CN112480191A - Separation and purification method of monomer A and B of dysphagia - Google Patents

Separation and purification method of monomer A and B of dysphagia Download PDF

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CN112480191A
CN112480191A CN202011373957.2A CN202011373957A CN112480191A CN 112480191 A CN112480191 A CN 112480191A CN 202011373957 A CN202011373957 A CN 202011373957A CN 112480191 A CN112480191 A CN 112480191A
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dysphagia
methanol
dichloromethane
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silica gel
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李俊
张高荣
周德雄
黄锡山
黄艳
邓胜平
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Guangxi Normal University
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Abstract

The invention discloses a separation and purification method of a monomer A and a monomer B of dysphagia rice, which takes dysphagia rice leaves as a raw material, and the method comprises the steps of ethanol extraction with specific concentration, macroporous adsorption resin adsorption, silica gel chromatographic column chromatography, and high performance liquid phase preparation C18Purifying by silica gel chromatography column to obtain two new monomer compounds. The method can effectively remove a large amount of impurities in the dysphagia miqueliana, and can obtain two dysphagia miqueliana glycosides at one time, thereby providing a material basis for the activity research of the dysphagia miqueliana glycosides and the development of new medicines with single component.

Description

Separation and purification method of monomer A and B of dysphagia
Technical Field
The invention relates to the technical field of separation and purification of active ingredients of traditional Chinese medicines, in particular to a separation and purification method of monomers A and B of dysphagia.
Background
Choking Miyayan (Streblus tonkinensis) belongs to Moraceae (Moraceae) and belongs to the genus Streblus (Streblus laurus). Belongs to the Moraceae (Moraceae) plant, and belongs to the genus Streblus (Streblus lour). Dysphagia due to the fact that the rice poplar is often used as a folk medicinal plant for treating diseases. Through research in the literature, no report on the chemical components and the biological activity of the miyangjie is found so far. Based on that the dysphagia miqueliana is taken as a medicinal plant commonly used by people, in order to better and deeply research components in the medicinal plant, develop and utilize the plant, a separation and purification process of dysphagia miqueliana glycoside A and B, which has the advantages of high extraction rate, low cost and easy industrial production, is found, and can lay a foundation for the research of the characteristic biological activity of dysphagia miqueliana and provide a premise for the research of structure-activity relationship.
Disclosure of Invention
Aiming at the problem that the separation and purification of the dysphagia-a monomer is not available at present, the invention provides a separation and purification method of dysphagia-a and-B monomers. The method can effectively remove a large amount of impurities in the dysphagia miqueliana, and can obtain two dysphagia miqueliana glycosides at one time, thereby providing a material basis for the activity research of the dysphagia miqueliana glycosides and the development of new medicines with single component.
The technical scheme for realizing the purpose of the invention is as follows:
a separation and purification method of monomer of dysphagia aspergilloside A and B comprises the following steps:
1) extracting dysphagia Miyana leaf with 10-15 mass ratios of 65-75% ethanol water solution, recovering ethanol, and diluting the remaining water with 10 times of distilled water to obtain dysphagia Miyana leaf crude extract water solution;
2) carrying out D101 type macroporous adsorption resin column chromatography on the crude extract aqueous solution obtained in the step 1), after full adsorption, washing with distilled water with 4-6 column volumes to remove unadsorbed impurities, then sequentially eluting with 20-35% ethanol aqueous solutions with 4-6 column volumes, discarding the eluent, then eluting with 38-45% ethanol aqueous solutions with 4-6 volume, and concentrating the eluent to obtain an eluted part rich in the icariside A and B;
3) dissolving the part of the sample eluted by 38% -45% ethanol water solution in the step 2) by using methanol, then carrying out silica gel chromatographic column chromatography, sequentially eluting by using 4-6 column volumes of mixed solution of 3% -10% of dichloromethane and 97% -90% of methanol in volume ratio as eluent, discarding 3% -5% of dichloromethane and 97% -95% of methanol mixed solution eluent, and collecting 10% of dichloromethane and 90% of methanol mixed solution eluent;
4) subjecting the eluate of 10% dichloromethane and 90% methanol mixture collected in step 3) to high performance liquid chromatography C18Performing column chromatography to obtain the icaritin A and B, which are new compounds and have the structural formulas shown as the following formulas respectively:
Figure BDA0002807637740000021
the extract of the dysphagia miqueliana in the step 1) is prepared by the following method: crushing dysphagia Miyana leaves, adding 65-75% ethanol water solution with 10-15 times of weight of the leaves, heating and refluxing for 2-3 times, concentrating under reduced pressure, and drying to obtain dysphagia Miyana leaf extract.
The macroporous resin in the step 2) is polystyrene resin type macroporous resin.
The model of the macroporous resin in the step 2) is D101, the preferred macroporous resin has large adsorption capacity, easy elution and good adsorption kinetics, and does not adsorb saccharides, proteins, inorganic acids, salts, alkalis and micromolecular hydrophilic organic matters, so that general glycoside substances can be separated from the substances, and a better separation effect can be obtained in a shorter time.
The silica gel chromatographic column in the step 3) is a normal phase silica gel chromatographic column.
The purification process in the step 3) is as follows: eluting with 38% -45% ethanol water solution in step 2), dissolving the sample rich in C and B with a small amount of methanol, performing silica gel column chromatography, and gradient eluting with 4-6 column volumes of mixed solution of 3% -10% dichloromethane and 97% -90% methanol as eluent.
The chromatographic column of the high performance liquid chromatography in the step 4) is a reversed-phase octadecylsilane chemically bonded silica chromatographic column, the specification is 20 x 250mm, the particle size of the filler is 5.0 mu m, the high performance liquid chromatography can be used at a higher temperature and under a lower pH condition, the stationary phase does not collapse, the column effect can be kept for a long time, and the service life of the column is prolonged.
The detection conditions of the high performance liquid chromatography are as follows:
stationary phase: chromatographic column with octadecylsilyl bonded silica gel as filler;
detection wavelength: 230 nm;
flow rate: 2.0-4.0 mL/min;
column temperature: 25-35 ℃;
mobile phase: the method comprises the following steps of (1) eluting with 85-80% of water as a mobile phase A and 15-20% of methanol as a mobile phase B, wherein the proportion of the mobile phase A to the mobile phase B is a volume ratio, and in the preparation process of high performance liquid chromatography, the selection of chromatographic conditions is very important and directly influences the retention time, the separation degree and the like of a substance chromatographic peak; the chromatographic conditions mainly comprise a chromatographic column (comprising filler, column length, column temperature and the like), a mobile phase (comprising components, flow rate and the like), a detector, a detection wavelength, column temperature and the like.
Performing high performance liquid chromatography C on the eluate of the mixture of 10% dichloromethane and 90% methanol collected in step 3) in step 4)18The column chromatography purification process comprises: adding 10% dichloromethane and 90% methanol mixed solution eluate to reverse phase C18Eluting with 15-20% methanol water solution in silica gel chromatographic column to obtain monomeric compounds of icaritin A and icaritin B.
In the technical scheme, the miyan dysphagia is a plant belonging to the genus magpie of the family Moraceae, and the medicinal material part is dry leaves.
The dysphagia oryzae contains not only dysphagia oryzae glycoside, but also flavonoid, alkaloids, saccharides, trace elements and other very complex components, so that separation of the dysphagia oryzae glycoside from other substances is difficult to realize, the content of the dysphagia oryzae glycoside is very low, the structure and the physicochemical properties are very similar, and a plurality of monomers of the dysphagia oryzae glycoside are difficult to obtain at one time by a simple separation method.
According to the method for separating and purifying the dysphagia miyagar monomer in the technical scheme, aiming at the physicochemical properties of each component in dysphagia miyagar, a large amount of impurities in the dysphagia miyagar can be effectively removed, the dysphagia miyagar monomer with higher purity can be obtained, the target preparation of the dysphagia miyagar can be realized, a plurality of dysphagia miyagar with known activity can be obtained at one time, and simultaneously, the trace glycosides are enriched and separated, so that the glycoside library can be enriched continuously, and a material basis is provided for the activity research of glycoside compounds and the development of new drugs with single components.
The method can effectively remove a large amount of impurities in the dysphagia miqueliana, and can obtain two dysphagia miqueliana glycosides at one time, thereby providing a material basis for the activity research of the dysphagia miqueliana glycosides and the development of new medicines with single component.
Drawings
FIG. 1 shows the reverse phases C of C and A of C in the examples18Preparing chromatogram by silica gel column chromatography;
FIG. 2 shows dysphagia A of the example1H NMR spectrum;
FIG. 3 shows dysphagia A of the example13C NMR spectrum;
FIG. 4 shows dysphagia B of the example1H NMR spectrum;
FIG. 5 shows dysphagia B of the example13C NMR spectrum.
Detailed Description
The invention will be further elucidated with reference to the drawings and examples, without however being limited thereto.
Example 1:
a separation and purification method of monomer of dysphagia aspergilloside A and B comprises the following steps:
1) taking 10kg of dry miyan choke leaf, adding 10 times of 65% ethanol water solution (volume ratio) of raw materials by mass ratio, sequentially heating and refluxing for 3 times for 3 hours, 2 hours and 2 hours, combining filtrates, and recovering ethanol under reduced pressure to obtain extract;
2) diluting the extract obtained in the step 1) by 50 times with distilled water, adsorbing the extract by a D101 macroporous adsorption resin chromatographic column, washing and washing by distilled water with 4 column volumes to remove unadsorbed impurities, sequentially eluting by 10% ethanol water solution and 30% ethanol water solution with 4 column volumes, discarding the eluent, eluting by 40% ethanol water solution, and concentrating the eluent to obtain an eluted part rich in the icariin A and B;
3) taking the 40% ethanol eluate obtained in the step 2), performing silica gel column chromatography, sequentially eluting with 4 column volumes of 3% dichloromethane and 97% methanol mixed solution and 10% dichloromethane and 90% methanol mixed solution (volume ratio), discarding 3% dichloromethane and 97% methanol mixed solution (volume ratio) eluate, and collecting 10% dichloromethane and 90% methanol mixed solution eluate;
4) subjecting the eluate of the mixture of 10% dichloromethane and 90% methanol collected in step 3) to reversed phase C18Performing silica gel column chromatography, eluting with water-methanol (80:20) to obtain first compound A (t)R21.80min) and a second compound B (t)R＝26.45min)。
In the step 4), the conditions for detecting and monitoring the high performance liquid chromatography are as follows:
stationary phase: chromatographic column with octadecylsilyl bonded silica gel as filler;
a detector: an ultraviolet detector;
detection wavelength: 230 nm;
flow rate: 3.0 mL/min;
column temperature: 25 ℃;
mobile phase: water was 80% for mobile phase a and methanol was 20% for mobile phase B.
By detecting the obtained first monomer compound a and the second monomer compound B under the above-mentioned detection conditions, the purity of the first monomer compound a was 99.5%, and the purity of the second monomer compound B was 99.7%.
Example 2:
a separation and purification method of monomer of dysphagia aspergilloside A and B comprises the following steps:
1) adding 12 times of 73% ethanol water solution (mass ratio) into 10kg of dried miyan dysphagia leaves, sequentially heating and reflux-extracting for 3 times (3 hr, 2 hr, and 2 hr), mixing filtrates, and recovering ethanol under reduced pressure to obtain extract;
2) suspending the extract in 50L water, adsorbing with D101 macroporous adsorbent resin chromatographic column, washing with water, and eluting with 20% and 50% ethanol to obtain 20% and 50% ethanol eluate respectively, wherein the 50% ethanol eluate is used as the extract of Choking leaf of Miyan that is rich in Chongxin A and Chongxin B;
3) collecting 625.0g of 50% ethanol eluate obtained in the step 2), performing silica gel column chromatography, sequentially eluting with 4 column volumes of 4% dichloromethane and 96% methanol mixed solution, 10% dichloromethane and 90% methanol mixed solution, and discarding 4% dichloromethane and 96% methanol mixed solution eluate, and collecting 10% dichloromethane and 90% methanol mixed solution eluate;
4) subjecting the eluate of the mixture of 10% dichloromethane and 90% methanol collected in step 3) to reversed phase C18Performing silica gel column chromatography, eluting with water-methanol (80:20) to obtain first compound A (t)R21.82min) and a second compound B (t)R＝26.43min)。
In step 4), the conditions for detection and monitoring by high performance liquid chromatography were the same as in example 1 except that the flow rate was 3.5ml/min and the column temperature was 30 ℃.
By detecting the obtained first monomer compound a and the second monomer compound B under the above-mentioned detection conditions, the purity of the first monomer compound a was 99.2%, and the purity of the second monomer compound B was 99.4%.
Example 3:
a separation and purification method of monomer of dysphagia aspergilloside A and B comprises the following steps:
1) taking 10kg of dry miyan choke leaf, adding 15 times of 75% ethanol water solution (mass ratio of raw materials), sequentially heating and refluxing for 3 times for 3 hours, 2 hours and 2 hours, combining filtrates, and recovering ethanol under reduced pressure to obtain extract;
2) suspending the extract obtained in the step 1) in 50L of water, adsorbing by a D101 macroporous adsorption resin chromatographic column, washing with water, and then eluting with 20% and 50% ethanol to obtain 20% and 50% ethanol eluate respectively, wherein the 50% ethanol eluate is used as the extract of the dysphagia miqueliana leaves rich in dysphagia glycoside A and B;
3) subjecting the 50% ethanol eluate obtained in step 2) to silica gel column chromatography, sequentially discarding the 5% dichloromethane and 95% methanol mixed solution eluate (volume ratio) and 4 column volumes of 5% dichloromethane and 95% methanol mixed solution eluate, 10% dichloromethane and 90% methanol mixed solution eluate, and collecting the 10% dichloromethane and 90% methanol mixed solution eluate;
4) subjecting the eluate of 10% dichloromethane and 90% methanol mixture collected in step 3) to reverse phase C18Performing silica gel column chromatography, eluting with water-methanol (80:20) to obtain first compound A (t)R21.81min) and a second compound B (t)R＝26.44min)。
In step 4), the conditions for detection and monitoring by high performance liquid chromatography were the same as in example 1 except that the flow rate was 4.0ml/min and the column temperature was 35 ℃.
By detecting the obtained first monomer compound a and the second monomer compound B under the above-mentioned detection conditions, the purity of the first monomer compound a was 99.6%, and the purity of the second monomer compound B was 99.8%.
As shown in FIG. 1, FIG. 2, FIG. 3, FIG. 4 and FIG. 5, the two obtained monomer compounds are subjected to infrared, mass and nuclear magnetic resonance spectroscopy (R), (B), (C1HNMR、13CNMR、DEPT、1H-1The spectrum techniques of HCOSY, HSQC, HMBC, ROESY), Mass Spectrum (MS) and optical rotation and the like identify the structures of the icariin A and B, which are new compounds, and the physicochemical data of the icariin A and B are shown as follows:
choxoside A [4- (3-hydroxy-but-1-enyl) -3,4-dimethyl-2- (3,4, 5-dihydroxy-6-hydroxymethy-l-tetrahydro-pyran-2-yloxymethyl) -cyclohex-2-enone, strigolycoside A]: colorless oil, dissolved in methanol. HRESIMS (positive) M/z 387.2012[ M + H ]]+,(calc.for C19H31O8,387.2019)；
Figure BDA0002807637740000061
1H-NMR(400MHz CD3OD):δH2.55(2H,dd,J＝7.4,6.1Hz,H-5),1.92(2H,t,6.8,H-6),6.26(1H,dd,J＝15.9,5.1Hz,H-7),6.37(1H,dd,J＝15.9,1.2Hz,H-8),4.44(1H,m,H-9),1.36(3H,m,H-10),1.24(3H,s,H-11),1.24(3H,s,H-12),4.67(1H,d,J＝9.7Hz,H-13a),4.24(1H,d,J＝9.7Hz,H-13b),4.35(1H,d,J＝7.8Hz,H-1′),3.17(1H,t,8.3,H-2′),3.28(1H,m,H-3′),3.28(1H,m,H-4′),3.37(1H,m,H-5′),3.88(1H,dd,J＝11.9,2.2Hz,H-6′a),3.70(1H,dd,J＝11.9,5.3Hz,H-6′b)；13C-NMR(100MHz CD3OD)δC 36.6(C-1),170.0(C-2),130.9(C-3),200.6(C-4,C＝O),35.0(C-5),37.6(C-6),143.9(C-7),124.1(C-8),68.8(C-9),23.5(C-10),27.4(C-11),27.4(C-12),64.4(C-13),104.1(C-1′),74.9(C-2′),77.8(C-3′),71.4(C-4′),78.0(C-5′),62.8(C-6′)。
Choxoside B [2- (4-p-Tolyl-pentyloxy) -tetrahydropyran-3, 4,5-triol, striglycoside B]: colorless needle crystals, dissolved in methanol. HRESIMS M/z 355.1766[ M + HCOO]-(calcd For C18H27O7,355.1780).
Figure BDA0002807637740000062
1H-NMR(400MHz CD3OD):δH 7.07(2H,m,H-2,6),7.06(2H,m,H-3,5),3.75(1H,dt,9.2,6.8,H-10a),3.49(1H,m,H-10b),2.63(1H,dt,12.0,7.2,H-7),2.28(3H,s,C-12),1.63(2H,m,H-8),1.48(2H,m,H-9),1.23(3H,d,7.2,H-11),4.14(1H,d,J＝7.6Hz,H-1′),3.14(1H,m,H-2′),3.48(1H,m,H-3′),3.46(1H,m,H-4′),3.82(2H,dd,11.6,5.6,H-5′)；13C-NMR(100MHz CD3OD)δC 145.5(C-1),127.9(C-2,6),129.9(C-3,5),136.3(C-4),40.6(C-7),35.7(C-8),29.0(C-9),70.9(C-10),23.0(C-11),21.4(C-12),105.1(C-1′),74.9(C-2′),77.8(C-3′),71.2(C-4′),66.9(C-5′)。

Claims (8)

1. A separation and purification method of a monomer A and a monomer B of dysphagia aspergilli is characterized by comprising the following steps:
1) extracting dysphagia Miyana leaf with 10-15 mass ratios of 65-75% ethanol water solution, recovering ethanol, and diluting the remaining water with 10 times of distilled water to obtain dysphagia Miyana leaf crude extract water solution;
2) subjecting the crude extract aqueous solution obtained in the step 1) to D101 type macroporous adsorption resin column chromatography, fully adsorbing, washing with distilled water of 4-6 column volumes to remove unadsorbed impurities, sequentially eluting with 20% -35% ethanol aqueous solutions of 4-6 column volumes, discarding the eluent, eluting with 38-45% ethanol aqueous solutions of 4-6 column volumes, and concentrating the eluent to obtain an eluted part rich in the icariin A and B;
3) dissolving the part of the sample eluted by 38% -45% ethanol water solution in the step 2) by using methanol, then carrying out silica gel chromatographic column chromatography, sequentially eluting by using mixed solution of 3% -10% dichloromethane and 97% -90% methanol which are respectively 4-6 column volumes as eluent, discarding mixed solution eluent of 3% -5% dichloromethane and 97% -95% methanol, and collecting mixed solution eluate of 10% dichloromethane and 90% methanol;
4) subjecting the eluate of 10% dichloromethane and 90% methanol mixture collected in step 3) to high performance liquid chromatography C18Performing column chromatography to obtain the icaritin A and B, which are new compounds and have the structural formulas shown as the following formulas respectively:
Figure FDA0002807637730000011
2. the method for separating and purifying the monomers of dysphagia aspergilloside A and B according to claim 1, wherein the extract of dysphagia aspergilloside in step 1) is prepared by the following method: pulverizing dysphagia Miyana leaf, adding 65-75% ethanol water solution 10-15 times of the leaf, heating and reflux extracting for 2-3 times, concentrating under reduced pressure, and drying to obtain dysphagia Miyana leaf extract.
3. The process of claim 1, wherein the macroporous resin used in step 2) is a polystyrene resin type macroporous resin.
4. The method for separating and purifying the monomeric units of dysphagia milacoside A and B according to claim 3, wherein the model number of the macroporous resin in the step 2) is D101.
5. The method for separating and purifying the monomeric units of dysphagia miyazaide A and B according to claim 1, wherein the silica gel chromatographic column in step 3) is a normal phase silica gel chromatographic column.
6. The method for separating and purifying the monomeric compounds of dysphagia aspergilloside A and B according to claim 1, wherein the purification process in step 3) is: eluting with 38% -45% ethanol water solution in step 2), dissolving the sample rich in C and B with a small amount of methanol, performing silica gel column chromatography, and gradient eluting with 4-6 column volumes of mixed solution of 3% -10% dichloromethane and 97% -90% methanol as eluent.
7. The method for separating and purifying the monomers of dysphagia aspergilloside A and B according to claim 1, wherein the high performance liquid chromatography column in step 4) is a reversed-phase octadecylsilane chemically bonded silica column, the specification is 20 x 250mm, and the particle size of the filler is 5.0 μm.
8. The method for separating and purifying C monomers of dysphagia according to claim 1, wherein the eluate of step 4) is subjected to HPLC C using a mixture of 10% dichloromethane and 90% methanol collected in step 3)18The column chromatography purification process comprises: adding 10% dichloromethane and 90% methanol mixed solution eluate to reverse phase C18Eluting with 15-20% methanol water solution in silica gel chromatographic column to obtain monomeric compounds of icaritin A and icaritin B.
CN202011373957.2A 2020-11-30 2020-11-30 Separation and purification method of monomer A and B of dysphagia Pending CN112480191A (en)

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