CN105753918B - method for extracting apigenin-7-o- β -D-glucuronide from broussonetia papyrifera leaves - Google Patents
method for extracting apigenin-7-o- β -D-glucuronide from broussonetia papyrifera leaves Download PDFInfo
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Abstract
the invention discloses a method for extracting apigenin-7-O- β -D-glucuronide from broussonetia papyrifera leaves, which belongs to the field of extraction of effective components of traditional Chinese medicines and comprises the steps of extraction, water precipitation, macroporous adsorption resin purification, polyamide purification, acid precipitation and industrial preparation chromatography purification.
Description
Technical Field
The invention belongs to a method for extracting effective components of traditional Chinese medicines, and particularly relates to a method for extracting apigenin glucuronide from broussonetia papyrifera leaves.
Background
Broussonetia papyrifera (L.) Vent is Moraceae plant, can be harvested leaves all the year round, is fresh or sun-dried, has light taste and cool property, has the functions of clearing heat and detoxicating, dispelling wind and arresting itching, healing sores and stopping bleeding, and is mainly used for treating dysentery, neurodermatitis, scabies, furuncle and incised wound bleeding, from the 20 th century and the 80 th century, people begin to research the chemistry and pharmacology of the Broussonetia papyrifera, separate a plurality of flavonoid compounds from the whole plant of the Broussonetia papyrifera, wherein the molecular formula of the apigenin-7-o- β -D-glucuronide is C21H18O11The structural formula is as follows:
apigenin-7-o- β -D-glucuronide can inhibit thrombosis and prevent senile dementia, has good curative effect on treating coronary heart disease and myocardial infarction, and is greatly beneficial to the pharmaceutical industry if apigenin-7-o- β -D-glucuronide with high purity can be simply and conveniently extracted from broussonetia papyrifera leaves, in patent document 201310179358.0, a method for extracting apigenin-7-o- β -D-glucuronide from broussonetia papyrifera leaves is also disclosed, but different from the technical scheme adopted by the invention, ultrafiltration membrane filtration and high-speed counter-current chromatography purification are adopted in the patent document.
Disclosure of Invention
the technical problem to be solved by the invention is to provide a simple, convenient and high-purity method for preparing apigenin-7-o- β -D-glucuronide from broussonetia papyrifera leaves.
The technical scheme adopted by the invention is as follows:
a method for extracting apigenin-7-o- β -D-glucuronide from broussonetia papyrifera leaves comprises the following steps:
A. extraction: weighing broussonetia papyrifera leaves, adding 10-15 times of 40-70% ethanol into the broussonetia papyrifera leaves, soaking for 1-3 hours, performing reflux extraction for three times, performing 2 hours each time, combining extracting solutions, and performing reduced pressure concentration at 40-60 ℃ to obtain a concentrated solution I;
B. water precipitation: adding 3-6 times of deionized water into the concentrated solution I, refrigerating at 4-10 deg.C, centrifuging, and filtering to obtain filtrate;
C. purifying with macroporous adsorption resin: purifying the filtrate obtained in the step B by using macroporous adsorption resin, and then concentrating under reduced pressure to obtain a concentrated solution II;
D. and (3) purifying the polyamide resin: purifying the concentrated solution II obtained in the step C by polyamide resin, and then concentrating under reduced pressure to obtain a concentrated solution III;
E. acid precipitation: d, regulating the pH value of the concentrated solution III obtained in the step D by using hydrochloric acid, standing for 24 hours, filtering, and washing a precipitate obtained after filtering by using acid water;
F. industrial preparative chromatographic purification: and E, dissolving the precipitate washed by the acid water in the step E by using 40-70% methanol, purifying by using an industrial preparative chromatography, collecting a target compound according to a chromatographic peak, and then concentrating under reduced pressure and freeze-drying to obtain the compound.
The macroporous adsorption resin is HZ816 macroporous adsorption resin; the polyamide is 30-40 meshes.
The macroporous adsorption resin purification steps are as follows: weighing macroporous adsorption resin according to the mass ratio of the resin to the crude drug of 1:1.5, loading wet resin into a column, loading the filtrate under the condition of pH of 3.5-4.0, wherein the crude drug concentration of the loading liquid medicine is 0.17g/ml, the loading flow rate is 2-4BV/h, and saturating for 1 hour after loading; washing with 10% ethanol with pH of 3.5-4.0 at flow rate of 4-6BV/h and eluting with 4-6 BV; eluting with 60% ethanol at flow rate of 6-8BV/h and eluting amount of 6-8BV/h, collecting eluate, and concentrating under reduced pressure at 40-60 deg.C to obtain concentrated solution II with crude drug concentration of 0.2-0.5 g/ml.
The polyamide resin purification steps are as follows: loading the concentrated solution II with a loading flow rate of 2-4BV/h and saturation for 1h, eluting with 14-16BV water at a flow rate of 4-6BV/h, then eluting with 10-12BV20% ethanol at a flow rate of 4-6BV/h to remove impurities, then eluting with 14-16BV 80% ethanol at a flow rate of 6-8BV/h, collecting the eluent, and concentrating under reduced pressure at 40-60 ℃ to obtain a concentrated solution III with a concentration of 3.0-4.0 g/ml.
The pH value in the acid precipitation step is 2.0-2.5, the mixture is placed at 4-10 ℃ for 24 hours, filtered, and the precipitate obtained after filtering is washed 3 times by acid water with the pH value of 2.0-2.5.
the purification steps of the high-pressure preparative chromatography comprise that the mass ratio of C18 filler to crude drug of the high-pressure preparative chromatography is 1:3, the purification is carried out for 1 time, the flow rate is 50ml/min with the mobile phase of 45:55 methanol to 1 per mill formic acid, apigenin-7-o- β -D-glucuronide liquid medicine is collected according to chromatographic peaks, and then the liquid medicine is decompressed, concentrated and freeze-dried to obtain the apigenin-7-o- β -D-glucuronide.
preferably, the method for extracting the apigenin-7-o- β -D-glucuronide from the broussonetia papyrifera leaves comprises the following steps:
A. extraction: weighing folium Broussonetiae, adding 10-15 times of 40-70% ethanol into folium Broussonetiae, soaking for 1-3 hr, reflux extracting for three times, each for 2 hr, mixing extractive solutions, and concentrating under reduced pressure at 40-60 deg.C to obtain concentrated solution I with crude drug concentration of 0.8-1.2 g/ml;
B. water precipitation: adding 3-6 times of deionized water into the concentrated solution I, refrigerating at 4-10 deg.C, centrifuging, filtering, and adjusting the concentration of the filtrate to 0.17 g/ml;
C. purifying with macroporous adsorption resin: purifying the filtrate obtained in the step B by using HZ816 macroporous adsorption resin, weighing the macroporous adsorption resin according to the mass ratio of the resin to the crude drug of 1:1.5, filling the wet resin into a column, loading the filtrate at the pH of 3.5-4.0 at the loading flow rate of 2-4BV/h, and saturating for 1 hour after loading; washing with 10% ethanol with pH of 3.5-4.0 at flow rate of 4-6BV/h and eluting with 4-6 BV; eluting with 60% ethanol at flow rate of 6-8BV/h and elution amount of 6-8BV/h, collecting eluate, and concentrating under reduced pressure at 40-60 deg.C to obtain concentrated solution II with crude drug concentration of 0.2-0.5 g/ml;
D. and (3) purifying the polyamide resin: selecting 30-40 mesh polyamide resin, wherein the mass ratio of the polyamide resin to the crude drug is 1:6, loading the concentrated solution II, the flow rate of loading is 2-4BV/h, saturating for 1h after loading, eluting with 14-16BV water at the flow rate of 4-6BV/h, then eluting with 10-12BV20% ethanol at the flow rate of 4-6BV/h, removing impurities, then eluting with 14-16BV 80% ethanol at the flow rate of 6-8BV/h, collecting the eluent, and concentrating under reduced pressure at 40-60 ℃ to obtain a concentrated solution III with the crude drug concentration of 3.0-4.0 g/ml;
E. acid precipitation: d, regulating the pH value of the concentrated solution III obtained in the step D to be 2.0-2.5 by using hydrochloric acid, standing at the temperature of 4-10 ℃ for 24 hours, filtering, and washing the precipitate obtained after filtering for 3 times by using acid water with the pH value of 2.0-2.5;
F. and E, industrial preparative chromatography purification, namely dissolving the precipitate washed by the acid water in the step E by 40-70% of methanol, purifying by using industrial preparative chromatography, wherein the mass ratio of C18 filler to crude drug of the industrial preparative chromatography is 1:3, purifying for 1 time, the mass ratio of methanol with a mobile phase of 45:55 to 1 thousandth of formic acid, the flow rate is 50ml/min, collecting apigenin-7-o- β -D-glucuronide liquid medicine according to chromatographic peaks, then concentrating under reduced pressure, and freeze-drying to obtain apigenin-7-o- β -D-glucuronide.
The process is also preferably
A. Extraction: weighing broussonetia papyrifera leaves, adding 13 times of 60% ethanol into the broussonetia papyrifera leaves, soaking for 1 hour, performing reflux extraction for three times, performing 2 hours each time, combining extracting solutions, and performing reduced pressure concentration at 60 ℃ to obtain a concentrated solution I with the crude drug concentration of 1 g/ml;
B. water precipitation: adding 5 times of deionized water into the concentrated solution I, refrigerating at 4-10 deg.C for 24 hr, centrifuging, filtering, and adjusting the concentration of the filtrate to 0.17 g/ml;
C. purifying with macroporous adsorption resin: purifying the filtrate obtained in the step B by using HZ816 macroporous adsorption resin, weighing the macroporous adsorption resin according to the mass ratio of the resin to the crude drug of 1:1.5, filling the wet resin into a column, loading the filtrate at the pH of 3.5-4.0 at the loading flow rate of 2BV/h, and saturating for 1 hour after loading; washing with 10% ethanol with pH of 3.5-4.0 at flow rate of 4BV/h and elution amount of 6 BV; eluting with 60% ethanol at flow rate of 6BV/h and elution amount of 8BV, collecting eluate, and concentrating under reduced pressure at 60 deg.C to obtain concentrated solution II with crude drug concentration of 0.2 g/ml;
D. and (3) purifying the polyamide resin: selecting 30-40 mesh polyamide resin, wherein the mass ratio of the polyamide resin to the crude drug is 1:6, loading the concentrated solution II, the loading flow rate is 2BV/h, saturating for 1h after loading, eluting with 16BV water at the flow rate of 4BV/h, then eluting with 12BV20% ethanol at the flow rate of 4BV/h, removing impurities, then eluting with 16BV 80% ethanol at the flow rate of 6BV/h, collecting eluent, and concentrating under reduced pressure at 60 ℃ to obtain concentrated solution III with the crude drug concentration of 4.0 g/ml;
E. acid precipitation: d, regulating the pH value of the concentrated solution III obtained in the step D to be 2.0-2.5 by using hydrochloric acid, standing at the temperature of 4-10 ℃ for 24 hours, filtering, and washing the precipitate obtained after filtering for 3 times by using acid water with the pH value of 2.0-2.5;
F. and E, industrial preparative chromatography purification, namely dissolving the precipitate washed by the acid water in the step E by 40-70% of methanol, purifying by using industrial preparative chromatography, wherein the mass ratio of C18 filler to crude drug of the industrial preparative chromatography is 1:3, purifying for 1 time, the mass ratio of methanol with a mobile phase of 45:55 to 1 thousandth of formic acid, the flow rate is 50ml/min, collecting apigenin-7-o- β -D-glucuronide liquid medicine according to chromatographic peaks, then concentrating under reduced pressure, and freeze-drying to obtain apigenin-7-o- β -D-glucuronide.
The resin is usually packed in a cylindrical resin column through which the solution is continuously passed, and the volume of the resin column loaded with the resin is called Bed Volume (BV), which is the basic unit of the resin column and the amount of various materials in operation is in BV. For example, the flow rate of the solution passing through the resin column is 2-4BV/h, i.e. the volume of the solution passing through the resin column per hour is 2-4 times of the volume of the resin bed. The handling capacity of the resin is also often calculated in BV units.
Due to the adoption of the technical scheme, the invention has the technical progress that:
the preparation method adopted by the invention is simple to operate, compared with the prior art, the method not only comprises the steps of extraction and filtration, purification of polyamide resin, purification of macroporous adsorption resin and acid precipitation, but also can be used for further washing off impurities, the purity of the obtained target is higher than 90%, and the yield of the product is also higher than 80% through a series of steps.
Detailed Description
The present invention will be described in further detail with reference to specific embodiments below:
example 1
the method for extracting apigenin-7-o- β -D-glucuronide from broussonetia papyrifera leaves comprises the following steps:
A. extraction: weighing 5kg of broussonetia papyrifera leaves, adding 13 times of 60% ethanol into the broussonetia papyrifera leaves, soaking for 1 hour, performing reflux extraction for three times, performing 2 hours each time, combining extracting solutions, and performing reduced pressure concentration at 60 ℃ to obtain a concentrated solution I with the crude drug concentration of 1 g/ml;
B. water precipitation: adding 5 times of deionized water into the concentrated solution I, refrigerating at 4 deg.C for 24 hr, centrifuging, filtering, and adjusting the concentration of the filtrate to 0.17 g/ml;
C. purifying with macroporous adsorption resin: purifying the filtrate obtained in the step B by using HZ816 macroporous adsorption resin, weighing the macroporous adsorption resin according to the mass ratio of the resin to the crude drug of the broussonetia papyrifera leaves being 1:1.5, filling the wet resin into a column, loading the filtrate at the pH of 3.5 at the loading flow rate of 2BV/h, and saturating the filtrate for 1 hour after loading; then 10 percent ethanol with pH of 3.5 is used for washing off impurities, the elution flow rate is 4BV/h, and the elution dosage is 6 BV; eluting with 60% ethanol at flow rate of 6BV/h and elution amount of 8BV, collecting eluate, and concentrating under reduced pressure at 60 deg.C to obtain concentrated solution II with crude drug concentration of 0.2 g/ml;
D. and (3) purifying the polyamide resin: selecting 30-mesh polyamide resin, wherein the mass ratio of the polyamide resin to crude drugs is 1:6, loading the concentrated solution II into a sample, wherein the sampling flow rate is 2BV/h, the sample is saturated for 1h after loading, eluting the sample by using 16BV water at the flow rate of 4BV/h, then eluting by using 12BV20% ethanol at the flow rate of 4BV/h, removing impurities, then eluting by using 16BV 80% ethanol at the flow rate of 6BV/h, collecting eluent, and concentrating the eluent under reduced pressure at the temperature of 60 ℃ to obtain a concentrated solution III with the crude drug concentration of 4.0 g/ml;
E. acid precipitation: d, regulating the pH value of the concentrated solution III obtained in the step D to be 2.5 by using hydrochloric acid, standing at the temperature of 7 ℃ for 24 hours, filtering, and washing a precipitate obtained after filtering for 3 times by using acid water with the pH value of 2.0;
F. and E, industrial preparative chromatographic purification, namely dissolving the precipitate washed by the acid water in the step E by using 60 percent methanol, purifying by using an industrial preparative chromatogram, wherein the mass ratio of a C18 filler to the crude drug of the industrial preparative chromatogram is 1:3, purifying for 1 time, the mass ratio of the methanol with a mobile phase of 45:55 to 1 thousandth formic acid, the flow rate is 50ml/min, collecting apigenin-7-o- β -D-glucuronide liquid medicine according to chromatographic peaks, then carrying out reduced pressure concentration and freeze drying to obtain 16.9g of apigenin-7-o- β -D-glucuronide, and the yield is 83.6 percent and the purity is 95.3 percent.
Example 2
the method for extracting apigenin-7-o- β -D-glucuronide from broussonetia papyrifera leaves comprises the following steps:
A. extraction: weighing 5kg of broussonetia papyrifera leaves, adding 10 times of 40% ethanol into the broussonetia papyrifera leaves, soaking for 3 hours, performing reflux extraction for three times, performing 2 hours each time, combining extracting solutions, and performing reduced pressure concentration at 40 ℃ to obtain a concentrated solution I with the crude drug concentration of 0.8 g/ml;
B. water precipitation: adding 3 times of deionized water into the concentrated solution I, refrigerating at 10 ℃, centrifuging and filtering, and adjusting the concentration of the crude drug in the filtrate to 0.17 g/ml;
C. purifying with macroporous adsorption resin: purifying the filtrate obtained in the step B by using HZ816 macroporous adsorption resin, weighing the macroporous adsorption resin according to the mass ratio of the resin to the crude drug of 1:1.5, filling the wet resin into a column, loading the filtrate under the condition of PH4.0 at the loading flow rate of 4BV/h, and saturating the filtrate for 1 hour after loading; washing with 10% ethanol with pH of 4.0 to remove impurities, wherein the elution flow rate is 4BV/h and the elution amount is 4 BV; eluting with 60% ethanol at flow rate of 8BV/h and elution amount of 6BV, collecting eluate, and concentrating under reduced pressure at 40 deg.C to obtain concentrated solution II with crude drug concentration of 0.5 g/ml;
D. and (3) purifying the polyamide resin: selecting 30-40 mesh polyamide resin, wherein the mass ratio of the polyamide resin to the crude drug is 1:6, loading the concentrated solution II, wherein the loading flow rate is 4BV/h, the sample is saturated for 1h, eluting with 14BV water at the flow rate of 6BV/h, then eluting with 10BV20% ethanol at the flow rate of 6BV/h, removing impurities, then eluting with 14BV 80% ethanol at the flow rate of 8BV/h, collecting eluent, and concentrating under reduced pressure at 40 ℃ to obtain a concentrated solution III with the crude drug concentration of 3.0 g/ml;
E. acid precipitation: d, regulating the pH value of the concentrated solution III obtained in the step D to be 2.0 by using hydrochloric acid, standing at the temperature of 10 ℃ for 24 hours, filtering, and washing precipitates obtained after filtering for 3 times by using acid water with the pH value of 2.0;
F. and E, industrial preparative chromatographic purification, namely dissolving the precipitate washed by the acid water in the step E with 40% methanol, purifying by using an industrial preparative chromatogram, wherein the mass ratio of a C18 filler to the crude drug of the industrial preparative chromatogram is 1:3, purifying for 1 time, the mass ratio of the methanol to the flow rate of 50 ml.
Example 3
the method for extracting apigenin-7-o- β -D-glucuronide from broussonetia papyrifera leaves comprises the following steps:
A. extraction: weighing 5kg of broussonetia papyrifera leaves, adding 15 times of 70% ethanol into the broussonetia papyrifera leaves, soaking for 2 hours, extracting for three times under reflux, extracting for 2 hours each time, combining the extracting solutions, and concentrating under reduced pressure at 50 ℃ to obtain a concentrated solution I with the crude drug concentration of 1.2 g/ml;
B. water precipitation: adding 6 times of deionized water into the concentrated solution I, refrigerating at 8 ℃, centrifuging and filtering, and adjusting the concentration of the crude drug in the filtrate to 0.17 g/ml;
C. purifying with macroporous adsorption resin: purifying the filtrate obtained in the step B by using HZ816 macroporous adsorption resin, weighing the macroporous adsorption resin according to the mass ratio of the resin to the crude drug of 1:1.5, filling the wet resin into a column, loading the filtrate under the condition of pH3.5 at the loading flow rate of 3BV/h, and saturating the filtrate for 1 hour after loading; washing with 10% ethanol with pH of 4.0 to remove impurities, wherein the elution flow rate is 5BV/h, and the elution dosage is 5 BV; eluting with 60% ethanol at flow rate of 7BV/h and with elution amount of 7BV, collecting eluate, and concentrating under reduced pressure at 50 deg.C to obtain concentrated solution II with crude drug concentration of 0.4 g/ml;
D. and (3) purifying the polyamide resin: selecting 40-mesh polyamide resin, wherein the mass ratio of the polyamide resin to the crude drug is 1:6, loading the concentrated solution II, the loading flow rate is 3BV/h, saturating for 1h after loading, eluting with 15BV water at the flow rate of 5BV/h, then eluting with 11BV20% ethanol at the flow rate of 5BV/h, removing impurities, then eluting with 15BV 80% ethanol at the flow rate of 7BV/h, collecting eluent, and concentrating under reduced pressure at 50 ℃ to obtain a concentrated solution III with the crude drug concentration of 3.5 g/ml;
E. acid precipitation: d, regulating the pH value of the concentrated solution III obtained in the step D to be 2.0 by using hydrochloric acid, standing at 4 ℃ for 24 hours, filtering, and washing a precipitate obtained after filtering for 3 times by using acid water with the pH value of 2.0;
F. and (3) performing industrial preparative chromatographic purification (adopting a dynamic axial compression column), dissolving the precipitate washed by acid water in the step E with 70% methanol, performing industrial preparative chromatographic purification, wherein the mass ratio of a C18 filler to the crude drug in the industrial preparative chromatographic is 1:3, purifying for 1 time, the mobile phase is methanol-1 thousandth of formic acid, the ratio of the methanol-1 thousandth of formic acid is 45:55, the flow rate is 50ml/min, collecting apigenin-7-o- β -D-glucuronide liquid medicine according to chromatographic peaks, then performing reduced pressure concentration, and freeze drying to obtain 17.1g of apigenin-7-o- β -D-glucuronide, wherein the yield is 84.5%, and the purity is 97.5%.
Claims (1)
1. A method for extracting apigenin-7-o- β -D-glucuronide from broussonetia papyrifera leaves is characterized by comprising the following steps:
A. extraction: weighing broussonetia papyrifera leaves, adding 13 times of 60% ethanol into the broussonetia papyrifera leaves, soaking for 1 hour, performing reflux extraction for three times, performing 2 hours each time, combining extracting solutions, and performing reduced pressure concentration at 60 ℃ to obtain a concentrated solution I with the crude drug concentration of 1 g/ml;
B. water precipitation: adding 5 times of deionized water into the concentrated solution I, refrigerating at 4-10 deg.C for 24 hr, centrifuging, filtering, and adjusting the concentration of the filtrate to 0.17 g/ml;
C. purifying with macroporous adsorption resin: purifying the filtrate obtained in the step B by using HZ816 macroporous adsorption resin, weighing the macroporous adsorption resin according to the mass ratio of the resin to the crude drug of 1:1.5, filling the wet resin into a column, loading the filtrate under the condition of pH3.5-4.0 at the loading flow rate of 2BV/h, and saturating for 1 hour after loading; washing with 10% ethanol with pH of 3.5-4.0 to remove impurities, wherein the flow rate of elution is 4BV/h, and the amount of elution is 6 BV; eluting with 60% ethanol at flow rate of 6BV/h and elution amount of 8BV, collecting eluate, and concentrating under reduced pressure at 60 deg.C to obtain concentrated solution II with crude drug concentration of 0.2 g/ml;
D. and (3) purifying the polyamide resin: selecting 30-40 mesh polyamide resin, wherein the mass ratio of the polyamide resin to the crude drug is 1:6, loading the concentrated solution II, the flow rate of loading is 2BV/h, saturating for 1h after loading, eluting with 16BV water at the flow rate of 4BV/h, then eluting with 12BV20% ethanol at the flow rate of 4BV/h, removing impurities, then eluting with 16BV 80% ethanol at the flow rate of 6BV/h, collecting eluent, and concentrating under reduced pressure at 60 ℃ to obtain concentrated solution III with the crude drug concentration of 4.0 g/ml;
E. acid precipitation: adjusting the pH value of the concentrated solution III obtained in the step D to 2.0-2.5 by using hydrochloric acid, standing at 4-10 ℃ for 24 hours, filtering, and washing the precipitate obtained after filtering by using acid water with the pH value of 2.0-2.5 for 3 times;
F. and E, industrial preparative chromatography purification, namely dissolving the precipitate washed by the acid water in the step E by 40-70% of methanol, purifying by using industrial preparative chromatography, wherein the mass ratio of C18 filler to crude drug of the industrial preparative chromatography is 1:3, purifying for 1 time, the mass ratio of methanol with a mobile phase of 45:55 to 1 thousandth of formic acid, the flow rate is 50ml/min, collecting apigenin-7-o- β -D-glucuronide liquid medicine according to chromatographic peaks, then concentrating under reduced pressure, and freeze-drying to obtain apigenin-7-o- β -D-glucuronide.
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