CN113402574B - Method for separating and purifying flavonoids compounds in ethyl acetate phase of polygonum multiflorum by high-speed counter-current chromatography - Google Patents
Method for separating and purifying flavonoids compounds in ethyl acetate phase of polygonum multiflorum by high-speed counter-current chromatography Download PDFInfo
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- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
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Abstract
The invention relates to a method for separating and purifying flavonoids compounds in polygonum multiflorum leaves by high-speed counter-current chromatography, which comprises the following steps: (1) Preparing a polygonum multiflorum ethyl acetate phase (2) by adopting a water-methanol-ethyl acetate-n-hexane solution with a volume ratio of 1; when the two-phase solvent system reaches the balance in the high-speed countercurrent column, dissolving the polygonum multiflorum ethyl acetate phase in the two-phase solvent system, and performing high-speed countercurrent chromatographic separation; during the high-speed counter-current chromatographic separation, detecting wave peaks by an ultraviolet detector, collecting from peak appearance until the peaks disappear, stopping collecting, respectively collecting different fractions, concentrating under reduced pressure, and freeze-drying to obtain myricitrin, quercetin and kaempferol-3-O-rhamnoside. The method for separating and purifying the flavonoid compound monomer has the advantages of high purity, small loss, simple operation, large preparation amount, economy and environmental protection.
Description
Technical Field
The invention relates to the field of natural product chemistry, in particular to a method for separating and purifying flavonoids compounds in ethyl acetate phase of polygonum multiflorum by high-speed counter-current chromatography.
Background
Polygonum multiflorum (Polygonum multiflorum Thunb.), also known as caulis Polygoni Multiflori, is the dried tuber of Polygonum multiflorum (Polygonaceae) Polygonum multiflorum (Fallopia Adans.) of Polygonaceae. The records are recorded in compendium of materia Medica and Chinese pharmacopoeia, and the compendium of materia Medica says that the characters are sweet and flat; it enters heart and liver meridians. Has effects of nourishing blood, tranquilizing mind, dispelling pathogenic wind, and dredging collaterals. Can be used for treating insomnia, dreaminess, blood deficiency, general pain, rheumatic arthralgia, and skin pruritus. "the study shows that: the fleece-flower root contains various bioactive substances, wherein the most important substances comprise active ingredients such as flavonoid compounds, stilbene glycoside compounds, anthraquinone compounds, polyphenol compounds, phospholipids, fatty acids and the like. Modern pharmacological research shows that the fleece-flower root has the functions of tranquilizing and allaying excitement, resisting chronic inflammation, resisting bacteria and the like, and the flavonoid compound in the fleece-flower root also has the functions of resisting oxidation, resisting aging, resisting cancer and reducing high blood pressure, high blood fat and high blood sugar.
The study of the chemical components of polygonum multiflorum by scholars at home and abroad is mostly concentrated on the tuber root and rattan thereof, and the tuber root and rattan of polygonum multiflorum contain a large amount of chemical active components such as flavonoids, stilbene glucoside compounds, polyphenols, anthraquinones, phospholipids and fatty acids [ study on the chemical components and pharmacological action of polygonum multiflorum, journal of Chinese experimental prescriptions, 13 th 2019 ], but after the tuber and rattan of polygonum multiflorum is removed, the rest of polygonum multiflorum is less studied (only the study on the chemical components of polygonum multiflorum leaves, traditional Chinese medicines, 6 th 2009, etc. [ study on the chemical components of polygonum multiflorum leaves, traditional Chinese medicines, etc. [ the study on the chemical components of polygonum multiflorum leaves, etc. ], and the separation is carried out to obtain flavonoids, steroids, glycosides and other compounds thereof.
Disclosure of Invention
The invention aims to provide a method for separating and purifying flavonoids compounds in the ethyl acetate phase of polygonum multiflorum by high-speed counter-current chromatography, which can separate and purify a plurality of flavonoid compound monomers from the ethyl acetate phase of polygonum multiflorum.
In order to solve the technical problem, the invention is realized as follows:
the method for separating and purifying flavonoids compounds in the ethyl acetate phase of polygonum multiflorum comprises the following steps:
(1) Preparation of ethyl acetate phase of polygonum multiflorum
Drying polygonum multiflorum leaves, and performing ultrasonic extraction for 1-3 times by taking ethanol as a solvent, wherein the extraction time is 1-4 h, and the solid-to-liquid ratio of the ultrasonic extraction is 1: 10-1: 20, carrying out suction filtration, combining filtrate, carrying out vacuum reduced pressure concentration to remove the solvent to obtain an ethanol extract of polygonum multiflorum, then adding ethyl acetate and water to carry out extraction for multiple times, and carrying out vacuum reduced pressure concentration to the completely extracted ethyl acetate phase to remove the solvent to obtain an ethyl acetate phase of polygonum multiflorum;
(2) High-speed countercurrent chromatography separation and purification
Adopting a water-methanol-ethyl acetate-n-hexane solution with a volume ratio of 1; when the two-phase solvent system reaches the balance in the high-speed countercurrent column, dissolving the polygonum multiflorum ethyl acetate phase in the two-phase solvent system, wherein the sample injection concentration is 5-20 mg/mL, and the sample injection volume is 10-30 mL, and performing high-speed countercurrent chromatographic separation; during the high-speed counter-current chromatographic separation, an ultraviolet detector with the wavelength of 200-300 nm is used for detecting, a single peak is taken as a unit, the collection is started from the appearance of the peak until the peak disappears, the collection is stopped, different fractions are respectively collected, and the reduced pressure concentration freeze drying is carried out, so that the myricitrin, the quercitrin and the kaempferol-3-O-rhamnoside are obtained.
In particular, the volume ratio of water-methanol-ethyl acetate-n-hexane is (2-3).
Specifically, in the step (2), the volume ratio of water-methanol-ethyl acetate-n-hexane is 2.
Specifically, in the step (2), when the high-speed countercurrent chromatography separation is performed, the rotation speed of the separation column is 850rpm, the flow rate of the mobile phase is 5mL/min, the wavelength of the ultraviolet detector is 254nm, the sample injection concentration is 11mg/mL, and the sample injection volume is 10mL.
Specifically, in the step (1), the ethanol solution obtained by ultrasonic extraction has a concentration of 80%.
In particular, in the step (1), the solid-to-liquid ratio of ultrasonic extraction is 1:10 to 1:20.
in particular, in the step (1), the solid-liquid ratio of the ultrasonic extraction is 1:15, the number of extractions was 2.
The method can separate and purify three flavonoid monomers, namely myricitrin, quercitrin and kaempferol-3-O-rhamnoside, and can separate and purify the three flavonoid monomers from the ethyl acetate phase of polygonum multiflorum at one time, so that the separation and purification of the flavonoid monomers are high in efficiency, simple to operate, low in comprehensive cost, large in separation amount, high in product purity and small in sample loss; the purity of the flavonoid monomer obtained by separation and purification reaches over 90 percent through High Performance Liquid Chromatography (HPLC), and the purity of the myricitrin, the quercetin and the kaempferol-3-O-rhamnoside of over 95 percent can be obtained through the purification of each fraction through preparative Liquid Chromatography.
Drawings
FIG. 1 is a chromatogram of a high-speed countercurrent chromatography separation and purification method of ethyl acetate phase of polygonum multiflorum by using water-methanol-ethyl acetate-n-hexane with a volume ratio of 2;
FIG. 2 is a high performance liquid chromatogram of separated and purified myricitrin;
FIG. 3 is a high performance liquid chromatogram of separated and purified quercetin;
FIG. 4 is a high performance liquid chromatogram of kaempferol-3-O-rhamnoside separated and purified.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more clearly understood, the following examples further illustrate the present invention in detail. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
The method for separating and purifying the flavonoid compounds in the ethyl acetate phase of the polygonum multiflorum provided by the invention is described in detail as follows:
the method comprises the following steps: preparation of ethyl acetate phase of polygonum multiflorum
Carrying out ultrasonic extraction on 1.0kg of dried polygonum multiflorum leaves by taking 90% ethanol as a solvent, wherein the extraction time is 2h, and the solid-to-liquid ratio of the ultrasonic extraction is 1:15, filtering, and repeatedly treating filter residues for 2 times; mixing filtrates, vacuum concentrating under reduced pressure until no ethanol smell exists to obtain extract of folium Polygoni Multiflori, and adding ethyl acetate and water for multiple extraction. And (3) carrying out vacuum reduced pressure concentration on the ethyl acetate phase after complete extraction to remove the solvent, thus obtaining the polygonum multiflorum ethyl acetate phase.
Step two: flavonoid monomer separation
Adopting water-methanol-ethyl acetate-n-hexane as a solvent system in a volume ratio of 1; when the two-phase solvent system reaches dynamic balance in a countercurrent column, dissolving the polygonum multiflorum ethyl acetate in the two-phase solvent system to prepare a separation sample, introducing the separation sample into a High-Speed countercurrent chromatograph, wherein the concentration of the separation sample is sample introduction concentration, the sample introduction concentration is 5-20 mg/mL, the sample introduction volume is 10-30 mL, and separating the polygonum multiflorum ethyl acetate phase by High-Speed Counter-Current Chromatography (HSCCC); during high-speed counter-current chromatographic separation, an ultraviolet detector monitors on line, the detection wavelength is 200-300 nm, corresponding peak components are respectively collected according to chromatographic peaks, and the corresponding high-purity compound is obtained by decompression, concentration and drying;
step three: purity determination and structure determination of flavonoid monomer
The collected fractions are respectively passed through 1 H-NMR (Nuclear Magnetic Resonance) and 13 C-NMR identification.
Example 1
The method comprises the following steps: preparation of ethyl acetate phase of polygonum multiflorum
Carrying out ultrasonic extraction on 1.0kg of dried polygonum multiflorum leaves by taking 90% ethanol as a solvent, wherein the extraction time is 2h, and the solid-to-liquid ratio of the ultrasonic extraction is 1:15, filtering, and repeatedly treating filter residues for 2 times; mixing filtrates, vacuum concentrating to remove ethanol smell to obtain ethanol extract, and extracting with ethyl acetate and water for several times. And (3) carrying out vacuum reduced pressure concentration on the ethyl acetate phase after complete extraction to remove the solvent, thus obtaining the polygonum multiflorum ethyl acetate phase.
Step two: flavonoid monomer separation
Adopting water-methanol-ethyl acetate-n-hexane with a volume ratio of 2; when the two-phase solvent system reaches dynamic balance in a countercurrent column, dissolving the polygonum multiflorum ethyl acetate in the two-phase solvent system to prepare a separation sample, introducing the separation sample into a High-Speed countercurrent chromatograph, wherein the concentration of the separation sample is sample introduction concentration, the sample introduction concentration is 11mg/mL, the sample introduction volume is 10mL, and the polygonum multiflorum ethyl acetate phase is subjected to High-Speed Counter-Current Chromatography (HSCCC) separation; during high-speed counter-current chromatography, an ultraviolet detector is used for on-line monitoring, the detection wavelength is 254nm, corresponding peak components are respectively collected according to chromatographic peaks, and the corresponding high-purity compound is obtained by reduced pressure concentration and drying, as shown in figure 1.
Myricitrin (I), quercitrin (II) and kaempferol-3-O-rhamnoside (III).
Step three: purity determination and structure determination of flavonoid monomer
The collected fractions are respectively passed through 1 H-NMR (Nuclear Magnetic Resonance) and 13 C-NMR identification is carried out, and the obtained monomer compounds are 30.93mg of myricitrin, 23.2mg of quercetin and 13.38mg of kaempferol-3-O-rhamnoside respectively; and (3) respectively detecting the collected fractions by HPLC (high performance liquid chromatography), calculating by using a chromatographic peak area normalization method, measuring the area of each impurity peak and the total chromatographic peak area, calculating the percentage of each impurity peak area and the sum of the impurity peak areas in the total peak area, and obtaining the sample purity, namely the percentage of the removed impurity peak sum. As shown in fig. 2, the peak area of the impurity peak is 5.1% and the total chromatographic peak area is 1 as calculated by the chromatographic peak area normalization method, the purity of the obtained myricitrin is 94.9%, the purity of the quercetin is 97.0% and the purity of the kaempferol-3-O-rhamnoside is 95.7% as known from the same principle; the high performance liquid chromatogram of myricitrin, quercetin and kaempferol-3-O-rhamnoside are shown in fig. 2-4.
Example 2
The method comprises the following steps: preparation of ethyl acetate phase of polygonum multiflorum
Carrying out ultrasonic extraction on 1.0kg of dried polygonum multiflorum leaves by using 85% ethanol as a solvent for 1h, wherein the solid-to-liquid ratio of the ultrasonic extraction is 1:20, filtering, and repeatedly treating filter residues for 1 time; mixing filtrates, vacuum concentrating to remove ethanol smell to obtain ethanol extract, and extracting with ethyl acetate and water for several times. And (3) carrying out vacuum reduced pressure concentration on the ethyl acetate phase after complete extraction to remove the solvent, thus obtaining the polygonum multiflorum ethyl acetate phase.
Step two: separation of flavonoid monomers
Adopting water-methanol-ethyl acetate-n-hexane with a volume ratio of 2; when the two-phase solvent system reaches dynamic balance in a countercurrent column, dissolving the ethyl acetate of polygonum multiflorum into the two-phase solvent system to prepare a separation sample, feeding the separation sample into a high-speed countercurrent chromatograph, wherein the concentration of the separation sample is the sample injection concentration, the sample injection concentration is 15mg/mL, the sample injection volume is 20mL, and performing HSCCC separation on the ethyl acetate phase of polygonum multiflorum; during high-speed counter-current chromatographic separation, an ultraviolet detector is used for on-line monitoring, the detection wavelength is 270nm, corresponding peak components are respectively collected according to chromatographic peaks, and the corresponding high-purity compound is obtained by reduced pressure concentration and drying.
Step three: purity determination and structure determination of flavonoid monomer
The purity of the monomeric compound is detected by using high performance liquid chromatography as in the third step of the embodiment 1.
Example 3
The method comprises the following steps: preparation of ethyl acetate phase of polygonum multiflorum
Carrying out ultrasonic extraction on 1.0kg of dried polygonum multiflorum leaves by using 95% ethanol as a solvent for 3h, wherein the solid-liquid ratio of the ultrasonic extraction is 1:10, filtering, and repeatedly treating filter residues for 2 times; mixing filtrates, vacuum concentrating under reduced pressure until no ethanol smell exists to obtain extract of folium Polygoni Multiflori, and adding ethyl acetate and water for multiple extraction. And (3) carrying out vacuum reduced pressure concentration on the ethyl acetate phase after complete extraction to remove the solvent, thus obtaining the polygonum multiflorum ethyl acetate phase.
Step two: flavonoid monomer separation
Adopting water-methanol-ethyl acetate-n-hexane with a volume ratio of 2; when the two-phase solvent system reaches dynamic balance in the countercurrent column, dissolving the polygonum multiflorum ethyl acetate in the two-phase solvent system to prepare a separation sample, feeding the separation sample into a high-speed countercurrent chromatograph, wherein the concentration of the separation sample is the sample injection concentration, the sample injection concentration is 20mg/mL, the sample injection volume is 20mL, and performing HSCCC separation on the polygonum multiflorum ethyl acetate phase; during high-speed counter-current chromatographic separation, an ultraviolet detector is used for on-line monitoring, the detection wavelength is 230nm, corresponding peak components are respectively collected according to chromatographic peaks, and the corresponding high-purity compound is obtained by reduced pressure concentration and drying.
Step three: purity determination and structure determination of flavonoid monomer
The purity of the monomeric compound is detected by using high performance liquid chromatography as in the third step of the embodiment 1.
Example 4
The method comprises the following steps: preparation of ethyl acetate phase of polygonum multiflorum
Carrying out ultrasonic extraction on 1.0kg of dried polygonum multiflorum leaves by taking 80% ethanol as a solvent, wherein the extraction time is 3h, and the solid-to-liquid ratio of the ultrasonic extraction is 1:20, filtering, and repeatedly treating filter residues for 2 times; mixing filtrates, vacuum concentrating to remove ethanol smell to obtain ethanol extract, and extracting with ethyl acetate and water for several times. And (3) carrying out vacuum reduced pressure concentration on the ethyl acetate phase after complete extraction to remove the solvent, thus obtaining the polygonum multiflorum ethyl acetate phase.
Step two: flavonoid monomer separation
Adopting water-methanol-ethyl acetate-n-hexane with a volume ratio of 2; when the two-phase solvent system reaches dynamic balance in a countercurrent column, dissolving the ethyl acetate of polygonum multiflorum into the two-phase solvent system to prepare a separation sample, feeding the separation sample into a high-speed countercurrent chromatograph, wherein the concentration of the separation sample is the sample injection concentration, the sample injection concentration is 20mg/mL, the sample injection volume is 10mL, and performing HSCCC separation on the ethyl acetate phase of polygonum multiflorum; during high-speed counter-current chromatographic separation, an ultraviolet detector is used for on-line monitoring, the detection wavelength is 300nm, corresponding peak components are respectively collected according to chromatographic peaks, and the corresponding high-purity compound is obtained by reduced pressure concentration and drying.
Step three: purity determination and structure determination of flavonoid monomer
The purity of the monomeric compound is detected by high performance liquid chromatography as in step three of the embodiment 1.
Example 5
The method comprises the following steps: preparation of ethyl acetate phase of polygonum multiflorum
Carrying out ultrasonic extraction on 1.0kg of dried polygonum multiflorum leaves by using 75% ethanol as a solvent for 2.5h, wherein the solid-liquid ratio of the ultrasonic extraction is 1:10, filtering, and repeatedly treating filter residues for 2 times; mixing filtrates, vacuum concentrating under reduced pressure until no ethanol smell exists to obtain extract of folium Polygoni Multiflori, and adding ethyl acetate and water for multiple extraction. And (3) carrying out vacuum reduced pressure concentration on the ethyl acetate phase after complete extraction to remove the solvent, thus obtaining the polygonum multiflorum ethyl acetate phase.
Step two: flavonoid monomer separation
Adopting water-methanol-ethyl acetate-n-hexane with a volume ratio of 2; when the two-phase solvent system reaches dynamic balance in a countercurrent column, dissolving the ethyl acetate of polygonum multiflorum into the two-phase solvent system to prepare a separation sample, feeding the separation sample into a high-speed countercurrent chromatograph for separation, wherein the concentration of the sample is the sample injection concentration, the sample injection concentration is 15mg/mL, the sample injection volume is 25mL, and performing HSCCC separation on the ethyl acetate of polygonum multiflorum; during high-speed counter-current chromatographic separation, an ultraviolet detector is used for on-line monitoring, the detection wavelength is 200nm, corresponding peak components are respectively collected according to chromatographic peaks, and the corresponding high-purity compound is obtained by reduced pressure concentration and drying.
Step three: purity determination and structure determination of flavonoid monomer
The purity of the monomeric compound is detected by high performance liquid chromatography as in step three of the embodiment 1.
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 and improvements made within the spirit and principle of the present invention are intended to be included within the scope of the present invention.
Claims (5)
1. A method for separating and purifying flavonoid compounds in an ethyl acetate phase of polygonum multiflorum by high-speed countercurrent chromatography is characterized by comprising the following steps:
(1) Preparation of ethyl acetate phase of polygonum multiflorum
Drying polygonum multiflorum leaves, performing ultrasonic extraction by using ethanol with the concentration of 75%, 80%, 85%, 90% or 95% as a solvent, performing suction filtration, combining filtrates, performing vacuum reduced pressure concentration to remove the solvent to obtain polygonum multiflorum leaf ethanol extract, adding ethyl acetate and water for multiple times of extraction, and performing vacuum reduced pressure concentration to remove the solvent from an extracted ethyl acetate phase to obtain polygonum multiflorum leaf ethyl acetate phase;
(2) High-speed countercurrent chromatography separation and purification
Adopting a water-methanol-ethyl acetate-n-hexane solution with a volume ratio of 2 to 3 to 5; when a two-phase solvent system reaches a balance in a high-speed countercurrent column, dissolving the polygonum multiflorum ethyl acetate phase in the two-phase solvent system, wherein the sample injection concentration is 5-20 mg/mL, and the sample injection volume is 10-30 mL, and performing high-speed countercurrent chromatographic separation; during the high-speed counter-current chromatography, detecting by using an ultraviolet detector with the wavelength of 200-300nm, collecting from peak appearance until the peak disappears by taking a single peak as a unit, respectively collecting different fractions, and performing reduced pressure concentration and freeze drying to obtain myricitrin, quercitrin and kaempferol-3-O-rhamnoside.
2. The method for separating and purifying flavonoids compounds in the ethyl acetate phase of polygonum multiflorum according to claim 1, wherein in the step (2), the volume ratio of water-methanol-ethyl acetate-n-hexane is 2.
3. The method for separating and purifying flavonoids compounds in the ethyl acetate phase of polygonum multiflorum thumb according to claim 1, wherein in the step (2), when the high-speed countercurrent chromatography is performed, the rotation speed of a separation column is 850rpm, the flow rate of a mobile phase is 5mL/min, the wavelength of an ultraviolet detector is 254nm, the sample injection concentration is 11mg/mL, and the sample injection volume is 10mL.
4. The method for separating and purifying flavonoids compounds in the ethyl acetate phase of polygonum multiflorum thumb according to claim 1, wherein in the step (1), the solid-to-liquid ratio of ultrasonic extraction is 1:10 to 1:20.
5. the method for separating and purifying flavonoids compounds in the ethyl acetate phase of polygonum multiflorum thumb according to claim 4, wherein in the step (1), the solid-to-liquid ratio of the ultrasonic extraction is 1:15, the number of extractions was 2.
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