CN105601694B - A method of extraction ginsenoside Rg 5 - Google Patents
A method of extraction ginsenoside Rg 5 Download PDFInfo
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Abstract
The present invention relates to a kind of methods of extraction ginsenoside Rg 5, include the steps that being extracted to ginseng pulverate using acid as secondary solvent, in extraction, one or more of water, alcohols, ketone can also be added into extraction system and be used as main solvent, the present invention is directly using ginseng pulverate as raw material, in extraction process, the extraction of ginsenoside, directionally hydrolyzing and dehydration fusion are completed in primary extraction, directly efficiently prepare the extract containing ginsenoside Rg 5, with easy to operate, extract yield is high, the mild feature of experiment condition.
Description
Technical field
The present invention relates to active ingredient of Chinese herbs extraction field more particularly to a kind of methods of extraction ginsenoside Rg 5, more
Body, it is related to a kind of method for directly extracting secondary ginsenoside Rg 5 from ginseng pulverate.
Background technology
Ginsenoside is the most representational main active of ginseng, is present in ginseng, American Ginseng, Radix Notoginseng, ring
In the panax species such as ginseng, it is divided into protopanoxadiol saponins, protopanaxatriol saponins and oleanolic acid saponins.Protoplast joins
Glycol saponins include mainly ginsenoside Rb1, Rb2, Rb3, Rc and Rd；Protopanaxatriol saponins include mainly ginsenoside
Re and Rg1；Oleanolic acid saponins mainly have ginsenoside Ro.Largely studies have shown that glycoside native compound is by sugar
The secondary glycosides that base modification obtains shows better human body absorbability and better drug effect.For example, protopanoxadiol saponins
The secondary ginseng sapoglycoside Rg 3 made of C-20 selective hydrolysis such as Rb1, Rb2, Rb3, Rc, Rd shows that raw material is not had
Expansion blood vessel, anticancer, Anti-tumor metastasis and other effects；In addition, ginseng sapoglycoside Rg 3 and other anticancer drugs (such as taxol) and chemotherapy
Drug (such as CTX) is used in combination, and can effectively improve the therapeutic effect to cancer, the life quality for improving people.
Ginsenoside Rg 5 is secondary ginsenoside made of secondary ginseng sapoglycoside Rg 3 is further dehydrated, and is had significant anti-
The invasion effect of B16 melanomas and antihepatocarcinoma effect, the lung inflammation that disappears effect, anti-free radical function；In addition, secondary grade ginseng soap
Glycosides Rg5, Rk1, which are also shown, significantly improves memory function, and ginsenoside Rg 5 and its metabolite Rh3 have inhibition chronic dermatitis
Effect.
Ginsenoside Rg 5 is the peculiar saponin(e of red ginseng, be in fresh ginseng repeatedly boiling, dry process by ginsenoside
Rg3 is dehydrated.The preparation of ginsenoside Rg 5 is mainly obtained by processed ginseng raw material to red ginseng or black ginseng.For example, 2011
Year, the mediate Research Teams of Jin Feng (Dalian Polytechnic University's journal, 2011:30(2)：109-112) from the rare saponin(e of 30g red ginsengs, lead to
The total 6.05g of mixture that column chromatography has detached ginsenoside Rg 5 and Rk1 is crossed, wherein Rg5 mass fractions are 66.4%, Rk1's
Mass fraction is 23.0%；Shin YW in 2006 et al. (Arch Pharm Res.2006,29 (8):685-90) from red ginseng
Ginsenoside Rg 5 is detached；Kim SJ in 2014 et al. (Journal of Ginseng Research, 2014,39:125-
134) 150g ethanol extracts are obtained from the black ginseng powder of 2Kg, is extracted further across ether defatting and water-saturated n-butanol
To 84.50g ginseng extracts, and pass through silica gel column chromatography separation and ODS chromatographic columns point from 60g n-butanol extracts therein
From 0.19g ginsenoside Rgs 5 have been obtained, content is considerably less；JoSK in 2015 et al. (European Food Research and
Technology,2015,240(1):White ginseng 251-256) is steamed into 30h, drying in 98 DEG C, then steams 45h, drying, is analyzed through HPLC
It is 17.56mg/g to obtain 5 content of ginsenoside Rg；Biomedgenomics Co., Ltd. (South Korea, disclosure in 2008
Number：CN101155521A ginseng) will be removed the peel and do not removed the peel, 1 to 3 times of water measured is added in ginseng, under a certain pressure, 110~
1~5h is handled in 130 DEG C of temperature ranges, obtains the raised processing of Panax ginseng product of Rg5 contents.
In addition, ginsenoside Rg 5 can also by being obtained to the processing of ginsenoside, such as Yang Ling in 2005 et al. (in
State's patent, Authorization Notice No.：CN1219791C) using 10g glycol saponins as raw material, with the acid reagents such as hydrochloric acid, sulfuric acid in 10~
The characteristics of 50 DEG C of thermotonus 2h~5 day, reversely prepare chromatographic isolation 1.43g Rk1 and 1.54g Rg5 through C-18, the method be
Using protopanoxadiol saponins as raw material, it is added under antioxidant and inert gas shielding and prepares ginsenoside Rg 5, operation fiber crops
Tired, preparation time is long；Quan K etc. (Natural Products Preveventive Medicine Nutrition, 2015,
It 1-6) is prepared for ginsenoside Rg 5 with ginseng sapoglycoside Rg 3, optimal conditions is that formic acid concn is 0.01%, and temperature is 120 DEG C, place
The reason time is 4h, obtains 15.1mg ginsenoside Rgs 5 from 100mg ginseng sapoglycoside Rg 3s at this time；(the Shanghai such as 2015 end of the year big friends
Traditional Chinese medicine magazine, 2015,49 (1):Ginsenoside Rg 5 and Rk1 91-95) are prepared for using ginsenoside, in optimised process
Condition, i.e. pressure 125MPa, 120 DEG C of reaction temperature, formic acid concn 0.05%, concentration of alcohol 50%, reaction time 2h, in product
The total content of Rg5 and Rk1 obtains 19.9%.
Currently, there has been no using ginseng as raw material, the relevant report of ginsenoside Rg 5 is directly therefrom extracted.
Invention content
One of technical scheme of the present invention is：A method of extraction ginsenoside Rg 5, including using acid as secondary solvent
The step of ginseng pulverate is extracted.
The present invention is added acid and is extracted as secondary solvent directly using ginseng pulverate as raw material, will in extraction process
Extraction, directionally hydrolyzing and the dehydration fusion of ginsenoside are completed in primary extraction, direct high efficiency extraction ginsenoside Rg 5.
Wherein, it is described acid be sulfuric acid, hydrochloric acid, phosphoric acid, nitric acid, citric acid, tartaric acid, malic acid, oxalic acid, lactic acid, formic acid,
The mixture of one or more of acetic acid, preferably hydrochloric acid or phosphoric acid.
Preferably, further include main solvent in extraction system, the main solvent is one in water, alcohols solvent, ketones solvent
Kind or several mixtures, the one kind or several of the alcohols solvent in methanol, ethyl alcohol, normal propyl alcohol, isopropanol, n-butanol
Kind；The ketones solvent is selected from acetone.
Specifically, when it is described acid be hydrochloric acid, sulfuric acid, phosphoric acid, nitric acid when, the main solvent be methanol, ethyl alcohol, normal propyl alcohol,
Any one in isopropanol, n-butanol or water single solvent or methanol, ethyl alcohol, normal propyl alcohol, isopropanol, n-butanol and water shape
At binary mixed solvent or methanol, ethyl alcohol, normal propyl alcohol, isopropanol, n-butanol in arbitrary two kinds and the ternary that is formed of water it is mixed
Bonding solvent；Preferably, when main solvent is binary or ternary mixed solvent, the volume of organic solvent accounts for total main solvent volume
70-100%.
When the acid is citric acid, tartaric acid, malic acid, oxalic acid, lactic acid, formic acid, acetic acid, the main solvent is first
Binary mixed solvent or methanol that any one and water in alcohol, ethyl alcohol, normal propyl alcohol, isopropanol, n-butanol are formed, ethyl alcohol, just
The ternary mixed solvent that arbitrary two kinds in propyl alcohol, isopropanol, n-butanol and water are formed.Preferably, when main solvent be binary or
When ternary mixed solvent, the volume of water accounts for the 60-80% of total main solvent volume.
When extraction, secondary solvent or secondary solvent are added into ginseng pulverate and main solvent forms extraction system, it is preferable that when
In extraction system when sour final concentration of 0.01-0.5mol/L (preferably 0.01-0.2mol/L), main solvent and secondary solvent can
Reach best synergistic effects, it can be ensured that good extraction effect and high Rg5 recovery rates.
Preferably, the feed liquid (g of ginseng pulverate and solvent:ML) than being 1:5-1:60, preferably 1:15-1:60.
Preferably, the extraction carries out 30min-6h under the conditions of 50-100 DEG C, is preferably carried out under the conditions of 60-100 DEG C
3-6h。
Further include the steps that being post-processed to extracting solution after extraction, the post-processing is specially：Separation of solid and liquid carries
It takes liquid, after liquid phase alkali neutralization, concentrates to obtain the final product.
Waste residue after separation of solid and liquid is preferably washed twice using water-saturated n-butanol, and cleaning solution is incorporated into liquid phase.
The preferable extracting method of the present invention is：According to 1:5-1:Main solvent is added into ginseng pulverate, and adds for 60 solid-liquid ratio
Enter secondary solvent acid to ensure final concentration of 0.01-0.5mol/L sour in system, normal pressure extracts under the conditions of 50-100 DEG C
30min-6h after extraction, is separated by solid-liquid separation, and alkali neutralization extracting solution is added into isolated extracting solution and is concentrated into
It does to obtain the final product.
The present invention more preferably extracting method is：According to 1:15-1:The mixed of alcohol and water is added into ginseng pulverate for 60 solid-liquid ratio
Bonding solvent, and acid is added to ensure final concentration of 0.01-0.2mol/L sour in system, normal pressure extracts under the conditions of 60-100 DEG C
3-6h after extraction, is separated by solid-liquid separation, and alkali neutralization extracting solution is added into isolated extracting solution and is concentrated to dryness
To obtain the final product.
Ginseng pulverate of the present invention is that panax species root any part is pulverized, and crosses 80~160 mesh and sieves
It arrives.
The panax species dawn known to those skilled in the art, the preferably described panax species of the present invention are selected from people
One or more of ginseng, American Ginseng, Radix Notoginseng, panax japonicus.
The present invention is extraction raw material with ginseng pulverate, in such a way that main solvent and secondary solvent are used cooperatively, is extracted normal
Pressure progress, primary to extract, without extracting repeatedly, and extraction time is short, it is not necessary that protective agent is added and resists in extraction process
Oxidant has easy to operate, extract yield height, the mild feature of experiment condition.
On the basis of common knowledge of the art, above-mentioned each optimum condition can be combined with each other each preferably up to the present invention
Embodiment.
Description of the drawings
Fig. 1 is the liquid chromatogram for the extract that embodiment 1 obtains.
Specific implementation mode
The following examples are used to illustrate the present invention, but are not intended to limit the scope of the present invention..Substance involved in embodiment
Commercially available acquisition, the operation being related to are this field routine operation unless otherwise specified.
Embodiment 1：
A kind of extracting method of ginsenoside Rg 5：Ginseng root is taken, 120 mesh sieve is smashed it through, takes 0.5g ginsengs
(the two volume ratio is 4 for powder, the n-butanol of 60 times of volumes of addition and the mixed solvent of water:1) hydrochloric acid, which is added, makes its acid concentration be
0.2mol/L extracts 4h in 60 DEG C of stirred in water bath.Extract is centrifuged, extraction fluid and solid, solid with water saturation just
Butanol washes twice repeatedly, merges with extracting solution, through being saturated Na2CO3After aqueous solution neutralizes, rotation is utilized at a temperature of less than 60 DEG C
Turn evaporimeter to be concentrated to dryness up to the extract containing ginsenoside Rg 5.
Embodiment 2：
A kind of extracting method of ginsenoside Rg 5：Ginseng root is taken, 100 mesh sieve is smashed it through, takes 0.5g ginsengs
Powder, be added the methanol of 20 times of volumes, n-butanol, water mixed solvent (three's volume ratio is 3:5:2) sulfuric acid, which is added, keeps its acid dense
Degree is 0.1mol/L, and 2h is extracted in 80 DEG C of stirred in water bath.Extract is centrifuged, extraction fluid and solid, solid is full with water
It washes twice with n-butanol, merges with extracting solution repeatedly, through being saturated Na2CO3It is sharp at a temperature of less than 60 DEG C after aqueous solution neutralizes
It is concentrated to dryness up to the extract containing ginsenoside Rg 5 with Rotary Evaporators.
Embodiment 3：
A kind of extracting method of ginsenoside Rg 5：Ginseng root is taken, 120 mesh sieve is smashed it through, takes 0.5g ginsengs
The ethyl alcohol of 15 times of volumes, the mixed solvent (5 of n-butanol, water is added in powder:3:2) hydrochloric acid, which, is added, makes its acid concentration be 0.06mol/
L extracts 6h in 70 DEG C of stirred in water bath.Extract is centrifuged, extraction fluid and solid, solid with water-saturated n-butanol repeatedly
It washes twice, merges with extracting solution, through being saturated Na2CO3After aqueous solution neutralizes, Rotary Evaporators are utilized at a temperature of less than 60 DEG C
It is concentrated to dryness up to the extract containing ginsenoside Rg 5.
Embodiment 4：
A kind of extracting method of ginsenoside Rg 5：Ginseng root is taken, 120 mesh sieve is smashed it through, takes 0.5g ginsengs
The isopropanol of 20 times of volumes, the mixed solvent (4 of n-butanol and water is added in powder:3:3) hydrochloric acid, which is added, makes its acid concentration be
0.01mol/L extracts 5h in 100 DEG C of stirred in water bath.Extract centrifuges, extraction fluid and solid, solid with water saturation just
Butanol washes twice repeatedly, merges with extracting solution, through being saturated Na2CO3After aqueous solution neutralizes, rotation is utilized at a temperature of less than 60 DEG C
Turn evaporimeter to be concentrated to dryness up to the extract containing ginsenoside Rg 5.
Embodiment 5：
A kind of extracting method of ginsenoside Rg 5：Ginseng root is taken, 100 mesh sieve is smashed it through, takes 0.5g ginsengs
The n-butanol of 40 times of volumes, the mixed solvent (1 of water is added in powder:4) tartaric acid, which, is added, makes its acid concentration be 0.2mol/L, 85
DEG C stirred in water bath extracts 5h.Extract is centrifuged, extraction fluid and solid, solid wash two repeatedly with water-saturated n-butanol
It is secondary, merge with extracting solution, through being saturated Na2CO3After aqueous solution neutralizes, it is concentrated into using Rotary Evaporators at a temperature of less than 60 DEG C
The dry extract containing ginsenoside Rg 5 to obtain the final product.
Embodiment 6：
The extracting method of the embodiment differs only in tartaric acid replacing with malic acid with embodiment 5.
Embodiment 7：
The extracting method of the embodiment differs only in tartaric acid replacing with lactic acid with embodiment 5.
Comparative example 1：
The extracting method of the comparative example is differed only in embodiment 1：After hydrochloric acid is added, the concentration of hydrochloric acid in system
For 1mol/L.
Comparative example 2：
The extracting method of the comparative example is differed only in embodiment 1：Solvent, n-butanol and water are replaced with into acetic acid second
Ester.
Comparative example 3：
The extracting method of the comparative example is differed only in embodiment 1：3h is extracted at 150 DEG C.
To embodiment 1-7, the extract of comparative example 2 carries out HPLC detections, and testing conditions are：
Chromatographic column：Pinnade (150 × 4.60mm, 5 μm)；
Mobile phase：A phases：Acetonitrile, B phases：Pure water (ultrasonic degassing processing)；
Gradient elution：0.00~10.00min, A：22%；10.00~20.00min, A：22%；20.00~
25.00min A:27%；25.00~45.00min, A:31%；45.00~60.00min, A:38%；60.00~
65.00min A:52%；65~75min, A:52%；75.00~75.10min, A:55%；75.00~75.10min, A:
55%；75.10~95.00min, A:90%；95.00~95.10min；
Flow velocity:1.0mL/min；
Detection wavelength:203nm；
Column temperature:Room temperature；
Sample size:20μL.
Detection method：Respectively by embodiment 1-7, the extract of comparative example 2 is dissolved in chromatography methanol, 0.45 μm of membrane filtration
Sample introduction is analyzed afterwards, is calculated by quality × 100% of quality/ginseng pulverate of recovery rate=ginsenoside Rg 5 of ginsenoside Rg 5.
Testing result is as shown in table 1：
Table 1：Embodiment 1-4, comparative example 1-3 results
| Serial number | Rg5 weight (g) | Rg5 recovery rates (%) |
| Embodiment 1 | 0.0105 | 2.1 |
| Embodiment 2 | 0.0115 | 2.3 |
| Embodiment 3 | 0.0170 | 3.4 |
| Embodiment 4 | 0.0140 | 2.8 |
| Embodiment 5 | 0.0090 | 1.8 |
| Embodiment 6 | 0.0085 | 1.7 |
| Embodiment 7 | 0.0095 | 1.9 |
| Comparative example 1 | 0 | 0 |
| Comparative example 2 | 0.0007 | 0.14 |
| Comparative example 3 | 0 | 0 |
Although above having used general explanation, specific implementation mode and experiment, the present invention is made to retouch in detail
It states, but on the basis of the present invention, it can be made some modifications or improvements, this is apparent to those skilled in the art
's.Therefore, these modifications or improvements without departing from theon the basis of the spirit of the present invention, belong to claimed
Range.
Claims (9)
1. a kind of method of extraction ginsenoside Rg 5, it is characterised in that：According to 1:5-1:60 solid-liquid ratio adds into ginseng pulverate
Enter main solvent, and secondary solvent acid is added to ensure final concentration of 0.01-0.2mol/L sour in system, in 60-100 DEG C of condition
Lower normal pressure extracts 2-6h, after extraction, is separated by solid-liquid separation, and alkali neutralization extracting solution is added simultaneously into isolated extracting solution
Be concentrated to dryness to get；
Wherein, the acid is sulfuric acid, hydrochloric acid, phosphoric acid, nitric acid, citric acid, tartaric acid, malic acid, oxalic acid, lactic acid, formic acid, acetic acid
One or more of mixture；The main solvent is in water, methanol, ethyl alcohol, normal propyl alcohol, isopropanol, n-butanol, acetone
One or more of mixtures.
2. according to the method described in claim 1, it is characterized in that：It is described when the acid is hydrochloric acid, sulfuric acid, phosphoric acid, nitric acid
Main solvent is the binary mixed solvent of one kind in alcohols solvent or any one and water formation in water or alcohols solvent, or
The arbitrary two kinds ternary mixed solvents formed with water in alcohols solvent；
When the acid is citric acid, tartaric acid, malic acid, oxalic acid, lactic acid, formic acid, acetic acid, the main solvent is alcohols solvent
In any one and water binary mixed solvent or alcohols solvent for being formed in arbitrary two kinds and the ternary mixing that is formed of water it is molten
Agent.
3. according to the method described in claim 2, it is characterized in that：When it is described acid be hydrochloric acid, sulfuric acid, phosphoric acid, nitric acid, and master it is molten
When agent is binary or ternary mixed solvent, organic solvent accounts for the 70-100% of main solvent volume.
4. according to the method described in claim 2, it is characterized in that：When it is described acid be citric acid, tartaric acid, malic acid, oxalic acid,
When lactic acid, formic acid, acetic acid, water accounts for the 60-80% of main solvent volume.
5. according to the method described in claim 1, it is characterized in that：Sour final concentration of 0.01-0.2mol/L in extraction system.
6. according to the method described in claim 1, it is characterized in that：Feed liquid (the g of ginseng pulverate and solvent:ML) than being 1:15-1:
60。
7. according to claim 1-6 any one of them methods, it is characterised in that：The extraction carries out under the conditions of 60-100 DEG C
3-6h。
8. according to the method described in claim 7, it is characterized in that：The ginseng pulverate is pulverized by the root of panax species
It arrives.
9. according to the method described in claim 8, it is characterized in that：The panax species be selected from ginseng, American Ginseng, Radix Notoginseng,
One or more of panax japonicus.
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