Laboratory of Insect Toxicology, South China Agricultural University, Guangzhou 510642, China.
Molecules. 2010 Nov 2;15(11):7775-91. doi: 10.3390/molecules15117775.
In a continuing effort to develop novel β-carbolines endowed with better insecticidal activity, a simple high-yielding method for the synthesis of harmine compounds starting from L-tryptophan has been developed and a series of 1,3-substituted β-carboline derivatives have been synthesized and evaluated for their cytotoxicity against insect cultured Sf9 cell line in vitro and insecticidal activities against 4th instar larvae of mosquitos, Culex pipiens quinquefasciatus and mustard aphid, Lipaphis erysimi. The results demonstrated that 1-phenyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (compound 2) and methyl 1-phenyl-β-carboline-3-carboxylate (compound 13) represented the best potential compounds, with Sf9 cells inhibition rates of 71.55% and 60.21% after 24 h treatment at concentrations of 50-200 mg/L, respectively. Both compounds 2 and 13 also showed strong insecticidal activity towards 4th instar larvae of mosquitos with LC(50) values of 20.82 mg/L and 23.98 mg/L, and their LC(90) values were 88.29 mg/L and 295.13 mg/L, respectively. Furthermore, the LC(50) values of compounds 2 and 13 against mustard aphids were 53.16 mg/L and 68.05 mg/L, and their LC(90) values were 240.10 mg/L and 418.63 mg/L after 48 h treatment. The in vitro cytotoxicity of these compounds was consistent with the insecticidal activity in vivo. The results indicated that the 1- and 3-positions of the β-carboline ring deserve further investigation to develop biorational insecticides based on the natural compound harmine as a lead compound.
为了开发具有更好杀虫活性的新型β-咔啉化合物，我们从 L-色氨酸出发开发了一种简单、高产的合成哈尔敏化合物的方法，并合成了一系列 1,3-取代的β-咔啉衍生物，评估了它们对昆虫培养 Sf9 细胞系的体外细胞毒性以及对蚊虫 4 龄幼虫、致倦库蚊和菜蚜的杀虫活性。结果表明，1-苯基-1,2,3,4-四氢-β-咔啉-3-羧酸（化合物 2）和 1-苯基-β-咔啉-3-羧酸甲酯（化合物 13）表现出最好的潜力，在浓度为 50-200 mg/L 时，24 h 处理后 Sf9 细胞抑制率分别为 71.55%和 60.21%。化合物 2 和 13 对 4 龄幼虫也表现出很强的杀虫活性，LC50 值分别为 20.82 mg/L 和 23.98 mg/L，LC90 值分别为 88.29 mg/L 和 295.13 mg/L。此外，化合物 2 和 13 对菜蚜的 LC50 值分别为 53.16 mg/L 和 68.05 mg/L，48 h 处理后的 LC90 值分别为 240.10 mg/L 和 418.63 mg/L。这些化合物的体外细胞毒性与体内杀虫活性一致。结果表明，β-咔啉环的 1-位和 3-位值得进一步研究，以天然化合物哈尔敏为先导化合物开发基于生物合理性的杀虫剂。
