CN114009443B - Use of pleuromutilins for combating phytopathogenic bacteria - Google Patents
Use of pleuromutilins for combating phytopathogenic bacteria Download PDFInfo
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- CN114009443B CN114009443B CN202111389716.1A CN202111389716A CN114009443B CN 114009443 B CN114009443 B CN 114009443B CN 202111389716 A CN202111389716 A CN 202111389716A CN 114009443 B CN114009443 B CN 114009443B
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- pathogenic bacteria
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- 241000894006 Bacteria Species 0.000 title claims description 12
- 230000003032 phytopathogenic effect Effects 0.000 title description 4
- 230000001580 bacterial effect Effects 0.000 claims abstract description 15
- ZRZNJUXESFHSIO-UHFFFAOYSA-N Pleuromutilin Natural products CC1C(O)C(C)(C=C)CC(OC(=O)CO)C2(C)C(C)CCC31C2C(=O)CC3 ZRZNJUXESFHSIO-UHFFFAOYSA-N 0.000 claims abstract description 14
- -1 pleuromutilin compound Chemical class 0.000 claims abstract description 9
- 241000207199 Citrus Species 0.000 claims abstract description 8
- 235000020971 citrus fruits Nutrition 0.000 claims abstract description 8
- 244000061456 Solanum tuberosum Species 0.000 claims abstract description 6
- 235000002595 Solanum tuberosum Nutrition 0.000 claims abstract description 6
- 241000233647 Phytophthora nicotianae var. parasitica Species 0.000 claims abstract description 5
- ZRZNJUXESFHSIO-VYTKZBNOSA-N pleuromutilin Chemical compound C([C@H]([C@]1(C)[C@@H](C[C@@](C)(C=C)[C@@H](O)[C@@H]2C)OC(=O)CO)C)C[C@]32[C@H]1C(=O)CC3 ZRZNJUXESFHSIO-VYTKZBNOSA-N 0.000 claims description 9
- MFBPRQKHDIVLOJ-AFFLPQGKSA-N 133868-46-9 Chemical compound Cl.CC(C)[C@@H](N)C(=O)NCC(C)(C)SCC(=O)O[C@@H]1C[C@@](C)(C=C)[C@@H](O)[C@H](C)[C@@]23CC[C@@H](C)[C@]1(C)[C@@H]2C(=O)CC3 MFBPRQKHDIVLOJ-AFFLPQGKSA-N 0.000 claims description 8
- 235000007164 Oryza sativa Nutrition 0.000 claims description 8
- 235000009566 rice Nutrition 0.000 claims description 8
- 240000007594 Oryza sativa Species 0.000 claims 1
- 244000052616 bacterial pathogen Species 0.000 abstract description 17
- 150000001875 compounds Chemical class 0.000 abstract description 7
- 201000010099 disease Diseases 0.000 abstract description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 6
- 238000012827 research and development Methods 0.000 abstract description 6
- 241000196324 Embryophyta Species 0.000 abstract description 4
- 241000531155 Pectobacterium Species 0.000 abstract description 2
- 241000589634 Xanthomonas Species 0.000 abstract description 2
- 241000589655 Xanthomonas citri Species 0.000 abstract description 2
- 239000003814 drug Substances 0.000 description 12
- 230000000844 anti-bacterial effect Effects 0.000 description 9
- 229940079593 drug Drugs 0.000 description 9
- 230000005764 inhibitory process Effects 0.000 description 8
- 241000209094 Oryza Species 0.000 description 7
- 244000000005 bacterial plant pathogen Species 0.000 description 7
- 239000002609 medium Substances 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000001963 growth medium Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 208000035143 Bacterial infection Diseases 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 241000589652 Xanthomonas oryzae Species 0.000 description 3
- 239000003899 bactericide agent Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000009630 liquid culture Methods 0.000 description 3
- 239000001888 Peptone Substances 0.000 description 2
- 108010080698 Peptones Proteins 0.000 description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 230000003698 anagen phase Effects 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- 235000015278 beef Nutrition 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000001717 pathogenic effect Effects 0.000 description 2
- 235000019319 peptone Nutrition 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- 238000004659 sterilization and disinfection Methods 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 1
- 208000031295 Animal disease Diseases 0.000 description 1
- 241000192125 Firmicutes Species 0.000 description 1
- 241000204031 Mycoplasma Species 0.000 description 1
- 235000007685 Pleurotus columbinus Nutrition 0.000 description 1
- 240000001462 Pleurotus ostreatus Species 0.000 description 1
- 235000001603 Pleurotus ostreatus Nutrition 0.000 description 1
- 241000520892 Xanthomonas axonopodis Species 0.000 description 1
- 241001148118 Xanthomonas sp. Species 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 238000011482 antibacterial activity assay Methods 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000003113 dilution method Methods 0.000 description 1
- 229930004069 diterpene Natural products 0.000 description 1
- 150000004141 diterpene derivatives Chemical class 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 239000000447 pesticide residue Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 238000001243 protein synthesis Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- 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
- A01N45/00—Biocides, pest repellants or attractants, or plant growth regulators, containing compounds having three or more carbocyclic rings condensed among themselves, at least one ring not being a six-membered ring
- A01N45/02—Biocides, pest repellants or attractants, or plant growth regulators, containing compounds having three or more carbocyclic rings condensed among themselves, at least one ring not being a six-membered ring having three carbocyclic rings
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- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention belongs to the field of pharmaceutical chemistry, and discloses a pleuromutilin compound for preventing and treating bacterial blight pathogenic bacteria Xanthomonas oryzaeUse of zae ACCC 11602, citrus canker pathogen Xanthomonas axonopodis pv.citri and potato black shank pathogen Pectobacterium atrosepticaACCC 19901 in plant diseases. The compounds on the market such as pleuromutilins and the like have the characteristics of broad spectrum, high efficiency and the like as anti-plant pathogenic bacteria agents, and have further research and development values.
Description
Technical Field
The invention belongs to the field of natural pharmaceutical chemistry, and discloses application of pleuromutilin compounds in preventing and treating agricultural bacterial diseases caused by rice bacterial leaf blight pathogenic bacteria Xanthomonas oryzae ACCC 11602, citrus canker pathogenic bacteria Xanthomonas axonopodis pv.
Background
Bacterial diseases are the most difficult diseases to control for crops, and cause huge losses for agriculture worldwide every year. There are about 500 bacterial crop diseases worldwide, while there are about 70 main bacterial crop diseases in our country. Among them, xanthomonas (Xanthomonas sp.) bacteria, such as bacterial leaf blight pathogenic bacteria of rice and citrus canker pathogenic bacteria, are two plant pathogenic bacteria which are strong in vitality, highly pathogenic and cause significant economic losses. It is estimated that worldwide potato yield is reduced by 25% due to bacterial disease. However, the existing chemical pesticides for preventing and treating plant bacterial diseases have been worldwide difficult due to the problems of 3R such as resistance (resistance), re-growth (resistance) and pesticide residue exceeding (residual) of plant diseases caused by long-term use and abuse. Therefore, there is an urgent need to explore and develop novel efficient bactericides as alternative bactericides to cope with the problems currently faced in the pesticide field.
Because the medicines on the market are subjected to systematic pharmacodynamic, biological and toxicity researches, compared with the research and development of brand new medicines, the research and development of the new medicines for the old has the advantages of relatively high success rate, short research and development period, low development cost and the like. Pleuromutilins are a broad-spectrum diterpene antibiotics produced by Pleurotus ostreatus, and the effect of inhibiting bacterial growth is achieved by inhibiting the protein synthesis of bacteria. Current pleuromutilin antibiotics are mainly used for the treatment of human or animal diseases caused by most gram-positive bacteria, mycoplasma and some gram-negative bacteria. In the process of screening a large amount of antibacterial compounds, the pleuromutilin compounds are found to have excellent inhibition effect on rice bacterial leaf blight pathogenic bacteria Xanthomonas oryzae ACCC 11602 and citrus canker pathogenic bacteria Xanthopodispv. However, no report has been made on the activity against plant pathogenic bacteria, and thus, it can be further developed as a lead into a novel agent against plant pathogenic bacteria.
Disclosure of Invention
The invention aims to provide a pleuromutilin bactericide which is used for preventing and controlling plant diseases caused by rice bacterial leaf blight pathogenic bacteria, citrus canker pathogenic bacteria and potato black shank pathogenic bacteria.
In order to achieve the above purpose, the present invention provides the following technical methods:
inhibition of rice bacterial blight pathogen Xanthomonas oryzae ACCC 11602, citrus canker pathogen Xanthomonas axonopodis pv.Citri and potato black shank pathogen Pectobacterium atrosepticaACCC 19901 by pleuromutilin, valnemulin hydrochloride compounds 100, 50, 25, … … μg/mL were determined by two-fold dilution, wherein the Minimum Inhibitory Concentration (MIC) was defined as the minimum concentration at which the inhibition was greater than 90%.
The pleuromutilin compound provided by the invention has the following advantages as a novel anti-plant pathogenic bacteria agent:
1) Broad bactericidal spectrum. The pleuromutilin compound has an inhibiting effect on bacteria of different species such as bacterial leaf blight pathogenic bacteria, citrus canker pathogenic bacteria, potato black shank pathogenic bacteria and the like.
2) The bactericidal activity is high. The MIC value of valnemulin hydrochloride on rice bacterial leaf blight pathogenic bacteria is as low as 0.78 mug/mL, and the valnemulin hydrochloride can be used as a new plant pathogenic bacteria killing guide for carrying out biological rationality design and development.
3) The new action of the commercialized medicament against plant pathogenic bacteria belongs to an old medicament new use strategy, and the research and development cost and period of the medicament are greatly reduced.
Detailed Description
The foregoing invention is further described in the following detailed description of the invention in order that the same may be better understood. But this should not be construed as limiting the invention. The experimental methods described in the following examples are conventional, unless otherwise specified.
Example 1: the compounds pleuromutilin, valnemulin hydrochloride are commercially available as pleuromutilin CAS:125-65-5, purity >98%; valnemulin hydrochloride CAS:133868-46-9 with purity >98%. The structural formula is as follows:
example 2: antibacterial activity assay for pleuromutilins
The strain used in this experiment was a laboratory-80℃strain frozen with 30% glycerol. The frozen strain was taken out, streaked on NB solid medium (beef extract: 3g, peptone: 5g, yeast powder: 1g, sucrose: 10g, agar: 15g, distilled water: 1L, pH7.0; sterilization at 121℃for 20 min), and cultured at constant temperature of 28℃until single colony developed. Respectively picking single colony on the solid culture medium to NB liquid culture medium (beef extract: 3g, peptone: 5g, yeast powder: 1g, sucrose: 10g, distilled water: 1L, 12)Sterilization at 1 ℃ for 20 min), shaking culture at 28 ℃ and 180rpm on a constant temperature shaking table to logarithmic growth phase. Diluting the strain in logarithmic growth phase with NB liquid medium to about 10 6 CFU/mL was ready for use. The compounds are respectively dissolved by DMSO, added into a liquid culture medium, and evenly mixed to prepare a liquid culture medium containing liquid with the concentration of 200 mug/mL. Taking 50 mu L of the drug-containing culture medium and the same volume of the drug-containing culture medium containing about 10 6 CFU/mL bacterial cultures were added to wells of 96-well plates at a final dosing concentration of 100. Mu.g/mL. A control was made of 100. Mu.L of the same concentration of bacterial liquid containing an equivalent amount of DMSO. Culturing 96-well plate in 28 deg.C incubator for 24-48 hr until bacteria liquid of control group grows out, and measuring OD value (OD) 600 ). And the OD values of 100. Mu.L of the liquid medium and the reagent at a concentration of 100. Mu.g/mL were additionally measured, and the OD values caused by the medium and the reagent themselves were corrected. The calculation formula for the corrected OD value and the inhibition rate is as follows:
corrected OD = sterile medium OD-sterile culture OD;
inhibition ratio = (corrected control culture broth OD value-corrected drug-containing culture broth OD value)/corrected control culture broth OD value x 100%
The drug-containing liquid medium of the compound was diluted in a 96-well plate by a double dilution method to obtain 50. Mu.L of the drug-containing medium of a serial concentration, and then the inhibition ratio corresponding to the serial concentration was measured according to the same test method as described above. All experiments were set up in triplicate, the inhibition of the compounds determined is shown in table 1 and the mic values are shown in table 2.
TABLE 1 antibacterial Activity of pleuromutilins on phytopathogenic bacteria
Note that: "/" indicates that the antibacterial activity of the compound was not measured
TABLE 2 MIC values of pleuromutilins for phytopathogenic bacteria
As shown in the biological test results of tables 1 and 2, the activity of the pleuromutilin compound related to the invention on plant pathogenic bacteria is obviously stronger than that of the commercial drug of thiabendazole, and the pleuromutilin compound has excellent antibacterial activity. Wherein the MIC value of valnemulin hydrochloride on pathogenic bacteria of bacterial leaf blight of rice is as low as 0.78 mug/mL.
In conclusion, the pleuromutilin compound disclosed by the invention has excellent inhibition effect on plant pathogenic bacteria, has the characteristics of broad spectrum, high activity and the like, and has further research and development values.
Claims (1)
1. The application of the pleuromutilin compound in preventing and controlling potato black shank bacteria, rice bacterial leaf blight bacteria and citrus canker bacteria, wherein the pleuromutilin compound is pleuromutilin and valnemulin hydrochloride, and has the following molecular structure characteristics:
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111389716.1A CN114009443B (en) | 2021-11-22 | 2021-11-22 | Use of pleuromutilins for combating phytopathogenic bacteria |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111389716.1A CN114009443B (en) | 2021-11-22 | 2021-11-22 | Use of pleuromutilins for combating phytopathogenic bacteria |
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| CN114009443A CN114009443A (en) | 2022-02-08 |
| CN114009443B true CN114009443B (en) | 2023-05-05 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117281117B (en) * | 2023-09-19 | 2024-08-30 | 贵州大学 | Pleuromutilin suspending agent and preparation method thereof |
| CN117223712B (en) * | 2023-09-19 | 2024-08-02 | 贵州大学 | Pleuromutilin wettable powder and preparation method thereof |
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Effective date of registration: 20231025 Address after: 530000 Quality Control Center Building, No.1 Chuangxin Road West Section, Xixiangtang District, Nanning City, Guangxi Zhuang Autonomous Region Patentee after: Guangxi Tianyuan Biochemical Co.,Ltd. Address before: 730000 Lanzhou University, 222 Tianshui South Road, Chengguan District, Lanzhou City, Gansu Province Patentee before: LANZHOU University |