CN114133422B - Cucurbitane triterpenoid compound and preparation method and application thereof - Google Patents
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- CN114133422B CN114133422B CN202111543716.2A CN202111543716A CN114133422B CN 114133422 B CN114133422 B CN 114133422B CN 202111543716 A CN202111543716 A CN 202111543716A CN 114133422 B CN114133422 B CN 114133422B
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Abstract
The invention relates to the field of compounds prepared by plant extraction, and provides a cucurbitane triterpenoid compound which has a chemical structure shown in a formula I and is named as 23, 24-dihydroxy cucurbitane terpene F-24-methoxy-16,25-diacetate according to a naming rule. Experimental results show that the 23, 24-dihydroxy cucurbitane terpene F-24-methoxy-16,25-diacetate provided by the invention has IC effect on glioma 50 The value can be as low as 10 mug/mL or less.
Description
Technical Field
The invention relates to the field of compounds prepared by plant extraction, in particular to a cucurbitane triterpenoid compound and a preparation method and application thereof.
Background
Glioma is a relatively common primary tumor in brain, the root of the glioma is mainly from glial cells in brain tissues, and the glial cells have gene mutation under the action of various internal factors and external factors and have uncontrollable proliferation, so that the glioma is formed. Due to the space occupying effect of glioma, the patient can have symptoms of headache, nausea, vomiting, epilepsy, blurred vision and the like.
Adriamycin is currently a commonly used drug for the treatment of gliomas, its pharmaceutically active IC 50 Values greater than 20. Mu.g/mL indicate that the pharmaceutical activity is not very desirable.
Disclosure of Invention
In view of the above, the invention aims to provide a cucurbitane triterpenoid compound, a preparation method and an application thereof, and IC of the compound aiming at glioma 50 The value can be as low as 10 mug/mL or less.
In order to achieve the above purpose, the invention provides the following technical scheme:
the invention provides a cucurbitane triterpenoid compound, which has a chemical structure shown in a formula I:
the invention provides a preparation method of a cucurbitane triterpenoid compound, which comprises the following steps:
(1) Mixing rhizomes of the Chelidonium majus with an ethanol water solution, heating, soaking, extracting and concentrating to obtain an extract;
(2) Mixing the extract obtained in the step (1) with water, and then extracting with n-butyl alcohol to obtain an extract;
(3) Performing column chromatography on the extract obtained in the step (2) to sequentially obtain 6 different chromatographic parts Fr.A-Fr.F; eluent of the column chromatography is dichloromethane and methanol;
volume ratios of dichloromethane to methanol in the eluents corresponding to fr.a to fr.f are 50;
(4) Performing liquid chromatography separation on the Fr.B chromatography part obtained in the step (3) to sequentially obtain 8 different fractions A-H; wherein the fraction E is crude product of cucurbitane triterpenoid;
the liquid chromatographic separation adopts equal gradient elution; the eluent for the isocratic elution is methanol and water; the volume ratio of the methanol to the water is 75;
(5) And (4) purifying the crude product of the tropane triterpenoid in the step (4) to obtain the tropane triterpenoid.
Preferably, the rhizomes of the Jinfoshan hemsleya amabilis in the step (1) are in powder form.
Preferably, the number of heating impregnation extraction in the step (1) is 1 to 5.
Preferably, the heating impregnation extraction in the step (1) is heating reflux extraction.
Preferably, the mass concentration of the ethanol water solution in the step (1) is 40-60%.
Preferably, the heating impregnation extraction in the step (1) is heating reflux extraction.
Preferably, the purification in step (5) is a liquid chromatography separation.
Preferably, the mobile phase of the liquid chromatographic separation is methanol and water.
Preferably, the volume ratio of methanol to water is 55.
The invention also provides application of the cucurbitane triterpenoid compound in the technical scheme or the cucurbitane triterpenoid compound prepared by the preparation method in the technical scheme in preparation of a medicine for treating glioma.
The invention provides a cucurbitane triterpenoid compound which has a structure shown in a formula I and is named as 23, 24-dihydroxy cucurbitane terpene F-24-methoxy-16,25-diacetate according to a naming rule. Experimental results show that the 23, 24-dihydroxy cucurbitane terpene F-24-methoxy-16,25-diacetate provided by the invention has IC effect on glioma 50 The value can be as low as 10 mug/mL or less.
Drawings
FIG. 1 is a chemical structural diagram of cucurbitane triterpenoids prepared in example 1 of the invention;
FIG. 2 shows cucurbitane triterpenoids prepared in example 1 of the present invention 1 H-NMR spectrum;
FIG. 3 shows the cucurbitane triterpenoids prepared in example 1 of the present invention 13 C-APT spectrum.
Detailed Description
The invention provides a cucurbitane triterpenoid compound, which has a chemical structure shown in a formula I:
the cucurbitane triterpenoid compound with the structure shown in the formula I is named as 23, 24-dihydroxy cucurbitane terpene F-24-methoxyl-16, 25-diacetate according to the naming rule. The 23, 24-dihydroxy cucurbitane terpene F-24-methoxy-16,25-diacetate provided by the invention is white powder, is easily soluble in methanol and pyridine, and has IC (integrated Circuit) effect on glioma 50 The value can be as low as 10 mug/mL or less.
The invention also provides a preparation method of the cucurbitane triterpenoid compound in the scheme, which comprises the following steps:
(1) Mixing rhizomes of the Jinfo mountain hemsleya amabilis with an ethanol water solution, heating, dipping, extracting and concentrating to obtain an extract;
(2) Mixing the extract obtained in the step (1) with water, and then extracting with n-butanol to obtain an extract;
(3) Performing column chromatography on the extract obtained in the step (2) to sequentially obtain 6 different chromatographic parts Fr.A-Fr.F; eluent of the column chromatography is dichloromethane and methanol;
volume ratios of dichloromethane to methanol in the eluents corresponding to fr.a to fr.f are 50;
(4) Performing liquid chromatography separation on the Fr.B chromatography part obtained in the step (3) to sequentially obtain 8 different fractions A-H; wherein the fraction E is crude product of cucurbitane triterpenoid;
the liquid chromatographic separation adopts equal gradient elution; the eluent for the isocratic elution is methanol and water; the volume ratio of the methanol to the water is 75;
(5) And (5) purifying the crude product of the tropane triterpenoid in the step (4) to obtain the tropane triterpenoid.
The invention mixes the rhizomes of the Chelidonium majus with an ethanol water solution, and then carries out heating, dipping, extraction and concentration to obtain an extract.
In the present invention, the rhizomes of the Chelidonium majus are preferably in a powder form. In the present invention, the particle size of the powder is not particularly limited, and may be a particle size obtained by extracting a plant rhizome as a target extract, which is well known to those skilled in the art.
In the present invention, the heating immersion extraction is preferably heating reflux extraction. In the present invention, the number of times of the heating immersion extraction is preferably 1 to 5 times, and more preferably 2 to 3 times. In the present invention, the time for each heating reflux extraction is preferably 1 to 5 hours, more preferably 2 to 4 hours. In the present invention, the mass concentration of the ethanol aqueous solution is preferably 40 to 60%, and more preferably 45 to 55%. In the invention, the ratio of the mass of the rhizome powder of the Jinfo mountain hemsleya amabilis to the volume of the ethanol water solution is preferably 10 kg/(12-20) L during each heating reflux extraction. The invention controls the time and times of each heating reflux extraction and the concentration and the dosage of the ethanol in the above ranges, which is beneficial to realizing the full extraction of the cucurbitane triterpenoid in the Jinfo mountain hemsleya amabilis.
The invention does not particularly specify the concentration mode after the hot dipping extraction, and the ethanol and the water in the dipping solution can be removed by adopting the concentration mode which is well known to a person skilled in the art. In the invention, the ethanol is an organic solvent, and is mutually soluble with a subsequent extractant n-butyl alcohol, and simultaneously the ethanol and the water are mutually soluble, so that the extraction operation is difficult to perform; meanwhile, because the boiling point of the ethanol is relatively close to the boiling point of the water, the water is removed together in the process of removing the concentrated ethanol.
After obtaining the extract, the invention mixes the extract with water, and then carries out n-butyl alcohol extraction to obtain the extract.
The amount of water used in the invention is not particularly specified, and the extract can be dispersed by using the amount of water well known to a person skilled in the art. The dosage of the n-butyl alcohol is not specially specified, and the dosage of the extracting agent well known to a person skilled in the art is adopted to realize the full extraction of the extracted substances. In the invention, the cucurbitane triterpenoid is insoluble in water and soluble in n-butyl alcohol, and the n-butyl alcohol is slightly soluble in water, so that the cucurbitane triterpenoid can be extracted into the n-butyl alcohol by using the n-butyl alcohol as an extracting agent.
After the extraction is completed, the present invention preferably concentrates the extracted product to obtain an extract. In the present invention, the extracted product is an n-butanol phase. In the present invention, since n-butanol is slightly soluble in water, impurities and water are separated out by extraction.
The present invention does not specify the concentration of the extracted product, and the n-butanol phase may be removed by a concentration method known to those skilled in the art. In the invention, the n-butanol in the extract is compatible with the mobile phase methanol in the subsequent column chromatography, so that the polarity of the mobile phase in the column chromatography process is influenced, and the subsequent separation effect is further influenced, therefore, the n-butanol in the extracted product needs to be removed before the column chromatography. In the invention, because the n-butanol is slightly soluble in water, trace water enters the n-butanol phase, but because the boiling points of the water and the n-butanol are not greatly different, the water is removed at the same time of removing the n-butanol.
After the extract is obtained, the extract is subjected to column chromatography to sequentially obtain 6 different chromatographic parts Fr.A-Fr.F; in the invention, the eluent of the column chromatography is dichloromethane and methanol; volume ratios of dichloromethane to methanol in the eluents from fr.a to fr.f are 50. The volume ratio of the dichloromethane to the methanol in the eluent is limited to the range, so that the further separation of the cucurbitane triterpenoid is facilitated, and the cucurbitane triterpenoid appears in the eluent with the volume ratio of the dichloromethane to the methanol being 20.
After a Fr.B chromatographic part is obtained, performing liquid chromatographic separation on the Fr.B chromatographic part to sequentially obtain 8 different fractions A-H; wherein the fraction E is crude product of cucurbitane triterpenoid.
In the present invention, the liquid chromatography separation employs isocratic elution; the eluent for the isocratic elution is methanol and water; the volume ratio of methanol to water is 75.
In the invention, the retention time of A to H is preferably 6 to 11min, 15.631mim, 18.383min, 23.782min, 25.231min, 30.231min, 41.249min and 42.999min in sequence. In the present invention, the retention time of the 8 different fractions is at the above time, and further separation of cucurbitane triterpenoids can be sufficiently achieved.
After the crude product of the tropane triterpenoid is obtained, the crude product of the tropane triterpenoid is purified to obtain the tropane triterpenoid.
In the present invention, the purification is preferably a liquid chromatography separation. In the present invention, the mobile phase for the liquid chromatography separation is preferably methanol and water. In the present invention, the volume ratio of the mobile phase methanol and water of the liquid chromatography is preferably 55. The invention has no special regulation on the retention time of the tropane triterpenoid, and can realize the purification of a crude product of the tropane triterpenoid to obtain a pure product under the condition that the volume ratio of mobile phase methanol to water is 55. In the embodiment of the invention, the retention time of the tropane triterpenoid is preferably 72.39min. In the embodiment of the invention, the compound with the retention time of 72.39min is a pure product of cucurbitane triterpenoid.
The invention also provides application of the cucurbitane triterpenoid compound in the technical scheme or the cucurbitane triterpenoid compound prepared by the preparation method in the technical scheme in preparation of a medicine for treating glioma.
The application of the invention is not specially specified, and the cucurbitane triterpenoid is taken as the main component of the drug for treating glioma by adopting an application mode well known to those skilled in the art.
Example 1
The cucurbitane triterpenoid has a chemical structure as follows:
the preparation method of the cucurbitane triterpenoid comprises the following steps:
(1) Taking 10.0kg of dried root tubers of the Jinfo mountain snow gall, crushing, adding 15L of ethanol water solution with the mass concentration of 50%, heating, refluxing and extracting for 3h, filtering to obtain solids, repeating the extraction method for 2 times, heating, refluxing and extracting for 3 times for the dried root tubers of the Jinfo mountain snow gall, combining extracting solutions, and concentrating under reduced pressure to obtain the extract with the total amount of 1010g; dispersing the obtained extract with appropriate amount of water, extracting with n-butanol, concentrating the extractive solution under reduced pressure to dry, and weighing to obtain total n-butanol extract 230g;
(2) Subjecting the n-butanol fraction to silica gel column chromatography, performing gradient elution with dichloromethane and methanol, and changing the gradient after each gradient elution is colorless to obtain 6 parts from fr.a to fr.f, wherein the 6 parts from fr.a to fr.f correspond to the eluents of dichloromethane and methanol in a volume ratio of 50;
(3) Taking a Fr.B (corresponding eluent is dichloromethane and methanol with the volume ratio of 20);
(4) And (3) purifying the fraction 5, namely the fraction E by using semi-preparative high performance liquid chromatography and using methanol and water in a volume ratio of 55 to 45 as an eluent, collecting the eluent with retention time of 72.39min, and concentrating the eluent to obtain a pure product of the cucurbitane triterpenoid, namely 23,24-dihydrocucurbitacin F-24-methoxy-16 and 25-diacetate. It is white and readily soluble in methanol.
Preparation of the Compound of the invention example 1 1 The H-NMR spectrum is shown in FIG. 2, which shows 13 The C-APT spectrum is shown in FIG. 3. The peaks in fig. 2 and 3 were assigned by analyzing the maps in fig. 2 and 3, and the peak assignments in fig. 2 and 3 are shown in table 1. The numbers in Table 1 are shown in FIG. 2 and FIG. 3It can be seen that the chemical structural formula of the compound prepared in this example is shown in fig. 1.
Table 1 preparation of compound of example 1 1 H-NMR and 13 attribution of each peak of C-APT
23,24-dihydrocucurbitacin F-24-methoxy-16,25-diacetate was subjected to an in vitro antitumor drug efficacy test using the MTT colorimetric method for an in vitro cytotoxicity test.
23,24-dihydrocucurbitacin F-24-methoxy-16,25-diacetate is used as an experimental group, adriamycin (antibiotic) is used as a control group, and the MTT method is adopted to detect the cytotoxic activity of the compound to drug-resistant C6 glioma cells; 2X 104 cells in logarithmic growth phase were seeded in 96-well plates at 100. Mu.L/well, placed at 37 ℃ and 5% CO 2 Culturing in an incubator for 24h, and respectively arranging a control group, a blank group, an experimental group with different concentration gradients and a blank group for selecting glioma cells, wherein each group is provided with 6 multiple wells. Adding drugs into the experimental groups to the final concentrations of 2 mu g/mL, 4 mu g/mL, 8 mu g/mL, 16 mu g/mL and 32 mu g/mL respectively, continuing to culture for 24, 48 and 72 hours, adding 5mg/mLMTT solution to each well for 20 mu L, continuing to culture for 4 hours, discarding the supernatant, adding 150 mu L DMSO solution to each well, slightly shaking for 10min to dissolve the DMSO solution, detecting the absorbance at the wavelength of 570nm by combining with a microplate reader, and calculating IC 50 . Calculating IC from absorbance values 50 . The inhibitory effect of the compound prepared in example 1 and doxorubicin on glioma under in vitro conditions is shown in table 2.
TABLE 2 inhibition of glioma by the compound prepared in example 1 and doxorubicin in vitro
| Group of | Compound (I) | IC 50 μg/mL |
| Experimental group | 23,24-dihydrocucurbitacin F-24-methoxy-16,25-diacetate | 6.7±0.94 |
| Control group | Adriamycin | 25.7±1.81 |
As can be seen from the table 2, the compound provided by the invention has a certain in vitro inhibition effect on glioma under the same conditions, and the inhibition effect is superior to that of adriamycin in the prior art, so that the compound prepared by the invention can be used as a raw material for preparing a medicament for preventing and treating glioma, and has a good application value.
The description is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, it is possible to make various improvements and modifications without departing from the principle of the present invention, and these improvements and modifications should also be construed as the protection scope of the present invention.
Claims (10)
1. A cucurbitane triterpenoid compound is characterized by having a chemical structure shown as a formula I:
2. the method for preparing cucurbitane triterpenoids in claim 1, comprising the following steps:
(1) Mixing rhizomes of the Jinfo mountain hemsleya amabilis with an ethanol water solution, heating, dipping, extracting and concentrating to obtain an extract;
(2) Mixing the extract obtained in the step (1) with water, and then extracting with n-butanol to obtain an extract;
(3) Performing column chromatography on the extract obtained in the step (2) to sequentially obtain 6 different chromatographic parts Fr.A-Fr.F; eluent of the column chromatography is dichloromethane and methanol;
volume ratios of dichloromethane to methanol in the eluents corresponding to fr.a to fr.f are 50;
(4) Performing liquid chromatography separation on the Fr.B chromatography part obtained in the step (3) to sequentially obtain 8 different fractions A-H; wherein the fraction E is crude product of cucurbitane triterpenoid;
the liquid chromatographic separation adopts equal gradient elution; the eluent for the isocratic elution is methanol and water; the volume ratio of the methanol to the water is 75;
(5) And (4) purifying the crude product of the tropane triterpenoid in the step (4) to obtain the tropane triterpenoid.
3. The method according to claim 2, wherein the rhizomes of Chelidonium majus in step (1) are in a powder form.
4. The method as claimed in claim 2, wherein the number of heating impregnation extractions in the step (1) is 1 to 5.
5. The production method according to claim 2 or 4, wherein the heating immersion extraction in the step (1) is heating reflux extraction.
6. The preparation method according to claim 2, wherein the mass concentration of the ethanol aqueous solution in the step (1) is 40 to 60%.
7. The production method according to claim 2, wherein the purification in the step (5) is a liquid chromatography separation.
8. The method of claim 7, wherein the mobile phase for liquid chromatography is methanol and water.
9. The method according to claim 8, wherein the volume ratio of methanol to water is 55.
10. Use of the cucurbitane triterpenoid of claim 1 or prepared by the preparation method of any one of claims 2 to 9 in preparation of a medicament for treating glioma.
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