CN105061182A - Method for extracting, separating and purifying emodin and physcion from polygonum cuspidatum - Google Patents
Method for extracting, separating and purifying emodin and physcion from polygonum cuspidatum Download PDFInfo
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Abstract
The invention relates to a method for extracting, separating and purifying emodin and physcion from polygonum cuspidatum. The method is characterized by using the medicinal material polygonum cuspidatum as a raw material and comprises the following steps: (1) extraction; (2) extraction; (3) high performance liquid chromatographic separation analysis; (4) semi-preparative separation and purification; (5) compound purity detection and structure identification. The method has the advantages that two high-purity components are obtained by using semi-preparative high performance liquid chromatography for separation and purification and using methanol-water as a mobile phase and are identified respectively to be emodin and physcion; the process is environment-friendly in course, does not have severe harm to the environment and is low in comprehensive cost.
Description
Technical field
The invention belongs to chemical field, specifically relate to a kind of method of extracting and developing purifying Schuttgelb and rheochrysidin from giant knotweed.
Background technology
Giant knotweed is polygonaceae arsesmart giant knotweed
polygonumcuspidatumsieb.etZucc. dry rhizome, cold in nature, bitter, return liver, lung, gallbladder channel, have expelling wind and removing dampness, expelling phlegm for arresting cough, effect clearing heat and detoxicating, promoting blood circulation and removing blood stasis, tcm clinical practice be used for the treatment of jaundice due to damp-heat, cough due to lung-heat, sore and toxic, arthralgia, through diseases such as amenorrhoea pain, burn due to hot liquid or fire, wounies.The multiple pharmacological effect such as pharmacological research shows that giant knotweed has cardiac stimulant, protects the liver, antibacterial, antiviral, antitumor, anti-oxidant, anti-inflammatory.Chemical constitution study shows that its main component has trans-resveratrol, polydatin, Schuttgelb, rheochrysidin etc.The anthraquinone analog compound such as Schuttgelb and rheochrysidin has anti-inflammatory, antibacterial, antiviral and antitumor action.According to the literature, in separation and purification giant knotweed, the method for anthraquinone analog compound mainly contains repeatedly silica gel column chromatography and high-speed countercurrent chromatography, and the operating process of silica gel column chromatography is loaded down with trivial details, and the rate of recovery is lower, often uses the organic solvent that the toxicity such as chloroform, benzene is stronger; In high-speed countercurrent chromatography, the selection and comparison difficulty of solvent systems, lacks theoretical direction.Therefore, the method setting up anthraquinone analog compound in a kind of efficient extracting and developing purifying giant knotweed fast for in-depth giant knotweed pharmacological research and improve quality control system and all have great importance.The invention provides a kind of method of efficient, quick, easy extracting and developing purifying Schuttgelb and rheochrysidin from giant knotweed.
Summary of the invention
The object of the present invention is to provide a kind of method of efficient, quick, easy extracting and developing purifying Schuttgelb and rheochrysidin from giant knotweed.
The solution of the present invention is as follows:
From giant knotweed, the method for extracting and developing purifying Schuttgelb and rheochrysidin, the steps include:
(1) extract: pulverized by Rhizoma Polygoni Cuspidati, extract with organic solvent, filter, extracting solution obtains crude extract through concentrating under reduced pressure.
(2) extract: be distributed in by giant knotweed crude extract in petroleum ether-ethyl acetate-methanol-water (2:5:6:10, V/V), jolting, reach by organic phase and aqueous phase separation after partition equilibrium, organic phase and aqueous phase respectively concentrating under reduced pressure obtain sample 1 and sample 2.
(3) high performance liquid chromatography compartment analysis: carry out compartment analysis to the composition of sample 1 with analysis mode high performance liquid chromatograph, chromatographic column is C
18post (250mm × 4.6mmI.D., 5 μm), moving phase is methanol-water (90:10, V/V), and flow velocity is 1.0mL/min, and determined wavelength is 254nm, and column temperature is room temperature.
(4) semi-preparative separation and purification: carry out separation and purification to the composition in sample 1 with Semipreparative chromatography instrument, chromatographic column is C
18post (250mm × 25.4mmI.D., 10 μm), moving phase is methanol-water (85:15, V/V), and determined wavelength is 254nm, and column temperature is room temperature.According to color atlas manual collection target components cut, concentrating under reduced pressure is except desolventizing.
(5) purity detecting of compound and Structural Identification: by each target components cut after concentrating under reduced pressure with dissolve with methanol, its purity high performance liquid chromatography detects, chromatographic condition is shown in step (3), and analytical results shows that the purity of 2 kinds of compounds all reaches more than 98%.Schuttgelb and rheochrysidin respectively through spectral analysis of the nuclear magnetic resonance 2 kinds of compounds.
Foregoing method, preferred scheme is, step (1) extracting method is cold soaking, ultrasonic and reflux (preferably ultrasonic).
Foregoing method, preferred scheme is, step (1) Extraction solvent is water, ethanol, ether and sherwood oil (preferred alcohol).
Foregoing method, preferred scheme is, the concentration of step (1) extraction ethanol-water solution is 50 ~ 95%(preferably 95%).
Foregoing method, preferred scheme is, when step (1) is extracted, the consumption of solvent is 6-15 times amount (preferably 8 times amount).
Foregoing method, preferred scheme is, step (1) extraction time is 2-5 time (preferably 4 times).
Foregoing method, preferred scheme is, step (1) extraction time is 15-60 minute (preferably 30 minutes).
Foregoing method, preferred scheme is, step (2) carries out all kinds of SOLVENTS in the solvent systems (petroleum ether-ethyl acetate-methanol-water) used in extracting and enriching process volume ratio to anthraquinone is the preferred 2:5:6:10 of 2:5:1:9,2:5:4:6,2:5:6:4 and 2:5:6:10().
Foregoing method, preferred scheme is, the concentration of step (3) high performance liquid chromatography compartment analysis methyl alcohol used is 85%-95%(preferably 90%).
Foregoing method, preferred scheme is, the concentration of step (4) Semipreparative chromatography separation and purification methyl alcohol used is respectively 90%-80%(preferably 85%).
Foregoing method, preferred scheme is, step (4) separation and purification methanol-water solution carries out wash-out, and the flow velocity of elutriant is the preferred 25mL/min of 20-30mL/min().
The present invention relates to a kind of method of extracting and developing purifying Schuttgelb and rheochrysidin from giant knotweed, step is: (1) extracts: pulverized by Rhizoma Polygoni Cuspidati, extract with organic solvent, and filter, extracting solution obtains crude extract through concentrating under reduced pressure.(2) extract: be distributed in by crude extract in petroleum ether-ethyl acetate-methanol-water (2:5:6:10, V/V), jolting, reach by organic phase and aqueous phase separation after partition equilibrium, organic phase and aqueous phase respectively concentrating under reduced pressure obtain sample 1 and sample 2.(3) high performance liquid chromatography compartment analysis: carry out compartment analysis to the composition of sample 1 with analysis mode high performance liquid chromatograph, chromatographic column is C
18post (250mm × 4.6mmI.D., 5 μm), moving phase is methanol-water (90:10, V/V); Flow velocity is 1.0mL/min, and determined wavelength is 254nm, and column temperature is room temperature.(4) semi-preparative separation and purification: carry out separation and purification to the composition in crude extract with Semipreparative chromatography instrument, chromatographic column is C
18post (250mm × 25.4mmI.D., 10 μm), moving phase is methanol-water (85:15, V/V), and determined wavelength is 254nm, and column temperature is room temperature.According to color atlas manual collection target components cut, concentrating under reduced pressure is except desolventizing.(5) purity detecting of compound and Structural Identification: by after each target components cut concentrating under reduced pressure with dissolve with methanol, its purity high performance liquid chromatography detects, chromatographic condition is shown in step (3), and analytical results shows that the purity of 2 kinds of compounds all reaches more than 98%.Schuttgelb and rheochrysidin respectively through spectral analysis of the nuclear magnetic resonance 2 kinds of compounds.This technological process environmental protection, to environment without serious harm, comprehensive cost is low.
The present invention is extracting and developing purifying Schuttgelb and rheochrysidin from giant knotweed, is first extracted by anthraquinone component with 95% ethanol ultrasonic extraction, and strong polar component can be made not to be dissolved; Be distributed in by crude extract in petroleum ether-ethyl acetate-methanol-water solution, jolting, Schuttgelb and rheochrysidin are mainly distributed in organic phase; Next, with analysis mode high performance liquid chromatograph, compartment analysis is carried out to the composition in organic phase; Then, with Semipreparative chromatography instrument, separation and purification is carried out to the composition of organic phase and just can obtain 2 kinds of compounds; Finally, measure by the purity of high performance liquid chromatography to compound, identify according to the structure of spectral analysis of the nuclear magnetic resonance to compound.The method gained target compound purity is high, and foreign matter content is extremely low, this point can from Fig. 3 to Fig. 4 find out.In addition, also there is following advantage:
(1) with the chemical composition in 95% ethanol ultrasonic extraction giant knotweed have that extraction efficiency is high, the fast and simple operation and other advantages of speed.In giant knotweed the traditional extraction process of anthraquinone be adopt sulphuric acid hydrolysis, the method for benzene, chloroform or extracted with diethyl ether, the efficiency of this extracting method is high, but is the use of the stronger organic solvent of toxicity, to environment and human body all unfriendly.
(2) crude extract is distributed in that to carry out enrichment to Schuttgelb and rheochrysidin in petroleum ether-ethyl acetate-methanol-water (2:5:6:10, V/V) system be the principle that make use of " similar mix ".The polarity of Schuttgelb and rheochrysidin is less, is mainly distributed in organic phase, and the polarity of trans-resveratrol, polydatin and emodin-8-O-β-D-glucosule is comparatively large, is mainly distributed in aqueous phase.Like this, just according to the polarity of material, crude extract can be divided into sample 1 and sample 2 two portions by simple extracting operation, sample 1 is mainly containing Schuttgelb and rheochrysidin, and its composition is simply too much compared with crude extract, reduces preparative C to greatest extent
18the contaminated degree of post.
(3) by high performance liquid chromatography, compartment analysis is carried out to the composition of giant knotweed crude extract, make moving phase isocratic elution with methanol-water and can realize baseline separation to 2 kinds of target compounds at short notice.
(4) carry out separation and purification by Semipreparative chromatography method to compound, can obtain 2 kinds of high-purity monomer compounds, method is simple to operate, and efficiency is high, and process cycle is short, saves reagent, reduces production cost.
(5) measure the purity preparing gained compound by high performance liquid chromatography, the method accurately, fast.
(6) ethanol, sherwood oil, ethyl acetate, first alcohol and water is only used in extracting and developing, purge process, do not use environment and the large organic solvent such as chloroform, benzene of harm, methanol-water eluent can be reused repeatedly after underpressure distillation is reclaimed, environmental protection.
(7) optimize the condition (composition of elutriant and flow velocity) of chromatography method, the purity of compound and purification efficiency are all greatly improved.
Accompanying drawing explanation
Fig. 1 is the analysis mode high-efficient liquid phase chromatogram of giant knotweed crude extract.
Fig. 2 is the Semipreparative chromatography figure of giant knotweed crude extract.
Fig. 3 is high-efficient liquid phase chromatogram and the ultraviolet spectrogram of Schuttgelb.
Fig. 4 is high-efficient liquid phase chromatogram and the ultraviolet spectrogram of rheochrysidin.
In figures 1-4, I: Schuttgelb; II: rheochrysidin.
Embodiment
Describe technical scheme of the present invention in detail below in conjunction with embodiment and accompanying drawing, but protection domain is not by this restriction.In embodiment, equipment used or raw material all can obtain from market.Agents useful for same is all purchased from Jinan reagent head factory, and water used is deionized water.
embodiment:from giant knotweed, the method for extracting and developing purifying Schuttgelb and rheochrysidin, the steps include:
(1) extract: pulverized by Rhizoma Polygoni Cuspidati, with 8 times amount 95% ethanol ultrasonic extraction 4 times, each 30 minutes, filter, by extracting solution merging, concentrating under reduced pressure obtains crude extract.
(2) extract: be distributed in by crude extract in petroleum ether-ethyl acetate-methanol-water (2:5:6:10, V/V), jolting, reach by organic phase and aqueous phase separation after partition equilibrium, organic phase and aqueous phase respectively concentrating under reduced pressure obtain sample 1 and sample 2.
(3) high performance liquid chromatography compartment analysis: carry out compartment analysis to the composition of sample 1 with analysis mode high performance liquid chromatograph, chromatographic column is C
18post (250mm × 4.6mmI.D., 5 μm), moving phase is methanol-water (90:10, V/V); Flow velocity is 1.0mL/min, and determined wavelength is 254nm, and column temperature is room temperature.
(4) semi-preparative separation and purification: carry out separation and purification to the composition in crude extract with Semipreparative chromatography instrument, chromatographic column is C
18post (250mm × 25.4mmI.D., 10 μm), moving phase is methanol-water (85:15, V/V), and determined wavelength is 254nm, and column temperature is room temperature.According to color atlas manual collection target components cut, concentrating under reduced pressure is except desolventizing.
(5) purity detecting of compound and Structural Identification: by after each target components cut concentrating under reduced pressure with dissolve with methanol, its purity high performance liquid chromatography detects, chromatographic condition is shown in step (3), and analytical results shows that the purity of 2 kinds of compounds all reaches more than 98%.Schuttgelb and rheochrysidin respectively through spectral analysis of the nuclear magnetic resonance 2 kinds of compounds.
Contriver makes moving phase by using the methyl alcohol of different concns, adopt different types of elution, the flow velocity controlling methanol-water eluent is the preferred 25mL/min of 20-30mL/min(), optimized the purification condition realizing the object of the invention, regarding assay result is as follows:
The Semipreparative chromatography separation condition of table one sample 1
In embodiment 1, in elutriant, the concentration of methyl alcohol is higher, and elution time is shorter, and between Schuttgelb and the impurity composition near it, separating effect is not ideal enough, and the purity of gained Schuttgelb is lower.In embodiment 2, the moderate concentration of methyl alcohol in elutriant, good separation between each composition, disengaging time is also comparatively suitable.In embodiment 3, in elutriant, the concentration of methyl alcohol is lower, good separation between Schuttgelb and the impurity composition near it, but disengaging time is oversize.Embodiment 4 adopts methanol-water gradient elution, also can obtain good separating effect within the suitable time, but causes being difficult to realize recycling because the concentration of elutriant constantly changes.
Fig. 2 is the Semipreparative chromatography figure of the sample 1 when selecting embodiment 2 system, and as seen from the figure, each component separating is good, and disengaging time is also comparatively suitable.According to color atlas manual collection each peak component, after recycling design, corresponding high-purity compound can be obtained.Through high performance liquid chromatography area normalization method analytical test, purity higher than 98%, this point can from Fig. 3 to Fig. 4 find out.
Confirm that the chemical structural formula of 2 compounds that institute's extraction purification obtains is as follows through spectral analysis of the nuclear magnetic resonance:
The qualification result of 2 compounds is as follows:
Schuttgelb:
1h-NMR (400MHz, CDCl
3) δ ppm:12.8 (1H, s, 3-OH), 12.3 (1H, s, 1-OH), 12.1 (1H, s, 8-OH), 7.6 (1H, s, 5-H), 7.3 (1H, d,
j=2.4Hz, 4-H), 7.1 (1H, s, 7-H), 6.7 (1H, d,
j=2.4Hz, 2-H), 2.5 (3H, s, CH
3).
13c-NMR (100MHz, CDCl
3) δ ppm:190.1 (C-9), 181.7 (C-10), 165.0 (C-6), 164.9 (C-8), 161.9 (C-1), 148.7 (C-3), 135.5 (C-10a), 133.2 (C-4a), 124.5 (C-2), 120.9 (C-4), 113.8 (C-9a), 109.4 (C-5), 109.3 (C-8a), 108.4 (C-7), 22.0 (-CH
3).
Rheochrysidin:
1h-NMR (400MHz, CDCl
3): δ ppm:12.3 (1H, s, 1-OH), 12.1 (1H, s, 8-OH), 7.6 (1H, s, 5-H), 7.4 (1H, d,
j=2.4Hz, 4-H), 7.1 (1H, s, 7-H), 6.7 (1H, d,
j=2.4Hz, 2-H), 4.0 (3H, s ,-OCH
3), 2.5 (3H, s ,-CH
3).
13c-NMR (100MHz, CDCl
3) δ ppm:190.8 (C-9), 182.1 (C-10), 166.6 (C-8), 165.2 (C-1), 162.5 (C-3), 148.4 (C-6), 135.2 (C-10a), 133.2 (C-4a), 124.5 (C-7), 121.2 (C-5), 113.7 (C-9a), 110.3 (C-8a), 108.2 (C-2), 106.8 (C-4), 56.1 (-OCH
3), 22.1 (-CH
3).
It should be pointed out that embodiment is the more representational example of the present invention, obvious technical scheme of the present invention is not limited to above-described embodiment.A lot of distortion can also be had.Those of ordinary skill in the art, mentions or associates disclosed in from then in file, all should think the claimed scope of this patent.
Claims (10)
1. the method for extracting and developing purifying Schuttgelb and rheochrysidin from giant knotweed, it is characterized in that, step is:
(1) extract: pulverized by Rhizoma Polygoni Cuspidati, extract with organic solvent, filter, extracting solution obtains crude extract through concentrating under reduced pressure;
(2) extract: be distributed in by crude extract in petroleum ether-ethyl acetate-methanol-water (2:5:6:10, V/V), jolting, reach by organic phase and aqueous phase separation after partition equilibrium, organic phase and aqueous phase respectively concentrating under reduced pressure obtain sample 1 and sample 2;
(3) high performance liquid chromatography compartment analysis: carry out compartment analysis to the composition of sample 1 with analysis mode high performance liquid chromatograph, chromatographic column is C
18post (250mm × 4.6mmI.D., 5 μm), moving phase is methanol-water (90:10, V/V); Flow velocity is 1.0mL/min, and determined wavelength is 254nm, and column temperature is room temperature;
(4) semi-preparative separation and purification: carry out separation and purification to the composition in crude extract with Semipreparative chromatography instrument, chromatographic column is C
18post (250mm × 25.4mmI.D., 10 μm), moving phase is methanol-water (85:15, V/V), and determined wavelength is 254nm, and column temperature is room temperature; According to color atlas manual collection target components cut, concentrating under reduced pressure is except desolventizing;
(5) purity detecting of compound and Structural Identification: by after each target components cut concentrating under reduced pressure with dissolve with methanol, its purity high performance liquid chromatography detects, chromatographic condition is shown in step (3), and analytical results shows that the purity of 2 kinds of compounds all reaches more than 98%; Schuttgelb and rheochrysidin respectively through spectral analysis of the nuclear magnetic resonance 2 kinds of compounds.
2. method according to claim 1, is characterized in that, step (1) extracting method is cold soaking, ultrasonic and reflux (preferably ultrasonic).
3. method according to claim 1, is characterized in that, step (1) Extraction solvent is water, ethanol, ether and sherwood oil (preferred alcohol).
4. method according to claim 1, is characterized in that, the concentration of step (1) extraction ethanol-water solution is 50 ~ 95%(preferably 95%).
5. method according to claim 1, is characterized in that, in step (1) leaching process, the consumption of solvent is 6 times amount-15 times amount (preferably 8 times amount).
6. method according to claim 1, is characterized in that, step (1) extraction time is 2-5 time (preferably 4 times).
7. method according to claim 1, is characterized in that, step (1) extraction time is 15-60 minute (preferably 30 minutes).
8. method according to claim 1, it is characterized in that, step (2) carries out all kinds of SOLVENTS in the solvent systems (petroleum ether-ethyl acetate-methanol-water) used in extracting and enriching process volume ratio to Schuttgelb and rheochrysidin is the preferred 2:5:6:10 of 2:5:1:9,2:5:4:6,2:5:6:10 and 2:5:6:4().
9. method according to claim 1, is characterized in that, step (3) high performance liquid chromatography compartment analysis methanol-water eluent carries out wash-out, and type of elution has 95% methanol-water isocratic elution/90% methanol-water isocratic elution/85% methanol-water isocratic elution.
10. method according to claim 1, it is characterized in that, the semi-preparative separation and purification methanol-water eluent of step (4) carries out wash-out, and type of elution has methanol-water gradient elution/90% methanol-water isocratic elution/85% methanol-water isocratic elution/80% methanol-water isocratic elution (controlling methanol-water eluent flow velocity is the preferred 25mL/min of 20-30mL/min().
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104876900A (en) * | 2015-05-18 | 2015-09-02 | 徐州医学院 | Method for extracting, separating and purifying costunolide and dehydrocostus lactone from elecampane |
| CN106018629A (en) * | 2016-08-09 | 2016-10-12 | 云南海沣药业有限公司 | Bushy knotweed leaf fingerprint HPLC method and its use in bushy knotweed leaf capsule quality control |
| CN107353191A (en) * | 2017-07-21 | 2017-11-17 | 江西天祥通用航空股份有限公司 | A kind of method for extracting Physcion |
| CN109608321A (en) * | 2019-01-14 | 2019-04-12 | 淮海工学院 | A kind of preparation method of natural origin rheum emodin |
-
2015
- 2015-09-08 CN CN201510567562.9A patent/CN105061182A/en active Pending
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| 罗建明等: "HPLC 法同时测定虎杖根中4种蒽醌类成分的含量", 《中药材》 * |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104876900A (en) * | 2015-05-18 | 2015-09-02 | 徐州医学院 | Method for extracting, separating and purifying costunolide and dehydrocostus lactone from elecampane |
| CN106018629A (en) * | 2016-08-09 | 2016-10-12 | 云南海沣药业有限公司 | Bushy knotweed leaf fingerprint HPLC method and its use in bushy knotweed leaf capsule quality control |
| CN107353191A (en) * | 2017-07-21 | 2017-11-17 | 江西天祥通用航空股份有限公司 | A kind of method for extracting Physcion |
| CN109608321A (en) * | 2019-01-14 | 2019-04-12 | 淮海工学院 | A kind of preparation method of natural origin rheum emodin |
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