic field. 53 signals were observed in both 13C-NMR and DEPT spectra, and the carboxyl carbon signal [δc 169.5 (C-9p), 168.9 (C-9f)] and agricon in the low-field region olefine quaternary carbon signal of (aglycone) [δc 168.2 (C-7), 161.2 (C-2), 156.7 (C-5), 156.4 (C-9), 149.6 (C-3 '), 147.4 (C-4'), 147.1 (C-5 '), 146.0 (C-3), 119.5 (C-1'), 112.9 (C-10)] and olefine methine carbon signal) [δc 133.9 (C-4), 113.8 (C-6 '), 109.4 (C-2'), 105.4 (C-6), 97.4 (C-8)]. The methoxy signal [δc 57.1 (petunidin-OCH ₃ )] is combined with the olefine quaternary carbon [δc 149.6 (C-3 ′)] of aglycon in the HMBC spectrum. As a result of confirming the cross-peak of aglycone, aglycone was identified as petunidin.

The proton coupling pattern and the coupling value of two phenolic acids identified in the IH-NMR spectrum are calculated, and the identified signals are carbon signals through the HSQC and HMBC spectra. As a result of identifying (carbon signal), δc 168.9 (C-9f), 146.9 (C-4f), 146.7 (C-7f), 127.5 (C-3f), 122.9 (C-6f), 116.5 (C- 5f), 115.1 (C-2f), 115.0 (C-8f), 114.9 (C-1f), 49.8 (feruloyl-OCH ₃ ) signals were structurally identified as feruloyl and olefin methine protons (olefin) It was confirmed that the methine protons (H-7f, H-8f) were trans by coupling at 16.0 Hz.

As a result of structural identification of the other signals in the same manner, δc 169.5 (C-9p), 163.6 (C-4p), 146.7 (C-7p), 131.2 (C-2p, 6p), 127.0 (C-1p), The signals of 116.8 (C-3p, 5p) and 115.0 (C-8p) were structurally identified as para-coumaroyl. COSY is measured based on the anmeric proton signal of sugar molecules bound to aglycone, and each connected proton signal is carbon signal and gross based on HSQC spectrum. As a result of the cross-peak, the sugar bound to the aglycone contained glucose [(102.5 (C-1``), 78.1 (C-5 ''), 77.5 (C-3). ''), 74.7 (C-2``), 70.8 (C-4 ''), 67.2 (C-6 ''), (102.2, (C-1 '' '), 78.5 (C-5' ' '), 77.7 (C-3' ''), 74.7 (2 '' '), 72.0 (C-4' ''), 62.0 (C-6 '' ')]. Two molecules and one rhamnose. Molecules [102.1 (C-1 '' ''), 75.2 (C-4 '' ''), 71.9 (C-3 '' ''), 70.2 (C-2 '' ''), 67.7 (C- 5 '' ''), 17.8 (C-6 '' '')]. The HMBC spectra show glucose's anmeric proton signal [δH 5.62 (d, 8.0 Hz). , H-1 '')] and Oglycone's olefin quaternary carbon signal Correlation with [δc 146.0 (C-3)] was confirmed, and oxygenated methylene signal [δH 4.05 (1H, 11.0 Hz, H-6``a)] rhamnose ) Is combined with the anmeric carbon [102.1 (C-1 '' '')] and the H-6''a signal is reduced to about 2 ppm by glycosidation shift. Olefin methine protons of phenolic acid, para-coumaroyl identified in IH-NMR and 13C-NMR spectra (H-7p) , H-8p) was found to be a trans bond at 16.0 Hz. In addition, carboxyl carbon [169.5 (C-9p)] was used as the oxygenated methine proton of rhamnose [δH 4.88 (dd, 9.5, 9.5 Hz, H-4 '' ''. )] And the interaction (correlation) was confirmed by HMBC, it was confirmed that the acylated (acylated) from the chemical shift. It was confirmed that the carbon connected from HSQC was δc 75.2 (C-4`` '') and also shifted to about 2 ppm (typically around 73 ppm) to the low field. It was. Aglycon 5 carbon contains another glucose anmeric proton signal [δH 5.24 (d, 8.8 Hz, H-1 ′ ''), which is an aglycone olefin quaternary carbon signal [δc]. 156.7 (C-5)] were correlated with the HMBC spectrum. Phenolic acid and feruloyl were also found to be trans, with olefin methine protons (H-7f, H-8f) at 16.0 Hz, carboxyl carbon) [δc 168.9 (C-9f)] interacts with the oxygenated methine proton of glucose [δH 5.27 (1H, dd, 8.0, 8.0 Hz, H-4 ′ '')] It was confirmed by the spectrum (spectrum), the HSQC spectrum (chemical), the chemical shift (chemical shift), coupling pattern (coupling pattern) was confirmed as a result of binding to the 4 '' 'of glucose was confirmed. In order to determine the mass value of the identified compound, FAB-MS (positive) experiments were carried out. [M + H] m / z: 1110 [M + H] + 933 [M-feruloly + H] +, 787 The values of [M-coumaroyl + H) +, 641 [M-rhamnose + H] +, and 479 [M-glucose + H] were confirmed, and the measured mass values and fragmentation patterns were identified. Consistent with the structure.

A general structure identified by the above-described bar results, the novel compounds isolated by extraction from the colored potato is independent petunidin-3- O - [6- O - (4-O- Ep -coumaroyl- α-L -rhamnopyranosyl) - β- D- glucopyranosyl] -5 -O- (4- OE- feruloyl) -β -D -glucopyranoside was identified, which turned out to be a novel compound that has not been reported to date [see Figure 1].

The Applicant named the novel compound Petunanin JY, and shows the structure in Chemical Formula 1.

Experimental example. Characteristics of New Compound Petunanin JY

1) Antioxidant Activity Assay of Novel Compound Pethunanin JY

Antioxidant activity assay of the novel compound pethunanin JY was measured using the method by Nagai et al.

0.208 mL of sodium phosphate buffer (pH 7.0) was mixed with 0.083 mL of pethunanin JY prepared for each concentration, and 0.208 mL of 2.5% (w / v) linoleic acid was added again. Oxidation induction was initiated by adding 0.021 mL of 0.1M 2,2'-azobis (2-amidinopropane) dihydrochloride to reaction at 37 ° C in the dark, and then oxidizing linoleic acid every 50 minutes up to 200 minutes. It was.

0.1 mL of the reaction solution described above was mixed with 4.7 mL of 75% ethanol, 0.1 mL of 30% ammonium thiocyanate, and 0.1 mL of 0.02M ferrous chloride containing 3.5% HCl. After standing for a minute, peroxide production was measured by absorbance at 500 nm using a UV-1200 UV / VIS spectrometer (Shimadzu, Kyoto, Japan). As a control, only linoleic acid was added without adding a sample. As a control of antioxidant activity evaluation, tocopherol (α-tocopherol) (VE) and ascorbic acid (VC) were prepared using 100 ppm level. Final inhibition rate (%) was calculated for each concentration after 200 minutes [FIGS. 2 and 3].

Assay of antioxidant activity in the early stage of linoleic acid peroxidation of the novel compound petuninin JY showed lower activity than the control treated with 100 ppm of ascorbic acid and tocopherol when treated with 10 ppm and 25 ppm final concentrations of petuninin JY. In the case of 50 ppm or more, ascorbic acid and tocopherol showed higher inhibitory activity. Ascorbic acid and tocopherol showed a tendency to lower the inhibitory activity after 100 minutes, whereas in the case of pethunanin JY, the activity was maintained from the initial reaction to 150 minutes.

Therefore, in the case of ascorbic acid or tocopherol, induction of lipid peroxidation inhibiting activity is changed to oxidized form and the inhibitory activity is lowered as the reaction time elapses. It can be confirmed that it exhibits lipid peroxidation inhibitory activity and is expected to play a role as a novel antioxidant.

2) DPPH Radical Scavenging Activity of the New Compound, Petunanin JY

The DPPH radical scavenging activity assay of the novel compound pethunanin JY was measured by modifying the method by Okada and Okada et al. 0.1 mL of 1.0 mM DPPH radical solution was added and mixed with 0.8 mL of 99% ethanol and 0.1 mL of Pethunanin JY concentration sample, and left to stand for 30 minutes in the dark. UV-1200 UV Absorbance at 517 nm was measured using a / VIS spectrometer (Shimadzu, Kyoto, Japan) and assayed.

At this time, initial (Ai), blank (Ab) without substrate and DPPH were measured, and absorbance (As) was measured after sample addition. RC50 (㎍ / mL) decreased the value of control group without compound by 50%. The concentration of the compound was shown and compared with the existing antioxidants tocopherol (VE) and ascorbic acid (VC).

Table 1: DPPH free radical scavenging activity of pethunanin JY

Compounds DPPH radical scavenging activity
(RC ₅₀ μg / mL) Petunanin JY 94.32 ± 0.95 α-tocopherol (VE) 92.13 ± 0.42 Ascorbic acid (VC) 46.25 ± 0.37

Free radical scavenging activity of pethunanin JY using 1,1-diphenyl-2-picrylhydrazyl (DPPH) was measured and the RC ₅₀ value was about 94 µg / mL. Indicated. In the case of ascorbic acid, the radical scavenging activity of pethunanin JY was similar to that of tocopherol compared to that of RC ₅₀ of 46.25 μg mL ⁻¹ and tocopherol of 92.13 μg mL ⁻¹ .

In case of pethunanin JY, lipid peroxidation inhibitory activity is higher than radical scavenging activity, and it is evaluated that it shows high antioxidant effect by breaking the radical chain rather than directly blocking radical formation. do.

3) Hydroxy Radical Scavenging Activity Assay of Novel Compound Pethunanin JY

The hydroxy radical scavenging activity assay of the novel compound, pethunanin JY, is carried out by deoxyribose, which is oxidized by hydroxy radicals and converted to malonaldehyde, by the Fenton reaction. A method of measuring the degree of (chromagen) formation was used.

0.45 mL 0.2 M sodium phosphate buffer (pH 7.0), 0.15 mL 10 mM 2-deoxyribose, 0.15 mL 10 mM FeSO ₄ EDTA, 0.15 mL 10 mM H ₂ O ₂ , 0.525 mL H ₂ O In addition, 0.075 mL of petuninin JY concentration samples were placed in an Eppendorf tube and reacted at 37 ° C for 4 hours in a dark state, followed by 0.75 mL of 2.8% (w / v) trichloroacetic acid. ) And 0.75 mL of 1.0% (w / v) TBA were added to terminate the reaction. The reaction solution was treated with boiling water for 10 minutes, cooled to room temperature, and assayed by measuring absorbance at 520 nm using a UV-1200 UV / VIS spectrometer (Shimadzu, Kyoto, Japan).

The hydroxy radical scavenging activity assay was calculated as the rate of inhibiting the oxidation of 2-deoxyribose by the hydroxy radical with the addition of pethunanin JY concentration, and the control was determined by adding sterile water instead of the sample. The IC ₅₀ (μg / mL) was expressed as the concentration of the sample which reduced the value of the control group without the addition of petanin JY by 50%, and compared with the existing antioxidants tocopherol (VE) and ascorbic acid (VC).

Table 2: Hydroxy radical scavenging activity of pethunanin JY

Compounds Petunanin JY α-tocopherol (VE) Ascorbic acid (VC) Hydroxyl radical scavenging activity
(IC ₅₀ μg / mL) 113.3 ± 2.14 43.2 ± 0.52 533.5 ± 3.86

Hydroxy radicals (OH) are known to play a major role in biooxidation because they are very reactive in active oxygen. In particular, the hydroxy radicals indiscriminately attack the purine and pyrimidine bases of DNA, and variously modify them, as well as the deoxyribose moiety, which causes the cleavage of DNA chains. There is a lot of evidence that free radicals are involved in the development and progression of cancer, arteriosclerosis, autoimmune diseases, arthritis, lung diseases, diabetes, myocardial infarction, brain and neurological diseases.

Therefore, the results of examining the hydroxy radical scavenging activity to confirm whether the novel compound pethunanin JY can be applied to the prevention and treatment of various diseases due to the antioxidant effect, the concentration required to inhibit the production of hydroxy radicals by 50% It was about 113.3 ㎍ / mL, which showed less hydroxy radical scavenging activity than ascorbic acid, although it did not reach the tocopherol control.

4) Determination of Superoxide Scavenging Activity of the New Compound Pethunanin JY

The superoxide radicals scavenging activity of the novel compound pethunanin JY was assayed using nitro-blue tetrazolium (NBT) reduction method.

It consists of 0.02 mL of 3 mM xanthine, 0.48 mL of 0.05 mM sodium carbonate buffer (pH 10.5), 0.02 mL of 3 mM ethylenediaminetetraacetic acid disodium salt (EDTA), 0.02 mL of 0.15% bovine serum albumin, and 0.02 mL of 0.75 mM NBT. Pethunanine JY was treated at 10, 25, 50, and 100 ㎍ / mL, respectively, and the mixture was incubated at 25 ° C for 10 minutes. Then, 1.0 mL of XOD (6mU / mL) was added to start the reaction. After reacting for 20 minutes at 25 ℃. Thereafter, 0.02 mL of 6 mM CuCl was added to terminate the reaction, and the absorbance was measured at 560 nm. The concentration of the compound (IC ₅₀ , 50% inhibition concentration) was shown to reduce the inhibitory activity against NBT reduction by 50% according to the amount of sample added by concentration, catechin ((+)-catechin) and allopurinol (Sigma). ), Ascorbic acid (VC) was used as a control.

[Table 3] Inhibitory effect of superoxide anion radicals of pethunanin JY

Compounds Petunanin JY (+)-catechin allopurinol Ascorbic acid Xanthine oxidase
inhibition activity
(IC ₅₀ μg / mL) 23.7 ± 2.5 7.2 ± 0.5 3.45 ± 0.24 ND  Mean ± S.E obtained from three experiments

Inhibition of xanthine oxidase activity of petuninin JY showed that IC ₅₀ values for superoxide scavenging activity were 3.45 ㎍ / a for allopurinol and catechin, each containing a large amount of hydroxy group. While mL and 7.2 μg / mL were shown, petuninin JY showed 23.7 μg / mL, which showed somewhat lower activity, but showed a better aspect than ascorbic acid.

The above results are believed to be due to the quantitative difference of the hydroxyl groups contained in each compound, it can be seen that the pethunanin JY shows a high activity of antioxidant and quentin oxidase inhibitory activity. Quentin oxidase inhibitors have been used as a treatment for hyperuricemia causing gout, kidney stones, ischemia and cardiomyopathy, and there is an urgent need for developing inhibitors for the aging age.

Therefore, if the colored potato such as pethunanin JY and its useful product, anthocyanin, are applied to industrial and medicinal applications, it can be used as a safe and effective health functional material that can cure and prevent various diseases.

5) Anticancer Activity and Toxicity Assessment of Normal Cells

Inhibition of cell growth inhibition of the human cancer cell line by pethunanin JY by SRB (Sulfo Rhodamine B) method. The cancer cell line was a prostate cancer cell line LNCaP, colon cancer cell line HCT-15, gastric cancer cell line ACHN, lung cancer cell line A549, leukemia cell line MOLT-4F was used.

To confirm the toxicity to normal cells, hepatocyte line 293 (human embryo liver) was purchased from Korea Cell Line Bank (KCLB) and used as a control. The cancer cell line was cultured using RPMI 1640 medium containing 10% fetal bovine serum, and the cultured cells were maintained by dispensing once or twice a week.

The cell concentration used for measuring anticancer activity was 3,000 to 6,000 cells / mL, and all the reagents used in the above method were dissolved in 100% DMSO, and diluted in stages to reduce the concentration of petuninan JY to 30, 10, 5, 2.5, 1, 0.1 µg / mL was prepared. The Tz plate is required to measure the number of cells, divide them into 96-well plates at a constant concentration, and display the basic absorbance of the cells after one day, with the same cell concentration as the plate to be treated. The other plate was fixed using 50% TCA. The plate to be treated with the sample was treated with five concentrations by adjusting the final concentration of the sample to 0.1% DMSO. The Tz plate was washed with tap water after 1 hour, and the plate treated with the sample was fixed with 50 μL of 50% TCA per well after 2 days, and washed with tap water after 1 hour. . The washed plate was dried at room temperature, and then 0.4 μl SRB solution was added to 100 μL per well, and then washed with 1% acetic acid solution after 30 minutes, and dried again at room temperature. Then, 10 mM Tris base (pH: 10.5) was added to 100 μL per well to dissolve again, and the absorbance was measured at 540 nm using an ELISA reader. At this time, the concentration of the compound that inhibits the growth of cancer cells by 50% was expressed as GI 50 (µg / mL), and adriamycin was used as a control.

[Table 4] Cell Growth Inhibition Activity of Human Cancer Cell Lines by Pethunanin JY

Compounds GI ₅₀ (μg / mL) Prostate (LNCaP) Colon
(HCT-15) Renal
(ACHN) Colon
(SW-620) Lung
(A549) Leukaemia
(MOLT-4F) Petunanin JY 17.64 > 30 28.61 > 30 > 30 16.77 Adriamycin 0.13 0.16 0.13 <0.03 <0.03 0.05

As a result of assaying the effect of petuninin JY on the growth of human cancer cell line by SRB method, prostate cancer was not found in lung cancer cell line A549 cell, colon cancer cell line HCT-15 and SW-620 while petuninin JY showed no activity. For cell lines LNCaP and leukemia cell line MOLT-4F, the GI ₅₀ (µg / mL) values were 17.64 and 16.77 µg / mL, respectively, showing excellent cytotoxic effects and weak activity against renal cancer cell line (ACHN). .

In order to confirm the toxicity of pethunanin JY to normal liver cell line 293, we examined the inhibitory effect on the growth of sample according to the concentration of the sample. Inhibition of growth was less than 2%.

This can be said that the pethunanin JY shows a high inhibitory effect on cancer cell lines, but little growth inhibitory effect on normal cells.

Recent studies have shown that anthocyanin-rich extracts contain 5-Flurouracil (5-Fu), an antagonist for colon cancer, to prevent side effects that damage normal cells, such as epithelial cells of the small intestine, as well as cancer cells. (50μg / mL or more) in combination not only increases the growth inhibition efficiency of cancer cells by 30% but also suppresses adverse effects on normal cells, but it is reported that it does not significantly affect concentrations below 50μg / mL. .

In view of the above results, it is thought that the novel compound pethunanin JY exhibits activity on specific cancer cell lines, and it shows high anticancer activity against specific cancer cell lines and does not significantly affect normal cells. It is expected to be used as a combination treatment stabilizer and a synergist to increase the treatment efficiency to secure the stability of existing anticancer drugs.

As confirmed above, the novel compound pechuanin JY of the present invention represented by Formula 1 exhibits excellent antioxidant and anticancer effects, and thus may be formulated as a pharmaceutical composition for treating and preventing cancer.

Formulation Example 1 Manufacturing Method of Syrup

A syrup containing the compound of Formula 1 of the present invention and a pharmaceutically acceptable salt thereof as an active ingredient of 2% (weight / volume) is prepared by the following method.

Acid addition salts, saccharin and sugars of the compound of formula 1 were dissolved in 80 g of warm water. After the solution was cooled, a solution consisting of glycerin, saccharin, spices, ethanol, sorbic acid and distilled water was prepared and mixed thereto. Water was added to this mixture to 100 ml. The addition salt can be replaced with other salts according to the examples.

The components of the syrup are as follows.

Hydrochloride of a compound of formula 1

Saccharin: 0.8 g ·················

25.4 g of sugar

Glycerin ... 8.0 g

Spices ············ 0.04 g

Ethanol 4.0 g

0.4 g of sorbic acid

Distilled water ·····················

Formulation Example 2 Manufacturing Method

A tablet containing 15 mg of active ingredient is prepared by the following method.

250 g of hydrochloride of the compound of formula 1 were mixed with 175.9 g of lactose, 180 g of potato starch and 32 g of colloidal silicic acid. 10% gelatin solution was added to the mixture, which was then ground and passed through a 14 mesh sieve. It was dried and the mixture obtained by adding 160 g of potato starch, 50 g of talc and 5 g of magnesium stearate was made into a tablet.

The components of the tablet are as follows.

Hydrochloride of the compound of formula 1 ... 250 g

Lactose ························ 175.9 g

Potato starch ··········· 180 g

Colloidal silicic acid 32 g

10% gelatin solution

Potato starch · 160 g

Talc · 50 g

Magnesium stearate ... 5 g

Formulation Example 3 Preparation of Injection Solution

Injection solution containing 10 mg of the active ingredient was prepared by the following method.

1 g of a compound of the general formula (1), hydrochloride, 0.6 g of sodium chloride, and 0.1 g of ascorbic acid were dissolved in distilled water to make 100 ml. The solution was bottled and sterilized by heating at 20 ° C. for 30 minutes.

The components of the injection solution are as follows.

Hydrochloride of the compound of formula 1 ... 1 g

Sodium Chloride ・ ・ ・ ・ 0.6 g

0.1 g of ascorbic acid

Distilled water ·············

As confirmed above, the novel compound Pethunanin JY of the present invention represented by Formula 1 exhibits an excellent antioxidant effect and thus may be prepared as a cosmetic composition capable of inhibiting skin aging by the antioxidant effect.

Formulation Example 1: Softener (Skin Lotion)

According to the conventional method with the following ingredients and contents were prepared in the flexible cosmetic water.

Hydrochloride of the compound of formula 1 0.5 g

Colored potato extract comprising a compound of formula 1 · 5.0 g

6.0 g of 1,3-butylene glycol

Glycerin ... ・ ・ ・ ・ 4.0 g

Oleo-alcohol ················· 0.1 g

Polysorbate ················ 20.5 g

Ethanol 15.0 g

Benzophenone-9 0.05 g

Incense, preservative trace

Purified Water To 100

Formulation Example 2. Nutrients (Milk Lotion)

Nutrients were prepared according to a conventional method with the following ingredients and contents.

Hydrochloride of a compound of formula 1 1.0 g

Colored potato extract comprising a compound of formula 110.0 g

Propylene Glycol 6.0 g

Glycerin ・ ・ ・ ・ ・ ・ ・ 4.0 g

Triethanolamine 1.2 g

Tocophenylacetate ・ ・ ・ 3.0 g

Liquid paraffin 5.0 g 5.0 g

Squalane 3.0 g

Macadamia nut oil 2.0 g

Polysorbate 60 1.5 g

Sorbitan sesquioleate 1.0 g

Carboxyvinyl Polymers 1.0 g

BH ... 0.01 g

EDTA-2Na ..... 0.01 g

Incense, preservative trace

Purified Water To 100

Formulation Example 3. Nutrition Cream

The nutrition cream was prepared according to a conventional method with the following ingredients and contents.

Hydrochloride of the compound of formula 1 ····· 2.5 g

Colored potato extract comprising the compound of formula 1 ... 2.0 g

Cetostearyl alcohol ... 2.0 g

Glyceryl stearate 1.5 g

Trioctanoine ············ 5.0 g

Polysorbate 60 1.2 g

Sorbitan stearate 0.5 g

Squalane 5.0 g 5.0 g

Liquid paraffin 3.0 g 3.0 g

Cyclomethicone ····· 3.0 g

BH T · 0.05 g ···············

Delta-tocopherol ... 0.2 g

Concentrated glycerin ············ 4.0 g

1,3-butylene glycol 2.0 g

Xanthan Gum · 0.1 g

EDTA-2Na ... ·················· 0.05 g

Incense, preservative trace

Purified Water To 100

Formulation Example 4 Massage Cream

Massage cream was prepared according to a conventional method with the following ingredients and contents.

Hydrochloride of a compound of formula 1 1.0 g

Colored potato extract comprising the compound of formula 1 ... 0.5 g

Propylene Glycol 6.0 g

Glycerin ... 4.0 g

Triethanolamine 0.5 g

Beeswax 2.0 g

Tocopheryl Acetate ・ ・ ・ ・ 0.1g

Polysorbate 60 ... 3.0 g

Sorbitan sesquioleate 2.5 g

Cetearyl Alcohol ... 2.0 g

Liquid paraffin 30.0 g ··········

Carboxyvinyl Polymers 0.5 g

Incense, preservative trace

Purified Water To 100

Formulation Example 5 Pack

The pack was prepared according to a conventional method with the following ingredients and contents.

Hydrochloride of the compound of formula 1 · 1.0 g

Colored potato extract comprising the compound of formula 1 ... 1.0 g

Propylene Glycol 2.0 g

Glycerin ················ 4.0 g

Carboxy vinyl polymer0.3 g 0.3 g

Ethanol 7.0 g

Fiji-40 Hydrogenated Castor Oil 0.8 g

Triethanolamine 0.3 g 0.3 g

BH ... 0.01 g

EDTA-2Na ..... 0.01 g

Incense, preservative trace

Purified Water To 100

As confirmed above, the novel compound pethunanin JY of the present invention represented by Formula 1 exhibits excellent antioxidant and anticancer effects, and thus may be prepared as a health functional food for preventing cancer or various diseases.

Preparation Example 1 Candy

Candy was prepared at the following preparation costs.

Colored potato extract comprising the compound of formula 1 ... 10.5 g

50.0 g of sugar

Starch syrup 24.0 g

0.5 g of spices ······

15 g of water

Preparation Example 2

Fruits were prepared at the following preparation ratios.

Colored potato extract comprising a compound of formula 1 ... 10.5 g

66.4 g of sugar

Glucose ... 19.0 g

Sucrose Fatty Acid Ester 0.2 g

0.2 g of fragrance

3.7 g of water

Figure 1 shows the HPLC chromatogram (detected at 530 nm) of the novel compound of the present invention isolated from S. tuberosum L. cv Jayoung.

2 and 3 are graphs showing the antioxidant activity of the novel compound pethunanin JY of the present invention.

Claims (13)

The novel compounds represented by the following formula (1) or salts thereof. [Formula 1]

The method according to claim 1, The compound of Formula 1 or a salt thereof is a novel compound or a salt thereof, characterized in that separated from Solanum tuberosum L. cv Jayoung. Colored potato extract, characterized in that it comprises a compound represented by the formula (1) or a salt thereof. Extracting the colored potatoes with an alcohol containing acid and concentrating under reduced pressure to obtain an alcohol extract, Concentrating the alcohol extract, dissolved in a mixed solvent of acid-containing water and alcohol, performing chromatography (chromatography) and concentrating the fractions for each solvent to obtain a concentrate, Collecting the active fraction by dissolving the active fraction concentrate in which the active fraction in the concentrate is concentrated in an acid-containing alcohol and performing chromatography; and Separating the active fraction by chromatography, removing a solvent, and freeze drying to obtain a target compound. Method for producing a compound of formula 1 characterized in that comprises a. [Formula 1]

The method of claim 4, The acid in the acid-containing alcohol and water containing water is characterized in that it comprises 0.1 to 5% (w / w). The method of claim 4, The alcohol is a production method, characterized in that selected from alcohols having 1 to 3 carbon atoms. The method of claim 4, The acid is an inorganic acid selected from hydrochloric acid, bromic acid, sulfuric acid, phosphoric acid, or citric acid, acetic acid, lactic acid, tartaric acid, maleic acid, fumaric acid, formic acid, propionic acid, oxalic acid, Method for producing an organic acid selected from trifluoroacetic acid, benzoic acid, gluconic acid, methanesulfonic acid, glycolic acid, succinic acid, 4-toluenesulfonic acid, galluxuronic acid, embonic acid, glutamic acid and aspartic acid. An anticancer agent comprising the compound represented by the formula (1) of claim 1 or a pharmaceutically acceptable salt thereof, or a colored potato extract including the same as an active ingredient. A pharmaceutical composition showing an anticancer effect, comprising a compound represented by the formula (1) of claim 1 or a pharmaceutically acceptable salt thereof, or a colored potato extract comprising the same as an active ingredient. delete A food additive having a preventive function of cancer, comprising a compound represented by the formula (1) of claim 1 or a food acceptable salt thereof, or a colored potato extract comprising the same as an active ingredient. A health functional food having a preventive function of cancer, comprising the food additive of claim 11. A cosmetic having an antioxidant activity, comprising a compound represented by the formula (1) of claim 1 or a pharmaceutically acceptable salt thereof, or a colored potato extract including the same as an active ingredient.

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