KR100743672B1 - Piericidin a1 with competitive inhibitory activity of acyl homoserine lactone - Google Patents

Abstract

A substance, piericidin A1, having competitive inhibitory activity of acyl homoserine lactone is provided to block the quorum sensing of plant pathogenic bacteria or fungi by inhibiting activity of acyl homoserine lactone as a signal material of quorum sensing. A composition for inhibiting plant disease comprises the substance, piericidin A1, having competitive inhibitory activity of acyl homoserine lactone, represented by the formula(1) or its pharmaceutically acceptable salt as an effective ingredient, wherein the plant disease is caused by infection of Erwinia carotovora or Agrobacterium tumefaciens; and the piericidin A1 is produced by Kitasatospora sp. AR030054(KCTC10904BP).

Description

Piericidine A1 with competitive inhibitory activity of acyl homoserine lactone

FIG. 1 is a photograph of a plate that produced low support that inhibits violet pigment production when well-diffusion assay with the supernatant of AR030054 strain culture.

FIG. 2 is a magnification of 400 times with AR030054 strain photograph and optical microscope on Bennett's medium.

3 is a genus Kitasatospora sp.) The results of sequence similarity analysis are shown in a Phylogenetic tree.

4 is an HPLC chromatogram of isolated active material.

5 is a ¹³ C-NMR spectrum measured at 300 MHz by dissolving the isolated active material in methanol.

6 is a ¹ H-NMR spectrum measured at 300 MHz by dissolving the isolated active material in methanol.

7 is a ¹ H- ¹ H COSY spectrum measured at 400 MHz by dissolving the isolated active material in methanol.

8 is an HMBC spectrum measured at 500 MHz by dissolving the isolated active material in methanol.

9 is an HMQC spectrum measured at 500 MHz by dissolving the isolated active material in methanol.

10 is a JEOL JMS-SX 102A spectrum measured at 70 eV with ESI-MS.

11 is in accordance with the concentration of the isolated active material (1 μ M, 5 μ M , 10 μ M, 50 μ M, 100 μ M, 500 μ M, 750 μ M, 1000 μ M) acyl homoserine lactone competitive inhibition Photo of active experimental results.

Figure 12 is a photograph confirming whether soft rot inhibition hagoseo injected into the potato surface and then added to the culture medium of Winiah control such that each 0 μ M, 5 μ M, 50 μ M, 500 μ M of the active substance of the formula (1) Caro sat see.

Figure 13 is a photograph confirming whether soft rot inhibition hagoseo injected into the cabbage surface was added to the culture medium of Winiah control such that each 0 μ M, 5 μ M, 10 μ M, 100 μ M of the active substance of the formula (1) Caro sat see.

The present invention has a competitive inhibitory activity of acyl homoserine lactone, which is a bacterial quantitative sensing signaling material, which has been isolated from Kitasatospora sp . AR030054 ( Kitasatospora sp . AR030054) [KCTC10904BP] . It relates to sidin a ₁ (piericidin a _1), can be used for the treatment or prevention of an infectious plant diseases caused by various bacterial organisms.

Signaling between cells is generally a response to the environment, and bacteria take a unique approach. Bacteria communicate with each other by synthesizing specific substances in response to changes in the environment, releasing and absorbing them out of cells, and this signal transmission is called "Quorum Sensing", which mediates signal transduction. A substance called autoinducer is mainly acyl homoserine lactones (AHLs) compound. Acyl homoserine lactones include oxo hexanoyl homoserine lactone (N-β-oxo-hexanoyl-L-homoserine lactone), oxo octanoyl homoserine lactone (N-β-oxo-octanoyl-L-homoserine lactone), oxo decanoyl N-β-oxo-decanoyl-L-homoserine lactone, hexanoyl homoserine lactone, N-butanoyl-homoserine lactone, oxo dode Canoyl homoserine lactone (N-β-oxo-dodecanoyl-L-homoserine lactone).

In this context, the term "adequacy recognition" is used. "Quorum" means "quorum". In other words, when the number of bacteria is small, such signal transmission does not occur, but when the concentration increases and the concentration of AHLs exceeds a certain level, they detect their density. The word 'Quorum' is used because this signal transmission is for the detection of populations. Therefore, when signal transduction agents reach a certain concentration, they bind to regulatory proteins to promote or inhibit the expression of specific genes, resulting in not only the onset but also bioluminescence, biofilm formation, and resistance to antibiotics.

Representative examples of pathogenicity by controlling the production of various pathogens due to the appropriate density recognition strategy are as follows. Pseudomonas Pseudomonas, a causative agent of respiratory infections in patients with fibrocystic cystosis aeruginosa) and Burke holde Ria Sepharose cyano (Burkholderia cepacia), and the opportunity for ever mammalian pathogen Serratia rikwi Pacific Enschede (Serratia liquefacience), control of pathogens Pseudomonas aero dihydro pillar (Aeromonas hydrophila), or Vibrio angwil rarum (Vibrio anguillarum ), phytopathogen Erwinia carotovora or Agrobacterium tumefaciens .

Meanwhile, microorganisms present in foods, especially in refrigerated or frozen foods, do not usually cause pathogenicity, but may generate pathogenic substances by generating a signal substance due to any environmental change. On the other hand, the possibility of detecting the bacteria present in the sample and quantifying the amount of the bacteria by investigating the signal substances in the sample has also been reported. In addition to these foods, it is known that proper density recognition is involved in causing pathogenicity with various plants and animals including humans, crops, fish, and the like.

Titration recognition blockage and disturbance strategies include the inhibition of acyl homoserine lactone synthesis step, inactivation through enzymatic degradation of acyl homoserine lactone, and acyl homoserine lactone inhibitors for perturbation of appropriate density recognition signaling. Four studies have been applied for the inhibition of acyl homoserine lactone itself [Korean Patent Application Nos. 2001-73348, 2002-17167, 2002-68797, 2003-73319]. . However, the strains applied to date were Bacillus thuringiensis , Arthrobacter sp., Rhodococcus sp.

The present invention provides a plant disease agents containing pieri when Dean A ₁ (piericidin A ₁₎ isolated from an acyl homoserine lactone, Kita Sato sports rasok (Kitasatospora sp.) For competitive inhibition as a as an active ingredient.

In another aspect, the present invention provides a method for producing pieri when Dean A ₁ (piericidin A ₁₎ culturing the Kita Sato spokes la in AR030054.

The present invention is characterized by a plant disease inhibitor comprising as an active ingredient a compound of the formula (1) or a pharmaceutically acceptable salt thereof having a competitive inhibitory activity of acyl homoserine lactone.

The present invention is characterized by the genus Kitasatospora sp . AR030054 (KCTC10904BP), which produces the compound of Formula 1 having the competitive inhibitory activity of acyl homoserine lactone.

Referring to the present invention in more detail as follows.

To search for microorganisms with competitive inhibitory activity of acyl homoserine lactone (AHLs), Chromobacterium violaceum wild type strain Chromobacterium violaseum , a mini-Tn5 variant of ATCC 31532 CV026 was used. Chromobacterium violaceum produces a purple pigment by its acyl homoserine lactone, but it is a chromobacterium violaseum. CV026 is a mutant strain that does not produce purple pigment without artificially adding AHLs by mutating the gene of AHLs synthase of the strain. Hexanoyl homo is a representative AHLs through well-diffusion assay using the strain. Microorganisms that produce competitive inhibitors against serine lactone ( N -hexanoyl homoserine lactone) were searched. Among the microorganisms producing a competitive inhibitor of the acyl homoserine lactone, Escherichia coli, Salmonella typhimurium , Staphylococcus aureus , Bacillus subtilis , Candida albicans Microorganisms exhibiting antimicrobial activity were excluded, and only microorganisms that produced titrant recognition inhibitors that regulate pathogenicity through perturbation of optimum density recognition of bacteria were selected.

In addition, the selected microorganisms were identified by analyzing the morphological, physiological and biochemical characteristics and 16S rDNA sequences, and were identified as Kitasatospora sp. , Which was identified as Kitatospora sp. AR030054 ( Kitasatospora sp . AR030054). In addition, the strain was deposited with the Korea Biotechnology Research Institute Gene Bank on January 25, 2006, and the accession number was assigned to KCTC10904BP.

The genus Kitasatospora sp . ) The supernatant of the culture medium of AR030054, especially the ethyl acetate extract of the supernatant, acted as a competitive inhibitor of acyl homoserine lactone.

In addition, it was confirmed that the result of separating the active material and then a Dean pieri when A ₁ (piericidin A ₁₎ of the formula (1) material from the culture medium, it was confirmed that the function as a competitive inhibitor of the compound of formula (1) acyl-homoserine lactone.

[Formula 1]

Kitasatospora genus AR030054 of the present invention ( Kitasatospora sp . AR030054) A culture of [KCTC10904BP] or a compound of Formula 1 isolated therefrom, or a pharmaceutically acceptable salt thereof, acts as a competitive inhibitor of acyl homoserine lactone, a signaling agent of cell titration recognition, and is used as a food, crop, fish It can be used as an anti-infective agent or plant disease inhibitor of infectious diseases caused by infection of microorganisms such as bacteria from various animals and plants including humans and hosts.

In one embodiment, Kita Sato spokes la in AR030054 (Kitasatospora with the acyl homoserine lactone competitive inhibition activity of (acyl homoserine lactone) according to the present invention sp . AR030054) Competitive inhibitory activity of acyl homoserine lactone, such as culture solution of [KCTC10904BP], supernatant of the culture solution, organic solvent extract of the supernatant, compound of formula 1 isolated therefrom or a pharmaceutically acceptable salt thereof The active ingredient having can be used alone or dissolved in distilled water, or formulated with other excipients can be used as plant disease inhibitors. For example, the active ingredient may be formulated with a conventional adjuvant such as sodium dodecyl sulfate (SDS), sodium lignin sulfonate (SLS), and kaolin. Can be.

In addition, the plant disease inhibitor of the present invention may be mixed with other conventional synthetic pesticides or biopesticides or mixed with fertilizers.

The throughput of the plant disease inhibitor according to the present invention is a range that does not deviate significantly from the conventional pesticide throughput, for example, the chemical liquid is sprayed until it evenly flows down the surface of the plant. In addition, it is effective to treat at any stage of growth from the seed of the plant to the maturity stage, and at any concentration of less than 1 mM, it does not affect the germination or growth of the plant. It was confirmed that no. The plant disease inhibitor of the present invention can be treated by conventional pharmaceutical treatment methods such as spraying, irrigation or dipping.

The amount of the plant disease inhibitor used in the present invention may be appropriately adjusted according to the type of plant to be treated, the type and condition of the plant disease, treatment time and method, etc., but preferably, competitive inhibitory activity of acyl homoserine lactone. a to less than 1 mM in an amount from 5 μ M based on the active ingredient has, preferably from 10 μ M is within the concentration range of less than 500 μ M.

The plant disease inhibitors of the present invention can be used for the treatment or prevention of infectious plant diseases caused by various bacterial organisms. Infections with Gram-negative bacteria, including Erwinia carotovora or Agrobacterium tumefaciens infections of plants.

Hereinafter, the present invention will be described in more detail with reference to Examples, but the following Examples are intended to illustrate the present invention and do not limit the present invention.

Example  One: Active strain  Selection

(1) Selection of acyl homoserine lactone competitive inhibitory activity strain

Over 4,500 strains isolated from soil were identified in G.S.S. Incubated for 7 days at 28 ℃, 140 rpm in a liquid medium and stored at -4 ℃ as a culture medium, the supernatant after thawing and centrifugation immediately before the experiment was used in this experiment.

D-glucose 20 g Soluble starch 10 g Soybean meal 25 g Beef extract 1 g Yeast extract 4 g Sodium chloride 2 g Calcium carbonate 2 g Potassium phosphate 0.025 g D.W. 1L pH 7.2

In order to detect acyl homoserine lactone competitive inhibitors, a well-diffusion assay was performed by the following method.

As a test strain to search for acyl homoserine lactone competitive inhibitors, chromobacterium violaseum CV026 was used. Also hexanoyl homoserine lactone (N -hexanoyl homoserin lactone, HHL) were stored at -20 ℃ at a concentration of 10 μ M in the solution was added 0.1% acetic acid in ethyl acetate.

Chromobacterium violaseum in LB medium on prepared LB agar plates 5 ml of LB semi-solid medium mixed with CV026 and HHL was dispensed. The Chromobacterium violaseum CV026 was dispensed so that the final OD value was 0.2 by liquid culture in LB medium, and HHL was dispensed so that the final concentration was 100 nM.

After the medium was completely solidified, a well of 7 mm diameter was made in the medium, and 50 μl of the culture supernatant was dropped into each well. After culturing for one day at 30 ℃ was observed.

58 strains were selected from 4,500 culture supernatants by the well-diffusion assay, and 41 strains were selected by reproducibility experiments, which are shown in Table 2.

(2) antimicrobial activity measurement

The strain used to determine the antimicrobial activity of the active strains was Escherichia Coli) KCTC 1924, Salmonella typhimurium Head Stadium (Salmonella typhimurium) KCTC 1926, Staphylococcus aureus (Staphylococcus aureus) KCTC 1916, Staphylococcus aureus (Staphylococcus aureus) KCTC 1928, Bacillus subtilis (Bacillus subtilis) KCTC 1021, Candida albicans ) KCTC 7965.

Candida albicans (Candida albicans ) KCTC 7965 is cultured in yeast liquid medium at 30 ℃ for one day and dispensed in yeast semi-solid agar medium, and after dividing in yeast agar medium to make a well of diameter 7 mm and then in each well Table 2 50 µl of the culture supernatant of 41 strains was dropped. This was observed after incubation at 30 ° C. for one day.

The remaining strain if the culture medium after culturing for a day at 30 ℃ in LB liquid medium dispensed in LB semi-solid agar medium, and dispensed in a LB agar culture medium in good Candida albicans (Candida albicans), create the same well and KCTC 7965 strains After dropping the supernatant of the culture solution was observed after culturing for one day at 30 ℃.

Among the 41 strains, 15 strains of Table 2 except for the antimicrobial strains were selected through the antimicrobial activity experiment.

Antibacterial activity (+,-no) Strain without antimicrobial activity 1916 1928 1021 1924 1926  G010008 - - - - - V  G010070 - - + - -  G010089 + + + - -  G010155 - - + - -  G010186 - - + - -  G010234 - - - - - V  G010245 - - + - -  G010248 - - + - -  G010250 - - + - -  G010296 - - - - - V  G010297 - - + + -  G010303 - - + - -  G010321 + + + - -  G010371 - - - - - V  G010377 - - + - -  G010378 - - - - - V  G010512 + - + - -  G010549 + - - - -  G010598 - - - - - V  G010601 - - - - - V  G011055 - - + - -  M002389 - - + - -  AR030054 - - - - - V  M002466 + - - - -  M005331 + - - - -  M005369 + + + + -  M005399 - - - - - V  M005412 - - - - - V  M005470 - - - - - V  M005971 - - - - - V  M008481 - - - - - V  M008506 - - + - -  M008514 + + + + -  M008563 - - + - -  M009628 - - - - - V  M009975 + + + - -  M010122 + + + - -  M010127 - - - - - V  M010128 + + + - -  M010138 - - + - -  G011085 - - + + -

(3) Active strain  Selection

Among the 15 strains selected from Table 2, the AR030054 strain having the highest acyl homoserine lactone competitive inhibitory activity was selected. FIG. 1 is a photograph of a plate that produced low support that inhibits violet pigment production when well-diffusion assay with the supernatant of AR030054 strain culture.

Example  2: Active strain  Sympathy

(1) Morphological, Physiological and Biochemical Identification

The morphological, physiological and biochemical properties of the strain AR030054 selected in Example 1 were referred to by the Manual of Determinative Bacteriology and the Manual for the Identification of Medical Bacteria. After checking the strain was identified.

2 shows an AR030054 strain photograph showing gray color on Bennett's medium and an image enlarged 400 times by an optical microscope. The optimum growth temperature was 25 ℃, the strain was not grown below 4 ℃ and above 40 ℃. It grew up to pH 5.5 ~ 9.5 and showed optimal growth at pH 7. The best growth was achieved at 0% NaCl, and growth was not observed at more than 8%.

In order to determine the phenotype of the AR030054 strain, experiments using ISP (International Streptomyces Project) medium 2 to 5 showed that the mycelia of ISP medium 2, 3, 4, 5 were dark gray, gray, gray, and light yellow, respectively. Formed. The substrate mycelia formed greenish black, grayish brown, dark grayish brown and light brown, respectively.

In addition, AR030054 strains do not form melanoid pigments, have nitrate reducing activity, and have examined glucose magnetization, resulting in glucose, arabinose, sucrose, fructose, rhamnose, inositol, raffinose, mannitol, lactose and galactose. Was available.

(2) Molecular Genetic Identification

The 16S rDNA sequence of the AR030054 strain was analyzed in a conventional manner. Primer was used by Bioneer 27F and 1492R primer at a concentration of 10 pmol, PCR was carried out for 30 cycles at 94 ℃, 1 minute, annealing 54 ℃, 45 seconds, 72 ℃, 3 minutes, denatured sequencer ( The sequence was analyzed by Applied Biosystems model 310 automatic DNA sequencer.

The AR030054 strain had a 16S rDNA sequence of SEQ ID NO: 1 and was blasted by National Center for Biotechnology Information (NCBI) Kitasatospora kifunensis DSM 6307 ^T , Kitasatospora nipponensis 99% similarity with HKI 0315 ^T respectively. Also in the genus Kitasatospora sp.) The results of sequence similarity analysis are shown on the Phylogenetic tree in FIG. 3, and the AR030054 strain is Kitasatospora. nipponensis ) HKI 0315 ^T and Kitasatospora azatica NBRC 13803 ^T were found to be closest to each other.

Therefore, through the results of (1) and (2) of Example 2, the AR030054 strain is a genus Kitasatospora. sp . ) Was found to be a new strain, and this was genus AR030054 ( Kitasatospora sp . AR030054). In addition, the strain was deposited with the Korea Biotechnology Research Institute Gene Bank on January 25, 2006, and the accession number was assigned to KCTC 10904BP.

Example  3: separation of active substance

First, Kitasatospora genus AR030054 ( Kitasatospora sp . AR030054) [KCTC10904BP] was incubated for 10 days at 28 ° C. and 140 rpm using GSS medium of Table 1 for 7 days. The supernatant was separated by centrifugation for 10 L at 6,000 rpm for 30 minutes, and then the supernatant was extracted with ethyl acetate and concentrated under reduced pressure (318.4 mg). Next, silica gel column chromatography was performed. At this time, the silica gel powder was manufactured by Merck Co., Ltd., while chloroform and methanol were separated by flowing 50: 1 ~ 1: 1, concentrated under reduced pressure and dissolved in distilled water to confirm the active fraction through well-diffusion analysis. (59.1 mg). The active fraction is separated on a silica gel TLC plate (0.5 mm × 1 mm) using a developing solution in which chloroform and methanol are mixed at a ratio of 8: 1 (v / v). Next separated on ODS TLC plate using 68 (v / v)% acetonitrile developing solution (1 mg). In each separation step, a well-diffusion assay described in (1) of Example 1 was performed to use a high acyl homoserine lactone competitive inhibitory activity in the next separation step.

It was confirmed by HPLC whether or not pure purification of the finally obtained 1 mg of the compound. At this time, the column was YMC ODS, Φ250 × 4.6 mm, and was analyzed at a flow rate of 0.5 ml / min with 68 (v / v)% acetonitrile. The active peak appeared at 40.7 minutes (FIG. 4) and the UV absorption was found to show the maximum peak at 210 nm.

Example  4: Identification of active substance

¹³ C-NMR and ¹ H-NMR were performed on the active material of Example 3, and the results are shown in FIGS. 5 and 6. ¹ H- ¹ H COSY spectrum results are shown in FIG. In addition, it is shown in Figure 8 by measuring the Hetero Multiple Bond Correlation (HMBC) spectrum. Hetero multiple quantum correlation (HMQC) spectra were measured and shown in FIG. 9. Molecular weight was measured at 70 eV by ESI-MS for molecular weight measurement, and JEOL JMS-SX 102A spectrum is shown in FIG. 10.

Through the resulting active material was found to be pieri when Dean A ₁ (piericidin A ₁₎ of the formula (1), and showed the following physico-chemical characteristics of the active material are shown in Table 3.

[Formula 1]

Exterior   White powder Molecular formula C ₂₅ H ₃₇ NO ₄ Molecular Weight   415 g / mol UV λ _max (nm)   210 HPLC (Rt) a (minute)   40.7 Soluble Solvent   Methanol, DMSO, ethyl acetate

Example  5: Pierreicidin  A _One Activity measurement

11 is in accordance with the concentration of the isolated active material (1 μ M, 5 μ M , 10 μ M, 50 μ M, 100 μ M, 500 μ M, 750 μ M, 1000 μ M) acyl homoserine lactone competitive inhibition The results of the active experiment. At this time, in the 5 μ M except 1 μ M 1000 μ M concentrations far got a competitive inhibitory activity displayed homoserine lactone, 1000 μ M concentration began to occur preventing the growth rings. The results show that pierycidin A ₁ exhibits homoserine lactone competitive inhibitory activity without showing antimicrobial activity at less than 1 mM. That is, it shows the possibility of using it as a new and useful plant disease inhibitor which does not cause antibiotic resistance by inhibiting bacterial titration recognition without showing antimicrobial activity as an antibiotic or antimicrobial agent.

Example  6: Plant disease Inhibitory ability  Measure

As plant pathogenic strains, Erwinia carotovora , which is known to be pathogenic due to autoinducers , was used. Potatoes were used as crops to be applied. Experiments were carried out by treating the potato with varying concentrations of the pathogen Erwinia carotobora and the active substance isolated in Example 3.

The pathogen, Erwinia carotobora, was cultured in LB broth medium for 30 ° C. for 16 hours. 1% of the culture was inoculated in fresh LB broth medium and cultured at 30 ° C. for 16 hours. The OD value of the Erwinia carotobora culture cultured as described above was adjusted to 1, and serially diluted from 10 ⁻¹ to 10 ⁻⁴ to inoculate 10 μl of potatoes. Potato was used as it is without processing anything. The incidence of the disease was visually observed, and after 20 hours, the diseased symptom of the form of obliteranous disease appeared brown, and it was judged that the disease occurred in the potato.

The concentration of the pathogen 10 ^-1 10 ^-2 10 ^-3 10 ^-4 Soft area size +++ ++ ± -

Active substance of the formula (1) was diluted to a final concentration of 0 μ M, 5 μ M, 50 μ M, 500 μ M such that the melting were charged into a 10 ^-2 dilution of the culture solution of the control Winiah Caro Sat See with distilled water, the mixture 10 μl of the prepared solution was inoculated with a small wound on the surface of the potato cut with the pipette tip, and the occurrence of the disease was confirmed 20 hours later. In this case, the greater the number of +, the more severe the incidence of choking disease, which was determined by measuring the dried part with the naked eye as described above.

Active substance concentration 0 μ M 5 μ M 50 μ M 500 μ M Soft area size ++ + - -

In Table 4 and Table 5, the size of the soft part by the pathogen Erwinia carotobora is-no soft part, + is soft part about 1 cm or less, ++ is about 1.5 cm, +++ is about 2 cm Indicates.

Table 5 did appear as, the active substance concentration at which the pathogen Mermaid Winiah Caro sat see concentration ¹⁰ to ^2, Example 3 is more than 5 μ M is rot inhibited generation was confirmed (Fig. 12)

The OD value of the Erwinia carotobora culture medium cultured in the same manner as above was adjusted to 1, and serially diluted from 10 ⁻¹ to 10 ⁻⁴ to inoculate 10 μl into the cabbage. Chinese cabbage was used as it is without any processing. The incidence of the disease was observed with the naked eye. After 20 hours, the diseased symptom appeared as brownish symptom.

The concentration of the pathogen 10 ^-1 10 ^-2 10 ^-3 10 ^-4 Soft area size +++ ++ ± -

Above and diluted with distilled water to an active material of formula (1) in the same way to a final concentration of 0 μ M, 5 μ M, 10 μ M, 100 μ M such that the melting were charged into a 10 ^-2 dilution of the culture solution of the control Winiah Caro sat see that Thereafter, 10 μl of the mixed solution was inoculated with a slight wound on the surface of the cabbage cut with a pipette tip, and the occurrence of the disease was confirmed 20 hours later. In this case, the greater the number of +, the more severe the incidence of choking disease, which was determined by measuring the dried part with the naked eye as described above.

Active substance concentration 0 μ M 5 μ M 10 μ M 100 μ M Soft area size ++ + ± -

In Table 6 and Table 7, the size of the soft part by the pathogen Erwinia carotobora is-no soft part, ± is soft part about 0.2 cm, + is about 0.5 cm, ++ is about 1 cm, ++ + Represents about 1.5 cm.

When the table shown in figured as 6, the pathogen Mermaid Winiah Caro sat see concentration ¹⁰ to ^2, the active substance concentration in Example 3 is more than 5 μ M is rot inhibited generation was confirmed (Fig. 13).

As described above, pieri when Dean A ₁ isolated from the invention Kita Sato spokes la in AR030054 (Kitasatospora sp. AR030054) [ KCTC10904BP] Because of the competitive inhibition activity of the acyl homoserine lactone (acyl homoserine lactone) It can be used as a bacterial quantum sensing inhibitor, and thus can be used for the treatment or prevention of infectious plant diseases caused by various bacterial organisms.

Attach sequence list electronic file

Claims (3)

For infectious plant diseases caused by bacteria that secrete acyl homoserine lactone as a signaling material, Plant Disease inhibitor acceptable salt pieri when Dean A ₁ (piericidin A ₁₎ or a pharmaceutical of the formula (1) having a competitive inhibitory activity of the acyl homoserine lactone as an active ingredient. [Formula 1]

The method according to claim 1, The plant disease is Erwinia carotovora ) or Agrobacterium tumefaciens tumefaciens ) Plant disease inhibitor, characterized in that the plant disease caused by infection. Kitasatospora genus AR030054 ( Kitasatospora sp . Culturing the AR030054) [KCTC10904BP] A method of producing a Dean pieri when A ₁ (piericidin A ₁₎ of the formula (I). [Formula 1]

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