CN111269204B - Compound with antitumor activity and preparation method and application thereof - Google Patents
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Abstract
The invention discloses a compound with anti-tumor activity, which is obtained by separating bran-fried largehead atractylodes rhizome through the analysis of wave spectrum and mass spectrum data through the systematic and intensive research on chemical components of the bran-fried largehead atractylodes rhizome. In-vivo and in-vitro anti-tumor activity researches show that the compound with anti-tumor activity provided by the invention has strong inhibitory activity on various tumor cells such as lung adenocarcinoma, human brain glioma, human colon cancer or human liver cancer.
Description
Technical Field
The invention relates to a compound with anti-tumor activity, in particular to an atractylone polymeric compound with anti-tumor activity separated from rhizoma atractylodis and a preparation method thereof, belonging to the technical field of medicines.
Background
The traditional Chinese medicine has application history for thousands of years, and the processing of the traditional Chinese medicine is one of the characteristics of the traditional Chinese medicine. The traditional Chinese medicine processing technology can greatly change the substance basis of the medicine, and the changed substance basis group can also generate corresponding biological effect on the human body, thereby generating different clinical treatment effects. The discovery of chemical components with unique structure and activity from traditional Chinese medicine products is a method and idea with great effort.
The white atractylodes rhizome is a dried rhizome of white atractylodes rhizome Atracyylodes macrocephala Koidz of Compositae, is one of the famous Chinese medicines, namely Zhe eight flavors, and has the effects of tonifying qi and spleen, eliminating dampness and promoting diuresis, and stopping sweating and preventing miscarriage. Clinically, the application difference of the raw and processed white atractylodes rhizome is large, the raw white atractylodes rhizome is good at strengthening the spleen and drying dampness, and the property of the raw white atractylodes rhizome is mild after being stir-fried with bran and is good at strengthening the spleen and replenishing qi. Modern researches have proved that rhizoma Atractylodis Macrocephalae has significant antitumor activity, Chinese medicine rhizoma Atractylodis has inhibitory effect on gastric cancer SGC-7901SP and transplanted sarcoma S180 cells, and volatile oil has inhibitory effect on mouse H22 liver cancer lymphatic channel metastasis. However, the modern research has not yet completely clarified the substance basis of anti-tumor before and after processing of rhizoma Atractylodis Macrocephalae.
Disclosure of Invention
The purpose of the invention is as follows: the invention aims to carry out intensive and systematic research on processed rhizoma atractylodis macrocephalae and develop a novel compound with anti-tumor activity, and the invention also aims to provide a preparation method of the compound.
The technical scheme is as follows: in order to achieve the above purpose, the invention adopts the technical scheme that:
a compound with anti-tumor activity has a molecular formula of C31H40O2The structural formula is as follows:
the preparation method of the compound with the antitumor activity comprises the following steps:
(1) preparation of bran-fried bighead atractylodes rhizome: preheating wheat bran and crude rhizoma Atractylodis Macrocephalae, adding wheat bran into the pan, adding rhizoma Atractylodis Macrocephalae slices when smoking, parching until rhizoma Atractylodis is brown, and adding fragrance; obtaining bran-fried bighead atractylodes rhizome;
(2) extracting rhizoma atractylodis macrocephalae stir-fried with bran: taking the white atractylodes rhizome stir-fried with bran in the step (1), performing ultrasonic extraction by using methanol, combining extracting solutions, recovering a solvent under reduced pressure, and drying to obtain an extract;
(3) adding water into the extract obtained in the step (2) for dispersion, adding equal volume of n-hexane for extraction, combining the extract liquor, and recovering the solvent under reduced pressure to obtain an n-hexane extract;
(4) subjecting the n-hexane extract obtained in the step (3) to silica gel column chromatography, and performing gradient elution by using a n-hexane-chloroform mixed solvent system to obtain 18 fractions Fr.1-Fr.18;
(5) subjecting the Fr.5 fraction to gel column chromatography, eluting with chloroform-methanol solvent system, and recovering solvent to obtain Fr.5.1-Fr.5.10 fraction;
(6) detecting with thin layer chromatography TLC, collecting Fr.5.3 fraction, separating with gel column chromatography, eluting with chloroform-methanol solvent, purifying, and recovering solvent to obtain the compound.
As a preferred embodiment, the above-mentioned method for preparing a compound having an antitumor activity comprises the steps of:
(1) preparation of bran-fried bighead atractylodes rhizome: preheating a pot with wheat bran and crude bighead atractylodes rhizome in a weight ratio of 1:4, putting the wheat bran into the pot, putting bighead atractylodes rhizome slices when smoking, continuously stir-frying until the bighead atractylodes rhizome is brown, and overflowing fragrance; obtaining bran-fried bighead atractylodes rhizome;
(2) extracting rhizoma atractylodis macrocephalae stir-fried with bran: taking the white atractylodes rhizome stir-fried with bran in the step (1), crushing to obtain powder, sieving with a 40-mesh sieve, adding 6-12 times of methanol by volume of medicinal material, performing ultrasonic extraction for 2 times, each time for 1-2 hours, combining the extracting solutions, recovering the solvent under reduced pressure, and drying to obtain an extract;
(3) adding water into the extract obtained in the step (2) for dispersion, adding equal volume of n-hexane for extraction for 2 times, combining the extract liquor, and recovering the solvent under reduced pressure to obtain an n-hexane extract;
(4) subjecting the n-hexane extract obtained in the step (3) to silica gel column chromatography, and performing gradient elution by using a n-hexane-chloroform mixed solvent system with a volume ratio of 100:1-1:100 to obtain 18 fractions Fr.1-Fr.18;
(5) subjecting the Fr.5 fraction to gel column chromatography, eluting with chloroform-methanol solvent system at volume ratio of 5:2, collecting 1 fraction per 100mL, and recovering solvent to obtain Fr.5.1-Fr.5.10 fraction;
(6) detecting with thin layer chromatography TLC, collecting Fr.5.3 fraction, separating with gel column chromatography, eluting again with chloroform-methanol solvent at volume ratio of 5:2, purifying, and recovering solvent to obtain the compound.
The compound with antitumor activity is applied to preparing antitumor drugs. Preferably, the tumor is lung adenocarcinoma, human brain glioma, human colon cancer or human liver cancer.
A pharmaceutical preparation having antitumor activity, which comprises the compound having antitumor activity of the present invention.
Preferably, the pharmaceutical preparation with anti-tumor activity is in the form of tablets, capsules, injections, powder injections, granules, fat emulsions, microcapsules, dropping pills, ointments or transdermal controlled release patches.
When the compound with anti-tumor activity provided by the invention is prepared into tablets, the compound with anti-tumor activity and lactose or corn starch are added with lubricant magnesium stearate if necessary, mixed evenly, granulated and then tabletted to prepare the tablets.
When the compound with anti-tumor activity provided by the invention is prepared into capsules, the compound with anti-tumor activity and carrier lactose or corn starch are uniformly mixed, granulated and then encapsulated to prepare the capsules.
When the compound with anti-tumor activity provided by the invention is prepared into granules, the compound with anti-tumor activity and diluent lactose or corn starch are uniformly mixed, granulated, dried and prepared into granules.
When the compound with the anti-tumor activity is prepared into powder injection, the compound with the anti-tumor activity is frozen, dried and sterilized to prepare the powder injection.
When the compound with antitumor activity provided by the invention is prepared into injection, the compound with antitumor activity is taken and added with normal saline to be dissolved, then activated carbon is added, the mixture is uniformly stirred, heated for 30 minutes at 80 ℃, filtered, adjusted in pH value, filtered by a sintered glass funnel or other filters until the mixture is clear, filled and sterilized for 30 minutes at 100-115 ℃ to prepare the injection.
The compound with anti-tumor activity provided by the invention is prepared by adding a carrier according to a conventional pharmaceutical method when being prepared into dosage forms such as a fat emulsion, an ointment or a transdermal controlled release patch.
Has the advantages that: compared with the prior art, the compound with antitumor activity provided by the invention has the following advantages:
the chemical components of the white atractylodes rhizome stir-fried with bran are systematically and deeply researched, and the analysis of wave spectrum and mass spectrum data shows that the compound with the anti-tumor activity is obtained by separating the white atractylodes rhizome stir-fried with bran, is a new compound and is named as atractylodin I. In-vivo and in-vitro anti-tumor activity researches show that the compound with anti-tumor activity provided by the invention has very strong anti-tumor activity on various tumor cells, including lung adenocarcinoma, human brain glioma, human colon cancer or human liver cancer, and makes good technical progress.
The preparation method of the compound with the antitumor activity provided by the invention has the advantages of reasonable process design and strong operability, and the prepared compound with the antitumor activity has high purity.
Drawings
FIG. 1 is a HRMS profile of a compound with anti-tumor activity.
FIG. 2 is a schematic representation of 1H-1H COSY and HMBC of compounds having anti-tumor activity.
FIG. 3 is a 1H-NMR chart of a compound having an antitumor activity.
FIG. 4 is a 13C-NMR chart of a compound having an antitumor activity.
Detailed Description
The invention will be better understood from the following examples. However, those skilled in the art will readily appreciate that the specific material ratios, process conditions and results thereof described in the examples are illustrative only and should not be taken as limiting the invention as detailed in the claims.
Example 1
1. The invention provides a preparation method of the compound:
(1) preparation of bran-fried bighead atractylodes rhizome: preheating a pot special for processing wheat bran and crude bighead atractylodes rhizome in a weight ratio of 1:4, putting the wheat bran into the pot, continuously stir-frying bighead atractylodes rhizome slices until the bighead atractylodes rhizome turns brown when smoking, and overflowing fragrance; parching at 200 deg.C for 26 min.
(2) Extracting rhizoma atractylodis macrocephalae stir-fried with bran: pulverizing the rhizoma Atractylodis Macrocephalae processed with bran in step (1), sieving with 40 mesh sieve, collecting rhizoma Atractylodis Macrocephalae powder 2.0kg, ultrasonic extracting with 10L and 8L methanol for 2 times (each time for 2 hr), mixing extractive solutions, recovering solvent under reduced pressure, and drying to obtain extract 208.7 g.
(3) And (3) adding 2L of the extract obtained in the step (2) into water for dispersing, adding 2L of n-hexane for extracting for 2 times, combining the extract liquor, and recovering the solvent under reduced pressure to obtain 40.37g of an n-hexane extract component.
(4) Subjecting the n-hexane extract obtained in the step (3) to silica gel column chromatography: silica 820g, Catalog #40930-25, L26inch by D3.5 inch, gradient elution with n-hexane-chloroform mixed solvent (volume ratio 100:1-1:100), collection of 1 fraction per 200mL, silica gel Thin Layer Chromatography (TLC) detection (chloroform: methanol 50:1) to combine the components, and then 18 fractions from Fr.1 to Fr.18 are obtained. Wherein the Fr.5 fraction was 77.4mg after drying.
(5) Subjecting the Fr.5 fraction to gel column chromatography (sepheix LH-2045g), eluting with chloroform-methanol (volume ratio of 5:2) solvent system, collecting fractions 1/100 mL, and drying by TLC to obtain 10 fractions total of Fr.5.1-Fr.5.10, wherein the Fr.5.3 fraction is 27.8 mg.
(6) Performing TLC detection on silica gel (chloroform: methanol 50:1), subjecting the Fr.5.3 fraction to gel column chromatography (sepheidex LH-2045g), eluting again with chloroform-methanol (volume ratio 5:2) solvent system, purifying, performing TLC detection, mixing fractions to obtain Fr.5.3.5, and recovering solvent to obtain 12.1mg of the compound.
2. Analysis and characterization of compound spectral data
The compound is white powder, and is easily soluble in chloroform. The UV spectrum (MeOH) absorbs at 230 and 297nm, suggesting that the compound may be a terpenoid. As shown in FIG. 1, [ M + H ] is visible at M/z445.3134 in ESI-HRMS (pos) spectra]+ ion peak, indicating a molecular weight of 444. As shown in fig. 3 and 4, in combination1H- -NMR and13C-NMR spectra and of FIG. 21H-1Schematic diagrams of H COSY and HMBC, as analyzed in table 1. The molecular formula is presumed to be C31H40O2The unsaturation was calculated to be 12.
1H-and 13C-NMR data (500 and 125MHz, CDCL3) for the compounds of Table 1
| No. | δH | δC | No. | δH | |
| 1,1' | 1.58,4H,m | 42.0 | 9,9' | 2.41,2H,m | 39.2 |
| 2,2' | 1.60,4H,m | 23.6 | 10,10' | 36.7 | |
| 3,3' | 2.20,4H,m | 37.3 | 11,11' | 114.3 | |
| 4,4' | 150.0 | 12,12' | 145.0 | ||
| 5,5' | 2.10,2H,m | 45.7 | 13,13' | 1.87,6H,s | 17.6 |
| 6,6' | 2.29,4H,m | 21.2 | 14,14' | 0.76,6H,s | 8.0 |
| 7,7' | 116.6 | 15,15' | 4.84,2H,d；4.68,2H,d | 107.1 | |
| 8,8' | 146.9 | 16 | 3.82,2H,s | 23.9 |
。
EXAMPLE 2 the present invention provides an assay for the antitumor activity of a compound
The invention adopts MTT (tetrazolium salt) method to determine the killing effect of the compound atractylodin I prepared in example 1 on tumor cells.
(1) Tumor cells: lung adenocarcinoma cells A549, human brain glioma cells U87, human colon cancer cells SW480 and human liver cancer cells Hepg 2.
(2) The specific operation method of the experiment comprises the following steps: tumor cells were cultured in DMEM medium (fetal bovine serum containing 10% L-glutamine, 100. mu.g/mL penicillin, 100. mu.g/mL streptomycin). Tumor cells in logarithmic growth phase were taken and digested with 0.25% trypsin at a concentration of 10X 104Each mL of the suspension was collected by placing 180L of the suspension in a 96-well plate, each group was provided with 3 parallel wells, and a blank well, in which no cells were inoculated, and a control well, which was a culture medium containing no compound, were provided. At 37 ℃ with 5% CO2After culturing for 24h under the condition, adding the test compound atractylodin I (the sample is dissolved in DMSO, gradually diluted by a culture medium, and the final concentration of DMSO in the cell Chinese medicinal liquid is less than or equal to 1%) into the culture solution to make the final concentration of the compound be 0, 10, 30, 50, 70 and 90 muM. The solution was continued at 37 ℃ with 5% CO2Co-culturing in an incubator for 48 h. Adding 20 mu LMTT solution (5mg/mL in PBS, continuing the culture for 4h, terminating the culture, carefully removing the supernatant, adding 150 mu LDMSO to each well, shaking the shaker for 10min to completely dissolve the crystals, measuring the absorbance (A) of each well at 570nm with a microplate reader, and calculating the cell survival inhibition rate [% cell survival inhibition rate [ [1- (experiment group A-blank group A)/(control group A-blank group A ])]X 100%. Data were processed using the SPSS software analysis system.
(3) The experimental results are as follows: the experimental data of the survival inhibition rate of the compound on the tumor cells at different concentrations are shown in Table 2. The results show that the compound obtained by separation has better growth inhibition effect on the tumor cells, and IC of lung adenocarcinoma cells A549, human brain glioma cells U87, human colon cancer cells SW480 and human liver cancer cells Hepg25028.94. mu.M, 32.81. mu.M, 48.62. mu.M and 30.63. mu.M, respectively.
TABLE 2 Effect of atractylodin I on the inhibition of survival of individual tumor cells (X + -SD, n ═ 3)
The anti-tumor experiments show that the novel polymer, atractylodin I, separated from the white atractylodes rhizome stir-fried with bran has the effect of resisting various tumors.
The above embodiments are merely illustrative of the technical concept and features of the present invention, and the present invention is not limited thereto, and equivalent changes and modifications made according to the spirit of the present invention should be covered thereby.
Claims (7)
1. A compound having an antitumor activity, characterized in that it has the molecular formula C31H40O2The structural formula is as follows:
2. the process for preparing a compound having antitumor activity according to claim 1, comprising the steps of:
(1) preparation of bran-fried bighead atractylodes rhizome: preheating wheat bran and crude rhizoma Atractylodis Macrocephalae, adding wheat bran into the pan, adding rhizoma Atractylodis Macrocephalae slices when smoking, parching until rhizoma Atractylodis is brown, and adding fragrance; obtaining bran-fried bighead atractylodes rhizome;
(2) extracting rhizoma atractylodis macrocephalae stir-fried with bran: taking the powder of the white atractylodes rhizome stir-fried with bran in the step (1), performing ultrasonic extraction by using methanol, combining extracting solutions, recovering a solvent under reduced pressure, and drying to obtain an extract;
(3) adding water into the extract obtained in the step (2) for dispersion, adding equal volume of n-hexane for extraction, combining the extract liquor, and recovering the solvent under reduced pressure to obtain an n-hexane extract;
(4) subjecting the n-hexane extract obtained in the step (3) to silica gel column chromatography, and performing gradient elution by using a n-hexane-chloroform mixed solvent system to obtain 18 fractions Fr.1-Fr.18;
(5) subjecting the Fr.5 fraction to gel column chromatography, eluting with chloroform-methanol solvent system, and recovering solvent to obtain Fr.5.1-Fr.5.10 fraction;
(6) detecting with thin layer chromatography TLC, collecting Fr.5.3 fraction, separating with gel column chromatography, eluting with chloroform-methanol solvent, purifying, and recovering solvent to obtain the compound.
3. The process for the preparation of a compound with antitumor activity according to claim 2, characterized in that it comprises the following steps:
(1) preparation of bran-fried bighead atractylodes rhizome: preheating a pot by taking wheat bran and crude bighead atractylodes rhizome in a weight ratio of 1:4, putting the wheat bran into the pot, putting bighead atractylodes rhizome slices when smoking, continuously stir-frying until the bighead atractylodes rhizome is brown, and overflowing fragrance; obtaining bran-fried bighead atractylodes rhizome;
(2) extracting rhizoma atractylodis macrocephalae stir-fried with bran: taking the white atractylodes rhizome stir-fried with bran in the step (1), crushing to obtain powder, sieving with a 40-mesh sieve, adding 6-12 times of methanol by volume of medicinal material, performing ultrasonic extraction for 2 times, each time for 1-2 hours, combining the extracting solutions, recovering the solvent under reduced pressure, and drying to obtain an extract;
(3) adding water into the extract obtained in the step (2) for dispersion, adding equal volume of n-hexane for extraction for 2 times, combining the extract liquor, and recovering the solvent under reduced pressure to obtain an n-hexane extract;
(4) subjecting the n-hexane extract obtained in the step (3) to silica gel column chromatography, and performing gradient elution by using a n-hexane-chloroform mixed solvent system with a volume ratio of 100:1-1:100 to obtain 18 fractions Fr.1-Fr.18;
(5) subjecting the Fr.5 fraction to gel column chromatography, eluting with chloroform-methanol solvent system at volume ratio of 5:2, collecting 1 fraction per 100mL, and recovering solvent to obtain Fr.5.1-Fr.5.10 fraction;
(6) detecting with thin layer chromatography TLC, collecting Fr.5.3 fraction, separating with gel column chromatography, eluting again with chloroform-methanol solvent at volume ratio of 5:2, purifying, and recovering solvent to obtain the compound.
4. The use of a compound of claim 1 having anti-tumor activity in the preparation of an anti-tumor medicament.
5. The use of the compound having anti-tumor activity according to claim 4 in the preparation of an anti-tumor medicament, wherein the tumor is lung adenocarcinoma, human brain glioma, human colon cancer or human liver cancer.
6. A pharmaceutical preparation having an antitumor activity, comprising the compound having an antitumor activity according to claim 1.
7. The pharmaceutical preparation with anti-tumor activity according to claim 6, wherein the preparation is in the form of tablet, capsule, injection, powder injection, granule, fat emulsion, microcapsule, drop pill, ointment or transdermal controlled release patch.
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| CN109912551A (en) * | 2019-04-08 | 2019-06-21 | 大理大学 | Sesquiterpene eudesmanolide class compound and its pharmaceutical composition and preparation method and application |
| CN110305089A (en) * | 2019-08-09 | 2019-10-08 | 大理大学 | A kind of method of one-step synthesis antimalarial Sesquiterpene eudesmanolide dimer class compound |
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| CN109912551A (en) * | 2019-04-08 | 2019-06-21 | 大理大学 | Sesquiterpene eudesmanolide class compound and its pharmaceutical composition and preparation method and application |
| CN110305089A (en) * | 2019-08-09 | 2019-10-08 | 大理大学 | A kind of method of one-step synthesis antimalarial Sesquiterpene eudesmanolide dimer class compound |
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