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Application of luotonin A derivative in treatment of plant virus disease

A technology for plant virus disease, cameline, applied in the direction of chemicals, applications, biocides, etc. for biological control

Active Publication Date: 2022-01-28
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Cameline A has biological activity on specific human cancer cells. So far there is no report on the prevention and treatment of plant virus and bacterial diseases by cameline A, and camelline A is enough to be a good lead compound for the development of new drugs

Method used

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  • Application of luotonin A derivative in treatment of plant virus disease
  • Application of luotonin A derivative in treatment of plant virus disease
  • Application of luotonin A derivative in treatment of plant virus disease

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0008] Example 1: Experimental data of the structural formulas of cameline A derivatives I-1 to I-17

[0009] I-1: white solid, melting point 208-210°C. 1 H NMR (400MHz, DMSO-d 6 )δ8.78(s, 1H), 8.32-8.27(m, 2H), 8.18(d, J=8.1Hz, 1H), 7.98-7.89(m, 3H), 7.78(t, J=7.5Hz, 1H ), 7.68-7.62(m, 1H), 5.33(s, 2H). 13 C NMR (100MHz, DMSO-d 6 )δ160.2, 153.6, 152.0, 149.5, 148.8, 135.0, 132.3, 131.5, 133.0, 130.2, 129.0, 128.8, 128.5, 127.7, 126.4, 48.0.

[0010] I-2: Pale red solid, melting point 272-274°C. 1 H NMR (400MHz, DMSO-d 6 )δ8.66(s, 1H), 8.30(d, J=7.8Hz, 1H), 8.18(d, J=8.7Hz, 1H), 7.96-7.93(m, 3H), 7.78-7.74(m, 1H ), 7.67-7.61(m, 1H), 5.31(s, 2H), 2.58(s, 3H).

[0011] I-3: Yellow-green solid, melting point 280-282°C. 1 H NMR (400MHz, DMSO-d 6 )δ8.55(s, 1H), 8.29(d, J=7.6Hz, 1H), 7.97-7.88(m, 2H), 7.68-7.60(m, 2H), 7.54(s, 1H), 5.28(s , 2H), 4.00 (d, J=10.1Hz, 6H).

[0012] I-4: white solid, melting point > 300°C. 1 H NMR (400MHz, DMSO-d 6 )δ8.74(s, 1H), 8.35(d, J=2...

Embodiment 2

[0026] Embodiment 2: the assay of anti-tobacco mosaic virus activity, assay procedure is as follows:

[0027] 1. Virus purification and concentration determination:

[0028] Virus purification and concentration determination were carried out in accordance with the SOP specification for tobacco mosaic virus compiled by the Bioassay Laboratory of the Institute of Elements, Nankai University. After the crude virus extract was centrifuged twice with polyethylene glycol, the concentration was measured and refrigerated at 4°C for later use.

[0029] 2. Compound solution preparation:

[0030] After weighing, the original drug was dissolved in DMF to prepare 1×10 5 μg / mL mother solution, and then diluted with 1‰ Tween 80 aqueous solution to the required concentration; Ningnanmycin preparation was directly diluted with water.

[0031] 3. In vivo protection:

[0032] Select Shanxi tobacco with uniform growth at the 3-5 leaf stage, spray the whole plant, and repeat each treatment 3 t...

Embodiment 3

[0042] Embodiment 3: antibacterial activity test, assay procedure is as follows:

[0043] In vitro bactericidal test, bacterial growth rate determination method (plate method):

[0044] Dissolve a certain amount of medicine in an appropriate amount of acetone, then dilute it with an aqueous solution containing 200 μg / mL emulsifier to the required concentration, then draw 1 mL of the medicine solution into the petri dish, then add 9 mL of medium, shake well and make 50 μg / mL mL of the drug-containing plate, and a plate with 1 mL of sterilized water added as a blank control. Use a hole puncher with a diameter of 4mm to cut out the bacterial plate along the outer edge of the hyphae, and move it to the plate containing the medicine. Each treatment was repeated three times. Place the culture dish in a constant temperature incubator at 24±1°C. After 48 hours, investigate the expanded diameters of the bacteria discs of each treatment, calculate the average value, and compare with ...

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Abstract

The invention relates to application of a luotonin A derivative in treatment of plant viruses and pathogenic bacteria, and finds that the luotonin A derivatives I-1-I-17 show good anti-plant virus and pathogenic bacteria activity for the first time, and can well inhibit tobacco mosaic virus (TMV) and 14 plant pathogens including cucumber fusarium wilt, peanut brown spot, Apple Ring Rot, wheat sheath blight, Corn southern leaf blight, Colletetrichum orbicalare, Fussrium moniliforme, Alternaria solani Sorauer, Wheat Scab, Pyricularia grisea, phytophthora capsici, sclerotinia rot of colza, Borrytis cinerea and Pellicularia sasakii Ito.

Description

technical field [0001] The invention relates to the application of camelline A derivatives in treating plant viruses and bacterial diseases, and belongs to the technical field of agricultural protection. Background technique [0002] Cameline A is an alkaloid isolated from Artemisia camelus. In 2003, the Hecht research group of the University of Virginia (J.Am.Chem.Soc.2003, 125, 13628-13629.) found that cameline A showed an inhibitory effect on mouse tumor cell P388 cell line in vitro, and its IC 50 It was 1.8 μg / mL. At the end of 2003, the research group (Bioorg.Med.Chem2004, 12, 6287-6299.) proved that cameline A can stabilize the "DNA-topo I" joint between DNA phosphodiester backbone and topoisomerase I. Valence binary complex. This proves that its mechanism of action is similar to that of camptothecin, which can inhibit the activity of topoisomerase I. In 2004, the Zhongze Ma research group of Toho University in Japan (Bioorg.Med.Chem.Lett.2004, 14, 1193-1196.) repo...

Claims

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Application Information

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IPC IPC(8): A01N43/90A01P3/00A01P1/00
CPCA01N43/90
Inventor 汪清民郝亚男刘玉秀王兹稳宋红健李永强
Owner NANKAI UNIV
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