Ginkgolic acid derivative as well as preparation method and application thereof

Abstract

The invention discloses a ginkgolic acid derivative as well as a preparation method and application thereof, and belongs to the technical field of chemical synthesis. The preparation method comprises the following steps: mixing and stirring formic acid and ginkgolic acid, keeping the temperature below 50 DEG C, reacting for 30 minutes, cooling to room temperature, adding distilled water, and continuously stirring to obtain a reaction mixture; pouring the reaction mixture into ice water, extracting, washing an organic layer with water, drying, and concentrating under reduced pressure to obtain a mixture; dissolving the obtained mixture in a THF-aqueous solution, adding sodium periodate and triethyl benzyl ammonium chloride, continuously stirring at room temperature, diluting with distilled water, extracting, washing an organic layer with water, drying, evaporating, and purifying by column chromatography to obtain the ginkgolic acid derivative. The ginkgolic acid derivative prepared by the invention can destroy cell membranes of germs, increase permeability of the membranes and inhibit growth of the germs.

Description

Technical Field

[0001] The invention belongs to the technical field of chemical synthesis, and specifically relates to a ginkgolic acid derivative and a preparation method and application thereof. Background Art

[0002] Ginkgo biloba exocarp extract, as a plant natural product with wide application value, has received increasing attention in recent years. Ginkgo acid is one of the main active ingredients in Ginkgo biloba exocarp and has significant biological activities, including antibacterial, antioxidant and anti-inflammatory properties. By optimizing the extraction process of ginkgolic acid, its extraction efficiency and purity can be improved, providing a basis for subsequent applications.

[0003] In the agricultural field, crop pathogenic fungi pose a serious threat to the growth and yield of crops. Although traditional chemical pesticides are effective, their use brings about problems such as environmental pollution and pesticide residues. Therefore, the development of new plant-derived antibacterial agents has become a research hotspot. Ginkgo acid and its derivatives have become potential biological control agents due to their natural sources and biocompatibility. Summary of the invention

[0004] The purpose of the present invention is to provide a ginkgolic acid derivative and a preparation method and application thereof. The ginkgolic acid derivative can destroy the cell membrane of pathogens, increase the permeability of the membrane, and inhibit the growth of pathogens.

[0005] In order to solve the above technical problems, the technical solution adopted by the present invention is as follows: A method for preparing a ginkgolic acid derivative comprises the following steps: S1, mixing formic acid and ginkgolic acid, keeping the temperature below 50°C, reacting for 30 minutes, cooling to room temperature, adding distilled water, and continuing to stir to obtain a reaction mixture; S2. The reaction mixture obtained in step S1 was poured into ice water, extracted with ethyl acetate, and the organic layer was washed with water and anhydrous Na 2 SO 4 Drying and concentrating under reduced pressure to obtain a mixture; S3, dissolving the mixture obtained in step S2 in THF-water solution, adding sodium periodate and triethylbenzyl ammonium chloride, stirring continuously at room temperature, diluting with distilled water, extracting with ethyl acetate, washing the organic layer with water, and 2 SO 4 Drying, evaporation and column chromatography purification gave the ginkgolic acid derivatives.

[0006] Preferably, in step S1, formic acid and ginkgo acid are stirred and reacted at 40°C.

[0007] Preferably, the reduced pressure concentration process parameters in step S2 are: vacuum degree of 58 MPa, temperature of 50°C.

[0008] Preferably, the volume ratio of THF to distilled water in the THF-water solution in step S3 is 1:1.

[0009] Preferably, in step S3, stirring is continued at room temperature for 30 min, and the stirring rate is 1600 rpm.

[0010] Preferably, the eluent in the column chromatography in step S3 is hexane and ethyl acetate prepared in a volume ratio of 1.5:8.5.

[0011] The present invention also provides a ginkgolic acid derivative prepared by the preparation method.

[0012] The present invention also provides a ginkgolic acid derivative prepared by the preparation method or the use of the ginkgolic acid derivative in an antibacterial agent.

[0013] The present invention also provides a ginkgolic acid derivative prepared by the preparation method or application of the ginkgolic acid derivative in a product for inhibiting wheat fusarium head blight.

[0014] The antibacterial mechanism of the ginkgo acid derivatives prepared in this application on wheat fusarium rust: (1) Ginkgo acid derivatives can increase the leakage of nucleic acids and proteins and the conductivity of the bacterial solution of wheat fusarium rust, indicating that the derivatives can destroy the cell membrane of the pathogen mycelium, increase the permeability of the cell membrane, cause damage to the cell membrane, and thus inhibit the growth of the pathogen.

[0015] (2) Ginkgo acid derivatives can increase the MDA enzyme activity in the fungus culture of wheat ergot and the degree of lipid peroxidation in the bacterial cell membrane, indicating that the compound has a strong inhibitory effect on wheat ergot.

[0016] (3) Ginkgo acid derivatives can increase the activity of CAT enzymes in the fungus culture of wheat fusarium rust, promote the increase of protective enzyme activity, and cause changes and damage to the mycelial structure of wheat fusarium rust, showing that the compound has an inhibitory effect on wheat fusarium rust.

[0017] Compared with the prior art, the present invention has the following advantages and technical effects: The present invention provides a ginkgolic acid derivative and a preparation method thereof. The ginkgolic acid derivative has a strong inhibitory effect on wheat fusarium rust, and the inhibition rate of the ginkgolic acid derivative on wheat fusarium rust reaches 86.72%. 50 The value is 1.0231 mg˙mL -1. This preparation method not only solves the problems of chemical pesticides easily generating resistance, killing beneficial organisms and causing environmental pollution in agricultural production, but also realizes the green and environmentally friendly application of natural product derivatives in the field of pesticides. By utilizing the biological activity and chemical properties of natural products such as ginkgolic acid, structural modification and optimization are carried out, and the new fungicide compounds obtained have higher activity and lower toxicity, which can effectively replace some traditional chemical pesticides and provide strong support for the sustainable development of agriculture.

[0018] The technical solution of the present invention is further described in detail below through the accompanying drawings and embodiments. BRIEF DESCRIPTION OF THE DRAWINGS

[0019] Figure 1 The chemical structural formula of the ginkgolic acid derivative 5CHO-2pHA provided in Example 1; Figure 2 The infrared absorption spectrum of the ginkgolic acid derivative 5CHO-2pHA provided in Example 1; Figure 3 The mass spectrometry fragment structure of the ginkgo acid derivative 5CHO-2pHA provided in Example 1, wherein: Figure 3 A in the figure is the fragment structure when the mass-to-charge ratio is 92. Figure 3 B in the figure is the fragment structure when the mass-to-charge ratio is 106. Figure 3 The C in the figure is the fragment structure when the mass-to-charge ratio is 119; Figure 4 The chemical structure of the ginkgolic acid derivative 5CHO-2pHA analyzed by multi-stage mass spectrometry; Figure 5 The mass spectrometry analysis diagram of the ginkgo acid derivative 5CHO-2pHA provided in Example 1; Figure 6 This is the secondary mass spectrometry analysis diagram of the ginkgo acid derivative 5CHO-2pHA provided in Example 1, with a collision energy of 200; Figure 7 This is the secondary mass spectrometry analysis diagram of the ginkgo acid derivative 5CHO-2pHA provided in Example 1, with a collision energy of 150; Figure 8 This is the secondary mass spectrometry analysis diagram of the ginkgo acid derivative 5CHO-2pHA provided in Example 1, with a collision energy of 100; Fig. 9 This is the secondary mass spectrometry analysis diagram of the ginkgo acid derivative 5CHO-2pHA provided in Example 1, with a collision energy of 70; Fig.10 This is the secondary mass spectrometry analysis diagram of the ginkgo acid derivative 5CHO-2pHA provided in Example 1, with a collision energy of 50; Fig.11This is the secondary mass spectrometry analysis diagram of the ginkgo acid derivative 5CHO-2pHA provided in Example 1, with a collision energy of 20; Fig.12 The results of the inhibition of the ginkgolic acid derivative 5CHO-2pHA on wheat fusarium rust provided in Example 1 are as follows: Fig.12 A in the table is PDA medium without 5CHO-2pHA, a derivative of ginkgolic acid. Fig.12 B is the PDA medium to which 0.5 mg·mL-1 ginkgolic acid derivative 5CHO-2pHA was added. Fig.12 C in the figure is the PDA medium with a concentration of 1 mg·mL-1 after adding the ginkgolic acid derivative 5CHO-2pHA. Fig.12 D in the figure is the PDA medium with a concentration of 2 mg·mL-1 after adding the ginkgolic acid derivative 5CHO-2pHA. Fig.12 E in the figure is the PDA medium with a concentration of 4 mg·mL-1 after adding the ginkgolic acid derivative 5CHO-2pHA. Fig.12 F in the figure is PDA medium with a concentration of 8 mg·mL-1 after adding 5CHO-2pHA, a derivative of ginkgolic acid; Fig.13 This is a graph showing the effect of the ginkgolic acid derivative 5CHO-2pHA provided in Example 1 on cell conductivity; Fig.14 This is a graph showing the effect of the ginkgolic acid derivative 5CHO-2pHA provided in Example 1 on the leakage of pathogenic nucleic acid; Fig.15 This is a graph showing the effect of the ginkgolic acid derivative 5CHO-2pHA provided in Example 1 on bacterial protein leakage; Fig.16 This is a graph showing the effect of the ginkgolic acid derivative 5CHO-2pHA provided in Example 1 on MDA activity; Fig.17 This is a graph showing the effect of the ginkgolic acid derivative 5CHO-2pHA provided in Example 1 on the CAT activity of pathogens. DETAILED DESCRIPTION

[0020] The technical solution of the present invention is further described below through the accompanying drawings and embodiments.

[0021] Unless otherwise defined, technical or scientific terms used in the present invention shall have the common meanings understood by one having ordinary skills in the field to which the present invention belongs.

[0022] In the present invention, unless otherwise specified, other test materials and instruments and equipment are conventional test materials in the art and can be purchased through commercial channels.

[0023] Example 1 This embodiment provides a ginkgolic acid derivative, and the preparation method comprises the following steps: S1. Mix 3.4 mL of formic acid and 1.0 g of ginkgolic acid at 40° C., keep the temperature below 50° C., react for 30 min, cool to room temperature, add 1 mL of distilled water, continue stirring, and obtain a reaction mixture; S2. The reaction mixture obtained in step S1 was poured into ice water, extracted with 7.5 mL of ethyl acetate, and the organic layer was washed with water and anhydrous Na 2 SO 4 Dry, vacuum concentrate at 58 MPa and 50°C to obtain a mixture; S3, dissolving the mixture obtained in step S2 in 3.75 mL of THF-water solution (volume ratio: THF: distilled water = 1:1), adding 1.1 g of sodium periodate and 25 mg of triethylbenzyl ammonium chloride, stirring continuously for 30 min at room temperature, stirring at a rate of 1600 rpm, diluting with 25 mL of distilled water, extracting with ethyl acetate, washing the organic layer with water, and removing anhydrous Na 2 SO 4 The product was dried, evaporated, and purified by column chromatography, wherein the column chromatography eluent was hexane and ethyl acetate in a volume ratio of 1.5:8.5, to obtain the ginkgo acid derivative 5CHO-2pHA.

[0024] The effect of the ginkgo acid derivative 5CHO-2pHA provided in Example 1 above was verified by the following test: 1. The ginkgolic acid derivative 5CHO-2pHA provided in Example 1 was subjected to infrared spectroscopy analysis. The results are as follows: Figure 2 .

[0025] Depend on Figure 2 It can be seen that the characteristic peak of aromatic ring skeleton vibration appears at 1607.30 cm -1 、1577.44cm -1 and 1453.09cm -1 According to the fingerprint area 900~650cm -1 There are four characteristic absorption peaks between them, proving the existence of aromatic rings. -1 and 2854.37cm -1 The characteristic absorption peak appeared at 725 cm-1, and the peak shape was sharp, which proved the existence of side chain hydrocarbon methyl and methylene. The OH out-of-plane bending vibration absorption of phenol was at 725 cm-1. -1 The stretching vibration of the CO bond of phenol is located at 1299.46 cm -1 , proving the existence of phenolic hydroxyl groups. The characteristic absorption peak of 5-(10,12-tetradecadienyl)-2-hydroxybenzoic acid is at 1718.42 cm -1 This is the main difference from ginkgolic acid.

[0026] 2. Determination of the mass spectrometry fragments of the ginkgo acid derivative 5CHO-2pHA provided in Example 1, the structural formula is as follows Figure 3 .

[0027] 3. The ginkgo acid derivative 5CHO-2pHA provided in Example 1 was analyzed by multi-stage mass spectrometry. The chemical structure is as follows: Figure 4 .

[0028] 4. The ginkgo acid derivative 5CHO-2pHA provided in Example 1 was subjected to mass spectrometry analysis. The results are as follows: Figure 5 .

[0029] 5. The ginkgo acid derivative 5CHO-2pHA provided in Example 1 was subjected to secondary mass spectrometry analysis. The results are as follows: Figure 6-11 .

[0030] comprehensive Figure 3-Figure 11 The infrared spectrum analysis results showed that the structure of 5-(10,12-tetradecadienal)-2-hydroxybenzoic acid (abbreviated as 5CHO-2pHA) was relatively complex, so multi-level mass spectrometry was used to further determine its structure. Figure 5-Figure 11 It can be seen that the collision energy (COLLISION ENERGY) of the multi-level mass spectrometer is selected to decrease gradually from 200, COLLISION ENERGY: 200→150→100→70→40→20→. Figure 5 and Figure 6 It can be seen that when the collision energy is greater than 100, due to the greater impact force, the probability of decomposing the target molecule into small molecular fragments is higher, and the resulting ion fragments are meaningless. Figure 8 ) and 70 ( Fig. 9 ), the mass-to-charge ratios (m / z) of the ion fragments obtained are: 92, 106, 119, 133, 147, 161, 175, 189, etc. Among them, it can be seen that the difference between two adjacent values ​​is 14, which is CH 2 Mass-to-charge ratio (m / z). According to the molecular weight mass-to-charge ratio of ion fragments and the basic information of the target derivative structure compared with the mass spectrum database, the following can be obtained: Figure 3 The fragment structure shown The mass-to-charge ratio of each ion fragment differs by 14. When the mass-to-charge ratio (m / z) is 133, add “-CH 2 -”; when the mass-to-charge ratio (m / z) is 147, add “-CH 2 -"; mass-to-charge ratio (m / z): 161, add "-CH 2 -"; mass-to-charge ratio (m / z): 175, add "-CH 2-”; when the mass-to-charge ratio (m / z) is 189, add “-CH 2 -”… and so on, we get Figure 1 The structural formula of the derivative compound is shown.

[0031] 6. The inhibitory effect of ginkgolic acid derivative 5CHO-2pHA on wheat fusarium rust was determined. Fig.12 .

[0032] Depend on Fig.12 It can be seen that as the concentration of the ginkgolic acid derivative 5CHO-2pHA added to the PDA medium continues to increase, the inhibitory effect of the ginkgolic acid derivative 5CHO-2pHA on wheat fusarium rust is also continuously enhanced.

[0033] 7. The toxicity of the ginkgo acid derivative 5CHO-2pHA provided in Example 1 to wheat fusarium was tested. The test scheme was as follows: The results are shown in Table 1.

[0034] Table 1 Toxicity test of ginkgolic acid derivative 5CHO-2pHA against wheat fusarium

[0035] As shown in Table 1, the toxicity of the target derivative 5CHO-2pHA to wheat fusarium was tested, and the EC 50 The value is 1.0231 mg·mL -1 .

[0036] 8. The malondialdehyde (MDA) content of wheat fusarium was determined. The results are shown in Table 2.

[0037] Table 2 Malondialdehyde content of wheat fusarium

[0038] 9. Determine the conductivity of the 5CHO-2pHA derivative of ginkgo acid provided in Example 1 to cells. The test scheme is as follows: Inoculate the bacterial cake of wheat fusarium into 50 mL PDB medium and heat at 25°C and 180 r·min -1 The target derivative 5CHO-2pHA was added to the PDB medium after 3 days to make the medium concentration EC 50 The culture medium with the same amount of dimethyl sulfoxide was used as the control and the shaking culture was continued. The conductivity of the supernatant was measured after 0h, 1h, 2h, 3h, 4h, 5h, 6h, 12h, and 24h. Each treatment was repeated 3 times. The results are shown in Fig.13 .

[0039] Depend on Fig.13It can be seen that the conductivity of the control group showed an upward trend at 2h, and then gradually stabilized. The conductivity of the wheat fusarium treated with the target derivative 5CHO-2pHA increased significantly at 2h. Although the conductivity decreased slightly at 24h, within 24h, the conductivity of each treatment was greater than that of the control group. The test results show that the target derivative 5CHO-2pHA has a significant effect on the conductivity of wheat fusarium, which is because the target derivative 5CHO-2pHA destroys the cell membrane of wheat fusarium, causing the cytoplasm to leak out, resulting in an increase in conductivity.

[0040] 10. The effect of the ginkgolic acid derivative 5CHO-2pHA provided in Example 1 on the leakage of pathogenic nucleic acid was determined. The test scheme was as follows: the bacterial cake of wheat fusarium was inoculated into 50 mL PDB medium and the mixture was heated at 25°C and 180 r·min -1 The target derivative 5CHO-2pHA was added to the PDB medium after 3 days to make the medium concentration EC 50 , the medium with the same amount of dimethyl sulfoxide added was used as the control, and the shaking culture was continued. After 0h, 3h, 6h, 12h, and 24h, 2mL of bacterial solution was taken and centrifuged at 10000rmp for 10min, and the absorbance of the supernatant was measured at a wavelength of 260nm. The nucleic acid leakage was measured by OD 260 The result is as follows. Fig.14 .

[0041] Depend on Fig.14 It can be seen that the nucleic acid leakage of wheat fusarium sphaeroides increased significantly with the extension of the action time of the target derivative 5CHO-2pHA, indicating that the target compound can destroy the integrity of the cell membrane.

[0042] 11. The effect of the ginkgolic acid derivative 5CHO-2pHA provided in Example 1 on the protein leakage of pathogens was determined. The experimental scheme was as follows: the bacterial cake of wheat fusarium was inoculated into 50 mL PDB medium and the mixture was heated at 25°C and 180 r·min -1 The target derivative 5CHO-2pHA was added to the PDB medium after 3 days to make the medium concentration EC 50 The culture medium with an equal amount of dimethyl sulfoxide was used as a control and the shaking culture was continued. 2 mL of bacterial solution was taken at 0, 3, 6, 12, and 24 hours after centrifugation at 10,000 rpm for 10 minutes, and the absorbance of the supernatant was measured at a wavelength of 280 nm. The protein leakage was measured by OD 280 The result is as follows. Fig.15 .

[0043] Depend on Fig.15It can be seen that from 0h to 12h, the leakage of bacterial liquid protein in the treatment group showed a significant upward trend. This shows that the target derivative 5CHO-2pHA destroyed the integrity of the cell membrane of wheat fusarium, causing a large amount of mycelial protein to leak out, resulting in an increase in the leakage of bacterial liquid protein. From 12h to 24h, the mycelial protein content of the treatment group did not change significantly and tended to be stable. During the measurement period, the leakage of each treatment was greater than that of the control group.

[0044] 12. The effect of the ginkgolic acid derivative 5CHO-2pHA provided in Example 1 on the MDA activity was determined. The test scheme was as follows: This test used the Solarbio malondialdehyde (MDA) content detection kit, which contained one bottle each of reagent 1, reagent 2, reagent 3 and extract.

[0045] Sample preparation: Mix about 0.1 g of mycelium with 1 mL of extract and homogenize in an ice bath. -1 Centrifuge for 10 minutes, remove the supernatant, and place on ice for determination. Prepare the MDA determination working solution: Before use, mix one bottle of reagent 2 with 20 mL of reagent 1 and store at 2-8°C for one month.

[0046] The sample and working liquid were mixed in the proportions shown in Table 2 and kept in a water bath at 100°C for 60 min. Then, they were placed in an ice bath and heated at 10000 r / min. -1 Centrifuge at room temperature for 10 minutes. Take 200 µL of the supernatant and place it in a 96-well plate. Measure the absorbance of each sample at 532 nm and 600 nm (each sample tube corresponds to a blank tube, and each group of treatments is repeated 3 times). Fig.16 .

[0047] Depend on Fig.16 It can be seen that when cells are damaged, the degree of membrane lipidation increases and the content of the main product malondialdehyde (MDA) increases. Therefore, the content of malondialdehyde (MDA) can reflect the state of oxidative damage to the cell membrane to a certain extent. Fig.16 It can be seen that the malondialdehyde content in the mycelium of the treatment group was significantly higher than that of the control group, and the malondialdehyde content in the control group was only slightly increased. After 24 hours of treatment with the target derivative 5CHO-2pHA, the malondialdehyde content in the mycelium of the treatment group increased by 1.89 times. The above results show that the target derivative 5CHO-2pHA can cause lipid peroxidation in the cell membrane of wheat fusarium, increase the malondialdehyde content, cause cell membrane damage, and thus inhibit the growth of wheat fusarium.

[0048] 13. The effect of the ginkgolic acid derivative 5CHO-2pHA provided in Example 1 on the CAT activity of pathogens was determined. The test scheme was as follows: This test uses the Solarbio catalase (CAT) activity kit, which contains one bottle of reagent 1, one bottle of reagent 2, and one bottle of extract.

[0049] Sample preparation: weigh about 0.1 g of mycelium and add 1 mL of extract solution and homogenize in an ice bath. -1 Centrifuge for 10 minutes, remove the supernatant, and place on ice for testing. Prepare CAT working solution: add 25µL of reagent 2 to 5mL of reagent 1, stir evenly, and prepare immediately.

[0050] 10 µL of sample and 190 µL of working solution were added to a 96-well plate, mixed immediately and timed. After 5 CHO-2 pHA, the initial absorbance A1 at 240 nm and the absorbance A2 after 1 minute were recorded. Calculation. 1 μmol H catalyzed per g tissue per minute in the reaction system 2 O 2 Degradation is defined as one unit of enzyme activity. The CAT activity calculation formula is as follows: CAT (U / g mass) = 764.5 × ΔA / W; (ΔA=A1-A2) (W: sample quality) Depend on Fig.17 It can be seen that CAT can eliminate the H produced in the disproportionation reaction. 2 O 2 Protect cells from damage. Fig.17 It can be seen that the CAT enzyme showed an overall trend of first increasing and then decreasing. At 6h, the CAT enzyme activity increased significantly, indicating that the CAT enzyme activity showed an upward trend to eliminate H 2 O 2 To protect the damaged cells, the enzyme activity reached the highest value at 12h. After that, due to the serious damage of the cells in the treatment group, the CAT enzyme activity showed a downward trend, which proved that the CAT enzyme activity could no longer effectively eliminate the H produced in the dismutation reaction. 2 O 2 , the protection against wheat fusarium rust was weakened. This indicates that the target derivative 5CHO-2pHA has a certain inhibitory effect on the growth of wheat fusarium rust.

[0051] Finally, it should be noted that the above embodiments are only used to illustrate the technical solution of the present invention rather than to limit it. Although the present invention has been described in detail with reference to the preferred embodiments, those skilled in the art should understand that they can still modify or replace the technical solution of the present invention with equivalents, and these modifications or equivalent replacements cannot cause the modified technical solution to deviate from the spirit and scope of the technical solution of the present invention.

Claims

1. A method for preparing a ginkgo acid derivative, characterized in that: The steps include: S1, mixing formic acid and ginkgolic acid, keeping the temperature below 50°C, reacting for 30 minutes, cooling to room temperature, adding distilled water, and continuing to stir to obtain a reaction mixture; S2, the reaction mixture obtained in step S1 is poured into ice water, extracted with ethyl acetate, the organic layer is washed with water, dried over anhydrous Na2SO4, and concentrated under reduced pressure to obtain a mixture; S3. Dissolve the mixture obtained in step S2 in THF-water solution, add sodium periodate and triethylbenzyl ammonium chloride, continue stirring at room temperature, dilute with distilled water, extract with ethyl acetate, wash the organic layer with water, dry with anhydrous Na2SO4, evaporate, and purify by column chromatography to obtain a ginkgolic acid derivative.

2. The preparation method according to claim 1, characterized in that: In step S1, formic acid and ginkgo acid are stirred and reacted at 40°C.

3. The preparation method according to claim 1, characterized in that: The reduced pressure concentration process parameters in step S2 are: vacuum degree of 58 MPa, temperature of 50°C.

4. The preparation method according to claim 1, characterized in that: The volume ratio of THF to distilled water in the THF-water solution in step S3 is 1:

1.

5. The preparation method according to claim 1, characterized in that: In step S3, stirring is continued at room temperature for 30 min at a stirring rate of 1600 rpm.

6. The preparation method according to claim 1, characterized in that: The eluent in the column chromatography in step S3 is hexane and ethyl acetate prepared in a volume ratio of 1.5:8.

5.

7. The ginkgolic acid derivative prepared by the preparation method according to any one of claims 1 to 6.

8. Use of the ginkgolic acid derivative prepared by the preparation method according to any one of claims 1 to 6 or the ginkgolic acid derivative according to claim 7 in an antibacterial agent.

9. Use of the ginkgolic acid derivative prepared by the preparation method according to any one of claims 1 to 6 or the ginkgolic acid derivative according to claim 7 in a product for inhibiting wheat fusarium head blight.

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