CN112194704B - Steroid saponin compound and preparation method and application thereof - Google Patents
Steroid saponin compound and preparation method and application thereof Download PDFInfo
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- C07—ORGANIC CHEMISTRY
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- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
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Abstract
The invention provides a steroid saponin compound (23R,25R) -26-O-beta-D-glucopyranosyl-1 beta, 3 beta, 23 beta, 26-tetrahydroxy-furostan-5, 20(22) -diene-3-O-beta-D-glucopyranoside steroid saponin compound and a preparation method and application thereof. Researches show that the steroid saponin compound has a remarkable inhibiting effect on U251, A172 and LN229 human malignant glioma cells, and the half effective inhibiting concentration (IC50 value) is 3.58-24.12 mu mol/L; also, the growth of primary cultured human glial cells was not substantially affected at concentrations as high as 100. mu. mol/L. The compound of the invention is expected to become a new medicine for treating glioma, and provides a lead compound for developing new anti-glioma drugs.
Description
Technical Field
The invention relates to the technical field of medicines, in particular to a steroid saponin compound (23R,25R) -26-O-beta-D-glucopyranosyl-1 beta, 3 beta, 23 beta, 26-tetrahydroxy-furostan-5, 20(22) -diene-3-O-beta-D-glucopyranoside steroid saponin compound and a preparation method and application thereof.
Background
Human glioblastoma is the most common one of intracranial tumors, has high disability rate and mortality rate, and has a 5-year survival rate of only 20-30 percent, but has no obvious limit basically to normal brain tissues, so the human glioblastoma is difficult to completely remove by adopting an operation and is easy to relapse even after the removal. Moreover, malignant glioma is not sensitive to radiotherapy and chemotherapy, and is difficult to be effectively treated by radiotherapy and chemotherapy. The chemotherapy drugs for treating glioma clinically at present mainly comprise nitrosourea alkylating agents, namely nimustine (ACNU), carmustine, lomustine, procarbazine, methotrexate, cyclophosphamide, teniposide and the like, but the drugs have very limited effect on malignant glioma, usually not more than 50 percent, can not prolong the survival time obviously, and are easy to cause serious side effects such as liver injury, bone marrow suppression and the like. In addition, more than 50% of gliomas are resistant to commonly used chemotherapeutic drugs. Compared with other tumors, glioma clinically needs an effective and safe treatment medicament, so the development of a novel safe and efficient chemotherapeutic medicament is an urgent requirement for treating the disease.
The Zhugen Qin is one of the special Chinese medicines of Qinbaiqi in Qinling mountains of Shaanxi, is a plant of Tupisra of Liliaceae (Liliaceae) and Tupiss (T. chinensis), the root and stem of the Zhugen Qin are used as medicines, mainly distributed in Shaanxi, Hubei and other places, and mostly used in folk medicine from ancient times, and has the effects of clearing heat and purging fire, promoting qi circulation and relieving pain, dispelling wind and removing dampness, promoting blood circulation and removing blood stasis and the like. More than 20 plants of the same genus have been found in the world, and about 12 plants exist in China. In the research of the plants, researchers separate and obtain various natural active chemical components through a modern research method, wherein the natural active chemical components comprise flavonoids, polysaccharides, cardiac glycosides, steroid saponins and the like, and the components have various pharmacological effects of resisting tumors, resisting inflammation, inhibiting bacteria, sobering up, enhancing immune function and the like. However, the research on the pharmacological activity of the plants mainly stays at the level of total extracts or total saponins, and the research on monomer compounds is relatively less, so that the pharmacological action and action mechanism are not completely clarified.
Disclosure of Invention
Aiming at the problems in the prior art, the invention provides a steroid saponin compound (23R,25R) -26-O-beta-D-glucopyranosyl-1 beta, 3 beta, 23 beta, 26-tetrahydroxy-furostan-5, 20(22) -diene-3-O-beta-D-glucopyranoside steroid saponin compound and a preparation method and application thereof.
The invention is realized by the following technical scheme:
a steroid saponin compound has a chemical structural formula shown in formula I:
the preparation method of the steroid saponin compound comprises the following steps:
(1) extraction: taking dried rhizome of Tupistra chinensis Franch as a raw material, crushing the raw material, extracting for several times by ethanol water solution under reflux, combining extracting solutions, recovering solvent water under reduced pressure to obtain an ethanol extract, dispersing the ethanol extract in water, degreasing by petroleum ether, extracting for several times by water-saturated n-butyl alcohol, and recovering the solvent water to obtain the n-butyl alcohol extract.
(2) Separation: the n-butanol extract is sequentially eluted by 0%, 60% and 95% ethanol water solution by adopting a macroporous adsorption resin column, the extract of the 60% elution part is subjected to silica gel column chromatography, gradient elution is carried out by using chloroform-methanol-water mixed solvent, thin layer chromatography detection is carried out, fractions containing the compound of the formula I are collected, Sephadex LH-20 gel column chromatography is carried out, methanol is used as a mobile phase for elution to remove polysaccharide and other impurities, and the fractions are combined; and finally, separating and purifying by a high performance liquid chromatograph, and eluting by using a methanol-water mixed solvent as a mobile phase to obtain a pure product.
Preferably, the volume ratio of methanol to water in the methanol-water mixed solvent is 66: 34.
The steroid saponin compound is applied to the preparation of the medicament for treating glioma.
Preferably, the glioma is U251MG, a172 or LN 229.
Preferably, the half effective inhibition concentration of the steroid saponin compounds is 3.58-24.12 mu mol/L.
Compared with the prior art, the invention has the following beneficial technical effects:
the invention extracts and separates a steroid saponin compound (23R,25R) -26-O-beta-D-glucopyranosyl-1 beta, 3 beta, 23 beta, 26-tetrahydroxy-furost-5,20(22) -diene-3-O-beta-D-glucopyranoside ((23R,25R) -26-O-beta-D-glucopyranosyl-1 beta, 3 beta, 23 beta, 26-tetrahydroxy-furost-5,20(22) -diene-3-O-beta-D-glucopyranoside) from Tupistra chinensis, and researches show that, the steroid saponin compound has a remarkable inhibiting effect on U251, A172 and LN229 human malignant glioma cells, and the half effective inhibiting concentration (IC50 value) is 3.58-24.12 mu mol/L; also, the growth of primary cultured human glial cells was not substantially affected at concentrations as high as 100. mu. mol/L. The compound of the invention is expected to become a new medicine for treating glioma, and provides a lead compound for developing new anti-glioma drugs.
Detailed Description
The present invention will now be described in further detail with reference to specific examples, which are intended to be illustrative, but not limiting, of the invention.
The invention provides a research personnel for extracting and separating steroid saponin compounds from Tupistra chinensis Baker, and the chemical structure of the compounds is determined by adopting high-resolution mass spectrometry, two-dimensional nuclear magnetic resonance spectroscopy and other spectroscopic techniques and a chemical method, and is shown as the formula I:
the chemical name of the structure is (23R,25R) -26-O-beta-D-glucopyranosyl-1 beta, 3 beta, 23 beta, 26-tetrahydroxy-furostan-5, 20(22) -diene-3-O-beta-D-glucopyranoside ((23R,25R) -26-O-beta-D-glucopyranosyl-1 beta, 3 beta, 23 beta, 26-tetrahydroxy-furost-5,20(22) -diene-3-O-beta-D-glucopyranoside), the structure is a steroidal saponin compound separated from Tupistra chinensis, and the compound is hereinafter referred to as TCSS.
The preparation method of the compound TCSS with the formula I comprises the following specific steps:
(1) extraction: taking dried rhizome of Tupistra chinensis Franch as a raw material, crushing the raw material, adding 70% ethanol which is 3-5 times of the weight of the raw material according to the weight-volume ratio, and performing reflux extraction for 3 times, 3 hours each time. Mixing the extracting solutions, recovering the solvent under reduced pressure to obtain an ethanol extract, dispersing the extract in water in a weight-volume ratio of 4-8 times, degreasing with petroleum ether, extracting with water-saturated n-butanol for 3 times, and recovering the solvent to obtain the n-butanol extract.
(2) Separation: the n-butanol extract is sequentially eluted by 0%, 60% and 95% ethanol water solution by adopting a macroporous adsorption resin column, the extract of 60% elution part is subjected to silica gel column chromatography, gradient elution is carried out by using chloroform-methanol-water mixed solvent with the volume ratio of 8:2: 1-6.5: 3.5:1, thin layer chromatography detection is carried out, the fraction containing the compound of the formula I is collected, Sephadex LH-20 gel column chromatography is carried out, the polysaccharide and other impurities are removed by using methanol as mobile phase elution, and the fraction is combined. And finally, separating and purifying by a high performance liquid chromatograph, and eluting by using a methanol-water mixed solvent with a volume ratio of 66:34 as a mobile phase to obtain a pure product.
Example 1: extraction and isolation of compounds
Collecting whole grass of Tupistra chinensis under shade in the region of the back beam of Qinling cattle (Yingchi town) in Shaanxi province as a raw material, drying the raw material in the shade, slicing the raw material, weighing 7.5kg, crushing, adding 55 liters of ethanol with the concentration of 70 percent for reflux extraction, and extracting for 3 times in total, wherein each time lasts for 3 hours. The extracts were combined and the solvent recovered under reduced pressure to give 1450 g of ethanol extract. The extract was dispersed in 10L water and extracted with petroleum ether at equal volume for 4 times, 10L each time. Extracting the extracted water phase with n-butanol of the same volume for 4 times, 4 liters each time, combining n-butanol extraction liquid, and recovering the solvent under reduced pressure to obtain 430 g of n-butanol extract. Subjecting n-butanol extract to macroporous adsorption column chromatography, sequentially eluting with 0%, 60% and 95% ethanol water solution (volume fraction), concentrating under reduced pressure, transferring and volatilizing to obtain extracts of different parts, and detecting by TLC to obtain extract containing target component compound (saponin) of formula I mainly concentrated in extract (320g) of 60% eluting part. Repeatedly separating and purifying by Sephadex LH-20 gel column and C18 reverse phase column, and finally separating by semi-preparative HPLC (Dian P680) to obtain the compound of formula I. And separating and purifying by high performance liquid chromatography (Daian company) (HPLC conditions are: YMC-Pack R & D ODS-A chromatographic column, 5 μm 250 × 20mm, 66% methanol as mobile phase, flow rate of 5mL/min, 24 deg.C, 206nm ultraviolet detection) to obtain 260 mg of pure product.
Example 2:
collecting whole grass of Tupistra chinensis under shade in the region of the back beam of Qinling cattle (Yingchi town) in Shaanxi province as a raw material, drying the raw material in the shade, slicing the raw material in the shade, weighing 5kg, crushing, adding 10 liters of 70% ethanol for reflux extraction, and extracting for 3 times and 2 hours each time. The extracts were combined and the solvent was recovered under reduced pressure to give 1110 g of an ethanol extract. The extract was dispersed in 6 liters of water and extracted 3 times with 6 liters of petroleum ether each time. Extracting the extracted water phase with n-butanol for 3 times, each time for 3L, mixing n-butanol extractive solutions, and recovering solvent under reduced pressure to obtain total saponin extract 320 g. Performing macroporous adsorption column chromatography on the n-butanol extract, sequentially eluting with 0%, 60% and 95% ethanol water solution (volume fraction), concentrating under reduced pressure, transferring and volatilizing to obtain extracts of various parts, and detecting by TLC to obtain the target component (saponin) and the compound of formula I mainly concentrated in the extract (240g) of 60% elution part. Repeatedly separating and purifying by Sephadex LH-20 gel column and C18 reverse phase column, and separating by semi-preparative HPLC (Dian P680) to obtain compound monomer compound of formula I. And separating and purifying with high performance liquid chromatography (Daian company) (HPLC conditions are: YMC-Pack R & D ODS-A chromatographic column, 5 μm 250 × 20mm, 66% methanol as mobile phase, flow rate of 5mL/min, 24 deg.C, 206nm ultraviolet detection) to obtain 120 mg of pure product.
Example 3:
collecting whole grass of Tupistra chinensis under shade in the region of the back beam of Qinling cattle (Yingchi town) in Shaanxi province as a raw material, drying the raw material in the shade, slicing the raw material in the shade, weighing 1kg of the raw material, crushing the crushed raw material, adding 4 liters of ethanol with the concentration of 70 percent to perform reflux extraction, and performing extraction for 3 times each time for 3 hours. Mixing the extractive solutions, and recovering solvent under reduced pressure to obtain 160 g of ethanol extract. The extract was dispersed in 1 liter of water and extracted 3 times with 1 liter of petroleum ether each time. Extracting the extracted water phase with n-butanol for 3 times, each time for 1L, mixing n-butanol extractive solutions, and recovering solvent under reduced pressure to obtain total saponin extract 65 g. Performing macroporous adsorption column chromatography on the n-butanol extract, sequentially eluting with 0%, 60% and 95% ethanol water solution (volume fraction), concentrating under reduced pressure, transferring and volatilizing to obtain extracts of various parts, and detecting by TLC to obtain the target component (saponin) compound of formula I mainly concentrated in the extract (49g) of 60% eluting part. Repeatedly separating and purifying by Sephadex LH-20 gel column and C18 reverse phase column, and separating by semi-preparative HPLC (Dian P680) to obtain compound monomer compound of formula I. And separating and purifying by high performance liquid chromatography (Daian company) (HPLC conditions are: YMC-Pack R & D ODS-A chromatographic column, 5 μm 250 × 20mm, 66% methanol as mobile phase, flow rate of 5mL/min, 24 deg.C, 206nm ultraviolet detection) to obtain pure product 40 mg.
Structural identification of compounds
Example 1 the compound of formula I TCSS is an amorphous white powder of formula C39H62O15，
Acetic anhydride-concentrateThe identification reaction of sulfuric acid (Liebermann-Burchard) and the identification reaction of purple ring (Molish) are positive. In addition, the compound reacts with anisaldehydide reagent to show yellow color, and the Ehrlich reagent reacts to show red color, which shows that the compound is a steroid saponin compound with an F ring opened, namely the furostanol alcohol steroid saponin. From the above analysis results, it was confirmed that the structure of the compound Z-1 was (23R,25R) -26-O- β -D-glucopyranosyl-1 β,3 β,23 β, 26-tetrahydroxy-furosta-5, 20(22) -diene-3-O- β -D-glucopyranoside. The spectral data are as follows:
ESI-MS (Positive ion mode) M/z 793[ M + Na ]]+; ESI-MS (negative ion mode) M/z:769[ M-H]-; HR-ESI-MS (positive ion mode) M/z 793.3951[ M + Na ]]+ (calculated value C)39H62O15Na: 793.3986). The 1H and 13C NMR data are shown in Table 1.
TABLE 1 example 1 preparation of a compound of formula I1H-NMR(CD3OD,800MHz, δ in ppm, J in Hz) and13C-NMR(CD3OD,200MHz, delta in ppm, J in Hz) data
Research on in vitro anti-glioma effect of compound
In vitro anti-glioma assays were performed on compound TCSS of formula I of example 1 using three human glioblastoma cell lines, U251MG, a172 and LN229, respectively. To test the selectivity of TCSS for glioma and for toxicity to normal nerve cells for the compound of formula I of example 1, primary cultured human glial cells were also taken and the cytotoxicity of TCSS was determined. The test is carried out by a conventional CCK-8 method.
The specific method comprises the following steps: according to the growth rate of cells, the cells in the logarithmic growth phase are inoculated on a 96-well culture plate at 5000 cells/hole, after 24 hours of adherent growth, the original culture solution is discarded, a proper amount of stock solution of a compound to be detected is diluted into a primary screening solution of 100 mu M, 100 mu L/hole is administrated, each concentration is 4 holes, and then the cells are placed in a constant temperature incubator at 37 ℃ for culturing for 48 hours. Adding the CCK-8 reagent into a 96-well plate, reacting for 2 hours in an incubator at 10 mu L/well, then taking out the culture plate, setting the detection wavelength of an enzyme-labeling instrument to 450nm in advance, measuring and recording the absorbance of each well, and calculating the inhibition rate of a detected object on cell growth according to the following formula:
the cell inhibition rate (control OD value-administration OD value)/control OD value × 100%
The half effective inhibitory concentration IC50 value was calculated by the Logit method. The test results are shown in Table 2.
TABLE 2 EXAMPLE 1 inhibition of TCSS, a compound of formula I, on 3 glioblastoma cells and primary cultured human glial cells (IC)50Value, μmol/L)
As can be seen, the compound TCSS of the formula I in example 1 has a remarkable inhibitory effect on 3 human malignant glioma cells, and the IC50 value is close to the normal use range, which shows that the compound TCSS has a better effect on various tumor cells. Example 1 compound TCSS of formula I does not affect the growth of primary cultured human glial cells (IC50 value >100 μmol/L), and it was found in the specific experiments that the inhibition rate of human glial cells was only 7.7% (P >0.05) even at the concentration of TCSS of 100 μmol/L, but the inhibition rate of positive control nimustine hydrochloride (ACNU) at the concentration of 100 μmol/L was 31.8% (P <0.05), and it can be seen that compound TCSS of formula I of example 1 is basically non-toxic to normal glial cells, and can be used for preparing drugs for treating gliomas.
The inventor also extracts another compound (23S,25R) -26-O-beta-D-glucopyranosyl-1 beta, 3 beta, 23 alpha, 26-tetrahydroxy-furosta-5, 20(22) -diene-3-O-beta-D-glucopyranoside from Tupistra chinensis, as shown in a formula II.
The compound of formula II is an isomer of the compound TCSS of formula I, but surprisingly, the compound TCSS of formula I of the present invention has anti-glioma activity, but the compound of formula II of its isomer has no activity of inhibiting tumor cells.
Claims (6)
1. The steroid saponin compound is characterized in that the chemical structural formula is shown in the formula I:
2. the method for preparing the steroid saponin compound according to claim 1, comprising:
(1) extraction: taking dried rhizome of Tupistra chinensis Franch as a raw material, crushing the raw material, performing reflux extraction for a plurality of times by adopting an ethanol water solution, combining extracting solutions, recovering solvent water under reduced pressure to obtain an ethanol extract, dispersing the ethanol extract in water, degreasing by adopting petroleum ether, extracting by using water-saturated n-butyl alcohol for a plurality of times, and recovering the solvent water to obtain an n-butyl alcohol extract;
(2) separation: the n-butanol extract is sequentially eluted by 0%, 60% and 95% ethanol water solution by adopting a macroporous adsorption resin column, the extract of the 60% elution part is subjected to silica gel column chromatography, gradient elution is carried out by using chloroform-methanol-water mixed solvent, thin layer chromatography detection is carried out, fractions containing the compound of the formula I are collected, Sephadex LH-20 gel column chromatography is carried out, methanol is used as a mobile phase for elution to remove polysaccharide and other impurities, and the fractions are combined; and finally, separating and purifying by a high performance liquid chromatograph, and eluting by using a methanol-water mixed solvent as a mobile phase to obtain a pure product.
3. The method for preparing steroid saponin compounds according to claim 2, wherein the volume ratio of methanol to water in the methanol-water mixed solvent is 66: 34.
4. Use of steroidal saponins according to claim 1 in the preparation of medicaments for the treatment of glioma.
5. The use of claim 4, wherein the glioma is U251MG, A172 or LN 229.
6. The use according to claim 4, wherein the half effective inhibitory concentration of the steroid saponin compound is 3.58-24.12 μmol/L.
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