CN112806376B - Application of 5-methoxyindole or molecular structure analogue thereof in inhibiting phytopathogen - Google Patents

Application of 5-methoxyindole or molecular structure analogue thereof in inhibiting phytopathogen Download PDF

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CN112806376B
CN112806376B CN202110056950.6A CN202110056950A CN112806376B CN 112806376 B CN112806376 B CN 112806376B CN 202110056950 A CN202110056950 A CN 202110056950A CN 112806376 B CN112806376 B CN 112806376B
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methoxyindole
fusarium graminearum
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高学文
孔孟孟
高璐
梁静
伍辉军
顾沁
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Nanjing Agricultural University
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    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
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Abstract

The invention discloses application of 5-methoxyindole or a molecular structure analogue thereof in inhibiting phytopathogen. The application of 5-methoxyindole or its derivative shown in formula I in inhibiting phytopathogen; wherein R is selected from H and-R2NHR3；R2Is selected from- (CH)2)nN is 1, 2 or 3; r3Selected from H, or-COCH3(ii) a The plant pathogenic bacteria are selected from bacteria, fungi or oomycetes. The invention discovers for the first time that 5-methoxyindole, 5-methoxyindole ammonia has an inhibiting effect on the growth of bacteria, fungi and oomycetes, and 5-methoxyindole, 5-methoxyindole ammonia has a more industrialized prospect as a cheap and easily available chemical raw material.

Description

Application of 5-methoxyindole or molecular structure analogue thereof in inhibiting phytopathogen
Technical Field
The invention belongs to the field of plant protection, and relates to application of 5-methoxyindole and molecular structure analogues thereof in inhibiting phytopathogens.
Background
The 5-methoxyindole is white-like crystal with molecular formula of C9H9NO, mainly used as a pharmaceutical intermediate. 5-methoxytryptamine is an organic compound having the formula C11H14N2O, mainly used as a pharmaceutical intermediate. At present, 5-methoxyindole and molecular structure analogues thereof have no antibacterial activity.
Figure BDA0002900970060000011
Disclosure of Invention
The invention aims to overcome the defects in the prior art and provides application of 5-methoxyindole and molecular structure analogues thereof in inhibiting phytopathogens.
The purpose of the invention can be realized by the following technical scheme:
the application of 5-methoxyindole shown in formula I or its molecular structure analogue in inhibiting phytopathogen; wherein R is selected from H or-CH2CH2NH2(ii) a The plant pathogenic bacteria are selected from bacteria, fungi or oomycetes;
Figure BDA0002900970060000012
preferably, the bacterium is Pantoea ananatis or Ralstonia solanacearum.
As a preferred aspect of the present invention, the fungus is Fusarium graminearum.
Preferably, the oomycete is phytophthora nicotianae.
The application of 5-methoxyindole and molecular structure analogue shown in formula I in the preparation of preparations for inhibiting phytopathogen; wherein R is selected from H and-CH2CH2NH2(ii) a The plant pathogenic bacteria are selected from bacteria, fungi or oomycetes;
Figure BDA0002900970060000021
preferably, the bacterium is Pantoea ananatis or Ralstonia solanacearum.
As a preferred aspect of the present invention, the fungus is Fusarium graminearum.
Preferably, the oomycete is phytophthora nicotianae.
A preparation for inhibiting phytopathogen contains 5-methoxyindole or its molecular structure analog shown in formula I.
A method for inhibiting phytopathogens comprises applying the preparation.
Has the advantages that:
the application patent discovers, through research, that 5-methoxyindole and 5-methoxyfenoxam have broad-spectrum bacteriostatic activity on various plant pathogenic bacteria and fungi, and analyzes a molecular mechanism of the 5-methoxyindole for inhibiting the plant pathogenic fungi (fusarium graminearum). Experimental results show that the 5-methoxyindole can inhibit generation and germination of conidia of fusarium graminearum, and can efficiently induce generation of deformity of fusarium graminearum hypha and conidia, so that the pathogenic capability of fusarium graminearum is reduced. In addition, the experimental results also show that the treatment of hyphae and conidia of fusarium graminearum by 5-methoxyindole can induce the large accumulation of ROS in hyphae and conidia, thereby further proving that the inhibition effect of 5-methoxyindole on the pathogenicity of fusarium graminearum is realized by inducing the large accumulation of ROS in the conidia and the hyphae. The discovery shows that the compounds have great application prospect in preventing and treating plant diseases in agricultural production. 5-methoxyindole and 5-methoxyindole as cheap and easily available drug synthesis intermediates have ideal industrialization prospect.
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FIG. 1.5-Methoxyindole and 5-Methoxyindole to inhibit the growth of Pantoea ananatis DZ-12
FIG. 2.5-Methoxyindole and 5-Methoxylamine inhibit the growth of bacterial blight of rice PXO99(Xoo)
FIG. 3.5-Methoxyindole and 5-Methoxylamine inhibit the growth of bacterial blight of rice RS105(Xoc)
FIG. 4.5-Methoxyindole and 5-Methoxytryptophan inhibit the growth of Fusarium graminearum PH-1
FIG. 5.5-Methoxyindole and 5-Methoxytryptophan inhibit the growth of Phytophthora nicotianae var. nicotianae
FIG. 6.5-Methoxyindole inhibits Fusarium graminearum F.graminearum PH-1 sporulation and conidium germination
FIG. 7.5-Methoxyindole-induced malformation of hyphae and conidia of Fusarium graminearum PH-1
FIG. 8.5-Methoxyindole induces the massive accumulation of ROS in the hyphae of Fusarium graminearum F.graminearum PH-1
FIG. 9.5-Methoxyindole induces the massive accumulation of conidia ROS of Fusarium graminearum F.graminearum PH-1
Detailed Description
Example 15 inhibition of growth of Pantoea ananatis DZ-12 by Methoxyindole and 5-Methoxyindole
The experimental steps are as follows: activating DZ-12 strain with LB liquid culture medium at 28 deg.C and 200rpm overnight, transferring the strain solution to 20ml LB liquid mixed culture medium with 5-Methoxyindole (5-Methoxyindole) and 5-Methoxytryptamine (5-Methoxytryptamine) concentrations of 0, 0.5, 1, 2, 4mM according to 1%, and adjusting OD600The OD was measured every 2 hours at 0.1, 28 ℃ and 200rpm600And recording the values, repeating the experiment for three times, and making the average value of the growth values in 24 hours into a growth curve.
The experimental results are as follows: to investigate whether 5-methoxyindole and 5-methoxyindole inhibit the growth of Pantoea ananatis DZ-12, we set 5-methoxyindole and 5-methoxyindole with different concentration gradients (0, 0.5, 1, 2, 4mM) to be added to LB liquid medium, culture DZ-12 in LB liquid mixed drug medium, and measure OD of DZ-12 strain600Numerical values. The results show that the growth ability of DZ-12 is affected under the condition that the concentration of 5-methoxyindole is 0.5, 1, 2 and 4mM, and the effect is stronger when the concentration is larger. The growth profile of DZ-12 was almost completely inhibited at a concentration of 4mM 5-methoxyindole (1A). Under the condition that the concentration of 5-methoxytryptamine is 0.5, 1, 2 and 4mM, the growth capacity of DZ-12 is influenced, the larger the influence is, but the inhibition effect of 5-methoxyindole on DZ-12 is not strong (figure 1B).
Example 25 inhibition of Xanthomonas oryzae pv. oryzicola PXO99(Xoo) by Methoxyindole and 5-Methoxyindole
The experimental steps are as follows: activating Xoo strain with LB liquid culture medium at 28 deg.C overnight at 200rpm, transferring the strain solution to 20ml LB liquid mixed culture medium with 5-Methoxyindole (5-Methoxyindole) and 5-Methoxytryptamine (5-Methoxytryptamine) concentrations of 0, 0.5, 1, 2, 4mM, and adjusting OD600The OD was measured every 2 hours at 0.1, 37 ℃ and 200rpm600And recording the values, repeating the experiment for three times, and making the average value of the growth values in 24 hours into a growth curve.
The experimental results are as follows: to investigate whether 5-methoxyindole and 5-methoxyindole inhibit the growth of rice bacterial blight strain PXO99 (Xoo). We set different concentration gradient (0, 0.5, 1, 2, 4mM) 5-methoxyindole and 5-methoxyfenox LB liquid mixed culture medium, culture rice bacterial strain P.albuginea PXO99(Xoo) in LB liquid culture medium, measure strain OD600Numerical values. To study the effect of 5-methoxyindole and 5-methoxytryptamine on the growth of Xanthomonas PXO99, we set different concentration gradients for the two drugs, culture PXO99 strain in LB liquid medium, and measure the OD of the strain600Numerical values. The results show that the growth of the strain is inhibited under the condition that the concentration of 5-methoxyindole and 5-methoxytryptamine is 0.5, 1, 2 and 4mM, and the bacteriostatic effect is gradually enhanced along with the increase of the concentrations of the two drugs (figure 2A and figure 2B).
Example 35 inhibition of Xanthomonas oryzae pv. oryzicola RS105(Xoc) by methoxyindole and 5-methoxyindole
The experimental steps are as follows: xoc strain was activated overnight at 200rpm in LB liquid medium 28 ℃, and the inoculum was transferred to 20mL of LB liquid mixed medium containing 5-Methoxyindole (5-Methoxyindole) and 5-Methoxytryptamine (5-Methoxytryptamine) at concentrations of 0, 0.5, 1, 2, 4mM in an amount of 1%, and OD was adjusted600The OD was measured every 2 hours at 0.1, 37 ℃ and 200rpm600And recording the values, repeating the experiment for three times, and making the average value of the growth values in 24 hours into a growth curve.
The experimental results are as follows: to study 5-methoxy groupWhether the growth of rice bacterial leaf blight RS105(Xoc) is inhibited by the indole group and the 5-methoxylphosphine. We set up different concentration gradient (0, 0.5, 1, 2, 4mM) LB liquid mixed culture medium of 5-methoxy indole and 5-methoxy tryptophan, culture RS105(Xoc) strain in LB liquid culture medium, measure strain OD600Numerical values. To investigate whether 5-methoxyindole and 5-methoxytryptamine also inhibited the growth of Xanthomonas RS105(Xoc), mixed liquid media of different concentration gradients of two drugs were set, RS105(Xoc) was cultured in LB liquid mixed liquid media, and OD of strain RS105(Xoc) was measured600Numerical values. The results show that the growth of the strain is inhibited under the condition that the concentration of 5-methoxyindole and 5-methoxytryptamine is 0.5, 1, 2 and 4mM, and the bacteriostatic effect is gradually enhanced along with the increase of the concentrations of the two drugs (figure 3A and figure 3B).
Example 45 inhibition of Fusarium graminearum PH-1 by Methoxyindole and 5-Methoxytryptophan
The experimental steps are as follows: the PH-1 strain was activated by culturing in PDA solid medium at 25 ℃ for 3 days. Respectively arranging solid drug mixing plates of 0, 0.5, 1, 2, 4mM of 5-Methoxyindole (5-Methoxyindole) and 5-Methoxytryptamine (5-Methoxytryptamine), putting the activated PH-1 bacteria plate in the center of the plate, putting the plate into an incubator at 25 ℃ for culture, and repeating the experimental design for three times.
The experimental results are as follows: to investigate whether 5-methoxyindole and 5-methoxytryptophan inhibit the growth of Fusarium graminearum PH-1. A PDA solid mixed culture medium with different concentration gradients (0, 0.5, 1, 2, 4mM) of 5-methoxyindole and 5-methoxytryptophan ammonia is set, a fusarium graminearum PH-1 strain is cultured in the PDA solid culture medium, and the growth condition of PH-1 is observed after 4 days. The experimental results show that both 5-methoxyindole and 5-methoxytryptophan inhibit the growth of fusarium graminearum PH-1 at concentrations of 0.5, 1, 2 and 4mM, the growth of PH-1 is inhibited more strongly with increasing concentration, and the bacteriostatic effect of 5-methoxyindole is more remarkable than that of 5-methoxytryptamine (FIG. 4A). The colony diameters on the plates were measured and subjected to significance analysis, and the results also prove that both 5-methoxyindole and 5-methoxyindole inhibit the growth of Fusarium PH-1, and that the bacteriostatic effect of 5-methoxyindole is the best (FIG. 4B).
Example 55-Methoxyindole and 5-Methoxyindole inhibitors of Phytophthora nicotianae var. nicotianae
The experimental steps are as follows: the Phytophthora nicotianae strain was activated by culturing at 25 ℃ for 3 days in V8 solid medium. Preparing a V8 solid culture plate, respectively arranging a V8 solid mixed drug plate with 0, 0.5, 1, 2, 4mM of 5-Methoxyindole (5-Methoxyindole) and 5-Methoxytryptamine (5-Methoxytryptamine), placing an activated phytophthora nicotianae dish in the center of the V8 solid mixed drug plate, placing the mixed drug plate into an incubator at 25 ℃ for culture, and repeating the experimental design for three times.
The experimental results are as follows: to investigate whether 5-methoxyindole and 5-methoxytryptophan inhibit the growth of Phytophthora nicotianae. A V8 solid mixed drug culture medium of 5-methoxyindole and 5-methoxyfenox with different concentration gradients (0, 0.5, 1, 2 and 4mM) is set, a tobacco phytophthora strain is cultured in a V8 solid culture medium, and the growth condition of the tobacco phytophthora is observed after 4 days. The experimental result shows that 5-methoxyindole and 5-methoxytryptophan have the bacteriostatic action on phytophthora nicotianae when the concentration is 0.5, 1, 2 and 4mM, and the growth of the phytophthora nicotianae is inhibited more strongly along with the increase of the concentration, and the bacteriostatic effect of the 5-methoxyindole is more obvious than that of the 5-methoxytryptamine (figure 5A). The colony diameters on the plates were measured and subjected to significance analysis, and the results also prove that both 5-methoxyindole and 5-methoxyindole inhibit the growth of Fusarium PH-1, and that the bacteriostatic effect of 5-methoxyindole is the best (FIG. 5B).
Example 65 inhibition of Fusarium graminearum F.graminearum PH-1 production by methoxyindole and conidium germination
The experimental steps are as follows: the PH-1 strain was activated by culturing in PDA solid medium at 25 ℃ for 3 days. Respectively setting CMC and YPDA liquid mixed culture medium of 0, 0.5, 1, 2, 4mM 5-Methoxyindole (5-Methoxyindole), respectively placing activated PH-1 bacteria dish in the CMC and YPDA liquid mixed culture medium, respectively placing in a shaking table at 200rpm, culturing in dark at 25 ℃ for 3d, and repeating three times of experimental design.
Experimental results to study whether 5-methoxyindole inhibits the sporulation and conidium germination of Fusarium graminearum, CMC and YPDA liquid mixed culture medium with different concentration gradients (0, 0.5, 1, 2, 4mM) of 5-methoxyindole is set, the Fusarium graminearum is cultured in the CMC and YPDA liquid mixed culture medium, hyphae and conidium are collected after 3d, and the sporulation and conidium germination conditions of the Fusarium graminearum are counted under a microscope. The experimental result shows that the 5-methoxyindole not only has the sporulation inhibition effect on fusarium graminearum when the concentration is 0.5, 1, 2 and 4 mM. And the stronger the inhibition on the sporulation of fusarium graminearum with the increase of the concentration (fig. 6A), the stronger the inhibition on the germination of conidia, and the inhibition effect is enhanced with the increase of the concentration of 5-methoxyindole (fig. 6B). The experimental data demonstrate that 5-methoxyindole inhibits the production of Fusarium and conidium germination.
Example 75-Methoxyindole induces hyphal and conidia malformation in Fusarium graminearum F
The experimental steps are as follows: the PH-1 strain was activated by culturing in PDA solid medium at 25 ℃ for 3 days. Respectively setting (0.1 and 1mM) CMC and YPDA liquid mixed culture medium of 5-Methoxyindole (5-Methoxyindole), respectively placing the activated PH-1 bacteria dish in the CMC and YPDA liquid mixed culture medium, respectively placing the bacteria dish in a shaking table at 200rpm, culturing in the dark at 25 ℃ for 3d, and repeating the experimental design three times.
The experimental result shows whether 5-methoxyindole influences the shapes of hyphae and conidia of fusarium graminearum, CMC and YPDA liquid mixed culture mediums with different concentrations (0.1 and 1mM) of 5-methoxyindole are set, the fusarium graminearum is cultured in the CMC and YPDA liquid mixed culture mediums, and the change of the hyphae and the conidia structures of the fusarium graminearum is observed in a laser confocal microscope after 3 d. The experimental results show that after the fusarium graminearum is treated by the 5-methoxyindole, compared with the control, the 5-methoxyindole not only induces the hypha of the fusarium graminearum to generate the deformity (fig. 7A), but also induces the conidium of the fusarium graminearum to generate the deformity with high efficiency (fig. 7B), and through statistics on the conidium deformity of the fusarium graminearum treated by the 5-methoxyindole, the 5-methoxyindole also proves that the conidium of the fusarium graminearum can be induced to generate the deformity with high efficiency (fig. 7C), so that the pathogenicity of the fusarium graminearum is inhibited.
Example 85-Methoxyindole induces the Mass accumulation of hyphal ROS of Fusarium graminearum F
The experimental steps are as follows: the PH-1 strain was activated by culturing in PDA solid medium at 25 ℃ for 3 days. Setting (1mM) CMC and YPDA liquid mixed culture medium of 5-Methoxyindole (5-Methoxyindole), respectively placing activated Fusarium graminearum dishes in the CMC and YPDA liquid mixed culture medium, placing in a shaking table at 200rpm, culturing in dark at 25 ℃ for 3d, collecting hyphae, and treating the hyphae with DCFH-DA (dichlorofluoroflaveacetate). The experiment was designed in triplicate.
The result of the experiment shows that ROS (reactive oxygen species) is a series of reactive oxygen species generated by aerobic cells in a metabolic process, and comprises the following steps: o-, HO and HO-,. OH, etc. High concentrations of ROS content can cause cell damage and even cell death. DCFH-DA (dichlorofluorescein diacetate) is a specific dye for ROS and excites green fluorescence at the appropriate wavelength. To investigate whether 5-methoxyindole induces a large accumulation of the hyphal ROS of fusarium graminearum, thereby inhibiting its pathogenicity. After treating Fusarium graminearum 3d with (1mM) 5-methoxyindole (5-methoxyindole), hyphae were treated with a fluorescent stain such as DCFH-DA (dichlorofluoroflaveacetate), and fluorescence within the hyphae was observed under a confocal laser microscope. Experimental results showed that the fluorescence of fusarium graminearum f.graminearum hyphae treated with 5-methoxyindole was very strong compared to the control (fig. 8A and 8B), which was also demonstrated by counting the fluorescence intensity per area of hyphae (fig. 8C). Therefore, experiments prove that the 5-methoxyindole can inhibit pathogenicity of fusarium graminearum f.graminearum by inducing a large amount of ROS accumulation in mycelium.
Example 95-Methoxyindole induces the massive accumulation of conidia ROS of Fusarium graminearum F
The experimental steps are as follows: the activated Fusarium graminearum strain was cultured in PDA solid medium at 25 ℃ for 3 days. Respectively setting (0.1mM) CMC and YPDA liquid mixed culture medium of 5-Methoxyindole (5-Methoxyindole), respectively placing activated fusarium graminearum discs in the CMC and YPDA liquid mixed culture medium, respectively placing in a shaking table at 200rpm, culturing in dark at 25 ℃ for 3d, collecting conidia, and treating hyphae with DCFH-DA (dichlorofluoroyellow diacetate). The experiment was designed in triplicate.
Experimental results to investigate whether 5-methoxyindole induces the accumulation of a large amount of ROS in conidia of Fusarium graminearum, thereby inhibiting the pathogenicity thereof. We treated Fusarium graminearum 3d with (0.1mM) 5-methoxyindole (5-methoxyindole), and then the collected conidia of the fungus were treated with a fluorescent stain DCFH-DA (dichlorofluoroflaveacetate), and then observed the fluorescence within the hyphae under a confocal laser microscope. The experimental results show that the fluorescence intensity of the F.graminearum conidia treated with 5-methoxyindole is not only very strong compared to the control (FIGS. 9A and 9B), but it can also be found that the probability of detecting fluorescent conidia is also greatly increased (9D). The results demonstrate that treatment of Fusarium graminearum with melatonin and 5-methoxyindole can enhance the fluorescence intensity per area of conidia by making statistics of the fluorescence intensity per area of conidia (FIG. 9C). Thus, experiments prove that the 5-methoxyindole can inhibit the pathogenicity of fusarium graminearum F.graminearum by inducing the large accumulation of ROS in conidia.

Claims (3)

1. The application of 5-methoxyindole shown in formula I or its molecular structure analogue in inhibiting phytopathogen; wherein R is selected from H or-CH2CH2NH2(ii) a The plant pathogenic bacteria are selected from bacteria, fungi or oomycetes; the bacteria are Pantoea ananatis or Ralstonia solanacearum; the fungus is fusarium graminearum; the oomycetes are phytophthora nicotianae;
Figure FDA0003340769670000011
2. the application of 5-methoxyindole shown in formula I or its molecular structure analogue in preparing preparation for inhibiting phytopathogen; wherein R is selected from H and-CH2CH2NH2；
The bacteria are Pantoea ananatis or Ralstonia solanacearum; the fungus is fusarium graminearum; the oomycetes are phytophthora nicotianae;
Figure FDA0003340769670000012
3. a method of inhibiting phytopathogens comprising applying a composition comprising a compound of claim 1; the plant pathogenic bacteria are selected from bacteria, fungi or oomycetes; the bacteria are Pantoea ananatis or Ralstonia solanacearum; the fungus is fusarium graminearum; the oomycetes are phytophthora nicotianae.
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CN107318846A (en) * 2017-07-11 2017-11-07 重庆大学 Epiphysin suppresses the new application and novel plant oomycetes bactericide of plant Oomycete disease
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CN108684677A (en) * 2018-05-08 2018-10-23 江苏省农业科学院 Application of the epiphysin in preventing and treating bacterial leaf streak of rice
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CN1365971A (en) * 2002-02-19 2002-08-28 中国农业大学 Antibacterial activity, induction, separation and synthesis of N-acyltryptamine derivative as plant protecting chemical
CN107318846A (en) * 2017-07-11 2017-11-07 重庆大学 Epiphysin suppresses the new application and novel plant oomycetes bactericide of plant Oomycete disease
CN108684677A (en) * 2018-05-08 2018-10-23 江苏省农业科学院 Application of the epiphysin in preventing and treating bacterial leaf streak of rice
CN108530335A (en) * 2018-05-21 2018-09-14 华南农业大学 A kind of Benzazole compounds and its preparation method and application
CN111544430A (en) * 2020-05-18 2020-08-18 华南农业大学 Application of melatonin in preparation of medicine for inhibiting and/or killing bacteria

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