CN113519526A - Application of flavanone in inhibiting tobacco black shank bacteria - Google Patents
Application of flavanone in inhibiting tobacco black shank bacteria Download PDFInfo
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- CN113519526A CN113519526A CN202010306422.7A CN202010306422A CN113519526A CN 113519526 A CN113519526 A CN 113519526A CN 202010306422 A CN202010306422 A CN 202010306422A CN 113519526 A CN113519526 A CN 113519526A
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/04—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aldehyde or keto groups, or thio analogues thereof, directly attached to an aromatic ring system, e.g. acetophenone; Derivatives thereof, e.g. acetals
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Abstract
The flavanone compounds can be used for inhibiting tobacco phytophthora parasitica. The invention belongs to the technical field of bactericidal active compounds. The invention aims to solve the technical problem that the method for inhibiting tobacco black shank bacteria mainly by using the traditional chemical pesticide bactericide poses great threats to food safety and ecological environment. The flavanone substance is applied to plant diseases caused by the tobacco black shank as a bacteriostatic agent; the flavanone is a flavonoid compound derived from naringenin, phloretin, liquiritigenin or hesperetin with 2-phenyldihydrochromone as mother nucleus. Indoor toxicity measurement proves that the flavanone substances have good inhibitory activity on tobacco black shank bacteria, and can be used as a natural, pollution-free and environment-friendly high-efficiency bactericide. Not only can solve the problems of pathogenic bacteria drug resistance and pesticide residue caused by excessive dependence on a single bactericide, but also can not cause environmental pollution.
Description
Technical Field
The invention belongs to the technical field of bactericidal active compounds, and particularly relates to an application of flavanone substances in inhibition of tobacco phytophthora parasitica.
Background
Tobacco black shank is a devastating tobacco root disease caused by phytophthora parasitica. Phytophthora parasitica not only has a broad host range, but also, as a typical root pathogen, represents most of the Phytophthora species. Therefore, phytophthora parasitica has been studied as an oomycete pathogenic model species in recent years. The phytophthora parasitica can damage almost all cultivated tobaccos, is extremely destructive, causes serious loss to tobacco production in the world, is almost difficult to control once the disease occurs, and is one of the most destructive diseases damaging the tobacco production at present. At present, chemical prevention is mainly used for preventing and treating the diseases in production, and the long-term use of chemical prevention and treatment means for preventing and treating the diseases can enhance the drug resistance of pathogenic bacteria, and along with the long-term continuous increase of the using amount of the traditional bactericide, the chemical residue in crops rises, so that the food safety is greatly threatened, and meanwhile, the environment is also greatly polluted. With the improvement of the living standard of human beings and the progress of science and technology, the search for a low-residue, pollution-free and environment-friendly method for preventing and treating plant diseases is urgent.
Flavanones are a large class of flavonoids, and refer to compounds derived from 2-phenyldihydrochromone as a parent nucleus. The flavanone is 2-phenyldihydrochromone, also known as flavanone. The plants are mostly hydroxy derivatives thereof, and the mother nucleus may have methoxy or other substituents. The flavanone is colorless compound, has chiral carbon atom in molecule, and thus has optical activity, single bond between C2-C3, and carbonyl at C4 site with typical ketone property (different from flavone). When treated with alkali, chalcone is produced by ring opening, flavanone is converted by acidification, and the two are isomers, and are often coexisted in plants. The molecular structural formula is:
naringenin, phloretin, hesperetin and liquiritigenin all belong to flavanone substances.
Naringenin: naringin aglycone belongs to flavanone compound, has the functions of antibiosis, anti-inflammation, free radical elimination, antioxidation, cough relieving, phlegm eliminating, blood fat reducing, cancer resistance, tumor resistance, spasmolysis, cholagogue, liver disease prevention and treatment, platelet coagulation inhibition, atherosclerosis resistance and the like, and can be widely applied to the fields of medicine, food and the like.
Phloretin: also called trihydroxy phenol acetone 2,4, 6-trihydroxy-3- (4-hydroxyphenyl) propiophenone, is mainly distributed in the pericarp and root bark of succulent fruits such as apple, pear, etc. Has antioxidant, free radical scavenging, antitumor, anticancer, antidiabetic, antiparkinson, antiinflammatory, and immunosuppressive effects.
Hesperetin: also called 4-methoxy-3, 5',7' -trihydroxy flavanone, belongs to flavanone compounds. Mainly comes from young fruits of citrus in the family of rutaceae, and is not widely applied at present.
Liquiritigenin: also known as glycyrrhizin, belongs to flavanone compounds. Mainly exists in the root and stem of liquorice, the content of the timonacic substance in the domestic liquorice with skin is about 7 to 10 percent, and the content of the timonacic substance in the liquorice with skin is about 5 to 9 percent. At present, the method is widely applied to sweetening and seasoning of cans, seasonings, candies, biscuits and preserves (Guangdong preserved fruits).
At present, there is no report about flavanone as an inhibitor for preventing and treating tobacco black shank at home and abroad.
Disclosure of Invention
The invention aims to solve the technical problem that the food safety and the ecological environment are greatly threatened by the conventional method for inhibiting the tobacco black shank taking the traditional chemical pesticide bactericide as the main part, and provides the application of the flavanone substances in inhibiting the tobacco black shank.
The flavanone substance is applied to plant diseases caused by the tobacco black shank as a bacteriostatic agent; the flavanone substances are flavonoid compounds derived from 2-phenyldihydrochromone serving as a parent nucleus.
Further limiting, the flavonoid compound derived by taking the 2-phenyldihydrochromone as the mother nucleus is naringenin, phloretin, liquiritigenin or hesperetin.
Further limited, the effective bacteriostasis concentration of the naringenin as the bacteriostat is 20.19mg/L to 200 mg/L.
Further limited, the effective bacteriostasis concentration of the phloretin as the bacteriostat is 30.91 mg/L-200 mg/L.
Further limit, when the liquiritigenin is used as a bacteriostatic agent, the effective bacteriostatic concentration is 48.93 mg/L-200 mg/L.
Further limited, the effective bacteriostasis concentration of the hesperetin as the bacteriostat is 34.91 mg/L-200 mg/L.
Compared with the prior art, the invention has the remarkable effects as follows:
1. the invention can be used for various bacteriostatic substances, and can avoid the problem of drug resistance enhancement of bacteria caused by long-term use of a single bactericide in disease control.
2. Indoor toxicity measurement proves that the flavanone substances represented by naringenin have good inhibitory activity on a plurality of representative oomycetes.
3. The compound flavanone substance is derived from plants, has the advantages of greenness, naturalness, no toxicity, harmlessness, no residue, environmental safety, friendliness, easy degradation, easy extraction and low production cost, has excellent and stable bacteriostatic action and bacteriostatic effect, has higher inhibitory toxicity on pathogenic oomycetes to be tested than other contrast flavonoid medicaments, and is suitable for the requirements of chemical control on plant diseases and green sustainable development of agricultural production.
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FIG. 1 is a comparison graph of the variation trend of hypha diameter in the bacteriostasis process of tobacco black shank bacteria by naringenin, phloretin, liquiritigenin, hesperetin (a control group of flavonols such as kaempferol, quercetin, rutin and the like);
FIG. 2 is a graph showing the inhibition rate of naringenin, phloretin, liquiritigenin and hesperetin against tobacco black shank bacteria varying with the concentration of bacteriostatic agent;
FIG. 3 is a graph of the effect of naringenin on the germination of tobacco phytophthora parasitica sporangia as a function of bacteriostatic concentration;
FIG. 4 is a microscopic view of the effect of naringenin on the germination of tobacco blackleg bacterium sporangia;
FIG. 5 is a graph showing the effect of naringenin on germination of tobacco phytophthora parasitica dormant spores;
FIG. 6 is a microscopic observation picture of the effect of naringenin on germination of tobacco phytophthora parasitica dormant spores.
Detailed Description
The following examples are provided to aid understanding of the present invention, but are not intended to limit the scope of the present invention.
The first embodiment is as follows: the flavanone substance of the present embodiment is used for inhibiting tobacco black shank bacteria by applying the flavanone substance as a bacteriostatic agent to plant diseases caused by tobacco black shank bacteria; the flavanone substances are flavonoid compounds derived by taking 2-phenyldihydrochromone as a parent nucleus; the flavonoid derived from 2-phenyldihydrochromone as mother nucleus is naringenin, phloretin, liquiritigenin or hesperetin.
The bacteriostatic effect of the first embodiment is illustrated by the following verification test:
the experiment I and the in-vitro bacteriostatic experiment comprise the following specific steps:
firstly, preparing a bacteriostatic agent: respectively adding 40mg of naringenin (or phloretin, liquiritigenin and hesperetin) into 1mL of absolute ethyl alcohol (analytically pure) to be completely dissolved to obtain bacteriostatic solution, sucking 0.5mL of the bacteriostatic solution from 40mg/mL into a new 1.5mL PE tube according to a half-and-half dilution method, adding 0.5mL of absolute ethyl alcohol into the new 1.5mL PE tube, and shaking up, so as to prepare bacteriostatic agent solutions of 40mg/mL, 20mg/mL, 10mg/mL, 5mg/mL, 2.5mg/mL, 1.25mg/mL and 0.625 mg/mL; naringenin, phloretin, liquiritigenin, and hesperetin are all purchased from standard products of Solebao corporation;
secondly, preparing a PDA culture medium: cleaning and peeling potatoes, cutting the potatoes into small pieces, weighing 200g, adding water, boiling, filtering the potato pieces into a beaker by using gauze after the potato pieces are boiled thoroughly, adding 20g of glucose and 16g of agar, uniformly stirring, fixing the volume to 1L, subpackaging, sterilizing at 121 ℃ for 30 minutes, and cooling to 45-50 ℃ for later use;
thirdly, preparing an antibacterial flat plate: heating and melting the PDA culture medium in the second step, measuring 50mL of PDA liquid culture medium by using a measuring cylinder, adding 0.5mL of bacteriostatic agent solutions with different concentrations obtained in the first step into the PDA liquid culture medium, namely naringenin solution (or phloretin solution, liquiritigenin solution and hesperetin solution), adding 0.5mL of flavonols (kaempferol, quercetin and rutin) into a control group, adding 0.5mL of absolute ethyl alcohol into a blank control group (control), uniformly shaking, and pouring the plate for later use, wherein three plates can be obtained from every 50mL of culture medium, and the concentration gradients of the three plates are 400mg/L, 200mg/L, 100mg/L, 50mg/L, 25mg/L, 12.5mg/L and 6.25mg/L in sequence;
fourthly, preparing a pathogenic bacteria plate: putting the phytophthora parasitica in the PDA culture medium of the step two, and culturing for 14d at 28 ℃;
fifthly, in vitro bacteriostasis: adopting a growth rate method, punching the fungus cakes on the pathogenic bacteria plates in the fourth step by using a puncher (with the diameter of 0.5cm) after autoclaving, taking the center of strain hyphae as an original point when punching the fungus cakes, punching the fungus cakes with the same radius, and then moving the fungus cakes to the center of the bacteriostatic flat plate in the third step, wherein the moving process ensures sterility;
sixthly, the method comprises the following steps: culturing: culturing the culture dish in an incubator at 28 deg.C, observing and measuring the growth condition of hyphae 7d after treatment, simultaneously photographing and recording, measuring diameter processing data by adopting a cross method (fungus cakes at different radii), and calculating the inhibition rate.
Inhibition (%) - (control hypha diameter-treated hypha diameter)/control hypha diameter × 100
Regression line equation: y-bx + a
a is the average of inhibition-b is the average of log concentration
As a result: repeating the above treatments for 4 times to obtain a graph of the inhibition rate of naringenin, phloretin, liquiritigenin and hesperetin on tobacco black shank bacteria with the change of the concentration of the bacteriostatic agent as shown in figure 1, a hypha diameter change trend graph as shown in figure 2 and in-vitro bacteriostatic action data as shown in table 1.
TABLE 1 inhibition of growth of tobacco black shank hyphae by flavanone type substances results (7d)
| Flavanone compounds | Regression equation | Coefficient of correlation r | EC50(mg/L) |
| Naringenin | Y＝0.3913X-0.0107 | 0.9762 | 20.19 |
| Phloretin | Y＝0.3817X-0.0688 | 0.972 | 30.92 |
| Liquiritigenin | Y＝0.3719X-0.1282 | 0.9028 | 48.93 |
| Hesperetin | Y＝0.352X-0.0431 | 0.97 | 34.91 |
As can be seen from FIG. 1, the tobacco Heiytophthora parasitica is more sensitive to naringenin, EC50The lowest value indicates that the bacteriostatic effect is most obvious, and the EC of liquiritigenin50The value was highest among the four agents. The flavonol components have no inhibiting effect on tobacco black shank bacteria.
As can be seen from FIG. 2, when the concentrations of the phloretin and the liquiritigenin bacteriostatic solutions respectively reach 400mg/L, hypha of the tobacco phytophthora parasitica vegetative mass hardly grows, meanwhile, the lower-concentration liquiritigenin has no obvious inhibition on the hypha, and the high-concentration liquiritigenin has obvious inhibition on the hypha growth. The hesperetin at 200mg/L is not as remarkable in inhibition of hypha growth as other three bacteriostatic solutions, which indicates that the Heiguobium tabacum has stronger tolerance to hesperetin.
And (2) test II: effect of naringenin on the formation of sporangia and the germination of zoospores in tobacco
The difference between this test and test one is that: the first test only explores the influence of the bacteriostatic liquid on the growth of the tobacco black shank, the first test screens naringenin with the best bacteriostatic effect from the first test to further research, explores the influence of naringenin on the reproduction of the tobacco black shank, and comprises the following specific test steps:
firstly, preparing a V8 liquid culture medium, namely adding 3.4g of calcium carbonate powder into 340mL of V8 mixed fruit and vegetable juice, centrifuging for 5min at 4 ℃ and 4000rpm, measuring 300mL of fruit and vegetable juice without solid suspension, adding 2700mL of deionized water into the fruit and vegetable juice to prepare a 3L V8 liquid culture medium, subpackaging, sterilizing at 121 ℃ for 30min, and cooling to 45-50 ℃ for later use; the V8 fruit and vegetable juice is purchased from American 'Jinbao V8 vegetable juice 100%' 340mL canned standard product;
secondly, preparing a bacteriostatic agent: according to a half-dilution method, 0.5mL of the bacteriostatic solution left in the step one in the test one is sucked into a new 1.5mL PE tube, and then 0.5mL of absolute ethyl alcohol is added and shaken up, so that bacteriostatic agent solutions of 1.25mg/mL, 0.625mg/mL, 0.3125mg/mL, 0.15625mg/mL and 0.078125mg/mL are prepared by analogy; the naringenin is purchased from standard products of Solebao company;
thirdly, inducing mycelium formation: transferring the tobacco phytophthora parasitica to a PDA (personal digital assistant) culture medium, continuously culturing for 14 days in the dark at 28 ℃, punching bacterial cakes on the edges of bacterial colonies by using a puncher with the diameter of 5mm, placing the bacterial cakes in sterile and clean culture dishes, placing 7-10 bacterial cakes in each culture dish, adding 15mL of V8 liquid culture medium obtained in the first step, and taking every three culture dishes as a group to obtain 7 groups in total; culturing for 48h in a dark environment at 28 ℃;
fourthly, inducing the formation of sporangia: pouring out the V8 culture medium after mycelium is formed, washing the mycelium with sterile water, weighing 50mL of sterile water, adding 0.5mL of 1.25mg/mL of bacteriostatic solution to prepare 12.5mg/L solution, and respectively adding the solution into the culture dish treated in the third step, wherein the concentration gradient of the solution is 12.5mg/L, 6.25mg/L, 3.125mg/L, 1.5625mg/L and 0.78125mg/L in sequence; adding 0.5mL of absolute ethyl alcohol into 50mL of sterilized water in a control group; after illumination for 72h at 28 ℃, sporangium formation can be observed under a microscope and counted;
fifthly, collecting dormant spores: repeating the operation of the fourth step, but not adding the bacteriostatic agent, placing the culture dish into a refrigerator at 4 ℃ for 30min after the sporangium germinates in a large amount to stimulate spore germination, collecting liquid in the culture dish, centrifuging for 3min at 4 ℃ and 3000rpm, pouring out supernatant, adding 1mL of sterile water, sucking the sterile water by using a liquid-moving gun, uniformly dispersing the zoospores deposited at the bottom of the centrifugal tube into the sterile water to obtain zoospore suspension, observing under a 40-fold microscope, and controlling the concentration of the zoospore suspension to be within the range of 40-fold1×106Per mL;
sixthly, culturing: mixing the prepared zoospore suspension (1 × 10)6piece/mL) is shaken on a vortex instrument for 10min, 20 mu L of each zoospore suspension and bacteriostatic solution (12.5mg/L, 6.25mg/L, 3.125mg/L, 1.5625mg/L and 0.78125mg/L) are taken and dripped on a concave glass at the same time, the zoospore suspension and the bacteriostatic solution are subjected to moisture preservation and culture at the temperature of 20 ℃ in the dark, the number of germinated resting spores is observed under a microscope after 3h, each concentration is repeated four times, and the germination rate of 100 resting spores is calculated every time.
The spore germination inhibition rate is (control spore germination rate-treated spore germination rate)/the control spore germination rate is multiplied by 100%.
The rate of inhibition of sporangial formation ═ (number of control sporangia-number of treated sporangia)/number of control sporangia × 100%.
Regression line equation: y-bx + a
a is the average of inhibition-b is the average of log concentration
As a result: repeating each treatment 4 times to obtain a graph of the effect of naringenin on the germination of sporangium of phytophthora parasitica as shown in FIG. 3 and a microscopic observation graph as shown in FIG. 4; a graph showing the influence of naringenin on the germination of dormant spores of phytophthora parasitica as shown in fig. 5 and a microscopic observation chart as shown in fig. 6 were obtained, as well as reproduction inhibition data of phytophthora parasitica as shown in table 2.
TABLE 2 naringenin inhibition of reproduction of tobacco black shank bacteria
| State of phytophthora | Regression equation | Coefficient of correlation r | EC50(mg/L) |
| Sporangial germination | Y＝1.0113X+0.0847 | 0.8446 | 2.574 |
| Dormant spore germination | Y＝0.4894x | 0.914 | 10.51 |
As can be seen from FIGS. 3 to 4, the germination of phytophthora nicotianae sporangia is very sensitive to naringenin, and has a good inhibitory effect.
From fig. 5-6, it can be seen that naringenin also has a good inhibitory effect on dormant spores, and can achieve the trace and efficient target.
Claims (6)
1. The application of the flavanone substances in inhibiting the tobacco phytophthora parasitica is characterized in that the flavanone substances are applied to plant diseases caused by the tobacco phytophthora parasitica as bacteriostats; the flavanone substances are flavonoid compounds derived from 2-phenyldihydrochromone serving as a parent nucleus.
2. The application of the flavanone substances in inhibiting tobacco black shank bacteria according to claim 1, wherein the flavonoid compound derived from 2-phenyldihydrochromone as a mother nucleus is naringenin, phloretin, liquiritigenin or hesperetin.
3. The application of the flavanone substances in inhibiting tobacco black shank bacteria according to claim 1, wherein the effective inhibitory concentration of naringenin as a bacteriostatic agent is 20.19 mg/L-200 mg/L.
4. The application of the flavanone substances in inhibiting tobacco black shank bacteria according to claim 1, wherein the effective bacteriostasis concentration of phloretin as a bacteriostat is 30.91 mg/L-200 mg/L.
5. The application of the flavanone substances in inhibiting tobacco black shank according to claim 1, wherein the effective bacteriostatic concentration of liquiritigenin as a bacteriostatic agent is 48.93 mg/L-200 mg/L.
6. The application of the flavanone substances in inhibiting tobacco black shank bacteria according to claim 1, wherein the effective bacteriostasis concentration of hesperetin as a bacteriostat is 34.91 mg/L-200 mg/L.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114788524A (en) * | 2022-01-25 | 2022-07-26 | 中国农业科学院烟草研究所(中国烟草总公司青州烟草研究所) | Bacteriostatic microemulsion preparation and preparation method and application thereof |
| CN116965411A (en) * | 2023-09-19 | 2023-10-31 | 浙江大学海南研究院 | Application of flavonoid compound in preparation of pesticide |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114788524A (en) * | 2022-01-25 | 2022-07-26 | 中国农业科学院烟草研究所(中国烟草总公司青州烟草研究所) | Bacteriostatic microemulsion preparation and preparation method and application thereof |
| CN114788524B (en) * | 2022-01-25 | 2024-05-31 | 中国农业科学院烟草研究所(中国烟草总公司青州烟草研究所) | Antibacterial microemulsion preparation and preparation method and application thereof |
| CN116965411A (en) * | 2023-09-19 | 2023-10-31 | 浙江大学海南研究院 | Application of flavonoid compound in preparation of pesticide |
| CN116965411B (en) * | 2023-09-19 | 2024-01-09 | 浙江大学海南研究院 | Application of flavonoid compound in preparation of pesticide |
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