CN107400108B - A kind of bicoumarin derivative and the preparation method and application thereof - Google Patents
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Abstract
The invention discloses a kind of bicoumarin derivatives and the preparation method and application thereof.The molecular formula of the bicoumarin derivative is C22H18O7, structural formula is shown in formula I.The preparation method of the bicoumarin derivative is the following steps are included: (1) carries out Spawn incubation to Aspergillusclavatus (Aspergillus clavatus) R7 in bacterium culture medium；(2) fermented and cultured is carried out to strain obtained in step (1) in the fermentation medium, then it is extracted with ethanol water or methanol aqueous solution, it is concentrated under reduced pressure, it is extracted again with organic solvent, it is most further purified afterwards through silica gel column chromatography, Sephdex LH-20 gel filtration chromatography and recrystallization, obtains bicoumarin derivative.Bicoumarin derivative produced by the present invention has very strong inhibition tomato Fusarium oxysporum, citrus Penicillium notatum and musae effect, can be used as microorganism disinfectant use in agriculture, and raw material can be mass produced, and have a extensive future.
Description
Technical field
The invention belongs to biological chemical field, in particular to a kind of bicoumarin derivative and the preparation method and application thereof.
Background technique
Fungal diseases of plants is one of an important factor for harming the crops healthy growth.According to statistics, the whole world is every year because of disease
Caused by the average loss of farm output account for about the 10%~15% of total output.Prevention and treatment fungal diseases of plants traditionally mainly uses
Chemical synthesis fungicide also causes seriously to pollute although significant effect to environment, while being formed and being remained in crop surface, prestige
Coerce human health.In recent years, with the development of the social economy, living standards of the people are continuously improved, to foodstuffs such as veterinary antibiotics
The demand of industrial crops is continuously increased, therefore develops that toxicity is low, and degradable novel green disinfectant use in agriculture is extremely urgent.
Plant endogenesis epiphyte colonizes in inside plants and forms unique metabolic way, can generate novel bioactive substance, together
When its metabolite it is generally non-toxic or low-toxic to plant, be the valuable source of green disinfectant use in agriculture exploitation.However, being so far
Only, there is not yet obtaining the bicoumarin compound of important anti-fungal activity of plant pathogenic from plant endogenesis epiphyte as agriculture
With the use of fungicide.
Summary of the invention
The primary purpose of the present invention is that the shortcomings that overcoming the prior art and deficiency, provide a kind of bicoumarin derivative.
Another object of the present invention is to provide the preparation methods of the bicoumarin derivative.
A further object of the present invention is to provide the applications of the bicoumarin derivative.
The purpose of the invention is achieved by the following technical solution: a kind of bicoumarin derivative, molecular formula C22H18O7,
Structural formula is shown in formula I:
The bicoumarin derivative is a kind of white, needle-shaped crystals, entitled 4,4 '-dimethoxy -5, and 5 '-diformazans
Base -7,7 '-oxygen connects bicoumarin.
The preparation method of the bicoumarin derivative, comprising the following steps:
(1) Spawn incubation is carried out to Aspergillusclavatus (Aspergillus clavatus) R7 in bacterium culture medium；
(2) fermented and cultured is carried out to the strain obtained in step (1) in the fermentation medium, then with ethanol water or
Methanol aqueous solution is extracted, and is concentrated under reduced pressure, then extracted with organic solvent, is obtained bicoumarin derivative；
(Aspergillus clavatus) R7 of Aspergillusclavatus described in step (1) was preserved in extensively on May 11st, 2017
East saves Culture Collection, address: 5 building, the building of compound the 59th of Xianlie Middle Road, Guangzhou City 100, deposit number: GDMCC
NO:60179；For Myoporum bontiodes (Myoporum bontioides A.Gray) endogenetic fungus.
Preferably, bacterium culture medium described in step (1) contains the component of following weight percent: glucose 1.0~
3.5%, yeast extract 0.02~1.5%, peptone 0.01~1.5%, agar 1.0~2.5%, sodium chloride 0.2~2.0% is remaining
Amount is water；Test tube slant is made in bacterium culture medium when use.
Preferably, the condition of Spawn incubation described in step (1) are as follows: cultivated 3~10 days at 20~35 DEG C.
Preferably, fermentation medium described in step (2) contains the component of following weight percent: rice 30.0~
70.0%, sodium chloride 1.0~3.0%, surplus is water.
Preferably, the condition of fermented and cultured described in step (2) are as follows: cultivated 30~60 days at 25~30 DEG C.
Preferably, ethanol water described in step (2) is that 80~100:0~20 match ethyl alcohol by volume with water
The ethanol-water mixture arrived.
Preferably, methanol aqueous solution described in step (2) is that 80~100:0~20 match methanol by volume with water
The methanol-water mixture arrived.
Preferably, the number of extraction described in step (2) is 2~4 times.
Preferably, organic solvent described in step (2) is one of ethyl acetate and n-butanol.
Preferably, the number of extraction described in step (2) is 2~4 times.
The preparation method of the bicoumarin derivative further includes by bicoumarin derivative obtained in step (2)
It is further purified by silica gel column chromatography, Sephdex LH-20 gel filtration chromatography and recrystallization.
Preferably, the silica gel column chromatography is to carry out chromatographic isolation in 200~300 mesh silicagel columns.
Preferably, the silica gel column chromatography uses the mixed solvent of petroleum ether-ethyl acetate to carry out gradient for eluant, eluent
Elution；The percentage by volume of the ethyl acetate is stepped up from 0 to 100%.
Preferably, the Sephdex LH-20 gel filtration chromatography uses chloroform and methanol mixed solution for mobile phase；Institute
The chloroform and methanol volume ratio stated are 2:3.
Preferably, the recrystallization is to be recrystallized in chloroform, acetone or ethyl acetate.
Application of the bicoumarin derivative in preparation prevention and treatment phytopathogen disinfectant use in agriculture.
Preferably, the phytopathogen is tomato Fusarium oxysporum (Fusarium oxysporum), citrus Penicillium notatum
(Penicillium italicum) or musae (Colletotrichum musae).
Preferably, the phytopathogen disinfectant use in agriculture can add all kinds of solvents and/or auxiliary agent, be made spray or
Pulvis is used as microorganism disinfectant use in agriculture.
The present invention has the following advantages and effects with respect to the prior art: bicoumarin (bicoumarin) of the present invention is spread out
Biology has very strong inhibition tomato Fusarium oxysporum (Fusarium oxysporum), citrus Penicillium notatum (Penicillium
Italicum) and the effect of musae (Colletotrichum musae), it can be used as microorganism disinfectant use in agriculture, and
Raw material can be mass produced, and have a extensive future.
Specific embodiment
Below with reference to embodiment, the present invention is described in further detail, and embodiments of the present invention are not limited thereto.
Aspergillusclavatus involved in the present invention (Aspergillus clavatus) R7 is deposited in Guangdong Province microorganism fungus kind guarantor
Hiding center, deposit number: GDMCC NO:60179, preservation date: on May 11st, 2017, preservation address: Xianlie Middle Road, Guangzhou City
No. 100 5 building, the buildings of compound the 59th.
Embodiment 1
Bicoumarin derivative is prepared by following steps:
(1) first in bacterium culture medium to Myoporum bontiodes (Myoporum bontioides A.Gray) endogenetic fungus Aspergillusclavatus
(Aspergillus clavatus) R7 carries out Spawn incubation, and bacterium culture medium used is to contain 1.0% (weight percent of glucose
Number, similarly hereinafter), yeast extract 0.02%, peptone 0.01, agar 1.0%, sodium chloride 0.2%, remaining is water.Use when system
At test tube slant, above-mentioned strain is cultivated 10 days at 28 DEG C；
(2) again to Aspergillusclavatus (Aspergillus clavatus) R7 carry out fermented and cultured, fermentation medium used be containing
Have rice 70% (weight percent, similarly hereinafter), sodium chloride 1.0% and water surplus, the stationary culture 30 days at 25 DEG C of room temperature.
(3) by the bacterial strain ethanol-water mixture fermented in step (2) (volume ratio of ethyl alcohol and water is 100:0) leaching
It mentions 3 times, after reduced pressure, is extracted with ethyl acetate 3 times (ethyl acetate can be replaced with n-butanol), concentrated extract, 200~
Chromatographic isolation is carried out in 300 mesh silicagel columns, is eluted with petroleum ether-ethyl acetate mixed solvent, wherein volume shared by ethyl acetate
Percentage is stepped up from 0 to 100%；Merge the eluent of 100% ethyl acetate, then with Sephdex LH-20 gel column layer
Analysis uses mobile phase volume ratio for chloroform: methanol=2:3 is separated, and is separated, and obtained solid uses chloroform (can use third again
Ketone, ethyl acetate replacement) carry out recrystallization purifying repeatedly, obtain white, needle-shaped crystals, as the bicoumarin derivative (4,
4 '-dimethoxys -5,5 '-dimethyl -7,7 '-oxygen connects bicoumarin).
Embodiment 2
Bicoumarin derivative is prepared by following steps:
(1) first Myoporum bontiodes endogenetic fungus Aspergillusclavatus (Aspergillus clavatus) R7 is carried out in bacterium culture medium
Spawn incubation, bacterium culture medium used are to contain glucose 3.5% (weight percent, similarly hereinafter), yeast extract 1.5%, peptone
1.5%, agar 2.5%, sodium chloride 2.0%, remaining is water.Test tube slant is made into when use, above-mentioned strain is at 28 DEG C
Culture 3 days；
(2) again to Aspergillusclavatus (Aspergillus clavatus) R7 carry out fermented and cultured, fermentation medium used be containing
There are rice 30.0% (weight percent, similarly hereinafter), sodium chloride 3.0% and water surplus, stationary culture 60 days at 20 DEG C；
(3) bacterial strain for fermenting step (2) is extracted 4 times with methanol-water mixture (volume ratio 95:5), is concentrated under reduced pressure
Afterwards, with extracting n-butyl alcohol 4 times (n-butanol can be replaced with ethyl acetate), concentrated extract, in 200~300 mesh silicagel columns into
Row chromatographic isolation, with the elution of petroleum ether-ethyl acetate mixed solvent, wherein percentage by volume shared by ethyl acetate gradually increases from 0
It is added to 100%；；The eluent for merging 100% ethyl acetate uses Sephdex LH-20 gel filtration chromatography using mobile phase volume again
Than for chloroform: methanol=2:3 is separated, and obtained solid is weighed with chloroform (can be replaced with acetone, ethyl acetate) repeatedly again
Crystallization purifying obtains white, needle-shaped crystals, as the bicoumarin derivative (4,4 '-dimethoxy -5,5 '-dimethyl -7,
7 '-oxygen connect bicoumarin).
Embodiment 3
Bicoumarin derivative is prepared by following steps:
(1) first Myoporum bontiodes endogenetic fungus Aspergillusclavatus (Aspergillus clavatus) R7 is carried out in bacterium culture medium
Spawn incubation, bacterium culture medium used are to contain glucose 2.5% (weight percent, similarly hereinafter), yeast extract 0.5%, peptone
1.0%, agar 1.5%, sodium chloride 1.5%, remaining is water.Test tube slant is made into when use, above-mentioned strain is at 28 DEG C
Culture 3 days；
(2) again to Aspergillusclavatus (Aspergillus clavatus) R7 carry out fermented and cultured, fermentation medium used be containing
There are rice 50.0% (weight percent, similarly hereinafter), sodium chloride 2.5% and water surplus, stationary culture 45 days at 30 DEG C；
(3) bacterial strain for fermenting step (2) is extracted 2 times with ethanol-water mixture (volume ratio 80:20), is depressurized dense
After contracting, with extracting n-butyl alcohol 2 times (n-butanol can be replaced with ethyl acetate), concentrated extract, in 200~300 mesh silicagel columns
Carry out chromatographic isolation, with petroleum ether-ethyl acetate mixed solvent elution, wherein percentage by volume shared by ethyl acetate from 0 gradually
Increase to 100%；；The eluent for merging 100% ethyl acetate uses Sephdex LH-20 gel filtration chromatography using mobile phase body again
Product is than being chloroform: methanol=2:3 is separated, and obtained solid is carried out repeatedly with chloroform (can be replaced with acetone, ethyl acetate) again
Recrystallization purifying obtains white, needle-shaped crystals, as described bicoumarin derivative (4,4 '-dimethoxy -5,5 '-dimethyl -
7,7 '-oxygen connect bicoumarin).
Through detecting, 4,4 '-dimethoxy -5 of embodiment 1,2 and 3 gained compound, 5 '-dimethyl -7,7 '-oxygen Lian Shuanxiang
The spectral data of legumin is as follows: C22H18O7, m.p.174.7-175.3 DEG C；HR-ESI-MS m/z315.1129([M+H]+,
calcd.for 315.1125).1H-NMR(600MHz,CD3COCD3) and13C-NMR(150MHz,CD3COCD3) it is shown in Table 1.
Table 1. 4,4 '-dimethoxy -5,5 '-dimethyl -7,7 '-oxygen connects bicoumarin1H-NMR(600MHz,
CD3COCD3) and13C-NMR(150MHz,CD3COCD3)
| No. | δC | δH,Mult.(J in Hz) |
| 2 | 162.1,C | 7.61,s |
| 3 | 88.6,CH | 5.7,s |
| 4 | 169.5,C | |
| 5 | 137.9,C | |
| 6 | 119.6,CH | 6.92,d(2.4) |
| 7 | 155.5,C | |
| 8 | 105.4,CH | 7.05,d(2.4) |
| 9 | 57.2,CH3 | 3.94,s |
| 10 | 23.5,CH3 | 2.56,s |
| 4a | 109.4,C | |
| 8a | 156.4,C | |
| 2’ | 162.1,C | 7.61,s |
| 3’ | 88.6,CH | 5.7,s |
| 4’ | 169.5,C | |
| 5’ | 137.9,C | |
| 6’ | 119.6,CH | 6.92,d(2.4) |
| 7’ | 155.5,C | |
| 8’ | 105.4,CH | 7.05,d(2.4) |
| 9’ | 57.2,CH3 | 3.94,s |
| 10’ | 23.5,CH3 | 2.56,s |
| 4’a | 109.4,C | |
| 8’a | 156.4,C |
The structural formula of embodiment 1,2 and 3 gained compounds is as follows:
Embodiment 4
The compounds of this invention tests tomato Fusarium oxysporum, citrus Penicillium notatum and musae bacteriostatic activity:
1 gained compound of embodiment (4,4 '-dimethoxys -5,5 '-dimethyl -7,7 '-oxygen are measured using doubling dilution
Even bicoumarin) to tomato Fusarium oxysporum (Fusarium oxysporum), citrus Penicillium notatum (Penicillium italicum)
With the minimal inhibitory concentration (MIC) of musae (Colletotrichum musae).Strain to be tested is in 28 DEG C of constant temperature incubations
It is cultivated in case for 24 hours, observes the growing state of bacterium in test tube, concentration corresponding to the test tube without bacterium growth is that its minimum is antibacterial
Concentration.Triazolone makees positive control.It the results are shown in Table 2.
Table 2. 4,4 '-dimethoxy -5,5 '-dimethyl -7,7 '-oxygen connects the anti-fungal activity of plant pathogenic of bicoumarin
(MIC, μM)
Embodiment 5
The compounds of this invention tests tomato Fusarium oxysporum greenhouse field bactericidal activity:
The compounds of this invention (4,4 '-dimethoxys -5,5 '-dimethyl -7,7 '-oxygen connects bicoumarin) is according to " pesticide field
Between pharmacodynamic test criterion ", tested in greenhouse its to tomato wilt bacterium infection tomato leaf control efficiency.Compound concentration is
The 4 of 200,400,800ppm, 4 '-dimethoxy -5,5 '-dimethyl -7,7 '-oxygen connect bicoumarin (embodiment 1 is made) solution,
It is carried out in preventative leaf surface spraying test in the tomato leaf to infection tomato wilt bacterium, when concentration is 800,400,200ppm
When, the compounds of this invention is respectively 96%, 92%, 87% to the bacteriostasis rate of tomato wilt bacterium；To infection tomato wilt
The tomato leaf of bacterium carries out in therapeutic leaf surface spraying test, and when concentration is 800ppm, the compounds of this invention is to tomato wilt
The bacteriostasis rate of bacterium is 75%.The result shows that the compounds of this invention has preferable bactericidal activity to tomato wilt bacterium.
Embodiment 6
The compounds of this invention tests the bactericidal activity of Glorosprium musarum Cookeet Mass preservation after Banana:
Compound concentration is the 4 of 200,400,800ppm, 4 '-dimethoxy -5,5 '-dimethyl -7, and 7 '-oxygen connect bicoumarin
(embodiment 1 is made) solution, carries out preventative any of several broadleaf plants body to the banana of infection Glorosprium musarum Cookeet Mass and sprays, not spray of the present inventionization
Conjunction object preparation is blank control.After natural air drying, it is put into indoor 18 DEG C~20 DEG C and saves 14 days, when concentration is 800ppm, warp
Healthy fruit > 68% after the sprinkling of the compounds of this invention preparation, the blank control healthy fruit for not spraying the compounds of this invention preparation are
10%.
Embodiment 7
The compounds of this invention tests the bactericidal activity of Penicillium italicum bacterium preservation after citrus is adopted:
Compound concentration is the 4 of 200,400,800ppm, 4 '-dimethoxy -5,5 '-dimethyl -7, and 7 '-oxygen connect bicoumarin
(embodiment 1 is made) solution carries out preventative epidermis sprinkling to the citrus of infection Penicillium italicum bacterium, not spray of the present inventionization
Conjunction object preparation is blank control.After natural air drying, it is put into indoor 18 DEG C~20 DEG C and saves 14 days, when concentration is 800ppm, warp
Healthy fruit > 65% after the sprinkling of the compounds of this invention preparation, the blank control healthy fruit for not spraying the compounds of this invention preparation are
10%.
Embodiment 4~7 the experimental results showed that the compounds of this invention to tomato Fusarium oxysporum, citrus Penicillium notatum and banana anthrax
Bacterium has very strong inhibition growth, can add all kinds of solvents, auxiliary agent, and spray is made or pulvis is used as disinfectant use in agriculture.
The above embodiment is a preferred embodiment of the present invention, but embodiments of the present invention are not by above-described embodiment
Limitation, other any changes, modifications, substitutions, combinations, simplifications made without departing from the spirit and principles of the present invention,
It should be equivalent substitute mode, be included within the scope of the present invention.
Claims (7)
1. a kind of bicoumarin derivative, it is characterised in that: its molecular formula is C22H18O7, structural formula is shown in formula I:
2. the method for preparing bicoumarin derivative described in claim 1, which comprises the following steps:
(1) Spawn incubation is carried out to Aspergillusclavatus (Aspergillus clavatus) R7 in bacterium culture medium；
(2) fermented and cultured is carried out to the strain obtained in step (1) in the fermentation medium, then uses ethanol water or methanol
Aqueous solution is extracted, and is concentrated under reduced pressure, then extracted with organic solvent, is obtained bicoumarin derivative；
(Aspergillus clavatus) R7 of Aspergillusclavatus described in step (1) is preserved in Guangdong Province on May 19th, 2017
Culture Collection, address: 5 building, the building of compound the 59th of Xianlie Middle Road, Guangzhou City 100, deposit number: GDMCC NO:
60179；
Bacterium culture medium described in step (1) contains the component of following weight percent: glucose 1.0~3.5%, yeast extract
0.02~1.5%, peptone 0.01~1.5%, agar 1.0~2.5%, sodium chloride 0.2~2.0%, surplus is water；
Fermentation medium described in step (2) contains the component of following weight percent: rice 30.0~70.0%, sodium chloride
1.0~3.0%, surplus is water；
Ethanol water described in step (2) is that 80~100:0~20 matches obtained alcohol-water by volume for ethyl alcohol and water
Mixed liquor；
Methanol aqueous solution described in step (2) is that 80~100:0~20 matches obtained methanol-water by volume for methanol and water
Mixed liquor；
Organic solvent described in step (2) is one of ethyl acetate and n-butanol；
The condition of Spawn incubation described in step (1) are as follows: cultivated 3~10 days at 20~35 DEG C；
The condition of fermented and cultured described in step (2) are as follows: cultivated 30~60 days at 25~30 DEG C；
The preparation method of the bicoumarin derivative further includes that bicoumarin derivative obtained in step (2) is passed through silicon
Plastic column chromatography, Sephdex LH-20 gel filtration chromatography and recrystallization are further purified；
The silica gel column chromatography is to carry out chromatographic isolation in 200~300 mesh silicagel columns；The silica gel column chromatography uses petroleum
Ether-ethyl acetate mixed solvent is that eluant, eluent carries out gradient elution；The percentage by volume of the ethyl acetate gradually increases from 0
It is added to 100%；
The Sephdex LH-20 gel filtration chromatography uses chloroform and methanol mixed solution for mobile phase；The chloroform and
Methanol volume ratio is 2:3；
The recrystallization is to be recrystallized in chloroform, acetone or ethyl acetate.
3. according to the method described in claim 2, it is characterized by:
The number of extraction described in step (2) is 2~4 times；
The number of extraction described in step (2) is 2~4 times.
4. application of the bicoumarin derivative described in claim 1 in preparation prevention and treatment phytopathogen disinfectant use in agriculture.
5. bicoumarin derivative according to claim 4 answering in preparation prevention and treatment phytopathogen disinfectant use in agriculture
With, it is characterised in that:
The phytopathogen is tomato Fusarium oxysporum, citrus Penicillium notatum or musae.
6. bicoumarin derivative according to claim 5 answering in preparation prevention and treatment phytopathogen disinfectant use in agriculture
With, it is characterised in that:
The phytopathogen disinfectant use in agriculture is spray or pulvis made of addition auxiliary agent.
7. bicoumarin derivative according to claim 6 answering in preparation prevention and treatment phytopathogen disinfectant use in agriculture
With, it is characterised in that:
The auxiliary agent is solvent.
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