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Application of dehydrogenized derivatives of tylophorine in inhibiting activity of tobacco mosaic virus

A tobacco mosaic disease, anti-tobacco mosaic technology, applied in the application field of seraphine dehydrogenation derivatives in anti-tobacco mosaic virus activity, can solve the problems of high toxicity, poor water solubility, and impact on the central nervous system, Achieve excellent anti-plant virus activity

Inactive Publication Date: 2019-03-05
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although phenanthrene and indolizidine alkaloids have very good biological activity, they also have the disadvantages of high central nervous system toxicity, poor water solubility, and instability to light and heat, which affect its practical application.

Method used

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  • Application of dehydrogenized derivatives of tylophorine in inhibiting activity of tobacco mosaic virus
  • Application of dehydrogenized derivatives of tylophorine in inhibiting activity of tobacco mosaic virus
  • Application of dehydrogenized derivatives of tylophorine in inhibiting activity of tobacco mosaic virus

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 19

[0012] Example 1 Synthesis of 9-dehydrosylmenine hydrochloride (compound 1) (method 1)

[0013]

[0014] Add 0.2g (0.52mmol) of Intermediate 1 and 20mL of ethyl formate to a 35mL microwave reactor, set T=100°C, P=100W, P max =250psi, react for 1h. Desolvation under reduced pressure, dichloromethane dilution, 3mol / L hydrochloric acid washing, water washing, saturated brine washing, anhydrous sodium sulfate drying, normal pressure column chromatography (dichloromethane:methanol=40:1), precipitation to obtain intermediate Body 2 white solid 0.2g, yield 95%.

[0015] Add 0.2g (0.49mmol) of intermediate 2 and 20mL of anhydrous toluene to a 50mL reaction flask, add 0.75g (4.89mmol) of phosphorus oxychloride under stirring at room temperature, heat and reflux for 1h, filter with suction, and wash the filter cake with a small amount of methanol , to obtain 0.2 g of orange-yellow solid, yield 95%, melting point: 255-256 ° C; 1 H NMR (300MHz, CDCl 3 )δ11.07(s, 1H), 8.05(s, 1H), 7...

Embodiment 2

[0016] Example 2 Synthesis of 9,13a,14-dehydrosilomenine hydrochloride (compound 2) (method 2)

[0017]

[0018] Add 39.3 mg (0.1 mmol) of sylphenamine and 50 mL of chloroform into a clean and transparent 100 mL round bottom flask, and replace the air in the system with argon three times. The reaction was stirred at room temperature under direct sunlight until conversion was complete. After desolvation under reduced pressure, normal-pressure column chromatography was performed on a basic alumina column (dichloromethane:methanol=40:1 elution) to obtain a yellow-green solid. 1 HNMR (400MHz, DMSO-d 6 )δ10.42(s, 1H), 9.05(s, 1H), 8.00(s, 2H), 7.59(s, 2H), 5.02-4.87(m, 2H), 4.12-3.98(m, 12H), 3.58 -3.48(m, 3H), 2.63-2.53(m, 2H). 13 C NMR (100MHz, DMSO) δ152.7, 150.6, 149.8, 149.4, 149.1, 138.2, 137.9, 127.5, 123.9, 123.2, 119.3, 118.5, 116.2, 106.1, 104.6, 104.4, 104.3, 57.9, 56.5, 5 , 55.9, 30.9, 21.9. HRMS (ESI) calcd for C 24 h 24 NO 4 (M-Cl) + 390.1700, found 390.170...

Embodiment 3

[0019] Embodiment 3: Conventional in vivo bioassay measures the activity of anti-tobacco mosaic virus

[0020] 1. Virus purification and concentration determination:

[0021] Virus purification and concentration determination were carried out in accordance with the SOP specification for tobacco mosaic virus compiled by the Laboratory of Bioassay, 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.

[0022] 2. Compound solution preparation:

[0023] After weighing, the original drug was dissolved in DMF to prepare 1×10 5 μg / mL stock solution, and then diluted to the required concentration with aqueous solution containing 1‰ Tween 80.

[0024] 3. In vivo protection:

[0025] Select Shanxi tobacco with uniform growth at the 3-5 leaf stage, spray the whole plant, and repeat each treatment 3 times, and set a 1‰ Tween 80 aqueous solution as a ...

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Abstract

The invention relates to an application of dehydrogenized derivatives represented by the formula (I) of tylophorine in inhibiting the activity of tobacco mosaic virus. Tylophorine dehydrogenized derivatives (compound 1 and compound 2) have excellent activity on resisting plant viruses and can both well inhibit tobacco mosaic virus (TMV).

Description

technical field [0001] The present invention relates to the application of dehydrogenated derivatives of sylphenine in the aspect of resisting plant tobacco mosaic virus disease. Background technique [0002] In 1935, the first phenanthrene and indolizidine alkaloid, tylophorine, was isolated and identified (Indian J.Med.Res., 1935, 22, 433-441), due to its unique The chemical structure and remarkable biological activity have attracted extensive attention of chemists at home and abroad. For the first time, our research group discovered that this type of alkaloid has very good inhibitory activity against the extremely harmful tobacco mosaic virus (TMV), and based on this, extensive structural modification and transformation have been carried out to optimize the efficient plant virus disease Prevention and control agent NK-007. Although phenanthrene and indolizidine alkaloids have very good biological activity, they also have the disadvantages of high central nervous system ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A01N43/90A01P1/00C07D471/04
CPCA01N43/90C07D471/04
Inventor 汪清民闫长存刘玉秀王兹稳宋红健
Owner NANKAI UNIV
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