CN112079897A - Two steroid compounds and preparation method and application thereof - Google Patents
Two steroid compounds and preparation method and application thereof Download PDFInfo
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- CN112079897A CN112079897A CN202010840423.XA CN202010840423A CN112079897A CN 112079897 A CN112079897 A CN 112079897A CN 202010840423 A CN202010840423 A CN 202010840423A CN 112079897 A CN112079897 A CN 112079897A
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Abstract
The invention provides two steroid compounds, namely compounds 1 and 2, and the structural formulas of the compounds are shown in figure 1. The steroid compound is extracted from Ganoderma lucidum (Ganoderma lingzhi): the ganoderma lucidum fruit body dry powder is firstly extracted and concentrated by 95 percent ethanol to obtain a crude extract, then extracted and concentrated by ethyl acetate, and then the ethyl acetate extract is subjected to column chromatography by ethanol-water macroporous resin column, wherein the components are subjected to normal phase silica gel column chromatography by petroleum ether-ethyl acetate and petroleum ether-dichloromethane, and are subjected to RP-18 reverse phase silica gel column chromatography by methanol-water, and finally the ganoderma lucidum fruit body dry powder is obtained after separation and purification by high performance liquid chromatography. The steroid compound can be used for preparing antitumor and anticancer drugs. The compound provided by the invention provides a material basis for the research and development of novel antitumor drugs, and is beneficial to the further development of the medicinal value of ganoderma lucidum.
Description
Technical Field
The invention belongs to the field of natural pharmaceutical chemistry, and relates to a preparation method of two steroid compounds and application of the two steroid compounds in preparation of antitumor drugs.
Background
Cancer becomes the leading cause of death of diseases of residents in China, and the morbidity and mortality rate rise year by year, thus posing a great threat to public health. Most of traditional antitumor drugs are cytotoxic drugs, and although the traditional antitumor drugs have a certain clinical curative effect, the defects of strong toxic and side effects, poor selectivity, easy generation of drug resistance and the like are difficult to overcome, so that novel antitumor drugs with high efficiency, low toxicity and strong specificity need to be continuously developed, and the living quality of cancer patients is improved. The structural diversity and the characteristic of easy combination with biological macromolecules of the natural product determine incomparable advantages of the natural product in the process of participating in life physiology, and the natural product has important position irreplaceable in the research and development of new drugs and is an important source for finding drug lead structures and candidate drugs. Ganoderma lucidum has a long medicinal history in China as an important medicinal large-scale fungus resource, and secondary metabolites of Ganoderma lucidum are reported to have various structural types and various biological activities. Therefore, the discovery of metabolites with antitumor activity from ganoderma lucidum is of great significance for the deep development of medicinal value of ganoderma lucidum and the research and development of novel antitumor drugs.
Disclosure of Invention
In order to further develop the medicinal value of ganoderma lucidum, the invention provides two steroid compounds extracted from ganoderma lucidum fruiting bodies, which have antitumor activity.
The invention also aims to provide a preparation method of the steroid compound.
The invention also aims to provide the application of the steroid compound in treating tumors.
In order to achieve the purpose, the invention adopts the following technical scheme.
The two steroid compounds, referred to as compounds 1 and 2, have the structural formulas shown in figure 1.
The two steroids belong to the ergostane class (ergostane) and have an epoxy ring between the 7 and 8 positions and a peroxy ring structure fragment between the 5 and 9 positions, respectively.
The preparation method of the steroid compound comprises the following steps:
(1) drying fruiting body of Ganoderma lucidum, pulverizing, extracting with ethanol, and concentrating the extractive solution to obtain crude extract;
(2) suspending the crude extract in water, extracting with ethyl acetate, and concentrating the ethyl acetate extract phase to obtain ethyl acetate extract;
(3) subjecting the ethyl acetate extract to D101 macroporous resin column chromatography, and eluting with 30%, 50% and 95% v/v ethanol-water in sequence to obtain 3 components A-C;
(4) performing normal-phase silica gel column chromatography on the component C, and performing gradient elution by using 20: 1-1: 3 v/v petroleum ether-ethyl acetate to obtain components C1-C9;
(5) subjecting the component C5 to RP-18 reverse phase silica gel column chromatography, and performing gradient elution by using 70-100% v/v methanol-water to obtain components C5-1 and C5-2;
(6) subjecting the component C5-1 to normal phase silica gel column chromatography, and performing gradient elution with petroleum ether-dichloromethane at a ratio of 2: 1-1: 2 v/v; wherein the main fraction is purified by YMC-Pack ODS-A high performance liquid chromatography column, isocratically eluted with 95% v/v acetonitrile-water solution with detection wavelength of 210 and 254nm, the fraction with retention time of 19.0 min is collected, and the solvent is removed to obtain compound 1;
(7) subjecting the component C6 to RP-18 reverse phase silica gel column chromatography, and performing gradient elution by using 60-100% v/v methanol-water to obtain components C6-1-C6-3;
(8) subjecting the component C6-1 to normal phase silica gel column chromatography, and performing gradient elution with dichloromethane-methanol at a ratio of 200: 1-20: 1 v/v to obtain components C6-1-C6-4-4;
(9) passing the component C6-1-2 through YMC-Pack ODS-A high performance liquid chromatography column, isocratically eluting with 90% v/v acetonitrile-water solution, detecting wavelength at 210 and 254nm, collecting the component with retention time of 27.5 min, and removing solvent to obtain compound 2.
In the step (1), the material-liquid ratio of ganoderma lucidum to ethanol is 1: 2-1: 4 (w/v).
In the step (1), the ganoderma lucidum is crushed to the particle size diameter of less than 3 mm.
In the step (1), the leaching times are 3-5 times, and each time is 7-10 days.
In the step (1), the mixture is concentrated to 1/50-1/70 of the original volume.
In the step (2), the volume ratio of the crude extract to water is 1: 1-1: 2.
In the step (2), the volume ratio of the ethyl acetate to the water is 0.8: 1-1.2: 1.
In the step (2), the extraction times of the ethyl acetate are 3-5 times.
In the steps (6) and (9), the flow rate of the high performance liquid phase eluent is 3.0 mL/min.
The application of the two steroid compounds in preparing anti-tumor and anti-cancer drugs. The tumor is selected from, but not limited to, breast cancer and lung cancer.
The invention has the following advantages:
the invention provides two steroid compounds extracted from ganoderma lucidum, a preparation method thereof and application thereof in preparing antitumor drugs. The two steroids belong to the lanostane class, having epoxy bonds between the 7 and 8 positions and peroxy bonds between the 5 and 9 positions, respectively. The two steroids can obviously inhibit the growth of tumor cells A549 and MCF-7 and cause the death of the tumor cells. The extracted compound provides a material basis for the research and development of novel antitumor drugs, and is favorable for further development of the medicinal value of ganoderma lucidum.
Drawings
FIG. 1 is a structural formula of compounds 1 and 2.
Figure 2 is a high resolution mass spectrum of compound 1.
Fig. 3 is a hydrogen spectrum of compound 1.
Fig. 4 is a carbon spectrum of compound 1.
FIG. 5 is a two-dimensional COSY spectrum of Compound 1.
Figure 6 is a two-dimensional HSQC spectrum of compound 1.
Fig. 7 is a two-dimensional HMBC spectrum of compound 1.
Figure 8 is a two-dimensional NOESY spectrum of compound 1.
FIG. 9 is a comparison of calculated carbon spectrum data for two possible configuration epoxy structures of Compound 1.
Figure 10 is the calculated ECD data for compounds 1 and 2.
Fig. 11 is a high resolution mass spectrum of compound 2.
Fig. 12 is a hydrogen spectrum of compound 2.
Fig. 13 is a carbon spectrum of compound 2.
Figure 14 is a two-dimensional COSY spectrum of compound 2.
Figure 15 is a two-dimensional HSQC spectrum of compound 2.
Fig. 16 is a two-dimensional HMBC spectrum of compound 2.
Figure 17 is a two-dimensional NOESY spectrum of compound 2.
Figure 18 is hydrogen and carbon spectral data for compounds 1 and 2.
FIG. 19 shows experimental data for in vitro tumor cell growth inhibition of compounds 1 and 2.
Detailed Description
The present invention will be further described with reference to the following examples and drawings, but the present invention is not limited to the following examples.
Example 1 preparation of compounds 1 and 2.
10.2 kg dry fruiting body of Ganoderma lucidum, pulverizing to particle size less than 3 mm, soaking in 95% ethanol for extraction for 4 times (10L each time for 7 days). Mixing the ethanol extractive solutions, and concentrating under reduced pressure to obtain 443 g crude extract; the crude extract was suspended in 1.0L of water and then extracted 5 times with 0.7L of ethyl acetate each time. Mixing ethyl acetate extract phases, and concentrating under reduced pressure to obtain 293 g of ethyl acetate extract; performing D101 macroporous resin column chromatography on the extract, and eluting with ethanol-water (v/v, 30%, 50% and 95%) to obtain 3 components A-C; performing normal-phase silica gel column chromatography on the component C, performing gradient elution by using petroleum ether-ethyl acetate (v/v, 20: 1-1: 3), analyzing the components of an eluent according to thin-layer chromatography, and collecting to obtain components C1-C8; RP-18 reverse phase silica gel column chromatography is carried out on the component C5, and gradient elution is carried out by methanol-water (v/v, 70% -100%) to obtain 2 components C5-1 and C5-2. Performing RP-18 reverse phase silica gel column chromatography on the component C6, performing gradient elution by using methanol-water (v/v, 60% -100%) to obtain 3 components C6-1-C6-3, and performing normal phase silica gel column chromatography on the component C6-1, and performing gradient elution by using dichloromethane-methanol (v/v, 200: 1-20: 1) to obtain components C6-1-C6-4-4.
The component C5-1 is treated by normal phase silicA gel column chromatography (gradient elution of petroleum ether-dichloromethane of v/v, 2: 1-1: 2), purified by preparative liquid chromatography (chromatographic column: YMC-Pack ODS-A, 10X 250 mm, flow rate: 3.0 mL/min, detection wavelength of 210 and 254 nm), isocratically eluted with acetonitrile-water (v/v, 95%), the component with retention time of 19.0 min is collected, and the solvent is removed to obtain the pure product of new component compound 1 extracted from GanodermA lucidum, which is 10.8 mg.
The component C6-1-2 was purified by preparative liquid chromatography (column: YMC-Pack ODS-A, 10X 250 mm, flow rate: 3.0 mL/min, detection wavelength: 210 and 254 nm), isocratic eluted with acetonitrile-water (v/v, 90%), fractions with retention time of 27.5 min were collected, and the solvent was removed to obtain 4.4 mg of A pure product of Compound 2, A new component extracted from GanodermA lucidum.
Physical properties of the new ingredient compound 1: white amorphous powder, easily soluble in acetonitrile, dimethyl sulfoxide and chloroform, insoluble in water; specific optical rotation [ alpha ]]D24-20.4 (c 0.60, CHCl3), circular dichroic ECD (c 0.3 mg/mL, MeOH)λ(△)206 (7.5), 221 (–1.9),235 (3.4), 266 (–7.5), 392 (3.0) nm。
Physical properties of the new ingredient compound 2: white amorphous powder, easily soluble in acetonitrile, dimethyl sulfoxide and chloroform, insoluble in water; specific optical rotation [ alpha ]]D24-15.5 (c 0.20, CHCl3), circular dichroic ECD (c 0.3 mg/mL, MeOH)λ(△)235 (–7.8) nm。
Example 2 structural identification of compound 1.
The hydrogenated molecular ion peak M/z 425.3045 ([ M + H ] 425.3045) was obtained by analyzing the high-resolution mass spectrum (FIG. 2)]+,Theoretical value 425.3050), and the molecular formula of the new component is determined to be C by combining the data of carbon spectrum (figure 4)28H40O3. By further analysis of its hydrogen spectrum (fig. 3) and carbon spectrum, the compound was determined to be an ergostane type (ergostane) steroid. The planar structure of the compound is finally determined by analyzing the two-dimensional nuclear magnetic spectrum of the compound, including COSY, HSQC and HMBC (figures 5-7). Part of the relative configuration was determined by analyzing the two-dimensional NOESY data (fig. 8), the configuration of 7, 8-oxirane was established by comparing experimental carbon spectrum data with the calculated carbon spectrum data of the two possible isomers (fig. 9), and finally the absolute configuration of compound 1 was determined by comparing the experimental curve with the calculated curve for the circular dichroism ECD (fig. 10). Compound 1 was identified as (22E) -7 β,8 β -epoxy-ergosta-4, 22-diene-3, 6-dione. Its hydrogen spectrum and carbonThe spectral data are shown in FIG. 18.
Example 3 structural identification of compound 2.
Analysis of the high-resolution mass spectrum (FIG. 11) gave a hydrogenated molecular ion peak M/z 427.3208 ([ M + H ]]+Theoretical value 427.3207), and the molecular formula of the new component is determined to be C by combining the data of carbon spectrum (figure 13)28H42O3. By further analysis of its hydrogen spectrum (fig. 12) and carbon spectrum, the compound was determined to be an ergostane type (ergostane) steroid. The planar structure and relative configuration were determined by analyzing the two-dimensional nuclear magnetic spectrum including COSY, HSQC, HMBC and NOESY (fig. 14-17). The absolute configuration of compound 2 was finally determined by comparing its ECD experimental curve with the calculated curve (figure 10). Compound 2 was identified as (22E) -3 β -hydroxy-5 α,9 α -peroxy-ergosta-6, 8(14), 22-triene. The hydrogen spectrum and carbon spectrum data are shown in FIG. 18.
Example 4 compounds 1 and 2 have in vitro anti-tumor activity.
MTT method is adopted to test the in vitro inhibitory activity of the compound 1 and 2 tumor cells, and the screened tumor cell strains are A549 and MCF-7. The specific process is as follows: two compounds were prepared as 1 mg/mL stock solutions in DMSO and then diluted in media at fold-rate to a concentration gradient of 1.56-50. mu.g/mL. A549 cells were cultured in RPMI-1640 (Gibco) medium and MCF-7 cells were cultured in DMEM (Gibco) medium and placed in a cell culture chamber containing 5% CO2 at 37 ℃. Cells in the logarithmic growth phase were seeded in 96-well plates (100. mu.L/well, 0.4-0.6X 104 cells/well) and then incubated at 37 ℃ for 24 hours. The old medium was discarded, and then fresh medium containing different concentrations of compounds 1 and 2 was added and incubated at 37 ℃ for 48 hours. After completion of the incubation, 10. mu.L of 3- (4, 5-dimethylthiazol-2-yl) -2, 5-diphenyl-triazolium bromide (MTT) solution (5 mg/mL, Sigma) was added to each well, followed by incubation at 37 ℃ for 4 hours. After discarding the supernatant, 100. mu.L of DMSO solution was added to each well to dissolve the crystals sufficiently. Finally, the absorbance of each well was measured at 490 nm wavelength using a SPARK microplate reader. Doxorubicin was used as a positive control.
The test results show that the compounds 1 and 2 shown in FIG. 1 have obvious growth on two tumor cellsLong inhibitory activity, Compound 2 slightly superior to Compound 1, their IC50The values are shown in FIG. 19. Therefore, the compounds 1 and 2 shown in figure 1 can be used for preparing antitumor drugs.
Claims (10)
1. The structural formulas of the two steroid compounds are shown in figure 1.
2. A process for the preparation of a steroid compound as claimed in claim 1, characterised by the steps of:
(1) drying fruiting body of Ganoderma lucidum, pulverizing, extracting with ethanol, and concentrating the extractive solution to obtain crude extract;
(2) suspending the crude extract in water, extracting with ethyl acetate, and concentrating the ethyl acetate extract phase to obtain ethyl acetate extract;
(3) subjecting the ethyl acetate extract to D101 macroporous resin column chromatography, and eluting with 30%, 50% and 95% v/v ethanol-water in sequence to obtain 3 components A-C;
(4) performing normal-phase silica gel column chromatography on the component C, and performing gradient elution by using 20: 1-1: 3 v/v petroleum ether-ethyl acetate to obtain components C1-C9;
(5) subjecting the component C5 to RP-18 reverse phase silica gel column chromatography, and performing gradient elution by using 70-100% v/v methanol-water to obtain components C5-1 and C5-2;
(6) subjecting the component C5-1 to normal phase silica gel column chromatography, and performing gradient elution with petroleum ether-dichloromethane at a ratio of 2: 1-1: 2 v/v; wherein the main fraction is purified by YMC-Pack ODS-A high performance liquid chromatography column, isocratically eluted with 95% v/v acetonitrile-water solution with detection wavelength of 210 and 254nm, the fraction with retention time of 19.0 min is collected, and the solvent is removed to obtain compound 1;
(7) subjecting the component C6 to RP-18 reverse phase silica gel column chromatography, and performing gradient elution by using 60-100% v/v methanol-water to obtain components C6-1-C6-3;
(8) subjecting the component C6-1 to normal phase silica gel column chromatography, and performing gradient elution with dichloromethane-methanol at a ratio of 200: 1-20: 1 v/v to obtain components C6-1-C6-4-4;
(9) passing the component C6-1-2 through YMC-Pack ODS-A high performance liquid chromatography column, isocratically eluting with 90% v/v acetonitrile-water solution, detecting wavelength at 210 and 254nm, collecting the component with retention time of 27.5 min, and removing solvent to obtain compound 2.
3. The method according to claim 2, wherein the ratio of Ganoderma lucidum to ethanol in step (1) is 1:2 to 1:4 (w/v).
4. The method according to claim 2, wherein in the step (1), the Ganoderma lucidum is pulverized to a particle size of less than 3 mm in diameter.
5. The method according to claim 2, wherein in the step (1), the leaching is performed 3 to 5 times for 7 to 10 days.
6. The method of claim 2, wherein in step (1), the concentrate is 1/50-1/70 in bulk.
7. The preparation method according to claim 2, wherein in the step (2), the volume ratio of the crude extract to water is 1: 1-1: 2.
8. The preparation method according to claim 2, wherein in the step (2), the volume ratio of the ethyl acetate to the water is 0.8:1 to 1.2: 1; and the extraction times of the ethyl acetate are 3-5 times.
9. Use of a steroid compound according to claim 1 in the manufacture of an anti-tumour, anti-cancer medicament.
10. The use according to claim 9, wherein the tumors are lung and breast cancer.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115611963A (en) * | 2022-09-19 | 2023-01-17 | 沈阳药科大学 | Preparation and application of steroid compound in ailanthus leaves |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103239459A (en) * | 2012-02-02 | 2013-08-14 | 北京北大维信生物科技有限公司 | Use of sterol derivative in preparation of medicines for preventing and/or treating and/or adjunctively treating cancers |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103239459A (en) * | 2012-02-02 | 2013-08-14 | 北京北大维信生物科技有限公司 | Use of sterol derivative in preparation of medicines for preventing and/or treating and/or adjunctively treating cancers |
Non-Patent Citations (2)
| Title |
|---|
| DONG LIU ET AL.: ""Nigerasterols A and B, Antiproliferative Sterols from the Mangrove-Derived Endophytic Fungus Aspergillus niger MA-132"", 《HELVETICA CHIMICA ACTA》 * |
| JIN-HAI YU ET AL.: ""Cytotoxic ergostane-type steroids from Ganoderma lingzhi"", 《STEROIDS》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115611963A (en) * | 2022-09-19 | 2023-01-17 | 沈阳药科大学 | Preparation and application of steroid compound in ailanthus leaves |
| CN115611963B (en) * | 2022-09-19 | 2024-04-26 | 沈阳药科大学 | Preparation and application of steroid compounds in ailanthus altissima leaves |
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Application publication date: 20201215 |