CN103641810B - Polyketone compound, preparation method and application thereof - Google Patents

Polyketone compound, preparation method and application thereof Download PDF

Info

Publication number
CN103641810B
CN103641810B CN201310729537.7A CN201310729537A CN103641810B CN 103641810 B CN103641810 B CN 103641810B CN 201310729537 A CN201310729537 A CN 201310729537A CN 103641810 B CN103641810 B CN 103641810B
Authority
CN
China
Prior art keywords
polyketides
fusarium
preparation
substratum
polyketone compound
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
CN201310729537.7A
Other languages
Chinese (zh)
Other versions
CN103641810A (en
Inventor
张应烙
李帅
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Zhejiang Normal University CJNU
Original Assignee
Zhejiang Normal University CJNU
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Zhejiang Normal University CJNU filed Critical Zhejiang Normal University CJNU
Priority to CN201310729537.7A priority Critical patent/CN103641810B/en
Publication of CN103641810A publication Critical patent/CN103641810A/en
Application granted granted Critical
Publication of CN103641810B publication Critical patent/CN103641810B/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D311/00Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/76Benzo[c]pyrans
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/14Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
    • A01N43/16Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12NMICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N1/00Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
    • C12N1/14Fungi; Culture media therefor
    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12PFERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P17/00Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
    • C12P17/02Oxygen as only ring hetero atoms
    • C12P17/06Oxygen as only ring hetero atoms containing a six-membered hetero ring, e.g. fluorescein

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Health & Medical Sciences (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Microbiology (AREA)
  • Biochemistry (AREA)
  • General Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Mycology (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Virology (AREA)
  • Botany (AREA)
  • Biomedical Technology (AREA)
  • Medicinal Chemistry (AREA)
  • Plant Pathology (AREA)
  • Dentistry (AREA)
  • Environmental Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

The invention discloses a polyketone compound. The chemical structure formula of the polyketone compound is shown in the specification. The invention also discloses a preparation method of the polyketone compound. The preparation method comprises the steps of performing fermentation culture on fusarium ZS07 (Fusarium proliferatum ZS07) with a preservation number of CCTCC NO:M2013257; filtering the obtained fermentation solution, extracting the filtered solution by using ethyl acetate, concentrating in vacuum and drying to obtain a crude extract; performing silica gel column chromatography fragmentation on the crude extract, and performing gradient elution by using dichloromethane/methyl alcohol; and concentrating an elution part F2 and then recrystallizing to obtain a polyketone compound. The polyketone compound can be used as an herbicide and in particular can be used for suppressing growth of amaranthus retroflexus radicles.

Description

Polyketides and its production and use
Technical field
The present invention relates to biological technical field, particularly relate to preparation and the weeding application of katydid's commensal gut bacteria strain and new active metabolite thereof.
Background technology
Amaranthus retroflexus (Amaranthus retroflexus L) is the typical pernicious invasive weed of China, and serious harm dry field farming thing, affects crop yield.Chemical herbicide was once the major measure of control Amaranthus retroflexus harm, but the life-time service of chemical herbicide causes environmental pollution, many negative impacts such as disruption of ecological balance.Crave for the background of safe and effective, free of contamination new herbicides the mankind under, research that is efficient, environmental protection microbial herbicide is more and more subject to the attention of expert and scholar in world wide.
Insect fungal component is that a class studies less particular surroundings microorganism.Relative to Lu Sheng soil derived microbial, it has the diversity originated widely and enrich, simultaneously fungal component with the long-term common evolutionary process of host in define unique physiological property and pathways metabolism, be the ideal source of new active metabolite.
A kind of existing compound, its structural formula is as shown in Equation 1; At document Ma S M, Zhan J, Xie X, et al.Redirectingthe cyclization steps of fungal polyketide synthase [J] .Journal of the American Chemical Society, 2008, corresponding informing is had in 130 (1): 38-39, but there are no weeding activity and other any purposes reports.
Bacterial strain F.Proliferatum (FJ 648201) is a kind of crop pathogenic bacterium in agriculture production, can cause maize kernel rot (Lu Weihong, Huang Siliang, department victory beautiful, etc.; Chinese Plants pathology meeting Annual Conference collection of thesis in 2010), F.Proliferatum can produce fumonisin, various toxicity (the Molecular biodiversity ofmycotoxigenic fungi that threaten food safety.Int.J.Food microbiol.2013 with species specificity can be caused to livestock and poultry and laboratory animal, 167,57-66).
Publication number is that the patent of 101928672A informs: fusarium prolifertum can induce dragon tree to produce dragon's blood.
Publication number is that the patent of 103271022A informs: swollen leg honeybee is carried fusarium prolifertum and can be used for preventing and treating poplar ten spot buprestid beetle larva;
The article that the Ji Zhiqin of Xibei Univ. of Agricultural & Forest Science & Technology delivers informs: the meta-bolites of celastrus angulatus endogenetic fungus fusarium prolifertum has obvious fungicidal activity to various agricultural pathogenic fungi.
Summary of the invention
The technical problem to be solved in the present invention is to provide a kind of polyketides and uses thereof.
In order to solve the problems of the technologies described above, the invention provides a kind of polyketides, its chemical structural formula is:
The present invention also provides a kind of fusarium prolifertum ZS07 (Fusarium proliferatum ZS07) simultaneously, and its preserving number is: CCTCC NO:M2013257.
The present invention also provides the preparation method of above-mentioned polyketides simultaneously, comprises the steps:
1) be, that the fusarium prolifertum ZS07 (Fusarium proliferatum ZS07) of CCTCC NO:M2013257 is inoculated on ME substratum by preserving number, on shaking table, cultivate 2 ~ 3 days 160 ~ 200rpm (being preferably 180rpm), 27.5 ~ 28.5 DEG C (being preferably 28 DEG C), obtain seed liquor;
2), seed liquor to be inoculated in ME substratum (generally speaking, the seed liquor of 10ml is inoculated in the ME substratum of 350 ~ 450ml), 160 ~ 200rpm (being preferably 180rpm), 27.5 ~ 28.5 DEG C (being preferably 28 DEG C) fermentation, 6.5 ~ 7.5 days (being preferably 7 days); Obtain fermented liquid;
3), by step 2) gained filtering fermentation liquor, filtrate ethyl acetate (for isopyknic ethyl acetate) extracts, and vacuum concentration drying (in the vacuum tightness of 0.1 negative pressure, 45 DEG C of dry 30-50 minute), obtains crude extract;
4), by step 3) gained crude extract carries out silica gel column chromatography segmentation, adopt methylene chloride/methanol to carry out gradient elution, the volume ratio of described methylene dichloride and methyl alcohol is followed successively by 100:0,100:1,100:2,100:4,100:8,100:16,100:32; Thus obtain 7 elution fraction F1 ~ F7 respectively;
5), by concentrated for elution fraction F2 (distillation and concentration) recrystallization afterwards, polyketides is obtained.
Improvement as the preparation method of polyketides of the present invention: ME substratum is: malt extract 20g, sucrose 20g, peptone 1g, distilled water is settled to 1L.
The present invention also provides the purposes of above-mentioned polyketides simultaneously: as weedicide.
Improvement as the purposes of polyketides of the present invention: the growth suppressing Amaranthus retroflexus young root.
The present invention adopts culture dish-filter paper enzyme to measure new compound to the restraining effect of Amaranthus retroflexus seed young root.
The present invention relates to preparation and the weeding application of the new active metabolite of a kind of katydid's commensal gut bacterium.Be separated from healthy katydid's enteron aisle and obtain symbiotic effects bacterial strain Fusarium proliferatum ZS07, this bacterial strain is preserved in China typical culture collection center (CCTCC), and its deposit number is CCTCC NO:M2013257.Described compound is novel compound, has no report before.Described purposes is embodied in this novel compound and invasive weed Amaranthus retroflexus young root can be suppressed to grow.Strain fermentation culture condition of the present invention is simple, and new compound extraction process is clear and definite, suppresses Amaranthus retroflexus young root growth result obvious.Can be used as agricultural herbicide.
Polyketides of the present invention is as usage during weedicide and consumption: be diluted to 0.05 ~ 0.1g/L and spray; The consumption (significant quantity) of per hectare is about 50 ~ 100g.
Accompanying drawing explanation
Below in conjunction with accompanying drawing, the specific embodiment of the present invention is described in further detail.
Fig. 1 is cultural characteristic and the spore shape characteristic pattern of katydid's commensal gut bacterium (F.Proliferatum ZS07) bacterial strain;
The cultural characteristic figure of Zuo Tuwei katydid's commensal gut bacterium (F.Proliferatum ZS07) bacterial strain;
Right figure is katydid's commensal gut bacterium (F.Proliferatum ZS07) bacterial strain spore shape characteristic pattern.
Fig. 2 is the weeding activity comparison diagram of polyketides and 2,4-D.
Embodiment
The experimental technique used in following embodiment is ordinary method if no special instructions.
Described reagent all can obtain from commercial channels.
Embodiment 1, bacterial strain screening:
In November, 2012 catches healthy katydid's sample from suburb, Jinhua, and sample is taken back laboratory as early as possible and processed.
Substratum is MEA substratum: malt extract 20g, sucrose 20g, agar 20g, peptone 1g, and distilled water is settled to 1L, pH 7.0.1.1 normal atmosphere, sterilizing 20min (for conventional sterilant) at 121 DEG C.
Method: aseptically use 75% (volume %) alcohol surface sterilization 2min after the hungry 24h of healthy Tettigonionidae, dissect after rinsed with sterile water 3 times, get enteron aisle to add a small amount of sterilized water and grind in mortar and obtain suspension, with sterilized water respectively gradient dilution 10 1, 10 2, 10 3doubly, get each gradient dilution liquid 0.2mL and coat on MEA culture medium flat plate, in 28 DEG C of thermostat containers, cultivate 2-3 days.After bacterium colony grows, a small amount of mycelia of picking is transferred in new MEA culture medium flat plate purifying and obtains single bacterium colony, by this bacterium colony---and fungal component ZS07 is inoculated into MEA slant tube and saves backup.
Embodiment 2, identification of strains
ITS rDNA analyzes:
According to BioTeke novel quick-speed plant genome DNA extracting reagent kit specification sheets, extract the fungal component ZS07 genomic dna of above-described embodiment 1 gained, adopt ITS universal primer ITS1 (5 '-TCCGTAGGTGAACCTGCGG-3 ' forward) and ITS4 (5 '-TCCTCCGCTTATTGATATGC-3 ', the rDNA ITS district's gene order that oppositely) increases purifying.
Sequencing result carries out similarity-rough set by blast program; Analytical results shows, symbiotic effects ZS07 and bacterial strain F.Proliferatum (FJ 648201) has higher similarity, and similarity is 99.5%.In conjunction with this bacterium morphological feature, identify that this bacterium is F.Proliferatum.
This bacterium is carried out preservation, depositary institution: China typical culture collection center; Preservation name is called: sickle-like bacteria ZS07 (Fusarium proliferatum ZS07), preservation address: Wuhan, China Wuhan University; Preservation date: 2013.06.13; Preserving number is: CCTCC NO:M2013257.
The preparation of embodiment 3, polyketide
By the mycelium block (0.5 × 0.5cm of fresh sickle-like bacteria ZS07 (Fusarium proliferatum ZS07) 2, about 0.5g) and be inoculated into every bottle containing in the 250mL Erlenmeyer flask of 150mL ME substratum, inoculate 5 ~ 6 bottles, cultivate 2 ~ 3 days under 180rpm, 28 DEG C of conditions as seed liquor.
Remarks illustrate: sickle-like bacteria ZS07 after Fructus Hordei Germinatus solid medium (MEA substratum) activation of routine, fresh sickle-like bacteria ZS07.
10mL seed liquor is inoculated in the 1000mL Erlenmeyer flask of the ME substratum that 400mL is housed, 180rpm, 28 DEG C of condition bottom fermentations 7 days.
The two-layer filtered through gauze of fermented liquid, filtrate uses equal-volume extraction into ethyl acetate, and extraction times is 3 times, and vacuum concentration drying (in the vacuum tightness of 0.1 negative pressure, 45 DEG C of dry 30-50 minute), obtains crude extract 40.5g.
Above-mentioned ME substratum is: malt extract 20g, sucrose 20g, peptone 1g, and distilled water is settled to 1L, natural PH, then 1.1 normal atmosphere, sterilizing 20min (for conventional sterilant) at 121 DEG C.
(described silicagel column selects 200 ~ 300 object silica gel to carry out silica gel column chromatography segmentation to this 40.5g crude extract, weight is 150g), adopt methylene chloride/methanol gradient elution, the volume ratio of methylene chloride/methanol is followed successively by 100:0,100:1,100:2,100:4,100:8,100:16,100:32, the consumption of often kind of elutriant is respectively about 1500ml, about 1200ml, about 1000ml, about 1000ml, about 800ml, about 800ml, about 800ml; Thus obtain 7 elution fraction F1-F7 respectively.In methyl alcohol, carry out recrystallization after the 2nd of gained kind of elution fraction F2 is carried out distillation and concentration (in 45 DEG C of dry 40-55 minute), the light yellow crystal of gained is polyketides.
The Structural Identification of embodiment 4, polyketide
The polyketides of embodiment 3 gained is light yellow crystal, and ESI-MS show that compound molecular weight is m/z 357 [M+H] +, molecular formula is C 19h 16o 7. 1h-NMR, 13c-NMR determines this compound structure in conjunction with 2D-NMR spectrum analysis.
Its chemical structural formula is:
Spectral data is: 1h NMR (Acetone-d 6) δ: 2.43 (3H, s, H-18), 4.25 (2H, s, H-10), 6.30 (1H, d, J=2.3Hz, H-8), 6.32 (1H, d, J=2.3Hz, H-16), 6.51 (1H, d, J=2.3Hz, H-14), 6.59 (1H, d, J=2.3Hz, H-4), 6.62 (1H, s, H-6), 11.14 (1H, s, 3-OH), 3.93 (3H, s, OCH 3). 13c NMR (Acetone-d 6) δ: 21.5 (C-18), 47.8 (C-10), 55.4 (5-OCH 3), 100.1 (C-2), 100.4 (C-14), 101.3 (C-4), 102.9 (C-6), 107.0 (C-8), 111.0 (C-16), 118.9 (C-12), 139.5 (C-7), 141.2 (C-17), 152.4 (C-9), 156.4 (C-13), 160.8 (C-15), 163.4 (C-3), 166.9 (C-5), 167.1 (C-1), 198.9 (C-11).
The polyketides of embodiment 5, embodiment 3 gained is to the restraining effect of Amaranthus retroflexus young root
Get proper amount of acetone and this compound dissolution is mixed with 10 μ g/mL, 1 μ g/mL diluent, add 5ml diluent in the culture dish being covered with filter paper, make filter paper and liquid fully saturated, after acetone volatilization, add 5ml sterilized water.Blank acetone does same process.Same concentration (that is, 10 μ g/mL, 1 μ g/mL) 2,4-D is as positive control.Choosing 150, the Amaranthus retroflexus seed (10, every ware) just showed money or valuables one carries unintentionally is placed on the filter paper of above-mentioned process, 27 DEG C, 80% relative humidity, timing illumination (12h illumination, 12h dark) condition artificial climate incubator cultivate 4d.Measure young root length, represent result with average root growth inhibition ratio, each process repeats 3 wares.
Average production inhibiting rate (%)=[contrast average root length-process average root is long]/contrast average root long × 100%.
As shown in Figure 2, result shows that this polyketides has restraining effect to Amaranthus retroflexus growth to experimental result.When concentration is 1 μ g/mL, new compound is 42.1% to the inhibiting rate that Amaranthus retroflexus young root grows, a little more than the positive control 2,4-D (40.1%) of comparable sodium.When concentration increases to 10 μ g/mL, new compound and positive drug all show stronger Amaranthus retroflexus young root growth inhibitory activity, and wherein this compound is 67.1% to Amaranthus retroflexus young root inhibiting rate, and under the same terms, positive drug 2,4-D inhibiting rate is 72.7%.
Above result prompting, this polyketides has inhibit activities to the growth of Amaranthus retroflexus young root, can as weedicide.
Comparative example 1, the compound described in the formula 1 of informing in background technology to be detected according to method described in embodiment 5, no matter be when concentration is 1 μ g/mL, or when concentration is 10 μ g/mL, the inhibiting rate of the compound described in formula 1 to Amaranthus retroflexus young root is 0%.That is, the compound described in formula 1 does not have inhibit activities to the growth of Amaranthus retroflexus young root, can not as weedicide.
Finally, it is also to be noted that what enumerate above is only several specific embodiments of the present invention.Obviously, the invention is not restricted to above embodiment, many distortion can also be had.All distortion that those of ordinary skill in the art can directly derive from content disclosed by the invention or associate, all should think protection scope of the present invention.
<110> Zhejiang Normal University
 
<120> polyketides and its production and use
 
<160> 2
 
<210> 1
<211> 19
<212> DNA
<213> artificial sequence
 
<220>
<223> primer I TS1
 
<400> 1
tccgtaggtg aacctgcgg 19
 
 
<210> 2
<211> 20
<212> DNA
<213> artificial sequence
 
<220>
<223> primer I TS4
 
<400> 2
tcctccgctt attgatatgc 20
 
 
 

Claims (6)

1. polyketides, is characterized in that chemical structural formula is:
2. fusarium prolifertum ZS07 (Fusarium proliferatum ZS07), its preserving number is: CCTCC NO:M2013257.
3. the preparation method of polyketides as claimed in claim 1, is characterized in that comprising the steps:
1) be, that the fusarium prolifertum ZS07 (Fusarium proliferatum ZS07) of CCTCC NO:M2013257 is inoculated on ME substratum by preserving number, on shaking table, 160 ~ 200rpm, 27.5 ~ 28.5 DEG C cultivate 2 ~ 3 days, obtain seed liquor;
2), by seed liquor be inoculated in ME substratum, 160 ~ 200rpm, 27.5 ~ 28.5 DEG C fermentation 6.5 ~ 7.5 days; Obtain fermented liquid;
3), by step 2) gained filtering fermentation liquor, filtrate is extracted with ethyl acetate, and vacuum concentration is dry, obtains crude extract;
4), by step 3) gained crude extract carries out silica gel column chromatography segmentation, adopt methylene chloride/methanol to carry out gradient elution, the volume ratio of described methylene dichloride and methyl alcohol is followed successively by 100:0,100:1,100:2,100:4,100:8,100:16,100:32; Thus obtain 7 elution fraction F1 ~ F7 respectively;
5), by concentrated for elution fraction F2 rear recrystallization, polyketides is obtained.
4. the preparation method of polyketides according to claim 3, is characterized in that: described ME substratum is: malt extract 20g, sucrose 20g, peptone 1g, distilled water is settled to 1L.
5. the purposes of polyketides as claimed in claim 1, is characterized in that: as weedicide.
6. the purposes of polyketides according to claim 5, is characterized in that: the growth suppressing Amaranthus retroflexus young root.
CN201310729537.7A 2013-12-25 2013-12-25 Polyketone compound, preparation method and application thereof Expired - Fee Related CN103641810B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201310729537.7A CN103641810B (en) 2013-12-25 2013-12-25 Polyketone compound, preparation method and application thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201310729537.7A CN103641810B (en) 2013-12-25 2013-12-25 Polyketone compound, preparation method and application thereof

Publications (2)

Publication Number Publication Date
CN103641810A CN103641810A (en) 2014-03-19
CN103641810B true CN103641810B (en) 2015-03-25

Family

ID=50247133

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201310729537.7A Expired - Fee Related CN103641810B (en) 2013-12-25 2013-12-25 Polyketone compound, preparation method and application thereof

Country Status (1)

Country Link
CN (1) CN103641810B (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110357788B (en) * 2019-06-17 2023-01-03 宁波大学 Polyketone compound and preparation method and application thereof
CN113278531B (en) * 2021-04-25 2023-07-04 中国热带农业科学院热带生物技术研究所 Inducer for inducing Hainan dragon tree to rapidly generate dragon's blood and preparation method and application thereof

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1785993A (en) * 2005-12-14 2006-06-14 南开大学 Preparation method of non natural isocumarin and its 3,4-dihydro derivative and use thereof
CN101880633A (en) * 2010-06-25 2010-11-10 河北省农林科学院植物保护研究所 Fusarium proliferatum, and bacterium agent and application thereof

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1785993A (en) * 2005-12-14 2006-06-14 南开大学 Preparation method of non natural isocumarin and its 3,4-dihydro derivative and use thereof
CN101880633A (en) * 2010-06-25 2010-11-10 河北省农林科学院植物保护研究所 Fusarium proliferatum, and bacterium agent and application thereof

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
3株镰刀菌的鉴定、对野生燕麦的致病力及其对5种作物的影响;朱海霞等;《中国生物防治》;20101115;第26卷(第S1期);第84-89页 *
Classification, Prediction, and Verification of the Regioselectivity of Fungal Polyketide Synthase Product Template Domains;Yanran Li et al.;《Journal of Biological Chemistry》;20100517;第285卷(第30期);第22764-22773页 *
Redirecting the Cyclizaiton Steps of Fungal Polyketide Synthase;Suzanne M. Ma et al.;《J. Am. Chem. Soc》;20071212;第130卷(第1期);第38-39页 *

Also Published As

Publication number Publication date
CN103641810A (en) 2014-03-19

Similar Documents

Publication Publication Date Title
CN100584938C (en) Plants endogenetic fungus and application thereof
CN106399129B (en) One plant of trichoderma harzianum strain and its application
Barimani et al. A new anthracnose disease of pyrethrum caused by C olletotrichum tanaceti sp. nov
CN102286383A (en) Talaromyces flavus and application of same in prevention of plant pathogens
CN102204570A (en) Application of alternaria alternate metabolic products in cucumber rhizoctonia solani prevention and control
CN102217656A (en) Application of alternaria alternata metabolite to controlling Botrytis cirerea
CN111793566B (en) China fir endophytic fungi and biological control application thereof
CN105441331B (en) One plant of myrothecium roidium and its application
CN101444231B (en) Schizophyllum commune protein extract, and preparation method and application thereof
CN104195064A (en) Paddy rice endophytic actinomycete realizing in-vitro efficient antagonism on rice blast pathogen
CN111808888B (en) Chinese fir endophytic fungi fermentation filtrate and extract thereof, and preparation method and application of Chinese fir endophytic fungi fermentation filtrate and extract
CN101942403A (en) Bacillus pumilus as well as culture method and application thereof
CN103641810B (en) Polyketone compound, preparation method and application thereof
CN101487022B (en) Preparation of fermentation liquor for inhibiting liver cancer cell growth
CN117106639A (en) Streptomyces nojirimensis strain and application of fermentation liquor thereof in preventing and controlling pepper anthracnose
CN104893986B (en) Dragonfly enterobacteriaceae Aspergillus terreus QT122 and its metabolite and application
CN105713841A (en) Fusarium oxysporum and application of fusarium oxysporum in germination pretreatment of fagopyrum tataricum seeds
CN109077068A (en) A kind of application of fungi rod method in prevention and control exotic invasive weed Yellow calla
Kim et al. Laboratory and field evaluations of entomopathogenic Lecanicillium attenuatum CNU-23 for control of green peach aphid (Myzus persicae)
CN105586297B (en) Bacillus amyloliquefaciens plant subspecies WK1 bacterial strain and its application
CN103642700B (en) One strain aureobasidium pullulans and application thereof
CN110679611A (en) Application of fusarium proliferatum in prevention and control of invasive plant xanthium sibiricum
CN106754396B (en) A kind of Chinese toon endogenetic fungus TS8 and its secondary metabolite, preparation method and application
CN109161484A (en) A kind of application of toVerticilliumdahliaActivitie Activitie S of Relative in prevention and control exotic invasive weed Italy Siberian cocklebur
CN101619292B (en) Endophyte with insecticidal active substances and application in biological control

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C14 Grant of patent or utility model
GR01 Patent grant
CF01 Termination of patent right due to non-payment of annual fee
CF01 Termination of patent right due to non-payment of annual fee

Granted publication date: 20150325

Termination date: 20161225