Application of Hyrtinadine alkaloids and derivatives thereof in prevention and treatment of plant viral and bacterial diseases

A technology for plant virus diseases and plant pathogens, applied in the direction of chemicals, biocides, and fungicides for biological control, which can solve the problem that the biological activity of natural products has not been discovered, and the structural modification and derivation of alkaloid systems have not been reported. and other issues, to achieve a good effect of anti-plant virus and bacteria activity

Active Publication Date: 2020-02-07
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] Although many articles have reported the synthesis of hyrtinadine A, the biological activity of this natural product, especially its agricultural activity, has not been found yet. For this alkaloid Systematic structural modification and derivation have not been reported. Therefore, hyrtinadine A and its derivatives have broad research prospects

Method used

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  • Application of Hyrtinadine alkaloids and derivatives thereof in prevention and treatment of plant viral and bacterial diseases
  • Application of Hyrtinadine alkaloids and derivatives thereof in prevention and treatment of plant viral and bacterial diseases
  • Application of Hyrtinadine alkaloids and derivatives thereof in prevention and treatment of plant viral and bacterial diseases

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Example 1: Experimental data of Hyrtinadine alkaloids and derivatives I-1 to I-6

[0023] I-1: Earthy yellow solid, yield 48%, melting point 296-297°C. 1 H NMR (400MHz, DMSO-d 6 )δ11.42(s, 1H, NH), 11.33(s, 1H, NH), 9.00(s, 2H, Ar-H), 8.88(s, 2H, OH), 8.13(d, J=2.4Hz, 1H, Ar-H), 7.99(s, 1H, Ar-H), 7.82(d, J=2.4Hz, 1H, Ar-H), 7.31(d, J=8.4Hz, 1H, Ar-H), 7.28(d, J=8.8Hz, 1H, Ar-H), 7.22(s, 1H, Ar-H), 6.76-6.67(m, 2H, Ar-H). 13 C NMR (100MHz, DMSO-d 6 )δ161.1, 154.0, 152.3, 152.1, 131.9, 131.8, 129.2, 126.9, 125.9, 125.5, 124.7, 114.6, 113.1, 112.7, 112.6, 112.5, 109.0, 106.7, 103.1. 20 h 15 N 4 o 2 [M+H] + 343.1190, found 343.1190.

[0024] I-2: Yellow solid, yield 90%, melting point 267-269°C. 1 H NMR (400MHz, DMSO-d 6 )δ11.55(s, 1H, NH), 11.45(s, 1H, NH), 9.12(s, 2H, Ar-H), 8.19(d, J=2.8Hz, 1H, Ar-H), 8.12( d, J=2.4Hz, 1H, Ar-H), 7.88(d, J=2.4Hz, 1H, Ar-H), 7.40(d, J=3.6Hz, 1H, Ar-H), 7.38(d, J=3.6Hz, 2H, Ar-H), 6.85(d, J=8.8Hz, 2H, Ar-H), 3.84(s, 6H, CH 3...

Embodiment 2

[0029] Embodiment 2: the mensuration of anti-tobacco mosaic virus activity, assay procedure is as follows

[0030] 1. Virus purification and concentration determination:

[0031] 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.

[0032] 2. Compound solution preparation:

[0033] 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.

[0034] 3. In vivo protection:

[0035] Select Shanxi tobacco with uniform growth at the 3-5 leaf stage, spray the whole plant, and repeat each treatmen...

Embodiment 3

[0045] Embodiment 3: antibacterial activity test, assay procedure is as follows:

[0046] In vitro bactericidal test, bacterial growth rate determination method (plate method):

[0047] Dissolve a certain amount of medicine in an appropriate amount of acetone, then dilute it with an aqueous solution containing 200ug / mL emulsifier to the required concentration, then draw 1mL of the medicine solution into the petri dish, then add 9mL of medium, shake well and make 50ug / mL mL of the drug-containing plate, and a plate with 1 mL of sterilized water added as a blank control. Use a puncher with a diameter of 4mm to cut out the bacterial plate along the outer edge of the hyphae, and move it to the drug-containing plate. 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 the blank control...

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Abstract

The invention relates to application of hyrtinadine alkaloids and derivatives I-1 to I-6 thereof in prevention and treatment of plant viruses and pathogenic bacteria. The hyrtinadine alkaloids and thederivatives I-1 to I-6 thereof show especially excellent plant virus resisting activity, can well inhibit tobacco mosaic virus (TMV), and also show good plant pathogenic bacterium resisting activity.

Description

technical field [0001] The invention relates to the application of hyrtinadine alkaloids and derivatives thereof in the prevention and treatment of plant virus and bacterial diseases, and belongs to the technical field of agricultural protection. Background technique [0002] Hyrtinadine alkaloids are a class of natural products mainly found and isolated from sponges. The main characteristic of the chemical structure of this kind of alkaloids is the indole bipyrimidine structure in the molecule, of course, there are some exceptions. So far, only four such alkaloids have been reported in the literature, namely hyrtinadine A, hyrtinadine B, hyrtinadine C and hyrtinadine D, and their structures are shown in Formula 1. [0003] [0004] Structural formula one [0005] Hyrtinadine A is a novel pyrimidine-bisindole alkaloid isolated from Okinawa marine sponge Hyrtios sp. by Japanese scholar Kobayashi for the first time in 2007 (J.Nat.Prod., 2007, 70:423-424.) . In 2008, the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/14C07F5/02A01P1/00A01P3/00
CPCC07D403/14C07F5/025
Inventor 汪清民刘玉秀董吉王兹稳宋红健李永强
Owner NANKAI UNIV
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