CN105481809B - A kind of isolation and purification method of tanshin polyphenolic acid B and the preparation method of B magnesium tanphenolate - Google Patents
A kind of isolation and purification method of tanshin polyphenolic acid B and the preparation method of B magnesium tanphenolate Download PDFInfo
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Abstract
The present invention relates to the preparation method of a kind of isolation and purification method of tanshin polyphenolic acid B and B magnesium tanphenolate, the isolation and purification method of the tanshin polyphenolic acid B is included using the red sage root or Wite red-rooted salvia root medicinal material as raw material, through solvent extraction extraction, magnesium salts complexing seperation purifying, the purifying of MCI posts, crystallization and re-crystallization step.The present invention uses B magnesium tanphenolate complexometry, can save the chromatography process of macroporous absorbent resin or polyamide column chromatography, purification process is simpler and time saving, and cost is lower.The preparation method of B magnesium tanphenolate is simple, and cost is low, and high income, and purity is high, and purity is up to 98%, more suitable for big production.
Description
Technical field
The present invention relates to a kind of method that tanshin polyphenolic acid B is isolated and purified from the extraction medicinal extract of the red sage root or Wite red-rooted salvia root medicinal material with
And its preparation method of magnesium salts.
Background technology
Salviamiltiorrhizabung has the effect of promoting blood circulation, cool blood to disappear carbuncle, relieving restlessness that clears away heart-fire.Modern pharmacological research shows, red sage root energy
Coronary artery dilator, increase CBF, resist myocardial ischemia, improve microcirculation, reduce myocardial oxygen consumption, improve heart function, drop blood
Many effects such as pressure, reducing blood lipid, anticoagulation, antithrombotic, anti-oxidant, liver protection.
Tanshin polyphenolic acid B is one of red sage root primary water-soluble composition.Pharmacological research shows that tanshin polyphenolic acid B is removing free radical, protection
Cardiac-cerebral ischemia reperfusion injury and protection kidney etc. have stronger pharmacological action.
Existing tanshin polyphenolic acid B isolation and purification method mainly passes through macroporous absorbent resin separation or high speed adverse current chromatogram point
From.The major defect of macroporous absorbent resin separation is that time-consuming for elution, and workload is big, and production cost is high.Chinese patent document
CN1528756A (application numbers：03151476.6) disclose it is a kind of from the red sage root extract tanshin polyphenolic acid B process, by it is several from
The method that tanshin polyphenolic acid B is extracted in the red sage root carries out organic assembling, have developed a set of new technology for being adapted to isolate and purify tanshin polyphenolic acid B.
First extracted with water, then with flocculate with chitosan, then carry out alcohol precipitation, then extracted respectively with petroleum ether and ethyl acetate,
The tanshin polyphenolic acid B of higher degree is finally obtained using silica gel column chromatography.The above method uses silica gel column chromatography separating purification danshinolic acid
B, obtained purity are 50%-96% tanshin polyphenolic acid B；But process is complicated, extremely adsorb larger, operating process is cumbersome, it is difficult to expands
It is big to arrive production.Xiao Wang etc. are described in Journal of Separation Science 2007,30,3214-3217 and adopted
Tanshin polyphenolic acid B can be purified to by the technique that tanshin polyphenolic acid B is isolated and purified with high speed adverse current chromatogram, display pH gradient adverse current chromatogram
94.1%, and it is raw to may be applied to high-volume；But the use of high-speed counter-current chromatograph has certain limitation.
The content of the invention
For deficiency of the prior art, the invention provides one kind, quick separating is pure from the red sage root or Wite red-rooted salvia root medicinal material
Change the method for tanshin polyphenolic acid B and the preparation method of B magnesium tanphenolate, this method simple process, efficiency high, product purity are reachable
98%.
Technical scheme is as follows：
A kind of isolation and purification method of tanshin polyphenolic acid B, including using the red sage root or Wite red-rooted salvia root medicinal material as raw material, extract through solvent extraction
Take, magnesium salts complexing seperation purifying, MCI posts purifying, crystallization and re-crystallization step, obtain tanshin polyphenolic acid B；
The solvent extraction extraction step is：The red sage root or Wite red-rooted salvia root medicinal material powder are surpassed at room temperature with 70-80wt% ethanol
Sound extraction, filtering, concentrate is concentrated to give by filtrate decompression, and concentrate adds aqueous suspension, is removed with dichloromethane or ethyl acetate extraction
Decontamination, dichloromethane or ethyl acetate layer are discarded, water layer adjusts pH=1~2 with acid solution, then is extracted with ethyl acetate, second
Acetoacetic ester extract is concentrated under reduced pressure, and obtains tanshin polyphenolic acid B crude extract.
, according to the invention it is preferred to, in solvent extraction extraction step：The quality and 70- of the red sage root or Wite red-rooted salvia root medicinal material powder
The volume ratio of 80wt% ethanol is 1：(8-12)g/mL；Acetic acid ethyl acetate extract is concentrated under reduced pressure into medicinal extract shape, no ethanol flavor.
, according to the invention it is preferred to, magnesium salts complexing seperation purification step is：By MgCl2Distilled water is dissolved in, is configured to dense
Spend the MgCl for 0.01wt%~1wt%2The aqueous solution；By MgCl2The aqueous solution is added to the red phenol obtained by solvent extraction extraction step
In sour B crude extracts, stir at room temperature, the NaHCO that concentration is 0.1wt%~1wt% is added dropwise3Solution, after being added dropwise, continue to stir
Mix 1~2 minute；Add isometric dichloromethane or ethyl acetate extracts 2 times, the aqueous solution after extraction, with 1N~2.5N's
Hydrochloric acid adjusts pH=1~2, then is extracted 3 times with ethyl acetate, combined ethyl acetate extract, is concentrated under reduced pressure；
The concentrate is repeated into aforesaid operations, repurity 1 time, obtains tanshin polyphenolic acid B sample after purification.
, according to the invention it is preferred to, in magnesium salts complexing seperation purification step：Described MgCl2Contained by solution
MgCl2Molal quantity is the half of tanshin polyphenolic acid B molal quantity in tanshin polyphenolic acid B crude extract；
Preferably, described NaHCO3Contained NaHCO in solution3Molal quantity be equal to tanshin polyphenolic acid B crude extract in red phenol
Sour B molal quantitys, NaHCO used3With MgCl2Mole ratio be 2:1.
, according to the invention it is preferred to, MCI column purification steps are：By the tanshin polyphenolic acid B sample of magnesium salts complexing seperation after purification
Product, cross MCI pillars, the 10wt%-20wt% methanol solution removal of impurity, 30wt%-60wt% methanol solutions elution tanshin polyphenolic acid B sample
Product, concentrate tanshin polyphenolic acid B sample eluent；
Tanshin polyphenolic acid B sample eluent after concentration is repeated into above-mentioned MCI column purification steps, the pellet after must being further purified
Phenolic acid B sample.
, according to the invention it is preferred to, in MCI column purification steps：It is described water-soluble except the preferred 20wt% methanol of eluent is used mixedly
Liquid；The preferred 30wt% methanol solutions of solution used in the elution tanshin polyphenolic acid B sample.
, according to the invention it is preferred to, crystallization is with re-crystallization step：Tanshin polyphenolic acid B sample obtained by MCI column purification steps is molten
Solution is in dichloromethane:Methanol volume ratio=1:9~9:1, mixed solution in crystallized and recrystallized, obtain tanshin polyphenolic acid B.
, according to the invention it is preferred to, in crystallization and re-crystallization step, described dichloromethane:The volume ratio of methanol is preferred
(2~3):(8~7).
According to the present invention, a kind of preparation method of salvianolic acid B magnesium salt complex, step is as follows：
(1) preparation of magnesium hydroxide and magnesium bicarbonate：
Take MgCl2Distilled water is dissolved in, is configured to the MgCl that concentration is 1wt%~5wt%2The aqueous solution, 1wt% is then added dropwise
~5wt% NaOH the aqueous solution, untill white precipitate is not regenerated, filtering precipitation, neutrality is precipitated to distill water washing；Take
Mg(OH)2It is added to the water, is passed through CO260~90min is to solution clarification, and 10~20min of ultrasound removes unnecessary CO in solution2, it is molten
Liquid is filtered to remove insoluble granule, produces magnesium bicarbonate solution；Magnesium bicarbonate solution must matching while using.
(2) preparation of salvianolic acid B magnesium salt complex：
The tanshin polyphenolic acid B sample of above-mentioned preparation is added in magnesium bicarbonate solution, stirring makes its dissolving；With isometric dichloromethane
Alkane or ethyl acetate extract 2 times, and except oil-soluble impurities, the water layer after extraction is concentrated under reduced pressure under the conditions of 40 DEG C, remove in water layer
The dichloromethane or ethyl acetate of residual, aqueous solution freeze-drying, produce salvianolic acid B magnesium salt complex.
According to the preparation method of salvianolic acid B magnesium salt complex of the present invention, it is preferred that contained bicarbonate in magnesium bicarbonate solution
The molal quantity of magnesium and the mole ratio of tanshin polyphenolic acid B are 2:1.Magnesium bicarbonate solution used should be freshly prepared, matching while using.
According to the present invention, a kind of preparation method of salvianolic acid B magnesium salt complex, step is as follows：
Take MgCl2Distilled water is dissolved in, is configured to the MgCl that concentration is 0.01wt%~1wt%2The aqueous solution；By above-mentioned preparation
Tanshin polyphenolic acid B be added to MgCl2In the aqueous solution, it is stirred at room temperature, NaHCO is added dropwise3The aqueous solution；After being added dropwise, filter, freezing is dry
It is dry, produce salvianolic acid B magnesium salt complex.
According to the preparation method of salvianolic acid B magnesium salt complex of the present invention, it is preferred that described MgCl2It is contained in solution
MgCl2Molal quantity is 1 with tanshin polyphenolic acid B mole ratio:2.Wherein, described NaHCO3Contained NaHCO in solution3Rub
That number is 1 with tanshin polyphenolic acid B mole ratio:1.
Beneficial effects of the present invention：
The present invention uses B magnesium tanphenolate complexometry, can save the chromatography of macroporous absorbent resin or polyamide column chromatography
Process, purification process is simpler and time saving, and cost is lower.The preparation method of B magnesium tanphenolate is simple, and cost is low, and yield
Height, purity is high, and purity is up to 98%, more suitable for big production.
Brief description of the drawings
Fig. 1 is the HPLC figures for the tanshin polyphenolic acid B crude extract that the step of the embodiment of the present invention 1 (1) obtains.
Fig. 2 is the HPLC figures for the tanshin polyphenolic acid B sample that the step of the embodiment of the present invention 1 (2) magnesium salts complexometry obtains after purification.
Fig. 3 be the step of the embodiment of the present invention 1 (3) MCI after purification tanshin polyphenolic acid B sample HPLC figure.
Fig. 4 is the HPLC figures of the tanshin polyphenolic acid B obtained after the step of the embodiment of the present invention 1 (4) recrystallizes.
Fig. 5 is the HPLC figures for the B magnesium tanphenolate that the embodiment of the present invention 2 obtains.
Fig. 6 is the B magnesium tanphenolate that the embodiment of the present invention 3 obtains1H-NMR collection of illustrative plates.
Fig. 7 is the B magnesium tanphenolate that the embodiment of the present invention 3 obtains13C-NMR collection of illustrative plates.
Embodiment
Below by specific embodiment and with reference to accompanying drawing, the invention will be further described, but not limited to this.
Embodiment 1：High-purity danshinolic acid A preparation
(1) extraction of tanshin polyphenolic acid B：Red rooted salvia powder about 500g is taken, adds 75wt% ethanol, the quality of red rooted salvia powder
Volume ratio with ethanol is 1：12g/mL；Ultrasonic extraction 2 times, 30 minutes every time, filtering, merging filtrate, it is concentrated under reduced pressure, concentrate
Add suitable quantity of water, isometric dichloromethane abstraction impurity removal, water layer adjusts pH=2 with 2.5N hydrochloric acid, then is extracted with isometric ethyl acetate
Take 2 times, acetic acid ethyl acetate extract is concentrated under reduced pressure under the conditions of 45 DEG C, obtains tanshin polyphenolic acid B crude extract.
(2) magnesium salts complexometry purifies：By NaHCO3With MgCl2Mol ratio is 2：1 solution is added to tanshin polyphenolic acid B coarse extraction
In, making its dissolving, isometric ethyl acetate extracts 2 removal of impurities, discards ethyl acetate layer, and water layer adjusts pH=2 with acid solution,
Extracted 3 times with isometric ethyl acetate again, combined ethyl acetate extract, be concentrated under reduced pressure, obtain concentrate；
Concentrate is repeated into aforesaid operations, obtains the tanshin polyphenolic acid B sample of purifying.
(3) MCI is purified：The tanshin polyphenolic acid B sample of purifying in (2) is subjected to MCI post separations, first washed with 20wt% methanol solutions
Remove it is miscellaneous, then 30wt% methanol solutions elution tanshin polyphenolic acid B.
The tanshin polyphenolic acid B eluent eluted, which repeats, carries out a MCI post separation, obtains purity up to 91% danshinolic acid
B samples.
(4) recrystallize：Tanshin polyphenolic acid B sample in step (3) is dissolved in methanol:Dichloromethane=3:The heat of 8 (volume ratios)
Dissolved in solution, place crystallization.Crystallization is filtered out, then carries out secondary crystallization, obtains content of danshinolic acid B up to 98%.
Embodiment 2：It is prepared by B magnesium tanphenolate
Take MgCl2Distilled water is dissolved in, is configured to the MgCl that concentration is 1wt%2The aqueous solution, 1wt% NaOH water is then added dropwise
Solution, untill white precipitate is not regenerated, filtering precipitation, neutrality is precipitated to distill water washing；Take Mg (OH)2Add water
In, it is passed through CO260~90min is to solution clarification, and ultrasonic 10min removes unnecessary CO in solution2, solution is filtered to remove insoluble
Particle, produce magnesium bicarbonate solution；Magnesium bicarbonate solution must matching while using.
Made from embodiment 1 98% tanshin polyphenolic acid B sample 20mg is added in freshly prepd magnesium bicarbonate solution, shaken
Make its dissolving.Extracted with isometric ethyl acetate, combining extraction liquid, be concentrated under reduced pressure and be evaporated, produce high-purity danshinolic acid B magnesium salts.
1H-NMR(600MHz,D2O)δ:6.74 (dd, J=29.3,13.8Hz, 3H), 6.67 (t, J=9.4Hz, 1H), 6.62 (dd, J
=18.9,9.3Hz, 2H), 6.54 (t, J=8.7Hz, 2H), 6.49 (d, J=8.1Hz, 1H), 6.21 (dd, J=31.4,
8.0Hz, 1H), 6.07 (s, 1H), 5.89 (d, J=8.1Hz, 1H), 5.63 (t, J=12.6Hz, 1H), 5.60-5.52 (m,
1H), 4.78 (dd, J=9.6,3.3Hz, 1H), 4.73-4.67 (m, 1H), 3.91 (d, J=4.5Hz, 1H), 2.89 (dt, J=
13.5,6.9Hz, 1H), 2.83-2.66 (m, 2H), 2.38 (dd, J=14.1,11.6Hz, 1H) .13C-NMR (151MHz, D2O)
δ:177.4,176.5,172.5,168.3,147.8,146.1,144.0,143.0,142.7,142.1,141.7,130.2,
129.3,124.1,122.7,121.7,121.3,120.1,117.93,117.4,116.7,116.4,116.2,116.1,
115.8,113.9,112.9,86.1,77.5,76.3,56.6,36.7,36.1.
Embodiment 3：It is prepared by B magnesium tanphenolate
Take MgCl2Distilled water is dissolved in, is configured to the MgCl that concentration is 0.05wt%2The aqueous solution；It is prepared by embodiment 1
98% tanshin polyphenolic acid B sample 20mg is added to MgCl2In the aqueous solution, it is stirred at room temperature, NaHCO is added dropwise3The aqueous solution；After being added dropwise, take out
Filter, freeze-drying, produces salvianolic acid B magnesium salt complex.
Described MgCl2Contained MgCl in solution2Molal quantity is 1 with tanshin polyphenolic acid B mole ratio:2.Wherein, it is described
NaHCO3Contained NaHCO in solution3Molal quantity and tanshin polyphenolic acid B mole ratio be 1:1.
Claims (6)
1. a kind of isolation and purification method of tanshin polyphenolic acid B, including using the red sage root or Wite red-rooted salvia root medicinal material as raw material, extract through solvent extraction
Take, magnesium salts complexing seperation purifying, MCI posts purifying, crystallization and re-crystallization step, obtain tanshin polyphenolic acid B；
The solvent extraction extraction step is：By the red sage root or Wite red-rooted salvia root medicinal material powder, with 70-80wt% ethanol, ultrasound carries at room temperature
Take, filter, filtrate decompression is concentrated to give concentrate, concentrate adds aqueous suspension, and impurity elimination is removed with dichloromethane or ethyl acetate extraction
Matter, dichloromethane or ethyl acetate layer are discarded, water layer adjusts pH=1 ~ 2 with acid solution, then is extracted with ethyl acetate, ethyl acetate
Extract is concentrated under reduced pressure, and obtains tanshin polyphenolic acid B crude extract；
Magnesium salts complexing seperation purification step is：By MgCl2Distilled water is dissolved in, is configured to the MgCl that concentration is 0.01wt% ~ 1wt%2
The aqueous solution；By MgCl2The aqueous solution is added in the tanshin polyphenolic acid B crude extract obtained by solvent extraction extraction step, is stirred at room temperature, drop
Add NaHCO of the concentration for the wt % of 0.1 wt % ~ 13Solution, after being added dropwise, continue stirring 1 ~ 2 minute；Add isometric two
Chloromethanes or ethyl acetate extract 2 times, the aqueous solution after extraction, adjust pH=1 ~ 2 with 1N ~ 2.5N hydrochloric acid, then extract with ethyl acetate
Take 3 times, combined ethyl acetate extract, be concentrated under reduced pressure；
The concentrate is repeated into aforesaid operations, repurity 1 time, obtains tanshin polyphenolic acid B sample after purification；
MCI column purification steps are：By the tanshin polyphenolic acid B sample of magnesium salts complexing seperation after purification, MCI pillars, 10 wt %-20 are crossed
The wt % methanol solution removal of impurity, 30 wt %-60 wt % methanol solutions elution tanshin polyphenolic acid B sample, concentrates tanshin polyphenolic acid B sample elution
Liquid；
Tanshin polyphenolic acid B sample eluent after concentration is repeated into above-mentioned MCI column purification steps, the danshinolic acid after must being further purified
B samples；
Crystallize with re-crystallization step and be：Tanshin polyphenolic acid B sample obtained by MCI column purification steps is dissolved in dichloromethane:Methanol volume
Than=1:9~9:Crystallized and recrystallized in 1 mixed solution, obtain tanshin polyphenolic acid B.
2. the isolation and purification method of tanshin polyphenolic acid B according to claim 1, it is characterised in that in solvent extraction extraction step：
The quality of the red sage root or Wite red-rooted salvia root medicinal material powder and the volume ratio of 70-80wt% ethanol are 1：（8-12）g/mL.
3. the isolation and purification method of tanshin polyphenolic acid B according to claim 1, it is characterised in that magnesium salts complexing seperation purifies
In step：Described MgCl2Contained MgCl in solution2Molal quantity is two of tanshin polyphenolic acid B molal quantity in tanshin polyphenolic acid B crude extract
/ mono-；
Described NaHCO3Contained NaHCO in solution3Molal quantity be equal to tanshin polyphenolic acid B crude extract in tanshin polyphenolic acid B molal quantity,
NaHCO used3With MgCl2Mole ratio be 2:1.
4. the isolation and purification method of tanshin polyphenolic acid B according to claim 1, it is characterised in that in MCI column purification steps：Institute
It is 20wt% methanol aqueous solutions to state except eluent is used mixedly；Solution used in the elution tanshin polyphenolic acid B sample is 30wt% methanol solutions.
5. the isolation and purification method of tanshin polyphenolic acid B according to claim 1, it is characterised in that in crystallization and re-crystallization step,
Described dichloromethane:The volume ratio of methanol is (2 ~ 3): (8~7).
6. a kind of preparation method of salvianolic acid B magnesium salt complex, step are as follows：
Tanshin polyphenolic acid B is prepared using the method described in claim any one of 1-5, takes MgCl2Distilled water is dissolved in, being configured to concentration is
0.01wt% ~ 1wt% MgCl2The aqueous solution；The tanshin polyphenolic acid B of acquisition is added to MgCl2In the aqueous solution, it is stirred at room temperature, is added dropwise
NaHCO3The aqueous solution；After being added dropwise, filter, freeze-drying, produce salvianolic acid B magnesium salt complex.
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| CN117756890B (en) * | 2024-01-03 | 2024-06-14 | 河北雄安重生生物科技有限公司 | Preparation for repairing coliform by umbilical cord mesenchymal stem cells, preparation method thereof and application of preparation in weight losing |
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| CN102432467B (en) * | 2011-09-30 | 2014-01-15 | 吴谢军 | Salvianolic acid A magnesium salt, preparation method and use of the salvianolic acid A magnesium salt, and salvianolic acid A magnesium salt-containing freeze-dried powder injection composition |
| CN104130226B (en) * | 2014-04-01 | 2018-07-17 | 王平 | A kind of preparation method of high-content salvianolic acid B from salvia miltiorrhiza |
| CN104974119B (en) * | 2014-04-01 | 2018-10-19 | 中国科学院上海药物研究所 | A kind of high-purity danshinolic acid B magnesium and preparation method thereof |
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