CN109053852B - Method for separating and purifying lily saponin monomer - Google Patents
Method for separating and purifying lily saponin monomer Download PDFInfo
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Abstract
The invention provides a method for separating and purifying a lily saponin monomer. The invention takes dried lily fleshy scaly leaves as raw materials, and the raw materials are extracted by ethanol with specific concentration, roughly separated by macroporous adsorption resin, then subdivided by a Sephadex LH-20 gel chromatographic column under the condition of monitoring by a high performance liquid chromatograph, and finally purified by a reverse silica gel chromatographic column to obtain three monomer compounds. The invention can effectively remove a large amount of impurities in lily through the combination of the optimum process and parameter conditions, and can obtain a plurality of lily saponins with known activity at one time, thereby providing a material basis for activity research of saponin compounds and development of new drugs with single component.
Description
Technical Field
The invention relates to the technical field of separation and purification of active ingredients of traditional Chinese medicines, in particular to a method for separating and purifying a lily saponin monomer.
Background
Bulbus Lilii is widely distributed in China, and the medicine has sweet and cold taste, has effects of nourishing yin, clearing lung-heat, clearing heart fire and tranquilizing mind, and can be used for treating yin deficiency, chronic cough, blood-stained sputum, palpitation, vexation, insomnia, dreaminess and listlessness etc., and is a product used as medicine and food. According to records in compendium of materia medica, lily has the efficacies of tonifying heart and lung, reinforcing kidney, nourishing brain, clearing heart fire, soothing nerves, moistening lung dryness, conditioning spleen and stomach, tonifying qi, regulating middle warmer, clearing heat, relieving cough, nourishing yin, stopping bleeding, relieving summer heat and the like. Bulbus Lilii mainly contains steroid saponin, alkaloids, phenolic acid glyceride, phospholipid, polysaccharide, amino acids and flavonoids. Wherein, the steroid saponin compound is the main active component, and has biological activities of anti-depression, antioxidation, anti-inflammation, anticancer, and the like. In order to reveal the material basis of treating diseases by traditional Chinese medicines taking saponin compounds as main active ingredients and fully utilize the pharmacological activity of lily steroid saponin monomer compounds, lily saponin monomers need to be separated and purified, but the existence of a large number of saponin compounds with similar structures in lily makes the separation of the steroid saponin monomer compounds very difficult, and the saponin compounds are generally absorbed only at the ultraviolet tail end, which brings difficulty to the on-line detection of the saponin compounds by utilizing high performance liquid chromatography, so how to realize the separation and purification of the saponin monomers in lily is a problem which troubles research and development personnel.
Disclosure of Invention
The invention provides a method for separating and purifying a lily saponin monomer, aiming at the problem that the existing separation and extraction method can not realize the separation and purification of the lily saponin monomer.
The lily is lily, which is a liliaceae plant, such as red sage root, lily or lilium tenuifolium, and the medicinal material part is dry fleshy scaly leaves.
In order to solve the technical problems, the technical scheme provided by the invention is as follows:
a method for separating and purifying a lily saponin monomer comprises the following steps:
adding the extract of lily bulb leaves into a chromatographic column filled with nonpolar macroporous adsorption resin, eluting with 3-5 column volumes of water, 8-12% of ethanol solution and 38-41% of ethanol solution respectively, discarding the eluent, eluting with 3-5 column volumes of 79-82% of ethanol solution, collecting the eluent, and evaporating to obtain a dry extract;
adding the dry extract into a gel chromatographic column filled with Sephadex LH-20, eluting with a methanol solution or an ethanol solution with the volume concentration of 49-53%, detecting and monitoring by high performance liquid chromatography, counting the next part with the ultraviolet absorption peak value of a main peak as a sectional basis and the ultraviolet absorption value lower than 5 milliamperes to obtain 5 components, and recording the components as a component 1, a component 2, a component 3, a component 4 and a component 5 according to the collection time sequence;
and step three, respectively purifying the component 3, the component 4 and the component 5 to obtain 3 corresponding monomer compounds.
Compared with the prior art, the invention has the following beneficial effects:
besides saponins, lily contains very complex components such as saccharides, flavonoids, alkaloids, trace elements and the like, so that the separation of lily saponins from other substances is difficult to realize, the content of saponins in lily is very low, the structure and the physicochemical properties are very similar, and a plurality of monomers of lily saponins are difficult to obtain by a simple separation method at one time. According to the method for separating and purifying the lily saponin monomer, provided by the invention, aiming at the physicochemical properties of each component in lily, a large amount of impurities in lily are effectively removed through the sequential collocation of the steps I to III and the combination of proper parameters, so that the lily saponin monomer with higher purity is obtained. The method for separating and purifying the lily saponin monomer can realize the target preparation of the lily saponin, can obtain a plurality of lily saponins with known activity at one time, and simultaneously enrich and separate trace saponins, thereby continuously enriching saponin libraries and providing a material basis for activity research of saponin compounds and development of new drugs with single components.
Preferably, in the first step, the extract of lily bulb leaves is prepared by the following method: crushing lily bulb leaves, adding an ethanol solution with the volume concentration of 65-70% and the volume which is 4-5 times that of the lily bulb leaves, heating, refluxing and extracting for 2-3 times, concentrating under reduced pressure, and drying to obtain an extract of the lily bulb leaves.
By the extraction method, a large amount of impurities in the lily bulb scale leaves can be removed, and the extract is ensured to mainly contain saponin, flavone and other components.
Preferably, in the first step, the macroporous resin is polystyrene resin type macroporous resin.
More preferably, in the first step, the model of the macroporous resin is D101.
The preferred macroporous resin has large adsorption capacity, easy elution and good adsorption kinetics performance, and does not adsorb protein, saccharides, inorganic acid, alkali, salt and micromolecular hydrophilic organic matters, so that common saponin substances can be separated from the substances, and a better separation effect can be obtained in a shorter time.
Preferably, in the third step, the reverse silica gel chromatographic column is an octadecylsilane bonded silica gel chromatographic column.
Preferably, in the second step, the conditions for detecting and monitoring by high performance liquid chromatography are as follows:
stationary phase: chromatographic column with octadecylsilyl bonded silica gel as filler;
detection wavelength: 203 nm;
flow rate: 0.8-1.2 ml/min;
column temperature: 25-35 ℃;
mobile phase: water is used as a mobile phase A, acetonitrile is used as a mobile phase B, and gradient elution is carried out, wherein the gradient elution sequence is as follows:
for 0-5 min, the mobile phase A is 92%, and the mobile phase B is 8%;
5-12 min, wherein the mobile phase A is 92-80%, and the mobile phase B is 8-20%;
12-25 min, the mobile phase A is 80-45%, and the mobile phase B is 20-55%;
25-30 min, wherein the mobile phase A is 45-5%, and the mobile phase B is 55-95%;
and (3) 30-35 min, wherein the mobile phase A is 5% and the mobile phase B is 95%.
The ratio of the mobile phase A to the mobile phase B is a volume ratio.
In the high performance liquid chromatography separation process, the selection and combination of the chromatographic conditions are important because it directly affects the time of appearance of peaks, peak shapes, etc. of the substances; 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, detection wavelength and the like. The chromatographic conditions provided by the invention can optimize the peak time, peak shape, separation effect and the like of the substances, and realize the high-efficiency separation of the lily saponin monomers.
Preferably, the chromatographic column is an Agilent SB-C18 chromatographic column with the specification of 2.1X 100mm and the particle size of the filler of 1.8 μm.
The preferable chromatographic column can be used under the conditions of higher temperature and lower pH, the stationary phase can not generate the phenomenon of phase collapse, the column effect can be kept for a long time, and the service life of the column is prolonged.
Preferably, in the third step, the purification step of the component 3 is: and adding the component 3 into a reverse silica gel chromatographic column, and eluting with an acetonitrile aqueous solution with the volume concentration of 25-27% to obtain a first monomer compound.
Preferably, in the third step, the purification step of the component 4 is: and (3) adding the component 4 into a reverse silica gel chromatographic column, eluting with an acetonitrile aqueous solution with the volume concentration of 36-40%, and obtaining a second monomer compound.
Preferably, in the third step, the purification step of the component 5 is as follows: and (3) adding the component 5 into a reverse silica gel chromatographic column, eluting with 48-52% by volume acetonitrile aqueous solution, and obtaining a third monomer compound.
The component 3, the component 4 and the component 5 are respectively purified by the method, so that a first monomer compound, a second monomer compound and a third monomer compound with higher purity can be obtained.
Drawings
In order to more clearly illustrate the technical solutions in the embodiments of the present invention, the drawings needed to be used in the embodiments will be briefly described below, and it is obvious that the drawings in the following description are only some embodiments of the present invention, and it is obvious for those skilled in the art that other drawings can be obtained according to these drawings without creative efforts.
FIG. 1 is a high performance liquid chromatogram of a first monomer compound prepared in example 3 of the present invention;
FIG. 2 is a high performance liquid chromatogram of a second monomeric compound prepared in example 3 of the present invention;
FIG. 3 is a high performance liquid chromatogram of a third monomer compound prepared in example 3 of the present invention.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail with reference to the following embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
Example 1
A method for separating and purifying a lily saponin monomer comprises the following steps:
crushing dried lily bulb leaves, adding 65% ethanol solution with the volume 4 times that of the lily bulb leaves, heating and refluxing for 2 times, and decompressing and recovering the ethanol solution to obtain an ethanol extract of the lily bulb leaves;
step two, adding the alcohol extract of the lily bulb leaves into a chromatographic column filled with D101 macroporous adsorption resin, eluting with 3 column volumes of water, 8 volume percent of ethanol solution and 38 volume percent of ethanol solution respectively, discarding the eluent, eluting with 4 column volumes of 82 volume percent of ethanol solution, collecting the eluent, and evaporating to dryness to obtain a dry extract;
adding the dry extract into a gel chromatographic column filled with Sephadex LH-20, eluting with 49% methanol solution or ethanol solution, detecting and monitoring by high performance liquid chromatography, taking the ultraviolet absorption peak value of a main peak as a sectional basis, counting the ultraviolet absorption value lower than 5 milliamperes into the next part to obtain 5 components, and recording the components as component 1, component 2, component 3, component 4 and component 5 according to the collection time sequence;
step four, adding the component 3 into a reverse silica gel chromatographic column, and eluting with an acetonitrile aqueous solution with the volume concentration of 25% to obtain a first monomer compound;
adding the component 4 into a reverse silica gel chromatographic column, and eluting with acetonitrile water solution with the volume concentration of 40% to obtain a second monomer compound;
and adding the component 5 into a reverse silica gel chromatographic column, and eluting with 48% by volume of acetonitrile aqueous solution to obtain a third monomer compound.
In the second step, the detection and monitoring conditions of the high performance liquid chromatography are as follows:
a chromatographic column: agilent SB-C18, 2.1 × 100mm, 1.8 μm;
detection wavelength: 203 nm;
flow rate: 0.8 ml/min;
column temperature: 25 ℃;
mobile phase: water is used as a mobile phase A, acetonitrile is used as a mobile phase B, and gradient elution is carried out, wherein the gradient elution sequence is as follows:
| time min | Water | Acetonitrile% | |
| 0 | 92 | 8 | |
| 5 | 92 | 8 | |
| 12 | 80 | 20 | |
| 25 | 45 | 55 | |
| 30 | 5 | 95 | |
| 35 | 5 | 95 |
By detecting the obtained first monomer compound, second monomer compound and third monomer compound under the above detection conditions, the purity of the first monomer compound is 98.6%, the purity of the second monomer compound is 95.7% and the purity of the third monomer compound is 93.0%.
The purity of the first, second and third monomeric compounds was 100% as determined by evaporation light detection (ELSD). The detection conditions are as follows: temperature of the drift tube: 70 ℃; temperature of the evaporating tube: 65 ℃ of: gas flow rate: 2.2L/min.
Example 2
A method for separating and purifying a lily saponin monomer comprises the following steps:
crushing dried lily bulb leaves, adding 68% ethanol solution with the volume 5 times that of the lily bulb leaves, heating and refluxing for 2 times, and decompressing and recovering the ethanol solution to obtain an ethanol extract of the lily bulb leaves;
step two, adding the alcohol extract of the lily bulb leaves into a chromatographic column filled with D101 macroporous adsorption resin, eluting with 4 column volumes of water, 12 volume percent of ethanol solution and 41 volume percent of ethanol solution respectively, discarding the eluent, eluting with 3 column volumes of 79 volume percent of ethanol solution, collecting the eluent, and evaporating to dryness to obtain a dry extract;
adding the dry extract into a gel chromatographic column filled with Sephadex LH-20, eluting with a methanol solution or an ethanol solution with the volume concentration of 53%, detecting and monitoring by high performance liquid chromatography, taking the ultraviolet absorption peak value of a main peak as a sectional basis, counting the ultraviolet absorption value lower than 5 milliamperes into the next part to obtain 5 components, and recording the components as a component 1, a component 2, a component 3, a component 4 and a component 5 according to the collection time sequence;
step four, adding the component 3 into a reverse silica gel chromatographic column, and eluting with 27 volume percent acetonitrile aqueous solution to obtain a first monomer compound;
adding the component 4 into a reverse silica gel chromatographic column, and eluting with an acetonitrile aqueous solution with the volume concentration of 36% to obtain a second monomer compound;
and adding the component 5 into a reverse silica gel chromatographic column, and eluting with 52% acetonitrile water solution by volume to obtain a third monomer compound.
In the second step, the conditions for detection and monitoring of the HPLC were the same as in example 1 except that the flow rate was 1.2ml/min and the column temperature was 35 ℃.
The purity of the first monomer compound, the purity of the second monomer compound, and the purity of the third monomer compound were measured by using the conditions of the high performance liquid chromatography, and the purity of the first monomer compound was 98.7%, the purity of the second monomer compound was 95.6%, and the purity of the third monomer compound was 92.9%.
The purity of the first, second and third monomeric compounds was 100% as determined by evaporation light detection (ELSD). The detection conditions are as follows: temperature of the drift tube: 70 ℃; temperature of the evaporating tube: 65 ℃ of: gas flow rate: 2.2L/min.
Example 3
A method for separating and purifying a lily saponin monomer comprises the following steps:
crushing dried lily bulb leaves, adding 70% ethanol solution with the volume 4 times that of the lily bulb leaves, heating and refluxing for 3 times, and decompressing and recovering the ethanol solution to obtain an ethanol extract of the lily bulb leaves;
step two, adding the alcohol extract of the lily bulb leaves into a chromatographic column filled with D101 macroporous adsorption resin, eluting with 5 column volumes of water, 10 volume percent of ethanol solution and 40 volume percent of ethanol solution respectively, discarding the eluent, eluting with 5 column volumes of 80 volume percent of ethanol solution, collecting the eluent, and evaporating to dryness to obtain a dry extract;
adding the dry extract into a gel chromatographic column filled with Sephadex LH-20, eluting with a methanol solution or an ethanol solution with the volume concentration of 50%, detecting and monitoring by high performance liquid chromatography, taking the ultraviolet absorption peak value of a main peak as a sectional basis, counting the ultraviolet absorption value lower than 5 milliamperes into the next part to obtain 5 components, and recording the components as a component 1, a component 2, a component 3, a component 4 and a component 5 according to the collection time sequence;
step four, adding the component 3 into a reverse silica gel chromatographic column, and eluting with 26% acetonitrile aqueous solution by volume concentration to obtain a first monomer compound;
adding the component 4 into a reverse silica gel chromatographic column, and eluting with 38% acetonitrile aqueous solution by volume concentration to obtain a second monomer compound;
and adding the component 5 into a reverse silica gel chromatographic column, and eluting with a 50% acetonitrile aqueous solution by volume concentration to obtain a third monomer compound.
In the second step, the conditions for detection and monitoring by HPLC were the same as in example 1 except that the flow rate was 1.0ml/min and the column temperature was 30 ℃.
The obtained first monomer compound, second monomer compound and third monomer compound were detected under the detection conditions of the high performance liquid chromatography as shown in fig. 1-3, where the peak-off time of the first monomer compound was 18.423min, the peak-off time of the second monomer compound was 22.428min, and the peak-off time of the third monomer compound was 25.559 min. The purity of the first monomer compound was found to be 98.8%, the purity of the second monomer compound was found to be 95.8%, and the purity of the third monomer compound was found to be 93.1%.
The purity of the first, second and third monomeric compounds was 100% as determined by evaporation light detection (ELSD). The detection conditions are as follows: temperature of the drift tube: 70 ℃; temperature of the evaporating tube: 65 ℃; gas flow rate: 2.2L/min.
The three monomeric compounds obtained were identified by Mass Spectrometry (MS) and nuclear magnetic resonance spectroscopy (NMR).
The first monomeric compound was identified as protobioside and the mass spectral data were as follows:1H NMR(600MHz，C5D5N)δ：0.88(3H,s,H-18)，1.04(3H,s,H-19)，1.32(3H,d,J＝6.7,H-21)，0.97(3H,d,J＝6.6,H-27)，4.97(1H,d,J＝7.1)，6.35(1H,br s)，1.75(3H,d,6.3)，5.01(3H,d,overlapped)。13the CNMR results are shown in Table 1.
The second monomeric compound was identified as (25R) -3 β,17 α -dihydroxy-5 α -spirostan-6-one 3-O- α -L-rha- (L → 2) - β -D-glucuronimer with the following mass spectra data:1H NMR(600MHz，C5D5N)δ：0.79(3H,s,H-18)，0.87(3H,s,H-19)，1.20(3H,d,J＝7.2,H-21)，0.66(3H,d,J＝5.4,H-27)，5.02(1H,d,J＝7.4)，6.30(1H,br s)，1.75(3H,d,J＝6.2)。13the C NMR results are shown in Table 1.
Determining the second monomer compound as (3 beta, 5 alpha, 25R) -3- [ [2-O- (6-Deoxy-alpha-L-mannopyranosyl) -beta-D-glucopyranosyl]oxy]spirostan-6-one, mass spectral data as follows:1H NMR(600MHz，C5D5N)δ：0.76(3H,s,H-18)，0.75(3H,s,H-19)，1.12(3H,d,J＝6.9,H-19)，0.67(3H,d,J＝5.8,H-27)，4.93(1H,d,overlapped)，6.33(1H,br s)，1.75(3H,d,J＝6.2)。13the C NMR results are shown in Table 1.
TABLE 113C NMR numberSummary of the contents
The 3 compounds are determined by mass spectrum, nuclear magnetic experiments and literature data to obtain 3 known compounds, and the compound information is shown in table 2.
TABLE 2 Compound information summary sheet
In conclusion, the method for separating and purifying the lily saponin monomer provided by the invention obtains three monomer compounds with higher purity through one separation process by combining the selected specific separation method with the optimal combination of process parameters, provides a material basis for the research and development of single components of the lily saponin, does not need special equipment in the separation and purification process, is simple and convenient in process operation, has high extraction efficiency, and has wide application prospect.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents or improvements made within the spirit and principle of the present invention should be included in the scope of the present invention.
Claims (9)
1. A method for separating and purifying a lily saponin monomer is characterized by comprising the following steps:
adding the extract of lily bulb leaves into a chromatographic column filled with nonpolar macroporous adsorption resin, eluting with 3-5 column volumes of water, 8-12% of ethanol solution and 38-41% of ethanol solution respectively, discarding the eluent, eluting with 3-5 column volumes of 79-82% of ethanol solution, collecting the eluent, and evaporating to obtain a dry extract;
adding the dry extract into a gel chromatographic column filled with Sephadex LH-20, eluting with a methanol solution or an ethanol solution with the volume concentration of 49-53%, detecting and monitoring by high performance liquid chromatography, collecting to obtain 5 components, and recording as a component 1, a component 2, a component 3, a component 4 and a component 5 according to the collection time sequence; wherein, the detection wavelength of the high performance liquid chromatography is 203nm, and the stationary phase: a chromatographic column with octadecylsilane chemically bonded silica as filler; flow rate: 0.8-1.2 ml/min; column temperature: at the temperature of 25-35 ℃,
mobile phase: water is used as a mobile phase A, acetonitrile is used as a mobile phase B, and gradient elution is carried out, wherein the gradient elution sequence is as follows:
for 0-5 min, the mobile phase A is 92%, and the mobile phase B is 8%;
5-12 min, wherein the mobile phase A is 92-80%, and the mobile phase B is 8-20%;
12-25 min, the mobile phase A is 80-45%, and the mobile phase B is 20-55%;
25-30 min, wherein the mobile phase A is 45-5%, and the mobile phase B is 55-95%;
30-35 min, wherein the mobile phase A is 5% and the mobile phase B is 95%;
and step three, purifying the component 3, the component 4 and the component 5 by reverse silica gel chromatographic columns respectively to obtain a first monomer compound, a second monomer compound and a third monomer compound, wherein the structural formulas of the first monomer compound, the second monomer compound and the third monomer compound are respectively shown as a formula I, a formula II and a formula III:
2. the method for separating and purifying lily saponin monomers as claimed in claim 1, wherein in the first step, the extract of lily bulb leaves is prepared by the following method: crushing lily bulb leaves, adding an ethanol solution with the volume concentration of 65-70% and the volume which is 4-5 times that of the lily bulb leaves, heating, refluxing and extracting for 2-3 times, concentrating under reduced pressure, and drying to obtain an extract of the lily bulb leaves.
3. The method for separating and purifying a lily saponin monomer as claimed in claim 1 or 2, wherein in the first step, the macroporous resin is polystyrene resin type macroporous resin.
4. The method for separating and purifying a lily saponin monomer as claimed in claim 3, wherein in the first step, the model of the macroporous resin is D101.
5. The method for separating and purifying a lily saponin monomer as claimed in claim 1, wherein in the third step, the reverse silica gel chromatographic column is an octadecylsilane bonded silica gel chromatographic column.
6. The method for separating and purifying a lily saponin monomer according to claim 1, wherein the high performance liquid chromatography column is an Agilent SB-C18 column, the specification of which is 2.1 x 100mm, and the particle size of the filler is 1.8 μm.
7. The method for separating and purifying a lily saponin monomer according to claim 1, wherein in the third step, the purification step of the component 3 is as follows: and adding the component 3 into a reverse silica gel chromatographic column, and eluting with an acetonitrile aqueous solution with the volume concentration of 25-27% to obtain a first monomer compound.
8. The method for separating and purifying a lily saponin monomer according to claim 1, wherein in the third step, the purification step of the component 4 is as follows: and adding the component 4 into a reverse silica gel chromatographic column, and eluting with an acetonitrile aqueous solution with the volume concentration of 36-40% to obtain a second monomer compound.
9. The method for separating and purifying a lily saponin monomer according to claim 1, wherein in the third step, the purification step of the component 5 is as follows: and adding the component 5 into a reverse silica gel chromatographic column, and eluting with an acetonitrile aqueous solution with the volume concentration of 48-52% to obtain a third monomer compound.
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