CN107935928B - Total diphenylpyrazole and preparation method and application thereof - Google Patents
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Abstract
The invention discloses total diphenylpyrazole and a preparation method and application thereof. The invention belongs to the field of natural pharmaceutical chemistry, and is characterized in that kudzu root is dried and crushed, extracted by alcoholic solution, filtered and concentrated under reduced pressure to obtain slurry which is a kudzu root alcohol total extract; suspending the total extract with water, sequentially extracting with cyclohexane and ethyl acetate, and removing ethyl acetate by vacuum evaporation to obtain ethyl acetate part; dissolving the ethyl acetate part with absolute ethyl alcohol, placing the ethyl acetate part in an oil bath at the temperature of 80 ℃, adding hydrazine hydrate while stirring, refluxing for 2-8h, stopping the reaction when the solution is detected to contain at least two compounds of the compounds 1-6, and evaporating the solvent under reduced pressure to obtain the total diphenylpyrazole. The invention proves that the total diphenylpyrazole contained in the composition has better activity of inhibiting the proliferation of androgen-dependent and androgen-independent prostate cancer cells. The method is applied to preparing the medicine for preventing and treating the prostatic cancer, has simple preparation method and lower cost, and meets the requirement of medicine development.
Description
Technical Field
The invention belongs to the field of natural medicinal chemistry, and particularly relates to total diphenylpyrazole for preventing and treating prostate cancer, which is prepared from kudzu root as a raw material, and a preparation method and application thereof; the total diphenylpyrazole is obtained by modifying pueraria isoflavone serving as a raw material.
Background
(ii) prostate cancer research progress
Prostate cancer is one of the major cancers affecting male health. In the western developed society, its morbidity and mortality are second only to lung cancer. The incidence of prostate cancer in men in China is low before. However, with the improvement of living standard in recent years, the dietary structure is gradually close to that of the western, and the incidence rate of prostate cancer in China tends to rise. Epidemiological data show that the incidence of prostate cancer in china increases from 1.71/10 million men in 1993 to 7.9/10 million men in 2005 and is rising at a rate of 10% per year. This means that the incidence of prostate cancer in our country may double after 10 years, and prostate cancer, a male disease, will become more and more common.
Currently, the major chemotherapeutic agents for prostate cancer include steroidal antiandrogens (e.g., cyproterone acetate), and non-steroidal antiandrogens (e.g., flutamide and bicalutamide). The former class of drugs brings about severe hepatotoxicity and cardiovascular dysfunction due to the additive effect with hormones in the body; the latter class of drugs has fewer side effects, but fails to function with variations in androgen receptors over prolonged use. Therefore, the search for new anti-prostate cancer drugs is urgent.
General research of kudzu root
1. Overview
Kudzu root (Radix Puerariae), also known as Pueraria Lobata, is the dried root of Pueraria lobata (Willd.) Ohwi, a perennial deciduous vine of Pueraria of Leguminosae, originally recorded in Shennong Ben Cao Jing, and listed as a Chinese product, and has the effects of promoting eruption of measles, relieving muscles and fever, invigorating yang, relieving diarrhea, promoting the production of body fluid, and quenching thirst. It is used clinically in treating headache, dizziness, myocardial infarction, angina pectoris, hypertension, coronary heart disease and other diseases. The Pueraria plants are many in variety, about 30 kinds are in the world, and 11 kinds of Pueraria plants are in common in China. With the exception of Tibet, Qinghai and Xinjiang, Pueraria lobata is distributed in most provinces of China, and is concentrated in Guangdong, Sichuan and the like.
2. Chemical composition research
Since 1927 Zuomu research on radix Puerariae, the research on radix Puerariae has been 80 years old. At present, the domestic and foreign reports mainly separate the following compounds such as isoflavone, flavonoid, coumarin, triterpenoid and the like from the kudzuvine root, wherein the isoflavone is the main component.
3. Study of pharmacological actions
The plants are widely distributed in China and have wide application in many areas. Is often used for treating headache, dizziness, myocardial infarction, angina, hypertension, coronary heart disease and other diseases in China. Modern pharmacological research shows that the kudzuvine root has the activities of resisting arrhythmia, reducing blood sugar, reducing blood fat, resisting thrombus, protecting cardiac muscle, resisting oxidation, regulating estrogen, enhancing immunity and the like. Isoflavone is the main active ingredient, and the active reports about the plants mainly focus on the research on isoflavone compounds at present.
4. Derivatization study of isoflavones
Isoflavone compound has poor water solubility and fat solubility, so that the bioavailability is very low. Many physical methods, such as co-dissolution, solid dispersion, etc., can improve the solubility of such compounds, but most of them use chemical methods to modify their structure to change the problem.
Since isoflavones contain two benzene rings (ring A and ring B), electrophilic reactions are easy to occur, most of structural modifications of isoflavone compounds are substitution reactions around the benzene rings, and acylation, esterification, etherification and the like of phenolic hydroxyl groups. The structural modifications of isoflavonoids reported in the literature are mostly concentrated on the 3 'position, the 4' position, the 2 position and the 7 position. For example: the derivative product of 7-hydroxy-4' -methyl isoflavone (7 position is substituted by different groups) has anti-osteoporosis activity; the genistein is used as a lead compound, and the synthesized product 5-hydroxy-4' -nitro-7-substituted oxyisoflavone has anti-tumor activity; when the hydroxyl at the 4' position of the daidzein is replaced by methoxy and ethoxycarbonyl methylene, the anti-anoxia effect of the daidzein is obviously enhanced. In recent years, modification of the C ring to introduce a nitrogen heterocycle has been carried out, and a compound having a high activity has been desired.
Disclosure of Invention
The primary object of the present invention is to provide a total diphenylpyrazole.
The invention also aims to provide the preparation method of the total diphenylpyrazole, namely the total diphenylpyrazole disclosed by the invention is obtained by taking total isoflavone in kudzuvine root as a raw material and carrying out chemical conversion on the total isoflavone.
The invention further aims to provide application of the total diphenylpyrazole in preparing a medicament for preventing and treating prostatic cancer.
The purpose of the invention is realized by the following technical scheme:
total diphenylpyrazole contains at least two of compounds 1-6, wherein the structures of the compounds 1-6 are shown in figure 2.
Preferably, the total diphenylpyrazole contains compounds 1-6.
The preparation method of the total diphenylpyrazole comprises the following steps:
(1) drying and pulverizing radix Puerariae, extracting with alcoholic solution, filtering, and concentrating under reduced pressure to obtain slurry as total extract of puerarin;
(2) suspending the total extract with water, sequentially extracting with cyclohexane and ethyl acetate, and removing ethyl acetate by vacuum evaporation to obtain ethyl acetate part;
(3) dissolving the ethyl acetate part with absolute ethyl alcohol, carrying out oil bath, adding hydrazine hydrate while stirring, refluxing for 2-8h, stopping the reaction when the solution is detected to contain at least two compounds of the compounds 1-6, and evaporating the solvent under reduced pressure to obtain a total diphenylpyrazole mixture.
The alcoholic solution in the step (1) is preferably an ethanol solution or a methanol solution.
The preferable concentration of the alcoholic solution in the step (1) is 70-100% by volume percent.
The extraction mode in the step (1) is one of ultrasonic, percolation or heating reflux.
The heating reflux condition in the step (1) is preferably 70-80 ℃.
The extraction in the step (1) is preferably carried out at least 3 times, and each extraction time is 1-2 h.
The oil bath temperature in step (4) is preferably 80 ℃.
The refluxing time in the step (4) is preferably 4 h.
The total diphenylpyrazole has the activity of inhibiting androgen-dependent and androgen-independent prostate cancer cells, and can be used for preparing medicines for preventing and treating prostate cancer.
The dosage form of the medicine for preventing and treating the prostatic cancer is tablets, injections, aerosols or nano preparations.
The main principle of the invention is as follows: hydrazine hydrate is used as alkali to open the ring of isoflavone to obtain intermediate compound containing dicarbonyl structure, and hydrazine hydrate is also used as nucleophilic reagent to attack potential intermediate compound containing dicarbonyl structure to produce nucleophilic addition ring reaction and finally produce proton exchange reaction to obtain target compound.
Compared with the prior art, the invention has the following advantages and effects:
(1) radix Puerariae (Radix Puerariae) is a traditional Chinese medicine in China, is widely distributed and is easily obtained;
(2) compared with the conventional modification method, the method obtains the total diphenylpyrazole by combined modification, and has the advantages of simple preparation method and lower cost;
(3) the total diphenylpyrazole obtained by the invention has good activity of resisting prostatic cancer, high efficiency and low toxicity, and meets the requirement of drug development.
Drawings
FIG. 1 is an HPLC chromatogram before and after the reaction of the ethyl acetate fraction of Pueraria lobata of example 1.
a is an HPLC spectrogram before reaction;
and b is an HPLC spectrogram after the reaction.
FIG. 2 is a structural diagram of compounds 1-6.
Detailed Description
The present invention will be described in further detail with reference to examples and drawings, but the present invention is not limited thereto.
Example 1
(1) Preparation of total diphenylpyrazoles
A. Drying radix Puerariae (3kg, commercially available), pulverizing, sieving with 100 mesh sieve, percolating with 95% ethanol at room temperature for 3 times (2 hr each time), and filtering to obtain total extractive solution.
B. Distilling the total extractive solution under reduced pressure to dry to obtain total extract (220g), suspending the total extract in deionized water, sequentially extracting with cyclohexane and ethyl acetate to obtain ethyl acetate extractive solution. Then, the ethyl acetate extract was concentrated under reduced pressure to constant weight to obtain a slurry, i.e., an ethyl acetate extract (isoflavone-containing extract, 24 g). The purpose of the first cyclohexane extraction is to reduce the small polar impurities in the total extract.
C. Dissolving the ethyl acetate part with absolute ethyl alcohol, placing the ethyl acetate part in an oil bath at the temperature of 80 ℃, adding 6ml of hydrazine hydrate while stirring, refluxing for 4h, terminating the reaction, and then evaporating the solvent by using a rotary evaporator under reduced pressure until the weight is constant to obtain a total derivative product (25.2g), namely the total diphenylpyrazole.
(2) Analyzing the total diphenylpyrazole obtained in step (1)
Dissolving the ethyl acetate part and the total derivative product (before and after reaction) obtained in the step (1) in methanol respectively to prepare a solution of 20mg/ml, and carrying out chromatographic analysis by using HPLC (high performance liquid chromatography), wherein the analysis conditions are as follows: c18 reversed phase semi-preparative column (5 μm, 9.4X 250mm), ultraviolet detection wavelength of 210nm, flow rate of 1ml/min, gradient system: a is water, B is acetonitrile; 0-5 min: a 10% (v/v) acetonitrile solution; 5-53 min: 10% (v/v) → 100% (v/v) acetonitrile solution; 53-57 min: 100% (v/v) acetonitrile solution; and (3) obtaining a spectrogram by dissolving 100% (v/v) → 10% (v/v) of acetonitrile in the solvent for 57-60 min (see figure 1).
Analyzing and identifying the main components of the total diphenylpyrazole mixture by using a chromatography method and a wave spectrum analysis method, and determining that the total diphenylpyrazole is mainly as follows: 3- (2-hydroxy-4-methoxy) -4- (4-methoxy) -pyrazole (compound 1), 3- (2, 4-dihydroxy) -4- (4-methoxy) -pyrazole (compound 2), 3- (2-hydroxy-4-methoxy) -4- (4-hydroxyphenyl) -pyrazole (compound 3), 3- (2, 4-dihydroxy) -4- (4-hydroxyphenyl) -pyrazole (compound 4), 3- (2-hydroxy-4-methoxy) -4- (4-hydroxyphenyl) -pyrazole (compound 5), 3- (2-hydroxy-4-O- β -D-hydroxyphenyl) -4- (4-hydroxyphenyl) -pyrazole (compound 4).
(Compound 6). The structure of the compound 1-6 is shown as the formula 1-6, and the spectrum data is as follows:
compound 1: a white powder of a white color, a white powder,
vanillin-concentrated sulfuric acid reaction shows red, bismuth potassium iodide reaction is positive, ESI-MS M/z:297.3[ M + H ]]+,295.3[M-H]-, UV(MeOH)λmax：106,260.8nm；IR(KBr)νmax：2959,1615,1530,1438cm-1。
Compound 2: the color is colorless and the shape of a sheet,
vanillin-concentrated sulfuric acid reaction shows red color, potassium bismuth iodide reaction shows positive, ESI-MS M/z:283.2[ M + H ]]+,281.3[M-H]-, UV(MeOH)λmax：205.4,261.4nm；IR(KBr)νmax：2956,1616,1534,1437 cm-1。
Compound 3: the crystal is colorless powder crystal, and the crystal is transparent,
the vanillin-concentrated sulfuric acid reaction shows red, the bismuth potassium iodide reaction shows positive, the ESI-MS M/z is 283.3[ M + H ]]+,281.3[M-H] -,UV(MeOH)λmax：205.4,260nm。
Compound 4: a white powder of a white color, a white powder,
vanillin-concentrated sulfuric acid reaction shows red, potassium bismuth iodide reaction is positive, ESI-MS M/z is 269.2[ M + H ]]+,267.2[M-H]-, UV(MeOH)λmax：204.6,261.6nm；IR(KBr)νmax：1605,1505,1430cm-1。
Compound 5:
vanillin-concentrated sulfuric acid reaction shows red color, potassium bismuth iodide reaction shows positive, ESI-MS M/z:313.3[ M + H ]]+,311.7[M-H]-,UV(MeOH) λmax：205.8,239nm；IR(KBr)νmax：1633,1527，1435cm-1。
Compound 6: a brown block-shaped solid is obtained,
the vanillin-concentrated sulfuric acid reaction shows red, the bismuth potassium iodide reaction is positive, and the molish reaction is positive. ESI-MS M/z 431.2 [ M + H ]]+,429.6[M-H]-,UV(MeOH)λmax：205.3，261.4nm。
The structural diagrams of compounds 1-6 are shown in FIG. 2.
(3) Detecting the activity of the total diphenylpyrazole obtained in the step (1)
And (2) detecting the inhibition effect of the total diphenylpyrazole obtained in the step (1) on the proliferation of androgen sensitive (LNCaP) prostate cancer cells and androgen insensitive (DU145, PC3) by adopting an MTT method.
Respectively taking cell strains (LNCaP, DU145 and PC3) in logarithmic growth phase, carrying out trypsinization, counting, diluting the cell suspension to 3-5 multiplied by 10 per milliliter4Individual cells, seeded into 96 wellsPlates were inoculated for 24h and then total diphenylpyrazole obtained in step (1) was added to give final concentrations of 0.1, 0.2, 0.4, 0.8, 1.6 and 3.2. mu.g.mL-1The control group was added with PBS containing the same amount, each group was provided with 3 parallel wells and placed in 5% CO2Culturing for 72h in an incubator with saturated humidity at 37 ℃; 20ul of MTT solution (5 mg/ml) was added to each well 4 hours before the termination of the experiment, and the culture was continued for 4 hours. Carefully discarding the supernatant of the culture medium, adding 150. mu.l DMSO into each well, and shaking to dissolve the crystals; the OD value of each hole under the wavelength of 570nm is detected on an enzyme-linked detector, the average of the OD values of each hole is taken, and the growth inhibition rate is calculated according to the following formula. The results were processed with SPSS 18.0 software to determine the median inhibitory rate IC50。
The experimental results are as follows: IC of Total Diphenylpyrazole to LNCaP, DU145, PC350The values are respectively: 15.28 +/-2.32, 21.54 +/-3.43 and 23.51 +/-1.71. Therefore, the total diphenylpyrazole shows mild inhibition effect on proliferation of androgen sensitive (LNCaP) prostate cancer cells and androgen insensitive (DU145, PC3) prostate cancer cells.
Comparative example 1
Comparison of ethanol extract and methanol extract of Pueraria lobata
(1) Preparation of total diphenylpyrazole comprising the following steps:
A. drying radix Puerariae raw material (150g, commercially available), pulverizing, sieving with 100 mesh sieve, percolating with 95% methanol at room temperature for 2 hr for 3 times, and filtering to obtain total extractive solution
B. Distilling the total extractive solution under reduced pressure to dry to obtain total extract (19.2g), suspending the total extract in deionized water, sequentially extracting with cyclohexane and ethyl acetate to obtain ethyl acetate extractive solution. Then, the ethyl acetate extract was concentrated under reduced pressure to constant weight to obtain a slurry, i.e., an ethyl acetate extract (isoflavone-containing extract, 3 g).
C. Dissolving the ethyl acetate part with absolute ethyl alcohol, placing the ethyl acetate part in an oil bath at the temperature of 80 ℃, adding 10ml of hydrazine hydrate while stirring, refluxing for 4h, terminating the reaction, and then evaporating the solvent by using a rotary evaporator under reduced pressure until the weight is constant to obtain a total derivative product (3.1g), namely a total diphenylpyrazole mixture.
(2) Analysis results
Analyzing the total diphenylpyrazole mixture obtained in step (1)
In the same manner as in step (2) of example 1, it was confirmed that the total diphenylpyrazole obtained in this example contained compounds 1 to 6.
The above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and all such changes, modifications, substitutions, combinations, and simplifications are intended to be included in the scope of the present invention.
Claims (2)
1. The application of total diphenylpyrazole in preparing a medicament for preventing and treating prostatic cancer is characterized in that: the total diphenylpyrazole contains compounds 1 to 6; the structural formulas of compounds 1-6 are shown below:
wherein the preparation method of the total diphenylpyrazole comprises the following steps:
(1) drying and pulverizing radix Puerariae, extracting with alcoholic solution, filtering, and concentrating under reduced pressure to obtain slurry as total extract of puerarin;
(2) suspending the total extract with water, sequentially extracting with cyclohexane and ethyl acetate, and removing ethyl acetate by vacuum evaporation to obtain ethyl acetate part;
(3) dissolving the ethyl acetate part with absolute ethyl alcohol, carrying out oil bath, adding hydrazine hydrate while stirring, refluxing for 2-8h, stopping the reaction when the solution is detected to contain at least two compounds of the compounds 1-6, and evaporating the solvent under reduced pressure to obtain a total diphenylpyrazole mixture;
wherein the alcoholic solution in the step (1) is an ethanol solution or a methanol solution, and the volume percentage of the alcoholic solution is 70-100%; the extraction mode of the step (1) is one of ultrasonic, percolation or heating reflux; the heating reflux in the step (1) is carried out at 70-80 ℃ for 4 h; extracting for at least 3 times in the step (1), wherein the extraction time is 1-2 h; the oil bath temperature in the step (4) is 80 ℃.
2. The use of total diphenylpyrazole according to claim 1 in the medicine for the prevention and treatment of prostate cancer, wherein said medicine is in the form of tablet, injection, aerosol or nano-formulation.
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| CN104844514A (en) * | 2015-05-21 | 2015-08-19 | 山东大学 | Diarylpyrazole compound as well as preparation method and application thereof |
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| CN101020662A (en) * | 2007-03-15 | 2007-08-22 | 陕西师范大学 | Compound 3,4-diaryl pyrazole and its prepn and medicinal use |
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| CN103183640A (en) * | 2011-12-30 | 2013-07-03 | 沈阳药科大学 | Diaryl pyrazole compound, and preparation method and purpose thereof |
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