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Application of topsentin alkaloids in anti-plant viruses and bacteria

A technology for alkaloids and tobacco mosaic virus, which is applied in botanical equipment and methods, chemicals for biological control, applications, etc., and can solve the problem of harsh rearrangement reaction conditions, low natural content of alkaloids, and insufficient research on biological activities. in-depth questions

Active Publication Date: 2021-04-02
NANKAI UNIV
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  • Summary
  • 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 anti-plant viruses and bacteria
  • Application of topsentin alkaloids in anti-plant viruses and bacteria
  • Application of topsentin alkaloids in anti-plant viruses and bacteria

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0059] I-1: Yellow solid, melting point 291-293°C, 1 H NMR (400MHz, DMSO-d 6 +1%TFA) δ12.54(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, 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,...

Embodiment 2

[0067] Embodiment 2: the assay of anti-tobacco mosaic virus activity, assay procedure is as follows:

[0068] 1. Virus purification and concentration determination:

[0069] 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.

[0070] 2. Compound solution preparation:

[0071] 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.

[0072] 3. In vitro effect:

[0073] Rub inoculation of leaves of Shanxi tobacco at the right age, rinse with running water, the virus concentration is 10 μg...

Embodiment 3

[0084] Embodiment 3: antibacterial activity test, assay procedure is as follows:

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

[0086] 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 cont...

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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 species of known marine organisms accounts for more than 80% of the earth's organisms (J Antibiot (Tokyo), 1994, 47, 1425-1433). More than 7,000 kinds of marine natural products have been isolated from sharks, corals and other marine organisms, and the newly discovered compounds are still increasing at an accelerated rate. Among 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% of the compounds have novel structures. It has remarkable activity and is very likely to be developed into a drug (Chem. Rev. 2015, 115, 9655-9706...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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