Rzemieniecki Tomasz, Kleiber Tomasz, Pernak Juliusz
Department of Chemical Technology, Poznan University of Technology Berdychowo 4 Poznan 60-965 Poland
Department of Agronomy, Horticulture and Bioengineering, Poznan University of Life Sciences Zgorzelecka 4 Poznan 60-198 Poland.
RSC Adv. 2021 Aug 13;11(44):27530-27540. doi: 10.1039/d1ra04805h. eCollection 2021 Aug 9.
The use of highly efficient methods and natural raw materials in syntheses of new biologically active substances addresses the current challenges in this area: ensuring the highest possible efficacy at low concentrations and reducing negative environmental impact. In the present study, we applied this strategy to obtain a new group of ionic liquids containing the indole-3-acetate anion, which is a well-known plant growth hormone, and a cation derived from a cinchona alkaloid - quinine or quinidine. A comparison of the derivatization kinetics of both alkaloids was also carried out, and the use of a quaternary quinidine derivative as a source of biologically active ionic liquids is described here for the first time. The structures of the obtained compounds were fully confirmed based on spectral methods. According to analyses of the effects of the obtained compounds on the growth and development of lettuce plants ( L.), the ionic liquids obtained with indole-3-acetate anions exhibited activity at a concentration of 0.5 mg dm, and the length of the alkyl substituent in the alkaloid-derived cation or the chirality of this cation is crucial in determining the biological activity of the compound. In the cases of several salts containing the 1-alkylquininium cation, we recorded significant, beneficial changes in micronutrient content, which directly translated into plant nutritional value, while no signs of phytotoxicity were observed. Analyses of relevant physicochemical properties (, with differential scanning calorimetry, thermogravimetric analysis and solubility analysis) as well as microbial toxicity tests were also performed to evaluate the environmental impacts of the products. The promising results of our study indicate significant potential for application of these new ionic liquids derived from cinchona alkaloids.
在新型生物活性物质的合成中使用高效方法和天然原料，解决了该领域当前面临的挑战：在低浓度下确保尽可能高的功效，并减少对环境的负面影响。在本研究中，我们应用此策略获得了一组新的离子液体，其含有吲哚 - 3 - 乙酸根阴离子（一种著名的植物生长激素）和源自金鸡纳生物碱（奎宁或奎尼丁）的阳离子。还对两种生物碱的衍生化动力学进行了比较，并且首次在此描述了使用季铵化奎尼丁衍生物作为生物活性离子液体的来源。基于光谱方法充分证实了所得化合物的结构。根据对所得化合物对生菜（L.）生长和发育影响的分析，含有吲哚 - 3 - 乙酸根阴离子的离子液体在浓度为0.5 mg dm时表现出活性，生物碱衍生阳离子中烷基取代基的长度或该阳离子的手性对于确定化合物的生物活性至关重要。在几种含有1 - 烷基奎宁鎓阳离子的盐的情况下，我们记录了微量营养素含量的显著有益变化，这直接转化为植物的营养价值，同时未观察到植物毒性迹象。还进行了相关物理化学性质的分析（通过差示扫描量热法、热重分析和溶解度分析）以及微生物毒性测试，以评估产品对环境的影响。我们研究的有前景的结果表明，这些源自金鸡纳生物碱的新型离子液体具有巨大的应用潜力。
