High-activity asiatic striga lactone derivative and preparation and application thereof

A plant and compound technology, applied in the field of plant hormones and chemical synthesis, can solve the problems of restricting large-scale promotion and use, many intermediate steps in synthesis, and high production costs, and achieve the effects of convenient synthesis, promoting leaf aging, and simple structure

Active Publication Date: 2018-11-30
TSINGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the most widely used and effective SLs analog is GR24. The existing GR24 synthesis route mainly uses 1-indanone as a raw material, but due to many int

Method used

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  • High-activity asiatic striga lactone derivative and preparation and application thereof
  • High-activity asiatic striga lactone derivative and preparation and application thereof
  • High-activity asiatic striga lactone derivative and preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Embodiment 1, the preparation of strigolactone structural analogue SL1 shown in formula I

[0043] according to figure 1 The shown synthetic route diagram prepares the strigolactone structural analogue SL1 shown in formula I.

[0044] Starting lactone 1 (0.79 g, 8.05 mmol) was dissolved in CCl 4 (39mL), NBS (1.58g, 8.8mmol) and BPO (20mg, 0.083mmol) were added sequentially under stirring at room temperature, and heated to reflux for 2 hours. The reaction solution was filtered, and the filter cake was filtered with CCl 4 After washing, the filtrate was concentrated to give light yellow oil 2.

[0045] Bromide 2 was dissolved in DCM (32mL), and 2-nitrophenol (1.12g, 8.05mmol), tetrabutylammonium bromide (2.59g, 8.05mmol) and potassium carbonate (1.33g, 9.62mmol) were added successively under stirring at room temperature ) in aqueous solution (24mL), react overnight at room temperature. The reaction solution was diluted with EtOAc, and the organic phase was successive...

Embodiment 2

[0046] Example 2, SL1 promotes the interaction between Arabidopsis SMXL7 and AtD14

[0047] 1) Take 20ml 6×His-Flag-SMXL7 insect cell culture medium, centrifuge, discard the supernatant, and resuspend the cell pellet with 1mL buffer (50mM Tris-HCl pH7.0, 150mM NaCl, 0.5% Tween 20).

[0048] 2) Broken cells: liquid nitrogen-room temperature water was repeatedly frozen and thawed three times. After freezing and thawing, centrifuge (4°C, maximum speed for 10 minutes).

[0049] 3) After centrifugation, take the supernatant and incubate with Flag gel (Sigma) to combine, the condition is: 4°C, 1h.

[0050] 4) After the reaction, wash the unbound protein with buffer, then add 10 μg GST-D14 and 0, 1, 3, 5, 10 μM GR24 and SL1 for incubation, the condition is: 25°C, 1h.

[0051]5) After the reaction, discard the supernatant, and wash the unbound protein with buffer. Take 120uL 0.2mg / mlflag peptide to compete for elution, the conditions are: 4°C, 30min.

[0052] 6) After the reaction...

Embodiment 3

[0055] Example 3, SL1 inhibits the elongation of Arabidopsis hypocotyl

[0056] 1) Preparation of MS medium (0.6% agar) (1L formulation): 4.43g MS powder (Phytotechlab), 20g sucrose, 6g agar, pH 5.9-6.0. High-pressure steam sterilization at 121°C for 15 minutes.

[0057] 2) Sow the seeds of Col-0 and max2-3 (SALK_092836) in the MS medium supplemented with 0, 1, 3, 5, 10 μM of GR24 or SL1, and keep away from light at 4°C for three days.

[0058] 3) Take out the plate and put it in the plant room to grow for 7 days, the conditions are: low light and full light, 18-22°C.

[0059] 4) the seedlings are pulled out, placed on a 1% agar plate, scanned into a picture format, and the hypocotyl lengths of the seedlings under different treatments are measured with Digimizer software, and significant analysis is carried out with the ANOVA method of the SPSS software (results see Figure 5 ).

[0060] Depend on Figure 5 It can be seen that SL1 inhibits the elongation of the hypocotyl o...

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Abstract

The invention provides an asiatic striga lactone analogue, a preparation method therefor and application of the asiatic striga lactone analogue. The asiatic striga lactone analogue has a structural formula represented by a formula I shown in the description. The asiatic striga lactone analogue provided by the invention has a significant role in the aspects of regulating and controlling the growthand development of plants, promoting the germination of parasitic weed seeds, promoting the stretching of mycelia of arbuscular mycorrhizae, and the like. Natural asiatic striga lactones are complicated in molecular structure and high in artificial synthesis cost. Therefore, the design and synthesis of analogues of the asiatic striga lactones have important scientific and application values. The invention reports preparation and application of the asiatic striga lactone analogue with simple structure and high bioactivity.

Description

technical field [0001] The invention relates to the fields of plant hormones and chemical synthesis, in particular to a highly active strigolactone structural analogue and its preparation and application. Background technique [0002] Strigolactones (SLs) are a class of terpenoid lactone small molecules and a new type of plant hormones. More than 40 years ago, people extracted Strigol from cotton root exudate for the first time, which can induce the germination of Striga and Liedang seeds. With the development of extraction and determination technology, nearly 20 kinds of SLs have been detected in plants, including Strigol, Orbanchol, Sorgolactone, etc. 5-Deoxystrigol was isolated as the first fungal branching factor from lotus japonicus root thorn secretion, and has been found in many species of monocotyledonous and dicotyledonous plants. found in plants. [0003] After continuous scientific research, it has been proved that SLs can be used as a new type of plant endogen...

Claims

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Application Information

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IPC IPC(8): C07D307/60A01N43/08A01P21/00
CPCA01N43/08C07D307/60
Inventor 闫建斌李玉文李素华陈林海南发俊谢道昕
Owner TSINGHUA UNIV
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