CN107501225B - Flavonoid compound and preparation method and application thereof - Google Patents
Flavonoid compound and preparation method and application thereof Download PDFInfo
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- CN107501225B CN107501225B CN201710848541.3A CN201710848541A CN107501225B CN 107501225 B CN107501225 B CN 107501225B CN 201710848541 A CN201710848541 A CN 201710848541A CN 107501225 B CN107501225 B CN 107501225B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/40—Separation, e.g. from natural material; Purification
Abstract
The invention discloses a flavonoid compound and a preparation method and application thereof. The flavonoid is separated from Cassia tora L and has a molecular formula of C20H18O6The compound was named: 6,4' -dimethoxy-7- (3-hydroxypropan-1-onyl) -flavone, with the English name: 6,4' -dimethoxy-7- (3-hydroxypropan1-one) -flavanone, having the following structure:. The preparation method comprises the steps of extract extraction, silica gel column chromatography, high pressure liquid chromatography separation and gel column chromatography. The application is the application of the flavonoid compound in preparing the anti-tobacco mosaic virus medicine. The compound has good application prospect in preparing the anti-tobacco mosaic virus medicament. The compound has simple structure and good activity, and can be used as a guiding compound of a tobacco mosaic virus resistant medicament.
Description
Technical Field
The invention belongs to the technical field of phytochemistry, and particularly relates to a flavonoid compound and a preparation method and application thereof.
Background
Cassia seed, semen Cassiae (Cassia tora L.) (Cassia leschenaultiana DC.) Is leguminous (Leguminosae)) Cassia (Cassia) plant, also called as Indian sweet oil, old beef vine, senna, short tusifos hemsleyana root and Chinese honeylocust fruit, belongs to annual or perennial shrubby herb, is 30-80 cm high, sometimes up to 1 m in height, has upright stem, branches and dense twigs, and is yellow and soft. Cassia tora is grown on hilly grassland, shrubs and roadside with elevation of 500-2200 m, in southern areas such as Yunnan, Sichuan, Guangdong and Guangxi, and in countries such as India, Burma, Vietnam and IndonesiaThe seeds have the effects of invigorating stomach, promoting urination, and eliminating edema. The flavonoids generally refer to a series of compounds formed by connecting two benzene rings (A-and B-rings) with phenolic hydroxyl groups through a central three-carbon atom, wherein the basic parent nucleus is 2-phenyl chromone, and the structure of the compounds is usually connected with functional groups such as the phenolic hydroxyl group, the methoxy group, the methyl group, the isopentenyl group and the like. Flavones are widely found in some plants and berries in nature, and the total number is about 4 thousand. Flavone is a strong antioxidant, and has effects in scavenging oxygen free radicals in vivo, improving blood circulation, reducing cholesterol, inhibiting exudation of inflammatory biological enzyme, promoting wound healing, and relieving pain. The invention separates a flavonoid compound with activity of resisting tobacco mosaic virus from cassia brachycarpa, and the compound has not been reported yet.
Disclosure of Invention
The first purpose of the invention is to provide a flavonoid compound; the second purpose is to provide a preparation method of the flavonoid compound; the third purpose is to provide the application of the flavonoid compound.
The first purpose of the invention is realized by that the flavonoid compound is separated from the cassia tora, and the molecular formula of the flavonoid compound is C20H18O6The compound was named: 6,4' -dimethoxy-7- (3-hydroxypropan-1-onyl) -flavone, with the English name: 6,4' -dimethoxy-7- (3-hydroxypropan1-one) -flavanone, having the following structure:
the second object of the present invention is achieved by using Cassia tora (A) short leafCassia leschenaultiana DC.) The preparation method comprises the following steps of extracting extractum, performing silica gel column chromatography, performing high-pressure liquid chromatography separation and performing gel column chromatography, and specifically comprises the following steps:
A. extracting the extractum: taking the raw materials Cassia acutifolia, (B)Cassia leschenaultiana DC.) The whole plant is taken as raw materialOr crushing and cutting the raw materials into small sections, adding an organic solvent with the mass concentration of 70-100% and the weight of 2-4 times that of the raw materials, soaking and extracting for 24-72 hours for 3-5 times, combining the extracting solutions, filtering and concentrating into an extract;
B. silica gel column chromatography: performing silica gel column chromatography on the extract by using 150-200 mesh silica gel dry method which is 2-5 times of the weight of the extract, performing gradient elution by using chloroform-methanol solution with volume ratio of 20: 1-5: 5, merging the same parts, collecting eluent of each part and concentrating;
C. high-pressure liquid chromatography separation: and further separating and purifying 8:2 part of the eluent by using high pressure liquid chromatography to obtain the target flavonoid compound.
The structure of the prepared compound was identified by the following method:
the compound is orange yellow jelly, and HRESI-MS shows that the peak of the quasi-molecular ion is 377.1008 [ M + Na ]]+(calculated 377.1001), combined1H NMR and DEPT spectra confirm that the molecular formula is C20H18O6The unsaturation degree was 12.
The infrared spectrum shows hydroxyl groups (3430 cm)-1) Carbonyl (1686 and 1663 cm)-1) And aromatic rings (1610, 1571 and 1452 cm)-1) The resonance absorption peak of (1). The maximum absorption of the ultraviolet spectrum at 210, 269 and 368nm also indicates that aromatic ring structures possibly exist in the compound.
Process for preparing compounds1H and13c NMR spectra (see Table 1, FIG. 1 and FIG. 2) show that they contain 20 carbons and 18 hydrogens, including 1,2,4, 5-tetrasubstituted benzene ring (C-5-C-10, H-5, H-6), 1, 4-disubstituted benzene ring (C-1 '-C-6'; H-2',6' and H-3',5'), 1α,βUnsaturated carbonyl (C-2, C-3, C-4, H-3), 1 3-hydroxypropan-1-one group (C-1'' to C-3'', H)2-2'' and H2-3 "), two methoxy groups (d C56.2 q and 55.9 q,d H3.81 s and 3.79 s). According to the typical 2 benzene rings,α,βUnsaturated carbonyl and double bond signals, which are presumed to be flavonoids. HMBC correlation according to H-3 and C-2, C-4, C-10, C-1', H-5 and C-4, C-9, C-10, H-8 and C-6, C-7, C-9, C-10, and H-2',6' and C-2 (e.g., as in the case of HMBC correlationFig. 3) further confirmed that the compound has a flavonoid structure.
After the parent compound is identified, the remaining substituents, 3-hydroxypropan-1-one and methoxy, can be considered as substituents on the flavone. Two methoxyhydrogens (A), (B) can be observed in the HMBC spectrum of the compound (as shown in FIG. 3)d H3.81 and 3.79) in connection with HMBC at C-6 and C-4', it can be speculated that two methoxy groups are substituted at the C-6 and C-4' positions, respectively; by H2-2'' (d H2.93) and C-7, and H-8 (C: (C-H)d H7.44) and C-1'' HMBC, it was confirmed that the hydroxypropyl substitution was at the C-7 position. In addition the proton signal on the benzene ring is typical [ H-5,d H7.20 s;H-8,d H7.44 s,H-2′,6′,d H7.74 (d) 8.8;H-3′,5′,d H6.85 (t)8.8]it was also confirmed that the A ring of the flavone compound of the present invention is disubstituted at the 6, 7-position and the B ring is monosubstituted at the 4' -position. To this end, the structure of the compound was determined and the compound was named: 6,4' -dimethoxy-7- (3-hydroxypropan-1-onyl) -flavone.
Infrared, ultraviolet and mass spectral data of compounds: the spectrum of violet light (methanol),λ max(logε) 368 (3.81), 269(3.92), 210 (4.40); infrared spectroscopy (potassium bromide pellet):ν max3430、1686、1663、1610、1571、1452、1265、1157、1069 cm-1;1h and13c NMR data (500 and 125 MHz in CDCl as solvent)3) See Table-1; positive ion mode ESIMSm/z377 [M+Na]+(ii) a Positive ion mode HRESIMSm/z377.1008 [M+Na]+(calculated 377.1001, C20H18NaO6)。
Of the compounds of Table 11H NMR and13c NMR data (CDCl)3)
The third purpose of the invention is realized by the application of the flavonoid compound in preparing the anti-tobacco mosaic virus medicine.
The compound of the invention is separated for the first time, is determined to be a flavonoid compound by a nuclear magnetic resonance and mass spectrometry method, and represents the specific structure of the flavonoid compound. Through the experiment of resisting tobacco mosaic virus, the relative inhibition rate reaches 48.2%, and the tobacco mosaic virus resisting activity is very good and is far higher than the relative inhibition rate (33.8%) of a positive control nanningmycin. The results show that the compound has good application prospect in the preparation of the anti-tobacco mosaic virus medicine. The compound has simple structure and good activity, and can be used as a guiding compound of a tobacco mosaic virus resistant medicament.
Drawings
FIG. 1 is a nuclear magnetic resonance carbon spectrum of a compound;
FIG. 2 is a nuclear magnetic resonance hydrogen spectrum of a compound;
figure 3 is the major HMBC correlation of compounds.
Detailed Description
The present invention is further illustrated by the following examples and the accompanying drawings, but the present invention is not limited thereto in any way, and any modifications or alterations based on the teaching of the present invention are within the scope of the present invention.
All percentages used in the present invention are mass percentages unless otherwise indicated.
The flavonoid compound is separated from the cassia tora breve and has the molecular formula of C20H18O6The compound was named: 6,4' -dimethoxy-7- (3-hydroxypropan-1-onyl) -flavone, with the English name: 6,4' -dimethoxy-7- (3-hydroxypropan1-one) -flavanone, having the following structure:
the preparation method of the flavonoid compound is that cassia tora (L.) (Cassia leschenaultiana DC.) The preparation method comprises the following steps of extracting extractum, performing silica gel column chromatography, performing high-pressure liquid chromatography separation and performing gel column chromatography, and specifically comprises the following steps:
A. extracting the extractum: get the originalCassia occidentalis (A. Ex Fr.) KuntzeCassia leschenaultiana DC.) Taking the whole plant as a raw material or crushing and cutting the plant into small sections, adding an organic solvent with the mass concentration of 70-100% and the weight of 2-4 times of that of the raw material, soaking and extracting for 24-72 hours, extracting for 3-5 times, combining the extracting solutions, filtering and concentrating into an extract;
B. silica gel column chromatography: performing silica gel column chromatography on the extract by using 150-200 mesh silica gel dry method which is 2-5 times of the weight of the extract, performing gradient elution by using chloroform-methanol solution with volume ratio of 20: 1-5: 5, merging the same parts, collecting eluent of each part and concentrating;
C. high-pressure liquid chromatography separation: and further separating and purifying 8:2 part of the eluent by using high pressure liquid chromatography to obtain the target flavonoid compound.
The organic solvent in the step A is methanol with the mass percentage concentration of 80-100%, ethanol with the mass percentage concentration of 80-100% or acetone with the mass percentage concentration of 70-100%.
The method also comprises a silica gel sample mixing step before the silica gel column chromatography.
The silica gel sample mixing is to mix the sample with 80-100 mesh silica gel with the weight 0.8-1.5 times of the extract after dissolving the silica gel sample with pure methanol, pure ethanol or pure acetone with the weight 1.5-3 times of the extract.
The volume ratio of the chloroform-methanol solution in the step B is 20:1, 9:1, 8:2, 7:3, 6:4 and 5: 5.
The high pressure liquid chromatography in step C adopts 21.2mm × 250mm, 5μC of m18Chromatographic column with flow rate of 20mL/min, mobile phase of 60% methanol, ultraviolet detector with detection wavelength of 368nm, and sample introduction rate of 200 per timeμAnd L, collecting a chromatographic peak of 28.6min, accumulating for multiple times and evaporating to dryness.
After the high pressure liquid chromatography separation and purification step, the obtained compound is dissolved by pure methanol again, and then the pure methanol is used as a mobile phase to be separated by gel column chromatography for further separation and purification.
The application of the flavonoid compound is the application of the flavonoid compound in preparing a medicament for resisting tobacco mosaic virus.
The invention is further illustrated by the following specific examples:
example 1
The Cassia tora sample is from Yunan Yuanjiang, 2.0 kg of the Cassia tora sample is crushed and extracted with 95% methanol for 5 times, each time for 24 hours, the extracting solutions are combined, filtered and concentrated under reduced pressure to obtain an extract, and 98 g of the extract is obtained. Dissolving the extract with 2.0 times of pure methanol, mixing with 120 g of 80 mesh crude silica gel, loading 0.6 kg of 160 mesh silica gel into column, performing silica gel column chromatography, gradient eluting with chloroform-methanol at volume ratio of 20:1, 9:1, 8:2, 7:3, 6:4, 5:5, monitoring by TLC, mixing the same fractions to obtain 6 fractions, separating the chloroform-methanol eluate at volume ratio of 8:2 by using an agilent 1100 semi-preparative high performance liquid chromatography, using 60% methanol as mobile phase, and mixing with Zorbax SB-C18 (21.2 × 250mm, 5:5 mm)μm) The preparation column is stationary phase, flow rate is 20ml/min, ultraviolet detector detection wavelength is 368nm, and each sample introduction is 200μL, collecting a chromatographic peak of 28.6min, accumulating for multiple times and then evaporating to dryness; dissolving the obtained product with pure methanol again, taking the pure methanol as a mobile phase, and carrying out SephadexLH-20 gel column chromatography separation to obtain the new compound.
Example 2
Cassia tora samples are from Yunnan time, 4.0kg of Cassia tora is sampled and cut into pieces, the cut pieces are extracted by 95 percent ethanol for 4 times, each time, the extraction time is 48 hours, the extracting solutions are combined, filtered and concentrated under reduced pressure to obtain extract 181 g. Dissolving the extract with 2.0 times of pure methanol, mixing with 200 g of 100 mesh crude silica gel, loading 1.0 kg of 200 mesh silica gel into column, performing silica gel column chromatography, gradient eluting with chloroform-methanol at volume ratio of 20:1, 9:1, 8:2, 7:3, 6:4, and 5:5, monitoring by TLC, mixing the same parts to obtain 6 parts, wherein the chloroform-acetone eluate at volume ratio of 8:2 is separated by ANJIERAN 1100 semi-preparative high performance liquid chromatography, using 60% methanol as mobile phase, and Zorbax SB-C18 (21.2 × 250mm, 5:5 mm)μm) preparing column as stationary phase, flow rate of 20ml/min, ultraviolet detector detection wavelength of 368nm, and sample introduction of 200 per timeμL, collecting a chromatographic peak of 28.6min, accumulating for multiple times and then evaporating to dryness; dissolving the obtained product with pure methanol again, taking the pure methanol as a mobile phase, and carrying out SephadexLH-20 gel column chromatography separation to obtain the new compound.
Example 3
The Cassia tora sample is from Yunan Dali, 6 kg of the Cassia tora sample is crushed, extracted by 80% acetone for 3 times with ultrasonic, each time for 72 hours, the extracting solutions are combined, filtered and concentrated under reduced pressure to obtain 305 g of extract. Dissolving the extract with 1.6 times of pure methanol, mixing with 320g of 90 mesh crude silica gel, loading 1.6 kg of 180 mesh silica gel into column, performing silica gel column chromatography, gradient eluting with chloroform-methanol at volume ratio of 20:1, 9:1, 8:2, 7:3, 6:4, 5:5, monitoring by TLC, mixing the same fractions to obtain 6 fractions, separating the chloroform-acetone eluate at volume ratio of 8:2 by using an agilent 1100 semi-preparative high performance liquid chromatography, using 60% methanol as mobile phase, and mixing with Zorbax SB-C18 (21.2 × 250mm, 5:5 mm)μm) preparing column as stationary phase, flow rate of 20ml/min, ultraviolet detector detection wavelength of 368nm, and sample introduction of 200 per timeμL, collecting a chromatographic peak of 28.6min, accumulating for multiple times and then evaporating to dryness; dissolving the obtained product with pure methanol again, taking the pure methanol as a mobile phase, and carrying out SephadexLH-20 gel column chromatography separation to obtain the new compound.
Example 4
The compound prepared in example 1 was taken as an orange gum.
HRESI-MS shows that the peak of the excimer ion is 377.1008 [ M + Na ]]+(calculated 377.1001), combined1The molecular formula of the compound is C determined by HNMR and DEPT spectra20H18O6The unsaturation degree was 12.
The infrared spectrum shows hydroxyl groups (3430 cm)-1) Carbonyl (1686 and 1663 cm)-1) And aromatic rings (1610, 1571 and 1452 cm)-1) The resonance absorption peak of (1). The maximum absorption of the ultraviolet spectrum at 210, 269 and 368nm also indicates that aromatic ring structures possibly exist in the compound.
Process for preparing compounds1H and13c NMR spectra (see Table 1, FIG. 1 and FIG. 2) show that they contain 20 carbons and 18 hydrogens, including 1,2,4, 5-tetrasubstituted benzene ring (C-5-C-10, H-5, H-6), 1, 4-disubstituted benzene ring (C-1 '-C-6'; H-2',6' and H-3',5'), 1α,βUnsaturated carbonyl (C-2, C-3, C-4, H-3), 1 3-hydroxypropan-1-one group (C-1'' to C-3'', H)2-2'' and H2-3 "), two methoxy groups (d C56.2 q and 55.9 q,d H3.81 s and 3.79 s). According to the typical 2 benzene rings,α,βUnsaturated carbonyl and double bond signals, which are presumed to be flavonoids. The compounds were further confirmed to have flavonoid structures based on HMBC correlations between H-3 and C-2, C-4, C-10, C-1', H-5 and C-4, C-9, C-10, H-8 and C-6, C-7, C-9, C-10, and H-2',6' and C-2 (see FIG. 3).
After the parent compound is identified, the remaining substituents, 3-hydroxypropan-1-one and methoxy, can be considered as substituents on the flavone. Two methoxyhydrogens (A), (B) can be observed in the HMBC spectrum of the compound (as shown in FIG. 3)d H3.81 and 3.79) in connection with HMBC at C-6 and C-4', it can be speculated that two methoxy groups are substituted at the C-6 and C-4' positions, respectively; by H2-2'' (d H2.93) and C-7, and H-8 (C: (C-H)d H7.44) and C-1'' HMBC, it was confirmed that the hydroxypropyl substitution was at the C-7 position. In addition the proton signal on the benzene ring is typical [ H-5,d H7.20 s;H-8,d H7.44 s,H-2′,6′,d H7.74 (d) 8.8;H-3′,5′,d H6.85 (t)8.8]it was also confirmed that the A ring of the flavone compound of the present invention is disubstituted at the 6, 7-position and the B ring is monosubstituted at the 4' -position. To this end, the structure of the compound was determined and the compound was named: 6,4' -dimethoxy-7- (3-hydroxypropan-1-onyl) -flavone.
Example 5
The compound prepared in example 2 was taken as an orange gum. The measurement method was the same as in example 4, and it was confirmed that the compound prepared in example 2 was 6,4' -dimethoxy-7- (3-hydroxypropan-1-onyl) -flavone, which is the flavonoid compound.
Example 6
The compound prepared in example 3 was taken as an orange gum. The measurement method was the same as in example 4, and it was confirmed that the compound prepared in example 3 was 6,4' -dimethoxy-7- (3-hydroxypropan-1-onyl) -flavone, which is the flavonoid compound.
Example 7
Any flavonoid compound prepared in the examples 1-3 is used for carrying out the activity test of the tobacco mosaic virus, and the test conditions are as follows:
the activity of the compound of the invention against tobacco mosaic virus is measured by a half-leaf method when the mass concentration of the medicament is 50 mg/L. Selecting leaves suitable for testing (normal leaves, no disease and no insect) on plants of 5-6-year-old flue-cured tobacco, uniformly spraying fine carborundum on the leaves, and using a writing brush to apply a standby tobacco mosaic virus source (3.0 multiplied by 10)-3) Uniformly smearing on the leaves scattered with carborundum, immediately placing the selected leaves in a culture dish containing liquid medicine for processing for 20 min after all the selected leaves are disinfected, taking out the leaves, wiping off water drops and the liquid medicine on the leaves, restoring and arranging two half leaves in a glass jar paved with toilet paper for moisture preservation, covering the glass jar, controlling the temperature to be (23 +/-2) DEG C, placing the glass jar in a greenhouse for natural light irradiation, and enabling the dead spots to be visible for 2-3 d.
XI%=(CK-T)/CK×100%
X: relative inhibition ratio (%), CK: the number of dead spots of half leaf after being soaked in clear water is one, and the number of dead spots of half leaf after being soaked in liquid medicine is one.
The result shows that the relative inhibition rate of the compound is 48.2 percent and is far higher than the relative inhibition rate of the control ningnanmycin by 33.8 percent, which indicates that the compound has better activity against tobacco mosaic virus.
Claims (3)
1. A method for preparing flavonoid compound is characterized in that the flavonoid compound has activity of resisting tobacco mosaic virus, and the molecular formula of the flavonoid compound is C20H18O6The compound was named: 6,4' -dimethoxy-7- (3-hydroxypropyl-1-keto) -flavone, the structural formula is:
the flavonoids compounds are prepared from cassia tora serving as a raw material by the steps of extract extraction, silica gel column chromatography, high-pressure liquid chromatography separation and gel column chromatography, and specifically comprise the following steps:
A. extracting the extractum: taking raw material cassia tora, taking the whole plant as a raw material or crushing and cutting the raw material into small sections, adding an organic solvent which is 2-4 times of the weight of the raw material, wherein the organic solvent is methanol with the mass percentage concentration of 80-100%, ethanol with the mass percentage concentration of 80-100% or acetone with the mass percentage concentration of 70-100%, soaking and extracting for 24-72 hours, extracting for 3-5 times, combining the extracting solutions, filtering and concentrating into an extract;
B. silica gel column chromatography: performing silica gel column chromatography on the extract by using 150-200 mesh silica gel dry method which is 2-5 times of the weight of the extract, performing gradient elution by using chloroform-methanol solutions with volume ratios of 20:1, 9:1, 8:2, 7:3, 6:4 and 5:5, merging the same parts, collecting eluent of each part and concentrating;
C. high-pressure liquid chromatography separation: separating 8:2 part of the eluate by using Escheren 1100 semi-preparative high performance liquid chromatography with C of 21.2mm × 250mm and 5 μm18The chromatographic column is a fixed phase, the flow rate is 20mL/min, the mobile phase is 60% methanol, the detection wavelength of an ultraviolet detector is 368nm, 200 mu L of sample introduction is carried out each time, a chromatographic peak of 28.6min is collected, evaporation is carried out after multiple accumulation, the obtained product is dissolved by pure methanol again, then the pure methanol is used as the mobile phase, and Sephadex LH-20 gel column chromatography is used for separation and purification, so that the target flavonoid compound is obtained.
2. The method according to claim 1, further comprising a silica gel sample-mixing step before the silica gel column chromatography.
3. The preparation method according to claim 2, wherein the silica gel sample is prepared by dissolving pure methanol, pure ethanol or pure acetone in an amount of 1.5-3 times the weight of the extract, and then mixing the dissolved silica gel sample with 80-100 mesh silica gel in an amount of 0.8-1.5 times the weight of the extract.
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