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Application of Topsentin alkaloids in resistance to plant viruses and germs

A technology against plant viruses and plant pathogens, applied in botany equipment and methods, chemicals for biological control, applications, etc., can solve the problems of insufficient research on biological activity, low total yield, low natural content of alkaloids, etc. question

Active Publication Date: 2018-03-20
NANKAI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

3-Acetylindole (11) reacts with copper bromide to obtain 3-bromoacetylindole (12), and then undergoes nucleophilic substitution with 1,1-dimethylhydrazine to obtain the key intermediate quaternary ammonium salt (13) , rearrangement of the quaternary ammonium salt (13) under heating conditions and then coupling to obtain the alkaloid Topsentin A (Deoxytopsentin, 1), the total yield of this route is low, and the rearrangement reaction conditions are harsh (structural formula 2) (Bull.SOC. Chim. Belg. 1987, 96, 809-812)
[0050] Due to the low natural content of Topsentin alkaloids and the difficulty of synthesis, the research on biological activity is not deep enough, mainly focusing on anticancer activity, and the research on antiviral and bactericidal aspects is still in its infancy. Applications in the

Method used

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  • Application of Topsentin alkaloids in resistance to plant viruses and germs
  • Application of Topsentin alkaloids in resistance to plant viruses and germs
  • Application of Topsentin alkaloids in resistance to plant viruses and germs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Example 1: Experimental data of Topsentin alkaloids I-1~I-8

[0059] I-1: yellow solid, melting point 291-293°C, 1 H NMR(400MHz, DMSO-d 6 +1%TFA) δ 12.54 (s, 1H), 11.67 (s, 1H), 8.80 (s, 1H), 8.35-8.27 (m, 1H), 8.14 (s, 2H), 8.04 (d, J= 7.7Hz, 1H), 7.67-7.58 (m, 1H), 7.53 (d, J=7.9Hz, 1H), 7.37-7.32 (m, 2H), 7.23 (dt, J=14.9, 6.9Hz, 2H). 13 CNMR(100MHz, DMSO-d 6 +1%TFA)δ171.5, 140.6, 138.7, 136.8, 136.4, 130.9, 125.7, 125.7, 124.1, 124.1, 123.0, 121.2, 120.4, 119.3, 115.8, 113.5, 112.8, 112.2, 110.7, 102.3. HRMS (ESI )calcd for C 20 H 15 N 4 O(M+H) + 327.1240, found 327.1248.

[0060] I-2: Yellow solid, melting point 227°C (decomposition), 1 H NMR(400MHz, DMSO-d 6 +1%TFA)δ12.46(s, 1H), 11.74(s, 1H), 11.12(br, TFA), 8.92(s, 1H), 8.33(m, 1H), 8.11(s, 1H), 8.04 (s, 1H), 8.02 (d, J = 7.2Hz, 1H), 7.71 (s, 1H), 7.61-7.59 (m, 1H), 7.35-7.32 (m, 2H), 7.29 (s, 1H). 13 CNMR(100MHz, DMSO-d 6 +1%TFA)δ174.1, 143.4, 137.9, 137.4, 136.6, 132.6, 132.5, 126.4, 125.5, 123.6, 122.9, 122.5, 12...

Embodiment 2

[0067] Example 2: Determination of anti-tobacco mosaic virus activity, the determination procedure is as follows:

[0068] 1. Virus purification and concentration determination:

[0069] Virus purification and concentration determination shall be implemented in accordance with the SOP specifications 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 determined, and it was refrigerated at 4°C for later use.

[0070] 2. Compound solution preparation:

[0071] After weighing, add DMF to dissolve the original medicine to make 1×10 5 μg / mL mother liquor, then diluted with 1‰ Tween 80 aqueous solution to the required concentration; Ningnanmycin preparations were directly diluted with water.

[0072] 3. In vitro effects:

[0073] The appropriate age leaves of Shanxi tobacco were inoculated by friction, washed with running water, and the virus concentration was 1...

Embodiment 3

[0084] Example 3: Antibacterial activity test, the determination procedure is as follows:

[0085] A. In vitro sterilization test, bacterial growth rate determination method (plate method):

[0086] Dissolve a certain amount of medicament in an appropriate amount of acetone, and then dilute it with an aqueous solution containing 200ug / mL emulsifier to the required concentration, then draw 1mL of the drug solution into the petri dish, and then add 9mL of medium respectively, shake it and make 50ug / mL of medicine-containing plate, with 1 mL of sterilized water added as a blank control. Use a punch with a diameter of 4 mm to cut the bacterial disc along the outer edge of the mycelium and move it to the medicated plate. Each treatment was repeated three times. Place the petri dish in a constant temperature incubator at 24±1°C for culture. After 48 hours, investigate the expanded diameter of each treatment plate, calculate the average value, and compare with the blank control to cal...

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Abstract

The invention relates to application of Topsentin alkaloids from I-1 to I-8 in application of resistance to plant viruses and germs. Topsentin alkaloids from I-1 to I-8 show especially excellent anti-plant virus activity and can well inhibit tobacco mosaic viruses (TMV). The compounds also show good anti-plant germ activity. (A structural formula of the compounds is described in the specification).

Description

Technical field [0001] The invention relates to the application of Topsentin alkaloids in resisting plant viruses and germs, and belongs to the technical field of agricultural protection. Background technique [0002] The ocean is a natural treasure house of human material resources. The total number of known marine organisms accounts for more than 80% of the earth’s organisms (J Antibiot (Tokyo), 1994, 47, 1425-1433). At present, there are many kinds of sea squirts, sea squirts, sea squirts, More than 7,000 marine natural products have been isolated from marine organisms such as sharks and corals, and newly discovered compounds are still increasing at an acceleration. The discovered compounds include terpenoids, polypeptides, steroids, polyethers, alkaloids, macrolides, polysaccharides and other compounds. About 50% have various biological activities, and more than 0.1% have novel structures. The activity is significant, and it is very likely to develop into a medicine (Chem. R...

Claims

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Application Information

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IPC IPC(8): A01N43/50A01P1/00
CPCA01N43/50
Inventor 汪清民冀晓霏刘玉秀王兹稳
Owner NANKAI UNIV
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