CN106892919A - The preparation method of dehydroevodiamine and its purposes of anti-agriculture pathogen - Google Patents
The preparation method of dehydroevodiamine and its purposes of anti-agriculture pathogen Download PDFInfo
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
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- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
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Abstract
The present invention relates to 1 extracting and developing of the natural indole quinazoline Alkaloid dehydroevodiamine with pesticide uses, the method for purifying.There is provided using Evodia（Evodia）Plant evodia rutaecarpa（E.rutaecarpa(Juss.)Benth）, Shi Hu（E.rutaecarpa var.officinalis(Dode)Huang）, thin hair evodia rutaecarpa（E.rutaecarpa var.bodinieri(Dode)Huang）, Fructus seu Radix Evodiae austrosinensis（E.austrosinensis）, smelly peppery Wu's cornel（E.fargesii）And smelly wingceltis Wu cornel（E.daniellii）It is fresh（Or it is dry）The extracting and developing of fruit, the production technology of purifying dehydroevodiamine.The invention further relates to the activity analysis to the anti-agriculture disease fungus of the compound, bacterium, it is found that the compound has strong inhibitory activity to agriculture pathogenetic bacteria, with good DEVELOPMENT PROSPECT.
Description
Technical field
The invention provides the preparation method of the dehydroevodiamine being worth with pesticide developing and its in anti-agriculture cause of disease
Purposes in bacterium.Its separation method and method for crystallising are quick, simple, practical, and with conventional Technical comparing, method is novel, has
Obvious novelty.
Background technology
Rutaceae（Rutaceae）Evodia（Evodia）The whole world there are about 150 kinds, be distributed in Asia, eastern Africa and
Oceania.There is 20 kind of 5 mutation in China, wherein most is conventional Chinese herbal medicine among the people, main product is in Guizhou, Yunnan, Guangxi, Guangdong, lake
North, Hunan, Jiangxi, Sichuan, Anhui, zhejiang and other places, early in《Sheng Nong's herbal classic》In just have the record of evodia rutaecarpa, applicating history is swung
Long, clinical effectiveness significantly, the effect of with eliminating cold to stop pain, stopping nausea and vomiting by lowering the adverse flow of QI, supporing yang antidiarrheal, soothing liver-qi stagnation, promoting qi circulation and relieving pain, quite by people
Concern.
The main chemical compositions of Evodia：Alkaloids, bitter principle class, flavonoids, Benzofurantone, drop sequiterpene
Class, volatile oil etc., main active is rutaecarpin, Rutaecarpine and dehydroevodiamine in fruit.Such compound
Primary pharmacological activity has expansion of blood vessels, step-down, cardiac stimulant, antidiarrheal, contraction uterus, desinsection, antibacterial, antiviral, antiulcer, cholinolytic
Esterase, anti-amnesia and antitumor action.
The content of the invention
Extracting and developing, the method for purifying the invention provides dehydroevodiamine are to take Evodia（Evodia）Plant
Thing evodia rutaecarpa（E. rutaecarpa (Juss.) Benth）, Shi Hu（E. rutaecarpa var. officinalis
(Dode) Huang）, thin hair evodia rutaecarpa（E. rutaecarpa var. bodinieri(Dode) Huang）, Fructus seu Radix Evodiae austrosinensis
（E. austrosinensis）, smelly peppery Wu's cornel（E. fargesii）And smelly wingceltis Wu cornel（E. daniellii）It is fresh（Or it is dry）Really
It is real, or its pulverized product, with water, methyl alcohol, ethanol, acetone equal solvent or secondly kind, the extraction of various mixed solvents, 70 DEG C of extract solution
Below it is concentrated in vacuo to dry（Or organic solvent-free）, add water to suitable volume, removal precipitation（If any precipitation）, upper conventional treatment
Good adsorption column, washes decontamination with water, near colourless, then with the ethanol of 5-50%（Or methyl alcohol）Wash-out, and collect this fractions
Liquid, less than 70 DEG C be concentrated in vacuo to it is dry（Or organic solvent-free）, suitable volume is added water to, decolourized with proper amount of active carbon, decolourize
It is concentrated in vacuo to dry below 70 DEG C of solution afterwards, obtains final product dehydroevodiamine crude product, dehydroevodiamine crude product adds appropriate 20%
Ethanol（Or 20% methyl alcohol, 20% acetone）, wash away pigment, solid anhydrous solvent such as methyl alcohol, ethanol, acetone or mixed liquor,
Or they and chloroform（Or ethyl acetate）Mixed liquor dissolving, appropriate chloroform is added afterwards（Or ethyl acetate）, placing makes it
Crystallization and recrystallization.
1st, it is above-mentioned from crude drug extract the medicinal extract containing dehydroevodiamine used by solvent can be water, ethanol, methyl alcohol,
Acetone, you can be used alone, it is also possible to which two or more solvent merging is used.
2nd, it is above-mentioned to use refluxing extraction from crude drug medicinal extract of the extraction containing dehydroevodiamine, it is also possible to be carried with diacolation
Take or extracted with apparatus,Soxhlet's.
3rd, the filler used by above-mentioned filling adsorption column can be nonpolar or low pole resin, for example：Styrene type（Bag
Include methyl styrene type, ethyl styrene type）Or acrylonitrile type interpolymer resin, or cationic ion-exchange resin, silicon
The fillers such as glue, gel, ODS.
The invention provides the dehydroevodiamine to agriculture disease fungus, the inhibitory activity of bacterium, the compound
There is strong inhibitory activity to agriculture pathogenetic bacteria.
The Structural Identification of dehydroevodiamine
The chemical structural formula 1 or 2 of dehydroevodiamine
Yellow particle shape is crystallized, m.p.215-217 DEG C（Chloroform-methanol）, thermosol do not dissolve in chloroform, the mixed solvent of methyl alcohol
Acetone.The aobvious brownish red of improvement Dragendorff's reagent, it is probably alkaloid to point out the compound.Infrared spectrum shows NH（3413
cm-1）, carbonyl（1706 cm-1）, phenyl ring（1610,1498 cm-1）, double bond（1544 cm-1）.ESI-MS shows the compound
Quasi-molecular ion peak is 302 [M+H-Cl]+（100）, show that its molecular weight is 301.The chemical combination is can determine that with reference to hydrogen spectrum, carbon spectrum
The molecular formula of thing is [C19H16N3O]+, degree of unsaturation is 14.
Hydrogen spectrum display δH12.80 (1H, s) be NH proton signal, δH (8H is m) by 8 fragrant hydrogen to 7.27-8.34
Two groups of Hydrogen Protons of molecular two Spin Systems of matter, δH 3.34 (2H, t, J=7.2,6.9Hz) and δH 4.47 (2H,
T, J=7.2,6.9Hz) to be 2 have fitting relations methylene hydrogen signal, δH 4.41 (3H s) is N-CH3Hydrogen signal.
Carbon spectrum 19 carbon signals of display, wherein 1 carbonyl δC 158.3, δC 113.7-150.1 has 15 aromatic carbon signals, 2 methylene
δC 42.2 and δC 18.6 and 1 N-methyl carbon signal δC 41.1。
Physicochemical constant and spectral data are consistent with the dehydroevodiamine of document report, it is thus determined that the compound
It is dehydroevodiamine.
The NMR data full ownership of the dehydroevodiamine of table 1
| No. C | ||
| NH | 12.80 (1H, s) | |
| 2 | 130.3 | |
| 3 | 150.1 | |
| 5 | 4.47 (2H, m) | 42.2 |
| 6 | 3.34 (2H, m) | 18.6 |
| 7 | 120.2 | |
| 8 | 123.4 | |
| 9 | 7.88 (1H, d, J=8.1) | 121.6 |
| 10 | 6.90 (1H, J=7.2, 8.1) | 121.7 |
| 11 | 7.25 (1H, J=7.2, 8.4) | 128.8 |
| 12 | 6.82 (1H, d, J=8.4) | 113.7 |
| 13 | 141.6 | |
| 15 | 139.8 | |
| 16 | 8.19 (1H, d, J=8.1) | 118.6 |
| 17 | 8.13 (1H, dd, J=8.1, 6.9) | 136.7 |
| 18 | 7.80 (1H, J=6.3, 6.9) | 128.7 |
| 19 | 8.34 (1H, d, J=6.3) | 127.8 |
| 20 | 118.8 | |
| 21 | 158.3 | |
| 41.1 |
Brief description of the drawings：
Can be reported as APPENDIX MATERIALSThe using figure below.
The IR spectrums of Fig. 1, dehydroevodiamine 1
Fig. 2, dehydroevodiamine 11H H NMR spectroscopies
Fig. 3, dehydroevodiamine 113C H NMR spectroscopies
The ESI-MS spectrums of Fig. 4, dehydroevodiamine 1
Fig. 5, dehydroevodiamine 21H H NMR spectroscopies
Fig. 6, dehydroevodiamine 213C H NMR spectroscopies
The ESI-MS spectrums of Fig. 7, dehydroevodiamine 2
Specific embodiment：
With reference to specific embodiment, the invention will be further described, but present disclosure is not restricted to cited reality
Apply mode.
Embodiment 1.
Real 2 Kg of fresh fruit of evodia rutaecarpa, plus the d of 70% ethanol, 3500 mL soaking at room temperature 7 are taken, leaching extract solution, the dregs of a decoction add 70% ethanol
3000 mL, the d of soaking at room temperature 7, leaching extract solution, the dregs of a decoction add the mL of 70% ethanol 3000, the d of soaking at room temperature 7, leaching extract solution to close
And the extract solution of all leachings, extract solution is concentrated under reduced pressure into 200 mL at 50 DEG C, and removes the ethanol of residual, plus equivalent water,
Filter off precipitation, upper processed good D101 type macroporous resin columns（3 Kg D101 type macroreticular resins are placed in the glass column of Φ=10 cm
It is interior）, routinely wash away impurity with water, near colourless, then with 5% ethanol elution near colourless, and collect this elution fractions, 50
DEG C be concentrated under reduced pressure into 100 mL, add water to 500 mL, with the g of Powdered Activated Carbon 5,10' is boiled in heating, filter while hot yellow is molten
Liquid, 50 DEG C are concentrated under reduced pressure into dry, obtain final product dehydroevodiamine crude product, and dehydroevodiamine crude product adds the methyl alcohol of 30 mL 20% to filter
Depigmentation, solid is dissolved with 30 mL methyl alcohol, adds 90 mL chloroforms, and placement crystallizes it, uses chloroform-methanol（V/V=3:1）Weight
Both the g of dehydroevodiamine 1.7 is obtained after crystallization.
Embodiment 2.
Real 500 g of dry fruit of evodia rutaecarpa are taken, is put into the round-bottomed flask of 5 L, plus the mL of 70% methyl alcohol 4000, round-bottomed flask is put into
In water-bath, 1 h, leaching extract solution are heated to reflux, the dregs of a decoction add the mL of 70% methyl alcohol 3000, are heated to reflux 1 h, leaching extract solution,
The dregs of a decoction add the mL of 70% methyl alcohol 3000, are heated to reflux 1 h, and leaching extract solution merges the extract solution of all leachings, and extract solution is at 45 DEG C
Be concentrated under reduced pressure into 200 mL, and remove the methyl alcohol of residual, plus equivalent water, filter off precipitation, upper processed good AB type macropore trees
Fat post（2 Kg AB type macroreticular resins are placed in the glass column of Φ=10 cm）, impurity is routinely washed away with water, near colourless, then use
10% ethanol elution then with 30% ethanol elution near colourless, and collects this elution fractions, 45 DEG C of decompressions near colourless
100 mL are concentrated into, 500 mL are added water to, with the g of Powdered Activated Carbon 5, heating is boiled 10', yellow solution, 45 DEG C are filtered to obtain while hot
It is concentrated under reduced pressure into dry, obtains final product dehydroevodiamine crude product, dehydroevodiamine crude product adds the methyl alcohol of 30 mL 20% to filter pigment,
Solid is dissolved with 30 mL methyl alcohol, adds 90 mL chloroforms, and placement crystallizes it, uses chloroform-methanol（V/V=2:1）After recrystallization both
Obtain the g of dehydroevodiamine 1.1.
Embodiment 3.
Real 2 Kg of fresh fruit of Shi Hu, plus the d of 80% methyl alcohol, 3500 mL soaking at room temperature 7 are taken, leaching extract solution, the dregs of a decoction add 80% methyl alcohol
3000 mL, the d of soaking at room temperature 7, leaching extract solution, the dregs of a decoction add the mL of 80% methyl alcohol 3000, the d of soaking at room temperature 7, leaching extract solution to close
And the extract solution of all leachings, extract solution is concentrated under reduced pressure into 200 mL at 60 DEG C, and removes the methyl alcohol of residual, plus equivalent water,
Filter off precipitation, upper processed good cation exchange resin column（2 Kg resin cations are placed in the glass column of Φ=10 cm）,
Routinely wash away impurity with water, near colourless, then with 20% methyl alcohol be eluted to it is near colourless, be then eluted to methyl alcohol it is near colourless, and
Collect this elution fractions, 60 DEG C are concentrated under reduced pressure into dry, obtain final product dehydroevodiamine crude product, and dehydroevodiamine crude product adds 15
The methyl alcohol of mL 20% filters pigment, and solid is dissolved with 20 mL methyl alcohol, adds 60 mL chloroforms, and placement crystallizes it, with chloroform-first
Alcohol（V/V=1:1）Both the g of dehydroevodiamine 0.9 is obtained after recrystallization.
Embodiment 4.
Real 500 g of dry fruit of Shi Hu are taken, is put into the round-bottomed flask of 5 L, plus the mL of 50% ethanol 4000, round-bottomed flask is put into water
In bath, 1 h, leaching extract solution are heated to reflux, the dregs of a decoction add the mL of 50% ethanol 3000, are heated to reflux 1 h, leaching extract solution, medicine
Slag adds the mL of 50% ethanol 3000, is heated to reflux 1 h, and leaching extract solution merges the extract solution of all leachings, and extract solution subtracts at 50 DEG C
Pressure is concentrated into 200 mL, and removes the ethanol of residual, plus equivalent water, filter off precipitation, upper processed good AB type macroreticular resins
Post（2 Kg AB type macroreticular resins are placed in the glass column of Φ=10 cm）, impurity is routinely washed away with water, near colourless, with 50%
Ethanol elution collects this elution fractions near colourless, and 50 DEG C are concentrated under reduced pressure into 100 mL, add water to 500 mL, use powder
10' is boiled in the g of activated carbon 5, heating, filters to obtain yellow solution while hot, and 50 DEG C are concentrated under reduced pressure into dry, obtain final product dehydroevodiamine thick
Product, dehydroevodiamine crude product adds the methyl alcohol of 30 mL 20% to filter pigment, and solid is dissolved with 20 mL methyl alcohol, adds 70 mL chlorine
Imitative, placement crystallizes it, uses chloroform-methanol（V/V=2:1）Both the g of dehydroevodiamine 1.0 is obtained after recrystallization.
Embodiment 5.
Real 500 g of fresh fruit of thin hair evodia rutaecarpa are taken, water seepage pressure effects are used, the mL of percolate 5000 is obtained, 800 mL are concentrated under reduced pressure into,
Upper processed good D101 type macroporous resin columns（3 KgD101 type macroreticular resins are placed in the glass column of Φ=12 cm）, it is normal with water
Rule wash away impurity, near colourless, then with 30% ethanol elution near colourless, and collect this elution fractions, and 40 DEG C of decompressions are dense
100 mL are reduced to, 500 mL are added water to, with the g of Powdered Activated Carbon 5, heating is boiled 10', yellow solution is filtered to obtain while hot, and 40 DEG C subtract
Pressure is concentrated to dryness, and obtains final product dehydroevodiamine crude product, and dehydroevodiamine crude product adds the methyl alcohol of 12 mL 20% to filter pigment, Gu
Body is dissolved with 10 mL methyl alcohol, adds 30 mL chloroforms, and placement crystallizes it, uses chloroform-methanol（V/V=3:1）Both obtained after recrystallization
The g of dehydroevodiamine 0.7.
Embodiment 6.
Real 4 Kg of Fructus seu Radix Evodiae austrosinensis dry fruit are taken, is extracted 3 times with 80% alcohol reflux, 3 hours every time, merge alcohol extract, 55 DEG C of decompressions are dense
Contracted to obtain thick medicinal extract about 800g, is dissolved in water to suspension, and petroleum ether is used successively（60-90℃）, chloroform, ethyl acetate and water saturation
Extracting n-butyl alcohol, medicinal extract is condensed into respectively and obtains petroleum ether part 14g, chloroform extract 209g, ethyl acetate extract 26g, positive fourth
Alcohol position 210g, water position 316g.N-butanol portion iterates through silica gel column chromatography, gel filtration chromatography, reversed phase column chromatography and weight
The means such as crystallization, obtain the g of dehydroevodiamine 1.5.
Embodiment 7.
Smelly peppery Wu's cornel dry fruit reality 0.5Kg is taken, through petroleum ether cold soaking 7 days, oil ethereal extract 27g is obtained；The dregs of a decoction after degreasing, with 60%
Alcohol reflux is extracted 3 times, 3 hours every time, merges alcohol extract, and be concentrated under reduced pressure to obtain thick medicinal extract about 1.1Kg；The sour water for plus 2% pinch it is molten extremely
Suspension, sour water is extracted with ethyl acetate, and obtains ethyl acetate extract 163g；Sour water ammonification scale after extraction to PH9-10,
Extracted with chloroform, obtain TA compared with the chloroform medicinal extract 66g for concentrating；Last buck is adjusted to neutrality extracting n-butyl alcohol, obtains positive fourth
Alcohol medicinal extract 193g.N-butanol portion iterates through the means such as silica gel column chromatography, gel filtration chromatography, reversed phase column chromatography and recrystallization,
Obtain the g of dehydroevodiamine 0.75.
Embodiment 8.
The fresh fruit reality 1Kg of smelly wingceltis Wu cornel, plus the d of 80% methyl alcohol, 1750 mL soaking at room temperature 7 are taken, leaching extract solution, the dregs of a decoction add 80% first
The mL of alcohol 1500, the d of soaking at room temperature 7, leaching extract solution, the dregs of a decoction add the mL of 80% methyl alcohol 1500, the d of soaking at room temperature 7, leaching extract solution,
Merge the extract solution of all leachings, extract solution is concentrated under reduced pressure into 100 mL at 50 DEG C, and remove the methyl alcohol of residual, plus equivalent
Water, filters off precipitation, upper processed good cation exchange resin column（1 Kg resin cations are placed in the glass column of Φ=10 cm
It is interior）, impurity is routinely washed away with water, near colourless, then it is eluted near colourless with 20% methyl alcohol, then it is eluted to nearly nothing with methyl alcohol
Color, and collect this elution fractions, 50 DEG C are concentrated under reduced pressure into dry, obtain final product dehydroevodiamine crude product, dehydroevodiamine crude product
Plus 7.5 the methyl alcohol of mL 20% filter pigment, solid is dissolved with 10 mL methyl alcohol, adds 30 mL chloroforms, and placement crystallizes it, uses
Chloroform-methanol（V/V=3:1）Both the g of dehydroevodiamine 0.3 is obtained after recrystallization.
Embodiment 9.
The antimicrobial spectrum for preparing gained dehydroevodiamine by embodiment 1-8 is determined：
Measure object includes Sclerotinia sclerotiorum, fusarium graminearum, botrytis cinerea pers, grape anthracnose, rice banded sclerotial blight
Germ, southern corn leaf blight, fusarium moniliforme, Pyricularia oryzae, rice leaf spot bacteria, xanthomonas oryzae pv. oryzicola, mandarin orange
The common agriculture pathogen of 12 kinds of tangerine ulcer bacteria and brassicaceous vegetable black rot etc..All confession examination pathogens are field and adopt
Collection isolated strains.
Dehydroevodiamine is dissolved in DMSO, the mother liquor that concentration is 5000 μ g/mL is configured to.
Appropriate dehydroevodiamine mother liquor or isometric DMSO are added into heating and melting and 55 DEG C of PSA culture mediums are cooled to
In, the pastille flat board of final concentration of 10 μ g/mL is made in the culture dish that a diameter of 9cm is poured into after mixing.With the punching of diameter 5mm
Device is beaten at the fungus colony edge of preculture and takes bacterium dish, and is seeded in the middle of pastille flat board, each 3 repetition for the treatment of.25 DEG C are fallen
Culture is put to determine colony diameter and simultaneously calculate inhibiting rate to control close to plate, crossing method is covered with.Inhibiting rate（%）=（Control bacterium colony
Diameter ﹣ agent-feeding treatment colony diameters）/ control colony diameter × 100.Colony diameter=crossing method measure diameter average value-
5mm。
The pastille of final concentration of 10 μ g/mL will be made in dehydroevodiamine mother liquor or isometric DMSO addition NB nutrient solutions
Nutrient solution, with spectrophotometer by the bacterial cultures OD of preculture to exponential phase600Value is adjusted to 0.02, and by 1:200
Ratio is added in pastille nutrient solution, each 3 repetition for the treatment of.28 DEG C of 175rpm shake training makes control length to exponential phase, with point
Light photometric determination OD600And calculate inhibiting rate.Inhibiting rate（%）=（Control OD600Value ﹣ agent-feeding treatments OD600Value）/ control OD600Value
×100。
Result of the test
Dehydroevodiamine antimicrobial spectrum as obtained by prepared by embodiment 1-8 is as shown in table 1.Result can be seen that dehydrogenation from table
Rutaecarpin is weaker to agriculture disease fungus activity, and has stronger inhibitory activity to agriculture pathogenetic bacteria.
Table 1 presses the inhibiting rate of the dehydroevodiamine to agriculture pathogen of embodiment 1-8 preparations
| Pathogen | 10 μ g/mL inhibiting rates（%） |
| Sclerotinia sclerotiorum | 13.78 |
| Fusarium graminearum | 6.19 |
| Botrytis cinerea pers | 6.76 |
| Grape anthracnose | 2.29 |
| Rhizoctonia solani Kuhn | 5.28 |
| Southern corn leaf blight | 23.15 |
| Fusarium moniliforme | 3.95 |
| Pyricularia oryzae germ | 6.73 |
| Rice leaf spot bacteria | 98.84 |
| Xanthomonas oryzae pv. oryzicola | 92.43 |
| Citrus processing | 82.57 |
| Brassicaceous vegetable black rot | 43.89 |
Embodiment 10.
Gained dehydroevodiamine is prepared by embodiment 1-8 to determine the virulence regression equation of agriculture pathogenetic bacteria：
Measure object includes rice leaf spot bacteria, xanthomonas oryzae pv. oryzicola, citrus processing and brassicaceous vegetable
The common agriculture pathogenetic bacteria of 4 kinds of black rot etc..It is all to be field collection isolated strains for examination pathogen.
Dehydroevodiamine is dissolved in DMSO, concentration is configured to and is the mother liquor of 5000 μ g/mL, and use DMSO doubling dilutions
It is stand-by into 7 series concentration gradients.Pastille is made during each concentration dehydroevodiamine or isometric DMSO are added into NB nutrient solutions
Nutrient solution, with spectrophotometer by the bacterial cultures OD of preculture to exponential phase6000.02 is adjusted to, bacterium solution is added and is contained
In medicine nutrient solution, each 3 repetition for the treatment of.28 DEG C of 175 rpm shakes training to control exponential phase, uses spectrophotometric determination
OD600And calculate inhibiting rate.Inhibiting rate（%）=（Control OD600Value ﹣ agent-feeding treatments OD600Value）/ control OD600Value × 100.According to each
Concentration inhibiting rate calculates virulence regression equation using DPS v7.05.
Result of the test
Dehydroevodiamine as obtained by prepared by embodiment 1-8 is as shown in table 2 to the virulence regression equation of agriculture pathogenetic bacteria.From
To can be seen that dehydroevodiamine strong to agriculture pathogenetic bacteria inhibition for result in table.
Table 2 presses the virulence regression equation of the dehydroevodiamine to agriculture pathogenetic bacteria of embodiment 1-8 preparations
| Pathogen | Virulence regression equation | R values | ||
| Rice leaf spot bacteria | y=4.9976+4.6601x | 1.0012 | 1.8859 | 0.9852 |
| Xanthomonas oryzae pv. oryzicola | y=3.0445+2.9642x | 4.5678 | 12.3607 | 0.9913 |
| Citrus processing | y=2.6240+2.9593x | 6.3516 | 17.2162 | 0.9956 |
| Brassicaceous vegetable black rot | y=0.7503+4.1715x | 10.4414 | 21.1824 | 0.9858 |
Claims (6)
1. it is a kind of to be used for from Rutaceae Evodia plant evodia rutaecarpa（E. rutaecarpa (Juss.) Benth）, Shi Hu（E.
rutaecarpa var. officinalis(Dode) Huang）, thin hair evodia rutaecarpa（E. rutaecarpa var.bodinieri(Dode) Huang）, Fructus seu Radix Evodiae austrosinensis（E. austrosinensis）, smelly peppery Wu's cornel（E. fargesii）And it is smelly
Wingceltis Wu's cornel（E. daniellii）Fruit in prepare the method for dehydroevodiamine, it is characterised in that above fruit is passed through
Water, methyl alcohol, ethanol, acetone or its mixed solvent are extracted, the dehydrogenation Wu after extract solution concentration in the aqueous solution of the extract of gained
The compositions such as fruit of medicinal cornel alkali cross the chromatographic column equipped with adsorbent, collect the ethanol of 5-50% or the methanol-eluted fractions of 5-50%, concentrate back
Ethanol or methyl alcohol are received, with activated carbon decolorizing, then the solution after decolourizing is concentrated to dry, dehydroevodiamine crude product, dehydrogenation Wu is obtained final product
Fruit of medicinal cornel alkali crude product adds appropriate methyl alcohol or ethanol, acetone solution, adds appropriate chloroform or ethyl acetate afterwards, placement make its crystallization and
Recrystallization.
2. according to a kind of method for preparing dehydroevodiamine described in claim 1, it is characterised in that Evodia plant Wu
Contain dehydroevodiamine in the fruit extract of the fruit of medicinal cornel, Shi Hu, thin hair evodia rutaecarpa, Fructus seu Radix Evodiae austrosinensis, smelly peppery Wu's cornel and smelly wingceltis Wu cornel
Composition crosses the chromatographic column equipped with adsorbent, first washes removal of impurities with water.
3., according to a kind of method for preparing dehydroevodiamine described in claim 2, it is characterised in that after water elution, use
The ethanol of 5-50% or the methyl alcohol of 5-50% are eluted, collect concentrate this part, with activated carbon decolorizing after, then concentrate decolouring after
Solution obtains final product dehydroevodiamine crude product to dry.
4. according to a kind of method for preparing dehydroevodiamine described in claim 3, it is characterised in that dehydroevodiamine is thick
Product methanol-chloroform, ethanol-chloroform, acetone-chloroform, or methanol-ethyl acetate, EtOH-EtOAc, acetone and ethyl acetate
Mixed solvent crystallization and recrystallize to obtain dehydroevodiamine sterling.
5. a kind of method for preparing dehydroevodiamine described in claim 1-4 any one, it is characterised in that described layer
The adsorbent that analysis post is selected, can be nonpolar or low pole macroreticular resin, or cationic ion-exchange resin.
6. the dehydroevodiamine for being prepared according to claim 1-5 methods describeds, it is characterised in that described compound is used to make
Purposes in terms of standby disinfectant use in agriculture, controlling object includes rice leaf spot bacteria, xanthomonas oryzae pv. oryzicola, c itrus canker
Germ, brassicaceous vegetable black rot.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201710111803.8A CN106892919A (en) | 2017-02-28 | 2017-02-28 | The preparation method of dehydroevodiamine and its purposes of anti-agriculture pathogen |
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| CN111333628A (en) * | 2020-04-20 | 2020-06-26 | 大连医科大学附属第一医院 | Indole alkaloid, preparation method and application as hypoglycemic drug |
| CN108373470B (en) * | 2018-04-10 | 2021-01-19 | 南昌大学 | Method for separating evodiamine and rutaecarpine from fructus evodiae |
| CN112438272A (en) * | 2020-12-03 | 2021-03-05 | 兰州大学 | Evodiamine analog and application thereof in preventing and treating plant pathogenic fungi |
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| CN109232560A (en) * | 2018-10-11 | 2019-01-18 | 江苏省中国科学院植物研究所 | The preparation method in Rett Xining and its purposes of anti-agriculture pathogen |
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| CN109232560A (en) * | 2018-10-11 | 2019-01-18 | 江苏省中国科学院植物研究所 | The preparation method in Rett Xining and its purposes of anti-agriculture pathogen |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108373470B (en) * | 2018-04-10 | 2021-01-19 | 南昌大学 | Method for separating evodiamine and rutaecarpine from fructus evodiae |
| CN111333628A (en) * | 2020-04-20 | 2020-06-26 | 大连医科大学附属第一医院 | Indole alkaloid, preparation method and application as hypoglycemic drug |
| CN111333628B (en) * | 2020-04-20 | 2022-05-10 | 大连医科大学附属第一医院 | Indole alkaloid, preparation method and application as hypoglycemic drug |
| CN112438272A (en) * | 2020-12-03 | 2021-03-05 | 兰州大学 | Evodiamine analog and application thereof in preventing and treating plant pathogenic fungi |
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