CN110547296A - Application of atractylenolide I and analogs thereof in preventing and treating agricultural diseases - Google Patents

Application of atractylenolide I and analogs thereof in preventing and treating agricultural diseases Download PDF

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Publication number
CN110547296A
CN110547296A CN201910873021.7A CN201910873021A CN110547296A CN 110547296 A CN110547296 A CN 110547296A CN 201910873021 A CN201910873021 A CN 201910873021A CN 110547296 A CN110547296 A CN 110547296A
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China
Prior art keywords
atractylenolide
analogues
preventing
application
diseases
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CN201910873021.7A
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Chinese (zh)
Inventor
刘映前
孙钰
赵文斌
吴争荣
秦芳
王仁轩
杨程杰
彭静文
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Lanzhou University
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Lanzhou University
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Priority to CN201910873021.7A priority Critical patent/CN110547296A/en
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    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/12Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings condensed with a carbocyclic ring

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

The invention belongs to the field of natural medicinal chemistry, and discloses application of atractylenolide I and analogues (B1-B4) thereof in preventing and treating diseases caused by rhizoctonia solani, sclerotinia sclerotiorum, botrytis cinerea, fusarium graminearum and pyricularia grisea, particularly application of atractylenolide I in preparing agricultural bactericide

Description

Application of atractylenolide I and analogs thereof in preventing and treating agricultural diseases
Technical Field
The invention belongs to the field of natural medicinal chemistry, discloses a new application of atractylenolide I and analogues thereof, and particularly relates to an application of atractylenolide I in preventing and treating diseases caused by sclerotinia sclerotiorum, rhizoctonia solani, botrytis cinerea, fusarium graminearum and rice blast.
Background
Plant diseases are one of the main factors influencing agricultural production, and according to the estimation of the grain and agriculture organization of the United nations, the annual loss of grain and cotton production all over the world is more than 10 percent due to the diseases. At present, chemical agents are mainly used for preventing and treating plant diseases in various countries in the world, however, due to long-term use of the chemical agents, a series of serious problems such as residue, pollution, drug resistance of harmful organisms, damage to non-target organisms and even damage to ecological balance are caused, so research and development of novel pesticides with high efficiency, low toxicity and low residue, which can effectively control plant pathogenic bacteria, become the primary target of pesticide creation at present. The finding of bacteriostatic and bactericidal active substances from plants is one of the important ways for researching and developing green bactericides at present.
atractylodes macrocephala lactone I (Atractylenylolide I), Atractylodes macrocephala lactone II (Atractylenylolide II), Atractylodes macrocephala lactone III (Atractylenylolide III) and atractylone (Atractylenone) are the main active ingredients in the volatile oil of Atractylodes macrocephala (Atractylodes macrocephala-la koedz) of Compositae. The research in recent years shows that the bighead atractylodes rhizome has the effects of diuresis, antibiosis, anti-aging, anti-tumor and the like, also has a certain effect on nervous system, uterine smooth muscle and gastrointestinal movement, and also has the function of regulating immunity. With respect to bactericidal activity, studies have shown that: the Atractylodis rhizoma has different degrees of inhibition effects on Escherichia coli, Shigella sonnei, Shigella freundii, Proteus, typhoid bacillus, paratyphoid bacillus, Pseudomonas aeruginosa, Vibrio cholerae, gram-positive bacteria and human type tubercle bacillus. However, no research report about the atractylenolide compound in the aspect of preventing and treating plant pathogenic fungi is found. Based on the above, the invention takes the atractylenolide I and the analogues thereof as research objects, and performs bactericidal activity evaluation on the atractylenolide I, and finds that the atractylenolide I shows a certain inhibition effect on sclerotinia sclerotiorum, rhizoctonia solani, botrytis cinerea, fusarium graminearum and pyricularia oryzae, and particularly has strong bacteriostatic activity on rhizoctonia solani, so that the atractylenolide I can be further developed as a bactericidal lead compound. Meanwhile, the atractylenolide is used as a lead compound to create a novel bactericide, and has the advantages of natural pesticides, so that atractylenolide I and analogues thereof have good development prospects as the bactericide for preventing and treating important crop diseases.
Disclosure of Invention
The invention aims to provide a natural source bactericide for agricultural production aiming at the defects in the prior art. The application of atractylenolide I and its analogues in preventing and treating diseases caused by Sclerotinia sclerotiorum, Rhizoctonia solani, Gibberella tritici, Botrytis cinerea and Magnaporthe grisea.
In order to achieve the purpose, the invention provides the following technical method: a medicine for preventing and treating diseases caused by Sclerotinia sclerotiorum, Rhizoctonia solani, Gibberella graminis, Botrytis cinerea and Magnaporthe grisea contains therapeutically effective compounds (B1) - (B4), such as atractylenolide compounds represented by formula I.
Structural formula I
The atractylenolide I and the analogues thereof as novel agricultural bactericides have the following advantages:
1) The bactericidal activity is higher. In particular, the disease caused by Rhizoctonia solani, EC thereof50Can reach 0.0325mg/mL, and can be developed as a new sterilization precursor.
2) Atractylenolide I and its analogues are natural active ingredients. The bactericide has the characteristics of low toxicity, low residue, environmental compatibility, difficult resistance generation and the like, can be developed into a botanical pesticide for producing green and pollution-free agricultural products, and belongs to a novel biological pesticide.
The foregoing and other aspects of the present invention will become more apparent from the following detailed description, given by way of example only, for purposes of illustrating the invention. This is not to be construed as limiting the invention.
Detailed Description
Example 1: the chemical formulas (B1) to (B4) are obtained by separation, and the structural identification of the chemical formulas is consistent with that reported in the literature. Atractylenolide I (B1) CAS: 73069-13-3, purity > 98%; atractylenolide II (B2) CAS: 73069-14-4, purity > 98%; atractylenolide III (B3) CAS: 73030-71-4; atractylone (B4) CAS: 6989-21-5, purity > 98%.
Example 2: indoor bacteriostatic activity determination and result
The plant pathogenic bacteria used in the experiment are strains preserved at 4 ℃ in a laboratory, and the adopted culture medium is a potato agar glucose culture medium (PDA for short). The PDA culture medium formula comprises: potato (peeled) 200g, glucose 20g, agar 15g, distilled water 1000mL, natural pH.
The configuration method comprises the following steps: cleaning and peeling potatoes, weighing 200g of potatoes, cutting the potatoes into small pieces, adding water, boiling the potatoes thoroughly (boiling for 20-30 minutes and being capable of being punctured by a glass rod), filtering the potatoes by four layers of gauze, adding water into a beaker to 1000mL, adding 15-20g of agar according to experimental requirements, adding 20g of glucose, stirring the mixture to fully dissolve the agar, subpackaging the mixture in a triangular flask, sterilizing the mixture for 20 minutes at 121 ℃, and cooling the mixture for later use.
Experimental methods
1) A hypha growth rate method is adopted.
1. Firstly, 10 plant pathogenic bacteria are cultured on a PDA (personal digital assistant) plate at 25 ℃ for 3-6 days for activation.
2. Heating PDA culture medium to melt, cooling to 45-50 deg.C, adding atractylenolide compounds with different concentrations, and making into tablet with drug.
3. According to the aseptic operation procedure, a hole puncher is used for beating a circular fungus cake (the diameter is 5mm) at the edge of each bacterial strain hypha cultured for 3-6 days (the growth conditions are consistent as much as possible), then a inoculation needle is used for picking the circular fungus cake to the center of a medicine-containing flat plate, and then a culture dish is placed in an incubator (25 ℃) for culture.
4. And (4) observing and measuring the growth condition of the hyphae after the blank control group is fully grown, measuring the diameter by adopting a cross method, processing data and calculating the inhibition rate.
5. Inhibition (%) × (control hypha diameter-treated hypha diameter)/(control hypha diameter-cake diameter) × 100
6. Each treatment was repeated 3 times.
TABLE 1 bacteriostatic Activity of atractylenolide I and its analogues on phytopathogenic fungi
TABLE 2 bacteriostatic Activity of atractylenolide I & atractylenolide II on Rhizoctonia solani
Note that three replicates were set for each treatment in the experiment and the data in the table are the average of the three replicates.
As can be seen from the bioassay results in Table 1, the atractylenolide I and the analogues thereof have good inhibitory activity on sclerotium napellus, rhizoctonia solani, botrytis cinerea, gibberella zeae and rice blast, wherein the inhibitory activity on rhizoctonia solani is more than 50% under the condition that the concentration of the atractylenolide I and the atractylenolide II is 0.05 mg/mL. Atractylodes macrocephala lactone I was calculated on the basis of the bioassay results of Table 1&EC of Atractylodes macrocephala lactone II on Rhizoctonia solani50The value is obtained. The results show that the activity of atractylenolide I to rhizoctonia solani is best, and the EC of atractylenolide I is best50The value was 0.0325 mg/mL. In conclusion, the atractylenolide compound provided by the invention has a simple structure, and some compounds show significant inhibitory activity to agricultural germs, and have further research value.

Claims (6)

1. The invention relates to application of atractylenolide I and analogues thereof in preventing and treating agricultural diseases, and relates to new application of atractylenolide I and analogues thereof (B1-B4). Atractylenolide I and its analogues have the following molecular structures.
2. The use of atractylenolide I and its analogues (B1-B4) according to claim 1 for the control of Sclerotinia sclerotiorum caused diseases.
3. The use of atractylenolide I and its analogues (B1-B4) according to claim 1 for the control of diseases caused by Rhizoctonia solani.
4. The use of atractylenolide I and its analogues (B1-B4) according to claim 1 for the control of diseases caused by Botrytis cinerea.
5. The use of atractylenolide I and its analogues (B1-B4) according to claim 1 for the control of diseases caused by wheat scab.
6. The use of atractylenolide I and its analogues (B1-B4) according to claim 1 for the control of diseases caused by Pyricularia oryzae.
CN201910873021.7A 2019-09-16 2019-09-16 Application of atractylenolide I and analogs thereof in preventing and treating agricultural diseases Pending CN110547296A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114945352A (en) * 2020-01-17 2022-08-26 联合利华知识产权控股有限公司 Topical compositions comprising hydroxamic acid and atractylenolide

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102726457A (en) * 2012-06-25 2012-10-17 浙江农林大学 Novel agricultural sterilization purpose of white atractylodes rhizome extracts

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102726457A (en) * 2012-06-25 2012-10-17 浙江农林大学 Novel agricultural sterilization purpose of white atractylodes rhizome extracts

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
李滢等: "生白术化学成分研究", 《中国现代中药》 *
武汉医学院等: "《营养与食品卫生学》", 31 July 1981, 人民卫生出版社 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114945352A (en) * 2020-01-17 2022-08-26 联合利华知识产权控股有限公司 Topical compositions comprising hydroxamic acid and atractylenolide

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Application publication date: 20191210