CN103922913B - A kind of Chalcone Compounds and its preparation method and application - Google Patents
A kind of Chalcone Compounds and its preparation method and application Download PDFInfo
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- CN103922913B CN103922913B CN201410138654.0A CN201410138654A CN103922913B CN 103922913 B CN103922913 B CN 103922913B CN 201410138654 A CN201410138654 A CN 201410138654A CN 103922913 B CN103922913 B CN 103922913B
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- Prior art keywords
- silica gel
- medicinal extract
- beggarweed
- chalcone compounds
- liquid chromatography
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- 0 CC([C@](Cc1c2O)[C@](CC(c(cc*(O)c3)c3O)=O)c1ccc2O)=I Chemical compound CC([C@](Cc1c2O)[C@](CC(c(cc*(O)c3)c3O)=O)c1ccc2O)=I 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/04—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aldehyde or keto groups, or thio analogues thereof, directly attached to an aromatic ring system, e.g. acetophenone; Derivatives thereof, e.g. acetals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
- C07C49/83—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
Abstract
The invention discloses a kind of Chalcone Compounds and its preparation method and application.Described Chalcone Compounds is separated to obtain from renal lobe beggarweed, and its molecular formula is C
20h
20o
5, there is following structure:
the preparation method of described Chalcone Compounds is with renal lobe beggarweed complete stool for raw material, through medicinal extract extraction, silica gel column chromatography, high pressure liquid chromatography separating step, be specially: with methyl alcohol supersound extraction after renal lobe beggarweed complete stool is pulverized, extracting solution merges, and filter, concentrating under reduced pressure becomes medicinal extract; Medicinal extract silica gel dry column-packing carries out silica gel column chromatography; Be that the chloroform-acetone solution of 1:0 ~ 1:2 carries out gradient elution with volume proportion; Namely the 8:2 part of elutriant obtains described Chalcone Compounds with high pressure liquid chromatography separation and purification further.The present invention proves to have good cytoactive to tobacco mosaic virus (TMV) through test.The compounds of this invention structure is simple, and synthetic easily realizes, and the activity of compound is good, can be used as the guiding compound of resisting tobacco mosaic virus.
Description
Technical field
The invention belongs to technical field of phytochemistry, be specifically related to a kind of Chalcone Compounds extracted from renal lobe beggarweed and preparation method thereof and application.
Background technology
Renal lobe beggarweed is pulse family undershrub, is mainly distributed in Yunnan, Shaanxi, Sichuan, Hubei, Hunan, Jiangxi, Fujian, Zhejiang, Jiangsu; In Korea, also there is distribution in Japan.Renal lobe beggarweed is China's conventional Chinese medicinal materials among the people, root and over-ground part complete stool medicinal, there is the effects such as expelling wind and activating blood circulation, diuresis, desinsection.Domestic and international research shows, renal lobe beggarweed main active ingredient is flavonoid compound, comprises flavones, isoflavones, cinnamophenone etc.Cinnamophenone refers to the compound containing 1,3-diphenylprop ketenes structure in molecule.They are distributed in the root of multiple medicinal plant, leaf and skin in a large number.Because its molecular structure has larger flexibility, can with multiple receptors bind, present biological activity widely, as antitumor, suppress and scavenging activated oxygen, antibacterial, parasiticide, antiviral, antiulcer agent etc.Existing research simultaneously confirms, its pharmacological action and chemical structure closely related, more Chalcone Compounds can be researched and developed further, therefrom find effective lead compound and active group.The present invention is separated and obtains a kind of new Chalcone Compounds with activity of resisting tobacco mosaic virus from renal lobe beggarweed, and this compound it is not yet seen relevant report.
Summary of the invention
The first object of the present invention is to provide a kind of Chalcone Compounds; Second object is the preparation method providing described Chalcone Compounds; 3rd object is to provide described Chalcone Compounds preparing the application in resisting tobacco mosaic disease medicine.
The first object of the present invention is achieved in that described compound is separated to obtain from renal lobe beggarweed, and its molecular formula is C
20h
20o
5, there is following structure:
This compound is yellow jelly, called after beggarweed phenyl styryl ketone A.Chemical name is: 2-((1
s, 2
r)-4,5-dihydroxy-2-(prop-1-en-2-yl)-2,3-dihydro-1H-inden-1-yl)-1-(2,4-dihydroxyphenyl) ethanone.
The second object of the present invention is achieved in that the preparation method of described Chalcone Compounds is with renal lobe beggarweed for raw material, through medicinal extract extraction, silica gel column chromatography, high pressure liquid chromatography separating step, is specially:
A, medicinal extract extract: get renal lobe beggarweed sample complete stool, be crushed to 2 ~ 40 orders, by 90 ~ 99% methyl alcohol supersound extraction 3 ~ 5 times, and each 30 ~ 60 min, united extraction liquid, filtration, concentrating under reduced pressure becomes medicinal extract;
B, silica gel column chromatography: 160 ~ 200 order silica gel dry column-packings of medicinal extract weight ratio 2 ~ 3 times amount carry out silica gel column chromatography; Be that the chloroform-acetone solution of 1:0 ~ 1:2 carries out gradient elution with volume proportion, merge identical part, collect each several part elutriant and concentrated;
C, high pressure liquid chromatography are separated: namely the 8:2 part of step B elutriant obtains described Chalcone Compounds with high pressure liquid chromatography separation and purification further.
The structure of the Chalcone Compounds prepared with aforesaid method measures out by the following method:
The compounds of this invention is yellow jelly; Specific rotatory power
for-2.86 (solvent is methyl alcohol,
c0.20) UV spectrum (solvent is methyl alcohol),
λ max(log ε) 210 (4.62), 225 (4.46), 290 (4.16); Infrared spectra (pressing potassium bromide troche)
ν max3392,3142,3085,2954,2876,1643,1602,1565,1468,1347,1196,1062,871 cm
-1; High resolution mass spectrum (HRESIMS) provides quasi-molecular ion peak
m/z[339.1238 M-H]
-(calculated value 339.1232).In conjunction with
1h and
13c NMR spectrum provides a molecular formula C
20h
20o
5, degree of unsaturation is 11.From
1h and
13cNMR composes (attribution data is in Table-1) signal can find out in compound have 1,2,3, a 4-quaternary phenyl ring and one 1 ', 2 ', 3 '-trisubstituted phenyl ring, phenyl ring has four hydroxyls replace; In addition, one group of end group double bond, two methylene radical, two methynes, a methyl and a ketone carbonyl signals is also had in compound.These data show that this compound is three ring phenyl styryl ketone structures, 2 ' ' position namely on the isopentene group that replaces of common phenyl styryl ketone phenyl ring 2-position and
β-carbon defines five yuan of carbocyclic rings.H
3-5 ' ' (
δ h1.69) and H
2-4 ' ' (
δ h4.86) with C-2 ' ' and C-3 ' '; H-2 ' ' (
δ h3.19) and C-1, C-1 ' ', C-2, C-4 ' ', C-5 ' ', C-
αwith
c-β; H
2-
α(
δ h2.97 and 2.92) with C-1 ', C-
β, C-1, C=O, and C-2 ' '; H-
β(
δ h3.84) and C-1, C-1 ' ', C-
α, C-2, and C-2 ' '; H-1 ' ' (
δ h2.94) and C-1, C-2, C-2 ' ', C-
β, and between C-3 ' ', there is HMBC relevant (Fig. 1); In addition, H
2-
α/ H-
β/ H-2 ' '/H
2-1 ' ' between exist
1h-
1h COSY, these data also confirm this phenyl styryl ketone structure.Its Relative configuration is then contrasted determined by the coupling constant of ROESY Correlated Spectroscopy, specific rotation and hydrogen spectrum and known compound.So far the structure of this compound is determined.
table-1. compounds
1
h NMR and
13
c NMR data (CD
3
)
2
cO)
The third object of the present invention is achieved in that the preparation be applied to by described Chalcone Compounds in Tobacco mosaic medicine.
The compounds of this invention is separated first, is determined as Chalcone Compounds by nucleus magnetic resonance and measuring method of mass spectrum, and characterizes its concrete structure.Through the experiment to resisting tobacco mosaic virus, its relative inhibition reaches 52.1%, has good activity of resisting tobacco mosaic virus, higher than the relative inhibition (31.2%) of positive reference substance Nanning mycin.Above result discloses compound of the present invention preparing in resisting tobacco mosaic virus medicine good application prospect.The compounds of this invention structure is simple active good, can be used as the guiding compound of resisting tobacco mosaic virus medicine.
Accompanying drawing explanation
Fig. 1 is the carbon-13 nmr spectra of compound;
Fig. 2 is the proton nmr spectra of compound;
The HSQC Correlated Spectroscopy of Fig. 3 compound;
The HMBC Correlated Spectroscopy of Fig. 4 compound;
Fig. 5 compound
1h-
1h COSY Correlated Spectroscopy;
The ROESY Correlated Spectroscopy of Fig. 6 compound;
Fig. 7 is the main of compound
1h-
1h COSY with HMBC is relevant.
Embodiment
Below in conjunction with embodiment and accompanying drawing, the present invention is further illustrated, but limited the present invention never in any form, and any conversion done based on training centre of the present invention or improvement, all fall into protection scope of the present invention.
Except as otherwise noted, the percentage ratio adopted in the present invention is mass percent.
Chalcone Compounds C of the present invention
20h
20o
5preparation method comprise medicinal extract extraction, silica gel column chromatography, high pressure liquid chromatography separating step, specifically comprise:
A, medicinal extract extract: get renal lobe beggarweed sample, be crushed to 20 ~ 40 orders, by 90 ~ 99% methyl alcohol supersound extraction 3 ~ 5 times, and each 30 ~ 60 min, united extraction liquid, filtration, concentrating under reduced pressure becomes medicinal extract;
B, silica gel column chromatography: 160 ~ 200 order silica gel dry column-packings of medicinal extract weight ratio 2 ~ 3 times amount carry out silica gel column chromatography; Be that the chloroform-acetone solution of 1:0 ~ 1:2 carries out gradient elution with volume proportion, merge identical part, collect each several part elutriant and concentrated;
C, high pressure liquid chromatography are separated: namely the 8:2 part of step B elutriant obtains described Chalcone Compounds with high pressure liquid chromatography separation and purification further.
The solvent methanol concentration of described step A is 95%.
The medicinal extract of described step B before silica gel column chromatography rough segmentation, with after the pure dissolve with methanol of weight ratio 1.5 ~ 3 times amount with 80 ~ 100 order silica gel mixed samples of weight ratio 0.8 ~ 1.2 times.
The chloroform-acetone solution volume proportion of described step B is 1:0,20:1,9:1,8:2,7:3,6:4,1:1,1:2.
The separation and purification of described step C mesohigh liquid chromatography is employing 21.2 mm × 250 mm, 5
μthe C of m
18chromatographic column, flow velocity is 20 mL/min, and moving phase is the methyl alcohol of 58%, and UV-detector determined wavelength is 390 nm, each sample introduction 200
μl, collects the chromatographic peak of 21.4 min, repeatedly cumulative rear evaporate to dryness.
Material after the separation and purification of described step C mesohigh liquid phase chromatography uses pure dissolve with methanol again, then with pure methyl alcohol for moving phase, is separated with gel filtration chromatography, with further separation and purification.
Chalcone Compounds of the present invention is preparing the application in resisting tobacco mosaic virus medicine.
The present invention is raw materials used not to be limited by area and kind, and all can realize the present invention, to derive from the renal lobe beggarweed sample in Yunnan, the present invention will be further described below:
embodiment 1
Renal lobe beggarweed sample source is in In Xishuangbanna of Yunnan.Renal lobe beggarweed is sampled 2.2 kg and is crushed to 30 orders, the supersound extraction 3 times of the methyl alcohol with 95%, extracts 30min at every turn, and extracting solution merges, and filter, concentrating under reduced pressure becomes medicinal extract, obtains medicinal extract 88.5 g.With the thick silica gel mixed sample of 100 order of 120 g after the pure dissolve with methanol of medicinal extract weight ratio 2.5 times amount, the 160 order silica gel dress posts of 1.5 kg carry out silica gel column chromatography, be 1:0 with volume proportion, 20:1, 9:1, 8:2, 7:3, 6:4, 1:1, chloroform-acetone the gradient elution of 1:2, TLC monitoring merges identical part, obtain 8 parts, wherein volume proportion is the prompt logical sequence 1,100 half preparative high-performance liquid chromatographic separation of chloroform-acetone elution fraction peace of 8:2, methyl alcohol with 58% is moving phase, Zorbax SB-C18 (21.2 × 250 mm, 5 μm) preparative column is stationary phase, flow velocity is 20 ml/min, UV-detector determined wavelength is 290 nm, each sample introduction 200 μ L, collect the chromatographic peak of 21.4 min, repeatedly cumulative rear evaporate to dryness, products therefrom uses pure dissolve with methanol again, then with pure methyl alcohol for moving phase, is separated, obtains this new compound with Sephadex LH-20 gel filtration chromatography.
embodiment 2
Renal lobe beggarweed sampling 3.5kg, in Yunnan Dehong, is crushed to 40 orders, the supersound extraction 5 times of the methyl alcohol with 90% by renal lobe beggarweed sample source, extracts 45 min at every turn, and extracting solution merges, and filter, concentrating under reduced pressure becomes medicinal extract, obtains medicinal extract 158 g.With the thick silica gel mixed sample of 80 order of 300 g after the pure dissolve with methanol of medicinal extract weight ratio 2.0 times amount, the 200 order silica gel dress posts of 1.5 kg carry out silica gel column chromatography, be 1:0 with volume proportion, 20:1, 9:1, 8:2, 7:3, 6:4, 1:1, chloroform-acetone the gradient elution of 1:2, TLC monitoring merges identical part, obtain 8 parts, wherein volume proportion is the prompt logical sequence 1,100 half preparative high-performance liquid chromatographic separation of chloroform-acetone elution fraction peace of 8:2, methyl alcohol with 58% is moving phase, Zorbax SB-C18 (21.2 × 250 mm, 5 μm) preparative column is stationary phase, flow velocity is 20 ml/min, UV-detector determined wavelength is 290 nm, each sample introduction 200 μ L, collect the chromatographic peak of 21.4 min, repeatedly cumulative rear evaporate to dryness, products therefrom uses pure dissolve with methanol again, then with pure methyl alcohol for moving phase, is separated, obtains this new compound with Sephadex LH-20 gel filtration chromatography.
embodiment 3
Renal lobe beggarweed, in Honghe, Yunnan, is sampled 5 kg and is crushed to 60 orders by renal lobe beggarweed sample source, the supersound extraction 3 times of the methyl alcohol with 99%, extracts 60 min at every turn, and extracting solution merges, and filter, concentrating under reduced pressure becomes medicinal extract, obtains medicinal extract 350 g.With the thick silica gel mixed sample of 90 order of 500 g after the pure dissolve with methanol of medicinal extract weight ratio 1.6 times amount, the 180 order silica gel dress posts of 1.8 kg carry out silica gel column chromatography, be 1:0 with volume proportion, 20:1, 9:1, 8:2, 7:3, 6:4, 1:1, chloroform-acetone the gradient elution of 1:2, TLC monitoring merges identical part, obtain 8 parts, wherein volume proportion is the prompt logical sequence 1,100 half preparative high-performance liquid chromatographic separation of chloroform-acetone elution fraction peace of 8:2, methyl alcohol with 58% is moving phase, Zorbax SB-C18 (21.2 × 250 mm, 5 μm) preparative column is stationary phase, flow velocity is 20 ml/min, UV-detector determined wavelength is 290 nm, each sample introduction 200 μ L, collect the chromatographic peak of 21.4 min, repeatedly cumulative rear evaporate to dryness, products therefrom uses pure dissolve with methanol again, then with pure methyl alcohol for moving phase, is separated, obtains this new compound with Sephadex LH-20 gel filtration chromatography.
embodiment 4
Compound prepared by Example 1 is yellow jelly.
Measuring method is: with nucleus magnetic resonance, in conjunction with other spectroscopic technique qualification structure.
The compounds of this invention is yellow jelly; Specific rotatory power
for-2.86 (
c0.20, MeOH) UV spectrum (solvent is methyl alcohol),
λ max(log ε) 210 (4.62), 225 (4.46), 290 (4.16); Infrared spectra (pressing potassium bromide troche)
ν max3392,3142,3085,2954,2876,1643,1602,1565,1468,1347,1196,1062,871 cm
-1; High resolution mass spectrum (HRESIMS) provides quasi-molecular ion peak
m/z[339.1238 M-H]
-(calculated value 339.1232).In conjunction with
1h and
13c NMR spectrum provides a molecular formula C
20h
20o
5, degree of unsaturation is 11.From
1h and
13cNMR composes (attribution data is in Table-1) signal can find out in compound have 1,2,3, a 4-quaternary phenyl ring and one 1 ', 2 ', 3 '-trisubstituted phenyl ring, phenyl ring has four hydroxyls replace; In addition, one group of end group double bond, two methylene radical, two methynes, a methyl and a ketone carbonyl signals is also had in compound.These data show that compound is three ring phenyl styryl ketone structures, 2 ' ' position namely on the isopentene group that replaces of common phenyl styryl ketone phenyl ring 2-position and
β-carbon defines five yuan of carbocyclic rings.H
3-5 ' ' (
δ h1.69) and H
2-4 ' ' (
δ h4.86) with C-2 ' ' and C-3 ' '; H-2 ' ' (
δ h3.19) and C-1, C-1 ' ', C-2, C-4 ' ', C-5 ' ', C-
αwith
c-β; H
2-
α(
δ h2.97 and 2.92) with C-1 ', C-
β, C-1, C=O, and C-2 ' '; H-
β(
δ h3.84) and C-1, C-1 ' ', C-
α, C-2, and C-2 ' '; H-1 ' ' (
δ h2.94) and C-1, C-2, C-2 ' ', C-
β, and between C-3 ' ', there is HMBC relevant (Fig. 1); In addition, H
2-
α/ H-
β/ H-2 ' '/H
2-1 ' ' between exist
1h-
1h COSY, these data also confirm this phenyl styryl ketone structure.Its Relative configuration is then contrasted determined by the coupling constant of ROESY Correlated Spectroscopy, specific rotation and hydrogen spectrum and known compound.So far the structure of this compound is determined.
embodiment 5
Compound prepared by Example 2 is yellow jelly.Measuring method is identical with embodiment 4, confirms that compound prepared by embodiment 2 is described Chalcone Compounds---beggarweed phenyl styryl ketone A.
embodiment 6
Compound prepared by Example 3 is yellow jelly.Measuring method is identical with embodiment 4, confirms that compound prepared by embodiment 3 is described Chalcone Compounds---beggarweed phenyl styryl ketone A.
embodiment 7
Arbitrary Chalcone Compounds prepared by Example 1 ~ 3 carries out activity of resisting tobacco mosaic virus test, and test situation is as follows:
Adopt half leaf method, when the mass concentration of medicament is 50 mg/L, activity of resisting tobacco mosaic virus mensuration is carried out to the compounds of this invention.5 ~ 6 age flue-cured tobacco plant on, choose the blade (leaf capable normal, anosis without worm) being applicable to test, first blade evenly sprinkled fine emery powder, with writing brush by tobacco mosaic virus (TMV) source (3.0 × 10 for subsequent use
-3) be evenly put on sprinkled with silicon carbide blade on, connect after poison terminates until the blade of all middle choosings, be placed on immediately in the culture dish filling liquid and process 20 min, take out, wipe the globule and liquid on blade, being restored by two and half leaves is emitted in the glass jar being covered with toilet paper moisturizing, and cover glass cover, temperature control (23 ± 2) DEG C, be placed on greenhouse natural light irradiation, 2 ~ 3 d and visible withered spot. each process set second half leaf as contrast, be provided with in addition 1 group be the process of commodity Ningnanmycin as a comparison, press formulae discovery relative inhibition.
XI％=(CK-T)／CK×100％
X: relative inhibition (%), CK: be soaked in the withered spot number (individual) that half in clear water connects malicious leaf, T is soaked in the withered spot number (individual) that half in liquid connects malicious leaf.
The relative inhibition of result bright compound is 52.1%, far above the relative inhibition 31.2% of contrast Ningnanmycin, illustrates that compound has good activity of resisting tobacco mosaic virus.
Claims (5)
1. Chalcone Compounds is preparing the application in resisting tobacco mosaic virus medicine, and described Chalcone Compounds is separated to obtain from renal lobe beggarweed, and its molecular formula is C
20h
20o
5, there is following structure:
。
2. application according to claim 1, is characterized in that the preparation method of described Chalcone Compounds with renal lobe beggarweed complete stool for raw material, through medicinal extract extraction, silica gel column chromatography, high pressure liquid chromatography separating step, is specially:
A, medicinal extract extract: get renal lobe beggarweed sample, be crushed to 20 ~ 40 orders, by 90 ~ 99% methyl alcohol supersound extraction 3 ~ 5 times, and each 30 ~ 60min, united extraction liquid, filtration, concentrating under reduced pressure becomes medicinal extract;
B, silica gel column chromatography: 160 ~ 200 order silica gel dry column-packings of medicinal extract weight ratio 2 ~ 3 times amount carry out silica gel column chromatography; Be that the chloroform-acetone solution of 1:0,20:1,9:1,8:2,7:3,6:4,1:1,1:2 carries out gradient elution with volume proportion, merge identical part, collect each several part elutriant and concentrated;
C, high pressure liquid chromatography are separated: the 8:2 part of step B elutriant uses high pressure liquid chromatography separation and purification further, high pressure liquid chromatography separation and purification adopts 21.2mm × 250mm, the C18 chromatographic column of 5 μm, flow velocity is 20mL/min, moving phase is the methyl alcohol of 58%, and UV-detector determined wavelength is 290nm, each sample introduction 200 μ L, collect the chromatographic peak of 21.4min, repeatedly namely cumulative rear evaporate to dryness obtains described Chalcone Compounds.
3. application according to claim 2, is characterized in that in described step A, methanol concentration is 95%.
4. application according to claim 2, is characterized in that in described step B, medicinal extract is before silica gel column chromatography rough segmentation, with 80 ~ 100 order silica gel mixed samples by weight ratio 0.8 ~ 1.2 times after the pure dissolve with methanol of weight ratio 1.5 ~ 3 times amount.
5. application according to claim 2, is characterized in that the material after the separation and purification of described step C mesohigh liquid chromatography uses pure dissolve with methanol again, then with pure methyl alcohol for moving phase, is separated with gel filtration chromatography, with further separation and purification.
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