CN105801656B - The method that Rg1, Re and Rb1 are purified from arasaponin - Google Patents
The method that Rg1, Re and Rb1 are purified from arasaponin Download PDFInfo
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- CN105801656B CN105801656B CN201410839697.1A CN201410839697A CN105801656B CN 105801656 B CN105801656 B CN 105801656B CN 201410839697 A CN201410839697 A CN 201410839697A CN 105801656 B CN105801656 B CN 105801656B
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- ethyl alcohol
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Abstract
The present invention relates to a kind of method that Rg1, Re and Rb1 are purified from arasaponin, this method is mainly the use in Rg1, Re and Rb1 purification by monodisperse polymer silica gel, and Rg1, Re and Rb1, high separation purifies from arasaponin.
Description
Technical field
The present invention relates to field of medicine invention, and in particular to one kind from arasaponin purify ginsenoside Rg1, Re with
The method of Rb1.
Background technology
Arasaponin derives from pseudo-ginseng, and main component includes notoginsenoside R, ginsenoside Rg1, ginsenoside
Re, ginsenoside Rb1 and ginsenoside Rd.It is usually used in promoting blood circulation, promotes blood circulation active, to hyperlipidemia, hypercoagulable blood, to high blood
The pharmacological action of pressure, at the same have the effects that resist myocardial ischemia, antiatherosclerosis, antithrombotic, anti-cardiac-cerebral ischemia, clinic is main
It to be prepared into full ingredient based on preparation, have no single component or wherein combination preparation.
There are prevention and treatment to cardiovascular and cerebrovascular disease.Patent application CN101116669, discloses ginsenoside
Rg3, ginseng saponin Rh 2 and several compositions of ginsenoside the III auxiliary that caused leucocyte reduces after chemicotherapy is prevented are used
Medicine.
Patent application CN 1305479C disclose the low polarity ginsenoside such as ginsenoside Rg 5, Rk1, Rg3, Rh2, Rg5
Composition and its feature with anticancer activity.
Ginsenoside Rg1 has substantially the biosynthesis effect and the effect of the biosynthesis to DNA of protein or lipid
Same tendency；The contraction in guinea pig in vitro uterus caused by phatidylcholine can be reduced；There are reducing heart rate and amphicheirality's blood pressure to make to rat
With (falling after rising)；There are diastole animal blood vessels and antifatigue effect.
Ginsenoside Re：Inhibit nervous centralis, promote DNA, RNA synthesis.The effect of plasma corticosterone is raised, expands blood
Pipe.The contraction in guinea pig in vitro uterus caused by acetylcholine can be reduced.There are reducing heart rate and Bipolar blood pressure to rat (after first rising
Drop) effect.Behavior and electroencephalogram to cat show medium inhibition.There is antifatigue effect.
Ginsenoside Rb1 is soluble easily in water, methanol, ethyl alcohol, insoluble in ether, benzene.Central nervous system, cardiovascular system
System, digestive system, immune system, internal system, urogenital system have extensive effect, so as to improve human body power, intelligence
The mobility of power, enhancing body is to the nonspecific resistance of destructive stimulus.
Arasaponin purification process is aided with the common removal of impurities means such as aluminium oxide, activated carbon based on chromatographic purifying technique,
Primary product includes each saponins and sapogenin, and purity is about 85%, has no for the wherein extraction of each component, purification process.
Current not disclosed notoginsenoside R, ginsenoside Rb1 are purified to more than 95% extraction process.
Silica gel and polymer for the filler of matrix be in the essential two kinds of performances of chromatographic isolation and analysis field each other
The chromatographic media of supplement.Silica matrix mechanical strength is big, column effect is high, good resolution, be widely used to organic compound and in
Property molecule analysis and extensive prepare in production；And polymer substrate filler then have good chemical stability and without with than
The resistance to acid and alkali of plan, therefore long lifespan, can on-line cleaning the large scale purification of biomolecule is suitble to separate.Research has shown that, due to
In the difference of material in silica gel and polymer chromatography filler, they have extremely strong mutual in terms of to target molecule separation selectivity
Benefit property if some with polymer filler are difficult separated substance, can but obtain good separation on silica filler；On the contrary, one
It is difficult a bit separated substance on silica filler, and can be efficiently separated with polymer filler.
Some parameter that monodisperse refers to substance has homogeneous property.Such as monodisperse system typically refers to dispersed phase kind
The dispersion of single and Unusually narrow particle size distribution (i.e. the grain size overwhelming majority is equal), particle diameter distribution are in normal distribution, and monodisperse is small
Ball refers to the highly uniform bead of shape size.
For existing ginsenoside Rg1, ginsenoside Re and ginsenoside Rb1's purity is not high the problem of, inventor pass through
Substantial amounts of research, finally proposes the present invention.
The content of the invention
The object of the present invention is to provide the methods that ginsenoside Rg1, Re and Rb1 are purified from arasaponin.
Ginsenoside Rg1 of the present invention, Re and Rb1 preparation method of composition, which is characterized in that comprise the following steps：
1) after taking arasaponin that ethyl alcohol is added to dissolve, neopelex is added in, after dissolving, is loaded into nonpolar big
On macroporous adsorbent resin, with ethanol elution, gained eluent is collected, is concentrated and dried；
2) take dry product obtained by step 1) that ethyl alcohol is added to dissolve, be loaded into the chromatographic column using monodisperse polymer silica gel as filler
On, gradient elution, eluent UV detector on-line checking ginsenoside Rg1, Re are made with 80%-50% ethyl alcohol at a constant temperature
With Rb1 contents；
3) Fractional Collections eluent, using ultraviolet absorptivity as foundation, discard no ginsenoside Rg1, Re and Rb1 part and
Impurity peak area is higher than 5% part, remaining merging, gained collection liquid is concentrated and dried to get ginsenoside Rg1, Re and Rb1.
Preferably, step 2) the monodisperse polymer silica gel is the monodisperse polymer silica gel of amino sealing.
Preferably, the monodisperse polymer silicagel column of step 2) the amino sealing, chromatographic column blade diameter length ratio are 1:5-50.
Preferably, the step 1) nonpolar macroporous adsorption resin is the nonpolar macroporous suction that ethyl styrene is skeleton
Attached resin.
Preferably, the step 1) nonpolarity macroporous adsorptive resins chromatographic column, chromatographic column blade diameter length ratio are 1:5-20.
Preferably, step 1) the neopelex addition is the 0.5-3% of ethyl alcohol weight.
Preferably, the step 2) dry product adds ethyl alcohol to dissolve, concentration of alcohol 50-70%.
Preferably, ethyl alcohol constant temperature elutes in the step 2), and temperature is 10-60 DEG C.
Preferably, UV detector on-line checking in the step 2), UV absorption wavelength are 200-210nm.
Preferably, arasaponin in the step 1), refer to carry using water from Radix Notoginseng or alcohol extracting obtained by, wherein containing
Notoginsenoside R, ginsenoside Rg1, ginsenoside Re, ginsenoside Rb and ginsenoside Rd.
Raw material sources：
Arasaponin：PANAX NOTOGINSENOSIDES, molecular formula C47H80O17, from the activity of Radix Notoginseng extraction
Effective ingredient.【Preparation】XUESAITONG ZHUSHEYE, XUESHUANTONG ZHUSHEYE, Radix Notoginseng total glucosides tablet, notoginseng total saponin capsule.【Character】This product is
Faint yellow amorphous powder, bitter, micro-sweet.Arasaponin is to be extracted according to extracting and developing technology from high-quality Radix Notoginseng effectively
Medicinal ingredient include more than 20 kinds of saponin(e active material, 17 kinds of trace elements, albumen, abundant vitamin, polysaccharide etc..【Function
It cures mainly】Promoting blood circulation is promoted blood circulation active, is played an important role of to inhibit platelet aggregation and is increased heart and brain blood flow.
Silica gel is a kind of high activity sorbing material, belongs to amorphous substance, and main component is silica, chemical molecular formula
For mSiO2·nH2O.Itself there is no toxicity, chemical property is stablized, do not burn.Not soluble in water and any solvent, except highly basic, hydrogen
It does not react outside fluoric acid with any substance.It is main to be used as drier, moisture-proof pearl, eliminating smell agent and various adsorbents and purification
Kerosene, absorption aromatic hydrocarbons etc., produce in the essential industries such as melamine, phthalic anhydride, maleic anhydride, butadiene rubber, acrylonitrile product
In be used as catalyst and catalyst carrier.
The polarity of polar binding phase aminopropyl Aminopropyl (- Si (CH2) 3NH2) is bonded in high-purity silica gel matrix
Adsorbent, while there is two kinds of mechanisms of action of hydrogen bond and anion exchange, end group sealing.Due to the work of propyl being connected with amino
With so that amino shows low pole, therefore can be used to separate nonpolar point of compound from polarity sample, but it is highly polar also
It is the key property of amino.
The work that the present invention is purified by the monodisperse polymer silica gel of nonpolar macroporous adsorption resin combination amino sealing
Process, the composition high separation of the monomer component ginsenoside Rg1 that can be will be present in pseudo-ginseng, Re and Rb1 purify
After obtain, the effect of said composition tool is alleviated with the treatment symptoms such as angina pectoris and arrythmias, have to the treatment of angiocardiopathy
It has the certain significance.
The method provided by the invention that ginsenoside Rg1, Re and Rb1 are purified from arasaponin has the following advantages：
1st, in arasaponin purification process, the monodisperse using nonpolar macroporous adsorption resin combination amino sealing gathers
Silica gel absorption ginsenoside Rg1, ginsenoside Re and ginsenoside Rb1 are closed, can obtain the ginsenoside of purity more than 90%
Rg1, ginsenoside Re and ginsenoside Rb1.
2nd, this technology purifying resulting composition safety testing shows that toxicity is extremely low.Acute toxicity median lethal dose half
Lethal dose LD50 is 858.37mg/kg, and 95% credible is limited to 774.29~961.59mg/kg.
Specific embodiment
It is further illustrated the present invention below by embodiment.It should be understood that the embodiment of the present invention is for illustrating
The present invention rather than limitation of the present invention.The simple modifications that essence according to the present invention carries out the present invention belong to the present invention
Claimed scope.Unless otherwise indicated, the percentage of the amount of alcohol in the present invention is percentage by volume, and v/v represents solution
Volume ratio, BV be column volume multiple, as 1BV be 1 times of column volume.
Embodiment 1：The preparation method of arasaponin
Pseudo-ginseng 1000g is taken, adds in 60 DEG C of the 60% ethyl alcohol heating and refluxing extraction 2 times of 5 times of three seven weight, first time 3
Hour, second 2 it is small when, merge extracting solution, filtering, filtrate is concentrated into relative density as 1.20, after concentrate degreasing, gained leaching
Cream crosses D101 macroporous absorbent resins absorption-elution, and concentration, drying after the oxidized aluminium of eluent, activated carbon adsorption decoloration obtain three
Seven total saposins.
Embodiment 2：The preparation method of arasaponin
Radix Notoginseng is taken to be ground into coarse powder 1000g, when adding 80% ethyl alcohol 8000ml extractions 7 small, collects extracting solution, filtering takes filter
Liquid recycles ethyl alcohol to no alcohol taste, adds water that the solution of every 1ml crude drugs containing 0.5g is made, crosses macroporous resin column and alumina adsorption, uses
65% ethanol elution, eluent concentration, drying, obtains arasaponin.
Embodiment 3：The preparation method of arasaponin
Radix Notoginseng is taken, 20 mesh coarse powder are made, is extracted 2 times with ethyl alcohol, adds 10 times 70% of ethyl alcohol every time, when extraction 3 is small every time,
Merge extracting solution, filtration takes filtrate recycling ethanol to cross the large pore resin absorption column absorption of 8 times of three seven weight to no alcohol taste, collect
Eluent, adsorption bleaching, recycling design, concentration, low temperature drying obtain arasaponin.
Embodiment 4：
1) after arasaponin is taken to add concentration for the dissolving of 20% ethyl alcohol, the dodecyl benzene sulfonic acid of ethyl alcohol weight 1% is added in
Sodium after dissolving, is loaded into blade diameter length ratio as 1:10th, using ethyl styrene as on the nonpolar macroporous adsorption resin of skeleton, 3 times of cylinders
60% ethanol elution of product is collected gained eluent, is concentrated and dried；
2) take dry product obtained by step 2) that 60% ethyl alcohol is added to dissolve, be loaded into using the monodisperse polymer silica gel of amino sealing as
On the chromatographic column of filler, blade diameter length ratio 1:10, gradient elution is made under 20 DEG C of constant temperature with 80%-50% ethyl alcohol, eluent is purple
External detector on-line checking ginsenoside Rg1, Re and Rb1 contents, UV absorption wavelength are 203nm；
3) Fractional Collections eluent, using ultraviolet absorptivity as foundation, discard no ginsenoside Rg1, Re and Rb1 part and
Impurity peak area is higher than 5% part, merges rest part (testing result is shown in Table 1), puts 60 DEG C and is concentrated in vacuo drying to get ginseng
Saponin(e Re and ginsenoside Rd.
As a result detect：Ginsenoside Rg1, ginsenoside Re and ginsenoside Rb1's composition ratio are 1:0.5:1, purity
About 92%.
Embodiment 5：
1) after arasaponin is taken to add concentration for the dissolving of 20% ethyl alcohol, the detergent alkylate sulphur of ethyl alcohol weight 0.5% is added in
Sour sodium after dissolving, is loaded into blade diameter length ratio as 1:5th, using ethyl styrene as on the nonpolar macroporous adsorption resin of skeleton, 3 times of columns
50% ethanol elution of volume is collected gained eluent, is concentrated and dried；
2) take dry product obtained by step 2) that 70% ethyl alcohol is added to dissolve, be loaded into using the monodisperse polymer silica gel of amino sealing as
On the chromatographic column of filler, blade diameter length ratio 1:5, gradient elution is made under 10 DEG C of constant temperature with 80%-50% ethyl alcohol, eluent is with ultraviolet
Detector on-line checking ginsenoside Rg1, Re and Rb1 contents, UV absorption wavelength are 200nm；
3) Fractional Collections eluent, using ultraviolet absorptivity as foundation, discard no ginsenoside Rg1, Re and Rb1 part and
Impurity peak area is higher than 5% part, merges rest part, puts 60 DEG C and is concentrated in vacuo drying to get ginsenoside Re and ginseng soap
Glycosides Rd.
As a result detect：Ginsenoside Rg1, ginsenoside Re and ginsenoside Rb1's composition ratio are 1:0.5:1, purity
About 90%.
Embodiment 6：
1) after arasaponin is taken to add concentration for the dissolving of 30% ethyl alcohol, the dodecyl benzene sulfonic acid of ethyl alcohol weight 3% is added in
Sodium after dissolving, is loaded into blade diameter length ratio as 1:20th, using ethyl styrene as on the nonpolar macroporous adsorption resin of skeleton, 3 times of cylinders
40% ethanol elution of product is collected gained eluent, is concentrated and dried；
2) take dry product obtained by step 2) that 50% ethyl alcohol is added to dissolve, be loaded into using the monodisperse polymer silica gel of amino sealing as
On the chromatographic column of filler, blade diameter length ratio 1:50, gradient elution is made under 60 DEG C of constant temperature with 80%-50% ethyl alcohol, eluent is purple
External detector on-line checking ginsenoside Rg1, Re and Rb1 contents, UV absorption wavelength are 210nm；
3) Fractional Collections eluent, using ultraviolet absorptivity as foundation, discard no ginsenoside Rg1, Re and Rb1 part and
Impurity peak area is higher than 5% part, merges rest part, puts 60 DEG C and is concentrated in vacuo drying to get ginsenoside Re and ginseng soap
Glycosides Rd.
As a result detect：Ginsenoside Rg1, ginsenoside Re and ginsenoside Rb1's composition ratio are 1:0.5:1, purity
About 95%.
Experimental example 1：Piecewise acquisition HPLC determination datas, content detection data are shown in Table 1 in 4 operating process of embodiment.
Table 1：UV absorbance detection result
1 the results show of table：Use the monodisperse polymer silica gel purification point of nonpolar macroporous adsorption resin combination amino sealing
From arasaponin, ginsenoside Rg1, ginsenoside Re and ginsenoside Rb1 go out the Cmax high period in eluent,
There is obvious deviation with the high crest segment of impurity, therefore technical solution of the present invention purifies and separates ginsenoside Rg1, ginsenoside can be utilized
Re and ginsenoside Rb1.
Experimental example 2：The acute toxicity tests
With reference to 2010 editions《Chinese Pharmacopoeia》Acute toxicity test method carries out toxicity test to 1 sample of the embodiment of the present invention.With
Weighted regression probability method (Bliss methods) calculates, and experimental result is shown in Table 2.
3. acute toxicity result (n=10) of table
Table 2 the result shows that：Median lethal dose LD50 is 858.37mg/kg, and 95% credible is limited to 774.29~961.59mg/
Kg, toxicity safe using the ginsenoside Rg1 of purification ＆ isolation of the present invention, ginsenoside Re and ginsenoside Rb1's composition
It is minimum.
Although above having used general explanation, specific embodiment and experiment, the present invention is made to retouch in detail
It states, but on the basis of the present invention, some modifications can be made to it or are improved, this is aobvious and easy to those skilled in the art
See.Therefore, these modifications or improvements without departing from theon the basis of the spirit of the present invention, belong to claimed
Scope.
Claims (9)
1. the method for Rg1, Re and Rb1 are purified from arasaponin, which is characterized in that comprise the following steps：
1) after taking arasaponin that ethyl alcohol is added to dissolve, neopelex is added in, after dissolving, is loaded into nonpolar macroporous suction
On attached resin, with ethanol elution, gained eluent is collected, is concentrated and dried；
2) take dry product obtained by step 1) that ethyl alcohol is added to dissolve, be loaded into the chromatography using amino sealing monodisperse polymer silica gel as filler
On column, gradient elution is made with 80%-50% ethyl alcohol at a constant temperature, eluent with UV detector on-line checking ginsenoside Rg1,
Re and Rb1 contents；
3) Fractional Collections eluent using ultraviolet absorptivity as foundation, discards no ginsenoside Rg1, Re and Rb1 parts and impurity
Peak area is higher than 5% part, remaining merging, gained collection liquid is concentrated and dried to get ginsenoside Rg1, Re and Rb1.
2. the method as described in claim 1, which is characterized in that the monodisperse polymer silicagel column of step 2) the amino sealing,
Chromatographic column blade diameter length ratio is 1:5-50.
3. the method as described in claim 1, which is characterized in that the step 1) nonpolar macroporous adsorption resin is ethylo benzene
Ethylene is the nonpolar macroporous adsorption resin of skeleton.
4. the method as described in claim 1, which is characterized in that the step 1) nonpolarity macroporous adsorptive resins chromatographic column, chromatographic column
Blade diameter length ratio is 1:5-20.
5. the method as described in claim 1, which is characterized in that step 1) the neopelex addition is ethyl alcohol
The 0.5-3% of weight.
6. the method as described in claim 1, which is characterized in that the step 2) dry product adds ethyl alcohol to dissolve, and concentration of alcohol is
50-70%.
7. the method as described in claim 1, it is characterised in that：Ethyl alcohol constant temperature elutes in the step 2), temperature 10-60
℃。
8. the method as described in claim 1, which is characterized in that UV detector on-line checking in the step 2), ultraviolet suction
Receipts wavelength is 200-210nm.
9. the method as described in claim 1, it is characterised in that：Arasaponin in the step 1) refers to adopt from Radix Notoginseng
Carried with water or alcohol extracting obtained by, wherein containing notoginsenoside R, ginsenoside Rg1, ginsenoside Re, ginsenoside Rb and ginseng soap
Glycosides Rd.
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| CN106432392A (en) * | 2016-08-31 | 2017-02-22 | 吉林紫鑫药业股份有限公司 | Preparation method of ginsenoside Rg1 and ginsenoside Re |
| CN113666983B (en) * | 2021-09-30 | 2022-08-02 | 昆药集团股份有限公司 | Saponin monomeric compound, separation method thereof and application of saponin monomeric compound in preparation of Xuesaitong medicine |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101463061A (en) * | 2007-12-21 | 2009-06-24 | 中国医学科学院药物研究所 | Ginseng saponin Rg1 and Rb1 in pseudo-ginseng and preparation of total saponin thereof |
| CN101575357A (en) * | 2008-05-09 | 2009-11-11 | 澳门大学 | Method for preparing notoginsenoside R1 and ginsenoside Rg1, Re, Rb1 and Rd |
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2014
- 2014-12-30 CN CN201410839697.1A patent/CN105801656B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101463061A (en) * | 2007-12-21 | 2009-06-24 | 中国医学科学院药物研究所 | Ginseng saponin Rg1 and Rb1 in pseudo-ginseng and preparation of total saponin thereof |
| CN101575357A (en) * | 2008-05-09 | 2009-11-11 | 澳门大学 | Method for preparing notoginsenoside R1 and ginsenoside Rg1, Re, Rb1 and Rd |
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