Non-food bioactive natural forest products as insecticide candidates: Preparation, biological evaluation and molecular docking studies of novel N-(1,3-thiazol-2-yl)carboxamides fused (+)-nootkatone from Chamaecyparis nootkatensis [D. Don] Spach
Non-food bioactive natural forest products as insecticide candidates: Preparation, biological evaluation and molecular docking studies of novel N-(1,3-thiazol-2-yl)carboxamides fused (+)-nootkatone from Chamaecyparis nootkatensis [D. Don] Spach
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DOI：
10.1016/j.indcrop.2020.112864
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发表时间：
2020-11-15
影响因子：
5.9
通讯作者：
Yang, Ruige
中科院分区：
文献类型：
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作者：
Guo, Yong;Liu, Zhiyan;Yang, Ruige
（+）-努卡酮是一种非食用的具有生物活性的天然双环倍半萜酮，是从Chamaparis nootkatensis中分离得到的[D.唐] Spach作为一种可再生森林资源。为了继续从非食品生物活性产物中开发合成天然衍生的杀虫剂，我们通过分子杂交制备了30个N-（1，3-噻唑-2-基）甲酰胺稠合（+）-诺卡酮的小型文库，并通过H-1/C-13 NMR、HR-MS和IR光谱进行了表征。测定了它们对粘虫（Mythimna separata步行者）和小菜蛾（Plutella xylostella Linnaeus）的杀虫活性。化合物B6、B7、B 9、B19-21和B24对粘虫有较好的杀虫活性。与植物源杀虫剂印楝素相比，其LC_（50）为0.55 ~ 0.68 mg/mL。特别地，化合物B 9对M.印楝素的含量更高。B21对小菜蛾的杀虫活性是印楝素的1.37倍。通过乙酰胆碱酯酶（AChE）抑制活性和分子对接研究，推测AChE可能是B 9的杀虫靶标。分离。此外，三个显著的化合物B 9、B21和B24对正常哺乳动物细胞表现出低的溶血和细胞毒活性。这些发现将为进一步开发（+）-诺卡酮衍生物作为潜在的合成天然衍生杀虫剂用于害虫管理提供见解。
(+)-Nootkatone, a non-food bioactive natural bicyclic sesquiterpene ketone, is isolated from Chamaecyparis nootkatensis [D. Don] Spach as a renewable forest resource. In continuation of our effort to develop synthetic natural derived insecticides from non-food bioactive products, a small library of thirty N-(1,3- thiazol-2-yl) carboxamides fused (+)-nootkatone was prepared by molecular hybridization and characterized by H-1/C-13 NMR, HR-MS, and IR spectroscopy. Their insecticidal activities against Mythimna separata Walker and Plutella xylostella Linnaeus were evaluated. Compounds B6, B7, B9, B19-21 and B24 showed better insecticidal activity against M. separata than the botanical insecticide azadirachtin, and their LC50 values ranged from 0.55 -0.68 mg/mL. Particularly, compound B9 exhibited 1.87-fold more pronounced insecticidal activity against M. separata than azadirachtin. The insecticidal activity of B21 against P. xylostella was 1.37-fold of that of azadirachtin. Through acetylcholinesterase (AChE) inhibitory activity and molecular docking studies, AChE may be the insecticidal target of B9 against M. separata. In addition, three pronounced compounds B9, B21 and B24 exhibited low hemolytic and cytotoxic activities on normal mammalian cells. These findings will give insights into the further development of (+)-nootkatone derivatives as potentially synthetic natural derived insecticides for pest management.