CN113717145A - Double-naphtho r-pyrone compound and application thereof in resisting plant anthrax - Google Patents
Double-naphtho r-pyrone compound and application thereof in resisting plant anthrax Download PDFInfo
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Abstract
The invention provides a double naphtho r-pyrone compound and application thereof in resisting plant anthrax, the compound with the structural types shown in formulas (1) to (4) or pharmaceutically acceptable salt thereof has the activity of inhibiting the plant anthrax and can be used as an effective component for preventing and treating plant anthrax diseases; the implementation example proves that the compound provided by the invention has a strong inhibiting effect on various plant anthrax bacteria, and the effective amount of the bis-naphtho-pyrone compound is 4-32 mu g/mL, preferably 4-16 mu g/mL.
Description
Technical Field
The invention relates to the technical field of bioengineering, in particular to a dinaphtho r-pyrone compound and application thereof in resisting plant anthrax.
Background
Anthracnose is a kind of plant pathogenic bacteria which are frequently infected on garden plants and crops, and often damages plant leaves or tender stems, and the main pathogenic bacteria of the anthracnose is Colletotrichum gloeosporioide (Colletotrichum gloeosporioide). Pathogenic bacteria can infect leaves through epidermal tissues such as wounds and skin holes, so that the leaves can have symptoms such as blackish brown specks at the edges of the leaves, blackening and withering, inward curling of the leaves, retrogradation of terminal buds and the like, and plant death can be caused in severe cases. Currently, anthracnose is mainly controlled by a chemical method, such as patent CN105613022A "a method for preventing and treating anthracnose of paphiopedilum", but the problems of pesticide residue, environmental pollution and the like can occur when a large amount of chemical pesticides are used for a long time. An antibacterial lead compound is searched from a natural resource treasury and is used for preventing and controlling plant anthrax, and the antibacterial lead compound becomes an important way and a research hotspot for creating biological inoculants.
In view of the above, the invention provides an application of a novel dinaphtho r-pyrone compound in the prevention and control of colletotrichum gloeosporioides, and the compound has the effect of inhibiting the activity of colletotrichum gloeosporioides pathogenic bacteria and can be used as an effective component in a microbial agent.
Disclosure of Invention
Aiming at the problems, the invention provides a dinaphtho r-pyrone compound and application thereof in resisting plant anthrax.
The double naphtho r-pyrone compound comprises a compound 1, a compound 2, a compound 3 or a compound 4; the structural formulas of the compound 1, the compound 2, the compound 3 and the compound 4 are sequentially shown as formulas (1) to (4):
further, the bis-naphtho r-pyrone compound is easily soluble in acetone, dichloromethane and DMSO (dimethyl sulfoxide), is soluble in methanol and acetonitrile, and has an ultraviolet absorption wavelength of preferably 210-280 nm.
Further, the application of the bis-naphtho r-pyrone compound or the pharmaceutically acceptable salt thereof in preparing bactericides.
Further, the pharmaceutically acceptable salt is an inorganic acid salt or an organic acid salt of the compound having the structure represented by formula (1) to formula (4).
Further, the inorganic acid salt is hydrochloride, sulfate, phosphate, hydrobromide or hydroiodide.
Further, the organic acid salt is tartrate, citrate, formate, acetate, oxalate, butyrate, oxalate, maleate, succinate, adipate, alginate, citrate, aspartate, benzenesulfonate, camphorate, camphorsulfonate, digluconate, cyclopentanepropionate, dodecylsulfate, ethanesulfonate, glucoheptonate, glycerophosphate, hemisulfate, heptanoate, hexanoate, fumarate, 2-hydroxyethanesulfonate, lactate, methanesulfonate, nicotinate, 2-naphthalenesulfonate, pamoate, pectinate, 3-phenylpropionate, picrate, pivalate, propionate, succinate, thiocyanate, p-toluenesulfonate or undecanoate.
Further, the bacteria are anthrax bacteria.
Further, the anthrax bacteria include Colletotrichum gloeosporioide (Colletotrichum mucilaginose), banana Colletotrichum musae (Colletotrichum coccoides), potato Colletotrichum coccoides, and Mahonia fortunei (Colletotrichum fioriniae).
Furthermore, the bactericide is in the form of an emulsifiable concentrate, a suspending agent, powder, granules or an aqueous solution.
Further, the bactericide comprises a bis-naphtho r-pyrone compound or pharmaceutically acceptable salts thereof and auxiliary materials.
Further, the content of the bis-naphtho r-pyrone compounds in the bactericide is 4-32 mu g/mL.
Furthermore, the auxiliary materials comprise one or more of diluent, adhesive, disintegrating agent, lubricant, pH regulator, cosolvent and antioxidant.
Further, the diluent is starch, dextrin, sugar powder, lactose, microcrystalline cellulose and/or compressible starch.
Further, the binder is water, ethanol, starch slurry, syrup, maltose and/or cellulose derivatives.
Further, the disintegrant is dry starch, sodium carboxymethyl starch, cellulose derivative, surfactant and/or crospovidone.
Further, the lubricant is stearic acid, talcum powder, hydrogenated vegetable oil, polyethylene glycol and/or lauryl magnesium sulfate;
further, the pH regulator is an acetate, citrate and/or phosphate buffer system.
Further, the cosolvent is sodium benzoate, sodium salicylate, urethane, urea, nicotinamide and/or acetamide.
Further, the antioxidant is inert gas and/or metal chelate.
Further, the preparation method of the compounds with the structures shown in the formulas (1) to (4) comprises the following steps:
1) inoculating plant endophytic fungi into a solid culture medium for fermentation culture to obtain a fermentation product;
2) mixing the fermentation product obtained in the step 1) with an organic extraction solvent, and then extracting to obtain a total extract;
3) sequentially carrying out silica gel adsorption and elution on the total extract obtained in the step 2), and obtaining corresponding sub-components by combining thin layer analysis;
4) and (3) sequentially carrying out chromatographic column separation and solvent evaporation on the corresponding sub-components obtained in the step 3) to obtain compounds with structures shown in formulas (1) to (4).
Further, the plant endophyte comprises Plenodomus tracheiphilus, oryza sativa (Claviceps virens), Chaetomium viridans (Chaetomium virescens) and/or Haematococcus nanensis (Fusarium sp.), preferably Plenodomus tracheiphilus.
Further, the amount of the plant endophytic fungi inoculated to the solid medium is not particularly limited, and may be selected from those known to those skilled in the art.
Further, the step of inoculating the plant endophytic fungi into the solid culture medium for culture is to firstly inoculate the plant endophytic fungi into a potato glucose agar culture medium (PDA culture medium) for amplification culture, and inoculate the plant endophytic fungi into a rice culture medium for fermentation when the plant endophytic fungi are in a logarithmic phase, so as to obtain a fermentation product.
Further, the rice culture medium comprises: rice and water; the mass-volume ratio of the rice to the water is 60-80 g: 80-100 mL.
Further, the temperature of the fermentation culture is 25 +/-5 ℃; the fermentation time is 30-35 days.
Further, the organic extraction solvent is ethyl acetate, acetone, methanol, ethanol, dichloromethane or a dichloromethane/methanol mixed solvent with a volume ratio of 3: 1-1: 3.
Further, the extraction is a normal-temperature soaking method and/or a normal-temperature ultrasonic method; the extraction times are 2-3.
Furthermore, the specific modes of the normal-temperature soaking method and the normal-temperature ultrasonic method are not particularly limited, and any well-known extraction mode in the field can be selected.
Furthermore, the silica gel of the silica gel column is silica gel for sample mixing and silica gel for separation.
Furthermore, the mesh number of the silica gel for sample mixing is 60-100 meshes; the mesh number of the silica gel for separation is 200-300 meshes.
Further, the elution is gradient elution; the eluent for gradient elution is petroleum ether-ethyl acetate, cyclohexane-acetone, petroleum ether-acetone, chloroform-methanol or dichloromethane-methanol mixed solvent.
Further, the method of gradient elution in the present invention is not particularly limited, and a gradient elution method well known to those skilled in the art may be used.
Further, the method of thin layer analysis according to the present invention is not particularly limited, and any analysis method known to those skilled in the art may be used.
Further, the chromatographic column is preferably a reverse phase silica gel semi-preparative column.
Further, the mobile phase of the chromatographic column is methanol and water (the ratio of methanol to water is 40-100: 60-0); the flow rate of the mobile phase was 2.0 mL/min.
Further, the temperature for evaporating the solvent is 40-50 ℃.
Compared with the prior art, the invention has the beneficial effects that:
(1) the dinaphtho r-pyrone compound and the pharmaceutically acceptable salt thereof have strong inhibiting effect on plant anthrax, wherein the anthrax comprises colletotrichum gloeosporioides, banana anthrax, potato anthrax and mahonia fortunei.
(2) The preparation method of the invention obtains the high-purity compound monomer by performing fermentation culture on the strain and preferably performing separation and purification on the fermentation product by an extraction and separation method.
Drawings
FIG. 1 is a drawing showing Compound 1 of the present invention1H nuclear magnetic spectrogram;
FIG. 2 shows Compound 1 of the present invention13C nuclear magnetic spectrum;
FIG. 3 is a mass spectrum of Compound 1 of the present invention;
FIG. 4 is a drawing showing Compound 2 of the present invention1H nuclear magnetic spectrogram;
FIG. 5 shows Compound 2 of the present invention13C nuclear magnetic spectrum;
FIG. 6 is a mass spectrum of Compound 2 of the present invention;
FIG. 7 shows Compound 3 of the present invention1H nuclear magnetic spectrum
FIG. 8 is a drawing showing a scheme of Compound 3 of the present invention13C nuclear magnetic spectrum;
FIG. 9 is a mass spectrum of Compound 3 of the present invention;
FIG. 10 is a drawing of Compound 4 of the present invention1H nuclear magnetic spectrum
FIG. 11 is a drawing showing that Compound 4 of the present invention13C nuclear magnetic spectrum;
FIG. 12 is a mass spectrum of Compound 4 of the present invention;
Detailed Description
In order to better understand the technical content of the invention, specific examples are provided below to further illustrate the invention.
EXAMPLE 1 preparation of Binaphtho r-pyrones
Strain: plenodomas tracheiphilus;
the preparation method comprises the following steps:
1) fermentation: inoculating the strain to a PDA culture medium for amplification culture, inoculating the strain to a rice culture medium in a clean bench when the mangrove endophytic fungi is in a logarithmic phase, standing and fermenting for 30 days at room temperature in 50 bottles to obtain a fermentation product; the rice culture medium in each bottle is obtained by mixing 60g of rice and 80mL of distilled water and then carrying out autoclaving;
2) preparation of crude fraction of bis-naphtho-pyrone: soaking and extracting the fermentation product obtained in the step 1) with ethyl acetate for 3 times, recovering the solvent to obtain 8g of extract, uniformly mixing the extract at the ethyl acetate part on silica gel (60-100 meshes), and performing column chromatography on the mixture by using common column chromatography silica gel (sample: the weight ratio of the silica gel is 1: 20) the separation was performed and then eluted with a dichloromethane-methanol (1:0, 100:1, 100:2, 20:1, 10:1, 1:1) gradient, and in bound thin layer analysis, the developing solvent for thin layer analysis was a dichloromethane-methanol mixed system (dichloromethane: methanol is 10:1), each gradient elutes 3-5 column volumes, 9 subfractions are obtained after eluent is combined (Fr-A, Fr-B, Fr-C, Fr-D, Fr-E, Fr-F, Fr-G, Fr-H and Fr-I flow out in sequence according to gradient sequence), wherein the components Fr-B, Fr-D, Fr-E, Fr-F are target components to be further prepared and purified.
3) A method for purifying a compound represented by the formula (1): dissolving the component Fr-B in the step 2) with chromatographic methanol, standing, precipitating crystals, performing suction filtration with a sand core suction filtration device, rinsing with chromatographic methanol for 2-3 times, and collecting in a clean sample bottle to obtain a monomer compound 1;
4) a method for purifying a compound represented by the formula (2): dissolving the component Fr-D in the step 2) by using chromatographic methanol, performing chromatographic separation after passing through a 0.22-micron filter membrane, wherein the liquid chromatographic condition is 80-10% of methanol, collecting a chromatographic peak with retention time of 13.0min, and evaporating by using a rotary evaporator to obtain a monomer compound 2 (the purity is higher than 98%);
5) a method for purifying a compound represented by the formula (3): dissolving the component Fr-E in the step 2) with chromatographic methanol, centrifuging, performing chromatographic separation after a 0.22-micron filter membrane, wherein the liquid chromatographic condition is 80% methanol-20% water, collecting a chromatographic peak with retention time of 20.1min, and evaporating by using a rotary evaporator to obtain a monomeric compound 3 (the purity is higher than 95%);
6) a method for purifying a compound represented by the formula (4): dissolving the component Fr-F in the step 2) with chromatographic methanol, centrifuging, performing chromatographic separation after a 0.22-micron filter membrane, performing liquid chromatography under the conditions of 70% methanol-30% water, collecting a chromatographic peak with retention time of 18.5min, and evaporating by using a rotary evaporator to obtain a monomeric compound 4 (the purity is higher than 95%).
Taking the compounds 1-4 obtained in the steps 3), 4), 5) and 6) for nuclear magnetic and mass spectrometry, wherein the nuclear magnetic spectrum data are shown as follows:
nuclear magnetic spectroscopy data for compound 1:
brown crystalline powder, HR-ESI-MS (M/z 519.1301[ M + H ]]+,calcd.519.1300)
13C NMR(125MHz,DMSO-d6)δ:198.1(C-4,4’),164.9(C-5,5’),160.0(C-8,8’),158.7(C-6,6’),154.9(C-10a,10a’),141.5(C-9a,9a’),107.1(C-5a,5a’),104.2(C-9,9’),101.6(C-4a,4a’),100.0(C-7,7’),98.5(C-10,10’),72.9(C-2,2’),42.7(C-3,3’),20.5(C-2-CH3,2’-CH3)；
1H NMR(500MHz,DMSO-d6)δ:1.29(6H,d,J＝6.0Hz,CH3-2,2’),2.67(2H,dd,J＝17.5,3.0Hz,H-3),2.83(2H,dd,J＝17.5,12.0Hz,H-3’),4.47(2H,ddq,J＝11.0,6.0,2.5Hz,H-2,2’),5.66(2H,s,H-10,10’),6.46(2H,s,H-7,7’),9.77(2H,s,H-6,6’),14.99(2H,s,H-5,5’)
Nuclear magnetic spectroscopy data for compound 2:
brown crystalline powder, HR-ESI-MS (M/z 547.1605[ M + H ]]+,calcd.547.1603)
13C NMR(125MHz,DMSO-d6)δ:201.5(C-4),199.9(C-4’),165.4(C-5),164.6(C-5’),159.8(C-8),159.7(C-8’),158.6(C-6),158.5(C-6’),154.5(C-10a),154.2(C-10a’),141.4(C-9a),141.4(C-9a’),107.0(C-5a),106.9(C-5a’),104.4(C-9),104.2(C-9’),100.9(C-4a),100.3(C-4a’),99.8(C-7,7’),98.1(C-10,10’),77.4(C-2),74.7(C-2’),45.3(C-3),43.5(C-3’),19.2(2-CH3),16.1(2’-CH3),9.5(3-CH3),9.4(3’-CH3)；
1H NMR(500MHz,DMSO-d6)δ:1.06(3H,d,J＝7.5Hz,3’-CH3),1.12(3H,d,J＝7.0Hz,3-CH3),1.19(3H,d,J＝6.5Hz,2’-CH3),1.31(3H,d,J＝6.5Hz,2-CH3),2.69(1H,dq,J＝7.0,3.0Hz,H-3),2.77(1H,dq,J＝7.0,4.0Hz,H-3’),4.20(1H,dq,J＝7.0,5.0Hz,H-2),4.54(1H,dq,J＝7.0,3.0Hz,H-2’),5.66(1H,s,H-10),5.68(H,s,H-10’),6.44(2H,s,H-7,7’),9.74(1H,s,6’-OH),9.77(1H,s,6-OH),15.0(2H,s,5’-OH,5-OH)
Nuclear magnetic spectroscopy data for compound 3:
brown crystalline powder, HR-ESI-MS (M/z 547.1606[ M + H ]]+,calcd.547.1603)
13C NMR(125MHz,DMSO-d6)δ:9.6(3-CH3,3’-CH3),19.3(2-CH3,2’-CH3),45.4(C-3,3’),77.5(C-2,2’),98.3(C-10,10’),99.9(C-7,7’),101.0(C-4a,4a’),104.3(C-9,9’),107.0(C-5a,5a’),141.5(C-9a,9a’),154.6(C-10a,10a’),158.6(C-6,6’),159.9(C-8,8’),164.7(C-5,5’),200.0(C-4,4’)；
1H NMR(500MHz,DMSO-d6)δ:1.11(6H,d,J＝7.0Hz,3-CH3,3’-CH3),1.30(6H,d,J＝6.0Hz,2-CH3,2’-CH3),2.77(2H,dq,J＝11.0,6.0Hz,H-3,3’),4.18(2H,dq,J＝11.0,6.0Hz,H-2,2’),5.64(2H,s,H-10,10’),6.44(2H,s,H-7,7’),9.74(2H,s,6-OH,6’-OH),15.0(2H,s,5-OH,5’-OH)
Nuclear magnetic spectroscopy data for compound 4:
brown crystalline powder, HR-ESI-MS (M/z 517.1133[ M + H ]]+,calcd.517.1101)
13C NMR(125MHz,DMSO-d6)δ:198.1(C-4),183.1(C-4’),169.2(C-2’),163.1(C-5,5’),159.7(C-8’),159.0(C-8),158.9(C-6’),158.1(C-6),155.5(C-10a’),152.0(C-10a),141.3(C-9a),139.8(C-9a’),106.8(C-9),106.6(C-9’),106.0(C-3’),105.8(C-5a),104.3(C-5a’),101.8(C-4a,4a’),100.5(C-10),100.3(C-10’),99.2(C-7),97.8(C-7’),72.6(C-2),43.2(C-3),20.6(2-CH3),20.1(2’-CH3)
1H NMR(500MHz,DMSO-d6)δ:1.26(3H,d,J＝6.5Hz,2-CH3),2.25(3H,s,2’-CH3),2.59(1H,dd,J＝17.0,3.0Hz,Hb-3),2.71(1H,dd,J＝17.0,3.0Hz,Ha-3),4.42(1H,s,H-2),5.54(1H,s,H-3’),6.13(1H,s,H-10),6.15(1H,s,H-10’),6.36(1H,s,H-7),6.53(1H,s,H-7’),9.57(1H,s,8-OH),9.67(1H,s,8’-OH)
Example 2 anti-anthrax Activity assay
1. Test strains: colletotrichum gloeosporioides (Colletotrichum gloeosporioide), Banana Colletotrichum musae (Colletotrichum coccoides), Potato Colletotrichum (Colletotrichum coccoides), Mahonia fortunei (Colletotrichum fioriniae);
2. the experimental steps are as follows: inoculating test strains to PDA culture medium, culturing for one week, picking out small amount of bacterial blocks, inoculating to PDB culture medium (potato glucose broth culture medium), shake culturing at 28 deg.C in shaking table for 3d, and diluting to 10%4Adding each hypha/mL into a 96-well plate in sequence, dissolving the compound by DMSO respectively, obtaining compound solutions with different concentration gradients (2, 4, 8, 16, 32 mu g/mL) by adopting a double dilution method, adding 100 mu L of the compound solution into each well, adding 10 mu L of 10% resazurin solution into each well, standing and culturing for 48 hours at 28 ℃, measuring the absorbance value of Ex/Em which is 544/590nm, calculating the MIC value, taking carbendazim as a positive control, and repeating all treatments for three times.
TABLE 1 Minimum Inhibitory Concentrations (MIC) of Compounds 1-4 against four test pathogenic anthrax bacteria
The results show that the compounds 1-4 can inhibit the activities of colletotrichum gloeosporioides, banana colletotrichum gloeosporioides, potato colletotrichum gloeosporioides and Chinese mahonia gloeosporioides, and the inhibition effect is equivalent to carbendazim, wherein the inhibition effect of the compound 1 is optimal.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.
Claims (10)
1. The bis-naphtho r-pyrone compound is characterized by comprising a compound 1, a compound 2, a compound 3 or a compound 4; the structural formulas of the compound 1, the compound 2, the compound 3 and the compound 4 are sequentially shown as formulas (1) to (4):
2. the use of the bis-naphtho r-pyrones of claim 1 or pharmaceutically acceptable salts thereof in the preparation of fungicides.
3. The use of the bis-naphtho r-pyrones compound or the pharmaceutically acceptable salt thereof according to claim 2 in the preparation of fungicides, wherein the pharmaceutically acceptable salt is an inorganic acid salt or an organic acid salt of the compound having the structure represented by formula (1) to formula (4).
4. The use of the dinaphtho r-pyrones or the pharmaceutically acceptable salts thereof as claimed in claim 2 in the preparation of a bactericide, wherein the bactericide is in the form of an emulsifiable concentrate, a suspension, a powder, a granule or an aqueous solution.
5. The use of the bis-naphtho r-pyrones or their pharmaceutically acceptable salts in the preparation of fungicides according to claim 4, wherein said fungicides comprise bis-naphtho r-pyrones or their pharmaceutically acceptable salts and adjuvants.
6. The use of the bis-naphtho r-pyrones or pharmaceutically acceptable salts thereof in the preparation of fungicides as claimed in claim 5, wherein said adjuvants comprise one or more of diluents, binders, disintegrants, lubricants, p H regulators, co-solvents and antioxidants.
7. Use of the bis-naphtho r-pyrones or pharmaceutically acceptable salts thereof according to any one of claims 2 to 6 for the preparation of a fungicide wherein the bacterium is anthrax; the anthrax bacteria include Colletotrichum gloeosporioide, Colletotrichum musae, Colletotrichum cocodes and Colletotrichum capitatum.
8. The process for the preparation of the bis-naphtho r-pyrones according to any one of claims 1 to 6, comprising the steps of:
1) inoculating plant endophytic fungi to a potato glucose agar culture medium for amplification culture, and inoculating the plant endophytic fungi to a rice culture medium for fermentation culture when the plant endophytic fungi is in a logarithmic phase to obtain a fermentation product;
2) mixing the fermentation product obtained in the step 1) with an organic extraction solvent, and then extracting to obtain a total extract;
3) sequentially carrying out silica gel adsorption and elution on the total extract obtained in the step 2), and obtaining corresponding sub-components by combining thin layer analysis;
4) and (3) carrying out chromatographic column separation on the corresponding sub-components obtained in the step 3), and evaporating the solvent to dryness at 40-50 ℃ to obtain the compound monomers with the structures shown in the formulas (1) to (4).
9. The method of claim 8, wherein the plant endophytic fungi comprise plenodomaus tracheipilus, oryza sativa (cladoceps virens), Chaetomium viridans (Chaetomium virescens) and/or mangrove endophytic fungi of the south China sea (Fusarium sp.).
10. The method of claim 8, wherein the fermentation temperature is 25 ± 5 ℃; the fermentation time is 30-35 days.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111120361.6A CN113717145B (en) | 2021-09-18 | 2021-09-18 | Dinaphtho r-pyrone compound and application thereof in resisting plant anthrax |
| PCT/CN2021/137671 WO2023040090A1 (en) | 2021-09-18 | 2021-12-14 | Dinaphtho r-pyrone compounds and application thereof against plant anthracnose |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2023040090A1 (en) * | 2021-09-18 | 2023-03-23 | 中国热带农业科学院热带作物品种资源研究所 | Dinaphtho r-pyrone compounds and application thereof against plant anthracnose |
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| CN113717145B (en) * | 2021-09-18 | 2023-05-26 | 中国热带农业科学院热带作物品种资源研究所 | Dinaphtho r-pyrone compound and application thereof in resisting plant anthrax |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2023040090A1 (en) * | 2021-09-18 | 2023-03-23 | 中国热带农业科学院热带作物品种资源研究所 | Dinaphtho r-pyrone compounds and application thereof against plant anthracnose |
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| CN113717145B (en) | 2023-05-26 |
| WO2023040090A1 (en) | 2023-03-23 |
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