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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
Industrial Crops and Products ( IF 5.6 ) Pub Date : 2020-08-24 , DOI: 10.1016/j.indcrop.2020.112864
Yong Guo , Zhiyan Liu , Enhua Hou , Nannan Ma , Jiangping Fan , Cheng-Yun Jin , Ruige Yang

(+)-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 1H/13C NMR, HR-MS, and IR spectroscopy. Their insecticidal activities against Mythimna separata Walker and Plutella xylostella Linnaeus were evaluated. Compounds B6, B7, B9, B1921 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.



中文翻译:

非食品生物活性天然林产品作为杀虫剂的候选物:来自新奇木(Chamecyparis nootkatensis)的新型N-(1,3-噻唑-2-基)羧酰胺融合(+)- Nootkatone的制备,生物学评估和分子对接研究[D. 唐] Spach

(+)-Nootkatone,一种非食用生物活性天然双环倍半萜烯酮,是从Chamaecyparis nootkatensis分离的[D. 唐]斯帕奇作为可再生森林资源。为了继续努力从非食品生物活性产品开发合成的天然杀虫剂,通过分子杂交制备了一个由30种N-(1,3-噻唑-2-基)羧酰胺融合的(+)-Nootkatone组成的小型文库,并对其进行了表征由1个H / 13 C NMR,HR-MS,和IR光谱。评估了它们对Mythimna separata Walker和Plutella xylostella Linnaeus的杀虫活性。化合物B6B7B9B1921B24对植物分离虫的杀虫活性优于植物性杀虫剂印ach素,其LC 50值为0.55-0.68 mg / mL。特别地,化合物B9显示出比印za素更强的对分离支原体的杀虫活性是其1.87倍。B21小菜蛾的杀虫活性是za素的1.37倍。通过乙酰胆碱酯酶(AChE)的抑制活性和分子对接研究,AChE可能是B9分离支原体的杀虫靶标。此外,三种明显的化合物B9B21B24对正常哺乳动物细胞表现出较低的溶血和细胞毒活性。这些发现将为进一步开发(+)-Nootkatone衍生物作为潜在的合成天然杀虫剂进行有害生物管理提供见识。

更新日期:2020-08-25
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