CN105200112B - A kind of preparation method of Armillaria luteo-virens fructification resisting liver cancer activity sterols component - Google Patents
A kind of preparation method of Armillaria luteo-virens fructification resisting liver cancer activity sterols component Download PDFInfo
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- CN105200112B CN105200112B CN201510589295.5A CN201510589295A CN105200112B CN 105200112 B CN105200112 B CN 105200112B CN 201510589295 A CN201510589295 A CN 201510589295A CN 105200112 B CN105200112 B CN 105200112B
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Abstract
The invention discloses a kind of preparation methods of Armillaria luteo-virens fructification resisting liver cancer activity phytosterin compound, invented technology is simple, the rate of recovery is high, repeated preferable, stable and controllable for quality, and influence of the invention using cell growth curve as basic index criterion component and sample to cellular physiological activities such as adherent, breedings, visual result, easily judgement；Obtained Armillaria luteo-virens fructification resisting liver cancer activity group lease making further separate and crystallization treatment and NMR carbon spectrum, hydrogen spectrum analysis, determine contain ergosterol and 5 α-ergosta-7,22-dien-3 beta -ols.
Description
Technical field
The present invention relates to pharmaceutical chemistry and biomedicine technical field more particularly to a kind of anti-livers of Armillaria luteo-virens fructification
Cancer
The preparation method and applications of reactive sterol class component.
Background technique
Liver cancer cells (hepatocellular carcinoma, HCC, hereinafter referred to as liver cancer) be a kind of grade malignancy it is high,
The dangerous tumour of prognosis, survival rate only has 7% or so within 5 years, is the global 5th most common malignant tumour, in whole world tumour
Third position is in the lethality of patient.China's onset of liver cancer number accounts for about more than half of whole world, and age of onset tends to be young
Change.Liver cancer annual death rate in China's is 20/,100,000 or so at present, occupies the 2nd of the various mortality of malignant tumors in China, and close
It is in rising trend always over 10 years.Liver cancer has become the big killer for seriously threatening the health of our people and life, dangerous
Property can not be ignored.
Studies have shown that some Chinese medicine compound prescriptions or single the effective elements of the medicine can induce apoptosis of tumor cells, anticancer therapeutic
It is related with herb induction apoptosis of tumor cells.Armillaria luteo-virens fructification is the rare wild edible medicinal for being grown on Qinghai-Tibet Platean
Bacterium.At present it is limited studies have shown that in Armillaria luteo-virens fructification contain more rich protein, amino acid, carbohydrate, alkaloid
With a small amount of organic acid, flavones, cardiac glycoside, steroidal triterpenes, glycoside, saponin(e, volatile oil, cumarin terpene, tannin, phenols chemical combination
Object etc., such compound have anti influenza, prevention and treatment neuritis, athlete's foot, promote child development, the anti-oxidant and biologies such as antitumor
Activity.
" Armillaria luteo-virens fructification standardizes component preparation method and its controls in lung cancer Chinese patent application CN 103494843A
Application in treatment " and CN 103494843A relate to Armillaria luteo-virens fructification standardization component preparation method and its in lung
Application in cancer and liver cancer, and the not yet explicitly specific chemical composition in component.In document to Armillaria luteo-virens fructification chemistry at
The research divided is same, and there is a serious shortage in the supply.
Summary of the invention
Technical problem to be solved by the invention is to provide a kind of simple processes, a kind of Armillaria luteo-virens easy to implement
The preparation method of entity resisting liver cancer activity sterols component.
Another technical problem to be solved by this invention is to provide the Armillaria luteo-virens reactive sterol class component in liver cancer
Application in treating.
To solve the above problems, a kind of Armillaria luteo-virens fructification resisting liver cancer activity sterols component of the present invention
Preparation method, comprising the following steps:
(1) Armillaria luteo-virens acetone extract is dissolved with methanol by the solid-to-liquid ratio of 1g:50mL~100mL, is filtered
To filtrate, the upper micro-porous resin post separation of the filtrate is eluted with 90%~100% methanol solution of 3~5 times of column volumes, is collected
The eluate is simultaneously dried under reduced pressure to get Armillaria luteo-virens fructification sterols component；
(2) it is mixed that 10~20 times of n-hexane-ethyl acetates of its volume are added in the Armillaria luteo-virens fructification sterols component
It closes liquid to be dissolved, 0.45 μm of organic filter membrane is crossed after dissolution, obtains the sample of the sterols component of fructification containing Armillaria luteo-virens
Solution；The sample solution of the sterols of fructification containing the Armillaria luteo-virens component is preparing color using 10 μm of silica gel as isolation medium
It separates and is dried under reduced pressure in spectrum to get Fr1, Fr2, Fr3, Fr4, Fr5 totally 5 component samples；
(3) 5 component samples are carried out in the steps below using the real-time n cell analyzer of iCelligence
Anti-liver cancer cell model discrimination:
1. confirmation iCelligence test macro correctly connects, 37 DEG C, 5%CO2Incubator is working properly；
2. culture medium is added by 150 holes μ L/ in 8 porocyte plates, it is placed at room temperature for 15 minutes and is placed on iCelligence test
Baseline is surveyed on platform；The culture medium refers to the low sugar DMEM culture medium containing 10% fetal calf serum；
3. it is molten to divide sample with DMSO to be configured to the sample that concentration is 5mg/mL each of described 5 component samples
Liquid；
4. by the human liver cancer cell HepG2 of logarithmic growth phase, after being digested according to a conventional method with pancreatin, with the rate of 950rpm
It is centrifuged 5min, cell is resuspended in the culture medium, and cell concentration is adjusted to 2.85 × 104A/mL, obtains logarithmic growth
The human liver cancer cell HepG2 suspension of phase, and by 345 holes μ L/, 10000 cells in every hole amount by the people of the logarithmic growth phase
Hepatocellular carcinoma H22 suspension is inoculated in the corresponding aperture of 8 porocyte plates, is placed at room temperature for 30min；
5. adding concentration described in 5 μ L to add for the sample solution of 5mg/mL, every hole by every hole in two batches 5 component samples
The amount of the human liver cancer cell HepG2 suspension of logarithmic growth phase described in 345 μ L is inoculated in the corresponding aperture of 8 porocyte plates, and
It is placed in the iCelligence testboard, is put into the incubator and starts to detect；Two Armillaria luteo-virens are obtained after 45h
The Activity determination figure of entity anti-liver cancer and anti-standardization component；Wherein ordinate is cell index, and abscissa is that real-time cell proliferation is dynamic
State effect；
6. standardizing the Activity determination figure of component according to two Armillaria luteo-virens fructification anti-liver cancer and anti-, work as cell Proliferation
Curve, which is presented, rises trend that is gentle or not rising, then illustrates that cell division is slowed or shut off, i.e., cell not can be carried out normally
Division, so that it is determined that No. 4 component has external inhibition human liver cancer cell adherent and proliferation activity.
(1) (2) the middle condition being concentrated under reduced pressure refers to that vacuum degree is 0.06~0.09MPa, temperature to the step with the step
It is 50~70 DEG C.
(1) middle micro-porous resin column refers to MCI type resin column to the step.
(2) middle n-hexane-ethyl acetate mixed liquor refers to n-hexane and ethyl acetate by 1mL:0.2mL~1mL to the step
Ratio mixing solution.
(2) the middle condition for preparing chromatographic isolation refers to that column size is 250 × 50mm to the step；Oneself is positive using A
Alkane, the binary-mobile phase system that B is ethyl acetate are separated: 0~45min, 88%A~88%A；Detection wavelength is 260nm；
Applied sample amount is 1.0g.
The resulting active group of preparation method of Armillaria luteo-virens fructification resisting liver cancer activity sterols component as described above
Application point in the treatment of liver cancer, it is characterised in that: the active component as effective component according to a conventional method with can pharmaceutically connect
All kinds of pharmaceutical formulations are made in any carrier received.
Compared with the prior art, the present invention has the following advantages:
1, the present invention uses two conventional methods of micro-porous resin and process-scale chromatography, separates from Armillaria luteo-virens fructification
The sterols component (referring to Fig. 1) with resisting liver cancer activity is arrived, not only simple process, and easy to implement.
2, the present invention utilizes iCELLigence system detection, can Real-time and Dynamic Detection cell is adherent and breeding, provide
The cytological effect map of high information quantity provides a large amount of, important dynamic response information；Unmarked, hurtless measure detection of electrons is not
Cell can be interfered to grow and analyze；Can the growth of high precision/accuracy quantitative measurement cell, provide dynamic higher than 2 orders of magnitude
State range；Whole experiment process automatic data collection is analyzed in real time, is substantially improved only in the result of final point analysis；It is training
It supports in hole and detects cell quality, achieved the purpose that living cells quality control (referring to Fig. 3).
3, the present invention determines component to the shadow of the cellular physiological activities such as adherent, breeding by basic index of cell growth curve
It rings, visual result, easily judgement；Resulting sterols active component can be used for researching and developing preparation anti-liver cancer and anti-therapeutic agent.
4, the present invention has expanded the raw material sources of medicines resistant to liver cancer, expands the purposes of Armillaria luteo-virens fructification, makes Huang
Green halimasch fructification becomes the active principle raw material of medicines resistant to liver cancer, significantly improves the added value of Armillaria luteo-virens fructification.
5, present invention process is simple, the rate of recovery is high, repeated preferable, stable and controllable for quality, obtained Armillaria luteo-virens
Fructification resisting liver cancer activity group lease making further separate and crystallization treatment and NMR carbon spectrum, hydrogen spectrum analysis, judgement contain ergosterol
With 5 α-ergosta-7,22-dien-3 beta -ols.
Detailed description of the invention
Specific embodiments of the present invention will be described in further detail with reference to the accompanying drawing.
Fig. 1 is the chromatographic fractionation figure in triplicate of Armillaria luteo-virens fructification sterols component of the present invention.
Fig. 2 is the structural formula of compound contained by Armillaria luteo-virens fructification resisting liver cancer activity sterols component of the present invention.
Fig. 3 is that the resisting liver cancer activity of separating obtained 5 components of Armillaria luteo-virens fructification sterols component of the present invention detects
Figure.
Specific embodiment
A kind of preparation method of the Armillaria luteo-virens fructification resisting liver cancer activity sterols component of embodiment 1, including following step
It is rapid:
(1) Armillaria luteo-virens acetone extract 50g is dissolved by the solid-to-liquid ratio of 1g:50mL with methanol, and filter is obtained by filtration
Liquid, the upper micro-porous resin post separation of the filtrate, is eluted with 100% methanol solution of 3 times of column volumes, collects the eluate and through subtracting
It press dry dry to get Armillaria luteo-virens fructification sterols component 34.6g；
Wherein:
The condition of reduced pressure refers to that vacuum degree is 0.06MPa, and temperature is 70 DEG C.
Micro-porous resin column refers to MCI type resin column.
(2) 10 times of n-hexane-ethyl acetate mixed liquors of its volume are added in the Armillaria luteo-virens fructification sterols component
It is dissolved, 0.45 μm of organic filter membrane is crossed after dissolution, obtains the sample solution of the sterols component of fructification containing Armillaria luteo-virens；
The sample solution of the sterols of fructification containing the Armillaria luteo-virens component is in the preparation chromatography using 10 μm of silica gel as isolation medium
Separate and be dried under reduced pressure to get Fr1, Fr2 ..., Fr5 totally 5 component samples (0.5g~16.4g)；
Wherein:
The condition of reduced pressure refers to that vacuum degree is 0.06MPa, and temperature is 70 DEG C.
The condition of preparation chromatographic isolation refers to that column size is 250 × 50mm；Using A for n-hexane, B is ethyl acetate
Binary-mobile phase system separated: 0~45min, 88%A~88%A；Detection wavelength is 260nm；Applied sample amount is 1.0g.
N-hexane-ethyl acetate mixed liquor refers to the solution that n-hexane and ethyl acetate are mixed in the ratio of 1mL:1mL.
(3) 5 component samples are carried out in the steps below using the real-time n cell analyzer of iCelligence
Anti-liver cancer cell model discrimination:
1. confirmation iCelligence test macro correctly connects, 37 DEG C, 5%CO2Incubator is working properly；
2. culture medium is added by 150 holes μ L/ in 8 porocyte plates, it is placed at room temperature for 15 minutes and is placed on iCelligence test
Baseline is surveyed on platform；The culture medium refers to the low sugar DMEM culture medium containing 10% fetal calf serum；
3. it is molten to divide sample with DMSO to be configured to the sample that concentration is 5mg/mL each of described 5 component samples
Liquid；
4. by the human liver cancer cell HepG2 of logarithmic growth phase, after being digested according to a conventional method with pancreatin, with the rate of 950rpm
It is centrifuged 5min, cell is resuspended in the culture medium, and cell concentration is adjusted to 2.85 × 104A/mL, obtains logarithmic growth
The human liver cancer cell HepG2 suspension of phase, and by 345 holes μ L/, 10000 cells in every hole amount by the people of the logarithmic growth phase
Hepatocellular carcinoma H22 suspension is inoculated in the corresponding aperture of 8 porocyte plates, is placed at room temperature for 30min；
5. adding concentration described in 5 μ L to add for the sample solution of 5mg/mL, every hole by every hole in two batches 5 component samples
The amount of the human liver cancer cell HepG2 suspension of logarithmic growth phase described in 345 μ L is inoculated in the corresponding aperture of 8 porocyte plates, and
It is placed in the iCelligence testboard, is put into the incubator and starts to detect；Two Armillaria luteo-virens are obtained after 45h
The Activity determination figure of entity anti-liver cancer and anti-standardization component；Wherein ordinate is cell index, and abscissa is that real-time cell proliferation is dynamic
State effect；
6. standardizing the Activity determination figure of component according to two Armillaria luteo-virens fructification anti-liver cancer and anti-, work as cell Proliferation
Curve, which is presented, rises trend that is gentle or not rising, then illustrates that cell division is slowed or shut off, i.e., cell not can be carried out normally
Division, so that it is determined that No. 4 component has external inhibition human liver cancer cell adherent and proliferation activity.
Obtained Armillaria luteo-virens fructification resisting liver cancer activity group lease making further separates and crystallization treatment and NMR carbon
Spectrum, hydrogen spectrum analysis determine to contain ergosterol and 5 α-ergosta-7,22-dien-3 beta -ols.
A kind of preparation method of the Armillaria luteo-virens fructification resisting liver cancer activity sterols component of embodiment 2, including following step
It is rapid:
(1) Armillaria luteo-virens acetone extract 100g is dissolved with methanol by the solid-to-liquid ratio of 1g:100mL, is obtained by filtration
Filtrate, the upper micro-porous resin post separation of the filtrate, is eluted with 90% methanol solution of 5 times of column volumes, collects the eluate and pass through
It is dried under reduced pressure to get Armillaria luteo-virens fructification sterols component 65.8g；
Wherein:
The condition of reduced pressure refers to that vacuum degree is 0.09MPa, and temperature is 50 DEG C.
Micro-porous resin column refers to MCI type resin column.
(2) 20 times of n-hexane-ethyl acetates mixing of its volume is added in the Armillaria luteo-virens fructification sterols component
Liquid is dissolved, and 0.45 μm of organic filter membrane is crossed after dissolution, and the sample for obtaining the sterols component of fructification containing Armillaria luteo-virens is molten
Liquid；The sample solution of the sterols of fructification containing the Armillaria luteo-virens component is using 10 μm of silica gel as the preparation chromatography of isolation medium
Upper separation and be dried under reduced pressure to get Fr1, Fr2 ..., Fr5 totally 5 component samples (1.2g~31.4g)；
Wherein:
The condition of reduced pressure refers to that vacuum degree is 0.09MPa, and temperature is 50 DEG C.
The condition of chromatographic isolation is prepared with embodiment 1.
N-hexane-ethyl acetate mixed liquor refers to the solution that n-hexane and ethyl acetate are mixed in the ratio of 1mL:0.2mL.
By 5 component samples using the real-time n cell analyzer of iCelligence by step described in embodiment 1 into
Row anti-liver cancer cell model discrimination determines that No. 4 component has external inhibition human liver cancer cell adherent and proliferation activity.
A kind of preparation method of the Armillaria luteo-virens fructification resisting liver cancer activity sterols component of embodiment 3, including following step
It is rapid:
(1) Armillaria luteo-virens acetone extract 200g is dissolved by the solid-to-liquid ratio of 1g:80mL with methanol, and filter is obtained by filtration
Liquid, the upper micro-porous resin post separation of the filtrate, is eluted with 95% methanol solution of 4 times of column volumes, collects the eluate and through subtracting
It press dry dry to get Armillaria luteo-virens fructification sterols component 122.8g；
Wherein:
The condition of reduced pressure refers to that vacuum degree is 0.08MPa, and temperature is 60 DEG C.
Micro-porous resin column refers to MCI type resin column.
(2) 3 times of n-hexane-ethyl acetates mixing of its volume is added in the Armillaria luteo-virens fructification sterols component
Liquid is dissolved, and 0.45 μm of organic filter membrane is crossed after dissolution, and the sample for obtaining the sterols component of fructification containing Armillaria luteo-virens is molten
Liquid；The sample solution of the sterols of fructification containing the Armillaria luteo-virens component is using 10 μm of silica gel as the preparation chromatography of isolation medium
Upper separation and be dried under reduced pressure to get Fr1, Fr2 ..., Fr5 totally 5 component samples (2.0g~61.4g)；
Wherein:
The condition of reduced pressure refers to that vacuum degree is 0.08MPa, and temperature is 60 DEG C.
The condition of chromatographic isolation is prepared with embodiment 1.
N-hexane-ethyl acetate mixed liquor refers to the solution that n-hexane and ethyl acetate are mixed in the ratio of 1mL:0.5mL.
By 5 component samples using the real-time n cell analyzer of iCelligence by step described in embodiment 1 into
Row anti-liver cancer cell model discrimination determines that No. 4 component has external inhibition human liver cancer cell adherent and proliferation activity.
The preparation method of Armillaria luteo-virens fructification resisting liver cancer activity sterols component is resulting in above-described embodiment 1~3
Active component is made all kinds of pharmaceutical formulations with pharmaceutically acceptable any carrier according to a conventional method as effective component and is applied to
In liver cancer treatment.
Claims (2)
1. a kind of preparation method of Armillaria luteo-virens fructification resisting liver cancer activity sterols component, which is characterized in that including following
Step:
(1) Armillaria luteo-virens acetone extract is dissolved by the solid-to-liquid ratio of 1g:50mL~100mL with methanol, and filter is obtained by filtration
Liquid, the upper micro-porous resin post separation of the filtrate, is eluted with 90%~100% methanol solution of 3~5 times of column volumes, collects this and wash
De- object is simultaneously dried under reduced pressure to get Armillaria luteo-virens fructification sterols component；
(2) 10~20 times of n-hexane-ethyl acetate mixed liquors of its volume are added in the Armillaria luteo-virens fructification sterols component
It is dissolved, 0.45 μm of organic filter membrane is crossed after dissolution, obtains the sample solution of the sterols component of fructification containing Armillaria luteo-virens；
The sample solution of the sterols of fructification containing the Armillaria luteo-virens component is in the preparation chromatography using 10 μm of silica gel as isolation medium
It separates and is dried under reduced pressure to get Fr1, Fr2, Fr3, Fr4, Fr5 totally 5 component samples, the separation ginseng of 5 component samples
Chromatographic fractionation figure as shown in Figure 1；
(3) 5 component samples are carried out in vitro in the steps below using the real-time n cell analyzer of iCelligence
The screening of anti-liver cancer and anti-cell model:
1. confirmation iCelligence test macro correctly connects, 37 DEG C, 5%CO2Incubator is working properly；
2. culture medium is added by 150 holes μ L/ in 8 porocyte plates, it is placed at room temperature for 15 minutes and is placed on iCelligence testboard
Survey baseline；The culture medium refers to the low sugar DMEM culture medium containing 10% fetal calf serum；
3. dividing sample to be configured to the sample solution that concentration is 5mg/mL with DMSO each of described 5 component samples；
4. the human liver cancer cell HepG2 of logarithmic growth phase after being digested according to a conventional method with pancreatin, is centrifuged with the rate of 950rpm
Cell is resuspended in the culture medium, and cell concentration is adjusted to 2.85 × 10 by 5min4A/mL, obtains logarithmic growth phase
Human liver cancer cell HepG2 suspension, and by 345 holes μ L/, 10000 cells in every hole amount by the human liver cancer of the logarithmic growth phase
Cell HepG2 suspension is inoculated in the corresponding aperture of 8 porocyte plates, is placed at room temperature for 30min；
5. adding concentration described in 5 μ L to add 345 μ for the sample solution of 5mg/mL, every hole by every hole in two batches 5 component samples
The amount of the human liver cancer cell HepG2 suspension of logarithmic growth phase described in L is inoculated in the corresponding aperture of 8 porocyte plates, is placed in
The iCelligence testboard, is put into the incubator and starts to detect；Two Armillaria luteo-virens fructifications are obtained after 45h
The Activity determination figure of anti-liver cancer and anti-standardization component；Wherein ordinate is cell index, and abscissa is real-time cell proliferation dynamics effect
It answers；
6. the Activity determination figure of component is standardized according to two Armillaria luteo-virens fructification anti-liver cancer and anti-, when cell Proliferation curve
It presenting and rises trend that is gentle or not rising, then illustrate that cell division is slowed or shut off, i.e., cell not can be carried out normal division,
So that it is determined that No. 4 component has external inhibition human liver cancer cell adherent and proliferation activity；
Wherein, (1) (2) the middle condition being concentrated under reduced pressure refers to that vacuum degree is 0.06~0.09MPa, temperature to the step with the step
It is 50~70 DEG C；(1) middle micro-porous resin column refers to MCI type resin column to the step；The step (2) in n-hexane-ethyl acetate
Mixed liquor refers to the solution that n-hexane and ethyl acetate are mixed in the ratio of 1mL:0.2mL~1mL；The step (2) in prepare color
It composes isolated condition and refers to that column size is 250 × 50mm；Use A for binary mobile phase body that n-hexane, B are ethyl acetate
System is separated: 0~45min, 88%A~88%A；Detection wavelength is 260nm；Applied sample amount is 1.0g.
2. the resulting active component of Armillaria luteo-virens fructification resisting liver cancer activity sterols component preparation method as described in claim 1
Application in the treatment of liver cancer, it is characterised in that: the active component as effective component according to a conventional method with it is pharmaceutically acceptable
Any carrier all kinds of pharmaceutical formulations are made.
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|---|---|---|---|---|
| CN103494844A (en) * | 2013-10-10 | 2014-01-08 | 中国科学院西北高原生物研究所 | Yellow mushroom standardized component manufacturing method and application of components to treatment of liver cancer |
| CN104892708A (en) * | 2015-05-27 | 2015-09-09 | 中国科学院西北高原生物研究所 | Method for scale preparation of adenosine chemical reference substance from armillaria luteo-virens fruiting body |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103494844A (en) * | 2013-10-10 | 2014-01-08 | 中国科学院西北高原生物研究所 | Yellow mushroom standardized component manufacturing method and application of components to treatment of liver cancer |
| CN104892708A (en) * | 2015-05-27 | 2015-09-09 | 中国科学院西北高原生物研究所 | Method for scale preparation of adenosine chemical reference substance from armillaria luteo-virens fruiting body |
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