AU2021240121A1 - Compound for controlling plant pathogenic bacteria and application thereof - Google Patents
Compound for controlling plant pathogenic bacteria and application thereof Download PDFInfo
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Abstract
Disclosed is a compound for controlling plant pathogenic bacteria and an
application thereof. The compound is hydroxychavicol; tests show that
hydroxychavicol has bactericidal activity; when a test concentration of the compound
5 is 1000 pmol/L, it has a good bacteriostatic effect on Xanthomonas oryzae pv. oryzae,
Xanthomonas oryzae pv. oryzicola, Xanthomonas citri subsp. citri, Acidovorax
citrulli, Ralstonia solanacearum, Xanthomonas fragariae, Xanthomonas campestris
pv. mangiferaeindicae, Xanthomonas campestris pv. campestris, and Pectobacterium
carotovorum subsp. brasiliense with an inhibition rate of more than 90%; meanwhile,
10 results of in vivo experiments showed that the compound had a good inhibitory effect
on a pathogenicity of Pectobacterium carotovorum subsp. brasiliense, and also had a
good control effect on Xanthomonas campestris pv. mangiferaeindicae and
Acidovorax citrulli. These results indicate that hydroxychavicol has a broad-spectrum
bactericidal effect on plant pathogenic bacteria. This invention lays a foundation for
15 further utilizing the endemic plant Piper austrosinense in China to create new
environment-friendly botanicalpesticides.
16
Description
The present invention relates to the technical field of plant disease control, and particularly to a compound for controlling plant pathogenic bacteria and an application thereof.
Piper austrosinense is a woody climbing vine of Pepper in Piperaceae, which is mainly distributed in Guangxi, Hainan, Guangdong and coastal islands. As "Chinese Materia Medica" records, the piper austrosinense has an efficacy of detumescence and analgesia, and is mainly used for a toothache and a traumatic injury. hydroxychavicol is a component with good bactericidal activity separated from the piper austrosinense by the project team by a biological activity tracking method, and its chemical structural formula is shown in Formula I.
0
(formula I) According to searches, protocatechualdehyde, an active component of the piper austrosinense, has been used in medicine as an antibacterial agent, however, at present, there is no report on an agricultural activity of hydroxychavicol at home and abroad, and there is no report on in inhibitory effect of hydroxychavicol on the plant pathogenic bacteria.
In view of the deficiency of the prior art, the present invention provides the compound for controlling the plant pathogenic bacteria and the application thereof.
A solution of the present invention includes the following aspects:
provided is the compound for controlling the plant pathogenic bacteria, the compound is hydroxychavicol, and a structural formula of the compound is shown as Formula I:
On the one hand, provided is an application of hydroxychavicol in controlling bacterial plant diseases. Preferably, the disease is a plant bacterial disease. More preferably, pathogenic bacteria of the disease are Xanthomonas oryzae pv .oryzae, Xanthomonas oryzae pv. oryzicola, Xanthomonas citri subsp. citri, Acidovorax citrulli, Ralstonia solanacearum, Xanthomonas fragariae, Xanthomonas campestrispv. campestris, Pectobacterium carotovorum subsp. carotovorum, Pectobacterium carotovorum subsp. brasiliense and/or Xanthomonas campestris pv. mangiferaeindicae.
Results of in vivo experiments showed that hydroxychavicol had a good inhibitory effect on a pathogenicity of Pectobacterium carotovorum subsp. brasiliense, and also had a good control effect on Xanthomonas campestris pv. mangiferaeindicaeand Acidovorax citrulli.
On the other hand, provided is a fungicide or bacteriostatic agent for controlling plant diseases, an active ingredient of which is hydroxychavicol, optionally supplemented by an auxiliary agent.
According to actual needs, the above formulations can be prepared into a suspension concentrate, an emulsion in water, a microemulsion, an emulsifiable concentrate, a wettable powder or a water dispersible granule by conventional methods in the field.
Further, provided is a method of extracting hydroxychavicol from branches and leaves of the piper austrosinense, which comprises:
S1: collecting the branches and the leaves of the piper austrosinense, drying in the shade, crushing and sieving to obtain a dry powder, performing a first cold soaking with an ethanol solution, and filtering to obtain a first filtrate and a filter residue; performing a second cold soaking and extracting on the filter residue with the ethanol solution until the filtrate is colorless to obtain a second filtrate, merging the first filtrate and the second filtrate, and concentrating to dryness to obtain an ethanol extract of the piper austrosinense; S2: adding a water to suspend the ethanol extract of the piper austrosinense, extracting with a petroleum ether, concentrating to dryness to obtain a petroleum ether extract; S3: applying the petroleum ether extract to a column by a petroleum ether wet method, and eluting in a petroleum ether-ethyl acetate system to obtain nine fractions; and S4: a fraction 3 is eluted by the petroleum ether-ethyl acetate system to obtain the hydroxychavicol.
Preferably, in step Sl, a volume concentration of the ethanol solution is 90% to 95%; a duration of the first cold soaking is 6 to 7 days; a mass ratio of the dry powder to the ethanol solution is 1:(9-10); a mass ratio of the filter residue to the ethanol solution is 1:(9-10).
Preferably, in step S3, a volume ratio of the petroleum ether to the ethyl acetate is (2.5-3):1; and in step S4, the volume ratio of the petroleum ether to the ethyl acetate is (9-10):1. The present invention achieves the following the advantageous effects: Tests show that, at a concentration of 1000 pmol/L, the hydroxychavicol provided by the present invention has a significant inhibitory effect on many diseases of important crops, especially several vegetable and tropical fruit diseases, has a good bacteriostatic effect on Xanthomonas oryzae pv. oryzae, Xanthomonas oryzae pv. oryzicola, Xanthomonas citri subsp. citri, Acidovorax citrulli, Ralstonia solanacearum, Xanthomonas fragariae, Xanthomonas campestris pv. mangiferaeindicae, Xanthomonas campestris pv. campestris, and Pectobacterium carotovorum subsp. brasiliense with an inhibition rate of more than 90%, and has a certain bacteriostatic effect on Pectobacteriumcarotovorum subsp. carotovorum with an inhibition rate of 53.80%. Results of in vivo experiments showed that the compound had a good inhibitory effect on the pathogenicity of Pectobacterium carotovorum subsp. brasiliense, and also had a good control effect on Xanthomonas campestrispv. mangiferaeindicaeand Acidovorax citrulli. In a word, the compound provided by the present invention has a significant inhibitory effect on plant pathogenic bacteria, and a natural bactericidal active substance for agricultural disease control is provided; the compound can be used to control many diseases of important crops such as bacterial blight of rice and a mango bacterial black spot; as a fungicide or bacteriostatic agent, it has characteristics of high efficiency, low toxicity and safety, which meet the requirements of pesticide creation at present.
In order to help better understand the technical content of the present invention, specific examples are provided below to further explain the present invention.
The experimental methods used in the examples of the present invention are conventional methods unless otherwise specified.
The materials, reagents and the like used in the examples of the present invention are commercially available unless otherwise specified. Example 1 preparation and identification of hydroxychavicol A preparation method of hydroxychavicol comprises: S: collecting the branches and leaves of the piper austrosinense, naturally drying in the shade, crushing and sieving with a 40-mesh screen to obtain 2 kg of dry powder, performing the first cold soaking in a solution of 95% ethanol by volume (a mass ratio of the dry powder to 95% ethanol being 1:10) for 7 days, filtering to obtain the first filtrate and the filter residue; performing the second cold soaking and the extracting on the filter residue with the solution of 95% ethanol by volume (a mass ratio of the filter residue to 95% ethanol being 1:10), extracting for 3 to 5 times, until the filtrate is colorless to obtain the second filtrate, merging the first filtrate and the second filtrate, and concentrating to dryness in a rotary film evaporator under a reduced pressure to obtain 302.14 g of the ethanol extract of the piper austrosinense. S2: Adding the water to suspend the ethanol extract of the piper austrosinense, extracting with petroleum ether and ethyl acetate sequentially, concentrating to dryness under the reduced pressure to obtain 103.85 g petroleum ether extract and 128.29 g of ethyl acetate extract, respectively. S3: Applying the petroleum ether extract to the column (silica gel column) by the petroleum ether wet method, and eluting in the petroleum ether-ethyl acetate (volume ratio 2.5:1) system, merging with similar fractions by a TLC detection to obtain the nine fractions according to polarities. S4: the fraction 3 is eluted by the petroleum ether-ethyl acetate (volume ratio 10: 1) system to obtain a compound 1 (128 mg). A chemical structure of the compound 1 was identified as hydroxychavicol by MS, H NMR and 1C NMR, and the spectral data are as follows:
ESI-MS m/z: 173 [M + Na], 149 [M - H]-; IH-NMR (500 MHz, CDC 3) 6H: 6.75 (lH, d, J= 7.8 Hz, H-5), 6.67 (IH, s, H-2), 6.57 (lH, d, J= 7.8 Hz, H-6), 5.88 (lH, m, H-8), 5.02 (2H, m, H-9), 3.20 (2H, d, J 6.4 Hz, H-7); and 1C-NMR (125 MHz, CDC 3) 6C: 133.4 (C-1), 115.9 (C-2), 143.6 (C-3), 141.8 (C-4), 116.2 (C-5), 121.2 (C-6), 39.5 (C-7), 137.8 (C-8), 115.7 (C-9). The above data are consistent with those reported in the literature (Yoshizawa Y, Kawaii S, Kanauchi M, et al. Chavicol and related compounds as nematocides [J]. Bioscience, biotechnology, and biochemistry, 1993, 57 (9): 1572-1574.), so it is identified as hydroxychavicol with purity > 95%.
The above hydroxychavicol can also be obtained by a chemical synthesis. The compound 1 is brown clots (fragments) with a melting point of 42-46°C, and is soluble in an acetone and other organic solvents. Example 2 The differences between this example and Example 1 are that:
in step S1, a volume concentration of the ethanol solution is 90%; a duration of the first cold soaking is 6 days; a mass ratio of the dry powder to the ethanol solution is 1:9; a mass ratio of the filter residue to the ethanol solution is 1:9.
In step S3, a volume ratio of the petroleum ether to the ethyl acetate is 3: 1; and
in step S4, a volume ratio of the petroleum ether to the ethyl acetate is 9:1.
The experimental results of this example are the same as those of Example 1. Example 3 Measurement of inhibitory activity of hydroxychavicol against plant pathogenic bacteria In the research of agricultural bactericidal active substances of the piper austrosinense, the inventor found that the hydroxychavicol has the effect of controlling plant pathogenic bacteria by the activity tracking method. By taking the following experiment as an example, a role of hydroxychavicol in controlling plant diseases was verified. 1. Test strains Xanthomonas oryzae, Xanthomonas oryzae, Xanthomonas citri subsp. citri, Acidovorax citrulli, Ralstonia solanacearum, Xanthomonas fragariae, Xanthomonas campestris, Pectobacterium carotovorum subsp. Carotovorum, Pectobacterium carotovorum subsp. Brasiliense, Xanthomonas campestrispv. mangiferaeindicae.All the above strains were provided by a research group of pesticide chemical biology and application in Chinese Academy of Tropical Agricultural Sciences Environment and Plant Protection Institute. 2. Test method 2.1 In vitro activity detection In order to evaluate the an agricultural bactericidal activity of the hydroxychavicol, a bacteriostatic activity of the compound of the present invention to the plant pathogenic bacteria is evaluated by adopting a 96-well plate method to measure a minimum inhibitory concentration and a sub-inhibitory concentration of the compound to the plant pathogenic bacteria. The method refers to a method by Shi Chao (Shi Chao et al. Antibacteria Activity of Protocatechualdehude Against Cronobacter Sakazakii and Its Possible Mechanism of Action [J]. Modern Food Science and Technology, 2017, 33 (07): 105-111, 62.), wherein a prepared bacterial suspension was added into a 96-well ELISA plate with 10 pL per well. A sample control group was added with 10 pL bacteria suspension and 200 pL liquid culture medium (control group); a blank control group was added with 200 pL liquid culture medium, and a compound solution test group was set with 200 pL per well. After blowing and mixing the pharmaceutical solution and the bacteria suspension evenly, the sample was placed in an incubator with vibration (500 r/min); a culture temperature was set at 28 to 30°C; a culture time was 18 to 24 hours, and an absorbance of the bacteria solution was measured by a microplate reader. The inhibitory effect of the compound on pathogenic bacteria was calculated by the following formula. Bacteriostatic rate(%) {(control group OD6 0 0 -blank control group OD6 0 0 )-(test group D 6 00-compound solution control OD6 0 0 )}/(control group OD6 0 0 -blank control group OD6 0 0) x 100%
Data analysis: the results of bacteriostatic activity of the hydroxychavicol against 10 kinds of test plant pathogenic bacteria are shown in Table 1; the results show that when a concentration of the test hydroxychavicol is 1000 pmol/L, it has a good bacteriostatic effect on Xanthomonas oryzae pv. oryzae, Xanthomonas oryzae pv. oryzicola, Xanthomonas citri subsp. citri, Acidovorax citrulli, Ralstonia solanacearum, Xanthomonas fragariae, Xanthomonas campestris pv. mangiferaeindicae, Xanthomonas campestris pv. campestris, and Pectobacterium carotovorum subsp. brasiliensewith an inhibition rate of more than 90%, and has a certain bacteriostatic effect on Pectobacteriumcarotovorum subsp. carotovorum with the inhibition rate of
53.80%. Table 1 Bacteriostatic activity of hydroxychavicol against 10 kinds of plant pathogenic bacteria Inhibition Inhibition Test strains Test strains rate (%) rate (%) Xanthomonas Xanthomonas oryzae pv. 95.06 campestris pv. 98.63 oryzae campestris Pectobacterium Xanthomonas oryzae pv. carotovorum 99.24 53.80 oryzicola subsp. carotovorum Pectobacterium Xanthomonas citri subsp. 99.03 carotovorum 90.97 citri subsp. brasiliense Xanthomonas Acidovorax citrulli 97.71 campestris pv. 99.58 mangiferaeindicae Xanthomonas Ralstonia solanacearum 97.56 97.39 fragariae
According to the above screening results, the minimum inhibitory concentration (MIC) and sub-inhibitory concentration (SIC) of hydroxychavicol against 8 kinds of pathogenic bacteria such as Xanthomonas oryzae pv. oryzae (shown in Table 2) were measured, and the results showed that hydroxychavicol had a good bacteriostatic activity against Xanthomonas oryzae pv. oryzae, and its MIC was 340 pmol/L and SIC was 100 pmol/L; and the sub-inhibitory concentration against potato bacterial soft rot was 6 pmol/L. Table 2 Minimum inhibitory concentration and sub-inhibitory concentration of hydroxychavicol against 8 kinds of pathogenic bacteria such as Xanthomonas oryzae pv. oryzae Test bacteria MIC (pmol/L) SIC (pmol/L) Xanthomonas oryzae pv. oryzae 340 100 Xanthomonas oryzae pv. 666 260 oryzicola Xanthomonas citri subsp. citri 650 12.5 Xanthomonas campestris pv. 800 100 campestris Pectobacterium carotovorum 1400 100 subsp. carotovorum Pectobacterium carotovorum 1000 6 subsp. brasiliense Xanthomonas campestris pv. 666 41.63 mangiferaeindicae Xanthomonas fragariae 1000 80 2.2 Tissue test The test of hydroxychavicol on potato bacterial soft rot refers to a method of Habibeh et al. (Habibeh Hajian-Maleki et al. Efficiency of essential oils against Pectobacterium carotovorum subsp. carotovorum causative potato soft rot and their possible application as coatingsin storage [J]. Postharvest Biology and Technology, 2019, 156.), the specific operations of which are as follows: purchasing healthy, fresh, untreated potatoes with a uniform shape and size, after washing and drying, weighing them separately, then soaking in 1% sodium hypochlorite for 30 minutes, followed by rinsing with water and air-drying for later use; diluting hydroxychavicol with acetone to sub-inhibitory concentration, mixing Pectobacterium carotovorum subsp. brasiliense with the agent evenly for testing, punching holes on the potato with a pipette gun head, adding a medicine-carrying bacteria solution, and repeating every treatment three times. The treated potatoes were stored in a wet box with Kasugamycin as an agent control and clear water as a control. After 48 hours, rotten parts were dug out and weighed, and the inhibition rate was calculated. Inhibition rate (%) = (control rot weight-treated rot weight)/control rot weight x 100%. In vivo tissue method of potato showed that hydroxychavicol at the concentration of 6 pmol/L showed a good inhibitory effect on the pathogenicity of Pectobacterium carotovorum subsp. brasiliense, and the inhibition rate reached 82.79%. It is equivalent to that of the control agent Kasugamycin with no obvious difference. Table 3 Effect of hydroxychavicol on pathogenicity of Pectobacteriumcarotovorum subsp. brasilienseat sub-inhibitory concentration
Concentration Test samples of chemical Rot weight (g) Inhibition rate (%) (pmol/L) hydroxychavicol 6 5.02±3.87b 82.79 4% 15 3.60±0.85b 87.66 Kasugamycin Clear water - 29.17±7.12a control 2.3 Potting test 2.3.1 Potting test on bacterial fruit blotch 2 mL of hydroxychavicol with different concentrations (1000 pmol/L, 500 pmol/L and 250 pmol/L), diluted 4% Kasugamycin aqueous solution (converted to an effective component concentration of 500 pmol/L) and clear water were evenly sprayed on melon (varieties: Xizhoumi 25) seedlings, then each pot was sprayed and inoculated with fruit a blotch bacterial suspension (concentration of 1 x 109 CFU/mL); each treatment was repeated to 4 pots with 5 seedlings per pot, and the seedlings were incubated with moisture and light; a disease incidence was observed at 7 days and 14 days of the incubation, and the disease index (Formula 1) and the control effect (formula 2) are calculated [refer to: Identification of Bacillus sp. BJ-6 for biocontrol of bacterial fruit blotch of melon, Huihui JIA]. Grading of leaf diseases [refer to Pesticide-Guidelinesfor the field efficacy trials (II) "Fungicides against bacterial angular leaf spot of cucumber"]: Grade 0: no disease spots; Grade 1: an area of disease spots accounts for less than 5% of a whole leaf area; Grade 3: the area of disease spots accounts for 6- 10 % of the whole leaf area; Grade 5: the area of disease spots accounts for 11-20% of the whole leaf area; Grade 7: the area of disease spots accounts for 21-50% of the whole leaf area; Grade 9: the area of disease spots accounts for more than 51% of the whole leaf area; Efficacy calculation formula: Disease index = E (number of diseased leaves at all grades x relative grade value)/(total number of investigated leaves x highest disease grade value) x 100 (1) Control effect (%) = (control disease index-treatment disease index)/control disease index x 100 (2) Data analysis: The results of the potting test on bacterial fruit blotch showed that hydroxychavicol also has a relatively strong control effect on bacterial fruit blotch, under the treatment of a maximum test concentration of 1000 pmol/L, the control effect of hydroxychavicol on bacterial fruit blotch was 71.42%, which had no significant difference with the control agent 2% Kasugamycin aqueous solution; when its concentration was reduced to 250 pmol/L, its control effect on bacterial fruit blotch could still reach 65.44%.
Table 4 Potting test of hydroxychavicol on bacterial fruit blotch
Test concentration Test agent (pmol/L) Disease index Control effect
1000 5.82±0.44 71.42 hydroxychavicol 500 7.04±0.23 65.44 250 8.64±0.77 57.53 200Kasugamycin50 500 6.32±0.43 68.99 aqueous solution CK / 20.38±0.34
/ 2.3.2 Potting test onXanthomonas campestrispv. Mangiferaeindicae When a color of sprouted leaves of potted mango turn yellow-green, five treatments, namely, agents with concentration 1, concentration 2, concentration 3, diluted 4% Kasugamycin aqueous solution (converted into effective component concentration of 500 pmol/L) and clear water were evenly sprayed on mango seedling leaves (variety: Tainong), after drying naturally, Xanthomonas campestrispv. mangiferaeindicae(the concentration of bacterial suspension was adjusted to 1 x 109 CFU/ml) was sprayed and inoculated; 1% Tween-80 was added during the spraying; each treatment was repeated to 4 pots; the seedlings were incubated with moisture and light for 10 days and 20 days; the disease index is investigated (Formula 1), and the control effect is calculated (Formula 2). Grading standard of bacterial angular leaf spot disease[refers to Pesticide-Guidelines for the field efficacy trials (IH) "Fungicides against canker of citrus"]: Grade 0: no disease spots; Grade 1: 1-5 disease spots per leaf; Grade 3: 6-10 disease spots per leaf; Grade 5: 11-15 disease spots per leaf; Grade 7: 16-20 disease spots per leaf; Grade 9: 21 or more disease spots per leaf; Efficacy calculation formula:
Disease index = E (number of diseased leaves at all grades x relative grade value)/(total number of investigated leaves x 9) x 100 (1) Control effect (%) = (disease index after pesticide application in blank control area-disease index after test in pharmaceutical treatment area)/disease index after pesticide application in blank control area x 100 (2) Data analysis: The results showed that hydroxychavicol had a relatively strong control effect on mango bacterial black spot; when the test concentrations of hydroxychavicol were 1000 pmol/L and 500 pmol/L, the control effects on mango bacterial black spot were 76.75% and 67.73%, respectively, which was significantly better than that of the control agent 2% Kasugamycin aqueous solution; when the test concentration of hydroxychavicol was reduced to 250 pmol/L, the control effect on mango bacterial black spot was still 60.32%, and there was no significant difference with the control agent 2% Kasugamycin aqueous solution. Table 5 Potting test of hydroxychavicol on mango bacterial black spot Test concentration Test agent (pmol/L) Disease index Control effect
1000 4.32±0.38 76.75 hydroxychavicol 500 5.98±0.14 67.73 250 7.35±0.1 60.32 2%oKasugamycin50 500 6.68±0.61 63.85 aqueous solution CK / 18.55±0.72 /
The above descriptions are merely the preferred embodiments of the present invention and are not intended to limit the present invention; any modification, equivalent replacement, improvement, etc. made within the spirit and principles of the present invention should be included in the scope of protection of the present invention.
Claims (10)
1. A compound for controlling plant pathogenic bacteria, which is characterized in that the compound is hydroxychavicol, and a structural formula of the compound is shown as Formula I:
0
I."
I
2. An application of hydroxychavicol in controlling plant bacterial diseases.
3. The application of claim 2, which is characterized in that the pathogenic bacteria of the disease are Xanthomonas oryzae pv. oryzae, Xanthomonas oryzae pv. oryzicola, Xanthomonas citri subsp. citri, Acidovorax citrulli, Ralstonia solanacearum, Xanthomonas fragariae, Xanthomonas campestris pv. campestris, Pectobacterium carotovorum subsp. carotovorum, Pectobacterium carotovorum subsp. brasilienseand/orXanthomonas campestrispv. mangiferaeindicae.
4. The application of claim 3, which is characterized in that the pathogenic bacteria of the disease are Pectobacterium carotovorum subsp. brasiliense, Xanthomonas campestris pv. mangiferaeindicae and/or Acidovorax citrulli.
5. A bactericide for controlling bacterial plant diseases, which is characterized in that an active ingredient of the bactericide is hydroxychavicol, and is optionally supplemented by an auxiliary agent.
6. A bacteriostatic agent for controlling the bacterial plant diseases, which is characterized in that an active ingredient of the bacteriostatic agent is hydroxychavicol, and is optionally supplemented by an auxiliary agent.
7. The bactericide of claim 5 or the bacteriostatic agent of claim 6, which is characterized in that dosage forms of the fungicide or the bacteriostatic agent are suspension concentrate, emulsion in water, microemulsion, emulsifiable concentrate, wettable powder or water dispersible granule.
8. A preparation method of hydroxychavicol, which is characterized in comprising:
S1: collecting the branches and the leaves of the piper austrosinense, drying in the shade, crushing and sieving to obtain a dry powder, performing a first cold soaking with an ethanol solution, and filtering to obtain a first filtrate and a filter residue; performing a second cold soaking and extracting on the filter residue with the ethanol solution until the filtrate is colorless to obtain a second filtrate, merging the first filtrate and the second filtrate, and concentrating to dryness to obtain an ethanol extract of the piper austrosinense; S2: adding a water to suspend the ethanol extract of the piper austrosinense, extracting with a petroleum ether, concentrating to dryness to obtain a petroleum ether extract; S3: applying the petroleum ether extract to a column by a petroleum ether wet method, and eluting in a petroleum ether-ethyl acetate system to obtain nine fractions; and S4: a fraction 3 is eluted by the petroleum ether-ethyl acetate system to obtain hydroxychavicol.
9. The preparation method of claim 8, which is characterized in that in step Sl, a volume concentration of the ethanol solution is 90% to 95%; a duration of the first cold soaking is 6 to 7 days; a mass ratio of the dry powder to the ethanol solution in the first cold soaking is 1:(9-10); and a mass ratio of the filter residue to the ethanol solution in the second cold soaking is 1:(9-10).
10. The preparation method of claim 8, which is characterized in that in step S3, a volume ratio of the petroleum ether to the ethyl acetate is (2.5-3):1; in step S4, the volume ratio of the petroleum ether to the ethyl acetate is (9-10):1.
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