Cytotoxic and insecticidal activities of derivatives of harmine, a natural insecticidal component isolated from Peganum harmala.
Cytotoxic and insecticidal activities of derivatives of harmine, a natural insecticidal component isolated from Peganum harmala.
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从骆驼蓬中分离出的天然杀虫成分骆驼蓬碱衍生物的细胞毒性和杀虫活性
DOI：
10.3390/molecules15117775
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发表时间：
2010-11-02
期刊：
影响因子：
--
通讯作者：
Zhong G
中科院分区：
文献类型：
--
作者：
Zeng Y;Zhang Y;Weng Q;Hu M;Zhong G
为了开发新的具有更好杀虫活性的β-咔啉类化合物，我们以L-色氨酸为起始原料，发展了一种简便、高产率的去氢骆驼蓬碱类化合物的合成方法，合成了一系列1，3-取代的β-咔啉衍生物，并评价了它们对昆虫培养的Sf 9细胞系的体外细胞毒性和对4龄蚊幼虫的杀虫活性，致倦库蚊和芥菜蚜。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）是最具潜力的化合物，在50-200 mg/L浓度下作用24 h，对Sf 9细胞的抑制率分别为71.55%和60.21%。化合物2和13对4龄蚊幼虫的LC 50分别为20.82 mg/L和23.98 mg/L，LC 90分别为88.29 mg/L和295.13 mg/L。化合物2和13对芥菜蚜虫的LC 50分别为53.16 mg/L和68.05 mg/L，处理48 h后的LC 90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-位结构值得进一步研究，以天然化合物去氢骆驼蓬碱为先导化合物开发生物合理的杀虫剂。
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 LC50 values of 20.82 mg/L and 23.98 mg/L, and their LC90 values were 88.29 mg/L and 295.13 mg/L, respectively. Furthermore, the LC50 values of compounds 2 and 13 against mustard aphids were 53.16 mg/L and 68.05 mg/L, and their LC90 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.
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影响因子：
6.1
作者：
Herraiz, T;Chaparro, C
通讯作者：
Chaparro, C
影响因子：
4.1
作者：
Herraiz, Tomas;Chaparro, Carolina
通讯作者：
Chaparro, Carolina
影响因子：
3.6
作者：
SUSILO, R;ROMMELSPACHER, H
通讯作者：
ROMMELSPACHER, H
影响因子：
4.8
作者：
Rizwan-ul-Haq, Muhammad;Hu, Qiong Bo;Zhang, Wan Li
通讯作者：
Zhang, Wan Li
影响因子：
4.2
作者：
Glennon, RA;Dukat, M;Mattson, MV
通讯作者：
Mattson, MV