JP5673026B2 - Anti-cancer agent, food, medicine containing 4-vinyl guaiacol polymerized compound or pharmaceutically acceptable salt thereof - Google Patents

Description

The present invention relates to an anticancer agent, food, or pharmaceutical comprising 4 -vinylguaiacol polymer or a pharmaceutically acceptable salt thereof.

  Ferulic acid is one of the secondary metabolites of plants. For example, ferulic acid is a precursor of lignin and lignan, which are the main components of trees, and is a relatively abundant component in nature. Ferulic acid is contained in a large amount in the skin layer of rice bran and potato. These are all ingredients that have dietary experience and are highly safe for humans.

  Examples of the prior art related to the physiological function of ferulic acid include, for example, a cell differentiation promoting agent containing ferulic acid as an active ingredient (Patent Document 1), and a skin whitening external preparation containing ferulic acid as an active ingredient (Patent Document 2). Antioxidants containing ferulic acid as an active ingredient (Patent Document 3), fish egg coloring assistant comprising ferulic acid and nicotinamide (Patent Document 4), antibacterial agent containing ferulic acid as an active ingredient (Patent Document 5) ) The effect of ferulic acid to prevent Alzheimer's disease (Non-Patent Document 1) is known.

  In addition, several methods for producing 4-vinyl guaiacol using ferulic acid as a raw material have been disclosed. 4-Vinylguaiacol is known to be produced in a small amount during shochu, awamori or beer production, and is involved in brewing the aroma of these alcoholic beverages. It is said that ferulic acid decarboxylase produced by microorganisms such as koji molds acts on ferulic acid derived from liquor raw materials to produce 4-vinyl guaiacol. Therefore, a method for producing shochu specifying yeast used for fermentation (Patent Document 6), a method for producing distilled liquor specifying lactic acid bacteria (Patent Document 7), and barley shochu limited to wheat as the main raw material used for fermentation and its A production method (Patent Document 8) or ferulic acid decarboxylase (Patent Document 9) is disclosed.

In addition, 4-vinyl guaiacol is not only a constituent component of aroma, but related art is also found because vanillin is produced from 4-vinyl guaiacol (Patent Document 10).
However, in any of the above-described known techniques, there is no description about the production of 4-vinyl guaiacol polymerization compound, and even the possibility thereof is not suggested.

Further, a chemical synthesis method of 4-vinyl guaiacol polymerized compound from ferulic acid is also known (Non-patent Document 2). In this method, only ferulic acid is heated to a melting point or higher and maintained at 205 ° C. A 4-vinyl guaiacol polymerization compound is obtained. Therefore, it is clear that the target reaction does not proceed under temperature conditions below the melting point. In addition, this method is difficult to control such as sealing and degassing in the process, and there are significant problems in workability and safety in performing mass synthesis.
In addition, there is a report (Non-patent Document 3) of obtaining a 4-vinyl guaiacol polymerization compound from a lignin-related compound, but ferulic acid is not used in this method, and the reaction conditions are as high as 250 ° C. Similarly, although there is a report (Non-patent Document 4) for obtaining a 4-vinyl guaiacol polymerized compound, ferulic acid is not used in this method, and benzene is used as a solvent under acidic conditions.

  Prior art relating to ferulic acid derivatives is also shown. An ultraviolet absorber (Patent Document 11) containing a ferulic acid ester derivative as an active ingredient and a skin external medicine (Patent Document 12) containing a ferulic acid ester of a phytosterol as an active ingredient are known.

  Thus, since ferulic acid and derivatives thereof have many excellent utilities, technical disclosures for efficiently producing them as raw materials and lead compounds have been made. Examples of ferulic acid production methods include production by condensation reaction of vanillin and malonic acid (Non-patent Document 5), production method from rice bran (Patent Document 13), and production method using eugenol as a raw material (patent) Document 14), a production method with an enzyme from coniferyl aldehyde (Patent Document 15) is known.

  In other words, due to the high value of ferulic acid as a raw material and precursor, an efficient production method of ferulic acid has progressed. In fact, ferulic acid is supplied not only as a reagent but also as a food additive at low cost. Yes. Under such circumstances, there is a demand for a method for producing a useful ferulic acid-related substance by a safer, simpler and more efficient method.

JP-A-5-310526 JP-A-6-256137 JP-A-9-221667 JP 2000-325049 A JP 2000-247900 A JP 2007-267679 A JP 2008-75 A JP 2009-273401 A Japanese Patent No. 4252120 JP-A-5-244965 JP 2003-128632 A JP-A-8-81352 Japanese Patent Publication No. 7-78032 Japanese Patent No. 9-154591 Japanese Patent No. 10-15596

British Journal of Pharmacology, 133, 89-96 (2001) J. et al. Agricultural and Food Chemistry, 40, 1666-1670 (1192) Journal of Wood Chemistry and Technology, 27, 121-133 (2007) Polymer Journal, 13, no. 6, 563-568 (1981) Journal of the American Chemical Society, 74, 5346-5348 (1952)

  In view of the above-described situation regarding ferulic acid and useful compounds using the compound, the present inventors have conducted a search for ferulic acid-related compounds and conducted extensive studies to establish the production method. Was first discovered to produce 4-vinyl guaiacol polymerized compound or a pharmaceutically acceptable salt thereof having an excellent anticancer activity not found in ferulic acid, which is a raw material, by heat-treating under alkaline conditions. The present invention has been completed.

Accordingly, the present invention relates to an anticancer agent containing 4-vinyl guaiacol polymer having excellent anticancer activity and a pharmaceutically acceptable salt thereof as an active ingredient, and a food and pharmaceutical containing the 4-vinyl guaiacol polymer. The purpose is to provide.

The gist of the present invention is as follows:
[1] The following formula (1 ) obtained by heat-treating ferulic acid under alkaline conditions

An anticancer agent comprising at least one compound selected from the group consisting of a 4-vinylguaiacol polymerized compound represented by the formula:
[2] a food or pharmaceutical, characterized by containing a pre-Symbol 4-vinyl guaiacol polymer compound obtained as and one or more compounds thereof pharmaceutically selected from the group consisting acceptable salts.

According to the present invention, it is possible to provide a method for efficiently and safely producing 4-vinyl guaiacol polymer having excellent anticancer activity or a pharmaceutically acceptable salt thereof.
The present invention provides an anticancer agent containing the 4-vinyl guaiacol polymer or a pharmaceutically acceptable salt thereof as an active ingredient, and further a food and medicine containing the 4-vinyl guaiacol polymer represented by the formula (1). Can be provided.

FIG. 1 shows the results of HPLC analysis performed in Example 1. The upper figure shows the result before the production reaction, the lower figure shows the result after the production reaction, and “A” shows the peak of the 4-vinyl guaiacol polymerized compound.

  Hereinafter, the present invention will be described in detail.

  The 4-vinyl guaiacol polymerization compound of the present invention has the formula (1):

The structural formula is represented by:

  In the present invention, the 4-vinylguaiacol polymerization compound represented by the formula (1) may be a pharmaceutically acceptable salt. Examples of the pharmaceutically acceptable salt include alkali metal salts such as lithium salt, sodium salt and potassium salt; alkaline earth metal salts such as magnesium salt, calcium salt and barium salt; aluminum salt; aluminum hydroxide salt and the like Metal hydroxide salts of; amine salts such as alkylamine salts, dialkylamine salts, trialkylamine salts, alkylenediamine salts, cycloalkylamine salts, arylamine salts, aralkylamine salts, heterocyclic amine salts; α-amino acid salts And amino acid salts such as ω-amino acid salts; peptide salts or primary, secondary, tertiary or quaternary amine salts derived therefrom. These pharmacologically acceptable salts can be used alone or in admixture of two or more.

  The 4-vinyl guaiacol polymerization compound represented by the formula (1) or a pharmaceutically acceptable salt (hereinafter abbreviated as 4-vinyl guaiacol polymerization compound which is an active ingredient in the present invention) is a precursor. It is a compound with strong anticancer activity not found in some ferulic acid.

  The 4-vinyl guaiacol polymerization compound, which is an active ingredient in the product of the present invention, can be produced by heat-treating a composition containing ferulic acid under alkaline conditions.

  The synthesis method of 4-vinyl guaiacol polymerization compound which is an active ingredient in the product of the present invention is known as shown in Non-Patent Document 2. However, a high temperature of 200 ° C. or higher is necessary, and there are significant cost obstacles for industrialization such as degassing during the reaction. On the other hand, the production method of the present invention is a method for producing ferulic acid, which can be obtained at a relatively low cost, by heat treatment at 90 to 150 ° C. under alkaline conditions. The synthesis method described in Non-Patent Document 2 This is an efficient and safe manufacturing method.

  In the production method of the present invention, ferulic acid is required as a precursor of the 4-vinyl guaiacol polymerization compound. Ferulic acid may be of natural origin or may be a chemically synthesized chemical product with high purity. When natural ferulic acid is used, it does not have to be completely purified, and the desired reaction proceeds thereafter to finally obtain the 4-vinyl guaiacol polymerized compound. It may be a mixture containing. However, from the viewpoint of the recovered amount, a mixture containing 5% by weight or more of ferulic acid is desirable as a raw material. Such raw materials include rice bran and potato extracts or high purity food additive ferulic acid.

  A pure ferulic acid product or a ferulic acid-containing mixture is dissolved in a suitable solvent. At this time, since the solubility of ferulic acid is remarkably low if the solvent is only water, it may be dissolved only in a mixed solution of water and an organic solvent or in an organic solvent. There is no restriction | limiting in particular in the compounding ratio of water and an organic solvent, and the kind of organic solvent, Ferulic acid should just fully melt | dissolve. Desirably, it is desirable from the viewpoint of safety and cost to use only methanol or ethanol, or a mixture of water and methanol or water and ethanol. As the solvent, ethanol or water-containing ethanol is desirable from the viewpoint of safety and legal regulations when it is used for food without sufficiently applying final purification.

  The ferulic acid-containing solution obtained above is adjusted to be alkaline. For example, after preparing a ferulic acid-containing solution, a pH adjuster may be added to adjust the pH of the ferulic acid-containing solution, or the pH of the solvent may be adjusted in advance when preparing the ferulic acid-containing solution. good. If the pH of the ferulic acid-containing solution is finally 7.1 or more, the target production reaction proceeds. However, when the pH exceeds 13.0, other reactions and decomposition of the target compound occur at the same time. The final recovery amount of the 4-vinyl guaiacol polymerization compound which is an active ingredient in the product of the present invention is lowered. Therefore, the pH of the ferulic acid-containing solution at the start of the reaction is desirably 7.1 to 13.0. There is no restriction | limiting in the density | concentration of ferulic acid in a ferulic acid containing solution, and even if it does not fully melt | dissolve before reaction, it may melt | dissolve at the time of reaction. Since the higher the concentration of ferulic acid, there is a merit such that the amount of solvent used is smaller. Therefore, the concentration is preferably near the concentration at which ferulic acid is saturated with respect to each solvent.

  Although there is no restriction | limiting in particular in the pH adjuster which can be used in order to adjust the said ferulic acid containing solution to alkalinity, Sodium hydroxide, potassium hydroxide, sodium hydrogencarbonate, etc. are desirable from the surface of safety | security, efficiency, and cost. A buffer solution may be used when the pH change during the reaction is suppressed as much as possible, but this is not always a necessary technique.

  The ferulic acid-containing solution adjusted to be alkaline as described above is subjected to heat treatment. In order to efficiently advance a desired production reaction, the heating temperature is preferably 90 ° C. or higher. Further, considering the boiling point of the solvent, pressure heating is desirable. For example, the ferulic acid-containing solution is put in an open container and the container is heated at a high temperature, the ferulic acid-containing solution is put in a sealed container and heated, and heated under pressure using a retort device or an autoclave, at least partially. It is necessary that the solution temperature reaches 90 ° C. or higher. From the viewpoint of recovery efficiency of the 4-vinyl guaiacol polymerization compound and the like, it is more preferable that the solution temperature is uniformly 90 to 150 ° C. If the solution temperature exceeds 150 ° C., the recovery efficiency is low and not suitable. The heating time is not limited as in the case of the heating temperature, and may be a time condition in which the target production reaction proceeds efficiently. In particular, the heating time depends on the heating temperature, and it is desirable to set the heating time according to the heating temperature. For example, when heating a ferulic acid containing solution at around 130 ° C., a heating time of 5 minutes to 300 minutes is desirable. In addition, the heat treatment may be performed once, or may be repeatedly performed in a plurality of times, and may be determined from the viewpoint of efficiency.

  The completion of the formation reaction of 4-vinyl guaiacol polymerized compound or a pharmacologically acceptable salt thereof by the heat treatment is, for example, the analysis of 4-vinyl guaiacol polymerized compound or a pharmaceutically acceptable salt thereof by component analysis by HPLC. What is necessary is just to confirm and confirm the production amount.

  The ferulic acid is treated by heat-treating the ferulic acid-containing solution under alkaline conditions, and the mixture contains a 4-vinylguaiacol polymerized compound represented by the formula (1) or a pharmaceutically acceptable salt. Is obtained. When it is obtained in a process using only safe raw materials, it can be used in a mixture state. For example, when naturally derived ferulic acid is dissolved in an ethanol solvent, baking soda is added, and the mixture is reacted by heating, the mixture can be used as one of food ingredients.

  When improvement in flavor and further enhancement of functionality are desired, the 4-vinylguaiacol polymerized compound represented by the formula (1) or a pharmaceutically acceptable salt is concentrated to increase the concentration, or purified and purified. Goods can be obtained. Concentration and purification can be performed by a known method. The 4-vinyl guaiacol polymerized compound represented by the above formula (1) or a pharmaceutically acceptable salt is extracted by a solvent extraction method such as chloroform, ethyl acetate, ethanol, methanol, or a supercritical extraction method using carbon dioxide gas. To concentrate. It is also possible to perform concentration and purification using column chromatography. A membrane treatment method such as a recrystallization method or an ultrafiltration membrane can also be applied. Finally, when the solvent is removed by drying under reduced pressure or lyophilization, a pure 4-vinyl guaiacol polymerized compound represented by the formula (1) or a pharmaceutically acceptable salt can be obtained.

  Since the 4-vinyl guaiacol polymerized compound represented by the formula (1) or a pharmaceutically acceptable salt has excellent anticancer activity as described later, an anticancer agent containing this compound as an active ingredient is used. Can be provided. The anticancer agent may contain other active ingredients.

  For example, in the case of food, such as water, alcohol, starch, protein, fiber, sugar, lipid, vitamin, mineral, flavoring, coloring, sweetener, seasoning, stabilizer, preservative, etc. 4-vinyl guaiacol polymerization represented by the above formula (1) in combination with raw materials or materials usually blended in foods, or in the case of pharmaceuticals, in combination with carriers, excipients, diluents, stabilizers, etc. A compound or pharmaceutically acceptable salt can be used. In particular, considering the physiologically active field of the present compound, it is preferably used in the field of health maintenance and promotion such as cancer prevention and cancer treatment, and further in the field of disease healing.

  The further effect and efficacy possessed by the 4-vinylguaiacol polymerized compound represented by the formula (1) or a pharmaceutically acceptable salt can be used within a range that can be inferred from the obtained physiological activity data.

  When the 4-vinyl guaiacol polymerized compound represented by the formula (1) or a pharmaceutically acceptable salt is used for pharmaceutical use, for example, the 4-vinyl guaiacol polymerized compound represented by the formula (1) or a pharmaceutical The intake of the salt acceptable to the above is not particularly limited as long as the desired improvement, treatment or prevention effect can be obtained, and usually the mode, the age, sex, constitution and other conditions of the patient, the type of the disease In addition, it is appropriately selected depending on the degree thereof. For example, the 4-vinyl guaiacol polymerized compound represented by formula (1) or a pharmaceutically acceptable salt is preferably about 0.1 mg to 1,000 mg per day, Can be taken in 4 divided doses.

  The 4-vinyl guaiacol polymerized compound represented by the formula (1) or a pharmaceutically acceptable salt can be used for foods such as functional foods, health foods, health-oriented foods and the like. The form of the food may be any form such as a beverage, alcoholic beverage, jelly, confectionery, etc. For example, among confectionery, hard candy, soft candy, gummy that is excellent in storage and carrying due to its capacity, etc. Examples include candy and tablets, but there is no particular limitation.

  In addition, when the 4-vinylguaiacol polymerized compound represented by the above formula (1) or a pharmaceutically acceptable salt is orally administered or ingested as a pharmaceutical or a food, it is based on a conventional method, tablets and pills , Capsules, fine granules, granules and the like. If necessary, the granules of capsules containing tablets, pills, granules, granules can be sugar-coated with sugars such as sucrose, sugar alcohols such as maltitol, gelatin, hydroxypropylcellulose, hydroxypropylmethylcellulose, etc. It can also be coated. In addition, the tablets, pills, capsules, fine granules, granules, etc. may be coated with a film of gastric or enteric substance, or a known solubilization may be performed to improve the solubility of the preparation. Processing can also be performed. Based on a conventional method, it may be used in an injection or a drip.

  Since the above-mentioned pharmaceuticals or foods are excellent in safety, not only for humans, for example, non-human animals such as rats, mice, guinea pigs, rabbits, sheep, pigs, cows, horses, cats It may be added to therapeutic agents, preventive agents or feeds for mammals such as dogs, monkeys and chimpanzees, birds, amphibians and reptiles.

  EXAMPLES Next, although this invention is demonstrated in detail based on an Example, this invention is not limited only to this Example.

(Example 1: Production of 4-vinyl guaiacol polymerization compound)
A mixed liquid (pH = 7.3) in which 500 mg of ferulic acid (manufactured by Wako Pure Chemical Industries, Ltd.) was dissolved in 10 mL of ethanol and 10 mL of 5% aqueous sodium hydrogen carbonate solution (manufactured by Wako Pure Chemical Industries, Ltd.) was added. The mixture was heated at 130 ° C. for 40 minutes in an autoclave (trade name “SANYO LABO AUTOCLAVE”, manufactured by Sanyo Electric Co., Ltd.). 1 mL of the resulting post-reaction composition was made up to 50 mL with methanol, and 10 μL of this was analyzed by HPLC.
HPLC analysis was performed under the following conditions.
Column: Column for reverse phase “Develosil (registered trademark) C-30-UG-5” (4.6 mm.d. × 250 mm)
Mobile phase: A: H ₂ O (0.1% trifluoroacetic acid (TFA)), B: Acetonitrile (0.1% TFA)
Flow rate: 1 mL / min
Injection: 10 μL
Detection: 254 nm
Gradient (% by volume): 30 minutes from 80% A / 20% B to 20% A / 80% B, 5 minutes from 20% A / 80% B to 100% B, 10 minutes at 100% B (all linear)

  The obtained chromatogram is shown in FIG. The upper figure shows the chromatogram before the production reaction, and the lower figure shows the chromatogram after the production reaction. In the figure above, the ferulic acid peak is shown. As shown in the figure below, ferulic acid decreased due to the formation reaction, and several increased peaks were confirmed, confirming the generation of a plurality of compounds. Especially, it turns out that the compound shown by the peak of A is produced | generated from ferulic acid.

(Example 2: Isolation and structure determination of 4-vinylguaiacol polymerization compound)
Of the reaction product obtained in Example 1, the compound contained in the peak indicated by A in FIG. 1 was isolated by preparative HPLC. When dried according to a conventional method, 301 mg of a yellow powdery compound (hereinafter, UHA7004) was obtained.

Subsequently, when the molecular weight of the UHA7004 was measured by high resolution electron ionization-mass spectrometry, the measured value was UHA7004: 300.3495. From the comparison with the theoretical value, the following molecular formula was obtained. It was.
UHA7004
Theoretical value C18H20O4 (M ⁺ ): 300.3490
Molecular formula C ₁₈ H ₂₀ O ₄

  Next, the UHA7004 is subjected to nuclear magnetic resonance (NMR) measurement, and it is confirmed from analysis of 1H-NMR, 13C-NMR and various two-dimensional NMR data that the UHA7004 has a structure represented by the formula (1). did. From this, it was shown that the 4-vinyl guaiacol polymerization compound represented by the formula (1) can be efficiently produced by the method of the present invention.

  In addition, about each NMR measurement value, each site | part of UHA7004 represented by Formula (1) is shown.

1H nuclear magnetic resonance spectrum and 13C nuclear magnetic resonance spectrum are shown in Table 1, respectively.
Values are δ and ppm, measured with methanol-d3.

Moreover, the physicochemical properties of UHA7004 are as follows.
(Properties)
Yellow powder (soluble)
Water: Insoluble methanol: Soluble ethanol: Soluble DMSO: Soluble chloroform: Soluble ethyl acetate: Soluble

(Example 3: Anticancer activity of UHA7004)
Next, in order to see the anticancer effect of UHA7004, a cancer cell growth inhibition test using HL-60 cells (Human proneolytic leukemia cells: human myelocytic leukemia cells) was performed.

For the culture of HL-60 cells, a high nutrient medium “RPMI-1690” containing 4 mM glutamine (L-Glutamine, manufactured by Sigma-Aldrich Japan Co., Ltd.) and 10% FBS (Foetal Bovine Serum, manufactured by Biological Industries, Inc.) ( Sigma Aldrich Japan Co., Ltd.) was used. In the test, a 96-well plate for cell culture (manufactured by Corning Japan Co., Ltd.) was used, and HL-60 cells, the number of cells of which was adjusted to 5 × 10 ⁵ cells / mL, were seeded at 100 μL per well.

  Two types of samples, ferulic acid and UHA7004 which is the product of the present invention, were used. For sample preparation, each compound was dissolved in dimethoxysulfoxide (DMSO, manufactured by Wako Pure Chemical Industries, Ltd.) to prepare 50 μM, 100 μM, 500 μM, 1000 μM, and 2000 μM. This was added so that the final concentrations in the culture medium of HL-60 cells were 0.5 μM, 1 μM, 5 μM, 10 μM, and 20 μM, respectively, and the test was started. A negative control was prepared by adding the same amount of DMSO as a solvent.

The number of viable cells was quantified by the MTT method using “Cell counting kit-8” (trade name, manufactured by Dojin Dou Molecular Technology Co., Ltd.). After 24 hours from the start of the test, 10 μL of the cell counting kit-8 solution was added to each well and stirred well. After a light-shielding reaction at 37 ° C. and 5% CO ₂ for 1 hour, absorbance was measured at a measurement wavelength of 450 nm using a plate reader (“BIO-RAD Model 680”, manufactured by Bio-Rad Laboratories). The cell viability was calculated based on the obtained data. The cell viability is a value calculated by setting the number of viable cells in a culture solution to which only DMSO as a solvent is added as 100% and the number of viable cells in each compound concentration as a relative value. From the relationship between the concentration of each compound and the cell viability, a concentration IC ₅₀ (50% inhibitory concentration) that suppresses cell proliferation by 50% was calculated (Table 2). From these results, UHA7004 was found to have a strong ability to suppress cancer cell growth. This effect was not observed at all in ferulic acid, and the significance of converting ferulic acid into a 4-vinyl guaiacol polymerized compound was strongly suggested.

(Example 4: Difference in production amount of UHA7004 depending on heating temperature)
A mixed solution (pH = 7.3) of 50 mg of ferulic acid, 1 mL of ethanol, and 1 mL of 5% aqueous sodium hydrogen carbonate solution was heated in an autoclave at 70 ° C., 90 ° C., 110 ° C., and 130 ° C. for 20 minutes. 1 mL of the post-reaction composition obtained under each temperature condition was diluted to 50 mL with methanol and analyzed by HPLC in the same manner as in Example 1.

  As a result, generation of UHA7004 was confirmed under conditions other than 70 ° C. The production ratio of UHA7004 from ferulic acid was not produced at 70 ° C., extremely small at 90 ° C., 5% by weight at 110 ° C., and 44% by weight at 130 ° C. That is, heating at 130 ° C. was the most efficient.

(Example 5: Preparation of extract containing UHA7004)
A mixed solution (pH = 7.3) prepared by adding 1 g of ferulic acid as a food additive, 20 mL of ethanol, and 20 mL of 5% sodium bicarbonate aqueous solution was heated at 130 ° C. for 60 minutes in an autoclave. The resulting reaction solution was heated under reduced pressure to dryness to obtain 11 g of UHA7004-containing extract. The obtained UHA7004-containing extract was confirmed by the same method as in Example 2, and 0.6 g of UHA7004 was contained. This work was repeated as necessary.

(Example 6: Food containing UHA7004)
1 g of UHA7004-containing extract obtained in Example 5 was dissolved in 100 mL of ethanol in advance, 500 g of sugar and 400 g of starch syrup were mixed and dissolved in this, and after mixing 100 g of fresh cream, 20 g of butter, 70 g of condensed milk, and 1.0 g of emulsifier, The pressure was reduced by −550 mmHg in a vacuum kettle and concentrated under a condition of 115 ° C. to obtain a milk hard candy having a moisture value of 3.0% by weight. This milk hard candy is not only easy to eat as a confectionery, but also as a functional food that reduces the risk of cancer spread in cancer patients, reduces the risk of developing cancer, and prevents cancer. Can also be used.

(Example 7: Drug containing UHA7004)
UHA7004 obtained by the same method as in Examples 1 and 2 was dissolved in ethanol, adsorbed onto microcrystalline cellulose, and then dried under reduced pressure. This was tableted according to a conventional method. The formulation is as follows: UHA7004 10 parts, corn starch 23 parts, lactose 12 parts, carboxymethylcellulose 8 parts, microcrystalline cellulose 32 parts, polyvinylpyrrolidone 4 parts, magnesium stearate 3 parts, talc 8 parts It is. This tableted product can be effectively used as a pharmaceutical for the purpose of healing cancer.

Claims (3)

Formula more obtained to a heat treatment ferulic acid under alkaline conditions (1) represented by the 4-vinyl guaiacol polymerizable compounds and one or more compounds selected from a pharmaceutically group consisting acceptable salts Containing an anticancer agent.

Formula more obtained to a heat treatment ferulic acid under alkaline conditions (1) represented by the 4-vinyl guaiacol polymerizable compounds and one or more compounds selected from a pharmaceutically group consisting acceptable salts food characterized by containing a.

One or more compounds selected from the group consisting of a 4-vinylguaiacol polymerized compound represented by the following formula (1) obtained by heat-treating ferulic acid under alkaline conditions and a pharmaceutically acceptable salt thereof: A pharmaceutical product characterized by containing.

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