CN105348356B - A kind of method preparing 20-glucose-ginsenoside Rf's monomer from Panax Japonicus Var. Major - Google Patents
A kind of method preparing 20-glucose-ginsenoside Rf's monomer from Panax Japonicus Var. Major Download PDFInfo
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- CN105348356B CN105348356B CN201510752697.2A CN201510752697A CN105348356B CN 105348356 B CN105348356 B CN 105348356B CN 201510752697 A CN201510752697 A CN 201510752697A CN 105348356 B CN105348356 B CN 105348356B
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Abstract
The invention discloses a kind of method preparing 20 glucose ginsenoside Rf's monomers from Panax Japonicus Var. Major, the preparation component containing 20 glucose ginsenoside Rf's monomers, utilizing high speed adverse current chromatogram method to separate 20 glucose ginsenoside Rf's monomers from the component containing 20 glucose ginsenoside Rf's monomers, wherein high speed adverse current chromatogram condition is: the solvent system separated as high speed adverse current chromatogram using the n-butanol ethyl acetate water that volume ratio is 4～6: 1: 5～7.Inventor finds that column chromatography combines high speed adverse current chromatogram (HSCCC) and separates 20 glucose ginsenoside Rfs, and its process is simple, greatly reduces the consumption of organic reagent, and obtains the purity of monomer more than 95%.The present invention is the new method using high speed adverse current chromatogram (HSCCC) method to separate 20 glucose ginsenoside Rf's monomers first.20 glucose ginsenoside Rf's monomers that the present invention obtains can be used for preparing pharmaceutical composition, health food and other products.
Description
Technical field
The present invention relates to a kind of method preparing 20-glucose-ginsenoside Rf's monomer from Panax Japonicus Var. Major, belong to
In field of natural medicinal chemistry.
Background technology
Panax Japonicus Var. Major system Araliaceae Panax Japonicus Var. Major Panax japonicus C.A.Mey.var.major (Burk.)
C.Y.Wu et K.M.Feng or Panax bipinnatifidus Panax japonicus C.A.Mey.var.
The dry rhizome of bipinnatifidus (Seem.) C.Y.Wu et K.M.Feng.Autumn excavates, and removes thick
Skin and fibrous root, be dried；Or be dried after steaming (boiling) thoroughly.There is tonifying lung yin-nourishing, stasis-dispelling and pain-killing, stop blooding it
Function；For deficiency of both qi and yin, dysphoria with smothery sensation is thirsty, cough due to consumptive disease, injury from falling down, joint pain, hemoptysis,
Spit blood, bleeding from five sense organs or subcutaneous tissue, uterine bleeding, traumatism and bleeding.
Up to the present people get multiple saponins compound from Panax Japonicus Var. Major, mainly include ginseng
Saponin(e Ro, panax japonicus saponin IVa, panax japonicus saponin V, ginsenoside Re, ginsenoside Rd, people
Ginseng saponin(e Rg1, ginsenoside Rg2, Panax Japonicus Var. Major glycosides F1, F2, F3, F4, F5, F6,20-glucose
The saponins compounds such as-ginsenoside Rf, wherein ginsenoside Ro, panax japonicus saponin Iva, panax japonicus
Saponin(e V, ginsenoside Re, ginsenoside Rd study more, and about 20-glucose-ginseng soap
The report of glycosides Rf is the most little.
Because different saponin monomers has different biologically actives, such as ginsenoside Rg1It is all
The ginsenoside that in ginsenoside, anti-fatigue active is the strongest, and ginsenoside Rb2There is the strongest reducing blood lipid
Effect.Often relate to reach out for various saponin monomer during developing new drug or health food,
Therefore invention can obtain the new method of monomer saponin simply and is one and significantly works.
The method utilizing column chromatography can get 20-glucose-ginsenoside Rf from Panax Japonicus Var. Major, but its mistake
Journey is relatively complicated, and the organic solvent of use is more, and the monomer purity obtained is relatively low, and productivity is low.
Summary of the invention
The technical problem to be solved in the present invention is to overcome existing defect, it is provided that a kind of system from Panax Japonicus Var. Major
The method of standby 20-glucose-ginsenoside Rf's monomer, the monomer purity that the method obtains is higher, and productivity is high.
In order to solve above-mentioned technical problem, the invention provides following technical scheme:
A kind of method preparing 20-glucose-ginsenoside Rf's monomer from Panax Japonicus Var. Major, preparation is containing 20-
The component of glucose-ginsenoside Rf's monomer, utilize high speed adverse current chromatogram method from containing 20-glucose-
The component of ginsenoside Rf's monomer separates 20-glucose-ginsenoside Rf's monomer, wherein high-speed counter-current
Chromatographic condition is: inverse as high speed using n-butanol-ethyl acetate-water that volume ratio is 4～6: 1: 5～7
The solvent system that flow chromatography separates.
In such scheme preferably, wherein high speed adverse current chromatogram condition is: with volume ratio for 4: 1:
The solvent system that the n-butanol-ethyl acetate-water of 5 separates as high speed adverse current chromatogram.
In such scheme preferably, the condition that high speed adverse current chromatogram separates also includes: flow velocity is 2
mL·min-1, rotating speed is 800r min-1, detection wavelength is 203nm.
In such scheme preferably, high speed adverse current chromatogram is utilized to separate 20-glucose-ginsenoside Rf
The concrete operations of monomer are: take n-butanol 1200mL, ethyl acetate 300mL, water 1500mL, put
In the separatory funnel of 2000mL, vibration shakes up, and stands overnight, and above phase is fixing phase, and lower phase is flowing
Phase, accurately weighs described component 170mg containing 20-glucose-ginsenoside Rf's monomer, uses 10mL
Lower phased soln, as sample solution, with 30mL min-1It is filled with fixing mutually in high speed adverse current chromatogram, fortune
Row 20min, with 2mL min-1Import flowing phase, to the constant volume flowed out, inject sample molten
Liquid, collects the efflux containing 20-glucose-ginsenoside Rf, decompression and solvent recovery, obtains described 20-
Glucose-ginsenoside Rf's monomer.
In any of the above-described scheme preferably, preparation is described containing 20-glucose-ginsenoside Rf's monomer
The method of component be: take Rhizoma panacis majoris extract in order to dichloromethane that volume ratio is 5～7:1:0.4～1:
Methyl alcohol: water carries out silica gel column chromatography mutually for flowing, obtains containing 20-glucose-ginsenoside Rf's part；
Again by containing 20-glucose-ginsenoside Rf part with volume ratio as 1:1.5～2.5 methanol-water be flowing
Carry out ODS column chromatography for separation mutually, obtain containing 20-glucose-ginsenoside Rf's component.
In any of the above-described scheme preferably, preparation is described containing 20-glucose-ginsenoside Rf's monomer
The method of component be: taking Rhizoma panacis majoris extract in order to volume ratio is the dichloromethane of 6:1:0.5: methyl alcohol:
Water carries out silica gel column chromatography mutually for flowing, obtains containing 20-glucose-ginsenoside Rf's part；To contain again
20-glucose-ginsenoside Rf's part methanol-water with volume ratio as 1:2 is had to carry out ODS mutually for flowing
Column chromatography for separation, obtains containing 20-glucose-ginsenoside Rf's component.
In any of the above-described scheme preferably, the preparation method of described Rhizoma panacis majoris extract is: by pearl
Ginseng is pulverized, and by water or hydrous ethanol solution refluxing extraction, aqueous extract directly macroporous absorbent resin excessively adsorbs,
Ethanol extract reclaims ethanol extremely without crossing macroporous absorbent resin absorption after alcohol taste, and ethanol or methyl alcohol desorption subtract
Pressure recycling design obtains described Rhizoma panacis majoris extract.
In any of the above-described scheme preferably, the preparation method of described Rhizoma panacis majoris extract is: take pearl
Join 10 kilograms, 70% ethanol water refluxing extraction 3 times, ethanol consumption is respectively 10,8,8 times (V/V),
Return time is respectively 1.5h, 1.0h, 1.0h, merges No. three extracts, recycling design, obtains after drying
Described Rhizoma panacis majoris extract 1400g.
Beneficial effects of the present invention: inventor finds that column chromatography combines high speed adverse current chromatogram (HSCCC) and separates
20-glucose-ginsenoside Rf, its process is simple, greatly reduces the consumption of organic reagent, and obtains list
The purity of body is more than 95%.The present invention is to use high speed adverse current chromatogram (HSCCC) method to separate 20-first
The new method of glucose-ginsenoside Rf's monomer.The 20-glucose that the present invention obtains-ginsenoside Rf is single
Body can be used for preparing pharmaceutical composition, health food and other products.
Detailed description of the invention
Hereinafter the preferred embodiments of the present invention are illustrated, it will be appreciated that preferred reality described herein
Execute example be merely to illustrate and explain the present invention, be not intended to limit the present invention.
Embodiment 1
Panax Japonicus Var. Major 10 kilograms, 70% ethanol water refluxing extraction 3 times, ethanol consumption is respectively 10,8,8
Times (V/V), return time is respectively 1.5h, 1.0h, 1.0h, merges No. three extracts, recycling design,
Obtain Rhizoma panacis majoris extract 1400g after drying.
Taking Rhizoma panacis majoris extract 50g, separate with silica gel column chromatography, flowing is dichloromethane mutually: methyl alcohol:
Water (6:1:0.5, volume ratio), obtains the component B 10g containing 20-glucose-ginsenoside Rf；By component
B ODS column chromatography for separation, flowing is methanol-water (1:2, volume ratio) mutually, obtains containing 20-grape
The component I 8g of sugar-ginsenoside Rf；Component I high speed adverse current chromatogram (HSCCC) is separated,
With solvent burden ratio as n-butanol-ethyl acetate-water (4: 1: 5, volume ratio) is as preparative adverse current chromatogram
The solvent system separated, flow velocity is 2mL min-1, rotating speed is 800r min-1, detection wavelength is
203nm。
Concrete operations are as follows: take n-butanol 1200mL, ethyl acetate 300mL, water 1500mL, put
In the separatory funnel of 2000mL, vibration shakes up, and stands overnight.Above phase is fixing phase, and lower phase is stream
Dynamic phase, accurately weighs component I powder 170mg, with phased soln under 10mL, as sample solution, standby
With.
With 30mL min-1It is filled with fixing mutually in HSCCC, runs 20min；With 2mL min-1Lead
Enter the phase that flows, to the constant volume flowed out, inject sample solution.Connect according to HSCCC chromatographic peak
Take every section of stream part, collect the efflux containing 20-glucose-ginsenoside Rf, decompression and solvent recovery, obtain
Described 20-glucose-ginsenoside Rf's monomer.
20-glucose-the ginsenoside Rf obtained being detected with HPLC-ELSD, its purity is 99.5%.
The chromatographic condition of HPLC-ELSD is as follows.
Chromatographic column: Agilent Eclipse XDB-C18 (ODS, 4.6 × 250mm, 5 μm)；
Flowing phase: acetonitrile-water (20:80)；Flow velocity: 1.0mL/min；Column temperature: 30 DEG C；
Sample size: 20 μ L；ELSD detector drift tube temperature: 109 DEG C；Ram state: close；
Nebulizer gas pressure: 2.56bar；Multiplication factor: 1.0 times.
The nuclear magnetic data of the 20-glucose-ginsenoside Rf obtained:
13C NMR(C5D5N, 150MHz) δC: 39.58 (C-1), 27.91 (C-2), 78.81 (C-3),
40.34 (C-4), 61.53 (C-5), 80.03 (C-6), 45.06 (C-7), 41.30 (C-8), 50.08 (C-9),
39.79 (C-10), 31.07 (C-11), 70.29 (C-12), 49.32 (C-13), 51.52 (C-14), 30.82 (C-15),
26.76 (C-16), 51.65 (C-17), 17.71 (C-18), 17.64 (C-19), 83.40 (C-20), 22.43 (C-21),
36.24 (C-22), 23.33 (C-23), 126.12 (C-24), 131.05 (C-25), 25.90 (C-26),
17.89 (C-27), 32.20 (C-28), 16.89 (C-29), 17.28 (C-30).(6-glu:103.97 C-1 '),
79.45 (C-2 ') 78.20 (C-3 '), 71.83 (C-4 '), 80.07 (C-5 '), 63.04 (C-6 ').2 '-glu:
103.97 (C-1 "), 76.16 (C-2 "), 78.39 (C-3 "), 72.48 (C-4 "), 79.71 (C-5 "), 63.49 (C-6 ").
20-glu:98.37 (C-1 " '), 75.26 (C-2 " '), 78.55 (C-3 " '), 71.83 (C-4 " '), 78.00 (C-5 " '),
63.04(C-6″′)。
1H NMR(C5D5N, 600MHz) δH: 5.807 (1H, d, J=7.2,6-glu-H-1'), 5.125 (1H,
M, H-24), 5.053 (1H, d, J=7.8,20-glu-H-1 " '), 4.787 (1H, d, J=7.8,2'-glu-
H-1 "), 4.371 (1H, s, 6-glu-H-6 ' a), 4.357 (1H, s, 20-glu-H-6 " ' a), 4.344 (1H,
S, 2 '-glu-H-6 " a), 4.331 (1H, s, 6-glu-H-6 ' b), 4.253 (1H, m, 20-glu-H-
6 " ' b), 4.231 (1H, m, 2 '-glu-H-6 " b), 4.085 (1H, m, H-12 α), 3.341 (1H, m,
H-3 α), 1.869 (3H, s, H-28), 1.472 (9H, s, H-26,27,29), 1.003 (3H, s,
H-18), 0.830 (3H, s, H-19), 0.675 (3H, s, H-30).
Embodiment 2
Taking Panax Japonicus Var. Major total extract 50g, separate with silica gel column chromatography, flowing is ethyl acetate mutually: methyl alcohol:
Water (7:1:0.5, volume ratio), obtains component B9.1g containing 20-glucose-ginsenoside Rf；By component
B ODS column chromatography for separation, flowing is methanol-water (1:1.5, volume ratio) mutually, obtains containing 20-Portugal
The component I 7.3g of grape sugar-ginsenoside Rf；Component I high speed adverse current chromatogram (HSCCC) is carried out point
From, with solvent burden ratio as n-butanol-ethyl acetate-water (4: 1: 5, volume ratio) as preparative adverse current
The solvent system of chromatographic isolation, flow velocity is 2mL min-1, rotating speed is 800r min-1, detect wavelength
For 203nm.
Concrete operations are as follows: take n-butanol 1200mL, ethyl acetate 300mL, water 1500mL, put
In the separatory funnel of 2000mL, vibration shakes up, and stands overnight.Above phase is fixing phase, and lower phase is stream
Dynamic phase, accurately weighs component I powder 170mg, with phased soln under 10mL, as sample solution, standby
With.
With 30mL min-1It is filled with fixing mutually in HSCCC, runs 20min；With 2mL min-1Lead
Enter the phase that flows, to the constant volume flowed out, inject sample solution.Connect according to HSCCC chromatographic peak
Take every section of stream part, collect the efflux containing 20-glucose-ginsenoside Rf, decompression and solvent recovery, obtain
Described 20-glucose-ginsenoside Rf's monomer.
20-glucose-the ginsenoside Rf obtained being detected with HPLC-ELSD, its purity is 98.2%.
Embodiment 3
Taking Panax Japonicus Var. Major total extract 50g, separate with silica gel column chromatography, flowing is ethyl acetate mutually: ethanol:
Water (7:1:1, volume ratio), obtains component B8.5g containing 20-glucose-ginsenoside Rf；By component B
Using ODS column chromatography for separation, flowing is methanol-water (1:1.5, volume ratio) mutually, obtains containing 20-grape
The component I 6.9g of sugar-ginsenoside Rf；Component I high speed adverse current chromatogram (HSCCC) is separated,
With solvent burden ratio as n-butanol-ethyl acetate-water (4: 1: 5, volume ratio) is as preparative adverse current chromatogram
The solvent system separated, flow velocity is 2mL min-1, rotating speed is 800r min-1, detection wavelength is
203nm。
Concrete operations are as follows: take n-butanol 1200mL, ethyl acetate 300mL, water 1500mL, put
In the separatory funnel of 2000mL, vibration shakes up, and stands overnight.Above phase is fixing phase, and lower phase is stream
Dynamic phase, accurately weighs component I powder 170mg, with phased soln under 10mL, as sample solution, standby
With.
With 30mL min-1It is filled with fixing mutually in HSCCC, runs 20min；With 2mL min-1Lead
Enter the phase that flows, to the constant volume flowed out, inject sample solution.Connect according to HSCCC chromatographic peak
Take every section of stream part, collect the efflux containing 20-glucose-ginsenoside Rf, decompression and solvent recovery, obtain
Described 20-glucose-ginsenoside Rf's monomer.
20-glucose-the ginsenoside Rf obtained being detected with HPLC-ELSD, its purity is 98.0%.
Embodiment 4
Taking Panax Japonicus Var. Major total extract 50g, separate with silica gel column chromatography, flowing is dichloromethane mutually: methyl alcohol:
Water (5:1:0.4, volume ratio), obtains component B9.7g containing 20-glucose-ginsenoside Rf；By component
B ODS column chromatography for separation, flowing is methanol-water (1:2.5, volume ratio) mutually, obtains containing 20-Portugal
The component I 8.1g of grape sugar-ginsenoside Rf；Component I high speed adverse current chromatogram (HSCCC) is carried out point
From, with solvent burden ratio as n-butanol-ethyl acetate-water (6:1:7, volume ratio) divides as preparative adverse current chromatogram
From solvent system, flow velocity is 2mL min-1, rotating speed is 800r min-1, detection wavelength is 203nm.
Concrete operations are as follows: take n-butanol 1200mL, ethyl acetate 200mL, water 1400mL, put
In the separatory funnel of 2000mL, vibration shakes up, and stands overnight.Above phase is fixing phase, and lower phase is stream
Dynamic phase, exact ingredient I powder 170mg, with phased soln under 10mL, as sample solution, standby.
With 30mL min-1It is filled with fixing mutually in HSCCC, runs 20min；With 2mL min-1Lead
Enter the phase that flows, to the constant volume flowed out, inject sample solution.Connect according to HSCCC chromatographic peak
Take every section of stream part, collect the efflux containing 20-glucose-ginsenoside Rf, decompression and solvent recovery, obtain
Described 20-glucose-ginsenoside Rf's monomer.
20-glucose-the ginsenoside Rf obtained being detected with HPLC-ELSD, purity is 95.5%.
Last it is noted that the foregoing is only the preferred embodiments of the present invention, it is not used to limit
The present invention processed, although being described in detail the present invention with reference to previous embodiment, for this area
For technical staff, the technical scheme described in foregoing embodiments still can be modified by it, or
Person carries out equivalent to wherein portion of techniques feature.All within the spirit and principles in the present invention, made
Any modification, equivalent substitution and improvement etc., should be included within the scope of the present invention.
Claims (1)
1. the method preparing 20-glucose-ginsenoside Rf's monomer from Panax Japonicus Var. Major, it is characterised in that: Panax Japonicus Var. Major 10 is public
Jin, 70% ethanol water refluxing extraction 3 times, ethanol consumption is respectively 10,8,8 times (V/V), return time be respectively 1.5h,
1.0h, 1.0h, merge No. three extracts, recycling design, obtain Rhizoma panacis majoris extract 1400g after drying；Take Panax Japonicus Var. Major to carry
Taking thing 50g, separate with silica gel column chromatography, flowing is the dichloromethane of 6:1:0.5 for volume ratio mutually: methyl alcohol: water, obtains
Component B 10g containing 20-glucose-ginsenoside Rf；Component B is used ODS column chromatography for separation, and flowing is volume mutually
Than the methanol-water for 1:2, obtain the component I 8g containing 20-glucose-ginsenoside Rf；By component I high-speed counter-current
Chromatogram separates, and with n-butanol-ethyl acetate-water that solvent volume ratio is 4: 1: 5, divides as preparative adverse current chromatogram
From solvent system, flow velocity is 2mL min-1, rotating speed is 800r min-1, detection wavelength is 203nm.
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| CN201510752697.2A CN105348356B (en) | 2015-11-09 | 2015-11-09 | A kind of method preparing 20-glucose-ginsenoside Rf's monomer from Panax Japonicus Var. Major |
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