CN109111422A - Macrolides compound and its application in preparation prevention and treatment plant-pathogenic pathogenic bacteria drug - Google Patents
Macrolides compound and its application in preparation prevention and treatment plant-pathogenic pathogenic bacteria drug Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C05G—MIXTURES OF FERTILISERS COVERED INDIVIDUALLY BY DIFFERENT SUBCLASSES OF CLASS C05; MIXTURES OF ONE OR MORE FERTILISERS WITH MATERIALS NOT HAVING A SPECIFIC FERTILISING ACTIVITY, e.g. PESTICIDES, SOIL-CONDITIONERS, WETTING AGENTS; FERTILISERS CHARACTERISED BY THEIR FORM
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- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
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- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
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- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/02—Oxygen as only ring hetero atoms
- C12P17/08—Oxygen as only ring hetero atoms containing a hetero ring of at least seven ring members, e.g. zearalenone, macrolide aglycons
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- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
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Abstract
The present invention relates to macrolides brefeldin A (BFA) compounds, these compounds from three July 1st strain endogenetic fungus secondary metabolite, by solid fermentation, sterling compound is obtained after separation, and carries out Structural Identification using nuclear magnetic resonance (NMR) and high resolution mass spectrum.Present invention discover that this series compound has the activity of antagonism Radix Notoginseng pathomycete, and has carried out field and returned plant experiment, the pesticide candidate compound with prevention and treatment Radix Notoginseng plant root rot pathogenic bacteria can be developed into.
Description
Technical field:
The invention belongs to technical field of pesticide, are related to macrolides compound and cause a disease in preparation prevention and treatment plant-pathogenic
Purposes in bacterium.
Background technique:
Three, seventh is that China's traditional Chinese medicine, has the pharmacological activity such as anti-inflammatory, hemostasis, anti-aging, antitumor, have huge
Medical value and the market space.But Radix Notoginseng belongs to perennial shade plant, disease occurs frequently in growth course, wherein Radix Notoginseng
Root rot is to influence the main factor of Radix Notoginseng yield.At present to the prevention and treatment of root rot still without mature effective method, forefathers
Some researchs were made to the generation and prevention and treatment of the disease.Pathogen is to cause Panax notoginseng root that one of the main reason for rotting occurs, very
Bacterium pathogen specifically includes that column spore bacterium, Fusarium oxysporum, Fusarium solani, Rhizoctonia solani Kuhn, Verticillium sp bacterium, Phoma sp
Bacterium, bacterial disease opportunistic pathogen is based on pseudomonad.Common fungicide and the residual recall rate of agriculture are shown in figure in the plantation of China Radix Notoginseng at present
1.Common fungicide is largely chemical synthesis insecticide, although these insecticide effects are obvious, it is easy to remain in
It in Panax notoginseng root and soil, not only causes damages to human health, the pollution that will also result in environment is used for a long time.So finding
A kind of degradation cycle is short, the natural metabolites of microorganism secretion, with the new pesticide of environment harmonious coexistence very it is necessary to.It is interior
Raw bacterium is a kind of microbial resources with Important Economic value, and type is abundant, widely distributed, substantially in each plant
All containing endophyte adaptable therewith.Containing multiple metabolic pathways in endophyte, metabolite is abundant, to phytoremediation,
Element circular, biodegrade and bioconversion play an important role, and Radix Notoginseng endogenetic fungus promotes Panax notoginseng Growth in balance ecological environment
It plays an important role in the process.Currently, existing 89 plants of endogenetic fungus are separated from the root of Radix Notoginseng, stem, leaf and seed,
63.4% bacterial strain has the activity of at least one plant Radix Notoginseng pathogenic bacteria of antagonism.Therefore, we have antagonism three from the fermentation liquid of bacterial strain
Seven pathogenic bacteria angles are set out, and the metabolin of isolated strains finds the compound of novel compromise between security and drug cost, as
Develop the candidate compound of Radix Notoginseng pesticide.
Summary of the invention:
It is an object of the invention to: in view of the above problems, provide a series of macrolides compounds (BFA system
Column compound) and its preparing the application in prevention and treatment plant-pathogenic pathogenic bacteria drug.The macrolides compound pair
Radix Notoginseng pathomycete has preventive effect high, and inhibiting effect is few with residual by force, and the advantages such as green non-pollution greatly reduce pathogenic bacteria
Radix becomes the very promising pesticide candidate compound on prevention and treatment notoginseng root rot.
In order to achieve the above-mentioned object of the invention, The technical solution adopted by the invention is as follows:
The macrolides compound structure:
Compound of the present invention derives from the solid fermentation object of one plant of Radix Notoginseng endogenetic fungus, and by the following method
It obtains:
Radix Notoginseng endogenetic fungus (is named as Z1-1031), and separation healthy Panax notoginseng root from 3 years extracts postgenome,
NCBI comparison result shows that this bacterium of Preliminary Identification is Penicillium sp..
The fresh colony cultivated 7-10 days is prepared into 107Cfu/ml spore suspension is inoculated in 121 DEG C, sterilizes 30 points
In the solid rice medium of clock, 28 DEG C of (100ml water) stationary culture 30-40 days.It is extracted 3-4 times with isometric ethyl acetate,
After obtaining total medicinal extract, methanol: water (8:2-9:1) continues to dissolve, with isometric hexamethylene extraction 3-4 all over so as to remove depolarization compared with
Small fatty acid compound.Then pass through silicagel column, reverse phase ODS column, LH-20 gel column, the equal separation means of half preparation solution
Sample is isolated and purified, obtains sterling BFA series compound as described above.
Specific separation method is as follows: using (25 × 10cm) glass column, 200-300 mesh silica gel is as stationary phase, CH2Cl2-
MeOH (100:1to 1:1) gradient elution obtains 4 flow points, is respectively designated as A-D.B flow point (the stream under 25:1-10:1 gradient
Point) use MeOH-H2O (1:9to 10:0) is mobile phase, and reversed ODS column continues to separate, and obtains B1-B15 flow point.Wherein B4-
B12 (flow point under 3:7-8:2 gradient) shows certain antibacterial activity, so carrying out next step separation to B4-B12, uses
LH-20 gel column separates B4, obtains B4-1 to B4-5 flow point, and wherein B4-2 further uses half preparation liquid phase point
From compound 1 is obtained, liquid-phase condition is (CH3CN–H2O, v/v 25:75-24:76,3.0mL/min), wavelength 210nm.Change
Object 2 and 3 is closed equally using half preparation liquid phase (CH3CN-H2O, v/v 22:78-21:79,3.0 mL/min) respectively from flow point B4-4
It is obtained in B4-5.The isolated compound 4 and 5 from B4-1 flow point, partly preparing liquid-phase condition is (CH3CN–H2O,v/v
20:80-19:81,3.0mL/min).Compound 6 is the crystal being precipitated in B7 flow point.B12 flow point further uses gel column LH-
Then 20 separation half prepare liquid phase (CH3CN-H2O, v/v 35:65-34:66,3.0mL/min) compound 7 is prepared.Its
In, the mobile phase acetonitrile CH in half preparation process3Methanol MeOH replacement can be used in CN, and the methylene chloride in preparation process can
To use chloroform to replace.
The solid rice medium are as follows: 100ml water, 75 grams of rice, 12 DEG C sterilize 30 minutes.
The present invention has apparent short of money by the macrolides compound that the solid fermentation object of Radix Notoginseng endogenetic fungus obtains
The function of anti-Radix Notoginseng pathogenic bacteria, can be used for preparing the pesticide of Radix Notoginseng.
Radix Notoginseng endogenetic fungus of the present invention is mould (Penicillium sp.), and the strain is in China Microbiological
The common micro-organisms center preservation of culture presevation administration committee, preservation address: in Yard 1, BeiChen xi Road, Chaoyang District, Beijing City 3
Institute of microbiology of the academy of sciences of state, preservation date: on 07 07th, 2017, deposit number: CGMCC No.14134.
Detailed description of the invention
Fig. 1 is common fungicide and the residual recall rate of agriculture (%) in Radix Notoginseng；
Fig. 2 is three plants of Radix Notoginseng pathogenic bacteria of BFA series compound antagonism.
Specific embodiment
Embodiment 1
Compound source: BFA series compound derives from the solid fermentation object of one plant of Radix Notoginseng endogenetic fungus.It is raw in Radix Notoginseng
Fungi (this plant of bacterium is named as Z1-1031), separation healthy Panax notoginseng root from 3 years, extracts postgenome, this bacterium of Preliminary Identification
For Penicillium sp..The fresh colony cultivated 7-10 days is prepared into 107Cfu/ml spore suspension, is inoculated in 121
DEG C, in 30 minutes solid rice mediums of sterilizing, 28 DEG C stationary culture 30-40 days.3-4 is extracted with isometric ethyl acetate
Time, after obtaining total medicinal extract, 90% methanol-water continues to dissolve, with isometric hexamethylene extraction 3-4 all over smaller to remove depolarization
Fatty acid compound.Then pass through silicagel column, reverse phase ODS column, LH-20 gel column, the equal separation means pair of half preparation solution
Sample is isolated and purified, and sterling BFA series compound is obtained.
(25 × 10cm) glass column is used, 200-300 mesh silica gel is as stationary phase, CH2Cl2-MeOH(100:1to 1:1)
Gradient elution obtains 4 flow points, is respectively designated as A-D.B flow point (flow point under 25:1-10:1 gradient) uses MeOH-H2O
(1:9to 10:0) is mobile phase, and reversed ODS column continues to separate, and obtains B1-B15 flow point.Wherein B4-B12 (3:7-8:2 gradient
Under flow point) show certain antibacterial activity, so to B4-B12 carry out next step separation, using LH-20 gel column to B4
It is separated, obtains B4-1 to B4-5 flow point, wherein B4-2 further uses the isolated compound 1 of half preparation liquid phase, liquid
Phase condition is (CH3CN–H2O, v/v 25:75-24:76,3.0mL/min), wavelength 210nm.Compound 2 and 3 equally uses
Half preparation liquid phase (CH3CN-H2O, v/v 22:78-21:79,3.0mL/min) it is obtained from flow point B4-4 and B4-5 respectively.From
Isolated compound 4 and 5 in B4-1 flow point, partly preparing liquid-phase condition is (CH3CN–H2O,v/v 20:80-19:81,3.0mL/
min).Compound 6 is the crystal being precipitated in B7 flow point.B12 flow point further uses gel column LH-20 separation, then half prepares
Liquid phase (CH3CN-H2O, v/v 35:65-34:64,3.0 mL/min) compound 7 is prepared.
Embodiment 2
The identification of compound: obtained sterling compound takes 5mg or so, is sent to sequencing center and carries out nuclear-magnetism and mass spectrum survey
Examination consults pertinent literature and the detailed parsing to data, determines compound accurate molecular weight and structure.BFA series compound is
Macrolide antibiotics, the present invention isolate 2 compound Brefeldin A (6) and 7- acetylation 7-O-acetyl-
Brefeldin A (7) and 5 BFA open loop analogs are respectively designated as BrefeldinE1-E5 (1-5), they belong to same
Series compound, spectral data are shown in Table 1-3.It is from Penicillium decumbens metabolite that BFA is reported for the first time.
Later, it was also separated from P.simplicissimum, P. cyaneum and Eupenicillium brefeldianum successively
It arrives.BFA has become the lead compound of anticancer drug, and endoplasmic reticulum can be interfered to lead to egg to the Protein transport of golgiosome
It is white to degrade in endoplasmic reticulum, but almost few people study in application agriculturally.
Table 11H(600MHz)and 13C(150MHz)NMR Spectroscopic Data of New Compounds
1-3in CD3OD
Table 21H(600MHz)and 13C(150MHz)NMR Spectroscopic Data of New Compounds
4-5in CD3OD
Table 31H(400MHz)and 13C(150MHz)NMR Spectroscopic Data of Compounds 6-7in
DMSO
Embodiment 3
BFA series compound activity: the detection of anti-Radix Notoginseng pathogenic activity is carried out to BFA series compound, using 96 holes
Plate-turbidimetry, by BFA series compound to Radix Notoginseng pathogenic bacteria (Fusarium solani, Alternaria panax,
Cylindrocarpon didynum) make antagonism test.Spore is washed down from inclined-plane and spore suspension is made by fungi, hemocytometer
Number plate counts, and is diluted to spore concentration 107cfu/ml.It draws the good spore suspension 0.4ml of above-mentioned dilution and 40ml liquid is added
In PDB culture medium, it is mixed into suspension.Experimental group :+2 μ L sample (compound 1-7) of 198 μ L suspension, 3 parallel；Blank
Medium controls :+2 μ L sample of 198 μ L blank cultures；DMSO control group :+2 μ LDMSO of 198 μ L suspension；Positive control
(G418) group :+2 μ L G418 of 198 μ L suspension.96 orifice plates are placed in 28 DEG C of incubators and are cultivated, are measured at 600nm after 48h
OD value.As a result as shown in Figure 2.Screening active ingredients the experimental results showed that, BFA (6) and 7- acetylation BFA (7) cause a disease to Radix Notoginseng root-rot
Bacterium has preferable antagonism, and concrete outcome is shown in Fig. 2.So selecting the master of BFA that wherein effect is best as field Hui Zhi
Want object.
Embodiment 4
The field BFA Hui Zhi becomes notoginseng root rot candidate pesticide.BFA is dissolved using water, is configured to the molten of 0.1mg/L
Liquid, every plant of Radix Notoginseng face pouring root 30-50mL.Each processing is inoculated with 50 plants of Radix Notoginseng seedlings, is planted on new native (0 year soil).Select water
For negative control, Radix Notoginseng seedling was recorded every 1 month deposits seedling rate, and Radix Notoginseng Agronomic parameter index observes altogether 6 months.By text
Mountain Radix Notoginseng research institute, academy of agricultural science Institute of Medical Plants of Yunnan Province assist to complete.The explanation of experimental result table 4, BFA
The death rate of Radix Notoginseng can be significantly reduced since 3rd month, raising deposits seedling rate, shows good application potential.
Embodiment 5
The content detection of main saponin(e Rg1/Re/Rb1/Rd/R1 in Radix Notoginseng.Using Agilent1260 analysis instrument；Two
Pole pipe array detector；Agilent analytical column (3.0 × 150mm)；Mobile phase: acetonitrile-water, gradient elution；Flow velocity 0.5ml/
min；Detection wavelength 203nm；30 DEG C of conditions of column temperature are tested and analyzed.Using external standard method, standard items linear relationship is measured
As shown in table 5.Using monomer saponin linear equation obtained in above-mentioned experiment (table 5), according to the absorption value meter of sample detection
Calculate content of each monomer saponin in Radix Notoginseng.The results show that generating Ginsenoside Rg1/Re/ in the Radix Notoginseng of experiment 6 months
Content of the Rb1/Rd/R1 in Radix Notoginseng dry matter be respectively as follows: CK class mean be 5.19%, 0.98%, 2.79%, 0.61%,
0.61%；Adding compound class mean is 8.01%, 1.00%, 2.83%, 0.43%, 0.85%.Significance analysis result is aobvious
Show in addition compound group Radix Notoginseng, tri- kinds of saponin(es of Rg1/Rb1/R1 dramatically increase.
4 1-6 month field Hui Zhi of table deposit seedling rate statistics
The linear equation of the main saponin content detection of 5 Radix Notoginseng of table 5.
Claims (10)
1. such as the macrolides compound of flowering structure:
2. the preparation method of macrolides compound as described in claim 1, which is characterized in that 7-10 days new will be cultivated
Fresh bacterium colony is prepared into spore suspension, is inoculated in solid rice medium, and stationary culture 30-40 days；With isometric acetic acid second
Ester extract 3-4 times, after obtaining total medicinal extract, methanol: water (8:2-9:1) continues to dissolve, with isometric hexamethylene extraction 3-4 all over so as to
Except the lesser fatty acid compound of depolarization, then pass through silicagel column, reverse phase ODS column, LH-20 gel column, half prepares liquid phase
Etc. separation means sample is isolated and purified, obtain sterling BFA series compound.
3. preparation method as claimed in claim 2, which is characterized in that separated with the following method, 200-300 mesh silica gel
As stationary phase, CH2Cl2- MeOH or CHCl3- MeOH 100:1-1:1 gradient elution obtains 4 flow points, is respectively designated as A-D；
B flow point uses MeOH-H2O 1:9-10:0 is mobile phase, and reversed ODS column continues to separate, and obtains B1-B15 flow point；Use LH-20
Gel column separates B4, obtains B4-1 to B4-5 flow point, and wherein it is isolated to further use half preparation liquid phase by B4-2
Compound 1, liquid-phase condition are the CH that volume ratio is 25:75-24:763CN–H2O or MeOH-H2O；Compound 2 and 3 equally uses
Half preparation liquid phase is obtained from flow point B4-4 and B4-5 respectively, and mobile phase volume is than the CH for 22:78-21:793CN-H2O or
MeOH-H2O；The isolated compound 4 and 5 from B4-1 flow point, it is 20:80-19:81 that half preparation liquid phase mobile phase, which is volume ratio,
CH3CN–H2O or MeOH-H2O, compound 6 are the crystal being precipitated in B7 flow point, and B12 flow point further uses gel column LH-20
Separation, then compound 7 is prepared in half preparation liquid phase, and mobile phase is the CH that volume ratio is 35:65-34:663CN-H2O or
MeOH-H2O。
4. preparation method as claimed in claim 2, which is characterized in that the rice medium are as follows: 100ml distilled water, 75
Gram rice, 121 DEG C sterilize 30 minutes.
5. a kind of composition, which is characterized in that include macrolides compound described in claim 1.
6. composition described in macrolides compound described in claim 1 or claim 5 prevents and treats phytopathy in preparation
Application in originality pathogenic bacteria and its diseases related drug.
7. application as claimed in claim 6, which is characterized in that the pathogenic bacteria are fungi.
8. application as claimed in claim 6, which is characterized in that it is described it is diseases related for maize ear rot, brown streak, brown spot,
Bacterial wilt, black rot, black spot or root rot.
9. the application as described in claim 6-8 any one, which is characterized in that with a effective amount of described in claim 1ization
The material for closing compositions-treated pathogenic bacteria described in object or claim 5 or preventing pathogenic bacteria from invading, the material are to plant
Object, soil or seed.
10. macrolides compound as described in claim 1, which is characterized in that the compound can be with Radix Notoginseng probiotics
Or organic fertilizer is used in combination.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115074255A (en) * | 2022-06-24 | 2022-09-20 | 自然资源部第三海洋研究所 | Fusarium and application of fermentation compound thereof in preventing and treating necrosis apoptosis-related diseases |
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| CN104877910A (en) * | 2014-02-27 | 2015-09-02 | 中国科学院沈阳应用生态研究所 | Plant endophytic fungus Eupenicillium brefeldianum F4a and its application |
| CN105924451A (en) * | 2016-04-27 | 2016-09-07 | 国家海洋局第三海洋研究所 | Macrolide compound with tea pathomycete prevention activity, and preparation method and use thereof |
| CN106831696A (en) * | 2017-02-20 | 2017-06-13 | 广西大学 | Derivative of macrolides and its preparation method and application |
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2017
- 2017-10-13 CN CN201710949864.1A patent/CN109111422A/en active Pending
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| CN104877910A (en) * | 2014-02-27 | 2015-09-02 | 中国科学院沈阳应用生态研究所 | Plant endophytic fungus Eupenicillium brefeldianum F4a and its application |
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Cited By (1)
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| CN115074255A (en) * | 2022-06-24 | 2022-09-20 | 自然资源部第三海洋研究所 | Fusarium and application of fermentation compound thereof in preventing and treating necrosis apoptosis-related diseases |
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Application publication date: 20190101 |