CN101805385B - Neoflavonoid compounds separated and purified from Tridax procumbens and preparation method thereof - Google Patents

Neoflavonoid compounds separated and purified from Tridax procumbens and preparation method thereof Download PDF

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CN101805385B
CN101805385B CN2009100958700A CN200910095870A CN101805385B CN 101805385 B CN101805385 B CN 101805385B CN 2009100958700 A CN2009100958700 A CN 2009100958700A CN 200910095870 A CN200910095870 A CN 200910095870A CN 101805385 B CN101805385 B CN 101805385B
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CN101805385A (en
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袁珂
徐润生
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Zhejiang A&F University ZAFU
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Zhejiang Forestry College
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Abstract

The invention relates to a veoflavonoid compounds separated and purified from Tridax procumbens and a preparation method thereof. The Neoflavonoid compounds are separated and purified from the Tridax procumbens by a chemical separation, purification and chromatographic separation technology. The preparation method comprises the steps of percolation extraction, macroporous resin adsorption, chromatographic separation by silica gel columns, and the like, and three Neoflavonoid compounds, i.e. 8,3'-dihydroxy-3,7,4'-trimethoxy-6-O-beta-D-glucose flavonoid, 8,3'-dihydroxy -3,7,4'-trimethoxy-6-O-[alpha-L-rhamnosyl-(1->2)]-beta-D-glucose flavonoid and 8,3'-dihydroxy -3,7,4'-trimethoxy flavones are separated from the Tridax procumbens. In the preparation method, the wild Tridax procumbens is used as a raw material which is particularly rich in sources, and a preparation process is simpler, economical and safe, and has high yield. Preliminary activity studies show that the prepared veoflavonoid compounds have stronger antibacterial activity and oxidation resisting activity.

Description

Flavonoid compound of separation and purification and preparation method thereof from plumage awns chrysanthemum
Technical field
The invention belongs to flavonoid compound and preparation method thereof technical field, be specially flavonoid compound of separation and purification from plumage awns chrysanthemum and preparation method thereof.。
Background technology
Flavonoid compound is one type and extensively is present in botanic important biomolecule active substance, has effects such as anti-oxidant, anti-ageing, antiviral, antitumor, antibiotic.Biological resistance of oxidation and its disease resistance, resistance and delay senility closely related, thereby from natural phant the searching good antioxidant to be applied in medicine, food, healthcare products, the makeup etc. be one of current research focus.
Plumage awns chrysanthemum (Tridaxprocumbens.L) is composite family long handle Chrysanthemum per nnial herb, and is sweet little, bitter cold, and plumage awns chrysanthemum leaf and flower have the effect of Azelaic Acid, through being usually used in incised wound, scratch, traumatic wounds hemostasis, can also effectively stop alopecia simultaneously.Plumage awns chrysanthemum originates in the american torrid zone area, after propagate in states such as India, South East Asia Mainland and Indonesia, China introduces ground such as Guangdong, Taiwan and Hainan.About neoflavonoid of separation and purification from plumage awns chrysanthemum and preparation method thereof, through the document retrieval, Shang Weijian studies report.
Summary of the invention
To the problems referred to above that exist in the prior art; The objective of the invention is to design the technical scheme of neoflavonoid that a kind of separation and purification from plumage awns chrysanthemum is provided and preparation method thereof; Its preparation technology is simple; Yield is high, and the monomeric compound that makes has stronger bacteriostatic activity and anti-oxidant activity.
The neoflavonoid of described separation and purification from plumage awns chrysanthemum, chemical name is: 8,3 '-dihydroxyl-3,7,4 '-trimethoxy-6-O-β-D-glucose flavonoid glycoside, have structural formula shown in (I):
Figure G2009100958700D00011
The neoflavonoid of described separation and purification from plumage awns chrysanthemum, chemical name is: 8,3 '-dihydroxyl-3,7,4 '-trimethoxy-6-O-[α-L-rhamanopyranosyl-(1 → 2)]-β-D-glucose flavonoid glycoside, have structural formula shown in (II):
Figure G2009100958700D00021
The neoflavonoid of described separation and purification from plumage awns chrysanthemum, chemical name is: 8,3 '-dihydroxyl 3,7,4 '-the trimethoxy flavones, have structural formula shown in (III):
Figure G2009100958700D00022
The preparation method of said compound I, II, III is characterized in that may further comprise the steps:
1) gets exsiccant plumage awns chrysanthemum herb meal and make raw material, use 70% ethanol percolate extraction, collect percolate;
2) the percolate film under vacuum is concentrated into nothing alcohol flavor, reclaims ethanol, obtain medicinal extract;
3) medicinal extract is added suitable quantity of water and carry out ultra-sonic dispersion, use sherwood oil, ETHYLE ACETATE, n-butanol extraction successively, each position extraction liquid concentrating under reduced pressure of gained is obtained petroleum ether part, ethyl acetate extract, n-butanol portion and water position;
4a) with the ethyl acetate extract ultra-sonic dispersion of step 3) gained in water, through Diaion HP-20 macroporous adsorbent resin column chromatography, use H successively 2O, 10%MeOH, 20%MeOH, 40%MeOH, 60%MeOH, 70%Me 2CO carries out wash-out, obtains each wash-out position; The 40%MeOH wash-out position of Diaion post is again through Sephadex LH-20 gel adsorbent resin column chromatography, then with H 2O, 20%MeOH, 40%MeOH, 60%MeOH, 70%Me 2CO carries out wash-out;
Silica gel column chromatography is passed through at the 40%MeOH wash-out position of Sephadex post; With volume ratio 5-7: 1-3: 1 ethyl acetate, alcohol and water carries out wash-out; The dry light yellow bullion that gets compound I of elutriant vacuum concentration; Through methanol-water mixed solvent recrystallization, get the light yellow crystallization of compound I again;
Wash-out through silica gel column chromatography, is carried out with the ethyl acetate, alcohol and water of volume ratio 6-8: 1-3: 1-3 in the 20%MeOH wash-out position of Sephadex post, the elutriant vacuum concentration dry the light yellow unformed powder of compound I I;
4b) petroleum ether part is passed through silica gel column chromatography; With volume ratio 20: 1-1: 10 petroleum ether-ethyl acetate gradient elution; TLC examines knowledge, gets 8 parts after same stream part merges, and wherein is that the 4th part of principal constituent is passed through silica gel column chromatography again with the compound III; And then with volume ratio 4-6: 1 petroleum ether-ethyl acetate carries out wash-out, the elutriant vacuum concentration dry the light yellow crystallization of compound III.
Above-mentioned steps 1) plumage awns chrysanthemum herb meal is with 70% ethanol percolate extraction of 3 times of amounts in.
Above-mentioned steps 4a) the 40%MeOH wash-out position of Sephadex post is carried out wash-out through silica gel column chromatography with 6: 2: 1 ethyl acetate, alcohol and water of volume ratio in;
The 20%MeOH wash-out position of Sephadex post is carried out wash-out through silica gel column chromatography with 7: 2: 2 ethyl acetate, alcohol and water of volume ratio.
Above-mentioned steps 4b) volume ratio 15 of PetroChina Company Limited.'s ether-ETHYLE ACETATE: 1-1: 5.
Neoflavonoid of above-mentioned separation and purification from plumage awns chrysanthemum and preparation method thereof is a raw material with wild plumage awns chrysanthemum, and it is abundant especially to originate, and preparation technology is simpler, economy, safety, and yield is high; 3 new flavone compounds that make all have stronger bacteriostatic activity, anti-oxidant activity and antitumor action, have good value of exploiting and utilizing, for research and development are from now on laid a good foundation.
The percentage composition that relates in the present specification, unless otherwise indicated, solid matter is a weight ratio, liquid substance is a volume ratio.
Embodiment
Combine embodiments of the invention and pharmacological testing at present, the present invention is described further.
3 new flavone compounds I of the present invention, II, III, its preparation method may further comprise the steps:
1) gets exsiccant plumage awns chrysanthemum herb meal 10kg, with 3 times of amount ethanol percolate extraction of 70% 3 times, filter merging filtrate at every turn;
2) be evaporated to nothing alcohol flavor, the total medicinal extract 0.8kg after must concentrating with Reduced Pressure Concentration Device;
3) total medicinal extract is added suitable quantity of water and carry out ultra-sonic dispersion, use sherwood oil, ETHYLE ACETATE, n-butanol extraction successively, each position extraction liquid of gained is carried out concentrating under reduced pressure obtain petroleum ether part, ethyl acetate extract, n-butanol portion and water position;
4a) the gained ethyl acetate extract is got the 130g ultra-sonic dispersion in water,, use H successively through macroporous adsorbent resin Diaion HP-20 column chromatography 2O, 10%MeOH, 20%MeOH, 40%MeOH, 60%MeOH, 70%Me 2The CO wash-out; Wherein after the 40%MeOH wash-out part concentrating under reduced pressure drying of Diaion post, be dissolved in after the less water through gel polymeric adsorbent Sephadex LH-20 column chromatography, with H 2O, 20%MeOH, 40%MeOH, 60%MeOH, 70%Me 2The CO wash-out,
Wherein after the 40%MeOH wash-out position concentrating under reduced pressure drying of Sephadex LH-20 post; Pass through 160-200 order silica gel column chromatography after being dissolved in less water; With 6: 2: 1 ethyl acetate, alcohol and water wash-out of volume ratio; Get the light yellow bullion of compound I,, get the light yellow crystallization 1.68g of compound I through methanol-water mixed solvent recrystallization.
Wherein after the 20%MeOH wash-out position concentrating under reduced pressure drying of Sephadex LH-20 post; Pass through 160-200 order silica gel column chromatography after being dissolved in less water; With 7: 2: 2 ethyl acetate, alcohol and water wash-out of volume ratio, get the light yellow unformed powder 1.03g of compound I I;
4b) petroleum ether part is passed through 160-200 order silica gel column chromatography; With volume ratio 20: 1-1: 10 petroleum ether-ethyl acetate gradient elution; TLC examines knowledge, gets 8 parts after same stream part merges, and wherein is that the 4th part of principal constituent is passed through silica gel column chromatography again with the compound III; And then carry out wash-out with 5: 1 petroleum ether-ethyl acetate of volume ratio, the elutriant vacuum concentration dry the light yellow crystallization 0.58g of compound III.
In the above-mentioned steps: MeOH representes methyl alcohol, Me 2CO representes acetone.TLC inspection knowledge is meant: thin layer plate is 0.5%CMC-Na-silica gel G F 254Plate, developping agent are ethyl acetate, alcohol and water (7: 2: 3), developer a: uv lamp (254nm) is observed fluorescence down; Or developer b:2%FeCl 3-2%K 3Fe (CN) 6Spray, 105 ℃ were toasted 2～5 minutes.
Structure is identified: mainly utilize spectroscopic techniques, comprise infrared (IR), high resolution electrospray ionization mass spectrometry (HRESI-MS), electrospray ionization mass spectrometry (ESI-MS), nuclear magnetic resonance spectrum ( 1H-NMR, 13C-NMR, DEPT, 1H- 1H COSY, HSQC, HMBC) analyze the structure that (table 1-3) identifies 3 new flavone compounds I, II, III.
Compound I: molecular formula is: C 24H 26O 13, light yellow crystallization, 255-257 ℃ (MeOH); Meet iron trichloride-Tripotassium iron hexacyanide reagent and show blue, show pink with hydrochloric acid-magnesium powder reagent react, the Molish reaction shows positive.HRESI-MS (m/z): 545.1274 [M+Na] + 1H NMR (400MHz), 13C NMR (100MHz), DEPT, HMBC see table 1.
Compound I I: molecular formula is: C 30H 36O 17, light yellow unformed powder, 300-302 ℃ (MeOH); Meet iron trichloride-Tripotassium iron hexacyanide reagent and show blue, show pink with hydrochloric acid-magnesium powder reagent react, the Molish reaction shows positive.HRESI-MS (m/z): 691.1846 [M+Na] + 1H NMR (400MHz), 13C NMR (100MHz), DEPT, HMBC see table 2.
Compound III: molecular formula is: C 18H 16O 8, light yellow crystallization, 236-238 ℃ (MeOH); Meet iron trichloride-Tripotassium iron hexacyanide reagent and show blue, show pink with hydrochloric acid-magnesium powder reagent react, negative with the Molish reagent react. 1H NMR (400MHz), 13C NMR (100MHz), DEPT, HMBC see table 3.
Table 1. compound I 13C-NMR, 1H-NMR spectroscopic data (MeOH-d 4, TMS, δ ppm, J, Hz)
Figure G2009100958700D00051
Table 2. compound I I's 13C-NMR, 1H-NMR spectroscopic data (MeOH-d 4, TMS, δ ppm, J, Hz)
Figure G2009100958700D00061
Table 3. compound III 13C-NMR, 1H-NMR spectroscopic data (MeOH-d 4, TMS, δ ppm, J, Hz)
Figure G2009100958700D00071
Nomenclature in the foregoing description is following: IR is an ir spectra; HRESI-MS is the high resolution electrospray ionization mass spectrometry; 1H-NMR is a proton nmr spectra; 13C-NMR is a carbon-13 nmr spectra; DEPT is that undistorted polarization transfer strengthens method; 1H- 1H COSY is the relevant spectrum of two-dimentional hydrogen hydrogen, and HSQC is the hydrocarbon directly related spectrum of two dimension; HMBC is the hydrocarbon long-range relevant spectrum of two dimension; δ is chemical shift, and unit is ppm; J is a coupling constant, and unit is Hz; TMS is an internal standard substance; MeOH-d 4Be deuterated methanol; Molish reagent is the ethanolic soln of the naphthyl alcohol of the vitriol oil-2%.
For further specifying the effect of the present invention in field of medicaments, explain through the part pharmacological tests below.
1, bacteriostatic activity test-results:
1) preparation of solution: take by weighing 5mg respectively and separate 3 monomeric compound I, II, the III that obtains, adding distil water is settled to and gets mass concentration in the 5mL volumetric flask is 1.0mgmL -1The aqueous solution, successively the dilution be 800,400,200,100,50,25,12.5 μ gmL -1The aqueous solution, and do blank with sterilized distilled water.
The substratum that supplies germ experiment to use is beef-protein medium, and filling a prescription is 0.5g Carnis Bovis seu Bubali cream, 1.0g peptone, 0.5g NaCl, 2g agar, 100mL water.The fungi experiment uses substratum to be the potato glucose substratum.Prescription soaks juice for 2g glucose, 2g agar, 100mL 20% yam.
2) activation of the sterilization of material and bacterial classification: will test required petridish and other equipment and put dry sterilization 2h in 160 ℃ of loft drier; Substratum and the test tube that installs zero(ppm) water are put in the high-pressure steam sterilizing pan, and moist heat sterilization 2h is subsequent use.
Supply the bacterial classification of examination to move all and insert on the corresponding test tube slant substratum, every kind is repeated to connect 2.Bacterium is put and cultivates 24h in 37 ℃ of constant incubators, and mould is put in 28 ℃ of incubators and cultivates 48h.Every kind of bacterial strain is got 2 and is supplied test usefulness, puts 0 ℃～4 ℃ refrigerator and cooled and hides.
3) preparation of strains tested suspension-s: get the test tube that fills the 10mL sterilized water and come on the test-tube stand successively; Each picking 2 ring of 3 bacterial classifications that carry out overactivation in advance are dissolved in respectively in 3 sterilized water test tubes, process bacteria suspension, then; Dilution bacterium liquid, making its mycetome is 10 7～10 8ML -1, promptly get and supply to try bacterial classification.
4) bacteriostatic experiment: bacteriostatic activity is measured and is adopted the dull and stereotyped filter paper method of agar diffusion, judges bacteriostasis according to the inhibition zone diameter size.Filter paper diameter 6.0mm, subsequent use behind the sterilizing-drying.Add in the sterile petri dish with the various bacteria suspensions of aseptic pipette, extract 0.1mL, soak into the filter paper of 3 new flavone compounds sample solutions, its check mark is placed on media surface with the tweezers gripping.The bacterium petridish that contains of putting filter paper well is cultivated in thermostat container respectively.37 ℃ on bacterium, 24h, 28 ℃ in mould, 48h then take out, and measure and write down the diameter of inhibition zone.The data SPSS 10.0 analyzes, and relatively adopts the t check between group.
5) minimal inhibitory concentration (MIC) is measured the mensuration employing doubling dilution of result: MIC.With 800,400,200,100,50,25,12.5 μ gmL -13 new flavone compounds sample solutions of series concentration move in each plate with the 2mL transfer pipet respectively; Each concentration repeats 3 wares; Pour about 10mL abundant mixing in the substratum of high-temperature sterilization into; After the cooled and solidified, every ware adds the 0.1mL bacteria suspension, evenly cultivates with aseptic spreader coating.Take out, observations is a minimum with the strength of solution of not growing bacterium, and the result sees table 4.
Fungistatic effect MIC (the μ gmL of 3 new flavone compounds of table 4 -1)
Experimental strain Compound I Compound I I Compound III
Streptococcus aureus 25 12.5 25
Intestinal bacteria 50 25 50
Aspergillus flavus 100 100 400
Can be known that by table 4 aqueous solution of compound I, II, III all has restraining effect in various degree to supplying the examination bacterial classification, 3 new flavone compounds have stronger restraining effect to streptococcus aureus, intestinal bacteria, and strengthen with the increase fungistatic effect of concentration.Compound III (reaches 400 μ gmL in concentration to the inhibition effect of Aspergillus flavus is relatively low -1The time just Aspergillus flavus is just had certain restraining effect).
This test-results shows that 3 new flavone compounds of the present invention have stronger bacteriostatic activity.
2, anti-oxidant activity test-results:
Though it is existing such as thiocyanate-(thiocyanate) method, thiobarbituricacid (TBA) method etc. to be used to estimate the method for plant resistance of oxidation so far.But these methods or formality are quite loaded down with trivial details time-consuming, or the expensive of required reagent or large-scale instrument, still lack a kind of sensitivity, simple effective ways.1, (1,1-Diphenyl-2-picryl-hydrazyl DPPH) is a kind of stable organic free radical to 1-phenylbenzene picryl phenylhydrazine, can represent the power of its oxidation-resistance to the removing ability of DPPH radical through detection of biological reagent.In recent years, existing abroad people's Preliminary Exploitation DPPH solution absorbency changes as the spectrophotometry of removing the radical ability.The resistance of oxidation of DPPH spectrophotometry in order to 3 new flavone compounds I in the test evaluation plumage awns chrysanthemum, II, III adopted in this test.
1) experiment condition: measuring temperature is 37 ℃; Vibrations: 30s vibrations direction level; DPPH compound concentration: 0.2molmL -1Tecan Infinite M200 ELIASA (Switzerland); Enzyme plate: 96 orifice plates.
2) preparation of sample solution: get compound I, II, each 25mg of III respectively, with anhydrous alcohol solution and constant volume in the measuring bottle of 25mL.Get 4mL then respectively, 3mL, 2mL, 1mL in the 5mL measuring bottle, is configured to 0.10mgmL with the absolute ethyl alcohol constant volume -1, 0.08mgmL -1, 0.06mgmL -1, 0.04mgmL -1, 0.02mgmL -1
3) measure the result: add absolute ethyl alcohol+DPPH with point sample with the liquid-transfering gun equal-volume, sample+absolute ethyl alcohol, sample+DPPH is point sample respectively, and parallel point sample is three times respectively.Measure with Infinite M 200 ELIASAs, the mensuration wavelength is 517nm, measures the result and sees table 5.
Anti-oxidant result behind 3 new flavone compounds reactions of table 5 20min
Figure G2009100958700D00091
In 3 new flavone compounds, compound I and compound I I belong to flavonoid glycoside, and compound III is a Flavone aglycone; The three compares; Compound III will be higher than compound I and compound I I to the clearance rate of DPPH, and promptly the anti-oxidant activity of Flavone aglycone is higher than flavonoid glycoside, and this possibly be that Flavone aglycone and sugar are combined into glycosides its antioxygenic activity is reduced; In addition, 3 new flavone compounds strengthen with concentration rising resistance of oxidation in the compound concentration scope.
Test-results shows that 3 new flavone compounds I, II, III of separation and purification have stronger anti-oxidant activity from plumage awns chrysanthemum.
The invention has the advantages that: raw material of the present invention is wild, and it is abundant especially to originate, and preparation technology is simpler, economy, safety, and yield is high; 3 new flavone compounds that make all have stronger bacteriostatic activity, anti-oxidant activity and antitumor action, and good development prospect is arranged.

Claims (9)

1. the flavonoid compound of separation and purification from plumage awns chrysanthemum, chemical name is: 8,3 '-dihydroxyl-3,7,4 '-trimethoxy-6-O-β-D-glucose flavonoid glycoside, have structural formula shown in (I):
Figure FSB00000669789000011
2. the flavonoid compound of separation and purification from plumage awns chrysanthemum, chemical name is: 8,3 '-dihydroxyl-3,7,4 '-trimethoxy-6-O-[α-L-rhamanopyranosyl-(1 → 2)]-β-D-glucose flavonoid glycoside, have structural formula shown in (II):
Figure FSB00000669789000012
3. the flavonoid compound of separation and purification from plumage awns chrysanthemum, chemical name is: 8,3 '-dihydroxyl-3,7,4 '-the trimethoxy flavones, have structural formula shown in (III):
Figure FSB00000669789000013
4. the preparation method of compound I according to claim 1 is characterized in that may further comprise the steps:
1) gets exsiccant plumage awns chrysanthemum herb meal and make raw material, use 70% ethanol percolate extraction, collect percolate;
2) the percolate film under vacuum is concentrated into nothing alcohol flavor, reclaims ethanol, obtain medicinal extract;
3) medicinal extract is added suitable quantity of water and carry out ultra-sonic dispersion, use sherwood oil, ETHYLE ACETATE, n-butanol extraction successively, each position extraction liquid concentrating under reduced pressure of gained is obtained petroleum ether part, ethyl acetate extract, n-butanol portion and water position;
4) with the ethyl acetate extract ultra-sonic dispersion of step 3) gained in water, through Diaion HP-20 macroporous adsorbent resin column chromatography, use H successively 2O, 10%MeOH, 20%MeOH, 40%MeOH, 60%MeOH, 70%Me 2CO carries out wash-out, obtains each wash-out position;
5) Sephadex LH-20 gel adsorbent resin column chromatography is passed through at the 40%MeOH wash-out position of Diaion post in the step 4) again, then with H 2O, 20%MeOH, 40%MeOH, 60%MeOH, 70%Me 2CO carries out wash-out; Silica gel column chromatography is passed through at the 40%MeOH wash-out position of Sephadex post; With volume ratio 5-7: 1-3: 1 ethyl acetate, alcohol and water carries out wash-out; The dry light yellow bullion that gets compound I of elutriant vacuum concentration again through methanol-water mixed solvent recrystallization, gets the light yellow crystallization of compound I.
5. like the preparation method of the said compound I I of claim 2, it is characterized in that may further comprise the steps:
1) gets exsiccant plumage awns chrysanthemum herb meal and make raw material, use 70% ethanol percolate extraction, collect percolate;
2) the percolate film under vacuum is concentrated into nothing alcohol flavor, reclaims ethanol, obtain medicinal extract;
3) medicinal extract is added suitable quantity of water and carry out ultra-sonic dispersion, use sherwood oil, ETHYLE ACETATE, n-butanol extraction successively, each position extraction liquid concentrating under reduced pressure of gained is obtained petroleum ether part, ethyl acetate extract, n-butanol portion and water position;
4) with the ethyl acetate extract ultra-sonic dispersion of step 3) gained in water, through Diaion HP-20 macroporous adsorbent resin column chromatography, use H successively 2O, 10%MeOH, 20%MeOH, 40%MeOH, 60%MeOH, 70%Me 2CO carries out wash-out, obtains each wash-out position;
5) Sephadex LH-20 gel adsorbent resin column chromatography is passed through at the 40%MeOH wash-out position of Diaion post in the step 4) again, then with H 2O, 20%MeOH, 40%MeOH, 60%MeOH, 70%Me 2CO carries out wash-out, and wash-out through silica gel column chromatography, is carried out with the ethyl acetate, alcohol and water of volume ratio 6-8: 1-3: 1-3 in the 20%MeOH wash-out position of Sephadex post, the elutriant vacuum concentration dry the light yellow amorphous powder of compound I I.
6. like the preparation method of the said compound III of claim 3, it is characterized in that may further comprise the steps:
1) gets exsiccant plumage awns chrysanthemum herb meal and make raw material, use 70% ethanol percolate extraction, collect percolate;
2) the percolate film under vacuum is concentrated into nothing alcohol flavor, reclaims ethanol, obtain medicinal extract;
3) medicinal extract is added suitable quantity of water and carry out ultra-sonic dispersion, use sherwood oil, ETHYLE ACETATE, n-butanol extraction successively, each position extraction liquid concentrating under reduced pressure of gained is obtained petroleum ether part, ethyl acetate extract, n-butanol portion and water position;
4) petroleum ether part is passed through silica gel column chromatography; With volume ratio 20: 1-1: 10 petroleum ether-ethyl acetate gradient elution; TLC examines knowledge, gets 8 parts after same stream part merges, and wherein is that the 4th part of principal constituent is passed through silica gel column chromatography again with the compound III; And then with volume ratio 4-6: 1 petroleum ether-ethyl acetate carries out wash-out, the elutriant vacuum concentration dry the light yellow crystallization of compound III.
7. like the preparation method of claim 4,5 or 6 said compounds, it is characterized in that plumage awns chrysanthemum herb meal is with 70% ethanol percolate extraction of 3 times of amounts in the step 1).
8. like the preparation method of the said compound of claim 4, it is characterized in that the volume ratio 6: 2: 1 of ethyl acetate, alcohol and water in the step 5).
9. like the preparation method of the said compound of claim 5, it is characterized in that the volume ratio 7: 2: 2 of ethyl acetate, alcohol and water in the step 5).
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