CN106967135B - Preparation method of galloyl paeoniflorin monomer - Google Patents
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- CN106967135B CN106967135B CN201611254972.9A CN201611254972A CN106967135B CN 106967135 B CN106967135 B CN 106967135B CN 201611254972 A CN201611254972 A CN 201611254972A CN 106967135 B CN106967135 B CN 106967135B
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Abstract
The invention relates to a preparation method of galloyl paeoniflorin monomer, which comprises the following steps: a, extraction: pulverizing dried radix Paeoniae Rubra into coarse powder, and extracting with ethanol under reflux to obtain concentrated extract; b, extraction: extracting the concentrated extract with ethyl acetate to obtain crude product of galloyl paeoniflorin; c, preparation: filtering with nanometer organic membrane, preparing with C18, and extracting with ethyl acetate to obtain galloyl paeoniflorin monomer product with purity of 98% or more. The method is rapid, simple and convenient, has low cost, and is suitable for industrialized production, and the obtained galloyl paeoniflorin monomer has high purity and stable property.
Description
Technical Field
The invention relates to a method for separating and purifying active ingredients of traditional Chinese medicines, in particular to a method for extracting and separating galloyl paeoniflorin from red paeony root dry roots, and belongs to the technical field of separation and purification of traditional Chinese medicines.
Background
Galloyl paeoniflorin, the english name Galloylpaeoniflorin, CAS: 122965-41-7, molecular formula C30H32O15Molecular weight of 632.57, and structural formula as follows:
recent research reports indicate that the red peony root extract has an effect on the concentration of calcium ions in central cranial nerves. The red peony root is clinically applied to dysthymia, tumor resistance, immunoregulation, blood vessel protection, liver protection and the like, and is consistent with the functions of strengthening the spleen, tonifying healthy qi and enhancing the immunity which are known by the traditional Chinese medicine theory. The pharmacological activity test of the foreign scholars on the extract of red paeony root shows that the red paeony root has the functions of central cranial nerve, immunity, menstruation, atherosclerosis resistance and tumor resistance.
Galloyl paeoniflorin is an important active compound in red paeony root and is a characteristic component of the red paeony root. The compound has the function of inhibiting arachidonic acid (arachidonic acid AA) from generating enzyme. In vitro studies, galloyl paeoniflorin was found to reduce the rate of cell proliferation in a dose-dependent and time-dependent manner, and induce apoptosis in the cells. The galloyl paeoniflorin starts an apoptosis signal by inhibiting the function of mitochondria, and finally the cell undergoes apoptosis. Therefore, the extraction and separation of high-purity galloyl paeoniflorin from the original plant has important significance for controlling the quality index of the medicinal material, clarifying the pharmacological action of the medicinal material and searching a lead compound for the development of new drugs.
Application publication No. CN104072550A discloses a separation method of monoterpene and saponin components in a Chinese medicinal composition plant drug intermediate, which comprises the following steps: sequentially extracting with petroleum ether, ethyl acetate and n-butanol, purifying with macroporous adsorbent resin to obtain 30% and 70% ethanol eluate, separating 30% ethanol eluate to obtain pure paeoniflorin R1, pure paeoniflorin, separating 70% ethanol eluate to obtain pure paeoniflorin, pure benzoylpaeoniflorin, pure galloyl paeoniflorin, pure methyl paeoniflorin, pure ginsenoside Rg1, pure ginsenoside Rc, pure ginsenoside Rb1, pure ginsenoside Rb2, etc. Although the method can obtain the pure galloyl paeoniflorin, the purity of the galloyl paeoniflorin is low, and a monomer with the HPLC purity of more than 98.5 percent cannot be obtained by the process.
The publication number is CN1799581, the cortex moutan active ingredients and the preparation method thereof, the percentage content of the active ingredients is 10-25% of paeoniflorin, 40-55% of galloyl paeoniflorin and 30-45% of paeoniflorin; the preparation method comprises pulverizing cortex moutan, extracting under heating, concentrating the extractive solution to obtain extract, mixing with silica gel, separating with normal phase silica gel column, concentrating and drying the eluate to obtain sample, and separating with preparative liquid chromatography to obtain effective components. The separation and purification of galloyl paeoniflorin has no pertinence, and the separation process is complex, which is not beneficial to the stability of galloyl paeoniflorin.
Disclosure of Invention
The invention aims to overcome the defects that no extraction and purification process aiming at the galloyl paeoniflorin monomer exists in the prior art, and the galloyl paeoniflorin monomer obtained by separation by the prior method has low purity and unstable property, and provides the preparation method of the galloyl paeoniflorin monomer, which is quick, simple and convenient, has low cost, is suitable for industrial production, and has high purity and stable property.
In order to solve the technical problems, the invention is realized by the following technical scheme:
a preparation method of galloyl paeoniflorin monomer comprises the following steps:
A. extraction:
pulverizing the dry root of red peony root into coarse powder, adding 65-75% ethanol solution by mass percent, carrying out reflux extraction, filtering the extract, and removing ethanol to obtain a concentrated extract with the relative density of 1.30-1.40 at 45-50 ℃;
B. and (3) extraction:
b, adding water into the thick extract obtained in the step A for dispersing to obtain a dispersion solution, then adding petroleum ether for extraction, removing petroleum ether extract, adding ethyl acetate into a water phase for extraction, collecting ethyl acetate extract, and concentrating to dryness to obtain a crude product of the food acyl paeoniflorin;
C. preparation:
and D, according to the proportion of the crude product of the galloyl paeoniflorin to methanol =1g to 3ml, completely dissolving the crude product of the galloyl paeoniflorin obtained in the step B by using methanol, filtering by using a nano organic membrane after completely dissolving, performing high-pressure preparation separation on the filtrate by using C18 reverse phase chromatographic packing, collecting a corresponding chromatographic peak, recovering the methanol, adding ethyl acetate into the residual water solution for extraction, collecting the obtained ethyl acetate extract, adding anhydrous sodium sulfate for dehydration, concentrating under reduced pressure at 40-45 ℃ until no ethyl acetate exists to obtain a white solid, and drying the white solid under reduced pressure at 45 ℃ to obtain the galloyl paeoniflorin monomer product. The high pressure in the high-pressure preparation and separation of the C18 reversed phase chromatographic packing in the step is 4-5 MPa.
In the step A, 10-15L of ethanol is added into every 1Kg of red peony root.
In the step B, when water is added for dispersion, the volume of the added water is 10-15 times of the volume of the concentrated extract.
In the step B, when petroleum ether is added for extraction, the adding amount is 2-3 times of the volume of the dispersion solution each time, and when ethyl acetate is added into the water phase for extraction, the using amount of the ethyl acetate is 2-3 times of the volume of the water phase each time.
In the step C, the aperture of the nano organic membrane is 220 nm-450 nm.
In the step C, the mobile phase separated by the C18 reverse phase chromatographic packing high pressure preparation is a solvent with methanol and water in a volume ratio of 45: 55; the detection wavelength is 220 nm-230 nm.
And C, adding ethyl acetate which is 1-2 times of the water solution into the residual water solution for extraction each time when the residual water solution is added with ethyl acetate for extraction.
The pressure for vacuum concentration and vacuum drying in the above steps can be-0.1 MPa.
The invention has the following beneficial effects:
the method comprises the steps of extracting the concentrated extract extracted from red peony root by using specific ethyl acetate, dissolving by using methanol, filtering by using a nano organic membrane, and carrying out high-pressure preparation and separation on the filtrate by using C18 reversed phase chromatographic packing to obtain a galloyl paeoniflorin monomer product with the purity of more than or equal to 98%. The whole process is simple and convenient to operate, stable in process, low in cost, high in separation efficiency and high in product purity, and is suitable for industrial production of high-purity galloyl paeoniflorin monomers.
According to the invention, through long-term experimental study, the galloyl paeoniflorin monomer product with the purity of more than or equal to 98% can be obtained only by the steps of ethyl acetate extraction, methanol dissolution, nano organic membrane filtration and high-pressure preparation of filtrate by C18 reversed phase chromatographic packing, and the problems of long preparation process and poor stability of the galloyl paeoniflorin monomer caused by complicated operation steps in the prior art are solved.
The obtained crude galloyl paeoniflorin is dissolved by methanol and then filtered by a nano organic membrane, so that the normal operation of the high-pressure liquid phase preparation in a working environment with the pressure of 4-5MPa is ensured.
The C18 reversed phase chromatographic packing is prepared and separated under high pressure: a: methanol B: water, A: b45: 55V/V is a mobile phase; the detection wavelength is 220 nm.
Drawings
FIG. 1 is an HPLC chromatogram of the galloyl paeoniflorin monomer product of example 1 of the present invention.
Detailed Description
The present invention will be described in further detail with reference to specific embodiments.
It should not be understood that the scope of the above-described subject matter of the present invention is limited to the following examples.
In the following examples, the purity of the final product galloyl paeoniflorin monomer was checked by reversed phase analytical liquid chromatography (RP-HPLC), and the chromatographic conditions were as follows:
octadecylsilane chemically bonded silica is used as a filling agent; methanol and water (20: 80) are taken as mobile phases; the column temperature is 30 ℃; the flow rate is 1.0 ml/min; the detection wavelength was 220 nm.
Example 1
A preparation method of galloyl paeoniflorin monomer comprises the following steps:
A. extraction:
pulverizing 250g of radix Paeoniae Rubra dry root into coarse powder, adding 70% ethanol solution 2.5L, reflux extracting for 3 times, each for 1.5 hr, filtering the extractive solution, mixing filtrates, concentrating under reduced pressure, and recovering ethanol to obtain concentrated extract with relative density of 1.32 (50 deg.C) and volume of 160 ml.
B. And (3) extraction:
adding 1.6L of the concentrated extract obtained in the step A into water for dispersing, extracting with petroleum ether for 3 times, removing the petroleum ether extract, extracting the water phase with ethyl acetate for 5 times, combining the ethyl acetate extract, and recovering the filtrate to dryness to obtain 20g of brown crude galloyl paeoniflorin; when petroleum ether is added for extraction, the adding amount is 2 times of the volume of the dispersion solution each time, and when ethyl acetate is added into the water phase for extraction, the using amount of the ethyl acetate is 3 times of the volume of the water phase each time.
C. Preparation:
completely dissolving the brown solid obtained in the step B by using 60ml of methanol, and filtering by using a nano organic membrane after complete dissolution, wherein the aperture of the nano organic membrane is 380 nm; and (3) performing high-pressure preparation and separation on the filtrate by using C18 reverse phase chromatographic packing, wherein A: methanol B: water, A: b45: 55V/V is a mobile phase; detecting wavelength at 220nm, collecting corresponding chromatographic peak, recovering methanol, extracting the residual water solution with ethyl acetate, dehydrating the obtained ethyl acetate phase with anhydrous sodium sulfate, concentrating at 45 deg.C under reduced pressure until there is no ethyl acetate to obtain white solid, and drying at 45 deg.C under reduced pressure to obtain 0.8g of galloyl paeoniflorin with purity of 98% or more.
Example 2
A preparation method of galloyl paeoniflorin monomer, which takes red paeony root as a raw material to obtain the galloyl paeoniflorin monomer through extraction, extraction and preparation, comprises the following main steps:
A. extraction:
pulverizing 250g of radix Paeoniae Rubra dry root into coarse powder, adding 2.5L of 65% ethanol solution, reflux extracting for 2 hr for 4 times, filtering the extractive solution, mixing filtrates, concentrating under reduced pressure, and recovering ethanol to obtain concentrated extract with relative density of 1.35 (50 deg.C) and volume of 120 ml.
B. And (3) extraction:
adding 1.2L of the concentrated extract obtained in the step A into water for dispersing, extracting with petroleum ether for 3 times, removing the petroleum ether extract, extracting the water phase with ethyl acetate for 6 times, combining the ethyl acetate extract, and recovering the filtrate to dryness to obtain a brown crude product of galloyl paeoniflorin, wherein 20.5g of galloyl paeoniflorin is obtained; when petroleum ether is added for extraction, the adding amount is 3 times of the volume of the dispersion solution each time, and when ethyl acetate is added into the water phase for extraction, the using amount of the ethyl acetate is 2 times of the volume of the water phase each time.
C. Preparation:
and B, completely dissolving the brown solid obtained in the step B by using 61ml of methanol, filtering by using a nano organic membrane after complete dissolution, wherein the aperture of the nano organic membrane is 450nm, and performing high-pressure preparation and separation on the filtrate by using C18 reverse phase chromatographic packing, wherein A: methanol B: water, A: b45: 55V/V is mobile phase; detecting wavelength at 220nm, collecting corresponding chromatographic peak, recovering methanol, extracting the residual water solution with ethyl acetate, dehydrating the obtained ethyl acetate phase with anhydrous sodium sulfate, concentrating at 45 deg.C under reduced pressure until there is no ethyl acetate to obtain white solid, and drying at 40 deg.C under reduced pressure to obtain 0.85g galloyl paeoniflorin with purity of 98% or more.
Example 3
A preparation method of galloyl paeoniflorin monomer, which takes red paeony root as a raw material to obtain the galloyl paeoniflorin monomer through extraction, extraction and preparation, comprises the following main steps:
A. extraction:
pulverizing 250g of radix Paeoniae Rubra dry root into coarse powder, adding 2.5L of 75% ethanol solution, reflux extracting for 2 hr for 4 times, filtering the extractive solution, mixing filtrates, concentrating under reduced pressure, and recovering ethanol to obtain concentrated extract with relative density of 1.30 (50 deg.C) and volume of 160 ml.
B. And (3) extraction:
adding 2.4L of water into the concentrated extract obtained in the step A to disperse to obtain dispersion liquid, extracting with petroleum ether for 4 times, removing petroleum ether extract, extracting the water phase with ethyl acetate for 4 times, combining ethyl acetate extract, and recovering the filtrate to dryness to obtain crude brown galloyl paeoniflorin 19.55 g; when petroleum ether is added for extraction, the adding amount is 2 times of the volume of the dispersion solution each time, and when ethyl acetate is added into the water phase for extraction, the using amount of the ethyl acetate is 2 times of the volume of the water phase each time.
C. Preparation:
and B, completely dissolving the brown solid obtained in the step B by using 60ml of methanol, filtering by using a nano organic membrane after complete dissolution, wherein the aperture of the nano organic membrane is 220nm, and performing high-pressure preparation and separation on the filtrate by using C18 reverse phase chromatographic packing, wherein A: methanol B: water, A: b45: 55V/V is mobile phase; detecting wavelength at 220nm, collecting corresponding chromatographic peak, recovering methanol, extracting the residual water solution with ethyl acetate, dehydrating the obtained ethyl acetate phase with anhydrous sodium sulfate, concentrating at 45 deg.C under reduced pressure until there is no ethyl acetate to obtain white solid, and drying at 45 deg.C under reduced pressure to obtain 0.78g of galloyl paeoniflorin with purity of 98% or more.
Example 4
A preparation method of galloyl paeoniflorin monomer comprises the following steps:
A. extraction:
pulverizing 1kg of dried radix Paeoniae Rubra into coarse powder, adding 75% ethanol solution 15L, reflux extracting for 4 times, each for 2 hr, filtering the extractive solution, mixing filtrates, concentrating under reduced pressure, and recovering ethanol to obtain concentrated extract with relative density of 1.38 (50 deg.C) and volume of 400 ml.
B. And (3) extraction:
adding 3L of the concentrated extract obtained in the step A into water for dispersing, extracting with petroleum ether for 4 times, removing the petroleum ether extract, extracting the water phase with ethyl acetate for 4 times, combining the ethyl acetate extract, and recovering the filtrate to dryness to obtain 80g of brown crude galloyl paeoniflorin;
C. preparation:
and B, completely dissolving the brown solid obtained in the step B by 230ml of methanol, filtering by using a nano organic membrane after complete dissolution, and separating the filtrate by using C18 reversed phase chromatographic packing under high pressure, wherein A: methanol B: water, A: b45: 55V/V is a mobile phase; detecting wavelength at 220nm, collecting corresponding chromatographic peak, recovering methanol, extracting the residual water solution with 2 times of ethyl acetate, dehydrating the obtained ethyl acetate phase with anhydrous sodium sulfate, concentrating under reduced pressure at 40 deg.C until no ethyl acetate is obtained to obtain white solid, and drying under reduced pressure at 45 deg.C to obtain 3.33 g of galloyl paeoniflorin with purity of 98% or more.
Claims (5)
1. A preparation method of galloyl paeoniflorin monomer is characterized by comprising the following steps:
A. extraction:
pulverizing the dry root of red peony root into coarse powder, adding 65-75% ethanol solution by mass percent, carrying out reflux extraction, filtering the extract, and removing ethanol to obtain a concentrated extract with the relative density of 1.30-1.40 at 45-50 ℃;
B. and (3) extraction:
b, adding water into the thick extract obtained in the step A for dispersing to obtain a dispersion solution, then adding petroleum ether for extraction, removing petroleum ether extract, adding ethyl acetate into a water phase for extraction, collecting ethyl acetate extract, and concentrating to dryness to obtain a crude product of galloyl paeoniflorin;
C. preparation:
b, completely dissolving the crude galloyl paeoniflorin obtained in the step B by using methanol according to the proportion that the crude galloyl paeoniflorin is methanol =1g:3ml, filtering by using a nano organic membrane after complete dissolution, performing high-pressure preparation separation on the filtrate by using C18 reverse phase chromatographic packing, collecting a corresponding chromatographic peak, recovering the methanol, adding ethyl acetate into the residual water solution for extraction, collecting the obtained ethyl acetate extract, adding anhydrous sodium sulfate for dehydration, concentrating under reduced pressure at 40-45 ℃ until no ethyl acetate exists to obtain a white solid, and drying the white solid under reduced pressure at 45 ℃ to obtain a galloyl paeoniflorin monomer product; in the step C, the aperture of the nano organic membrane is 220 nm-450 nm; the mobile phase separated by the C18 reversed phase chromatographic packing high-pressure preparation is a solvent with methanol and water in a volume ratio of 45: 55; the detection wavelength is 220 nm-230 nm.
2. The method for preparing galloyl paeoniflorin monomer according to claim 1, wherein: in the step A, 10-15L of ethanol is added into every 1kg of red paeony root.
3. The method for preparing galloyl paeoniflorin monomer according to claim 1, wherein: in the step B, when water is added for dispersion, the volume of the added water is 10-15 times of the volume of the concentrated extract.
4. The method for preparing galloyl paeoniflorin monomer according to claim 1, wherein: in the step B, when petroleum ether is added for extraction, the adding amount is 2-3 times of the volume of the dispersion solution each time, and when ethyl acetate is added into the water phase for extraction, the using amount of the ethyl acetate is 2-3 times of the volume of the water phase each time.
5. The method for preparing galloyl paeoniflorin monomer according to claim 1, wherein: and C, adding ethyl acetate which is 1-2 times of the water solution into the residual water solution for extraction each time when the residual water solution is added with ethyl acetate for extraction.
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104072550A (en) * | 2013-03-25 | 2014-10-01 | 河北以岭医药研究院有限公司 | Separation method of monoterpene and saponins components in traditional Chinese medicine composition vegetable drug midbody |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104072550A (en) * | 2013-03-25 | 2014-10-01 | 河北以岭医药研究院有限公司 | Separation method of monoterpene and saponins components in traditional Chinese medicine composition vegetable drug midbody |
Non-Patent Citations (2)
| Title |
|---|
| Galloylpaeoniflorin, A New Acylated Monoterpene Glucoside from Paeony Root;Sam Sik Kang et al.;《Arch. Pharm. Res.》;19910331;第14卷(第1期);正文第53页Isolation部分 * |
| 基于HPLC-DAD-Q-TOF-MS/MS的白芍和赤芍主要成分定性定量研究;刘杰 等;《中国中药杂志》;20150531;第40卷(第9期);第1763页左栏第1段、第1764-1766页图1和表1 * |
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