CN101830957A - Process for preparing ginsenosides Rh2 and Rh3 from stems and leaves of pseudoginseng root - Google Patents
Process for preparing ginsenosides Rh2 and Rh3 from stems and leaves of pseudoginseng root Download PDFInfo
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- CN101830957A CN101830957A CN200910094196A CN200910094196A CN101830957A CN 101830957 A CN101830957 A CN 101830957A CN 200910094196 A CN200910094196 A CN 200910094196A CN 200910094196 A CN200910094196 A CN 200910094196A CN 101830957 A CN101830957 A CN 101830957A
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Abstract
The invention relates to a process for preparing ginsenosides Rh2 and Rh3 by using stems and leaves of pseudoginseng root as raw materials, which comprises the following technical flows: (1), extracting saponin from the leaves of the pseudoginseng root, namely cooking the stems and leaves of the pseudoginseng root with water for extraction, absorbing, eluting and concentrating to obtain a thin extract of the ginsenosides of the pseudoginseng root; (2), preparing diol saponins, namely absorbing, eluting, concentrating, drying and crushing the thin extract of the ginsenosides of the pseudoginseng root to obtain the diol saponins; and (3), acid hydrolysis, namely, performing acid hydrolysis on the diol saponins, absorbing, washing with water, eluting, concentrating and drying to obtain a mixture which contains the ginsenosides Rh2 and Rh3. The process of the invention is simple and feasible, high in purification rate and good in quality, and reaches industry standards.
Description
Technical field
The present invention relates to plant amedica effective ingredient process for extracting, be specifically related to utilize the method for notoginseng haulm for feedstock production ginsenoside Rh 2, Rg3.
Background technology:
Genseng is a Chinese medicine renowned in the world, before more than 4000 years, our ancestors have just utilized the genseng disease preventing and treating, the beginning of the nineties in last century, Japanese scholar's Beichuan merit find in the genseng a kind of active substance--panaxoside Rg 3 has the effect that optionally suppresses tumor cell invasion and transfer.Have more than 40 kind of saponin in the genseng, but Rg3 do not exist in ginseng crude drug fresh or seasoning, the content in red ginseng only is 3/100000ths.Panaxoside Rg 3 not only has anti-cancer and anticancer effect, also have to improve immune, protect the liver, pharmacological actions such as antifatigue, protection cranial nerve cell and antithrombotic.
Along with going deep into that genseng is studied, Japanese scholar has found ginsenoside Rh 2 first from red ginseng.This saponin is a kind of secondary glucoside, be fresh ginseng when being processed into red ginseng owing to generate after some glycol group saponin degradation, its content in red ginseng about 100,000/about.Rh2 just was found antitumour activity before 10 years, but since content very little, extract and to be difficult for, to cost an arm and a leg, therefore be not utilized always.Along with clinical test results is come out by report successively, Rh2 is regarded as the natural anti-cancer material of now tool potentiality for the very surprising satisfaction of anticancer curative effect.Studies have shown that Rh2 has cancer cells suppresses and the effect of anti-metastasis, and effect is very obvious.Rh2 not only has the growth that suppresses all cancer cells, the function of inducing differentiation cancer cells and anti-metastasis, simultaneously to the human body nontoxicity.Rh2 makes withered, the dead effect of cancer cells nuclear, is different from any chemicotherapy method and medicine.Rh2 still has the effect of the very outstanding various immunity functions of lifting to human body, and the HUMAN HEALTH cell is had no toxic side effect, only specializes in and hits cancer cells.
Pseudo-ginseng [Panaxnotoginseng (BurK.) F.H.Chen] is all the araliaceae ginseng plant with genseng, there are some researches show that notoginseng haulm also is the important source of ginsenoside-Rh2 and panaxoside Rg 3.
According to preliminary investigation, at present the notoginseng haulm of gathering every year is only had an appointment and 5% is utilized, and is mainly used in the raw material purposes of preparation other medicines and preparation makeup or the like, and some is used to prepare the teabag drink, nourishing takes care of health, and most of notoginseng haulm resource is dropped.Therefore to effective utilization of notoginseng haulm, therefrom extract valuable ginsenoside Rh 2 and panaxoside Rg 3, promote the well-being of mankind, have very important practical sense.
" chemical research and application " the 16th volume the 1st phase " Folium Notoginseng glycoside prepares anticancer active constituent 20 (R)-ginsenoside-Rh2 and panaxoside Rg 3 " of publishing in February, 2004, technological expression is: utilize Folium Notoginseng glycoside to be raw material, obtain by acetolysis and column chromatography for separation.Its technology is: 12 gram Sanchi Leaf general glycosides, adds in 300 milliliter of 50% acetic acid aqueous solution, and 70 ℃ of heating in water bath 6 hours, adding 5% sodium carbonate solution is down stirred in cooling.Filter, filtrate is used n-butanol extraction.Precipitation is with methyl alcohol-chloroform dissolving, carry out silica gel column chromatography, with chloroform-methanol-ethyl acetate-water (2: 2: 4: 1, lower floor) wash-out, thin-layer chromatography is checked, merge same composition, obtain the main component that contains compound 1, again with silica gel column chromatography (chloroform-methanol 9: 1) processing method such as separation and purification again.There is many-sided problem in the disclosed notoginseng haulm that utilizes for the method that raw material extracts ginsenoside Rh 2 and Rg3, each step of this method has been used number of chemical reagent, as yellow soda ash neutralizing acid, n-butanol extraction, methyl alcohol-chloroform dissolving, with chloroform-methanol-ethyl acetate-water (2: 2: 4: 1, lower floor) wash-out etc., these nothing/organic solvents will partly be brought in the product, influence quality product.Technology is complicated, and cost is higher also to be outwardness.
Summary of the invention:
The purpose of this invention is to provide a kind of is the processing method of feedstock production ginsenoside Rh 2, Rg3 with the notoginseng haulm, and this processing method is simple, the purification rate height, and good product quality meets industry standard.
Technical process:
(1) extracts the pseudo-ginseng total saponin from leaves
Notoginseng haulm → poach extraction → absorption → wash-out → concentrate → the rare medicinal extract of pseudo-ginseng total saponin from leaves,
The notoginseng haulm boiling is extracted three times, each time 1.5-5 hour, 75～100 ℃ of temperature, the extraction after-filtration that finishes merges three filtrates and goes up the absorption of ADS3 macroporous adsorptive resins, washes with water, 10-95% ethanolic soln wash-out, elutriant is evaporated to does not have the alcohol flavor, promptly gets the rare medicinal extract of pseudo-ginseng total saponin from leaves
(2) preparation of glycol group saponin
The rare medicinal extract of pseudo-ginseng total saponin from leaves → absorption → wash-out → concentrate → drying → pulverizing → glycol group saponin,
The rare medicinal extract of pseudo-ginseng total saponin from leaves adds water 1-5 and doubly dilutes, and last AB8 resin column absorption is washed to neutrality, uses the 70-80% ethanol elution, and the elutriant concentrate drying promptly gets glycol group saponin,
(3) acid hydrolysis
Glycol group saponin → acid hydrolysis → absorption → washing → wash-out → concentrate drying → contain mixture of panaxoside Rg 3 and ginsenoside Rh 2,
Glycol group saponin is carried out acid hydrolysis, the acid hydrolysis condition is as follows: adopt a kind of in acetic acid or oxalic acid or hydrochloric acid or sulfuric acid or the phosphoric acid, wherein, with acetic acid or oxalic acid is commonly used, concentration is 0.1-10mol/L, 20～95 ℃ of temperature, 1 hour～5 days time, after acid hydrolysis finishes, last resin column AB8 absorption, be washed to neutrality, can be PH6.5-PH7.5, from low to high in proper order with 10% to 95% ethanol elution, elutriant mixes by concentration, concentrate drying, products obtained therefrom are and contain panaxoside Rg 3 and ginsenoside Rh 2 mixture.
In the glycol group saponin Rf2 under optimum conditions acid hydrolysis be transformed into Rh2, to change thaumatropy after the acid hydrolysis under optimum conditions be Rg3 for Rb1, Rb2, Rb3, Rc, Rb in the glycol group saponin.Its reaction formula is as follows:
Rb1 R1＝GLC
2-GLC R2＝GLC
6-GLC
Rb2 R1＝GLC
2-GLC R2＝GLC
6-Ara(p)
Rc R1＝GLC
2-GLC R2＝GLC
6-Ara(+)
Rd R1＝GLC
2-GLC R2＝GLC
RF2 R1＝GLC R2＝GLC
The ginsenoside Rh 2 structural formula
[structural formula] owing to the sterie configuration difference of its C-20 position, ginsenoside Rh 2 all has two kinds of configurations at 20, i.e. 20 (R) types and 20 (S) type.Structural formula is as scheming:
20 (S)-ginsenoside Rh
220 (R)-ginsenoside Rh
2
[molecular formula] C
36H
62O
8
[physical behavior] colourless needle crystal, fusing point mp ° c218～220, specific optical rotation [a]
22 D(in methyl alcohol)+21.8 (0.93), infrared spectra
Be soluble in
In the organic solvent such as methyl alcohol, ethanol.
Panaxoside Rg 3 structural formulas
[structural formula] is owing to the sterie configuration difference of its C-20 position, panaxoside Rg
3At 20 two kinds of configurations are arranged all, i.e. 20 (R) types and 20 (S) type.Its structural formula is as follows:
20 (S)-panaxoside Rgs
220 (R)-panaxoside Rgs
3
[molecular formula] C
42H
72O
13
[physical behavior] colourless needle crystal, 20 (S)-panaxoside Rgs
3Be soluble in methyl alcohol, and 20 (R)-panaxoside Rgs
3Be insoluble in methyl alcohol, be soluble in pyridine.
From following table as can be seen, the prepared product of technical scheme of the present invention meets concerned countries and industry product specification of quality.
The key technical indexes:
The present invention is further described below in conjunction with embodiment, but be not limited to embodiment.
Embodiment:
Embodiment 1,
(1) extracts the pseudo-ginseng total saponin from leaves
Notoginseng haulm → poach extraction → absorption → wash-out → concentrate → the rare medicinal extract of pseudo-ginseng total saponin from leaves,
The notoginseng haulm boiling is extracted three times, and each 2 hours time, 90 ℃ of temperature are extracted the after-filtration that finishes, merge three filtrates and go up the absorption of ADS3 macroporous adsorptive resins, wash 70% ethanolic soln wash-out with water, elutriant is evaporated to does not have the alcohol flavor, promptly gets the rare medicinal extract of pseudo-ginseng total saponin from leaves
(2) preparation of glycol group saponin
The rare medicinal extract of pseudo-ginseng total saponin from leaves → absorption → wash-out → concentrate → drying → pulverizing → glycol group saponin,
The rare medicinal extract of pseudo-ginseng total saponin from leaves adds 3 times of dilutions of water, and last AB8 resin column absorption is washed to neutrality, carries out wash-out with 70% ethanol, and the elutriant concentrate drying promptly gets glycol group saponin,
(3) acid hydrolysis
Glycol group saponin → acid hydrolysis → absorption → washing → wash-out → concentrate drying → contain mixture of panaxoside Rg 3 and ginsenoside Rh 2,
Glycol group saponin is carried out acid hydrolysis, the acid hydrolysis condition is as follows: the employing acetate concentration is 1mol/L, 95 ℃ of temperature, 2 hours time is after acid hydrolysis finishes, last resin column AB8 absorption, be washed to PH7.0, order is carried out wash-out with 30%, 50%, 60%, 75%, 85% ethanol, and elutriant mixes, concentrate drying, products obtained therefrom are and contain panaxoside Rg 3 and ginsenoside Rh 2 mixture.Products obtained therefrom Rg3 and Rh2 content are respectively 30% and 40%, and this product is panaxoside Rg 3 and Rh2.
Embodiment 2,
(1) extracts the pseudo-ginseng total saponin from leaves
Notoginseng haulm → poach extraction → absorption → wash-out → concentrate → the rare medicinal extract of pseudo-ginseng total saponin from leaves,
The notoginseng haulm boiling is extracted three times, and each 5 hours time, 75 ℃ of temperature are extracted the after-filtration that finishes, merge three filtrates and go up the absorption of ADS3 macroporous adsorptive resins, wash 20% ethanolic soln wash-out with water, elutriant is evaporated to does not have the alcohol flavor, promptly gets the rare medicinal extract of pseudo-ginseng total saponin from leaves
(2) preparation of glycol group saponin
The rare medicinal extract of pseudo-ginseng total saponin from leaves → absorption → wash-out → concentrate → drying → pulverizing → glycol group saponin,
The rare medicinal extract of pseudo-ginseng total saponin from leaves adds 5 times of dilutions of water, and last AB8 resin column absorption is washed to neutrality, carries out wash-out with 80% ethanol, and the elutriant concentrate drying promptly gets glycol group saponin,
(3) acid hydrolysis
Glycol group saponin → acid hydrolysis → absorption → washing → wash-out → concentrate drying → contain mixture of panaxoside Rg 3 and ginsenoside Rh 2,
Glycol group saponin is carried out acid hydrolysis, the acid hydrolysis condition is as follows: the employing concentration of oxalic acid is 8mol/L, 35 ℃ of temperature, 4 days time is after acid hydrolysis finishes, last resin column AB8 absorption, be washed to PH6.8, order is carried out wash-out with 10%, 60%, 80%, 95% ethanol, and elutriant mixes, concentrate drying, products obtained therefrom are and contain panaxoside Rg 3 and ginsenoside Rh 2 mixture.Products obtained therefrom Rg3 and Rh2 content are respectively 30% and 40%, and this product is panaxoside Rg 3 and Rh2.
Through product being detected, meet country and industry standard by country and industry standard.
Claims (2)
1. notoginseng haulm prepares the processing method of ginsenoside Rh 2, Rg3, it is characterized in that: prepare by following technical process:
(1) extracts the pseudo-ginseng total saponin from leaves
Notoginseng haulm → poach extraction → absorption → wash-out → concentrate → the rare medicinal extract of pseudo-ginseng total saponin from leaves,
The notoginseng haulm boiling is extracted three times, each time 1.5-5 hour, 75～100 ℃ of temperature, the extraction after-filtration that finishes merges three filtrates and goes up the absorption of ADS3 macroporous adsorptive resins, washes with water, 10-95% ethanolic soln wash-out, elutriant is evaporated to does not have the alcohol flavor, promptly gets the rare medicinal extract of pseudo-ginseng total saponin from leaves
(2) preparation of glycol group saponin
The rare medicinal extract of pseudo-ginseng total saponin from leaves → absorption → wash-out → concentrate → drying → pulverizing → glycol group saponin,
The rare medicinal extract of pseudo-ginseng total saponin from leaves adds water 1-5 and doubly dilutes, and last AB8 resin column absorption is washed to neutrality, uses the 70-80% ethanol elution, and the elutriant concentrate drying promptly gets glycol group saponin,
(3) acid hydrolysis
Glycol group saponin → acid hydrolysis → absorption → washing → wash-out → concentrate drying → contain mixture of panaxoside Rg 3 and ginsenoside Rh 2,
Glycol group saponin is carried out acid hydrolysis, the acid hydrolysis condition is as follows: adopt a kind of in acetic acid or oxalic acid or hydrochloric acid or sulfuric acid or the phosphoric acid, concentration is 0.1-10mol/L, 20～95 ℃ of temperature, 1 hour～5 days time, after acid hydrolysis finished, last resin column AB8 absorption was washed to neutrality, press concentration from low to high in proper order with 10% to 95% ethanol elution, elutriant mixes, and concentrate drying, products obtained therefrom are and contain panaxoside Rg 3 and ginsenoside Rh 2 mixture.
2. notoginseng haulm according to claim 1 prepares the processing method of ginsenoside Rh 2, Rg3, it is characterized in that: acetic acid or oxalic acid are selected in acid hydrolysis for use.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102993258A (en) * | 2012-12-17 | 2013-03-27 | 烟台荣昌制药股份有限公司 | Method for preparing ginsenoside Rg3 through hydrolyzing total saponins of panax ginseng |
| CN105218613A (en) * | 2015-10-23 | 2016-01-06 | 昆明学院 | One is rapidly and efficiently hydrolyzed Folium Notoginseng total arasaponins and prepares ginsenoside Rg3, the method for Rh2 |
| CN110669093A (en) * | 2019-09-11 | 2020-01-10 | 江苏吉生源生物科技有限公司 | Method for extracting ginsenoside Rg3 |
| CN111118096A (en) * | 2020-01-07 | 2020-05-08 | 陕西岳达德馨生物制药有限公司 | Enzymatic preparation method of saponin |
| CN112843111A (en) * | 2021-03-01 | 2021-05-28 | 北京泛亚同泽生物医学研究院有限公司 | Pharmaceutical composition for treating metabolism-related fatty liver disease and preparation method and application thereof |
| CN117323270A (en) * | 2023-11-29 | 2024-01-02 | 江西康一参生物科技有限公司 | Anti-inflammatory multifunctional ginseng composition and application thereof |
-
2009
- 2009-03-12 CN CN200910094196A patent/CN101830957A/en active Pending
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102993258A (en) * | 2012-12-17 | 2013-03-27 | 烟台荣昌制药股份有限公司 | Method for preparing ginsenoside Rg3 through hydrolyzing total saponins of panax ginseng |
| CN102993258B (en) * | 2012-12-17 | 2015-08-26 | 烟台荣昌制药股份有限公司 | A kind of method being hydrolyzed Radix Ginseng total saponins and preparing ginsenoside Rg3 |
| CN105218613A (en) * | 2015-10-23 | 2016-01-06 | 昆明学院 | One is rapidly and efficiently hydrolyzed Folium Notoginseng total arasaponins and prepares ginsenoside Rg3, the method for Rh2 |
| CN110669093A (en) * | 2019-09-11 | 2020-01-10 | 江苏吉生源生物科技有限公司 | Method for extracting ginsenoside Rg3 |
| CN111118096A (en) * | 2020-01-07 | 2020-05-08 | 陕西岳达德馨生物制药有限公司 | Enzymatic preparation method of saponin |
| CN112843111A (en) * | 2021-03-01 | 2021-05-28 | 北京泛亚同泽生物医学研究院有限公司 | Pharmaceutical composition for treating metabolism-related fatty liver disease and preparation method and application thereof |
| CN117323270A (en) * | 2023-11-29 | 2024-01-02 | 江西康一参生物科技有限公司 | Anti-inflammatory multifunctional ginseng composition and application thereof |
| CN117323270B (en) * | 2023-11-29 | 2024-03-19 | 江西康一参生物科技有限公司 | Anti-inflammatory multifunctional ginseng composition and application thereof |
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Application publication date: 20100915 |