CN104770372A - Application of tenuazonic acid in preparation of microbial source fungicide - Google Patents
Application of tenuazonic acid in preparation of microbial source fungicide Download PDFInfo
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- CN104770372A CN104770372A CN201510099629.0A CN201510099629A CN104770372A CN 104770372 A CN104770372 A CN 104770372A CN 201510099629 A CN201510099629 A CN 201510099629A CN 104770372 A CN104770372 A CN 104770372A
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- tenuazonic acid
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Abstract
The invention discloses application of tenuazonic acid in preparation of microbial source fungicide. The tenuazonic acid has a structural formula as described in the specification and a molecular formula of C10H15NO3 with a molecular weight of 197. The tenuazonic acid has inhibition activity to phytopathogens. According to identification results and biological activity experiment results, the tenuazonic acid has substantial bacteriostatic activity to Valsa mali, Phomopsis vexan and Venturia nashicola. When the tenuazonic acid with a concentration of 100 [mu]g/mL is applied, the inhibition rates of Valsa mali, Phomopsis vexan and Venturia nashicola are 95.9%, 77.6% and 100.0%, respectively; thus, it is proved that the tenuazonic acid has potential in development of the microbial source fungicide.
Description
Technical field
The invention belongs to microbial pesticide field, be specifically related to the Substance that is separated in meadow sweet endogenetic fungus fermentating metabolism thing and application prospect thereof.
Background technology
The active substance exploitation biogenic pesticide obtained with the metabolite of microorganism or be separated from microorganism is one of the study hotspot and direction of New pesticides discovery.The Avermectin such as with insecticidal activity, the jinggangmeisu with bactericidal activity and there is the bialaphos (Bialaphos, streptomycete produce) etc. of activity of weeding.
Tenuazonic acid (Tenuazonic acid) be at first nineteen fifty-seven Rosett etc. from
alternaria tenuisbe separated in culturing filtrate and obtain, structure is determined in nineteen fifty-nine by Stickings.Thereafter, exist
a. longipes, A. linicola, A. brassicicola, A. RaphaniAspergillus, sp., Pyricularia oryzae,
phoma sorghinain have people to be separated to obtain this material.
About tenuazonic acid, be a kind of toxin that alternaric bacteria (Alternania) is secreted, there is certain antitumor, antiviral and activity of weeding, also cause the extensive concern of people as a kind of guide of weed killer herbicide.The people such as Qiang Sheng report it to the pathogenic broad spectrum activity of weeds and the safety to some crop, show the potentiality that it is developed as Mirobial source herbicide; The people such as Qin Jianchun report its prawn ovum
brine shrimplethal raw survey, shows higher cytotoxic activity.But current nobody reports its inhibitory action to phytopathogen.
Summary of the invention
The object of the present invention is to provide in a kind of meadow sweet endogenetic fungus fermentation product to be separated and identify Substance---tenuazonic acid, this material has the activity of Suppressing phytopathogens, is preparing the application in microbial source fungicide.
Be separated in meadow sweet endogenetic fungus fermentation product of the present invention and identify Substance---tenuazonic acid, its structural formula is:
Molecular formula is C
10h
15nO
3, molecular weight is 197.
The qualification carried out through applicant and biological activity test prove, tenuazonic acid has the activity of Suppressing phytopathogens.Under 100 μ g/mL concentration, 95.9%, 77.6%, 100.0% is respectively to the inhibiting rate of Phomopsis vexanus, pear cucumerinum and Valsa mali, shows the potentiality that it is developed as microbial source fungicide.
Accompanying drawing explanation
Fig. 1 is the Mycelial growth lab diagram of tenuazonic acid to Phomopsis vexanus under 100 μ g/mL concentration.
Fig. 2 is the Mycelial growth lab diagram of tenuazonic acid to pear cucumerinum under 100 μ g/mL concentration.
Fig. 3 is the Mycelial growth lab diagram of tenuazonic acid to Valsa mali under 100 μ g/mL concentration.
Fig. 4 is tenuazonic acid nuclear magnetic resonnance
1h NMR spectrogram.
Fig. 5 is tenuazonic acid nuclear magnetic resonnance
13c NMR spectrogram.
Fig. 6 is tenuazonic acid nuclear magnetic resonnance H-H COSY spectrogram.
Fig. 7 is tenuazonic acid nuclear magnetic resonnance hsqc spectrum figure.
Fig. 8 is tenuazonic acid high resolution mass spectrum figure.
The antibacterial tests of tenuazonic acid of the present invention is as follows:
1. plant pathogenic fungi
Valsa mali, Phomopsis vexanus, pear cucumerinum;
2. the cultivation of pathogenic microorganism
With the slant culture of a small amount of pathogen of transfer needle picking, access the activation of potato dextrose agar solid culture medium flat board respectively, cultivate 5 days in (28 ± 1) DEG C insulating box;
3. suppress mycelial growth rate method to measure antibacterial activity
In the aseptic triangular flask of 100 mL, the aseptic mixed culture medium (ultimate density be 100 μ g/mLs) of preparation containing Substance, getting 10mL, to be placed in diameter be make flat board in 9 cm sterile petri dish, put into for examination pathogen bacterium cake (diameter is 6 mm) in each medium plane after cooling, the mycelia face of bacterium cake is attached to media surface, flat board is placed in 28 ± 1 DEG C and cultivates 48-96 h.Right-angled intersection method is adopted to measure colony growth diameter, with following formulae discovery inhibiting rate:
。
Table 1 is the Mycelial growth experimental data of Substance to Phomopsis vexanus, pear cucumerinum and Valsa mali under 100 μ g/mL concentration;
as seen from Figure 1, tenuazonic acid is to the inhibitory action of Phomopsis vexanus; As seen from Figure 2, tenuazonic acid is to the inhibitory action of pear cucumerinum; As seen from Figure 3, tenuazonic acid is to the inhibitory action of Valsa mali.
Embodiment
1, Substance extraction and isolation:
1) meadow sweet endogenetic fungus XXB07 is at 28 DEG C, fermented and cultured 5 days in 160r/min shaking table, and zymotic fluid obtains ferment filtrate by suction filtration;
2) by ferment filtrate extracting n-butyl alcohol 3 times, merge n-butanol phase, 60 DEG C of reduced pressure concentrations obtain n-butyl alcohol extract;
3) n-butyl alcohol extract is by 2 silica gel column layers, and thin layer chromatography and HPLC instruct the cut collected and have bacteriostatic activity;
4) above-mentioned bacteriostatic activity cut merges, and high pressure prepares liquid-phase collection Substance.
2, Substance antibacterial experiment:
1) plant pathogenic microorganisms is cultivated
Access the activation of potato dextrose agar solid culture medium flat board respectively with the slant culture of a small amount of Valsa mali of transfer needle picking, Phomopsis vexanus, pear cucumerinum, cultivate 5 days in (28 ± 1) DEG C insulating box;
2) mycelial growth rate method is suppressed to measure antibacterial activity
The aseptic mixed culture medium (ultimate density be 100 μ g/mLs) of preparation containing Substance in the aseptic triangular flask of 100 mL, getting 10mL, to be placed in diameter be make flat board in 9 cm sterile petri dish, put into for examination pathogen bacterium cake (diameter is 6 mm) in each medium plane after cooling, the mycelia face of bacterium cake is attached to media surface, flat board is placed in 28 ± 1 DEG C and cultivates 48-96 h.Right-angled intersection method is adopted to measure colony growth diameter, with following formulae discovery inhibiting rate:
。
3. compound identification:
Carrying out mass spectrum, proton nmr spectra and carbon spectrum and two dimensional NMR analysis to being separated the Substance obtained, seeing Fig. 4-8.Consult bibliography, comprehensively analyze the data obtained and SPECTROSCOPIC CHARACTERIZATION, eventually pass multiple database and carry out looking into newly, this compound is tenuazonic acid (Tenuazonic acid), and its structure is:
The molecular formula drawn by nuclear magnetic resoance spectrum and high resolution mass spectrum is C
10h
15nO
3, molecular weight is 197.Proved by antibacterial experiment: tenuazonic acid has the activity of Suppressing phytopathogens.
Claims (2)
1. tenuazonic acid is preparing the application in microbial source fungicide, and the structural formula of described tenuazonic acid is:
Its molecular formula is C
10h
15nO
3, molecular weight is 197;
It is characterized in that: tenuazonic acid has the activity of Suppressing phytopathogens.
2. tenuazonic acid according to claim 1 is preparing the application in microbial source fungicide, it is characterized in that, described phytopathogen is Valsa mali or Phomopsis vexanus or pear cucumerinum.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510099629.0A CN104770372A (en) | 2015-03-07 | 2015-03-07 | Application of tenuazonic acid in preparation of microbial source fungicide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510099629.0A CN104770372A (en) | 2015-03-07 | 2015-03-07 | Application of tenuazonic acid in preparation of microbial source fungicide |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105524848A (en) * | 2016-02-02 | 2016-04-27 | 福建农林大学 | Fungus strain for producing substance having antiviral activity and application of fungus strain |
| CN112961782A (en) * | 2021-01-29 | 2021-06-15 | 湖南省烟草公司长沙市公司 | Pediococcus kaoliang, microbial inoculum and herbicide containing same and application thereof |
Citations (2)
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| JPS4848633A (en) * | 1971-10-21 | 1973-07-10 | ||
| JPH0848633A (en) * | 1994-08-08 | 1996-02-20 | Nikken Food Kk | Method for producing natural or synthetic spin-trapping agent |
-
2015
- 2015-03-07 CN CN201510099629.0A patent/CN104770372A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4848633A (en) * | 1971-10-21 | 1973-07-10 | ||
| JPH0848633A (en) * | 1994-08-08 | 1996-02-20 | Nikken Food Kk | Method for producing natural or synthetic spin-trapping agent |
Non-Patent Citations (5)
| Title |
|---|
| GUI-HUA LU ET AL: "Synthesis and bioactivity of novel strobilurin derivatives containing the pyrrolidine-2,4-dione moiety", 《CHINESE CHEMICAL LETTERS》 * |
| XIAN-FENG WANG ET AL: "Synthesis, characterization and biological activity of novel (5-RS,6-S)-5-sec-butyl-3-(1-substituted-amino)ethylidene-1H-pyrrolidine-2,4-diones", 《ARKIVOC》 * |
| ZHAO-YONG ZHU ET AL: "Synthesis, Characterization and Biological Activities of Novel (E)-3-(1-(Alkyloxyamino)ethylidene)-1-alkylpyrrolidine-2,4-dione Derivatives", 《BULL. KOREAN CHEM. SOC.》 * |
| ZHAO-YONG ZHU ET AL: "Synthesis, Characterization, and Biological Activities of Novel (Z)-3-((E)-1-(Alkyloxyimino)ethyl)-5-arylidene-4-hydroxypyrroline-2-one Derivatives", 《JOURNAL OF HETEROCYCLIC CHEMISTRY》 * |
| 司腾飞: "1-[1-(吡咯啉-2-酮-3-基)亚乙基]-4-烃基氨基脲类化合物的合成和生物活性研究", 《中国优秀硕士学位论文全文数据库》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105524848A (en) * | 2016-02-02 | 2016-04-27 | 福建农林大学 | Fungus strain for producing substance having antiviral activity and application of fungus strain |
| CN105524848B (en) * | 2016-02-02 | 2019-06-07 | 福建农林大学 | One plant of fungal bacterial strain for producing antiviral active substance and its application |
| CN112961782A (en) * | 2021-01-29 | 2021-06-15 | 湖南省烟草公司长沙市公司 | Pediococcus kaoliang, microbial inoculum and herbicide containing same and application thereof |
| CN112961782B (en) * | 2021-01-29 | 2023-11-10 | 湖南省烟草公司长沙市公司 | Epicoccocus sorghum, microbial inoculum and herbicide containing same and application thereof |
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