CN103554209A - Method for preparing ginsenoside Rg1 from pseudo-ginseng - Google Patents
Method for preparing ginsenoside Rg1 from pseudo-ginseng Download PDFInfo
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- CN103554209A CN103554209A CN201310572043.2A CN201310572043A CN103554209A CN 103554209 A CN103554209 A CN 103554209A CN 201310572043 A CN201310572043 A CN 201310572043A CN 103554209 A CN103554209 A CN 103554209A
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- ginsenoside
- organic solvent
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Abstract
The invention provides a method for preparing ginsenoside Rg1 from pseudo-ginseng. The method is characterized by comprising the specific steps of cleaning, slicing, drying and grinding fresh pseudo-ginseng root to obtain pseudo-ginseng powder; heating, refluxing and extracting the pseudo-ginseng powder through an organic solvent, and combining extracting solutions; implementing rotary evaporation to the combined extracting solution and recovering the solvent to obtain a pseudo-ginseng extract; dissolving the pseudo-ginseng extract through an organic solvent, mixing a sample through chromatography silica gel, applying onto a silica gel column through a dry method after the organic solvent completely volatizes, implementing gradient elution through methylene dichloride and methanol, collecting an elution part containing the ginsenoside Rg1, and recovering the solvent to obtain a crude product containing the Rg1; dissolving the crude product containing the Rg1 through acetic ether, cooling to separate out a crystal, and filtering to obtain a Rg1 pure product. The method is simple and convenient in process, simple to operate, low in requirement on apparatus and equipment, and can prepare the Rg1 pure product; and the method, which is few in processing step and high in product yield, is suitable for industrial production.
Description
Technical field
The present invention relates to a kind of novel method of preparing ginsenoside Rg1 from pseudo-ginseng, relate in particular to a kind of preparation method who extracts separated and purified ginsenoside Rg1 from pseudo-ginseng, belong to natural radioactivity product preparation method technical field.
Background technology
Pseudo-ginseng is dry root ，Shi China rare traditional Chinese medicine of panax araliaceae plant panax notoginseng (Burk) F.H.chen, and this product has loose stasis of blood hemostasis, subduing swelling and relieving pain.For spitting of blood, to spit blood, bleeding from five sense organs or subcutaneous tissue, has blood in stool, uterine bleeding, traumatic hemorrhage, chest ventral spine pain, treating swelling and pain by traumatic injury.Be mainly used in now the treatment of the heart, cerebrovascular system disease.Complicated component in pseudo-ginseng, separated nearly hundred kinds of compositions from his root, leaf, carpopodium, bud, rhizome, mainly contain saponins, volatile oil, amino acids, flavonoid, sterols, carbohydrate, organic acid, CYCLIC DIPEPTIDES, inorganic acids, but its main effective constituent is arasaponin.
In recent years domestic and international research shows, the biological activity of monomer is most important, because getting rid of the existence of other compositions, be easy to illustrate his definite pharmacological action and analysis mechanisms, structure activity study by various of monomer saponin(e is easy to find active stronger compound, in pseudo-ginseng, monomeric compound focuses mostly in Rg1, Rb1, Re, the higher composition of Ra equal size at present, now proved that ginsenoside Rg1 is effective for senile dementia treatment, Re and Rg2 anti-arrhythmia are stronger, and antitumor Rh2 and Rg3 are stronger.Different just because of monomer saponin effect, have and need to make monomer saponin preparation.From medicinal material, find the method for extracting with separating monomer and be even more important, a kind of simple process, method simple to operate are the targets of separating monomer.
Ginsenoside Rg1: molecular formula: C
42h
720
14, molecular weight 801.03,
Structural formula is:
Anti-ageing, anti-oxidant, raising immunizing power that ginsenoside Rg1 has, the functions such as memory, have pharmacological action widely to cardiovascular and cerebrovascular, neural system, immunity system.Ginsenoside Rg1 is panaxitriol structure, is first to find from ginseng, and in ginseng, content is lower, but content is higher in pseudo-ginseng.Separation and purification sterling in plant, the one, complex process, the 2nd, component content is few, needs reasonable and simple and direct technique, can make purifying compounds become feasible.The relevant ginsenoside Rg1's of preparation method has multiple, and some with alcohol reflux, upper silica gel or alumina column carry out separation, some ultrasonic wave refluxing extraction of using, and extract is separated with acid-base precipitation, more separated with column chromatography silica gel or alumina column.What also have obtains total saponins with D101 macroporous resin, the separated sterling that obtains of recycle silicon glue post, and some patent applied fors, but above technical process is long, and complicated operation, obtains sterling Rg1 more difficult.
Summary of the invention
The object of this invention is to provide a kind of simple process, simple to operation, product yield is high, and process experimental results show that process stabilizing tens of times, effectively from pseudo-ginseng, prepares ginsenoside Rg1's novel method.
In order to achieve the above object, the invention provides a kind of method of preparing ginsenoside Rg1 from pseudo-ginseng, it is characterized in that, concrete steps are:
The first step: Radix Notoginseng powder is cleaned, cuts into slices, dries, is ground into fresh Radix Notoginseng;
Second step: the Radix Notoginseng powder that the first step is obtained is placed in round-bottomed flask or refluxing extraction device, by organic solvent heating and refluxing extraction at least one times, united extraction liquid;
The 3rd step: the extracting solution rotary evaporation that second step is obtained reclaims solvent, obtains Radix Notoginseng extract;
The 4th step: the Radix Notoginseng extract organic solvent dissolution that the 3rd step is obtained, with silica gel for chromatography, mix sample, after organic solvent volatilization is clean, silicagel column in dry method, through methylene dichloride and methyl alcohol gradient elution, thin-layer chromatography chromatogram detects wash-out process, collects the wash-out part that contains ginsenoside Rg1, reclaim after solvent, obtain the crude product that contains Rg1;
The 5th step: by the crude product that contains Rg1 obtaining, dissolve with vinyl acetic monomer, while being cooled to 5 ℃-10 ℃, crystallize out, filters, and obtains Rg1 sterling.
Preferably, the organic solvent in described second step is methyl alcohol, and the volume ratio of Radix Notoginseng powder and organic solvent is 1:2-3, and the time of each reflux is 1-3 hour, and the number of times of heating and refluxing extraction is 4-5 time.
Preferably, the temperature of the rotary evaporation in described the 3rd step is that 0-50 ℃, pressure are 0.07-0.1Mpa.
Preferably, organic solvent in described the 4th step is methyl alcohol, the weightmeasurement ratio of Radix Notoginseng extract and methyl alcohol is 20g:200ml (w/v), Radix Notoginseng extract is 20g:1200g (w/w) with mixing sample by the weight ratio of silica gel, and the methylene dichloride that wash-out is used and the volume ratio of methyl alcohol are 7:1-1:1.
Preferably, in described the 5th step, by high performance liquid chromatography (HPLC), measure content, actual conditions is: C18250 * 4.6mm chromatographic column, and the acetonitrile that the volume ratio of take is 19.5:80.5 and water are moving phase, flow velocity 1.0ml/min, detection wavelength is 210nm.
Preferably, in described the 4th step, silica gel used is 200-300 order column chromatography silica gel.
Preferably, the testing conditions of the thin-layer chromatography chromatogram in described the 4th step is: adopt GF254 plate, developping agent is the mixed solution of trichloromethane, vinyl acetic monomer, first alcohol and water, the volume ratio of described trichloromethane, vinyl acetic monomer, first alcohol and water is 15:40:22:10, take ginsenoside Rg1's reference substance as contrast, upright ascending development, with 10% ethanol solution of sulfuric acid spraying, develop the color or develop the color with iodine vapor, 105 ℃ of heating 10 minutes, aobvious violet spot during 10% ethanol solution of sulfuric acid, during iodine vapor colour developing, it is yellow spotting.
In preparation method of the present invention, ginsenoside Rg1's yield is 0.8% (to be dried medicinal material), and purity is 98%, and the ginsenoside Rg1 of gained can be used for pharmaceutical industries and other purposes.
Compared with prior art, the invention has the beneficial effects as follows:
Simple process of the present invention, simple to operate, instrument and equipment requires low, and one time solvent refluxing extracts, and it is separated that extract is once gone up silica gel column chromatography, can obtain Rg1 sterling; Because processing step is few, product yield is high, is applicable to suitability for industrialized production.
Embodiment
For the present invention is become apparent, hereby with preferred embodiment, be described in detail below.
Embodiment
By fresh Radix Notoginseng 5.5kg, clean section, dry, put and in pulverizer, be ground into Radix Notoginseng powder, about 5kg, above-mentioned Radix Notoginseng powder is placed in to refluxing extraction device, adds chemical pure methyl alcohol, the volume ratio of Radix Notoginseng powder and methyl alcohol is 1:2.3, refluxing extraction four times is extracted 3 hours at every turn, extracts the extracting liquid filtering of gained at every turn, united extraction liquid, under the condition that is 0.08Mpa at 50 ℃, pressure, use Rotary Evaporators decompression and solvent recovery, obtain extract medicinal extract 20g, extraction yield is 0.4%.By extract medicinal extract 200ml dissolve with methanol, with 1200g200-300 order column chromatography silica gel, mix sample, after heating in water bath makes methyl alcohol volatilization dry, pack diameter of phi 10cm into, be added with in advance in the chromatographic column of the blank 200-300 order of 3kg column chromatography silica gel, first use methylene dichloride: methyl alcohol (7:1V/V) wash-out, progressively increase again the ratio of methyl alcohol in elutriant, use successively methylene dichloride: methyl alcohol (7:2V/V), methylene dichloride: methyl alcohol (7:3V/V), methylene dichloride: methyl alcohol (7:4V/V), methylene dichloride: methyl alcohol (7:5V/V), methylene dichloride: the elutriant wash-out of methyl alcohol (7:6V/V), after the elutriant of every kind of ratio uses a certain non-mass-tone band in chromatographic separation column bottom and elutes, change again a kind of new ratio elutriant, until finally use methylene dichloride: the elutriant wash-out of methyl alcohol (1:1V/V), TLC thin layer chromatography detects wash-out process, (silica-gel plate GF254 plate, developping agent is trichloromethane, vinyl acetic monomer, the mixed solution of first alcohol and water, described trichloromethane, vinyl acetic monomer, the volume ratio of first alcohol and water is 15:40:22:10, take ginsenoside Rg1's reference substance as contrast, upright ascending development, 10% sulfuric acid ethanol spraying colour developing, 105 ℃ are heated 10 minutes, sample and reference substance show identical purple plague purpura point.Press 250ml/ stream part and receive, while being eluted to 57-74 stream part, occur Rg1 spot, merge, under the condition that is 0.08Mpa at 50 ℃, pressure, with Rotary Evaporators decompression and solvent recovery, obtain Rg1 crude product, with vinyl acetic monomer, dissolve, be placed at 8 ℃ of temperature, crystallize out, filters, and obtains Rg1 sterling.Product yield is 0.8%, and through HPLC, detecting purity is 98%.The actual conditions of HPLC is: C18250 * 4.6mm chromatographic column, and the acetonitrile that the volume ratio of take is 19.5:80.5 and water are moving phase, flow velocity 1.0ml/min, detection wavelength is 210nm.
The ginsenoside Rg1's of gained structure is differentiated: white powder, mp191-193 ℃, [α] D
20+ 26.0
0, ultimate analysis C
42h
720
14.2H
20 theoretical value: C60.28, H9.09: experimental value C60.32, H9.06.FD-MS：839[M+K]
+，823[M+Na]
+，821[M+K-H
20]
+，805[M+Na-H
20]
+，677[M+K-162]
+，661[M+Na-162]
+，839[M+2K]
+.EI-MS：m／e
797,770,752,710,525,483,482,465,464,423,422,405,404,389,331,295,289,271,269,229,211,202,187,169,153,109 etc.
1hNMR δ (ppm): 0.95-1.18 (6CH
3) 1.59 Hes
1.99-2.10 (10 * OCOCH
3), 4.79,4.68 (each 1H, J is 7.5Hz), 5.13
deng.The POP data of compound and ginsenoside Rg1's POP data are basically identical.
Claims (7)
1. from pseudo-ginseng, prepare ginsenoside Rg1's a method, it is characterized in that, concrete steps are:
The first step: Radix Notoginseng powder is cleaned, cuts into slices, dries, is ground into fresh Radix Notoginseng;
Second step: the Radix Notoginseng powder that the first step is obtained is placed in round-bottomed flask or refluxing extraction device, by organic solvent heating and refluxing extraction at least one times, united extraction liquid;
The 3rd step: the extracting solution rotary evaporation that second step is obtained reclaims solvent, obtains Radix Notoginseng extract;
The 4th step: the Radix Notoginseng extract organic solvent dissolution that the 3rd step is obtained, with silica gel for chromatography, mix sample, after organic solvent volatilization is clean, silicagel column in dry method, through methylene dichloride and methyl alcohol gradient elution, thin-layer chromatography chromatogram detects wash-out process, collects the wash-out part that contains ginsenoside Rg1, reclaim after solvent, obtain the crude product that contains Rg1;
The 5th step: by the crude product that contains Rg1 obtaining, dissolve with vinyl acetic monomer, while being cooled to 5 ℃-10 ℃, crystallize out, filters, and obtains Rg1 sterling.
2. the method for preparing ginsenoside Rg1 from pseudo-ginseng as claimed in claim 1, it is characterized in that, the organic solvent in described second step is methyl alcohol, and the volume ratio of Radix Notoginseng powder and organic solvent is 1:2-3, the time of each reflux is 1-3 hour, and the number of times of heating and refluxing extraction is 4-5 time.
3. the method for preparing ginsenoside Rg1 from pseudo-ginseng as claimed in claim 1, is characterized in that, the temperature of the rotary evaporation in described the 3rd step is that 0-50 ℃, pressure are 0.07-0.1Mpa.
4. the method for preparing ginsenoside Rg1 from pseudo-ginseng as claimed in claim 1, it is characterized in that, organic solvent in described the 4th step is methyl alcohol, the weightmeasurement ratio of Radix Notoginseng extract and methyl alcohol is 20g:200ml, Radix Notoginseng extract is 20g:1200g with mixing sample by the weight ratio of silica gel, and the methylene dichloride that wash-out is used and the volume ratio of methyl alcohol are 7:1-1:1.
5. the method for preparing ginsenoside Rg1 from pseudo-ginseng as claimed in claim 1, it is characterized in that, in described the 5th step, use high effective liquid chromatography for measuring content, actual conditions is: C18250 * 4.6mm chromatographic column, the acetonitrile that the volume ratio of take is 19.5:80.5 and water are moving phase, flow velocity 1.0ml/min, detection wavelength is 210nm.
6. the method for preparing ginsenoside Rg1 from pseudo-ginseng as claimed in claim 1, is characterized in that, in described the 4th step, silica gel used is 200-300 order column chromatography silica gel.
7. the method for preparing ginsenoside Rg1 from pseudo-ginseng as claimed in claim 1, it is characterized in that, the testing conditions of the thin-layer chromatography chromatogram in described the 4th step is: adopt GF254 plate, developping agent is trichloromethane, vinyl acetic monomer, the mixed solution of first alcohol and water, described trichloromethane, vinyl acetic monomer, the volume ratio of first alcohol and water is 15:40:22:10, take ginsenoside Rg1's reference substance as contrast, upright ascending development, with 10% ethanol solution of sulfuric acid spraying, develop the color or develop the color with iodine vapor, 105 ℃ of heating 10 minutes, aobvious violet spot during 10% ethanol solution of sulfuric acid, during iodine vapor colour developing, for yellow spotting.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104693263A (en) * | 2015-04-01 | 2015-06-10 | 江苏省中医药研究院 | Notoginsenoside compound with antineoplastic activity and preparation method and application thereof |
| CN107595908A (en) * | 2017-09-26 | 2018-01-19 | 云南金七制药有限公司 | A kind of extracting method that notoginsenoside is extracted from fresh pseudo-ginseng |
| CN111072747A (en) * | 2019-12-26 | 2020-04-28 | 王传涛 | Ginsenoside and ultrasonic extraction method thereof |
| CN116920005A (en) * | 2023-07-18 | 2023-10-24 | 常州大学 | Pseudo-ginseng ginsenoside extract and preparation method thereof |
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| CN102108091A (en) * | 2009-12-28 | 2011-06-29 | 云南本草精素生物科技有限公司 | Method for preparing two ginsenoside monomers |
| CN102453072A (en) * | 2010-10-26 | 2012-05-16 | 中国医学科学院药物研究所 | Preparation method of ginsenoside Rg1 |
| CN103232515A (en) * | 2013-05-15 | 2013-08-07 | 南京泽朗医药科技有限公司 | Cyclocarya paliurus glucoside I preparation method |
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2013
- 2013-11-15 CN CN201310572043.2A patent/CN103554209B/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102108091A (en) * | 2009-12-28 | 2011-06-29 | 云南本草精素生物科技有限公司 | Method for preparing two ginsenoside monomers |
| CN102453072A (en) * | 2010-10-26 | 2012-05-16 | 中国医学科学院药物研究所 | Preparation method of ginsenoside Rg1 |
| CN103232515A (en) * | 2013-05-15 | 2013-08-07 | 南京泽朗医药科技有限公司 | Cyclocarya paliurus glucoside I preparation method |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104693263A (en) * | 2015-04-01 | 2015-06-10 | 江苏省中医药研究院 | Notoginsenoside compound with antineoplastic activity and preparation method and application thereof |
| CN104693263B (en) * | 2015-04-01 | 2016-08-24 | 江苏省中医药研究院 | A kind of arasaponin compound with anti-tumor activity and preparation method and application |
| CN107595908A (en) * | 2017-09-26 | 2018-01-19 | 云南金七制药有限公司 | A kind of extracting method that notoginsenoside is extracted from fresh pseudo-ginseng |
| CN111072747A (en) * | 2019-12-26 | 2020-04-28 | 王传涛 | Ginsenoside and ultrasonic extraction method thereof |
| CN116920005A (en) * | 2023-07-18 | 2023-10-24 | 常州大学 | Pseudo-ginseng ginsenoside extract and preparation method thereof |
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