Solanidine Compounds with Spacer Arms for Pest Control
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Solution Overview
Problem
Natural glycoalkaloids, such as chaconine and solanine, while effective against pests, face challenges due to resistance mechanisms developed by certain species, and there is a need for compounds with increased stability and biological properties to enhance their efficacy and explore new uses beyond traditional applications.
Innovation Solution
Development of new compounds with a spacer arm between saccharide units and solanidine, using O-glycosidic or S-glycosidic bonds, which increases stability and flexibility, potentially overcoming steric hindrance and enhancing cytotoxic activity, and a process involving copper-catalyzed alkyne-azide cycloaddition for synthesis.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If natural glycoalkaloids (chaconine and solanine) are used for pest control, then they exhibit toxic and repellent properties against aphids and other pests, but certain species have developed resistance mechanisms to these compounds
Solution Approach 1:
The patent modifies the chemical structure of natural glycoalkaloids by introducing a spacer arm between the saccharide units and solanidine aglycone. This structural parameter change creates new compounds with altered biological properties that overcome pest resistance while maintaining toxic and repellent activities. The spacer arm modification allows the compounds to bypass resistance mechanisms developed against natural glycoalkaloids.
Solution Approach 2:
The invention creates composite molecular structures combining solanidine aglycone with modified saccharide units connected via a triazole-containing spacer arm. This composite approach integrates different functional elements (aglycone core, flexible spacer, saccharide moieties) to produce compounds with enhanced and novel biological activities that differ from natural glycoalkaloids, thereby overcoming resistance.
2Reliability
If a spacer arm is introduced between saccharide units and solanidine, then stability and biological properties are increased, but the molecular structure becomes more complex
Solution Approach 1:
The triazole-containing spacer arm acts as an intermediary element between the solanidine aglycone and saccharide units. This mediator provides flexibility and appropriate spatial separation, preventing steric hindrance while maintaining the biological activity of the aglycone. The spacer arm serves as a flexible link that connects the functional components without compromising their individual roles.
Solution Approach 2:
The molecule is segmented into distinct functional domains: the solanidine aglycone core, the triazole-containing spacer arm, and the saccharide units. This segmentation allows each component to fulfill its specific function independently while contributing to the overall stability and biological activity of the compound.
3Volume of moving object
If the saccharide part is positioned close to the aglycone part, then the molecular structure is more compact, but steric hindrance limits the inhibitory activity on enzymes
Solution Approach 1:
The spacer arm serves as a necessary intermediary that maintains optimal distance between the saccharide part and aglycone part. This intermediate structure prevents steric hindrance by ensuring sufficient spatial separation, allowing the aglycone to access and inhibit target enzymes (acetylcholinesterase and butyrylcholinesterase) effectively without being blocked by the saccharide units.
4Reliability
If natural glycoalkaloids are used, then they exhibit cytotoxic activity by acting on the cell membrane, but they are rather rigid molecules which limits their flexibility
Solution Approach 1:
The introduction of the triazole-containing spacer arm transforms the rigid structure of natural glycoalkaloids into a more dynamic and flexible molecule. The spacer arm provides rotational freedom and conformational flexibility, allowing the molecule to adapt to different binding configurations on cell membranes and enzymes, thereby enhancing cytotoxic activity and membrane disruption capabilities.
Applied Scientific Principles
This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.
Function Achieved in This Case
The new compounds demonstrate improved stability and biological properties, effectively inhibiting enzymes and exhibiting membranolytic properties, offering enhanced efficacy as insecticides, particularly against aphids, with a process yielding high purity and high yield, expanding their application in phytosanitary protection.
Implementation Method 1
a compound of formula (II) is reacted, in the presence of a catalyst, with a compound of formula (III)... the coupling by copper-catalyzed alkyne-azide cycloaddition (CuAAC)
Data Source
Figure 1A~1B
Figure 2~3
AI summary
The invention relates to novel solanidine-derived compounds, the synthesis method thereof and the uses of same in the fields of phytosanitary protection and health. In particular, the invention relates to novel compounds having toxic and/or repellent properties in relation to aphids, as well as other properties.